# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013

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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


data_B3NB(DL)A
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-(D~0.54~L~0.46~)-alaninate methanol disolvate
;
_chemical_name_common            ?
_chemical_melting_point          401
_chemical_formula_moiety         'C23 H27 N2 O4, C10 H9 N2 O5, 2(C H4 O)'
_chemical_formula_sum            'C35 H44 N4 O11'
_chemical_formula_weight         696.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.936(2)
_cell_length_b                   12.200(3)
_cell_length_c                   34.428(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3333.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    80(2)
_cell_measurement_reflns_used    1857
_cell_measurement_theta_min      2.8340
_cell_measurement_theta_max      31.6963

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      80(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11859
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.1155
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         30.00
_reflns_number_total             8550
_reflns_number_gt                4827
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+4.2426P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         8550
_refine_ls_number_parameters     499
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1684
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1927(4) 0.2739(2) 0.17418(10) 0.0347(8) Uani 1 1 d . . .
O2 O 0.2560(4) -0.3060(3) 0.32322(10) 0.0363(8) Uani 1 1 d . . .
O3 O 0.2893(5) -0.4255(3) 0.26118(10) 0.0428(9) Uani 1 1 d . . .
O4 O 0.2375(5) 0.0965(3) 0.29529(10) 0.0458(10) Uani 1 1 d . . .
N1 N 0.1586(6) 0.0174(3) 0.23837(12) 0.0314(9) Uani 1 1 d . . .
N2 N 0.1266(6) -0.0880(3) 0.10955(12) 0.0417(12) Uani 1 1 d . . .
H2A H 0.1204 -0.1486 0.0932 0.050 Uiso 1 1 calc R . .
C1 C 0.2054(6) -0.1392(4) 0.28567(15) 0.0314(11) Uani 1 1 d . . .
H1A H 0.1978 -0.0946 0.3082 0.038 Uiso 1 1 calc R . .
C2 C 0.2357(7) -0.2513(4) 0.28806(15) 0.0343(12) Uani 1 1 d . . .
C3 C 0.2505(7) -0.3174(4) 0.25460(15) 0.0351(12) Uani 1 1 d . . .
C4 C 0.2239(6) -0.2712(4) 0.21824(14) 0.0323(11) Uani 1 1 d . . .
H4A H 0.2287 -0.3149 0.1954 0.039 Uiso 1 1 calc R . .
C5 C 0.1900(7) -0.1593(4) 0.21594(15) 0.0334(11) Uani 1 1 d . . .
C6 C 0.1866(6) -0.0956(3) 0.24853(14) 0.0293(10) Uani 1 1 d . . .
C7 C 0.1424(7) -0.0922(4) 0.18006(14) 0.0317(11) Uani 1 1 d . . .
C8 C 0.1584(7) 0.0279(4) 0.19508(14) 0.0309(11) Uani 1 1 d . . .
H8A H 0.0584 0.0716 0.1866 0.037 Uiso 1 1 calc R . .
C9 C 0.2075(6) 0.1047(4) 0.26053(16) 0.0341(11) Uani 1 1 d . . .
C10 C 0.2238(7) 0.2128(3) 0.23910(14) 0.0348(12) Uani 1 1 d . . .
H10D H 0.2930 0.2628 0.2552 0.042 Uiso 1 1 calc R . .
H10E H 0.1101 0.2457 0.2370 0.042 Uiso 1 1 calc R . .
C11 C 0.3023(6) 0.2087(4) 0.19767(14) 0.0328(11) Uani 1 1 d . . .
H11A H 0.4164 0.2435 0.1983 0.039 Uiso 1 1 calc R . .
C12 C 0.2523(7) 0.2931(4) 0.13505(15) 0.0407(13) Uani 1 1 d . . .
H12A H 0.3769 0.2969 0.1351 0.049 Uiso 1 1 calc R . .
H12B H 0.2085 0.3643 0.1256 0.049 Uiso 1 1 calc R . .
C13 C 0.1948(8) 0.2020(4) 0.10790(15) 0.0409(13) Uani 1 1 d . . .
H13A H 0.1188 0.2196 0.0875 0.049 Uiso 1 1 calc R . .
C14 C 0.2463(7) 0.0994(4) 0.11148(15) 0.0357(12) Uani 1 1 d . . .
C15 C 0.1870(9) 0.0081(4) 0.08554(15) 0.0460(15) Uani 1 1 d . . .
H15A H 0.2806 -0.0157 0.0685 0.055 Uiso 1 1 calc R . .
H15B H 0.0940 0.0347 0.0689 0.055 Uiso 1 1 calc R . .
C16 C -0.0447(7) -0.0697(5) 0.12611(16) 0.0467(15) Uani 1 1 d . . .
H16A H -0.1313 -0.1074 0.1103 0.056 Uiso 1 1 calc R . .
H16B H -0.0713 0.0095 0.1270 0.056 Uiso 1 1 calc R . .
C17 C -0.0379(7) -0.1177(4) 0.16698(16) 0.0408(14) Uani 1 1 d . . .
H17A H -0.0589 -0.1977 0.1666 0.049 Uiso 1 1 calc R . .
H17B H -0.1215 -0.0822 0.1842 0.049 Uiso 1 1 calc R . .
C18 C 0.3202(6) 0.0889(3) 0.18456(14) 0.0283(10) Uani 1 1 d . . .
H18A H 0.4098 0.0567 0.2015 0.034 Uiso 1 1 calc R . .
C19 C 0.3781(6) 0.0661(4) 0.14213(15) 0.0315(11) Uani 1 1 d . . .
H19A H 0.4858 0.1061 0.1370 0.038 Uiso 1 1 calc R . .
C20 C 0.4098(7) -0.0576(3) 0.13970(16) 0.0374(13) Uani 1 1 d . . .
H20A H 0.4641 -0.0757 0.1146 0.045 Uiso 1 1 calc R . .
H20B H 0.4863 -0.0805 0.1609 0.045 Uiso 1 1 calc R . .
C21 C 0.2439(7) -0.1175(3) 0.14315(15) 0.0346(12) Uani 1 1 d . . .
H21A H 0.2665 -0.1981 0.1422 0.042 Uiso 1 1 calc R . .
C22 C 0.2223(7) -0.2429(4) 0.35736(15) 0.0422(13) Uani 1 1 d . . .
H22A H 0.2392 -0.2887 0.3804 0.063 Uiso 1 1 calc R . .
H22B H 0.1056 -0.2167 0.3567 0.063 Uiso 1 1 calc R . .
H22C H 0.2990 -0.1800 0.3583 0.063 Uiso 1 1 calc R . .
C23 C 0.3185(10) -0.4915(4) 0.22727(17) 0.0540(18) Uani 1 1 d . . .
H23A H 0.3431 -0.5670 0.2352 0.081 Uiso 1 1 calc R . .
H23B H 0.4145 -0.4619 0.2128 0.081 Uiso 1 1 calc R . .
H23C H 0.2179 -0.4906 0.2108 0.081 Uiso 1 1 calc R . .
O5 O 0.2018(13) -0.2763(6) 0.0701(2) 0.048(2) Uani 0.541(6) 1 d PU A 1
O6 O 0.0531(12) -0.1806(6) 0.0279(2) 0.059(2) Uani 0.541(6) 1 d PU A 1
O51 O 0.0862(16) -0.2661(8) 0.0698(3) 0.055(3) Uani 0.459(6) 1 d PU A 2
O61 O 0.2498(16) -0.1799(7) 0.0284(3) 0.077(3) Uani 0.459(6) 1 d PU A 2
O7 O 0.1530(5) -0.5736(3) 0.04009(11) 0.0493(10) Uani 1 1 d . . .
O8 O -0.2072(5) -0.9026(3) 0.05388(13) 0.0541(11) Uani 1 1 d . . .
O9 O -0.4758(6) -0.9070(3) 0.04989(14) 0.0588(12) Uani 1 1 d . . .
N4 N -0.3459(7) -0.8580(4) 0.04883(12) 0.0401(11) Uani 1 1 d . A .
C24 C 0.1432(8) -0.2617(4) 0.03726(17) 0.0419(14) Uani 1 1 d . . .
C25 C 0.1475(7) -0.3583(4) 0.00910(17) 0.0381(13) Uani 1 1 d . . .
H251 H 0.2459 -0.4054 0.0161 0.046 Uiso 0.459(6) 1 calc PR A 2
H25 H 0.0852 -0.4352 0.0178 0.046 Uiso 0.541(6) 1 d PR A 1
C28 C -0.1975(9) -0.5724(5) 0.0331(2) 0.0651(19) Uani 1 1 d . . .
H28 H -0.0950 -0.5329 0.0303 0.078 Uiso 0.541(6) 1 calc PR A 1
C29 C -0.1966(8) -0.6849(4) 0.03859(17) 0.0474(15) Uani 1 1 d . A .
H29 H -0.0933 -0.7239 0.0403 0.057 Uiso 1 1 calc R . .
C30 C -0.3500(8) -0.7396(4) 0.04165(15) 0.0370(12) Uani 1 1 d . . .
C31 C -0.5020(7) -0.6866(4) 0.04023(17) 0.0402(14) Uani 1 1 d . A .
H31 H -0.6036 -0.7271 0.0432 0.048 Uiso 1 1 calc R . .
C32 C -0.5082(9) -0.5745(5) 0.0345(2) 0.0565(17) Uani 1 1 d . . .
H281 H -0.6130 -0.5373 0.0325 0.068 Uiso 0.459(6) 1 calc PR A 2
C33 C -0.3557(10) -0.5174(5) 0.0316(2) 0.067(2) Uani 1 1 d . A .
H33A H -0.3577 -0.4400 0.0287 0.080 Uiso 1 1 calc R . .
N31 N 0.0020(10) -0.4189(6) 0.0151(3) 0.031(2) Uani 0.459(6) 1 d P . 2
H31A H -0.0952 -0.3887 0.0090 0.037 Uiso 0.459(6) 1 calc PR A 2
C261 C 0.167(4) -0.326(3) -0.0289(9) 0.056(5) Uani 0.459(6) 1 d PU . 2
H26A H 0.2865 -0.3293 -0.0360 0.084 Uiso 0.459(6) 1 calc PR A 2
H26B H 0.1266 -0.2502 -0.0318 0.084 Uiso 0.459(6) 1 calc PR A 2
H26C H 0.1019 -0.3742 -0.0459 0.084 Uiso 0.459(6) 1 calc PR A 2
C271 C 0.0008(12) -0.5218(8) 0.0299(3) 0.027(3) Uani 0.459(6) 1 d P . 2
N3 N 0.2934(9) -0.4211(5) 0.0145(2) 0.0290(18) Uani 0.541(6) 1 d P . 1
H3 H 0.3894 -0.3918 0.0070 0.035 Uiso 0.541(6) 1 calc PR A 1
C26 C 0.131(3) -0.313(2) -0.0372(7) 0.043(3) Uani 0.541(6) 1 d PU . 1
H26D H 0.1333 -0.3752 -0.0551 0.064 Uiso 0.541(6) 1 calc PR A 1
H26E H 0.2248 -0.2634 -0.0430 0.064 Uiso 0.541(6) 1 calc PR A 1
H26F H 0.0240 -0.2731 -0.0403 0.064 Uiso 0.541(6) 1 calc PR A 1
C27 C 0.3001(11) -0.5227(6) 0.0301(3) 0.030(2) Uani 0.541(6) 1 d P . 1
O100 O 0.1723(9) -0.4159(4) 0.13053(14) 0.101(2) Uani 1 1 d . . .
H100 H 0.1897 -0.3714 0.1124 0.151 Uiso 1 1 calc R . .
C100 C 0.0017(10) -0.4490(7) 0.1300(3) 0.091(3) Uani 1 1 d . . .
H10C H -0.0481 -0.4310 0.1048 0.136 Uiso 1 1 calc R . .
H10A H -0.0599 -0.4106 0.1506 0.136 Uiso 1 1 calc R . .
H10B H -0.0052 -0.5283 0.1344 0.136 Uiso 1 1 calc R . .
O200 O 0.5985(9) -0.2842(4) 0.14823(16) 0.099(2) Uani 1 1 d . . .
H200 H 0.6495 -0.3137 0.1669 0.149 Uiso 1 1 calc R . .
C200 C 0.5570(13) -0.3659(8) 0.1199(2) 0.108(4) Uani 1 1 d . . .
H20E H 0.4736 -0.3362 0.1017 0.162 Uiso 1 1 calc R . .
H20C H 0.5101 -0.4304 0.1330 0.162 Uiso 1 1 calc R . .
H20D H 0.6588 -0.3868 0.1056 0.162 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.038(2) 0.0217(15) 0.044(2) 0.0059(15) 0.0034(18) -0.0005(14)
O2 0.039(2) 0.0337(17) 0.0362(19) 0.0066(16) 0.0013(18) 0.0006(16)
O3 0.058(2) 0.0223(16) 0.048(2) 0.0043(16) -0.002(2) 0.0022(17)
O4 0.072(3) 0.0304(18) 0.035(2) -0.0046(16) -0.003(2) -0.012(2)
N1 0.039(2) 0.0212(18) 0.034(2) 0.0035(17) 0.003(2) -0.0027(18)
N2 0.065(3) 0.029(2) 0.031(2) 0.0007(19) -0.005(2) -0.016(2)
C1 0.029(3) 0.029(2) 0.036(3) 0.001(2) 0.002(2) -0.004(2)
C2 0.040(3) 0.030(2) 0.033(3) 0.005(2) -0.003(3) -0.010(2)
C3 0.037(3) 0.026(2) 0.042(3) 0.000(2) 0.003(3) -0.001(2)
C4 0.040(3) 0.024(2) 0.033(3) -0.003(2) 0.002(2) -0.003(2)
C5 0.041(3) 0.026(2) 0.034(3) 0.003(2) -0.001(3) -0.007(2)
C6 0.027(2) 0.020(2) 0.041(3) -0.004(2) -0.002(2) -0.0043(19)
C7 0.040(3) 0.023(2) 0.032(3) -0.003(2) -0.003(2) -0.011(2)
C8 0.035(3) 0.021(2) 0.036(3) 0.003(2) 0.001(2) 0.000(2)
C9 0.034(3) 0.027(2) 0.042(3) -0.002(2) 0.003(2) -0.006(2)
C10 0.045(3) 0.018(2) 0.041(3) -0.003(2) 0.008(3) 0.000(2)
C11 0.031(3) 0.022(2) 0.045(3) -0.003(2) 0.003(2) 0.001(2)
C12 0.052(3) 0.025(2) 0.045(3) 0.005(2) 0.009(3) 0.003(2)
C13 0.054(4) 0.030(2) 0.039(3) 0.006(2) 0.003(3) -0.004(3)
C14 0.040(3) 0.028(2) 0.039(3) 0.005(2) 0.002(3) -0.004(2)
C15 0.077(4) 0.029(2) 0.032(3) 0.003(2) 0.005(3) -0.021(3)
C16 0.051(4) 0.052(3) 0.037(3) 0.000(3) -0.009(3) -0.020(3)
C17 0.044(3) 0.036(3) 0.042(3) 0.002(3) -0.004(3) -0.011(2)
C18 0.035(3) 0.0149(18) 0.035(3) -0.0013(19) -0.001(2) 0.0018(19)
C19 0.026(2) 0.027(2) 0.041(3) 0.003(2) 0.003(2) -0.003(2)
C20 0.058(3) 0.014(2) 0.040(3) -0.001(2) 0.004(3) -0.001(2)
C21 0.047(3) 0.019(2) 0.038(3) -0.002(2) 0.000(3) -0.006(2)
C22 0.049(3) 0.041(3) 0.037(3) 0.004(2) 0.003(3) 0.003(3)
C23 0.093(5) 0.019(2) 0.049(3) -0.003(2) 0.005(4) 0.004(3)
O5 0.078(6) 0.031(3) 0.035(4) 0.005(3) -0.011(5) 0.014(5)
O6 0.101(6) 0.029(4) 0.046(4) -0.006(3) -0.014(5) 0.025(4)
O51 0.076(7) 0.040(5) 0.050(5) -0.012(4) -0.007(7) -0.028(6)
O61 0.118(7) 0.038(4) 0.073(6) -0.011(4) 0.015(6) -0.040(5)
O7 0.062(3) 0.0336(19) 0.052(2) 0.0074(19) 0.008(2) 0.003(2)
O8 0.050(3) 0.045(2) 0.067(3) 0.003(2) -0.010(2) -0.003(2)
O9 0.054(3) 0.034(2) 0.088(4) 0.003(2) 0.022(2) -0.006(2)
N4 0.048(3) 0.039(2) 0.033(2) -0.002(2) 0.006(2) 0.002(2)
C24 0.056(4) 0.024(2) 0.045(3) -0.001(2) -0.011(3) 0.001(3)
C25 0.028(3) 0.014(2) 0.072(4) -0.002(2) -0.001(3) 0.000(2)
C28 0.068(5) 0.054(4) 0.073(5) 0.006(4) -0.012(4) -0.018(4)
C29 0.051(4) 0.037(3) 0.054(4) 0.008(3) 0.000(3) -0.005(3)
C30 0.052(3) 0.026(2) 0.033(3) 0.001(2) 0.000(3) -0.009(2)
C31 0.035(3) 0.033(3) 0.053(4) 0.004(3) 0.011(3) -0.004(2)
C32 0.072(4) 0.030(3) 0.067(4) 0.011(3) 0.014(4) 0.001(3)
C33 0.083(5) 0.034(3) 0.084(5) 0.009(3) 0.007(5) -0.004(4)
N31 0.009(4) 0.014(4) 0.070(7) 0.000(4) -0.003(4) -0.003(3)
C261 0.072(13) 0.056(10) 0.040(13) -0.005(9) -0.012(9) 0.001(10)
C271 0.020(5) 0.017(5) 0.044(7) -0.010(5) -0.003(5) -0.002(4)
N3 0.021(4) 0.019(3) 0.046(5) 0.000(3) 0.005(3) -0.008(3)
C26 0.047(9) 0.049(8) 0.032(10) -0.002(7) -0.024(6) 0.016(6)
C27 0.032(5) 0.023(4) 0.034(5) 0.008(4) -0.002(4) -0.010(4)
O100 0.181(7) 0.068(3) 0.053(3) 0.004(3) -0.002(4) -0.041(4)
C100 0.062(5) 0.084(6) 0.127(8) -0.002(6) 0.038(5) 0.007(4)
O200 0.155(6) 0.065(3) 0.077(4) 0.006(3) -0.025(4) 0.036(4)
C200 0.131(9) 0.137(8) 0.055(5) -0.013(6) -0.014(6) 0.051(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.430(6) . ?
O1 C12 1.447(6) . ?
O2 C2 1.391(6) . ?
O2 C22 1.430(6) . ?
O3 C3 1.373(5) . ?
O3 C23 1.437(6) . ?
O4 C9 1.224(6) . ?
N1 C9 1.366(6) . ?
N1 C6 1.439(5) . ?
N1 C8 1.496(6) . ?
N2 C16 1.491(7) . ?
N2 C15 1.513(6) . ?
N2 C21 1.528(6) . ?
N2 H2A 0.9300 . ?
C1 C2 1.391(6) . ?
C1 C6 1.393(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.412(7) . ?
C3 C4 1.389(7) . ?
C4 C5 1.394(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.365(6) . ?
C5 C7 1.529(7) . ?
C7 C17 1.532(7) . ?
C7 C21 1.536(7) . ?
C7 C8 1.559(6) . ?
C8 C18 1.527(7) . ?
C8 H8A 1.0000 . ?
C9 C10 1.517(6) . ?
C10 C11 1.557(7) . ?
C10 H10D 0.9900 . ?
C10 H10E 0.9900 . ?
C11 C18 1.536(6) . ?
C11 H11A 1.0000 . ?
C12 C13 1.522(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.323(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.503(7) . ?
C14 C19 1.541(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.525(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.556(7) . ?
C18 H18A 1.0000 . ?
C19 C20 1.532(6) . ?
C19 H19A 1.0000 . ?
C20 C21 1.511(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.237(10) . ?
O6 C24 1.263(9) . ?
O51 C24 1.208(12) . ?
O61 C24 1.344(10) . ?
O7 C27 1.366(9) . ?
O7 C271 1.408(11) . ?
O8 N4 1.240(6) . ?
O9 N4 1.192(6) . ?
N4 C30 1.466(6) . ?
C24 C25 1.526(7) . ?
C25 C261 1.38(3) . ?
C25 N31 1.387(9) . ?
C25 N3 1.401(8) . ?
C25 C26 1.69(2) . ?
C25 H251 1.0000 . ?
C25 H25 1.1020 . ?
C28 C29 1.385(8) . ?
C28 C33 1.424(10) . ?
C28 C271 1.694(12) . ?
C28 H28 0.9500 . ?
C29 C30 1.393(8) . ?
C29 H29 0.9500 . ?
C30 C31 1.369(8) . ?
C31 C32 1.383(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.400(9) . ?
C32 C27 1.654(11) 1_455 ?
C32 H281 0.9500 . ?
C33 H33A 0.9500 . ?
N31 C271 1.354(13) . ?
N31 H25 0.6954 . ?
N31 H31A 0.8800 . ?
C261 H26A 0.9800 . ?
C261 H26B 0.9800 . ?
C261 H26C 0.9800 . ?
N3 C27 1.352(10) . ?
N3 H3 0.8800 . ?
C26 H26D 0.9800 . ?
C26 H26E 0.9800 . ?
C26 H26F 0.9800 . ?
C27 C32 1.654(11) 1_655 ?
O100 C100 1.412(9) . ?
O100 H100 0.8400 . ?
C100 H10C 0.9800 . ?
C100 H10A 0.9800 . ?
C100 H10B 0.9800 . ?
O200 C200 1.432(9) . ?
O200 H200 0.8400 . ?
C200 H20E 0.9800 . ?
C200 H20C 0.9800 . ?
C200 H20D 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.7(4) . . ?
C2 O2 C22 115.8(4) . . ?
C3 O3 C23 116.1(4) . . ?
C9 N1 C6 124.5(4) . . ?
C9 N1 C8 119.3(4) . . ?
C6 N1 C8 109.0(4) . . ?
C16 N2 C15 112.4(5) . . ?
C16 N2 C21 107.5(4) . . ?
C15 N2 C21 113.8(4) . . ?
C16 N2 H2A 107.6 . . ?
C15 N2 H2A 107.6 . . ?
C21 N2 H2A 107.6 . . ?
C2 C1 C6 116.6(5) . . ?
C2 C1 H1A 121.7 . . ?
C6 C1 H1A 121.7 . . ?
C1 C2 O2 122.9(5) . . ?
C1 C2 C3 121.9(5) . . ?
O2 C2 C3 115.2(4) . . ?
O3 C3 C4 124.9(4) . . ?
O3 C3 C2 115.7(4) . . ?
C4 C3 C2 119.4(4) . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 C7 110.7(4) . . ?
C4 C5 C7 128.2(4) . . ?
C5 C6 C1 122.3(4) . . ?
C5 C6 N1 110.4(4) . . ?
C1 C6 N1 127.3(4) . . ?
C5 C7 C17 111.1(4) . . ?
C5 C7 C21 115.5(4) . . ?
C17 C7 C21 101.9(4) . . ?
C5 C7 C8 102.4(4) . . ?
C17 C7 C8 111.4(4) . . ?
C21 C7 C8 114.9(4) . . ?
N1 C8 C18 106.1(4) . . ?
N1 C8 C7 104.4(3) . . ?
C18 C8 C7 116.6(4) . . ?
N1 C8 H8A 109.8 . . ?
C18 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
O4 C9 N1 122.5(4) . . ?
O4 C9 C10 122.0(4) . . ?
N1 C9 C10 115.5(4) . . ?
C9 C10 C11 116.8(4) . . ?
C9 C10 H10D 108.1 . . ?
C11 C10 H10D 108.1 . . ?
C9 C10 H10E 108.1 . . ?
C11 C10 H10E 108.1 . . ?
H10D C10 H10E 107.3 . . ?
O1 C11 C18 114.8(4) . . ?
O1 C11 C10 104.9(4) . . ?
C18 C11 C10 109.7(4) . . ?
O1 C11 H11A 109.1 . . ?
C18 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O1 C12 C13 110.8(4) . . ?
O1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 122.8(5) . . ?
C14 C13 H13A 118.6 . . ?
C12 C13 H13A 118.6 . . ?
C13 C14 C15 123.3(5) . . ?
C13 C14 C19 121.5(5) . . ?
C15 C14 C19 115.1(4) . . ?
C14 C15 N2 110.4(4) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 105.3(5) . . ?
N2 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
N2 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 103.1(4) . . ?
C16 C17 H17A 111.2 . . ?
C7 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C7 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C8 C18 C11 108.4(4) . . ?
C8 C18 C19 112.6(4) . . ?
C11 C18 C19 118.2(4) . . ?
C8 C18 H18A 105.5 . . ?
C11 C18 H18A 105.5 . . ?
C19 C18 H18A 105.5 . . ?
C20 C19 C14 109.5(4) . . ?
C20 C19 C18 106.0(4) . . ?
C14 C19 C18 113.3(4) . . ?
C20 C19 H19A 109.3 . . ?
C14 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C21 C20 C19 109.2(4) . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 111.0(4) . . ?
C20 C21 C7 115.1(4) . . ?
N2 C21 C7 105.0(4) . . ?
C20 C21 H21A 108.5 . . ?
N2 C21 H21A 108.5 . . ?
C7 C21 H21A 108.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 O7 C271 117.8(6) . . ?
O9 N4 O8 122.9(4) . . ?
O9 N4 C30 118.7(5) . . ?
O8 N4 C30 118.4(5) . . ?
O51 C24 O5 44.5(6) . . ?
O51 C24 O6 93.4(9) . . ?
O5 C24 O6 124.0(7) . . ?
O51 C24 O61 118.6(8) . . ?
O5 C24 O61 94.5(8) . . ?
O6 C24 O61 73.6(7) . . ?
O51 C24 C25 124.2(7) . . ?
O5 C24 C25 117.5(5) . . ?
O6 C24 C25 117.1(6) . . ?
O61 C24 C25 114.5(7) . . ?
C261 C25 N31 113.0(16) . . ?
C261 C25 N3 101.0(14) . . ?
N31 C25 N3 112.1(5) . . ?
C261 C25 C24 112.5(16) . . ?
N31 C25 C24 107.3(6) . . ?
N3 C25 C24 110.9(5) . . ?
C261 C25 C26 11(2) . . ?
N31 C25 C26 104.5(11) . . ?
N3 C25 C26 111.7(9) . . ?
C24 C25 C26 110.0(10) . . ?
C261 C25 H251 107.9 . . ?
N31 C25 H251 107.9 . . ?
N3 C25 H251 7.0 . . ?
C24 C25 H251 107.9 . . ?
C26 C25 H251 118.6 . . ?
C261 C25 H25 123.8 . . ?
N31 C25 H25 29.7 . . ?
N3 C25 H25 82.5 . . ?
C24 C25 H25 118.3 . . ?
C26 C25 H25 120.0 . . ?
H251 C25 H25 78.2 . . ?
C29 C28 C33 118.4(6) . . ?
C29 C28 C271 111.5(6) . . ?
C33 C28 C271 130.1(6) . . ?
C29 C28 H28 120.8 . . ?
C33 C28 H28 120.8 . . ?
C271 C28 H28 9.4 . . ?
C28 C29 C30 118.8(6) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
C31 C30 C29 122.8(4) . . ?
C31 C30 N4 119.4(5) . . ?
C29 C30 N4 117.8(5) . . ?
C30 C31 C32 120.2(5) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C33 118.1(6) . . ?
C31 C32 C27 115.1(6) . 1_455 ?
C33 C32 C27 126.8(6) . 1_455 ?
C31 C32 H281 120.9 . . ?
C33 C32 H281 120.9 . . ?
C27 C32 H281 6.2 1_455 . ?
C32 C33 C28 121.7(5) . . ?
C32 C33 H33A 119.1 . . ?
C28 C33 H33A 119.1 . . ?
C271 N31 C25 123.8(7) . . ?
C271 N31 H25 72.1 . . ?
C25 N31 H25 51.8 . . ?
C271 N31 H31A 118.1 . . ?
C25 N31 H31A 118.1 . . ?
H25 N31 H31A 169.4 . . ?
C25 C261 H26A 109.5 . . ?
C25 C261 H26B 109.5 . . ?
H26A C261 H26B 109.5 . . ?
C25 C261 H26C 109.5 . . ?
H26A C261 H26C 109.5 . . ?
H26B C261 H26C 109.5 . . ?
N31 C271 O7 120.3(8) . . ?
N31 C271 C28 111.6(8) . . ?
O7 C271 C28 128.1(7) . . ?
N31 C271 H25 30.1 . . ?
O7 C271 H25 90.2 . . ?
C28 C271 H25 141.7 . . ?
C27 N3 C25 125.9(7) . . ?
C27 N3 H3 117.1 . . ?
C25 N3 H3 117.1 . . ?
C25 C26 H26D 109.5 . . ?
C25 C26 H26E 109.5 . . ?
H26D C26 H26E 109.5 . . ?
C25 C26 H26F 109.5 . . ?
H26D C26 H26F 109.5 . . ?
H26E C26 H26F 109.5 . . ?
N3 C27 O7 118.9(7) . . ?
N3 C27 C32 115.0(7) . 1_655 ?
O7 C27 C32 126.1(6) . 1_655 ?
C100 O100 H100 109.5 . . ?
O100 C100 H10C 109.5 . . ?
O100 C100 H10A 109.5 . . ?
H10C C100 H10A 109.5 . . ?
O100 C100 H10B 109.5 . . ?
H10C C100 H10B 109.5 . . ?
H10A C100 H10B 109.5 . . ?
C200 O200 H200 109.5 . . ?
O200 C200 H20E 109.5 . . ?
O200 C200 H20C 109.5 . . ?
H20E C200 H20C 109.5 . . ?
O200 C200 H20D 109.5 . . ?
H20E C200 H20D 109.5 . . ?
H20C C200 H20D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O2 -179.6(4) . . . . ?
C6 C1 C2 C3 1.3(7) . . . . ?
C22 O2 C2 C1 7.8(7) . . . . ?
C22 O2 C2 C3 -173.1(5) . . . . ?
C23 O3 C3 C4 5.8(8) . . . . ?
C23 O3 C3 C2 -175.0(5) . . . . ?
C1 C2 C3 O3 176.7(5) . . . . ?
O2 C2 C3 O3 -2.5(7) . . . . ?
C1 C2 C3 C4 -4.0(8) . . . . ?
O2 C2 C3 C4 176.8(5) . . . . ?
O3 C3 C4 C5 -178.2(5) . . . . ?
C2 C3 C4 C5 2.6(7) . . . . ?
C3 C4 C5 C6 1.5(8) . . . . ?
C3 C4 C5 C7 -174.4(5) . . . . ?
C4 C5 C6 C1 -4.3(8) . . . . ?
C7 C5 C6 C1 172.2(4) . . . . ?
C4 C5 C6 N1 176.7(5) . . . . ?
C7 C5 C6 N1 -6.7(6) . . . . ?
C2 C1 C6 C5 2.9(7) . . . . ?
C2 C1 C6 N1 -178.4(5) . . . . ?
C9 N1 C6 C5 -155.0(5) . . . . ?
C8 N1 C6 C5 -5.1(6) . . . . ?
C9 N1 C6 C1 26.2(8) . . . . ?
C8 N1 C6 C1 176.0(5) . . . . ?
C6 C5 C7 C17 -104.0(5) . . . . ?
C4 C5 C7 C17 72.2(7) . . . . ?
C6 C5 C7 C21 140.6(4) . . . . ?
C4 C5 C7 C21 -43.2(7) . . . . ?
C6 C5 C7 C8 15.0(6) . . . . ?
C4 C5 C7 C8 -168.8(5) . . . . ?
C9 N1 C8 C18 42.2(6) . . . . ?
C6 N1 C8 C18 -109.5(4) . . . . ?
C9 N1 C8 C7 165.9(4) . . . . ?
C6 N1 C8 C7 14.2(5) . . . . ?
C5 C7 C8 N1 -16.9(5) . . . . ?
C17 C7 C8 N1 101.9(5) . . . . ?
C21 C7 C8 N1 -143.0(4) . . . . ?
C5 C7 C8 C18 99.8(5) . . . . ?
C17 C7 C8 C18 -141.5(4) . . . . ?
C21 C7 C8 C18 -26.3(6) . . . . ?
C6 N1 C9 O4 -20.5(8) . . . . ?
C8 N1 C9 O4 -167.5(5) . . . . ?
C6 N1 C9 C10 158.9(4) . . . . ?
C8 N1 C9 C10 11.9(7) . . . . ?
O4 C9 C10 C11 139.5(5) . . . . ?
N1 C9 C10 C11 -39.9(7) . . . . ?
C12 O1 C11 C18 -66.8(5) . . . . ?
C12 O1 C11 C10 172.8(4) . . . . ?
C9 C10 C11 O1 133.3(4) . . . . ?
C9 C10 C11 C18 9.5(6) . . . . ?
C11 O1 C12 C13 88.3(5) . . . . ?
O1 C12 C13 C14 -65.0(7) . . . . ?
C12 C13 C14 C15 178.3(5) . . . . ?
C12 C13 C14 C19 -4.0(8) . . . . ?
C13 C14 C15 N2 -129.2(6) . . . . ?
C19 C14 C15 N2 52.9(6) . . . . ?
C16 N2 C15 C14 77.6(6) . . . . ?
C21 N2 C15 C14 -45.0(6) . . . . ?
C15 N2 C16 C17 -140.7(4) . . . . ?
C21 N2 C16 C17 -14.7(5) . . . . ?
N2 C16 C17 C7 35.2(5) . . . . ?
C5 C7 C17 C16 -165.1(4) . . . . ?
C21 C7 C17 C16 -41.5(5) . . . . ?
C8 C7 C17 C16 81.5(5) . . . . ?
N1 C8 C18 C11 -70.9(5) . . . . ?
C7 C8 C18 C11 173.3(4) . . . . ?
N1 C8 C18 C19 156.4(4) . . . . ?
C7 C8 C18 C19 40.7(6) . . . . ?
O1 C11 C18 C8 -73.9(5) . . . . ?
C10 C11 C18 C8 43.9(5) . . . . ?
O1 C11 C18 C19 55.7(6) . . . . ?
C10 C11 C18 C19 173.5(4) . . . . ?
C13 C14 C19 C20 179.1(5) . . . . ?
C15 C14 C19 C20 -3.0(6) . . . . ?
C13 C14 C19 C18 61.0(6) . . . . ?
C15 C14 C19 C18 -121.1(5) . . . . ?
C8 C18 C19 C20 -60.7(5) . . . . ?
C11 C18 C19 C20 171.6(4) . . . . ?
C8 C18 C19 C14 59.4(5) . . . . ?
C11 C18 C19 C14 -68.3(5) . . . . ?
C14 C19 C20 C21 -54.2(5) . . . . ?
C18 C19 C20 C21 68.3(5) . . . . ?
C19 C20 C21 N2 62.4(5) . . . . ?
C19 C20 C21 C7 -56.7(6) . . . . ?
C16 N2 C21 C20 -136.3(4) . . . . ?
C15 N2 C21 C20 -11.1(6) . . . . ?
C16 N2 C21 C7 -11.3(5) . . . . ?
C15 N2 C21 C7 113.9(4) . . . . ?
C5 C7 C21 C20 -84.7(5) . . . . ?
C17 C7 C21 C20 154.8(4) . . . . ?
C8 C7 C21 C20 34.3(6) . . . . ?
C5 C7 C21 N2 153.0(4) . . . . ?
C17 C7 C21 N2 32.5(4) . . . . ?
C8 C7 C21 N2 -88.1(5) . . . . ?
O51 C24 C25 C261 160.5(17) . . . . ?
O5 C24 C25 C261 -147.7(16) . . . . ?
O6 C24 C25 C261 45.2(16) . . . . ?
O61 C24 C25 C261 -38.2(17) . . . . ?
O51 C24 C25 N31 35.6(11) . . . . ?
O5 C24 C25 N31 87.4(9) . . . . ?
O6 C24 C25 N31 -79.8(9) . . . . ?
O61 C24 C25 N31 -163.1(8) . . . . ?
O51 C24 C25 N3 -87.2(11) . . . . ?
O5 C24 C25 N3 -35.4(10) . . . . ?
O6 C24 C25 N3 157.4(7) . . . . ?
O61 C24 C25 N3 74.1(9) . . . . ?
O51 C24 C25 C26 148.8(13) . . . . ?
O5 C24 C25 C26 -159.4(12) . . . . ?
O6 C24 C25 C26 33.4(13) . . . . ?
O61 C24 C25 C26 -49.9(12) . . . . ?
C33 C28 C29 C30 1.4(10) . . . . ?
C271 C28 C29 C30 -179.7(6) . . . . ?
C28 C29 C30 C31 -1.4(9) . . . . ?
C28 C29 C30 N4 -177.9(5) . . . . ?
O9 N4 C30 C31 6.5(8) . . . . ?
O8 N4 C30 C31 -172.9(5) . . . . ?
O9 N4 C30 C29 -176.8(5) . . . . ?
O8 N4 C30 C29 3.8(7) . . . . ?
C29 C30 C31 C32 1.9(9) . . . . ?
N4 C30 C31 C32 178.3(6) . . . . ?
C30 C31 C32 C33 -2.3(10) . . . . ?
C30 C31 C32 C27 175.6(6) . . . 1_455 ?
C31 C32 C33 C28 2.4(11) . . . . ?
C27 C32 C33 C28 -175.2(7) 1_455 . . . ?
C29 C28 C33 C32 -2.0(11) . . . . ?
C271 C28 C33 C32 179.4(8) . . . . ?
C261 C25 N31 C271 122.2(18) . . . . ?
N3 C25 N31 C271 8.9(12) . . . . ?
C24 C25 N31 C271 -113.1(10) . . . . ?
C26 C25 N31 C271 130.0(13) . . . . ?
C25 N31 C271 O7 0.0(15) . . . . ?
C25 N31 C271 C28 -179.4(8) . . . . ?
C27 O7 C271 N31 -8.2(12) . . . . ?
C27 O7 C271 C28 171.2(9) . . . . ?
C29 C28 C271 N31 164.8(8) . . . . ?
C33 C28 C271 N31 -16.5(13) . . . . ?
C29 C28 C271 O7 -14.6(13) . . . . ?
C33 C28 C271 O7 164.1(9) . . . . ?
C261 C25 N3 C27 -131.5(18) . . . . ?
N31 C25 N3 C27 -10.9(11) . . . . ?
C24 C25 N3 C27 109.1(8) . . . . ?
C26 C25 N3 C27 -127.8(13) . . . . ?
C25 N3 C27 O7 3.4(12) . . . . ?
C25 N3 C27 C32 -177.5(7) . . . 1_655 ?
C271 O7 C27 N3 6.5(11) . . . . ?
C271 O7 C27 C32 -172.5(8) . . . 1_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.93 1.86 2.734(9) 154.6 .
N2 H2A O51 0.93 1.67 2.588(10) 169.9 .
N31 H31A O61 0.88 1.97 2.776(14) 151.9 4_445
N3 H3 O6 0.88 1.98 2.813(11) 158.0 4_545
O100 H100 O51 0.84 2.12 2.861(13) 147.7 .
O100 H100 O5 0.84 1.86 2.698(9) 173.1 .
O200 H200 O4 0.84 1.92 2.756(6) 170.4 3_645

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065

#===== end

# start Validation Reply Form
_vrf_PLAT770_B3NBDLA             
;
PROBLEM: Suspect C-H Bond in CIF: C271 -- H25 .. 1.32 Ang.
RESPONSE: The C271 and H25 belong to opposite enantiomers of
the disordered alanine derivative.
;
_database_code_depnum_ccdc_archive 'CCDC 930480'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

# end Validation Reply Form



data_B3NB(DL)S
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-(D~0.54~L~0.46~)-serinate methanol 1.57-solvate
;
_chemical_name_common            ?
_chemical_melting_point          411
_chemical_formula_moiety         'C10 H9 N2 O6, C23 H27 N2 O4, 1.57(C H4 O)'
_chemical_formula_sum            'C34.57 H42.28 N4 O11.57'
_chemical_formula_weight         698.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.890(2)
_cell_length_b                   12.081(3)
_cell_length_c                   34.782(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3315.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4370
_cell_measurement_theta_min      2.8311
_cell_measurement_theta_max      28.7305

_exptl_crystal_description       plate
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1481
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22554
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_av_sigmaI/netI    0.1151
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4098
_reflns_number_gt                1933
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4098
_refine_ls_number_parameters     696
_refine_ls_number_restraints     486
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3106(4) 0.1926(3) 0.17679(10) 0.0389(9) Uani 1 1 d . . .
O2 O 0.2445(4) 0.7716(3) 0.32393(9) 0.0409(9) Uani 1 1 d . . .
O3 O 0.2089(5) 0.8921(3) 0.26293(10) 0.0412(9) Uani 1 1 d . . .
O4 O 0.2851(5) 0.3658(3) 0.29669(10) 0.0472(10) Uani 1 1 d . . .
N1 N 0.3544(5) 0.4486(3) 0.23995(11) 0.0322(10) Uani 1 1 d . . .
N2 N 0.4046(6) 0.5522(4) 0.11372(12) 0.0458(13) Uani 1 1 d . . .
H2A H 0.4173 0.6118 0.0980 0.055 Uiso 1 1 calc R . .
C1 C 0.3036(6) 0.6046(4) 0.28677(15) 0.0346(13) Uani 1 1 d . . .
H1A H 0.3103 0.5605 0.3086 0.042 Uiso 1 1 calc R . .
C2 C 0.2678(6) 0.7181(5) 0.28953(14) 0.0360(13) Uani 1 1 d . . .
C3 C 0.2565(6) 0.7826(4) 0.25634(15) 0.0377(14) Uani 1 1 d . . .
C4 C 0.2888(6) 0.7388(4) 0.22051(14) 0.0360(13) Uani 1 1 d . . .
H4A H 0.2851 0.7831 0.1987 0.043 Uiso 1 1 calc R . .
C5 C 0.3272(6) 0.6263(4) 0.21775(14) 0.0345(13) Uani 1 1 d . . .
C6 C 0.3286(6) 0.5609(4) 0.25073(14) 0.0314(12) Uani 1 1 d . . .
C7 C 0.3773(7) 0.5597(4) 0.18301(14) 0.0332(13) Uani 1 1 d . . .
C8 C 0.3528(6) 0.4386(4) 0.19729(13) 0.0311(12) Uani 1 1 d . . .
H8A H 0.4489 0.3931 0.1889 0.037 Uiso 1 1 calc R . .
C9 C 0.3053(7) 0.3593(4) 0.26192(18) 0.0391(14) Uani 1 1 d . . .
C10 C 0.2723(7) 0.2536(4) 0.24061(14) 0.0404(14) Uani 1 1 d . . .
H10A H 0.1933 0.2101 0.2557 0.049 Uiso 1 1 calc R . .
H10B H 0.3778 0.2125 0.2396 0.049 Uiso 1 1 calc R . .
C11 C 0.2012(7) 0.2608(4) 0.19893(14) 0.0361(13) Uani 1 1 d . . .
H11A H 0.0871 0.2289 0.1985 0.043 Uiso 1 1 calc R . .
C12 C 0.2554(8) 0.1737(4) 0.13757(15) 0.0452(15) Uani 1 1 d . . .
H12A H 0.1326 0.1700 0.1368 0.054 Uiso 1 1 calc R . .
H12B H 0.2996 0.1034 0.1286 0.054 Uiso 1 1 calc R . .
C13 C 0.3151(7) 0.2641(4) 0.11172(14) 0.0392(14) Uani 1 1 d . . .
H13A H 0.3909 0.2457 0.0923 0.047 Uiso 1 1 calc R . .
C14 C 0.2678(7) 0.3682(4) 0.11457(15) 0.0401(14) Uani 1 1 d . . .
C15 C 0.3370(8) 0.4585(4) 0.08917(15) 0.0464(15) Uani 1 1 d . . .
H15A H 0.2481 0.4860 0.0724 0.056 Uiso 1 1 calc R . .
H15B H 0.4272 0.4292 0.0732 0.056 Uiso 1 1 calc R . .
C16 C 0.5748(7) 0.5299(5) 0.13139(15) 0.0463(16) Uani 1 1 d . . .
H16A H 0.6644 0.5644 0.1165 0.056 Uiso 1 1 calc R . .
H16B H 0.5964 0.4510 0.1330 0.056 Uiso 1 1 calc R . .
C17 C 0.5631(7) 0.5805(5) 0.17100(15) 0.0431(15) Uani 1 1 d . . .
H17A H 0.5880 0.6591 0.1702 0.052 Uiso 1 1 calc R . .
H17B H 0.6410 0.5447 0.1886 0.052 Uiso 1 1 calc R . .
C18 C 0.1905(6) 0.3824(4) 0.18677(13) 0.0303(12) Uani 1 1 d . . .
H18A H 0.1026 0.4160 0.2029 0.036 Uiso 1 1 calc R . .
C19 C 0.1362(7) 0.4042(4) 0.14451(15) 0.0371(13) Uani 1 1 d . . .
H19A H 0.0286 0.3664 0.1394 0.045 Uiso 1 1 calc R . .
C20 C 0.1102(7) 0.5301(4) 0.14114(16) 0.0371(14) Uani 1 1 d . . .
H20A H 0.0320 0.5553 0.1608 0.044 Uiso 1 1 calc R . .
H20B H 0.0629 0.5481 0.1162 0.044 Uiso 1 1 calc R . .
C21 C 0.2830(7) 0.5876(4) 0.14619(14) 0.0403(14) Uani 1 1 d . . .
H21A H 0.2664 0.6679 0.1449 0.048 Uiso 1 1 calc R . .
C22 C 0.2676(7) 0.7064(5) 0.35797(14) 0.0465(15) Uani 1 1 d . . .
H22A H 0.2511 0.7521 0.3802 0.070 Uiso 1 1 calc R . .
H22B H 0.3804 0.6765 0.3583 0.070 Uiso 1 1 calc R . .
H22C H 0.1869 0.6469 0.3582 0.070 Uiso 1 1 calc R . .
C23 C 0.1802(8) 0.9579(4) 0.22935(16) 0.0550(17) Uani 1 1 d . . .
H23A H 0.1574 1.0330 0.2368 0.082 Uiso 1 1 calc R . .
H23B H 0.0849 0.9290 0.2154 0.082 Uiso 1 1 calc R . .
H23C H 0.2790 0.9560 0.2133 0.082 Uiso 1 1 calc R . .
N4 N -0.1426(7) 1.3487(4) 0.05185(13) 0.0408(12) Uani 1 1 d . . .
O5 O 0.5552(17) 0.7021(9) 0.0510(4) 0.103(4) Uani 0.540(6) 1 d PU A 1
O6 O 0.285(2) 0.7308(10) 0.0721(3) 0.086(4) Uani 0.540(6) 1 d PU A 1
O7 O 0.356(2) 0.7590(18) -0.0325(6) 0.060(5) Uani 0.540(6) 1 d PU A 1
H7 H 0.2622 0.7863 -0.0361 0.090 Uiso 0.540(6) 1 calc PR A 1
O8 O 0.352(4) 1.081(2) 0.0340(6) 0.058(7) Uani 0.540(6) 1 d PU A 1
O9 O -0.022(3) 1.396(2) 0.0599(5) 0.040(4) Uani 0.540(6) 1 d PU A 1
O10 O -0.266(4) 1.397(3) 0.0594(9) 0.050(5) Uani 0.540(6) 1 d PU A 1
N3 N 0.2370(13) 0.9147(8) 0.0309(3) 0.050(3) Uani 0.540(6) 1 d PU A 1
H3 H 0.1462 0.8754 0.0318 0.060 Uiso 0.540(6) 1 calc PR A 1
C24 C 0.419(3) 0.7535(16) 0.0548(7) 0.069(6) Uani 0.540(6) 1 d PU A 1
C25 C 0.407(3) 0.8591(18) 0.0286(6) 0.066(6) Uani 0.540(6) 1 d PU A 1
H25 H 0.4888 0.9122 0.0393 0.079 Uiso 0.540(6) 1 calc PR A 1
C26 C 0.4626(17) 0.8380(11) -0.0110(4) 0.068(4) Uani 0.540(6) 1 d PU A 1
H26A H 0.5778 0.8099 -0.0104 0.081 Uiso 0.540(6) 1 calc PR A 1
H26B H 0.4643 0.9077 -0.0248 0.081 Uiso 0.540(6) 1 calc PR A 1
C27 C 0.2267(13) 1.0258(7) 0.0314(3) 0.026(2) Uani 0.540(6) 1 d PU A 1
C28 C 0.0600(16) 1.0745(10) 0.0303(4) 0.033(3) Uani 0.540(6) 1 d PU A 1
C29 C 0.040(2) 1.184(2) 0.0403(7) 0.038(4) Uani 0.540(6) 1 d PU A 1
H29 H 0.1334 1.2279 0.0458 0.046 Uiso 0.540(6) 1 calc PR A 1
C30 C -0.161(2) 1.235(2) 0.0422(7) 0.027(4) Uani 0.540(6) 1 d PU A 1
C31 C -0.2621(18) 1.1748(14) 0.0289(4) 0.038(3) Uani 0.540(6) 1 d PU A 1
H31 H -0.3707 1.2043 0.0272 0.046 Uiso 0.540(6) 1 calc PR A 1
C32 C -0.2477(19) 1.0673(11) 0.0154(4) 0.047(3) Uani 0.540(6) 1 d PU A 1
H32 H -0.3415 1.0297 0.0059 0.056 Uiso 0.540(6) 1 calc PR A 1
C33 C -0.0819(18) 1.0150(11) 0.0167(4) 0.037(3) Uani 0.540(6) 1 d PU A 1
H33 H -0.0693 0.9421 0.0086 0.045 Uiso 0.540(6) 1 calc PR A 1
O51 O -0.5333(16) 0.7177(10) 0.0695(3) 0.041(3) Uani 0.460(6) 1 d PU A 2
O61 O -0.8061(11) 0.6907(7) 0.0528(3) 0.042(2) Uani 0.460(6) 1 d PU A 2
O71 O -0.603(2) 0.7464(17) -0.0254(6) 0.045(5) Uani 0.460(6) 1 d PU A 2
H71 H -0.5157 0.7736 -0.0338 0.067 Uiso 0.460(6) 1 calc PR A 2
O81 O -0.631(3) 1.088(2) 0.0266(6) 0.020(3) Uani 0.460(6) 1 d PU A 2
O91 O 0.004(3) 1.400(3) 0.0489(6) 0.044(4) Uani 0.460(6) 1 d PU A 2
O101 O -0.296(4) 1.386(3) 0.0545(11) 0.047(5) Uani 0.460(6) 1 d PU A 2
N31 N -0.5160(14) 0.9138(9) 0.0331(3) 0.037(3) Uani 0.460(6) 1 d PU A 2
H31A H -0.4261 0.8742 0.0355 0.044 Uiso 0.460(6) 1 calc PR A 2
C241 C -0.6735(17) 0.7483(12) 0.0533(5) 0.020(3) Uani 0.460(6) 1 d PU A 2
C251 C -0.677(2) 0.8597(15) 0.0311(5) 0.029(4) Uani 0.460(6) 1 d PU A 2
H251 H -0.7612 0.9078 0.0433 0.035 Uiso 0.460(6) 1 calc PR A 2
C261 C -0.7294(15) 0.8436(9) -0.0119(3) 0.037(3) Uani 0.460(6) 1 d PU A 2
H26C H -0.7116 0.9106 -0.0267 0.045 Uiso 0.460(6) 1 calc PR A 2
H26D H -0.8471 0.8212 -0.0141 0.045 Uiso 0.460(6) 1 calc PR A 2
C271 C -0.5003(15) 1.0229(10) 0.0313(3) 0.029(3) Uani 0.460(6) 1 d PU A 2
C281 C -0.3313(17) 1.0721(11) 0.0319(4) 0.038(3) Uani 0.460(6) 1 d PU A 2
C291 C -0.319(2) 1.1843(16) 0.0393(5) 0.034(4) Uani 0.460(6) 1 d PU A 2
H291 H -0.4114 1.2299 0.0444 0.041 Uiso 0.460(6) 1 calc PR A 2
C301 C -0.114(2) 1.229(3) 0.0381(8) 0.017(4) Uani 0.460(6) 1 d PU A 2
C311 C -0.008(3) 1.178(3) 0.0338(8) 0.038(5) Uani 0.460(6) 1 d PU A 2
H311 H 0.0995 1.2071 0.0380 0.046 Uiso 0.460(6) 1 calc PR A 2
C321 C -0.021(2) 1.0659(15) 0.0221(5) 0.038(3) Uani 0.460(6) 1 d PU A 2
H321 H 0.0754 1.0257 0.0153 0.046 Uiso 0.460(6) 1 calc PR A 2
C331 C -0.182(2) 1.0174(13) 0.0209(4) 0.034(3) Uani 0.460(6) 1 d PU A 2
H331 H -0.1907 0.9448 0.0123 0.041 Uiso 0.460(6) 1 calc PR A 2
O100 O 0.801(3) 0.763(2) 0.1091(6) 0.082(4) Uani 0.273(17) 1 d PDU B 1
H100 H 0.8107 0.7521 0.0859 0.122 Uiso 0.273(17) 1 calc PR B 1
C100 C 0.918(5) 0.860(3) 0.1213(13) 0.083(4) Uani 0.273(17) 1 d PDU B 1
H101 H 0.8764 0.8924 0.1447 0.125 Uiso 0.273(17) 1 calc PR B 1
H102 H 0.9196 0.9153 0.1015 0.125 Uiso 0.273(17) 1 calc PR B 1
H103 H 1.0311 0.8329 0.1254 0.125 Uiso 0.273(17) 1 calc PR B 1
O110 O 0.776(3) 0.822(3) 0.1036(6) 0.081(4) Uani 0.256(16) 1 d PDU C 2
H110 H 0.7880 0.8122 0.0804 0.122 Uiso 0.256(16) 1 calc PR C 2
C110 C 0.949(4) 0.824(3) 0.1231(13) 0.084(4) Uani 0.256(16) 1 d PDU C 2
H111 H 1.0338 0.7998 0.1053 0.125 Uiso 0.256(16) 1 calc PR C 2
H112 H 0.9476 0.7760 0.1450 0.125 Uiso 0.256(16) 1 calc PR C 2
H113 H 0.9737 0.8984 0.1312 0.125 Uiso 0.256(16) 1 calc PR C 2
O120 O 0.874(3) 0.9428(17) 0.1402(6) 0.082(4) Uani 0.237(9) 1 d PDU D 6
H120 H 0.8224 0.9014 0.1548 0.123 Uiso 0.237(9) 1 calc PR D 6
C120 C 0.914(5) 0.885(3) 0.1053(8) 0.084(4) Uani 0.237(9) 1 d PDU D 6
H121 H 1.0322 0.8659 0.1051 0.126 Uiso 0.237(9) 1 calc PR D 6
H122 H 0.8892 0.9313 0.0836 0.126 Uiso 0.237(9) 1 calc PR D 6
H123 H 0.8473 0.8184 0.1037 0.126 Uiso 0.237(9) 1 calc PR D 6
O200 O 0.168(4) 0.870(3) 0.1327(9) 0.059(5) Uani 0.174(12) 1 d PDU E 3
H200 H 0.1540 0.8280 0.1145 0.088 Uiso 0.174(12) 1 calc PR E 3
C200 C 0.365(6) 0.893(4) 0.1380(13) 0.064(4) Uani 0.174(12) 1 d PDU E 3
H201 H 0.4249 0.8244 0.1391 0.096 Uiso 0.174(12) 1 calc PR E 3
H202 H 0.3827 0.9336 0.1615 0.096 Uiso 0.174(12) 1 calc PR E 3
H203 H 0.4055 0.9364 0.1167 0.096 Uiso 0.174(12) 1 calc PR E 3
O210 O 0.4722(16) 0.8868(9) 0.1387(3) 0.055(4) Uani 0.454(15) 1 d PDU F 5
H210 H 0.4961 0.9017 0.1611 0.082 Uiso 0.454(15) 1 calc PR F 5
C210 C 0.248(3) 0.8783(17) 0.1338(6) 0.071(4) Uani 0.454(15) 1 d PDU F 5
H211 H 0.2034 0.9508 0.1289 0.106 Uiso 0.454(15) 1 calc PR F 5
H212 H 0.2002 0.8495 0.1571 0.106 Uiso 0.454(15) 1 calc PR F 5
H213 H 0.2210 0.8301 0.1127 0.106 Uiso 0.454(15) 1 calc PR F 5
O220 O 0.545(4) 0.926(3) 0.1303(9) 0.066(4) Uani 0.176(9) 1 d PDU G 7
H220 H 0.5438 0.9157 0.1536 0.099 Uiso 0.176(9) 1 calc PR G 7
C220 C 0.738(4) 0.915(4) 0.1146(13) 0.082(4) Uani 0.176(9) 1 d PDU G 7
H221 H 0.7360 0.8906 0.0883 0.122 Uiso 0.176(9) 1 calc PR G 7
H222 H 0.7984 0.8624 0.1300 0.122 Uiso 0.176(9) 1 calc PR G 7
H223 H 0.7932 0.9858 0.1161 0.122 Uiso 0.176(9) 1 calc PR G 7

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.039(2) 0.035(2) 0.043(2) -0.0055(17) 0.0019(19) 0.0039(17)
O2 0.041(2) 0.050(2) 0.031(2) -0.0097(19) 0.0035(17) 0.0018(19)
O3 0.044(2) 0.037(2) 0.042(2) -0.0064(18) -0.0007(18) -0.0010(19)
O4 0.063(3) 0.050(2) 0.029(2) 0.0030(18) 0.006(2) 0.000(2)
N1 0.033(2) 0.031(3) 0.032(2) -0.001(2) -0.001(2) 0.003(2)
N2 0.075(4) 0.035(3) 0.027(3) -0.002(2) -0.001(3) -0.013(3)
C1 0.024(3) 0.043(3) 0.037(3) -0.001(3) -0.002(2) -0.002(3)
C2 0.025(3) 0.050(4) 0.033(3) -0.010(3) 0.001(2) -0.003(3)
C3 0.034(3) 0.041(4) 0.038(3) -0.005(3) -0.004(3) -0.002(3)
C4 0.034(3) 0.037(3) 0.038(3) -0.004(3) -0.001(3) -0.006(3)
C5 0.032(3) 0.037(3) 0.035(3) -0.004(3) -0.001(3) -0.001(3)
C6 0.026(3) 0.036(3) 0.032(3) -0.002(3) 0.001(2) -0.004(3)
C7 0.043(3) 0.028(3) 0.028(3) -0.003(2) 0.000(3) -0.006(3)
C8 0.024(3) 0.033(3) 0.037(3) 0.000(2) -0.001(2) 0.000(2)
C9 0.029(3) 0.039(4) 0.049(4) 0.002(3) -0.004(3) 0.001(3)
C10 0.041(3) 0.033(3) 0.048(3) 0.000(3) 0.001(3) 0.003(3)
C11 0.035(3) 0.030(3) 0.044(3) -0.002(2) -0.002(3) -0.003(3)
C12 0.055(4) 0.037(3) 0.043(3) -0.010(3) -0.006(3) -0.003(3)
C13 0.039(3) 0.045(4) 0.033(3) -0.006(3) -0.009(3) 0.002(3)
C14 0.047(4) 0.035(3) 0.038(3) -0.012(3) -0.008(3) 0.008(3)
C15 0.063(4) 0.035(3) 0.041(3) -0.008(3) 0.002(3) -0.005(3)
C16 0.045(3) 0.052(4) 0.041(4) -0.004(3) 0.000(3) -0.021(3)
C17 0.048(4) 0.043(4) 0.037(3) -0.008(3) 0.011(3) -0.019(3)
C18 0.024(3) 0.029(3) 0.038(3) 0.001(2) 0.003(2) -0.002(2)
C19 0.038(3) 0.026(3) 0.048(3) -0.007(3) -0.008(3) -0.004(3)
C20 0.037(3) 0.033(3) 0.041(3) 0.001(3) -0.007(3) -0.003(3)
C21 0.061(4) 0.030(3) 0.030(3) 0.000(2) 0.001(3) -0.005(3)
C22 0.044(3) 0.064(4) 0.031(3) -0.007(3) 0.000(3) 0.007(3)
C23 0.066(4) 0.035(3) 0.065(4) -0.003(3) -0.006(3) 0.006(3)
N4 0.052(3) 0.034(3) 0.037(3) 0.004(2) -0.005(3) 0.008(3)
O5 0.105(7) 0.077(7) 0.128(8) 0.011(6) 0.002(6) 0.026(6)
O6 0.123(9) 0.061(6) 0.073(7) 0.008(6) -0.006(7) 0.016(6)
O7 0.054(8) 0.051(7) 0.076(9) 0.000(6) -0.005(6) 0.021(6)
O8 0.065(9) 0.045(8) 0.063(11) -0.010(7) 0.004(8) 0.006(7)
O9 0.043(6) 0.033(4) 0.043(8) -0.004(6) -0.008(6) -0.004(5)
O10 0.052(9) 0.052(7) 0.044(7) 0.000(6) 0.006(6) 0.002(6)
N3 0.052(6) 0.028(5) 0.068(6) 0.006(4) 0.011(5) 0.001(5)
C24 0.080(10) 0.042(8) 0.086(10) -0.013(7) 0.006(9) 0.019(8)
C25 0.055(9) 0.060(9) 0.084(9) -0.002(7) -0.002(8) 0.005(8)
C26 0.068(7) 0.045(7) 0.090(8) -0.001(6) 0.001(6) -0.002(6)
C27 0.034(5) 0.013(5) 0.031(5) -0.003(4) -0.007(4) -0.008(4)
C28 0.040(6) 0.022(5) 0.037(6) 0.005(4) -0.004(5) 0.001(5)
C29 0.040(8) 0.033(5) 0.043(7) 0.005(5) -0.002(6) 0.006(6)
C30 0.024(8) 0.025(5) 0.033(6) -0.002(5) 0.003(7) -0.003(7)
C31 0.035(7) 0.031(5) 0.048(7) 0.001(5) 0.014(5) -0.002(6)
C32 0.043(6) 0.042(5) 0.056(6) -0.001(5) -0.002(5) -0.008(5)
C33 0.028(5) 0.028(5) 0.056(5) -0.006(4) -0.001(5) -0.005(5)
O51 0.038(6) 0.044(6) 0.042(6) 0.010(5) 0.002(5) -0.010(5)
O61 0.035(5) 0.034(5) 0.056(5) 0.012(4) -0.002(4) -0.002(4)
O71 0.051(9) 0.031(7) 0.052(7) -0.005(6) -0.002(7) -0.018(7)
O81 0.032(6) 0.011(5) 0.018(5) 0.000(4) 0.002(5) -0.006(4)
O91 0.042(7) 0.041(5) 0.049(9) 0.003(7) -0.003(6) -0.002(5)
O101 0.044(9) 0.053(7) 0.042(8) -0.004(6) 0.006(7) 0.004(7)
N31 0.038(6) 0.033(6) 0.040(5) -0.010(5) -0.006(5) -0.001(5)
C241 0.008(6) 0.017(6) 0.035(7) 0.000(5) 0.006(5) 0.002(5)
C251 0.021(7) 0.027(7) 0.038(6) -0.002(5) 0.009(6) -0.012(6)
C261 0.036(6) 0.034(6) 0.041(6) -0.001(5) 0.002(5) 0.000(5)
C271 0.037(5) 0.025(5) 0.025(5) 0.000(4) 0.000(5) -0.006(5)
C281 0.036(6) 0.040(6) 0.037(6) 0.001(5) 0.011(5) -0.006(5)
C291 0.038(7) 0.024(5) 0.041(7) 0.000(6) 0.012(6) -0.001(6)
C301 0.009(8) 0.016(5) 0.027(6) -0.005(5) 0.012(6) -0.004(7)
C311 0.040(9) 0.030(6) 0.044(8) 0.005(6) -0.013(7) 0.004(7)
C321 0.036(7) 0.027(6) 0.052(6) 0.004(5) -0.006(5) -0.003(6)
C331 0.029(6) 0.026(5) 0.047(5) -0.005(5) -0.003(5) -0.003(5)
O100 0.081(6) 0.082(7) 0.082(6) 0.007(6) 0.008(5) -0.001(6)
C100 0.084(6) 0.086(6) 0.080(6) 0.001(5) 0.005(5) 0.001(5)
O110 0.080(6) 0.086(6) 0.077(6) -0.003(5) 0.007(5) 0.002(5)
C110 0.084(6) 0.085(6) 0.082(6) 0.001(5) 0.003(5) 0.003(5)
O120 0.085(6) 0.083(6) 0.077(6) -0.002(5) 0.000(5) 0.000(5)
C120 0.086(6) 0.085(6) 0.080(6) -0.001(5) 0.002(5) 0.001(5)
O200 0.057(8) 0.059(7) 0.059(7) 0.001(6) -0.002(7) 0.002(7)
C200 0.062(7) 0.067(6) 0.063(6) -0.002(5) 0.000(6) 0.004(6)
O210 0.046(6) 0.067(5) 0.052(5) -0.007(4) 0.000(5) 0.015(5)
C210 0.077(8) 0.066(6) 0.071(6) 0.005(5) 0.000(7) 0.005(7)
O220 0.061(7) 0.069(6) 0.068(6) -0.004(5) 0.004(6) 0.004(6)
C220 0.082(6) 0.084(6) 0.079(6) -0.001(5) 0.002(5) 0.001(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.420(6) . ?
O1 C12 1.450(6) . ?
O2 C2 1.372(6) . ?
O2 C22 1.434(6) . ?
O3 C3 1.394(6) . ?
O3 C23 1.431(6) . ?
O4 C9 1.223(6) . ?
N1 C9 1.378(6) . ?
N1 C6 1.421(6) . ?
N1 C8 1.489(6) . ?
N2 C16 1.501(7) . ?
N2 C15 1.515(6) . ?
N2 C21 1.542(7) . ?
N2 H2A 0.9100 . ?
C1 C6 1.375(7) . ?
C1 C2 1.403(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.396(7) . ?
C3 C4 1.378(7) . ?
C4 C5 1.396(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(6) . ?
C5 C7 1.504(7) . ?
C7 C21 1.519(7) . ?
C7 C17 1.545(7) . ?
C7 C8 1.558(6) . ?
C8 C18 1.495(6) . ?
C8 H8A 0.9800 . ?
C9 C10 1.499(7) . ?
C10 C11 1.557(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.532(6) . ?
C11 H11A 0.9800 . ?
C12 C13 1.491(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.315(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.506(7) . ?
C14 C19 1.534(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.510(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.554(7) . ?
C18 H18A 0.9800 . ?
C19 C20 1.539(7) . ?
C19 H19A 0.9800 . ?
C20 C21 1.540(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N4 O9 1.14(2) . ?
N4 O10 1.16(3) . ?
N4 O101 1.30(4) . ?
N4 O91 1.31(3) . ?
N4 C30 1.42(3) . ?
N4 C301 1.54(3) . ?
O5 C24 1.25(2) . ?
O6 C24 1.25(2) . ?
O7 C26 1.47(2) . ?
O7 H7 0.8200 . ?
O8 C27 1.20(3) . ?
N3 C27 1.344(13) . ?
N3 C25 1.504(18) . ?
N3 H3 0.8600 . ?
C24 C25 1.57(3) . ?
C25 C26 1.47(2) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.441(15) . ?
C28 C29 1.37(3) . ?
C28 C33 1.412(17) . ?
C29 C30 1.71(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.17(3) . ?
C31 C32 1.38(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.454(18) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
O51 C241 1.29(2) . ?
O61 C241 1.257(16) . ?
O71 C261 1.61(2) . ?
O71 H71 0.8200 . ?
O81 C271 1.31(3) . ?
N31 C271 1.325(15) . ?
N31 C251 1.430(18) . ?
N31 H31A 0.8600 . ?
C241 C251 1.55(2) . ?
C251 C261 1.562(19) . ?
C251 H251 0.9800 . ?
C261 H26C 0.9700 . ?
C261 H26D 0.9700 . ?
C271 C281 1.460(17) . ?
C281 C291 1.38(2) . ?
C281 C331 1.40(2) . ?
C291 C301 1.71(3) . ?
C291 H291 0.9300 . ?
C301 C311 1.05(3) . ?
C311 C321 1.41(4) . ?
C311 H311 0.9300 . ?
C321 C331 1.40(2) . ?
C321 H321 0.9300 . ?
C331 H331 0.9300 . ?
O100 C100 1.56(3) . ?
O100 H100 0.8200 . ?
C100 H101 0.9600 . ?
C100 H102 0.9600 . ?
C100 H103 0.9600 . ?
O110 C110 1.52(3) . ?
O110 H110 0.8200 . ?
C110 H111 0.9600 . ?
C110 H112 0.9600 . ?
C110 H113 0.9600 . ?
O120 C120 1.44(3) . ?
O120 H120 0.8200 . ?
C120 H121 0.9600 . ?
C120 H122 0.9600 . ?
C120 H123 0.9600 . ?
O200 C200 1.59(3) . ?
O200 H200 0.8200 . ?
C200 H201 0.9600 . ?
C200 H202 0.9600 . ?
C200 H203 0.9600 . ?
O210 C210 1.776(18) . ?
O210 H210 0.8200 . ?
C210 H211 0.9600 . ?
C210 H212 0.9600 . ?
C210 H213 0.9600 . ?
O220 C220 1.62(3) . ?
O220 H220 0.8200 . ?
C220 H221 0.9600 . ?
C220 H222 0.9600 . ?
C220 H223 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.8(4) . . ?
C2 O2 C22 116.4(4) . . ?
C3 O3 C23 115.8(4) . . ?
C9 N1 C6 124.1(4) . . ?
C9 N1 C8 119.1(4) . . ?
C6 N1 C8 109.9(4) . . ?
C16 N2 C15 114.3(4) . . ?
C16 N2 C21 107.9(4) . . ?
C15 N2 C21 113.6(4) . . ?
C16 N2 H2A 106.9 . . ?
C15 N2 H2A 106.9 . . ?
C21 N2 H2A 106.9 . . ?
C6 C1 C2 117.9(5) . . ?
C6 C1 H1A 121.1 . . ?
C2 C1 H1A 121.1 . . ?
O2 C2 C3 116.7(5) . . ?
O2 C2 C1 123.2(5) . . ?
C3 C2 C1 120.1(5) . . ?
C4 C3 O3 124.3(5) . . ?
C4 C3 C2 121.4(5) . . ?
O3 C3 C2 114.3(5) . . ?
C3 C4 C5 118.5(5) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 C7 110.9(4) . . ?
C4 C5 C7 129.3(5) . . ?
C1 C6 C5 122.1(5) . . ?
C1 C6 N1 128.9(4) . . ?
C5 C6 N1 109.0(4) . . ?
C5 C7 C21 115.5(4) . . ?
C5 C7 C17 112.3(4) . . ?
C21 C7 C17 101.6(4) . . ?
C5 C7 C8 102.3(4) . . ?
C21 C7 C8 114.6(4) . . ?
C17 C7 C8 110.9(4) . . ?
N1 C8 C18 106.7(4) . . ?
N1 C8 C7 103.9(4) . . ?
C18 C8 C7 117.0(4) . . ?
N1 C8 H8A 109.6 . . ?
C18 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
O4 C9 N1 122.3(5) . . ?
O4 C9 C10 121.4(5) . . ?
N1 C9 C10 116.2(5) . . ?
C9 C10 C11 118.4(4) . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
O1 C11 C18 116.2(4) . . ?
O1 C11 C10 104.7(4) . . ?
C18 C11 C10 109.3(4) . . ?
O1 C11 H11A 108.8 . . ?
C18 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
O1 C12 C13 110.9(4) . . ?
O1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 124.4(5) . . ?
C14 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C13 C14 C15 123.1(5) . . ?
C13 C14 C19 121.0(5) . . ?
C15 C14 C19 116.0(4) . . ?
C14 C15 N2 109.8(4) . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
N2 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 104.3(5) . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.8(4) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 108.7(4) . . ?
C8 C18 C19 113.0(4) . . ?
C11 C18 C19 116.0(4) . . ?
C8 C18 H18A 106.1 . . ?
C11 C18 H18A 106.1 . . ?
C19 C18 H18A 106.1 . . ?
C14 C19 C20 108.6(4) . . ?
C14 C19 C18 114.1(4) . . ?
C20 C19 C18 106.0(4) . . ?
C14 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C19 C20 C21 108.6(4) . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.3 . . ?
C7 C21 C20 115.5(4) . . ?
C7 C21 N2 104.5(4) . . ?
C20 C21 N2 110.0(4) . . ?
C7 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
N2 C21 H21A 108.9 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O9 N4 O10 113(2) . . ?
O9 N4 O101 126(2) . . ?
O10 N4 O101 14(3) . . ?
O9 N4 O91 18.9(15) . . ?
O10 N4 O91 121(2) . . ?
O101 N4 O91 132(2) . . ?
O9 N4 C30 128.7(15) . . ?
O10 N4 C30 116.9(18) . . ?
O101 N4 C30 104.7(19) . . ?
O91 N4 C30 121.9(15) . . ?
O9 N4 C301 114.9(14) . . ?
O10 N4 C301 131.7(18) . . ?
O101 N4 C301 119.0(19) . . ?
O91 N4 C301 106.8(15) . . ?
C30 N4 C301 15.1(12) . . ?
C26 O7 H7 109.5 . . ?
C27 N3 C25 120.1(11) . . ?
C27 N3 H3 120.0 . . ?
C25 N3 H3 120.0 . . ?
O6 C24 O5 132(2) . . ?
O6 C24 C25 114.2(19) . . ?
O5 C24 C25 113(2) . . ?
C26 C25 N3 113.0(14) . . ?
C26 C25 C24 112.7(16) . . ?
N3 C25 C24 112.7(17) . . ?
C26 C25 H25 105.9 . . ?
N3 C25 H25 105.9 . . ?
C24 C25 H25 105.9 . . ?
C25 C26 O7 114.7(15) . . ?
C25 C26 H26A 108.6 . . ?
O7 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
O7 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
O8 C27 N3 120.7(16) . . ?
O8 C27 C28 121.7(16) . . ?
N3 C27 C28 117.6(10) . . ?
C29 C28 C33 119.0(13) . . ?
C29 C28 C27 119.3(12) . . ?
C33 C28 C27 121.6(10) . . ?
C28 C29 C30 117.8(17) . . ?
C28 C29 H29 121.1 . . ?
C30 C29 H29 121.1 . . ?
C31 C30 N4 140(2) . . ?
C31 C30 C29 113(2) . . ?
N4 C30 C29 105.4(16) . . ?
C30 C31 C32 131.3(18) . . ?
C30 C31 H31 114.4 . . ?
C32 C31 H31 114.4 . . ?
C31 C32 C33 118.1(12) . . ?
C31 C32 H32 120.9 . . ?
C33 C32 H32 120.9 . . ?
C28 C33 C32 120.1(12) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C261 O71 H71 109.5 . . ?
C271 N31 C251 122.3(12) . . ?
C271 N31 H31A 118.8 . . ?
C251 N31 H31A 118.8 . . ?
O61 C241 O51 124.1(13) . . ?
O61 C241 C251 117.2(12) . . ?
O51 C241 C251 118.6(13) . . ?
N31 C251 C241 110.9(14) . . ?
N31 C251 C261 109.8(11) . . ?
C241 C251 C261 111.9(12) . . ?
N31 C251 H251 108.0 . . ?
C241 C251 H251 108.0 . . ?
C261 C251 H251 108.0 . . ?
C251 C261 O71 101.9(13) . . ?
C251 C261 H26C 111.4 . . ?
O71 C261 H26C 111.4 . . ?
C251 C261 H26D 111.4 . . ?
O71 C261 H26D 111.4 . . ?
H26C C261 H26D 109.3 . . ?
O81 C271 N31 122.1(15) . . ?
O81 C271 C281 118.5(14) . . ?
N31 C271 C281 119.3(12) . . ?
C291 C281 C331 117.0(13) . . ?
C291 C281 C271 117.7(13) . . ?
C331 C281 C271 124.8(12) . . ?
C281 C291 C301 111.7(15) . . ?
C281 C291 H291 124.1 . . ?
C301 C291 H291 124.1 . . ?
C311 C301 N4 136(2) . . ?
C311 C301 C291 125(3) . . ?
N4 C301 C291 98.5(13) . . ?
C301 C311 C321 123(3) . . ?
C301 C311 H311 118.4 . . ?
C321 C311 H311 118.4 . . ?
C331 C321 C311 118.2(17) . . ?
C331 C321 H321 120.9 . . ?
C311 C321 H321 120.9 . . ?
C321 C331 C281 123.9(14) . . ?
C321 C331 H331 118.1 . . ?
C281 C331 H331 118.1 . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H101 109.5 . . ?
O100 C100 H102 109.5 . . ?
H101 C100 H102 109.5 . . ?
O100 C100 H103 109.5 . . ?
H101 C100 H103 109.5 . . ?
H102 C100 H103 109.5 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H111 109.5 . . ?
O110 C110 H112 109.5 . . ?
H111 C110 H112 109.5 . . ?
O110 C110 H113 109.5 . . ?
H111 C110 H113 109.5 . . ?
H112 C110 H113 109.5 . . ?
C120 O120 H120 109.5 . . ?
O120 C120 H121 109.5 . . ?
O120 C120 H122 109.5 . . ?
H121 C120 H122 109.5 . . ?
O120 C120 H123 109.5 . . ?
H121 C120 H123 109.5 . . ?
H122 C120 H123 109.5 . . ?
C200 O200 H200 109.5 . . ?
O200 C200 H201 109.5 . . ?
O200 C200 H202 109.5 . . ?
H201 C200 H202 109.5 . . ?
O200 C200 H203 109.5 . . ?
H201 C200 H203 109.5 . . ?
H202 C200 H203 109.5 . . ?
C210 O210 H210 109.5 . . ?
O210 C210 H211 109.5 . . ?
O210 C210 H212 109.5 . . ?
H211 C210 H212 109.5 . . ?
O210 C210 H213 109.5 . . ?
H211 C210 H213 109.5 . . ?
H212 C210 H213 109.5 . . ?
C220 O220 H220 109.5 . . ?
O220 C220 H221 109.5 . . ?
O220 C220 H222 109.5 . . ?
H221 C220 H222 109.5 . . ?
O220 C220 H223 109.5 . . ?
H221 C220 H223 109.5 . . ?
H222 C220 H223 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C3 -175.9(4) . . . . ?
C22 O2 C2 C1 3.2(6) . . . . ?
C6 C1 C2 O2 -178.4(4) . . . . ?
C6 C1 C2 C3 0.7(7) . . . . ?
C23 O3 C3 C4 5.1(7) . . . . ?
C23 O3 C3 C2 -174.2(5) . . . . ?
O2 C2 C3 C4 175.7(5) . . . . ?
C1 C2 C3 C4 -3.5(7) . . . . ?
O2 C2 C3 O3 -5.0(6) . . . . ?
C1 C2 C3 O3 175.8(4) . . . . ?
O3 C3 C4 C5 -176.8(5) . . . . ?
C2 C3 C4 C5 2.4(7) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C3 C4 C5 C7 -175.9(5) . . . . ?
C2 C1 C6 C5 3.1(7) . . . . ?
C2 C1 C6 N1 -175.1(5) . . . . ?
C4 C5 C6 C1 -4.2(7) . . . . ?
C7 C5 C6 C1 173.5(4) . . . . ?
C4 C5 C6 N1 174.3(5) . . . . ?
C7 C5 C6 N1 -8.0(6) . . . . ?
C9 N1 C6 C1 22.2(8) . . . . ?
C8 N1 C6 C1 172.5(5) . . . . ?
C9 N1 C6 C5 -156.2(5) . . . . ?
C8 N1 C6 C5 -5.8(5) . . . . ?
C6 C5 C7 C21 142.7(4) . . . . ?
C4 C5 C7 C21 -39.9(8) . . . . ?
C6 C5 C7 C17 -101.5(5) . . . . ?
C4 C5 C7 C17 76.0(7) . . . . ?
C6 C5 C7 C8 17.5(5) . . . . ?
C4 C5 C7 C8 -165.1(5) . . . . ?
C9 N1 C8 C18 44.2(6) . . . . ?
C6 N1 C8 C18 -107.9(4) . . . . ?
C9 N1 C8 C7 168.4(4) . . . . ?
C6 N1 C8 C7 16.4(5) . . . . ?
C5 C7 C8 N1 -19.6(5) . . . . ?
C21 C7 C8 N1 -145.4(4) . . . . ?
C17 C7 C8 N1 100.3(4) . . . . ?
C5 C7 C8 C18 97.7(5) . . . . ?
C21 C7 C8 C18 -28.0(6) . . . . ?
C17 C7 C8 C18 -142.3(4) . . . . ?
C6 N1 C9 O4 -23.6(8) . . . . ?
C8 N1 C9 O4 -171.5(5) . . . . ?
C6 N1 C9 C10 154.5(5) . . . . ?
C8 N1 C9 C10 6.6(7) . . . . ?
O4 C9 C10 C11 146.1(5) . . . . ?
N1 C9 C10 C11 -32.0(7) . . . . ?
C12 O1 C11 C18 -67.6(5) . . . . ?
C12 O1 C11 C10 171.7(4) . . . . ?
C9 C10 C11 O1 129.1(5) . . . . ?
C9 C10 C11 C18 4.0(6) . . . . ?
C11 O1 C12 C13 86.2(5) . . . . ?
O1 C12 C13 C14 -64.0(7) . . . . ?
C12 C13 C14 C15 177.0(5) . . . . ?
C12 C13 C14 C19 -3.2(8) . . . . ?
C13 C14 C15 N2 -126.8(5) . . . . ?
C19 C14 C15 N2 53.4(6) . . . . ?
C16 N2 C15 C14 77.5(6) . . . . ?
C21 N2 C15 C14 -46.8(6) . . . . ?
C15 N2 C16 C17 -141.8(4) . . . . ?
C21 N2 C16 C17 -14.4(5) . . . . ?
N2 C16 C17 C7 35.3(5) . . . . ?
C5 C7 C17 C16 -166.8(5) . . . . ?
C21 C7 C17 C16 -42.8(5) . . . . ?
C8 C7 C17 C16 79.4(5) . . . . ?
N1 C8 C18 C11 -71.4(5) . . . . ?
C7 C8 C18 C11 172.8(4) . . . . ?
N1 C8 C18 C19 158.3(4) . . . . ?
C7 C8 C18 C19 42.5(6) . . . . ?
O1 C11 C18 C8 -71.8(5) . . . . ?
C10 C11 C18 C8 46.4(5) . . . . ?
O1 C11 C18 C19 56.8(6) . . . . ?
C10 C11 C18 C19 175.0(4) . . . . ?
C13 C14 C19 C20 179.1(5) . . . . ?
C15 C14 C19 C20 -1.1(6) . . . . ?
C13 C14 C19 C18 61.1(6) . . . . ?
C15 C14 C19 C18 -119.1(5) . . . . ?
C8 C18 C19 C14 58.0(6) . . . . ?
C11 C18 C19 C14 -68.4(6) . . . . ?
C8 C18 C19 C20 -61.4(5) . . . . ?
C11 C18 C19 C20 172.1(4) . . . . ?
C14 C19 C20 C21 -56.5(5) . . . . ?
C18 C19 C20 C21 66.5(5) . . . . ?
C5 C7 C21 C20 -84.0(5) . . . . ?
C17 C7 C21 C20 154.1(4) . . . . ?
C8 C7 C21 C20 34.5(6) . . . . ?
C5 C7 C21 N2 154.9(4) . . . . ?
C17 C7 C21 N2 33.1(5) . . . . ?
C8 C7 C21 N2 -86.5(5) . . . . ?
C19 C20 C21 C7 -55.4(6) . . . . ?
C19 C20 C21 N2 62.6(5) . . . . ?
C16 N2 C21 C7 -12.3(5) . . . . ?
C15 N2 C21 C7 115.5(4) . . . . ?
C16 N2 C21 C20 -136.9(4) . . . . ?
C15 N2 C21 C20 -9.1(6) . . . . ?
C27 N3 C25 C26 -90.6(18) . . . . ?
C27 N3 C25 C24 140.2(15) . . . . ?
O6 C24 C25 C26 -127.3(19) . . . . ?
O5 C24 C25 C26 46(3) . . . . ?
O6 C24 C25 N3 2(3) . . . . ?
O5 C24 C25 N3 175.0(16) . . . . ?
N3 C25 C26 O7 -65(2) . . . . ?
C24 C25 C26 O7 65(2) . . . . ?
C25 N3 C27 O8 -8(2) . . . . ?
C25 N3 C27 C28 174.9(12) . . . . ?
O8 C27 C28 C29 -14(2) . . . . ?
N3 C27 C28 C29 163.8(15) . . . . ?
O8 C27 C28 C33 162.2(16) . . . . ?
N3 C27 C28 C33 -20.4(17) . . . . ?
C33 C28 C29 C30 9(3) . . . . ?
C27 C28 C29 C30 -175.0(15) . . . . ?
O9 N4 C30 C31 -168(3) . . . . ?
O10 N4 C30 C31 28(4) . . . . ?
O101 N4 C30 C31 20(4) . . . . ?
O91 N4 C30 C31 -146(3) . . . . ?
C301 N4 C30 C31 -142(11) . . . . ?
O9 N4 C30 C29 -6(2) . . . . ?
O10 N4 C30 C29 -171(2) . . . . ?
O101 N4 C30 C29 -178(2) . . . . ?
O91 N4 C30 C29 16(2) . . . . ?
C301 N4 C30 C29 20(7) . . . . ?
C28 C29 C30 C31 -11(3) . . . . ?
C28 C29 C30 N4 -178.2(17) . . . . ?
N4 C30 C31 C32 167(2) . . . . ?
C29 C30 C31 C32 6(3) . . . . ?
C30 C31 C32 C33 -1(3) . . . . ?
C29 C28 C33 C32 -3(2) . . . . ?
C27 C28 C33 C32 -179.1(11) . . . . ?
C31 C32 C33 C28 -2.0(19) . . . . ?
C271 N31 C251 C241 -151.4(13) . . . . ?
C271 N31 C251 C261 84.5(16) . . . . ?
O61 C241 C251 N31 -177.8(13) . . . . ?
O51 C241 C251 N31 -1.3(19) . . . . ?
O61 C241 C251 C261 -54.8(19) . . . . ?
O51 C241 C251 C261 121.7(15) . . . . ?
N31 C251 C261 O71 72.9(16) . . . . ?
C241 C251 C261 O71 -50.7(15) . . . . ?
C251 N31 C271 O81 -2(2) . . . . ?
C251 N31 C271 C281 -177.4(11) . . . . ?
O81 C271 C281 C291 19(2) . . . . ?
N31 C271 C281 C291 -164.8(13) . . . . ?
O81 C271 C281 C331 -152.2(16) . . . . ?
N31 C271 C281 C331 23.6(19) . . . . ?
C331 C281 C291 C301 -7(2) . . . . ?
C271 C281 C291 C301 -178.9(14) . . . . ?
O9 N4 C301 C311 -1(4) . . . . ?
O10 N4 C301 C311 -172(4) . . . . ?
O101 N4 C301 C311 -179(4) . . . . ?
O91 N4 C301 C311 17(4) . . . . ?
C30 N4 C301 C311 -159(11) . . . . ?
O9 N4 C301 C291 168.0(13) . . . . ?
O10 N4 C301 C291 -3(3) . . . . ?
O101 N4 C301 C291 -10(3) . . . . ?
O91 N4 C301 C291 -173.7(14) . . . . ?
C30 N4 C301 C291 10(7) . . . . ?
C281 C291 C301 C311 -3(4) . . . . ?
C281 C291 C301 N4 -173.7(14) . . . . ?
N4 C301 C311 C321 177(2) . . . . ?
C291 C301 C311 C321 11(5) . . . . ?
C301 C311 C321 C331 -8(4) . . . . ?
C311 C321 C331 C281 -2(3) . . . . ?
C291 C281 C331 C321 9(2) . . . . ?
C271 C281 C331 C321 -179.3(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.91 1.66 2.570(12) 172.8 1_655
N2 H2A O6 0.91 1.99 2.762(12) 141.8 .
O7 H7 O5 0.82 1.72 2.50(2) 159.5 4_465
O71 H71 O61 0.82 1.83 2.64(2) 169.9 4_565
O100 H100 O7 0.82 1.90 2.71(3) 172.6 4_565
O110 H110 O71 0.82 2.21 3.00(3) 160.2 4_665
O120 H120 O4 0.82 1.94 2.69(2) 152.9 3_655
O200 H200 O6 0.82 2.15 2.85(3) 143.3 .
O210 H210 O4 0.82 2.31 2.963(12) 137.3 3_655
O220 H220 O4 0.82 2.27 2.96(3) 141.6 3_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 930481'
#######################################################################
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

#==== end



data_B3NB(DL)T
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-(D~0.84~L~0.16~)-threoninate ethanol
solvate 0.79-hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C23 H27 N2 O4, C11 H11 N2 O6, C2 H6 O, 0.79(H2 O)'
_chemical_formula_sum            'C36 H45.61 N4 O11.81'
_chemical_formula_weight         723.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.938(2)
_cell_length_b                   12.330(3)
_cell_length_c                   35.775(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3501.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    947
_cell_measurement_theta_min      2.4681
_cell_measurement_theta_max      87.3628

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54175
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10739
_diffrn_reflns_av_R_equivalents  0.1385
_diffrn_reflns_av_sigmaI/netI    0.2288
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         77.92
_reflns_number_total             6474
_reflns_number_gt                2594
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0877P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rmad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_number_reflns         6474
_refine_ls_number_parameters     598
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.1631
_refine_ls_R_factor_gt           0.0888
_refine_ls_wR_factor_ref         0.2306
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_restrained_S_all      0.822
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7947(7) -0.2721(4) 0.68023(12) 0.0352(11) Uani 1 1 d . . .
O2 O 0.7614(7) 0.3060(4) 0.81822(12) 0.0418(13) Uani 1 1 d . . .
O3 O 0.7308(7) 0.4208(4) 0.75846(14) 0.0439(13) Uani 1 1 d . . .
O4 O 0.7814(8) -0.0941(4) 0.79543(12) 0.0515(16) Uani 1 1 d . . .
N1 N 0.8466(8) -0.0190(5) 0.73935(15) 0.0305(13) Uani 1 1 d . . .
N2 N 0.8878(7) 0.0731(5) 0.61534(15) 0.0355(14) Uani 1 1 d . . .
H2A H 0.9026 0.1311 0.5991 0.043 Uiso 1 1 calc R . .
C1 C 0.8050(10) 0.1397(6) 0.78337(19) 0.0370(16) Uani 1 1 d . . .
H1A H 0.8072 0.0968 0.8054 0.044 Uiso 1 1 calc R . .
C2 C 0.7807(10) 0.2516(6) 0.78523(18) 0.0357(17) Uani 1 1 d . . .
C3 C 0.7664(10) 0.3124(6) 0.75283(19) 0.0371(17) Uani 1 1 d . . .
C4 C 0.7942(10) 0.2666(6) 0.71823(18) 0.0363(16) Uani 1 1 d . . .
H4A H 0.7935 0.3102 0.6963 0.044 Uiso 1 1 calc R . .
C5 C 0.8239(10) 0.1531(5) 0.71584(19) 0.0364(17) Uani 1 1 d . . .
C6 C 0.8262(10) 0.0926(6) 0.74812(17) 0.0354(16) Uani 1 1 d . . .
C7 C 0.8709(9) 0.0862(6) 0.68252(17) 0.0309(15) Uani 1 1 d . . .
C8 C 0.8410(9) -0.0322(5) 0.69768(17) 0.0295(14) Uani 1 1 d . . .
H8A H 0.9364 -0.0797 0.6896 0.035 Uiso 1 1 calc R . .
C9 C 0.7980(11) -0.1012(6) 0.76113(18) 0.0382(17) Uani 1 1 d . . .
C10 C 0.7650(11) -0.2093(6) 0.74178(17) 0.0394(17) Uani 1 1 d . . .
H10A H 0.6901 -0.2528 0.7581 0.047 Uiso 1 1 calc R . .
H10B H 0.8734 -0.2487 0.7399 0.047 Uiso 1 1 calc R . .
C11 C 0.6846(9) -0.2052(6) 0.70193(17) 0.0334(15) Uani 1 1 d . . .
H11A H 0.5685 -0.2368 0.7024 0.040 Uiso 1 1 calc R . .
C12 C 0.7337(11) -0.2924(6) 0.64283(19) 0.0432(18) Uani 1 1 d . . .
H12A H 0.6090 -0.2930 0.6430 0.052 Uiso 1 1 calc R . .
H12B H 0.7727 -0.3648 0.6345 0.052 Uiso 1 1 calc R . .
C13 C 0.7937(10) -0.2089(6) 0.61596(19) 0.0375(16) Uani 1 1 d . . .
H13A H 0.8667 -0.2295 0.5962 0.045 Uiso 1 1 calc R . .
C14 C 0.7464(10) -0.1050(7) 0.61925(18) 0.0391(17) Uani 1 1 d . . .
C15 C 0.8151(11) -0.0218(6) 0.59285(18) 0.0405(18) Uani 1 1 d . . .
H15A H 0.7242 0.0046 0.5762 0.049 Uiso 1 1 calc R . .
H15B H 0.9043 -0.0545 0.5771 0.049 Uiso 1 1 calc R . .
C16 C 1.0537(10) 0.0462(6) 0.6315(2) 0.0370(17) Uani 1 1 d . . .
H16A H 1.1460 0.0751 0.6158 0.044 Uiso 1 1 calc R . .
H16B H 1.0676 -0.0333 0.6339 0.044 Uiso 1 1 calc R . .
C17 C 1.0529(10) 0.1012(6) 0.67032(19) 0.0387(18) Uani 1 1 d . . .
H17A H 1.1317 0.0649 0.6877 0.046 Uiso 1 1 calc R . .
H17B H 1.0827 0.1790 0.6685 0.046 Uiso 1 1 calc R . .
C18 C 0.6787(9) -0.0872(6) 0.68900(17) 0.0337(15) Uani 1 1 d . . .
H18A H 0.5922 -0.0510 0.7051 0.040 Uiso 1 1 calc R . .
C19 C 0.6226(10) -0.0653(6) 0.64745(19) 0.0383(17) Uani 1 1 d . . .
H19A H 0.5117 -0.1014 0.6429 0.046 Uiso 1 1 calc R . .
C20 C 0.6006(9) 0.0559(7) 0.6438(2) 0.0376(18) Uani 1 1 d . . .
H20A H 0.5480 0.0733 0.6195 0.045 Uiso 1 1 calc R . .
H20B H 0.5258 0.0829 0.6639 0.045 Uiso 1 1 calc R . .
C21 C 0.7701(9) 0.1100(6) 0.64659(17) 0.0329(16) Uani 1 1 d . . .
H21A H 0.7539 0.1902 0.6445 0.040 Uiso 1 1 calc R . .
C22 C 0.7842(12) 0.2460(7) 0.85164(19) 0.053(2) Uani 1 1 d . . .
H22A H 0.7725 0.2945 0.8732 0.079 Uiso 1 1 calc R . .
H22B H 0.8969 0.2135 0.8517 0.079 Uiso 1 1 calc R . .
H22C H 0.6991 0.1886 0.8531 0.079 Uiso 1 1 calc R . .
C23 C 0.7127(14) 0.4867(6) 0.7259(2) 0.058(3) Uani 1 1 d . . .
H23A H 0.6845 0.5610 0.7333 0.087 Uiso 1 1 calc R . .
H23B H 0.6226 0.4575 0.7101 0.087 Uiso 1 1 calc R . .
H23C H 0.8188 0.4869 0.7119 0.087 Uiso 1 1 calc R . .
O5 O 0.9588(8) 0.2102(6) 0.55847(18) 0.0408(16) Uani 0.836(7) 1 d PU A 1
O6 O 0.6964(9) 0.2555(6) 0.57317(18) 0.0455(17) Uani 0.836(7) 1 d PU A 1
O51 O 0.940(5) 0.257(3) 0.5743(10) 0.045(5) Uani 0.164(7) 1 d PU A 2
O61 O 0.678(5) 0.202(3) 0.5578(10) 0.048(5) Uani 0.164(7) 1 d PU A 2
O7 O 0.7401(8) 0.2171(4) 0.47867(16) 0.0371(15) Uani 0.836(7) 1 d P A 1
H7A H 0.6572 0.2429 0.4671 0.056 Uiso 0.836(7) 1 calc PR A 1
O71 O 0.899(4) 0.219(2) 0.4814(8) 0.036(7) Uani 0.164(7) 1 d PU A 2
H71 H 0.9905 0.2187 0.4697 0.054 Uiso 0.164(7) 1 calc PR A 2
O8 O 0.8076(7) 0.5829(4) 0.51969(14) 0.0411(12) Uani 1 1 d . . .
O9 O 0.4332(8) 0.8734(4) 0.56998(16) 0.0497(15) Uani 1 1 d . . .
O10 O 0.1624(7) 0.8676(4) 0.56212(14) 0.0432(13) Uani 1 1 d . . .
N4 N 0.3054(9) 0.8298(5) 0.55851(15) 0.0372(14) Uani 1 1 d . A .
C24 C 0.8213(11) 0.2650(6) 0.5544(2) 0.0376(17) Uani 1 1 d . . .
C25 C 0.8284(10) 0.3533(5) 0.52406(19) 0.0341(15) Uani 1 1 d . A .
H25B H 0.7286 0.4028 0.5244 0.041 Uiso 0.164(7) 1 calc PR A 2
H25A H 0.9265 0.4015 0.5296 0.041 Uiso 0.836(7) 1 d PR A 1
C26 C 0.8591(13) 0.2997(6) 0.4853(2) 0.046(2) Uani 1 1 d . . .
H26B H 0.7375 0.2804 0.4822 0.056 Uiso 0.164(7) 1 calc PR A 2
H26A H 0.9744 0.2670 0.4854 0.056 Uiso 0.836(7) 1 d PR A 1
C27 C 0.8537(12) 0.3821(6) 0.45345(19) 0.046(2) Uani 1 1 d . A .
H27A H 0.8710 0.3447 0.4296 0.069 Uiso 1 1 calc R . .
H27B H 0.9428 0.4361 0.4571 0.069 Uiso 1 1 calc R . .
H27C H 0.7438 0.4183 0.4533 0.069 Uiso 1 1 calc R . .
N3 N 0.6812(10) 0.4176(5) 0.52474(18) 0.0353(17) Uani 0.836(7) 1 d P A 1
H3A H 0.5845 0.3832 0.5268 0.042 Uiso 0.836(7) 1 calc PR A 1
C28 C 0.6744(11) 0.5272(6) 0.5225(2) 0.0262(17) Uani 0.836(7) 1 d P A 1
C29 C 0.5018(9) 0.5744(6) 0.5229(2) 0.0318(15) Uani 1 1 d . . .
H29A H 0.6093 0.5406 0.5218 0.038 Uiso 0.164(7) 1 calc PR A 2
C30 C 0.4828(10) 0.6777(6) 0.5391(2) 0.0369(17) Uani 1 1 d . A .
H30A H 0.5774 0.7155 0.5488 0.044 Uiso 1 1 calc R . .
C31 C 0.3231(10) 0.7233(5) 0.54060(17) 0.0312(14) Uani 1 1 d . . .
C32 C 0.1847(10) 0.6728(5) 0.5275(2) 0.0375(16) Uani 1 1 d . A .
H32A H 0.0763 0.7048 0.5297 0.045 Uiso 1 1 calc R . .
C33 C 0.2067(11) 0.5699(6) 0.5104(2) 0.047(2) Uani 1 1 d . . .
H33A H 0.1128 0.5329 0.5000 0.057 Uiso 0.836(7) 1 calc PR A 1
C34 C 0.3641(10) 0.5241(6) 0.50892(19) 0.0364(17) Uani 1 1 d . A .
H34A H 0.3768 0.4548 0.4977 0.044 Uiso 1 1 calc R . .
N31 N 0.978(6) 0.406(4) 0.5284(13) 0.060(13) Uani 0.164(7) 1 d PU A 2
H31A H 1.0739 0.3736 0.5331 0.072 Uiso 0.164(7) 1 calc PR A 2
C281 C 0.960(6) 0.527(4) 0.5244(14) 0.039(11) Uani 0.164(7) 1 d PU A 2
O100 O 0.417(3) 0.2823(19) 0.6586(6) 0.092(5) Uani 0.338(9) 1 d PDU B 1
H100 H 0.3597 0.3158 0.6745 0.138 Uiso 0.338(9) 1 calc PR B 1
C100 C 0.399(5) 0.335(2) 0.6218(7) 0.089(4) Uani 0.338(9) 1 d PDU B 1
H10C H 0.4547 0.2890 0.6030 0.107 Uiso 0.338(9) 1 calc PR B 1
H10D H 0.2770 0.3367 0.6156 0.107 Uiso 0.338(9) 1 calc PR B 1
C110 C 0.464(5) 0.446(2) 0.6175(10) 0.090(4) Uani 0.338(9) 1 d PDU B 1
H11B H 0.5100 0.4552 0.5923 0.135 Uiso 0.338(9) 1 calc PR B 1
H11C H 0.5533 0.4587 0.6360 0.135 Uiso 0.338(9) 1 calc PR B 1
H11D H 0.3728 0.4983 0.6215 0.135 Uiso 0.338(9) 1 calc PR B 1
O101 O 0.377(2) 0.4799(15) 0.6393(5) 0.091(4) Uani 0.452(11) 1 d PDU C 2
H101 H 0.3423 0.4615 0.6606 0.137 Uiso 0.452(11) 1 calc PR C 2
C101 C 0.272(3) 0.429(2) 0.6106(7) 0.087(4) Uani 0.452(11) 1 d PDU C 2
H10E H 0.2680 0.3498 0.6157 0.105 Uiso 0.452(11) 1 calc PR C 2
H10F H 0.3281 0.4385 0.5861 0.105 Uiso 0.452(11) 1 calc PR C 2
C111 C 0.094(3) 0.469(3) 0.6073(8) 0.088(5) Uani 0.452(11) 1 d PDU C 2
H11E H 0.0353 0.4296 0.5875 0.133 Uiso 0.452(11) 1 calc PR C 2
H11F H 0.0949 0.5470 0.6012 0.133 Uiso 0.452(11) 1 calc PR C 2
H11G H 0.0348 0.4584 0.6311 0.133 Uiso 0.452(11) 1 calc PR C 2
O121 O 0.031(5) 0.460(4) 0.6322(12) 0.094(5) Uani 0.210(11) 1 d PDU D 4
H121 H 0.0544 0.4704 0.6548 0.141 Uiso 0.210(11) 1 calc PR D 4
C121 C 0.183(7) 0.414(5) 0.6123(13) 0.089(5) Uani 0.210(11) 1 d PDU D 4
H12C H 0.2642 0.4736 0.6077 0.107 Uiso 0.210(11) 1 calc PR D 4
H12D H 0.1466 0.3858 0.5877 0.107 Uiso 0.210(11) 1 calc PR D 4
C131 C 0.269(7) 0.325(4) 0.6339(15) 0.090(4) Uani 0.210(11) 1 d PDU D 4
H13B H 0.2360 0.2543 0.6236 0.135 Uiso 0.210(11) 1 calc PR D 4
H13C H 0.2361 0.3287 0.6602 0.135 Uiso 0.210(11) 1 calc PR D 4
H13D H 0.3916 0.3333 0.6318 0.135 Uiso 0.210(11) 1 calc PR D 4
O1W O 0.676(6) 0.403(3) 0.6340(8) 0.069(6) Uani 0.34(4) 1 d PU E 2
H11W H 0.7174 0.3563 0.6194 0.104 Uiso 0.34(4) 1 d PR E 2
H12W H 0.5715 0.4256 0.6352 0.104 Uiso 0.34(4) 1 d PR E 2
O11W O 0.931(7) 0.405(4) 0.6411(12) 0.071(7) Uani 0.164(7) 1 d PU A 6
H13W H 0.9425 0.3345 0.6424 0.107 Uiso 0.164(7) 1 d PR A 6
H14W H 0.8372 0.4289 0.6364 0.107 Uiso 0.164(7) 1 d PR A 6
O12W O 0.751(7) 0.415(3) 0.6366(9) 0.068(6) Uani 0.29(4) 1 d PU F 5
H15W H 0.8581 0.3774 0.6347 0.103 Uiso 0.29(4) 1 d PR F 5
H16W H 0.7528 0.4718 0.6287 0.103 Uiso 0.29(4) 1 d PR F 5

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.043(3) 0.033(2) 0.030(2) -0.0037(19) 0.006(2) -0.001(2)
O2 0.044(3) 0.053(3) 0.029(2) -0.009(2) 0.002(2) -0.005(3)
O3 0.059(4) 0.031(2) 0.041(3) -0.006(2) 0.003(3) 0.006(3)
O4 0.086(5) 0.049(3) 0.020(2) -0.001(2) 0.006(3) -0.004(3)
N1 0.029(3) 0.040(3) 0.022(3) 0.005(2) -0.001(2) 0.002(3)
N2 0.037(4) 0.043(3) 0.026(3) 0.002(3) -0.003(3) 0.002(3)
C1 0.035(4) 0.049(4) 0.027(3) 0.000(3) 0.001(3) -0.009(4)
C2 0.030(4) 0.053(4) 0.024(3) -0.006(3) -0.001(3) -0.009(3)
C3 0.040(4) 0.039(4) 0.033(3) -0.001(3) 0.003(3) -0.002(3)
C4 0.040(4) 0.040(3) 0.029(3) 0.005(3) 0.000(3) -0.007(4)
C5 0.040(4) 0.036(3) 0.033(3) 0.005(3) 0.006(4) -0.010(4)
C6 0.038(4) 0.042(4) 0.026(3) -0.001(3) 0.001(3) -0.009(4)
C7 0.028(4) 0.045(4) 0.019(3) 0.001(3) 0.005(3) 0.000(3)
C8 0.033(4) 0.027(3) 0.029(3) -0.001(3) -0.005(3) 0.003(3)
C9 0.046(5) 0.040(4) 0.029(3) 0.000(3) 0.003(3) -0.001(4)
C10 0.052(5) 0.036(3) 0.030(3) 0.002(3) 0.001(3) -0.004(4)
C11 0.023(3) 0.044(4) 0.034(3) 0.003(3) 0.004(3) 0.004(3)
C12 0.049(5) 0.044(4) 0.037(3) -0.006(3) -0.010(4) -0.002(4)
C13 0.047(4) 0.037(3) 0.029(3) -0.004(3) -0.006(4) -0.004(4)
C14 0.035(4) 0.056(4) 0.026(3) -0.001(3) -0.011(3) -0.001(4)
C15 0.049(5) 0.050(4) 0.023(3) -0.002(3) 0.003(3) -0.004(4)
C16 0.036(4) 0.039(4) 0.036(4) 0.002(3) 0.007(3) -0.001(3)
C17 0.048(5) 0.044(4) 0.024(3) 0.000(3) 0.007(3) 0.000(4)
C18 0.027(4) 0.045(4) 0.029(3) -0.003(3) 0.009(3) 0.003(4)
C19 0.034(4) 0.047(4) 0.034(4) -0.002(3) -0.005(3) 0.002(3)
C20 0.024(4) 0.060(5) 0.028(3) 0.003(3) 0.000(3) 0.003(4)
C21 0.032(4) 0.039(3) 0.028(3) 0.002(3) -0.007(3) 0.006(3)
C22 0.059(6) 0.069(5) 0.030(4) -0.012(4) -0.003(4) 0.010(5)
C23 0.092(8) 0.039(4) 0.044(4) 0.005(3) -0.003(5) 0.007(5)
O5 0.042(4) 0.044(4) 0.037(3) 0.006(3) 0.008(3) 0.016(3)
O6 0.043(4) 0.056(4) 0.038(3) 0.009(3) 0.013(3) 0.004(4)
O51 0.042(8) 0.047(8) 0.046(8) -0.001(7) 0.003(7) 0.009(7)
O61 0.046(8) 0.056(8) 0.043(8) 0.003(7) 0.006(7) -0.001(7)
O7 0.040(4) 0.026(3) 0.045(3) 0.002(3) -0.001(3) -0.001(3)
O71 0.052(12) 0.021(10) 0.034(10) 0.004(8) 0.004(9) 0.006(8)
O8 0.043(3) 0.028(2) 0.052(3) -0.002(2) -0.002(3) -0.002(3)
O9 0.049(3) 0.042(3) 0.058(3) -0.008(3) -0.027(3) 0.007(3)
O10 0.041(3) 0.047(3) 0.042(3) 0.000(2) 0.011(3) 0.012(3)
N4 0.042(4) 0.040(3) 0.029(3) 0.003(2) -0.003(3) 0.000(3)
C24 0.037(4) 0.035(3) 0.040(4) -0.001(3) -0.005(4) 0.006(4)
C25 0.032(4) 0.037(3) 0.034(3) 0.005(3) -0.001(3) 0.000(3)
C26 0.069(6) 0.032(4) 0.038(4) 0.005(3) 0.000(4) 0.000(4)
C27 0.066(6) 0.036(4) 0.035(4) 0.005(3) -0.006(4) 0.001(4)
N3 0.045(4) 0.025(3) 0.036(3) 0.002(3) 0.008(4) 0.007(4)
C28 0.030(4) 0.023(3) 0.025(3) -0.003(3) -0.001(3) -0.010(4)
C29 0.031(4) 0.027(3) 0.037(3) 0.006(3) 0.004(3) -0.001(3)
C30 0.038(4) 0.033(4) 0.040(4) 0.005(3) -0.008(3) -0.006(3)
C31 0.040(4) 0.026(3) 0.027(3) 0.002(3) -0.003(3) 0.005(3)
C32 0.025(4) 0.037(3) 0.051(4) 0.007(3) 0.003(4) 0.000(3)
C33 0.039(5) 0.043(4) 0.060(5) -0.001(4) -0.017(4) -0.020(4)
C34 0.043(5) 0.034(3) 0.033(4) -0.002(3) -0.005(3) 0.006(3)
N31 0.058(15) 0.063(15) 0.059(15) -0.001(10) 0.001(10) -0.004(10)
C281 0.038(14) 0.040(13) 0.039(13) 0.000(9) 0.000(9) -0.003(9)
O100 0.095(7) 0.090(7) 0.090(7) -0.006(6) 0.005(6) 0.003(6)
C100 0.095(6) 0.091(6) 0.083(6) -0.008(5) 0.008(5) 0.001(5)
C110 0.098(7) 0.091(6) 0.082(6) -0.009(6) 0.008(6) 0.000(6)
O101 0.098(7) 0.092(6) 0.084(6) -0.004(6) 0.000(6) -0.004(6)
C101 0.097(6) 0.090(5) 0.075(5) -0.010(4) 0.007(5) -0.001(5)
C111 0.097(7) 0.092(7) 0.076(6) -0.011(6) 0.004(6) -0.004(6)
O121 0.099(8) 0.096(8) 0.088(8) -0.003(7) 0.003(7) -0.001(7)
C121 0.096(7) 0.091(6) 0.080(6) -0.007(5) 0.004(5) -0.001(5)
C131 0.095(6) 0.091(6) 0.084(6) -0.007(5) 0.005(5) 0.000(5)
O1W 0.074(10) 0.072(8) 0.062(7) -0.018(6) 0.010(8) 0.004(8)
O11W 0.075(11) 0.071(9) 0.068(9) -0.010(8) 0.000(8) -0.004(8)
O12W 0.079(11) 0.066(8) 0.060(8) -0.021(7) 0.005(9) 0.000(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.431(8) . ?
O1 C12 1.445(8) . ?
O2 C2 1.366(8) . ?
O2 C22 1.417(9) . ?
O3 C3 1.380(9) . ?
O3 C23 1.428(9) . ?
O4 C9 1.237(8) . ?
N1 C9 1.335(9) . ?
N1 C6 1.421(9) . ?
N1 C8 1.500(8) . ?
N2 C16 1.476(10) . ?
N2 C21 1.526(9) . ?
N2 C15 1.533(9) . ?
N2 H2A 0.9300 . ?
C1 C2 1.395(10) . ?
C1 C6 1.399(9) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(10) . ?
C3 C4 1.379(9) . ?
C4 C5 1.422(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(9) . ?
C5 C7 1.497(10) . ?
C7 C17 1.520(10) . ?
C7 C21 1.542(9) . ?
C7 C8 1.576(9) . ?
C8 C18 1.488(10) . ?
C8 H8A 1.0000 . ?
C9 C10 1.525(10) . ?
C10 C11 1.563(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.528(10) . ?
C11 H11A 1.0000 . ?
C12 C13 1.487(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.340(10) . ?
C13 H13A 0.9500 . ?
C14 C19 1.491(10) . ?
C14 C15 1.497(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.546(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.575(9) . ?
C18 H18A 1.0000 . ?
C19 C20 1.510(11) . ?
C19 H19A 1.0000 . ?
C20 C21 1.505(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.292(10) . ?
O6 C24 1.203(10) . ?
O51 C24 1.19(4) . ?
O61 C24 1.38(4) . ?
O7 C26 1.409(10) . ?
O7 H7A 0.8400 . ?
O71 C26 1.05(3) . ?
O71 H71 0.8400 . ?
O8 C28 1.265(9) . ?
O8 C281 1.41(5) . ?
O9 N4 1.219(8) . ?
O10 N4 1.233(8) . ?
N4 C31 1.469(8) . ?
C24 C25 1.539(10) . ?
C25 N31 1.36(5) . ?
C25 N3 1.412(10) . ?
C25 C26 1.555(10) . ?
C25 H25B 1.0000 . ?
C25 H25A 1.0001 . ?
C26 C27 1.527(10) . ?
C26 H26B 1.0000 . ?
C26 H26A 1.0001 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N3 C28 1.355(10) . ?
N3 H3A 0.8800 . ?
C28 C29 1.489(11) . ?
C29 C34 1.353(10) . ?
C29 C30 1.407(10) . ?
C29 H29A 0.9500 . ?
C30 C31 1.388(11) . ?
C30 H30A 0.9500 . ?
C31 C32 1.346(10) . ?
C32 C33 1.420(11) . ?
C32 H32A 0.9500 . ?
C33 C34 1.372(12) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
N31 C281 1.49(7) . ?
N31 H25A 0.4138 . ?
N31 H31A 0.8800 . ?
O100 C100 1.477(18) . ?
O100 H100 0.8400 . ?
C100 C110 1.469(19) . ?
C100 H10C 0.9900 . ?
C100 H10D 0.9900 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
C110 H11D 0.9800 . ?
C110 H12W 1.0914 . ?
O101 C101 1.464(17) . ?
O101 H101 0.8400 . ?
C101 C111 1.507(18) . ?
C101 H10E 0.9900 . ?
C101 H10F 0.9900 . ?
C111 H11E 0.9800 . ?
C111 H11F 0.9800 . ?
C111 H11G 0.9800 . ?
O121 C121 1.51(2) . ?
O121 H121 0.8400 . ?
C121 C131 1.51(2) . ?
C121 H12C 0.9900 . ?
C121 H12D 0.9900 . ?
C131 H13B 0.9800 . ?
C131 H13C 0.9800 . ?
C131 H13D 0.9800 . ?
O1W H11W 0.8399 . ?
O1W H12W 0.8799 . ?
O1W H14W 1.3204 . ?
O1W H15W 1.4765 . ?
O1W H16W 1.0632 . ?
O11W H13W 0.8720 . ?
O11W H14W 0.8188 . ?
O11W H15W 0.7075 . ?
O12W H11W 0.9857 . ?
O12W H12W 1.4295 . ?
O12W H14W 0.7082 . ?
O12W H15W 0.9724 . ?
O12W H16W 0.7569 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 113.4(6) . . ?
C2 O2 C22 117.3(6) . . ?
C3 O3 C23 116.9(6) . . ?
C9 N1 C6 125.0(6) . . ?
C9 N1 C8 119.3(6) . . ?
C6 N1 C8 108.7(5) . . ?
C16 N2 C21 109.1(5) . . ?
C16 N2 C15 111.7(6) . . ?
C21 N2 C15 112.4(6) . . ?
C16 N2 H2A 107.8 . . ?
C21 N2 H2A 107.8 . . ?
C15 N2 H2A 107.8 . . ?
C2 C1 C6 118.1(7) . . ?
C2 C1 H1A 121.0 . . ?
C6 C1 H1A 121.0 . . ?
O2 C2 C3 116.6(7) . . ?
O2 C2 C1 122.9(6) . . ?
C3 C2 C1 120.4(6) . . ?
C4 C3 O3 124.1(6) . . ?
C4 C3 C2 121.1(7) . . ?
O3 C3 C2 114.8(6) . . ?
C3 C4 C5 119.0(7) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 119.0(7) . . ?
C6 C5 C7 111.5(6) . . ?
C4 C5 C7 129.2(6) . . ?
C5 C6 C1 122.0(7) . . ?
C5 C6 N1 110.0(6) . . ?
C1 C6 N1 128.0(6) . . ?
C5 C7 C17 113.5(6) . . ?
C5 C7 C21 115.4(6) . . ?
C17 C7 C21 103.3(5) . . ?
C5 C7 C8 101.5(5) . . ?
C17 C7 C8 110.8(6) . . ?
C21 C7 C8 112.6(6) . . ?
C18 C8 N1 106.4(6) . . ?
C18 C8 C7 118.7(6) . . ?
N1 C8 C7 103.7(5) . . ?
C18 C8 H8A 109.2 . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
O4 C9 N1 123.8(7) . . ?
O4 C9 C10 119.6(6) . . ?
N1 C9 C10 116.6(6) . . ?
C9 C10 C11 117.1(6) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 113.8(5) . . ?
O1 C11 C10 103.1(5) . . ?
C18 C11 C10 108.6(6) . . ?
O1 C11 H11A 110.4 . . ?
C18 C11 H11A 110.4 . . ?
C10 C11 H11A 110.4 . . ?
O1 C12 C13 111.8(6) . . ?
O1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 121.0(7) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C19 123.9(7) . . ?
C13 C14 C15 119.9(7) . . ?
C19 C14 C15 116.2(7) . . ?
C14 C15 N2 109.2(5) . . ?
C14 C15 H15A 109.8 . . ?
N2 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
N2 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C17 104.4(6) . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C7 C17 C16 102.0(6) . . ?
C7 C17 H17A 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C7 C17 H17B 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.2 . . ?
C8 C18 C11 110.1(6) . . ?
C8 C18 C19 111.3(6) . . ?
C11 C18 C19 117.2(6) . . ?
C8 C18 H18A 105.8 . . ?
C11 C18 H18A 105.8 . . ?
C19 C18 H18A 105.8 . . ?
C14 C19 C20 110.1(6) . . ?
C14 C19 C18 113.3(6) . . ?
C20 C19 C18 106.5(6) . . ?
C14 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C21 C20 C19 109.2(6) . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 111.5(6) . . ?
C20 C21 C7 115.7(6) . . ?
N2 C21 C7 103.7(5) . . ?
C20 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 O7 H7A 109.5 . . ?
C26 O71 H71 109.5 . . ?
C28 O8 C281 116(2) . . ?
O9 N4 O10 124.3(6) . . ?
O9 N4 C31 117.5(7) . . ?
O10 N4 C31 118.1(7) . . ?
O51 C24 O6 108.3(19) . . ?
O51 C24 O5 38.4(18) . . ?
O6 C24 O5 125.7(7) . . ?
O51 C24 O61 124(2) . . ?
O6 C24 O61 38.6(16) . . ?
O5 C24 O61 112.9(17) . . ?
O51 C24 C25 117.1(19) . . ?
O6 C24 C25 119.5(7) . . ?
O5 C24 C25 114.7(7) . . ?
O61 C24 C25 119.4(16) . . ?
N31 C25 N3 117(2) . . ?
N31 C25 C24 107(2) . . ?
N3 C25 C24 110.8(7) . . ?
N31 C25 C26 100(2) . . ?
N3 C25 C26 112.6(7) . . ?
C24 C25 C26 109.5(6) . . ?
N31 C25 H25B 113.2 . . ?
N3 C25 H25B 3.5 . . ?
C24 C25 H25B 113.2 . . ?
C26 C25 H25B 113.2 . . ?
N31 C25 H25A 9.6 . . ?
N3 C25 H25A 107.9 . . ?
C24 C25 H25A 108.0 . . ?
C26 C25 H25A 107.9 . . ?
H25B C25 H25A 104.6 . . ?
O71 C26 C27 122.4(18) . . ?
O7 C26 C27 109.6(7) . . ?
O71 C26 C25 124.7(18) . . ?
O7 C26 C25 110.6(7) . . ?
C27 C26 C25 112.2(6) . . ?
O71 C26 H26B 92.8 . . ?
C27 C26 H26B 92.8 . . ?
C25 C26 H26B 92.8 . . ?
O7 C26 H26A 108.8 . . ?
C27 C26 H26A 107.2 . . ?
C25 C26 H26A 108.2 . . ?
H26B C26 H26A 142.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 N3 C25 126.3(8) . . ?
C28 N3 H3A 116.9 . . ?
C25 N3 H3A 116.9 . . ?
O8 C28 N3 120.9(8) . . ?
O8 C28 C29 123.9(6) . . ?
N3 C28 C29 115.2(7) . . ?
C34 C29 C30 118.7(7) . . ?
C34 C29 C28 124.1(7) . . ?
C30 C29 C28 117.2(7) . . ?
C34 C29 H29A 120.6 . . ?
C30 C29 H29A 120.6 . . ?
C28 C29 H29A 3.4 . . ?
C31 C30 C29 118.7(7) . . ?
C31 C30 H30A 120.7 . . ?
C29 C30 H30A 120.7 . . ?
C32 C31 C30 123.0(6) . . ?
C32 C31 N4 119.2(7) . . ?
C30 C31 N4 117.8(7) . . ?
C31 C32 C33 117.6(7) . . ?
C31 C32 H32A 121.2 . . ?
C33 C32 H32A 121.2 . . ?
C34 C33 C32 119.7(7) . . ?
C34 C33 H33A 120.1 . . ?
C32 C33 H33A 120.1 . . ?
C29 C34 C33 122.2(7) . . ?
C29 C34 H34A 118.9 . . ?
C33 C34 H34A 118.9 . . ?
C25 N31 C281 113(4) . . ?
C25 N31 H25A 23.9 . . ?
C281 N31 H25A 93.8 . . ?
C25 N31 H31A 123.7 . . ?
C281 N31 H31A 123.7 . . ?
H25A N31 H31A 140.0 . . ?
O8 C281 N31 125(4) . . ?
O8 C281 H25A 110.4 . . ?
N31 C281 H25A 15.2 . . ?
C100 O100 H100 109.5 . . ?
C110 C100 O100 118(2) . . ?
C110 C100 H10C 107.8 . . ?
O100 C100 H10C 107.8 . . ?
C110 C100 H10D 107.8 . . ?
O100 C100 H10D 107.8 . . ?
H10C C100 H10D 107.1 . . ?
C100 C110 H11B 109.5 . . ?
C100 C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
C100 C110 H11D 109.5 . . ?
H11B C110 H11D 109.5 . . ?
H11C C110 H11D 109.5 . . ?
C100 C110 H12W 90.0 . . ?
H11B C110 H12W 105.7 . . ?
H11C C110 H12W 23.4 . . ?
H11D C110 H12W 130.3 . . ?
C101 O101 H101 109.5 . . ?
O101 C101 C111 116.4(19) . . ?
O101 C101 H10E 108.2 . . ?
C111 C101 H10E 108.2 . . ?
O101 C101 H10F 108.2 . . ?
C111 C101 H10F 108.2 . . ?
H10E C101 H10F 107.3 . . ?
C101 C111 H11E 109.5 . . ?
C101 C111 H11F 109.5 . . ?
H11E C111 H11F 109.5 . . ?
C101 C111 H11G 109.5 . . ?
H11E C111 H11G 109.5 . . ?
H11F C111 H11G 109.5 . . ?
C121 O121 H121 109.5 . . ?
O121 C121 C131 113(2) . . ?
O121 C121 H12C 108.9 . . ?
C131 C121 H12C 108.9 . . ?
O121 C121 H12D 108.9 . . ?
C131 C121 H12D 108.9 . . ?
H12C C121 H12D 107.7 . . ?
C121 C131 H13B 109.5 . . ?
C121 C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
C121 C131 H13D 109.5 . . ?
H13B C131 H13D 109.5 . . ?
H13C C131 H13D 109.5 . . ?
H11W O1W H12W 128.1 . . ?
H11W O1W H14W 80.4 . . ?
H12W O1W H14W 146.4 . . ?
H11W O1W H15W 59.2 . . ?
H12W O1W H15W 172.4 . . ?
H14W O1W H15W 26.5 . . ?
H11W O1W H16W 102.3 . . ?
H12W O1W H16W 107.0 . . ?
H14W O1W H16W 42.6 . . ?
H15W O1W H16W 67.3 . . ?
H13W O11W H14W 117.9 . . ?
H13W O11W H15W 68.3 . . ?
H14W O11W H15W 50.5 . . ?
H11W O12W H12W 77.2 . . ?
H11W O12W H14W 115.7 . . ?
H12W O12W H14W 160.4 . . ?
H11W O12W H15W 80.9 . . ?
H12W O12W H15W 156.0 . . ?
H14W O12W H15W 42.7 . . ?
H11W O12W H16W 116.8 . . ?
H12W O12W H16W 85.6 . . ?
H14W O12W H16W 75.5 . . ?
H15W O12W H16W 113.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C3 -176.9(8) . . . . ?
C22 O2 C2 C1 6.4(12) . . . . ?
C6 C1 C2 O2 -179.0(7) . . . . ?
C6 C1 C2 C3 4.4(12) . . . . ?
C23 O3 C3 C4 3.7(13) . . . . ?
C23 O3 C3 C2 -179.3(8) . . . . ?
O2 C2 C3 C4 175.9(8) . . . . ?
C1 C2 C3 C4 -7.3(13) . . . . ?
O2 C2 C3 O3 -1.2(11) . . . . ?
C1 C2 C3 O3 175.6(7) . . . . ?
O3 C3 C4 C5 -177.8(7) . . . . ?
C2 C3 C4 C5 5.4(13) . . . . ?
C3 C4 C5 C6 -0.8(13) . . . . ?
C3 C4 C5 C7 -174.4(8) . . . . ?
C4 C5 C6 C1 -1.9(13) . . . . ?
C7 C5 C6 C1 172.8(7) . . . . ?
C4 C5 C6 N1 176.2(7) . . . . ?
C7 C5 C6 N1 -9.1(10) . . . . ?
C2 C1 C6 C5 0.1(13) . . . . ?
C2 C1 C6 N1 -177.6(8) . . . . ?
C9 N1 C6 C5 -155.8(8) . . . . ?
C8 N1 C6 C5 -5.6(9) . . . . ?
C9 N1 C6 C1 22.2(13) . . . . ?
C8 N1 C6 C1 172.3(8) . . . . ?
C6 C5 C7 C17 -100.0(8) . . . . ?
C4 C5 C7 C17 74.0(11) . . . . ?
C6 C5 C7 C21 141.0(7) . . . . ?
C4 C5 C7 C21 -45.0(12) . . . . ?
C6 C5 C7 C8 18.8(9) . . . . ?
C4 C5 C7 C8 -167.2(8) . . . . ?
C9 N1 C8 C18 43.0(9) . . . . ?
C6 N1 C8 C18 -109.1(6) . . . . ?
C9 N1 C8 C7 169.0(6) . . . . ?
C6 N1 C8 C7 16.9(8) . . . . ?
C5 C7 C8 C18 97.1(7) . . . . ?
C17 C7 C8 C18 -142.2(6) . . . . ?
C21 C7 C8 C18 -27.0(8) . . . . ?
C5 C7 C8 N1 -20.7(7) . . . . ?
C17 C7 C8 N1 100.1(6) . . . . ?
C21 C7 C8 N1 -144.7(6) . . . . ?
C6 N1 C9 O4 -24.8(13) . . . . ?
C8 N1 C9 O4 -172.1(8) . . . . ?
C6 N1 C9 C10 156.3(7) . . . . ?
C8 N1 C9 C10 9.0(11) . . . . ?
O4 C9 C10 C11 145.0(8) . . . . ?
N1 C9 C10 C11 -36.0(11) . . . . ?
C12 O1 C11 C18 -70.1(8) . . . . ?
C12 O1 C11 C10 172.5(5) . . . . ?
C9 C10 C11 O1 128.7(7) . . . . ?
C9 C10 C11 C18 7.6(9) . . . . ?
C11 O1 C12 C13 90.0(8) . . . . ?
O1 C12 C13 C14 -64.3(10) . . . . ?
C12 C13 C14 C19 -4.7(11) . . . . ?
C12 C13 C14 C15 177.2(7) . . . . ?
C13 C14 C15 N2 -128.2(7) . . . . ?
C19 C14 C15 N2 53.6(9) . . . . ?
C16 N2 C15 C14 77.0(8) . . . . ?
C21 N2 C15 C14 -46.1(8) . . . . ?
C21 N2 C16 C17 -17.5(7) . . . . ?
C15 N2 C16 C17 -142.4(6) . . . . ?
C5 C7 C17 C16 -167.4(6) . . . . ?
C21 C7 C17 C16 -41.7(7) . . . . ?
C8 C7 C17 C16 79.2(7) . . . . ?
N2 C16 C17 C7 36.6(7) . . . . ?
N1 C8 C18 C11 -70.8(6) . . . . ?
C7 C8 C18 C11 172.8(5) . . . . ?
N1 C8 C18 C19 157.4(5) . . . . ?
C7 C8 C18 C19 41.1(8) . . . . ?
O1 C11 C18 C8 -70.1(7) . . . . ?
C10 C11 C18 C8 44.1(7) . . . . ?
O1 C11 C18 C19 58.5(8) . . . . ?
C10 C11 C18 C19 172.7(6) . . . . ?
C13 C14 C19 C20 179.1(7) . . . . ?
C15 C14 C19 C20 -2.8(9) . . . . ?
C13 C14 C19 C18 60.0(10) . . . . ?
C15 C14 C19 C18 -121.9(7) . . . . ?
C8 C18 C19 C14 60.3(8) . . . . ?
C11 C18 C19 C14 -67.7(9) . . . . ?
C8 C18 C19 C20 -60.8(7) . . . . ?
C11 C18 C19 C20 171.1(6) . . . . ?
C14 C19 C20 C21 -54.7(8) . . . . ?
C18 C19 C20 C21 68.5(7) . . . . ?
C19 C20 C21 N2 61.2(7) . . . . ?
C19 C20 C21 C7 -57.0(8) . . . . ?
C16 N2 C21 C20 -133.4(6) . . . . ?
C15 N2 C21 C20 -8.9(8) . . . . ?
C16 N2 C21 C7 -8.2(7) . . . . ?
C15 N2 C21 C7 116.3(6) . . . . ?
C5 C7 C21 C20 -82.0(8) . . . . ?
C17 C7 C21 C20 153.5(6) . . . . ?
C8 C7 C21 C20 33.9(8) . . . . ?
C5 C7 C21 N2 155.6(6) . . . . ?
C17 C7 C21 N2 31.1(7) . . . . ?
C8 C7 C21 N2 -88.5(6) . . . . ?
O51 C24 C25 N31 -2(3) . . . . ?
O6 C24 C25 N31 132(2) . . . . ?
O5 C24 C25 N31 -45(2) . . . . ?
O61 C24 C25 N31 177(3) . . . . ?
O51 C24 C25 N3 -130(2) . . . . ?
O6 C24 C25 N3 4.0(10) . . . . ?
O5 C24 C25 N3 -172.7(7) . . . . ?
O61 C24 C25 N3 49(2) . . . . ?
O51 C24 C25 C26 105(2) . . . . ?
O6 C24 C25 C26 -120.8(9) . . . . ?
O5 C24 C25 C26 62.5(9) . . . . ?
O61 C24 C25 C26 -76(2) . . . . ?
N31 C25 C26 O71 98(3) . . . . ?
N3 C25 C26 O71 -138(3) . . . . ?
C24 C25 C26 O71 -14(3) . . . . ?
N31 C25 C26 O7 165(2) . . . . ?
N3 C25 C26 O7 -71.0(8) . . . . ?
C24 C25 C26 O7 52.7(9) . . . . ?
N31 C25 C26 C27 -73(2) . . . . ?
N3 C25 C26 C27 51.8(10) . . . . ?
C24 C25 C26 C27 175.5(8) . . . . ?
N31 C25 N3 C28 13(2) . . . . ?
C24 C25 N3 C28 135.4(7) . . . . ?
C26 C25 N3 C28 -101.6(9) . . . . ?
C281 O8 C28 N3 -9(2) . . . . ?
C281 O8 C28 C29 172(2) . . . . ?
C25 N3 C28 O8 -0.6(12) . . . . ?
C25 N3 C28 C29 178.6(7) . . . . ?
O8 C28 C29 C34 148.0(8) . . . . ?
N3 C28 C29 C34 -31.1(11) . . . . ?
O8 C28 C29 C30 -32.2(11) . . . . ?
N3 C28 C29 C30 148.7(7) . . . . ?
C34 C29 C30 C31 1.0(10) . . . . ?
C28 C29 C30 C31 -178.9(6) . . . . ?
C29 C30 C31 C32 0.6(11) . . . . ?
C29 C30 C31 N4 178.4(6) . . . . ?
O9 N4 C31 C32 -179.9(7) . . . . ?
O10 N4 C31 C32 2.6(9) . . . . ?
O9 N4 C31 C30 2.2(9) . . . . ?
O10 N4 C31 C30 -175.3(6) . . . . ?
C30 C31 C32 C33 -2.3(11) . . . . ?
N4 C31 C32 C33 180.0(6) . . . . ?
C31 C32 C33 C34 2.4(11) . . . . ?
C30 C29 C34 C33 -0.8(11) . . . . ?
C28 C29 C34 C33 179.1(7) . . . . ?
C32 C33 C34 C29 -0.9(12) . . . . ?
N3 C25 N31 C281 -13(5) . . . . ?
C24 C25 N31 C281 -138(3) . . . . ?
C26 C25 N31 C281 108(4) . . . . ?
C28 O8 C281 N31 7(5) . . . . ?
C25 N31 C281 O8 5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.93 1.81 2.705(9) 161.9 .
N2 H2A O51 0.93 1.81 2.73(4) 170.5 .
O7 H7A O5 0.84 1.91 2.749(9) 174.9 4_456
O71 H71 O61 0.84 2.04 2.80(5) 150.6 4_556
O100 H100 O4 0.84 1.91 2.74(3) 171.2 3_656
O101 H101 O4 0.84 1.98 2.80(2) 167.6 3_656
O121 H121 O4 0.84 2.34 3.06(4) 143.6 3_656
O1W H12W O101 0.88 1.69 2.57(5) 174.9 .

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        77.92
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.087


#===== end

# start Validation Reply Form
_vrf_PLAT312_B3NBDLT             
;
PROBLEM: Strange C-O-H Geometry (C-O .LT. 1.25 Ang) ..... O71
RESPONSE: It probably results from unsolved disorder of beta carbon atom
of the disordered threonine derivative
;
_database_code_depnum_ccdc_archive 'CCDC 930482'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

# end Validation Reply Form




data_B3NBLV
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-L-valinate brucine pentahydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C23 H27 N2 O4, C23 H26 N2 O4, C12 H13 N2 O5, 5(H2 O)
;
_chemical_formula_sum            'C58 H76 N6 O18'
_chemical_formula_weight         1145.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.904(2)
_cell_length_b                   12.189(3)
_cell_length_c                   15.721(3)
_cell_angle_alpha                106.65(2)
_cell_angle_beta                 103.48(2)
_cell_angle_gamma                98.91(3)
_cell_volume                     1370.6(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3092
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.00

_exptl_crystal_description       plate
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             610
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21879
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_sigmaI/netI    0.1172
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6600
_reflns_number_gt                4152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6600
_refine_ls_number_parameters     739
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1149(4) 0.5406(2) 0.88145(18) 0.0206(6) Uani 1 1 d . . .
O2 O -0.2302(4) -0.1768(2) 0.53384(17) 0.0199(7) Uani 1 1 d . . .
O3 O -0.2288(4) -0.2444(2) 0.67578(18) 0.0235(7) Uani 1 1 d . . .
O4 O -0.2191(4) 0.2497(2) 0.59492(18) 0.0239(7) Uani 1 1 d . . .
N1 N -0.1215(4) 0.2348(3) 0.7381(2) 0.0165(7) Uani 1 1 d . . .
N2 N -0.0177(5) 0.2576(3) 1.0457(2) 0.0201(8) Uani 1 1 d . . .
H2 H -0.0006 0.2138 1.0853 0.024 Uiso 1 1 calc R . .
C1 C -0.1764(5) 0.0294(4) 0.6248(3) 0.0159(9) Uani 1 1 d . . .
H1 H -0.1818 0.0541 0.5723 0.019 Uiso 1 1 calc R . .
C2 C -0.1998(5) -0.0883(4) 0.6163(3) 0.0185(9) Uani 1 1 d . . .
C3 C -0.1926(5) -0.1246(3) 0.6939(3) 0.0185(9) Uani 1 1 d . . .
C4 C -0.1540(5) -0.0413(4) 0.7819(3) 0.0175(9) Uani 1 1 d . . .
H4 H -0.1445 -0.0652 0.8349 0.021 Uiso 1 1 calc R . .
C5 C -0.1297(5) 0.0776(3) 0.7910(2) 0.0155(9) Uani 1 1 d . . .
C6 C -0.1446(5) 0.1110(3) 0.7133(3) 0.0168(9) Uani 1 1 d . . .
C7 C -0.0672(5) 0.1835(3) 0.8779(3) 0.0166(9) Uani 1 1 d . . .
C8 C -0.0988(6) 0.2862(4) 0.8392(2) 0.0183(9) Uani 1 1 d . . .
H8 H 0.0098 0.3532 0.8683 0.022 Uiso 1 1 calc R . .
C9 C -0.1834(5) 0.2936(4) 0.6806(3) 0.0176(9) Uani 1 1 d . . .
C10 C -0.2076(6) 0.4145(4) 0.7240(3) 0.0217(10) Uani 1 1 d . . .
H10A H -0.3043 0.4289 0.6787 0.026 Uiso 1 1 calc R . .
H10B H -0.0961 0.4722 0.7336 0.026 Uiso 1 1 calc R . .
C11 C -0.2530(5) 0.4413(3) 0.8176(3) 0.0184(9) Uani 1 1 d . . .
H11 H -0.3709 0.4634 0.8097 0.022 Uiso 1 1 calc R . .
C12 C -0.1506(6) 0.5934(4) 0.9679(3) 0.0224(10) Uani 1 1 d . . .
H12A H -0.2811 0.5859 0.9566 0.027 Uiso 1 1 calc R . .
H12B H -0.0907 0.6784 0.9934 0.027 Uiso 1 1 calc R . .
C13 C -0.0843(6) 0.5349(4) 1.0379(3) 0.0245(10) Uani 1 1 d . . .
H13 H 0.0080 0.5806 1.0934 0.029 Uiso 1 1 calc R . .
C14 C -0.1494(6) 0.4228(4) 1.0251(3) 0.0219(10) Uani 1 1 d . . .
C15 C -0.0748(6) 0.3657(3) 1.0940(3) 0.0214(10) Uani 1 1 d . . .
H15A H -0.1670 0.3429 1.1230 0.026 Uiso 1 1 calc R . .
H15B H 0.0294 0.4224 1.1437 0.026 Uiso 1 1 calc R . .
C16 C 0.1559(6) 0.2889(4) 1.0242(3) 0.0220(10) Uani 1 1 d . . .
H16A H 0.2576 0.2819 1.0712 0.026 Uiso 1 1 calc R . .
H16B H 0.1784 0.3705 1.0228 0.026 Uiso 1 1 calc R . .
C17 C 0.1307(6) 0.2005(4) 0.9292(3) 0.0200(9) Uani 1 1 d . . .
H17A H 0.1561 0.1252 0.9343 0.024 Uiso 1 1 calc R . .
H17B H 0.2098 0.2319 0.8969 0.024 Uiso 1 1 calc R . .
C18 C -0.2644(5) 0.3321(4) 0.8479(3) 0.0181(9) Uani 1 1 d . . .
H18 H -0.3678 0.2707 0.7995 0.022 Uiso 1 1 calc R . .
C19 C -0.3012(5) 0.3415(3) 0.9413(3) 0.0185(9) Uani 1 1 d . . .
H19 H -0.4129 0.3701 0.9420 0.022 Uiso 1 1 calc R . .
C20 C -0.3325(5) 0.2162(4) 0.9453(3) 0.0191(9) Uani 1 1 d . . .
H20A H -0.3756 0.2143 0.9992 0.023 Uiso 1 1 calc R . .
H20B H -0.4245 0.1617 0.8882 0.023 Uiso 1 1 calc R . .
C21 C -0.1575(5) 0.1779(3) 0.9541(2) 0.0169(9) Uani 1 1 d . . .
H21 H -0.1793 0.0952 0.9548 0.020 Uiso 1 1 calc R . .
C22 C -0.2361(6) -0.1397(4) 0.4545(3) 0.0249(10) Uani 1 1 d . . .
H22A H -0.2583 -0.2089 0.3992 0.037 Uiso 1 1 calc R . .
H22B H -0.1215 -0.0863 0.4647 0.037 Uiso 1 1 calc R . .
H22C H -0.3327 -0.0988 0.4454 0.037 Uiso 1 1 calc R . .
C23 C -0.2310(7) -0.2820(4) 0.7543(3) 0.0311(11) Uani 1 1 d . . .
H23A H -0.2571 -0.3682 0.7344 0.047 Uiso 1 1 calc R . .
H23B H -0.3235 -0.2543 0.7808 0.047 Uiso 1 1 calc R . .
H23C H -0.1138 -0.2490 0.8013 0.047 Uiso 1 1 calc R . .
O1A O 0.2107(4) 0.9325(2) 0.55223(19) 0.0259(7) Uani 1 1 d . . .
O2A O 0.3388(4) 0.5005(3) 0.90791(17) 0.0258(7) Uani 1 1 d . . .
O3A O 0.2903(4) 0.3207(2) 0.76222(18) 0.0222(7) Uani 1 1 d . . .
O4A O 0.3417(5) 0.8792(3) 0.8434(2) 0.0377(9) Uani 1 1 d . . .
N1A N 0.1931(5) 0.7363(3) 0.7037(2) 0.0211(8) Uani 1 1 d . . .
N2A N 0.0152(5) 0.5028(3) 0.3960(2) 0.0215(8) Uani 1 1 d . . .
C1A C 0.2690(5) 0.6290(4) 0.8180(3) 0.0218(10) Uani 1 1 d . . .
H1A H 0.2905 0.6960 0.8717 0.026 Uiso 1 1 calc R . .
C2A C 0.2903(5) 0.5207(4) 0.8246(3) 0.0197(9) Uani 1 1 d . . .
C3A C 0.2578(5) 0.4217(3) 0.7453(3) 0.0194(9) Uani 1 1 d . . .
C4A C 0.1982(5) 0.4294(4) 0.6585(3) 0.0186(9) Uani 1 1 d . . .
H4A H 0.1732 0.3621 0.6046 0.022 Uiso 1 1 calc R . .
C5A C 0.2149(5) 0.6351(4) 0.7297(3) 0.0185(9) Uani 1 1 d . . .
C6A C 0.1748(5) 0.5376(3) 0.6503(3) 0.0165(9) Uani 1 1 d . . .
C7A C 0.0985(5) 0.5671(4) 0.5649(3) 0.0179(9) Uani 1 1 d . . .
C8A C 0.1525(5) 0.7047(3) 0.6013(3) 0.0176(9) Uani 1 1 d . . .
H8A H 0.0493 0.7364 0.5766 0.021 Uiso 1 1 calc R . .
C9A C 0.2789(6) 0.8495(4) 0.7589(3) 0.0263(11) Uani 1 1 d . . .
C10A C 0.2901(6) 0.9363(4) 0.7073(3) 0.0239(10) Uani 1 1 d . . .
H10C H 0.3817 1.0086 0.7491 0.029 Uiso 1 1 calc R . .
H10D H 0.1736 0.9583 0.6948 0.029 Uiso 1 1 calc R . .
C11A C 0.3354(6) 0.8961(4) 0.6149(3) 0.0232(10) Uani 1 1 d . . .
H11A H 0.4603 0.9384 0.6233 0.028 Uiso 1 1 calc R . .
C12A C 0.2396(6) 0.9155(4) 0.4630(3) 0.0311(11) Uani 1 1 d . . .
H12C H 0.3696 0.9266 0.4702 0.037 Uiso 1 1 calc R . .
H12D H 0.1976 0.9757 0.4381 0.037 Uiso 1 1 calc R . .
C13A C 0.1429(6) 0.7946(4) 0.3950(3) 0.0252(10) Uani 1 1 d . . .
H13A H 0.0498 0.7878 0.3418 0.030 Uiso 1 1 calc R . .
C14A C 0.1829(6) 0.6981(4) 0.4068(3) 0.0208(9) Uani 1 1 d . . .
C15A C 0.0784(6) 0.5750(4) 0.3435(3) 0.0242(10) Uani 1 1 d . . .
H15C H -0.0259 0.5806 0.2972 0.029 Uiso 1 1 calc R . .
H15D H 0.1556 0.5360 0.3095 0.029 Uiso 1 1 calc R . .
C16A C -0.1361(5) 0.5390(4) 0.4288(3) 0.0202(9) Uani 1 1 d . . .
H16C H -0.2525 0.4887 0.3855 0.024 Uiso 1 1 calc R . .
H16D H -0.1340 0.6223 0.4346 0.024 Uiso 1 1 calc R . .
C17A C -0.1055(5) 0.5227(4) 0.5233(3) 0.0193(9) Uani 1 1 d . . .
H17C H -0.1453 0.4388 0.5169 0.023 Uiso 1 1 calc R . .
H17D H -0.1687 0.5704 0.5617 0.023 Uiso 1 1 calc R . .
C18A C 0.3207(5) 0.7622(4) 0.5833(3) 0.0201(9) Uani 1 1 d . . .
H18A H 0.4236 0.7506 0.6280 0.024 Uiso 1 1 calc R . .
C19A C 0.3362(6) 0.7017(4) 0.4874(3) 0.0224(10) Uani 1 1 d . . .
H19A H 0.4514 0.7417 0.4818 0.027 Uiso 1 1 calc R . .
C20A C 0.3423(6) 0.5742(4) 0.4822(3) 0.0220(10) Uani 1 1 d . . .
H20C H 0.3732 0.5337 0.4257 0.026 Uiso 1 1 calc R . .
H20D H 0.4350 0.5747 0.5370 0.026 Uiso 1 1 calc R . .
C21A C 0.1603(5) 0.5094(4) 0.4798(3) 0.0182(9) Uani 1 1 d . . .
H21A H 0.1661 0.4272 0.4773 0.022 Uiso 1 1 calc R . .
C22A C 0.3529(7) 0.5957(4) 0.9891(3) 0.0334(12) Uani 1 1 d . . .
H22D H 0.3872 0.5718 1.0439 0.050 Uiso 1 1 calc R . .
H22E H 0.2371 0.6166 0.9844 0.050 Uiso 1 1 calc R . .
H22F H 0.4439 0.6639 0.9948 0.050 Uiso 1 1 calc R . .
C23A C 0.2699(6) 0.2216(4) 0.6826(3) 0.0271(11) Uani 1 1 d . . .
H23D H 0.2965 0.1552 0.7022 0.041 Uiso 1 1 calc R . .
H23E H 0.3528 0.2420 0.6488 0.041 Uiso 1 1 calc R . .
H23F H 0.1466 0.1996 0.6420 0.041 Uiso 1 1 calc R . .
O5 O 0.2327(4) 0.0846(3) 1.12745(18) 0.0250(7) Uani 1 1 d . . .
O6 O 0.0258(4) 0.1642(3) 1.17974(18) 0.0227(7) Uani 1 1 d . . .
O7 O 0.1495(4) -0.1406(2) 1.20353(19) 0.0242(7) Uani 1 1 d . . .
O8 O 0.6367(4) -0.5039(3) 1.1964(2) 0.0357(8) Uani 1 1 d . . .
O9 O 0.3889(4) -0.4897(3) 1.2289(2) 0.0372(8) Uani 1 1 d . . .
N3 N 0.3578(5) 0.0306(3) 1.2852(2) 0.0182(7) Uani 1 1 d . . .
H3 H 0.4709 0.0632 1.3170 0.022 Uiso 1 1 calc R . .
N4 N 0.5258(5) -0.4477(3) 1.2141(2) 0.0255(9) Uani 1 1 d . . .
C24 C 0.1585(6) 0.1174(4) 1.1888(3) 0.0209(9) Uani 1 1 d . . .
C25 C 0.2273(5) 0.1026(3) 1.2841(3) 0.0179(9) Uani 1 1 d . . .
H25 H 0.1223 0.0617 1.2978 0.021 Uiso 1 1 calc R . .
C26 C 0.3026(6) 0.2253(4) 1.3597(3) 0.0199(9) Uani 1 1 d . . .
H26 H 0.2049 0.2684 1.3543 0.024 Uiso 1 1 calc R . .
C27 C 0.4603(6) 0.2981(4) 1.3444(3) 0.0245(10) Uani 1 1 d . . .
H27A H 0.5028 0.3751 1.3939 0.037 Uiso 1 1 calc R . .
H27B H 0.4223 0.3092 1.2842 0.037 Uiso 1 1 calc R . .
H27C H 0.5573 0.2568 1.3454 0.037 Uiso 1 1 calc R . .
C28 C 0.3466(6) 0.2178(4) 1.4574(3) 0.0236(10) Uani 1 1 d . . .
H28A H 0.3943 0.2973 1.5031 0.035 Uiso 1 1 calc R . .
H28B H 0.4362 0.1711 1.4644 0.035 Uiso 1 1 calc R . .
H28C H 0.2376 0.1800 1.4673 0.035 Uiso 1 1 calc R . .
C29 C 0.3065(6) -0.0848(4) 1.2382(3) 0.0187(9) Uani 1 1 d . . .
C30 C 0.4560(5) -0.1478(3) 1.2296(2) 0.0164(9) Uani 1 1 d . . .
C31 C 0.4267(5) -0.2634(3) 1.2299(2) 0.0175(9) Uani 1 1 d . . .
H31 H 0.3207 -0.2991 1.2398 0.021 Uiso 1 1 calc R . .
C32 C 0.5572(6) -0.3246(4) 1.2153(3) 0.0187(9) Uani 1 1 d . . .
C33 C 0.7127(6) -0.2765(4) 1.1990(3) 0.0210(10) Uani 1 1 d . . .
H33 H 0.7991 -0.3209 1.1886 0.025 Uiso 1 1 calc R . .
C34 C 0.7378(6) -0.1619(4) 1.1984(3) 0.0234(10) Uani 1 1 d . . .
H34 H 0.8423 -0.1270 1.1868 0.028 Uiso 1 1 calc R . .
C35 C 0.6105(5) -0.0973(4) 1.2146(3) 0.0206(9) Uani 1 1 d . . .
H35 H 0.6302 -0.0181 1.2154 0.025 Uiso 1 1 calc R . .
O1W O -0.4193(4) 0.1523(3) 0.1296(2) 0.0357(8) Uani 1 1 d . . .
H11W H -0.3416 0.1773 0.1851 0.054 Uiso 1 1 d R . .
H12W H -0.5325 0.1319 0.1292 0.054 Uiso 1 1 d R . .
O2W O -0.0575(5) -0.1070(3) -0.0227(2) 0.0374(8) Uani 1 1 d . . .
H21W H 0.0261 -0.0508 0.0213 0.056 Uiso 1 1 d R . .
H22W H -0.1603 -0.0919 -0.0124 0.056 Uiso 1 1 d R . .
O3W O -0.1443(4) 0.2610(2) 0.30078(18) 0.0245(7) Uani 1 1 d . . .
H31W H -0.0741 0.3225 0.3397 0.037 Uiso 1 1 d R . .
H32W H -0.0887 0.2291 0.2611 0.037 Uiso 1 1 d R . .
O4W O -0.2439(4) 0.1236(3) 0.4057(2) 0.0312(8) Uani 1 1 d . . .
H41W H -0.2003 0.1740 0.3818 0.047 Uiso 1 1 d R . .
H42W H -0.2042 0.1544 0.4670 0.047 Uiso 1 1 d R . .
O5W O -0.3769(5) -0.0576(3) 0.0099(2) 0.0468(9) Uani 1 1 d . . .
H51W H -0.4637 -0.0786 -0.0424 0.070 Uiso 1 1 d R . .
H52W H -0.3897 0.0058 0.0463 0.070 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0219(17) 0.0152(16) 0.0219(15) 0.0040(12) 0.0069(13) -0.0002(12)
O2 0.0266(17) 0.0163(16) 0.0145(15) 0.0039(12) 0.0041(12) 0.0042(13)
O3 0.0332(19) 0.0162(17) 0.0213(15) 0.0062(13) 0.0066(13) 0.0093(13)
O4 0.0296(18) 0.0195(17) 0.0178(15) 0.0030(13) 0.0026(13) 0.0050(14)
N1 0.0157(19) 0.0144(19) 0.0185(17) 0.0049(15) 0.0047(14) 0.0023(14)
N2 0.025(2) 0.023(2) 0.0155(17) 0.0086(15) 0.0075(15) 0.0109(16)
C1 0.010(2) 0.023(2) 0.016(2) 0.0097(18) 0.0031(16) 0.0056(17)
C2 0.011(2) 0.024(3) 0.019(2) 0.0034(19) 0.0054(17) 0.0097(18)
C3 0.020(2) 0.012(2) 0.023(2) 0.0045(18) 0.0064(18) 0.0067(18)
C4 0.012(2) 0.022(2) 0.022(2) 0.0103(19) 0.0067(17) 0.0057(18)
C5 0.015(2) 0.017(2) 0.0116(19) 0.0016(17) 0.0020(16) 0.0027(17)
C6 0.014(2) 0.012(2) 0.023(2) 0.0033(18) 0.0045(17) 0.0034(17)
C7 0.020(2) 0.014(2) 0.015(2) 0.0043(17) 0.0041(17) 0.0049(17)
C8 0.020(2) 0.020(2) 0.014(2) 0.0055(18) 0.0033(17) 0.0039(18)
C9 0.013(2) 0.018(2) 0.021(2) 0.0073(19) 0.0045(17) -0.0015(16)
C10 0.027(3) 0.018(2) 0.023(2) 0.0076(19) 0.011(2) 0.0061(19)
C11 0.015(2) 0.015(2) 0.023(2) 0.0028(18) 0.0042(18) 0.0045(17)
C12 0.028(3) 0.019(2) 0.022(2) 0.0051(19) 0.012(2) 0.0051(19)
C13 0.028(3) 0.023(3) 0.020(2) 0.0023(19) 0.006(2) 0.007(2)
C14 0.022(3) 0.031(3) 0.016(2) 0.0067(19) 0.0103(18) 0.012(2)
C15 0.030(3) 0.014(2) 0.020(2) 0.0015(18) 0.0100(19) 0.0097(19)
C16 0.025(3) 0.025(2) 0.016(2) 0.0092(18) 0.0031(18) 0.0080(19)
C17 0.024(2) 0.015(2) 0.021(2) 0.0033(17) 0.0076(18) 0.0079(18)
C18 0.019(2) 0.018(2) 0.019(2) 0.0057(18) 0.0050(18) 0.0085(18)
C19 0.022(2) 0.019(2) 0.019(2) 0.0091(18) 0.0075(18) 0.0071(18)
C20 0.020(2) 0.024(2) 0.017(2) 0.0092(18) 0.0101(18) 0.0062(18)
C21 0.024(2) 0.015(2) 0.0122(19) 0.0052(17) 0.0036(17) 0.0065(18)
C22 0.028(3) 0.025(3) 0.016(2) 0.0000(19) 0.0030(19) 0.0064(19)
C23 0.049(3) 0.018(3) 0.030(3) 0.012(2) 0.012(2) 0.010(2)
O1A 0.0262(18) 0.0237(17) 0.0300(17) 0.0132(14) 0.0068(14) 0.0068(13)
O2A 0.0295(18) 0.0293(18) 0.0130(15) 0.0069(13) -0.0020(13) 0.0042(14)
O3A 0.0256(17) 0.0204(17) 0.0202(15) 0.0081(13) 0.0040(13) 0.0064(13)
O4A 0.052(2) 0.0257(19) 0.0225(17) -0.0001(14) -0.0045(16) 0.0123(16)
N1A 0.023(2) 0.017(2) 0.0224(18) 0.0063(15) 0.0061(16) 0.0065(16)
N2A 0.025(2) 0.022(2) 0.0196(18) 0.0090(16) 0.0065(16) 0.0080(16)
C1A 0.019(2) 0.026(3) 0.014(2) 0.0014(18) 0.0018(18) 0.0042(19)
C2A 0.014(2) 0.026(3) 0.018(2) 0.0081(19) 0.0024(17) 0.0040(18)
C3A 0.020(2) 0.015(2) 0.025(2) 0.0103(19) 0.0045(18) 0.0039(18)
C4A 0.017(2) 0.018(2) 0.022(2) 0.0070(18) 0.0082(18) 0.0026(17)
C5A 0.012(2) 0.018(2) 0.022(2) 0.0054(18) 0.0029(17) 0.0030(17)
C6A 0.012(2) 0.017(2) 0.019(2) 0.0052(18) 0.0039(17) 0.0025(17)
C7A 0.017(2) 0.015(2) 0.021(2) 0.0049(18) 0.0061(17) 0.0064(17)
C8A 0.015(2) 0.015(2) 0.019(2) 0.0032(17) 0.0016(17) 0.0006(17)
C9A 0.024(3) 0.016(3) 0.031(3) 0.000(2) 0.001(2) 0.007(2)
C10A 0.016(2) 0.014(2) 0.032(2) 0.0032(19) -0.0039(19) 0.0000(18)
C11A 0.017(2) 0.017(2) 0.034(3) 0.008(2) 0.003(2) 0.0049(18)
C12A 0.028(3) 0.031(3) 0.044(3) 0.022(2) 0.017(2) 0.004(2)
C13A 0.026(3) 0.024(3) 0.025(2) 0.009(2) 0.009(2) 0.003(2)
C14A 0.018(2) 0.024(3) 0.027(2) 0.011(2) 0.0143(19) 0.0075(19)
C15A 0.028(3) 0.030(3) 0.022(2) 0.015(2) 0.0112(19) 0.009(2)
C16A 0.018(2) 0.018(2) 0.023(2) 0.0090(18) 0.0028(18) 0.0034(18)
C17A 0.022(2) 0.014(2) 0.018(2) 0.0012(17) 0.0058(18) 0.0003(18)
C18A 0.013(2) 0.018(2) 0.030(2) 0.0108(19) 0.0035(19) 0.0035(17)
C19A 0.015(2) 0.021(2) 0.034(2) 0.011(2) 0.0099(19) 0.0027(18)
C20A 0.023(3) 0.023(2) 0.023(2) 0.0071(19) 0.0094(19) 0.0116(19)
C21A 0.020(2) 0.013(2) 0.021(2) 0.0039(17) 0.0069(18) 0.0041(17)
C22A 0.042(3) 0.038(3) 0.013(2) 0.001(2) 0.004(2) 0.009(2)
C23A 0.034(3) 0.021(3) 0.025(2) 0.007(2) 0.004(2) 0.010(2)
O5 0.0247(17) 0.0307(18) 0.0201(15) 0.0063(13) 0.0092(13) 0.0085(14)
O6 0.0227(17) 0.0295(18) 0.0194(14) 0.0086(13) 0.0069(13) 0.0143(13)
O7 0.0201(18) 0.0209(17) 0.0308(16) 0.0078(13) 0.0066(14) 0.0050(13)
O8 0.041(2) 0.0274(19) 0.050(2) 0.0146(16) 0.0205(17) 0.0246(16)
O9 0.040(2) 0.029(2) 0.057(2) 0.0216(17) 0.0268(18) 0.0148(16)
N3 0.0190(19) 0.0131(18) 0.0195(17) 0.0031(14) 0.0039(15) 0.0025(14)
N4 0.033(2) 0.025(2) 0.0207(18) 0.0084(16) 0.0092(17) 0.0101(18)
C24 0.022(2) 0.015(2) 0.024(2) 0.0073(18) 0.0045(19) 0.0029(18)
C25 0.016(2) 0.020(2) 0.022(2) 0.0089(18) 0.0082(18) 0.0092(18)
C26 0.020(2) 0.020(2) 0.020(2) 0.0088(19) 0.0038(18) 0.0062(18)
C27 0.028(3) 0.017(2) 0.026(2) 0.0052(19) 0.007(2) 0.0045(19)
C28 0.027(3) 0.024(3) 0.019(2) 0.0044(19) 0.0083(19) 0.007(2)
C29 0.019(2) 0.019(2) 0.019(2) 0.0080(18) 0.0060(18) 0.0034(18)
C30 0.022(2) 0.010(2) 0.0110(19) -0.0022(16) 0.0023(17) 0.0023(17)
C31 0.016(2) 0.022(2) 0.0103(19) 0.0008(17) 0.0059(16) -0.0004(17)
C32 0.017(2) 0.023(2) 0.0166(19) 0.0067(17) 0.0039(17) 0.0079(18)
C33 0.021(2) 0.025(3) 0.017(2) 0.0052(18) 0.0069(18) 0.0102(19)
C34 0.020(2) 0.022(3) 0.025(2) 0.0051(19) 0.0089(19) -0.0012(18)
C35 0.020(2) 0.019(2) 0.024(2) 0.0087(19) 0.0073(19) 0.0072(19)
O1W 0.0246(18) 0.051(2) 0.0255(16) 0.0100(15) 0.0057(14) 0.0003(16)
O2W 0.043(2) 0.033(2) 0.0280(17) 0.0038(15) 0.0047(15) 0.0064(16)
O3W 0.0230(17) 0.0237(17) 0.0220(15) 0.0012(13) 0.0088(13) 0.0013(13)
O4W 0.043(2) 0.0239(18) 0.0279(16) 0.0090(14) 0.0109(15) 0.0086(15)
O5W 0.045(2) 0.056(2) 0.0315(18) 0.0046(17) 0.0039(17) 0.0179(19)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.431(5) . ?
O1 C12 1.440(5) . ?
O2 C2 1.369(5) . ?
O2 C22 1.437(5) . ?
O3 C3 1.374(5) . ?
O3 C23 1.437(5) . ?
O4 C9 1.242(5) . ?
N1 C9 1.357(5) . ?
N1 C6 1.417(5) . ?
N1 C8 1.488(5) . ?
N2 C16 1.507(5) . ?
N2 C15 1.512(5) . ?
N2 C21 1.537(5) . ?
N2 H2 0.9300 . ?
C1 C2 1.381(6) . ?
C1 C6 1.399(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.405(5) . ?
C3 C4 1.393(5) . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 C7 1.502(5) . ?
C7 C17 1.535(6) . ?
C7 C21 1.542(5) . ?
C7 C8 1.568(6) . ?
C8 C18 1.520(6) . ?
C8 H8 1.0000 . ?
C9 C10 1.500(6) . ?
C10 C11 1.551(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.535(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.514(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.322(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.506(6) . ?
C14 C19 1.518(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.539(5) . ?
C18 H18 1.0000 . ?
C19 C20 1.531(6) . ?
C19 H19 1.0000 . ?
C20 C21 1.516(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1A C12A 1.436(5) . ?
O1A C11A 1.440(5) . ?
O2A C2A 1.380(5) . ?
O2A C22A 1.426(5) . ?
O3A C3A 1.381(5) . ?
O3A C23A 1.425(5) . ?
O4A C9A 1.225(5) . ?
N1A C9A 1.366(5) . ?
N1A C5A 1.428(5) . ?
N1A C8A 1.487(5) . ?
N2A C15A 1.475(5) . ?
N2A C16A 1.487(5) . ?
N2A C21A 1.505(5) . ?
C1A C5A 1.381(6) . ?
C1A C2A 1.387(6) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.402(6) . ?
C3A C4A 1.372(5) . ?
C4A C6A 1.396(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.386(5) . ?
C6A C7A 1.504(5) . ?
C7A C17A 1.534(6) . ?
C7A C21A 1.548(5) . ?
C7A C8A 1.561(6) . ?
C8A C18A 1.529(6) . ?
C8A H8A 1.0000 . ?
C9A C10A 1.511(6) . ?
C10A C11A 1.539(6) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C18A 1.541(6) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.505(6) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.316(6) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.517(6) . ?
C14A C19A 1.520(6) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A C17A 1.524(5) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.520(6) . ?
C18A H18A 1.0000 . ?
C19A C20A 1.542(6) . ?
C19A H19A 1.0000 . ?
C20A C21A 1.516(6) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21A 1.0000 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
O5 C24 1.245(5) . ?
O6 C24 1.269(5) . ?
O7 C29 1.229(5) . ?
O8 N4 1.227(4) . ?
O9 N4 1.225(5) . ?
N3 C29 1.333(5) . ?
N3 C25 1.455(5) . ?
N3 H3 0.8800 . ?
N4 C32 1.476(6) . ?
C24 C25 1.542(5) . ?
C25 C26 1.542(6) . ?
C25 H25 1.0000 . ?
C26 C27 1.522(6) . ?
C26 C28 1.526(5) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.516(6) . ?
C30 C35 1.382(6) . ?
C30 C31 1.394(5) . ?
C31 C32 1.387(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.389(6) . ?
C33 C34 1.383(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.396(6) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
O1W H11W 0.8787 . ?
O1W H12W 0.8890 . ?
O2W H21W 0.8718 . ?
O2W H22W 0.9001 . ?
O3W H31W 0.8330 . ?
O3W H32W 0.8800 . ?
O4W H41W 0.8751 . ?
O4W H42W 0.8844 . ?
O5W H51W 0.8795 . ?
O5W H52W 0.8557 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.2(3) . . ?
C2 O2 C22 115.6(3) . . ?
C3 O3 C23 115.7(3) . . ?
C9 N1 C6 125.9(3) . . ?
C9 N1 C8 119.5(3) . . ?
C6 N1 C8 109.2(3) . . ?
C16 N2 C15 112.2(3) . . ?
C16 N2 C21 107.3(3) . . ?
C15 N2 C21 113.3(3) . . ?
C16 N2 H2 108.0 . . ?
C15 N2 H2 108.0 . . ?
C21 N2 H2 108.0 . . ?
C2 C1 C6 117.7(4) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
O2 C2 C1 123.5(4) . . ?
O2 C2 C3 115.5(4) . . ?
C1 C2 C3 121.0(4) . . ?
O3 C3 C4 124.2(4) . . ?
O3 C3 C2 115.6(3) . . ?
C4 C3 C2 120.1(4) . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 119.9(4) . . ?
C6 C5 C7 110.9(3) . . ?
C4 C5 C7 128.9(4) . . ?
C5 C6 C1 122.2(4) . . ?
C5 C6 N1 110.3(3) . . ?
C1 C6 N1 127.5(4) . . ?
C5 C7 C17 111.4(3) . . ?
C5 C7 C21 116.1(3) . . ?
C17 C7 C21 101.8(3) . . ?
C5 C7 C8 102.2(3) . . ?
C17 C7 C8 112.0(3) . . ?
C21 C7 C8 113.7(3) . . ?
N1 C8 C18 106.5(3) . . ?
N1 C8 C7 104.4(3) . . ?
C18 C8 C7 117.2(3) . . ?
N1 C8 H8 109.4 . . ?
C18 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
O4 C9 N1 121.8(4) . . ?
O4 C9 C10 120.5(3) . . ?
N1 C9 C10 117.7(3) . . ?
C9 C10 C11 117.7(3) . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 113.4(3) . . ?
O1 C11 C10 105.6(3) . . ?
C18 C11 C10 110.1(3) . . ?
O1 C11 H11 109.2 . . ?
C18 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
O1 C12 C13 111.2(3) . . ?
O1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 122.8(4) . . ?
C14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 C19 123.8(4) . . ?
C15 C14 C19 114.7(4) . . ?
C14 C15 N2 110.0(3) . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
N2 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 104.8(3) . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.7(3) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 107.5(3) . . ?
C8 C18 C19 112.9(3) . . ?
C11 C18 C19 118.4(3) . . ?
C8 C18 H18 105.7 . . ?
C11 C18 H18 105.7 . . ?
C19 C18 H18 105.7 . . ?
C14 C19 C20 109.9(3) . . ?
C14 C19 C18 113.8(3) . . ?
C20 C19 C18 106.1(3) . . ?
C14 C19 H19 109.0 . . ?
C20 C19 H19 109.0 . . ?
C18 C19 H19 109.0 . . ?
C21 C20 C19 108.7(3) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 110.1(3) . . ?
C20 C21 C7 116.1(3) . . ?
N2 C21 C7 105.1(3) . . ?
C20 C21 H21 108.5 . . ?
N2 C21 H21 108.5 . . ?
C7 C21 H21 108.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12A O1A C11A 114.8(3) . . ?
C2A O2A C22A 116.3(3) . . ?
C3A O3A C23A 116.1(3) . . ?
C9A N1A C5A 124.0(3) . . ?
C9A N1A C8A 119.0(3) . . ?
C5A N1A C8A 109.8(3) . . ?
C15A N2A C16A 112.0(3) . . ?
C15A N2A C21A 112.6(3) . . ?
C16A N2A C21A 107.4(3) . . ?
C5A C1A C2A 116.8(4) . . ?
C5A C1A H1A 121.6 . . ?
C2A C1A H1A 121.6 . . ?
O2A C2A C1A 123.3(4) . . ?
O2A C2A C3A 115.0(4) . . ?
C1A C2A C3A 121.6(4) . . ?
C4A C3A O3A 124.4(4) . . ?
C4A C3A C2A 120.2(4) . . ?
O3A C3A C2A 115.4(3) . . ?
C3A C4A C6A 119.1(4) . . ?
C3A C4A H4A 120.4 . . ?
C6A C4A H4A 120.4 . . ?
C1A C5A C6A 122.7(4) . . ?
C1A C5A N1A 128.1(4) . . ?
C6A C5A N1A 109.2(3) . . ?
C5A C6A C4A 119.5(4) . . ?
C5A C6A C7A 110.9(3) . . ?
C4A C6A C7A 129.5(4) . . ?
C6A C7A C17A 114.5(3) . . ?
C6A C7A C21A 115.1(3) . . ?
C17A C7A C21A 100.6(3) . . ?
C6A C7A C8A 102.6(3) . . ?
C17A C7A C8A 110.4(3) . . ?
C21A C7A C8A 114.2(3) . . ?
N1A C8A C18A 106.4(3) . . ?
N1A C8A C7A 103.8(3) . . ?
C18A C8A C7A 116.4(3) . . ?
N1A C8A H8A 110.0 . . ?
C18A C8A H8A 110.0 . . ?
C7A C8A H8A 110.0 . . ?
O4A C9A N1A 123.3(4) . . ?
O4A C9A C10A 122.2(4) . . ?
N1A C9A C10A 114.4(4) . . ?
C9A C10A C11A 117.2(3) . . ?
C9A C10A H10C 108.0 . . ?
C11A C10A H10C 108.0 . . ?
C9A C10A H10D 108.0 . . ?
C11A C10A H10D 108.0 . . ?
H10C C10A H10D 107.2 . . ?
O1A C11A C10A 104.5(3) . . ?
O1A C11A C18A 114.0(3) . . ?
C10A C11A C18A 110.1(3) . . ?
O1A C11A H11A 109.4 . . ?
C10A C11A H11A 109.4 . . ?
C18A C11A H11A 109.4 . . ?
O1A C12A C13A 112.0(3) . . ?
O1A C12A H12C 109.2 . . ?
C13A C12A H12C 109.2 . . ?
O1A C12A H12D 109.2 . . ?
C13A C12A H12D 109.2 . . ?
H12C C12A H12D 107.9 . . ?
C14A C13A C12A 122.2(4) . . ?
C14A C13A H13A 118.9 . . ?
C12A C13A H13A 118.9 . . ?
C13A C14A C15A 123.3(4) . . ?
C13A C14A C19A 122.2(4) . . ?
C15A C14A C19A 114.5(3) . . ?
N2A C15A C14A 111.8(3) . . ?
N2A C15A H15C 109.3 . . ?
C14A C15A H15C 109.3 . . ?
N2A C15A H15D 109.3 . . ?
C14A C15A H15D 109.3 . . ?
H15C C15A H15D 107.9 . . ?
N2A C16A C17A 104.4(3) . . ?
N2A C16A H16C 110.9 . . ?
C17A C16A H16C 110.9 . . ?
N2A C16A H16D 110.9 . . ?
C17A C16A H16D 110.9 . . ?
H16C C16A H16D 108.9 . . ?
C16A C17A C7A 102.2(3) . . ?
C16A C17A H17C 111.3 . . ?
C7A C17A H17C 111.3 . . ?
C16A C17A H17D 111.3 . . ?
C7A C17A H17D 111.3 . . ?
H17C C17A H17D 109.2 . . ?
C19A C18A C8A 113.6(3) . . ?
C19A C18A C11A 118.5(3) . . ?
C8A C18A C11A 107.1(3) . . ?
C19A C18A H18A 105.5 . . ?
C8A C18A H18A 105.5 . . ?
C11A C18A H18A 105.5 . . ?
C18A C19A C14A 115.1(3) . . ?
C18A C19A C20A 105.8(3) . . ?
C14A C19A C20A 108.8(3) . . ?
C18A C19A H19A 109.0 . . ?
C14A C19A H19A 109.0 . . ?
C20A C19A H19A 109.0 . . ?
C21A C20A C19A 108.9(3) . . ?
C21A C20A H20C 109.9 . . ?
C19A C20A H20C 109.9 . . ?
C21A C20A H20D 109.9 . . ?
C19A C20A H20D 109.9 . . ?
H20C C20A H20D 108.3 . . ?
N2A C21A C20A 112.0(3) . . ?
N2A C21A C7A 105.9(3) . . ?
C20A C21A C7A 113.8(3) . . ?
N2A C21A H21A 108.3 . . ?
C20A C21A H21A 108.3 . . ?
C7A C21A H21A 108.3 . . ?
O2A C22A H22D 109.5 . . ?
O2A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
O2A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
O3A C23A H23D 109.5 . . ?
O3A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
O3A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C29 N3 C25 120.1(3) . . ?
C29 N3 H3 119.9 . . ?
C25 N3 H3 119.9 . . ?
O9 N4 O8 123.1(4) . . ?
O9 N4 C32 118.6(4) . . ?
O8 N4 C32 118.3(4) . . ?
O5 C24 O6 124.6(4) . . ?
O5 C24 C25 120.2(4) . . ?
O6 C24 C25 115.2(4) . . ?
N3 C25 C24 112.6(3) . . ?
N3 C25 C26 111.8(3) . . ?
C24 C25 C26 109.3(3) . . ?
N3 C25 H25 107.6 . . ?
C24 C25 H25 107.6 . . ?
C26 C25 H25 107.6 . . ?
C27 C26 C28 112.0(3) . . ?
C27 C26 C25 112.6(3) . . ?
C28 C26 C25 112.1(3) . . ?
C27 C26 H26 106.5 . . ?
C28 C26 H26 106.5 . . ?
C25 C26 H26 106.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O7 C29 N3 124.2(4) . . ?
O7 C29 C30 119.9(4) . . ?
N3 C29 C30 115.9(4) . . ?
C35 C30 C31 120.3(4) . . ?
C35 C30 C29 122.0(4) . . ?
C31 C30 C29 117.5(4) . . ?
C32 C31 C30 117.9(4) . . ?
C32 C31 H31 121.0 . . ?
C30 C31 H31 121.0 . . ?
C31 C32 C33 122.9(4) . . ?
C31 C32 N4 118.2(4) . . ?
C33 C32 N4 118.8(4) . . ?
C34 C33 C32 118.0(4) . . ?
C34 C33 H33 121.0 . . ?
C32 C33 H33 121.0 . . ?
C33 C34 C35 120.4(4) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C34 120.4(4) . . ?
C30 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
H11W O1W H12W 114.1 . . ?
H21W O2W H22W 104.2 . . ?
H31W O3W H32W 108.0 . . ?
H41W O4W H42W 109.0 . . ?
H51W O5W H52W 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 0.2(5) . . . . ?
C22 O2 C2 C3 -179.5(4) . . . . ?
C6 C1 C2 O2 -179.4(4) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C23 O3 C3 C4 2.0(6) . . . . ?
C23 O3 C3 C2 -176.8(4) . . . . ?
O2 C2 C3 O3 -4.1(5) . . . . ?
C1 C2 C3 O3 176.1(4) . . . . ?
O2 C2 C3 C4 177.0(3) . . . . ?
C1 C2 C3 C4 -2.7(6) . . . . ?
O3 C3 C4 C5 -176.3(4) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C3 C4 C5 C7 -172.3(4) . . . . ?
C4 C5 C6 C1 -2.7(6) . . . . ?
C7 C5 C6 C1 171.1(4) . . . . ?
C4 C5 C6 N1 177.9(3) . . . . ?
C7 C5 C6 N1 -8.4(5) . . . . ?
C2 C1 C6 C5 2.4(6) . . . . ?
C2 C1 C6 N1 -178.2(4) . . . . ?
C9 N1 C6 C5 -156.8(4) . . . . ?
C8 N1 C6 C5 -3.1(4) . . . . ?
C9 N1 C6 C1 23.8(6) . . . . ?
C8 N1 C6 C1 177.5(4) . . . . ?
C6 C5 C7 C17 -104.4(4) . . . . ?
C4 C5 C7 C17 68.7(5) . . . . ?
C6 C5 C7 C21 139.8(3) . . . . ?
C4 C5 C7 C21 -47.2(6) . . . . ?
C6 C5 C7 C8 15.4(4) . . . . ?
C4 C5 C7 C8 -171.6(4) . . . . ?
C9 N1 C8 C18 43.4(4) . . . . ?
C6 N1 C8 C18 -112.2(4) . . . . ?
C9 N1 C8 C7 168.1(3) . . . . ?
C6 N1 C8 C7 12.4(4) . . . . ?
C5 C7 C8 N1 -16.2(4) . . . . ?
C17 C7 C8 N1 103.2(3) . . . . ?
C21 C7 C8 N1 -142.1(3) . . . . ?
C5 C7 C8 C18 101.4(4) . . . . ?
C17 C7 C8 C18 -139.2(3) . . . . ?
C21 C7 C8 C18 -24.5(5) . . . . ?
C6 N1 C9 O4 -22.4(6) . . . . ?
C8 N1 C9 O4 -173.7(4) . . . . ?
C6 N1 C9 C10 157.6(4) . . . . ?
C8 N1 C9 C10 6.4(5) . . . . ?
O4 C9 C10 C11 150.5(4) . . . . ?
N1 C9 C10 C11 -29.5(5) . . . . ?
C12 O1 C11 C18 -70.5(4) . . . . ?
C12 O1 C11 C10 168.9(3) . . . . ?
C9 C10 C11 O1 122.7(4) . . . . ?
C9 C10 C11 C18 -0.1(5) . . . . ?
C11 O1 C12 C13 88.0(4) . . . . ?
O1 C12 C13 C14 -63.4(5) . . . . ?
C12 C13 C14 C15 177.1(4) . . . . ?
C12 C13 C14 C19 -2.2(6) . . . . ?
C13 C14 C15 N2 -124.6(4) . . . . ?
C19 C14 C15 N2 54.7(4) . . . . ?
C16 N2 C15 C14 75.7(4) . . . . ?
C21 N2 C15 C14 -46.0(4) . . . . ?
C15 N2 C16 C17 -141.2(3) . . . . ?
C21 N2 C16 C17 -16.1(4) . . . . ?
N2 C16 C17 C7 36.2(4) . . . . ?
C5 C7 C17 C16 -166.1(3) . . . . ?
C21 C7 C17 C16 -41.8(4) . . . . ?
C8 C7 C17 C16 80.0(4) . . . . ?
N1 C8 C18 C11 -70.9(4) . . . . ?
C7 C8 C18 C11 172.7(3) . . . . ?
N1 C8 C18 C19 156.7(3) . . . . ?
C7 C8 C18 C19 40.3(5) . . . . ?
O1 C11 C18 C8 -69.7(4) . . . . ?
C10 C11 C18 C8 48.3(4) . . . . ?
O1 C11 C18 C19 59.6(5) . . . . ?
C10 C11 C18 C19 177.7(3) . . . . ?
C13 C14 C19 C20 175.6(4) . . . . ?
C15 C14 C19 C20 -3.7(5) . . . . ?
C13 C14 C19 C18 56.8(5) . . . . ?
C15 C14 C19 C18 -122.5(4) . . . . ?
C8 C18 C19 C14 59.5(5) . . . . ?
C11 C18 C19 C14 -67.3(5) . . . . ?
C8 C18 C19 C20 -61.4(4) . . . . ?
C11 C18 C19 C20 171.8(3) . . . . ?
C14 C19 C20 C21 -55.0(4) . . . . ?
C18 C19 C20 C21 68.5(4) . . . . ?
C19 C20 C21 N2 63.1(4) . . . . ?
C19 C20 C21 C7 -56.0(4) . . . . ?
C16 N2 C21 C20 -135.5(3) . . . . ?
C15 N2 C21 C20 -11.2(4) . . . . ?
C16 N2 C21 C7 -9.9(4) . . . . ?
C15 N2 C21 C7 114.5(3) . . . . ?
C5 C7 C21 C20 -85.5(4) . . . . ?
C17 C7 C21 C20 153.3(3) . . . . ?
C8 C7 C21 C20 32.7(5) . . . . ?
C5 C7 C21 N2 152.6(3) . . . . ?
C17 C7 C21 N2 31.5(4) . . . . ?
C8 C7 C21 N2 -89.1(4) . . . . ?
C22A O2A C2A C1A 4.9(6) . . . . ?
C22A O2A C2A C3A -173.1(4) . . . . ?
C5A C1A C2A O2A -178.2(4) . . . . ?
C5A C1A C2A C3A -0.3(6) . . . . ?
C23A O3A C3A C4A 4.1(6) . . . . ?
C23A O3A C3A C2A -175.8(4) . . . . ?
O2A C2A C3A C4A 176.1(4) . . . . ?
C1A C2A C3A C4A -2.0(6) . . . . ?
O2A C2A C3A O3A -4.1(5) . . . . ?
C1A C2A C3A O3A 177.9(4) . . . . ?
O3A C3A C4A C6A -178.3(4) . . . . ?
C2A C3A C4A C6A 1.6(6) . . . . ?
C2A C1A C5A C6A 3.0(6) . . . . ?
C2A C1A C5A N1A -176.1(4) . . . . ?
C9A N1A C5A C1A 23.9(7) . . . . ?
C8A N1A C5A C1A 173.7(4) . . . . ?
C9A N1A C5A C6A -155.4(4) . . . . ?
C8A N1A C5A C6A -5.5(4) . . . . ?
C1A C5A C6A C4A -3.5(6) . . . . ?
N1A C5A C6A C4A 175.8(3) . . . . ?
C1A C5A C6A C7A 173.0(4) . . . . ?
N1A C5A C6A C7A -7.7(5) . . . . ?
C3A C4A C6A C5A 1.1(6) . . . . ?
C3A C4A C6A C7A -174.7(4) . . . . ?
C5A C6A C7A C17A -102.8(4) . . . . ?
C4A C6A C7A C17A 73.3(5) . . . . ?
C5A C6A C7A C21A 141.4(4) . . . . ?
C4A C6A C7A C21A -42.5(6) . . . . ?
C5A C6A C7A C8A 16.8(4) . . . . ?
C4A C6A C7A C8A -167.2(4) . . . . ?
C9A N1A C8A C18A 43.8(5) . . . . ?
C5A N1A C8A C18A -107.8(3) . . . . ?
C9A N1A C8A C7A 167.1(3) . . . . ?
C5A N1A C8A C7A 15.6(4) . . . . ?
C6A C7A C8A N1A -18.8(4) . . . . ?
C17A C7A C8A N1A 103.6(3) . . . . ?
C21A C7A C8A N1A -144.0(3) . . . . ?
C6A C7A C8A C18A 97.8(4) . . . . ?
C17A C7A C8A C18A -139.8(3) . . . . ?
C21A C7A C8A C18A -27.4(5) . . . . ?
C5A N1A C9A O4A -21.2(7) . . . . ?
C8A N1A C9A O4A -168.5(4) . . . . ?
C5A N1A C9A C10A 159.0(4) . . . . ?
C8A N1A C9A C10A 11.7(5) . . . . ?
O4A C9A C10A C11A 138.1(4) . . . . ?
N1A C9A C10A C11A -42.0(5) . . . . ?
C12A O1A C11A C10A 173.6(3) . . . . ?
C12A O1A C11A C18A -66.1(4) . . . . ?
C9A C10A C11A O1A 135.0(4) . . . . ?
C9A C10A C11A C18A 12.2(5) . . . . ?
C11A O1A C12A C13A 88.1(4) . . . . ?
O1A C12A C13A C14A -64.5(6) . . . . ?
C12A C13A C14A C15A 175.1(4) . . . . ?
C12A C13A C14A C19A -3.2(6) . . . . ?
C16A N2A C15A C14A 73.4(4) . . . . ?
C21A N2A C15A C14A -47.6(5) . . . . ?
C13A C14A C15A N2A -125.4(4) . . . . ?
C19A C14A C15A N2A 53.0(5) . . . . ?
C15A N2A C16A C17A -144.1(3) . . . . ?
C21A N2A C16A C17A -20.1(4) . . . . ?
N2A C16A C17A C7A 40.0(4) . . . . ?
C6A C7A C17A C16A -167.2(3) . . . . ?
C21A C7A C17A C16A -43.3(4) . . . . ?
C8A C7A C17A C16A 77.7(4) . . . . ?
N1A C8A C18A C19A 156.0(3) . . . . ?
C7A C8A C18A C19A 40.9(5) . . . . ?
N1A C8A C18A C11A -71.2(4) . . . . ?
C7A C8A C18A C11A 173.7(3) . . . . ?
O1A C11A C18A C19A 55.0(5) . . . . ?
C10A C11A C18A C19A 172.1(4) . . . . ?
O1A C11A C18A C8A -75.0(4) . . . . ?
C10A C11A C18A C8A 42.0(4) . . . . ?
C8A C18A C19A C14A 59.7(5) . . . . ?
C11A C18A C19A C14A -67.4(5) . . . . ?
C8A C18A C19A C20A -60.5(4) . . . . ?
C11A C18A C19A C20A 172.4(3) . . . . ?
C13A C14A C19A C18A 59.7(5) . . . . ?
C15A C14A C19A C18A -118.7(4) . . . . ?
C13A C14A C19A C20A 178.2(4) . . . . ?
C15A C14A C19A C20A -0.2(5) . . . . ?
C18A C19A C20A C21A 69.3(4) . . . . ?
C14A C19A C20A C21A -55.0(4) . . . . ?
C15A N2A C21A C20A -8.3(5) . . . . ?
C16A N2A C21A C20A -132.0(3) . . . . ?
C15A N2A C21A C7A 116.2(4) . . . . ?
C16A N2A C21A C7A -7.4(4) . . . . ?
C19A C20A C21A N2A 61.3(4) . . . . ?
C19A C20A C21A C7A -58.7(4) . . . . ?
C6A C7A C21A N2A 155.0(3) . . . . ?
C17A C7A C21A N2A 31.4(4) . . . . ?
C8A C7A C21A N2A -86.7(4) . . . . ?
C6A C7A C21A C20A -81.6(4) . . . . ?
C17A C7A C21A C20A 154.9(3) . . . . ?
C8A C7A C21A C20A 36.7(5) . . . . ?
C29 N3 C25 C24 -69.9(5) . . . . ?
C29 N3 C25 C26 166.6(3) . . . . ?
O5 C24 C25 N3 -10.2(5) . . . . ?
O6 C24 C25 N3 170.0(4) . . . . ?
O5 C24 C25 C26 114.7(4) . . . . ?
O6 C24 C25 C26 -65.1(5) . . . . ?
N3 C25 C26 C27 63.9(4) . . . . ?
C24 C25 C26 C27 -61.4(4) . . . . ?
N3 C25 C26 C28 -63.5(4) . . . . ?
C24 C25 C26 C28 171.2(3) . . . . ?
C25 N3 C29 O7 -11.2(6) . . . . ?
C25 N3 C29 C30 169.6(3) . . . . ?
O7 C29 C30 C35 141.2(4) . . . . ?
N3 C29 C30 C35 -39.5(5) . . . . ?
O7 C29 C30 C31 -33.7(5) . . . . ?
N3 C29 C30 C31 145.6(3) . . . . ?
C35 C30 C31 C32 0.3(5) . . . . ?
C29 C30 C31 C32 175.4(3) . . . . ?
C30 C31 C32 C33 -1.1(6) . . . . ?
C30 C31 C32 N4 -179.1(3) . . . . ?
O9 N4 C32 C31 -2.3(5) . . . . ?
O8 N4 C32 C31 176.3(4) . . . . ?
O9 N4 C32 C33 179.6(4) . . . . ?
O8 N4 C32 C33 -1.8(5) . . . . ?
C31 C32 C33 C34 0.6(6) . . . . ?
N4 C32 C33 C34 178.6(4) . . . . ?
C32 C33 C34 C35 0.6(6) . . . . ?
C31 C30 C35 C34 0.9(6) . . . . ?
C29 C30 C35 C34 -173.9(4) . . . . ?
C33 C34 C35 C30 -1.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O6 0.93 1.74 2.648(4) 165.3 .
N3 H3 O4W 0.88 2.24 3.109(5) 171.4 1_656
O3W H31W N2A 0.83 2.05 2.820(5) 152.5 .
O3W H32W O6 0.88 1.81 2.686(4) 179.7 1_554
O5W H51W O4A 0.88 1.95 2.827(4) 178.3 1_444
O5W H52W O1W 0.86 1.97 2.828(5) 179.7 .
O4W H41W O3W 0.88 1.96 2.816(4) 166.3 .
O4W H42W O4 0.88 2.05 2.874(4) 153.7 .
O1W H11W O3W 0.88 1.98 2.840(4) 167.5 .
O1W H12W O5 0.89 1.85 2.736(4) 178.2 1_454
O2W H21W O5 0.87 2.12 2.991(4) 179.0 1_554
O2W H22W O5W 0.90 1.91 2.810(5) 179.2 .
C8A H8A O2 1.00 2.63 3.619(5) 172.2 1_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 930483'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

#===== end


data_b3nbda
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-D-alaninate methanol 1.61-solvate
;
_chemical_name_common            ?
_chemical_melting_point          386
_chemical_formula_moiety         'C23 H27 N2 O4, C10 H9 N2 O5, 1.61(C H4 O)'
_chemical_formula_sum            'C34.61 H42.45 N4 O10.61'
_chemical_formula_weight         684.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.880(3)
_cell_length_b                   12.092(2)
_cell_length_c                   34.308(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3269.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13281
_cell_measurement_theta_min      2.8411
_cell_measurement_theta_max      36.8351

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1452
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50478
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         32.00
_reflns_number_total             6321
_reflns_number_gt                4596
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.4002P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6321
_refine_ls_number_parameters     492
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1790(2) -0.27224(13) 0.82684(5) 0.0230(3) Uani 1 1 d . . .
O2 O 0.2624(2) 0.30404(13) 0.67585(4) 0.0257(4) Uani 1 1 d . . .
O3 O 0.2964(2) 0.42596(13) 0.73738(5) 0.0271(4) Uani 1 1 d . . .
O4 O 0.2242(3) -0.10049(14) 0.70467(5) 0.0367(5) Uani 1 1 d . . .
N1 N 0.1514(2) -0.01710(14) 0.76150(5) 0.0186(4) Uani 1 1 d . . .
N2 N 0.1144(3) 0.09366(16) 0.89000(5) 0.0239(4) Uani 1 1 d . . .
H2A H 0.1091 0.1553 0.9062 0.029 Uiso 1 1 d . . .
C1 C 0.2063(3) 0.13816(19) 0.71360(7) 0.0220(5) Uani 1 1 d . . .
H1 H 0.2000 0.0924 0.6912 0.026 Uiso 1 1 d . . .
C2 C 0.2403(3) 0.25048(18) 0.71056(6) 0.0210(4) Uani 1 1 d . . .
C3 C 0.2530(3) 0.31769(17) 0.74420(7) 0.0225(4) Uani 1 1 d . . .
C4 C 0.2222(3) 0.27298(18) 0.78077(6) 0.0208(4) Uani 1 1 d . . .
H4 H 0.2266 0.3181 0.8034 0.025 Uiso 1 1 d . . .
C5 C 0.1846(3) 0.16045(17) 0.78369(6) 0.0200(4) Uani 1 1 d . . .
C6 C 0.1811(3) 0.09494(17) 0.75099(6) 0.0194(4) Uani 1 1 d . . .
C7 C 0.1335(3) 0.09524(17) 0.81929(6) 0.0194(4) Uani 1 1 d . . .
C8 C 0.1492(3) -0.02669(17) 0.80477(6) 0.0171(4) Uani 1 1 d . . .
H8 H 0.0481 -0.0705 0.8133 0.020 Uiso 1 1 d . . .
C9 C 0.1999(3) -0.10659(18) 0.73991(7) 0.0234(5) Uani 1 1 d . . .
C10 C 0.2188(3) -0.21413(18) 0.76186(7) 0.0234(5) Uani 1 1 d . . .
H10A H 0.2918 -0.2637 0.7462 0.028 Uiso 1 1 calc R . .
H10B H 0.1055 -0.2492 0.7635 0.028 Uiso 1 1 calc R . .
C11 C 0.2936(3) -0.20842(18) 0.80362(6) 0.0204(4) Uani 1 1 d . . .
H11 H 0.4076 -0.2445 0.8038 0.024 Uiso 1 1 d . . .
C12 C 0.2343(3) -0.29052(18) 0.86625(7) 0.0260(5) Uani 1 1 d . . .
H12A H 0.3597 -0.2955 0.8669 0.031 Uiso 1 1 calc R . .
H12B H 0.1878 -0.3616 0.8758 0.031 Uiso 1 1 calc R . .
C13 C 0.1767(3) -0.19826(19) 0.89270(7) 0.0247(5) Uani 1 1 d . . .
H13 H 0.0979 -0.2141 0.9129 0.030 Uiso 1 1 d . . .
C14 C 0.2332(3) -0.09518(19) 0.88877(6) 0.0242(5) Uani 1 1 d . . .
C15 C 0.1719(4) -0.0025(2) 0.91448(7) 0.0263(5) Uani 1 1 d . . .
H15A H 0.0764 -0.0289 0.9308 0.032 Uiso 1 1 calc R . .
H15B H 0.2647 0.0213 0.9320 0.032 Uiso 1 1 calc R . .
C16 C -0.0601(3) 0.0761(2) 0.87305(7) 0.0261(5) Uani 1 1 d . . .
H16A H -0.1468 0.1157 0.8885 0.031 Uiso 1 1 calc R . .
H16B H -0.0889 -0.0036 0.8725 0.031 Uiso 1 1 calc R . .
C17 C -0.0502(3) 0.12247(19) 0.83204(7) 0.0236(5) Uani 1 1 d . . .
H17A H -0.0705 0.2033 0.8320 0.028 Uiso 1 1 calc R . .
H17B H -0.1340 0.0863 0.8147 0.028 Uiso 1 1 calc R . .
C18 C 0.3122(3) -0.08715(17) 0.81620(6) 0.0187(4) Uani 1 1 d . . .
H18 H 0.4035 -0.0554 0.7994 0.022 Uiso 1 1 d . . .
C19 C 0.3666(3) -0.06412(18) 0.85840(6) 0.0202(4) Uani 1 1 d . . .
H19 H 0.4737 -0.1053 0.8641 0.024 Uiso 1 1 d . . .
C20 C 0.4014(3) 0.06044(19) 0.86074(7) 0.0232(5) Uani 1 1 d . . .
H20A H 0.4541 0.0788 0.8861 0.028 Uiso 1 1 calc R . .
H20B H 0.4806 0.0827 0.8398 0.028 Uiso 1 1 calc R . .
C21 C 0.2343(3) 0.12160(18) 0.85634(6) 0.0224(5) Uani 1 1 d . . .
H21 H 0.2577 0.2027 0.8569 0.027 Uiso 1 1 d . . .
C22 C 0.2375(3) 0.2386(2) 0.64148(6) 0.0261(5) Uani 1 1 d . . .
H22A H 0.2564 0.2845 0.6183 0.039 Uiso 1 1 calc R . .
H22B H 0.1212 0.2098 0.6411 0.039 Uiso 1 1 calc R . .
H22C H 0.3179 0.1767 0.6415 0.039 Uiso 1 1 calc R . .
C23 C 0.3265(4) 0.4926(2) 0.77106(8) 0.0353(6) Uani 1 1 d . . .
H23A H 0.3577 0.5676 0.7629 0.053 Uiso 1 1 calc R . .
H23B H 0.4191 0.4604 0.7864 0.053 Uiso 1 1 calc R . .
H23C H 0.2233 0.4956 0.7870 0.053 Uiso 1 1 calc R . .
O5 O 0.1595(4) 0.28013(17) 0.92908(6) 0.0661(9) Uani 1 1 d . . .
O6 O 0.0378(3) 0.17755(16) 0.97263(6) 0.0429(5) Uani 1 1 d . . .
O7 O 0.1492(2) 0.57348(13) 0.95849(5) 0.0246(4) Uani 1 1 d . . .
O8 O 0.4900(3) 0.91324(15) 0.95715(6) 0.0358(4) Uani 1 1 d . . .
O9 O 0.7572(3) 0.90119(16) 0.94326(5) 0.0390(5) Uani 1 1 d . . .
N3 N 0.2734(2) 0.42259(15) 0.98595(5) 0.0198(4) Uani 1 1 d . . .
H3 H 0.3704 0.3930 0.9933 0.024 Uiso 1 1 d . . .
N4 N 0.6205(3) 0.86003(16) 0.95273(6) 0.0265(5) Uani 1 1 d . . .
C24 C 0.1041(3) 0.26479(18) 0.96262(7) 0.0231(5) Uani 1 1 d . . .
C25 C 0.1191(3) 0.35939(17) 0.99226(7) 0.0206(4) Uani 1 1 d . . .
H25 H 0.0210 0.4102 0.9880 0.025 Uiso 1 1 d . . .
C26 C 0.1098(4) 0.3184(2) 1.03425(7) 0.0289(5) Uani 1 1 d . . .
H26A H 0.1148 0.3817 1.0521 0.043 Uiso 1 1 calc R . .
H26B H 0.2056 0.2689 1.0394 0.043 Uiso 1 1 calc R . .
H26C H 0.0031 0.2784 1.0382 0.043 Uiso 1 1 calc R . .
C27 C 0.2764(3) 0.52379(17) 0.96967(6) 0.0178(4) Uani 1 1 d . . .
C28 C 0.4483(3) 0.57555(18) 0.96596(6) 0.0186(4) Uani 1 1 d . . .
C29 C 0.4555(3) 0.69010(18) 0.96188(6) 0.0182(4) Uani 1 1 d . . .
H29 H 0.3548 0.7332 0.9618 0.022 Uiso 1 1 d . . .
C30 C 0.6132(3) 0.73950(19) 0.95791(6) 0.0217(4) Uani 1 1 d . . .
C31 C 0.7623(3) 0.6803(2) 0.95732(8) 0.0322(6) Uani 1 1 d . . .
H31 H 0.8688 0.7166 0.9546 0.039 Uiso 1 1 d . . .
C32 C 0.7531(3) 0.5673(2) 0.96081(11) 0.0425(7) Uani 1 1 d . . .
H32 H 0.8543 0.5246 0.9601 0.051 Uiso 1 1 d . . .
C33 C 0.5989(3) 0.5149(2) 0.96526(9) 0.0343(6) Uani 1 1 d . . .
H33 H 0.5951 0.4368 0.9679 0.041 Uiso 1 1 d . . .
O100 O 0.1030(19) 0.4221(10) 0.8616(3) 0.047(2) Uani 0.286(9) 1 d PDU A 1
H100 H 0.1638 0.3772 0.8740 0.071 Uiso 0.286(9) 1 calc PR A 1
C100 C -0.0444(16) 0.4339(13) 0.8796(4) 0.051(3) Uani 0.286(9) 1 d PDU A 1
H101 H -0.1348 0.4429 0.8603 0.077 Uiso 0.286(9) 1 calc PR A 1
H102 H -0.0403 0.4993 0.8964 0.077 Uiso 0.286(9) 1 calc PR A 1
H103 H -0.0673 0.3682 0.8955 0.077 Uiso 0.286(9) 1 calc PR A 1
O110 O 0.1792(15) 0.4158(6) 0.8707(2) 0.041(2) Uani 0.329(10) 1 d PDU B 3
H110 H 0.1840 0.3708 0.8894 0.061 Uiso 0.329(10) 1 calc PR B 3
C110 C 0.0202(18) 0.4485(9) 0.8658(5) 0.047(3) Uani 0.329(10) 1 d PDU B 3
H111 H -0.0504 0.4190 0.8869 0.071 Uiso 0.329(10) 1 calc PR B 3
H112 H -0.0221 0.4213 0.8407 0.071 Uiso 0.329(10) 1 calc PR B 3
H113 H 0.0154 0.5295 0.8662 0.071 Uiso 0.329(10) 1 calc PR B 3
O120 O 0.2940(11) 0.4104(7) 0.8691(2) 0.047(2) Uani 0.301(5) 1 d PDU C 2
H120 H 0.2454 0.4146 0.8908 0.071 Uiso 0.301(5) 1 calc PR C 2
C120 C 0.4614(13) 0.4057(11) 0.8744(4) 0.052(3) Uani 0.301(5) 1 d PDU C 2
H121 H 0.4870 0.3547 0.8958 0.079 Uiso 0.301(5) 1 calc PR C 2
H122 H 0.5043 0.4795 0.8808 0.079 Uiso 0.301(5) 1 calc PR C 2
H123 H 0.5158 0.3793 0.8504 0.079 Uiso 0.301(5) 1 calc PR C 2
O200 O 0.5803(5) 0.2891(3) 0.84871(11) 0.0621(12) Uani 0.699(5) 1 d PDU C 1
H200 H 0.6616 0.3023 0.8301 0.093 Uiso 0.70 1 d P C 1
C200 C 0.5672(10) 0.3660(5) 0.87663(16) 0.0728(18) Uani 0.699(5) 1 d PDU C 1
H201 H 0.4822 0.3427 0.8958 0.109 Uiso 0.699(5) 1 calc PR C 1
H202 H 0.5327 0.4365 0.8650 0.109 Uiso 0.699(5) 1 calc PR C 1
H203 H 0.6772 0.3750 0.8896 0.109 Uiso 0.699(5) 1 calc PR C 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0272(8) 0.0201(7) 0.0215(7) 0.0019(6) -0.0015(7) -0.0031(7)
O2 0.0339(9) 0.0254(8) 0.0179(7) 0.0051(6) 0.0033(7) -0.0014(8)
O3 0.0374(10) 0.0178(7) 0.0260(8) 0.0038(6) 0.0038(7) -0.0022(7)
O4 0.0656(14) 0.0240(8) 0.0204(8) -0.0018(7) 0.0084(9) 0.0008(9)
N1 0.0248(9) 0.0175(8) 0.0136(8) 0.0002(7) 0.0005(7) -0.0003(8)
N2 0.0338(11) 0.0216(9) 0.0163(8) 0.0003(7) 0.0045(8) -0.0008(9)
C1 0.0240(11) 0.0242(10) 0.0178(10) 0.0011(8) 0.0004(9) 0.0011(9)
C2 0.0239(11) 0.0231(10) 0.0160(9) 0.0033(8) 0.0035(9) 0.0001(9)
C3 0.0270(11) 0.0160(9) 0.0246(11) 0.0024(8) 0.0013(10) -0.0006(9)
C4 0.0251(11) 0.0191(9) 0.0184(10) -0.0002(8) 0.0009(9) 0.0010(9)
C5 0.0254(11) 0.0186(9) 0.0161(10) 0.0022(8) 0.0015(9) 0.0009(9)
C6 0.0230(11) 0.0175(9) 0.0179(9) 0.0032(8) 0.0018(8) 0.0006(9)
C7 0.0265(11) 0.0152(9) 0.0164(9) 0.0000(8) 0.0003(8) 0.0008(9)
C8 0.0199(10) 0.0180(9) 0.0133(9) -0.0010(8) 0.0025(8) -0.0015(8)
C9 0.0293(12) 0.0201(10) 0.0208(10) -0.0033(9) 0.0007(9) -0.0001(9)
C10 0.0312(12) 0.0170(9) 0.0219(10) -0.0041(8) -0.0004(10) 0.0018(9)
C11 0.0211(11) 0.0170(9) 0.0229(10) 0.0001(8) 0.0015(9) 0.0018(8)
C12 0.0331(13) 0.0200(10) 0.0248(11) 0.0047(9) -0.0043(10) 0.0006(10)
C13 0.0284(12) 0.0249(11) 0.0209(11) 0.0051(9) -0.0048(9) -0.0022(10)
C14 0.0301(12) 0.0251(10) 0.0173(9) 0.0017(8) -0.0046(9) 0.0002(10)
C15 0.0371(13) 0.0250(11) 0.0166(10) 0.0030(9) -0.0009(10) -0.0019(11)
C16 0.0285(12) 0.0251(11) 0.0247(11) 0.0005(10) 0.0068(10) 0.0016(10)
C17 0.0285(12) 0.0217(11) 0.0205(11) 0.0009(9) 0.0057(9) 0.0026(10)
C18 0.0192(10) 0.0177(9) 0.0192(10) -0.0006(8) 0.0024(8) -0.0001(8)
C19 0.0226(11) 0.0194(9) 0.0187(10) 0.0012(8) -0.0017(9) -0.0011(9)
C20 0.0253(12) 0.0250(11) 0.0194(10) -0.0010(9) -0.0042(9) -0.0053(9)
C21 0.0321(13) 0.0202(10) 0.0147(9) 0.0011(8) 0.0025(9) -0.0044(9)
C22 0.0270(12) 0.0327(12) 0.0187(10) 0.0035(9) -0.0008(9) -0.0031(10)
C23 0.0565(18) 0.0162(10) 0.0333(13) -0.0002(10) 0.0026(13) -0.0051(12)
O5 0.139(2) 0.0320(10) 0.0270(10) -0.0087(8) 0.0366(13) -0.0342(14)
O6 0.0665(14) 0.0287(10) 0.0335(10) -0.0080(9) 0.0200(10) -0.0253(10)
O7 0.0174(8) 0.0226(8) 0.0338(9) 0.0088(7) -0.0004(7) 0.0018(6)
O8 0.0414(11) 0.0235(9) 0.0426(11) 0.0006(8) -0.0074(9) -0.0064(8)
O9 0.0485(12) 0.0346(10) 0.0340(10) -0.0101(8) 0.0152(9) -0.0233(10)
N3 0.0222(9) 0.0164(8) 0.0208(8) 0.0030(7) -0.0004(7) 0.0004(8)
N4 0.0392(12) 0.0248(10) 0.0156(9) -0.0026(8) -0.0010(9) -0.0123(10)
C24 0.0297(12) 0.0182(10) 0.0215(11) 0.0011(9) 0.0036(9) -0.0033(9)
C25 0.0257(11) 0.0155(9) 0.0206(10) 0.0012(8) 0.0053(9) -0.0023(9)
C26 0.0475(15) 0.0209(11) 0.0183(10) -0.0017(9) 0.0070(11) -0.0056(11)
C27 0.0182(10) 0.0169(9) 0.0185(10) 0.0010(8) 0.0025(8) 0.0008(8)
C28 0.0169(10) 0.0176(9) 0.0213(10) 0.0032(9) -0.0006(8) 0.0001(8)
C29 0.0219(10) 0.0200(10) 0.0126(9) 0.0016(8) -0.0008(8) -0.0022(8)
C30 0.0267(11) 0.0238(10) 0.0147(9) 0.0009(8) -0.0023(9) -0.0086(9)
C31 0.0217(12) 0.0399(14) 0.0350(13) 0.0078(12) -0.0041(11) -0.0098(11)
C32 0.0155(11) 0.0381(14) 0.074(2) 0.0157(15) -0.0021(13) 0.0035(11)
C33 0.0210(12) 0.0232(11) 0.0588(19) 0.0108(12) -0.0029(12) 0.0031(10)
O100 0.054(5) 0.044(4) 0.043(4) -0.007(3) 0.014(4) 0.003(4)
C100 0.065(6) 0.049(5) 0.039(5) 0.008(4) 0.005(5) 0.012(5)
O110 0.068(5) 0.031(3) 0.024(3) 0.006(2) -0.011(3) 0.017(4)
C110 0.057(6) 0.033(4) 0.051(5) -0.003(4) -0.008(4) 0.005(4)
O120 0.065(4) 0.041(3) 0.037(3) 0.001(3) 0.010(3) -0.003(4)
C120 0.071(5) 0.048(5) 0.038(4) -0.001(4) 0.005(5) -0.016(5)
O200 0.082(3) 0.0447(19) 0.060(2) 0.0017(16) 0.0186(19) -0.0296(19)
C200 0.104(4) 0.076(4) 0.039(3) 0.006(3) 0.012(3) -0.028(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.430(3) . ?
O1 C12 1.437(3) . ?
O2 C2 1.367(3) . ?
O2 C22 1.434(3) . ?
O3 C3 1.373(3) . ?
O3 C23 1.429(3) . ?
O4 C9 1.226(3) . ?
N1 C9 1.366(3) . ?
N1 C6 1.421(3) . ?
N1 C8 1.489(3) . ?
N2 C15 1.505(3) . ?
N2 C16 1.508(3) . ?
N2 C21 1.530(3) . ?
N2 H2A 0.9301 . ?
C1 C2 1.388(3) . ?
C1 C6 1.399(3) . ?
C1 H1 0.9497 . ?
C2 C3 1.415(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.396(3) . ?
C4 H4 0.9494 . ?
C5 C6 1.374(3) . ?
C5 C7 1.508(3) . ?
C7 C21 1.533(3) . ?
C7 C17 1.548(3) . ?
C7 C8 1.561(3) . ?
C8 C18 1.529(3) . ?
C8 H8 1.0001 . ?
C9 C10 1.510(3) . ?
C10 C11 1.551(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.536(3) . ?
C11 H11 0.9989 . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.330(3) . ?
C13 H13 0.9495 . ?
C14 C15 1.506(3) . ?
C14 C19 1.527(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.517(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.536(3) . ?
C18 H18 0.9993 . ?
C19 C20 1.533(3) . ?
C19 H19 0.9986 . ?
C20 C21 1.518(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 0.9979 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.244(3) . ?
O6 C24 1.227(3) . ?
O7 C27 1.230(3) . ?
O8 N4 1.223(3) . ?
O9 N4 1.230(3) . ?
N3 C27 1.345(3) . ?
N3 C25 1.452(3) . ?
N3 H3 0.8801 . ?
N4 C30 1.469(3) . ?
C24 C25 1.535(3) . ?
C25 C26 1.525(3) . ?
C25 H25 0.9982 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.497(3) . ?
C28 C29 1.393(3) . ?
C28 C33 1.395(3) . ?
C29 C30 1.385(3) . ?
C29 H29 0.9494 . ?
C30 C31 1.376(4) . ?
C31 C32 1.374(4) . ?
C31 H31 0.9510 . ?
C32 C33 1.379(4) . ?
C32 H32 0.9502 . ?
C33 H33 0.9497 . ?
O100 C100 1.323(6) . ?
O100 H100 0.8400 . ?
C100 H101 0.9800 . ?
C100 H102 0.9800 . ?
C100 H103 0.9800 . ?
O110 C110 1.325(6) . ?
O110 H110 0.8400 . ?
C110 H111 0.9800 . ?
C110 H112 0.9800 . ?
C110 H113 0.9800 . ?
O120 C120 1.332(6) . ?
O120 H120 0.8400 . ?
C120 H121 0.9800 . ?
C120 H122 0.9800 . ?
C120 H123 0.9800 . ?
O200 C200 1.339(5) . ?
O200 H200 0.9187 . ?
C200 H201 0.9800 . ?
C200 H202 0.9800 . ?
C200 H203 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.57(18) . . ?
C2 O2 C22 115.96(17) . . ?
C3 O3 C23 116.21(18) . . ?
C9 N1 C6 124.86(18) . . ?
C9 N1 C8 118.83(18) . . ?
C6 N1 C8 109.20(17) . . ?
C15 N2 C16 112.37(19) . . ?
C15 N2 C21 113.96(19) . . ?
C16 N2 C21 107.65(17) . . ?
C15 N2 H2A 107.5 . . ?
C16 N2 H2A 107.6 . . ?
C21 N2 H2A 107.5 . . ?
C2 C1 C6 117.5(2) . . ?
C2 C1 H1 121.3 . . ?
C6 C1 H1 121.2 . . ?
O2 C2 C1 123.6(2) . . ?
O2 C2 C3 115.44(19) . . ?
C1 C2 C3 120.9(2) . . ?
O3 C3 C4 124.7(2) . . ?
O3 C3 C2 115.23(19) . . ?
C4 C3 C2 120.10(19) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 C7 110.76(18) . . ?
C4 C5 C7 128.62(19) . . ?
C5 C6 C1 122.0(2) . . ?
C5 C6 N1 110.23(18) . . ?
C1 C6 N1 127.7(2) . . ?
C5 C7 C21 115.12(19) . . ?
C5 C7 C17 111.54(18) . . ?
C21 C7 C17 101.89(18) . . ?
C5 C7 C8 102.37(16) . . ?
C21 C7 C8 114.83(18) . . ?
C17 C7 C8 111.42(19) . . ?
N1 C8 C18 106.45(17) . . ?
N1 C8 C7 104.21(16) . . ?
C18 C8 C7 115.88(18) . . ?
N1 C8 H8 110.0 . . ?
C18 C8 H8 109.9 . . ?
C7 C8 H8 110.1 . . ?
O4 C9 N1 122.1(2) . . ?
O4 C9 C10 121.9(2) . . ?
N1 C9 C10 116.06(19) . . ?
C9 C10 C11 117.39(19) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 114.78(17) . . ?
O1 C11 C10 104.54(18) . . ?
C18 C11 C10 109.77(18) . . ?
O1 C11 H11 109.2 . . ?
C18 C11 H11 109.3 . . ?
C10 C11 H11 109.1 . . ?
O1 C12 C13 111.17(18) . . ?
O1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 122.1(2) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 122.0(2) . . ?
C13 C14 C19 122.0(2) . . ?
C15 C14 C19 116.0(2) . . ?
N2 C15 C14 110.17(18) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 105.02(19) . . ?
N2 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
N2 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 103.37(19) . . ?
C16 C17 H17A 111.1 . . ?
C7 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C7 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C8 C18 C11 107.73(18) . . ?
C8 C18 C19 112.94(18) . . ?
C11 C18 C19 117.70(18) . . ?
C8 C18 H18 105.9 . . ?
C11 C18 H18 105.9 . . ?
C19 C18 H18 105.8 . . ?
C14 C19 C20 109.22(19) . . ?
C14 C19 C18 113.98(19) . . ?
C20 C19 C18 106.12(17) . . ?
C14 C19 H19 109.0 . . ?
C20 C19 H19 109.1 . . ?
C18 C19 H19 109.2 . . ?
C21 C20 C19 108.55(19) . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 N2 110.68(18) . . ?
C20 C21 C7 115.52(18) . . ?
N2 C21 C7 105.07(19) . . ?
C20 C21 H21 108.5 . . ?
N2 C21 H21 108.4 . . ?
C7 C21 H21 108.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 N3 C25 123.72(19) . . ?
C27 N3 H3 118.2 . . ?
C25 N3 H3 118.1 . . ?
O8 N4 O9 123.8(2) . . ?
O8 N4 C30 118.3(2) . . ?
O9 N4 C30 117.9(2) . . ?
O6 C24 O5 122.5(2) . . ?
O6 C24 C25 119.2(2) . . ?
O5 C24 C25 118.3(2) . . ?
N3 C25 C26 110.6(2) . . ?
N3 C25 C24 110.96(19) . . ?
C26 C25 C24 112.34(18) . . ?
N3 C25 H25 107.6 . . ?
C26 C25 H25 107.5 . . ?
C24 C25 H25 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 N3 124.0(2) . . ?
O7 C27 C28 120.42(18) . . ?
N3 C27 C28 115.56(19) . . ?
C29 C28 C33 119.1(2) . . ?
C29 C28 C27 117.47(19) . . ?
C33 C28 C27 123.4(2) . . ?
C30 C29 C28 118.4(2) . . ?
C30 C29 H29 120.9 . . ?
C28 C29 H29 120.7 . . ?
C31 C30 C29 122.9(2) . . ?
C31 C30 N4 118.7(2) . . ?
C29 C30 N4 118.4(2) . . ?
C32 C31 C30 118.1(2) . . ?
C32 C31 H31 121.0 . . ?
C30 C31 H31 121.0 . . ?
C31 C32 C33 120.9(2) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.5 . . ?
C32 C33 C28 120.7(2) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H101 109.5 . . ?
O100 C100 H102 109.5 . . ?
H101 C100 H102 109.5 . . ?
O100 C100 H103 109.5 . . ?
H101 C100 H103 109.5 . . ?
H102 C100 H103 109.5 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H111 109.5 . . ?
O110 C110 H112 109.5 . . ?
H111 C110 H112 109.5 . . ?
O110 C110 H113 109.5 . . ?
H111 C110 H113 109.5 . . ?
H112 C110 H113 109.5 . . ?
C120 O120 H120 109.5 . . ?
O120 C120 H121 109.5 . . ?
O120 C120 H122 109.5 . . ?
H121 C120 H122 109.5 . . ?
O120 C120 H123 109.5 . . ?
H121 C120 H123 109.5 . . ?
H122 C120 H123 109.5 . . ?
C200 O200 H200 115.5 . . ?
O200 C200 H201 109.5 . . ?
O200 C200 H202 109.5 . . ?
H201 C200 H202 109.5 . . ?
O200 C200 H203 109.5 . . ?
H201 C200 H203 109.5 . . ?
H202 C200 H203 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 3.9(3) . . . . ?
C22 O2 C2 C3 -175.6(2) . . . . ?
C6 C1 C2 O2 -177.9(2) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C23 O3 C3 C4 6.1(3) . . . . ?
C23 O3 C3 C2 -174.0(2) . . . . ?
O2 C2 C3 O3 -4.0(3) . . . . ?
C1 C2 C3 O3 176.5(2) . . . . ?
O2 C2 C3 C4 176.0(2) . . . . ?
C1 C2 C3 C4 -3.5(4) . . . . ?
O3 C3 C4 C5 -177.9(2) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C5 C7 -174.7(2) . . . . ?
C4 C5 C6 C1 -3.2(3) . . . . ?
C7 C5 C6 C1 173.3(2) . . . . ?
C4 C5 C6 N1 176.1(2) . . . . ?
C7 C5 C6 N1 -7.3(3) . . . . ?
C2 C1 C6 C5 1.9(3) . . . . ?
C2 C1 C6 N1 -177.4(2) . . . . ?
C9 N1 C6 C5 -154.8(2) . . . . ?
C8 N1 C6 C5 -4.9(3) . . . . ?
C9 N1 C6 C1 24.5(4) . . . . ?
C8 N1 C6 C1 174.4(2) . . . . ?
C6 C5 C7 C21 140.9(2) . . . . ?
C4 C5 C7 C21 -42.9(3) . . . . ?
C6 C5 C7 C17 -103.6(2) . . . . ?
C4 C5 C7 C17 72.6(3) . . . . ?
C6 C5 C7 C8 15.6(2) . . . . ?
C4 C5 C7 C8 -168.2(2) . . . . ?
C9 N1 C8 C18 43.3(3) . . . . ?
C6 N1 C8 C18 -108.6(2) . . . . ?
C9 N1 C8 C7 166.3(2) . . . . ?
C6 N1 C8 C7 14.3(2) . . . . ?
C5 C7 C8 N1 -17.4(2) . . . . ?
C21 C7 C8 N1 -142.90(19) . . . . ?
C17 C7 C8 N1 101.92(19) . . . . ?
C5 C7 C8 C18 99.2(2) . . . . ?
C21 C7 C8 C18 -26.3(3) . . . . ?
C17 C7 C8 C18 -141.49(19) . . . . ?
C6 N1 C9 O4 -23.7(4) . . . . ?
C8 N1 C9 O4 -171.0(2) . . . . ?
C6 N1 C9 C10 157.3(2) . . . . ?
C8 N1 C9 C10 10.0(3) . . . . ?
O4 C9 C10 C11 143.5(2) . . . . ?
N1 C9 C10 C11 -37.6(3) . . . . ?
C12 O1 C11 C18 -67.2(2) . . . . ?
C12 O1 C11 C10 172.53(18) . . . . ?
C9 C10 C11 O1 131.1(2) . . . . ?
C9 C10 C11 C18 7.5(3) . . . . ?
C11 O1 C12 C13 88.4(2) . . . . ?
O1 C12 C13 C14 -65.3(3) . . . . ?
C12 C13 C14 C15 178.2(2) . . . . ?
C12 C13 C14 C19 -2.9(4) . . . . ?
C16 N2 C15 C14 78.7(3) . . . . ?
C21 N2 C15 C14 -44.1(3) . . . . ?
C13 C14 C15 N2 -128.7(2) . . . . ?
C19 C14 C15 N2 52.4(3) . . . . ?
C15 N2 C16 C17 -140.57(19) . . . . ?
C21 N2 C16 C17 -14.3(2) . . . . ?
N2 C16 C17 C7 34.6(2) . . . . ?
C5 C7 C17 C16 -164.78(19) . . . . ?
C21 C7 C17 C16 -41.4(2) . . . . ?
C8 C7 C17 C16 81.5(2) . . . . ?
N1 C8 C18 C11 -71.4(2) . . . . ?
C7 C8 C18 C11 173.24(17) . . . . ?
N1 C8 C18 C19 156.87(17) . . . . ?
C7 C8 C18 C19 41.6(2) . . . . ?
O1 C11 C18 C8 -72.7(2) . . . . ?
C10 C11 C18 C8 44.6(2) . . . . ?
O1 C11 C18 C19 56.3(3) . . . . ?
C10 C11 C18 C19 173.69(19) . . . . ?
C13 C14 C19 C20 178.8(2) . . . . ?
C15 C14 C19 C20 -2.3(3) . . . . ?
C13 C14 C19 C18 60.3(3) . . . . ?
C15 C14 C19 C18 -120.7(2) . . . . ?
C8 C18 C19 C14 58.2(2) . . . . ?
C11 C18 C19 C14 -68.4(3) . . . . ?
C8 C18 C19 C20 -62.1(2) . . . . ?
C11 C18 C19 C20 171.37(19) . . . . ?
C14 C19 C20 C21 -54.9(2) . . . . ?
C18 C19 C20 C21 68.3(2) . . . . ?
C19 C20 C21 N2 63.2(2) . . . . ?
C19 C20 C21 C7 -56.1(2) . . . . ?
C15 N2 C21 C20 -11.8(3) . . . . ?
C16 N2 C21 C20 -137.1(2) . . . . ?
C15 N2 C21 C7 113.6(2) . . . . ?
C16 N2 C21 C7 -11.8(2) . . . . ?
C5 C7 C21 C20 -84.4(2) . . . . ?
C17 C7 C21 C20 154.67(19) . . . . ?
C8 C7 C21 C20 34.1(3) . . . . ?
C5 C7 C21 N2 153.29(18) . . . . ?
C17 C7 C21 N2 32.4(2) . . . . ?
C8 C7 C21 N2 -88.2(2) . . . . ?
C27 N3 C25 C26 -129.3(2) . . . . ?
C27 N3 C25 C24 105.3(2) . . . . ?
O6 C24 C25 N3 146.1(2) . . . . ?
O5 C24 C25 N3 -34.3(3) . . . . ?
O6 C24 C25 C26 21.8(3) . . . . ?
O5 C24 C25 C26 -158.6(3) . . . . ?
C25 N3 C27 O7 0.1(3) . . . . ?
C25 N3 C27 C28 179.62(19) . . . . ?
O7 C27 C28 C29 20.4(3) . . . . ?
N3 C27 C28 C29 -159.1(2) . . . . ?
O7 C27 C28 C33 -157.7(3) . . . . ?
N3 C27 C28 C33 22.8(3) . . . . ?
C33 C28 C29 C30 -1.0(3) . . . . ?
C27 C28 C29 C30 -179.20(19) . . . . ?
C28 C29 C30 C31 0.8(3) . . . . ?
C28 C29 C30 N4 178.6(2) . . . . ?
O8 N4 C30 C31 -172.8(2) . . . . ?
O9 N4 C30 C31 8.9(3) . . . . ?
O8 N4 C30 C29 9.3(3) . . . . ?
O9 N4 C30 C29 -169.0(2) . . . . ?
C29 C30 C31 C32 0.0(4) . . . . ?
N4 C30 C31 C32 -177.7(3) . . . . ?
C30 C31 C32 C33 -0.8(5) . . . . ?
C31 C32 C33 C28 0.6(5) . . . . ?
C29 C28 C33 C32 0.3(4) . . . . ?
C27 C28 C33 C32 178.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.93 1.75 2.647(3) 161.8 .
N3 H3 O6 0.88 1.96 2.797(3) 158.7 4_557
O100 H100 O5 0.84 2.22 2.916(15) 139.7 .
O110 H110 O5 0.84 1.76 2.593(8) 171.0 .
O120 H120 O5 0.84 2.20 2.801(8) 128.8 .
O200 H200 O4 0.92 1.90 2.740(4) 150.9 3_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        32.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 930484'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

#====== end



data_b3nbla
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-L-alaninate methanol disolvate
;
_chemical_name_common            ?
_chemical_melting_point          420
_chemical_formula_moiety         'C23 H27 N2 O4, C10 H9 N2 O5, 2(C H4 O)'
_chemical_formula_sum            'C35 H44 N4 O11'
_chemical_formula_weight         696.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.919(2)
_cell_length_b                   12.266(3)
_cell_length_c                   34.420(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3343.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15816
_cell_measurement_theta_min      3.1114
_cell_measurement_theta_max      36.8124

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            56803
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         35.00
_reflns_number_total             8128
_reflns_number_gt                6815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+2.5342P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         8128
_refine_ls_number_parameters     508
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2824(3) 1.26585(15) 0.32384(6) 0.0253(4) Uani 1 1 d . . .
O2 O 0.2722(3) 0.68437(17) 0.17750(5) 0.0280(4) Uani 1 1 d . . .
O3 O 0.2342(3) 0.56703(17) 0.23933(6) 0.0330(5) Uani 1 1 d . . .
O4 O 0.2590(4) 1.08437(19) 0.20351(6) 0.0475(7) Uani 1 1 d . . .
N1 N 0.3343(3) 1.00991(19) 0.26148(6) 0.0222(4) Uani 1 1 d . . .
N2 N 0.3493(3) 0.9120(2) 0.39112(6) 0.0253(5) Uani 1 1 d . . .
H2A H 0.3566 0.8526 0.4078 0.030 Uiso 1 1 calc R . .
C1 C 0.3042(4) 0.8521(2) 0.21465(7) 0.0233(5) Uani 1 1 d . . .
H1A H 0.3123 0.8958 0.1919 0.028 Uiso 1 1 calc R . .
C2 C 0.2815(4) 0.7399(2) 0.21227(7) 0.0239(5) Uani 1 1 d . . .
C3 C 0.2659(4) 0.6755(2) 0.24591(8) 0.0240(5) Uani 1 1 d . . .
C4 C 0.2833(4) 0.7230(2) 0.28244(7) 0.0235(5) Uani 1 1 d . . .
H4A H 0.2779 0.6796 0.3053 0.028 Uiso 1 1 calc R . .
C5 C 0.3088(3) 0.8357(2) 0.28501(7) 0.0206(4) Uani 1 1 d . . .
C6 C 0.3147(3) 0.8980(2) 0.25169(7) 0.0216(5) Uani 1 1 d . . .
C7 C 0.3469(3) 0.9036(2) 0.32032(7) 0.0208(4) Uani 1 1 d . . .
C8 C 0.3267(3) 1.0224(2) 0.30455(7) 0.0196(4) Uani 1 1 d . . .
H8A H 0.4234 1.0682 0.3136 0.023 Uiso 1 1 calc R . .
C9 C 0.2826(4) 1.0942(2) 0.23860(8) 0.0302(6) Uani 1 1 d . . .
C10 C 0.2588(4) 1.2026(2) 0.25903(8) 0.0271(5) Uani 1 1 d . . .
H10A H 0.1882 1.2497 0.2422 0.033 Uiso 1 1 calc R . .
H10B H 0.3707 1.2380 0.2614 0.033 Uiso 1 1 calc R . .
C11 C 0.1770(3) 1.1989(2) 0.29992(8) 0.0227(5) Uani 1 1 d . . .
H11A H 0.0620 1.2322 0.2985 0.027 Uiso 1 1 calc R . .
C12 C 0.2175(4) 1.2861(2) 0.36240(8) 0.0294(6) Uani 1 1 d . . .
H12A H 0.0927 1.2894 0.3615 0.035 Uiso 1 1 calc R . .
H12B H 0.2593 1.3575 0.3718 0.035 Uiso 1 1 calc R . .
C13 C 0.2712(4) 1.1982(2) 0.39034(8) 0.0267(5) Uani 1 1 d . . .
H13A H 0.3440 1.2168 0.4113 0.032 Uiso 1 1 calc R . .
C14 C 0.2201(4) 1.0952(2) 0.38671(7) 0.0243(5) Uani 1 1 d . . .
C15 C 0.2779(4) 1.0071(2) 0.41403(7) 0.0270(5) Uani 1 1 d . . .
H15A H 0.1816 0.9820 0.4300 0.032 Uiso 1 1 calc R . .
H15B H 0.3656 1.0364 0.4317 0.032 Uiso 1 1 calc R . .
C16 C 0.5246(4) 0.9351(3) 0.37598(8) 0.0312(6) Uani 1 1 d . . .
H16A H 0.6112 0.9018 0.3930 0.037 Uiso 1 1 calc R . .
H16B H 0.5452 1.0146 0.3744 0.037 Uiso 1 1 calc R . .
C17 C 0.5280(4) 0.8837(2) 0.33568(8) 0.0263(5) Uani 1 1 d . . .
H17A H 0.5534 0.8047 0.3372 0.032 Uiso 1 1 calc R . .
H17B H 0.6130 0.9195 0.3189 0.032 Uiso 1 1 calc R . .
C18 C 0.1603(3) 1.0805(2) 0.31319(7) 0.0204(4) Uani 1 1 d . . .
H18A H 0.0744 1.0465 0.2957 0.024 Uiso 1 1 calc R . .
C19 C 0.0977(3) 1.0592(2) 0.35508(8) 0.0218(5) Uani 1 1 d . . .
H19A H -0.0124 1.0975 0.3589 0.026 Uiso 1 1 calc R . .
C20 C 0.0687(4) 0.9356(2) 0.35837(8) 0.0235(5) Uani 1 1 d . . .
H20A H 0.0117 0.9185 0.3832 0.028 Uiso 1 1 calc R . .
H20B H -0.0043 0.9103 0.3368 0.028 Uiso 1 1 calc R . .
C21 C 0.2384(4) 0.8783(2) 0.35654(7) 0.0222(5) Uani 1 1 d . . .
H21A H 0.2190 0.7978 0.3578 0.027 Uiso 1 1 calc R . .
C22 C 0.3037(4) 0.7471(3) 0.14306(8) 0.0303(6) Uani 1 1 d . . .
H22A H 0.2944 0.6999 0.1202 0.046 Uiso 1 1 calc R . .
H22B H 0.4176 0.7782 0.1443 0.046 Uiso 1 1 calc R . .
H22C H 0.2207 0.8062 0.1412 0.046 Uiso 1 1 calc R . .
C23 C 0.2126(7) 0.5016(3) 0.27339(10) 0.0505(11) Uani 1 1 d . . .
H23A H 0.1899 0.4260 0.2658 0.076 Uiso 1 1 calc R . .
H23B H 0.1173 0.5296 0.2886 0.076 Uiso 1 1 calc R . .
H23C H 0.3156 0.5044 0.2891 0.076 Uiso 1 1 calc R . .
O5 O 0.3493(19) 0.7228(7) 0.4309(2) 0.037(2) Uani 0.56(3) 1 d PU A 1
O6 O 0.2712(16) 0.8312(5) 0.4784(2) 0.0355(18) Uani 0.56(3) 1 d PU A 1
O51 O 0.4096(18) 0.7411(12) 0.4330(4) 0.040(2) Uani 0.44(3) 1 d PU A 2
O61 O 0.207(2) 0.8129(10) 0.4697(4) 0.042(2) Uani 0.44(3) 1 d PU A 2
O7 O 0.3383(2) 0.42704(16) 0.46373(6) 0.0266(4) Uani 1 1 d . . .
O8 O 0.6438(3) 0.08917(19) 0.45254(7) 0.0374(5) Uani 1 1 d . . .
O9 O 0.9145(4) 0.0899(2) 0.44295(8) 0.0468(7) Uani 1 1 d . . .
N3 N 0.4720(3) 0.57870(18) 0.48621(7) 0.0241(4) Uani 1 1 d . . .
H3 H 0.5707 0.6085 0.4912 0.029 Uiso 1 1 calc R . .
N4 N 0.7802(4) 0.1359(2) 0.45095(7) 0.0294(5) Uani 1 1 d . . .
C24 C 0.3117(4) 0.7403(2) 0.46454(8) 0.0250(5) Uani 1 1 d . . .
C25 C 0.3196(4) 0.6433(2) 0.49307(8) 0.0279(6) Uani 1 1 d . A .
H25 H 0.2194 0.5957 0.4882 0.033 Uiso 1 1 calc R . .
C26 C 0.3134(6) 0.6810(3) 0.53528(10) 0.0488(10) Uani 1 1 d . . .
H26A H 0.3187 0.6175 0.5525 0.073 Uiso 1 1 calc R A .
H26B H 0.2079 0.7208 0.5399 0.073 Uiso 1 1 calc R . .
H26C H 0.4096 0.7291 0.5406 0.073 Uiso 1 1 calc R . .
C27 C 0.4683(3) 0.4764(2) 0.47267(7) 0.0194(4) Uani 1 1 d . . .
C28 C 0.6375(3) 0.4213(2) 0.46827(7) 0.0200(4) Uani 1 1 d . . .
C29 C 0.6344(3) 0.3079(2) 0.46350(7) 0.0197(4) Uani 1 1 d . . .
H29 H 0.5308 0.2688 0.4642 0.024 Uiso 1 1 calc R . .
C30 C 0.7858(4) 0.2542(2) 0.45770(7) 0.0226(5) Uani 1 1 d . . .
C31 C 0.9401(4) 0.3070(3) 0.45605(9) 0.0311(6) Uani 1 1 d . . .
H31 H 1.0417 0.2675 0.4519 0.037 Uiso 1 1 calc R . .
C32 C 0.9417(4) 0.4194(3) 0.46069(11) 0.0362(7) Uani 1 1 d . . .
H32 H 1.0456 0.4580 0.4597 0.043 Uiso 1 1 calc R . .
C33 C 0.7915(4) 0.4757(2) 0.46678(9) 0.0297(6) Uani 1 1 d . . .
H33 H 0.7941 0.5526 0.4700 0.036 Uiso 1 1 calc R . .
O100 O 0.3305(13) 0.5788(5) 0.37088(14) 0.072(3) Uani 0.727(18) 1 d PD B 1
H100 H 0.3019 0.6034 0.3927 0.109 Uiso 0.727(18) 1 calc PR B 1
C100 C 0.505(2) 0.5466(10) 0.3720(6) 0.073(3) Uani 0.727(18) 1 d PDU B 1
H101 H 0.5760 0.6110 0.3762 0.110 Uiso 0.727(18) 1 calc PR B 1
H102 H 0.5358 0.5120 0.3474 0.110 Uiso 0.727(18) 1 calc PR B 1
H103 H 0.5224 0.4948 0.3934 0.110 Uiso 0.727(18) 1 calc PR B 1
O110 O 0.435(3) 0.6219(16) 0.3684(4) 0.066(6) Uani 0.273(18) 1 d PD B 2
H110 H 0.4339 0.6518 0.3903 0.099 Uiso 0.273(18) 1 calc PR B 2
C110 C 0.500(6) 0.513(2) 0.3719(16) 0.070(5) Uani 0.273(18) 1 d PDU B 2
H111 H 0.6232 0.5159 0.3749 0.084 Uiso 0.273(18) 1 calc PR B 2
H112 H 0.4721 0.4713 0.3485 0.084 Uiso 0.273(18) 1 calc PR B 2
H113 H 0.4501 0.4776 0.3947 0.084 Uiso 0.273(18) 1 calc PR B 2
O200 O 0.9116(12) 0.7048(5) 0.35079(17) 0.089(3) Uani 0.875(17) 1 d PU C 1
H200 H 0.8780 0.6728 0.3307 0.134 Uiso 0.875(17) 1 calc PR C 1
C200 C 0.9457(15) 0.6267(7) 0.38029(17) 0.093(4) Uani 0.875(17) 1 d P C 1
H201 H 0.8496 0.6228 0.3982 0.140 Uiso 0.875(17) 1 calc PR C 1
H202 H 1.0471 0.6483 0.3947 0.140 Uiso 0.875(17) 1 calc PR C 1
H203 H 0.9639 0.5551 0.3684 0.140 Uiso 0.875(17) 1 calc PR C 1
O210 O 0.985(9) 0.664(4) 0.3511(14) 0.094(6) Uani 0.125(17) 1 d PU C 2
H210 H 0.9141 0.6317 0.3371 0.141 Uiso 0.125(17) 1 calc PR C 2
C210 C 1.071(7) 0.583(3) 0.3771(11) 0.060(14) Uani 0.125(17) 1 d P C 2
H211 H 1.1896 0.5766 0.3695 0.072 Uiso 0.125(17) 1 calc PR C 2
H212 H 1.0152 0.5123 0.3746 0.072 Uiso 0.125(17) 1 calc PR C 2
H213 H 1.0637 0.6083 0.4041 0.072 Uiso 0.125(17) 1 calc PR C 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0259(9) 0.0235(8) 0.0265(9) -0.0014(7) 0.0007(8) 0.0005(8)
O2 0.0337(10) 0.0311(10) 0.0193(8) -0.0064(7) -0.0028(8) 0.0009(9)
O3 0.0481(13) 0.0239(9) 0.0271(9) -0.0053(7) -0.0041(10) -0.0001(10)
O4 0.089(2) 0.0318(11) 0.0212(9) 0.0011(8) -0.0086(12) 0.0112(14)
N1 0.0256(10) 0.0245(10) 0.0164(8) -0.0002(8) -0.0011(8) 0.0017(9)
N2 0.0292(11) 0.0291(11) 0.0174(9) 0.0001(8) -0.0027(8) 0.0095(10)
C1 0.0263(12) 0.0255(11) 0.0182(10) -0.0017(9) -0.0018(9) 0.0035(10)
C2 0.0236(11) 0.0282(12) 0.0200(10) -0.0063(9) -0.0039(10) 0.0025(10)
C3 0.0269(12) 0.0212(11) 0.0238(11) -0.0032(9) -0.0015(10) 0.0041(10)
C4 0.0298(13) 0.0216(11) 0.0190(10) -0.0008(8) -0.0009(10) 0.0045(10)
C5 0.0226(11) 0.0216(10) 0.0177(9) -0.0016(8) -0.0016(9) 0.0048(9)
C6 0.0243(12) 0.0220(11) 0.0186(10) -0.0021(8) -0.0024(9) 0.0015(9)
C7 0.0235(11) 0.0221(11) 0.0167(9) -0.0016(8) -0.0003(9) 0.0061(9)
C8 0.0194(11) 0.0210(10) 0.0183(10) -0.0001(8) -0.0009(8) 0.0027(9)
C9 0.0431(16) 0.0254(12) 0.0220(11) 0.0030(10) 0.0001(12) 0.0029(12)
C10 0.0343(14) 0.0203(11) 0.0267(12) 0.0038(9) -0.0008(11) 0.0010(11)
C11 0.0207(11) 0.0209(11) 0.0264(11) 0.0013(9) -0.0014(9) 0.0031(9)
C12 0.0341(15) 0.0250(12) 0.0291(13) -0.0060(10) 0.0045(12) 0.0033(12)
C13 0.0252(12) 0.0317(13) 0.0232(11) -0.0034(10) 0.0021(10) 0.0045(11)
C14 0.0233(11) 0.0275(12) 0.0220(10) -0.0015(9) 0.0035(9) 0.0062(10)
C15 0.0350(14) 0.0271(12) 0.0188(10) -0.0031(9) 0.0000(10) 0.0085(12)
C16 0.0281(14) 0.0440(17) 0.0214(11) -0.0061(11) -0.0074(10) 0.0117(13)
C17 0.0243(13) 0.0317(13) 0.0230(11) -0.0030(10) -0.0028(10) 0.0096(11)
C18 0.0204(10) 0.0189(10) 0.0218(10) 0.0000(8) -0.0028(9) 0.0037(9)
C19 0.0186(11) 0.0217(11) 0.0250(11) 0.0010(9) 0.0013(9) 0.0046(9)
C20 0.0234(12) 0.0217(11) 0.0253(11) 0.0025(9) 0.0025(10) 0.0028(10)
C21 0.0279(12) 0.0214(10) 0.0171(9) 0.0003(8) -0.0025(9) 0.0041(10)
C22 0.0294(14) 0.0419(16) 0.0198(11) -0.0066(11) -0.0005(10) -0.0006(13)
C23 0.096(3) 0.0229(13) 0.0329(15) 0.0005(12) 0.0008(19) -0.004(2)
O5 0.069(6) 0.022(3) 0.0189(18) -0.0037(16) 0.003(3) 0.009(3)
O6 0.052(5) 0.020(2) 0.035(3) -0.0008(18) 0.010(3) 0.011(3)
O51 0.044(5) 0.035(5) 0.040(4) 0.012(3) 0.016(4) 0.013(4)
O61 0.050(6) 0.034(4) 0.042(4) 0.004(3) 0.010(4) 0.019(4)
O7 0.0148(8) 0.0223(9) 0.0427(11) -0.0069(8) -0.0030(8) 0.0018(7)
O8 0.0375(12) 0.0291(11) 0.0455(13) -0.0118(10) -0.0081(10) 0.0046(10)
O9 0.0548(16) 0.0374(13) 0.0483(14) 0.0137(11) 0.0257(12) 0.0249(12)
N3 0.0260(11) 0.0151(9) 0.0312(11) -0.0002(8) -0.0023(9) -0.0008(8)
N4 0.0391(14) 0.0298(11) 0.0193(9) 0.0012(8) 0.0027(10) 0.0140(11)
C24 0.0274(13) 0.0209(11) 0.0266(12) -0.0043(9) -0.0021(10) 0.0027(10)
C25 0.0318(14) 0.0200(11) 0.0319(13) -0.0003(10) 0.0065(11) 0.0031(11)
C26 0.081(3) 0.0371(17) 0.0286(15) 0.0028(13) 0.0162(18) 0.016(2)
C27 0.0198(11) 0.0185(10) 0.0199(10) 0.0003(8) -0.0008(8) -0.0003(8)
C28 0.0150(9) 0.0217(11) 0.0234(11) 0.0030(9) -0.0026(8) -0.0006(9)
C29 0.0187(10) 0.0218(11) 0.0185(10) 0.0008(8) -0.0016(8) 0.0026(9)
C30 0.0250(11) 0.0263(11) 0.0165(9) 0.0032(8) 0.0008(9) 0.0077(10)
C31 0.0202(12) 0.0414(16) 0.0317(14) 0.0072(12) 0.0002(10) 0.0095(12)
C32 0.0164(11) 0.0423(17) 0.0497(18) 0.0078(15) -0.0049(12) -0.0022(12)
C33 0.0176(11) 0.0282(13) 0.0434(16) 0.0052(12) -0.0070(11) -0.0026(10)
O100 0.138(7) 0.047(3) 0.033(2) -0.0078(19) 0.004(3) 0.011(4)
C100 0.104(6) 0.054(7) 0.062(4) 0.002(7) 0.027(4) 0.023(7)
O110 0.090(14) 0.055(9) 0.053(7) 0.028(6) 0.017(7) 0.031(9)
C110 0.090(9) 0.060(13) 0.059(7) -0.006(12) 0.027(7) 0.015(11)
O200 0.153(7) 0.050(3) 0.065(2) 0.007(2) -0.037(3) -0.044(4)
C200 0.146(9) 0.098(6) 0.036(3) 0.001(3) -0.010(4) -0.033(7)
O210 0.153(13) 0.062(11) 0.068(9) 0.011(10) -0.031(10) -0.042(10)
C210 0.09(3) 0.038(17) 0.050(19) 0.002(14) 0.04(2) 0.008(19)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.431(3) . ?
O1 C12 1.445(3) . ?
O2 C2 1.379(3) . ?
O2 C22 1.435(4) . ?
O3 C3 1.372(3) . ?
O3 C23 1.431(4) . ?
O4 C9 1.228(3) . ?
N1 C9 1.362(4) . ?
N1 C6 1.421(3) . ?
N1 C8 1.492(3) . ?
N2 C16 1.509(4) . ?
N2 C15 1.517(3) . ?
N2 C21 1.536(3) . ?
N2 H2A 0.9300 . ?
C1 C2 1.391(4) . ?
C1 C6 1.397(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.407(4) . ?
C3 C4 1.393(4) . ?
C4 C5 1.399(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.379(3) . ?
C5 C7 1.504(3) . ?
C7 C21 1.545(4) . ?
C7 C17 1.548(4) . ?
C7 C8 1.563(3) . ?
C8 C18 1.528(4) . ?
C8 H8A 1.0000 . ?
C9 C10 1.516(4) . ?
C10 C11 1.550(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.528(4) . ?
C11 H11A 1.0000 . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.332(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.504(4) . ?
C14 C19 1.523(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.524(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.547(4) . ?
C18 H18A 1.0000 . ?
C19 C20 1.537(4) . ?
C19 H19A 1.0000 . ?
C20 C21 1.518(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.214(9) . ?
O6 C24 1.254(7) . ?
O51 C24 1.333(12) . ?
O61 C24 1.231(9) . ?
O7 C27 1.234(3) . ?
O8 N4 1.224(4) . ?
O9 N4 1.235(4) . ?
N3 C27 1.338(3) . ?
N3 C25 1.463(4) . ?
N3 H3 0.8800 . ?
N4 C30 1.471(4) . ?
C24 C25 1.544(4) . ?
C25 C26 1.525(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.509(4) . ?
C28 C33 1.391(4) . ?
C28 C29 1.401(4) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(4) . ?
C31 C32 1.388(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O100 C100 1.438(14) . ?
O100 H100 0.8400 . ?
C100 H101 0.9800 . ?
C100 H102 0.9800 . ?
C100 H103 0.9800 . ?
O110 C110 1.437(14) . ?
O110 H110 0.8400 . ?
C110 H111 0.9800 . ?
C110 H112 0.9800 . ?
C110 H113 0.9800 . ?
O200 C200 1.422(9) . ?
O200 H200 0.8400 . ?
C200 H201 0.9800 . ?
C200 H202 0.9800 . ?
C200 H203 0.9800 . ?
O210 C210 1.50(6) . ?
O210 H210 0.8400 . ?
C210 H211 0.9800 . ?
C210 H212 0.9800 . ?
C210 H213 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.8(2) . . ?
C2 O2 C22 116.3(2) . . ?
C3 O3 C23 115.5(2) . . ?
C9 N1 C6 124.2(2) . . ?
C9 N1 C8 119.0(2) . . ?
C6 N1 C8 109.3(2) . . ?
C16 N2 C15 112.2(2) . . ?
C16 N2 C21 108.0(2) . . ?
C15 N2 C21 113.4(2) . . ?
C16 N2 H2A 107.7 . . ?
C15 N2 H2A 107.7 . . ?
C21 N2 H2A 107.7 . . ?
C2 C1 C6 117.4(2) . . ?
C2 C1 H1A 121.3 . . ?
C6 C1 H1A 121.3 . . ?
O2 C2 C1 123.1(2) . . ?
O2 C2 C3 115.6(2) . . ?
C1 C2 C3 121.2(2) . . ?
O3 C3 C4 124.9(2) . . ?
O3 C3 C2 115.1(2) . . ?
C4 C3 C2 119.9(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 C7 110.9(2) . . ?
C4 C5 C7 128.8(2) . . ?
C5 C6 C1 122.2(2) . . ?
C5 C6 N1 110.0(2) . . ?
C1 C6 N1 127.8(2) . . ?
C5 C7 C21 115.4(2) . . ?
C5 C7 C17 112.0(2) . . ?
C21 C7 C17 102.0(2) . . ?
C5 C7 C8 102.44(19) . . ?
C21 C7 C8 114.2(2) . . ?
C17 C7 C8 111.1(2) . . ?
N1 C8 C18 106.0(2) . . ?
N1 C8 C7 104.20(19) . . ?
C18 C8 C7 117.1(2) . . ?
N1 C8 H8A 109.7 . . ?
C18 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O4 C9 N1 122.7(3) . . ?
O4 C9 C10 121.5(3) . . ?
N1 C9 C10 115.8(2) . . ?
C9 C10 C11 116.6(2) . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 115.1(2) . . ?
O1 C11 C10 105.2(2) . . ?
C18 C11 C10 109.6(2) . . ?
O1 C11 H11A 108.9 . . ?
C18 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
O1 C12 C13 111.3(2) . . ?
O1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 122.2(3) . . ?
C14 C13 H13A 118.9 . . ?
C12 C13 H13A 118.9 . . ?
C13 C14 C15 122.0(3) . . ?
C13 C14 C19 122.4(2) . . ?
C15 C14 C19 115.6(2) . . ?
C14 C15 N2 109.9(2) . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
N2 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 104.7(2) . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.2(2) . . ?
C16 C17 H17A 111.1 . . ?
C7 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C7 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C8 C18 C11 108.1(2) . . ?
C8 C18 C19 112.3(2) . . ?
C11 C18 C19 117.9(2) . . ?
C8 C18 H18A 105.9 . . ?
C11 C18 H18A 105.9 . . ?
C19 C18 H18A 105.9 . . ?
C14 C19 C20 109.2(2) . . ?
C14 C19 C18 114.4(2) . . ?
C20 C19 C18 106.5(2) . . ?
C14 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C21 C20 C19 108.7(2) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 110.5(2) . . ?
C20 C21 C7 115.6(2) . . ?
N2 C21 C7 104.7(2) . . ?
C20 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C27 N3 C25 123.1(2) . . ?
C27 N3 H3 118.5 . . ?
C25 N3 H3 118.5 . . ?
O8 N4 O9 123.8(3) . . ?
O8 N4 C30 118.8(2) . . ?
O9 N4 C30 117.4(3) . . ?
O5 C24 O61 115.6(7) . . ?
O5 C24 O6 125.7(6) . . ?
O61 C24 O6 29.5(5) . . ?
O5 C24 O51 23.6(6) . . ?
O61 C24 O51 120.4(7) . . ?
O6 C24 O51 116.9(7) . . ?
O5 C24 C25 117.4(5) . . ?
O61 C24 C25 119.5(5) . . ?
O6 C24 C25 116.9(4) . . ?
O51 C24 C25 120.0(6) . . ?
N3 C25 C26 110.2(3) . . ?
N3 C25 C24 110.4(2) . . ?
C26 C25 C24 111.8(2) . . ?
N3 C25 H25 108.1 . . ?
C26 C25 H25 108.1 . . ?
C24 C25 H25 108.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 N3 124.4(2) . . ?
O7 C27 C28 119.7(2) . . ?
N3 C27 C28 115.8(2) . . ?
C33 C28 C29 119.2(2) . . ?
C33 C28 C27 124.5(2) . . ?
C29 C28 C27 116.2(2) . . ?
C30 C29 C28 118.3(2) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C29 C30 C31 123.3(2) . . ?
C29 C30 N4 117.8(3) . . ?
C31 C30 N4 118.8(3) . . ?
C30 C31 C32 117.9(3) . . ?
C30 C31 H31 121.1 . . ?
C32 C31 H31 121.1 . . ?
C31 C32 C33 120.2(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C28 121.1(3) . . ?
C32 C33 H33 119.4 . . ?
C28 C33 H33 119.4 . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H101 109.5 . . ?
O100 C100 H102 109.5 . . ?
H101 C100 H102 109.5 . . ?
O100 C100 H103 109.5 . . ?
H101 C100 H103 109.5 . . ?
H102 C100 H103 109.5 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H111 109.5 . . ?
O110 C110 H112 109.5 . . ?
H111 C110 H112 109.5 . . ?
O110 C110 H113 109.5 . . ?
H111 C110 H113 109.5 . . ?
H112 C110 H113 109.5 . . ?
C200 O200 H200 109.5 . . ?
O200 C200 H201 109.5 . . ?
O200 C200 H202 109.5 . . ?
H201 C200 H202 109.5 . . ?
O200 C200 H203 109.5 . . ?
H201 C200 H203 109.5 . . ?
H202 C200 H203 109.5 . . ?
C210 O210 H210 109.5 . . ?
O210 C210 H211 109.5 . . ?
O210 C210 H212 109.5 . . ?
H211 C210 H212 109.5 . . ?
O210 C210 H213 109.5 . . ?
H211 C210 H213 109.5 . . ?
H212 C210 H213 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 5.9(4) . . . . ?
C22 O2 C2 C3 -174.3(3) . . . . ?
C6 C1 C2 O2 -178.8(3) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C23 O3 C3 C4 2.2(5) . . . . ?
C23 O3 C3 C2 -178.0(3) . . . . ?
O2 C2 C3 O3 -3.4(4) . . . . ?
C1 C2 C3 O3 176.4(3) . . . . ?
O2 C2 C3 C4 176.3(3) . . . . ?
C1 C2 C3 C4 -3.9(4) . . . . ?
O3 C3 C4 C5 -177.5(3) . . . . ?
C2 C3 C4 C5 2.8(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C3 C4 C5 C7 -173.7(3) . . . . ?
C4 C5 C6 C1 -3.2(4) . . . . ?
C7 C5 C6 C1 172.1(2) . . . . ?
C4 C5 C6 N1 177.5(3) . . . . ?
C7 C5 C6 N1 -7.2(3) . . . . ?
C2 C1 C6 C5 2.1(4) . . . . ?
C2 C1 C6 N1 -178.7(3) . . . . ?
C9 N1 C6 C5 -154.1(3) . . . . ?
C8 N1 C6 C5 -4.9(3) . . . . ?
C9 N1 C6 C1 26.6(5) . . . . ?
C8 N1 C6 C1 175.9(3) . . . . ?
C6 C5 C7 C21 140.1(2) . . . . ?
C4 C5 C7 C21 -45.1(4) . . . . ?
C6 C5 C7 C17 -103.8(3) . . . . ?
C4 C5 C7 C17 71.0(4) . . . . ?
C6 C5 C7 C8 15.4(3) . . . . ?
C4 C5 C7 C8 -169.9(3) . . . . ?
C9 N1 C8 C18 41.0(3) . . . . ?
C6 N1 C8 C18 -110.1(2) . . . . ?
C9 N1 C8 C7 165.2(3) . . . . ?
C6 N1 C8 C7 14.1(3) . . . . ?
C5 C7 C8 N1 -17.1(3) . . . . ?
C21 C7 C8 N1 -142.7(2) . . . . ?
C17 C7 C8 N1 102.6(2) . . . . ?
C5 C7 C8 C18 99.6(2) . . . . ?
C21 C7 C8 C18 -25.9(3) . . . . ?
C17 C7 C8 C18 -140.7(2) . . . . ?
C6 N1 C9 O4 -21.4(5) . . . . ?
C8 N1 C9 O4 -167.8(3) . . . . ?
C6 N1 C9 C10 159.8(3) . . . . ?
C8 N1 C9 C10 13.3(4) . . . . ?
O4 C9 C10 C11 141.0(3) . . . . ?
N1 C9 C10 C11 -40.1(4) . . . . ?
C12 O1 C11 C18 -67.1(3) . . . . ?
C12 O1 C11 C10 172.2(2) . . . . ?
C9 C10 C11 O1 132.3(3) . . . . ?
C9 C10 C11 C18 8.0(4) . . . . ?
C11 O1 C12 C13 87.8(3) . . . . ?
O1 C12 C13 C14 -64.9(4) . . . . ?
C12 C13 C14 C15 178.3(3) . . . . ?
C12 C13 C14 C19 -2.6(4) . . . . ?
C13 C14 C15 N2 -127.4(3) . . . . ?
C19 C14 C15 N2 53.4(3) . . . . ?
C16 N2 C15 C14 76.8(3) . . . . ?
C21 N2 C15 C14 -45.9(3) . . . . ?
C15 N2 C16 C17 -141.6(2) . . . . ?
C21 N2 C16 C17 -16.0(3) . . . . ?
N2 C16 C17 C7 36.0(3) . . . . ?
C5 C7 C17 C16 -165.9(2) . . . . ?
C21 C7 C17 C16 -41.9(3) . . . . ?
C8 C7 C17 C16 80.2(3) . . . . ?
N1 C8 C18 C11 -71.6(2) . . . . ?
C7 C8 C18 C11 172.7(2) . . . . ?
N1 C8 C18 C19 156.8(2) . . . . ?
C7 C8 C18 C19 41.1(3) . . . . ?
O1 C11 C18 C8 -72.8(3) . . . . ?
C10 C11 C18 C8 45.5(3) . . . . ?
O1 C11 C18 C19 55.7(3) . . . . ?
C10 C11 C18 C19 174.1(2) . . . . ?
C13 C14 C19 C20 178.5(3) . . . . ?
C15 C14 C19 C20 -2.3(3) . . . . ?
C13 C14 C19 C18 59.4(3) . . . . ?
C15 C14 C19 C18 -121.4(2) . . . . ?
C8 C18 C19 C14 59.2(3) . . . . ?
C11 C18 C19 C14 -67.3(3) . . . . ?
C8 C18 C19 C20 -61.5(3) . . . . ?
C11 C18 C19 C20 172.0(2) . . . . ?
C14 C19 C20 C21 -55.6(3) . . . . ?
C18 C19 C20 C21 68.4(3) . . . . ?
C19 C20 C21 N2 62.8(3) . . . . ?
C19 C20 C21 C7 -55.9(3) . . . . ?
C16 N2 C21 C20 -135.3(2) . . . . ?
C15 N2 C21 C20 -10.4(3) . . . . ?
C16 N2 C21 C7 -10.2(3) . . . . ?
C15 N2 C21 C7 114.7(2) . . . . ?
C5 C7 C21 C20 -84.8(3) . . . . ?
C17 C7 C21 C20 153.5(2) . . . . ?
C8 C7 C21 C20 33.5(3) . . . . ?
C5 C7 C21 N2 153.4(2) . . . . ?
C17 C7 C21 N2 31.7(2) . . . . ?
C8 C7 C21 N2 -88.2(2) . . . . ?
C27 N3 C25 C26 122.9(3) . . . . ?
C27 N3 C25 C24 -113.2(3) . . . . ?
O5 C24 C25 N3 42.6(8) . . . . ?
O61 C24 C25 N3 -168.9(11) . . . . ?
O6 C24 C25 N3 -135.5(7) . . . . ?
O51 C24 C25 N3 15.9(10) . . . . ?
O5 C24 C25 C26 165.6(8) . . . . ?
O61 C24 C25 C26 -45.9(11) . . . . ?
O6 C24 C25 C26 -12.5(8) . . . . ?
O51 C24 C25 C26 138.9(10) . . . . ?
C25 N3 C27 O7 1.8(4) . . . . ?
C25 N3 C27 C28 -178.6(2) . . . . ?
O7 C27 C28 C33 161.2(3) . . . . ?
N3 C27 C28 C33 -18.5(4) . . . . ?
O7 C27 C28 C29 -15.6(3) . . . . ?
N3 C27 C28 C29 164.8(2) . . . . ?
C33 C28 C29 C30 0.4(4) . . . . ?
C27 C28 C29 C30 177.3(2) . . . . ?
C28 C29 C30 C31 -0.5(4) . . . . ?
C28 C29 C30 N4 -177.3(2) . . . . ?
O8 N4 C30 C29 -3.4(4) . . . . ?
O9 N4 C30 C29 174.8(2) . . . . ?
O8 N4 C30 C31 179.8(3) . . . . ?
O9 N4 C30 C31 -2.1(4) . . . . ?
C29 C30 C31 C32 0.3(4) . . . . ?
N4 C30 C31 C32 177.0(3) . . . . ?
C30 C31 C32 C33 0.0(5) . . . . ?
C31 C32 C33 C28 -0.2(5) . . . . ?
C29 C28 C33 C32 -0.1(4) . . . . ?
C27 C28 C33 C32 -176.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.93 1.67 2.589(13) 167.6 .
N2 H2A O5 0.93 1.78 2.695(10) 167.1 .
N3 H3 O61 0.88 1.97 2.743(9) 145.2 4_566
N3 H3 O6 0.88 2.04 2.884(9) 160.5 4_566
O100 H100 O5 0.84 2.00 2.722(9) 143.0 .
O110 H110 O51 0.84 1.84 2.67(2) 167.9 .
O200 H200 O4 0.84 1.93 2.739(6) 160.4 3_645
O210 H210 O4 0.84 2.04 2.87(5) 167.5 3_645

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        35.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 930485'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
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#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


#===== end



data_b3nb(dl)a1
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-(D~0.55~L~0.45~)-alaninate methanol disolvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N2 O4, C10 H9 N2 O5, 2(C H4 O)'
_chemical_formula_sum            'C35 H44 N4 O11'
_chemical_formula_weight         696.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.144(3)
_cell_length_b                   7.893(2)
_cell_length_c                   34.093(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.63(3)
_cell_angle_gamma                90.00
_cell_volume                     3267.7(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10844
_cell_measurement_theta_min      2.9815
_cell_measurement_theta_max      36.8511

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46658
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         30.00
_reflns_number_total             10056
_reflns_number_gt                9071
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+3.9284P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         10056
_refine_ls_number_parameters     1069
_refine_ls_number_restraints     307
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0828
_refine_ls_wR_factor_ref         0.2066
_refine_ls_wR_factor_gt          0.2016
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4666(2) 0.9893(4) 0.67461(8) 0.0245(6) Uani 1 1 d . . .
O2 O 1.0502(2) 1.0532(4) 0.82434(8) 0.0278(6) Uani 1 1 d . . .
O3 O 1.1681(2) 1.0847(5) 0.76187(9) 0.0303(7) Uani 1 1 d . . .
O4 O 0.6452(3) 1.0232(6) 0.79698(9) 0.0411(9) Uani 1 1 d . . .
N1 N 0.7232(3) 0.9516(5) 0.73915(9) 0.0214(7) Uani 1 1 d . . .
N2 N 0.8247(3) 0.9096(5) 0.60926(10) 0.0258(7) Uani 1 1 d . . .
H2A H 0.8849 0.8986 0.5928 0.031 Uiso 1 1 calc R . .
C1 C 0.8823(3) 0.9996(5) 0.78701(11) 0.0229(8) Uani 1 1 d . . .
H1A H 0.8385 0.9930 0.8099 0.027 Uiso 1 1 calc R . .
C2 C 0.9942(3) 1.0315(6) 0.78938(11) 0.0247(8) Uani 1 1 d . . .
C3 C 1.0591(3) 1.0422(6) 0.75537(12) 0.0245(8) Uani 1 1 d . . .
C4 C 1.0129(3) 1.0126(5) 0.71861(11) 0.0236(8) Uani 1 1 d . . .
H4A H 1.0568 1.0161 0.6957 0.028 Uiso 1 1 calc R . .
C5 C 0.8994(3) 0.9773(5) 0.71595(11) 0.0216(7) Uani 1 1 d . . .
C6 C 0.8363(3) 0.9774(6) 0.74942(11) 0.0221(8) Uani 1 1 d . . .
C7 C 0.8321(3) 0.9300(5) 0.68039(11) 0.0202(7) Uani 1 1 d . . .
C8 C 0.7114(3) 0.9505(5) 0.69562(10) 0.0192(7) Uani 1 1 d . . .
H8A H 0.6654 0.8518 0.6870 0.023 Uiso 1 1 calc R . .
C9 C 0.6366(3) 1.0002(6) 0.76142(12) 0.0251(8) Uani 1 1 d . . .
C10 C 0.5293(3) 1.0300(6) 0.73987(12) 0.0243(8) Uani 1 1 d . . .
H10A H 0.4848 1.1087 0.7558 0.029 Uiso 1 1 calc R . .
H10B H 0.4892 0.9209 0.7388 0.029 Uiso 1 1 calc R . .
C11 C 0.5330(3) 1.1014(5) 0.69776(11) 0.0207(7) Uani 1 1 d . . .
H11A H 0.4986 1.2165 0.6975 0.025 Uiso 1 1 calc R . .
C12 C 0.4457(3) 1.0445(6) 0.63480(12) 0.0264(8) Uani 1 1 d . . .
H12A H 0.4413 1.1697 0.6342 0.032 Uiso 1 1 calc R . .
H12B H 0.3739 0.9989 0.6257 0.032 Uiso 1 1 calc R . .
C13 C 0.5349(3) 0.9860(6) 0.60744(12) 0.0255(8) Uani 1 1 d . . .
H13A H 0.5167 0.9088 0.5870 0.031 Uiso 1 1 calc R . .
C14 C 0.6390(3) 1.0400(5) 0.61117(11) 0.0223(7) Uani 1 1 d . . .
C15 C 0.7285(3) 0.9742(6) 0.58488(11) 0.0261(8) Uani 1 1 d . . .
H15A H 0.7537 1.0662 0.5674 0.031 Uiso 1 1 calc R . .
H15B H 0.6990 0.8814 0.5683 0.031 Uiso 1 1 calc R . .
C16 C 0.8015(4) 0.7379(6) 0.62690(12) 0.0308(9) Uani 1 1 d . . .
H16A H 0.8348 0.6467 0.6110 0.037 Uiso 1 1 calc R . .
H16B H 0.7212 0.7177 0.6286 0.037 Uiso 1 1 calc R . .
C17 C 0.8540(4) 0.7449(6) 0.66752(12) 0.0266(9) Uani 1 1 d . . .
H17A H 0.9339 0.7209 0.6665 0.032 Uiso 1 1 calc R . .
H17B H 0.8188 0.6633 0.6855 0.032 Uiso 1 1 calc R . .
C18 C 0.6534(3) 1.1170(5) 0.68467(11) 0.0190(7) Uani 1 1 d . . .
H18A H 0.6875 1.2065 0.7016 0.023 Uiso 1 1 calc R . .
C19 C 0.6753(3) 1.1705(5) 0.64186(11) 0.0213(7) Uani 1 1 d . . .
H19A H 0.6363 1.2798 0.6365 0.026 Uiso 1 1 calc R . .
C20 C 0.7999(3) 1.1996(5) 0.63876(12) 0.0222(8) Uani 1 1 d . . .
H20A H 0.8173 1.2516 0.6131 0.027 Uiso 1 1 calc R . .
H20B H 0.8254 1.2771 0.6598 0.027 Uiso 1 1 calc R . .
C21 C 0.8574(3) 1.0287(5) 0.64274(11) 0.0213(7) Uani 1 1 d . . .
H21A H 0.9387 1.0479 0.6417 0.026 Uiso 1 1 calc R . .
C22 C 0.9863(4) 1.0295(6) 0.85918(12) 0.0294(9) Uani 1 1 d . . .
H22A H 1.0332 1.0475 0.8824 0.044 Uiso 1 1 calc R . .
H22B H 0.9567 0.9140 0.8596 0.044 Uiso 1 1 calc R . .
H22C H 0.9254 1.1109 0.8593 0.044 Uiso 1 1 calc R . .
C23 C 1.2325(3) 1.1112(9) 0.72752(14) 0.0394(12) Uani 1 1 d . . .
H23A H 1.3079 1.1415 0.7352 0.059 Uiso 1 1 calc R . .
H23B H 1.2001 1.2031 0.7119 0.059 Uiso 1 1 calc R . .
H23C H 1.2335 1.0070 0.7119 0.059 Uiso 1 1 calc R . .
O1A O -0.0283(2) 0.6133(4) 0.82495(8) 0.0275(6) Uani 1 1 d . . .
O2A O 0.5432(2) 0.5496(4) 0.67375(8) 0.0281(6) Uani 1 1 d . . .
O3A O 0.6653(2) 0.5135(5) 0.73590(9) 0.0296(7) Uani 1 1 d . . .
O4A O 0.1397(3) 0.5829(6) 0.70182(9) 0.0392(9) Uani 1 1 d . . .
N1A N 0.2229(3) 0.6485(5) 0.75969(9) 0.0221(7) Uani 1 1 d . . .
N2A N 0.3359(3) 0.6833(5) 0.88954(10) 0.0285(8) Uani 1 1 d . . .
H2AA H 0.3974 0.6900 0.9060 0.034 Uiso 1 1 calc R . .
C1A C 0.3776(3) 0.6025(5) 0.71137(11) 0.0232(8) Uani 1 1 d . . .
H1AA H 0.3321 0.6101 0.6886 0.028 Uiso 1 1 calc R . .
C2A C 0.4901(3) 0.5701(5) 0.70882(11) 0.0219(7) Uani 1 1 d . . .
C3A C 0.5571(3) 0.5546(5) 0.74278(12) 0.0235(8) Uani 1 1 d . . .
C4A C 0.5135(3) 0.5836(5) 0.77948(11) 0.0212(7) Uani 1 1 d . . .
H4AA H 0.5591 0.5795 0.8023 0.025 Uiso 1 1 calc R . .
C5A C 0.4012(3) 0.6188(5) 0.78240(11) 0.0209(7) Uani 1 1 d . . .
C6A C 0.3348(3) 0.6234(5) 0.74908(11) 0.0213(7) Uani 1 1 d . . .
C7A C 0.3364(3) 0.6667(6) 0.81827(11) 0.0213(8) Uani 1 1 d . . .
C8A C 0.2143(3) 0.6480(5) 0.80347(11) 0.0190(7) Uani 1 1 d . . .
H8AA H 0.1700 0.7476 0.8122 0.023 Uiso 1 1 calc R . .
C9A C 0.1344(3) 0.6011(6) 0.73763(12) 0.0251(8) Uani 1 1 d . . .
C10A C 0.0275(3) 0.5727(6) 0.75953(12) 0.0281(9) Uani 1 1 d . . .
H10C H -0.0189 0.4952 0.7436 0.034 Uiso 1 1 calc R . .
H10D H -0.0116 0.6825 0.7608 0.034 Uiso 1 1 calc R . .
C11A C 0.0347(3) 0.4999(5) 0.80162(12) 0.0239(8) Uani 1 1 d . . .
H11B H -0.0003 0.3852 0.8020 0.029 Uiso 1 1 calc R . .
C12A C -0.0461(3) 0.5572(7) 0.86471(12) 0.0303(9) Uani 1 1 d . . .
H12C H -0.0511 0.4321 0.8652 0.036 Uiso 1 1 calc R . .
H12D H -0.1168 0.6034 0.8741 0.036 Uiso 1 1 calc R . .
C13A C 0.0458(3) 0.6139(7) 0.89174(12) 0.0302(9) Uani 1 1 d . . .
H13B H 0.0297 0.6916 0.9122 0.036 Uiso 1 1 calc R . .
C14A C 0.1488(3) 0.5590(6) 0.88799(12) 0.0274(9) Uani 1 1 d . . .
C15A C 0.2409(3) 0.6204(7) 0.91380(12) 0.0316(10) Uani 1 1 d . . .
H15C H 0.2663 0.5268 0.9310 0.038 Uiso 1 1 calc R . .
H15D H 0.2140 0.7132 0.9307 0.038 Uiso 1 1 calc R . .
C16A C 0.3163(4) 0.8551(6) 0.87286(13) 0.0310(10) Uani 1 1 d . . .
H16C H 0.3552 0.9421 0.8887 0.037 Uiso 1 1 calc R . .
H16D H 0.2367 0.8817 0.8724 0.037 Uiso 1 1 calc R . .
C17A C 0.3610(3) 0.8502(6) 0.83144(12) 0.0269(9) Uani 1 1 d . . .
H17C H 0.4411 0.8737 0.8313 0.032 Uiso 1 1 calc R . .
H17D H 0.3228 0.9332 0.8143 0.032 Uiso 1 1 calc R . .
C18A C 0.1558(3) 0.4844(5) 0.81444(11) 0.0207(7) Uani 1 1 d . . .
H18B H 0.1881 0.3948 0.7973 0.025 Uiso 1 1 calc R . .
C19A C 0.1809(3) 0.4275(6) 0.85706(12) 0.0250(8) Uani 1 1 d . . .
H19B H 0.1415 0.3188 0.8624 0.030 Uiso 1 1 calc R . .
C20A C 0.3054(3) 0.3970(6) 0.85930(12) 0.0252(8) Uani 1 1 d . . .
H20C H 0.3251 0.3432 0.8847 0.030 Uiso 1 1 calc R . .
H20D H 0.3279 0.3199 0.8379 0.030 Uiso 1 1 calc R . .
C21A C 0.3647(3) 0.5644(6) 0.85551(11) 0.0253(8) Uani 1 1 d . . .
H21B H 0.4458 0.5428 0.8562 0.030 Uiso 1 1 calc R . .
C22A C 0.4770(4) 0.5723(6) 0.63919(12) 0.0305(9) Uani 1 1 d . . .
H22D H 0.5223 0.5548 0.6159 0.046 Uiso 1 1 calc R . .
H22E H 0.4468 0.6874 0.6388 0.046 Uiso 1 1 calc R . .
H22F H 0.4165 0.4901 0.6391 0.046 Uiso 1 1 calc R . .
C23A C 0.7324(3) 0.4839(8) 0.77010(14) 0.0371(11) Uani 1 1 d . . .
H23D H 0.8076 0.4565 0.7621 0.056 Uiso 1 1 calc R . .
H23E H 0.7020 0.3890 0.7850 0.056 Uiso 1 1 calc R . .
H23F H 0.7334 0.5859 0.7865 0.056 Uiso 1 1 calc R . .
O5 O 1.0109(4) 0.8698(7) 0.57228(13) 0.0380(11) Uani 0.793(5) 1 d PU A 1
O6 O 0.9226(4) 1.0297(9) 0.52935(15) 0.0654(18) Uani 0.793(5) 1 d P A 1
O51 O 1.0236(16) 0.967(3) 0.5722(6) 0.043(4) Uani 0.207(5) 1 d PU A 2
O61 O 0.9241(15) 0.848(3) 0.5272(6) 0.045(4) Uani 0.207(5) 1 d PU A 2
O8 O 1.6582(3) 0.5980(5) 0.54738(14) 0.0541(11) Uani 1 1 d . . .
O9 O 1.6594(3) 0.3262(5) 0.55012(12) 0.0454(10) Uani 1 1 d . . .
N4 N 1.6113(3) 0.4586(6) 0.54618(10) 0.0311(8) Uani 1 1 d . A .
C24 C 1.0050(3) 0.9420(6) 0.53963(13) 0.0291(9) Uani 1 1 d . . .
C25 C 1.1036(3) 0.9378(6) 0.51141(14) 0.0286(9) Uani 1 1 d . . .
H251 H 1.1497 0.8347 0.5161 0.034 Uiso 0.207(5) 1 calc PR A 2
H25 H 1.1500 1.0335 0.5169 0.034 Uiso 0.793(5) 1 d PR A 1
C26 C 1.0644(5) 0.9458(11) 0.46809(17) 0.0579(18) Uani 1 1 d . . .
H26A H 1.1284 0.9426 0.4509 0.087 Uiso 1 1 calc R A .
H26B H 1.0235 1.0512 0.4636 0.087 Uiso 1 1 calc R . .
H26C H 1.0166 0.8488 0.4624 0.087 Uiso 1 1 calc R . .
O7 O 1.3211(5) 0.9163(6) 0.54215(18) 0.0276(11) Uani 0.793(5) 1 d PU . 1
N3 N 1.1671(3) 0.7882(6) 0.51753(13) 0.0224(9) Uani 0.793(5) 1 d P . 1
H3 H 1.1365 0.6901 0.5118 0.027 Uiso 0.793(5) 1 calc PR A 1
C27 C 1.2700(4) 0.7883(6) 0.53139(15) 0.0201(10) Uani 0.793(5) 1 d P . 1
C28 C 1.3244(4) 0.6133(6) 0.53399(13) 0.0295(9) Uani 1 1 d U . .
H28 H 1.2861 0.7175 0.5309 0.035 Uiso 0.207(5) 1 calc PR A 2
C29 C 1.4388(3) 0.6106(6) 0.53673(12) 0.0268(8) Uani 1 1 d U A .
H29A H 1.4800 0.7128 0.5359 0.032 Uiso 1 1 calc R . .
C30 C 1.4910(3) 0.4571(6) 0.54069(12) 0.0271(8) Uani 1 1 d U . .
C31 C 1.4366(4) 0.3040(7) 0.54190(14) 0.0355(11) Uani 1 1 d . A .
H31A H 1.4764 0.2009 0.5445 0.043 Uiso 1 1 calc R . .
C32 C 1.3229(5) 0.3037(8) 0.53919(19) 0.0446(13) Uani 1 1 d . . .
H32A H 1.2829 0.2003 0.5396 0.053 Uiso 0.793(5) 1 calc PR A 1
C33 C 1.2673(4) 0.4616(7) 0.53582(17) 0.0408(12) Uani 1 1 d . A .
H33A H 1.1891 0.4632 0.5348 0.049 Uiso 1 1 calc R . .
O71 O 1.317(2) 0.968(3) 0.5423(8) 0.031(4) Uani 0.207(5) 1 d PU . 2
N31 N 1.1658(13) 1.082(2) 0.5156(5) 0.024(3) Uani 0.207(5) 1 d PU . 2
H31 H 1.1364 1.1783 0.5075 0.028 Uiso 0.207(5) 1 calc PR A 2
C271 C 1.2711(14) 1.089(2) 0.5315(5) 0.019(4) Uani 0.207(5) 1 d P . 2
O5A O 0.5257(4) 0.6396(10) 0.92798(13) 0.0654(17) Uani 0.885(6) 1 d PU B 1
O6A O 0.4242(3) 0.7532(7) 0.97310(12) 0.0456(12) Uani 0.885(6) 1 d P B 1
O5B O 0.512(4) 0.737(8) 0.9257(13) 0.060(5) Uani 0.115(6) 1 d PU B 2
O6B O 0.432(5) 0.617(10) 0.9650(19) 0.102(14) Uani 0.115(6) 1 d PU B 2
O8A O 1.1593(3) 0.3019(5) 0.95679(12) 0.0409(9) Uani 1 1 d . . .
O9A O 1.1484(3) 0.0343(6) 0.94476(10) 0.0447(10) Uani 1 1 d . . .
N4A N 1.1069(3) 0.1700(6) 0.95318(10) 0.0298(8) Uani 1 1 d . B .
C24A C 0.5112(3) 0.6884(6) 0.96196(12) 0.0268(8) Uani 1 1 d . . .
C25A C 0.6088(3) 0.6752(6) 0.99131(12) 0.0247(8) Uani 1 1 d . . .
H25B H 0.6524 0.5700 0.9864 0.030 Uiso 0.115(6) 1 calc PR B 2
H25A H 0.6573 0.7691 0.9868 0.030 Uiso 0.885(6) 1 d PR B 1
C26A C 0.5710(4) 0.6813(8) 1.03410(13) 0.0358(11) Uani 1 1 d . . .
H26D H 0.6352 0.6729 1.0516 0.054 Uiso 1 1 calc R B .
H26E H 0.5210 0.5865 1.0391 0.054 Uiso 1 1 calc R . .
H26F H 0.5326 0.7884 1.0389 0.054 Uiso 1 1 calc R . .
O7A O 0.8206(3) 0.6435(5) 0.95755(11) 0.0229(8) Uani 0.885(6) 1 d PU . 1
N3A N 0.6708(3) 0.5192(5) 0.98487(11) 0.0195(8) Uani 0.885(6) 1 d P . 1
H3A H 0.6409 0.4223 0.9918 0.023 Uiso 0.885(6) 1 calc PR B 1
C27A C 0.7714(3) 0.5168(5) 0.96884(12) 0.0163(8) Uani 0.885(6) 1 d P . 1
O7B O 0.825(3) 0.708(4) 0.9611(11) 0.029(5) Uani 0.115(6) 1 d PU . 2
N3B N 0.672(3) 0.827(6) 0.9804(12) 0.044(9) Uani 0.115(6) 1 d PU . 2
H3B H 0.6393 0.9255 0.9815 0.053 Uiso 0.115(6) 1 calc PR B 2
C27B C 0.778(3) 0.823(5) 0.9690(12) 0.030(8) Uani 0.115(6) 1 d PU . 2
C28A C 0.8231(3) 0.3424(5) 0.96499(13) 0.0231(8) Uani 1 1 d . . .
H28A H 0.7868 0.4483 0.9677 0.028 Uiso 0.115(6) 1 calc PR B 2
C29A C 0.9369(3) 0.3351(6) 0.96172(11) 0.0223(8) Uani 1 1 d . B .
H29B H 0.9798 0.4358 0.9619 0.027 Uiso 1 1 calc R . .
C30A C 0.9865(3) 0.1779(6) 0.95825(11) 0.0249(8) Uani 1 1 d . . .
C31A C 0.9291(4) 0.0286(6) 0.95754(15) 0.0368(11) Uani 1 1 d . B .
H31B H 0.9658 -0.0772 0.9553 0.044 Uiso 1 1 calc R . .
C32A C 0.8155(5) 0.0375(7) 0.9603(2) 0.0508(15) Uani 1 1 d . . .
H32C H 0.7732 -0.0636 0.9594 0.061 Uiso 0.885(6) 1 calc PR B 1
C33A C 0.7631(4) 0.1918(7) 0.96426(18) 0.0408(12) Uani 1 1 d . B .
H33B H 0.6852 0.1953 0.9665 0.049 Uiso 1 1 calc R . .
O100 O 1.1637(13) 0.8560(14) 0.6380(4) 0.088(3) Uani 0.536(13) 1 d PDU C 1
H100 H 1.1075 0.9011 0.6279 0.132 Uiso 0.536(13) 1 calc PR C 1
C100 C 1.2000(17) 0.726(2) 0.6139(6) 0.115(4) Uani 0.536(13) 1 d PDU C 1
H101 H 1.1390 0.6870 0.5972 0.172 Uiso 0.536(13) 1 calc PR C 1
H102 H 1.2268 0.6317 0.6301 0.172 Uiso 0.536(13) 1 calc PR C 1
H103 H 1.2599 0.7676 0.5975 0.172 Uiso 0.536(13) 1 calc PR C 1
O200 O 1.0416(5) 0.3424(11) 0.65146(19) 0.0687(18) Uani 0.786(12) 1 d PDU D 1
H200 H 1.0666 0.4050 0.6694 0.103 Uiso 0.786(12) 1 calc PR D 1
C200 C 1.1219(7) 0.3182(14) 0.6232(3) 0.067(2) Uani 0.786(12) 1 d PDU D 1
H201 H 1.1361 0.1967 0.6201 0.101 Uiso 0.786(12) 1 calc PR D 1
H202 H 1.1900 0.3754 0.6315 0.101 Uiso 0.786(12) 1 calc PR D 1
H203 H 1.0963 0.3655 0.5981 0.101 Uiso 0.786(12) 1 calc PR D 1
O110 O 1.1559(13) 1.0051(13) 0.6318(5) 0.106(3) Uani 0.464(13) 1 d PDU C 2
H110 H 1.1175 1.0211 0.6115 0.158 Uiso 0.464(13) 1 calc PR C 2
C110 C 1.175(3) 0.8327(17) 0.6364(10) 0.093(3) Uani 0.464(13) 1 d PDU C 2
H111 H 1.1704 0.8027 0.6642 0.140 Uiso 0.464(13) 1 calc PR C 2
H112 H 1.2493 0.8054 0.6269 0.140 Uiso 0.464(13) 1 calc PR C 2
H113 H 1.1205 0.7683 0.6213 0.140 Uiso 0.464(13) 1 calc PR C 2
O210 O 1.0181(19) 0.419(5) 0.6511(5) 0.075(4) Uani 0.214(12) 1 d PDU D 2
H210 H 1.0576 0.4546 0.6697 0.113 Uiso 0.214(12) 1 calc PR D 2
C210 C 1.0775(10) 0.4248(12) 0.6165(4) 0.071(3) Uani 0.214(12) 1 d PDU D 2
H211 H 1.1394 0.3454 0.6182 0.107 Uiso 0.214(12) 1 calc PR D 2
H212 H 1.1056 0.5399 0.6125 0.107 Uiso 0.214(12) 1 calc PR D 2
H213 H 1.0295 0.3932 0.5944 0.107 Uiso 0.214(12) 1 calc PR D 2
O300 O 0.6539(10) 0.6554(12) 0.8679(4) 0.083(3) Uani 0.458(10) 1 d PRDU E 1
H300 H 0.6114 0.6269 0.8860 0.125 Uiso 0.458(10) 1 calc PR E 1
C300 C 0.6922(16) 0.8281(16) 0.8746(6) 0.086(4) Uani 0.458(10) 1 d PDU E 1
H301 H 0.6296 0.9062 0.8727 0.129 Uiso 0.458(10) 1 calc PR E 1
H302 H 0.7468 0.8578 0.8548 0.129 Uiso 0.458(10) 1 calc PR E 1
H303 H 0.7258 0.8363 0.9008 0.129 Uiso 0.458(10) 1 calc PR E 1
O400 O 0.5473(8) 0.256(2) 0.8479(4) 0.085(3) Uani 0.458(10) 1 d PDU E 1
H400 H 0.5692 0.1793 0.8328 0.127 Uiso 0.458(10) 1 calc PR E 1
C400 C 0.6385(13) 0.311(3) 0.8731(5) 0.080(3) Uani 0.458(10) 1 d PDU E 1
H401 H 0.6697 0.4159 0.8627 0.120 Uiso 0.458(10) 1 calc PR E 1
H402 H 0.6953 0.2228 0.8738 0.120 Uiso 0.458(10) 1 calc PR E 1
H403 H 0.6115 0.3309 0.8997 0.120 Uiso 0.458(10) 1 calc PR E 1
O310 O 0.6615(10) 0.5418(11) 0.8681(4) 0.088(3) Uani 0.542(10) 1 d PDU E 2
H310 H 0.6164 0.5351 0.8866 0.133 Uiso 0.542(10) 1 calc PR E 2
C310 C 0.6797(15) 0.7199(15) 0.8583(5) 0.079(3) Uani 0.542(10) 1 d PDU E 2
H311 H 0.6531 0.7916 0.8797 0.119 Uiso 0.542(10) 1 calc PR E 2
H312 H 0.6396 0.7477 0.8341 0.119 Uiso 0.542(10) 1 calc PR E 2
H313 H 0.7586 0.7397 0.8546 0.119 Uiso 0.542(10) 1 calc PR E 2
O410 O 0.5252(10) 0.200(2) 0.8500(4) 0.088(3) Uani 0.542(10) 1 d PDU E 2
H410 H 0.5463 0.1221 0.8350 0.132 Uiso 0.542(10) 1 calc PR E 2
C410 C 0.6072(13) 0.226(3) 0.8810(4) 0.082(3) Uani 0.542(10) 1 d PDU E 2
H411 H 0.6464 0.3323 0.8764 0.122 Uiso 0.542(10) 1 calc PR E 2
H412 H 0.6598 0.1316 0.8810 0.122 Uiso 0.542(10) 1 calc PR E 2
H413 H 0.5705 0.2308 0.9064 0.122 Uiso 0.542(10) 1 calc PR E 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0204(12) 0.0249(14) 0.0282(14) 0.0016(11) -0.0054(10) -0.0036(11)
O2 0.0259(13) 0.0360(17) 0.0214(13) -0.0020(12) -0.0064(10) -0.0005(13)
O3 0.0179(12) 0.0415(19) 0.0315(15) -0.0031(13) -0.0041(10) 0.0003(13)
O4 0.0274(14) 0.071(3) 0.0244(14) -0.0139(17) 0.0013(11) 0.0039(17)
N1 0.0196(13) 0.0258(17) 0.0186(14) -0.0008(12) -0.0016(11) 0.0027(13)
N2 0.0283(16) 0.0302(18) 0.0189(14) -0.0032(13) -0.0017(12) 0.0098(14)
C1 0.0236(16) 0.0223(19) 0.0226(17) -0.0019(14) -0.0022(13) 0.0015(15)
C2 0.0216(16) 0.030(2) 0.0226(17) -0.0001(16) -0.0063(13) 0.0023(16)
C3 0.0165(15) 0.028(2) 0.0288(18) -0.0008(16) -0.0032(13) 0.0056(15)
C4 0.0184(15) 0.026(2) 0.0261(18) -0.0009(15) 0.0006(13) 0.0090(15)
C5 0.0173(15) 0.0255(19) 0.0219(17) -0.0014(14) -0.0024(12) 0.0038(15)
C6 0.0171(15) 0.0271(19) 0.0220(17) -0.0023(15) -0.0011(13) 0.0056(15)
C7 0.0167(15) 0.0245(19) 0.0194(16) -0.0014(14) -0.0027(12) 0.0046(14)
C8 0.0179(14) 0.0223(18) 0.0172(15) -0.0006(13) -0.0021(12) 0.0003(14)
C9 0.0196(16) 0.029(2) 0.0261(18) -0.0026(16) -0.0005(13) 0.0025(16)
C10 0.0164(15) 0.027(2) 0.0292(18) -0.0007(16) 0.0014(13) 0.0039(15)
C11 0.0181(15) 0.0195(17) 0.0246(17) -0.0016(14) 0.0019(13) 0.0010(14)
C12 0.0205(16) 0.027(2) 0.0313(19) 0.0053(17) -0.0069(14) 0.0012(16)
C13 0.0264(17) 0.027(2) 0.0233(17) 0.0032(15) -0.0072(14) 0.0040(16)
C14 0.0240(16) 0.0218(18) 0.0211(16) 0.0015(14) -0.0014(13) 0.0059(15)
C15 0.0276(18) 0.030(2) 0.0201(17) -0.0015(15) -0.0008(14) 0.0028(17)
C16 0.040(2) 0.030(2) 0.0224(19) -0.0067(16) -0.0018(17) 0.0130(19)
C17 0.0298(19) 0.027(2) 0.0227(18) -0.0030(15) -0.0023(15) 0.0116(17)
C18 0.0181(15) 0.0161(16) 0.0229(16) -0.0014(14) -0.0008(12) -0.0001(13)
C19 0.0175(15) 0.0193(17) 0.0270(18) 0.0014(14) -0.0021(13) 0.0006(14)
C20 0.0179(15) 0.0202(18) 0.0288(19) 0.0020(15) 0.0039(14) 0.0018(14)
C21 0.0184(15) 0.0244(19) 0.0211(16) -0.0008(14) -0.0014(12) 0.0040(15)
C22 0.0311(19) 0.033(2) 0.0236(18) -0.0022(17) -0.0035(15) 0.0008(18)
C23 0.0202(18) 0.062(3) 0.036(2) 0.004(2) -0.0016(16) 0.000(2)
O1A 0.0239(13) 0.0318(16) 0.0271(14) 0.0080(12) 0.0066(10) 0.0040(13)
O2A 0.0293(14) 0.0306(16) 0.0245(13) -0.0045(12) 0.0086(11) -0.0002(13)
O3A 0.0211(12) 0.0378(18) 0.0301(14) -0.0040(13) 0.0066(11) 0.0008(13)
O4A 0.0296(15) 0.061(2) 0.0272(15) -0.0059(16) -0.0011(12) -0.0092(16)
N1A 0.0174(13) 0.0261(17) 0.0227(15) -0.0042(13) 0.0022(11) -0.0005(13)
N2A 0.0228(15) 0.040(2) 0.0231(16) -0.0040(15) 0.0020(12) 0.0031(16)
C1A 0.0258(17) 0.0214(18) 0.0224(17) -0.0024(15) 0.0039(13) -0.0042(15)
C2A 0.0262(17) 0.0168(17) 0.0227(17) -0.0051(13) 0.0097(13) -0.0056(14)
C3A 0.0214(16) 0.0218(18) 0.0274(18) -0.0014(15) 0.0067(14) 0.0006(15)
C4A 0.0180(15) 0.0220(18) 0.0237(17) -0.0021(14) 0.0006(13) -0.0037(14)
C5A 0.0193(15) 0.0208(17) 0.0228(17) -0.0015(14) 0.0044(13) 0.0017(14)
C6A 0.0193(15) 0.0202(18) 0.0244(17) 0.0000(14) 0.0015(13) -0.0039(14)
C7A 0.0175(15) 0.028(2) 0.0185(16) -0.0013(14) 0.0025(12) 0.0006(15)
C8A 0.0169(14) 0.0194(18) 0.0206(16) -0.0009(13) 0.0013(12) 0.0004(13)
C9A 0.0203(16) 0.025(2) 0.0298(19) 0.0020(16) 0.0009(14) 0.0012(16)
C10A 0.0155(15) 0.037(2) 0.032(2) 0.0044(18) -0.0015(14) -0.0009(16)
C11A 0.0180(15) 0.0196(18) 0.034(2) 0.0031(15) -0.0008(14) 0.0002(14)
C12A 0.0209(17) 0.040(3) 0.0297(19) 0.0061(18) 0.0062(14) 0.0030(18)
C13A 0.0280(19) 0.037(2) 0.0256(19) 0.0069(18) 0.0086(15) 0.0033(19)
C14A 0.0266(18) 0.033(2) 0.0228(17) 0.0063(16) 0.0038(14) 0.0027(17)
C15A 0.0289(19) 0.045(3) 0.0209(18) 0.0030(18) 0.0052(15) 0.000(2)
C16A 0.030(2) 0.034(2) 0.029(2) -0.0093(18) 0.0022(16) -0.0032(19)
C17A 0.0243(18) 0.032(2) 0.0241(18) -0.0063(16) 0.0034(14) -0.0021(17)
C18A 0.0189(15) 0.0179(17) 0.0254(17) 0.0010(14) 0.0021(13) 0.0041(14)
C19A 0.0225(17) 0.025(2) 0.0271(18) 0.0052(15) 0.0022(14) 0.0027(16)
C20A 0.0229(17) 0.025(2) 0.0277(19) 0.0014(16) 0.0000(15) 0.0063(15)
C21A 0.0213(16) 0.033(2) 0.0216(17) -0.0040(16) 0.0019(13) 0.0056(16)
C22A 0.041(2) 0.029(2) 0.0215(18) -0.0038(16) 0.0068(16) -0.0024(19)
C23A 0.0190(17) 0.053(3) 0.039(2) 0.004(2) 0.0029(16) 0.000(2)
O5 0.031(2) 0.051(3) 0.032(2) 0.005(2) 0.0035(16) 0.020(2)
O6 0.036(2) 0.108(5) 0.053(3) 0.035(3) 0.019(2) 0.047(3)
O51 0.038(6) 0.056(7) 0.035(6) -0.005(6) 0.006(5) 0.005(6)
O61 0.041(7) 0.046(8) 0.047(7) -0.010(6) 0.004(6) -0.021(6)
O8 0.0390(19) 0.037(2) 0.085(3) -0.027(2) -0.0222(19) 0.0069(17)
O9 0.0336(17) 0.042(2) 0.060(2) 0.0252(18) 0.0083(16) 0.0144(16)
N4 0.0304(17) 0.040(2) 0.0227(16) -0.0033(15) -0.0017(13) 0.0148(17)
C24 0.0238(18) 0.032(2) 0.032(2) -0.0048(18) 0.0010(15) -0.0036(17)
C25 0.0156(15) 0.022(2) 0.048(2) 0.0066(18) 0.0010(15) -0.0009(15)
C26 0.039(3) 0.095(5) 0.040(3) 0.019(3) 0.012(2) 0.028(3)
O7 0.0259(19) 0.017(2) 0.040(2) -0.002(2) -0.0097(16) 0.0012(19)
N3 0.0155(17) 0.0147(19) 0.037(2) 0.0019(17) 0.0000(16) -0.0009(15)
C27 0.018(2) 0.017(2) 0.025(2) 0.0019(17) 0.0019(17) 0.0050(17)
C28 0.0268(19) 0.028(2) 0.034(2) -0.0049(17) -0.0042(16) 0.0057(17)
C29 0.0267(18) 0.028(2) 0.0257(18) -0.0056(16) -0.0053(14) 0.0070(16)
C30 0.0277(18) 0.031(2) 0.0230(17) -0.0013(16) -0.0030(14) 0.0074(17)
C31 0.039(2) 0.033(2) 0.034(2) 0.0106(19) 0.0020(18) 0.016(2)
C32 0.037(3) 0.037(3) 0.060(3) 0.014(3) -0.003(2) 0.003(2)
C33 0.028(2) 0.036(3) 0.059(3) 0.003(2) -0.004(2) 0.009(2)
O71 0.030(6) 0.022(8) 0.039(7) 0.008(7) -0.005(6) 0.004(7)
N31 0.025(6) 0.016(6) 0.030(6) 0.005(5) -0.001(5) -0.006(5)
C271 0.017(7) 0.015(8) 0.025(8) -0.003(6) -0.006(6) 0.004(6)
O5A 0.0324(19) 0.130(5) 0.034(2) -0.029(3) -0.0088(15) 0.037(3)
O6A 0.0255(17) 0.073(3) 0.038(2) -0.023(2) -0.0080(15) 0.028(2)
O5B 0.045(7) 0.091(8) 0.044(7) -0.014(7) -0.001(6) 0.016(7)
O6B 0.100(15) 0.105(16) 0.102(16) -0.003(9) -0.002(9) 0.002(9)
O8A 0.0245(15) 0.046(2) 0.052(2) 0.0081(18) 0.0020(14) 0.0036(15)
O9A 0.0377(17) 0.060(2) 0.0360(17) -0.0195(17) -0.0088(14) 0.0267(18)
N4A 0.0264(16) 0.041(2) 0.0217(16) 0.0019(15) -0.0012(13) 0.0100(17)
C24A 0.0237(18) 0.029(2) 0.0280(19) 0.0017(17) 0.0035(15) 0.0069(17)
C25A 0.0150(15) 0.027(2) 0.0318(19) -0.0031(16) 0.0016(14) 0.0029(15)
C26A 0.029(2) 0.052(3) 0.027(2) -0.010(2) -0.0006(16) 0.005(2)
O7A 0.0212(14) 0.0112(17) 0.0365(17) -0.0043(14) 0.0068(12) -0.0025(14)
N3A 0.0102(13) 0.0201(18) 0.0283(17) -0.0013(14) 0.0041(12) 0.0005(13)
C27A 0.0138(16) 0.0129(18) 0.0222(18) -0.0011(14) 0.0025(13) -0.0002(14)
O7B 0.028(8) 0.016(9) 0.044(8) -0.007(8) 0.004(7) -0.004(8)
N3B 0.042(11) 0.040(11) 0.050(12) 0.006(8) 0.004(8) 0.000(8)
C27B 0.031(11) 0.027(11) 0.031(11) -0.002(8) 0.000(8) 0.006(8)
C28A 0.0221(18) 0.0154(17) 0.032(2) 0.0011(15) 0.0047(15) 0.0011(14)
C29A 0.0193(16) 0.026(2) 0.0216(17) 0.0027(14) 0.0027(13) -0.0003(15)
C30A 0.0255(17) 0.031(2) 0.0179(16) 0.0053(15) 0.0027(13) 0.0048(17)
C31A 0.043(2) 0.023(2) 0.045(3) 0.0020(19) 0.011(2) 0.010(2)
C32A 0.045(3) 0.020(2) 0.088(4) -0.003(3) 0.026(3) -0.006(2)
C33A 0.026(2) 0.025(2) 0.071(4) 0.000(2) 0.012(2) -0.0042(19)
O100 0.087(4) 0.099(5) 0.078(4) 0.013(4) -0.013(4) -0.016(4)
C100 0.114(6) 0.118(6) 0.111(6) 0.011(5) -0.008(5) -0.012(6)
O200 0.064(3) 0.071(4) 0.071(3) -0.008(3) 0.006(3) -0.028(3)
C200 0.073(4) 0.074(5) 0.054(4) -0.011(4) 0.013(3) -0.020(4)
O110 0.101(5) 0.121(6) 0.095(5) 0.009(5) -0.004(5) -0.006(5)
C110 0.091(5) 0.103(5) 0.085(5) 0.011(5) -0.008(5) -0.013(5)
O210 0.072(6) 0.077(6) 0.077(6) -0.008(6) 0.004(5) -0.012(6)
C210 0.073(5) 0.074(6) 0.067(5) -0.009(5) 0.008(5) -0.014(5)
O300 0.079(4) 0.090(5) 0.081(5) -0.005(5) 0.004(4) 0.006(5)
C300 0.082(6) 0.088(6) 0.087(6) 0.007(5) 0.006(5) 0.002(5)
O400 0.078(5) 0.087(5) 0.088(5) -0.011(4) 0.003(4) 0.013(4)
C400 0.082(6) 0.084(6) 0.074(6) -0.012(5) -0.003(5) 0.011(5)
O310 0.077(4) 0.107(6) 0.082(5) 0.004(5) 0.010(4) 0.016(5)
C310 0.072(5) 0.087(5) 0.079(5) 0.003(5) 0.010(4) 0.009(5)
O410 0.080(5) 0.089(6) 0.096(5) -0.018(5) 0.008(4) 0.006(5)
C410 0.080(5) 0.087(5) 0.077(5) -0.014(5) 0.004(4) 0.013(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.430(5) . ?
O1 C12 1.445(5) . ?
O2 C2 1.377(4) . ?
O2 C22 1.438(5) . ?
O3 C3 1.382(5) . ?
O3 C23 1.430(5) . ?
O4 C9 1.229(5) . ?
N1 C9 1.359(5) . ?
N1 C6 1.429(5) . ?
N1 C8 1.490(5) . ?
N2 C16 1.510(6) . ?
N2 C15 1.515(5) . ?
N2 C21 1.528(5) . ?
N2 H2A 0.9300 . ?
C1 C2 1.383(5) . ?
C1 C6 1.403(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.412(6) . ?
C3 C4 1.387(5) . ?
C4 C5 1.408(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(5) . ?
C5 C7 1.502(5) . ?
C7 C21 1.536(5) . ?
C7 C17 1.549(6) . ?
C7 C8 1.569(5) . ?
C8 C18 1.535(5) . ?
C8 H8A 1.0000 . ?
C9 C10 1.507(5) . ?
C10 C11 1.543(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.538(5) . ?
C11 H11A 1.0000 . ?
C12 C13 1.510(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.339(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.508(5) . ?
C14 C19 1.530(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.519(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.545(5) . ?
C18 H18A 1.0000 . ?
C19 C20 1.536(5) . ?
C19 H19A 1.0000 . ?
C20 C21 1.524(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1A C11A 1.426(5) . ?
O1A C12A 1.444(5) . ?
O2A C2A 1.374(4) . ?
O2A C22A 1.431(5) . ?
O3A C3A 1.376(5) . ?
O3A C23A 1.434(6) . ?
O4A C9A 1.232(5) . ?
N1A C9A 1.357(5) . ?
N1A C6A 1.424(5) . ?
N1A C8A 1.497(5) . ?
N2A C16A 1.488(7) . ?
N2A C15A 1.511(5) . ?
N2A C21A 1.536(5) . ?
N2A H2AA 0.9300 . ?
C1A C2A 1.393(5) . ?
C1A C6A 1.402(5) . ?
C1A H1AA 0.9500 . ?
C2A C3A 1.414(6) . ?
C3A C4A 1.384(5) . ?
C4A C5A 1.396(5) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.387(5) . ?
C5A C7A 1.509(5) . ?
C7A C21A 1.540(6) . ?
C7A C17A 1.545(6) . ?
C7A C8A 1.569(5) . ?
C8A C18A 1.522(5) . ?
C8A H8AA 1.0000 . ?
C9A C10A 1.522(5) . ?
C10A C11A 1.547(6) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C11A C18A 1.535(5) . ?
C11A H11B 1.0000 . ?
C12A C13A 1.508(6) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C13A C14A 1.331(6) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.495(6) . ?
C14A C19A 1.533(6) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A C17A 1.519(6) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.548(5) . ?
C18A H18B 1.0000 . ?
C19A C20A 1.532(5) . ?
C19A H19B 1.0000 . ?
C20A C21A 1.511(6) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C21A H21B 1.0000 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
O5 C24 1.252(7) . ?
O6 C24 1.263(6) . ?
O51 C24 1.15(2) . ?
O61 C24 1.300(18) . ?
O8 N4 1.239(6) . ?
O9 N4 1.204(5) . ?
N4 C30 1.472(5) . ?
C24 C25 1.545(6) . ?
C25 N31 1.375(17) . ?
C25 N3 1.424(6) . ?
C25 C26 1.548(7) . ?
C25 H251 1.0000 . ?
C25 H25 0.9599 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O7 C27 1.239(7) . ?
N3 C27 1.332(6) . ?
N3 H3 0.8800 . ?
C27 C28 1.533(7) . ?
C28 C33 1.385(7) . ?
C28 C29 1.392(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.373(6) . ?
C29 H29A 0.9500 . ?
C30 C31 1.378(7) . ?
C31 C32 1.383(7) . ?
C31 H31A 0.9500 . ?
C32 C33 1.422(8) . ?
C32 C271 1.83(2) 1_545 ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
O71 C271 1.16(3) . ?
N31 C271 1.39(2) . ?
N31 H25 0.4332 . ?
N31 H31 0.8800 . ?
C271 C32 1.827(19) 1_565 ?
O5A C24A 1.235(6) . ?
O6A C24A 1.236(5) . ?
O5B C24A 1.30(5) . ?
O6B C24A 1.12(7) . ?
O8A N4A 1.226(6) . ?
O9A N4A 1.220(6) . ?
N4A C30A 1.476(5) . ?
C24A C25A 1.547(6) . ?
C25A N3A 1.461(5) . ?
C25A N3B 1.47(4) . ?
C25A C26A 1.535(6) . ?
C25A H25B 1.0000 . ?
C25A H25A 0.9601 . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?
O7A C27A 1.229(6) . ?
N3A C27A 1.343(5) . ?
N3A H3A 0.8800 . ?
C27A C28A 1.519(6) . ?
O7B C27B 1.10(5) . ?
N3B C27B 1.35(6) . ?
N3B H25A 0.5356 . ?
N3B H3B 0.8800 . ?
C27B C32A 1.78(4) 1_565 ?
C28A C29A 1.388(5) . ?
C28A C33A 1.395(6) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.385(6) . ?
C29A H29B 0.9500 . ?
C30A C31A 1.369(7) . ?
C31A C32A 1.386(7) . ?
C31A H31B 0.9500 . ?
C32A C33A 1.381(8) . ?
C32A C27B 1.78(4) 1_545 ?
C32A H32C 0.9500 . ?
C33A H33B 0.9500 . ?
O100 C100 1.389(9) . ?
O100 H100 0.8400 . ?
C100 H101 0.9800 . ?
C100 H102 0.9800 . ?
C100 H103 0.9800 . ?
O200 C200 1.392(8) . ?
O200 H200 0.8400 . ?
C200 H201 0.9800 . ?
C200 H202 0.9800 . ?
C200 H203 0.9800 . ?
O110 C110 1.390(9) . ?
O110 H110 0.8400 . ?
C110 H111 0.9800 . ?
C110 H112 0.9800 . ?
C110 H113 0.9800 . ?
O210 C210 1.390(9) . ?
O210 H210 0.8400 . ?
C210 H211 0.9800 . ?
C210 H212 0.9800 . ?
C210 H213 0.9800 . ?
O300 C300 1.457(10) . ?
O300 H300 0.8400 . ?
C300 H301 0.9800 . ?
C300 H302 0.9800 . ?
C300 H303 0.9800 . ?
O400 C400 1.459(10) . ?
O400 H400 0.8400 . ?
C400 H401 0.9800 . ?
C400 H402 0.9800 . ?
C400 H403 0.9800 . ?
O310 C310 1.462(10) . ?
O310 H310 0.8400 . ?
C310 H311 0.9800 . ?
C310 H312 0.9800 . ?
C310 H313 0.9800 . ?
O410 C410 1.458(10) . ?
O410 H410 0.8400 . ?
C410 H411 0.9800 . ?
C410 H412 0.9800 . ?
C410 H413 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 115.1(3) . . ?
C2 O2 C22 115.7(3) . . ?
C3 O3 C23 115.8(3) . . ?
C9 N1 C6 124.8(3) . . ?
C9 N1 C8 119.4(3) . . ?
C6 N1 C8 109.1(3) . . ?
C16 N2 C15 112.0(4) . . ?
C16 N2 C21 107.6(3) . . ?
C15 N2 C21 113.3(3) . . ?
C16 N2 H2A 107.9 . . ?
C15 N2 H2A 107.9 . . ?
C21 N2 H2A 107.9 . . ?
C2 C1 C6 117.2(4) . . ?
C2 C1 H1A 121.4 . . ?
C6 C1 H1A 121.4 . . ?
O2 C2 C1 123.3(4) . . ?
O2 C2 C3 115.4(3) . . ?
C1 C2 C3 121.3(3) . . ?
O3 C3 C4 124.3(4) . . ?
O3 C3 C2 115.2(3) . . ?
C4 C3 C2 120.5(3) . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 C7 111.4(3) . . ?
C4 C5 C7 128.7(3) . . ?
C5 C6 C1 122.4(3) . . ?
C5 C6 N1 109.8(3) . . ?
C1 C6 N1 127.9(3) . . ?
C5 C7 C21 115.9(3) . . ?
C5 C7 C17 111.7(3) . . ?
C21 C7 C17 101.8(3) . . ?
C5 C7 C8 102.1(3) . . ?
C21 C7 C8 114.9(3) . . ?
C17 C7 C8 110.8(3) . . ?
N1 C8 C18 106.0(3) . . ?
N1 C8 C7 104.5(3) . . ?
C18 C8 C7 115.8(3) . . ?
N1 C8 H8A 110.1 . . ?
C18 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
O4 C9 N1 122.4(4) . . ?
O4 C9 C10 121.4(4) . . ?
N1 C9 C10 116.2(3) . . ?
C9 C10 C11 118.4(3) . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
O1 C11 C18 114.9(3) . . ?
O1 C11 C10 105.4(3) . . ?
C18 C11 C10 109.7(3) . . ?
O1 C11 H11A 108.9 . . ?
C18 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
O1 C12 C13 111.6(3) . . ?
O1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 121.8(4) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C15 121.3(4) . . ?
C13 C14 C19 123.0(4) . . ?
C15 C14 C19 115.7(3) . . ?
C14 C15 N2 110.3(3) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 104.6(4) . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 102.8(3) . . ?
C16 C17 H17A 111.2 . . ?
C7 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C7 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C8 C18 C11 107.2(3) . . ?
C8 C18 C19 112.4(3) . . ?
C11 C18 C19 118.0(3) . . ?
C8 C18 H18A 106.2 . . ?
C11 C18 H18A 106.2 . . ?
C19 C18 H18A 106.2 . . ?
C14 C19 C20 109.3(3) . . ?
C14 C19 C18 114.3(3) . . ?
C20 C19 C18 106.6(3) . . ?
C14 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C21 C20 C19 108.2(3) . . ?
C21 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 N2 111.3(3) . . ?
C20 C21 C7 115.3(3) . . ?
N2 C21 C7 105.0(3) . . ?
C20 C21 H21A 108.3 . . ?
N2 C21 H21A 108.3 . . ?
C7 C21 H21A 108.3 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11A O1A C12A 114.7(3) . . ?
C2A O2A C22A 115.9(3) . . ?
C3A O3A C23A 115.8(3) . . ?
C9A N1A C6A 124.9(3) . . ?
C9A N1A C8A 119.2(3) . . ?
C6A N1A C8A 109.3(3) . . ?
C16A N2A C15A 112.9(4) . . ?
C16A N2A C21A 107.8(3) . . ?
C15A N2A C21A 113.2(4) . . ?
C16A N2A H2AA 107.6 . . ?
C15A N2A H2AA 107.6 . . ?
C21A N2A H2AA 107.6 . . ?
C2A C1A C6A 116.9(4) . . ?
C2A C1A H1AA 121.5 . . ?
C6A C1A H1AA 121.5 . . ?
O2A C2A C1A 123.1(4) . . ?
O2A C2A C3A 115.5(3) . . ?
C1A C2A C3A 121.4(3) . . ?
O3A C3A C4A 124.7(4) . . ?
O3A C3A C2A 115.1(3) . . ?
C4A C3A C2A 120.2(3) . . ?
C3A C4A C5A 118.8(3) . . ?
C3A C4A H4AA 120.6 . . ?
C5A C4A H4AA 120.6 . . ?
C6A C5A C4A 120.4(3) . . ?
C6A C5A C7A 110.7(3) . . ?
C4A C5A C7A 128.7(3) . . ?
C5A C6A C1A 122.0(3) . . ?
C5A C6A N1A 110.1(3) . . ?
C1A C6A N1A 127.9(3) . . ?
C5A C7A C21A 115.0(3) . . ?
C5A C7A C17A 111.7(3) . . ?
C21A C7A C17A 102.2(3) . . ?
C5A C7A C8A 102.4(3) . . ?
C21A C7A C8A 114.6(3) . . ?
C17A C7A C8A 111.2(3) . . ?
N1A C8A C18A 106.6(3) . . ?
N1A C8A C7A 104.1(3) . . ?
C18A C8A C7A 116.3(3) . . ?
N1A C8A H8AA 109.9 . . ?
C18A C8A H8AA 109.9 . . ?
C7A C8A H8AA 109.9 . . ?
O4A C9A N1A 122.1(4) . . ?
O4A C9A C10A 121.6(4) . . ?
N1A C9A C10A 116.3(4) . . ?
C9A C10A C11A 118.0(3) . . ?
C9A C10A H10C 107.8 . . ?
C11A C10A H10C 107.8 . . ?
C9A C10A H10D 107.8 . . ?
C11A C10A H10D 107.8 . . ?
H10C C10A H10D 107.1 . . ?
O1A C11A C18A 114.2(3) . . ?
O1A C11A C10A 105.0(3) . . ?
C18A C11A C10A 109.7(3) . . ?
O1A C11A H11B 109.3 . . ?
C18A C11A H11B 109.3 . . ?
C10A C11A H11B 109.3 . . ?
O1A C12A C13A 111.4(3) . . ?
O1A C12A H12C 109.3 . . ?
C13A C12A H12C 109.3 . . ?
O1A C12A H12D 109.3 . . ?
C13A C12A H12D 109.3 . . ?
H12C C12A H12D 108.0 . . ?
C14A C13A C12A 122.3(4) . . ?
C14A C13A H13B 118.8 . . ?
C12A C13A H13B 118.8 . . ?
C13A C14A C15A 122.3(4) . . ?
C13A C14A C19A 122.2(4) . . ?
C15A C14A C19A 115.5(4) . . ?
C14A C15A N2A 110.8(3) . . ?
C14A C15A H15C 109.5 . . ?
N2A C15A H15C 109.5 . . ?
C14A C15A H15D 109.5 . . ?
N2A C15A H15D 109.5 . . ?
H15C C15A H15D 108.1 . . ?
N2A C16A C17A 106.0(4) . . ?
N2A C16A H16C 110.5 . . ?
C17A C16A H16C 110.5 . . ?
N2A C16A H16D 110.5 . . ?
C17A C16A H16D 110.5 . . ?
H16C C16A H16D 108.7 . . ?
C16A C17A C7A 103.0(4) . . ?
C16A C17A H17C 111.2 . . ?
C7A C17A H17C 111.2 . . ?
C16A C17A H17D 111.2 . . ?
C7A C17A H17D 111.2 . . ?
H17C C17A H17D 109.1 . . ?
C8A C18A C11A 108.1(3) . . ?
C8A C18A C19A 112.9(3) . . ?
C11A C18A C19A 117.9(3) . . ?
C8A C18A H18B 105.6 . . ?
C11A C18A H18B 105.6 . . ?
C19A C18A H18B 105.6 . . ?
C20A C19A C14A 109.3(3) . . ?
C20A C19A C18A 106.0(3) . . ?
C14A C19A C18A 113.6(3) . . ?
C20A C19A H19B 109.3 . . ?
C14A C19A H19B 109.3 . . ?
C18A C19A H19B 109.3 . . ?
C21A C20A C19A 109.2(3) . . ?
C21A C20A H20C 109.8 . . ?
C19A C20A H20C 109.8 . . ?
C21A C20A H20D 109.8 . . ?
C19A C20A H20D 109.8 . . ?
H20C C20A H20D 108.3 . . ?
C20A C21A N2A 110.9(3) . . ?
C20A C21A C7A 115.3(3) . . ?
N2A C21A C7A 104.6(3) . . ?
C20A C21A H21B 108.6 . . ?
N2A C21A H21B 108.6 . . ?
C7A C21A H21B 108.6 . . ?
O2A C22A H22D 109.5 . . ?
O2A C22A H22E 109.5 . . ?
H22D C22A H22E 109.5 . . ?
O2A C22A H22F 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
O3A C23A H23D 109.5 . . ?
O3A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
O3A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O9 N4 O8 123.0(4) . . ?
O9 N4 C30 119.1(4) . . ?
O8 N4 C30 117.8(4) . . ?
O51 C24 O5 37.9(12) . . ?
O51 C24 O6 108.7(12) . . ?
O5 C24 O6 122.3(4) . . ?
O51 C24 O61 123.7(15) . . ?
O5 C24 O61 93.8(10) . . ?
O6 C24 O61 68.2(10) . . ?
O51 C24 C25 117.4(10) . . ?
O5 C24 C25 120.4(4) . . ?
O6 C24 C25 117.1(4) . . ?
O61 C24 C25 111.9(9) . . ?
N31 C25 N3 112.1(8) . . ?
N31 C25 C24 110.2(8) . . ?
N3 C25 C24 110.4(4) . . ?
N31 C25 C26 103.2(8) . . ?
N3 C25 C26 109.5(5) . . ?
C24 C25 C26 111.2(4) . . ?
N31 C25 H251 110.7 . . ?
N3 C25 H251 1.6 . . ?
C24 C25 H251 110.7 . . ?
C26 C25 H251 110.7 . . ?
N31 C25 H25 6.1 . . ?
N3 C25 H25 107.9 . . ?
C24 C25 H25 108.6 . . ?
C26 C25 H25 109.1 . . ?
H251 C25 H25 106.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C27 N3 C25 123.8(4) . . ?
C27 N3 H3 118.1 . . ?
C25 N3 H3 118.1 . . ?
O7 C27 N3 124.8(5) . . ?
O7 C27 C28 120.2(5) . . ?
N3 C27 C28 115.0(4) . . ?
C33 C28 C29 118.9(4) . . ?
C33 C28 C27 124.4(4) . . ?
C29 C28 C27 116.5(4) . . ?
C33 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 4.9 . . ?
C30 C29 C28 118.6(4) . . ?
C30 C29 H29A 120.7 . . ?
C28 C29 H29A 120.7 . . ?
C29 C30 C31 123.8(4) . . ?
C29 C30 N4 117.5(4) . . ?
C31 C30 N4 118.6(4) . . ?
C30 C31 C32 118.6(5) . . ?
C30 C31 H31A 120.7 . . ?
C32 C31 H31A 120.7 . . ?
C31 C32 C33 118.5(5) . . ?
C31 C32 C271 110.7(7) . 1_545 ?
C33 C32 C271 129.8(7) . 1_545 ?
C31 C32 H32A 120.8 . . ?
C33 C32 H32A 120.8 . . ?
C271 C32 H32A 13.8 1_545 . ?
C28 C33 C32 121.6(4) . . ?
C28 C33 H33A 119.2 . . ?
C32 C33 H33A 119.2 . . ?
C25 N31 C271 125.1(15) . . ?
C25 N31 H25 13.7 . . ?
C271 N31 H25 113.6 . . ?
C25 N31 H31 117.5 . . ?
C271 N31 H31 117.5 . . ?
H25 N31 H31 128.3 . . ?
O71 C271 N31 122(2) . . ?
O71 C271 C32 123.7(17) . 1_565 ?
N31 C271 C32 113.9(13) . 1_565 ?
O9A N4A O8A 123.7(4) . . ?
O9A N4A C30A 118.5(4) . . ?
O8A N4A C30A 117.8(4) . . ?
O6B C24A O5A 93(3) . . ?
O6B C24A O6A 56(4) . . ?
O5A C24A O6A 123.3(4) . . ?
O6B C24A O5B 104(4) . . ?
O5A C24A O5B 36(2) . . ?
O6A C24A O5B 101(2) . . ?
O6B C24A C25A 124(3) . . ?
O5A C24A C25A 118.0(4) . . ?
O6A C24A C25A 118.7(4) . . ?
O5B C24A C25A 129(2) . . ?
N3A C25A N3B 111.9(17) . . ?
N3A C25A C26A 109.2(4) . . ?
N3B C25A C26A 112.1(17) . . ?
N3A C25A C24A 110.6(3) . . ?
N3B C25A C24A 100.6(17) . . ?
C26A C25A C24A 112.2(3) . . ?
N3A C25A H25B 1.5 . . ?
N3B C25A H25B 110.5 . . ?
C26A C25A H25B 110.5 . . ?
C24A C25A H25B 110.5 . . ?
N3A C25A H25A 108.0 . . ?
N3B C25A H25A 7.6 . . ?
C26A C25A H25A 108.6 . . ?
C24A C25A H25A 108.1 . . ?
H25B C25A H25A 106.7 . . ?
C25A C26A H26D 109.5 . . ?
C25A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C25A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C27A N3A C25A 123.0(4) . . ?
C27A N3A H3A 118.5 . . ?
C25A N3A H3A 118.5 . . ?
O7A C27A N3A 124.3(4) . . ?
O7A C27A C28A 120.4(3) . . ?
N3A C27A C28A 115.2(4) . . ?
C27B N3B C25A 124(4) . . ?
C27B N3B H25A 115.6 . . ?
C25A N3B H25A 13.6 . . ?
C27B N3B H3B 118.0 . . ?
C25A N3B H3B 118.0 . . ?
H25A N3B H3B 125.2 . . ?
O7B C27B N3B 125(4) . . ?
O7B C27B C32A 128(4) . 1_565 ?
N3B C27B C32A 106(3) . 1_565 ?
C29A C28A C33A 118.9(4) . . ?
C29A C28A C27A 117.2(4) . . ?
C33A C28A C27A 123.9(4) . . ?
C29A C28A H28A 120.5 . . ?
C33A C28A H28A 120.5 . . ?
C27A C28A H28A 3.3 . . ?
C30A C29A C28A 118.6(4) . . ?
C30A C29A H29B 120.7 . . ?
C28A C29A H29B 120.7 . . ?
C31A C30A C29A 123.4(4) . . ?
C31A C30A N4A 117.8(4) . . ?
C29A C30A N4A 118.7(4) . . ?
C30A C31A C32A 117.5(4) . . ?
C30A C31A H31B 121.3 . . ?
C32A C31A H31B 121.3 . . ?
C33A C32A C31A 120.8(5) . . ?
C33A C32A C27B 134.8(14) . 1_545 ?
C31A C32A C27B 102.5(14) . 1_545 ?
C33A C32A H32C 119.6 . . ?
C31A C32A H32C 119.6 . . ?
C27B C32A H32C 21.1 1_545 . ?
C32A C33A C28A 120.8(4) . . ?
C32A C33A H33B 119.6 . . ?
C28A C33A H33B 119.6 . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H101 109.5 . . ?
O100 C100 H102 109.5 . . ?
H101 C100 H102 109.5 . . ?
O100 C100 H103 109.5 . . ?
H101 C100 H103 109.5 . . ?
H102 C100 H103 109.5 . . ?
C200 O200 H200 109.5 . . ?
O200 C200 H201 109.5 . . ?
O200 C200 H202 109.5 . . ?
H201 C200 H202 109.5 . . ?
O200 C200 H203 109.5 . . ?
H201 C200 H203 109.5 . . ?
H202 C200 H203 109.5 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H111 109.5 . . ?
O110 C110 H112 109.5 . . ?
H111 C110 H112 109.5 . . ?
O110 C110 H113 109.5 . . ?
H111 C110 H113 109.5 . . ?
H112 C110 H113 109.5 . . ?
C210 O210 H210 109.5 . . ?
O210 C210 H211 109.5 . . ?
O210 C210 H212 109.5 . . ?
H211 C210 H212 109.5 . . ?
O210 C210 H213 109.5 . . ?
H211 C210 H213 109.5 . . ?
H212 C210 H213 109.5 . . ?
C300 O300 H300 109.5 . . ?
O300 C300 H301 109.5 . . ?
O300 C300 H302 109.5 . . ?
H301 C300 H302 109.5 . . ?
O300 C300 H303 109.5 . . ?
H301 C300 H303 109.5 . . ?
H302 C300 H303 109.5 . . ?
C400 O400 H400 109.5 . . ?
O400 C400 H401 109.5 . . ?
O400 C400 H402 109.5 . . ?
H401 C400 H402 109.5 . . ?
O400 C400 H403 109.5 . . ?
H401 C400 H403 109.5 . . ?
H402 C400 H403 109.5 . . ?
C310 O310 H310 109.5 . . ?
O310 C310 H311 109.5 . . ?
O310 C310 H312 109.5 . . ?
H311 C310 H312 109.5 . . ?
O310 C310 H313 109.5 . . ?
H311 C310 H313 109.5 . . ?
H312 C310 H313 109.5 . . ?
C410 O410 H410 109.5 . . ?
O410 C410 H411 109.5 . . ?
O410 C410 H412 109.5 . . ?
H411 C410 H412 109.5 . . ?
O410 C410 H413 109.5 . . ?
H411 C410 H413 109.5 . . ?
H412 C410 H413 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 4.0(6) . . . . ?
C22 O2 C2 C3 -175.4(4) . . . . ?
C6 C1 C2 O2 -179.0(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C23 O3 C3 C4 4.9(7) . . . . ?
C23 O3 C3 C2 -174.5(4) . . . . ?
O2 C2 C3 O3 -4.3(6) . . . . ?
C1 C2 C3 O3 176.3(4) . . . . ?
O2 C2 C3 C4 176.2(4) . . . . ?
C1 C2 C3 C4 -3.2(7) . . . . ?
O3 C3 C4 C5 -177.4(4) . . . . ?
C2 C3 C4 C5 2.1(6) . . . . ?
C3 C4 C5 C6 1.8(6) . . . . ?
C3 C4 C5 C7 -175.5(4) . . . . ?
C4 C5 C6 C1 -4.7(7) . . . . ?
C7 C5 C6 C1 173.0(4) . . . . ?
C4 C5 C6 N1 175.5(4) . . . . ?
C7 C5 C6 N1 -6.7(5) . . . . ?
C2 C1 C6 C5 3.6(6) . . . . ?
C2 C1 C6 N1 -176.7(4) . . . . ?
C9 N1 C6 C5 -156.4(4) . . . . ?
C8 N1 C6 C5 -5.5(5) . . . . ?
C9 N1 C6 C1 23.9(7) . . . . ?
C8 N1 C6 C1 174.8(4) . . . . ?
C6 C5 C7 C21 140.8(4) . . . . ?
C4 C5 C7 C21 -41.7(6) . . . . ?
C6 C5 C7 C17 -103.2(4) . . . . ?
C4 C5 C7 C17 74.3(5) . . . . ?
C6 C5 C7 C8 15.2(4) . . . . ?
C4 C5 C7 C8 -167.3(4) . . . . ?
C9 N1 C8 C18 44.4(5) . . . . ?
C6 N1 C8 C18 -108.3(3) . . . . ?
C9 N1 C8 C7 167.3(4) . . . . ?
C6 N1 C8 C7 14.6(4) . . . . ?
C5 C7 C8 N1 -17.3(4) . . . . ?
C21 C7 C8 N1 -143.6(3) . . . . ?
C17 C7 C8 N1 101.7(3) . . . . ?
C5 C7 C8 C18 98.9(4) . . . . ?
C21 C7 C8 C18 -27.3(5) . . . . ?
C17 C7 C8 C18 -142.0(3) . . . . ?
C6 N1 C9 O4 -23.0(7) . . . . ?
C8 N1 C9 O4 -171.1(4) . . . . ?
C6 N1 C9 C10 155.2(4) . . . . ?
C8 N1 C9 C10 7.1(6) . . . . ?
O4 C9 C10 C11 144.7(5) . . . . ?
N1 C9 C10 C11 -33.5(6) . . . . ?
C12 O1 C11 C18 -67.2(4) . . . . ?
C12 O1 C11 C10 171.9(3) . . . . ?
C9 C10 C11 O1 128.3(4) . . . . ?
C9 C10 C11 C18 4.1(5) . . . . ?
C11 O1 C12 C13 87.9(4) . . . . ?
O1 C12 C13 C14 -64.2(5) . . . . ?
C12 C13 C14 C15 177.0(4) . . . . ?
C12 C13 C14 C19 -2.9(6) . . . . ?
C13 C14 C15 N2 -127.4(4) . . . . ?
C19 C14 C15 N2 52.6(5) . . . . ?
C16 N2 C15 C14 77.0(4) . . . . ?
C21 N2 C15 C14 -45.0(5) . . . . ?
C15 N2 C16 C17 -142.0(3) . . . . ?
C21 N2 C16 C17 -16.8(4) . . . . ?
N2 C16 C17 C7 36.8(4) . . . . ?
C5 C7 C17 C16 -166.8(3) . . . . ?
C21 C7 C17 C16 -42.6(4) . . . . ?
C8 C7 C17 C16 80.1(4) . . . . ?
N1 C8 C18 C11 -71.7(3) . . . . ?
C7 C8 C18 C11 173.0(3) . . . . ?
N1 C8 C18 C19 157.1(3) . . . . ?
C7 C8 C18 C19 41.8(4) . . . . ?
O1 C11 C18 C8 -72.1(4) . . . . ?
C10 C11 C18 C8 46.4(4) . . . . ?
O1 C11 C18 C19 55.9(5) . . . . ?
C10 C11 C18 C19 174.4(3) . . . . ?
C13 C14 C19 C20 178.4(4) . . . . ?
C15 C14 C19 C20 -1.5(5) . . . . ?
C13 C14 C19 C18 59.1(5) . . . . ?
C15 C14 C19 C18 -120.8(4) . . . . ?
C8 C18 C19 C14 58.7(4) . . . . ?
C11 C18 C19 C14 -66.9(4) . . . . ?
C8 C18 C19 C20 -62.2(4) . . . . ?
C11 C18 C19 C20 172.3(3) . . . . ?
C14 C19 C20 C21 -55.3(4) . . . . ?
C18 C19 C20 C21 68.6(4) . . . . ?
C19 C20 C21 N2 62.9(4) . . . . ?
C19 C20 C21 C7 -56.5(4) . . . . ?
C16 N2 C21 C20 -135.4(3) . . . . ?
C15 N2 C21 C20 -11.0(4) . . . . ?
C16 N2 C21 C7 -10.0(4) . . . . ?
C15 N2 C21 C7 114.4(3) . . . . ?
C5 C7 C21 C20 -83.7(4) . . . . ?
C17 C7 C21 C20 154.9(3) . . . . ?
C8 C7 C21 C20 35.1(5) . . . . ?
C5 C7 C21 N2 153.5(3) . . . . ?
C17 C7 C21 N2 32.1(4) . . . . ?
C8 C7 C21 N2 -87.7(4) . . . . ?
C22A O2A C2A C1A 3.2(6) . . . . ?
C22A O2A C2A C3A -177.4(4) . . . . ?
C6A C1A C2A O2A -178.9(4) . . . . ?
C6A C1A C2A C3A 1.7(6) . . . . ?
C23A O3A C3A C4A 6.2(6) . . . . ?
C23A O3A C3A C2A -175.2(4) . . . . ?
O2A C2A C3A O3A -2.8(5) . . . . ?
C1A C2A C3A O3A 176.7(4) . . . . ?
O2A C2A C3A C4A 175.9(4) . . . . ?
C1A C2A C3A C4A -4.7(6) . . . . ?
O3A C3A C4A C5A -177.9(4) . . . . ?
C2A C3A C4A C5A 3.5(6) . . . . ?
C3A C4A C5A C6A 0.5(6) . . . . ?
C3A C4A C5A C7A -175.2(4) . . . . ?
C4A C5A C6A C1A -3.6(6) . . . . ?
C7A C5A C6A C1A 172.8(4) . . . . ?
C4A C5A C6A N1A 175.5(4) . . . . ?
C7A C5A C6A N1A -8.2(5) . . . . ?
C2A C1A C6A C5A 2.4(6) . . . . ?
C2A C1A C6A N1A -176.4(4) . . . . ?
C9A N1A C6A C5A -155.4(4) . . . . ?
C8A N1A C6A C5A -4.3(5) . . . . ?
C9A N1A C6A C1A 23.6(7) . . . . ?
C8A N1A C6A C1A 174.6(4) . . . . ?
C6A C5A C7A C21A 141.3(4) . . . . ?
C4A C5A C7A C21A -42.7(6) . . . . ?
C6A C5A C7A C17A -102.8(4) . . . . ?
C4A C5A C7A C17A 73.2(5) . . . . ?
C6A C5A C7A C8A 16.3(4) . . . . ?
C4A C5A C7A C8A -167.7(4) . . . . ?
C9A N1A C8A C18A 43.7(5) . . . . ?
C6A N1A C8A C18A -109.3(3) . . . . ?
C9A N1A C8A C7A 167.1(4) . . . . ?
C6A N1A C8A C7A 14.1(4) . . . . ?
C5A C7A C8A N1A -17.7(4) . . . . ?
C21A C7A C8A N1A -143.0(3) . . . . ?
C17A C7A C8A N1A 101.7(3) . . . . ?
C5A C7A C8A C18A 99.2(4) . . . . ?
C21A C7A C8A C18A -26.1(5) . . . . ?
C17A C7A C8A C18A -141.4(3) . . . . ?
C6A N1A C9A O4A -24.3(7) . . . . ?
C8A N1A C9A O4A -172.7(4) . . . . ?
C6A N1A C9A C10A 156.2(4) . . . . ?
C8A N1A C9A C10A 7.7(6) . . . . ?
O4A C9A C10A C11A 146.5(5) . . . . ?
N1A C9A C10A C11A -34.0(6) . . . . ?
C12A O1A C11A C18A -68.0(4) . . . . ?
C12A O1A C11A C10A 171.7(3) . . . . ?
C9A C10A C11A O1A 128.1(4) . . . . ?
C9A C10A C11A C18A 4.9(6) . . . . ?
C11A O1A C12A C13A 88.4(5) . . . . ?
O1A C12A C13A C14A -64.7(6) . . . . ?
C12A C13A C14A C15A 177.6(4) . . . . ?
C12A C13A C14A C19A -2.9(7) . . . . ?
C13A C14A C15A N2A -127.4(5) . . . . ?
C19A C14A C15A N2A 53.0(5) . . . . ?
C16A N2A C15A C14A 77.7(5) . . . . ?
C21A N2A C15A C14A -45.0(5) . . . . ?
C15A N2A C16A C17A -139.8(4) . . . . ?
C21A N2A C16A C17A -14.0(4) . . . . ?
N2A C16A C17A C7A 34.2(4) . . . . ?
C5A C7A C17A C16A -164.2(3) . . . . ?
C21A C7A C17A C16A -40.7(4) . . . . ?
C8A C7A C17A C16A 82.0(4) . . . . ?
N1A C8A C18A C11A -71.1(4) . . . . ?
C7A C8A C18A C11A 173.4(3) . . . . ?
N1A C8A C18A C19A 156.6(3) . . . . ?
C7A C8A C18A C19A 41.1(4) . . . . ?
O1A C11A C18A C8A -72.0(4) . . . . ?
C10A C11A C18A C8A 45.6(4) . . . . ?
O1A C11A C18A C19A 57.6(5) . . . . ?
C10A C11A C18A C19A 175.2(4) . . . . ?
C13A C14A C19A C20A 177.7(4) . . . . ?
C15A C14A C19A C20A -2.7(5) . . . . ?
C13A C14A C19A C18A 59.6(5) . . . . ?
C15A C14A C19A C18A -120.8(4) . . . . ?
C8A C18A C19A C20A -61.3(4) . . . . ?
C11A C18A C19A C20A 171.4(4) . . . . ?
C8A C18A C19A C14A 58.7(4) . . . . ?
C11A C18A C19A C14A -68.6(5) . . . . ?
C14A C19A C20A C21A -54.5(4) . . . . ?
C18A C19A C20A C21A 68.3(4) . . . . ?
C19A C20A C21A N2A 62.4(4) . . . . ?
C19A C20A C21A C7A -56.2(4) . . . . ?
C16A N2A C21A C20A -136.6(3) . . . . ?
C15A N2A C21A C20A -11.0(5) . . . . ?
C16A N2A C21A C7A -11.7(4) . . . . ?
C15A N2A C21A C7A 113.9(4) . . . . ?
C5A C7A C21A C20A -84.6(4) . . . . ?
C17A C7A C21A C20A 154.2(3) . . . . ?
C8A C7A C21A C20A 33.8(5) . . . . ?
C5A C7A C21A N2A 153.3(3) . . . . ?
C17A C7A C21A N2A 32.1(4) . . . . ?
C8A C7A C21A N2A -88.2(4) . . . . ?
O51 C24 C25 N31 -52.6(17) . . . . ?
O5 C24 C25 N31 -95.9(9) . . . . ?
O6 C24 C25 N31 79.6(10) . . . . ?
O61 C24 C25 N31 155.5(13) . . . . ?
O51 C24 C25 N3 71.9(15) . . . . ?
O5 C24 C25 N3 28.5(6) . . . . ?
O6 C24 C25 N3 -156.0(5) . . . . ?
O61 C24 C25 N3 -80.0(11) . . . . ?
O51 C24 C25 C26 -166.4(15) . . . . ?
O5 C24 C25 C26 150.3(6) . . . . ?
O6 C24 C25 C26 -34.2(7) . . . . ?
O61 C24 C25 C26 41.7(12) . . . . ?
N31 C25 N3 C27 9.4(10) . . . . ?
C24 C25 N3 C27 -114.0(5) . . . . ?
C26 C25 N3 C27 123.3(5) . . . . ?
C25 N3 C27 O7 3.3(9) . . . . ?
C25 N3 C27 C28 -177.5(4) . . . . ?
O7 C27 C28 C33 157.0(6) . . . . ?
N3 C27 C28 C33 -22.3(7) . . . . ?
O7 C27 C28 C29 -19.5(7) . . . . ?
N3 C27 C28 C29 161.2(4) . . . . ?
C33 C28 C29 C30 0.8(7) . . . . ?
C27 C28 C29 C30 177.4(4) . . . . ?
C28 C29 C30 C31 0.4(6) . . . . ?
C28 C29 C30 N4 -176.0(4) . . . . ?
O9 N4 C30 C29 179.3(4) . . . . ?
O8 N4 C30 C29 0.9(6) . . . . ?
O9 N4 C30 C31 2.7(6) . . . . ?
O8 N4 C30 C31 -175.7(4) . . . . ?
C29 C30 C31 C32 -0.4(7) . . . . ?
N4 C30 C31 C32 176.0(4) . . . . ?
C30 C31 C32 C33 -0.8(8) . . . . ?
C30 C31 C32 C271 168.6(7) . . . 1_545 ?
C29 C28 C33 C32 -2.0(8) . . . . ?
C27 C28 C33 C32 -178.4(5) . . . . ?
C31 C32 C33 C28 2.0(9) . . . . ?
C271 C32 C33 C28 -165.1(9) 1_545 . . . ?
N3 C25 N31 C271 -12.5(19) . . . . ?
C24 C25 N31 C271 111.0(16) . . . . ?
C26 C25 N31 C271 -130.2(16) . . . . ?
C25 N31 C271 O71 1(3) . . . . ?
C25 N31 C271 C32 -171.8(12) . . . 1_565 ?
O6B C24A C25A N3A 78(5) . . . . ?
O5A C24A C25A N3A -38.3(7) . . . . ?
O6A C24A C25A N3A 144.5(5) . . . . ?
O5B C24A C25A N3A -80(3) . . . . ?
O6B C24A C25A N3B -164(5) . . . . ?
O5A C24A C25A N3B 80.1(18) . . . . ?
O6A C24A C25A N3B -97.1(18) . . . . ?
O5B C24A C25A N3B 38(4) . . . . ?
O6B C24A C25A C26A -44(5) . . . . ?
O5A C24A C25A C26A -160.6(6) . . . . ?
O6A C24A C25A C26A 22.3(7) . . . . ?
O5B C24A C25A C26A 157(3) . . . . ?
N3B C25A N3A C27A -3.5(18) . . . . ?
C26A C25A N3A C27A -128.3(4) . . . . ?
C24A C25A N3A C27A 107.8(4) . . . . ?
C25A N3A C27A O7A -1.1(7) . . . . ?
C25A N3A C27A C28A 179.3(4) . . . . ?
N3A C25A N3B C27B -5(5) . . . . ?
C26A C25A N3B C27B 118(4) . . . . ?
C24A C25A N3B C27B -123(4) . . . . ?
C25A N3B C27B O7B 12(7) . . . . ?
C25A N3B C27B C32A -179(3) . . . 1_565 ?
O7A C27A C28A C29A 21.9(6) . . . . ?
N3A C27A C28A C29A -158.4(4) . . . . ?
O7A C27A C28A C33A -157.5(5) . . . . ?
N3A C27A C28A C33A 22.1(6) . . . . ?
C33A C28A C29A C30A -0.6(6) . . . . ?
C27A C28A C29A C30A 179.9(4) . . . . ?
C28A C29A C30A C31A 0.6(6) . . . . ?
C28A C29A C30A N4A 177.6(4) . . . . ?
O9A N4A C30A C31A 7.1(6) . . . . ?
O8A N4A C30A C31A -174.6(4) . . . . ?
O9A N4A C30A C29A -170.1(4) . . . . ?
O8A N4A C30A C29A 8.2(5) . . . . ?
C29A C30A C31A C32A 0.4(7) . . . . ?
N4A C30A C31A C32A -176.7(5) . . . . ?
C30A C31A C32A C33A -1.2(9) . . . . ?
C30A C31A C32A C27B -167.8(14) . . . 1_545 ?
C31A C32A C33A C28A 1.1(10) . . . . ?
C27B C32A C33A C28A 162.6(19) 1_545 . . . ?
C29A C28A C33A C32A -0.1(8) . . . . ?
C27A C28A C33A C32A 179.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.93 1.71 2.621(6) 167.1 .
N2 H2A O51 0.93 1.91 2.78(2) 153.8 .
N2A H2AA O5B 0.93 1.58 2.49(4) 164.9 .
N2A H2AA O5A 0.93 1.77 2.662(6) 160.2 .
N3 H3 O6 0.88 2.02 2.804(7) 148.5 2_746
N31 H31 O61 0.88 1.93 2.77(2) 160.1 2_756
N3A H3A O6A 0.88 1.96 2.798(6) 157.5 2_647
O100 H100 O5 0.84 2.23 2.896(16) 135.8 .
O200 H200 O4A 0.84 1.99 2.816(8) 167.1 1_655
O110 H110 O51 0.84 1.80 2.59(3) 156.8 .
O210 H210 O4A 0.84 1.79 2.61(3) 164.1 1_655
O300 H300 O5A 0.84 1.78 2.589(13) 160.8 .
O400 H400 O4 0.84 1.97 2.801(16) 169.7 1_545
O410 H410 O4 0.84 1.94 2.718(14) 153.5 1_545

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 930486'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

#===== end



data_b3nb(dl)a/1pr
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-(D~0.73~L~0.27~)-alaninate propan-1-ol solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O5, C23 H27 N2 O4, C3 H8 O'
_chemical_formula_sum            'C36 H44 N4 O10'
_chemical_formula_weight         692.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.826(2)
_cell_length_b                   12.048(3)
_cell_length_c                   35.119(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3311.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3279
_cell_measurement_theta_min      2.5144
_cell_measurement_theta_max      77.8566

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5417
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11634
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         77.81
_reflns_number_total             6264
_reflns_number_gt                5265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+1.4944P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_number_reflns         6264
_refine_ls_number_parameters     616
_refine_ls_number_restraints     247
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1959
_refine_ls_wR_factor_gt          0.1715
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6862(4) 1.2786(2) 0.17518(7) 0.0350(6) Uani 1 1 d . . .
O2 O 0.7478(4) 0.7046(2) 0.32401(7) 0.0382(6) Uani 1 1 d . . .
O3 O 0.7909(4) 0.5800(2) 0.26455(7) 0.0375(6) Uani 1 1 d . . .
O4 O 0.7140(5) 1.1089(2) 0.29476(7) 0.0424(7) Uani 1 1 d . . .
N1 N 0.6477(4) 1.0242(2) 0.23883(7) 0.0274(6) Uani 1 1 d . . .
N2 N 0.6372(5) 0.9101(3) 0.11333(8) 0.0392(8) Uani 1 1 d . . .
H2A H 0.6341 0.8479 0.0977 0.047 Uiso 1 1 calc R . .
C1 C 0.6968(5) 0.8702(3) 0.28640(9) 0.0315(7) Uani 1 1 d . . .
H1A H 0.6874 0.9167 0.3082 0.038 Uiso 1 1 calc R . .
C2 C 0.7311(5) 0.7570(3) 0.28981(9) 0.0320(8) Uani 1 1 d . . .
C3 C 0.7495(5) 0.6883(3) 0.25735(10) 0.0316(7) Uani 1 1 d . . .
C4 C 0.7250(5) 0.7328(3) 0.22131(9) 0.0315(7) Uani 1 1 d . . .
H4A H 0.7333 0.6869 0.1994 0.038 Uiso 1 1 calc R . .
C5 C 0.6880(5) 0.8462(3) 0.21764(9) 0.0291(7) Uani 1 1 d . . .
C6 C 0.6769(5) 0.9122(3) 0.24949(9) 0.0283(7) Uani 1 1 d . . .
C7 C 0.6403(5) 0.9105(3) 0.18250(9) 0.0317(7) Uani 1 1 d . . .
C8 C 0.6548(5) 1.0325(3) 0.19664(9) 0.0300(7) Uani 1 1 d . . .
H8A H 0.5544 1.0761 0.1873 0.036 Uiso 1 1 calc R . .
C9 C 0.6941(5) 1.1143(3) 0.26039(10) 0.0333(7) Uani 1 1 d . . .
C10 C 0.7206(6) 1.2218(3) 0.23912(10) 0.0358(8) Uani 1 1 d . . .
H10A H 0.7952 1.2698 0.2548 0.043 Uiso 1 1 calc R . .
H10B H 0.6085 1.2594 0.2370 0.043 Uiso 1 1 calc R . .
C11 C 0.7992(5) 1.2153(3) 0.19862(9) 0.0310(7) Uani 1 1 d . . .
H11A H 0.9141 1.2515 0.1988 0.037 Uiso 1 1 calc R . .
C12 C 0.7462(6) 1.2962(3) 0.13692(10) 0.0389(8) Uani 1 1 d . . .
H12A H 0.8722 1.3030 0.1371 0.047 Uiso 1 1 calc R . .
H12B H 0.6984 1.3666 0.1270 0.047 Uiso 1 1 calc R . .
C13 C 0.6957(6) 1.2033(3) 0.11110(10) 0.0389(9) Uani 1 1 d . . .
H13A H 0.6184 1.2181 0.0909 0.047 Uiso 1 1 calc R . .
C14 C 0.7544(6) 1.1010(3) 0.11533(9) 0.0365(8) Uani 1 1 d . . .
C15 C 0.7014(7) 1.0064(3) 0.09005(10) 0.0417(10) Uani 1 1 d . . .
H15A H 0.8002 0.9822 0.0745 0.050 Uiso 1 1 calc R . .
H15B H 0.6103 1.0316 0.0725 0.050 Uiso 1 1 calc R . .
C16 C 0.4601(6) 0.9299(4) 0.12818(10) 0.0402(9) Uani 1 1 d . . .
H16A H 0.3744 0.8915 0.1121 0.048 Uiso 1 1 calc R . .
H16B H 0.4336 1.0102 0.1286 0.048 Uiso 1 1 calc R . .
C17 C 0.4601(5) 0.8824(3) 0.16842(9) 0.0343(8) Uani 1 1 d . . .
H17A H 0.4406 0.8012 0.1682 0.041 Uiso 1 1 calc R . .
H17B H 0.3718 0.9183 0.1844 0.041 Uiso 1 1 calc R . .
C18 C 0.8192(5) 1.0938(3) 0.18677(9) 0.0310(7) Uani 1 1 d . . .
H18A H 0.9086 1.0624 0.2040 0.037 Uiso 1 1 calc R . .
C19 C 0.8816(5) 1.0700(3) 0.14624(10) 0.0350(8) Uani 1 1 d . . .
H19A H 0.9904 1.1116 0.1418 0.042 Uiso 1 1 calc R . .
C20 C 0.9193(6) 0.9442(4) 0.14461(12) 0.0404(9) Uani 1 1 d . . .
H20A H 0.9773 0.9253 0.1204 0.048 Uiso 1 1 calc R . .
H20B H 0.9948 0.9225 0.1660 0.048 Uiso 1 1 calc R . .
C21 C 0.7497(6) 0.8834(3) 0.14741(9) 0.0351(8) Uani 1 1 d . . .
H21A H 0.7732 0.8018 0.1474 0.042 Uiso 1 1 calc R . .
C22 C 0.7239(6) 0.7708(4) 0.35713(10) 0.0441(10) Uani 1 1 d . . .
H22A H 0.7366 0.7245 0.3799 0.066 Uiso 1 1 calc R . .
H22B H 0.6091 0.8034 0.3567 0.066 Uiso 1 1 calc R . .
H22C H 0.8094 0.8303 0.3576 0.066 Uiso 1 1 calc R . .
C23 C 0.8311(8) 0.5150(3) 0.23228(12) 0.0486(10) Uani 1 1 d . . .
H23A H 0.8592 0.4393 0.2404 0.073 Uiso 1 1 calc R . .
H23B H 0.9293 0.5476 0.2191 0.073 Uiso 1 1 calc R . .
H23C H 0.7327 0.5131 0.2151 0.073 Uiso 1 1 calc R . .
C24 C 0.6314(6) 0.7348(3) 0.04267(11) 0.0377(9) Uani 1 1 d . . .
C25 C 0.6425(6) 0.6371(4) 0.01516(13) 0.0435(9) Uani 1 1 d . . .
H25B H 0.7415 0.5895 0.0227 0.052 Uiso 0.274(6) 1 calc PR A 2
H25A H 0.5568 0.5857 0.0236 0.052 Uiso 0.726(6) 1 d PR A 1
O5 O 0.7034(6) 0.7259(3) 0.07440(10) 0.0329(9) Uani 0.726(6) 1 d P A 1
O6 O 0.5298(6) 0.8122(4) 0.03453(11) 0.0420(10) Uani 0.726(6) 1 d P A 1
O7 O 0.6937(9) 0.4194(9) 0.0425(3) 0.0564(18) Uani 0.726(6) 1 d PU . 1
O8 O 1.0414(15) 0.0908(9) 0.0587(3) 0.071(3) Uani 0.726(6) 1 d PU . 1
O9 O 1.3196(17) 0.1058(10) 0.0573(5) 0.055(2) Uani 0.726(6) 1 d PU . 1
N4 N 1.1780(14) 0.1498(6) 0.0540(3) 0.0401(19) Uani 0.726(6) 1 d PU . 1
N3 N 0.7990(6) 0.5781(4) 0.01783(12) 0.0320(9) Uani 0.726(6) 1 d P . 1
H3A H 0.8930 0.6124 0.0108 0.038 Uiso 0.726(6) 1 calc PR A 1
C26 C 0.5907(12) 0.6652(7) -0.0243(2) 0.055(2) Uani 0.726(6) 1 d PU . 1
H26E H 0.6122 0.6016 -0.0410 0.083 Uiso 0.726(6) 1 calc PR A 1
H26A H 0.6570 0.7292 -0.0332 0.083 Uiso 0.726(6) 1 calc PR A 1
H26B H 0.4687 0.6835 -0.0248 0.083 Uiso 0.726(6) 1 calc PR A 1
C27 C 0.8129(7) 0.4722(4) 0.03047(14) 0.0319(11) Uani 0.726(6) 1 d P . 1
C28 C 0.9867(10) 0.4235(6) 0.0286(2) 0.0312(12) Uani 0.726(6) 1 d PU . 1
C29 C 1.0039(11) 0.3146(6) 0.0426(2) 0.0357(16) Uani 0.726(6) 1 d PU . 1
H29A H 0.9086 0.2765 0.0531 0.043 Uiso 0.726(6) 1 calc PR A 1
C30 C 1.1616(13) 0.2646(7) 0.0408(3) 0.0347(16) Uani 0.726(6) 1 d PU . 1
C31 C 1.3049(10) 0.3155(6) 0.0274(2) 0.0389(15) Uani 0.726(6) 1 d PU . 1
H31B H 1.4126 0.2793 0.0280 0.047 Uiso 0.726(6) 1 calc PR A 1
C32 C 1.2886(8) 0.4203(6) 0.0130(2) 0.0422(14) Uani 0.726(6) 1 d PU . 1
H32A H 1.3853 0.4570 0.0025 0.051 Uiso 0.726(6) 1 calc PR A 1
C33 C 1.1326(9) 0.4730(6) 0.01366(19) 0.0339(14) Uani 0.726(6) 1 d PU . 1
H33A H 1.1243 0.5460 0.0035 0.041 Uiso 0.726(6) 1 calc PR A 1
H31A H 0.3982 0.6035 0.0048 0.041 Uiso 0.274(6) 1 d PR A 2
C261 C 0.681(3) 0.6906(19) -0.0290(5) 0.056(4) Uani 0.274(6) 1 d PU . 2
H26F H 0.6409 0.6384 -0.0485 0.084 Uiso 0.274(6) 1 calc PR A 2
H26C H 0.8042 0.7027 -0.0322 0.084 Uiso 0.274(6) 1 calc PR A 2
H26D H 0.6207 0.7613 -0.0318 0.084 Uiso 0.274(6) 1 calc PR A 2
O51 O 0.586(2) 0.7328(11) 0.0729(3) 0.051(3) Uani 0.274(6) 1 d PU A 2
O61 O 0.750(2) 0.8208(11) 0.0324(4) 0.063(4) Uani 0.274(6) 1 d PU A 2
O71 O 0.639(3) 0.424(3) 0.0393(9) 0.059(5) Uani 0.274(6) 1 d PU . 2
O81 O 1.074(2) 0.1064(19) 0.0691(5) 0.034(3) Uani 0.274(6) 1 d PU . 2
O91 O 1.354(4) 0.091(3) 0.0570(13) 0.049(4) Uani 0.274(6) 1 d PU . 2
N41 N 1.211(4) 0.124(2) 0.0546(9) 0.039(4) Uani 0.274(6) 1 d PU . 2
N31 N 0.5054(16) 0.5764(11) 0.0149(3) 0.037(3) Uani 0.274(6) 1 d PU . 2
C271 C 0.506(2) 0.4727(14) 0.0281(4) 0.038(3) Uani 0.274(6) 1 d PU . 2
C281 C 1.3293(15) 0.4165(9) 0.0297(3) 0.034(3) Uani 0.274(6) 1 d PGU . 2
C291 C 1.3376(16) 0.3045(10) 0.0390(4) 0.031(3) Uani 0.274(6) 1 d PGU . 2
H29B H 1.4453 0.2699 0.0427 0.037 Uiso 0.274(6) 1 calc PR A 2
C301 C 1.188(2) 0.2430(9) 0.0427(5) 0.024(3) Uani 0.274(6) 1 d PGU . 2
C311 C 1.0305(17) 0.2936(13) 0.0372(6) 0.033(3) Uani 0.274(6) 1 d PGU . 2
H31C H 0.9284 0.2516 0.0397 0.040 Uiso 0.274(6) 1 calc PR A 2
C321 C 1.0222(15) 0.4057(13) 0.0279(6) 0.036(4) Uani 0.274(6) 1 d PGU . 2
H32B H 0.9144 0.4403 0.0242 0.043 Uiso 0.274(6) 1 calc PR A 2
C331 C 1.1716(19) 0.4671(9) 0.0242(4) 0.038(4) Uani 0.274(6) 1 d PGU . 2
H33B H 1.1660 0.5437 0.0179 0.045 Uiso 0.274(6) 1 calc PR A 2
O110 O 0.8197(7) 0.5954(3) 0.13509(10) 0.0494(11) Uani 0.853(9) 1 d PDU B 1
H11D H 0.7876 0.6347 0.1167 0.074 Uiso 0.853(9) 1 calc PR B 1
C110 C 0.9920(8) 0.5575(4) 0.12846(14) 0.0490(14) Uani 0.853(9) 1 d PD B 1
H11B H 0.9901 0.5007 0.1081 0.059 Uiso 0.853(9) 1 calc PR B 1
H11C H 1.0349 0.5214 0.1519 0.059 Uiso 0.853(9) 1 calc PR B 1
C120 C 1.1156(8) 0.6492(6) 0.11709(18) 0.0565(16) Uani 0.853(9) 1 d PDU B 1
H12C H 1.1211 0.7055 0.1376 0.068 Uiso 0.853(9) 1 calc PR B 1
H12D H 1.0738 0.6862 0.0937 0.068 Uiso 0.853(9) 1 calc PR B 1
C130 C 1.2936(11) 0.6020(7) 0.11001(18) 0.0620(17) Uani 0.853(9) 1 d PDU B 1
H13B H 1.3713 0.6622 0.1028 0.093 Uiso 0.853(9) 1 calc PR B 1
H13C H 1.2883 0.5472 0.0894 0.093 Uiso 0.853(9) 1 calc PR B 1
H13D H 1.3355 0.5663 0.1333 0.093 Uiso 0.853(9) 1 calc PR B 1
O112 O 0.719(4) 0.592(2) 0.1303(7) 0.059(4) Uani 0.147(9) 1 d PDU B 2
H112 H 0.6437 0.6312 0.1195 0.088 Uiso 0.147(9) 1 calc PR B 2
C112 C 0.876(3) 0.598(3) 0.1089(9) 0.059(5) Uani 0.147(9) 1 d PDU B 2
H11G H 0.8472 0.6335 0.0842 0.071 Uiso 0.147(9) 1 calc PR B 2
H11H H 0.9086 0.5206 0.1030 0.071 Uiso 0.147(9) 1 calc PR B 2
C122 C 1.037(4) 0.656(4) 0.1234(12) 0.057(4) Uani 0.147(9) 1 d PDU B 2
H12G H 1.0297 0.6565 0.1515 0.068 Uiso 0.147(9) 1 calc PR B 2
H12H H 1.0308 0.7338 0.1149 0.068 Uiso 0.147(9) 1 calc PR B 2
C132 C 1.214(6) 0.613(4) 0.1129(12) 0.056(4) Uani 0.147(9) 1 d PDU B 2
H13H H 1.3006 0.6638 0.1226 0.084 Uiso 0.147(9) 1 calc PR B 2
H13I H 1.2234 0.6069 0.0852 0.084 Uiso 0.147(9) 1 calc PR B 2
H13J H 1.2307 0.5391 0.1243 0.084 Uiso 0.147(9) 1 calc PR B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0422(14) 0.0315(12) 0.0313(11) 0.0045(10) -0.0003(11) -0.0034(12)
O2 0.0521(16) 0.0372(13) 0.0255(11) 0.0066(10) -0.0050(11) 0.0023(13)
O3 0.0523(16) 0.0260(12) 0.0344(11) 0.0023(10) -0.0025(12) 0.0002(12)
O4 0.070(2) 0.0351(14) 0.0222(10) -0.0020(10) -0.0085(12) 0.0035(14)
N1 0.0402(16) 0.0216(13) 0.0202(11) 0.0018(10) -0.0020(11) -0.0029(12)
N2 0.065(2) 0.0322(15) 0.0200(11) -0.0005(12) 0.0026(14) -0.0112(17)
C1 0.0412(19) 0.0293(16) 0.0240(14) 0.0044(13) -0.0010(14) -0.0057(15)
C2 0.0388(19) 0.0321(17) 0.0250(14) 0.0059(13) -0.0034(13) -0.0005(15)
C3 0.0394(18) 0.0242(15) 0.0311(15) 0.0017(13) -0.0051(14) 0.0011(15)
C4 0.0378(19) 0.0294(16) 0.0273(14) 0.0011(13) 0.0019(14) 0.0006(15)
C5 0.0376(18) 0.0248(15) 0.0248(14) 0.0027(12) -0.0011(14) -0.0002(14)
C6 0.0372(17) 0.0244(15) 0.0234(13) 0.0012(12) -0.0013(13) 0.0000(14)
C7 0.044(2) 0.0282(16) 0.0230(13) -0.0008(13) 0.0012(14) -0.0073(16)
C8 0.0407(19) 0.0296(16) 0.0198(13) 0.0042(12) 0.0021(13) -0.0015(16)
C9 0.0399(19) 0.0305(17) 0.0295(15) -0.0050(14) -0.0047(14) 0.0040(15)
C10 0.051(2) 0.0283(16) 0.0283(15) -0.0042(14) -0.0029(15) 0.0006(17)
C11 0.0374(18) 0.0261(16) 0.0295(15) 0.0011(13) -0.0056(14) -0.0004(15)
C12 0.051(2) 0.0312(17) 0.0346(17) 0.0087(15) 0.0068(16) -0.0079(17)
C13 0.055(2) 0.0342(18) 0.0271(14) 0.0052(14) 0.0018(16) -0.0066(19)
C14 0.055(2) 0.0313(17) 0.0231(13) 0.0015(13) 0.0071(15) -0.0048(17)
C15 0.070(3) 0.0313(18) 0.0235(14) 0.0025(13) 0.0043(17) -0.013(2)
C16 0.054(2) 0.038(2) 0.0283(16) 0.0016(16) -0.0095(16) -0.0105(19)
C17 0.046(2) 0.0326(18) 0.0243(14) 0.0036(13) -0.0023(14) -0.0109(17)
C18 0.0361(19) 0.0275(16) 0.0294(14) 0.0010(13) 0.0017(14) -0.0009(15)
C19 0.045(2) 0.0287(17) 0.0320(16) 0.0009(14) 0.0071(15) -0.0043(16)
C20 0.052(2) 0.0326(19) 0.0365(17) -0.0024(16) 0.0104(17) -0.0013(17)
C21 0.057(2) 0.0255(15) 0.0231(13) -0.0014(12) 0.0030(15) -0.0038(16)
C22 0.059(3) 0.048(2) 0.0255(15) 0.0075(16) -0.0033(16) -0.001(2)
C23 0.075(3) 0.0269(17) 0.044(2) -0.0033(16) 0.000(2) 0.000(2)
C24 0.052(2) 0.0289(17) 0.0318(17) -0.0017(14) -0.0046(16) 0.0036(17)
C25 0.044(2) 0.039(2) 0.047(2) -0.0113(18) -0.0059(18) 0.0067(19)
O5 0.041(2) 0.0320(18) 0.0262(15) -0.0008(13) -0.0082(15) 0.0037(17)
O6 0.056(3) 0.033(2) 0.0370(19) -0.0072(16) -0.0113(17) 0.0126(18)
O7 0.037(4) 0.052(3) 0.080(4) 0.024(3) 0.006(4) -0.011(4)
O8 0.088(6) 0.046(4) 0.079(6) 0.011(4) 0.021(5) -0.006(4)
O9 0.068(7) 0.049(4) 0.047(3) -0.008(2) -0.011(4) 0.034(3)
N4 0.061(5) 0.030(4) 0.029(2) 0.002(3) 0.007(3) 0.019(3)
N3 0.031(2) 0.028(2) 0.0373(19) -0.0028(17) 0.0033(16) -0.0028(18)
C26 0.061(5) 0.063(5) 0.042(3) -0.023(3) -0.017(4) 0.009(4)
C27 0.034(2) 0.031(2) 0.030(2) 0.0029(18) 0.0016(19) -0.009(2)
C28 0.039(3) 0.028(3) 0.027(2) 0.001(2) -0.005(2) 0.006(2)
C29 0.054(3) 0.023(3) 0.030(3) -0.007(2) 0.011(2) 0.000(3)
C30 0.055(4) 0.029(3) 0.021(2) 0.001(2) -0.004(2) 0.011(3)
C31 0.041(3) 0.038(3) 0.038(4) -0.007(3) -0.014(3) 0.004(3)
C32 0.037(3) 0.041(3) 0.049(4) -0.010(3) 0.004(3) -0.003(3)
C33 0.039(3) 0.032(3) 0.031(3) 0.003(2) -0.005(3) -0.006(2)
C261 0.070(9) 0.068(8) 0.030(6) -0.014(6) -0.005(8) -0.022(8)
O51 0.060(7) 0.048(6) 0.045(5) -0.008(5) 0.015(5) -0.017(6)
O61 0.083(8) 0.045(6) 0.061(6) -0.001(5) 0.021(6) -0.009(6)
O71 0.050(9) 0.057(6) 0.070(6) 0.015(5) 0.002(7) -0.001(8)
O81 0.028(5) 0.031(5) 0.042(6) -0.012(5) 0.004(5) 0.002(4)
O91 0.045(8) 0.055(8) 0.046(6) -0.006(6) 0.002(6) 0.015(7)
N41 0.043(7) 0.038(7) 0.035(5) 0.002(6) 0.005(5) 0.014(6)
N31 0.037(6) 0.030(5) 0.044(5) -0.012(4) -0.001(5) -0.006(5)
C271 0.049(7) 0.042(7) 0.024(5) 0.015(5) -0.001(5) 0.008(6)
C281 0.053(6) 0.027(5) 0.022(5) -0.006(5) -0.007(5) -0.007(5)
C291 0.032(6) 0.035(5) 0.026(6) 0.008(5) -0.011(5) -0.001(5)
C301 0.034(6) 0.024(6) 0.014(5) -0.001(4) 0.001(4) 0.009(5)
C311 0.042(5) 0.033(5) 0.025(4) -0.010(4) 0.001(4) 0.005(4)
C321 0.035(6) 0.035(6) 0.037(5) -0.004(5) -0.002(5) -0.001(5)
C331 0.052(7) 0.030(5) 0.031(7) -0.002(5) -0.015(6) -0.004(5)
O110 0.067(3) 0.0434(18) 0.0379(17) 0.0061(15) -0.0052(18) 0.002(2)
C110 0.072(4) 0.039(3) 0.036(2) 0.001(2) 0.000(2) 0.004(3)
C120 0.062(4) 0.058(3) 0.049(3) 0.010(3) -0.002(3) -0.006(3)
C130 0.063(4) 0.079(4) 0.045(3) -0.001(3) 0.006(3) -0.014(4)
O112 0.063(7) 0.057(6) 0.056(6) -0.001(6) -0.008(6) -0.002(6)
C112 0.062(7) 0.061(7) 0.055(7) 0.001(6) -0.001(6) -0.002(6)
C122 0.061(7) 0.057(6) 0.052(6) 0.003(5) 0.001(6) -0.005(6)
C132 0.060(6) 0.062(6) 0.045(5) 0.001(5) 0.001(6) -0.006(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.429(4) . ?
O1 C12 1.439(4) . ?
O2 C2 1.364(4) . ?
O2 C22 1.423(5) . ?
O3 C3 1.368(4) . ?
O3 C23 1.412(5) . ?
O4 C9 1.219(4) . ?
N1 C9 1.373(5) . ?
N1 C6 1.419(4) . ?
N1 C8 1.486(4) . ?
N2 C16 1.500(6) . ?
N2 C15 1.506(5) . ?
N2 C21 1.521(5) . ?
N2 H2A 0.9300 . ?
C1 C2 1.394(5) . ?
C1 C6 1.400(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.417(5) . ?
C3 C4 1.388(5) . ?
C4 C5 1.402(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(5) . ?
C5 C7 1.504(5) . ?
C7 C17 1.532(6) . ?
C7 C21 1.536(5) . ?
C7 C8 1.556(5) . ?
C8 C18 1.524(5) . ?
C8 H8A 1.0000 . ?
C9 C10 1.509(5) . ?
C10 C11 1.552(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.529(5) . ?
C11 H11A 1.0000 . ?
C12 C13 1.494(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.323(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.503(5) . ?
C14 C19 1.520(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.524(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.532(5) . ?
C18 H18A 1.0000 . ?
C19 C20 1.545(5) . ?
C19 H19A 1.0000 . ?
C20 C21 1.520(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O51 1.122(12) . ?
C24 O5 1.253(5) . ?
C24 O6 1.258(6) . ?
C24 O61 1.435(15) . ?
C24 C25 1.526(5) . ?
C25 N31 1.298(13) . ?
C25 N3 1.419(6) . ?
C25 C26 1.484(9) . ?
C25 C261 1.71(2) . ?
C25 H25B 1.0000 . ?
C25 H25A 0.9600 . ?
O7 C27 1.206(10) . ?
O8 N4 1.294(16) . ?
O9 N4 1.233(13) . ?
N4 C30 1.466(11) . ?
N3 C27 1.355(6) . ?
N3 H3A 0.8800 . ?
C26 H26E 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 C28 1.482(9) . ?
C28 C33 1.391(9) . ?
C28 C29 1.407(9) . ?
C29 C30 1.375(12) . ?
C29 H29A 0.9500 . ?
C30 C31 1.361(11) . ?
C31 C32 1.366(10) . ?
C31 H31B 0.9500 . ?
C32 C33 1.376(10) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C261 H26F 0.9800 . ?
C261 H26C 0.9800 . ?
C261 H26D 0.9800 . ?
O71 C271 1.26(3) . ?
O81 N41 1.21(4) . ?
O91 N41 1.19(4) . ?
N41 C301 1.51(3) . ?
N31 C271 1.332(19) . ?
N31 H25A 0.5167 . ?
N31 H31A 0.9686 . ?
C271 C281 1.54(2) 1_455 ?
C281 C291 1.3900 . ?
C281 C331 1.3900 . ?
C281 C271 1.54(2) 1_655 ?
C291 C301 1.3900 . ?
C291 H29B 0.9500 . ?
C301 C311 1.3900 . ?
C311 C321 1.3900 . ?
C311 H31C 0.9500 . ?
C321 C331 1.3900 . ?
C321 H32B 0.9500 . ?
C331 H33B 0.9500 . ?
O110 C110 1.442(8) . ?
O110 H11D 0.8400 . ?
C110 C120 1.522(7) . ?
C110 H11B 0.9900 . ?
C110 H11C 0.9900 . ?
C120 C130 1.525(7) . ?
C120 H12C 0.9900 . ?
C120 H12D 0.9900 . ?
C130 H13B 0.9800 . ?
C130 H13C 0.9800 . ?
C130 H13D 0.9800 . ?
O112 C112 1.444(10) . ?
O112 H112 0.8400 . ?
C112 C122 1.524(8) . ?
C112 H11G 0.9900 . ?
C112 H11H 0.9900 . ?
C122 C132 1.524(8) . ?
C122 H12G 0.9900 . ?
C122 H12H 0.9900 . ?
C132 H13H 0.9800 . ?
C132 H13I 0.9800 . ?
C132 H13J 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.5(3) . . ?
C2 O2 C22 116.5(3) . . ?
C3 O3 C23 115.7(3) . . ?
C9 N1 C6 124.4(3) . . ?
C9 N1 C8 119.1(3) . . ?
C6 N1 C8 108.8(3) . . ?
C16 N2 C15 112.0(4) . . ?
C16 N2 C21 107.2(3) . . ?
C15 N2 C21 113.4(3) . . ?
C16 N2 H2A 108.0 . . ?
C15 N2 H2A 108.0 . . ?
C21 N2 H2A 108.0 . . ?
C2 C1 C6 117.0(3) . . ?
C2 C1 H1A 121.5 . . ?
C6 C1 H1A 121.5 . . ?
O2 C2 C1 123.2(3) . . ?
O2 C2 C3 115.3(3) . . ?
C1 C2 C3 121.5(3) . . ?
O3 C3 C4 124.7(3) . . ?
O3 C3 C2 115.7(3) . . ?
C4 C3 C2 119.6(3) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 C7 110.7(3) . . ?
C4 C5 C7 129.0(3) . . ?
C5 C6 C1 122.5(3) . . ?
C5 C6 N1 110.2(3) . . ?
C1 C6 N1 127.3(3) . . ?
C5 C7 C17 112.3(3) . . ?
C5 C7 C21 114.2(3) . . ?
C17 C7 C21 101.9(3) . . ?
C5 C7 C8 102.0(3) . . ?
C17 C7 C8 112.2(3) . . ?
C21 C7 C8 114.6(3) . . ?
N1 C8 C18 106.9(3) . . ?
N1 C8 C7 104.6(3) . . ?
C18 C8 C7 116.6(3) . . ?
N1 C8 H8A 109.5 . . ?
C18 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
O4 C9 N1 122.5(4) . . ?
O4 C9 C10 121.2(3) . . ?
N1 C9 C10 116.2(3) . . ?
C9 C10 C11 117.7(3) . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 114.7(3) . . ?
O1 C11 C10 104.8(3) . . ?
C18 C11 C10 109.8(3) . . ?
O1 C11 H11A 109.1 . . ?
C18 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O1 C12 C13 111.7(3) . . ?
O1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 122.5(4) . . ?
C14 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
C13 C14 C15 122.9(4) . . ?
C13 C14 C19 122.4(4) . . ?
C15 C14 C19 114.6(3) . . ?
C14 C15 N2 110.8(3) . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N2 C16 C17 105.2(3) . . ?
N2 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
N2 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 102.5(3) . . ?
C16 C17 H17A 111.3 . . ?
C7 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C7 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C8 C18 C11 108.4(3) . . ?
C8 C18 C19 112.9(3) . . ?
C11 C18 C19 117.7(3) . . ?
C8 C18 H18A 105.6 . . ?
C11 C18 H18A 105.6 . . ?
C19 C18 H18A 105.6 . . ?
C14 C19 C18 114.1(3) . . ?
C14 C19 C20 109.9(3) . . ?
C18 C19 C20 106.2(3) . . ?
C14 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C21 C20 C19 107.7(4) . . ?
C21 C20 H20A 110.2 . . ?
C19 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
C19 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 N2 110.7(3) . . ?
C20 C21 C7 115.9(3) . . ?
N2 C21 C7 105.3(3) . . ?
C20 C21 H21A 108.3 . . ?
N2 C21 H21A 108.3 . . ?
C7 C21 H21A 108.3 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O51 C24 O5 45.5(8) . . ?
O51 C24 O6 91.7(9) . . ?
O5 C24 O6 123.4(4) . . ?
O51 C24 O61 117.3(9) . . ?
O5 C24 O61 89.7(7) . . ?
O6 C24 O61 79.4(7) . . ?
O51 C24 C25 127.0(8) . . ?
O5 C24 C25 118.1(4) . . ?
O6 C24 C25 117.6(4) . . ?
O61 C24 C25 111.2(6) . . ?
N31 C25 N3 115.5(7) . . ?
N31 C25 C26 84.1(7) . . ?
N3 C25 C26 114.3(5) . . ?
N31 C25 C24 113.1(7) . . ?
N3 C25 C24 113.2(4) . . ?
C26 C25 C24 113.6(4) . . ?
N31 C25 C261 110.7(10) . . ?
N3 C25 C261 95.5(10) . . ?
C26 C25 C261 27.5(7) . . ?
C24 C25 C261 107.1(8) . . ?
N31 C25 H25B 108.6 . . ?
N3 C25 H25B 13.1 . . ?
C26 C25 H25B 126.2 . . ?
C24 C25 H25B 108.6 . . ?
C261 C25 H25B 108.6 . . ?
N31 C25 H25A 20.1 . . ?
N3 C25 H25A 105.0 . . ?
C26 C25 H25A 104.2 . . ?
C24 C25 H25A 105.3 . . ?
C261 C25 H25A 130.4 . . ?
H25B C25 H25A 95.2 . . ?
O9 N4 O8 119.7(10) . . ?
O9 N4 C30 120.9(11) . . ?
O8 N4 C30 119.1(9) . . ?
C27 N3 C25 124.3(4) . . ?
C27 N3 H3A 117.9 . . ?
C25 N3 H3A 117.9 . . ?
C25 C26 H26E 109.5 . . ?
C25 C26 H26A 109.5 . . ?
H26E C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26E C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O7 C27 N3 123.3(7) . . ?
O7 C27 C28 121.1(7) . . ?
N3 C27 C28 115.6(5) . . ?
C33 C28 C29 116.9(7) . . ?
C33 C28 C27 126.9(6) . . ?
C29 C28 C27 116.2(6) . . ?
C30 C29 C28 118.6(6) . . ?
C30 C29 H29A 120.7 . . ?
C28 C29 H29A 120.7 . . ?
C31 C30 C29 123.9(7) . . ?
C31 C30 N4 117.6(9) . . ?
C29 C30 N4 118.5(8) . . ?
C30 C31 C32 117.9(7) . . ?
C30 C31 H31B 121.1 . . ?
C32 C31 H31B 121.1 . . ?
C31 C32 C33 120.2(6) . . ?
C31 C32 H32A 119.9 . . ?
C33 C32 H32A 119.9 . . ?
C32 C33 C28 122.4(6) . . ?
C32 C33 H33A 118.8 . . ?
C28 C33 H33A 118.8 . . ?
C25 C261 H26F 109.5 . . ?
C25 C261 H26C 109.5 . . ?
H26F C261 H26C 109.5 . . ?
C25 C261 H26D 109.5 . . ?
H26F C261 H26D 109.5 . . ?
H26C C261 H26D 109.5 . . ?
O91 N41 O81 138(3) . . ?
O91 N41 C301 117(3) . . ?
O81 N41 C301 100(2) . . ?
C25 N31 C271 121.5(12) . . ?
C25 N31 H25A 39.8 . . ?
C271 N31 H25A 89.7 . . ?
C25 N31 H31A 121.9 . . ?
C271 N31 H31A 116.6 . . ?
H25A N31 H31A 144.9 . . ?
O71 C271 N31 124(2) . . ?
O71 C271 C281 121.6(19) . 1_455 ?
N31 C271 C281 114.8(12) . 1_455 ?
O71 C271 H25A 104.7 . . ?
N31 C271 H25A 21.2 . . ?
C281 C271 H25A 132.2 1_455 . ?
C291 C281 C331 120.0 . . ?
C291 C281 C271 113.1(10) . 1_655 ?
C331 C281 C271 126.8(10) . 1_655 ?
C301 C291 C281 120.0 . . ?
C301 C291 H29B 120.0 . . ?
C281 C291 H29B 120.0 . . ?
C311 C301 C291 120.0 . . ?
C311 C301 N41 124.3(16) . . ?
C291 C301 N41 115.7(17) . . ?
C301 C311 C321 120.0 . . ?
C301 C311 H31C 120.0 . . ?
C321 C311 H31C 120.0 . . ?
C331 C321 C311 120.0 . . ?
C331 C321 H32B 120.0 . . ?
C311 C321 H32B 120.0 . . ?
C321 C331 C281 120.0 . . ?
C321 C331 H33B 120.0 . . ?
C281 C331 H33B 120.0 . . ?
C110 O110 H11D 109.5 . . ?
O110 C110 C120 114.0(5) . . ?
O110 C110 H11B 108.8 . . ?
C120 C110 H11B 108.8 . . ?
O110 C110 H11C 108.8 . . ?
C120 C110 H11C 108.8 . . ?
H11B C110 H11C 107.7 . . ?
C110 C120 C130 110.6(6) . . ?
C110 C120 H12C 109.5 . . ?
C130 C120 H12C 109.5 . . ?
C110 C120 H12D 109.5 . . ?
C130 C120 H12D 109.5 . . ?
H12C C120 H12D 108.1 . . ?
C120 C130 H13B 109.5 . . ?
C120 C130 H13C 109.5 . . ?
H13B C130 H13C 109.5 . . ?
C120 C130 H13D 109.5 . . ?
H13B C130 H13D 109.5 . . ?
H13C C130 H13D 109.5 . . ?
C112 O112 H112 109.5 . . ?
O112 C112 C122 123(3) . . ?
O112 C112 H11G 106.5 . . ?
C122 C112 H11G 106.5 . . ?
O112 C112 H11H 106.5 . . ?
C122 C112 H11H 106.5 . . ?
H11G C112 H11H 106.5 . . ?
C112 C122 C132 121(3) . . ?
C112 C122 H12G 107.1 . . ?
C132 C122 H12G 107.1 . . ?
C112 C122 H12H 107.1 . . ?
C132 C122 H12H 107.1 . . ?
H12G C122 H12H 106.8 . . ?
C122 C132 H13H 109.5 . . ?
C122 C132 H13I 109.5 . . ?
H13H C132 H13I 109.5 . . ?
C122 C132 H13J 109.5 . . ?
H13H C132 H13J 109.5 . . ?
H13I C132 H13J 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 1.6(6) . . . . ?
C22 O2 C2 C3 -177.8(4) . . . . ?
C6 C1 C2 O2 -177.8(4) . . . . ?
C6 C1 C2 C3 1.6(6) . . . . ?
C23 O3 C3 C4 8.1(6) . . . . ?
C23 O3 C3 C2 -172.0(4) . . . . ?
O2 C2 C3 O3 -3.5(5) . . . . ?
C1 C2 C3 O3 177.0(4) . . . . ?
O2 C2 C3 C4 176.3(4) . . . . ?
C1 C2 C3 C4 -3.1(6) . . . . ?
O3 C3 C4 C5 -178.1(4) . . . . ?
C2 C3 C4 C5 2.1(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 C7 -173.6(4) . . . . ?
C4 C5 C6 C1 -1.8(6) . . . . ?
C7 C5 C6 C1 173.1(4) . . . . ?
C4 C5 C6 N1 176.8(3) . . . . ?
C7 C5 C6 N1 -8.3(4) . . . . ?
C2 C1 C6 C5 0.8(6) . . . . ?
C2 C1 C6 N1 -177.6(4) . . . . ?
C9 N1 C6 C5 -153.7(4) . . . . ?
C8 N1 C6 C5 -5.0(4) . . . . ?
C9 N1 C6 C1 24.8(6) . . . . ?
C8 N1 C6 C1 173.5(4) . . . . ?
C6 C5 C7 C17 -103.2(4) . . . . ?
C4 C5 C7 C17 71.1(5) . . . . ?
C6 C5 C7 C21 141.3(3) . . . . ?
C4 C5 C7 C21 -44.4(6) . . . . ?
C6 C5 C7 C8 17.1(4) . . . . ?
C4 C5 C7 C8 -168.6(4) . . . . ?
C9 N1 C8 C18 41.8(5) . . . . ?
C6 N1 C8 C18 -108.8(3) . . . . ?
C9 N1 C8 C7 166.0(3) . . . . ?
C6 N1 C8 C7 15.4(4) . . . . ?
C5 C7 C8 N1 -18.9(4) . . . . ?
C17 C7 C8 N1 101.5(3) . . . . ?
C21 C7 C8 N1 -142.9(3) . . . . ?
C5 C7 C8 C18 98.8(3) . . . . ?
C17 C7 C8 C18 -140.8(3) . . . . ?
C21 C7 C8 C18 -25.1(4) . . . . ?
C6 N1 C9 O4 -23.9(6) . . . . ?
C8 N1 C9 O4 -169.7(4) . . . . ?
C6 N1 C9 C10 155.7(4) . . . . ?
C8 N1 C9 C10 10.0(5) . . . . ?
O4 C9 C10 C11 144.1(4) . . . . ?
N1 C9 C10 C11 -35.5(5) . . . . ?
C12 O1 C11 C18 -67.3(4) . . . . ?
C12 O1 C11 C10 172.3(3) . . . . ?
C9 C10 C11 O1 129.0(4) . . . . ?
C9 C10 C11 C18 5.4(5) . . . . ?
C11 O1 C12 C13 87.3(4) . . . . ?
O1 C12 C13 C14 -65.3(6) . . . . ?
C12 C13 C14 C15 178.6(4) . . . . ?
C12 C13 C14 C19 -1.5(6) . . . . ?
C13 C14 C15 N2 -126.7(4) . . . . ?
C19 C14 C15 N2 53.4(5) . . . . ?
C16 N2 C15 C14 76.4(5) . . . . ?
C21 N2 C15 C14 -45.1(5) . . . . ?
C15 N2 C16 C17 -140.9(3) . . . . ?
C21 N2 C16 C17 -15.8(4) . . . . ?
N2 C16 C17 C7 36.2(4) . . . . ?
C5 C7 C17 C16 -164.8(3) . . . . ?
C21 C7 C17 C16 -42.1(4) . . . . ?
C8 C7 C17 C16 81.1(4) . . . . ?
N1 C8 C18 C11 -70.6(3) . . . . ?
C7 C8 C18 C11 173.0(3) . . . . ?
N1 C8 C18 C19 157.2(3) . . . . ?
C7 C8 C18 C19 40.7(4) . . . . ?
O1 C11 C18 C8 -72.1(4) . . . . ?
C10 C11 C18 C8 45.6(4) . . . . ?
O1 C11 C18 C19 57.5(5) . . . . ?
C10 C11 C18 C19 175.2(3) . . . . ?
C13 C14 C19 C18 58.7(5) . . . . ?
C15 C14 C19 C18 -121.4(4) . . . . ?
C13 C14 C19 C20 177.8(4) . . . . ?
C15 C14 C19 C20 -2.3(5) . . . . ?
C8 C18 C19 C14 59.1(4) . . . . ?
C11 C18 C19 C14 -68.4(4) . . . . ?
C8 C18 C19 C20 -62.1(4) . . . . ?
C11 C18 C19 C20 170.4(3) . . . . ?
C14 C19 C20 C21 -55.2(4) . . . . ?
C18 C19 C20 C21 68.7(4) . . . . ?
C19 C20 C21 N2 63.6(4) . . . . ?
C19 C20 C21 C7 -56.2(4) . . . . ?
C16 N2 C21 C20 -136.6(3) . . . . ?
C15 N2 C21 C20 -12.4(4) . . . . ?
C16 N2 C21 C7 -10.7(4) . . . . ?
C15 N2 C21 C7 113.5(4) . . . . ?
C5 C7 C21 C20 -83.4(4) . . . . ?
C17 C7 C21 C20 155.2(3) . . . . ?
C8 C7 C21 C20 33.7(5) . . . . ?
C5 C7 C21 N2 154.0(3) . . . . ?
C17 C7 C21 N2 32.6(4) . . . . ?
C8 C7 C21 N2 -88.9(4) . . . . ?
O51 C24 C25 N31 46.6(14) . . . . ?
O5 C24 C25 N31 100.2(8) . . . . ?
O6 C24 C25 N31 -69.3(9) . . . . ?
O61 C24 C25 N31 -158.1(10) . . . . ?
O51 C24 C25 N3 -87.2(13) . . . . ?
O5 C24 C25 N3 -33.6(6) . . . . ?
O6 C24 C25 N3 156.9(5) . . . . ?
O61 C24 C25 N3 68.0(9) . . . . ?
O51 C24 C25 C26 140.3(13) . . . . ?
O5 C24 C25 C26 -166.1(6) . . . . ?
O6 C24 C25 C26 24.3(8) . . . . ?
O61 C24 C25 C26 -64.5(10) . . . . ?
O51 C24 C25 C261 168.8(15) . . . . ?
O5 C24 C25 C261 -137.6(10) . . . . ?
O6 C24 C25 C261 52.9(11) . . . . ?
O61 C24 C25 C261 -35.9(13) . . . . ?
N31 C25 N3 C27 -19.3(9) . . . . ?
C26 C25 N3 C27 -114.4(6) . . . . ?
C24 C25 N3 C27 113.4(5) . . . . ?
C261 C25 N3 C27 -135.3(8) . . . . ?
C25 N3 C27 O7 -3.7(10) . . . . ?
C25 N3 C27 C28 176.1(5) . . . . ?
O7 C27 C28 C33 176.5(9) . . . . ?
N3 C27 C28 C33 -3.3(9) . . . . ?
O7 C27 C28 C29 -1.8(10) . . . . ?
N3 C27 C28 C29 178.3(5) . . . . ?
C33 C28 C29 C30 0.1(9) . . . . ?
C27 C28 C29 C30 178.7(6) . . . . ?
C28 C29 C30 C31 2.4(10) . . . . ?
C28 C29 C30 N4 -177.7(8) . . . . ?
O9 N4 C30 C31 8.7(15) . . . . ?
O8 N4 C30 C31 -164.5(9) . . . . ?
O9 N4 C30 C29 -171.1(11) . . . . ?
O8 N4 C30 C29 15.6(13) . . . . ?
C29 C30 C31 C32 -3.7(11) . . . . ?
N4 C30 C31 C32 176.4(7) . . . . ?
C30 C31 C32 C33 2.5(10) . . . . ?
C31 C32 C33 C28 -0.1(10) . . . . ?
C29 C28 C33 C32 -1.2(10) . . . . ?
C27 C28 C33 C32 -179.6(6) . . . . ?
N3 C25 N31 C271 20.2(15) . . . . ?
C26 C25 N31 C271 134.4(13) . . . . ?
C24 C25 N31 C271 -112.5(12) . . . . ?
C261 C25 N31 C271 127.3(15) . . . . ?
C25 N31 C271 O71 -5(3) . . . . ?
C25 N31 C271 C281 173.7(10) . . . 1_455 ?
C331 C281 C291 C301 0.0 . . . . ?
C271 C281 C291 C301 178.1(12) 1_655 . . . ?
C281 C291 C301 C311 0.0 . . . . ?
C281 C291 C301 N41 -177.2(18) . . . . ?
O91 N41 C301 C311 178(3) . . . . ?
O81 N41 C301 C311 -22(3) . . . . ?
O91 N41 C301 C291 -5(4) . . . . ?
O81 N41 C301 C291 155.1(17) . . . . ?
C291 C301 C311 C321 0.0 . . . . ?
N41 C301 C311 C321 177(2) . . . . ?
C301 C311 C321 C331 0.0 . . . . ?
C311 C321 C331 C281 0.0 . . . . ?
C291 C281 C331 C321 0.0 . . . . ?
C271 C281 C331 C321 -177.8(13) 1_655 . . . ?
O110 C110 C120 C130 -179.1(5) . . . . ?
O112 C112 C122 C132 147(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.93 1.68 2.595(13) 167.8 .
N2 H2A O5 0.93 1.77 2.658(5) 159.4 .
N3 H3A O6 0.88 2.12 2.897(6) 146.4 4_565
N31 H31A O61 0.97 1.97 2.882(19) 155.6 4_465
O110 H11D O5 0.84 1.96 2.801(5) 177.7 .
O112 H112 O51 0.84 2.09 2.83(4) 146.0 .

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        77.81
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 930487'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97



#==== end



data_b3nb(dl)a/12pr1
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-(D~0.77~L~0.23~)-alaninate propan-1,2-diol solvate
;
_chemical_name_common            ?
_chemical_melting_point          414
_chemical_formula_moiety         'C10 H9 N2 O5, C23 H27 N2 O4, C3 H8 O2'
_chemical_formula_sum            'C36 H44 N4 O11'
_chemical_formula_weight         708.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.798(2)
_cell_length_b                   12.117(3)
_cell_length_c                   35.287(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3334.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12184
_cell_measurement_theta_min      2.8500
_cell_measurement_theta_max      35.4441

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            58567
_diffrn_reflns_av_R_equivalents  0.1496
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         35.53
_reflns_number_total             8277
_reflns_number_gt                4859
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         8277
_refine_ls_number_parameters     562
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3208(3) 0.22413(17) 0.17530(6) 0.0233(4) Uani 1 1 d . . .
O2 O 0.2491(3) 0.79744(18) 0.32317(6) 0.0265(5) Uani 1 1 d . . .
O3 O 0.2086(3) 0.92014(17) 0.26383(6) 0.0266(5) Uani 1 1 d . . .
O4 O 0.2811(4) 0.39557(19) 0.29439(6) 0.0318(6) Uani 1 1 d . . .
N1 N 0.3476(4) 0.47779(19) 0.23848(7) 0.0195(5) Uani 1 1 d . . .
N2 N 0.3660(4) 0.5905(2) 0.11350(7) 0.0257(6) Uani 1 1 d . . .
H2A H 0.3680 0.6522 0.0978 0.031 Uiso 1 1 calc R . .
C1 C 0.2994(4) 0.6315(2) 0.28569(8) 0.0210(6) Uani 1 1 d . . .
H1A H 0.3085 0.5855 0.3074 0.025 Uiso 1 1 calc R . .
C2 C 0.2662(4) 0.7444(2) 0.28888(8) 0.0217(6) Uani 1 1 d . . .
C3 C 0.2487(4) 0.8114(2) 0.25693(8) 0.0214(6) Uani 1 1 d . . .
C4 C 0.2712(4) 0.7680(2) 0.22067(8) 0.0205(6) Uani 1 1 d . . .
H4A H 0.2622 0.8137 0.1989 0.025 Uiso 1 1 calc R . .
C5 C 0.3075(4) 0.6557(2) 0.21729(8) 0.0193(6) Uani 1 1 d . . .
C6 C 0.3185(4) 0.5894(2) 0.24939(8) 0.0194(5) Uani 1 1 d . . .
C7 C 0.3563(4) 0.5910(2) 0.18238(8) 0.0209(6) Uani 1 1 d . . .
C8 C 0.3453(4) 0.4689(2) 0.19639(8) 0.0199(6) Uani 1 1 d . . .
H8A H 0.4474 0.4264 0.1874 0.024 Uiso 1 1 calc R . .
C9 C 0.3030(4) 0.3884(2) 0.25984(9) 0.0235(6) Uani 1 1 d . . .
C10 C 0.2799(4) 0.2803(2) 0.23885(9) 0.0237(6) Uani 1 1 d . . .
H10A H 0.2055 0.2321 0.2544 0.028 Uiso 1 1 calc R . .
H10B H 0.3934 0.2440 0.2371 0.028 Uiso 1 1 calc R . .
C11 C 0.2027(4) 0.2862(2) 0.19849(8) 0.0217(6) Uani 1 1 d . . .
H11A H 0.0885 0.2486 0.1984 0.026 Uiso 1 1 calc R . .
C12 C 0.2632(5) 0.2055(2) 0.13714(9) 0.0283(7) Uani 1 1 d . . .
H12A H 0.1368 0.1979 0.1370 0.034 Uiso 1 1 calc R . .
H12B H 0.3128 0.1356 0.1276 0.034 Uiso 1 1 calc R . .
C13 C 0.3140(5) 0.2983(2) 0.11105(9) 0.0258(6) Uani 1 1 d . . .
H13A H 0.3922 0.2842 0.0910 0.031 Uiso 1 1 calc R . .
C14 C 0.2515(4) 0.4000(2) 0.11552(8) 0.0241(6) Uani 1 1 d . . .
C15 C 0.3045(5) 0.4933(2) 0.08997(8) 0.0265(7) Uani 1 1 d . . .
H15A H 0.2061 0.5162 0.0741 0.032 Uiso 1 1 calc R . .
H15B H 0.3977 0.4684 0.0729 0.032 Uiso 1 1 calc R . .
C16 C 0.5424(5) 0.5744(3) 0.12871(9) 0.0281(7) Uani 1 1 d . . .
H16A H 0.6274 0.6149 0.1132 0.034 Uiso 1 1 calc R . .
H16B H 0.5732 0.4952 0.1289 0.034 Uiso 1 1 calc R . .
C17 C 0.5368(5) 0.6201(3) 0.16869(8) 0.0237(6) Uani 1 1 d . . .
H17A H 0.5548 0.7010 0.1687 0.028 Uiso 1 1 calc R . .
H17B H 0.6250 0.5849 0.1848 0.028 Uiso 1 1 calc R . .
C18 C 0.1793(4) 0.4067(2) 0.18630(7) 0.0182(5) Uani 1 1 d . . .
H18A H 0.0881 0.4378 0.2031 0.022 Uiso 1 1 calc R . .
C19 C 0.1204(4) 0.4291(2) 0.14556(8) 0.0227(6) Uani 1 1 d . . .
H19A H 0.0128 0.3865 0.1406 0.027 Uiso 1 1 calc R . .
C20 C 0.0800(5) 0.5526(3) 0.14366(9) 0.0251(6) Uani 1 1 d . . .
H20A H 0.0231 0.5703 0.1193 0.030 Uiso 1 1 calc R . .
H20B H 0.0016 0.5733 0.1646 0.030 Uiso 1 1 calc R . .
C21 C 0.2451(4) 0.6162(2) 0.14698(8) 0.0212(6) Uani 1 1 d . . .
H21A H 0.2180 0.6969 0.1467 0.025 Uiso 1 1 calc R . .
C22 C 0.2712(5) 0.7313(3) 0.35637(9) 0.0307(7) Uani 1 1 d . . .
H22A H 0.2559 0.7773 0.3790 0.046 Uiso 1 1 calc R . .
H22B H 0.3868 0.6995 0.3564 0.046 Uiso 1 1 calc R . .
H22C H 0.1861 0.6718 0.3565 0.046 Uiso 1 1 calc R . .
C23 C 0.1759(6) 0.9878(3) 0.23136(10) 0.0374(9) Uani 1 1 d . . .
H23A H 0.1509 1.0633 0.2396 0.056 Uiso 1 1 calc R . .
H23B H 0.0773 0.9583 0.2174 0.056 Uiso 1 1 calc R . .
H23C H 0.2770 0.9880 0.2149 0.056 Uiso 1 1 calc R . .
O5 O 0.3056(6) 0.7751(3) 0.07466(9) 0.0254(8) Uani 0.759(7) 1 d PU A 1
O6 O 0.4746(5) 0.6876(3) 0.03422(9) 0.0345(10) Uani 0.759(7) 1 d P A 1
O51 O 0.411(2) 0.7706(9) 0.0720(3) 0.031(3) Uani 0.241(7) 1 d PU A 2
O61 O 0.2611(18) 0.6785(9) 0.0309(3) 0.048(4) Uani 0.241(7) 1 d P A 2
O8 O -0.0491(5) 1.4025(3) 0.06217(10) 0.0575(9) Uani 1 1 d . . .
O9 O -0.3237(4) 1.3940(3) 0.05743(9) 0.0478(7) Uani 1 1 d . . .
N4 N -0.1798(5) 1.3528(3) 0.05450(8) 0.0335(7) Uani 1 1 d . B .
C24 C 0.3767(5) 0.7660(2) 0.04273(9) 0.0260(7) Uani 1 1 d . . .
C25 C 0.3681(5) 0.8639(3) 0.01499(10) 0.0313(8) Uani 1 1 d . . .
H25B H 0.2713 0.9088 0.0218 0.038 Uiso 0.230(7) 1 d PR B 2
H25A H 0.4542 0.9148 0.0235 0.038 Uiso 0.770(7) 1 d PR B 1
O7 O 0.3159(7) 1.0819(6) 0.0416(2) 0.0411(12) Uani 0.770(7) 1 d PU . 1
N3 N 0.2088(5) 0.9231(3) 0.01771(9) 0.0226(8) Uani 0.770(7) 1 d P . 1
H3A H 0.1143 0.8885 0.0111 0.027 Uiso 0.770(7) 1 calc PR B 1
C26 C 0.4154(9) 0.8347(5) -0.02447(14) 0.0394(14) Uani 0.770(7) 1 d PU . 1
H26A H 0.5357 0.8115 -0.0253 0.059 Uiso 0.770(7) 1 calc PR B 1
H26B H 0.3996 0.8992 -0.0409 0.059 Uiso 0.770(7) 1 calc PR B 1
H26C H 0.3422 0.7743 -0.0333 0.059 Uiso 0.770(7) 1 calc PR B 1
C27 C 0.1952(5) 1.0277(3) 0.02975(11) 0.0206(8) Uani 0.770(7) 1 d P . 1
C28 C 0.0116(5) 1.0814(3) 0.02737(9) 0.0278(7) Uani 1 1 d . . .
H28A H 0.1197 1.0453 0.0275 0.033 Uiso 0.230(7) 1 calc PR B 2
C29 C -0.0042(5) 1.1885(3) 0.04115(10) 0.0295(7) Uani 1 1 d . B .
H29A H 0.0934 1.2269 0.0504 0.035 Uiso 1 1 calc R . .
C30 C -0.1655(5) 1.2388(3) 0.04121(8) 0.0300(7) Uani 1 1 d . . .
C31 C -0.3074(6) 1.1867(3) 0.02883(14) 0.0472(11) Uani 1 1 d . B .
H31A H -0.4166 1.2214 0.0299 0.057 Uiso 1 1 calc R . .
C32 C -0.2889(6) 1.0804(3) 0.01439(17) 0.0601(15) Uani 1 1 d . . .
H32A H -0.3866 1.0426 0.0049 0.072 Uiso 0.770(7) 1 calc PR B 1
C33 C -0.1298(6) 1.0288(3) 0.01364(11) 0.0386(9) Uani 1 1 d . B .
H33A H -0.1195 0.9565 0.0035 0.046 Uiso 1 1 calc R . .
O71 O 0.373(2) 1.072(2) 0.0373(7) 0.036(4) Uani 0.230(7) 1 d PU . 2
N31 N 0.4990(15) 0.9220(10) 0.0142(3) 0.025(3) Uani 0.230(7) 1 d PU . 2
H31C H 0.5945 0.8941 0.0050 0.030 Uiso 0.230(7) 1 calc PR B 2
C261 C 0.321(3) 0.8088(15) -0.0303(5) 0.035(3) Uani 0.230(7) 1 d PU . 2
H26D H 0.4219 0.7701 -0.0401 0.053 Uiso 0.230(7) 1 calc PR B 2
H26E H 0.2899 0.8688 -0.0476 0.053 Uiso 0.230(7) 1 calc PR B 2
H26F H 0.2249 0.7570 -0.0282 0.053 Uiso 0.230(7) 1 calc PR B 2
C271 C 0.4986(18) 1.0267(11) 0.0272(4) 0.023(3) Uani 0.230(7) 1 d PU . 2
O101 O 0.1947(7) 0.9090(5) 0.13445(14) 0.0317(11) Uani 0.802(9) 1 d PDU C 1
H101 H 0.2478 0.9029 0.1138 0.048 Uiso 0.802(9) 1 calc PR C 1
O102 O -0.1062(6) 0.7778(3) 0.14840(13) 0.0384(10) Uani 0.802(9) 1 d PU C 1
H102 H -0.1572 0.8079 0.1666 0.058 Uiso 0.802(9) 1 calc PR C 1
C101 C 0.0273(7) 0.9465(4) 0.12741(13) 0.0306(11) Uani 0.802(9) 1 d PD C 1
H10C H 0.0297 0.9996 0.1061 0.037 Uiso 0.802(9) 1 calc PR C 1
H10D H -0.0157 0.9858 0.1501 0.037 Uiso 0.802(9) 1 calc PR C 1
C102 C -0.0943(7) 0.8532(4) 0.11785(13) 0.0351(12) Uani 0.802(9) 1 d PU C 1
H10E H -0.0500 0.8134 0.0950 0.042 Uiso 0.802(9) 1 calc PR C 1
C103 C -0.2768(10) 0.9014(8) 0.1086(2) 0.0488(17) Uani 0.802(9) 1 d PU C 1
H10F H -0.3552 0.8409 0.1023 0.073 Uiso 0.802(9) 1 calc PR C 1
H10G H -0.2684 0.9520 0.0870 0.073 Uiso 0.802(9) 1 calc PR C 1
H10H H -0.3205 0.9415 0.1307 0.073 Uiso 0.802(9) 1 calc PR C 1
O111 O 0.254(3) 0.906(2) 0.1296(7) 0.036(4) Uani 0.198(9) 1 d PDU C 2
H111 H 0.3274 0.8685 0.1176 0.054 Uiso 0.198(9) 1 calc PR C 2
O112 O -0.043(2) 0.8068(15) 0.1584(4) 0.034(3) Uani 0.198(9) 1 d PU C 2
H112 H -0.1315 0.7996 0.1718 0.050 Uiso 0.198(9) 1 calc PR C 2
C111 C 0.097(4) 0.902(3) 0.1101(10) 0.084(10) Uani 0.198(9) 1 d PDU C 2
H11B H 0.0952 0.8351 0.0941 0.101 Uiso 0.198(9) 1 calc PR C 2
H11C H 0.0916 0.9668 0.0929 0.101 Uiso 0.198(9) 1 calc PR C 2
C112 C -0.061(3) 0.9024(18) 0.1346(6) 0.038(4) Uani 0.198(9) 1 d PU C 2
H11D H -0.0529 0.9684 0.1515 0.046 Uiso 0.198(9) 1 calc PR C 2
C113 C -0.223(4) 0.911(4) 0.1143(10) 0.047(5) Uani 0.198(9) 1 d PU C 2
H11I H -0.2243 0.9791 0.0994 0.070 Uiso 0.198(9) 1 calc PR C 2
H11J H -0.3177 0.9115 0.1325 0.070 Uiso 0.198(9) 1 calc PR C 2
H11K H -0.2352 0.8473 0.0973 0.070 Uiso 0.198(9) 1 calc PR C 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0328(12) 0.0176(9) 0.0194(9) -0.0018(8) -0.0016(9) 0.0016(9)
O2 0.0377(13) 0.0256(11) 0.0160(9) -0.0054(8) 0.0032(9) 0.0006(10)
O3 0.0393(13) 0.0173(9) 0.0233(10) -0.0034(8) 0.0026(9) 0.0012(10)
O4 0.0542(17) 0.0256(11) 0.0156(9) 0.0041(8) 0.0029(10) -0.0005(12)
N1 0.0304(13) 0.0143(10) 0.0137(10) 0.0003(8) -0.0002(10) -0.0002(10)
N2 0.0471(17) 0.0164(11) 0.0136(10) -0.0024(9) 0.0019(11) -0.0039(12)
C1 0.0250(15) 0.0216(13) 0.0164(12) -0.0013(10) -0.0019(11) -0.0019(12)
C2 0.0245(15) 0.0232(14) 0.0173(12) -0.0054(10) 0.0040(11) -0.0056(12)
C3 0.0285(15) 0.0165(12) 0.0192(13) -0.0038(10) 0.0009(12) -0.0031(12)
C4 0.0252(15) 0.0166(12) 0.0199(13) -0.0008(10) 0.0005(11) -0.0011(12)
C5 0.0261(15) 0.0173(12) 0.0145(11) -0.0011(9) 0.0016(11) -0.0019(12)
C6 0.0256(14) 0.0128(11) 0.0198(12) -0.0005(10) -0.0004(11) -0.0014(12)
C7 0.0295(16) 0.0175(12) 0.0156(12) -0.0022(10) 0.0012(11) -0.0054(12)
C8 0.0294(16) 0.0158(12) 0.0145(12) 0.0001(9) -0.0012(11) -0.0022(12)
C9 0.0289(16) 0.0184(13) 0.0231(14) 0.0032(11) 0.0005(12) -0.0007(12)
C10 0.0314(17) 0.0164(12) 0.0234(13) 0.0025(11) -0.0019(12) -0.0018(12)
C11 0.0305(16) 0.0147(12) 0.0200(12) -0.0004(10) -0.0009(12) 0.0006(12)
C12 0.043(2) 0.0180(13) 0.0235(14) -0.0063(11) -0.0028(14) -0.0021(14)
C13 0.0395(18) 0.0173(12) 0.0206(13) -0.0033(10) -0.0010(13) -0.0019(14)
C14 0.0353(17) 0.0208(13) 0.0161(12) -0.0037(11) -0.0038(12) -0.0010(13)
C15 0.046(2) 0.0178(12) 0.0154(12) -0.0020(10) -0.0001(13) -0.0040(14)
C16 0.0416(19) 0.0234(15) 0.0193(14) -0.0035(12) 0.0076(13) -0.0044(15)
C17 0.0331(17) 0.0214(14) 0.0165(13) -0.0026(11) 0.0043(11) -0.0055(13)
C18 0.0247(15) 0.0131(11) 0.0168(11) -0.0001(9) 0.0007(11) -0.0002(12)
C19 0.0321(17) 0.0162(12) 0.0197(13) 0.0019(10) -0.0045(12) 0.0021(12)
C20 0.0347(18) 0.0186(13) 0.0221(14) -0.0004(11) -0.0074(13) 0.0014(13)
C21 0.0334(16) 0.0156(12) 0.0148(11) -0.0010(9) -0.0003(12) 0.0010(12)
C22 0.040(2) 0.0342(16) 0.0178(13) -0.0028(13) 0.0002(13) -0.0008(16)
C23 0.065(3) 0.0148(13) 0.0327(17) 0.0003(12) 0.0026(18) 0.0070(17)
O5 0.031(2) 0.0215(14) 0.0239(14) 0.0024(11) 0.0087(14) 0.0045(15)
O6 0.053(2) 0.0232(16) 0.0273(17) 0.0006(13) 0.0123(15) 0.0115(15)
O51 0.050(7) 0.020(4) 0.025(4) 0.000(4) -0.004(5) -0.007(5)
O61 0.068(9) 0.028(5) 0.047(7) 0.012(5) -0.036(6) -0.028(6)
O8 0.060(2) 0.0403(17) 0.072(2) -0.0252(16) -0.0279(17) 0.0105(16)
O9 0.0544(19) 0.0431(16) 0.0458(16) 0.0104(13) 0.0108(14) 0.0144(15)
N4 0.0468(19) 0.0349(15) 0.0187(12) -0.0007(11) -0.0029(13) 0.0058(16)
C24 0.0425(19) 0.0142(12) 0.0211(14) 0.0001(11) 0.0027(13) 0.0003(13)
C25 0.0366(19) 0.0224(15) 0.0349(17) 0.0114(13) 0.0084(15) 0.0054(15)
O7 0.025(3) 0.034(2) 0.064(3) -0.0193(19) -0.004(3) -0.007(3)
N3 0.0220(17) 0.0186(15) 0.0273(17) 0.0056(13) -0.0008(13) 0.0002(14)
C26 0.045(3) 0.048(3) 0.026(2) 0.013(2) 0.018(2) 0.016(3)
C27 0.0178(18) 0.0225(17) 0.0214(17) 0.0026(14) 0.0010(14) -0.0008(15)
C28 0.0393(19) 0.0242(15) 0.0200(14) 0.0001(12) 0.0062(13) -0.0085(15)
C29 0.0343(19) 0.0237(15) 0.0305(16) -0.0055(13) 0.0053(14) -0.0042(14)
C30 0.046(2) 0.0291(15) 0.0149(12) 0.0066(11) -0.0014(13) -0.0019(16)
C31 0.044(2) 0.0348(19) 0.063(3) 0.0219(19) -0.016(2) -0.0038(19)
C32 0.047(3) 0.0263(19) 0.107(4) 0.020(2) -0.038(3) -0.0058(19)
C33 0.050(2) 0.0228(16) 0.043(2) 0.0066(15) -0.0160(18) -0.0093(17)
O71 0.024(7) 0.033(5) 0.051(6) -0.009(5) 0.000(6) -0.004(6)
N31 0.018(5) 0.019(5) 0.036(6) -0.003(4) -0.007(4) -0.005(4)
C261 0.039(6) 0.032(6) 0.035(6) 0.006(5) -0.004(6) -0.010(6)
C271 0.025(6) 0.021(5) 0.023(5) -0.009(4) 0.008(5) 0.002(5)
O101 0.035(3) 0.0308(17) 0.0289(18) -0.0025(14) 0.006(2) -0.001(3)
O102 0.046(3) 0.0254(17) 0.044(2) 0.0018(16) 0.0155(19) -0.0003(17)
C101 0.046(3) 0.0194(19) 0.026(2) -0.0002(16) 0.0032(19) -0.001(2)
C102 0.052(3) 0.029(2) 0.024(2) -0.0112(17) 0.011(2) -0.012(2)
C103 0.050(5) 0.062(4) 0.034(3) 0.010(3) -0.011(3) -0.007(4)
O111 0.035(9) 0.032(6) 0.041(7) 0.013(6) 0.006(7) -0.002(8)
O112 0.038(6) 0.035(6) 0.028(5) 0.001(5) -0.002(5) -0.003(5)
C111 0.092(13) 0.077(13) 0.083(13) -0.002(9) 0.005(9) -0.008(9)
C112 0.055(7) 0.030(6) 0.030(6) 0.000(5) 0.003(6) -0.005(6)
C113 0.045(9) 0.055(7) 0.039(7) 0.009(6) -0.005(7) 0.000(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.437(4) . ?
O1 C11 1.443(4) . ?
O2 C2 1.377(3) . ?
O2 C22 1.430(4) . ?
O3 C3 1.376(4) . ?
O3 C23 1.432(4) . ?
O4 C9 1.234(4) . ?
N1 C9 1.365(4) . ?
N1 C6 1.425(4) . ?
N1 C8 1.489(4) . ?
N2 C16 1.490(5) . ?
N2 C15 1.518(4) . ?
N2 C21 1.543(4) . ?
N2 H2A 0.9300 . ?
C1 C6 1.386(4) . ?
C1 C2 1.397(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.396(4) . ?
C3 C4 1.394(4) . ?
C4 C5 1.395(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(4) . ?
C5 C7 1.509(4) . ?
C7 C17 1.529(5) . ?
C7 C21 1.551(4) . ?
C7 C8 1.562(4) . ?
C8 C18 1.540(4) . ?
C8 H8A 1.0000 . ?
C9 C10 1.515(4) . ?
C10 C11 1.548(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.533(4) . ?
C11 H11A 1.0000 . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.335(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.504(4) . ?
C14 C19 1.514(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.516(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.533(4) . ?
C18 H18A 1.0000 . ?
C19 C20 1.531(4) . ?
C19 H19A 1.0000 . ?
C20 C21 1.505(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.260(4) . ?
O6 C24 1.255(5) . ?
O51 C24 1.067(10) . ?
O61 C24 1.454(10) . ?
O8 N4 1.214(5) . ?
O9 N4 1.233(5) . ?
N4 C30 1.462(5) . ?
C24 C25 1.540(4) . ?
C25 N31 1.240(12) . ?
C25 N3 1.437(5) . ?
C25 C26 1.483(6) . ?
C25 C261 1.770(18) . ?
C25 H25B 0.9599 . ?
C25 H25A 0.9600 . ?
O7 C27 1.222(7) . ?
N3 C27 1.341(5) . ?
N3 H25B 0.5369 . ?
N3 H3A 0.8800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.575(5) . ?
C28 C33 1.362(5) . ?
C28 C29 1.392(5) . ?
C28 H28A 0.9500 . ?
C29 C30 1.398(5) . ?
C29 H29A 0.9500 . ?
C30 C31 1.347(6) . ?
C31 C32 1.393(7) . ?
C31 H31A 0.9500 . ?
C32 C33 1.390(6) . ?
C32 C271 1.837(15) 1_455 ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
O71 C271 1.18(2) . ?
N31 C271 1.349(18) . ?
N31 H25A 0.4867 . ?
N31 H31C 0.8800 . ?
C261 H26D 0.9800 . ?
C261 H26E 0.9800 . ?
C261 H26F 0.9800 . ?
C271 C32 1.837(15) 1_655 ?
O101 C101 1.404(7) . ?
O101 H101 0.8400 . ?
O102 C102 1.416(6) . ?
O102 H102 0.8400 . ?
C101 C102 1.513(7) . ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?
C102 C103 1.573(10) . ?
C102 H10E 1.0000 . ?
C103 H10F 0.9800 . ?
C103 H10G 0.9800 . ?
C103 H10H 0.9800 . ?
O111 C111 1.404(9) . ?
O111 H111 0.8400 . ?
O112 C112 1.44(3) . ?
O112 H112 0.8400 . ?
C111 C112 1.51(4) . ?
C111 H11B 0.9900 . ?
C111 H11C 0.9900 . ?
C112 C113 1.46(4) . ?
C112 H11D 1.0000 . ?
C113 H11I 0.9800 . ?
C113 H11J 0.9800 . ?
C113 H11K 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C11 114.4(2) . . ?
C2 O2 C22 116.5(2) . . ?
C3 O3 C23 116.6(2) . . ?
C9 N1 C6 124.3(2) . . ?
C9 N1 C8 119.4(2) . . ?
C6 N1 C8 109.6(2) . . ?
C16 N2 C15 112.8(3) . . ?
C16 N2 C21 108.3(2) . . ?
C15 N2 C21 112.5(3) . . ?
C16 N2 H2A 107.7 . . ?
C15 N2 H2A 107.7 . . ?
C21 N2 H2A 107.7 . . ?
C6 C1 C2 117.0(3) . . ?
C6 C1 H1A 121.5 . . ?
C2 C1 H1A 121.5 . . ?
O2 C2 C3 115.4(3) . . ?
O2 C2 C1 123.1(3) . . ?
C3 C2 C1 121.5(3) . . ?
O3 C3 C4 123.5(3) . . ?
O3 C3 C2 115.9(2) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 C7 110.5(2) . . ?
C4 C5 C7 128.9(3) . . ?
C1 C6 C5 122.3(3) . . ?
C1 C6 N1 128.0(2) . . ?
C5 C6 N1 109.7(2) . . ?
C5 C7 C17 111.7(2) . . ?
C5 C7 C21 114.5(3) . . ?
C17 C7 C21 102.4(2) . . ?
C5 C7 C8 102.7(2) . . ?
C17 C7 C8 111.7(3) . . ?
C21 C7 C8 114.3(2) . . ?
N1 C8 C18 106.0(2) . . ?
N1 C8 C7 104.3(2) . . ?
C18 C8 C7 115.9(2) . . ?
N1 C8 H8A 110.1 . . ?
C18 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
O4 C9 N1 121.6(3) . . ?
O4 C9 C10 121.8(3) . . ?
N1 C9 C10 116.5(3) . . ?
C9 C10 C11 117.1(2) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 114.4(2) . . ?
O1 C11 C10 104.4(2) . . ?
C18 C11 C10 110.4(2) . . ?
O1 C11 H11A 109.2 . . ?
C18 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
O1 C12 C13 111.9(3) . . ?
O1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 C19 123.0(3) . . ?
C15 C14 C19 115.5(3) . . ?
C14 C15 N2 110.0(2) . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
N2 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 105.1(3) . . ?
N2 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
N2 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 103.7(3) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C11 C18 C19 117.9(2) . . ?
C11 C18 C8 107.6(2) . . ?
C19 C18 C8 112.5(2) . . ?
C11 C18 H18A 106.0 . . ?
C19 C18 H18A 106.0 . . ?
C8 C18 H18A 106.0 . . ?
C14 C19 C20 109.6(3) . . ?
C14 C19 C18 114.4(3) . . ?
C20 C19 C18 106.0(2) . . ?
C14 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C21 C20 C19 108.7(3) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 111.1(2) . . ?
C20 C21 C7 116.1(2) . . ?
N2 C21 C7 103.6(3) . . ?
C20 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 N4 O9 123.0(3) . . ?
O8 N4 C30 118.4(3) . . ?
O9 N4 C30 118.6(3) . . ?
O51 C24 O6 96.9(8) . . ?
O51 C24 O5 40.6(8) . . ?
O6 C24 O5 123.2(3) . . ?
O51 C24 O61 118.1(8) . . ?
O6 C24 O61 75.9(6) . . ?
O5 C24 O61 92.7(6) . . ?
O51 C24 C25 125.9(6) . . ?
O6 C24 C25 117.3(3) . . ?
O5 C24 C25 118.8(3) . . ?
O61 C24 C25 110.6(5) . . ?
N31 C25 N3 115.5(6) . . ?
N31 C25 C26 84.9(7) . . ?
N3 C25 C26 113.4(4) . . ?
N31 C25 C24 114.5(6) . . ?
N3 C25 C24 112.3(3) . . ?
C26 C25 C24 113.7(3) . . ?
N31 C25 C261 111.5(9) . . ?
N3 C25 C261 94.0(8) . . ?
C26 C25 C261 27.7(6) . . ?
C24 C25 C261 107.0(6) . . ?
N31 C25 H25B 109.3 . . ?
N3 C25 H25B 12.1 . . ?
C26 C25 H25B 124.4 . . ?
C24 C25 H25B 108.2 . . ?
C261 C25 H25B 106.0 . . ?
N31 C25 H25A 21.0 . . ?
N3 C25 H25A 105.3 . . ?
C26 C25 H25A 105.9 . . ?
C24 C25 H25A 105.3 . . ?
C261 C25 H25A 132.1 . . ?
H25B C25 H25A 96.2 . . ?
C27 N3 C25 124.1(3) . . ?
C27 N3 H25B 107.0 . . ?
C25 N3 H25B 21.9 . . ?
C27 N3 H3A 117.9 . . ?
C25 N3 H3A 117.9 . . ?
H25B N3 H3A 132.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 N3 123.8(5) . . ?
O7 C27 C28 119.8(4) . . ?
N3 C27 C28 116.5(3) . . ?
O7 C27 H25B 105.1 . . ?
N3 C27 H25B 18.9 . . ?
C28 C27 H25B 135.0 . . ?
C33 C28 C29 119.3(4) . . ?
C33 C28 C27 124.2(3) . . ?
C29 C28 C27 116.6(3) . . ?
C33 C28 H28A 120.4 . . ?
C29 C28 H28A 120.4 . . ?
C27 C28 H28A 4.0 . . ?
C28 C29 C30 119.1(3) . . ?
C28 C29 H29A 120.4 . . ?
C30 C29 H29A 120.4 . . ?
C31 C30 C29 122.3(3) . . ?
C31 C30 N4 118.9(4) . . ?
C29 C30 N4 118.8(3) . . ?
C30 C31 C32 117.8(4) . . ?
C30 C31 H31A 121.1 . . ?
C32 C31 H31A 121.1 . . ?
C33 C32 C31 121.0(4) . . ?
C33 C32 C271 130.6(5) . 1_455 ?
C31 C32 C271 98.3(6) . 1_455 ?
C33 C32 H32A 119.5 . . ?
C31 C32 H32A 119.5 . . ?
C271 C32 H32A 36.1 1_455 . ?
C28 C33 C32 120.3(4) . . ?
C28 C33 H33A 119.8 . . ?
C32 C33 H33A 119.8 . . ?
C25 N31 C271 121.7(11) . . ?
C25 N31 H25A 45.1 . . ?
C271 N31 H25A 86.5 . . ?
C25 N31 H31C 119.2 . . ?
C271 N31 H31C 119.2 . . ?
H25A N31 H31C 141.9 . . ?
C25 C261 H26D 109.5 . . ?
C25 C261 H26E 109.5 . . ?
H26D C261 H26E 109.5 . . ?
C25 C261 H26F 109.5 . . ?
H26D C261 H26F 109.5 . . ?
H26E C261 H26F 109.5 . . ?
O71 C271 N31 123.0(17) . . ?
O71 C271 C32 131.1(16) . 1_655 ?
N31 C271 C32 104.4(9) . 1_655 ?
O71 C271 H25A 106.0 . . ?
N31 C271 H25A 20.2 . . ?
C32 C271 H25A 122.8 1_655 . ?
C101 O101 H101 109.5 . . ?
C102 O102 H102 109.5 . . ?
O101 C101 C102 112.4(5) . . ?
O101 C101 H10C 109.1 . . ?
C102 C101 H10C 109.1 . . ?
O101 C101 H10D 109.1 . . ?
C102 C101 H10D 109.1 . . ?
H10C C101 H10D 107.9 . . ?
O102 C102 C101 110.7(4) . . ?
O102 C102 C103 109.8(5) . . ?
C101 C102 C103 109.6(5) . . ?
O102 C102 H10E 108.9 . . ?
C101 C102 H10E 108.9 . . ?
C103 C102 H10E 108.9 . . ?
C102 C103 H10F 109.5 . . ?
C102 C103 H10G 109.5 . . ?
H10F C103 H10G 109.5 . . ?
C102 C103 H10H 109.5 . . ?
H10F C103 H10H 109.5 . . ?
H10G C103 H10H 109.5 . . ?
C111 O111 H111 109.5 . . ?
C112 O112 H112 109.5 . . ?
O111 C111 C112 116(3) . . ?
O111 C111 H11B 108.4 . . ?
C112 C111 H11B 108.4 . . ?
O111 C111 H11C 108.4 . . ?
C112 C111 H11C 108.4 . . ?
H11B C111 H11C 107.5 . . ?
O112 C112 C113 115(3) . . ?
O112 C112 C111 105(2) . . ?
C113 C112 C111 115(2) . . ?
O112 C112 H11D 107.0 . . ?
C113 C112 H11D 107.0 . . ?
C111 C112 H11D 107.0 . . ?
C112 C113 H11I 109.5 . . ?
C112 C113 H11J 109.5 . . ?
H11I C113 H11J 109.5 . . ?
C112 C113 H11K 109.5 . . ?
H11I C113 H11K 109.5 . . ?
H11J C113 H11K 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C3 -178.3(3) . . . . ?
C22 O2 C2 C1 1.5(4) . . . . ?
C6 C1 C2 O2 -178.2(3) . . . . ?
C6 C1 C2 C3 1.6(5) . . . . ?
C23 O3 C3 C4 5.2(5) . . . . ?
C23 O3 C3 C2 -174.9(3) . . . . ?
O2 C2 C3 O3 -3.0(4) . . . . ?
C1 C2 C3 O3 177.2(3) . . . . ?
O2 C2 C3 C4 177.0(3) . . . . ?
C1 C2 C3 C4 -2.8(5) . . . . ?
O3 C3 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C5 C7 -172.6(3) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C2 C1 C6 N1 -178.0(3) . . . . ?
C4 C5 C6 C1 -2.0(5) . . . . ?
C7 C5 C6 C1 172.5(3) . . . . ?
C4 C5 C6 N1 177.0(3) . . . . ?
C7 C5 C6 N1 -8.5(4) . . . . ?
C9 N1 C6 C1 24.4(5) . . . . ?
C8 N1 C6 C1 175.3(3) . . . . ?
C9 N1 C6 C5 -154.5(3) . . . . ?
C8 N1 C6 C5 -3.6(4) . . . . ?
C6 C5 C7 C17 -103.6(3) . . . . ?
C4 C5 C7 C17 70.3(4) . . . . ?
C6 C5 C7 C21 140.6(3) . . . . ?
C4 C5 C7 C21 -45.5(5) . . . . ?
C6 C5 C7 C8 16.2(3) . . . . ?
C4 C5 C7 C8 -169.9(3) . . . . ?
C9 N1 C8 C18 43.2(4) . . . . ?
C6 N1 C8 C18 -109.4(3) . . . . ?
C9 N1 C8 C7 166.0(3) . . . . ?
C6 N1 C8 C7 13.4(3) . . . . ?
C5 C7 C8 N1 -17.3(3) . . . . ?
C17 C7 C8 N1 102.6(3) . . . . ?
C21 C7 C8 N1 -141.8(3) . . . . ?
C5 C7 C8 C18 98.9(3) . . . . ?
C17 C7 C8 C18 -141.3(3) . . . . ?
C21 C7 C8 C18 -25.7(4) . . . . ?
C6 N1 C9 O4 -22.0(5) . . . . ?
C8 N1 C9 O4 -170.3(3) . . . . ?
C6 N1 C9 C10 157.3(3) . . . . ?
C8 N1 C9 C10 9.0(4) . . . . ?
O4 C9 C10 C11 143.9(3) . . . . ?
N1 C9 C10 C11 -35.4(4) . . . . ?
C12 O1 C11 C18 -67.2(3) . . . . ?
C12 O1 C11 C10 172.0(2) . . . . ?
C9 C10 C11 O1 128.6(3) . . . . ?
C9 C10 C11 C18 5.2(4) . . . . ?
C11 O1 C12 C13 88.0(3) . . . . ?
O1 C12 C13 C14 -64.9(4) . . . . ?
C12 C13 C14 C15 178.8(3) . . . . ?
C12 C13 C14 C19 -2.8(5) . . . . ?
C13 C14 C15 N2 -127.4(3) . . . . ?
C19 C14 C15 N2 54.1(4) . . . . ?
C16 N2 C15 C14 77.2(3) . . . . ?
C21 N2 C15 C14 -45.7(4) . . . . ?
C15 N2 C16 C17 -140.0(3) . . . . ?
C21 N2 C16 C17 -14.8(3) . . . . ?
N2 C16 C17 C7 35.1(3) . . . . ?
C5 C7 C17 C16 -164.3(3) . . . . ?
C21 C7 C17 C16 -41.4(3) . . . . ?
C8 C7 C17 C16 81.3(3) . . . . ?
O1 C11 C18 C19 56.8(4) . . . . ?
C10 C11 C18 C19 174.2(3) . . . . ?
O1 C11 C18 C8 -71.6(3) . . . . ?
C10 C11 C18 C8 45.8(3) . . . . ?
N1 C8 C18 C11 -71.1(3) . . . . ?
C7 C8 C18 C11 173.7(2) . . . . ?
N1 C8 C18 C19 157.5(2) . . . . ?
C7 C8 C18 C19 42.3(3) . . . . ?
C13 C14 C19 C20 178.5(3) . . . . ?
C15 C14 C19 C20 -3.1(4) . . . . ?
C13 C14 C19 C18 59.6(4) . . . . ?
C15 C14 C19 C18 -121.9(3) . . . . ?
C11 C18 C19 C14 -68.3(4) . . . . ?
C8 C18 C19 C14 57.7(3) . . . . ?
C11 C18 C19 C20 170.8(3) . . . . ?
C8 C18 C19 C20 -63.1(3) . . . . ?
C14 C19 C20 C21 -55.0(3) . . . . ?
C18 C19 C20 C21 68.9(3) . . . . ?
C19 C20 C21 N2 62.7(3) . . . . ?
C19 C20 C21 C7 -55.3(3) . . . . ?
C16 N2 C21 C20 -136.1(3) . . . . ?
C15 N2 C21 C20 -10.7(3) . . . . ?
C16 N2 C21 C7 -10.8(3) . . . . ?
C15 N2 C21 C7 114.6(3) . . . . ?
C5 C7 C21 C20 -85.2(3) . . . . ?
C17 C7 C21 C20 153.7(3) . . . . ?
C8 C7 C21 C20 32.8(4) . . . . ?
C5 C7 C21 N2 152.8(2) . . . . ?
C17 C7 C21 N2 31.7(3) . . . . ?
C8 C7 C21 N2 -89.2(3) . . . . ?
O51 C24 C25 N31 51.7(13) . . . . ?
O6 C24 C25 N31 -70.8(8) . . . . ?
O5 C24 C25 N31 99.6(8) . . . . ?
O61 C24 C25 N31 -155.1(9) . . . . ?
O51 C24 C25 N3 -82.5(12) . . . . ?
O6 C24 C25 N3 155.0(4) . . . . ?
O5 C24 C25 N3 -34.7(5) . . . . ?
O61 C24 C25 N3 70.7(7) . . . . ?
O51 C24 C25 C26 147.1(12) . . . . ?
O6 C24 C25 C26 24.5(6) . . . . ?
O5 C24 C25 C26 -165.1(5) . . . . ?
O61 C24 C25 C26 -59.8(8) . . . . ?
O51 C24 C25 C261 175.8(14) . . . . ?
O6 C24 C25 C261 53.2(9) . . . . ?
O5 C24 C25 C261 -136.4(8) . . . . ?
O61 C24 C25 C261 -31.1(11) . . . . ?
N31 C25 N3 C27 -19.3(8) . . . . ?
C26 C25 N3 C27 -114.9(5) . . . . ?
C24 C25 N3 C27 114.5(4) . . . . ?
C261 C25 N3 C27 -135.3(7) . . . . ?
C25 N3 C27 O7 -4.1(7) . . . . ?
C25 N3 C27 C28 174.9(3) . . . . ?
O7 C27 C28 C33 178.2(5) . . . . ?
N3 C27 C28 C33 -0.8(5) . . . . ?
O7 C27 C28 C29 -3.3(6) . . . . ?
N3 C27 C28 C29 177.7(3) . . . . ?
C33 C28 C29 C30 1.2(5) . . . . ?
C27 C28 C29 C30 -177.4(3) . . . . ?
C28 C29 C30 C31 0.9(5) . . . . ?
C28 C29 C30 N4 -177.9(3) . . . . ?
O8 N4 C30 C31 -173.0(4) . . . . ?
O9 N4 C30 C31 7.0(5) . . . . ?
O8 N4 C30 C29 5.8(4) . . . . ?
O9 N4 C30 C29 -174.2(3) . . . . ?
C29 C30 C31 C32 -2.2(6) . . . . ?
N4 C30 C31 C32 176.6(4) . . . . ?
C30 C31 C32 C33 1.5(7) . . . . ?
C30 C31 C32 C271 150.3(6) . . . 1_455 ?
C29 C28 C33 C32 -1.8(6) . . . . ?
C27 C28 C33 C32 176.6(4) . . . . ?
C31 C32 C33 C28 0.5(7) . . . . ?
C271 C32 C33 C28 -137.0(7) 1_455 . . . ?
N3 C25 N31 C271 20.6(14) . . . . ?
C26 C25 N31 C271 134.1(12) . . . . ?
C24 C25 N31 C271 -112.2(12) . . . . ?
C261 C25 N31 C271 126.2(13) . . . . ?
C25 N31 C271 O71 -6(3) . . . . ?
C25 N31 C271 C32 -173.1(9) . . . 1_655 ?
O101 C101 C102 O102 61.2(5) . . . . ?
O101 C101 C102 C103 -177.5(5) . . . . ?
O111 C111 C112 O112 -58(4) . . . . ?
O111 C111 C112 C113 174(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.93 1.73 2.652(11) 169.1 .
N2 H2A O5 0.93 1.77 2.665(4) 161.4 .
N3 H3A O6 0.88 2.14 2.914(5) 146.1 4_465
N31 H31C O61 0.88 2.02 2.863(16) 160.8 4_565
O101 H101 O5 0.84 2.13 2.799(6) 137.0 .
O102 H102 O4 0.84 1.99 2.824(4) 172.9 3
O111 H111 O51 0.84 2.10 2.88(3) 153.5 .
O112 H112 O4 0.84 2.03 2.716(17) 137.9 3

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        35.53
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 930488'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


#====== end



data_b3nb(dl)a/13pr1
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-(D~0.51~L~0.49~)-alaninate propan-1,3-diol solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O5, C23 H27 N2 O4, C3 H8 O2'
_chemical_formula_sum            'C36 H44 N4 O11'
_chemical_formula_weight         708.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.882(2)
_cell_length_b                   12.211(3)
_cell_length_c                   35.713(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3437.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2219
_cell_measurement_theta_min      2.8192
_cell_measurement_theta_max      28.7632

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10353
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_sigmaI/netI    0.1024
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4178
_reflns_number_gt                1893
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4178
_refine_ls_number_parameters     701
_refine_ls_number_restraints     735
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2160
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.904
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8038(6) 0.2455(3) 0.17704(12) 0.0677(12) Uani 1 1 d . . .
O2 O 0.7573(7) 0.8194(3) 0.31871(13) 0.0772(14) Uani 1 1 d . . .
O3 O 0.7219(7) 0.9398(3) 0.25991(13) 0.0846(16) Uani 1 1 d . . .
O4 O 0.7819(9) 0.4192(4) 0.29285(13) 0.101(2) Uani 1 1 d . . .
N1 N 0.8387(7) 0.4984(3) 0.23674(13) 0.0598(14) Uani 1 1 d . . .
N2 N 0.8638(9) 0.6007(4) 0.11306(14) 0.0728(17) Uani 1 1 d . . .
H2A H 0.8682 0.6592 0.0973 0.087 Uiso 1 1 calc R . .
C1 C 0.8006(8) 0.6553(5) 0.28223(17) 0.0592(15) Uani 1 1 d . . .
H1A H 0.8070 0.6116 0.3035 0.071 Uiso 1 1 calc R . .
C2 C 0.7734(9) 0.7666(4) 0.28543(18) 0.0606(16) Uani 1 1 d . . .
C3 C 0.7564(8) 0.8311(4) 0.25308(19) 0.0628(17) Uani 1 1 d . . .
C4 C 0.7785(9) 0.7854(4) 0.21899(18) 0.0612(16) Uani 1 1 d . . .
H4A H 0.7721 0.8294 0.1978 0.073 Uiso 1 1 calc R . .
C5 C 0.8106(8) 0.6741(4) 0.21493(16) 0.0545(14) Uani 1 1 d . . .
C6 C 0.8181(8) 0.6096(4) 0.24723(16) 0.0533(14) Uani 1 1 d . . .
C7 C 0.8520(8) 0.6068(4) 0.18122(17) 0.0554(15) Uani 1 1 d . . .
C8 C 0.8362(8) 0.4870(4) 0.19559(15) 0.0516(14) Uani 1 1 d . . .
H8A H 0.9337 0.4436 0.1872 0.062 Uiso 1 1 calc R . .
C9 C 0.7992(9) 0.4113(5) 0.2587(2) 0.0695(18) Uani 1 1 d . . .
C10 C 0.7682(10) 0.3045(4) 0.23892(18) 0.0656(17) Uani 1 1 d . . .
H10A H 0.6928 0.2608 0.2543 0.079 Uiso 1 1 calc R . .
H10B H 0.8753 0.2656 0.2374 0.079 Uiso 1 1 calc R . .
C11 C 0.6925(8) 0.3102(4) 0.19942(18) 0.0596(16) Uani 1 1 d . . .
H11A H 0.5808 0.2751 0.1998 0.072 Uiso 1 1 calc R . .
C12 C 0.7424(11) 0.2241(5) 0.1392(2) 0.077(2) Uani 1 1 d . . .
H12A H 0.6196 0.2186 0.1395 0.092 Uiso 1 1 calc R . .
H12B H 0.7878 0.1549 0.1304 0.092 Uiso 1 1 calc R . .
C13 C 0.7955(10) 0.3143(5) 0.11321(19) 0.0730(19) Uani 1 1 d . . .
H13A H 0.8700 0.2983 0.0938 0.088 Uiso 1 1 calc R . .
C14 C 0.7400(10) 0.4153(5) 0.11703(18) 0.0715(19) Uani 1 1 d . . .
C15 C 0.7951(13) 0.5048(5) 0.09108(19) 0.089(2) Uani 1 1 d . . .
H15A H 0.6995 0.5285 0.0760 0.106 Uiso 1 1 calc R . .
H15B H 0.8822 0.4774 0.0743 0.106 Uiso 1 1 calc R . .
C16 C 1.0386(10) 0.5830(6) 0.12816(18) 0.0722(19) Uani 1 1 d . . .
H16A H 1.0660 0.5056 0.1288 0.087 Uiso 1 1 calc R . .
H16B H 1.1221 0.6206 0.1129 0.087 Uiso 1 1 calc R . .
C17 C 1.0342(9) 0.6294(5) 0.16671(19) 0.0673(18) Uani 1 1 d . . .
H17A H 1.0572 0.7074 0.1662 0.081 Uiso 1 1 calc R . .
H17B H 1.1176 0.5938 0.1826 0.081 Uiso 1 1 calc R . .
C18 C 0.6711(8) 0.4276(4) 0.18637(16) 0.0558(15) Uani 1 1 d . . .
H18A H 0.5845 0.4599 0.2027 0.067 Uiso 1 1 calc R . .
C19 C 0.6114(8) 0.4487(4) 0.14607(19) 0.0615(17) Uani 1 1 d . . .
H19A H 0.5049 0.4094 0.1416 0.074 Uiso 1 1 calc R . .
C20 C 0.5799(9) 0.5724(4) 0.14319(19) 0.0690(18) Uani 1 1 d . . .
H20A H 0.5259 0.5893 0.1195 0.083 Uiso 1 1 calc R . .
H20B H 0.5050 0.5957 0.1632 0.083 Uiso 1 1 calc R . .
C21 C 0.7458(9) 0.6316(4) 0.14603(17) 0.0635(18) Uani 1 1 d . . .
H21A H 0.7238 0.7106 0.1450 0.076 Uiso 1 1 calc R . .
C22 C 0.7820(12) 0.7560(6) 0.35201(18) 0.088(2) Uani 1 1 d . . .
H22A H 0.7697 0.8024 0.3736 0.132 Uiso 1 1 calc R . .
H22B H 0.8937 0.7247 0.3518 0.132 Uiso 1 1 calc R . .
H22C H 0.6990 0.6985 0.3530 0.132 Uiso 1 1 calc R . .
C23 C 0.7012(15) 1.0071(5) 0.2280(2) 0.116(4) Uani 1 1 d . . .
H23A H 0.6758 1.0806 0.2357 0.174 Uiso 1 1 calc R . .
H23B H 0.6097 0.9795 0.2129 0.174 Uiso 1 1 calc R . .
H23C H 0.8040 1.0070 0.2135 0.174 Uiso 1 1 calc R . .
O5 O 0.2143(17) 0.2799(9) 0.4284(4) 0.072(3) Uani 0.487(7) 1 d P A 1
O6 O 0.0376(15) 0.1900(8) 0.4649(3) 0.094(4) Uani 0.487(7) 1 d P A 1
O51 O 0.094(2) 0.2728(9) 0.4307(4) 0.084(4) Uani 0.513(7) 1 d P A 2
O61 O 0.2560(18) 0.1843(7) 0.4707(4) 0.118(5) Uani 0.513(7) 1 d P A 2
O7 O 0.1679(9) 0.5748(4) 0.4606(2) 0.132(2) Uani 1 1 d . . .
O8 O 0.5549(10) 0.9040(5) 0.4380(2) 0.130(3) Uani 1 1 d . A .
O9 O 0.8221(11) 0.8956(4) 0.43953(17) 0.110(2) Uani 1 1 d . A .
N4 N 0.6812(13) 0.8527(5) 0.44400(18) 0.0857(19) Uani 1 1 d . . .
C24 C 0.1477(11) 0.2655(5) 0.4601(2) 0.0674(19) Uani 1 1 d . . .
C25 C 0.1512(10) 0.3636(5) 0.4881(2) 0.0710(19) Uani 1 1 d . . .
H25A H 0.2464 0.4101 0.4804 0.085 Uiso 0.487(7) 1 calc PR A 1
H25B H 0.0616 0.4117 0.4803 0.085 Uiso 0.513(7) 1 d PR A 2
N3 N 0.0113(13) 0.4243(7) 0.4841(3) 0.059(3) Uani 0.487(7) 1 d PU . 1
H3A H -0.0848 0.3947 0.4894 0.070 Uiso 0.487(7) 1 calc PR A 1
C26 C 0.192(3) 0.325(2) 0.5289(7) 0.100(5) Uani 0.487(7) 1 d PU . 1
H26A H 0.1920 0.3865 0.5455 0.149 Uiso 0.487(7) 1 calc PR A 1
H26B H 0.3010 0.2899 0.5294 0.149 Uiso 0.487(7) 1 calc PR A 1
H26C H 0.1067 0.2733 0.5369 0.149 Uiso 0.487(7) 1 calc PR A 1
C27 C 0.0116(16) 0.5271(9) 0.4724(4) 0.057(4) Uani 0.487(7) 1 d PU . 1
C28 C 0.842(2) 0.5835(15) 0.4700(5) 0.069(4) Uani 0.487(7) 1 d PU . 1
C29 C 0.845(2) 0.6944(15) 0.4595(5) 0.064(4) Uani 0.487(7) 1 d PU . 1
H29B H 0.9484 0.7273 0.4538 0.076 Uiso 0.487(7) 1 calc PR A 1
C30 C 0.699(2) 0.7548(15) 0.4576(7) 0.050(4) Uani 0.487(7) 1 d PU . 1
C31 C 0.540(3) 0.7037(18) 0.4648(7) 0.063(5) Uani 0.487(7) 1 d PU . 1
H31 H 0.4393 0.7419 0.4616 0.075 Uiso 0.487(7) 1 calc PR A 1
C32 C 0.540(3) 0.5964(19) 0.4766(8) 0.071(5) Uani 0.487(7) 1 d PU . 1
H32B H 0.4372 0.5627 0.4823 0.085 Uiso 0.487(7) 1 calc PR A 1
C33 C 0.687(3) 0.5389(17) 0.4802(6) 0.070(4) Uani 0.487(7) 1 d PU . 1
H33B H 0.6827 0.4679 0.4896 0.084 Uiso 0.487(7) 1 calc PR A 1
N31 N 0.2984(12) 0.4248(7) 0.4850(3) 0.058(3) Uani 0.513(7) 1 d PU . 2
H31B H 0.3896 0.3940 0.4930 0.070 Uiso 0.513(7) 1 calc PR A 2
C261 C 0.104(3) 0.3226(19) 0.5264(7) 0.100(5) Uani 0.513(7) 1 d PU . 2
H26D H 0.1033 0.3827 0.5437 0.149 Uiso 0.513(7) 1 calc PR A 2
H26E H 0.1857 0.2691 0.5345 0.149 Uiso 0.513(7) 1 calc PR A 2
H26F H -0.0064 0.2898 0.5256 0.149 Uiso 0.513(7) 1 calc PR A 2
C271 C 0.3157(16) 0.5239(9) 0.4714(4) 0.061(3) Uani 0.513(7) 1 d PU . 2
C281 C 0.481(2) 0.5792(16) 0.4728(6) 0.059(4) Uani 0.513(7) 1 d PU . 2
C291 C 0.500(3) 0.6810(16) 0.4579(6) 0.057(4) Uani 0.513(7) 1 d PU . 2
H29A H 0.4072 0.7159 0.4472 0.068 Uiso 0.513(7) 1 calc PR A 2
C301 C 0.649(2) 0.7309(13) 0.4584(6) 0.048(3) Uani 0.513(7) 1 d PU . 2
C311 C 0.796(2) 0.6835(16) 0.4730(5) 0.069(4) Uani 0.513(7) 1 d PU . 2
H31A H 0.8984 0.7209 0.4723 0.083 Uiso 0.513(7) 1 calc PR A 2
C321 C 0.786(2) 0.5856(14) 0.4876(5) 0.072(4) Uani 0.513(7) 1 d PU . 2
H32A H 0.8831 0.5500 0.4962 0.086 Uiso 0.513(7) 1 calc PR A 2
C331 C 0.619(2) 0.5334(16) 0.4901(5) 0.068(4) Uani 0.513(7) 1 d PU . 2
H33A H 0.6068 0.4686 0.5035 0.082 Uiso 0.513(7) 1 calc PR A 2
O101 O 1.162(4) 0.438(3) 0.3681(10) 0.152(7) Uani 0.229(9) 1 d PDU B 1
H101 H 1.2280 0.4057 0.3818 0.228 Uiso 0.229(9) 1 calc PR B 1
C101 C 1.017(4) 0.403(3) 0.3729(16) 0.150(5) Uani 0.229(9) 1 d PDU B 1
H10C H 1.0107 0.3814 0.3990 0.180 Uiso 0.229(9) 1 calc PR B 1
H10D H 1.0091 0.3363 0.3583 0.180 Uiso 0.229(9) 1 calc PR B 1
C102 C 0.852(4) 0.469(3) 0.3647(18) 0.150(4) Uani 0.229(9) 1 d PDU B 1
H10E H 0.8446 0.4913 0.3388 0.179 Uiso 0.229(9) 1 calc PR B 1
H10F H 0.8404 0.5319 0.3810 0.179 Uiso 0.229(9) 1 calc PR B 1
O103 O 0.568(4) 0.388(3) 0.3740(12) 0.147(4) Uani 0.229(9) 1 d PDU B 1
H103 H 0.5368 0.3993 0.3525 0.221 Uiso 0.229(9) 1 calc PR B 1
C103 C 0.724(5) 0.376(3) 0.374(2) 0.150(4) Uani 0.229(9) 1 d PDU B 1
H10G H 0.7492 0.3160 0.3578 0.179 Uiso 0.229(9) 1 calc PR B 1
H10H H 0.7527 0.3517 0.3995 0.179 Uiso 0.229(9) 1 calc PR B 1
O111 O 0.860(3) 0.437(2) 0.3854(7) 0.150(4) Uani 0.346(10) 1 d PDU C 2
H111 H 0.9206 0.4179 0.4029 0.226 Uiso 0.346(10) 1 calc PR C 2
C111 C 0.710(4) 0.433(4) 0.3949(8) 0.149(4) Uani 0.346(10) 1 d PDU C 2
H11B H 0.6973 0.4743 0.4179 0.179 Uiso 0.346(10) 1 calc PR C 2
H11C H 0.6830 0.3573 0.4005 0.179 Uiso 0.346(10) 1 calc PR C 2
C112 C 0.578(2) 0.476(3) 0.3662(10) 0.149(4) Uani 0.346(10) 1 d PDU C 2
H11D H 0.5787 0.5554 0.3644 0.179 Uiso 0.346(10) 1 calc PR C 2
H11E H 0.5932 0.4442 0.3416 0.179 Uiso 0.346(10) 1 calc PR C 2
O113 O 0.290(3) 0.419(3) 0.3665(9) 0.139(5) Uani 0.346(10) 1 d PDU C 2
H113 H 0.2151 0.3897 0.3789 0.208 Uiso 0.346(10) 1 calc PR C 2
C113 C 0.417(3) 0.432(3) 0.3862(8) 0.144(4) Uani 0.346(10) 1 d PDU C 2
H11F H 0.4446 0.3626 0.3977 0.173 Uiso 0.346(10) 1 calc PR C 2
H11G H 0.3879 0.4827 0.4062 0.173 Uiso 0.346(10) 1 calc PR C 2
O121 O 0.947(4) 0.539(2) 0.3984(9) 0.148(5) Uani 0.248(7) 1 d PDU D 3
H121 H 0.9665 0.5224 0.4203 0.222 Uiso 0.248(7) 1 calc PR D 3
C121 C 0.814(6) 0.495(3) 0.3884(16) 0.150(4) Uani 0.248(7) 1 d PDU D 3
H12C H 0.8085 0.4980 0.3613 0.180 Uiso 0.248(7) 1 calc PR D 3
H12D H 0.7201 0.5390 0.3978 0.180 Uiso 0.248(7) 1 calc PR D 3
C122 C 0.784(5) 0.375(2) 0.4007(14) 0.150(4) Uani 0.248(7) 1 d PDU D 3
H12E H 0.7768 0.3673 0.4277 0.180 Uiso 0.248(7) 1 calc PR D 3
H12F H 0.8706 0.3257 0.3910 0.180 Uiso 0.248(7) 1 calc PR D 3
O123 O 0.612(4) 0.313(2) 0.3502(8) 0.149(4) Uani 0.248(7) 1 d PDU D 3
H123 H 0.6636 0.3522 0.3353 0.223 Uiso 0.248(7) 1 calc PR D 3
C123 C 0.610(4) 0.358(3) 0.3812(12) 0.148(4) Uani 0.248(7) 1 d PDU D 3
H12G H 0.5384 0.3151 0.3977 0.178 Uiso 0.248(7) 1 calc PR D 3
H12H H 0.5567 0.4293 0.3784 0.178 Uiso 0.248(7) 1 calc PR D 3
O131 O 0.692(6) 0.478(3) 0.3801(16) 0.149(4) Uani 0.178(9) 1 d PDU E 4
H131 H 0.7026 0.4845 0.3574 0.223 Uiso 0.178(9) 1 calc PR E 4
C131 C 0.688(5) 0.380(4) 0.388(3) 0.149(4) Uani 0.178(9) 1 d PDU E 4
H13B H 0.7469 0.3729 0.4121 0.179 Uiso 0.178(9) 1 calc PR E 4
H13C H 0.7574 0.3424 0.3699 0.179 Uiso 0.178(9) 1 calc PR E 4
C132 C 0.522(6) 0.312(4) 0.3921(17) 0.148(4) Uani 0.178(9) 1 d PDU E 4
H13D H 0.5354 0.2376 0.3829 0.178 Uiso 0.178(9) 1 calc PR E 4
H13E H 0.4795 0.3107 0.4175 0.178 Uiso 0.178(9) 1 calc PR E 4
O133 O 0.275(7) 0.425(7) 0.3748(18) 0.141(5) Uani 0.178(9) 1 d PDU E 4
H133 H 0.2221 0.3835 0.3885 0.212 Uiso 0.178(9) 1 calc PR E 4
C133 C 0.410(7) 0.383(5) 0.3657(13) 0.144(4) Uani 0.178(9) 1 d PDU E 4
H13F H 0.4824 0.4422 0.3571 0.173 Uiso 0.178(9) 1 calc PR E 4
H13G H 0.3862 0.3380 0.3440 0.173 Uiso 0.178(9) 1 calc PR E 4

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.085(3) 0.053(2) 0.065(3) -0.003(2) 0.004(3) -0.001(2)
O2 0.097(3) 0.072(2) 0.063(3) -0.018(2) 0.017(3) 0.000(3)
O3 0.127(4) 0.053(2) 0.073(3) -0.019(2) 0.019(3) -0.005(3)
O4 0.181(6) 0.074(2) 0.047(3) 0.003(2) 0.012(4) -0.006(4)
N1 0.082(4) 0.052(2) 0.046(3) 0.005(2) 0.000(3) -0.005(3)
N2 0.119(5) 0.053(3) 0.047(3) -0.001(2) 0.005(4) -0.021(3)
C1 0.065(4) 0.067(3) 0.046(3) 0.003(3) -0.004(3) -0.004(3)
C2 0.072(4) 0.056(3) 0.054(4) -0.012(3) 0.013(4) -0.003(3)
C3 0.075(4) 0.050(3) 0.064(4) -0.007(3) -0.004(4) 0.002(3)
C4 0.079(4) 0.051(3) 0.053(4) 0.004(3) 0.003(4) -0.009(3)
C5 0.070(4) 0.046(3) 0.047(3) -0.003(2) 0.009(4) -0.003(3)
C6 0.073(4) 0.042(3) 0.044(3) -0.003(2) -0.008(3) -0.002(3)
C7 0.069(4) 0.047(3) 0.050(3) -0.007(3) 0.003(3) -0.016(3)
C8 0.059(4) 0.050(3) 0.046(3) -0.007(3) 0.004(3) 0.003(3)
C9 0.085(4) 0.053(3) 0.070(5) 0.007(3) 0.001(4) 0.012(3)
C10 0.088(5) 0.051(3) 0.058(4) 0.001(3) 0.002(4) 0.000(3)
C11 0.057(3) 0.055(3) 0.067(4) -0.004(3) 0.017(4) -0.005(3)
C12 0.087(5) 0.063(3) 0.081(5) -0.023(4) 0.002(5) -0.010(4)
C13 0.088(5) 0.069(4) 0.063(4) -0.006(3) -0.012(4) -0.010(4)
C14 0.098(5) 0.057(3) 0.060(4) -0.008(3) -0.009(4) -0.012(4)
C15 0.132(7) 0.074(4) 0.060(4) -0.005(4) 0.000(5) -0.020(5)
C16 0.087(5) 0.088(4) 0.042(4) -0.007(4) 0.018(4) -0.025(4)
C17 0.076(4) 0.059(3) 0.066(4) 0.005(3) 0.018(4) -0.016(3)
C18 0.064(4) 0.044(3) 0.059(4) -0.004(3) 0.008(3) 0.000(3)
C19 0.060(4) 0.056(3) 0.069(4) -0.009(3) -0.002(4) -0.011(3)
C20 0.094(5) 0.060(3) 0.054(4) 0.000(3) -0.028(4) -0.004(4)
C21 0.092(5) 0.054(3) 0.044(3) 0.001(3) -0.004(4) -0.012(3)
C22 0.119(7) 0.097(4) 0.048(4) -0.012(4) -0.002(5) 0.009(5)
C23 0.194(11) 0.041(3) 0.113(7) 0.009(4) 0.011(8) 0.017(5)
O5 0.074(7) 0.070(6) 0.072(8) -0.006(5) 0.018(7) 0.010(6)
O6 0.108(9) 0.078(6) 0.095(9) -0.021(6) 0.037(8) -0.035(6)
O51 0.127(11) 0.067(6) 0.057(7) -0.005(6) -0.014(9) 0.044(8)
O61 0.159(12) 0.063(5) 0.133(10) -0.014(6) -0.058(9) 0.041(7)
O7 0.118(5) 0.085(3) 0.194(7) 0.037(4) -0.038(6) 0.013(4)
O8 0.139(6) 0.108(4) 0.143(6) 0.023(4) -0.044(5) 0.039(4)
O9 0.151(6) 0.079(3) 0.099(5) 0.008(3) -0.008(5) -0.002(4)
N4 0.127(6) 0.071(4) 0.059(4) 0.000(3) -0.007(5) 0.010(5)
C24 0.088(5) 0.049(3) 0.065(5) 0.000(3) 0.018(5) 0.006(4)
C25 0.080(5) 0.063(3) 0.070(5) -0.001(3) 0.003(4) -0.007(4)
N3 0.061(5) 0.043(4) 0.071(6) -0.007(5) -0.002(5) -0.005(4)
C26 0.097(9) 0.111(6) 0.090(7) -0.017(6) -0.001(8) 0.012(8)
C27 0.050(6) 0.049(6) 0.073(8) 0.009(5) 0.000(6) 0.003(5)
C28 0.072(7) 0.070(6) 0.066(7) 0.000(6) -0.002(6) 0.005(6)
C29 0.066(7) 0.068(6) 0.057(7) 0.009(6) 0.008(6) 0.008(6)
C30 0.046(7) 0.052(7) 0.052(5) -0.005(6) -0.001(6) -0.011(6)
C31 0.061(8) 0.064(7) 0.063(8) -0.001(6) -0.003(6) 0.005(6)
C32 0.065(8) 0.068(7) 0.079(7) -0.004(6) -0.006(7) 0.001(7)
C33 0.066(8) 0.066(6) 0.078(8) -0.003(6) 0.001(7) 0.009(7)
N31 0.050(5) 0.054(4) 0.070(6) -0.008(5) -0.006(5) 0.009(4)
C261 0.098(9) 0.115(6) 0.086(7) -0.019(6) 0.009(8) -0.001(7)
C271 0.059(6) 0.064(6) 0.059(6) 0.002(5) -0.004(6) 0.018(5)
C281 0.059(8) 0.054(6) 0.064(6) -0.009(5) -0.010(6) 0.003(6)
C291 0.060(7) 0.059(7) 0.052(7) -0.010(6) 0.000(6) -0.005(6)
C301 0.049(7) 0.046(6) 0.050(5) -0.005(5) 0.000(6) -0.019(5)
C311 0.067(7) 0.073(6) 0.067(7) 0.001(6) -0.002(6) -0.005(6)
C321 0.070(7) 0.069(5) 0.077(7) -0.008(6) -0.013(6) 0.011(6)
C331 0.069(8) 0.068(5) 0.068(7) 0.003(6) 0.003(6) 0.000(6)
O101 0.154(9) 0.152(9) 0.149(9) 0.002(7) 0.001(7) -0.003(7)
C101 0.151(7) 0.150(7) 0.149(7) -0.001(6) 0.000(6) -0.001(6)
C102 0.152(6) 0.149(5) 0.148(6) 0.000(4) -0.001(4) -0.002(4)
O103 0.148(5) 0.146(5) 0.147(5) 0.000(4) 0.001(4) -0.002(4)
C103 0.151(5) 0.150(5) 0.148(5) 0.000(4) 0.000(4) -0.002(4)
O111 0.152(5) 0.150(5) 0.149(5) -0.001(4) -0.002(4) -0.001(4)
C111 0.152(5) 0.148(5) 0.148(5) 0.000(4) 0.000(4) -0.003(4)
C112 0.151(6) 0.148(5) 0.149(6) 0.000(4) 0.001(4) 0.000(4)
O113 0.146(7) 0.134(6) 0.136(7) -0.004(6) -0.001(6) -0.003(5)
C113 0.147(6) 0.142(6) 0.144(6) 0.000(5) -0.001(5) -0.002(5)
O121 0.150(7) 0.148(6) 0.147(7) 0.001(5) -0.002(5) -0.005(5)
C121 0.151(6) 0.150(5) 0.149(6) 0.000(4) -0.001(4) -0.001(4)
C122 0.150(6) 0.151(5) 0.149(6) -0.001(4) 0.000(4) -0.002(4)
O123 0.151(6) 0.148(6) 0.147(6) 0.001(5) 0.002(5) -0.006(5)
C123 0.150(5) 0.148(5) 0.147(5) 0.000(4) 0.000(4) -0.004(4)
O131 0.151(5) 0.148(5) 0.148(5) 0.000(4) -0.001(4) -0.003(4)
C131 0.151(5) 0.149(5) 0.148(5) 0.000(4) 0.000(4) -0.003(4)
C132 0.150(6) 0.148(6) 0.147(6) -0.001(5) 0.001(5) -0.004(5)
O133 0.145(7) 0.138(6) 0.140(7) 0.000(6) -0.002(6) -0.003(6)
C133 0.147(6) 0.143(5) 0.143(6) -0.001(4) 0.000(5) -0.003(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.425(7) . ?
O1 C12 1.458(8) . ?
O2 C2 1.359(7) . ?
O2 C22 1.432(7) . ?
O3 C3 1.376(7) . ?
O3 C23 1.416(8) . ?
O4 C9 1.230(8) . ?
N1 C9 1.358(7) . ?
N1 C6 1.418(6) . ?
N1 C8 1.477(7) . ?
N2 C16 1.495(10) . ?
N2 C15 1.510(8) . ?
N2 C21 1.547(8) . ?
N2 H2A 0.9100 . ?
C1 C6 1.375(8) . ?
C1 C2 1.381(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.405(8) . ?
C3 C4 1.350(8) . ?
C4 C5 1.390(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(7) . ?
C5 C7 1.494(8) . ?
C7 C21 1.540(9) . ?
C7 C17 1.551(9) . ?
C7 C8 1.556(7) . ?
C8 C18 1.525(8) . ?
C8 H8A 0.9800 . ?
C9 C10 1.504(9) . ?
C10 C11 1.533(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.516(8) . ?
C11 H11A 0.9800 . ?
C12 C13 1.500(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.316(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.497(9) . ?
C14 C19 1.506(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.489(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.536(8) . ?
C18 H18A 0.9800 . ?
C19 C20 1.534(8) . ?
C19 H19A 0.9800 . ?
C20 C21 1.498(10) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O5 C24 1.261(14) . ?
O6 C24 1.278(11) . ?
O51 C24 1.139(12) . ?
O61 C24 1.362(12) . ?
O7 C271 1.376(13) . ?
O7 C27 1.426(14) . ?
O8 N4 1.194(9) . ?
O9 N4 1.239(10) . ?
N4 C30 1.30(2) . ?
N4 C301 1.594(17) . ?
C24 C25 1.560(9) . ?
C25 N3 1.337(12) . ?
C25 N31 1.384(11) . ?
C25 C261 1.50(2) . ?
C25 C26 1.57(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9600 . ?
N3 C27 1.323(15) . ?
N3 H25B 0.4470 . ?
N3 H3A 0.8600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.51(2) 1_455 ?
C28 C33 1.39(3) . ?
C28 C29 1.40(3) . ?
C28 C27 1.51(2) 1_655 ?
C29 C30 1.37(3) . ?
C29 H29B 0.9300 . ?
C30 C31 1.42(3) . ?
C31 C32 1.38(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.36(3) . ?
C32 H32B 0.9300 . ?
C33 H33B 0.9300 . ?
N31 C271 1.310(14) . ?
N31 H31B 0.8600 . ?
C261 H26D 0.9600 . ?
C261 H26E 0.9600 . ?
C261 H26F 0.9600 . ?
C271 C281 1.47(2) . ?
C281 C291 1.36(3) . ?
C281 C331 1.37(3) . ?
C291 C301 1.33(2) . ?
C291 H29A 0.9300 . ?
C301 C311 1.39(3) . ?
C311 C321 1.31(2) . ?
C311 H31A 0.9300 . ?
C321 C331 1.47(3) . ?
C321 H32A 0.9300 . ?
C331 H33A 0.9300 . ?
O101 C101 1.23(2) . ?
O101 H101 0.8200 . ?
C101 C102 1.55(2) . ?
C101 H10C 0.9700 . ?
C101 H10D 0.9700 . ?
C102 C103 1.55(2) . ?
C102 H10E 0.9700 . ?
C102 H10F 0.9700 . ?
O103 C103 1.23(2) . ?
O103 H103 0.8200 . ?
C103 H10G 0.9700 . ?
C103 H10H 0.9700 . ?
O111 C111 1.23(2) . ?
O111 H111 0.8200 . ?
C111 C112 1.55(2) . ?
C111 H11B 0.9700 . ?
C111 H11C 0.9700 . ?
C112 C113 1.55(2) . ?
C112 H11D 0.9700 . ?
C112 H11E 0.9700 . ?
O113 C113 1.23(2) . ?
O113 H113 0.8200 . ?
C113 H11F 0.9700 . ?
C113 H11G 0.9700 . ?
O121 C121 1.23(2) . ?
O121 H121 0.8200 . ?
C121 C122 1.55(2) . ?
C121 H12C 0.9700 . ?
C121 H12D 0.9700 . ?
C122 C123 1.56(2) . ?
C122 H12E 0.9700 . ?
C122 H12F 0.9700 . ?
O123 C123 1.23(2) . ?
O123 H123 0.8200 . ?
C123 H12G 0.9700 . ?
C123 H12H 0.9700 . ?
O131 C131 1.23(2) . ?
O131 H131 0.8200 . ?
C131 C132 1.56(2) . ?
C131 H13B 0.9700 . ?
C131 H13C 0.9700 . ?
C132 C133 1.55(2) . ?
C132 H13D 0.9700 . ?
C132 H13E 0.9700 . ?
O133 C133 1.23(2) . ?
O133 H133 0.8200 . ?
C133 H13F 0.9700 . ?
C133 H13G 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.5(5) . . ?
C2 O2 C22 117.2(5) . . ?
C3 O3 C23 116.1(5) . . ?
C9 N1 C6 124.8(5) . . ?
C9 N1 C8 119.9(5) . . ?
C6 N1 C8 110.6(4) . . ?
C16 N2 C15 113.9(6) . . ?
C16 N2 C21 108.3(5) . . ?
C15 N2 C21 111.7(6) . . ?
C16 N2 H2A 107.5 . . ?
C15 N2 H2A 107.5 . . ?
C21 N2 H2A 107.5 . . ?
C6 C1 C2 119.3(6) . . ?
C6 C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 . . ?
O2 C2 C1 123.7(6) . . ?
O2 C2 C3 116.4(5) . . ?
C1 C2 C3 119.9(6) . . ?
C4 C3 O3 125.7(6) . . ?
C4 C3 C2 119.9(5) . . ?
O3 C3 C2 114.4(5) . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C4 C5 C6 118.2(5) . . ?
C4 C5 C7 131.4(5) . . ?
C6 C5 C7 110.2(4) . . ?
C1 C6 C5 121.2(5) . . ?
C1 C6 N1 129.7(5) . . ?
C5 C6 N1 109.1(5) . . ?
C5 C7 C21 115.5(5) . . ?
C5 C7 C17 112.0(5) . . ?
C21 C7 C17 101.3(5) . . ?
C5 C7 C8 103.5(5) . . ?
C21 C7 C8 114.3(5) . . ?
C17 C7 C8 110.6(5) . . ?
N1 C8 C18 105.7(5) . . ?
N1 C8 C7 103.8(4) . . ?
C18 C8 C7 116.4(5) . . ?
N1 C8 H8A 110.2 . . ?
C18 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
O4 C9 N1 122.5(6) . . ?
O4 C9 C10 121.1(6) . . ?
N1 C9 C10 116.4(6) . . ?
C9 C10 C11 117.1(5) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 114.8(5) . . ?
O1 C11 C10 104.5(5) . . ?
C18 C11 C10 111.7(5) . . ?
O1 C11 H11A 108.5 . . ?
C18 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
O1 C12 C13 110.4(5) . . ?
O1 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 122.1(7) . . ?
C14 C13 H13A 118.9 . . ?
C12 C13 H13A 118.9 . . ?
C13 C14 C15 121.6(7) . . ?
C13 C14 C19 123.3(6) . . ?
C15 C14 C19 115.1(6) . . ?
C14 C15 N2 110.4(5) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 N2 104.9(6) . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16B 110.8 . . ?
N2 C16 H16B 110.8 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 105.2(6) . . ?
C16 C17 H17A 110.7 . . ?
C7 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
C7 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C11 C18 C8 106.7(5) . . ?
C11 C18 C19 118.7(5) . . ?
C8 C18 C19 112.6(5) . . ?
C11 C18 H18A 106.0 . . ?
C8 C18 H18A 106.0 . . ?
C19 C18 H18A 106.0 . . ?
C14 C19 C20 109.2(5) . . ?
C14 C19 C18 113.2(5) . . ?
C20 C19 C18 106.1(5) . . ?
C14 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C21 C20 C19 109.3(6) . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 C7 115.8(5) . . ?
C20 C21 N2 110.8(5) . . ?
C7 C21 N2 104.2(5) . . ?
C20 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C271 O7 C27 117.6(7) . . ?
O8 N4 O9 120.2(7) . . ?
O8 N4 C30 129.8(12) . . ?
O9 N4 C30 109.8(11) . . ?
O8 N4 C301 114.6(10) . . ?
O9 N4 C301 125.2(10) . . ?
C30 N4 C301 15.6(11) . . ?
O51 C24 O5 46.7(7) . . ?
O51 C24 O6 85.7(12) . . ?
O5 C24 O6 120.2(10) . . ?
O51 C24 O61 123.2(9) . . ?
O5 C24 O61 95.1(10) . . ?
O6 C24 O61 82.2(8) . . ?
O51 C24 C25 122.5(8) . . ?
O5 C24 C25 117.5(7) . . ?
O6 C24 C25 118.8(7) . . ?
O61 C24 C25 111.8(8) . . ?
N3 C25 N31 112.6(6) . . ?
N3 C25 C261 94.5(12) . . ?
N31 C25 C261 117.3(11) . . ?
N3 C25 C24 110.0(7) . . ?
N31 C25 C24 112.2(7) . . ?
C261 C25 C24 108.8(10) . . ?
N3 C25 C26 115.9(12) . . ?
N31 C25 C26 93.9(12) . . ?
C261 C25 C26 26.1(10) . . ?
C24 C25 C26 111.4(10) . . ?
N3 C25 H25A 106.3 . . ?
N31 C25 H25A 12.4 . . ?
C261 C25 H25A 129.4 . . ?
C24 C25 H25A 106.3 . . ?
C26 C25 H25A 106.3 . . ?
N3 C25 H25B 12.2 . . ?
N31 C25 H25B 105.3 . . ?
C261 C25 H25B 106.7 . . ?
C24 C25 H25B 105.7 . . ?
C26 C25 H25B 127.4 . . ?
H25A C25 H25B 97.3 . . ?
C27 N3 C25 123.9(10) . . ?
C27 N3 H25B 103.3 . . ?
C25 N3 H25B 27.0 . . ?
C27 N3 H3A 118.0 . . ?
C25 N3 H3A 118.0 . . ?
H25B N3 H3A 134.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 O7 118.8(10) . . ?
N3 C27 C28 116.8(12) . 1_455 ?
O7 C27 C28 124.3(11) . 1_455 ?
N3 C27 H25B 17.0 . . ?
O7 C27 H25B 102.3 . . ?
C28 C27 H25B 132.7 1_455 . ?
C33 C28 C29 117.6(16) . . ?
C33 C28 C27 126.0(15) . 1_655 ?
C29 C28 C27 116.1(15) . 1_655 ?
C30 C29 C28 121.2(17) . . ?
C30 C29 H29B 119.4 . . ?
C28 C29 H29B 119.4 . . ?
N4 C30 C29 127.4(17) . . ?
N4 C30 C31 112.0(17) . . ?
C29 C30 C31 119.7(19) . . ?
C32 C31 C30 118(2) . . ?
C32 C31 H31 120.8 . . ?
C30 C31 H31 120.8 . . ?
C33 C32 C31 121(2) . . ?
C33 C32 H32B 119.4 . . ?
C31 C32 H32B 119.4 . . ?
C32 C33 C28 121.5(19) . . ?
C32 C33 H33B 119.2 . . ?
C28 C33 H33B 119.2 . . ?
C271 N31 C25 128.0(10) . . ?
C271 N31 H31B 116.0 . . ?
C25 N31 H31B 116.0 . . ?
C25 C261 H26D 109.5 . . ?
C25 C261 H26E 109.5 . . ?
H26D C261 H26E 109.5 . . ?
C25 C261 H26F 109.5 . . ?
H26D C261 H26F 109.5 . . ?
H26E C261 H26F 109.5 . . ?
N31 C271 O7 115.7(11) . . ?
N31 C271 C281 120.3(12) . . ?
O7 C271 C281 123.6(11) . . ?
C291 C281 C331 117.5(16) . . ?
C291 C281 C271 120.3(17) . . ?
C331 C281 C271 122.2(17) . . ?
C301 C291 C281 121(2) . . ?
C301 C291 H29A 119.6 . . ?
C281 C291 H29A 119.6 . . ?
C291 C301 C311 123.3(18) . . ?
C291 C301 N4 124.3(17) . . ?
C311 C301 N4 112.3(13) . . ?
C321 C311 C301 119.0(17) . . ?
C321 C311 H31A 120.5 . . ?
C301 C311 H31A 120.5 . . ?
C311 C321 C331 118.1(17) . . ?
C311 C321 H32A 120.9 . . ?
C331 C321 H32A 120.9 . . ?
C281 C331 C321 120.6(17) . . ?
C281 C331 H33A 119.7 . . ?
C321 C331 H33A 119.7 . . ?
C101 O101 H101 109.5 . . ?
O101 C101 C102 125(2) . . ?
O101 C101 H10C 106.2 . . ?
C102 C101 H10C 106.2 . . ?
O101 C101 H10D 106.2 . . ?
C102 C101 H10D 106.2 . . ?
H10C C101 H10D 106.4 . . ?
C101 C102 C103 97.4(18) . . ?
C101 C102 H10E 112.3 . . ?
C103 C102 H10E 112.3 . . ?
C101 C102 H10F 112.3 . . ?
C103 C102 H10F 112.3 . . ?
H10E C102 H10F 109.9 . . ?
C103 O103 H103 109.5 . . ?
O103 C103 C102 124(2) . . ?
O103 C103 H10G 106.2 . . ?
C102 C103 H10G 106.2 . . ?
O103 C103 H10H 106.2 . . ?
C102 C103 H10H 106.2 . . ?
H10G C103 H10H 106.4 . . ?
C111 O111 H111 109.5 . . ?
O111 C111 C112 116.7(19) . . ?
O111 C111 H11B 108.1 . . ?
C112 C111 H11B 108.1 . . ?
O111 C111 H11C 108.1 . . ?
C112 C111 H11C 108.1 . . ?
H11B C111 H11C 107.3 . . ?
C113 C112 C111 97.5(18) . . ?
C113 C112 H11D 112.3 . . ?
C111 C112 H11D 112.3 . . ?
C113 C112 H11E 112.3 . . ?
C111 C112 H11E 112.3 . . ?
H11D C112 H11E 109.9 . . ?
C113 O113 H113 109.5 . . ?
O113 C113 C112 116.7(19) . . ?
O113 C113 H11F 108.1 . . ?
C112 C113 H11F 108.1 . . ?
O113 C113 H11G 108.1 . . ?
C112 C113 H11G 108.1 . . ?
H11F C113 H11G 107.3 . . ?
C121 O121 H121 109.5 . . ?
O121 C121 C122 116.8(19) . . ?
O121 C121 H12C 108.1 . . ?
C122 C121 H12C 108.1 . . ?
O121 C121 H12D 108.1 . . ?
C122 C121 H12D 108.1 . . ?
H12C C121 H12D 107.3 . . ?
C121 C122 C123 97.3(18) . . ?
C121 C122 H12E 112.3 . . ?
C123 C122 H12E 112.3 . . ?
C121 C122 H12F 112.3 . . ?
C123 C122 H12F 112.3 . . ?
H12E C122 H12F 109.9 . . ?
C123 O123 H123 109.5 . . ?
O123 C123 C122 116.5(19) . . ?
O123 C123 H12G 108.2 . . ?
C122 C123 H12G 108.2 . . ?
O123 C123 H12H 108.2 . . ?
C122 C123 H12H 108.2 . . ?
H12G C123 H12H 107.3 . . ?
C131 O131 H131 109.5 . . ?
O131 C131 C132 124(2) . . ?
O131 C131 H13B 106.3 . . ?
C132 C131 H13B 106.3 . . ?
O131 C131 H13C 106.3 . . ?
C132 C131 H13C 106.3 . . ?
H13B C131 H13C 106.4 . . ?
C133 C132 C131 97.3(18) . . ?
C133 C132 H13D 112.3 . . ?
C131 C132 H13D 112.3 . . ?
C133 C132 H13E 112.3 . . ?
C131 C132 H13E 112.3 . . ?
H13D C132 H13E 109.9 . . ?
C133 O133 H133 109.5 . . ?
O133 C133 C132 125(2) . . ?
O133 C133 H13F 106.2 . . ?
C132 C133 H13F 106.2 . . ?
O133 C133 H13G 106.2 . . ?
C132 C133 H13G 106.2 . . ?
H13F C133 H13G 106.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 4.4(11) . . . . ?
C22 O2 C2 C3 -177.2(6) . . . . ?
C6 C1 C2 O2 -178.9(6) . . . . ?
C6 C1 C2 C3 2.8(11) . . . . ?
C23 O3 C3 C4 2.9(11) . . . . ?
C23 O3 C3 C2 -179.0(7) . . . . ?
O2 C2 C3 C4 177.0(6) . . . . ?
C1 C2 C3 C4 -4.6(10) . . . . ?
O2 C2 C3 O3 -1.3(9) . . . . ?
C1 C2 C3 O3 177.1(6) . . . . ?
O3 C3 C4 C5 -179.1(7) . . . . ?
C2 C3 C4 C5 2.9(11) . . . . ?
C3 C4 C5 C6 0.5(10) . . . . ?
C3 C4 C5 C7 -174.7(7) . . . . ?
C2 C1 C6 C5 0.6(10) . . . . ?
C2 C1 C6 N1 -176.7(7) . . . . ?
C4 C5 C6 C1 -2.3(10) . . . . ?
C7 C5 C6 C1 173.8(6) . . . . ?
C4 C5 C6 N1 175.5(6) . . . . ?
C7 C5 C6 N1 -8.3(8) . . . . ?
C9 N1 C6 C1 19.1(12) . . . . ?
C8 N1 C6 C1 174.7(7) . . . . ?
C9 N1 C6 C5 -158.5(7) . . . . ?
C8 N1 C6 C5 -2.9(8) . . . . ?
C4 C5 C7 C21 -43.5(10) . . . . ?
C6 C5 C7 C21 141.0(5) . . . . ?
C4 C5 C7 C17 71.7(10) . . . . ?
C6 C5 C7 C17 -103.8(6) . . . . ?
C4 C5 C7 C8 -169.1(7) . . . . ?
C6 C5 C7 C8 15.4(7) . . . . ?
C9 N1 C8 C18 46.2(7) . . . . ?
C6 N1 C8 C18 -110.8(5) . . . . ?
C9 N1 C8 C7 169.1(6) . . . . ?
C6 N1 C8 C7 12.2(7) . . . . ?
C5 C7 C8 N1 -16.1(7) . . . . ?
C21 C7 C8 N1 -142.5(5) . . . . ?
C17 C7 C8 N1 104.0(6) . . . . ?
C5 C7 C8 C18 99.6(6) . . . . ?
C21 C7 C8 C18 -26.9(7) . . . . ?
C17 C7 C8 C18 -140.4(6) . . . . ?
C6 N1 C9 O4 -18.7(11) . . . . ?
C8 N1 C9 O4 -172.2(7) . . . . ?
C6 N1 C9 C10 158.2(6) . . . . ?
C8 N1 C9 C10 4.7(10) . . . . ?
O4 C9 C10 C11 145.7(7) . . . . ?
N1 C9 C10 C11 -31.3(10) . . . . ?
C12 O1 C11 C18 -66.8(7) . . . . ?
C12 O1 C11 C10 170.5(5) . . . . ?
C9 C10 C11 O1 128.0(6) . . . . ?
C9 C10 C11 C18 3.2(9) . . . . ?
C11 O1 C12 C13 87.8(7) . . . . ?
O1 C12 C13 C14 -64.7(9) . . . . ?
C12 C13 C14 C15 179.5(7) . . . . ?
C12 C13 C14 C19 -3.7(11) . . . . ?
C13 C14 C15 N2 -126.9(7) . . . . ?
C19 C14 C15 N2 56.0(9) . . . . ?
C16 N2 C15 C14 76.3(9) . . . . ?
C21 N2 C15 C14 -46.8(8) . . . . ?
C15 N2 C16 C17 -138.6(5) . . . . ?
C21 N2 C16 C17 -13.7(6) . . . . ?
N2 C16 C17 C7 33.9(6) . . . . ?
C5 C7 C17 C16 -164.2(5) . . . . ?
C21 C7 C17 C16 -40.6(6) . . . . ?
C8 C7 C17 C16 80.9(6) . . . . ?
O1 C11 C18 C8 -72.5(6) . . . . ?
C10 C11 C18 C8 46.3(7) . . . . ?
O1 C11 C18 C19 56.0(8) . . . . ?
C10 C11 C18 C19 174.8(6) . . . . ?
N1 C8 C18 C11 -71.3(5) . . . . ?
C7 C8 C18 C11 174.2(5) . . . . ?
N1 C8 C18 C19 156.8(5) . . . . ?
C7 C8 C18 C19 42.2(6) . . . . ?
C13 C14 C19 C20 178.5(6) . . . . ?
C15 C14 C19 C20 -4.5(8) . . . . ?
C13 C14 C19 C18 60.5(8) . . . . ?
C15 C14 C19 C18 -122.4(6) . . . . ?
C11 C18 C19 C14 -67.5(7) . . . . ?
C8 C18 C19 C14 58.2(6) . . . . ?
C11 C18 C19 C20 172.7(6) . . . . ?
C8 C18 C19 C20 -61.6(6) . . . . ?
C14 C19 C20 C21 -54.4(7) . . . . ?
C18 C19 C20 C21 67.9(7) . . . . ?
C19 C20 C21 C7 -55.6(7) . . . . ?
C19 C20 C21 N2 62.8(7) . . . . ?
C5 C7 C21 C20 -86.0(6) . . . . ?
C17 C7 C21 C20 152.9(5) . . . . ?
C8 C7 C21 C20 34.0(8) . . . . ?
C5 C7 C21 N2 152.1(5) . . . . ?
C17 C7 C21 N2 30.9(5) . . . . ?
C8 C7 C21 N2 -87.9(6) . . . . ?
C16 N2 C21 C20 -136.8(5) . . . . ?
C15 N2 C21 C20 -10.5(7) . . . . ?
C16 N2 C21 C7 -11.6(6) . . . . ?
C15 N2 C21 C7 114.6(5) . . . . ?
O51 C24 C25 N3 36.6(16) . . . . ?
O5 C24 C25 N3 90.8(13) . . . . ?
O6 C24 C25 N3 -67.8(12) . . . . ?
O61 C24 C25 N3 -160.8(9) . . . . ?
O51 C24 C25 N31 -89.6(15) . . . . ?
O5 C24 C25 N31 -35.4(14) . . . . ?
O6 C24 C25 N31 166.0(10) . . . . ?
O61 C24 C25 N31 73.0(10) . . . . ?
O51 C24 C25 C261 138.9(17) . . . . ?
O5 C24 C25 C261 -166.9(15) . . . . ?
O6 C24 C25 C261 34.5(15) . . . . ?
O61 C24 C25 C261 -58.5(15) . . . . ?
O51 C24 C25 C26 166.6(17) . . . . ?
O5 C24 C25 C26 -139.3(15) . . . . ?
O6 C24 C25 C26 62.2(16) . . . . ?
O61 C24 C25 C26 -30.8(15) . . . . ?
N31 C25 N3 C27 10.4(15) . . . . ?
C261 C25 N3 C27 132.5(14) . . . . ?
C24 C25 N3 C27 -115.6(12) . . . . ?
C26 C25 N3 C27 116.9(16) . . . . ?
C25 N3 C27 O7 5.0(19) . . . . ?
C25 N3 C27 C28 -179.3(11) . . . 1_455 ?
C271 O7 C27 N3 -17.7(16) . . . . ?
C271 O7 C27 C28 167.0(13) . . . 1_455 ?
C33 C28 C29 C30 -3(3) . . . . ?
C27 C28 C29 C30 -177.7(18) 1_655 . . . ?
O8 N4 C30 C29 171.0(16) . . . . ?
O9 N4 C30 C29 -14(3) . . . . ?
C301 N4 C30 C29 157(8) . . . . ?
O8 N4 C30 C31 2(3) . . . . ?
O9 N4 C30 C31 177.5(16) . . . . ?
C301 N4 C30 C31 -11(5) . . . . ?
C28 C29 C30 N4 -170.6(18) . . . . ?
C28 C29 C30 C31 -3(3) . . . . ?
N4 C30 C31 C32 175(2) . . . . ?
C29 C30 C31 C32 5(4) . . . . ?
C30 C31 C32 C33 -2(4) . . . . ?
C31 C32 C33 C28 -4(4) . . . . ?
C29 C28 C33 C32 6(3) . . . . ?
C27 C28 C33 C32 -180(2) 1_655 . . . ?
N3 C25 N31 C271 -15.5(14) . . . . ?
C261 C25 N31 C271 -123.6(15) . . . . ?
C24 C25 N31 C271 109.3(11) . . . . ?
C26 C25 N31 C271 -135.6(14) . . . . ?
C25 N31 C271 O7 3.4(17) . . . . ?
C25 N31 C271 C281 175.7(13) . . . . ?
C27 O7 C271 N31 13.3(14) . . . . ?
C27 O7 C271 C281 -158.7(15) . . . . ?
N31 C271 C281 C291 178.3(16) . . . . ?
O7 C271 C281 C291 -10(3) . . . . ?
N31 C271 C281 C331 -4(3) . . . . ?
O7 C271 C281 C331 167.6(15) . . . . ?
C331 C281 C291 C301 3(3) . . . . ?
C271 C281 C291 C301 -178.8(19) . . . . ?
C281 C291 C301 C311 2(3) . . . . ?
C281 C291 C301 N4 -176.0(18) . . . . ?
O8 N4 C301 C291 12(2) . . . . ?
O9 N4 C301 C291 -169.7(17) . . . . ?
C30 N4 C301 C291 -180(100) . . . . ?
O8 N4 C301 C311 -166.2(14) . . . . ?
O9 N4 C301 C311 12(2) . . . . ?
C30 N4 C301 C311 2(5) . . . . ?
C291 C301 C311 C321 -1(3) . . . . ?
N4 C301 C311 C321 176.6(15) . . . . ?
C301 C311 C321 C331 -4(3) . . . . ?
C291 C281 C331 C321 -9(3) . . . . ?
C271 C281 C331 C321 173.7(16) . . . . ?
C311 C321 C331 C281 9(3) . . . . ?
O101 C101 C102 C103 177(6) . . . . ?
C101 C102 C103 O103 177(8) . . . . ?
O111 C111 C112 C113 169(4) . . . . ?
C111 C112 C113 O113 -157(4) . . . . ?
O121 C121 C122 C123 -179(5) . . . . ?
C121 C122 C123 O123 97(5) . . . . ?
O131 C131 C132 C133 25(11) . . . . ?
C131 C132 C133 O133 -124(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.91 1.74 2.640(12) 171.8 3_655
N2 H2A O5 0.91 1.85 2.712(13) 156.5 3_655
O101 H101 O5 0.82 2.27 2.93(4) 137.7 1_655
O111 H111 O51 0.82 2.45 3.17(3) 147.4 1_655
O113 H113 O51 0.82 2.52 3.29(4) 156.4 .
O121 H121 O7 0.82 2.24 2.86(3) 132.6 1_655
O123 H123 O4 0.82 1.96 2.77(3) 168.3 .
O131 H131 O4 0.82 2.52 3.28(6) 154.2 .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045

#===== end

# start Validation Reply Form
_vrf_PLAT241_b3nbdla/13pr1       
;
PROBLEM: Check High Ueq as Compared to Neighbors for O7
RESPONSE: It results from unsolved disorder of the O7 atom of the
disordered alanine derivative
;
_database_code_depnum_ccdc_archive 'CCDC 930489'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
# end Validation Reply Form


data_b3nb(dl)a/12bu1
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-(D~0.82~L~0.18~)-alaninate butanol-1,2-diol
0.82-solvate 0.27-hydrate
;
_chemical_name_common            ?
_chemical_melting_point          415
_chemical_formula_moiety         
'C10 H9 N2 O5, C23 H27 N2 O4, 0.82(C4 H10 O2), 0.27(H2 O)'
_chemical_formula_sum            'C36.28 H44.74 N4 O10.91'
_chemical_formula_weight         711.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.922(2)
_cell_length_b                   12.252(3)
_cell_length_c                   35.746(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3469.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1929
_cell_measurement_theta_min      2.8067
_cell_measurement_theta_max      28.8043

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1511
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10967
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4227
_reflns_number_gt                2065
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4227
_refine_ls_number_parameters     616
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1982(6) 1.2530(3) 0.67802(10) 0.0515(11) Uani 1 1 d . . .
O2 O 0.2377(6) 0.6724(3) 0.81693(10) 0.0600(13) Uani 1 1 d . . .
O3 O 0.2795(7) 0.5566(3) 0.75758(11) 0.0719(15) Uani 1 1 d . . .
O4 O 0.2267(8) 1.0726(3) 0.79284(11) 0.0809(18) Uani 1 1 d . . .
N1 N 0.1650(7) 0.9976(3) 0.73695(11) 0.0440(12) Uani 1 1 d . . .
N2 N 0.1595(8) 0.8998(4) 0.61213(12) 0.0545(15) Uani 1 1 d . . .
H2A H 0.1587 0.8418 0.5962 0.065 Uiso 1 1 calc R . .
C1 C 0.2004(9) 0.8393(4) 0.78134(15) 0.0492(16) Uani 1 1 d . . .
H1A H 0.1888 0.8817 0.8028 0.059 Uiso 1 1 calc R . .
C2 C 0.2274(9) 0.7282(4) 0.78388(15) 0.0519(17) Uani 1 1 d . . .
C3 C 0.2482(8) 0.6648(4) 0.75129(15) 0.0480(17) Uani 1 1 d . . .
C4 C 0.2303(9) 0.7128(4) 0.71661(16) 0.0526(18) Uani 1 1 d . . .
H4A H 0.2383 0.6709 0.6950 0.063 Uiso 1 1 calc R . .
C5 C 0.2004(9) 0.8237(4) 0.71423(14) 0.0460(15) Uani 1 1 d . . .
C6 C 0.1911(8) 0.8856(4) 0.74636(14) 0.0408(14) Uani 1 1 d . . .
C7 C 0.1606(8) 0.8912(4) 0.68028(14) 0.0413(14) Uani 1 1 d . . .
C8 C 0.1729(8) 1.0104(4) 0.69579(13) 0.0400(14) Uani 1 1 d . . .
H8A H 0.0754 1.0528 0.6872 0.048 Uiso 1 1 calc R . .
C9 C 0.2084(9) 1.0830(4) 0.75900(16) 0.0540(17) Uani 1 1 d . . .
C10 C 0.2304(9) 1.1911(4) 0.73997(15) 0.0515(17) Uani 1 1 d . . .
H10A H 0.2991 1.2370 0.7560 0.062 Uiso 1 1 calc R . .
H10B H 0.1203 1.2253 0.7381 0.062 Uiso 1 1 calc R . .
C11 C 0.3109(9) 1.1908(4) 0.70069(15) 0.0480(15) Uani 1 1 d . . .
H11A H 0.4211 1.2271 0.7017 0.058 Uiso 1 1 calc R . .
C12 C 0.2588(10) 1.2766(4) 0.64095(16) 0.0596(19) Uani 1 1 d . . .
H12A H 0.3806 1.2843 0.6415 0.072 Uiso 1 1 calc R . .
H12B H 0.2112 1.3453 0.6325 0.072 Uiso 1 1 calc R . .
C13 C 0.2119(9) 1.1881(4) 0.61395(15) 0.0527(17) Uani 1 1 d . . .
H13A H 0.1392 1.2043 0.5943 0.063 Uiso 1 1 calc R . .
C14 C 0.2707(8) 1.0883(4) 0.61728(15) 0.0518(16) Uani 1 1 d . . .
C15 C 0.2231(10) 0.9977(4) 0.59056(15) 0.059(2) Uani 1 1 d . . .
H15A H 0.1360 1.0231 0.5736 0.071 Uiso 1 1 calc R . .
H15B H 0.3208 0.9770 0.5758 0.071 Uiso 1 1 calc R . .
C16 C -0.0179(10) 0.9148(5) 0.62669(16) 0.0593(19) Uani 1 1 d . . .
H16A H -0.0473 0.9916 0.6275 0.071 Uiso 1 1 calc R . .
H16B H -0.0983 0.8771 0.6108 0.071 Uiso 1 1 calc R . .
C17 C -0.0176(9) 0.8666(5) 0.66544(15) 0.0561(19) Uani 1 1 d . . .
H17A H -0.0381 0.7885 0.6646 0.067 Uiso 1 1 calc R . .
H17B H -0.1030 0.9006 0.6810 0.067 Uiso 1 1 calc R . .
C18 C 0.3335(8) 1.0728(4) 0.68740(14) 0.0449(15) Uani 1 1 d . . .
H18A H 0.4201 1.0411 0.7037 0.054 Uiso 1 1 calc R . .
C19 C 0.3964(8) 1.0549(4) 0.64731(16) 0.0477(15) Uani 1 1 d . . .
H19A H 0.5014 1.0958 0.6437 0.057 Uiso 1 1 calc R . .
C20 C 0.4341(9) 0.9321(4) 0.64425(17) 0.0547(17) Uani 1 1 d . . .
H20A H 0.4916 0.9171 0.6209 0.066 Uiso 1 1 calc R . .
H20B H 0.5072 0.9098 0.6646 0.066 Uiso 1 1 calc R . .
C21 C 0.2716(9) 0.8693(4) 0.64584(16) 0.0520(18) Uani 1 1 d . . .
H21A H 0.2972 0.7911 0.6447 0.062 Uiso 1 1 calc R . .
C22 C 0.2110(10) 0.7336(5) 0.85022(15) 0.067(2) Uani 1 1 d . . .
H22A H 0.2187 0.6860 0.8715 0.101 Uiso 1 1 calc R . .
H22B H 0.1010 0.7664 0.8495 0.101 Uiso 1 1 calc R . .
H22C H 0.2952 0.7896 0.8522 0.101 Uiso 1 1 calc R . .
C23 C 0.2960(13) 0.4882(4) 0.72542(19) 0.095(3) Uani 1 1 d . . .
H23A H 0.3178 0.4145 0.7332 0.142 Uiso 1 1 calc R . .
H23B H 0.3880 0.5136 0.7103 0.142 Uiso 1 1 calc R . .
H23C H 0.1934 0.4904 0.7112 0.142 Uiso 1 1 calc R . .
O8 O 0.5700(11) 0.1084(7) 0.5657(3) 0.082(3) Uani 0.821(5) 1 d PD A 1
O9 O 0.8360(13) 0.1173(9) 0.5594(4) 0.092(3) Uani 0.821(5) 1 d PD A 1
N4 N 0.6959(11) 0.1603(7) 0.5563(4) 0.066(3) Uani 0.821(5) 1 d PD A 1
O5 O 0.2214(10) 0.7210(4) 0.57165(14) 0.0700(19) Uani 0.821(5) 1 d P A 1
O6 O 0.0591(10) 0.8063(4) 0.53237(16) 0.084(2) Uani 0.821(5) 1 d P A 1
O7 O 0.2005(18) 0.4151(10) 0.5373(2) 0.085(3) Uani 0.821(5) 1 d PU A 1
N3 N 0.3179(10) 0.5747(5) 0.51673(17) 0.063(2) Uani 0.821(5) 1 d P A 1
H3A H 0.4092 0.6099 0.5119 0.076 Uiso 0.821(5) 1 calc PR A 1
C26 C 0.1250(16) 0.6603(9) 0.4742(3) 0.087(4) Uani 0.821(5) 1 d PU A 1
H26A H 0.0054 0.6566 0.4700 0.130 Uiso 0.821(5) 1 calc PR A 1
H26B H 0.1812 0.6092 0.4581 0.130 Uiso 0.821(5) 1 calc PR A 1
H26C H 0.1645 0.7327 0.4690 0.130 Uiso 0.821(5) 1 calc PR A 1
C27 C 0.3326(12) 0.4680(6) 0.5267(2) 0.055(2) Uani 0.821(5) 1 d P A 1
C28 C 0.5089(11) 0.4170(6) 0.5261(2) 0.042(2) Uani 0.821(5) 1 d P A 1
C29 C 0.5244(11) 0.3145(6) 0.5406(2) 0.043(2) Uani 0.821(5) 1 d P A 1
H29A H 0.4308 0.2780 0.5501 0.052 Uiso 0.821(5) 1 calc PR A 1
C30 C 0.6812(13) 0.2659(5) 0.5410(2) 0.042(2) Uani 0.821(5) 1 d PD A 1
C31 C 0.8227(12) 0.3155(6) 0.5275(2) 0.053(2) Uani 0.821(5) 1 d P A 1
H31A H 0.9275 0.2816 0.5290 0.064 Uiso 0.821(5) 1 calc PR A 1
C32 C 0.8055(13) 0.4166(7) 0.5118(3) 0.070(3) Uani 0.821(5) 1 d P A 1
H32A H 0.8997 0.4513 0.5018 0.084 Uiso 0.821(5) 1 calc PR A 1
C33 C 0.6474(13) 0.4690(6) 0.5104(3) 0.058(3) Uani 0.821(5) 1 d P A 1
H33A H 0.6361 0.5372 0.4992 0.069 Uiso 0.821(5) 1 calc PR A 1
O51 O 0.089(4) 0.7371(18) 0.5656(8) 0.048(7) Uani 0.179(5) 1 d PU A 2
O61 O 0.264(4) 0.8175(17) 0.5287(6) 0.062(7) Uani 0.179(5) 1 d PU A 2
O71 O 0.190(10) 0.416(5) 0.5221(13) 0.081(6) Uani 0.179(5) 1 d PU A 2
O81 O -0.397(4) 0.078(3) 0.5628(19) 0.12(3) Uani 0.179(5) 1 d PDU A 2
O91 O -0.130(4) 0.096(3) 0.5635(15) 0.048(10) Uani 0.179(5) 1 d PDU A 2
N41 N -0.271(4) 0.136(2) 0.5582(11) 0.011(7) Uani 0.179(5) 1 d PDU A 2
N31 N 0.021(3) 0.5718(17) 0.5128(6) 0.034(6) Uani 0.179(5) 1 d PU A 2
H31B H -0.0741 0.5978 0.5052 0.041 Uiso 0.179(5) 1 calc PR A 2
C261 C 0.214(8) 0.686(5) 0.4703(17) 0.088(7) Uani 0.179(5) 1 d PU A 2
H26D H 0.2205 0.6274 0.4524 0.132 Uiso 0.179(5) 1 calc PR A 2
H26E H 0.3216 0.7216 0.4718 0.132 Uiso 0.179(5) 1 calc PR A 2
H26F H 0.1296 0.7370 0.4626 0.132 Uiso 0.179(5) 1 calc PR A 2
C271 C 0.035(4) 0.4695(19) 0.5242(7) 0.022(6) Uani 0.179(5) 1 d PU A 2
C281 C -0.136(4) 0.412(2) 0.5276(10) 0.060(8) Uani 0.179(5) 1 d PGU A 2
C291 C -0.128(4) 0.308(2) 0.5432(9) 0.060(8) Uani 0.179(5) 1 d PGU A 2
H29B H -0.0255 0.2803 0.5514 0.071 Uiso 0.179(5) 1 calc PR A 2
C301 C -0.274(5) 0.2456(19) 0.5466(10) 0.058(9) Uani 0.179(5) 1 d PGDU A 2
C311 C -0.428(4) 0.287(3) 0.5344(11) 0.060(9) Uani 0.179(5) 1 d PGU A 2
H31C H -0.5254 0.2452 0.5367 0.072 Uiso 0.179(5) 1 calc PR A 2
C321 C -0.436(4) 0.391(3) 0.5188(11) 0.064(9) Uani 0.179(5) 1 d PGU A 2
H32B H -0.5389 0.4184 0.5106 0.077 Uiso 0.179(5) 1 calc PR A 2
C331 C -0.290(5) 0.453(2) 0.5154(11) 0.062(9) Uani 0.179(5) 1 d PGU A 2
H33B H -0.2956 0.5225 0.5050 0.074 Uiso 0.179(5) 1 calc PR A 2
C24 C 0.1549(11) 0.7304(5) 0.54024(19) 0.0566(19) Uani 1 1 d . . .
C25 C 0.1617(10) 0.6329(5) 0.51371(18) 0.0606(19) Uani 1 1 d . A .
H25B H 0.2547 0.5858 0.5218 0.073 Uiso 0.179(5) 1 calc PR A 2
H25A H 0.0754 0.5834 0.5219 0.073 Uiso 0.821(5) 1 d PR A 1
O101 O 0.3333(11) 0.5819(5) 0.62986(17) 0.092(2) Uani 0.821(5) 1 d P A 1
H101 H 0.2984 0.6226 0.6134 0.138 Uiso 0.821(5) 1 calc PR A 1
O102 O 0.6454(9) 0.7021(4) 0.64837(15) 0.079(2) Uani 0.821(5) 1 d P A 1
H102 H 0.7000 0.6654 0.6633 0.118 Uiso 0.821(5) 1 calc PR A 1
C101 C 0.4995(17) 0.5506(8) 0.6217(3) 0.094(4) Uani 0.821(5) 1 d P A 1
H10C H 0.4990 0.5070 0.5991 0.112 Uiso 0.821(5) 1 calc PR A 1
H10D H 0.5409 0.5049 0.6419 0.112 Uiso 0.821(5) 1 calc PR A 1
C102 C 0.6167(14) 0.6423(9) 0.6166(3) 0.084(3) Uani 0.821(5) 1 d P A 1
H10E H 0.5602 0.6923 0.5992 0.101 Uiso 0.821(5) 1 calc PR A 1
C103 C 0.786(2) 0.6148(9) 0.5984(3) 0.124(5) Uani 0.821(5) 1 d P A 1
H10F H 0.7631 0.5900 0.5731 0.149 Uiso 0.821(5) 1 calc PR A 1
H10G H 0.8501 0.6818 0.5964 0.149 Uiso 0.821(5) 1 calc PR A 1
C104 C 0.8950(18) 0.5315(9) 0.6169(3) 0.107(4) Uani 0.821(5) 1 d P A 1
H10H H 0.9594 0.4934 0.5982 0.160 Uiso 0.821(5) 1 calc PR A 1
H10I H 0.8255 0.4805 0.6302 0.160 Uiso 0.821(5) 1 calc PR A 1
H10J H 0.9703 0.5671 0.6340 0.160 Uiso 0.821(5) 1 calc PR A 1
O1W O 0.730(5) 0.527(3) 0.6136(8) 0.089(10) Uani 0.179(5) 1 d PU A 2
O2W O 1.034(10) 0.611(5) 0.6235(19) 0.11(2) Uani 0.090(3) 1 d PU A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.058(3) 0.0432(19) 0.053(2) 0.0059(18) -0.002(2) 0.002(2)
O2 0.074(4) 0.053(2) 0.052(2) 0.015(2) -0.005(2) 0.001(2)
O3 0.109(5) 0.0383(19) 0.069(3) 0.006(2) -0.010(3) 0.005(3)
O4 0.144(6) 0.056(2) 0.042(2) -0.002(2) -0.012(3) -0.004(3)
N1 0.054(4) 0.036(2) 0.042(2) -0.001(2) -0.002(3) -0.003(3)
N2 0.074(4) 0.048(3) 0.041(3) -0.004(2) -0.002(3) -0.012(3)
C1 0.056(4) 0.046(3) 0.046(3) 0.000(3) -0.007(3) -0.003(3)
C2 0.056(5) 0.050(3) 0.050(3) 0.009(3) -0.002(4) 0.003(3)
C3 0.055(5) 0.036(2) 0.054(4) 0.000(3) -0.005(4) -0.004(3)
C4 0.066(5) 0.042(3) 0.050(3) 0.001(3) -0.001(4) -0.005(3)
C5 0.056(4) 0.040(3) 0.042(3) 0.003(2) -0.002(4) -0.008(3)
C6 0.048(4) 0.038(2) 0.037(3) 0.002(2) 0.003(3) -0.006(3)
C7 0.054(4) 0.035(2) 0.035(3) 0.002(2) -0.004(3) -0.007(3)
C8 0.046(4) 0.035(2) 0.039(3) 0.003(2) 0.003(3) 0.002(3)
C9 0.069(5) 0.047(3) 0.046(3) -0.003(3) -0.006(4) 0.009(4)
C10 0.068(5) 0.038(3) 0.049(3) -0.003(3) -0.002(4) 0.002(3)
C11 0.046(4) 0.036(3) 0.062(4) 0.001(3) 0.002(4) -0.005(3)
C12 0.069(5) 0.038(3) 0.072(4) 0.012(3) 0.010(4) 0.000(3)
C13 0.067(5) 0.042(3) 0.049(3) 0.010(3) 0.004(4) -0.005(3)
C14 0.054(5) 0.050(3) 0.051(3) 0.006(3) 0.002(3) -0.007(4)
C15 0.083(6) 0.048(3) 0.047(3) 0.009(3) 0.013(4) -0.005(4)
C16 0.079(6) 0.049(3) 0.050(4) -0.008(3) -0.015(4) -0.007(4)
C17 0.074(5) 0.050(3) 0.044(3) 0.009(3) -0.007(4) -0.022(4)
C18 0.047(4) 0.043(3) 0.045(3) 0.001(3) -0.003(3) 0.002(3)
C19 0.038(4) 0.046(3) 0.059(4) 0.003(3) 0.002(3) 0.002(3)
C20 0.059(5) 0.054(3) 0.051(3) -0.003(3) 0.005(4) 0.009(4)
C21 0.070(5) 0.038(3) 0.048(3) -0.003(3) -0.004(4) 0.008(3)
C22 0.079(6) 0.078(4) 0.044(3) 0.008(3) -0.001(4) 0.007(4)
C23 0.166(10) 0.035(3) 0.083(5) -0.011(3) -0.008(6) 0.005(5)
O8 0.097(6) 0.045(4) 0.103(6) 0.019(4) 0.036(5) 0.005(4)
O9 0.084(7) 0.096(7) 0.097(7) 0.010(5) -0.017(6) 0.043(6)
N4 0.076(8) 0.063(6) 0.059(5) -0.001(5) 0.000(5) 0.024(6)
O5 0.100(6) 0.060(3) 0.050(3) -0.006(3) -0.018(4) 0.018(4)
O6 0.119(6) 0.055(3) 0.078(4) -0.007(3) -0.028(4) 0.035(4)
O7 0.077(5) 0.061(3) 0.116(7) 0.026(6) 0.013(7) -0.015(4)
N3 0.063(5) 0.054(4) 0.072(4) -0.007(3) 0.006(4) -0.006(4)
C26 0.109(10) 0.087(7) 0.064(5) -0.005(5) -0.022(7) 0.009(7)
C27 0.063(6) 0.044(4) 0.059(5) 0.006(3) -0.011(5) -0.002(5)
C28 0.047(5) 0.036(4) 0.044(4) -0.009(3) 0.003(4) 0.002(4)
C29 0.050(6) 0.039(4) 0.040(4) -0.001(4) 0.002(4) 0.001(4)
C30 0.056(7) 0.039(4) 0.032(4) -0.002(3) -0.013(4) 0.011(4)
C31 0.045(6) 0.055(5) 0.061(5) -0.011(4) 0.005(5) 0.006(5)
C32 0.047(6) 0.064(5) 0.099(8) -0.004(5) 0.021(6) -0.011(6)
C33 0.061(7) 0.050(4) 0.063(5) 0.008(4) 0.015(5) 0.007(5)
O51 0.057(11) 0.037(9) 0.051(10) -0.014(8) 0.005(9) -0.009(8)
O61 0.068(11) 0.048(9) 0.070(10) -0.014(8) 0.010(9) -0.018(9)
O71 0.079(8) 0.067(8) 0.096(10) 0.010(8) 0.005(9) -0.012(7)
O81 0.12(3) 0.12(3) 0.12(3) 0.000(5) 0.001(5) -0.001(5)
O91 0.046(13) 0.049(12) 0.050(13) 0.002(9) 0.003(9) -0.005(9)
N41 0.014(8) 0.008(8) 0.010(8) 0.005(4) 0.000(5) -0.001(5)
N31 0.033(10) 0.027(9) 0.042(10) -0.004(8) 0.008(8) -0.008(8)
C261 0.097(11) 0.090(9) 0.077(9) -0.006(8) -0.008(8) 0.005(8)
C271 0.020(10) 0.024(9) 0.023(9) -0.004(8) -0.004(8) -0.006(8)
C281 0.061(10) 0.059(10) 0.060(10) -0.002(7) 0.003(7) 0.002(7)
C291 0.060(10) 0.058(10) 0.061(10) 0.000(7) 0.003(7) -0.001(7)
C301 0.059(11) 0.057(10) 0.059(10) -0.001(7) 0.000(7) -0.001(7)
C311 0.060(11) 0.061(11) 0.058(11) -0.001(7) 0.003(7) -0.001(7)
C321 0.061(11) 0.066(11) 0.065(10) -0.002(7) 0.000(7) 0.003(7)
C331 0.062(11) 0.060(10) 0.064(10) -0.001(7) 0.001(7) 0.000(7)
C24 0.074(6) 0.040(3) 0.056(4) -0.009(3) -0.011(5) 0.005(4)
C25 0.061(5) 0.054(3) 0.067(4) -0.009(3) 0.000(4) 0.013(4)
O101 0.105(6) 0.089(4) 0.082(4) 0.006(3) -0.016(4) -0.005(5)
O102 0.105(6) 0.056(3) 0.075(4) -0.001(3) -0.037(4) 0.001(4)
C101 0.113(11) 0.076(6) 0.092(7) -0.025(6) 0.012(8) 0.002(8)
C102 0.065(7) 0.114(8) 0.073(7) 0.016(6) -0.002(6) 0.007(7)
C103 0.176(16) 0.094(7) 0.104(8) -0.013(7) -0.004(10) -0.034(10)
C104 0.113(12) 0.104(8) 0.102(8) 0.013(7) 0.020(9) 0.026(9)
O1W 0.099(13) 0.094(13) 0.075(12) 0.002(9) -0.007(10) 0.006(10)
O2W 0.11(2) 0.10(2) 0.11(2) -0.003(10) 0.001(10) 0.000(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.426(7) . ?
O1 C12 1.439(7) . ?
O2 C2 1.368(6) . ?
O2 C22 1.422(6) . ?
O3 C3 1.368(6) . ?
O3 C23 1.429(7) . ?
O4 C9 1.225(6) . ?
N1 C9 1.354(7) . ?
N1 C6 1.428(6) . ?
N1 C8 1.481(6) . ?
N2 C16 1.510(9) . ?
N2 C15 1.512(7) . ?
N2 C21 1.543(7) . ?
N2 H2A 0.9100 . ?
C1 C6 1.375(7) . ?
C1 C2 1.380(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.410(7) . ?
C3 C4 1.379(7) . ?
C4 C5 1.382(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.378(7) . ?
C5 C7 1.502(7) . ?
C7 C21 1.537(8) . ?
C7 C17 1.538(9) . ?
C7 C8 1.566(6) . ?
C8 C18 1.513(8) . ?
C8 H8A 0.9800 . ?
C9 C10 1.500(8) . ?
C10 C11 1.542(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.533(7) . ?
C11 H11A 0.9800 . ?
C12 C13 1.498(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.314(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.512(8) . ?
C14 C19 1.520(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.506(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.533(7) . ?
C18 H18A 0.9800 . ?
C19 C20 1.537(7) . ?
C19 H19A 0.9800 . ?
C20 C21 1.500(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O8 N4 1.230(6) . ?
O9 N4 1.233(6) . ?
N4 C30 1.409(9) . ?
O5 C24 1.245(8) . ?
O6 C24 1.233(8) . ?
O7 C27 1.289(15) . ?
N3 C27 1.360(9) . ?
N3 C25 1.433(9) . ?
N3 H3A 0.8600 . ?
C26 C25 1.479(12) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.531(12) . ?
C28 C29 1.364(9) . ?
C28 C33 1.388(10) . ?
C29 C30 1.377(11) . ?
C29 H29A 0.9300 . ?
C30 C31 1.363(12) . ?
C31 C32 1.368(11) . ?
C31 H31A 0.9300 . ?
C32 C33 1.408(12) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
O51 C24 1.05(2) . ?
O61 C24 1.43(2) . ?
O71 C271 1.39(8) . ?
O81 N41 1.231(7) . ?
O91 N41 1.232(7) . ?
N41 C301 1.408(10) . ?
N31 C271 1.32(3) . ?
N31 C25 1.35(2) . ?
N31 H31B 0.8600 . ?
N31 H25A 0.5607 . ?
C261 C25 1.73(6) . ?
C261 H26D 0.9600 . ?
C261 H26E 0.9600 . ?
C261 H26F 0.9600 . ?
C271 C281 1.54(4) . ?
C281 C291 1.3900 . ?
C281 C331 1.3900 . ?
C291 C301 1.3900 . ?
C291 H29B 0.9300 . ?
C301 C311 1.3900 . ?
C311 C321 1.3900 . ?
C311 H31C 0.9300 . ?
C321 C331 1.3900 . ?
C321 H32B 0.9300 . ?
C331 H33B 0.9300 . ?
C24 C25 1.526(8) . ?
C25 H25B 0.9800 . ?
C25 H25A 0.9600 . ?
O101 C101 1.402(12) . ?
O101 H101 0.8200 . ?
O102 C102 1.370(11) . ?
O102 H102 0.8200 . ?
C101 C102 1.469(14) . ?
C101 H10C 0.9700 . ?
C101 H10D 0.9700 . ?
C102 C103 1.526(16) . ?
C102 H10E 0.9800 . ?
C103 C104 1.493(15) . ?
C103 H10F 0.9700 . ?
C103 H10G 0.9700 . ?
C104 H10H 0.9600 . ?
C104 H10I 0.9600 . ?
C104 H10J 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 115.0(5) . . ?
C2 O2 C22 116.8(4) . . ?
C3 O3 C23 116.9(4) . . ?
C9 N1 C6 124.6(5) . . ?
C9 N1 C8 119.1(4) . . ?
C6 N1 C8 109.2(4) . . ?
C16 N2 C15 112.9(5) . . ?
C16 N2 C21 107.2(4) . . ?
C15 N2 C21 113.5(5) . . ?
C16 N2 H2A 107.6 . . ?
C15 N2 H2A 107.6 . . ?
C21 N2 H2A 107.6 . . ?
C6 C1 C2 118.4(5) . . ?
C6 C1 H1A 120.8 . . ?
C2 C1 H1A 120.8 . . ?
O2 C2 C1 124.0(5) . . ?
O2 C2 C3 115.5(5) . . ?
C1 C2 C3 120.5(5) . . ?
O3 C3 C4 125.4(5) . . ?
O3 C3 C2 114.8(5) . . ?
C4 C3 C2 119.7(5) . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 C7 111.0(4) . . ?
C4 C5 C7 128.8(5) . . ?
C1 C6 C5 121.8(5) . . ?
C1 C6 N1 128.2(4) . . ?
C5 C6 N1 109.9(4) . . ?
C5 C7 C21 115.5(5) . . ?
C5 C7 C17 111.3(5) . . ?
C21 C7 C17 102.4(5) . . ?
C5 C7 C8 102.4(4) . . ?
C21 C7 C8 114.2(4) . . ?
C17 C7 C8 111.3(5) . . ?
N1 C8 C18 106.6(5) . . ?
N1 C8 C7 104.5(3) . . ?
C18 C8 C7 117.0(5) . . ?
N1 C8 H8A 109.5 . . ?
C18 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
O4 C9 N1 121.6(5) . . ?
O4 C9 C10 121.7(5) . . ?
N1 C9 C10 116.6(5) . . ?
C9 C10 C11 117.3(4) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 113.6(5) . . ?
O1 C11 C10 104.9(5) . . ?
C18 C11 C10 109.4(4) . . ?
O1 C11 H11A 109.6 . . ?
C18 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
O1 C12 C13 111.4(4) . . ?
O1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 121.8(6) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C15 122.5(6) . . ?
C13 C14 C19 123.1(5) . . ?
C15 C14 C19 114.3(5) . . ?
N2 C15 C14 110.1(4) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 N2 105.5(5) . . ?
C17 C16 H16A 110.6 . . ?
N2 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
N2 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 104.0(5) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C19 112.7(4) . . ?
C8 C18 C11 108.5(5) . . ?
C19 C18 C11 117.5(4) . . ?
C8 C18 H18A 105.7 . . ?
C19 C18 H18A 105.7 . . ?
C11 C18 H18A 105.7 . . ?
C14 C19 C18 114.1(5) . . ?
C14 C19 C20 109.9(5) . . ?
C18 C19 C20 105.6(4) . . ?
C14 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C21 C20 C19 109.4(5) . . ?
C21 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C20 C21 C7 115.6(5) . . ?
C20 C21 N2 109.9(5) . . ?
C7 C21 N2 104.7(5) . . ?
C20 C21 H21A 108.8 . . ?
C7 C21 H21A 108.8 . . ?
N2 C21 H21A 108.8 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 N4 O9 118.9(9) . . ?
O8 N4 C30 120.9(9) . . ?
O9 N4 C30 120.1(9) . . ?
C27 N3 C25 124.9(7) . . ?
C27 N3 H3A 117.5 . . ?
C25 N3 H3A 117.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 N3 119.4(10) . . ?
O7 C27 C28 122.6(8) . . ?
N3 C27 C28 117.9(8) . . ?
C29 C28 C33 120.4(8) . . ?
C29 C28 C27 117.0(7) . . ?
C33 C28 C27 122.6(7) . . ?
C28 C29 C30 118.9(7) . . ?
C28 C29 H29A 120.6 . . ?
C30 C29 H29A 120.6 . . ?
C31 C30 C29 123.1(6) . . ?
C31 C30 N4 118.5(8) . . ?
C29 C30 N4 118.4(8) . . ?
C30 C31 C32 117.9(8) . . ?
C30 C31 H31A 121.1 . . ?
C32 C31 H31A 121.1 . . ?
C31 C32 C33 121.1(8) . . ?
C31 C32 H32A 119.5 . . ?
C33 C32 H32A 119.5 . . ?
C28 C33 C32 118.6(7) . . ?
C28 C33 H33A 120.7 . . ?
C32 C33 H33A 120.7 . . ?
O81 N41 O91 118.9(11) . . ?
O81 N41 C301 125(3) . . ?
O91 N41 C301 116(3) . . ?
C271 N31 C25 117(2) . . ?
C271 N31 H31B 121.7 . . ?
C25 N31 H31B 121.7 . . ?
C271 N31 H25A 89.7 . . ?
C25 N31 H25A 37.1 . . ?
H31B N31 H25A 139.8 . . ?
C25 C261 H26D 109.5 . . ?
C25 C261 H26E 109.5 . . ?
H26D C261 H26E 109.5 . . ?
C25 C261 H26F 109.5 . . ?
H26D C261 H26F 109.5 . . ?
H26E C261 H26F 109.5 . . ?
N31 C271 O71 121(4) . . ?
N31 C271 C281 113(3) . . ?
O71 C271 C281 124(4) . . ?
N31 C271 H25A 23.0 . . ?
O71 C271 H25A 105.3 . . ?
C281 C271 H25A 130.4 . . ?
C291 C281 C331 120.0 . . ?
C291 C281 C271 114(2) . . ?
C331 C281 C271 126(2) . . ?
C301 C291 C281 120.0 . . ?
C301 C291 H29B 120.0 . . ?
C281 C291 H29B 120.0 . . ?
C291 C301 C311 120.0 . . ?
C291 C301 N41 123(3) . . ?
C311 C301 N41 117(3) . . ?
C321 C311 C301 120.0 . . ?
C321 C311 H31C 120.0 . . ?
C301 C311 H31C 120.0 . . ?
C311 C321 C331 120.0 . . ?
C311 C321 H32B 120.0 . . ?
C331 C321 H32B 120.0 . . ?
C321 C331 C281 120.0 . . ?
C321 C331 H33B 120.0 . . ?
C281 C331 H33B 120.0 . . ?
O51 C24 O6 80.3(17) . . ?
O51 C24 O5 55.8(16) . . ?
O6 C24 O5 122.4(7) . . ?
O51 C24 O61 119.3(16) . . ?
O6 C24 O61 75.0(11) . . ?
O5 C24 O61 94.3(12) . . ?
O51 C24 C25 128.1(14) . . ?
O6 C24 C25 118.0(6) . . ?
O5 C24 C25 118.3(6) . . ?
O61 C24 C25 112.5(10) . . ?
N31 C25 N3 116.2(11) . . ?
N31 C25 C26 86.6(11) . . ?
N3 C25 C26 110.7(7) . . ?
N31 C25 C24 114.9(11) . . ?
N3 C25 C24 111.9(6) . . ?
C26 C25 C24 114.2(6) . . ?
N31 C25 C261 113(2) . . ?
N3 C25 C261 93(2) . . ?
C26 C25 C261 27(2) . . ?
C24 C25 C261 106(2) . . ?
N31 C25 H25B 107.7 . . ?
N3 C25 H25B 15.1 . . ?
C26 C25 H25B 124.3 . . ?
C24 C25 H25B 107.7 . . ?
C261 C25 H25B 107.7 . . ?
N31 C25 H25A 20.6 . . ?
N3 C25 H25A 106.1 . . ?
C26 C25 H25A 107.1 . . ?
C24 C25 H25A 106.2 . . ?
C261 C25 H25A 132.9 . . ?
H25B C25 H25A 94.2 . . ?
C101 O101 H101 109.5 . . ?
C102 O102 H102 109.5 . . ?
O101 C101 C102 114.2(9) . . ?
O101 C101 H10C 108.7 . . ?
C102 C101 H10C 108.7 . . ?
O101 C101 H10D 108.7 . . ?
C102 C101 H10D 108.7 . . ?
H10C C101 H10D 107.6 . . ?
O102 C102 C101 114.2(9) . . ?
O102 C102 C103 109.1(9) . . ?
C101 C102 C103 116.0(10) . . ?
O102 C102 H10E 105.5 . . ?
C101 C102 H10E 105.5 . . ?
C103 C102 H10E 105.5 . . ?
C104 C103 C102 118.1(10) . . ?
C104 C103 H10F 107.8 . . ?
C102 C103 H10F 107.8 . . ?
C104 C103 H10G 107.8 . . ?
C102 C103 H10G 107.8 . . ?
H10F C103 H10G 107.1 . . ?
C103 C104 H10H 109.5 . . ?
C103 C104 H10I 109.5 . . ?
H10H C104 H10I 109.5 . . ?
C103 C104 H10J 109.5 . . ?
H10H C104 H10J 109.5 . . ?
H10I C104 H10J 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 3.0(10) . . . . ?
C22 O2 C2 C3 -177.7(6) . . . . ?
C6 C1 C2 O2 -179.5(6) . . . . ?
C6 C1 C2 C3 1.3(11) . . . . ?
C23 O3 C3 C4 0.5(11) . . . . ?
C23 O3 C3 C2 178.0(7) . . . . ?
O2 C2 C3 O3 -1.3(9) . . . . ?
C1 C2 C3 O3 178.0(6) . . . . ?
O2 C2 C3 C4 176.4(6) . . . . ?
C1 C2 C3 C4 -4.3(11) . . . . ?
O3 C3 C4 C5 -179.4(6) . . . . ?
C2 C3 C4 C5 3.2(11) . . . . ?
C3 C4 C5 C6 0.9(11) . . . . ?
C3 C4 C5 C7 -173.5(7) . . . . ?
C2 C1 C6 C5 2.9(11) . . . . ?
C2 C1 C6 N1 -179.7(6) . . . . ?
C4 C5 C6 C1 -4.1(11) . . . . ?
C7 C5 C6 C1 171.3(6) . . . . ?
C4 C5 C6 N1 178.1(6) . . . . ?
C7 C5 C6 N1 -6.5(8) . . . . ?
C9 N1 C6 C1 27.1(11) . . . . ?
C8 N1 C6 C1 177.1(7) . . . . ?
C9 N1 C6 C5 -155.3(6) . . . . ?
C8 N1 C6 C5 -5.3(8) . . . . ?
C6 C5 C7 C21 139.4(6) . . . . ?
C4 C5 C7 C21 -45.8(10) . . . . ?
C6 C5 C7 C17 -104.4(6) . . . . ?
C4 C5 C7 C17 70.5(9) . . . . ?
C6 C5 C7 C8 14.6(7) . . . . ?
C4 C5 C7 C8 -170.5(7) . . . . ?
C9 N1 C8 C18 41.5(7) . . . . ?
C6 N1 C8 C18 -110.4(5) . . . . ?
C9 N1 C8 C7 166.0(6) . . . . ?
C6 N1 C8 C7 14.1(7) . . . . ?
C5 C7 C8 N1 -16.7(7) . . . . ?
C21 C7 C8 N1 -142.4(5) . . . . ?
C17 C7 C8 N1 102.3(5) . . . . ?
C5 C7 C8 C18 100.9(5) . . . . ?
C21 C7 C8 C18 -24.8(7) . . . . ?
C17 C7 C8 C18 -140.1(5) . . . . ?
C6 N1 C9 O4 -22.4(11) . . . . ?
C8 N1 C9 O4 -169.7(6) . . . . ?
C6 N1 C9 C10 158.5(6) . . . . ?
C8 N1 C9 C10 11.2(9) . . . . ?
O4 C9 C10 C11 143.6(7) . . . . ?
N1 C9 C10 C11 -37.2(10) . . . . ?
C12 O1 C11 C18 -68.5(6) . . . . ?
C12 O1 C11 C10 172.0(4) . . . . ?
C9 C10 C11 O1 128.9(6) . . . . ?
C9 C10 C11 C18 6.6(9) . . . . ?
C11 O1 C12 C13 88.7(6) . . . . ?
O1 C12 C13 C14 -64.2(9) . . . . ?
C12 C13 C14 C15 179.3(6) . . . . ?
C12 C13 C14 C19 -2.9(10) . . . . ?
C16 N2 C15 C14 76.1(7) . . . . ?
C21 N2 C15 C14 -46.2(7) . . . . ?
C13 C14 C15 N2 -127.5(7) . . . . ?
C19 C14 C15 N2 54.5(8) . . . . ?
C15 N2 C16 C17 -139.6(5) . . . . ?
C21 N2 C16 C17 -13.8(6) . . . . ?
N2 C16 C17 C7 33.8(6) . . . . ?
C5 C7 C17 C16 -164.6(5) . . . . ?
C21 C7 C17 C16 -40.6(5) . . . . ?
C8 C7 C17 C16 81.9(5) . . . . ?
N1 C8 C18 C19 157.6(4) . . . . ?
C7 C8 C18 C19 41.2(6) . . . . ?
N1 C8 C18 C11 -70.5(5) . . . . ?
C7 C8 C18 C11 173.1(4) . . . . ?
O1 C11 C18 C8 -71.8(6) . . . . ?
C10 C11 C18 C8 45.0(7) . . . . ?
O1 C11 C18 C19 57.5(8) . . . . ?
C10 C11 C18 C19 174.4(5) . . . . ?
C13 C14 C19 C18 59.6(8) . . . . ?
C15 C14 C19 C18 -122.4(5) . . . . ?
C13 C14 C19 C20 178.0(6) . . . . ?
C15 C14 C19 C20 -4.0(7) . . . . ?
C8 C18 C19 C14 59.1(6) . . . . ?
C11 C18 C19 C14 -68.2(7) . . . . ?
C8 C18 C19 C20 -61.8(6) . . . . ?
C11 C18 C19 C20 171.0(6) . . . . ?
C14 C19 C20 C21 -54.9(6) . . . . ?
C18 C19 C20 C21 68.6(6) . . . . ?
C19 C20 C21 C7 -55.4(6) . . . . ?
C19 C20 C21 N2 62.8(6) . . . . ?
C5 C7 C21 C20 -86.2(6) . . . . ?
C17 C7 C21 C20 152.6(5) . . . . ?
C8 C7 C21 C20 32.2(7) . . . . ?
C5 C7 C21 N2 152.7(5) . . . . ?
C17 C7 C21 N2 31.6(5) . . . . ?
C8 C7 C21 N2 -88.9(6) . . . . ?
C16 N2 C21 C20 -136.2(5) . . . . ?
C15 N2 C21 C20 -10.8(6) . . . . ?
C16 N2 C21 C7 -11.5(5) . . . . ?
C15 N2 C21 C7 113.9(5) . . . . ?
C25 N3 C27 O7 -5.9(12) . . . . ?
C25 N3 C27 C28 176.2(6) . . . . ?
O7 C27 C28 C29 -5.8(12) . . . . ?
N3 C27 C28 C29 172.0(6) . . . . ?
O7 C27 C28 C33 171.8(9) . . . . ?
N3 C27 C28 C33 -10.4(11) . . . . ?
C33 C28 C29 C30 3.1(10) . . . . ?
C27 C28 C29 C30 -179.3(7) . . . . ?
C28 C29 C30 C31 0.0(11) . . . . ?
C28 C29 C30 N4 179.7(8) . . . . ?
O8 N4 C30 C31 -173.4(11) . . . . ?
O9 N4 C30 C31 4.5(17) . . . . ?
O8 N4 C30 C29 6.9(16) . . . . ?
O9 N4 C30 C29 -175.2(11) . . . . ?
C29 C30 C31 C32 -2.3(11) . . . . ?
N4 C30 C31 C32 178.0(9) . . . . ?
C30 C31 C32 C33 1.6(12) . . . . ?
C29 C28 C33 C32 -3.7(11) . . . . ?
C27 C28 C33 C32 178.8(8) . . . . ?
C31 C32 C33 C28 1.3(12) . . . . ?
C25 N31 C271 O71 -26(4) . . . . ?
C25 N31 C271 C281 172(2) . . . . ?
N31 C271 C281 C291 -174(2) . . . . ?
O71 C271 C281 C291 25(4) . . . . ?
N31 C271 C281 C331 9(3) . . . . ?
O71 C271 C281 C331 -153(3) . . . . ?
C331 C281 C291 C301 0.0 . . . . ?
C271 C281 C291 C301 -178(3) . . . . ?
C281 C291 C301 C311 0.0 . . . . ?
C281 C291 C301 N41 173(4) . . . . ?
O81 N41 C301 C291 178(5) . . . . ?
O91 N41 C301 C291 -3(6) . . . . ?
O81 N41 C301 C311 -10(7) . . . . ?
O91 N41 C301 C311 169(4) . . . . ?
C291 C301 C311 C321 0.0 . . . . ?
N41 C301 C311 C321 -173(4) . . . . ?
C301 C311 C321 C331 0.0 . . . . ?
C311 C321 C331 C281 0.0 . . . . ?
C291 C281 C331 C321 0.0 . . . . ?
C271 C281 C331 C321 177(3) . . . . ?
C271 N31 C25 N3 17(2) . . . . ?
C271 N31 C25 C26 128(2) . . . . ?
C271 N31 C25 C24 -116.7(19) . . . . ?
C271 N31 C25 C261 122(3) . . . . ?
C27 N3 C25 N31 -15.0(14) . . . . ?
C27 N3 C25 C26 -111.6(8) . . . . ?
C27 N3 C25 C24 119.8(7) . . . . ?
C27 N3 C25 C261 -132(2) . . . . ?
O51 C24 C25 N31 32(3) . . . . ?
O6 C24 C25 N31 -68.5(14) . . . . ?
O5 C24 C25 N31 98.8(14) . . . . ?
O61 C24 C25 N31 -152.9(17) . . . . ?
O51 C24 C25 N3 -104(2) . . . . ?
O6 C24 C25 N3 156.2(7) . . . . ?
O5 C24 C25 N3 -36.6(11) . . . . ?
O61 C24 C25 N3 71.7(14) . . . . ?
O51 C24 C25 C26 129(2) . . . . ?
O6 C24 C25 C26 29.4(12) . . . . ?
O5 C24 C25 C26 -163.4(9) . . . . ?
O61 C24 C25 C26 -55.1(15) . . . . ?
O51 C24 C25 C261 157(3) . . . . ?
O6 C24 C25 C261 57(2) . . . . ?
O5 C24 C25 C261 -136(2) . . . . ?
O61 C24 C25 C261 -28(3) . . . . ?
O101 C101 C102 O102 66.5(12) . . . . ?
O101 C101 C102 C103 -165.3(9) . . . . ?
O102 C102 C103 C104 72.4(13) . . . . ?
C101 C102 C103 C104 -58.2(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.91 1.77 2.65(2) 162.2 .
N2 H2A O5 0.91 1.79 2.671(7) 161.7 .
N3 H3A O6 0.86 2.23 2.976(9) 145.4 4_566
N31 H31B O61 0.86 2.05 2.86(4) 157.3 4_466
O101 H101 O5 0.82 2.01 2.832(8) 177.6 .
O102 H102 O4 0.82 2.02 2.821(6) 164.3 3_646
C15 H15B O8 0.97 2.57 3.191(11) 121.7 1_565
C15 H15A O9 0.97 2.69 3.577(12) 152.2 1_465
C15 H15B O81 0.97 2.60 3.32(4) 131.3 1_665
C15 H15A O91 0.97 2.32 3.20(3) 150.3 1_565

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 930490'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


#===== end


data_B3NB(DL)A/12bu2
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-(D~0.59~L~0.41~)-alaninate butanol-1,2-diol
solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O5, C23 H27 N2 O4, C4 H10 O2 '
_chemical_formula_sum            'C37 H46 N4 O11'
_chemical_formula_weight         722.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.837(2)
_cell_length_b                   12.202(3)
_cell_length_c                   35.412(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3386.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5703
_cell_measurement_theta_min      2.8344
_cell_measurement_theta_max      28.7437

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21156
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4152
_reflns_number_gt                2588
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+2.2471P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0073(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     652
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1954
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.8093(5) 1.2573(3) 0.67789(10) 0.0338(10) Uani 1 1 d . . .
O2 O -0.7531(5) 0.6716(3) 0.81793(10) 0.0341(10) Uani 1 1 d . . .
O3 O -0.7195(7) 0.5564(3) 0.75750(12) 0.0471(12) Uani 1 1 d . . .
O4 O -0.7584(7) 1.0739(4) 0.79388(11) 0.0547(14) Uani 1 1 d . . .
N1 N -0.8326(7) 0.9992(4) 0.73795(13) 0.0315(12) Uani 1 1 d . . .
N2 N -0.8624(7) 0.9017(4) 0.61220(14) 0.0385(13) Uani 1 1 d . . .
H2A H -0.8675 0.8420 0.5959 0.046 Uiso 1 1 calc R . .
C1 C -0.7919(7) 0.8405(4) 0.78273(15) 0.0270(13) Uani 1 1 d . . .
H1A H -0.7963 0.8837 0.8050 0.032 Uiso 1 1 calc R . .
C2 C -0.7674(8) 0.7280(5) 0.78420(16) 0.0338(14) Uani 1 1 d . . .
C3 C -0.7519(8) 0.6653(5) 0.75204(17) 0.0350(15) Uani 1 1 d . . .
C4 C -0.7745(8) 0.7128(5) 0.71678(17) 0.0344(14) Uani 1 1 d . . .
H4A H -0.7696 0.6695 0.6945 0.041 Uiso 1 1 calc R . .
C5 C -0.8047(8) 0.8256(5) 0.71462(16) 0.0319(13) Uani 1 1 d . . .
C6 C -0.8099(8) 0.8875(4) 0.74696(15) 0.0298(13) Uani 1 1 d . . .
C7 C -0.8516(8) 0.8942(5) 0.68122(16) 0.0306(13) Uani 1 1 d . . .
C8 C -0.8343(8) 1.0122(5) 0.69609(15) 0.0284(13) Uani 1 1 d . . .
H8A H -0.9362 1.0561 0.6883 0.034 Uiso 1 1 calc R . .
C9 C -0.7875(9) 1.0857(5) 0.75977(17) 0.0413(16) Uani 1 1 d . . .
C10 C -0.7688(9) 1.1936(5) 0.74068(17) 0.0354(15) Uani 1 1 d . . .
H10A H -0.6940 1.2402 0.7565 0.042 Uiso 1 1 calc R . .
H10B H -0.8824 1.2290 0.7399 0.042 Uiso 1 1 calc R . .
C11 C -0.6955(8) 1.1926(5) 0.69993(16) 0.0320(13) Uani 1 1 d . . .
H11A H -0.5813 1.2291 0.7002 0.038 Uiso 1 1 calc R . .
C12 C -0.7547(8) 1.2806(5) 0.64000(16) 0.0340(14) Uani 1 1 d . . .
H12A H -0.6292 1.2897 0.6396 0.041 Uiso 1 1 calc R . .
H12B H -0.8068 1.3503 0.6315 0.041 Uiso 1 1 calc R . .
C13 C -0.8046(8) 1.1899(5) 0.61305(16) 0.0310(13) Uani 1 1 d . . .
H13A H -0.8800 1.2069 0.5929 0.037 Uiso 1 1 calc R . .
C14 C -0.7494(7) 1.0899(5) 0.61609(15) 0.0316(13) Uani 1 1 d . . .
C15 C -0.8022(9) 1.0005(5) 0.58992(16) 0.0378(15) Uani 1 1 d . . .
H15A H -0.7047 0.9794 0.5737 0.045 Uiso 1 1 calc R . .
H15B H -0.8955 1.0268 0.5734 0.045 Uiso 1 1 calc R . .
C16 C -1.0411(8) 0.9203(6) 0.62862(14) 0.0327(15) Uani 1 1 d . . .
H16A H -1.0672 0.9995 0.6303 0.039 Uiso 1 1 calc R . .
H16B H -1.1290 0.8842 0.6129 0.039 Uiso 1 1 calc R . .
C17 C -1.0339(8) 0.8693(5) 0.66752(16) 0.0338(15) Uani 1 1 d . . .
H17A H -1.0542 0.7893 0.6662 0.041 Uiso 1 1 calc R . .
H17B H -1.1197 0.9027 0.6845 0.041 Uiso 1 1 calc R . .
C18 C -0.6726(7) 1.0745(5) 0.68643(15) 0.0294(13) Uani 1 1 d . . .
H18A H -0.5808 1.0423 0.7026 0.035 Uiso 1 1 calc R . .
C19 C -0.6163(8) 1.0557(5) 0.64553(16) 0.0330(14) Uani 1 1 d . . .
H19A H -0.5085 1.0975 0.6409 0.040 Uiso 1 1 calc R . .
C20 C -0.5790(8) 0.9335(5) 0.64207(18) 0.0380(15) Uani 1 1 d . . .
H20A H -0.5241 0.9179 0.6175 0.046 Uiso 1 1 calc R . .
H20B H -0.5005 0.9101 0.6624 0.046 Uiso 1 1 calc R . .
C21 C -0.7450(8) 0.8719(5) 0.64507(17) 0.0366(15) Uani 1 1 d . . .
H21A H -0.7199 0.7917 0.6438 0.044 Uiso 1 1 calc R . .
C22 C -0.7770(8) 0.7341(5) 0.85132(16) 0.0352(14) Uani 1 1 d . . .
H22A H -0.7693 0.6858 0.8734 0.053 Uiso 1 1 calc R . .
H22B H -0.8897 0.7689 0.8507 0.053 Uiso 1 1 calc R . .
H22C H -0.6886 0.7907 0.8529 0.053 Uiso 1 1 calc R . .
C23 C -0.7022(14) 0.4905(5) 0.7242(2) 0.068(3) Uani 1 1 d . . .
H23A H -0.6798 0.4143 0.7315 0.102 Uiso 1 1 calc R . .
H23B H -0.6071 0.5180 0.7090 0.102 Uiso 1 1 calc R . .
H23C H -0.8079 0.4940 0.7095 0.102 Uiso 1 1 calc R . .
O8 O -0.4702(17) 0.0946(14) 0.5576(4) 0.053(4) Uani 0.592(8) 1 d PD A 1
O9 O -0.1894(17) 0.1128(13) 0.5595(5) 0.040(4) Uani 0.592(8) 1 d PD A 1
N4 N -0.3375(17) 0.1541(11) 0.5558(5) 0.042(5) Uani 0.592(8) 1 d PD A 1
O5 O -0.8058(11) 0.7205(6) 0.57349(18) 0.0320(19) Uani 0.592(8) 1 d P A 1
O6 O -0.9674(10) 0.8084(6) 0.5320(2) 0.039(2) Uani 0.592(8) 1 d P A 1
O7 O -0.818(2) 0.413(2) 0.5367(8) 0.051(4) Uani 0.592(8) 1 d PU A 1
N3 N -0.7041(10) 0.5726(7) 0.5173(2) 0.032(2) Uani 0.592(8) 1 d P A 1
H3A H -0.6076 0.6074 0.5132 0.038 Uiso 0.592(8) 1 calc PR A 1
C26 C -0.910(2) 0.6595(12) 0.4739(4) 0.053(3) Uani 0.592(8) 1 d PU A 1
H26A H -1.0346 0.6541 0.4718 0.080 Uiso 0.592(8) 1 calc PR A 1
H26B H -0.8568 0.6075 0.4564 0.080 Uiso 0.592(8) 1 calc PR A 1
H26C H -0.8740 0.7341 0.4675 0.080 Uiso 0.592(8) 1 calc PR A 1
C27 C -0.6943(14) 0.4678(8) 0.5268(3) 0.030(2) Uani 0.592(8) 1 d P A 1
C28 C -0.5194(16) 0.4154(11) 0.5256(3) 0.029(2) Uani 0.592(8) 1 d PU A 1
C29 C -0.4989(18) 0.3103(12) 0.5411(4) 0.029(3) Uani 0.592(8) 1 d PU A 1
H29A H -0.5930 0.2726 0.5519 0.035 Uiso 0.592(8) 1 calc PR A 1
C30 C -0.347(2) 0.2654(10) 0.5404(4) 0.031(3) Uani 0.592(8) 1 d PDU A 1
C31 C -0.1970(17) 0.3149(11) 0.5270(3) 0.034(3) Uani 0.592(8) 1 d PU A 1
H31A H -0.0892 0.2798 0.5291 0.041 Uiso 0.592(8) 1 calc PR A 1
C32 C -0.2132(16) 0.4155(10) 0.5110(3) 0.035(2) Uani 0.592(8) 1 d PU A 1
H32A H -0.1161 0.4512 0.5007 0.042 Uiso 0.592(8) 1 calc PR A 1
C33 C -0.3725(16) 0.4661(10) 0.5096(3) 0.030(3) Uani 0.592(8) 1 d PU A 1
H33A H -0.3832 0.5357 0.4978 0.037 Uiso 0.592(8) 1 calc PR A 1
O51 O -0.9292(19) 0.7320(10) 0.5678(3) 0.046(3) Uani 0.408(8) 1 d PU A 2
O61 O -0.7522(16) 0.8148(10) 0.5287(3) 0.053(4) Uani 0.408(8) 1 d PU A 2
O71 O -0.865(4) 0.419(4) 0.5313(11) 0.047(5) Uani 0.408(8) 1 d PU A 2
O81 O -1.439(2) 0.1005(17) 0.5684(5) 0.025(4) Uani 0.408(8) 1 d PDU A 2
O91 O -1.158(3) 0.092(2) 0.5631(10) 0.053(7) Uani 0.408(8) 1 d PDU A 2
N41 N -1.299(2) 0.1386(13) 0.5562(8) 0.023(5) Uani 0.408(8) 1 d PDU A 2
N31 N -1.0012(15) 0.5727(10) 0.5142(3) 0.031(3) Uani 0.408(8) 1 d PU A 2
H31B H -1.0984 0.6022 0.5070 0.037 Uiso 0.408(8) 1 calc PR A 2
C261 C -0.811(3) 0.6730(18) 0.4697(6) 0.053(4) Uani 0.408(8) 1 d PU A 2
H26D H -0.8080 0.6089 0.4531 0.080 Uiso 0.408(8) 1 calc PR A 2
H26E H -0.6989 0.7090 0.4695 0.080 Uiso 0.408(8) 1 calc PR A 2
H26F H -0.8979 0.7245 0.4608 0.080 Uiso 0.408(8) 1 calc PR A 2
C271 C -0.999(2) 0.4700(14) 0.5256(5) 0.037(4) Uani 0.408(8) 1 d PU A 2
C281 C -1.1649(15) 0.4156(11) 0.5274(4) 0.032(3) Uani 0.408(8) 1 d PGU A 2
C291 C -1.1666(18) 0.3082(11) 0.5404(4) 0.035(4) Uani 0.408(8) 1 d PGU A 2
H29B H -1.0627 0.2732 0.5473 0.042 Uiso 0.408(8) 1 calc PR A 2
C301 C -1.320(2) 0.2519(10) 0.5435(5) 0.034(5) Uani 0.408(8) 1 d PGDU A 2
C311 C -1.4720(18) 0.3030(14) 0.5335(5) 0.039(5) Uani 0.408(8) 1 d PGU A 2
H31C H -1.5770 0.2645 0.5355 0.046 Uiso 0.408(8) 1 calc PR A 2
C321 C -1.4703(16) 0.4104(14) 0.5204(5) 0.041(5) Uani 0.408(8) 1 d PGU A 2
H32B H -1.5742 0.4454 0.5135 0.049 Uiso 0.408(8) 1 calc PR A 2
C331 C -1.3168(19) 0.4667(10) 0.5174(4) 0.040(4) Uani 0.408(8) 1 d PGU A 2
H33B H -1.3156 0.5401 0.5084 0.048 Uiso 0.408(8) 1 calc PR A 2
C24 C -0.8653(10) 0.7319(5) 0.5399(2) 0.0424(17) Uani 1 1 d . . .
C25 C -0.8572(9) 0.6334(5) 0.51335(18) 0.0411(17) Uani 1 1 d . A .
H25B H -0.7617 0.5855 0.5222 0.049 Uiso 0.408(8) 1 calc PR A 2
H25A H -0.9434 0.5838 0.5216 0.049 Uiso 0.592(8) 1 d PR A 1
O101 O -0.6807(10) 0.5809(6) 0.63104(18) 0.042(2) Uani 0.623(9) 1 d P B 1
H101 H -0.7203 0.6231 0.6145 0.063 Uiso 0.623(9) 1 calc PR B 1
O102 O -0.3787(13) 0.7118(8) 0.6497(3) 0.040(2) Uani 0.623(9) 1 d PU B 1
H102 H -0.3227 0.6743 0.6653 0.060 Uiso 0.623(9) 1 calc PR B 1
C101 C -0.5206(15) 0.5539(10) 0.6221(3) 0.039(3) Uani 0.623(9) 1 d PU B 1
H10C H -0.5232 0.5077 0.5991 0.047 Uiso 0.623(9) 1 calc PR B 1
H10D H -0.4730 0.5088 0.6428 0.047 Uiso 0.623(9) 1 calc PR B 1
C102 C -0.4007(16) 0.6500(9) 0.6151(3) 0.044(3) Uani 0.623(9) 1 d P B 1
H10E H -0.4632 0.6999 0.5975 0.052 Uiso 0.623(9) 1 calc PR B 1
C103 C -0.2319(15) 0.6242(11) 0.5955(3) 0.047(3) Uani 0.623(9) 1 d P B 1
H10F H -0.1607 0.6912 0.5958 0.057 Uiso 0.623(9) 1 calc PR B 1
H10G H -0.2561 0.6065 0.5688 0.057 Uiso 0.623(9) 1 calc PR B 1
C104 C -0.125(2) 0.5277(14) 0.6129(4) 0.043(3) Uani 0.623(9) 1 d PU B 1
H10H H -0.0606 0.4909 0.5928 0.064 Uiso 0.623(9) 1 calc PR B 1
H10I H -0.2016 0.4750 0.6250 0.064 Uiso 0.623(9) 1 calc PR B 1
H10J H -0.0450 0.5569 0.6317 0.064 Uiso 0.623(9) 1 calc PR B 1
O111 O 0.040(3) 0.6068(16) 0.6302(5) 0.098(7) Uani 0.377(9) 1 d PU B 2
H111 H 0.0451 0.6440 0.6103 0.148 Uiso 0.377(9) 1 calc PR B 2
O112 O -0.316(2) 0.6862(15) 0.6396(5) 0.047(4) Uani 0.377(9) 1 d PU B 2
H112 H -0.3933 0.6712 0.6552 0.071 Uiso 0.377(9) 1 calc PR B 2
C111 C -0.100(4) 0.533(3) 0.6278(7) 0.043(5) Uani 0.377(9) 1 d PU B 2
H11B H -0.1149 0.4975 0.6528 0.052 Uiso 0.377(9) 1 calc PR B 2
H11C H -0.0697 0.4742 0.6096 0.052 Uiso 0.377(9) 1 calc PR B 2
C112 C -0.280(4) 0.586(2) 0.6152(8) 0.074(7) Uani 0.377(9) 1 d PU B 2
H11D H -0.2683 0.6115 0.5884 0.089 Uiso 0.377(9) 1 calc PR B 2
C113 C -0.404(3) 0.5132(19) 0.6163(7) 0.066(7) Uani 0.377(9) 1 d PU B 2
H11E H -0.4179 0.4849 0.6423 0.079 Uiso 0.377(9) 1 calc PR B 2
H11F H -0.3768 0.4508 0.5994 0.079 Uiso 0.377(9) 1 calc PR B 2
C114 C -0.574(2) 0.5731(19) 0.6026(6) 0.048(4) Uani 0.377(9) 1 d PU B 2
H11G H -0.6694 0.5209 0.6031 0.072 Uiso 0.377(9) 1 calc PR B 2
H11H H -0.5587 0.6005 0.5768 0.072 Uiso 0.377(9) 1 calc PR B 2
H11I H -0.5995 0.6346 0.6195 0.072 Uiso 0.377(9) 1 calc PR B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.041(3) 0.037(2) 0.023(2) 0.0044(18) -0.0028(18) 0.001(2)
O2 0.043(2) 0.036(2) 0.024(2) 0.0065(19) 0.0037(18) -0.0015(19)
O3 0.072(3) 0.027(2) 0.042(3) 0.003(2) 0.007(2) 0.003(2)
O4 0.098(4) 0.045(3) 0.020(2) 0.005(2) -0.016(2) -0.014(3)
N1 0.049(3) 0.024(2) 0.021(2) 0.006(2) -0.003(2) -0.001(2)
N2 0.057(3) 0.033(3) 0.025(3) -0.001(2) 0.004(2) -0.007(3)
C1 0.030(3) 0.028(3) 0.022(3) 0.000(2) -0.004(2) -0.004(3)
C2 0.035(3) 0.039(3) 0.027(3) 0.008(3) -0.007(3) -0.001(3)
C3 0.043(4) 0.026(3) 0.036(3) 0.002(3) 0.000(3) -0.002(3)
C4 0.042(4) 0.030(3) 0.032(3) 0.002(3) 0.006(3) -0.005(3)
C5 0.035(3) 0.031(3) 0.029(3) 0.001(3) 0.004(3) -0.002(3)
C6 0.035(3) 0.028(3) 0.026(3) -0.005(3) 0.001(3) -0.007(3)
C7 0.038(3) 0.028(3) 0.025(3) 0.006(3) -0.002(3) -0.005(3)
C8 0.032(3) 0.029(3) 0.024(3) 0.000(2) 0.001(3) -0.001(3)
C9 0.061(4) 0.039(3) 0.025(3) 0.000(3) -0.009(3) -0.003(3)
C10 0.049(4) 0.027(3) 0.030(3) 0.000(3) -0.007(3) -0.004(3)
C11 0.029(3) 0.034(3) 0.033(3) 0.007(3) -0.001(3) -0.003(3)
C12 0.035(3) 0.032(3) 0.034(3) 0.005(3) -0.004(3) -0.006(3)
C13 0.034(3) 0.033(3) 0.026(3) 0.007(3) 0.005(3) -0.001(3)
C14 0.028(3) 0.043(4) 0.023(3) 0.004(3) 0.008(2) -0.001(3)
C15 0.051(4) 0.036(3) 0.027(3) 0.003(3) 0.007(3) -0.002(3)
C16 0.037(3) 0.046(4) 0.016(3) -0.003(3) -0.007(2) -0.010(3)
C17 0.047(4) 0.032(3) 0.023(3) 0.001(3) -0.004(3) -0.009(3)
C18 0.021(3) 0.036(3) 0.031(3) 0.005(3) -0.005(2) -0.001(3)
C19 0.036(3) 0.032(3) 0.031(3) 0.005(3) 0.003(3) -0.003(3)
C20 0.046(4) 0.036(4) 0.032(3) 0.005(3) 0.012(3) 0.002(3)
C21 0.049(4) 0.030(3) 0.032(3) 0.000(3) 0.008(3) 0.001(3)
C22 0.038(4) 0.039(3) 0.028(3) 0.005(3) 0.002(3) 0.000(3)
C23 0.142(9) 0.018(3) 0.044(4) -0.007(3) 0.012(5) 0.010(5)
O8 0.054(8) 0.055(7) 0.051(9) 0.005(7) 0.018(6) -0.010(6)
O9 0.057(9) 0.038(6) 0.025(5) 0.005(5) -0.022(6) 0.021(6)
N4 0.067(10) 0.041(8) 0.016(6) -0.010(5) 0.007(7) 0.030(8)
O5 0.038(5) 0.035(4) 0.023(4) -0.006(3) -0.007(3) 0.007(4)
O6 0.053(5) 0.032(4) 0.034(4) 0.002(3) -0.008(3) 0.014(4)
O7 0.048(10) 0.041(5) 0.063(9) 0.015(6) 0.003(8) -0.008(8)
N3 0.025(5) 0.036(5) 0.034(5) -0.010(4) 0.007(3) 0.000(4)
C26 0.068(9) 0.057(7) 0.036(6) -0.020(6) 0.001(7) -0.003(8)
C27 0.034(6) 0.029(5) 0.027(5) 0.002(4) -0.007(4) -0.002(5)
C28 0.034(5) 0.038(5) 0.014(4) -0.011(4) 0.010(4) -0.012(5)
C29 0.035(5) 0.042(6) 0.010(4) 0.000(4) 0.010(4) -0.005(5)
C30 0.052(7) 0.033(5) 0.009(4) -0.004(4) 0.004(5) 0.001(5)
C31 0.037(6) 0.039(5) 0.027(5) -0.006(5) -0.002(5) -0.003(5)
C32 0.038(6) 0.036(5) 0.032(5) -0.014(5) 0.002(5) -0.008(5)
C33 0.032(6) 0.035(5) 0.024(5) -0.013(4) 0.000(4) -0.010(4)
O51 0.060(7) 0.041(6) 0.036(6) 0.000(5) 0.002(6) -0.018(6)
O61 0.062(7) 0.040(6) 0.058(6) -0.006(5) 0.015(5) -0.012(5)
O71 0.047(11) 0.041(6) 0.053(8) 0.012(6) -0.005(8) -0.006(8)
O81 0.028(5) 0.026(5) 0.021(6) 0.002(4) 0.005(4) 0.000(4)
O91 0.044(9) 0.062(11) 0.054(11) 0.006(8) -0.010(7) 0.017(7)
N41 0.024(6) 0.021(6) 0.023(6) -0.003(4) -0.001(4) 0.001(4)
N31 0.024(6) 0.031(6) 0.038(6) 0.002(5) 0.003(5) 0.000(5)
C261 0.062(9) 0.051(7) 0.047(7) -0.010(6) 0.009(7) -0.005(8)
C271 0.039(7) 0.037(7) 0.036(7) -0.009(6) 0.006(6) -0.004(6)
C281 0.036(6) 0.038(6) 0.022(6) -0.005(5) 0.001(5) 0.005(5)
C291 0.035(6) 0.042(6) 0.029(6) -0.001(6) 0.005(5) -0.003(5)
C301 0.033(7) 0.039(7) 0.030(7) -0.006(6) 0.001(5) 0.009(6)
C311 0.034(7) 0.048(7) 0.034(7) -0.004(6) 0.004(6) 0.000(6)
C321 0.037(7) 0.047(7) 0.038(7) -0.005(6) 0.006(6) 0.002(6)
C331 0.039(7) 0.046(7) 0.033(6) -0.003(5) 0.003(6) 0.003(6)
C24 0.050(4) 0.033(4) 0.044(4) -0.003(3) -0.020(4) 0.003(3)
C25 0.051(4) 0.040(4) 0.032(3) -0.009(3) -0.013(3) 0.011(3)
O101 0.052(5) 0.043(4) 0.031(4) -0.003(3) 0.000(3) -0.003(4)
O102 0.056(6) 0.031(5) 0.034(5) -0.009(4) -0.011(4) -0.001(4)
C101 0.040(6) 0.039(6) 0.039(6) 0.013(5) -0.004(5) -0.001(5)
C102 0.066(8) 0.049(7) 0.016(5) -0.004(5) -0.013(5) 0.006(6)
C103 0.042(7) 0.066(8) 0.034(6) -0.001(6) 0.006(5) -0.001(6)
C104 0.052(7) 0.051(6) 0.025(7) 0.002(7) -0.003(6) 0.005(5)
O111 0.103(10) 0.088(10) 0.103(10) 0.002(8) 0.019(8) -0.013(8)
O112 0.059(8) 0.041(7) 0.042(7) -0.004(6) -0.007(6) -0.007(6)
C111 0.043(7) 0.046(7) 0.040(9) 0.002(8) -0.001(8) -0.002(6)
C112 0.078(11) 0.079(11) 0.066(10) 0.000(9) 0.007(9) 0.001(9)
C113 0.073(10) 0.058(10) 0.066(10) -0.006(8) -0.001(8) -0.011(8)
C114 0.040(7) 0.057(7) 0.049(8) 0.008(7) -0.006(6) 0.004(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.424(7) . ?
O1 C12 1.437(7) . ?
O2 C2 1.383(7) . ?
O2 C22 1.419(7) . ?
O3 C3 1.366(7) . ?
O3 C23 1.433(8) . ?
O4 C9 1.238(7) . ?
N1 C9 1.356(8) . ?
N1 C6 1.410(7) . ?
N1 C8 1.491(7) . ?
N2 C15 1.516(8) . ?
N2 C21 1.528(8) . ?
N2 C16 1.533(8) . ?
N2 H2A 0.9300 . ?
C1 C2 1.388(8) . ?
C1 C6 1.398(8) . ?
C1 H1A 0.9500 . ?
C2 C3 1.378(8) . ?
C3 C4 1.389(8) . ?
C4 C5 1.398(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.373(8) . ?
C5 C7 1.495(8) . ?
C7 C17 1.539(8) . ?
C7 C8 1.539(8) . ?
C7 C21 1.553(8) . ?
C8 C18 1.517(8) . ?
C8 H8A 1.0000 . ?
C9 C10 1.487(8) . ?
C10 C11 1.553(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.529(8) . ?
C11 H11A 1.0000 . ?
C12 C13 1.512(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.299(8) . ?
C13 H13A 0.9500 . ?
C14 C15 1.490(8) . ?
C14 C19 1.533(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.513(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.531(8) . ?
C18 H18A 1.0000 . ?
C19 C20 1.525(8) . ?
C19 H19A 1.0000 . ?
C20 C21 1.506(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O8 N4 1.270(7) . ?
O9 N4 1.272(7) . ?
N4 C30 1.465(10) . ?
O5 C24 1.286(10) . ?
O6 C24 1.260(9) . ?
O7 C27 1.23(3) . ?
N3 C27 1.325(13) . ?
N3 C25 1.417(10) . ?
N3 H3A 0.8800 . ?
C26 C25 1.492(15) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.513(17) . ?
C28 C29 1.405(16) . ?
C28 C33 1.423(15) . ?
C29 C30 1.313(18) . ?
C29 H29A 0.9500 . ?
C30 C31 1.402(17) . ?
C31 C32 1.358(16) . ?
C31 H31A 0.9500 . ?
C32 C33 1.393(16) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
O51 C24 1.109(13) . ?
O61 C24 1.402(13) . ?
O71 C271 1.24(4) . ?
O81 N41 1.268(7) . ?
O91 N41 1.269(7) . ?
N41 C301 1.463(11) . ?
N31 C271 1.32(2) . ?
N31 C25 1.351(13) . ?
N31 H31B 0.8800 . ?
N31 H25A 0.5400 . ?
C261 C25 1.66(2) . ?
C261 H26D 0.9800 . ?
C261 H26E 0.9800 . ?
C261 H26F 0.9800 . ?
C271 C281 1.46(2) . ?
C281 C291 1.3900 . ?
C281 C331 1.3900 . ?
C291 C301 1.3900 . ?
C291 H29B 0.9500 . ?
C301 C311 1.3900 . ?
C311 C321 1.3900 . ?
C311 H31C 0.9500 . ?
C321 C331 1.3900 . ?
C321 H32B 0.9500 . ?
C331 H33B 0.9500 . ?
C24 C25 1.527(9) . ?
C25 H25B 1.0000 . ?
C25 H25A 0.9524 . ?
O101 C101 1.335(14) . ?
O101 H101 0.8400 . ?
O102 C102 1.450(13) . ?
O102 H102 0.8400 . ?
C101 C102 1.523(16) . ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?
C102 C103 1.526(17) . ?
C102 H10E 1.0000 . ?
C103 C104 1.571(19) . ?
C103 H10F 0.9900 . ?
C103 H10G 0.9900 . ?
C104 H10H 0.9800 . ?
C104 H10I 0.9800 . ?
C104 H10J 0.9800 . ?
O111 C111 1.42(3) . ?
O111 H111 0.8400 . ?
O112 C112 1.52(3) . ?
O112 H112 0.8400 . ?
C111 C112 1.62(4) . ?
C111 H11B 0.9900 . ?
C111 H11C 0.9900 . ?
C112 C113 1.32(3) . ?
C112 H11D 1.0000 . ?
C113 C114 1.60(3) . ?
C113 H11E 0.9900 . ?
C113 H11F 0.9900 . ?
C114 H11G 0.9800 . ?
C114 H11H 0.9800 . ?
C114 H11I 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 115.8(5) . . ?
C2 O2 C22 116.2(4) . . ?
C3 O3 C23 116.6(5) . . ?
C9 N1 C6 126.2(5) . . ?
C9 N1 C8 119.1(5) . . ?
C6 N1 C8 109.2(4) . . ?
C15 N2 C21 113.5(5) . . ?
C15 N2 C16 111.3(5) . . ?
C21 N2 C16 107.2(4) . . ?
C15 N2 H2A 108.2 . . ?
C21 N2 H2A 108.2 . . ?
C16 N2 H2A 108.2 . . ?
C2 C1 C6 117.0(5) . . ?
C2 C1 H1A 121.5 . . ?
C6 C1 H1A 121.5 . . ?
C3 C2 O2 115.5(5) . . ?
C3 C2 C1 122.1(5) . . ?
O2 C2 C1 122.4(5) . . ?
O3 C3 C2 116.1(5) . . ?
O3 C3 C4 123.9(5) . . ?
C2 C3 C4 120.0(5) . . ?
C3 C4 C5 118.8(6) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 C7 110.1(5) . . ?
C4 C5 C7 129.5(5) . . ?
C5 C6 C1 121.8(5) . . ?
C5 C6 N1 110.3(5) . . ?
C1 C6 N1 127.9(5) . . ?
C5 C7 C17 111.5(5) . . ?
C5 C7 C8 103.4(5) . . ?
C17 C7 C8 112.0(5) . . ?
C5 C7 C21 115.0(5) . . ?
C17 C7 C21 101.8(5) . . ?
C8 C7 C21 113.5(5) . . ?
N1 C8 C18 105.7(5) . . ?
N1 C8 C7 104.0(4) . . ?
C18 C8 C7 117.7(5) . . ?
N1 C8 H8A 109.7 . . ?
C18 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O4 C9 N1 120.9(6) . . ?
O4 C9 C10 121.9(6) . . ?
N1 C9 C10 117.1(5) . . ?
C9 C10 C11 116.9(5) . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 115.1(5) . . ?
O1 C11 C10 105.9(5) . . ?
C18 C11 C10 110.0(5) . . ?
O1 C11 H11A 108.6 . . ?
C18 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
O1 C12 C13 111.6(5) . . ?
O1 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 123.3(6) . . ?
C14 C13 H13A 118.4 . . ?
C12 C13 H13A 118.4 . . ?
C13 C14 C15 122.9(6) . . ?
C13 C14 C19 122.6(6) . . ?
C15 C14 C19 114.4(5) . . ?
C14 C15 N2 110.2(5) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 N2 104.5(5) . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
N2 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.9(5) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 107.7(5) . . ?
C8 C18 C19 112.3(5) . . ?
C11 C18 C19 118.1(5) . . ?
C8 C18 H18A 106.0 . . ?
C11 C18 H18A 106.0 . . ?
C19 C18 H18A 106.0 . . ?
C20 C19 C18 106.1(5) . . ?
C20 C19 C14 110.0(5) . . ?
C18 C19 C14 114.0(5) . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C14 C19 H19A 108.9 . . ?
C21 C20 C19 108.5(5) . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 N2 110.4(5) . . ?
C20 C21 C7 115.8(5) . . ?
N2 C21 C7 105.2(5) . . ?
C20 C21 H21A 108.4 . . ?
N2 C21 H21A 108.4 . . ?
C7 C21 H21A 108.4 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 N4 O9 121.1(10) . . ?
O8 N4 C30 120.6(13) . . ?
O9 N4 C30 116.7(13) . . ?
C27 N3 C25 125.4(8) . . ?
C27 N3 H3A 117.3 . . ?
C25 N3 H3A 117.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 N3 123.7(15) . . ?
O7 C27 C28 119.3(15) . . ?
N3 C27 C28 117.0(10) . . ?
C29 C28 C33 117.4(11) . . ?
C29 C28 C27 118.5(10) . . ?
C33 C28 C27 124.1(11) . . ?
C30 C29 C28 118.5(11) . . ?
C30 C29 H29A 120.7 . . ?
C28 C29 H29A 120.7 . . ?
C29 C30 C31 125.9(11) . . ?
C29 C30 N4 115.1(13) . . ?
C31 C30 N4 119.0(13) . . ?
C32 C31 C30 116.9(11) . . ?
C32 C31 H31A 121.6 . . ?
C30 C31 H31A 121.6 . . ?
C31 C32 C33 119.9(11) . . ?
C31 C32 H32A 120.0 . . ?
C33 C32 H32A 120.0 . . ?
C32 C33 C28 121.2(11) . . ?
C32 C33 H33A 119.4 . . ?
C28 C33 H33A 119.4 . . ?
O81 N41 O91 121.5(11) . . ?
O81 N41 C301 110.7(16) . . ?
O91 N41 C301 125.8(17) . . ?
C271 N31 C25 121.0(12) . . ?
C271 N31 H31B 119.5 . . ?
C25 N31 H31B 119.5 . . ?
C271 N31 H25A 94.5 . . ?
C25 N31 H25A 34.1 . . ?
H31B N31 H25A 139.7 . . ?
C25 C261 H26D 109.5 . . ?
C25 C261 H26E 109.5 . . ?
H26D C261 H26E 109.5 . . ?
C25 C261 H26F 109.5 . . ?
H26D C261 H26F 109.5 . . ?
H26E C261 H26F 109.5 . . ?
O71 C271 N31 123(2) . . ?
O71 C271 C281 121(2) . . ?
N31 C271 C281 115.5(15) . . ?
O71 C271 H25A 104.2 . . ?
N31 C271 H25A 21.6 . . ?
C281 C271 H25A 134.3 . . ?
C291 C281 C331 120.0 . . ?
C291 C281 C271 116.8(11) . . ?
C331 C281 C271 123.2(11) . . ?
C281 C291 C301 120.0 . . ?
C281 C291 H29B 120.0 . . ?
C301 C291 H29B 120.0 . . ?
C291 C301 C311 120.0 . . ?
C291 C301 N41 113.1(13) . . ?
C311 C301 N41 126.9(14) . . ?
C321 C311 C301 120.0 . . ?
C321 C311 H31C 120.0 . . ?
C301 C311 H31C 120.0 . . ?
C311 C321 C331 120.0 . . ?
C311 C321 H32B 120.0 . . ?
C331 C321 H32B 120.0 . . ?
C321 C331 C281 120.0 . . ?
C321 C331 H33B 120.0 . . ?
C281 C331 H33B 120.0 . . ?
O51 C24 O6 84.9(10) . . ?
O51 C24 O5 48.6(8) . . ?
O6 C24 O5 121.1(8) . . ?
O51 C24 O61 122.4(9) . . ?
O6 C24 O61 78.7(7) . . ?
O5 C24 O61 96.3(8) . . ?
O51 C24 C25 124.6(9) . . ?
O6 C24 C25 118.2(6) . . ?
O5 C24 C25 118.0(6) . . ?
O61 C24 C25 111.6(8) . . ?
N31 C25 N3 114.7(7) . . ?
N31 C25 C26 84.6(9) . . ?
N3 C25 C26 116.2(8) . . ?
N31 C25 C24 112.5(8) . . ?
N3 C25 C24 112.7(6) . . ?
C26 C25 C24 113.3(8) . . ?
N31 C25 C261 111.3(10) . . ?
N3 C25 C261 93.4(10) . . ?
C26 C25 C261 29.2(8) . . ?
C24 C25 C261 110.6(9) . . ?
N31 C25 H25B 107.4 . . ?
N3 C25 H25B 14.0 . . ?
C26 C25 H25B 128.8 . . ?
C24 C25 H25B 107.4 . . ?
C261 C25 H25B 107.4 . . ?
N31 C25 H25A 18.5 . . ?
N3 C25 H25A 103.8 . . ?
C26 C25 H25A 102.9 . . ?
C24 C25 H25A 106.4 . . ?
C261 C25 H25A 128.7 . . ?
H25B C25 H25A 93.7 . . ?
C101 O101 H101 109.5 . . ?
C102 O102 H102 109.5 . . ?
O101 C101 C102 115.4(10) . . ?
O101 C101 H10C 108.4 . . ?
C102 C101 H10C 108.4 . . ?
O101 C101 H10D 108.4 . . ?
C102 C101 H10D 108.4 . . ?
H10C C101 H10D 107.5 . . ?
O102 C102 C101 109.6(9) . . ?
O102 C102 C103 112.9(10) . . ?
C101 C102 C103 116.8(10) . . ?
O102 C102 H10E 105.5 . . ?
C101 C102 H10E 105.5 . . ?
C103 C102 H10E 105.5 . . ?
C102 C103 C104 116.1(11) . . ?
C102 C103 H10F 108.3 . . ?
C104 C103 H10F 108.3 . . ?
C102 C103 H10G 108.3 . . ?
C104 C103 H10G 108.3 . . ?
H10F C103 H10G 107.4 . . ?
C103 C104 H10H 109.5 . . ?
C103 C104 H10I 109.5 . . ?
H10H C104 H10I 109.5 . . ?
C103 C104 H10J 109.5 . . ?
H10H C104 H10J 109.5 . . ?
H10I C104 H10J 109.5 . . ?
C111 O111 H111 109.5 . . ?
C112 O112 H112 109.5 . . ?
O111 C111 C112 116(2) . . ?
O111 C111 H11B 108.4 . . ?
C112 C111 H11B 108.4 . . ?
O111 C111 H11C 108.4 . . ?
C112 C111 H11C 108.4 . . ?
H11B C111 H11C 107.5 . . ?
C113 C112 O112 113(2) . . ?
C113 C112 C111 111(2) . . ?
O112 C112 C111 109(2) . . ?
C113 C112 H11D 107.8 . . ?
O112 C112 H11D 107.8 . . ?
C111 C112 H11D 107.8 . . ?
C112 C113 C114 107(2) . . ?
C112 C113 H11E 110.3 . . ?
C114 C113 H11E 110.3 . . ?
C112 C113 H11F 110.3 . . ?
C114 C113 H11F 110.3 . . ?
H11E C113 H11F 108.5 . . ?
C113 C114 H11G 109.5 . . ?
C113 C114 H11H 109.5 . . ?
H11G C114 H11H 109.5 . . ?
C113 C114 H11I 109.5 . . ?
H11G C114 H11I 109.5 . . ?
H11H C114 H11I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C3 -177.1(5) . . . . ?
C22 O2 C2 C1 4.3(8) . . . . ?
C6 C1 C2 C3 3.5(9) . . . . ?
C6 C1 C2 O2 -178.0(5) . . . . ?
C23 O3 C3 C2 -179.7(7) . . . . ?
C23 O3 C3 C4 2.5(10) . . . . ?
O2 C2 C3 O3 -1.8(8) . . . . ?
C1 C2 C3 O3 176.8(6) . . . . ?
O2 C2 C3 C4 176.1(6) . . . . ?
C1 C2 C3 C4 -5.3(10) . . . . ?
O3 C3 C4 C5 -179.1(6) . . . . ?
C2 C3 C4 C5 3.1(10) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
C3 C4 C5 C7 -172.6(6) . . . . ?
C4 C5 C6 C1 -2.4(9) . . . . ?
C7 C5 C6 C1 172.1(6) . . . . ?
C4 C5 C6 N1 176.8(6) . . . . ?
C7 C5 C6 N1 -8.8(7) . . . . ?
C2 C1 C6 C5 0.4(9) . . . . ?
C2 C1 C6 N1 -178.7(6) . . . . ?
C9 N1 C6 C5 -156.1(6) . . . . ?
C8 N1 C6 C5 -2.8(7) . . . . ?
C9 N1 C6 C1 23.0(11) . . . . ?
C8 N1 C6 C1 176.3(6) . . . . ?
C6 C5 C7 C17 -104.4(6) . . . . ?
C4 C5 C7 C17 69.3(9) . . . . ?
C6 C5 C7 C8 16.1(7) . . . . ?
C4 C5 C7 C8 -170.2(6) . . . . ?
C6 C5 C7 C21 140.3(5) . . . . ?
C4 C5 C7 C21 -46.0(9) . . . . ?
C9 N1 C8 C18 43.4(7) . . . . ?
C6 N1 C8 C18 -112.0(5) . . . . ?
C9 N1 C8 C7 168.0(6) . . . . ?
C6 N1 C8 C7 12.6(7) . . . . ?
C5 C7 C8 N1 -16.7(6) . . . . ?
C17 C7 C8 N1 103.5(5) . . . . ?
C21 C7 C8 N1 -141.9(5) . . . . ?
C5 C7 C8 C18 99.7(5) . . . . ?
C17 C7 C8 C18 -140.0(5) . . . . ?
C21 C7 C8 C18 -25.4(7) . . . . ?
C6 N1 C9 O4 -17.6(11) . . . . ?
C8 N1 C9 O4 -168.5(6) . . . . ?
C6 N1 C9 C10 160.3(6) . . . . ?
C8 N1 C9 C10 9.4(9) . . . . ?
O4 C9 C10 C11 142.3(7) . . . . ?
N1 C9 C10 C11 -35.6(9) . . . . ?
C12 O1 C11 C18 -66.5(6) . . . . ?
C12 O1 C11 C10 171.8(5) . . . . ?
C9 C10 C11 O1 130.3(6) . . . . ?
C9 C10 C11 C18 5.3(8) . . . . ?
C11 O1 C12 C13 86.1(6) . . . . ?
O1 C12 C13 C14 -61.9(8) . . . . ?
C12 C13 C14 C15 178.6(6) . . . . ?
C12 C13 C14 C19 -5.1(9) . . . . ?
C13 C14 C15 N2 -129.3(6) . . . . ?
C19 C14 C15 N2 54.1(7) . . . . ?
C21 N2 C15 C14 -45.4(7) . . . . ?
C16 N2 C15 C14 75.7(6) . . . . ?
C15 N2 C16 C17 -140.8(5) . . . . ?
C21 N2 C16 C17 -16.1(6) . . . . ?
N2 C16 C17 C7 36.1(6) . . . . ?
C5 C7 C17 C16 -164.9(5) . . . . ?
C8 C7 C17 C16 79.8(6) . . . . ?
C21 C7 C17 C16 -41.8(6) . . . . ?
N1 C8 C18 C11 -71.5(5) . . . . ?
C7 C8 C18 C11 173.0(5) . . . . ?
N1 C8 C18 C19 156.9(5) . . . . ?
C7 C8 C18 C19 41.4(7) . . . . ?
O1 C11 C18 C8 -73.1(6) . . . . ?
C10 C11 C18 C8 46.3(6) . . . . ?
O1 C11 C18 C19 55.3(7) . . . . ?
C10 C11 C18 C19 174.7(5) . . . . ?
C8 C18 C19 C20 -62.0(6) . . . . ?
C11 C18 C19 C20 171.8(5) . . . . ?
C8 C18 C19 C14 59.2(7) . . . . ?
C11 C18 C19 C14 -67.0(7) . . . . ?
C13 C14 C19 C20 179.7(5) . . . . ?
C15 C14 C19 C20 -3.7(7) . . . . ?
C13 C14 C19 C18 60.7(7) . . . . ?
C15 C14 C19 C18 -122.7(5) . . . . ?
C18 C19 C20 C21 68.8(6) . . . . ?
C14 C19 C20 C21 -54.9(6) . . . . ?
C19 C20 C21 N2 63.5(6) . . . . ?
C19 C20 C21 C7 -55.9(7) . . . . ?
C15 N2 C21 C20 -12.2(7) . . . . ?
C16 N2 C21 C20 -135.5(5) . . . . ?
C15 N2 C21 C7 113.5(5) . . . . ?
C16 N2 C21 C7 -9.8(6) . . . . ?
C5 C7 C21 C20 -85.7(6) . . . . ?
C17 C7 C21 C20 153.5(5) . . . . ?
C8 C7 C21 C20 33.0(7) . . . . ?
C5 C7 C21 N2 152.1(5) . . . . ?
C17 C7 C21 N2 31.4(6) . . . . ?
C8 C7 C21 N2 -89.1(6) . . . . ?
C25 N3 C27 O7 -7(2) . . . . ?
C25 N3 C27 C28 173.8(8) . . . . ?
O7 C27 C28 C29 -9(2) . . . . ?
N3 C27 C28 C29 169.8(9) . . . . ?
O7 C27 C28 C33 170.8(17) . . . . ?
N3 C27 C28 C33 -10.0(15) . . . . ?
C33 C28 C29 C30 0.5(15) . . . . ?
C27 C28 C29 C30 -179.3(11) . . . . ?
C28 C29 C30 C31 3.4(18) . . . . ?
C28 C29 C30 N4 -177.6(13) . . . . ?
O8 N4 C30 C29 22(2) . . . . ?
O9 N4 C30 C29 -172.4(17) . . . . ?
O8 N4 C30 C31 -158.8(16) . . . . ?
O9 N4 C30 C31 7(2) . . . . ?
C29 C30 C31 C32 -4.8(17) . . . . ?
N4 C30 C31 C32 176.2(13) . . . . ?
C30 C31 C32 C33 2.2(15) . . . . ?
C31 C32 C33 C28 1.4(16) . . . . ?
C29 C28 C33 C32 -2.9(15) . . . . ?
C27 C28 C33 C32 176.9(10) . . . . ?
C25 N31 C271 O71 -10(3) . . . . ?
C25 N31 C271 C281 176.4(11) . . . . ?
O71 C271 C281 C291 8(3) . . . . ?
N31 C271 C281 C291 -178.1(11) . . . . ?
O71 C271 C281 C331 -173(3) . . . . ?
N31 C271 C281 C331 0.8(19) . . . . ?
C331 C281 C291 C301 0.0 . . . . ?
C271 C281 C291 C301 178.9(14) . . . . ?
C281 C291 C301 C311 0.0 . . . . ?
C281 C291 C301 N41 177.7(19) . . . . ?
O81 N41 C301 C291 162.0(18) . . . . ?
O91 N41 C301 C291 -2(4) . . . . ?
O81 N41 C301 C311 -21(3) . . . . ?
O91 N41 C301 C311 176(3) . . . . ?
C291 C301 C311 C321 0.0 . . . . ?
N41 C301 C311 C321 -177(2) . . . . ?
C301 C311 C321 C331 0.0 . . . . ?
C311 C321 C331 C281 0.0 . . . . ?
C291 C281 C331 C321 0.0 . . . . ?
C271 C281 C331 C321 -178.8(14) . . . . ?
C271 N31 C25 N3 13.3(15) . . . . ?
C271 N31 C25 C26 129.6(13) . . . . ?
C271 N31 C25 C24 -117.3(12) . . . . ?
C271 N31 C25 C261 117.8(15) . . . . ?
C27 N3 C25 N31 -9.9(12) . . . . ?
C27 N3 C25 C26 -106.2(11) . . . . ?
C27 N3 C25 C24 120.7(9) . . . . ?
C27 N3 C25 C261 -125.3(11) . . . . ?
O51 C24 C25 N31 36.0(14) . . . . ?
O6 C24 C25 N31 -68.4(11) . . . . ?
O5 C24 C25 N31 93.1(10) . . . . ?
O61 C24 C25 N31 -156.8(9) . . . . ?
O51 C24 C25 N3 -95.6(14) . . . . ?
O6 C24 C25 N3 160.0(8) . . . . ?
O5 C24 C25 N3 -38.6(11) . . . . ?
O61 C24 C25 N3 71.5(9) . . . . ?
O51 C24 C25 C26 129.9(13) . . . . ?
O6 C24 C25 C26 25.5(13) . . . . ?
O5 C24 C25 C26 -173.1(10) . . . . ?
O61 C24 C25 C26 -63.0(12) . . . . ?
O51 C24 C25 C261 161.3(14) . . . . ?
O6 C24 C25 C261 56.9(14) . . . . ?
O5 C24 C25 C261 -141.7(12) . . . . ?
O61 C24 C25 C261 -31.6(13) . . . . ?
O101 C101 C102 O102 64.9(13) . . . . ?
O101 C101 C102 C103 -165.2(10) . . . . ?
O102 C102 C103 C104 77.8(14) . . . . ?
C101 C102 C103 C104 -50.6(14) . . . . ?
O111 C111 C112 C113 -176(2) . . . . ?
O111 C111 C112 O112 -50(3) . . . . ?
O112 C112 C113 C114 58(3) . . . . ?
C111 C112 C113 C114 -178.9(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.93 1.74 2.652(13) 166.1 .
N2 H2A O5 0.93 1.75 2.638(8) 158.9 .
N3 H3A O6 0.88 2.20 2.932(11) 141.1 4_566
N31 H31B O61 0.88 2.02 2.839(17) 154.5 4_466
O101 H101 O5 0.84 1.99 2.832(10) 177.2 .
O102 H102 O4 0.84 2.00 2.823(11) 167.1 3_446
C15 H15A O8 0.99 2.38 3.065(14) 125.6 1_565
C15 H15B O9 0.99 2.58 3.500(15) 154.7 1_465
C15 H15A O81 0.99 2.56 3.190(19) 121.4 1_665
C15 H15B O91 0.99 2.23 3.15(2) 153.0 1_565

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 930491'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97




#===== end

data_b3nb(dl)a/14bu1
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoy)-(D~0.57~L~0.43~)-alaninate butan-1,4-diol solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O5, C23 H27 N2 O4, C4 H10 O2'
_chemical_formula_sum            'C37 H46 N4 O11'
_chemical_formula_weight         722.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.906(2)
_cell_length_b                   12.047(3)
_cell_length_c                   35.802(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3409.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2369
_cell_measurement_theta_min      2.8295
_cell_measurement_theta_max      28.7828

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23523
_diffrn_reflns_av_R_equivalents  0.2097
_diffrn_reflns_av_sigmaI/netI    0.2431
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4203
_reflns_number_gt                1372
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4203
_refine_ls_number_parameters     717
_refine_ls_number_restraints     640
_refine_ls_R_factor_all          0.2015
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0602
_refine_ls_goodness_of_fit_ref   0.756
_refine_ls_restrained_S_all      0.717
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6899(4) 1.2511(2) 0.17689(8) 0.0307(9) Uani 1 1 d . . .
O2 O 0.7570(4) 0.6624(3) 0.31698(8) 0.0343(10) Uani 1 1 d . . .
O3 O 0.7979(4) 0.5452(3) 0.25762(8) 0.0408(10) Uani 1 1 d . . .
O4 O 0.7176(5) 1.0713(3) 0.29296(8) 0.0408(11) Uani 1 1 d . . .
N1 N 0.6501(5) 0.9902(3) 0.23737(9) 0.0266(11) Uani 1 1 d . . .
N2 N 0.6254(7) 0.8906(3) 0.11326(11) 0.0466(14) Uani 1 1 d . . .
H2A H 0.6202 0.8300 0.0972 0.056 Uiso 1 1 calc R . .
C1 C 0.7016(6) 0.8320(4) 0.28163(13) 0.0274(13) Uani 1 1 d . . .
H1A H 0.6940 0.8768 0.3034 0.033 Uiso 1 1 calc R . .
C2 C 0.7365(6) 0.7189(4) 0.28382(13) 0.0283(14) Uani 1 1 d . . .
C3 C 0.7535(7) 0.6532(4) 0.25139(14) 0.0348(15) Uani 1 1 d . . .
C4 C 0.7248(6) 0.7001(4) 0.21671(13) 0.0295(14) Uani 1 1 d . . .
H4A H 0.7308 0.6562 0.1947 0.035 Uiso 1 1 calc R . .
C5 C 0.6869(7) 0.8129(4) 0.21459(13) 0.0286(14) Uani 1 1 d . . .
C6 C 0.6787(6) 0.8762(4) 0.24647(13) 0.0261(13) Uani 1 1 d . . .
C7 C 0.6387(8) 0.8805(4) 0.18079(13) 0.0331(15) Uani 1 1 d . . .
C8 C 0.6551(7) 1.0032(4) 0.19540(11) 0.0288(14) Uani 1 1 d . . .
H8A H 0.5559 1.0479 0.1868 0.035 Uiso 1 1 calc R . .
C9 C 0.6980(6) 1.0795(4) 0.25933(14) 0.0322(14) Uani 1 1 d . . .
C10 C 0.7208(7) 1.1882(4) 0.23889(12) 0.0314(14) Uani 1 1 d . . .
H10A H 0.7929 1.2368 0.2545 0.038 Uiso 1 1 calc R . .
H10B H 0.6087 1.2243 0.2369 0.038 Uiso 1 1 calc R . .
C11 C 0.7988(7) 1.1840(4) 0.19939(12) 0.0305(14) Uani 1 1 d . . .
H11A H 0.9133 1.2192 0.2002 0.037 Uiso 1 1 calc R . .
C12 C 0.7510(7) 1.2723(4) 0.13942(11) 0.0342(15) Uani 1 1 d . . .
H12A H 0.8761 1.2753 0.1396 0.041 Uiso 1 1 calc R . .
H12B H 0.7081 1.3450 0.1307 0.041 Uiso 1 1 calc R . .
C13 C 0.6925(7) 1.1821(4) 0.11320(13) 0.0384(15) Uani 1 1 d . . .
H13A H 0.6145 1.1994 0.0939 0.046 Uiso 1 1 calc R . .
C14 C 0.7485(7) 1.0793(4) 0.11684(12) 0.0342(14) Uani 1 1 d . . .
C15 C 0.6896(8) 0.9879(4) 0.09070(12) 0.0454(17) Uani 1 1 d . . .
H15A H 0.5982 1.0162 0.0744 0.054 Uiso 1 1 calc R . .
H15B H 0.7847 0.9638 0.0746 0.054 Uiso 1 1 calc R . .
C16 C 0.4491(7) 0.9075(4) 0.12895(13) 0.0419(17) Uani 1 1 d . . .
H16A H 0.3637 0.8691 0.1134 0.050 Uiso 1 1 calc R . .
H16B H 0.4206 0.9874 0.1302 0.050 Uiso 1 1 calc R . .
C17 C 0.4567(7) 0.8569(4) 0.16817(12) 0.0370(16) Uani 1 1 d . . .
H17A H 0.4340 0.7761 0.1674 0.044 Uiso 1 1 calc R . .
H17B H 0.3739 0.8928 0.1850 0.044 Uiso 1 1 calc R . .
C18 C 0.8177(7) 1.0642(4) 0.18657(11) 0.0294(13) Uani 1 1 d . . .
H18A H 0.9066 1.0305 0.2029 0.035 Uiso 1 1 calc R . .
C19 C 0.8749(6) 1.0426(4) 0.14576(13) 0.0324(14) Uani 1 1 d . . .
H19A H 0.9835 1.0831 0.1413 0.039 Uiso 1 1 calc R . .
C20 C 0.9089(6) 0.9179(4) 0.14263(14) 0.0357(15) Uani 1 1 d . . .
H20A H 0.9637 0.9008 0.1184 0.043 Uiso 1 1 calc R . .
H20B H 0.9849 0.8934 0.1630 0.043 Uiso 1 1 calc R . .
C21 C 0.7408(7) 0.8584(4) 0.14541(13) 0.0364(15) Uani 1 1 d . . .
H21A H 0.7626 0.7768 0.1438 0.044 Uiso 1 1 calc R . .
C22 C 0.7266(7) 0.7252(4) 0.35049(11) 0.0386(15) Uani 1 1 d . . .
H22A H 0.7439 0.6775 0.3723 0.058 Uiso 1 1 calc R . .
H22B H 0.6100 0.7529 0.3504 0.058 Uiso 1 1 calc R . .
H22C H 0.8052 0.7880 0.3516 0.058 Uiso 1 1 calc R . .
C23 C 0.8270(8) 0.4793(4) 0.22495(13) 0.0597(19) Uani 1 1 d . . .
H23A H 0.8542 0.4030 0.2324 0.090 Uiso 1 1 calc R . .
H23B H 0.9216 0.5106 0.2107 0.090 Uiso 1 1 calc R . .
H23C H 0.7250 0.4792 0.2094 0.090 Uiso 1 1 calc R . .
O5 O 0.6878(11) 0.7118(6) 0.0705(2) 0.039(2) Uani 0.566(5) 1 d PU A 1
O6 O 0.5101(9) 0.8072(5) 0.03472(18) 0.048(2) Uani 0.566(5) 1 d PU A 1
O51 O 0.5675(14) 0.7243(8) 0.0661(3) 0.034(3) Uani 0.434(5) 1 d PU A 2
O61 O 0.7364(11) 0.8157(7) 0.0274(2) 0.050(3) Uani 0.434(5) 1 d PU A 2
C24 C 0.6239(10) 0.7303(5) 0.03867(18) 0.051(2) Uani 1 1 d U . .
C25 C 0.6300(9) 0.6363(5) 0.00921(16) 0.0499(18) Uani 1 1 d U A .
H25 H 0.5356 0.5846 0.0157 0.060 Uiso 0.566(5) 1 calc PR A 1
H251 H 0.7251 0.5912 0.0161 0.060 Uiso 0.434(5) 1 d PR A 2
O7 O 0.665(2) 0.4210(14) 0.0395(3) 0.053(3) Uani 0.566(5) 1 d PU A 1
O8 O 1.2915(16) 0.1084(14) 0.0627(5) 0.041(3) Uani 0.566(5) 1 d PDU A 1
O9 O 1.0183(19) 0.1011(15) 0.0624(6) 0.066(5) Uani 0.566(5) 1 d PDU A 1
N3 N 0.7783(10) 0.5742(6) 0.01220(18) 0.034(2) Uani 0.566(5) 1 d PU A 1
H3 H 0.8730 0.6044 0.0042 0.041 Uiso 0.566(5) 1 calc PR A 1
N4 N 1.1518(17) 0.1541(13) 0.0571(6) 0.046(5) Uani 0.566(5) 1 d PDU A 1
C26 C 0.5862(17) 0.6844(15) -0.0293(5) 0.064(4) Uani 0.566(5) 1 d PU A 1
H26D H 0.4638 0.6962 -0.0310 0.096 Uiso 0.566(5) 1 calc PR A 1
H26E H 0.6220 0.6323 -0.0488 0.096 Uiso 0.566(5) 1 calc PR A 1
H26F H 0.6449 0.7553 -0.0327 0.096 Uiso 0.566(5) 1 calc PR A 1
C27 C 0.7851(14) 0.4744(9) 0.0261(3) 0.037(3) Uani 0.566(5) 1 d PU A 1
C28 C 0.9551(18) 0.4188(13) 0.0258(5) 0.029(4) Uani 0.566(5) 1 d PU A 1
C29 C 0.978(2) 0.3155(16) 0.0403(6) 0.042(5) Uani 0.566(5) 1 d PU A 1
H29 H 0.8821 0.2778 0.0502 0.050 Uiso 0.566(5) 1 calc PR A 1
C30 C 1.129(2) 0.2641(15) 0.0412(5) 0.028(5) Uani 0.566(5) 1 d PU A 1
C31 C 1.284(2) 0.3160(14) 0.0268(4) 0.041(4) Uani 0.566(5) 1 d PU A 1
H31 H 1.3927 0.2827 0.0291 0.049 Uiso 0.566(5) 1 calc PR A 1
C32 C 1.258(2) 0.4172(12) 0.0099(4) 0.050(5) Uani 0.566(5) 1 d PU A 1
H32 H 1.3514 0.4534 -0.0016 0.061 Uiso 0.566(5) 1 calc PR A 1
C33 C 1.1007(19) 0.4684(16) 0.0092(5) 0.054(5) Uani 0.566(5) 1 d PU A 1
H33 H 1.0896 0.5386 -0.0026 0.065 Uiso 0.566(5) 1 calc PR A 1
O71 O 0.632(3) 0.4085(18) 0.0258(4) 0.045(4) Uani 0.434(5) 1 d PU A 2
O81 O 0.345(2) 0.090(2) 0.0623(8) 0.074(7) Uani 0.434(5) 1 d PDU A 2
O91 O 0.063(2) 0.0780(19) 0.0660(8) 0.054(6) Uani 0.434(5) 1 d PDU A 2
N31 N 0.4923(11) 0.5690(8) 0.0129(2) 0.026(3) Uani 0.434(5) 1 d PU A 2
H31A H 0.3923 0.5997 0.0098 0.031 Uiso 0.434(5) 1 calc PR A 2
N41 N 0.1984(18) 0.1243(19) 0.0573(8) 0.036(6) Uani 0.434(5) 1 d PDU A 2
C261 C 0.674(2) 0.6750(19) -0.0325(6) 0.064(5) Uani 0.434(5) 1 d PU A 2
H26A H 0.6749 0.6103 -0.0490 0.096 Uiso 0.434(5) 1 calc PR A 2
H26B H 0.7855 0.7105 -0.0328 0.096 Uiso 0.434(5) 1 calc PR A 2
H26C H 0.5884 0.7280 -0.0411 0.096 Uiso 0.434(5) 1 calc PR A 2
C271 C 0.4956(18) 0.4612(11) 0.0207(3) 0.031(4) Uani 0.434(5) 1 d PU A 2
C281 C 0.330(2) 0.4062(16) 0.0256(4) 0.035(5) Uani 0.434(5) 1 d PU A 2
C291 C 0.334(2) 0.2942(16) 0.0390(5) 0.033(5) Uani 0.434(5) 1 d PU A 2
H291 H 0.4384 0.2584 0.0445 0.039 Uiso 0.434(5) 1 calc PR A 2
C301 C 0.193(3) 0.244(2) 0.0433(7) 0.025(6) Uani 0.434(5) 1 d PU A 2
C311 C 0.029(3) 0.289(2) 0.0378(8) 0.031(7) Uani 0.434(5) 1 d PU A 2
H311 H -0.0711 0.2489 0.0434 0.037 Uiso 0.434(5) 1 calc PR A 2
C321 C 0.026(3) 0.397(2) 0.0236(7) 0.041(6) Uani 0.434(5) 1 d PU A 2
H321 H -0.0797 0.4299 0.0179 0.049 Uiso 0.434(5) 1 calc PR A 2
C331 C 0.173(3) 0.456(2) 0.0176(6) 0.040(6) Uani 0.434(5) 1 d PU A 2
H331 H 0.1682 0.5299 0.0082 0.048 Uiso 0.434(5) 1 calc PR A 2
O101 O -0.164(3) 0.5644(18) 0.1249(5) 0.073(3) Uani 0.340(5) 1 d PDU B 1
H101 H -0.2460 0.5977 0.1152 0.109 Uiso 0.340(5) 1 calc PR B 1
O104 O 0.4213(15) 0.4140(10) 0.0974(3) 0.067(3) Uani 0.340(5) 1 d PDU B 1
H104 H 0.5196 0.4029 0.0894 0.101 Uiso 0.340(5) 1 calc PR B 1
C101 C -0.010(3) 0.619(2) 0.1148(7) 0.066(3) Uani 0.340(5) 1 d PDU B 1
H10C H 0.0134 0.6844 0.1308 0.080 Uiso 0.340(5) 1 calc PR B 1
H10D H -0.0092 0.6420 0.0882 0.080 Uiso 0.340(5) 1 calc PR B 1
C102 C 0.121(3) 0.520(2) 0.1226(8) 0.062(3) Uani 0.340(5) 1 d PU B 1
H10E H 0.1041 0.4572 0.1051 0.074 Uiso 0.340(5) 1 calc PR B 1
H10F H 0.1122 0.4922 0.1486 0.074 Uiso 0.340(5) 1 calc PR B 1
C103 C 0.313(4) 0.588(3) 0.1147(7) 0.061(3) Uani 0.340(5) 1 d PU B 1
H10G H 0.3162 0.6208 0.0893 0.073 Uiso 0.340(5) 1 calc PR B 1
H10H H 0.3316 0.6473 0.1333 0.073 Uiso 0.340(5) 1 calc PR B 1
C104 C 0.417(5) 0.516(3) 0.1178(12) 0.060(3) Uani 0.340(5) 1 d PDU B 1
H10I H 0.4170 0.4956 0.1445 0.072 Uiso 0.340(5) 1 calc PR B 1
H10J H 0.5275 0.5527 0.1130 0.072 Uiso 0.340(5) 1 calc PR B 1
O111 O 0.0559(16) 0.6634(10) 0.1602(3) 0.078(4) Uani 0.334(4) 1 d PDU C 2
H111 H 0.1254 0.6493 0.1773 0.117 Uiso 0.334(4) 1 calc PR C 2
O114 O 0.6161(16) 0.5663(10) 0.1260(3) 0.066(3) Uani 0.334(4) 1 d PDU C 2
H114 H 0.6271 0.6151 0.1094 0.099 Uiso 0.334(4) 1 calc PR C 2
C111 C 0.027(3) 0.5651(15) 0.1385(6) 0.069(3) Uani 0.334(4) 1 d PDU C 2
H11B H 0.0590 0.4998 0.1537 0.083 Uiso 0.334(4) 1 calc PR C 2
H11C H -0.0959 0.5594 0.1333 0.083 Uiso 0.334(4) 1 calc PR C 2
C112 C 0.107(4) 0.560(2) 0.1071(7) 0.064(3) Uani 0.334(4) 1 d PU C 2
H11D H 0.0417 0.6053 0.0891 0.076 Uiso 0.334(4) 1 calc PR C 2
H11E H 0.0997 0.4823 0.0984 0.076 Uiso 0.334(4) 1 calc PR C 2
C113 C 0.289(4) 0.594(3) 0.1028(7) 0.061(3) Uani 0.334(4) 1 d PU C 2
H11F H 0.2998 0.6698 0.1135 0.073 Uiso 0.334(4) 1 calc PR C 2
H11G H 0.3115 0.6010 0.0757 0.073 Uiso 0.334(4) 1 calc PR C 2
C114 C 0.455(3) 0.513(3) 0.1220(18) 0.061(3) Uani 0.334(4) 1 d PDU C 2
H11I H 0.4184 0.4872 0.1470 0.073 Uiso 0.334(4) 1 calc PR C 2
H11J H 0.4698 0.4469 0.1061 0.073 Uiso 0.334(4) 1 calc PR C 2
O121 O -0.145(3) 0.5866(18) 0.1314(5) 0.068(3) Uani 0.326(5) 1 d PDU D 3
H121 H -0.2477 0.5873 0.1256 0.102 Uiso 0.326(5) 1 calc PR D 3
C121 C -0.044(3) 0.606(2) 0.0987(5) 0.068(3) Uani 0.326(5) 1 d PDU D 3
H12C H -0.0838 0.6754 0.0866 0.082 Uiso 0.326(5) 1 calc PR D 3
H12D H -0.0627 0.5445 0.0808 0.082 Uiso 0.326(5) 1 calc PR D 3
C122 C 0.152(4) 0.6167(17) 0.1069(7) 0.066(3) Uani 0.326(5) 1 d PU D 3
H12E H 0.2115 0.6363 0.0834 0.079 Uiso 0.326(5) 1 calc PR D 3
H12F H 0.1709 0.6778 0.1249 0.079 Uiso 0.326(5) 1 calc PR D 3
C123 C 0.222(3) 0.520(2) 0.1212(7) 0.060(3) Uani 0.326(5) 1 d PU D 3
H12G H 0.1972 0.4591 0.1034 0.072 Uiso 0.326(5) 1 calc PR D 3
H12H H 0.1630 0.5024 0.1448 0.072 Uiso 0.326(5) 1 calc PR D 3
O124 O 0.5399(19) 0.5235(12) 0.1008(4) 0.068(3) Uani 0.326(5) 1 d PDU D 3
H124 H 0.5457 0.5885 0.0924 0.102 Uiso 0.326(5) 1 calc PR D 3
C124 C 0.412(5) 0.518(3) 0.1290(9) 0.062(3) Uani 0.326(5) 1 d PDU D 3
H12I H 0.4348 0.5807 0.1463 0.074 Uiso 0.326(5) 1 calc PR D 3
H12J H 0.4343 0.4494 0.1434 0.074 Uiso 0.326(5) 1 calc PR D 3

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.033(2) 0.0276(19) 0.032(2) 0.0048(18) -0.001(2) 0.000(2)
O2 0.038(3) 0.036(2) 0.0288(19) 0.0039(19) 0.002(2) 0.0062(19)
O3 0.053(3) 0.027(2) 0.042(2) -0.0030(19) 0.002(2) 0.003(2)
O4 0.075(3) 0.029(2) 0.0187(17) -0.0017(17) -0.004(2) 0.000(2)
N1 0.039(3) 0.026(3) 0.014(2) 0.000(2) 0.009(2) -0.001(2)
N2 0.082(4) 0.032(3) 0.026(3) -0.007(2) 0.000(3) -0.025(3)
C1 0.026(3) 0.025(3) 0.031(3) -0.003(3) 0.008(3) -0.002(3)
C2 0.029(4) 0.034(3) 0.022(3) 0.008(3) 0.003(3) -0.002(3)
C3 0.045(4) 0.020(3) 0.040(3) 0.001(3) 0.004(4) 0.005(3)
C4 0.040(4) 0.019(3) 0.029(3) -0.004(3) 0.006(3) 0.003(3)
C5 0.038(4) 0.026(3) 0.022(3) 0.000(3) -0.001(3) -0.006(3)
C6 0.028(4) 0.022(3) 0.028(3) 0.007(3) 0.002(3) -0.004(3)
C7 0.054(4) 0.027(3) 0.018(3) -0.006(3) 0.005(3) 0.001(3)
C8 0.041(4) 0.022(3) 0.022(3) -0.002(3) 0.001(3) -0.006(3)
C9 0.034(4) 0.026(3) 0.037(3) -0.010(3) 0.010(3) 0.002(3)
C10 0.042(4) 0.020(3) 0.032(3) -0.004(3) -0.005(3) -0.004(3)
C11 0.034(4) 0.021(3) 0.037(3) 0.001(3) 0.006(3) -0.006(3)
C12 0.046(4) 0.028(3) 0.028(3) 0.006(3) 0.001(3) -0.010(3)
C13 0.051(4) 0.038(3) 0.026(3) 0.004(3) 0.004(3) -0.011(4)
C14 0.048(4) 0.035(4) 0.019(3) -0.005(3) 0.001(3) -0.011(4)
C15 0.069(5) 0.037(3) 0.031(3) 0.007(3) 0.000(4) -0.017(4)
C16 0.058(5) 0.037(4) 0.030(4) 0.002(3) -0.009(3) -0.012(3)
C17 0.057(5) 0.036(3) 0.017(3) 0.001(3) 0.003(3) -0.016(3)
C18 0.043(4) 0.024(3) 0.021(3) -0.003(2) 0.005(3) -0.004(3)
C19 0.040(4) 0.025(3) 0.032(3) 0.000(3) 0.007(3) -0.007(3)
C20 0.046(4) 0.033(4) 0.028(3) -0.001(3) 0.015(3) -0.012(3)
C21 0.057(5) 0.029(3) 0.023(3) -0.007(3) 0.006(4) -0.004(3)
C22 0.044(4) 0.047(3) 0.025(3) 0.008(3) 0.007(3) 0.003(3)
C23 0.090(5) 0.023(3) 0.065(4) -0.005(3) 0.004(4) 0.009(4)
O5 0.046(5) 0.043(4) 0.027(4) -0.003(3) 0.005(4) 0.001(5)
O6 0.061(5) 0.041(5) 0.043(4) -0.017(4) -0.014(4) 0.016(4)
O51 0.041(6) 0.037(6) 0.023(5) -0.004(5) 0.001(5) -0.021(5)
O61 0.066(7) 0.033(5) 0.050(5) -0.002(4) 0.021(5) -0.022(5)
C24 0.069(5) 0.040(4) 0.046(4) -0.004(4) -0.018(5) -0.002(4)
C25 0.059(5) 0.042(4) 0.049(4) -0.009(3) -0.003(4) 0.008(4)
O7 0.042(6) 0.058(5) 0.059(7) 0.004(6) 0.007(6) -0.002(5)
O8 0.036(7) 0.056(7) 0.030(6) -0.010(5) 0.000(7) 0.000(7)
O9 0.080(9) 0.060(8) 0.059(7) 0.024(6) 0.007(7) 0.001(7)
N3 0.028(5) 0.039(5) 0.037(4) -0.007(4) 0.002(4) 0.004(4)
N4 0.053(8) 0.055(8) 0.029(6) -0.014(6) -0.004(7) 0.015(7)
C26 0.067(8) 0.079(6) 0.046(6) 0.000(5) -0.007(7) 0.007(7)
C27 0.035(7) 0.045(6) 0.031(5) -0.007(5) -0.013(5) -0.009(6)
C28 0.031(8) 0.027(7) 0.029(6) -0.009(5) -0.006(6) -0.006(6)
C29 0.048(10) 0.035(9) 0.042(8) -0.009(7) -0.003(7) -0.002(7)
C30 0.029(9) 0.030(8) 0.026(7) -0.001(6) -0.004(8) -0.001(8)
C31 0.039(8) 0.043(8) 0.041(7) -0.003(6) -0.002(6) 0.005(7)
C32 0.045(9) 0.038(8) 0.068(8) 0.006(7) 0.006(7) -0.015(7)
C33 0.050(9) 0.051(8) 0.061(8) 0.011(7) 0.001(7) -0.004(7)
O71 0.041(7) 0.044(6) 0.051(8) 0.006(6) -0.002(6) -0.003(5)
O81 0.067(10) 0.081(10) 0.075(9) -0.017(7) 0.001(8) 0.016(8)
O91 0.035(8) 0.063(10) 0.065(9) 0.016(7) 0.016(7) -0.011(7)
N31 0.015(6) 0.026(5) 0.036(6) -0.009(5) 0.002(5) -0.012(5)
N41 0.044(9) 0.040(9) 0.025(8) -0.001(7) 0.004(8) 0.001(9)
C261 0.069(9) 0.076(7) 0.047(6) -0.001(6) -0.003(8) -0.001(8)
C271 0.033(8) 0.029(7) 0.030(7) 0.005(6) 0.006(6) -0.003(6)
C281 0.040(9) 0.038(8) 0.027(7) 0.011(7) -0.005(7) -0.001(7)
C291 0.039(9) 0.032(8) 0.026(8) 0.013(6) 0.000(7) -0.002(7)
C301 0.025(10) 0.027(9) 0.022(8) -0.003(7) 0.002(8) 0.012(8)
C311 0.025(10) 0.032(10) 0.036(9) 0.001(8) -0.007(8) 0.004(8)
C321 0.037(10) 0.045(10) 0.042(9) -0.003(7) 0.004(8) 0.001(8)
C331 0.048(11) 0.033(9) 0.040(9) 0.009(7) 0.009(8) -0.004(8)
O101 0.080(5) 0.066(5) 0.073(5) 0.001(5) -0.014(5) 0.012(5)
O104 0.075(5) 0.068(5) 0.059(5) 0.001(4) 0.009(4) -0.002(4)
C101 0.073(5) 0.061(5) 0.064(5) -0.002(4) -0.009(4) 0.010(4)
C102 0.071(5) 0.055(5) 0.059(5) -0.009(4) -0.005(5) 0.006(5)
C103 0.067(4) 0.057(4) 0.058(5) -0.001(4) 0.005(4) 0.000(4)
C104 0.068(4) 0.056(4) 0.057(5) -0.001(4) 0.009(4) -0.004(4)
O111 0.082(7) 0.071(6) 0.082(6) 0.005(6) -0.005(6) 0.020(6)
O114 0.077(6) 0.058(5) 0.062(6) 0.007(5) 0.014(5) -0.021(5)
C111 0.075(4) 0.065(4) 0.067(4) -0.003(4) -0.005(4) 0.007(4)
C112 0.070(4) 0.059(4) 0.062(4) -0.008(4) -0.001(4) 0.002(4)
C113 0.066(5) 0.057(4) 0.060(5) -0.006(4) 0.004(4) 0.000(4)
C114 0.068(5) 0.056(4) 0.058(5) 0.002(4) 0.012(4) -0.005(4)
O121 0.079(5) 0.061(5) 0.064(5) -0.004(4) -0.016(5) 0.014(5)
C121 0.075(5) 0.062(5) 0.067(5) -0.004(4) -0.005(4) 0.010(4)
C122 0.073(4) 0.062(4) 0.063(4) -0.002(4) -0.001(4) 0.002(4)
C123 0.066(5) 0.055(4) 0.057(4) -0.007(4) 0.002(4) -0.001(4)
O124 0.076(5) 0.063(4) 0.065(5) 0.007(4) 0.013(4) -0.003(4)
C124 0.068(4) 0.057(4) 0.059(5) -0.001(4) 0.010(4) -0.003(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.430(5) . ?
O1 C12 1.448(4) . ?
O2 C2 1.378(5) . ?
O2 C22 1.439(4) . ?
O3 C3 1.366(5) . ?
O3 C23 1.432(5) . ?
O4 C9 1.218(5) . ?
N1 C9 1.385(5) . ?
N1 C6 1.429(5) . ?
N1 C8 1.511(5) . ?
N2 C15 1.511(5) . ?
N2 C16 1.516(6) . ?
N2 C21 1.519(6) . ?
N2 H2A 0.9300 . ?
C1 C6 1.379(6) . ?
C1 C2 1.392(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.412(6) . ?
C3 C4 1.383(6) . ?
C4 C5 1.393(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.375(5) . ?
C5 C7 1.508(6) . ?
C7 C21 1.525(6) . ?
C7 C17 1.535(7) . ?
C7 C8 1.573(6) . ?
C8 C18 1.514(6) . ?
C8 H8A 1.0000 . ?
C9 C10 1.511(6) . ?
C10 C11 1.544(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.522(6) . ?
C11 H11A 1.0000 . ?
C12 C13 1.509(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.321(6) . ?
C13 H13A 0.9500 . ?
C14 C19 1.505(6) . ?
C14 C15 1.519(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.532(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.552(6) . ?
C18 H18A 1.0000 . ?
C19 C20 1.531(6) . ?
C19 H19A 1.0000 . ?
C20 C21 1.513(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.268(9) . ?
O6 C24 1.299(8) . ?
O51 C24 1.080(10) . ?
O61 C24 1.419(9) . ?
C24 C25 1.548(7) . ?
C25 N31 1.364(9) . ?
C25 N3 1.395(8) . ?
C25 C26 1.536(16) . ?
C25 C261 1.60(2) . ?
C25 H25 1.0000 . ?
C25 H251 0.9600 . ?
O7 C27 1.245(17) . ?
O8 N4 1.250(7) . ?
O9 N4 1.249(6) . ?
N3 C27 1.303(11) . ?
N3 H251 0.4870 . ?
N3 H3 0.8800 . ?
N4 C30 1.45(2) . ?
C26 H26D 0.9800 . ?
C26 H26E 0.9800 . ?
C26 H26F 0.9800 . ?
C27 C28 1.502(15) . ?
C28 C29 1.36(3) . ?
C28 C33 1.43(2) . ?
C29 C30 1.35(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.47(2) . ?
C31 C32 1.38(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.39(2) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O71 C271 1.26(2) . ?
O81 N41 1.249(7) . ?
O91 N41 1.249(7) . ?
N31 C271 1.329(13) . ?
N31 H31A 0.8800 . ?
N41 C301 1.53(3) . ?
C261 H26A 0.9800 . ?
C261 H26B 0.9800 . ?
C261 H26C 0.9800 . ?
C271 C281 1.477(19) . ?
C281 C331 1.41(3) . ?
C281 C291 1.43(3) . ?
C291 C301 1.28(3) . ?
C291 H291 0.9500 . ?
C301 C311 1.42(3) . ?
C311 C321 1.39(4) . ?
C311 H311 0.9500 . ?
C321 C331 1.38(3) . ?
C321 H321 0.9500 . ?
C331 H331 0.9500 . ?
O101 C101 1.434(11) . ?
O101 H101 0.8400 . ?
O104 C104 1.433(11) . ?
O104 H104 0.8400 . ?
C101 C102 1.61(4) . ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?
C102 C103 1.75(4) . ?
C102 H10E 0.9900 . ?
C102 H10F 0.9900 . ?
C103 C104 1.19(4) . ?
C103 H10G 0.9900 . ?
C103 H10H 0.9900 . ?
C104 H10I 0.9900 . ?
C104 H10J 0.9900 . ?
O111 C111 1.436(11) . ?
O111 H111 0.8400 . ?
O114 C114 1.434(11) . ?
O114 H114 0.8400 . ?
C111 C112 1.29(3) . ?
C111 H11B 0.9900 . ?
C111 H11C 0.9900 . ?
C112 C113 1.50(4) . ?
C112 H11D 0.9900 . ?
C112 H11E 0.9900 . ?
C113 C114 1.77(5) . ?
C113 H11F 0.9900 . ?
C113 H11G 0.9900 . ?
C114 H11I 0.9900 . ?
C114 H11J 0.9900 . ?
O121 C121 1.433(11) . ?
O121 H121 0.8400 . ?
C121 C122 1.59(3) . ?
C121 H12C 0.9900 . ?
C121 H12D 0.9900 . ?
C122 C123 1.39(3) . ?
C122 H12E 0.9900 . ?
C122 H12F 0.9900 . ?
C123 C124 1.53(5) . ?
C123 H12G 0.9900 . ?
C123 H12H 0.9900 . ?
O124 C124 1.431(11) . ?
O124 H124 0.8400 . ?
C124 H12I 0.9900 . ?
C124 H12J 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.9(4) . . ?
C2 O2 C22 116.0(3) . . ?
C3 O3 C23 115.8(4) . . ?
C9 N1 C6 125.0(4) . . ?
C9 N1 C8 118.5(4) . . ?
C6 N1 C8 108.8(4) . . ?
C15 N2 C16 113.7(4) . . ?
C15 N2 C21 113.6(4) . . ?
C16 N2 C21 107.8(4) . . ?
C15 N2 H2A 107.1 . . ?
C16 N2 H2A 107.1 . . ?
C21 N2 H2A 107.1 . . ?
C6 C1 C2 117.1(5) . . ?
C6 C1 H1A 121.4 . . ?
C2 C1 H1A 121.4 . . ?
O2 C2 C1 123.7(4) . . ?
O2 C2 C3 114.8(4) . . ?
C1 C2 C3 121.4(5) . . ?
O3 C3 C4 125.3(5) . . ?
O3 C3 C2 115.1(4) . . ?
C4 C3 C2 119.5(4) . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 C7 110.8(4) . . ?
C4 C5 C7 128.7(5) . . ?
C5 C6 C1 122.5(4) . . ?
C5 C6 N1 110.6(4) . . ?
C1 C6 N1 126.9(4) . . ?
C5 C7 C21 116.0(5) . . ?
C5 C7 C17 111.9(4) . . ?
C21 C7 C17 102.7(4) . . ?
C5 C7 C8 102.7(4) . . ?
C21 C7 C8 113.3(4) . . ?
C17 C7 C8 110.4(4) . . ?
N1 C8 C18 106.3(4) . . ?
N1 C8 C7 103.4(4) . . ?
C18 C8 C7 117.2(4) . . ?
N1 C8 H8A 109.9 . . ?
C18 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
O4 C9 N1 122.2(5) . . ?
O4 C9 C10 122.2(5) . . ?
N1 C9 C10 115.5(4) . . ?
C9 C10 C11 117.6(4) . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 115.2(4) . . ?
O1 C11 C10 104.9(4) . . ?
C18 C11 C10 110.3(4) . . ?
O1 C11 H11A 108.8 . . ?
C18 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
O1 C12 C13 110.3(4) . . ?
O1 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C19 124.5(5) . . ?
C13 C14 C15 121.1(5) . . ?
C19 C14 C15 114.5(5) . . ?
N2 C15 C14 109.6(4) . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 104.5(4) . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.5(4) . . ?
C16 C17 H17A 111.1 . . ?
C7 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C7 C17 H17B 111.1 . . ?
H17A C17 H17B 109.0 . . ?
C8 C18 C11 108.3(4) . . ?
C8 C18 C19 111.3(4) . . ?
C11 C18 C19 118.1(4) . . ?
C8 C18 H18A 106.1 . . ?
C11 C18 H18A 106.1 . . ?
C19 C18 H18A 106.1 . . ?
C14 C19 C20 110.8(4) . . ?
C14 C19 C18 113.9(4) . . ?
C20 C19 C18 106.5(4) . . ?
C14 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C21 C20 C19 107.8(4) . . ?
C21 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 N2 110.9(4) . . ?
C20 C21 C7 115.9(4) . . ?
N2 C21 C7 105.5(4) . . ?
C20 C21 H21A 108.1 . . ?
N2 C21 H21A 108.1 . . ?
C7 C21 H21A 108.1 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O51 C24 O5 48.4(6) . . ?
O51 C24 O6 82.0(10) . . ?
O5 C24 O6 120.0(7) . . ?
O51 C24 O61 124.5(8) . . ?
O5 C24 O61 97.7(7) . . ?
O6 C24 O61 83.4(6) . . ?
O51 C24 C25 125.7(9) . . ?
O5 C24 C25 118.2(6) . . ?
O6 C24 C25 118.0(6) . . ?
O61 C24 C25 108.4(7) . . ?
N31 C25 N3 110.1(6) . . ?
N31 C25 C26 97.5(8) . . ?
N3 C25 C26 117.4(8) . . ?
N31 C25 C24 110.1(7) . . ?
N3 C25 C24 111.5(6) . . ?
C26 C25 C24 109.3(8) . . ?
N31 C25 C261 115.9(10) . . ?
N3 C25 C261 92.6(8) . . ?
C26 C25 C261 26.1(8) . . ?
C24 C25 C261 115.4(9) . . ?
N31 C25 H25 8.4 . . ?
N3 C25 H25 106.0 . . ?
C26 C25 H25 106.0 . . ?
C24 C25 H25 106.0 . . ?
C261 C25 H25 124.0 . . ?
N31 C25 H251 105.3 . . ?
N3 C25 H251 10.9 . . ?
C26 C25 H251 128.3 . . ?
C24 C25 H251 105.4 . . ?
C261 C25 H251 103.5 . . ?
H25 C25 H251 99.9 . . ?
C27 N3 C25 124.0(9) . . ?
C27 N3 H251 108.3 . . ?
C25 N3 H251 21.9 . . ?
C27 N3 H3 118.0 . . ?
C25 N3 H3 118.0 . . ?
H251 N3 H3 130.8 . . ?
O9 N4 O8 119.7(17) . . ?
O9 N4 C30 114.9(14) . . ?
O8 N4 C30 125.1(17) . . ?
C25 C26 H26D 109.5 . . ?
C25 C26 H26E 109.5 . . ?
H26D C26 H26E 109.5 . . ?
C25 C26 H26F 109.5 . . ?
H26D C26 H26F 109.5 . . ?
H26E C26 H26F 109.5 . . ?
O7 C27 N3 126.3(13) . . ?
O7 C27 C28 117.2(13) . . ?
N3 C27 C28 116.5(11) . . ?
O7 C27 H251 109.2 . . ?
N3 C27 H251 17.6 . . ?
C28 C27 H251 133.4 . . ?
C29 C28 C33 115.9(15) . . ?
C29 C28 C27 121.5(15) . . ?
C33 C28 C27 122.6(14) . . ?
C30 C29 C28 123.1(19) . . ?
C30 C29 H29 118.4 . . ?
C28 C29 H29 118.4 . . ?
C29 C30 N4 122.6(18) . . ?
C29 C30 C31 122.5(17) . . ?
N4 C30 C31 114.9(15) . . ?
C32 C31 C30 113.9(14) . . ?
C32 C31 H31 123.0 . . ?
C30 C31 H31 123.0 . . ?
C31 C32 C33 122.3(15) . . ?
C31 C32 H32 118.9 . . ?
C33 C32 H32 118.9 . . ?
C32 C33 C28 122.0(16) . . ?
C32 C33 H33 119.0 . . ?
C28 C33 H33 119.0 . . ?
C271 N31 C25 125.9(10) . . ?
C271 N31 H31A 117.1 . . ?
C25 N31 H31A 117.1 . . ?
O81 N41 O91 128(2) . . ?
O81 N41 C301 113(2) . . ?
O91 N41 C301 118.7(18) . . ?
C25 C261 H26A 109.5 . . ?
C25 C261 H26B 109.5 . . ?
H26A C261 H26B 109.5 . . ?
C25 C261 H26C 109.5 . . ?
H26A C261 H26C 109.5 . . ?
H26B C261 H26C 109.5 . . ?
O71 C271 N31 122.5(15) . . ?
O71 C271 C281 120.9(16) . . ?
N31 C271 C281 116.5(13) . . ?
C331 C281 C291 119.4(17) . . ?
C331 C281 C271 124.4(16) . . ?
C291 C281 C271 116.2(15) . . ?
C301 C291 C281 117.6(18) . . ?
C301 C291 H291 121.2 . . ?
C281 C291 H291 121.2 . . ?
C291 C301 C311 127(2) . . ?
C291 C301 N41 117.4(18) . . ?
C311 C301 N41 116(2) . . ?
C321 C311 C301 115(2) . . ?
C321 C311 H311 122.5 . . ?
C301 C311 H311 122.5 . . ?
C331 C321 C311 122(2) . . ?
C331 C321 H321 119.1 . . ?
C311 C321 H321 119.1 . . ?
C321 C331 C281 119(2) . . ?
C321 C331 H331 120.5 . . ?
C281 C331 H331 120.5 . . ?
C101 O101 H101 109.5 . . ?
C104 O104 H104 109.5 . . ?
O101 C101 C102 99.1(19) . . ?
O101 C101 H10C 112.0 . . ?
C102 C101 H10C 112.0 . . ?
O101 C101 H10D 112.0 . . ?
C102 C101 H10D 112.0 . . ?
H10C C101 H10D 109.6 . . ?
C101 C102 C103 100.3(17) . . ?
C101 C102 H10E 111.7 . . ?
C103 C102 H10E 111.7 . . ?
C101 C102 H10F 111.7 . . ?
C103 C102 H10F 111.7 . . ?
H10E C102 H10F 109.5 . . ?
C104 C103 C102 104(4) . . ?
C104 C103 H10G 110.9 . . ?
C102 C103 H10G 110.9 . . ?
C104 C103 H10H 110.9 . . ?
C102 C103 H10H 110.9 . . ?
H10G C103 H10H 108.9 . . ?
C103 C104 O104 126(3) . . ?
C103 C104 H10I 105.8 . . ?
O104 C104 H10I 105.8 . . ?
C103 C104 H10J 105.8 . . ?
O104 C104 H10J 105.8 . . ?
H10I C104 H10J 106.2 . . ?
C111 O111 H111 109.5 . . ?
C114 O114 H114 109.5 . . ?
C112 C111 O111 115.4(18) . . ?
C112 C111 H11B 108.4 . . ?
O111 C111 H11B 108.4 . . ?
C112 C111 H11C 108.4 . . ?
O111 C111 H11C 108.4 . . ?
H11B C111 H11C 107.5 . . ?
C111 C112 C113 123(2) . . ?
C111 C112 H11D 106.6 . . ?
C113 C112 H11D 106.6 . . ?
C111 C112 H11E 106.6 . . ?
C113 C112 H11E 106.6 . . ?
H11D C112 H11E 106.5 . . ?
C112 C113 C114 121(2) . . ?
C112 C113 H11F 107.0 . . ?
C114 C113 H11F 107.0 . . ?
C112 C113 H11G 107.0 . . ?
C114 C113 H11G 107.0 . . ?
H11F C113 H11G 106.8 . . ?
O114 C114 C113 117(3) . . ?
O114 C114 H11I 108.1 . . ?
C113 C114 H11I 108.1 . . ?
O114 C114 H11J 108.1 . . ?
C113 C114 H11J 108.1 . . ?
H11I C114 H11J 107.3 . . ?
C121 O121 H121 109.5 . . ?
O121 C121 C122 113.8(19) . . ?
O121 C121 H12C 108.8 . . ?
C122 C121 H12C 108.8 . . ?
O121 C121 H12D 108.8 . . ?
C122 C121 H12D 108.8 . . ?
H12C C121 H12D 107.7 . . ?
C123 C122 C121 113(2) . . ?
C123 C122 H12E 109.0 . . ?
C121 C122 H12E 109.0 . . ?
C123 C122 H12F 109.0 . . ?
C121 C122 H12F 109.0 . . ?
H12E C122 H12F 107.8 . . ?
C122 C123 C124 118(3) . . ?
C122 C123 H12G 107.8 . . ?
C124 C123 H12G 107.8 . . ?
C122 C123 H12H 107.8 . . ?
C124 C123 H12H 107.8 . . ?
H12G C123 H12H 107.1 . . ?
C124 O124 H124 109.5 . . ?
O124 C124 C123 124(3) . . ?
O124 C124 H12I 106.3 . . ?
C123 C124 H12I 106.3 . . ?
O124 C124 H12J 106.3 . . ?
C123 C124 H12J 106.3 . . ?
H12I C124 H12J 106.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 4.9(7) . . . . ?
C22 O2 C2 C3 -175.1(4) . . . . ?
C6 C1 C2 O2 -177.8(5) . . . . ?
C6 C1 C2 C3 2.2(8) . . . . ?
C23 O3 C3 C4 4.4(8) . . . . ?
C23 O3 C3 C2 -175.9(4) . . . . ?
O2 C2 C3 O3 -3.8(7) . . . . ?
C1 C2 C3 O3 176.2(5) . . . . ?
O2 C2 C3 C4 175.9(5) . . . . ?
C1 C2 C3 C4 -4.1(8) . . . . ?
O3 C3 C4 C5 -177.5(5) . . . . ?
C2 C3 C4 C5 2.8(8) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C3 C4 C5 C7 -175.2(5) . . . . ?
C4 C5 C6 C1 -2.1(8) . . . . ?
C7 C5 C6 C1 174.0(5) . . . . ?
C4 C5 C6 N1 175.9(5) . . . . ?
C7 C5 C6 N1 -8.0(6) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
C2 C1 C6 N1 -176.8(5) . . . . ?
C9 N1 C6 C5 -153.8(5) . . . . ?
C8 N1 C6 C5 -5.3(6) . . . . ?
C9 N1 C6 C1 24.1(9) . . . . ?
C8 N1 C6 C1 172.6(5) . . . . ?
C6 C5 C7 C21 141.3(5) . . . . ?
C4 C5 C7 C21 -43.0(8) . . . . ?
C6 C5 C7 C17 -101.4(5) . . . . ?
C4 C5 C7 C17 74.3(7) . . . . ?
C6 C5 C7 C8 17.1(6) . . . . ?
C4 C5 C7 C8 -167.2(5) . . . . ?
C9 N1 C8 C18 42.3(6) . . . . ?
C6 N1 C8 C18 -108.6(4) . . . . ?
C9 N1 C8 C7 166.2(4) . . . . ?
C6 N1 C8 C7 15.4(6) . . . . ?
C5 C7 C8 N1 -18.9(6) . . . . ?
C21 C7 C8 N1 -144.8(4) . . . . ?
C17 C7 C8 N1 100.6(5) . . . . ?
C5 C7 C8 C18 97.6(5) . . . . ?
C21 C7 C8 C18 -28.3(6) . . . . ?
C17 C7 C8 C18 -142.9(4) . . . . ?
C6 N1 C9 O4 -24.9(8) . . . . ?
C8 N1 C9 O4 -170.6(5) . . . . ?
C6 N1 C9 C10 156.3(4) . . . . ?
C8 N1 C9 C10 10.6(7) . . . . ?
O4 C9 C10 C11 143.8(5) . . . . ?
N1 C9 C10 C11 -37.4(7) . . . . ?
C12 O1 C11 C18 -66.7(5) . . . . ?
C12 O1 C11 C10 171.8(3) . . . . ?
C9 C10 C11 O1 131.9(4) . . . . ?
C9 C10 C11 C18 7.3(6) . . . . ?
C11 O1 C12 C13 88.7(5) . . . . ?
O1 C12 C13 C14 -66.5(6) . . . . ?
C12 C13 C14 C19 -1.5(8) . . . . ?
C12 C13 C14 C15 179.7(4) . . . . ?
C16 N2 C15 C14 78.0(6) . . . . ?
C21 N2 C15 C14 -45.9(6) . . . . ?
C13 C14 C15 N2 -127.7(5) . . . . ?
C19 C14 C15 N2 53.4(6) . . . . ?
C15 N2 C16 C17 -140.6(4) . . . . ?
C21 N2 C16 C17 -13.6(5) . . . . ?
N2 C16 C17 C7 33.4(5) . . . . ?
C5 C7 C17 C16 -165.5(4) . . . . ?
C21 C7 C17 C16 -40.4(5) . . . . ?
C8 C7 C17 C16 80.7(5) . . . . ?
N1 C8 C18 C11 -71.3(5) . . . . ?
C7 C8 C18 C11 173.8(4) . . . . ?
N1 C8 C18 C19 157.3(4) . . . . ?
C7 C8 C18 C19 42.4(6) . . . . ?
O1 C11 C18 C8 -72.9(5) . . . . ?
C10 C11 C18 C8 45.6(5) . . . . ?
O1 C11 C18 C19 54.7(6) . . . . ?
C10 C11 C18 C19 173.2(4) . . . . ?
C13 C14 C19 C20 178.8(5) . . . . ?
C15 C14 C19 C20 -2.3(6) . . . . ?
C13 C14 C19 C18 58.8(6) . . . . ?
C15 C14 C19 C18 -122.3(4) . . . . ?
C8 C18 C19 C14 60.2(5) . . . . ?
C11 C18 C19 C14 -66.0(6) . . . . ?
C8 C18 C19 C20 -62.3(5) . . . . ?
C11 C18 C19 C20 171.6(5) . . . . ?
C14 C19 C20 C21 -55.3(5) . . . . ?
C18 C19 C20 C21 69.1(5) . . . . ?
C19 C20 C21 N2 62.6(5) . . . . ?
C19 C20 C21 C7 -57.6(6) . . . . ?
C15 N2 C21 C20 -10.8(5) . . . . ?
C16 N2 C21 C20 -137.8(4) . . . . ?
C15 N2 C21 C7 115.5(4) . . . . ?
C16 N2 C21 C7 -11.6(5) . . . . ?
C5 C7 C21 C20 -82.6(6) . . . . ?
C17 C7 C21 C20 155.1(4) . . . . ?
C8 C7 C21 C20 36.0(7) . . . . ?
C5 C7 C21 N2 154.3(4) . . . . ?
C17 C7 C21 N2 32.0(5) . . . . ?
C8 C7 C21 N2 -87.2(5) . . . . ?
O51 C24 C25 N31 30.4(15) . . . . ?
O5 C24 C25 N31 87.5(11) . . . . ?
O6 C24 C25 N31 -70.4(9) . . . . ?
O61 C24 C25 N31 -162.7(7) . . . . ?
O51 C24 C25 N3 -92.1(14) . . . . ?
O5 C24 C25 N3 -35.0(11) . . . . ?
O6 C24 C25 N3 167.1(7) . . . . ?
O61 C24 C25 N3 74.8(8) . . . . ?
O51 C24 C25 C26 136.4(13) . . . . ?
O5 C24 C25 C26 -166.5(9) . . . . ?
O6 C24 C25 C26 35.7(11) . . . . ?
O61 C24 C25 C26 -56.7(10) . . . . ?
O51 C24 C25 C261 163.9(13) . . . . ?
O5 C24 C25 C261 -139.0(10) . . . . ?
O6 C24 C25 C261 63.1(12) . . . . ?
O61 C24 C25 C261 -29.2(11) . . . . ?
N31 C25 N3 C27 -16.6(10) . . . . ?
C26 C25 N3 C27 -127.0(10) . . . . ?
C24 C25 N3 C27 105.9(8) . . . . ?
C261 C25 N3 C27 -135.5(11) . . . . ?
C25 N3 C27 O7 -2.1(15) . . . . ?
C25 N3 C27 C28 177.9(9) . . . . ?
O7 C27 C28 C29 -1(2) . . . . ?
N3 C27 C28 C29 178.7(14) . . . . ?
O7 C27 C28 C33 176.1(13) . . . . ?
N3 C27 C28 C33 -3.8(18) . . . . ?
C33 C28 C29 C30 4(3) . . . . ?
C27 C28 C29 C30 -178.6(17) . . . . ?
C28 C29 C30 N4 179.3(18) . . . . ?
C28 C29 C30 C31 1(3) . . . . ?
O9 N4 C30 C29 15(3) . . . . ?
O8 N4 C30 C29 -171(2) . . . . ?
O9 N4 C30 C31 -166.5(19) . . . . ?
O8 N4 C30 C31 8(3) . . . . ?
C29 C30 C31 C32 -5(2) . . . . ?
N4 C30 C31 C32 176.4(15) . . . . ?
C30 C31 C32 C33 5(2) . . . . ?
C31 C32 C33 C28 0(2) . . . . ?
C29 C28 C33 C32 -4(2) . . . . ?
C27 C28 C33 C32 178.4(14) . . . . ?
N3 C25 N31 C271 4.3(13) . . . . ?
C26 C25 N31 C271 127.2(12) . . . . ?
C24 C25 N31 C271 -119.1(10) . . . . ?
C261 C25 N31 C271 107.7(14) . . . . ?
C25 N31 C271 O71 0(2) . . . . ?
C25 N31 C271 C281 176.6(10) . . . . ?
O71 C271 C281 C331 -174.7(18) . . . . ?
N31 C271 C281 C331 9(2) . . . . ?
O71 C271 C281 C291 5(2) . . . . ?
N31 C271 C281 C291 -171.7(13) . . . . ?
C331 C281 C291 C301 0(3) . . . . ?
C271 C281 C291 C301 -179.8(18) . . . . ?
C281 C291 C301 C311 -3(4) . . . . ?
C281 C291 C301 N41 179.4(19) . . . . ?
O81 N41 C301 C291 -1(4) . . . . ?
O91 N41 C301 C291 172(3) . . . . ?
O81 N41 C301 C311 -179(3) . . . . ?
O91 N41 C301 C311 -6(4) . . . . ?
C291 C301 C311 C321 5(4) . . . . ?
N41 C301 C311 C321 -177(2) . . . . ?
C301 C311 C321 C331 -4(4) . . . . ?
C311 C321 C331 C281 1(3) . . . . ?
C291 C281 C331 C321 1(3) . . . . ?
C271 C281 C331 C321 -179.3(18) . . . . ?
O101 C101 C102 C103 -174.7(18) . . . . ?
C101 C102 C103 C104 -176(3) . . . . ?
C102 C103 C104 O104 55(6) . . . . ?
O111 C111 C112 C113 42(4) . . . . ?
C111 C112 C113 C114 71(5) . . . . ?
C112 C113 C114 O114 -163(3) . . . . ?
O121 C121 C122 C123 63(3) . . . . ?
C121 C122 C123 C124 178(2) . . . . ?
C122 C123 C124 O124 -67(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O51 0.93 1.74 2.660(10) 168.3 .
N2 H2A O5 0.93 1.80 2.688(8) 159.7 .
N3 H3 O6 0.88 2.06 2.867(10) 151.6 4_565
N31 H31A O61 0.88 2.08 2.846(12) 144.9 4_465
O101 H101 O5 0.84 2.17 2.88(3) 142.6 1_455
O104 H104 O7 0.84 2.13 2.830(18) 140.1 .
O111 H111 O4 0.84 1.89 2.691(12) 160.5 3_645
O114 H114 O51 0.84 2.09 2.895(16) 160.5 .
O121 H121 O124 0.84 2.05 2.83(3) 153.7 1_455

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 930492'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


#===== end


data_b3nbds2
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-D-serinate trihydrate
;
_chemical_name_common            ?
_chemical_melting_point          397
_chemical_formula_moiety         'C23 H27 N2 O4, C10 H9 N2 O6, 3(H2 O)'
_chemical_formula_sum            'C33 H42 N4 O13'
_chemical_formula_weight         702.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.944(2)
_cell_length_b                   12.520(3)
_cell_length_c                   33.073(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3289.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7419
_cell_measurement_theta_min      2.9444
_cell_measurement_theta_max      28.6833

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15365
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.00
_reflns_number_total             6926
_reflns_number_gt                5407
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6926
_refine_ls_number_parameters     475
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78325(17) 1.05677(9) 0.69561(4) 0.0244(3) Uani 1 1 d . . .
O2 O 0.63596(16) 0.47356(9) 0.83380(3) 0.0206(3) Uani 1 1 d . . .
O3 O 0.69243(16) 0.36424(9) 0.76843(3) 0.0199(3) Uani 1 1 d . . .
O4 O 0.70717(18) 0.86832(10) 0.81676(4) 0.0272(3) Uani 1 1 d . . .
N1 N 0.67921(19) 0.80471(11) 0.75285(4) 0.0170(3) Uani 1 1 d . . .
N2 N 0.7493(2) 0.72664(12) 0.61747(4) 0.0227(4) Uani 1 1 d . . .
H2A H 0.7466 0.6717 0.5995 0.027 Uiso 1 1 calc R . .
C1 C 0.6543(2) 0.64346(13) 0.79836(5) 0.0178(4) Uani 1 1 d . . .
H1A H 0.6383 0.6828 0.8219 0.021 Uiso 1 1 calc R . .
C2 C 0.6568(2) 0.53298(14) 0.79909(5) 0.0172(4) Uani 1 1 d . . .
C3 C 0.6841(2) 0.47327(13) 0.76363(5) 0.0173(4) Uani 1 1 d . . .
C4 C 0.7010(2) 0.52520(14) 0.72698(5) 0.0172(4) Uani 1 1 d . . .
H4A H 0.7154 0.4863 0.7033 0.021 Uiso 1 1 calc R . .
C5 C 0.6963(2) 0.63621(14) 0.72584(5) 0.0171(4) Uani 1 1 d . . .
C6 C 0.6765(2) 0.69372(13) 0.76116(5) 0.0166(4) Uani 1 1 d . . .
C7 C 0.6955(2) 0.70897(13) 0.68961(5) 0.0175(4) Uani 1 1 d . . .
C8 C 0.7159(2) 0.82203(14) 0.70925(5) 0.0171(4) Uani 1 1 d . . .
H8A H 0.6327 0.8711 0.6977 0.020 Uiso 1 1 calc R . .
C9 C 0.7166(2) 0.88309(14) 0.78011(5) 0.0198(4) Uani 1 1 d . . .
C10 C 0.7651(3) 0.98964(14) 0.76230(5) 0.0228(4) Uani 1 1 d . . .
H10A H 0.8278 1.0289 0.7826 0.027 Uiso 1 1 calc R . .
H10B H 0.6626 1.0293 0.7570 0.027 Uiso 1 1 calc R . .
C11 C 0.8705(2) 0.98811(14) 0.72310(5) 0.0196(4) Uani 1 1 d . . .
H11A H 0.9822 1.0180 0.7287 0.024 Uiso 1 1 calc R . .
C12 C 0.8764(3) 1.08107(15) 0.65935(6) 0.0302(5) Uani 1 1 d . . .
H12A H 0.9956 1.0835 0.6656 0.036 Uiso 1 1 calc R . .
H12B H 0.8433 1.1510 0.6496 0.036 Uiso 1 1 calc R . .
C13 C 0.8464(3) 0.99964(15) 0.62672(6) 0.0276(5) Uani 1 1 d . . .
H13A H 0.7948 1.0216 0.6029 0.033 Uiso 1 1 calc R . .
C14 C 0.8900(3) 0.89800(14) 0.63042(5) 0.0234(4) Uani 1 1 d . . .
C15 C 0.8497(3) 0.81592(16) 0.59858(5) 0.0270(5) Uani 1 1 d . . .
H15A H 0.9531 0.7878 0.5872 0.032 Uiso 1 1 calc R . .
H15B H 0.7853 0.8486 0.5770 0.032 Uiso 1 1 calc R . .
C16 C 0.5705(2) 0.75757(15) 0.62635(5) 0.0236(4) Uani 1 1 d . . .
H16A H 0.4960 0.7343 0.6048 0.028 Uiso 1 1 calc R . .
H16B H 0.5602 0.8343 0.6295 0.028 Uiso 1 1 calc R . .
C17 C 0.5297(2) 0.70075(15) 0.66551(5) 0.0198(4) Uani 1 1 d . . .
H17A H 0.4994 0.6268 0.6607 0.024 Uiso 1 1 calc R . .
H17B H 0.4381 0.7359 0.6797 0.024 Uiso 1 1 calc R . .
C18 C 0.8901(2) 0.87314(14) 0.70776(5) 0.0181(4) Uani 1 1 d . . .
H18A H 0.9570 0.8360 0.7283 0.022 Uiso 1 1 calc R . .
C19 C 0.9818(2) 0.85404(14) 0.66735(5) 0.0198(4) Uani 1 1 d . . .
H19A H 1.0941 0.8862 0.6688 0.024 Uiso 1 1 calc R . .
C20 C 0.9999(2) 0.73244(14) 0.66340(6) 0.0220(4) Uani 1 1 d . . .
H20A H 1.0731 0.7154 0.6408 0.026 Uiso 1 1 calc R . .
H20B H 1.0495 0.7033 0.6878 0.026 Uiso 1 1 calc R . .
C21 C 0.8276(2) 0.68424(14) 0.65663(5) 0.0190(4) Uani 1 1 d . . .
H21A H 0.8396 0.6066 0.6544 0.023 Uiso 1 1 calc R . .
C22 C 0.6194(3) 0.53254(15) 0.87080(5) 0.0258(4) Uani 1 1 d . . .
H22A H 0.6066 0.4837 0.8930 0.039 Uiso 1 1 calc R . .
H22B H 0.5224 0.5781 0.8692 0.039 Uiso 1 1 calc R . .
H22C H 0.7183 0.5753 0.8749 0.039 Uiso 1 1 calc R . .
C23 C 0.7228(3) 0.30271(14) 0.73254(5) 0.0227(4) Uani 1 1 d . . .
H23A H 0.7257 0.2282 0.7393 0.034 Uiso 1 1 calc R . .
H23B H 0.8287 0.3233 0.7209 0.034 Uiso 1 1 calc R . .
H23C H 0.6343 0.3155 0.7134 0.034 Uiso 1 1 calc R . .
O5 O 0.20779(17) -0.07791(11) 0.43593(4) 0.0298(3) Uani 1 1 d . . .
O6 O 0.48587(19) -0.04559(16) 0.43689(5) 0.0306(6) Uani 0.941(5) 1 d PU . .
O61 O 0.471(3) -0.096(2) 0.4534(8) 0.020(5) Uiso 0.059(5) 1 d PU . .
O7 O 0.3723(3) -0.15510(13) 0.52720(7) 0.0342(8) Uani 0.906(7) 1 d P A 1
H7A H 0.3326 -0.2108 0.5183 0.051 Uiso 0.906(7) 1 calc PR A 1
O71 O 0.291(3) -0.1414(16) 0.5480(8) 0.052(7) Uani 0.094(7) 1 d PU A 2
H71A H 0.2745 -0.1944 0.5341 0.078 Uiso 0.094(7) 1 calc PR A 2
O8 O 0.33835(17) 0.16976(11) 0.55048(4) 0.0276(3) Uani 1 1 d . A .
O9 O 0.6346(2) 0.41563(12) 0.63517(4) 0.0368(4) Uani 1 1 d . . .
O10 O 0.90478(19) 0.40452(12) 0.64216(4) 0.0375(4) Uani 1 1 d . . .
N3 N 0.4707(2) 0.06121(12) 0.50665(4) 0.0233(4) Uani 1 1 d . A .
H3A H 0.5651 0.0400 0.4968 0.028 Uiso 1 1 calc R . .
N4 N 0.7725(2) 0.38086(13) 0.62503(4) 0.0267(4) Uani 1 1 d . . .
C24 C 0.3427(3) -0.04185(15) 0.45192(6) 0.0250(4) Uani 1 1 d . A .
C25 C 0.3140(2) 0.01190(15) 0.49306(5) 0.0210(4) Uani 1 1 d . . .
H25A H 0.2278 0.0673 0.4901 0.025 Uiso 1 1 calc R A 1
C26 C 0.2529(4) -0.0712(2) 0.52270(8) 0.0257(7) Uani 0.906(7) 1 d PU A 1
H26A H 0.2333 -0.0378 0.5487 0.031 Uiso 0.906(7) 1 calc PR A 1
H26B H 0.1469 -0.1005 0.5133 0.031 Uiso 0.906(7) 1 calc PR A 1
C261 C 0.195(4) -0.053(3) 0.5324(10) 0.034(5) Uani 0.094(7) 1 d PU A 2
H26C H 0.1707 -0.0021 0.5539 0.041 Uiso 0.094(7) 1 calc PR A 2
H26D H 0.0883 -0.0781 0.5216 0.041 Uiso 0.094(7) 1 calc PR A 2
C27 C 0.4689(3) 0.13938(14) 0.53441(5) 0.0203(4) Uani 1 1 d . . .
C28 C 0.6354(2) 0.18637(14) 0.54640(5) 0.0186(4) Uani 1 1 d . A .
C29 C 0.6307(3) 0.26284(14) 0.57725(5) 0.0202(4) Uani 1 1 d . . .
H29A H 0.5285 0.2855 0.5880 0.024 Uiso 1 1 calc R A .
C30 C 0.7800(3) 0.30379(14) 0.59140(5) 0.0210(4) Uani 1 1 d . A .
C31 C 0.9358(3) 0.27364(15) 0.57646(6) 0.0242(5) Uani 1 1 d . . .
H31A H 1.0348 0.3017 0.5870 0.029 Uiso 1 1 calc R A .
C32 C 0.9388(3) 0.19989(15) 0.54509(5) 0.0243(4) Uani 1 1 d . A .
H32A H 1.0413 0.1791 0.5340 0.029 Uiso 1 1 calc R . .
C33 C 0.7907(2) 0.15703(14) 0.53010(5) 0.0212(4) Uani 1 1 d . . .
H33A H 0.7948 0.1082 0.5089 0.025 Uiso 1 1 calc R A .
O1W O 0.76377(17) 0.02510(10) 0.87765(4) 0.0302(3) Uani 1 1 d . . .
H11W H 0.8689 0.0225 0.8900 0.045 Uiso 1 1 d R . .
H12W H 0.7610 -0.0338 0.8593 0.045 Uiso 1 1 d R . .
O2W O 0.76865(19) 0.16498(11) 1.00276(4) 0.0383(4) Uani 1 1 d . . .
H21W H 0.7364 0.1150 0.9845 0.057 Uiso 1 1 d R . .
H22W H 0.8823 0.1636 1.0060 0.057 Uiso 1 1 d R . .
O3W O 0.61773(18) 0.01387(11) 0.95424(4) 0.0338(3) Uani 1 1 d . . .
H31W H 0.6586 0.0011 0.9252 0.051 Uiso 1 1 d R . .
H32W H 0.5035 0.0338 0.9489 0.051 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0294(8) 0.0174(6) 0.0263(7) 0.0020(5) -0.0001(6) 0.0042(6)
O2 0.0263(7) 0.0206(6) 0.0149(6) 0.0003(5) 0.0003(5) 0.0003(6)
O3 0.0258(8) 0.0156(6) 0.0184(6) -0.0022(5) 0.0004(5) 0.0008(6)
O4 0.0393(9) 0.0242(7) 0.0182(7) -0.0043(5) 0.0004(6) -0.0030(7)
N1 0.0213(9) 0.0153(7) 0.0146(7) -0.0032(6) 0.0009(6) -0.0006(7)
N2 0.0288(10) 0.0221(8) 0.0171(7) -0.0033(6) 0.0012(7) 0.0003(7)
C1 0.0178(10) 0.0189(9) 0.0168(8) -0.0054(7) 0.0018(7) 0.0006(8)
C2 0.0129(10) 0.0222(9) 0.0164(9) 0.0007(7) 0.0002(7) -0.0007(8)
C3 0.0143(10) 0.0149(9) 0.0226(9) -0.0013(7) -0.0024(7) -0.0022(8)
C4 0.0185(10) 0.0162(9) 0.0168(9) -0.0046(7) -0.0006(7) 0.0005(8)
C5 0.0144(10) 0.0184(9) 0.0185(9) -0.0007(7) -0.0005(7) -0.0016(8)
C6 0.0146(10) 0.0140(8) 0.0210(9) -0.0039(7) -0.0001(7) -0.0012(7)
C7 0.0199(10) 0.0154(9) 0.0171(9) -0.0023(7) 0.0009(7) 0.0003(8)
C8 0.0190(10) 0.0161(9) 0.0161(8) -0.0014(7) 0.0003(7) -0.0006(8)
C9 0.0166(10) 0.0190(9) 0.0240(10) -0.0061(7) 0.0006(8) -0.0001(8)
C10 0.0275(11) 0.0156(9) 0.0253(9) -0.0083(8) 0.0008(8) -0.0007(9)
C11 0.0166(10) 0.0170(9) 0.0253(9) -0.0019(8) -0.0026(8) -0.0021(8)
C12 0.0404(13) 0.0201(10) 0.0303(11) 0.0060(9) 0.0042(9) -0.0012(10)
C13 0.0330(12) 0.0270(10) 0.0228(10) 0.0061(8) 0.0028(9) -0.0010(10)
C14 0.0262(11) 0.0242(11) 0.0198(9) 0.0006(8) 0.0037(8) -0.0040(9)
C15 0.0336(12) 0.0265(10) 0.0210(9) 0.0030(8) 0.0032(8) -0.0018(10)
C16 0.0263(11) 0.0256(10) 0.0191(9) -0.0032(8) -0.0035(8) 0.0051(9)
C17 0.0214(11) 0.0188(9) 0.0190(9) -0.0047(8) -0.0009(8) -0.0010(8)
C18 0.0169(10) 0.0169(9) 0.0206(9) -0.0001(7) -0.0014(7) 0.0004(8)
C19 0.0177(10) 0.0198(9) 0.0220(9) 0.0011(8) 0.0032(8) -0.0020(8)
C20 0.0232(11) 0.0214(9) 0.0213(9) -0.0001(8) 0.0032(8) 0.0035(9)
C21 0.0236(11) 0.0160(9) 0.0174(9) 0.0014(7) 0.0016(7) 0.0032(8)
C22 0.0323(12) 0.0280(10) 0.0171(9) -0.0031(8) 0.0004(8) -0.0026(10)
C23 0.0277(11) 0.0182(9) 0.0222(9) -0.0038(8) 0.0022(8) -0.0004(9)
O5 0.0244(8) 0.0383(8) 0.0267(7) -0.0120(6) -0.0079(6) 0.0041(7)
O6 0.0262(9) 0.0387(12) 0.0269(9) -0.0074(9) 0.0087(7) -0.0056(7)
O7 0.0370(13) 0.0272(10) 0.0385(13) 0.0094(8) -0.0107(10) -0.0071(9)
O71 0.048(10) 0.056(9) 0.053(10) 0.005(7) -0.003(8) 0.002(8)
O8 0.0233(8) 0.0341(8) 0.0252(7) -0.0077(6) 0.0017(6) -0.0025(6)
O9 0.0367(10) 0.0419(9) 0.0318(8) -0.0161(7) 0.0021(7) 0.0015(8)
O10 0.0331(9) 0.0466(10) 0.0328(8) -0.0123(7) -0.0007(7) -0.0152(8)
N3 0.0201(9) 0.0235(9) 0.0263(8) -0.0053(7) -0.0027(7) -0.0007(7)
N4 0.0321(11) 0.0278(9) 0.0202(8) -0.0039(7) 0.0011(7) -0.0088(8)
C24 0.0284(12) 0.0234(10) 0.0232(10) -0.0018(8) -0.0051(8) 0.0031(9)
C25 0.0228(11) 0.0214(9) 0.0189(9) -0.0037(8) -0.0042(7) -0.0015(9)
C26 0.0282(18) 0.0309(15) 0.0181(14) -0.0018(10) -0.0018(10) -0.0058(13)
C261 0.032(10) 0.035(9) 0.035(9) 0.008(8) 0.006(8) -0.002(9)
C27 0.0247(11) 0.0199(9) 0.0163(9) 0.0050(8) -0.0023(8) -0.0018(9)
C28 0.0239(11) 0.0161(9) 0.0157(9) 0.0030(7) 0.0002(8) 0.0000(8)
C29 0.0245(11) 0.0199(9) 0.0162(9) 0.0006(8) 0.0022(8) 0.0005(8)
C30 0.0278(11) 0.0183(9) 0.0170(9) 0.0002(7) 0.0023(8) -0.0039(9)
C31 0.0226(11) 0.0271(11) 0.0228(10) 0.0045(8) 0.0002(8) -0.0073(9)
C32 0.0233(11) 0.0262(10) 0.0233(10) 0.0003(9) 0.0045(8) 0.0017(9)
C33 0.0258(11) 0.0192(9) 0.0187(9) -0.0024(7) 0.0014(8) -0.0021(9)
O1W 0.0282(8) 0.0330(7) 0.0295(7) -0.0081(6) -0.0044(6) 0.0033(7)
O2W 0.0374(9) 0.0375(8) 0.0399(8) -0.0049(7) 0.0049(7) 0.0077(7)
O3W 0.0341(9) 0.0411(8) 0.0263(7) 0.0032(7) 0.0021(6) 0.0069(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.430(2) . ?
O1 C12 1.442(2) . ?
O2 C2 1.378(2) . ?
O2 C22 1.435(2) . ?
O3 C3 1.376(2) . ?
O3 C23 1.435(2) . ?
O4 C9 1.228(2) . ?
N1 C9 1.365(2) . ?
N1 C6 1.417(2) . ?
N1 C8 1.487(2) . ?
N2 C16 1.501(3) . ?
N2 C15 1.509(2) . ?
N2 C21 1.532(2) . ?
N2 H2A 0.9100 . ?
C1 C2 1.384(2) . ?
C1 C6 1.393(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.408(2) . ?
C3 C4 1.382(2) . ?
C4 C5 1.391(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(2) . ?
C5 C7 1.505(2) . ?
C7 C17 1.543(3) . ?
C7 C21 1.545(2) . ?
C7 C8 1.566(2) . ?
C8 C18 1.525(3) . ?
C8 H8A 0.9800 . ?
C9 C10 1.508(3) . ?
C10 C11 1.543(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.534(2) . ?
C11 H11A 0.9800 . ?
C12 C13 1.504(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.325(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.506(3) . ?
C14 C19 1.525(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.513(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.541(2) . ?
C18 H18A 0.9800 . ?
C19 C20 1.535(2) . ?
C19 H19A 0.9800 . ?
C20 C21 1.513(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O5 C24 1.278(2) . ?
O6 O61 0.84(3) . ?
O6 C24 1.242(2) . ?
O61 C24 1.23(2) . ?
O7 C26 1.424(3) . ?
O7 H7A 0.8200 . ?
O71 C261 1.45(4) . ?
O71 H71A 0.8200 . ?
O8 C27 1.226(2) . ?
O9 N4 1.226(2) . ?
O10 N4 1.230(2) . ?
N3 C27 1.342(2) . ?
N3 C25 1.460(2) . ?
N3 H3A 0.8600 . ?
N4 C30 1.474(2) . ?
C24 C25 1.535(2) . ?
C25 C26 1.509(3) . ?
C25 C261 1.80(3) . ?
C25 H25A 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C261 H26C 0.9700 . ?
C261 H26D 0.9700 . ?
C27 C28 1.501(3) . ?
C28 C33 1.395(3) . ?
C28 C29 1.400(2) . ?
C29 C30 1.375(3) . ?
C29 H29A 0.9300 . ?
C30 C31 1.385(3) . ?
C31 C32 1.389(3) . ?
C31 H31A 0.9300 . ?
C32 C33 1.385(3) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
O1W H11W 0.9308 . ?
O1W H12W 0.9556 . ?
O2W H21W 0.9068 . ?
O2W H22W 0.9093 . ?
O3W H31W 1.0267 . ?
O3W H32W 0.9578 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.01(15) . . ?
C2 O2 C22 116.33(13) . . ?
C3 O3 C23 116.43(13) . . ?
C9 N1 C6 125.46(14) . . ?
C9 N1 C8 119.54(14) . . ?
C6 N1 C8 109.52(13) . . ?
C16 N2 C15 112.96(15) . . ?
C16 N2 C21 107.96(13) . . ?
C15 N2 C21 113.11(15) . . ?
C16 N2 H2A 107.5 . . ?
C15 N2 H2A 107.5 . . ?
C21 N2 H2A 107.5 . . ?
C2 C1 C6 117.73(16) . . ?
C2 C1 H1A 121.1 . . ?
C6 C1 H1A 121.1 . . ?
O2 C2 C1 123.56(16) . . ?
O2 C2 C3 115.21(14) . . ?
C1 C2 C3 121.22(16) . . ?
O3 C3 C4 124.29(16) . . ?
O3 C3 C2 115.98(15) . . ?
C4 C3 C2 119.74(15) . . ?
C3 C4 C5 119.42(16) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C6 C5 C4 120.08(16) . . ?
C6 C5 C7 110.93(14) . . ?
C4 C5 C7 128.78(15) . . ?
C5 C6 C1 121.72(15) . . ?
C5 C6 N1 110.21(15) . . ?
C1 C6 N1 128.05(15) . . ?
C5 C7 C17 111.97(15) . . ?
C5 C7 C21 115.97(14) . . ?
C17 C7 C21 101.65(13) . . ?
C5 C7 C8 102.49(13) . . ?
C17 C7 C8 111.28(15) . . ?
C21 C7 C8 113.82(14) . . ?
N1 C8 C18 105.70(14) . . ?
N1 C8 C7 104.49(13) . . ?
C18 C8 C7 117.37(15) . . ?
N1 C8 H8A 109.6 . . ?
C18 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
O4 C9 N1 122.02(16) . . ?
O4 C9 C10 122.28(16) . . ?
N1 C9 C10 115.68(14) . . ?
C9 C10 C11 117.12(14) . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10B 108.0 . . ?
C11 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
O1 C11 C18 113.74(14) . . ?
O1 C11 C10 105.28(14) . . ?
C18 C11 C10 110.14(15) . . ?
O1 C11 H11A 109.2 . . ?
C18 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
O1 C12 C13 111.87(16) . . ?
O1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 122.92(17) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C13 C14 C15 122.37(18) . . ?
C13 C14 C19 123.08(17) . . ?
C15 C14 C19 114.55(15) . . ?
C14 C15 N2 109.17(14) . . ?
C14 C15 H15A 109.8 . . ?
N2 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
N2 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C17 104.41(15) . . ?
N2 C16 H16A 110.9 . . ?
C17 C16 H16A 110.9 . . ?
N2 C16 H16B 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.17(15) . . ?
C16 C17 H17A 111.1 . . ?
C7 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
C7 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C8 C18 C11 106.93(15) . . ?
C8 C18 C19 113.08(15) . . ?
C11 C18 C19 118.71(14) . . ?
C8 C18 H18A 105.7 . . ?
C11 C18 H18A 105.7 . . ?
C19 C18 H18A 105.7 . . ?
C14 C19 C20 109.55(15) . . ?
C14 C19 C18 114.37(15) . . ?
C20 C19 C18 105.80(14) . . ?
C14 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C21 C20 C19 108.86(16) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 N2 110.75(14) . . ?
C20 C21 C7 115.48(14) . . ?
N2 C21 C7 104.57(14) . . ?
C20 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O61 O6 C24 69.1(16) . . ?
O6 O61 C24 70.9(18) . . ?
C26 O7 H7A 109.5 . . ?
C261 O71 H71A 109.5 . . ?
C27 N3 C25 120.65(16) . . ?
C27 N3 H3A 119.7 . . ?
C25 N3 H3A 119.7 . . ?
O9 N4 O10 123.52(15) . . ?
O9 N4 C30 118.39(16) . . ?
O10 N4 C30 118.07(17) . . ?
O61 C24 O6 40.0(15) . . ?
O61 C24 O5 121.3(11) . . ?
O6 C24 O5 126.10(17) . . ?
O61 C24 C25 109.3(11) . . ?
O6 C24 C25 120.49(18) . . ?
O5 C24 C25 113.40(17) . . ?
N3 C25 C26 111.44(16) . . ?
N3 C25 C24 109.37(16) . . ?
C26 C25 C24 108.75(17) . . ?
N3 C25 C261 114.6(11) . . ?
C26 C25 C261 18.7(11) . . ?
C24 C25 C261 121.4(12) . . ?
N3 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
C261 C25 H25A 91.1 . . ?
O7 C26 C25 111.2(2) . . ?
O7 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
O7 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
O71 C261 C25 108.8(19) . . ?
O71 C261 H26C 109.9 . . ?
C25 C261 H26C 109.9 . . ?
O71 C261 H26D 109.9 . . ?
C25 C261 H26D 109.9 . . ?
H26C C261 H26D 108.3 . . ?
O8 C27 N3 122.15(18) . . ?
O8 C27 C28 120.62(16) . . ?
N3 C27 C28 117.19(17) . . ?
C33 C28 C29 119.04(17) . . ?
C33 C28 C27 125.02(16) . . ?
C29 C28 C27 115.90(16) . . ?
C30 C29 C28 118.68(18) . . ?
C30 C29 H29A 120.7 . . ?
C28 C29 H29A 120.7 . . ?
C29 C30 C31 123.24(16) . . ?
C29 C30 N4 117.78(17) . . ?
C31 C30 N4 118.95(17) . . ?
C30 C31 C32 117.57(18) . . ?
C30 C31 H31A 121.2 . . ?
C32 C31 H31A 121.2 . . ?
C33 C32 C31 120.69(18) . . ?
C33 C32 H32A 119.7 . . ?
C31 C32 H32A 119.7 . . ?
C32 C33 C28 120.72(16) . . ?
C32 C33 H33A 119.6 . . ?
C28 C33 H33A 119.6 . . ?
H11W O1W H12W 105.8 . . ?
H21W O2W H22W 110.2 . . ?
H31W O3W H32W 99.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 -3.1(3) . . . . ?
C22 O2 C2 C3 175.89(16) . . . . ?
C6 C1 C2 O2 -179.83(16) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C23 O3 C3 C4 0.8(3) . . . . ?
C23 O3 C3 C2 -179.07(15) . . . . ?
O2 C2 C3 O3 -2.3(2) . . . . ?
C1 C2 C3 O3 176.80(16) . . . . ?
O2 C2 C3 C4 177.90(16) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
O3 C3 C4 C5 -177.73(16) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C7 -173.65(17) . . . . ?
C4 C5 C6 C1 -2.5(3) . . . . ?
C7 C5 C6 C1 172.70(17) . . . . ?
C4 C5 C6 N1 178.66(17) . . . . ?
C7 C5 C6 N1 -6.1(2) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 N1 -179.82(17) . . . . ?
C9 N1 C6 C5 -157.86(17) . . . . ?
C8 N1 C6 C5 -4.4(2) . . . . ?
C9 N1 C6 C1 23.4(3) . . . . ?
C8 N1 C6 C1 176.87(18) . . . . ?
C6 C5 C7 C17 -106.13(17) . . . . ?
C4 C5 C7 C17 68.6(2) . . . . ?
C6 C5 C7 C21 137.85(16) . . . . ?
C4 C5 C7 C21 -47.5(3) . . . . ?
C6 C5 C7 C8 13.2(2) . . . . ?
C4 C5 C7 C8 -172.08(19) . . . . ?
C9 N1 C8 C18 43.2(2) . . . . ?
C6 N1 C8 C18 -112.10(15) . . . . ?
C9 N1 C8 C7 167.64(16) . . . . ?
C6 N1 C8 C7 12.37(19) . . . . ?
C5 C7 C8 N1 -14.89(18) . . . . ?
C17 C7 C8 N1 104.95(15) . . . . ?
C21 C7 C8 N1 -140.92(15) . . . . ?
C5 C7 C8 C18 101.76(17) . . . . ?
C17 C7 C8 C18 -138.40(16) . . . . ?
C21 C7 C8 C18 -24.3(2) . . . . ?
C6 N1 C9 O4 -20.3(3) . . . . ?
C8 N1 C9 O4 -171.36(17) . . . . ?
C6 N1 C9 C10 161.41(17) . . . . ?
C8 N1 C9 C10 10.4(2) . . . . ?
O4 C9 C10 C11 145.02(18) . . . . ?
N1 C9 C10 C11 -36.7(2) . . . . ?
C12 O1 C11 C18 -69.5(2) . . . . ?
C12 O1 C11 C10 169.83(14) . . . . ?
C9 C10 C11 O1 128.60(17) . . . . ?
C9 C10 C11 C18 5.6(2) . . . . ?
C11 O1 C12 C13 88.25(19) . . . . ?
O1 C12 C13 C14 -63.5(3) . . . . ?
C12 C13 C14 C15 176.16(18) . . . . ?
C12 C13 C14 C19 -2.7(3) . . . . ?
C13 C14 C15 N2 -123.1(2) . . . . ?
C19 C14 C15 N2 55.8(2) . . . . ?
C16 N2 C15 C14 74.0(2) . . . . ?
C21 N2 C15 C14 -49.0(2) . . . . ?
C15 N2 C16 C17 -143.76(15) . . . . ?
C21 N2 C16 C17 -17.94(18) . . . . ?
N2 C16 C17 C7 37.69(17) . . . . ?
C5 C7 C17 C16 -167.06(14) . . . . ?
C21 C7 C17 C16 -42.63(17) . . . . ?
C8 C7 C17 C16 78.89(16) . . . . ?
N1 C8 C18 C11 -72.12(17) . . . . ?
C7 C8 C18 C11 171.88(14) . . . . ?
N1 C8 C18 C19 155.38(14) . . . . ?
C7 C8 C18 C19 39.4(2) . . . . ?
O1 C11 C18 C8 -71.07(18) . . . . ?
C10 C11 C18 C8 46.83(19) . . . . ?
O1 C11 C18 C19 58.3(2) . . . . ?
C10 C11 C18 C19 176.18(16) . . . . ?
C13 C14 C19 C20 175.36(19) . . . . ?
C15 C14 C19 C20 -3.6(2) . . . . ?
C13 C14 C19 C18 56.8(3) . . . . ?
C15 C14 C19 C18 -122.11(17) . . . . ?
C8 C18 C19 C14 60.09(19) . . . . ?
C11 C18 C19 C14 -66.4(2) . . . . ?
C8 C18 C19 C20 -60.57(19) . . . . ?
C11 C18 C19 C20 172.97(16) . . . . ?
C14 C19 C20 C21 -54.71(19) . . . . ?
C18 C19 C20 C21 69.03(18) . . . . ?
C19 C20 C21 N2 61.34(18) . . . . ?
C19 C20 C21 C7 -57.3(2) . . . . ?
C16 N2 C21 C20 -133.75(15) . . . . ?
C15 N2 C21 C20 -8.0(2) . . . . ?
C16 N2 C21 C7 -8.73(17) . . . . ?
C15 N2 C21 C7 117.01(16) . . . . ?
C5 C7 C21 C20 -85.17(19) . . . . ?
C17 C7 C21 C20 153.14(15) . . . . ?
C8 C7 C21 C20 33.4(2) . . . . ?
C5 C7 C21 N2 152.87(14) . . . . ?
C17 C7 C21 N2 31.17(16) . . . . ?
C8 C7 C21 N2 -88.57(16) . . . . ?
O6 O61 C24 O5 110.4(14) . . . . ?
O6 O61 C24 C25 -114.8(12) . . . . ?
O61 O6 C24 O5 -97.5(16) . . . . ?
O61 O6 C24 C25 83.9(16) . . . . ?
C27 N3 C25 C26 -80.5(2) . . . . ?
C27 N3 C25 C24 159.20(15) . . . . ?
C27 N3 C25 C261 -60.5(13) . . . . ?
O61 C24 C25 N3 47.9(15) . . . . ?
O6 C24 C25 N3 5.3(3) . . . . ?
O5 C24 C25 N3 -173.45(15) . . . . ?
O61 C24 C25 C26 -74.0(16) . . . . ?
O6 C24 C25 C26 -116.6(2) . . . . ?
O5 C24 C25 C26 64.6(2) . . . . ?
O61 C24 C25 C261 -89(2) . . . . ?
O6 C24 C25 C261 -131.8(14) . . . . ?
O5 C24 C25 C261 49.4(14) . . . . ?
N3 C25 C26 O7 -61.0(2) . . . . ?
C24 C25 C26 O7 59.6(2) . . . . ?
C261 C25 C26 O7 -165(4) . . . . ?
N3 C25 C261 O71 -64(2) . . . . ?
C26 C25 C261 O71 20(2) . . . . ?
C24 C25 C261 O71 71(2) . . . . ?
C25 N3 C27 O8 2.7(3) . . . . ?
C25 N3 C27 C28 -179.45(15) . . . . ?
O8 C27 C28 C33 179.71(18) . . . . ?
N3 C27 C28 C33 1.9(2) . . . . ?
O8 C27 C28 C29 1.8(2) . . . . ?
N3 C27 C28 C29 -176.04(15) . . . . ?
C33 C28 C29 C30 -2.2(2) . . . . ?
C27 C28 C29 C30 175.84(16) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C28 C29 C30 N4 -177.52(14) . . . . ?
O9 N4 C30 C29 -9.6(2) . . . . ?
O10 N4 C30 C29 168.39(17) . . . . ?
O9 N4 C30 C31 172.37(17) . . . . ?
O10 N4 C30 C31 -9.6(2) . . . . ?
C29 C30 C31 C32 1.3(3) . . . . ?
N4 C30 C31 C32 179.23(15) . . . . ?
C30 C31 C32 C33 -1.3(3) . . . . ?
C31 C32 C33 C28 -0.5(3) . . . . ?
C29 C28 C33 C32 2.3(3) . . . . ?
C27 C28 C33 C32 -175.58(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.91 1.69 2.5877(19) 170.0 4_556
O7 H7A O2W 0.82 1.88 2.704(2) 177.2 3_646
O71 H71A O2W 0.82 2.17 2.99(2) 179.6 3_646
O1W H11W O6 0.93 1.95 2.804(2) 150.9 2_655
O1W H12W O4 0.96 1.91 2.8478(17) 165.1 1_545
O2W H21W O3W 0.91 1.87 2.755(2) 165.2 .
O2W H22W O7 0.91 2.07 2.967(3) 166.8 2_655
O2W H22W O61 0.91 2.25 2.77(3) 115.4 2_655
O3W H31W O1W 1.03 1.81 2.7898(18) 159.3 .
O3W H32W O5 0.96 1.82 2.774(2) 176.0 2

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 930493'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


#====== end



data_b3nbls
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucinium N-(3-nitrobenzoyl)-L-serinate methanol solvate hydrate
;
_chemical_name_common            ?
_chemical_melting_point          430
_chemical_formula_moiety         'C23 H27 N2 O4, C10 H9 N2 O6, C H3 O, H2 O'
_chemical_formula_sum            'C34 H42 N4 O12'
_chemical_formula_weight         698.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.835(2)
_cell_length_b                   12.067(3)
_cell_length_c                   34.634(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3274.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3729
_cell_measurement_theta_min      2.8498
_cell_measurement_theta_max      28.7307

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17483
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_sigmaI/netI    0.1055
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3325
_reflns_number_gt                1858
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3325
_refine_ls_number_parameters     496
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.890
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6859(4) 1.3083(3) 0.17563(9) 0.0328(9) Uani 1 1 d . . .
O2 O 0.7640(4) 0.7308(3) 0.32292(9) 0.0344(9) Uani 1 1 d . . .
O3 O 0.7903(4) 0.6097(3) 0.26122(9) 0.0390(9) Uani 1 1 d . . .
O4 O 0.7252(4) 1.1350(3) 0.29614(10) 0.0407(10) Uani 1 1 d . . .
N1 N 0.6436(5) 1.0543(3) 0.23980(11) 0.0280(10) Uani 1 1 d . . .
N2 N 0.5644(5) 0.9519(3) 0.11378(11) 0.0327(11) Uani 1 1 d . . .
H2A H 0.5456 0.8915 0.0977 0.039 Uiso 1 1 calc R . .
C1 C 0.7002(6) 0.8978(4) 0.28624(14) 0.0272(12) Uani 1 1 d . . .
H1A H 0.6973 0.9433 0.3086 0.033 Uiso 1 1 calc R . .
C2 C 0.7349(6) 0.7850(4) 0.28868(14) 0.0306(13) Uani 1 1 d . . .
C3 C 0.7413(6) 0.7185(4) 0.25559(16) 0.0316(13) Uani 1 1 d . . .
C4 C 0.7018(6) 0.7636(4) 0.22000(14) 0.0305(13) Uani 1 1 d . . .
H4A H 0.7000 0.7180 0.1977 0.037 Uiso 1 1 calc R . .
C5 C 0.6650(6) 0.8759(4) 0.21702(14) 0.0280(13) Uani 1 1 d . . .
C6 C 0.6701(6) 0.9409(4) 0.24977(14) 0.0269(12) Uani 1 1 d . . .
C7 C 0.6077(6) 0.9420(4) 0.18306(14) 0.0278(12) Uani 1 1 d . . .
C8 C 0.6365(6) 1.0624(4) 0.19678(13) 0.0271(12) Uani 1 1 d . . .
H8A H 0.5377 1.1097 0.1889 0.033 Uiso 1 1 calc R . .
C9 C 0.7012(6) 1.1415(4) 0.26117(17) 0.0363(14) Uani 1 1 d . . .
C10 C 0.7348(6) 1.2479(4) 0.23948(14) 0.0337(13) Uani 1 1 d . . .
H10A H 0.8200 1.2910 0.2543 0.040 Uiso 1 1 calc R . .
H10B H 0.6277 1.2915 0.2394 0.040 Uiso 1 1 calc R . .
C11 C 0.7988(6) 1.2393(4) 0.19730(13) 0.0291(12) Uani 1 1 d . . .
H11A H 0.9167 1.2709 0.1958 0.035 Uiso 1 1 calc R . .
C12 C 0.7354(7) 1.3266(4) 0.13612(13) 0.0336(13) Uani 1 1 d . . .
H12A H 0.8614 1.3281 0.1343 0.040 Uiso 1 1 calc R . .
H12B H 0.6917 1.3994 0.1274 0.040 Uiso 1 1 calc R . .
C13 C 0.6681(6) 1.2387(4) 0.11057(14) 0.0342(13) Uani 1 1 d . . .
H13A H 0.5897 1.2596 0.0909 0.041 Uiso 1 1 calc R . .
C14 C 0.7101(6) 1.1333(4) 0.11332(14) 0.0295(12) Uani 1 1 d . . .
C15 C 0.6307(6) 1.0444(4) 0.08869(14) 0.0337(13) Uani 1 1 d . . .
H15A H 0.7167 1.0149 0.0704 0.040 Uiso 1 1 calc R . .
H15B H 0.5357 1.0763 0.0735 0.040 Uiso 1 1 calc R . .
C16 C 0.3978(6) 0.9759(4) 0.13371(14) 0.0338(13) Uani 1 1 d . . .
H16A H 0.3013 0.9421 0.1195 0.041 Uiso 1 1 calc R . .
H16B H 0.3784 1.0568 0.1357 0.041 Uiso 1 1 calc R . .
C17 C 0.4162(6) 0.9248(4) 0.17316(13) 0.0302(13) Uani 1 1 d . . .
H17A H 0.3869 0.8450 0.1726 0.036 Uiso 1 1 calc R . .
H17B H 0.3421 0.9626 0.1922 0.036 Uiso 1 1 calc R . .
C18 C 0.8042(6) 1.1176(4) 0.18437(14) 0.0295(12) Uani 1 1 d . . .
H18A H 0.8965 1.0815 0.1999 0.035 Uiso 1 1 calc R . .
C19 C 0.8459(6) 1.0939(4) 0.14186(14) 0.0313(13) Uani 1 1 d . . .
H19A H 0.9572 1.1297 0.1353 0.038 Uiso 1 1 calc R . .
C20 C 0.8648(6) 0.9677(4) 0.13797(14) 0.0308(13) Uani 1 1 d . . .
H20A H 0.9075 0.9489 0.1119 0.037 Uiso 1 1 calc R . .
H20B H 0.9479 0.9399 0.1572 0.037 Uiso 1 1 calc R . .
C21 C 0.6928(6) 0.9142(4) 0.14453(14) 0.0311(13) Uani 1 1 d . . .
H21A H 0.7063 0.8319 0.1427 0.037 Uiso 1 1 calc R . .
C22 C 0.7473(6) 0.7954(4) 0.35747(14) 0.0424(15) Uani 1 1 d . . .
H22A H 0.7706 0.7485 0.3800 0.064 Uiso 1 1 calc R . .
H22B H 0.6310 0.8248 0.3592 0.064 Uiso 1 1 calc R . .
H22C H 0.8289 0.8569 0.3568 0.064 Uiso 1 1 calc R . .
C23 C 0.8150(7) 0.5434(4) 0.22773(15) 0.0464(16) Uani 1 1 d . . .
H23A H 0.8487 0.4684 0.2355 0.070 Uiso 1 1 calc R . .
H23B H 0.9050 0.5760 0.2117 0.070 Uiso 1 1 calc R . .
H23C H 0.7085 0.5400 0.2129 0.070 Uiso 1 1 calc R . .
O5 O 0.5023(5) 0.7812(3) 0.06996(10) 0.0438(10) Uani 1 1 d . . .
O6 O 0.7710(4) 0.8090(3) 0.05159(10) 0.0448(10) Uani 1 1 d . . .
O7 O 0.5958(4) 0.7425(3) -0.03009(10) 0.0442(10) Uani 1 1 d . . .
H7A H 0.4974 0.7198 -0.0355 0.066 Uiso 1 1 calc R . .
O8 O 0.5844(5) 0.4169(3) 0.03281(11) 0.0456(10) Uani 1 1 d . . .
O9 O 0.2272(5) 0.1024(3) 0.06158(11) 0.0517(11) Uani 1 1 d . . .
O10 O -0.0404(5) 0.1021(3) 0.04861(10) 0.0467(11) Uani 1 1 d . . .
N3 N 0.4685(5) 0.5886(3) 0.03346(12) 0.0386(11) Uani 1 1 d . . .
H3A H 0.3753 0.6292 0.0348 0.046 Uiso 1 1 calc R . .
N4 N 0.0967(6) 0.1489(4) 0.05072(12) 0.0361(11) Uani 1 1 d . . .
C24 C 0.6348(7) 0.7530(4) 0.05253(15) 0.0345(14) Uani 1 1 d . . .
C25 C 0.6347(6) 0.6431(4) 0.03131(15) 0.0367(14) Uani 1 1 d . . .
H25A H 0.7206 0.5937 0.0440 0.044 Uiso 1 1 calc R . .
C26 C 0.6868(7) 0.6579(4) -0.01067(15) 0.0381(14) Uani 1 1 d . . .
H26A H 0.8102 0.6752 -0.0117 0.046 Uiso 1 1 calc R . .
H26B H 0.6688 0.5870 -0.0245 0.046 Uiso 1 1 calc R . .
C27 C 0.4558(7) 0.4776(4) 0.03346(16) 0.0367(14) Uani 1 1 d . . .
C28 C 0.2804(6) 0.4286(4) 0.03269(14) 0.0288(12) Uani 1 1 d . . .
C29 C 0.2679(6) 0.3170(4) 0.04141(12) 0.0333(13) Uani 1 1 d . . .
H29A H 0.3670 0.2754 0.0476 0.040 Uiso 1 1 calc R . .
C30 C 0.1099(7) 0.2669(4) 0.04097(13) 0.0290(13) Uani 1 1 d . . .
C31 C -0.0374(6) 0.3229(4) 0.03103(15) 0.0385(14) Uani 1 1 d . . .
H31A H -0.1456 0.2873 0.0314 0.046 Uiso 1 1 calc R . .
C32 C -0.0212(7) 0.4316(5) 0.02070(17) 0.0495(17) Uani 1 1 d . . .
H32A H -0.1195 0.4716 0.0128 0.059 Uiso 1 1 calc R . .
C33 C 0.1358(7) 0.4850(4) 0.02149(15) 0.0400(15) Uani 1 1 d . . .
H33A H 0.1435 0.5608 0.0143 0.048 Uiso 1 1 calc R . .
O100 O 1.1794(8) 0.7182(6) 0.10745(18) 0.091(3) Uani 0.689(8) 1 d PDU A 1
H100 H 1.1469 0.7648 0.0910 0.137 Uiso 0.689(8) 1 calc PR A 1
C100 C 1.0368(12) 0.6563(9) 0.1208(3) 0.105(3) Uani 0.841(12) 1 d PDU A 1
H101 H 1.0204 0.6699 0.1484 0.157 Uiso 0.841(12) 1 calc PR A 1
H102 H 1.0574 0.5772 0.1164 0.157 Uiso 0.841(12) 1 calc PR A 1
H103 H 0.9344 0.6793 0.1066 0.157 Uiso 0.841(12) 1 calc PR A 1
O110 O 0.786(3) 0.635(2) 0.1324(7) 0.109(7) Uani 0.215(8) 1 d PDU A 2
H110 H 0.6985 0.6048 0.1231 0.164 Uiso 0.215(8) 1 calc PR A 2
C110 C 0.933(5) 0.575(5) 0.1205(14) 0.108(5) Uani 0.159(12) 1 d PDU A 2
H111 H 1.0351 0.6207 0.1243 0.162 Uiso 0.159(12) 1 calc PR A 2
H112 H 0.9228 0.5558 0.0931 0.162 Uiso 0.159(12) 1 calc PR A 2
H113 H 0.9433 0.5069 0.1358 0.162 Uiso 0.159(12) 1 calc PR A 2
O120 O 1.082(6) 0.542(5) 0.1412(14) 0.104(6) Uani 0.096(7) 1 d PDU B 3
H120 H 1.0919 0.5983 0.1554 0.156 Uiso 0.096(7) 1 d PR B 3
O1W O 0.5134(10) 0.6209(7) 0.14005(18) 0.068(3) Uani 0.815(17) 1 d PU C 1
H11W H 0.5102 0.6659 0.1200 0.101 Uiso 0.815(17) 1 d PR C 1
H12W H 0.4409 0.6244 0.1594 0.101 Uiso 0.815(17) 1 d PR C 1
O11W O 0.435(5) 0.570(3) 0.1302(9) 0.076(5) Uani 0.185(17) 1 d PU C 2
H13W H 0.4076 0.6351 0.1156 0.114 Uiso 0.185(17) 1 d PR C 2
H14W H 0.3834 0.6091 0.1493 0.114 Uiso 0.185(17) 1 d PR C 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.035(2) 0.032(2) 0.031(2) -0.0004(18) -0.0035(17) 0.0004(16)
O2 0.036(2) 0.043(2) 0.023(2) 0.0063(19) -0.0022(17) 0.0009(17)
O3 0.043(2) 0.036(2) 0.038(2) 0.0015(19) 0.0029(18) 0.0004(18)
O4 0.056(3) 0.042(2) 0.024(2) -0.0006(18) -0.0092(19) 0.0010(19)
N1 0.033(2) 0.026(3) 0.025(3) 0.001(2) -0.003(2) 0.002(2)
N2 0.039(3) 0.031(3) 0.028(3) -0.001(2) 0.000(2) -0.005(2)
C1 0.022(3) 0.030(3) 0.030(3) -0.010(3) 0.004(2) -0.003(2)
C2 0.020(3) 0.049(4) 0.022(3) 0.006(3) 0.002(2) -0.004(3)
C3 0.035(3) 0.022(3) 0.038(4) 0.006(3) 0.004(3) 0.003(2)
C4 0.029(3) 0.029(3) 0.034(3) -0.001(3) 0.002(2) -0.002(3)
C5 0.023(3) 0.032(3) 0.029(3) -0.001(3) -0.002(2) -0.006(2)
C6 0.021(3) 0.035(3) 0.024(3) 0.001(3) -0.001(2) -0.002(2)
C7 0.028(3) 0.024(3) 0.031(3) 0.001(3) 0.000(2) -0.006(2)
C8 0.027(3) 0.029(3) 0.025(3) 0.000(2) 0.000(2) 0.004(2)
C9 0.031(3) 0.040(4) 0.038(4) 0.001(3) 0.005(3) 0.009(3)
C10 0.034(3) 0.029(3) 0.039(3) -0.005(3) 0.002(3) -0.001(3)
C11 0.027(3) 0.027(3) 0.033(3) 0.004(3) -0.002(2) -0.003(2)
C12 0.044(3) 0.030(3) 0.027(3) 0.008(3) 0.004(3) 0.000(3)
C13 0.031(3) 0.037(3) 0.034(3) 0.000(3) 0.003(2) -0.006(3)
C14 0.025(3) 0.034(3) 0.029(3) 0.001(3) 0.005(2) -0.005(3)
C15 0.039(3) 0.036(3) 0.026(3) 0.004(3) 0.001(3) -0.004(3)
C16 0.030(3) 0.034(3) 0.037(4) 0.002(3) -0.002(3) -0.001(3)
C17 0.037(3) 0.031(3) 0.023(3) 0.005(3) 0.005(2) -0.009(2)
C18 0.026(3) 0.029(3) 0.034(3) -0.001(3) 0.003(2) 0.001(2)
C19 0.028(3) 0.028(3) 0.037(4) 0.003(3) 0.011(3) -0.002(2)
C20 0.030(3) 0.033(3) 0.029(3) 0.001(3) 0.003(2) -0.004(3)
C21 0.036(3) 0.024(3) 0.033(3) 0.002(3) -0.006(3) 0.000(3)
C22 0.036(3) 0.052(4) 0.039(4) 0.002(3) -0.006(3) 0.001(3)
C23 0.067(4) 0.026(3) 0.046(4) -0.004(3) 0.007(3) 0.007(3)
O5 0.039(2) 0.043(2) 0.050(3) -0.014(2) 0.001(2) -0.0020(19)
O6 0.046(2) 0.034(2) 0.055(2) -0.0040(19) 0.000(2) -0.012(2)
O7 0.046(2) 0.041(2) 0.046(2) 0.006(2) 0.000(2) 0.001(2)
O8 0.039(2) 0.032(2) 0.066(3) 0.008(2) -0.002(2) 0.001(2)
O9 0.057(3) 0.035(2) 0.063(3) 0.004(2) -0.023(2) -0.005(2)
O10 0.044(3) 0.043(3) 0.053(3) -0.007(2) 0.009(2) -0.015(2)
N3 0.035(3) 0.029(3) 0.051(3) 0.003(2) -0.005(2) -0.002(2)
N4 0.036(3) 0.039(3) 0.033(3) 0.003(2) -0.004(2) 0.005(3)
C24 0.041(4) 0.030(3) 0.033(3) -0.001(3) -0.007(3) 0.003(3)
C25 0.037(3) 0.026(3) 0.048(4) 0.006(3) -0.003(3) -0.007(3)
C26 0.040(3) 0.025(3) 0.049(4) -0.006(3) -0.002(3) 0.006(3)
C27 0.050(4) 0.021(3) 0.038(4) 0.006(3) 0.006(3) -0.004(3)
C28 0.027(3) 0.027(3) 0.032(3) 0.000(3) 0.002(3) -0.001(3)
C29 0.041(3) 0.031(3) 0.028(3) 0.002(3) 0.003(3) 0.006(3)
C30 0.037(3) 0.022(3) 0.027(3) -0.005(2) -0.001(2) -0.007(3)
C31 0.027(3) 0.031(3) 0.057(4) 0.002(3) 0.001(3) 0.000(3)
C32 0.032(4) 0.035(4) 0.081(5) -0.002(4) -0.003(3) 0.009(3)
C33 0.043(4) 0.024(3) 0.053(4) -0.007(3) -0.004(3) 0.001(3)
O100 0.061(4) 0.131(5) 0.081(4) 0.061(4) -0.010(3) -0.025(4)
C100 0.087(5) 0.129(6) 0.097(5) 0.037(5) -0.006(4) -0.010(5)
O110 0.110(9) 0.111(9) 0.107(9) 0.006(7) 0.003(7) -0.002(7)
C110 0.103(7) 0.116(7) 0.105(7) 0.015(6) -0.003(6) -0.006(6)
O120 0.096(8) 0.116(8) 0.100(8) 0.019(7) -0.004(7) -0.007(7)
O1W 0.074(5) 0.077(5) 0.052(4) 0.006(4) 0.007(3) -0.005(4)
O11W 0.077(9) 0.081(9) 0.069(8) -0.002(7) 0.006(7) -0.004(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.428(5) . ?
O1 C12 1.439(5) . ?
O2 C2 1.373(5) . ?
O2 C22 1.434(5) . ?
O3 C3 1.381(5) . ?
O3 C23 1.423(5) . ?
O4 C9 1.229(6) . ?
N1 C9 1.363(6) . ?
N1 C6 1.427(6) . ?
N1 C8 1.494(5) . ?
N2 C16 1.505(6) . ?
N2 C15 1.507(5) . ?
N2 C21 1.534(6) . ?
N2 H2A 0.9300 . ?
C1 C6 1.386(6) . ?
C1 C2 1.390(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.400(7) . ?
C3 C4 1.382(6) . ?
C4 C5 1.388(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(6) . ?
C5 C7 1.490(6) . ?
C7 C21 1.529(6) . ?
C7 C8 1.546(6) . ?
C7 C17 1.552(6) . ?
C8 C18 1.534(6) . ?
C8 H8A 1.0000 . ?
C9 C10 1.510(6) . ?
C10 C11 1.548(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.537(6) . ?
C11 H11A 1.0000 . ?
C12 C13 1.478(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.318(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.505(6) . ?
C14 C19 1.528(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.506(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.535(6) . ?
C18 H18A 1.0000 . ?
C19 C20 1.536(6) . ?
C19 H19A 1.0000 . ?
C20 C21 1.512(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.248(6) . ?
O6 C24 1.263(6) . ?
O7 C26 1.416(5) . ?
O7 H7A 0.8400 . ?
O8 C27 1.245(6) . ?
O9 N4 1.226(5) . ?
O10 N4 1.216(5) . ?
N3 C27 1.344(6) . ?
N3 C25 1.460(6) . ?
N3 H3A 0.8800 . ?
N4 C30 1.467(6) . ?
C24 C25 1.517(7) . ?
C25 C26 1.521(7) . ?
C25 H25A 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.496(7) . ?
C28 C33 1.377(7) . ?
C28 C29 1.384(6) . ?
C29 C30 1.377(6) . ?
C29 H29A 0.9500 . ?
C30 C31 1.382(7) . ?
C31 C32 1.366(7) . ?
C31 H31A 0.9500 . ?
C32 C33 1.389(7) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
O100 C100 1.421(11) . ?
O100 H100 0.8400 . ?
C100 H101 0.9800 . ?
C100 H102 0.9800 . ?
C100 H103 0.9800 . ?
O110 C110 1.422(12) . ?
O110 H110 0.8400 . ?
C110 H111 0.9800 . ?
C110 H112 0.9800 . ?
C110 H113 0.9800 . ?
O120 H120 0.8401 . ?
O1W H11W 0.8802 . ?
O1W H12W 0.8798 . ?
O1W H13W 1.1961 . ?
O1W H14W 1.0774 . ?
O11W H11W 1.3479 . ?
O11W H12W 1.2087 . ?
O11W H13W 0.9633 . ?
O11W H14W 0.9118 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 115.0(4) . . ?
C2 O2 C22 116.5(4) . . ?
C3 O3 C23 117.2(4) . . ?
C9 N1 C6 124.1(4) . . ?
C9 N1 C8 120.2(4) . . ?
C6 N1 C8 108.0(4) . . ?
C16 N2 C15 114.9(4) . . ?
C16 N2 C21 107.9(3) . . ?
C15 N2 C21 113.2(4) . . ?
C16 N2 H2A 106.8 . . ?
C15 N2 H2A 106.8 . . ?
C21 N2 H2A 106.8 . . ?
C6 C1 C2 117.1(5) . . ?
C6 C1 H1A 121.4 . . ?
C2 C1 H1A 121.4 . . ?
O2 C2 C1 123.4(5) . . ?
O2 C2 C3 115.3(5) . . ?
C1 C2 C3 121.2(5) . . ?
O3 C3 C4 124.2(5) . . ?
O3 C3 C2 116.0(5) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 C7 110.7(4) . . ?
C4 C5 C7 130.1(5) . . ?
C5 C6 C1 122.7(5) . . ?
C5 C6 N1 110.0(4) . . ?
C1 C6 N1 127.2(4) . . ?
C5 C7 C21 116.1(4) . . ?
C5 C7 C8 102.5(4) . . ?
C21 C7 C8 114.3(4) . . ?
C5 C7 C17 113.2(4) . . ?
C21 C7 C17 101.5(4) . . ?
C8 C7 C17 109.6(4) . . ?
N1 C8 C18 106.0(4) . . ?
N1 C8 C7 104.5(4) . . ?
C18 C8 C7 116.5(4) . . ?
N1 C8 H8A 109.8 . . ?
C18 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
O4 C9 N1 122.4(5) . . ?
O4 C9 C10 121.2(5) . . ?
N1 C9 C10 116.3(5) . . ?
C9 C10 C11 118.0(4) . . ?
C9 C10 H10A 107.8 . . ?
C11 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
C11 C10 H10B 107.8 . . ?
H10A C10 H10B 107.1 . . ?
O1 C11 C18 114.9(4) . . ?
O1 C11 C10 104.8(4) . . ?
C18 C11 C10 110.3(4) . . ?
O1 C11 H11A 108.9 . . ?
C18 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
O1 C12 C13 111.3(4) . . ?
O1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 124.1(5) . . ?
C14 C13 H13A 118.0 . . ?
C12 C13 H13A 118.0 . . ?
C13 C14 C15 122.9(5) . . ?
C13 C14 C19 121.4(5) . . ?
C15 C14 C19 115.7(4) . . ?
C14 C15 N2 110.1(4) . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
N2 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 C17 104.7(4) . . ?
N2 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
N2 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.8(4) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C19 C18 C8 111.7(4) . . ?
C19 C18 C11 117.6(4) . . ?
C8 C18 C11 108.0(4) . . ?
C19 C18 H18A 106.3 . . ?
C8 C18 H18A 106.3 . . ?
C11 C18 H18A 106.3 . . ?
C14 C19 C18 114.5(4) . . ?
C14 C19 C20 108.6(4) . . ?
C18 C19 C20 106.8(4) . . ?
C14 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C21 C20 C19 108.9(4) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 C7 115.2(4) . . ?
C20 C21 N2 110.7(4) . . ?
C7 C21 N2 104.8(4) . . ?
C20 C21 H21A 108.6 . . ?
C7 C21 H21A 108.6 . . ?
N2 C21 H21A 108.6 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 O7 H7A 109.5 . . ?
C27 N3 C25 121.0(4) . . ?
C27 N3 H3A 119.5 . . ?
C25 N3 H3A 119.5 . . ?
O10 N4 O9 122.8(5) . . ?
O10 N4 C30 120.0(5) . . ?
O9 N4 C30 117.1(5) . . ?
O5 C24 O6 124.7(5) . . ?
O5 C24 C25 118.2(5) . . ?
O6 C24 C25 117.1(5) . . ?
N3 C25 C24 111.6(4) . . ?
N3 C25 C26 109.9(4) . . ?
C24 C25 C26 111.1(4) . . ?
N3 C25 H25A 108.0 . . ?
C24 C25 H25A 108.0 . . ?
C26 C25 H25A 108.0 . . ?
O7 C26 C25 113.8(4) . . ?
O7 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
O7 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
O8 C27 N3 121.8(5) . . ?
O8 C27 C28 120.7(5) . . ?
N3 C27 C28 117.5(5) . . ?
C33 C28 C29 118.9(5) . . ?
C33 C28 C27 124.4(4) . . ?
C29 C28 C27 116.5(5) . . ?
C30 C29 C28 119.3(5) . . ?
C30 C29 H29A 120.4 . . ?
C28 C29 H29A 120.4 . . ?
C29 C30 C31 122.6(5) . . ?
C29 C30 N4 119.2(5) . . ?
C31 C30 N4 118.2(5) . . ?
C32 C31 C30 117.2(5) . . ?
C32 C31 H31A 121.4 . . ?
C30 C31 H31A 121.4 . . ?
C31 C32 C33 121.6(5) . . ?
C31 C32 H32A 119.2 . . ?
C33 C32 H32A 119.2 . . ?
C28 C33 C32 120.3(5) . . ?
C28 C33 H33A 119.8 . . ?
C32 C33 H33A 119.8 . . ?
C100 O100 H100 109.5 . . ?
O100 C100 H101 109.5 . . ?
O100 C100 H102 109.5 . . ?
H101 C100 H102 109.5 . . ?
O100 C100 H103 109.5 . . ?
H101 C100 H103 109.5 . . ?
H102 C100 H103 109.5 . . ?
O100 C100 H120 106.7 . . ?
H101 C100 H120 46.7 . . ?
H102 C100 H120 66.9 . . ?
H103 C100 H120 142.3 . . ?
C110 O110 H110 109.5 . . ?
O110 C110 H111 109.5 . . ?
O110 C110 H112 109.5 . . ?
H111 C110 H112 109.5 . . ?
O110 C110 H113 109.5 . . ?
H111 C110 H113 109.5 . . ?
H112 C110 H113 109.5 . . ?
H11W O1W H12W 123.5 . . ?
H11W O1W H13W 48.4 . . ?
H12W O1W H13W 94.9 . . ?
H11W O1W H14W 106.9 . . ?
H12W O1W H14W 33.8 . . ?
H13W O1W H14W 64.9 . . ?
H11W O11W H12W 74.4 . . ?
H11W O11W H13W 41.8 . . ?
H12W O11W H13W 89.9 . . ?
H11W O11W H14W 86.2 . . ?
H12W O11W H14W 28.7 . . ?
H13W O11W H14W 81.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 3.6(6) . . . . ?
C22 O2 C2 C3 -176.1(4) . . . . ?
C6 C1 C2 O2 -178.8(4) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C23 O3 C3 C4 5.5(7) . . . . ?
C23 O3 C3 C2 -173.7(4) . . . . ?
O2 C2 C3 O3 -5.4(6) . . . . ?
C1 C2 C3 O3 174.9(4) . . . . ?
O2 C2 C3 C4 175.5(4) . . . . ?
C1 C2 C3 C4 -4.2(7) . . . . ?
O3 C3 C4 C5 -175.7(4) . . . . ?
C2 C3 C4 C5 3.4(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C3 C4 C5 C7 -175.2(5) . . . . ?
C4 C5 C6 C1 -4.1(7) . . . . ?
C7 C5 C6 C1 172.5(4) . . . . ?
C4 C5 C6 N1 174.8(4) . . . . ?
C7 C5 C6 N1 -8.6(5) . . . . ?
C2 C1 C6 C5 3.3(7) . . . . ?
C2 C1 C6 N1 -175.4(4) . . . . ?
C9 N1 C6 C5 -154.6(4) . . . . ?
C8 N1 C6 C5 -5.3(5) . . . . ?
C9 N1 C6 C1 24.2(7) . . . . ?
C8 N1 C6 C1 173.5(4) . . . . ?
C6 C5 C7 C21 143.4(4) . . . . ?
C4 C5 C7 C21 -40.5(7) . . . . ?
C6 C5 C7 C8 18.1(5) . . . . ?
C4 C5 C7 C8 -165.7(5) . . . . ?
C6 C5 C7 C17 -99.8(5) . . . . ?
C4 C5 C7 C17 76.3(6) . . . . ?
C9 N1 C8 C18 43.3(5) . . . . ?
C6 N1 C8 C18 -107.4(4) . . . . ?
C9 N1 C8 C7 166.9(4) . . . . ?
C6 N1 C8 C7 16.2(5) . . . . ?
C5 C7 C8 N1 -20.1(4) . . . . ?
C21 C7 C8 N1 -146.6(4) . . . . ?
C17 C7 C8 N1 100.3(4) . . . . ?
C5 C7 C8 C18 96.5(4) . . . . ?
C21 C7 C8 C18 -30.0(6) . . . . ?
C17 C7 C8 C18 -143.1(4) . . . . ?
C6 N1 C9 O4 -26.8(7) . . . . ?
C8 N1 C9 O4 -172.6(4) . . . . ?
C6 N1 C9 C10 153.1(4) . . . . ?
C8 N1 C9 C10 7.3(6) . . . . ?
O4 C9 C10 C11 147.0(5) . . . . ?
N1 C9 C10 C11 -32.9(6) . . . . ?
C12 O1 C11 C18 -67.4(5) . . . . ?
C12 O1 C11 C10 171.3(4) . . . . ?
C9 C10 C11 O1 128.2(4) . . . . ?
C9 C10 C11 C18 4.0(6) . . . . ?
C11 O1 C12 C13 87.6(5) . . . . ?
O1 C12 C13 C14 -62.8(6) . . . . ?
C12 C13 C14 C15 175.7(5) . . . . ?
C12 C13 C14 C19 -5.0(8) . . . . ?
C13 C14 C15 N2 -127.9(5) . . . . ?
C19 C14 C15 N2 52.7(5) . . . . ?
C16 N2 C15 C14 77.6(5) . . . . ?
C21 N2 C15 C14 -47.0(5) . . . . ?
C15 N2 C16 C17 -141.5(4) . . . . ?
C21 N2 C16 C17 -14.2(5) . . . . ?
N2 C16 C17 C7 34.8(5) . . . . ?
C5 C7 C17 C16 -167.1(4) . . . . ?
C21 C7 C17 C16 -42.0(4) . . . . ?
C8 C7 C17 C16 79.2(4) . . . . ?
N1 C8 C18 C19 159.1(4) . . . . ?
C7 C8 C18 C19 43.4(5) . . . . ?
N1 C8 C18 C11 -70.0(4) . . . . ?
C7 C8 C18 C11 174.2(4) . . . . ?
O1 C11 C18 C19 55.2(6) . . . . ?
C10 C11 C18 C19 173.4(4) . . . . ?
O1 C11 C18 C8 -72.4(5) . . . . ?
C10 C11 C18 C8 45.9(5) . . . . ?
C13 C14 C19 C18 60.7(6) . . . . ?
C15 C14 C19 C18 -119.9(5) . . . . ?
C13 C14 C19 C20 180.0(5) . . . . ?
C15 C14 C19 C20 -0.7(6) . . . . ?
C8 C18 C19 C14 59.1(5) . . . . ?
C11 C18 C19 C14 -66.6(6) . . . . ?
C8 C18 C19 C20 -61.1(5) . . . . ?
C11 C18 C19 C20 173.2(4) . . . . ?
C14 C19 C20 C21 -56.6(5) . . . . ?
C18 C19 C20 C21 67.4(5) . . . . ?
C19 C20 C21 C7 -56.3(5) . . . . ?
C19 C20 C21 N2 62.3(5) . . . . ?
C5 C7 C21 C20 -82.3(5) . . . . ?
C8 C7 C21 C20 36.7(6) . . . . ?
C17 C7 C21 C20 154.5(4) . . . . ?
C5 C7 C21 N2 155.8(4) . . . . ?
C8 C7 C21 N2 -85.2(5) . . . . ?
C17 C7 C21 N2 32.6(4) . . . . ?
C16 N2 C21 C20 -137.0(4) . . . . ?
C15 N2 C21 C20 -8.7(5) . . . . ?
C16 N2 C21 C7 -12.2(5) . . . . ?
C15 N2 C21 C7 116.1(4) . . . . ?
C27 N3 C25 C24 -148.9(5) . . . . ?
C27 N3 C25 C26 87.3(6) . . . . ?
O5 C24 C25 N3 2.9(7) . . . . ?
O6 C24 C25 N3 -178.0(4) . . . . ?
O5 C24 C25 C26 126.0(5) . . . . ?
O6 C24 C25 C26 -54.8(6) . . . . ?
N3 C25 C26 O7 73.9(5) . . . . ?
C24 C25 C26 O7 -50.2(6) . . . . ?
C25 N3 C27 O8 2.2(9) . . . . ?
C25 N3 C27 C28 -175.4(4) . . . . ?
O8 C27 C28 C33 -159.0(5) . . . . ?
N3 C27 C28 C33 18.7(8) . . . . ?
O8 C27 C28 C29 16.4(8) . . . . ?
N3 C27 C28 C29 -165.9(5) . . . . ?
C33 C28 C29 C30 -4.0(7) . . . . ?
C27 C28 C29 C30 -179.6(5) . . . . ?
C28 C29 C30 C31 1.9(7) . . . . ?
C28 C29 C30 N4 -179.2(4) . . . . ?
O10 N4 C30 C29 -176.3(4) . . . . ?
O9 N4 C30 C29 5.1(7) . . . . ?
O10 N4 C30 C31 2.6(7) . . . . ?
O9 N4 C30 C31 -176.0(5) . . . . ?
C29 C30 C31 C32 1.2(8) . . . . ?
N4 C30 C31 C32 -177.7(5) . . . . ?
C30 C31 C32 C33 -2.3(9) . . . . ?
C29 C28 C33 C32 2.9(8) . . . . ?
C27 C28 C33 C32 178.2(5) . . . . ?
C31 C32 C33 C28 0.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.93 1.68 2.604(5) 177.0 .
O7 H7A O6 0.84 1.89 2.723(5) 170.8 4_465
O100 H100 O7 0.84 2.15 2.798(7) 134.0 4_565
O110 H110 O11W 0.84 2.12 2.86(5) 146.9 .
O120 H120 O4 0.84 2.25 2.87(5) 131.0 3_745
O1W H11W O5 0.88 2.22 3.105(6) 179.3 .
O1W H12W O4 0.88 2.02 2.900(6) 179.1 3_645
O11W H13W O5 0.96 2.48 3.34(3) 148.1 .
O11W H14W O4 0.91 2.09 2.95(3) 156.0 3_645

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 930494'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97


#===== end


data_b/12pr
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucine propan-1,2-diol solvate 0.19-hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 N2 O4, C3 H8 O2, 0.19(H2 O)'
_chemical_formula_sum            'C26 H34.38 N2 O6.19'
_chemical_formula_weight         473.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.470(3)
_cell_length_b                   13.622(3)
_cell_length_c                   14.178(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2408.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2975
_cell_measurement_theta_min      2.8675
_cell_measurement_theta_max      28.8005

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7918
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2914
_reflns_number_gt                2261
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET)
(compiled Aug 14 2012,18:12:40)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1159P)^2^+0.4196P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0045(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2914
_refine_ls_number_parameters     433
_refine_ls_number_restraints     519
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4337(2) -0.1150(2) 0.1402(2) 0.0613(8) Uani 1 1 d . . .
O2 O 1.0233(2) -0.45559(19) 0.1234(2) 0.0600(8) Uani 1 1 d . . .
O3 O 1.13166(19) -0.2949(2) 0.1408(2) 0.0535(7) Uani 1 1 d . . .
O4 O 0.6213(2) -0.40981(19) 0.1004(3) 0.0613(8) Uani 1 1 d . . .
N1 N 0.6927(2) -0.2567(2) 0.0926(2) 0.0368(6) Uani 1 1 d . . .
N2 N 0.7689(3) 0.0725(2) 0.1164(2) 0.0468(8) Uani 1 1 d . . .
C1 C 0.8534(3) -0.3693(3) 0.1040(3) 0.0424(8) Uani 1 1 d . . .
H1A H 0.8143 -0.4269 0.0962 0.051 Uiso 1 1 calc R . .
C2 C 0.9637(3) -0.3712(3) 0.1181(3) 0.0433(8) Uani 1 1 d . . .
C3 C 1.0235(3) -0.2834(3) 0.1289(3) 0.0414(8) Uani 1 1 d . . .
C4 C 0.9711(3) -0.1946(3) 0.1257(2) 0.0388(8) Uani 1 1 d . . .
H4A H 1.0096 -0.1366 0.1325 0.047 Uiso 1 1 calc R . .
C5 C 0.8604(3) -0.1915(2) 0.1122(2) 0.0353(7) Uani 1 1 d . . .
C6 C 0.8039(3) -0.2779(3) 0.1021(2) 0.0377(7) Uani 1 1 d . . .
C7 C 0.7888(2) -0.1036(2) 0.1004(2) 0.0337(7) Uani 1 1 d . . .
C8 C 0.6749(2) -0.1495(2) 0.1082(2) 0.0326(7) Uani 1 1 d . . .
H8A H 0.6288 -0.1232 0.0583 0.039 Uiso 1 1 calc R . .
C9 C 0.6102(3) -0.3206(3) 0.1068(3) 0.0429(8) Uani 1 1 d . . .
C10 C 0.5034(3) -0.2734(3) 0.1291(3) 0.0461(9) Uani 1 1 d . . .
H10A H 0.4593 -0.3221 0.1604 0.055 Uiso 1 1 calc R . .
H10B H 0.4688 -0.2577 0.0697 0.055 Uiso 1 1 calc R . .
C11 C 0.5028(3) -0.1802(3) 0.1900(3) 0.0494(9) Uani 1 1 d . . .
H11A H 0.4714 -0.1953 0.2517 0.059 Uiso 1 1 calc R . .
C12 C 0.4093(3) -0.0254(4) 0.1888(5) 0.0788(16) Uani 1 1 d . . .
H12A H 0.4099 -0.0369 0.2563 0.095 Uiso 1 1 calc R . .
H12B H 0.3381 -0.0033 0.1712 0.095 Uiso 1 1 calc R . .
C13 C 0.4900(4) 0.0527(4) 0.1647(4) 0.0689(13) Uani 1 1 d . . .
H13A H 0.4678 0.1072 0.1304 0.083 Uiso 1 1 calc R . .
C14 C 0.5914(3) 0.0460(3) 0.1908(3) 0.0526(10) Uani 1 1 d . . .
C15 C 0.6753(3) 0.1195(3) 0.1638(3) 0.0571(10) Uani 1 1 d . . .
H15A H 0.6440 0.1678 0.1216 0.068 Uiso 1 1 calc R . .
H15B H 0.6998 0.1536 0.2199 0.068 Uiso 1 1 calc R . .
C16 C 0.7448(4) 0.0437(3) 0.0187(3) 0.0479(9) Uani 1 1 d . . .
H16A H 0.7711 0.0927 -0.0252 0.057 Uiso 1 1 calc R . .
H16B H 0.6681 0.0362 0.0098 0.057 Uiso 1 1 calc R . .
C17 C 0.8020(3) -0.0535(3) 0.0039(2) 0.0390(8) Uani 1 1 d . . .
H17A H 0.8770 -0.0437 -0.0115 0.047 Uiso 1 1 calc R . .
H17B H 0.7683 -0.0916 -0.0458 0.047 Uiso 1 1 calc R . .
C18 C 0.6179(3) -0.1407(3) 0.2037(2) 0.0409(8) Uani 1 1 d . . .
H18A H 0.6536 -0.1878 0.2454 0.049 Uiso 1 1 calc R . .
C19 C 0.6340(3) -0.0404(3) 0.2495(3) 0.0468(9) Uani 1 1 d . . .
H19A H 0.5988 -0.0401 0.3113 0.056 Uiso 1 1 calc R . .
C20 C 0.7550(3) -0.0281(3) 0.2635(3) 0.0491(10) Uani 1 1 d . . .
H20A H 0.7691 0.0295 0.3018 0.059 Uiso 1 1 calc R . .
H20B H 0.7840 -0.0850 0.2958 0.059 Uiso 1 1 calc R . .
C21 C 0.8079(3) -0.0169(3) 0.1681(2) 0.0399(8) Uani 1 1 d . . .
H21A H 0.8854 -0.0102 0.1779 0.048 Uiso 1 1 calc R . .
C22 C 0.9677(4) -0.5455(3) 0.1192(5) 0.0766(16) Uani 1 1 d . . .
H22A H 1.0180 -0.5988 0.1229 0.115 Uiso 1 1 calc R . .
H22B H 0.9290 -0.5495 0.0608 0.115 Uiso 1 1 calc R . .
H22C H 0.9183 -0.5496 0.1710 0.115 Uiso 1 1 calc R . .
C23 C 1.1931(3) -0.2076(3) 0.1507(4) 0.0577(11) Uani 1 1 d . . .
H23A H 1.2673 -0.2243 0.1589 0.086 Uiso 1 1 calc R . .
H23B H 1.1685 -0.1716 0.2048 0.086 Uiso 1 1 calc R . .
H23C H 1.1850 -0.1679 0.0952 0.086 Uiso 1 1 calc R . .
O51 O 0.9357(10) 0.2128(11) 0.1129(10) 0.116(3) Uani 0.469(8) 1 d PDU A 1
H51 H 0.8816 0.1802 0.1027 0.174 Uiso 0.469(8) 1 calc PR A 1
C241 C 1.0080(13) 0.2058(14) 0.0321(12) 0.138(3) Uani 0.469(8) 1 d PDU A 1
H24A H 1.0422 0.2690 0.0229 0.166 Uiso 0.469(8) 1 calc PR A 1
H24B H 0.9658 0.1919 -0.0238 0.166 Uiso 0.469(8) 1 calc PR A 1
C251 C 1.0942(10) 0.1282(10) 0.0412(10) 0.138(3) Uani 0.469(8) 1 d PDU A 1
H25C H 1.0503 0.0717 0.0289 0.166 Uiso 0.277(9) 1 d PR B 1
H25B H 1.1217 0.1306 -0.0220 0.166 Uiso 0.193(9) 1 d PR C 1
O61 O 1.0603(19) 0.0265(11) 0.051(2) 0.133(4) Uani 0.193(9) 1 d PDU A 1
H61A H 1.0811 -0.0038 0.0041 0.200 Uiso 0.193(9) 1 d PR C 1
C261 C 1.180(2) 0.166(2) 0.108(3) 0.137(3) Uani 0.193(9) 1 d PDU A 1
H26D H 1.2232 0.2050 0.0669 0.206 Uiso 0.193(9) 1 d PR C 1
H26E H 1.1573 0.2043 0.1611 0.206 Uiso 0.193(9) 1 d PR C 1
H26F H 1.2202 0.1102 0.1295 0.206 Uiso 0.193(9) 1 d PR C 1
O62 O 1.1773(15) 0.1246(16) -0.0306(13) 0.137(3) Uani 0.277(9) 1 d PDU A 1
H62 H 1.1633 0.0645 -0.0498 0.205 Uiso 0.277(9) 1 d PR B 1
C262 C 1.129(2) 0.123(2) 0.1434(11) 0.138(3) Uani 0.277(9) 1 d PDU A 1
H26J H 1.0748 0.0824 0.1719 0.207 Uiso 0.277(9) 1 d PR B 1
H26K H 1.1967 0.0899 0.1457 0.207 Uiso 0.277(9) 1 d PR B 1
H26L H 1.1337 0.1839 0.1772 0.207 Uiso 0.277(9) 1 d PR B 1
O1W O 0.849(2) 0.2725(19) 0.084(2) 0.113(4) Uani 0.186(4) 1 d PU D 2
H11W H 0.8232 0.2129 0.0924 0.169 Uiso 0.186(4) 1 d PR D 2
H12W H 0.7939 0.3080 0.0658 0.169 Uiso 0.186(4) 1 d PR D 2
O56 O 1.2996(19) 0.215(3) 0.066(3) 0.151(6) Uani 0.186(4) 1 d PDU D 2
H56A H 1.3319 0.2318 0.0184 0.226 Uiso 0.186(4) 1 calc PR D 2
O66 O 1.046(2) 0.176(2) 0.1237(19) 0.133(3) Uani 0.186(4) 1 d PDU D 2
H66 H 1.0087 0.2253 0.1238 0.200 Uiso 0.186(4) 1 calc PR D 2
C246 C 1.2228(19) 0.138(2) 0.042(3) 0.140(3) Uani 0.186(4) 1 d PDU D 2
H24E H 1.2279 0.0862 0.0884 0.168 Uiso 0.186(4) 1 calc PR D 2
H24F H 1.2430 0.1102 -0.0187 0.168 Uiso 0.186(4) 1 calc PR D 2
C256 C 1.1072(19) 0.171(2) 0.0360(19) 0.138(3) Uani 0.186(4) 1 d PDU D 2
H25A H 1.1123 0.2400 0.0159 0.166 Uiso 0.186(4) 1 calc PR D 2
C266 C 1.055(3) 0.120(4) -0.047(2) 0.137(4) Uani 0.186(4) 1 d PDU D 2
H26A H 1.1012 0.1248 -0.1012 0.206 Uiso 0.186(4) 1 calc PR D 2
H26B H 0.9877 0.1513 -0.0610 0.206 Uiso 0.186(4) 1 calc PR D 2
H26C H 1.0430 0.0525 -0.0320 0.206 Uiso 0.186(4) 1 calc PR D 2
O53 O 0.9380(14) 0.2091(17) 0.0748(14) 0.122(3) Uani 0.344(8) 1 d PDU E 3
H53B H 0.8844 0.1747 0.0804 0.183 Uiso 0.344(8) 1 calc PR E 3
O63 O 1.1908(13) 0.0580(13) 0.0256(13) 0.144(3) Uani 0.344(8) 1 d PDU E 3
H63A H 1.1585 0.0159 -0.0044 0.216 Uiso 0.344(8) 1 calc PR E 3
C243 C 1.0184(14) 0.1568(19) 0.0194(13) 0.135(3) Uani 0.344(8) 1 d PDU E 3
H24C H 1.0440 0.2001 -0.0300 0.162 Uiso 0.344(8) 1 calc PR E 3
H24D H 0.9843 0.1011 -0.0108 0.162 Uiso 0.344(8) 1 calc PR E 3
C253 C 1.1140(12) 0.1202(13) 0.0751(11) 0.137(3) Uani 0.344(8) 1 d PDU E 3
H25D H 1.0825 0.0765 0.1225 0.164 Uiso 0.344(8) 1 calc PR E 3
C263 C 1.1585(19) 0.2047(17) 0.1324(17) 0.135(3) Uani 0.344(8) 1 d PDU E 3
H26G H 1.1727 0.1829 0.1955 0.203 Uiso 0.344(8) 1 calc PR E 3
H26H H 1.1070 0.2571 0.1338 0.203 Uiso 0.344(8) 1 calc PR E 3
H26I H 1.2237 0.2276 0.1040 0.203 Uiso 0.344(8) 1 calc PR E 3

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0376(13) 0.0635(17) 0.083(2) -0.0173(16) -0.0091(14) 0.0051(13)
O2 0.0453(14) 0.0428(13) 0.092(2) 0.0016(15) -0.0071(16) 0.0077(12)
O3 0.0346(13) 0.0547(15) 0.0712(18) 0.0035(14) -0.0012(13) 0.0044(12)
O4 0.0534(15) 0.0400(14) 0.091(2) -0.0048(15) 0.0078(17) -0.0072(12)
N1 0.0363(14) 0.0362(14) 0.0380(14) -0.0032(12) -0.0008(13) -0.0012(12)
N2 0.0511(17) 0.0373(15) 0.0518(18) -0.0053(14) -0.0021(15) -0.0009(14)
C1 0.0419(18) 0.0332(16) 0.052(2) -0.0008(16) 0.0000(17) -0.0022(15)
C2 0.0390(18) 0.0406(18) 0.050(2) 0.0051(17) 0.0011(16) 0.0033(15)
C3 0.0332(17) 0.0464(19) 0.0445(18) -0.0005(16) -0.0003(15) 0.0020(15)
C4 0.0353(16) 0.0417(17) 0.0395(17) -0.0023(15) -0.0003(14) -0.0068(15)
C5 0.0356(16) 0.0370(16) 0.0333(16) 0.0013(14) -0.0008(14) -0.0024(14)
C6 0.0358(16) 0.0440(18) 0.0333(16) -0.0016(15) 0.0028(15) -0.0007(14)
C7 0.0295(14) 0.0363(16) 0.0353(16) -0.0031(14) -0.0007(13) -0.0020(13)
C8 0.0316(15) 0.0339(15) 0.0324(15) -0.0022(13) -0.0024(13) -0.0033(13)
C9 0.0383(17) 0.0431(18) 0.0471(19) -0.0011(17) -0.0021(16) -0.0102(15)
C10 0.0373(18) 0.051(2) 0.050(2) 0.0028(17) 0.0038(16) -0.0142(16)
C11 0.0361(17) 0.063(2) 0.049(2) -0.0062(18) 0.0069(17) -0.0122(18)
C12 0.037(2) 0.074(3) 0.126(5) -0.034(3) 0.008(3) 0.005(2)
C13 0.052(2) 0.059(2) 0.096(4) -0.022(3) -0.005(2) 0.016(2)
C14 0.046(2) 0.051(2) 0.061(2) -0.0250(19) 0.0071(19) 0.0009(18)
C15 0.058(2) 0.048(2) 0.065(2) -0.014(2) -0.002(2) 0.005(2)
C16 0.059(2) 0.0375(17) 0.048(2) 0.0006(16) -0.0045(19) -0.0004(18)
C17 0.0410(18) 0.0401(16) 0.0360(16) 0.0017(14) 0.0026(15) -0.0056(15)
C18 0.0357(17) 0.0519(19) 0.0350(16) -0.0066(15) 0.0036(15) -0.0050(16)
C19 0.044(2) 0.059(2) 0.0367(17) -0.0147(17) 0.0054(16) -0.0075(18)
C20 0.048(2) 0.060(2) 0.0397(18) -0.0153(17) -0.0045(17) -0.004(2)
C21 0.0361(17) 0.0410(17) 0.0426(18) -0.0026(15) -0.0043(15) -0.0054(15)
C22 0.065(3) 0.0368(19) 0.128(5) 0.003(3) -0.005(3) 0.007(2)
C23 0.0330(18) 0.061(2) 0.079(3) -0.002(2) -0.005(2) -0.0035(19)
O51 0.118(4) 0.096(4) 0.135(5) -0.014(5) 0.014(5) -0.034(4)
C241 0.137(5) 0.127(4) 0.151(5) -0.008(4) 0.007(4) -0.011(4)
C251 0.141(4) 0.128(4) 0.147(4) -0.007(3) 0.007(3) -0.006(3)
O61 0.138(7) 0.123(7) 0.139(7) -0.011(6) 0.009(6) -0.008(6)
C261 0.138(5) 0.130(5) 0.144(5) -0.005(4) 0.004(4) -0.006(4)
O62 0.138(5) 0.129(5) 0.144(5) -0.006(4) 0.010(4) -0.001(4)
C262 0.140(5) 0.131(5) 0.143(5) -0.005(4) 0.004(4) -0.006(4)
O1W 0.113(6) 0.097(6) 0.128(7) -0.011(6) 0.009(6) -0.024(6)
O56 0.153(8) 0.144(8) 0.156(9) -0.003(7) -0.001(7) -0.006(7)
O66 0.134(4) 0.123(4) 0.142(4) -0.007(4) 0.006(4) -0.012(4)
C246 0.141(5) 0.133(5) 0.147(5) -0.006(4) 0.004(4) -0.005(4)
C256 0.140(4) 0.130(4) 0.145(4) -0.006(4) 0.005(4) -0.005(4)
C266 0.138(6) 0.130(5) 0.143(6) -0.005(5) 0.004(5) -0.004(5)
O53 0.121(5) 0.108(4) 0.138(5) -0.010(5) 0.015(5) -0.023(4)
O63 0.141(5) 0.141(5) 0.150(5) -0.015(5) -0.001(5) -0.002(5)
C243 0.135(4) 0.125(4) 0.144(5) -0.007(4) 0.004(4) -0.012(4)
C253 0.139(4) 0.128(4) 0.142(4) -0.007(4) 0.003(4) -0.007(4)
C263 0.137(5) 0.128(5) 0.141(5) -0.007(5) 0.002(5) -0.010(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.425(5) . ?
O1 C12 1.435(6) . ?
O2 C2 1.371(4) . ?
O2 C22 1.409(5) . ?
O3 C3 1.369(4) . ?
O3 C23 1.421(5) . ?
O4 C9 1.227(4) . ?
N1 C9 1.362(4) . ?
N1 C6 1.423(4) . ?
N1 C8 1.493(4) . ?
N2 C16 1.470(5) . ?
N2 C15 1.491(5) . ?
N2 C21 1.502(5) . ?
C1 C2 1.390(5) . ?
C1 C6 1.390(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.418(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.394(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(5) . ?
C5 C7 1.503(4) . ?
C7 C17 1.538(5) . ?
C7 C21 1.540(5) . ?
C7 C8 1.556(4) . ?
C8 C18 1.534(5) . ?
C8 H8A 0.9800 . ?
C9 C10 1.512(5) . ?
C10 C11 1.535(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.545(5) . ?
C11 H11A 0.9800 . ?
C12 C13 1.503(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.322(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.498(6) . ?
C14 C19 1.537(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.518(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.525(5) . ?
C18 H18A 0.9800 . ?
C19 C20 1.530(6) . ?
C19 H19A 0.9800 . ?
C20 C21 1.513(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O51 C241 1.461(12) . ?
O51 H51 0.8200 . ?
O51 H11W 1.4320 . ?
C241 C251 1.513(13) . ?
C241 H24A 0.9700 . ?
C241 H24B 0.9700 . ?
C251 O62 1.454(12) . ?
C251 O61 1.455(12) . ?
C251 C261 1.513(13) . ?
C251 C262 1.514(13) . ?
C251 H25C 0.9600 . ?
C251 H25B 0.9601 . ?
O61 H25C 0.6993 . ?
O61 H61A 0.8200 . ?
C261 C262 1.00(5) . ?
C261 H26D 0.9600 . ?
C261 H26E 0.9600 . ?
C261 H26F 0.9601 . ?
C261 H26K 1.1830 . ?
C261 H26L 1.1631 . ?
O62 H25B 0.7084 . ?
O62 H62 0.8800 . ?
C262 H26E 1.1896 . ?
C262 H26F 1.1699 . ?
C262 H26J 0.9600 . ?
C262 H26K 0.9600 . ?
C262 H26L 0.9601 . ?
O1W H11W 0.8800 . ?
O1W H12W 0.8800 . ?
O56 C246 1.457(12) . ?
O56 H26D 0.9621 . ?
O56 H56A 0.8200 . ?
O66 C256 1.459(12) . ?
O66 H26L 1.3329 . ?
O66 H66 0.8200 . ?
C246 C256 1.513(13) . ?
C246 H24E 0.9700 . ?
C246 H24F 0.9700 . ?
C256 C266 1.515(13) . ?
C256 H25A 0.9800 . ?
C266 H26A 0.9600 . ?
C266 H26B 0.9600 . ?
C266 H26C 0.9600 . ?
O53 C243 1.459(12) . ?
O53 H11W 1.4532 . ?
O53 H53B 0.8200 . ?
O63 C253 1.458(12) . ?
O63 H25B 1.4750 . ?
O63 H62 1.1256 . ?
O63 H63A 0.8200 . ?
C243 C253 1.515(13) . ?
C243 H24C 0.9700 . ?
C243 H24D 0.9700 . ?
C253 C263 1.514(13) . ?
C253 H25D 0.9800 . ?
C263 H26G 0.9600 . ?
C263 H26H 0.9600 . ?
C263 H26I 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 114.9(4) . . ?
C2 O2 C22 117.4(3) . . ?
C3 O3 C23 116.6(3) . . ?
C9 N1 C6 126.3(3) . . ?
C9 N1 C8 119.4(3) . . ?
C6 N1 C8 109.2(3) . . ?
C16 N2 C15 112.3(3) . . ?
C16 N2 C21 108.0(3) . . ?
C15 N2 C21 112.5(3) . . ?
C2 C1 C6 117.3(3) . . ?
C2 C1 H1A 121.4 . . ?
C6 C1 H1A 121.4 . . ?
O2 C2 C1 124.0(3) . . ?
O2 C2 C3 114.6(3) . . ?
C1 C2 C3 121.3(3) . . ?
O3 C3 C4 125.0(3) . . ?
O3 C3 C2 115.8(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 C7 111.4(3) . . ?
C4 C5 C7 128.9(3) . . ?
C5 C6 C1 122.4(3) . . ?
C5 C6 N1 109.6(3) . . ?
C1 C6 N1 128.0(3) . . ?
C5 C7 C17 112.9(3) . . ?
C5 C7 C21 116.7(3) . . ?
C17 C7 C21 101.5(3) . . ?
C5 C7 C8 102.3(2) . . ?
C17 C7 C8 109.8(3) . . ?
C21 C7 C8 113.9(3) . . ?
N1 C8 C18 106.0(3) . . ?
N1 C8 C7 104.3(2) . . ?
C18 C8 C7 117.1(3) . . ?
N1 C8 H8A 109.7 . . ?
C18 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O4 C9 N1 122.5(3) . . ?
O4 C9 C10 122.4(3) . . ?
N1 C9 C10 115.1(3) . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C9 C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
O1 C11 C10 103.8(3) . . ?
O1 C11 C18 114.0(3) . . ?
C10 C11 C18 110.7(3) . . ?
O1 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C18 C11 H11A 109.4 . . ?
O1 C12 C13 110.5(4) . . ?
O1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 121.9(5) . . ?
C14 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C13 C14 C15 123.4(5) . . ?
C13 C14 C19 122.3(4) . . ?
C15 C14 C19 114.2(3) . . ?
N2 C15 C14 112.0(3) . . ?
N2 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C17 105.5(3) . . ?
N2 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
N2 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 102.3(3) . . ?
C16 C17 H17A 111.3 . . ?
C7 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C7 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C19 C18 C8 112.6(3) . . ?
C19 C18 C11 119.2(3) . . ?
C8 C18 C11 107.0(3) . . ?
C19 C18 H18A 105.6 . . ?
C8 C18 H18A 105.6 . . ?
C11 C18 H18A 105.6 . . ?
C18 C19 C20 106.5(3) . . ?
C18 C19 C14 114.2(3) . . ?
C20 C19 C14 109.0(3) . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C14 C19 H19A 109.0 . . ?
C21 C20 C19 109.0(3) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
N2 C21 C20 112.1(3) . . ?
N2 C21 C7 105.5(3) . . ?
C20 C21 C7 114.4(3) . . ?
N2 C21 H21A 108.2 . . ?
C20 C21 H21A 108.2 . . ?
C7 C21 H21A 108.2 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C241 O51 H51 109.5 . . ?
C241 O51 H11W 116.4 . . ?
H51 O51 H11W 32.8 . . ?
O51 C241 C251 114.6(9) . . ?
O51 C241 H24A 108.6 . . ?
C251 C241 H24A 108.6 . . ?
O51 C241 H24B 108.6 . . ?
C251 C241 H24B 108.6 . . ?
H24A C241 H24B 107.6 . . ?
O62 C251 O61 103.8(17) . . ?
O62 C251 C241 118.1(6) . . ?
O61 C251 C241 117.8(6) . . ?
O62 C251 C261 87.0(16) . . ?
O61 C251 C261 118.0(6) . . ?
C241 C251 C261 108.5(13) . . ?
O62 C251 C262 117.8(6) . . ?
O61 C251 C262 87.2(15) . . ?
C241 C251 C262 108.5(13) . . ?
C261 C251 C262 38(2) . . ?
O62 C251 H25C 104.5 . . ?
O61 C251 H25C 24.2 . . ?
C241 C251 H25C 98.1 . . ?
C261 C251 H25C 141.7 . . ?
C262 C251 H25C 107.4 . . ?
O62 C251 H25B 24.8 . . ?
O61 C251 H25B 102.8 . . ?
C241 C251 H25B 98.7 . . ?
C261 C251 H25B 108.7 . . ?
C262 C251 H25B 142.5 . . ?
H25C C251 H25B 93.5 . . ?
C251 O61 H25C 34.2 . . ?
C251 O61 H61A 108.2 . . ?
H25C O61 H61A 98.3 . . ?
C262 C261 C251 70.8(10) . . ?
C262 C261 H26D 172.9 . . ?
C251 C261 H26D 102.0 . . ?
C262 C261 H26E 74.9 . . ?
C251 C261 H26E 118.2 . . ?
H26D C261 H26E 109.5 . . ?
C262 C261 H26F 73.4 . . ?
C251 C261 H26F 107.8 . . ?
H26D C261 H26F 109.5 . . ?
H26E C261 H26F 109.5 . . ?
C262 C261 H26K 51.4 . . ?
C251 C261 H26K 96.6 . . ?
H26D C261 H26K 131.3 . . ?
H26E C261 H26K 100.1 . . ?
H26F C261 H26K 22.0 . . ?
C262 C261 H26L 52.1 . . ?
C251 C261 H26L 104.7 . . ?
H26D C261 H26L 132.1 . . ?
H26E C261 H26L 22.8 . . ?
H26F C261 H26L 99.1 . . ?
H26K C261 H26L 83.9 . . ?
C251 O62 H25B 34.7 . . ?
C251 O62 H62 96.1 . . ?
H25B O62 H62 88.1 . . ?
C261 C262 C251 70.7(11) . . ?
C261 C262 H26E 51.2 . . ?
C251 C262 H26E 104.1 . . ?
C261 C262 H26F 51.9 . . ?
C251 C262 H26F 97.1 . . ?
H26E C262 H26F 83.3 . . ?
C261 C262 H26J 173.8 . . ?
C251 C262 H26J 103.2 . . ?
H26E C262 H26J 131.1 . . ?
H26F C262 H26J 131.9 . . ?
C261 C262 H26K 74.4 . . ?
C251 C262 H26K 107.8 . . ?
H26E C262 H26K 99.7 . . ?
H26F C262 H26K 22.5 . . ?
H26J C262 H26K 109.5 . . ?
C261 C262 H26L 73.0 . . ?
C251 C262 H26L 117.1 . . ?
H26E C262 H26L 21.8 . . ?
H26F C262 H26L 98.6 . . ?
H26J C262 H26L 109.5 . . ?
H26K C262 H26L 109.5 . . ?
H11W O1W H12W 105.1 . . ?
C246 O56 H26D 41.9 . . ?
C246 O56 H56A 109.5 . . ?
H26D O56 H56A 122.4 . . ?
C256 O66 H26L 93.6 . . ?
C256 O66 H66 109.5 . . ?
H26L O66 H66 113.5 . . ?
O56 C246 C256 115.1(10) . . ?
O56 C246 H25B 135.8 . . ?
C256 C246 H25B 38.3 . . ?
O56 C246 H26D 40.9 . . ?
C256 C246 H26D 75.3 . . ?
H25B C246 H26D 106.0 . . ?
O56 C246 H26F 89.9 . . ?
C256 C246 H26F 96.6 . . ?
H25B C246 H26F 121.1 . . ?
H26D C246 H26F 85.6 . . ?
O56 C246 H24E 108.5 . . ?
C256 C246 H24E 108.5 . . ?
H25B C246 H24E 113.7 . . ?
H26D C246 H24E 115.4 . . ?
H26F C246 H24E 30.4 . . ?
O56 C246 H24F 108.5 . . ?
C256 C246 H24F 108.5 . . ?
H25B C246 H24F 70.9 . . ?
H26D C246 H24F 133.2 . . ?
H26F C246 H24F 137.5 . . ?
H24E C246 H24F 107.5 . . ?
O66 C256 C246 117.6(7) . . ?
O66 C256 C266 117.3(7) . . ?
C246 C256 C266 108.3(13) . . ?
O66 C256 H25C 81.5 . . ?
C246 C256 H25C 100.3 . . ?
C266 C256 H25C 49.1 . . ?
O66 C256 H25B 144.3 . . ?
C246 C256 H25B 73.1 . . ?
C266 C256 H25B 35.9 . . ?
H25C C256 H25B 62.8 . . ?
O66 C256 H26D 103.1 . . ?
C246 C256 H26D 36.9 . . ?
C266 C256 H26D 138.0 . . ?
H25C C256 H26D 134.4 . . ?
H25B C256 H26D 102.9 . . ?
O66 C256 H25A 103.9 . . ?
C246 C256 H25A 103.9 . . ?
C266 C256 H25A 103.9 . . ?
H25C C256 H25A 148.8 . . ?
H25B C256 H25A 106.1 . . ?
H26D C256 H25A 75.1 . . ?
C256 C266 H25C 66.3 . . ?
C256 C266 H25B 40.2 . . ?
H25C C266 H25B 77.9 . . ?
C256 C266 H62 82.5 . . ?
H25C C266 H62 78.7 . . ?
H25B C266 H62 45.0 . . ?
C256 C266 H26A 109.5 . . ?
H25C C266 H26A 137.7 . . ?
H25B C266 H26A 75.9 . . ?
H62 C266 H26A 59.3 . . ?
C256 C266 H26B 109.5 . . ?
H25C C266 H26B 111.3 . . ?
H25B C266 H26B 143.8 . . ?
H62 C266 H26B 166.6 . . ?
H26A C266 H26B 109.5 . . ?
C256 C266 H26C 109.5 . . ?
H25C C266 H26C 45.5 . . ?
H25B C266 H26C 101.6 . . ?
H62 C266 H26C 70.7 . . ?
H26A C266 H26C 109.5 . . ?
H26B C266 H26C 109.5 . . ?
C243 O53 H11W 141.9 . . ?
C243 O53 H53B 109.5 . . ?
H11W O53 H53B 37.1 . . ?
C253 O63 H25B 56.4 . . ?
C253 O63 H62 102.2 . . ?
H25B O63 H62 48.3 . . ?
C253 O63 H63A 109.5 . . ?
H25B O63 H63A 86.8 . . ?
H62 O63 H63A 54.0 . . ?
O53 C243 C253 114.9(10) . . ?
O53 C243 H25C 128.5 . . ?
C253 C243 H25C 51.6 . . ?
O53 C243 H25B 160.4 . . ?
C253 C243 H25B 55.5 . . ?
H25C C243 H25B 61.9 . . ?
O53 C243 H24C 108.5 . . ?
C253 C243 H24C 108.5 . . ?
H25C C243 H24C 123.0 . . ?
H25B C243 H24C 64.4 . . ?
O53 C243 H24D 108.5 . . ?
C253 C243 H24D 108.5 . . ?
H25C C243 H24D 56.9 . . ?
H25B C243 H24D 91.0 . . ?
H24C C243 H24D 107.5 . . ?
O63 C253 C263 117.4(7) . . ?
O63 C253 C243 117.2(7) . . ?
C263 C253 C243 108.5(13) . . ?
O63 C253 H25C 81.7 . . ?
C263 C253 H25C 159.3 . . ?
C243 C253 H25C 52.2 . . ?
O63 C253 H25B 62.4 . . ?
C263 C253 H25B 115.4 . . ?
C243 C253 H25B 60.2 . . ?
H25C C253 H25B 64.5 . . ?
O63 C253 H26F 68.0 . . ?
C263 C253 H26F 58.9 . . ?
C243 C253 H26F 165.5 . . ?
H25C C253 H26F 141.2 . . ?
H25B C253 H26F 116.6 . . ?
O63 C253 H26J 116.2 . . ?
C263 C253 H26J 83.8 . . ?
C243 C253 H26J 108.8 . . ?
H25C C253 H26J 95.2 . . ?
H25B C253 H26J 159.6 . . ?
H26F C253 H26J 78.3 . . ?
O63 C253 H26K 73.1 . . ?
C263 C253 H26K 66.3 . . ?
C243 C253 H26K 169.3 . . ?
H25C C253 H26K 131.1 . . ?
H25B C253 H26K 130.2 . . ?
H26F C253 H26K 17.5 . . ?
H26J C253 H26K 62.1 . . ?
O63 C253 H25D 103.9 . . ?
C263 C253 H25D 103.9 . . ?
C243 C253 H25D 103.9 . . ?
H25C C253 H25D 77.2 . . ?
H25B C253 H25D 140.4 . . ?
H26F C253 H25D 87.0 . . ?
H26J C253 H25D 20.2 . . ?
H26K C253 H25D 69.5 . . ?
C253 C263 H26D 80.7 . . ?
C253 C263 H26E 120.9 . . ?
H26D C263 H26E 141.0 . . ?
C253 C263 H26F 61.4 . . ?
H26D C263 H26F 69.3 . . ?
H26E C263 H26F 92.0 . . ?
C253 C263 H26L 91.0 . . ?
H26D C263 H26L 153.8 . . ?
H26E C263 H26L 31.3 . . ?
H26F C263 H26L 84.9 . . ?
C253 C263 H26G 109.5 . . ?
H26D C263 H26G 125.7 . . ?
H26E C263 H26G 21.7 . . ?
H26F C263 H26G 70.4 . . ?
H26L C263 H26G 35.0 . . ?
C253 C263 H26H 109.5 . . ?
H26D C263 H26H 116.9 . . ?
H26E C263 H26H 87.9 . . ?
H26F C263 H26H 169.0 . . ?
H26L C263 H26H 89.3 . . ?
H26G C263 H26H 109.5 . . ?
C253 C263 H26I 109.5 . . ?
H26D C263 H26I 29.1 . . ?
H26E C263 H26I 116.9 . . ?
H26F C263 H26I 80.4 . . ?
H26L C263 H26I 144.5 . . ?
H26G C263 H26I 109.5 . . ?
H26H C263 H26I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 -3.5(6) . . . . ?
C22 O2 C2 C3 176.1(4) . . . . ?
C6 C1 C2 O2 178.8(3) . . . . ?
C6 C1 C2 C3 -0.8(6) . . . . ?
C23 O3 C3 C4 0.2(6) . . . . ?
C23 O3 C3 C2 179.4(3) . . . . ?
O2 C2 C3 O3 1.4(5) . . . . ?
C1 C2 C3 O3 -179.0(4) . . . . ?
O2 C2 C3 C4 -179.4(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
O3 C3 C4 C5 179.3(4) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C7 -175.8(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C7 C5 C6 C1 175.9(3) . . . . ?
C4 C5 C6 N1 178.0(3) . . . . ?
C7 C5 C6 N1 -5.6(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C2 C1 C6 N1 -177.3(3) . . . . ?
C9 N1 C6 C5 -161.0(3) . . . . ?
C8 N1 C6 C5 -6.6(4) . . . . ?
C9 N1 C6 C1 17.5(6) . . . . ?
C8 N1 C6 C1 171.8(4) . . . . ?
C6 C5 C7 C17 -103.4(3) . . . . ?
C4 C5 C7 C17 72.7(4) . . . . ?
C6 C5 C7 C21 139.6(3) . . . . ?
C4 C5 C7 C21 -44.3(5) . . . . ?
C6 C5 C7 C8 14.6(4) . . . . ?
C4 C5 C7 C8 -169.4(3) . . . . ?
C9 N1 C8 C18 47.5(4) . . . . ?
C6 N1 C8 C18 -108.9(3) . . . . ?
C9 N1 C8 C7 171.7(3) . . . . ?
C6 N1 C8 C7 15.3(4) . . . . ?
C5 C7 C8 N1 -17.3(3) . . . . ?
C17 C7 C8 N1 102.8(3) . . . . ?
C21 C7 C8 N1 -144.2(3) . . . . ?
C5 C7 C8 C18 99.4(3) . . . . ?
C17 C7 C8 C18 -140.4(3) . . . . ?
C21 C7 C8 C18 -27.5(4) . . . . ?
C6 N1 C9 O4 -23.7(6) . . . . ?
C8 N1 C9 O4 -175.7(4) . . . . ?
C6 N1 C9 C10 157.4(3) . . . . ?
C8 N1 C9 C10 5.4(5) . . . . ?
O4 C9 C10 C11 144.7(4) . . . . ?
N1 C9 C10 C11 -36.4(5) . . . . ?
C12 O1 C11 C10 173.0(3) . . . . ?
C12 O1 C11 C18 -66.5(4) . . . . ?
C9 C10 C11 O1 132.8(3) . . . . ?
C9 C10 C11 C18 10.0(5) . . . . ?
C11 O1 C12 C13 90.1(5) . . . . ?
O1 C12 C13 C14 -66.9(7) . . . . ?
C12 C13 C14 C15 176.6(4) . . . . ?
C12 C13 C14 C19 -1.4(7) . . . . ?
C16 N2 C15 C14 75.0(4) . . . . ?
C21 N2 C15 C14 -47.0(5) . . . . ?
C13 C14 C15 N2 -125.2(4) . . . . ?
C19 C14 C15 N2 53.0(5) . . . . ?
C15 N2 C16 C17 -142.0(3) . . . . ?
C21 N2 C16 C17 -17.5(4) . . . . ?
N2 C16 C17 C7 36.6(3) . . . . ?
C5 C7 C17 C16 -166.5(3) . . . . ?
C21 C7 C17 C16 -40.8(3) . . . . ?
C8 C7 C17 C16 80.0(3) . . . . ?
N1 C8 C18 C19 156.3(3) . . . . ?
C7 C8 C18 C19 40.5(4) . . . . ?
N1 C8 C18 C11 -70.8(3) . . . . ?
C7 C8 C18 C11 173.4(3) . . . . ?
O1 C11 C18 C19 54.3(5) . . . . ?
C10 C11 C18 C19 170.9(3) . . . . ?
O1 C11 C18 C8 -74.9(4) . . . . ?
C10 C11 C18 C8 41.7(4) . . . . ?
C8 C18 C19 C20 -59.9(4) . . . . ?
C11 C18 C19 C20 173.5(3) . . . . ?
C8 C18 C19 C14 60.5(4) . . . . ?
C11 C18 C19 C14 -66.2(4) . . . . ?
C13 C14 C19 C18 58.4(5) . . . . ?
C15 C14 C19 C18 -119.8(4) . . . . ?
C13 C14 C19 C20 177.3(4) . . . . ?
C15 C14 C19 C20 -0.9(4) . . . . ?
C18 C19 C20 C21 69.0(4) . . . . ?
C14 C19 C20 C21 -54.7(4) . . . . ?
C16 N2 C21 C20 -133.8(3) . . . . ?
C15 N2 C21 C20 -9.3(4) . . . . ?
C16 N2 C21 C7 -8.7(4) . . . . ?
C15 N2 C21 C7 115.8(3) . . . . ?
C19 C20 C21 N2 61.7(4) . . . . ?
C19 C20 C21 C7 -58.4(4) . . . . ?
C5 C7 C21 N2 153.8(3) . . . . ?
C17 C7 C21 N2 30.7(3) . . . . ?
C8 C7 C21 N2 -87.2(3) . . . . ?
C5 C7 C21 C20 -82.5(4) . . . . ?
C17 C7 C21 C20 154.4(3) . . . . ?
C8 C7 C21 C20 36.5(4) . . . . ?
O51 C241 C251 O62 -172.5(16) . . . . ?
O51 C241 C251 O61 61(2) . . . . ?
O51 C241 C251 C261 -76(2) . . . . ?
O51 C241 C251 C262 -35.3(18) . . . . ?
O62 C251 C261 C262 -144.7(11) . . . . ?
O61 C251 C261 C262 -40.6(15) . . . . ?
C241 C251 C261 C262 96.6(9) . . . . ?
O62 C251 C262 C261 40.7(15) . . . . ?
O61 C251 C262 C261 144.8(11) . . . . ?
C241 C251 C262 C261 -96.7(9) . . . . ?
O56 C246 C256 O66 -84(4) . . . . ?
O56 C246 C256 C266 140(3) . . . . ?
O53 C243 C253 O63 173.2(19) . . . . ?
O53 C243 C253 C263 -51(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 930495'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_global
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97

#===== end



data_b/12bu
#TrackingRef '18754_web_deposit_cif_file_0_AgataBialonska_1363870110.Bialonska_cifs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
brucine butan-1,2-diol 0.84-solvate 0.16-hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 N2 O4, 0.84(C4 H10 O2), 0.16(H2 O)'
_chemical_formula_sum            'C26.37 H34.74 N2 O5.84'
_chemical_formula_weight         473.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.481(2)
_cell_length_b                   13.650(2)
_cell_length_c                   13.981(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2381.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13007
_cell_measurement_theta_min      3.1583
_cell_measurement_theta_max      77.8248

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          1.0618
_exptl_crystal_size_mid          0.1881
_exptl_crystal_size_min          0.1320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1015
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54175
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16748
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.53
_diffrn_reflns_theta_max         78.03
_reflns_number_total             5071
_reflns_number_gt                4952
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    
;
SIR2004 (Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B.,
Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori G.,
Spagna, R., J. Appl. Cryst. 2005. 38, 381-388.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. (2008). <i>Acta Cryst.</i> <b>A64</b>, 112-122.)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1085P)^2^+0.4228P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(18)
_refine_ls_number_reflns         5071
_refine_ls_number_parameters     384
_refine_ls_number_restraints     109
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56484(11) 0.38423(12) 0.86153(12) 0.0331(3) Uani 1 1 d . . .
O2 O -0.02352(12) 0.04574(10) 0.87120(12) 0.0304(3) Uani 1 1 d . . .
O3 O -0.13167(11) 0.20596(10) 0.85773(10) 0.0260(3) Uani 1 1 d . . .
O4 O 0.37565(12) 0.08973(11) 0.89720(12) 0.0319(3) Uani 1 1 d . . .
N1 N 0.30622(12) 0.24297(11) 0.90828(10) 0.0209(3) Uani 1 1 d . . .
N2 N 0.23059(13) 0.57283(11) 0.88991(12) 0.0246(3) Uani 1 1 d . . .
C1 C 0.14533(15) 0.13145(13) 0.89518(13) 0.0238(3) Uani 1 1 d . . .
H1A H 0.1850 0.0725 0.9023 0.029 Uiso 1 1 calc R . .
C2 C 0.03503(15) 0.12979(13) 0.87960(13) 0.0242(4) Uani 1 1 d . . .
C3 C -0.02388(15) 0.21756(14) 0.87076(13) 0.0232(4) Uani 1 1 d . . .
C4 C 0.02810(14) 0.30728(13) 0.87661(12) 0.0215(3) Uani 1 1 d . . .
H4A H -0.0111 0.3666 0.8709 0.026 Uiso 1 1 calc R . .
C5 C 0.13913(13) 0.30920(13) 0.89104(11) 0.0198(3) Uani 1 1 d . . .
C6 C 0.19530(14) 0.22263(13) 0.90001(12) 0.0212(3) Uani 1 1 d . . .
C7 C 0.21166(13) 0.39617(13) 0.90368(12) 0.0203(3) Uani 1 1 d . . .
C8 C 0.32466(13) 0.34964(12) 0.89398(12) 0.0197(3) Uani 1 1 d . . .
H8A H 0.3725 0.3752 0.9456 0.024 Uiso 1 1 calc R . .
C9 C 0.38771(15) 0.17884(14) 0.89207(13) 0.0240(4) Uani 1 1 d . . .
C10 C 0.49514(15) 0.22495(14) 0.86877(13) 0.0259(4) Uani 1 1 d . . .
H10A H 0.5383 0.1759 0.8336 0.031 Uiso 1 1 calc R . .
H10B H 0.5325 0.2382 0.9299 0.031 Uiso 1 1 calc R . .
C11 C 0.49511(15) 0.32051(15) 0.80985(14) 0.0272(4) Uani 1 1 d . . .
H11A H 0.5268 0.3071 0.7455 0.033 Uiso 1 1 calc R . .
C12 C 0.58900(18) 0.47475(18) 0.8151(2) 0.0414(5) Uani 1 1 d . . .
H12A H 0.5894 0.4645 0.7450 0.050 Uiso 1 1 calc R . .
H12B H 0.6615 0.4965 0.8344 0.050 Uiso 1 1 calc R . .
C13 C 0.50945(18) 0.55331(16) 0.83937(18) 0.0361(5) Uani 1 1 d . . .
H13A H 0.5326 0.6092 0.8743 0.043 Uiso 1 1 calc R . .
C14 C 0.40641(16) 0.54646(15) 0.81291(15) 0.0298(4) Uani 1 1 d . . .
C15 C 0.32275(17) 0.62020(14) 0.84247(15) 0.0300(4) Uani 1 1 d . . .
H15A H 0.3553 0.6684 0.8867 0.036 Uiso 1 1 calc R . .
H15B H 0.2974 0.6561 0.7852 0.036 Uiso 1 1 calc R . .
C16 C 0.25613(17) 0.54275(13) 0.98916(13) 0.0261(4) Uani 1 1 d . . .
H16A H 0.2288 0.5915 1.0356 0.031 Uiso 1 1 calc R . .
H16B H 0.3345 0.5360 0.9979 0.031 Uiso 1 1 calc R . .
C17 C 0.20033(15) 0.44410(13) 1.00285(12) 0.0227(3) Uani 1 1 d . . .
H17A H 0.1241 0.4529 1.0203 0.027 Uiso 1 1 calc R . .
H17B H 0.2363 0.4046 1.0528 0.027 Uiso 1 1 calc R . .
C18 C 0.38056(14) 0.35946(14) 0.79706(12) 0.0231(3) Uani 1 1 d . . .
H18A H 0.3437 0.3124 0.7532 0.028 Uiso 1 1 calc R . .
C19 C 0.36424(16) 0.46181(15) 0.75320(13) 0.0264(4) Uani 1 1 d . . .
H19A H 0.3996 0.4636 0.6890 0.032 Uiso 1 1 calc R . .
C20 C 0.24310(16) 0.47442(15) 0.73961(12) 0.0257(4) Uani 1 1 d . . .
H20A H 0.2285 0.5336 0.7009 0.031 Uiso 1 1 calc R . .
H20B H 0.2133 0.4170 0.7056 0.031 Uiso 1 1 calc R . .
C21 C 0.19100(14) 0.48423(13) 0.83739(12) 0.0223(4) Uani 1 1 d . . .
H21A H 0.1119 0.4910 0.8282 0.027 Uiso 1 1 calc R . .
C22 C 0.03454(19) -0.04418(15) 0.8709(2) 0.0403(5) Uani 1 1 d . . .
H22A H -0.0156 -0.0990 0.8646 0.060 Uiso 1 1 calc R . .
H22B H 0.0745 -0.0507 0.9309 0.060 Uiso 1 1 calc R . .
H22C H 0.0847 -0.0447 0.8169 0.060 Uiso 1 1 calc R . .
C23 C -0.19322(14) 0.29326(14) 0.84707(14) 0.0272(4) Uani 1 1 d . . .
H23A H -0.2688 0.2762 0.8381 0.041 Uiso 1 1 calc R . .
H23B H -0.1676 0.3298 0.7913 0.041 Uiso 1 1 calc R . .
H23C H -0.1855 0.3338 0.9045 0.041 Uiso 1 1 calc R . .
O5 O 0.0614(15) 0.7169(18) 0.8847(12) 0.032(2) Uani 0.402(7) 1 d PU A 1
H5A H 0.1070 0.6719 0.8892 0.048 Uiso 0.402(7) 1 calc PR A 1
O6 O -0.0108(3) 0.5648(3) 1.0307(3) 0.0382(13) Uani 0.402(7) 1 d PU A 1
H6 H -0.0499 0.5190 1.0506 0.057 Uiso 0.402(7) 1 calc PR A 1
C24 C 0.0043(17) 0.7224(14) 0.9667(13) 0.030(2) Uani 0.402(7) 1 d PU A 1
H24A H -0.0361 0.7848 0.9654 0.036 Uiso 0.402(7) 1 calc PR A 1
H24B H 0.0559 0.7268 1.0203 0.036 Uiso 0.402(7) 1 calc PR A 1
C25 C -0.0761(8) 0.6399(8) 0.9910(7) 0.0326(18) Uani 0.402(7) 1 d PU A 1
H25A H -0.1293 0.6633 1.0393 0.039 Uiso 0.402(7) 1 calc PR A 1
C26 C -0.1359(13) 0.5983(13) 0.8995(14) 0.032(2) Uani 0.402(7) 1 d PU A 1
H26A H -0.0828 0.5762 0.8515 0.039 Uiso 0.402(7) 1 calc PR A 1
H26B H -0.1807 0.5414 0.9177 0.039 Uiso 0.402(7) 1 calc PR A 1
C27 C -0.2071(13) 0.6796(14) 0.8563(8) 0.035(2) Uani 0.402(7) 1 d PU A 1
H27A H -0.2443 0.6542 0.7997 0.053 Uiso 0.402(7) 1 calc PR A 1
H27B H -0.1623 0.7355 0.8379 0.053 Uiso 0.402(7) 1 calc PR A 1
H27C H -0.2600 0.7007 0.9038 0.053 Uiso 0.402(7) 1 calc PR A 1
O51 O 0.0798(15) 0.7224(17) 0.8986(13) 0.046(3) Uani 0.441(7) 1 d PU B 2
H51 H 0.1170 0.6715 0.8926 0.069 Uiso 0.441(7) 1 calc PR B 2
O61 O -0.1104(4) 0.6159(3) 1.0597(3) 0.0508(14) Uani 0.441(7) 1 d PU B 2
H61 H -0.1186 0.5576 1.0775 0.076 Uiso 0.441(7) 1 calc PR B 2
C241 C 0.008(2) 0.7117(18) 0.9823(15) 0.049(4) Uani 0.441(7) 1 d PU B 2
H24C H 0.0499 0.7120 1.0422 0.059 Uiso 0.441(7) 1 calc PR B 2
H24D H -0.0438 0.7669 0.9845 0.059 Uiso 0.441(7) 1 calc PR B 2
C251 C -0.0508(8) 0.6178(7) 0.9727(7) 0.0370(18) Uani 0.441(7) 1 d PU B 2
H25B H 0.0015 0.5623 0.9719 0.044 Uiso 0.441(7) 1 calc PR B 2
C261 C -0.1191(15) 0.6109(16) 0.8924(16) 0.048(3) Uani 0.441(7) 1 d PU B 2
H26C H -0.1519 0.5449 0.8934 0.058 Uiso 0.441(7) 1 calc PR B 2
H26D H -0.0736 0.6144 0.8346 0.058 Uiso 0.441(7) 1 calc PR B 2
C271 C -0.2067(16) 0.6826(14) 0.8803(11) 0.053(3) Uani 0.441(7) 1 d PU B 2
H27D H -0.2506 0.6641 0.8250 0.079 Uiso 0.441(7) 1 calc PR B 2
H27E H -0.1763 0.7479 0.8698 0.079 Uiso 0.441(7) 1 calc PR B 2
H27F H -0.2514 0.6834 0.9379 0.079 Uiso 0.441(7) 1 calc PR B 2
O1W O 0.1604(12) 0.7697(9) 0.9129(10) 0.051(3) Uani 0.158(4) 1 d PU C 3

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0228(6) 0.0331(7) 0.0435(8) 0.0090(6) -0.0042(6) -0.0003(5)
O2 0.0290(6) 0.0195(6) 0.0427(8) -0.0019(5) -0.0023(6) -0.0034(5)
O3 0.0211(6) 0.0227(6) 0.0343(6) 0.0006(5) -0.0008(5) -0.0014(5)
O4 0.0328(7) 0.0216(6) 0.0414(8) 0.0001(6) -0.0020(6) 0.0055(5)
N1 0.0230(7) 0.0198(7) 0.0199(6) -0.0003(5) 0.0000(5) 0.0023(5)
N2 0.0284(7) 0.0185(6) 0.0269(7) 0.0036(6) -0.0015(6) -0.0004(6)
C1 0.0276(8) 0.0177(8) 0.0261(8) 0.0004(7) 0.0011(7) 0.0010(6)
C2 0.0286(9) 0.0185(8) 0.0255(8) 0.0005(6) -0.0018(6) -0.0020(6)
C3 0.0223(8) 0.0240(8) 0.0234(8) -0.0003(6) 0.0009(6) -0.0005(6)
C4 0.0237(8) 0.0204(8) 0.0204(7) 0.0007(6) 0.0007(6) 0.0015(6)
C5 0.0228(8) 0.0203(8) 0.0162(7) -0.0003(6) -0.0005(6) 0.0015(6)
C6 0.0241(8) 0.0210(8) 0.0186(7) -0.0001(6) -0.0003(6) -0.0001(6)
C7 0.0219(7) 0.0214(8) 0.0175(7) 0.0010(6) -0.0003(6) 0.0014(6)
C8 0.0210(7) 0.0208(7) 0.0173(7) 0.0021(6) -0.0005(6) -0.0002(6)
C9 0.0260(8) 0.0233(8) 0.0227(7) 0.0003(7) -0.0026(6) 0.0048(7)
C10 0.0246(8) 0.0285(9) 0.0245(8) -0.0005(7) 0.0003(7) 0.0060(7)
C11 0.0225(8) 0.0338(9) 0.0254(8) 0.0032(7) 0.0022(6) 0.0048(7)
C12 0.0243(9) 0.0383(11) 0.0615(14) 0.0142(11) 0.0010(9) -0.0016(8)
C13 0.0299(10) 0.0310(10) 0.0473(12) 0.0114(9) -0.0028(9) -0.0062(8)
C14 0.0300(9) 0.0288(9) 0.0307(9) 0.0122(8) 0.0004(7) -0.0029(7)
C15 0.0311(9) 0.0235(8) 0.0355(10) 0.0076(7) -0.0023(8) -0.0023(7)
C16 0.0333(9) 0.0198(8) 0.0252(8) -0.0015(6) -0.0047(7) 0.0004(7)
C17 0.0278(8) 0.0212(8) 0.0192(7) -0.0007(6) 0.0008(6) 0.0011(6)
C18 0.0237(8) 0.0270(8) 0.0185(7) 0.0014(6) 0.0006(6) 0.0034(6)
C19 0.0268(8) 0.0314(10) 0.0208(8) 0.0077(7) 0.0022(7) 0.0023(7)
C20 0.0276(9) 0.0304(9) 0.0190(7) 0.0061(7) -0.0010(7) 0.0046(7)
C21 0.0239(8) 0.0211(8) 0.0220(8) 0.0011(6) -0.0015(6) 0.0020(6)
C22 0.0382(11) 0.0198(9) 0.0629(15) -0.0017(9) -0.0066(10) -0.0018(8)
C23 0.0227(8) 0.0246(9) 0.0344(9) 0.0028(7) -0.0011(7) 0.0003(7)
O5 0.032(4) 0.032(3) 0.033(3) 0.011(3) 0.001(3) 0.009(3)
O6 0.0292(18) 0.033(2) 0.052(2) 0.0208(18) -0.0021(16) -0.0018(15)
C24 0.042(3) 0.023(4) 0.026(5) 0.007(3) 0.001(3) -0.011(3)
C25 0.028(4) 0.032(4) 0.038(4) 0.007(3) 0.003(3) 0.000(3)
C26 0.031(4) 0.013(4) 0.053(5) 0.007(3) -0.015(4) -0.012(3)
C27 0.037(3) 0.042(4) 0.027(4) 0.010(3) -0.006(3) 0.009(3)
O51 0.045(6) 0.035(3) 0.058(6) 0.009(5) 0.014(4) 0.012(4)
O61 0.084(3) 0.0295(19) 0.039(2) 0.0005(15) 0.021(2) -0.0041(19)
C241 0.064(5) 0.042(6) 0.042(7) 0.007(4) 0.012(5) 0.002(4)
C251 0.036(4) 0.027(4) 0.048(4) 0.002(3) 0.009(3) 0.000(3)
C261 0.050(6) 0.032(6) 0.063(4) 0.011(4) 0.002(4) -0.008(4)
C271 0.060(4) 0.037(3) 0.062(7) 0.016(5) -0.007(5) -0.006(3)
O1W 0.059(6) 0.041(5) 0.054(6) -0.003(5) 0.002(5) 0.008(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.427(3) . ?
O1 C12 1.428(3) . ?
O2 C2 1.365(2) . ?
O2 C22 1.425(2) . ?
O3 C3 1.367(2) . ?
O3 C23 1.426(2) . ?
O4 C9 1.228(3) . ?
N1 C9 1.361(2) . ?
N1 C6 1.417(2) . ?
N1 C8 1.488(2) . ?
N2 C15 1.477(2) . ?
N2 C16 1.482(2) . ?
N2 C21 1.499(2) . ?
C1 C6 1.394(2) . ?
C1 C2 1.394(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.411(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.401(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(2) . ?
C5 C7 1.503(2) . ?
C7 C21 1.540(2) . ?
C7 C17 1.540(2) . ?
C7 C8 1.553(2) . ?
C8 C18 1.530(2) . ?
C8 H8A 1.0000 . ?
C9 C10 1.517(3) . ?
C10 C11 1.543(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C18 1.536(2) . ?
C11 H11A 1.0000 . ?
C12 C13 1.500(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.341(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.508(3) . ?
C14 C19 1.519(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.528(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.539(3) . ?
C18 H18A 1.0000 . ?
C19 C20 1.534(3) . ?
C19 H19A 1.0000 . ?
C20 C21 1.520(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O5 C24 1.35(3) . ?
O5 H5A 0.8400 . ?
O6 C25 1.422(10) . ?
O6 H6 0.8400 . ?
C24 C25 1.55(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.586(19) . ?
C25 H25A 1.0000 . ?
C26 C27 1.54(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O51 C241 1.48(3) . ?
O51 H51 0.8400 . ?
O61 C251 1.427(11) . ?
O61 H61 0.8400 . ?
C241 C251 1.48(3) . ?
C241 H24C 0.9900 . ?
C241 H24D 0.9900 . ?
C251 C261 1.41(2) . ?
C251 H25B 1.0000 . ?
C261 C271 1.48(3) . ?
C261 H26C 0.9900 . ?
C261 H26D 0.9900 . ?
C271 H27D 0.9800 . ?
C271 H27E 0.9800 . ?
C271 H27F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 115.21(17) . . ?
C2 O2 C22 116.86(16) . . ?
C3 O3 C23 116.58(15) . . ?
C9 N1 C6 126.21(16) . . ?
C9 N1 C8 119.44(15) . . ?
C6 N1 C8 109.39(14) . . ?
C15 N2 C16 111.99(16) . . ?
C15 N2 C21 112.97(15) . . ?
C16 N2 C21 107.83(13) . . ?
C6 C1 C2 117.64(17) . . ?
C6 C1 H1A 121.2 . . ?
C2 C1 H1A 121.2 . . ?
O2 C2 C1 123.76(17) . . ?
O2 C2 C3 115.28(16) . . ?
C1 C2 C3 120.96(17) . . ?
O3 C3 C4 124.75(17) . . ?
O3 C3 C2 115.23(16) . . ?
C4 C3 C2 120.02(17) . . ?
C3 C4 C5 119.16(16) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C6 C5 C4 119.99(16) . . ?
C6 C5 C7 111.08(14) . . ?
C4 C5 C7 128.86(16) . . ?
C5 C6 C1 122.21(16) . . ?
C5 C6 N1 109.64(15) . . ?
C1 C6 N1 128.04(16) . . ?
C5 C7 C21 116.42(14) . . ?
C5 C7 C17 112.72(14) . . ?
C21 C7 C17 101.24(13) . . ?
C5 C7 C8 102.33(13) . . ?
C21 C7 C8 114.76(14) . . ?
C17 C7 C8 109.63(14) . . ?
N1 C8 C18 105.98(14) . . ?
N1 C8 C7 104.36(13) . . ?
C18 C8 C7 117.11(14) . . ?
N1 C8 H8A 109.7 . . ?
C18 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O4 C9 N1 122.40(18) . . ?
O4 C9 C10 122.15(17) . . ?
N1 C9 C10 115.44(16) . . ?
C9 C10 C11 117.74(15) . . ?
C9 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
C9 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
O1 C11 C18 114.57(16) . . ?
O1 C11 C10 104.17(15) . . ?
C18 C11 C10 110.80(15) . . ?
O1 C11 H11A 109.0 . . ?
C18 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
O1 C12 C13 112.07(19) . . ?
O1 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 122.8(2) . . ?
C13 C14 C19 122.5(2) . . ?
C15 C14 C19 114.72(17) . . ?
N2 C15 C14 111.72(15) . . ?
N2 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C17 105.27(15) . . ?
N2 C16 H16A 110.7 . . ?
C17 C16 H16A 110.7 . . ?
N2 C16 H16B 110.7 . . ?
C17 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C7 102.70(14) . . ?
C16 C17 H17A 111.2 . . ?
C7 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C7 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C8 C18 C11 106.92(14) . . ?
C8 C18 C19 111.84(14) . . ?
C11 C18 C19 118.92(16) . . ?
C8 C18 H18A 106.1 . . ?
C11 C18 H18A 106.1 . . ?
C19 C18 H18A 106.1 . . ?
C14 C19 C20 108.92(17) . . ?
C14 C19 C18 115.18(15) . . ?
C20 C19 C18 106.35(16) . . ?
C14 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C21 C20 C19 108.69(14) . . ?
C21 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
C21 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.3 . . ?
N2 C21 C20 111.76(15) . . ?
N2 C21 C7 106.25(13) . . ?
C20 C21 C7 113.64(15) . . ?
N2 C21 H21A 108.3 . . ?
C20 C21 H21A 108.3 . . ?
C7 C21 H21A 108.3 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 O5 H5A 109.5 . . ?
C25 O6 H6 109.5 . . ?
O5 C24 C25 119.2(16) . . ?
O5 C24 H24A 107.5 . . ?
C25 C24 H24A 107.5 . . ?
O5 C24 H24B 107.5 . . ?
C25 C24 H24B 107.5 . . ?
H24A C24 H24B 107.0 . . ?
O6 C25 C24 103.9(10) . . ?
O6 C25 C26 109.1(9) . . ?
C24 C25 C26 112.9(11) . . ?
O6 C25 H25A 110.3 . . ?
C24 C25 H25A 110.3 . . ?
C26 C25 H25A 110.3 . . ?
C27 C26 C25 109.2(13) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C241 O51 H51 109.5 . . ?
C251 O61 H61 109.5 . . ?
C251 C241 O51 108.2(18) . . ?
C251 C241 H24C 110.1 . . ?
O51 C241 H24C 110.1 . . ?
C251 C241 H24D 110.1 . . ?
O51 C241 H24D 110.1 . . ?
H24C C241 H24D 108.4 . . ?
C261 C251 O61 111.2(11) . . ?
C261 C251 C241 115.3(13) . . ?
O61 C251 C241 101.2(11) . . ?
C261 C251 H25B 109.6 . . ?
O61 C251 H25B 109.6 . . ?
C241 C251 H25B 109.6 . . ?
C251 C261 C271 119.6(17) . . ?
C251 C261 H26C 107.4 . . ?
C271 C261 H26C 107.4 . . ?
C251 C261 H26D 107.4 . . ?
C271 C261 H26D 107.4 . . ?
H26C C261 H26D 106.9 . . ?
C261 C271 H27D 109.5 . . ?
C261 C271 H27E 109.5 . . ?
H27D C271 H27E 109.5 . . ?
C261 C271 H27F 109.5 . . ?
H27D C271 H27F 109.5 . . ?
H27E C271 H27F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 O2 C2 C1 -5.2(3) . . . . ?
C22 O2 C2 C3 174.4(2) . . . . ?
C6 C1 C2 O2 178.49(17) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C23 O3 C3 C4 1.7(3) . . . . ?
C23 O3 C3 C2 -179.06(16) . . . . ?
O2 C2 C3 O3 1.8(2) . . . . ?
C1 C2 C3 O3 -178.63(17) . . . . ?
O2 C2 C3 C4 -178.97(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
O3 C3 C4 C5 179.38(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C7 -177.23(16) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C7 C5 C6 C1 177.30(16) . . . . ?
C4 C5 C6 N1 176.55(15) . . . . ?
C7 C5 C6 N1 -6.19(19) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C6 N1 -175.07(17) . . . . ?
C9 N1 C6 C5 -160.64(16) . . . . ?
C8 N1 C6 C5 -6.01(19) . . . . ?
C9 N1 C6 C1 15.6(3) . . . . ?
C8 N1 C6 C1 170.24(17) . . . . ?
C6 C5 C7 C21 140.90(15) . . . . ?
C4 C5 C7 C21 -42.1(2) . . . . ?
C6 C5 C7 C17 -102.74(17) . . . . ?
C4 C5 C7 C17 74.2(2) . . . . ?
C6 C5 C7 C8 14.92(18) . . . . ?
C4 C5 C7 C8 -168.13(17) . . . . ?
C9 N1 C8 C18 47.4(2) . . . . ?
C6 N1 C8 C18 -109.26(15) . . . . ?
C9 N1 C8 C7 171.59(14) . . . . ?
C6 N1 C8 C7 14.98(17) . . . . ?
C5 C7 C8 N1 -17.35(16) . . . . ?
C21 C7 C8 N1 -144.40(14) . . . . ?
C17 C7 C8 N1 102.49(15) . . . . ?
C5 C7 C8 C18 99.42(16) . . . . ?
C21 C7 C8 C18 -27.6(2) . . . . ?
C17 C7 C8 C18 -140.74(15) . . . . ?
C6 N1 C9 O4 -23.3(3) . . . . ?
C8 N1 C9 O4 -175.63(17) . . . . ?
C6 N1 C9 C10 157.67(16) . . . . ?
C8 N1 C9 C10 5.3(2) . . . . ?
O4 C9 C10 C11 145.99(19) . . . . ?
N1 C9 C10 C11 -35.0(2) . . . . ?
C12 O1 C11 C18 -66.1(2) . . . . ?
C12 O1 C11 C10 172.66(17) . . . . ?
C9 C10 C11 O1 131.57(16) . . . . ?
C9 C10 C11 C18 7.9(2) . . . . ?
C11 O1 C12 C13 89.1(2) . . . . ?
O1 C12 C13 C14 -65.0(3) . . . . ?
C12 C13 C14 C15 175.26(19) . . . . ?
C12 C13 C14 C19 -2.8(3) . . . . ?
C16 N2 C15 C14 75.5(2) . . . . ?
C21 N2 C15 C14 -46.5(2) . . . . ?
C13 C14 C15 N2 -125.4(2) . . . . ?
C19 C14 C15 N2 52.8(2) . . . . ?
C15 N2 C16 C17 -141.34(16) . . . . ?
C21 N2 C16 C17 -16.46(19) . . . . ?
N2 C16 C17 C7 35.75(18) . . . . ?
C5 C7 C17 C16 -165.38(14) . . . . ?
C21 C7 C17 C16 -40.28(17) . . . . ?
C8 C7 C17 C16 81.34(16) . . . . ?
N1 C8 C18 C11 -71.59(17) . . . . ?
C7 C8 C18 C11 172.53(15) . . . . ?
N1 C8 C18 C19 156.61(15) . . . . ?
C7 C8 C18 C19 40.7(2) . . . . ?
O1 C11 C18 C8 -74.13(19) . . . . ?
C10 C11 C18 C8 43.4(2) . . . . ?
O1 C11 C18 C19 53.6(2) . . . . ?
C10 C11 C18 C19 171.13(15) . . . . ?
C13 C14 C19 C20 177.61(19) . . . . ?
C15 C14 C19 C20 -0.6(2) . . . . ?
C13 C14 C19 C18 58.3(3) . . . . ?
C15 C14 C19 C18 -119.94(18) . . . . ?
C8 C18 C19 C14 60.0(2) . . . . ?
C11 C18 C19 C14 -65.5(2) . . . . ?
C8 C18 C19 C20 -60.78(18) . . . . ?
C11 C18 C19 C20 173.79(15) . . . . ?
C14 C19 C20 C21 -54.8(2) . . . . ?
C18 C19 C20 C21 69.93(19) . . . . ?
C15 N2 C21 C20 -9.5(2) . . . . ?
C16 N2 C21 C20 -133.84(16) . . . . ?
C15 N2 C21 C7 114.93(16) . . . . ?
C16 N2 C21 C7 -9.36(18) . . . . ?
C19 C20 C21 N2 61.92(19) . . . . ?
C19 C20 C21 C7 -58.3(2) . . . . ?
C5 C7 C21 N2 153.42(15) . . . . ?
C17 C7 C21 N2 30.85(17) . . . . ?
C8 C7 C21 N2 -87.11(17) . . . . ?
C5 C7 C21 C20 -83.27(19) . . . . ?
C17 C7 C21 C20 154.15(15) . . . . ?
C8 C7 C21 C20 36.2(2) . . . . ?
O5 C24 C25 O6 81.4(18) . . . . ?
O5 C24 C25 C26 -37(2) . . . . ?
O6 C25 C26 C27 179.8(11) . . . . ?
C24 C25 C26 C27 -65.2(17) . . . . ?
O51 C241 C251 C261 -63(2) . . . . ?
O51 C241 C251 O61 176.7(14) . . . . ?
O61 C251 C261 C271 55.9(18) . . . . ?
C241 C251 C261 C271 -59(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        78.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.071

#==== end of cif

_database_code_depnum_ccdc_archive 'CCDC 930496'