# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#
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#                                CCDC 
# 
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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, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_1.CIF
_database_code_depnum_ccdc_archive 'CCDC 898737'
#TrackingRef '13608_web_deposit_cif_file_0_DeliaHaynes_1346229442.submission.CIF'


_audit_update_record             
;
2012-08-28 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            \1
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O6, C6 H14 N2, 2(H2 O)'
_chemical_formula_sum            'C29 H32 N2 O8'
_chemical_formula_weight         536.57

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           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3417(10)
_cell_length_b                   12.4564(8)
_cell_length_c                   13.9070(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8180(10)
_cell_angle_gamma                90.00
_cell_volume                     2484.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6854
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.77

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   'SADABS, 2009'

_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  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14685
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.95
_reflns_number_total             5393
_reflns_number_gt                4673
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)'
_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^)+(0.0547P)^2^+1.0435P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5393
_refine_ls_number_parameters     384
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.052
_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
O3 O 0.44536(6) 0.82530(7) 0.37113(7) 0.0170(2) Uani 1 1 d . . .
O2 O 0.57960(6) 0.80177(8) 0.30743(7) 0.0193(2) Uani 1 1 d . . .
O5 O -0.04150(6) 0.73867(8) 0.44088(7) 0.0207(2) Uani 1 1 d . . .
O1 O 0.56320(6) 0.69794(7) 0.17182(7) 0.0191(2) Uani 1 1 d . . .
O4 O 0.07862(6) 0.79019(8) 0.36479(7) 0.0175(2) Uani 1 1 d . . .
O6 O -0.00753(6) 0.61986(8) 0.56864(7) 0.0198(2) Uani 1 1 d . . .
C2 C 0.43467(8) 0.71057(10) 0.22785(9) 0.0138(2) Uani 1 1 d . . .
C14 C 0.14090(8) 0.72244(10) 0.43206(9) 0.0138(2) Uani 1 1 d . . .
C15 C 0.11124(8) 0.66242(10) 0.50263(9) 0.0142(2) Uani 1 1 d . . .
N4A N 0.84554(7) 0.81817(9) 0.09754(8) 0.0149(2) Uani 1 1 d . . .
C22 C 0.29498(8) 0.64439(10) 0.50426(9) 0.0136(2) Uani 1 1 d . . .
C11 C 0.38393(8) 0.63878(10) 0.15431(9) 0.0147(2) Uani 1 1 d . . .
H11 H 0.4113 0.6076 0.1095 0.018 Uiso 1 1 calc R . .
N1A N 0.71095(7) 0.76741(9) 0.15072(8) 0.0167(2) Uani 1 1 d . . .
C12 C 0.26116(9) 0.78521(10) 0.35992(10) 0.0153(3) Uani 1 1 d . . .
H12A H 0.2061 0.8268 0.3169 0.018 Uiso 1 1 calc R . .
H12B H 0.3072 0.8373 0.4032 0.018 Uiso 1 1 calc R . .
C18 C 0.33175(9) 0.52281(10) 0.65369(10) 0.0166(3) Uani 1 1 d . . .
H18 H 0.3128 0.4865 0.7031 0.020 Uiso 1 1 calc R . .
C3 C 0.39363(8) 0.75672(10) 0.29583(9) 0.0135(2) Uani 1 1 d . . .
C23 C 0.01403(8) 0.67470(10) 0.50318(10) 0.0154(2) Uani 1 1 d . . .
C5 C 0.25065(8) 0.65902(10) 0.21065(9) 0.0137(2) Uani 1 1 d . . .
C1 C 0.53235(8) 0.73978(10) 0.23745(10) 0.0147(2) Uani 1 1 d . . .
C4 C 0.30343(8) 0.73170(10) 0.28875(9) 0.0136(2) Uani 1 1 d . . .
C20 C 0.44976(8) 0.56693(10) 0.58433(10) 0.0169(3) Uani 1 1 d . . .
H20 H 0.5118 0.5584 0.5860 0.020 Uiso 1 1 calc R . .
C16 C 0.17363(8) 0.59662(10) 0.57318(9) 0.0147(2) Uani 1 1 d . . .
H16 H 0.1540 0.5570 0.6203 0.018 Uiso 1 1 calc R . .
C17 C 0.26631(8) 0.58689(10) 0.57693(9) 0.0143(2) Uani 1 1 d . . .
C21 C 0.38944(8) 0.63169(10) 0.51100(10) 0.0163(3) Uani 1 1 d . . .
H21 H 0.4108 0.6687 0.4639 0.020 Uiso 1 1 calc R . .
C13 C 0.23080(8) 0.71357(10) 0.43107(9) 0.0135(2) Uani 1 1 d . . .
C6 C 0.15605(8) 0.63283(10) 0.19502(10) 0.0159(3) Uani 1 1 d . . .
H6 H 0.1262 0.6657 0.2367 0.019 Uiso 1 1 calc R . .
C7 C 0.10768(9) 0.56088(11) 0.12069(10) 0.0184(3) Uani 1 1 d . . .
H7 H 0.0448 0.5444 0.1118 0.022 Uiso 1 1 calc R . .
C10 C 0.29179(8) 0.61034(10) 0.14395(9) 0.0145(2) Uani 1 1 d . . .
C9 C 0.23976(9) 0.53569(11) 0.06781(10) 0.0183(3) Uani 1 1 d . . .
H9 H 0.2676 0.5029 0.0241 0.022 Uiso 1 1 calc R . .
C3A C 0.76229(9) 0.79784(11) 0.00357(10) 0.0188(3) Uani 1 1 d . . .
H3A1 H 0.7765 0.7415 -0.0388 0.023 Uiso 1 1 calc R . .
H3A2 H 0.7448 0.8642 -0.0381 0.023 Uiso 1 1 calc R . .
C8 C 0.14989(9) 0.51082(11) 0.05704(10) 0.0201(3) Uani 1 1 d . . .
H8 H 0.1159 0.4599 0.0068 0.024 Uiso 1 1 calc R . .
C8A C 0.86957(9) 0.71828(11) 0.16074(10) 0.0179(3) Uani 1 1 d . . .
H8A1 H 0.9282 0.7289 0.2201 0.022 Uiso 1 1 calc R . .
H8A2 H 0.8789 0.6582 0.1188 0.022 Uiso 1 1 calc R . .
C5A C 0.82653(9) 0.90731(11) 0.15944(11) 0.0203(3) Uani 1 1 d . . .
H5A1 H 0.8159 0.9751 0.1198 0.024 Uiso 1 1 calc R . .
H5A2 H 0.8809 0.9174 0.2237 0.024 Uiso 1 1 calc R . .
C2A C 0.68160(9) 0.76158(12) 0.03638(10) 0.0204(3) Uani 1 1 d . . .
H2A1 H 0.6268 0.8084 0.0043 0.024 Uiso 1 1 calc R . .
H2A2 H 0.6637 0.6870 0.0130 0.024 Uiso 1 1 calc R . .
C19 C 0.42163(9) 0.51271(10) 0.65740(10) 0.0177(3) Uani 1 1 d . . .
H19 H 0.4648 0.4695 0.7088 0.021 Uiso 1 1 calc R . .
C6A C 0.74008(10) 0.87936(12) 0.18516(13) 0.0279(3) Uani 1 1 d . . .
H6A1 H 0.7545 0.8855 0.2602 0.033 Uiso 1 1 calc R . .
H6A2 H 0.6888 0.9299 0.1499 0.033 Uiso 1 1 calc R . .
C7A C 0.78973(9) 0.69175(12) 0.19878(11) 0.0233(3) Uani 1 1 d . . .
H7A1 H 0.7686 0.6170 0.1801 0.028 Uiso 1 1 calc R . .
H7A2 H 0.8116 0.6983 0.2746 0.028 Uiso 1 1 calc R . .
O7 O 0.06563(8) 0.50455(9) 0.76123(9) 0.0262(2) Uani 1 1 d . . .
O8 O 0.60675(8) 0.52666(9) 0.06674(10) 0.0338(3) Uani 1 1 d D . .
H7W2 H 0.0773(15) 0.5614(19) 0.7984(17) 0.050(6) Uiso 1 1 d . . .
H4 H 0.0275(15) 0.7848(16) 0.3819(16) 0.045(6) Uiso 1 1 d . . .
H4A H 0.9014(13) 0.8395(15) 0.0789(14) 0.038(5) Uiso 1 1 d . . .
H7W1 H 0.0477(14) 0.5296(16) 0.7010(17) 0.040(6) Uiso 1 1 d . . .
H3 H 0.5002(16) 0.8295(18) 0.3611(17) 0.055(6) Uiso 1 1 d . . .
H1A H 0.6539(16) 0.7399(18) 0.1720(17) 0.058(7) Uiso 1 1 d . . .
H8W1 H 0.5710(18) 0.585(2) 0.094(2) 0.082(8) Uiso 1 1 d . . .
H8W2 H 0.585(2) 0.4565(18) 0.084(2) 0.109(11) Uiso 1 1 d D . .

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
O3 0.0130(4) 0.0210(5) 0.0183(5) -0.0033(4) 0.0071(4) -0.0033(4)
O2 0.0133(4) 0.0255(5) 0.0202(5) -0.0015(4) 0.0073(4) -0.0029(4)
O5 0.0129(4) 0.0285(5) 0.0222(5) 0.0047(4) 0.0081(4) 0.0032(4)
O1 0.0152(4) 0.0224(5) 0.0244(5) -0.0027(4) 0.0127(4) -0.0015(4)
O4 0.0116(4) 0.0234(5) 0.0187(5) 0.0045(4) 0.0068(4) 0.0028(4)
O6 0.0157(4) 0.0248(5) 0.0237(5) 0.0035(4) 0.0132(4) 0.0020(4)
C2 0.0115(5) 0.0153(6) 0.0157(6) 0.0049(5) 0.0062(5) 0.0015(4)
C14 0.0123(6) 0.0154(6) 0.0135(6) -0.0019(5) 0.0042(5) 0.0002(4)
C15 0.0126(6) 0.0167(6) 0.0152(6) -0.0034(5) 0.0071(5) -0.0011(5)
N4A 0.0128(5) 0.0169(5) 0.0175(5) -0.0011(4) 0.0084(4) -0.0004(4)
C22 0.0127(6) 0.0148(6) 0.0139(6) -0.0041(5) 0.0056(4) -0.0008(4)
C11 0.0145(6) 0.0164(6) 0.0149(6) 0.0029(5) 0.0074(5) 0.0026(5)
N1A 0.0127(5) 0.0226(6) 0.0169(5) -0.0018(4) 0.0076(4) -0.0021(4)
C12 0.0137(6) 0.0157(6) 0.0189(6) 0.0001(5) 0.0087(5) -0.0001(5)
C18 0.0177(6) 0.0158(6) 0.0164(6) -0.0003(5) 0.0060(5) -0.0010(5)
C3 0.0133(6) 0.0139(6) 0.0136(6) 0.0021(4) 0.0051(5) 0.0004(4)
C23 0.0127(6) 0.0190(6) 0.0160(6) -0.0030(5) 0.0069(5) -0.0012(5)
C5 0.0126(6) 0.0145(6) 0.0144(6) 0.0046(5) 0.0054(4) 0.0011(4)
C1 0.0126(6) 0.0160(6) 0.0169(6) 0.0044(5) 0.0069(5) 0.0022(5)
C4 0.0125(6) 0.0152(6) 0.0139(6) 0.0031(5) 0.0058(5) 0.0020(4)
C20 0.0112(6) 0.0191(6) 0.0204(6) -0.0042(5) 0.0056(5) 0.0009(5)
C16 0.0147(6) 0.0163(6) 0.0149(6) -0.0019(5) 0.0074(5) -0.0016(5)
C17 0.0146(6) 0.0140(6) 0.0148(6) -0.0032(5) 0.0057(5) -0.0005(4)
C21 0.0142(6) 0.0191(6) 0.0172(6) -0.0014(5) 0.0076(5) 0.0003(5)
C13 0.0130(6) 0.0152(6) 0.0134(6) -0.0023(5) 0.0061(5) -0.0013(4)
C6 0.0134(6) 0.0196(6) 0.0157(6) 0.0042(5) 0.0065(5) 0.0015(5)
C7 0.0114(6) 0.0234(7) 0.0196(6) 0.0036(5) 0.0046(5) -0.0019(5)
C10 0.0140(6) 0.0156(6) 0.0143(6) 0.0032(5) 0.0056(5) 0.0014(5)
C9 0.0189(6) 0.0199(6) 0.0173(6) -0.0005(5) 0.0077(5) 0.0004(5)
C3A 0.0162(6) 0.0262(7) 0.0147(6) 0.0008(5) 0.0062(5) -0.0004(5)
C8 0.0176(6) 0.0215(7) 0.0187(6) -0.0030(5) 0.0032(5) -0.0039(5)
C8A 0.0151(6) 0.0208(6) 0.0193(6) 0.0028(5) 0.0078(5) 0.0022(5)
C5A 0.0188(6) 0.0193(6) 0.0270(7) -0.0064(5) 0.0134(5) -0.0018(5)
C2A 0.0147(6) 0.0286(7) 0.0173(6) 0.0011(5) 0.0050(5) -0.0029(5)
C19 0.0162(6) 0.0151(6) 0.0194(6) 0.0001(5) 0.0034(5) 0.0030(5)
C6A 0.0241(7) 0.0282(8) 0.0397(9) -0.0152(7) 0.0216(7) -0.0080(6)
C7A 0.0147(6) 0.0307(7) 0.0245(7) 0.0110(6) 0.0069(5) 0.0011(5)
O7 0.0301(6) 0.0219(5) 0.0274(6) 0.0027(5) 0.0112(5) 0.0005(4)
O8 0.0364(6) 0.0257(6) 0.0489(7) -0.0005(5) 0.0271(6) -0.0015(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
O3 C3 1.3659(15) . ?
O3 H3 0.90(2) . ?
O2 C1 1.2520(16) . ?
O5 C23 1.2597(16) . ?
O1 C1 1.2790(16) . ?
O4 C14 1.3657(15) . ?
O4 H4 0.90(2) . ?
O6 C23 1.2722(16) . ?
C2 C11 1.3732(18) . ?
C2 C3 1.4295(17) . ?
C2 C1 1.5013(16) . ?
C14 C13 1.3885(17) . ?
C14 C15 1.4306(17) . ?
C15 C16 1.3723(17) . ?
C15 C23 1.5019(16) . ?
N4A C3A 1.4889(16) . ?
N4A C8A 1.4920(16) . ?
N4A C5A 1.4958(16) . ?
N4A H4A 1.01(2) . ?
C22 C13 1.4268(17) . ?
C22 C21 1.4274(16) . ?
C22 C17 1.4296(17) . ?
C11 C10 1.4141(17) . ?
C11 H11 0.9500 . ?
N1A C7A 1.4904(17) . ?
N1A C6A 1.4905(18) . ?
N1A C2A 1.4925(17) . ?
N1A H1A 1.07(2) . ?
C12 C4 1.5168(17) . ?
C12 C13 1.5232(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C18 C19 1.3672(18) . ?
C18 C17 1.4222(17) . ?
C18 H18 0.9500 . ?
C3 C4 1.3874(17) . ?
C5 C4 1.4248(17) . ?
C5 C6 1.4267(17) . ?
C5 C10 1.4293(17) . ?
C20 C21 1.3698(18) . ?
C20 C19 1.4095(19) . ?
C20 H20 0.9500 . ?
C16 C17 1.4094(17) . ?
C16 H16 0.9500 . ?
C21 H21 0.9500 . ?
C6 C7 1.3701(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4139(19) . ?
C7 H7 0.9500 . ?
C10 C9 1.4221(18) . ?
C9 C8 1.3685(18) . ?
C9 H9 0.9500 . ?
C3A C2A 1.5318(18) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C8 H8 0.9500 . ?
C8A C7A 1.5330(18) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C5A C6A 1.5315(18) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C19 H19 0.9500 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
O7 H7W2 0.86(2) . ?
O7 H7W1 0.84(2) . ?
O8 H8W1 1.06(3) . ?
O8 H8W2 1.000(18) . ?

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
C3 O3 H3 103.8(14) . . ?
C14 O4 H4 103.7(13) . . ?
C11 C2 C3 119.22(11) . . ?
C11 C2 C1 120.51(11) . . ?
C3 C2 C1 120.26(11) . . ?
O4 C14 C13 119.87(11) . . ?
O4 C14 C15 118.50(11) . . ?
C13 C14 C15 121.63(11) . . ?
C16 C15 C14 119.44(11) . . ?
C16 C15 C23 119.92(11) . . ?
C14 C15 C23 120.58(11) . . ?
C3A N4A C8A 109.30(10) . . ?
C3A N4A C5A 110.46(10) . . ?
C8A N4A C5A 109.75(10) . . ?
C3A N4A H4A 111.1(11) . . ?
C8A N4A H4A 108.3(11) . . ?
C5A N4A H4A 107.9(11) . . ?
C13 C22 C21 122.75(11) . . ?
C13 C22 C17 119.95(11) . . ?
C21 C22 C17 117.28(11) . . ?
C2 C11 C10 121.37(11) . . ?
C2 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C7A N1A C6A 110.17(11) . . ?
C7A N1A C2A 109.67(11) . . ?
C6A N1A C2A 109.29(11) . . ?
C7A N1A H1A 106.5(12) . . ?
C6A N1A H1A 113.0(12) . . ?
C2A N1A H1A 108.1(12) . . ?
C4 C12 C13 117.83(10) . . ?
C4 C12 H12A 107.8 . . ?
C13 C12 H12A 107.8 . . ?
C4 C12 H12B 107.8 . . ?
C13 C12 H12B 107.8 . . ?
H12A C12 H12B 107.2 . . ?
C19 C18 C17 120.89(12) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
O3 C3 C4 119.20(11) . . ?
O3 C3 C2 119.09(11) . . ?
C4 C3 C2 121.69(11) . . ?
O5 C23 O6 123.20(11) . . ?
O5 C23 C15 119.40(11) . . ?
O6 C23 C15 117.39(11) . . ?
C4 C5 C6 122.22(11) . . ?
C4 C5 C10 120.12(11) . . ?
C6 C5 C10 117.65(11) . . ?
O2 C1 O1 123.18(11) . . ?
O2 C1 C2 120.16(11) . . ?
O1 C1 C2 116.65(11) . . ?
C3 C4 C5 118.63(11) . . ?
C3 C4 C12 120.14(11) . . ?
C5 C4 C12 121.17(11) . . ?
C21 C20 C19 121.32(11) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C15 C16 C17 121.06(12) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 120.65(12) . . ?
C16 C17 C22 119.37(11) . . ?
C18 C17 C22 119.95(11) . . ?
C20 C21 C22 121.05(12) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C14 C13 C22 118.49(11) . . ?
C14 C13 C12 119.60(11) . . ?
C22 C13 C12 121.63(10) . . ?
C7 C6 C5 120.89(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.00(12) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C11 C10 C9 121.06(11) . . ?
C11 C10 C5 118.93(11) . . ?
C9 C10 C5 120.01(11) . . ?
C8 C9 C10 120.44(12) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N4A C3A C2A 108.70(10) . . ?
N4A C3A H3A1 109.9 . . ?
C2A C3A H3A1 109.9 . . ?
N4A C3A H3A2 109.9 . . ?
C2A C3A H3A2 109.9 . . ?
H3A1 C3A H3A2 108.3 . . ?
C9 C8 C7 119.96(12) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N4A C8A C7A 108.82(10) . . ?
N4A C8A H8A1 109.9 . . ?
C7A C8A H8A1 109.9 . . ?
N4A C8A H8A2 109.9 . . ?
C7A C8A H8A2 109.9 . . ?
H8A1 C8A H8A2 108.3 . . ?
N4A C5A C6A 109.14(11) . . ?
N4A C5A H5A1 109.9 . . ?
C6A C5A H5A1 109.9 . . ?
N4A C5A H5A2 109.9 . . ?
C6A C5A H5A2 109.9 . . ?
H5A1 C5A H5A2 108.3 . . ?
N1A C2A C3A 109.47(10) . . ?
N1A C2A H2A1 109.8 . . ?
C3A C2A H2A1 109.8 . . ?
N1A C2A H2A2 109.8 . . ?
C3A C2A H2A2 109.8 . . ?
H2A1 C2A H2A2 108.2 . . ?
C18 C19 C20 119.46(12) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
N1A C6A C5A 108.86(11) . . ?
N1A C6A H6A1 109.9 . . ?
C5A C6A H6A1 109.9 . . ?
N1A C6A H6A2 109.9 . . ?
C5A C6A H6A2 109.9 . . ?
H6A1 C6A H6A2 108.3 . . ?
N1A C7A C8A 109.21(11) . . ?
N1A C7A H7A1 109.8 . . ?
C8A C7A H7A1 109.8 . . ?
N1A C7A H7A2 109.8 . . ?
C8A C7A H7A2 109.8 . . ?
H7A1 C7A H7A2 108.3 . . ?
H7W2 O7 H7W1 102.6(19) . . ?
H8W1 O8 H8W2 104(2) . . ?

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
O4 C14 C15 C16 -177.83(11) . . . . ?
C13 C14 C15 C16 1.87(18) . . . . ?
O4 C14 C15 C23 -0.60(17) . . . . ?
C13 C14 C15 C23 179.09(11) . . . . ?
C3 C2 C11 C10 0.54(18) . . . . ?
C1 C2 C11 C10 -179.91(11) . . . . ?
C11 C2 C3 O3 177.81(11) . . . . ?
C1 C2 C3 O3 -1.74(17) . . . . ?
C11 C2 C3 C4 -0.69(18) . . . . ?
C1 C2 C3 C4 179.77(11) . . . . ?
C16 C15 C23 O5 177.09(12) . . . . ?
C14 C15 C23 O5 -0.12(18) . . . . ?
C16 C15 C23 O6 -2.04(18) . . . . ?
C14 C15 C23 O6 -179.24(11) . . . . ?
C11 C2 C1 O2 -176.97(11) . . . . ?
C3 C2 C1 O2 2.57(18) . . . . ?
C11 C2 C1 O1 2.65(17) . . . . ?
C3 C2 C1 O1 -177.81(11) . . . . ?
O3 C3 C4 C5 -179.23(10) . . . . ?
C2 C3 C4 C5 -0.74(18) . . . . ?
O3 C3 C4 C12 3.59(17) . . . . ?
C2 C3 C4 C12 -177.91(11) . . . . ?
C6 C5 C4 C3 -177.05(11) . . . . ?
C10 C5 C4 C3 2.30(17) . . . . ?
C6 C5 C4 C12 0.09(18) . . . . ?
C10 C5 C4 C12 179.44(11) . . . . ?
C13 C12 C4 C3 -119.68(13) . . . . ?
C13 C12 C4 C5 63.22(15) . . . . ?
C14 C15 C16 C17 -0.27(18) . . . . ?
C23 C15 C16 C17 -177.51(11) . . . . ?
C15 C16 C17 C18 176.74(12) . . . . ?
C15 C16 C17 C22 -1.65(18) . . . . ?
C19 C18 C17 C16 179.70(12) . . . . ?
C19 C18 C17 C22 -1.91(18) . . . . ?
C13 C22 C17 C16 2.06(17) . . . . ?
C21 C22 C17 C16 -179.83(11) . . . . ?
C13 C22 C17 C18 -176.35(11) . . . . ?
C21 C22 C17 C18 1.76(17) . . . . ?
C19 C20 C21 C22 -1.67(19) . . . . ?
C13 C22 C21 C20 178.04(12) . . . . ?
C17 C22 C21 C20 -0.01(18) . . . . ?
O4 C14 C13 C22 178.26(10) . . . . ?
C15 C14 C13 C22 -1.43(18) . . . . ?
O4 C14 C13 C12 4.18(17) . . . . ?
C15 C14 C13 C12 -175.51(11) . . . . ?
C21 C22 C13 C14 -178.53(11) . . . . ?
C17 C22 C13 C14 -0.53(17) . . . . ?
C21 C22 C13 C12 -4.58(18) . . . . ?
C17 C22 C13 C12 173.42(11) . . . . ?
C4 C12 C13 C14 -127.44(12) . . . . ?
C4 C12 C13 C22 58.67(16) . . . . ?
C4 C5 C6 C7 -178.60(12) . . . . ?
C10 C5 C6 C7 2.03(18) . . . . ?
C5 C6 C7 C8 -0.27(19) . . . . ?
C2 C11 C10 C9 -179.81(11) . . . . ?
C2 C11 C10 C5 1.00(18) . . . . ?
C4 C5 C10 C11 -2.44(17) . . . . ?
C6 C5 C10 C11 176.94(11) . . . . ?
C4 C5 C10 C9 178.37(11) . . . . ?
C6 C5 C10 C9 -2.25(17) . . . . ?
C11 C10 C9 C8 -178.45(12) . . . . ?
C5 C10 C9 C8 0.73(19) . . . . ?
C8A N4A C3A C2A 58.23(13) . . . . ?
C5A N4A C3A C2A -62.61(14) . . . . ?
C10 C9 C8 C7 1.1(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C3A N4A C8A C7A -64.70(13) . . . . ?
C5A N4A C8A C7A 56.57(13) . . . . ?
C3A N4A C5A C6A 56.22(14) . . . . ?
C8A N4A C5A C6A -64.36(14) . . . . ?
C7A N1A C2A C3A -62.89(14) . . . . ?
C6A N1A C2A C3A 57.98(14) . . . . ?
N4A C3A C2A N1A 4.59(15) . . . . ?
C17 C18 C19 C20 0.25(19) . . . . ?
C21 C20 C19 C18 1.56(19) . . . . ?
C7A N1A C6A C5A 56.17(15) . . . . ?
C2A N1A C6A C5A -64.39(14) . . . . ?
N4A C5A C6A N1A 6.70(16) . . . . ?
C6A N1A C7A C8A -63.95(14) . . . . ?
C2A N1A C7A C8A 56.38(14) . . . . ?
N4A C8A C7A N1A 6.09(15) . . . . ?

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
O7 H7W2 O4 0.86(2) 2.06(2) 2.9064(15) 168(2) 4_576
O4 H4 O5 0.90(2) 1.66(2) 2.5127(13) 158(2) .
N4A H4A O6 1.01(2) 1.54(2) 2.5461(13) 170.5(18) 4_675
N4A H4A O5 1.01(2) 2.569(19) 3.3069(14) 129.4(14) 4_675
O7 H7W1 O6 0.84(2) 2.06(2) 2.8914(15) 166.7(19) .
O3 H3 O2 0.90(2) 1.68(2) 2.5315(13) 157(2) .
N1A H1A O1 1.07(2) 1.49(2) 2.5389(14) 165(2) .
N1A H1A O2 1.07(2) 2.64(2) 3.4808(14) 134.7(16) .
O8 H8W1 O1 1.06(3) 1.80(3) 2.7978(15) 155(2) .
O8 H8W2 O3 1.000(18) 1.862(18) 2.8579(14) 174(3) 2_645

_diffrn_measured_fraction_theta_max 0.904
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.049


data_2.CIF
_database_code_depnum_ccdc_archive 'CCDC 898738'
#TrackingRef '13608_web_deposit_cif_file_0_DeliaHaynes_1346229442.submission.CIF'


_audit_update_record             
;
2012-08-28 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            \2
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O6, 2(C6 H13 N2), 3(H2 O)'
_chemical_formula_sum            'C35 H46 N4 O9'
_chemical_formula_weight         666.76

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           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8658(4)
_cell_length_b                   9.0624(3)
_cell_length_c                   26.4347(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.548(2)
_cell_angle_gamma                90.00
_cell_volume                     3306.16(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4220
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   'SADABS, 2009'

_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  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26197
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.25
_reflns_number_total             7912
_reflns_number_gt                5518
_reflns_threshold_expression     >2\sI)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)'
_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^)+(0.0510P)^2^+0.9022P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7912
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.38119(9) 0.99685(15) -0.22762(4) 0.0260(3) Uani 1 1 d . . .
C1 C 0.41276(12) 0.98339(19) -0.18116(6) 0.0167(3) Uani 1 1 d . . .
O2 O 0.50145(8) 0.98488(15) -0.16661(4) 0.0238(3) Uani 1 1 d . . .
C2 C 0.34050(12) 0.96315(18) -0.14286(6) 0.0147(3) Uani 1 1 d . . .
O3 O 0.46891(8) 0.96367(14) -0.07451(4) 0.0204(3) Uani 1 1 d . . .
C3 C 0.37343(12) 0.95023(18) -0.08995(6) 0.0151(3) Uani 1 1 d . . .
H3 H 0.4992(19) 0.969(3) -0.1040(10) 0.065(8) Uiso 1 1 d . . .
H4 H 0.2401(16) 0.765(3) 0.1155(9) 0.047(7) Uiso 1 1 d . . .
H1A H 0.4712(17) 0.976(2) -0.2667(8) 0.042(6) Uiso 1 1 d . . .
H8W1 H 0.2737(19) 0.520(3) 0.2294(9) 0.050(7) Uiso 1 1 d . . .
H9W2 H 0.1253(19) 0.211(3) 0.2267(9) 0.059(8) Uiso 1 1 d . . .
H1B H 0.0878(16) 1.014(3) 0.3316(9) 0.044(6) Uiso 1 1 d . . .
H7W1 H 0.118(2) 0.930(3) 0.2524(11) 0.064(8) Uiso 1 1 d . . .
H8W2 H 0.2086(18) 0.616(3) 0.2009(9) 0.056(8) Uiso 1 1 d . . .
H9W1 H 0.1390(19) 0.368(3) 0.2302(10) 0.063(9) Uiso 1 1 d . . .
H7W2 H 0.032(2) 0.862(3) 0.2712(11) 0.077(10) Uiso 1 1 d . . .
O4 O 0.26618(9) 0.78285(13) 0.08398(4) 0.0213(3) Uani 1 1 d . . .
C4 C 0.30953(12) 0.92415(18) -0.05353(6) 0.0147(3) Uani 1 1 d . . .
O5 O 0.19105(10) 0.80370(14) 0.16603(4) 0.0255(3) Uani 1 1 d . . .
C5 C 0.20948(12) 0.90810(18) -0.06951(6) 0.0143(3) Uani 1 1 d . . .
O6 O 0.17307(9) 1.02178(14) 0.20259(4) 0.0224(3) Uani 1 1 d . . .
C6 C 0.13949(12) 0.87281(18) -0.03520(6) 0.0170(3) Uani 1 1 d . . .
H6 H 0.1600 0.8591 -0.0002 0.020 Uiso 1 1 calc R . .
O7 O 0.09111(11) 0.89914(16) 0.28052(5) 0.0291(3) Uani 1 1 d . . .
C7 C 0.04356(12) 0.85834(19) -0.05182(6) 0.0193(4) Uani 1 1 d . . .
H7 H -0.0016 0.8350 -0.0282 0.023 Uiso 1 1 calc R . .
O8 O 0.22084(10) 0.51797(17) 0.20593(5) 0.0278(3) Uani 1 1 d . . .
C8 C 0.01061(12) 0.87759(19) -0.10355(6) 0.0188(4) Uani 1 1 d . . .
H8 H -0.0564 0.8687 -0.1146 0.023 Uiso 1 1 calc R . .
O9 O 0.09921(11) 0.29150(19) 0.23851(5) 0.0306(3) Uani 1 1 d . . .
C9 C 0.07568(12) 0.90922(19) -0.13785(6) 0.0177(4) Uani 1 1 d . . .
H9 H 0.0534 0.9212 -0.1727 0.021 Uiso 1 1 calc R . .
C10 C 0.17540(12) 0.92429(18) -0.12205(6) 0.0150(3) Uani 1 1 d . . .
C11 C 0.24313(12) 0.95160(18) -0.15768(6) 0.0160(3) Uani 1 1 d . . .
H11 H 0.2208 0.9622 -0.1926 0.019 Uiso 1 1 calc R . .
C12 C 0.35021(12) 0.90075(19) 0.00134(6) 0.0157(3) Uani 1 1 d . . .
H12A H 0.4214 0.9128 0.0030 0.019 Uiso 1 1 calc R . .
H12B H 0.3375 0.7970 0.0104 0.019 Uiso 1 1 calc R . .
C13 C 0.31355(11) 0.99869(18) 0.04215(6) 0.0148(3) Uani 1 1 d . . .
C14 C 0.27504(12) 0.93216(18) 0.08309(6) 0.0148(3) Uani 1 1 d . . .
C15 C 0.24386(12) 1.01740(19) 0.12423(6) 0.0154(3) Uani 1 1 d . . .
C16 C 0.25329(11) 1.16724(19) 0.12313(6) 0.0157(3) Uani 1 1 d . . .
H16 H 0.2328 1.2241 0.1503 0.019 Uiso 1 1 calc R . .
C17 C 0.29272(11) 1.23980(19) 0.08267(6) 0.0152(3) Uani 1 1 d . . .
C18 C 0.30275(12) 1.39546(19) 0.08236(6) 0.0186(4) Uani 1 1 d . . .
H18 H 0.2801 1.4520 0.1091 0.022 Uiso 1 1 calc R . .
C19 C 0.34457(12) 1.4653(2) 0.04421(6) 0.0200(4) Uani 1 1 d . . .
H19 H 0.3506 1.5697 0.0443 0.024 Uiso 1 1 calc R . .
C20 C 0.37886(13) 1.3809(2) 0.00460(6) 0.0198(4) Uani 1 1 d . . .
H20 H 0.4095 1.4292 -0.0214 0.024 Uiso 1 1 calc R . .
C21 C 0.36851(12) 1.23140(19) 0.00332(6) 0.0173(4) Uani 1 1 d . . .
H21 H 0.3914 1.1774 -0.0239 0.021 Uiso 1 1 calc R . .
C22 C 0.32412(11) 1.15404(19) 0.04197(6) 0.0147(3) Uani 1 1 d . . .
C23 C 0.19974(12) 0.9429(2) 0.16756(6) 0.0173(4) Uani 1 1 d . . .
N1A N 0.51768(11) 0.96366(17) -0.29068(5) 0.0214(3) Uani 1 1 d . . .
C2A C 0.61168(14) 0.9038(3) -0.26748(7) 0.0352(5) Uani 1 1 d . . .
H2A1 H 0.6016 0.8069 -0.2515 0.042 Uiso 1 1 calc R . .
H2A2 H 0.6407 0.9720 -0.2410 0.042 Uiso 1 1 calc R . .
C3A C 0.67937(14) 0.8868(3) -0.31002(7) 0.0335(5) Uani 1 1 d . . .
H3A1 H 0.7388 0.9460 -0.3015 0.040 Uiso 1 1 calc R . .
H3A2 H 0.6987 0.7821 -0.3124 0.040 Uiso 1 1 calc R . .
N4A N 0.63202(11) 0.93544(17) -0.35923(6) 0.0246(4) Uani 1 1 d . . .
C5A C 0.60242(18) 1.0895(2) -0.35598(9) 0.0419(6) Uani 1 1 d . . .
H5A1 H 0.5706 1.1216 -0.3893 0.050 Uiso 1 1 calc R . .
H5A2 H 0.6604 1.1519 -0.3478 0.050 Uiso 1 1 calc R . .
C6A C 0.53165(17) 1.1104(2) -0.31471(8) 0.0357(5) Uani 1 1 d . . .
H6A1 H 0.5587 1.1819 -0.2888 0.043 Uiso 1 1 calc R . .
H6A2 H 0.4688 1.1489 -0.3302 0.043 Uiso 1 1 calc R . .
C7A C 0.47447(14) 0.8587(2) -0.33023(7) 0.0263(4) Uani 1 1 d . . .
H7A1 H 0.4109 0.8958 -0.3452 0.032 Uiso 1 1 calc R . .
H7A2 H 0.4648 0.7608 -0.3149 0.032 Uiso 1 1 calc R . .
C8A C 0.54521(13) 0.8461(2) -0.37164(7) 0.0254(4) Uani 1 1 d . . .
H8A1 H 0.5642 0.7415 -0.3752 0.031 Uiso 1 1 calc R . .
H8A2 H 0.5122 0.8789 -0.4046 0.031 Uiso 1 1 calc R . .
N1B N 0.07566(11) 1.05680(16) 0.36461(5) 0.0203(3) Uani 1 1 d . . .
C2B C 0.08251(17) 1.2207(2) 0.36962(7) 0.0320(5) Uani 1 1 d . . .
H2B1 H 0.0420 1.2692 0.3415 0.038 Uiso 1 1 calc R . .
H2B2 H 0.1504 1.2535 0.3686 0.038 Uiso 1 1 calc R . .
C3B C 0.04572(15) 1.2608(2) 0.42155(7) 0.0277(4) Uani 1 1 d . . .
H3B1 H 0.0924 1.3289 0.4402 0.033 Uiso 1 1 calc R . .
H3B2 H -0.0173 1.3124 0.4156 0.033 Uiso 1 1 calc R . .
N4B N 0.03424(11) 1.12917(16) 0.45253(5) 0.0199(3) Uani 1 1 d . . .
C5B C 0.12424(13) 1.0433(2) 0.45609(6) 0.0237(4) Uani 1 1 d . . .
H5B1 H 0.1186 0.9590 0.4794 0.028 Uiso 1 1 calc R . .
H5B2 H 0.1786 1.1061 0.4704 0.028 Uiso 1 1 calc R . .
C6B C 0.14591(13) 0.9852(2) 0.40350(6) 0.0212(4) Uani 1 1 d . . .
H6B1 H 0.2132 1.0102 0.3971 0.025 Uiso 1 1 calc R . .
H6B2 H 0.1384 0.8767 0.4020 0.025 Uiso 1 1 calc R . .
C7B C -0.02532(13) 1.0091(2) 0.37154(6) 0.0240(4) Uani 1 1 d . . .
H7B1 H -0.0333 0.9028 0.3637 0.029 Uiso 1 1 calc R . .
H7B2 H -0.0722 1.0651 0.3483 0.029 Uiso 1 1 calc R . .
C8B C -0.04366(13) 1.0388(2) 0.42719(6) 0.0218(4) Uani 1 1 d . . .
H8B1 H -0.1064 1.0904 0.4282 0.026 Uiso 1 1 calc R . .
H8B2 H -0.0474 0.9438 0.4454 0.026 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 0.0196(6) 0.0453(9) 0.0136(6) 0.0020(5) 0.0047(5) 0.0004(6)
C1 0.0191(9) 0.0155(9) 0.0160(8) -0.0013(6) 0.0049(6) 0.0010(7)
O2 0.0158(6) 0.0383(8) 0.0179(6) -0.0014(5) 0.0045(5) -0.0005(5)
C2 0.0191(8) 0.0120(9) 0.0134(7) -0.0008(6) 0.0038(6) 0.0010(6)
O3 0.0143(6) 0.0312(8) 0.0157(6) -0.0017(5) 0.0016(5) 0.0003(5)
C3 0.0160(8) 0.0130(9) 0.0162(8) -0.0014(6) 0.0022(6) -0.0001(6)
O4 0.0330(7) 0.0145(7) 0.0175(6) 0.0005(5) 0.0084(5) -0.0012(5)
C4 0.0191(9) 0.0108(8) 0.0143(7) -0.0007(6) 0.0029(6) 0.0015(6)
O5 0.0378(8) 0.0201(7) 0.0201(6) 0.0014(5) 0.0109(5) -0.0032(6)
C5 0.0179(8) 0.0099(8) 0.0155(7) -0.0016(6) 0.0036(6) 0.0002(6)
O6 0.0296(7) 0.0216(7) 0.0174(6) -0.0014(5) 0.0096(5) -0.0018(5)
C6 0.0231(9) 0.0123(9) 0.0164(8) -0.0006(6) 0.0051(6) -0.0018(7)
O7 0.0397(9) 0.0312(9) 0.0184(6) -0.0035(6) 0.0131(6) -0.0090(7)
C7 0.0211(9) 0.0156(9) 0.0223(8) -0.0014(7) 0.0085(7) -0.0009(7)
O8 0.0299(8) 0.0264(8) 0.0254(7) 0.0023(6) -0.0056(6) -0.0013(6)
C8 0.0162(8) 0.0158(9) 0.0246(8) -0.0008(7) 0.0022(7) -0.0003(7)
O9 0.0360(8) 0.0258(8) 0.0318(7) -0.0011(6) 0.0121(6) 0.0027(7)
C9 0.0199(9) 0.0159(9) 0.0171(8) -0.0017(7) 0.0006(6) 0.0013(7)
C10 0.0180(8) 0.0124(8) 0.0151(7) -0.0011(6) 0.0034(6) 0.0001(6)
C11 0.0201(9) 0.0158(9) 0.0122(7) -0.0001(6) 0.0020(6) -0.0004(7)
C12 0.0193(9) 0.0151(9) 0.0129(7) -0.0008(6) 0.0019(6) 0.0022(7)
C13 0.0140(8) 0.0172(9) 0.0130(7) -0.0001(6) 0.0006(6) 0.0009(6)
C14 0.0156(8) 0.0137(9) 0.0150(7) -0.0005(6) 0.0015(6) 0.0009(6)
C15 0.0146(8) 0.0198(9) 0.0118(7) 0.0005(6) 0.0011(6) 0.0002(7)
C16 0.0133(8) 0.0202(9) 0.0138(7) -0.0030(6) 0.0020(6) 0.0005(7)
C17 0.0137(8) 0.0170(9) 0.0146(7) -0.0015(6) 0.0003(6) -0.0001(6)
C18 0.0197(9) 0.0185(10) 0.0176(8) -0.0024(7) 0.0020(6) 0.0017(7)
C19 0.0239(9) 0.0142(9) 0.0217(8) 0.0011(7) 0.0020(7) -0.0011(7)
C20 0.0230(9) 0.0198(10) 0.0173(8) 0.0033(7) 0.0056(7) -0.0015(7)
C21 0.0179(9) 0.0194(10) 0.0151(8) -0.0001(7) 0.0033(6) 0.0005(7)
C22 0.0122(8) 0.0165(9) 0.0153(7) 0.0009(6) -0.0001(6) 0.0014(6)
C23 0.0165(8) 0.0196(10) 0.0157(8) 0.0013(7) 0.0021(6) -0.0021(7)
N1A 0.0232(8) 0.0237(9) 0.0187(7) 0.0015(6) 0.0098(6) 0.0004(7)
C2A 0.0199(10) 0.0618(16) 0.0244(9) 0.0042(9) 0.0050(8) 0.0063(10)
C3A 0.0203(10) 0.0531(15) 0.0285(10) -0.0061(9) 0.0092(8) 0.0013(9)
N4A 0.0295(9) 0.0211(9) 0.0254(8) -0.0002(6) 0.0142(6) -0.0020(7)
C5A 0.0660(16) 0.0220(12) 0.0441(12) -0.0007(9) 0.0376(11) -0.0021(11)
C6A 0.0498(14) 0.0204(11) 0.0414(12) -0.0028(9) 0.0268(10) -0.0009(9)
C7A 0.0266(10) 0.0291(11) 0.0241(9) -0.0031(8) 0.0080(7) -0.0026(8)
C8A 0.0289(10) 0.0277(11) 0.0208(9) -0.0009(8) 0.0082(7) 0.0010(8)
N1B 0.0292(9) 0.0179(8) 0.0151(7) 0.0000(6) 0.0083(6) 0.0006(6)
C2B 0.0586(14) 0.0170(10) 0.0231(9) 0.0024(8) 0.0171(9) -0.0023(9)
C3B 0.0447(12) 0.0164(10) 0.0235(9) -0.0016(7) 0.0112(8) -0.0015(8)
N4B 0.0239(8) 0.0190(8) 0.0172(7) 0.0002(6) 0.0046(6) 0.0005(6)
C5B 0.0225(9) 0.0299(11) 0.0188(8) -0.0018(7) 0.0018(7) 0.0018(8)
C6B 0.0181(9) 0.0256(10) 0.0206(8) 0.0002(7) 0.0060(7) 0.0007(7)
C7B 0.0210(9) 0.0305(11) 0.0201(8) -0.0024(8) 0.0000(7) 0.0030(8)
C8B 0.0183(9) 0.0259(10) 0.0217(8) -0.0014(7) 0.0049(7) 0.0017(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 C1 1.2691(19) . ?
C1 O2 1.253(2) . ?
C1 C2 1.503(2) . ?
C2 C11 1.373(2) . ?
C2 C3 1.434(2) . ?
O3 C3 1.3527(19) . ?
O3 H3 0.92(3) . ?
C3 C4 1.390(2) . ?
O4 C14 1.359(2) . ?
O4 H4 0.95(2) . ?
C4 C5 1.418(2) . ?
C4 C12 1.519(2) . ?
O5 C23 1.268(2) . ?
C5 C6 1.427(2) . ?
C5 C10 1.431(2) . ?
O6 C23 1.254(2) . ?
C6 C7 1.366(2) . ?
C6 H6 0.9500 . ?
O7 H7W1 0.91(3) . ?
O7 H7W2 0.90(3) . ?
C7 C8 1.410(2) . ?
C7 H7 0.9500 . ?
O8 H8W1 0.91(3) . ?
O8 H8W2 0.91(3) . ?
C8 C9 1.370(2) . ?
C8 H8 0.9500 . ?
O9 H9W2 0.88(3) . ?
O9 H9W1 0.92(3) . ?
C9 C10 1.412(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(2) . ?
C13 C22 1.416(2) . ?
C14 C15 1.434(2) . ?
C15 C16 1.365(2) . ?
C15 C23 1.509(2) . ?
C16 C17 1.410(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.418(2) . ?
C17 C22 1.429(2) . ?
C18 C19 1.366(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.415(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.363(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.427(2) . ?
C21 H21 0.9500 . ?
N1A C2A 1.488(2) . ?
N1A C7A 1.495(2) . ?
N1A C6A 1.495(2) . ?
N1A H1A 0.95(2) . ?
C2A C3A 1.541(3) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A N4A 1.467(2) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
N4A C5A 1.460(3) . ?
N4A C8A 1.461(2) . ?
C5A C6A 1.548(3) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.543(2) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
N1B C2B 1.494(2) . ?
N1B C7B 1.493(2) . ?
N1B C6B 1.494(2) . ?
N1B H1B 0.98(2) . ?
C2B C3B 1.553(2) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B N4B 1.465(2) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
N4B C8B 1.465(2) . ?
N4B C5B 1.466(2) . ?
C5B C6B 1.543(2) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B C8B 1.541(2) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 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
O2 C1 O1 122.19(15) . . ?
O2 C1 C2 119.54(14) . . ?
O1 C1 C2 118.27(14) . . ?
C11 C2 C3 118.94(14) . . ?
C11 C2 C1 121.21(14) . . ?
C3 C2 C1 119.81(14) . . ?
C3 O3 H3 105.2(16) . . ?
O3 C3 C4 118.49(14) . . ?
O3 C3 C2 119.81(14) . . ?
C4 C3 C2 121.69(15) . . ?
C14 O4 H4 103.0(14) . . ?
C3 C4 C5 118.80(14) . . ?
C3 C4 C12 118.83(14) . . ?
C5 C4 C12 122.16(14) . . ?
C4 C5 C6 122.64(14) . . ?
C4 C5 C10 120.03(14) . . ?
C6 C5 C10 117.31(15) . . ?
C7 C6 C5 121.19(15) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
H7W1 O7 H7W2 109(2) . . ?
C6 C7 C8 120.94(15) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
H8W1 O8 H8W2 102(2) . . ?
C9 C8 C7 119.69(15) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
H9W2 O9 H9W1 105(2) . . ?
C8 C9 C10 120.88(15) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 120.93(14) . . ?
C9 C10 C5 119.96(15) . . ?
C11 C10 C5 119.08(15) . . ?
C2 C11 C10 121.40(14) . . ?
C2 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C4 C12 C13 118.47(14) . . ?
C4 C12 H12A 107.7 . . ?
C13 C12 H12A 107.7 . . ?
C4 C12 H12B 107.7 . . ?
C13 C12 H12B 107.7 . . ?
H12A C12 H12B 107.1 . . ?
C14 C13 C22 118.79(14) . . ?
C14 C13 C12 118.61(15) . . ?
C22 C13 C12 122.41(14) . . ?
O4 C14 C13 119.17(14) . . ?
O4 C14 C15 119.26(14) . . ?
C13 C14 C15 121.57(15) . . ?
C16 C15 C14 118.90(14) . . ?
C16 C15 C23 120.52(14) . . ?
C14 C15 C23 120.57(15) . . ?
C15 C16 C17 121.67(15) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 120.91(15) . . ?
C16 C17 C22 119.09(15) . . ?
C18 C17 C22 119.99(15) . . ?
C19 C18 C17 120.93(16) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.51(16) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.90(16) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 121.50(15) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C13 C22 C21 122.89(15) . . ?
C13 C22 C17 119.96(14) . . ?
C21 C22 C17 117.12(15) . . ?
O6 C23 O5 123.85(15) . . ?
O6 C23 C15 118.42(15) . . ?
O5 C23 C15 117.73(14) . . ?
C2A N1A C7A 109.40(15) . . ?
C2A N1A C6A 110.80(16) . . ?
C7A N1A C6A 109.18(15) . . ?
C2A N1A H1A 113.0(13) . . ?
C7A N1A H1A 106.8(13) . . ?
C6A N1A H1A 107.6(14) . . ?
N1A C2A C3A 107.86(15) . . ?
N1A C2A H2A1 110.1 . . ?
C3A C2A H2A1 110.1 . . ?
N1A C2A H2A2 110.1 . . ?
C3A C2A H2A2 110.1 . . ?
H2A1 C2A H2A2 108.4 . . ?
N4A C3A C2A 111.42(15) . . ?
N4A C3A H3A1 109.3 . . ?
C2A C3A H3A1 109.3 . . ?
N4A C3A H3A2 109.3 . . ?
C2A C3A H3A2 109.3 . . ?
H3A1 C3A H3A2 108.0 . . ?
C5A N4A C8A 108.24(16) . . ?
C5A N4A C3A 109.82(16) . . ?
C8A N4A C3A 108.72(15) . . ?
N4A C5A C6A 111.09(16) . . ?
N4A C5A H5A1 109.4 . . ?
C6A C5A H5A1 109.4 . . ?
N4A C5A H5A2 109.4 . . ?
C6A C5A H5A2 109.4 . . ?
H5A1 C5A H5A2 108.0 . . ?
N1A C6A C5A 107.90(16) . . ?
N1A C6A H6A1 110.1 . . ?
C5A C6A H6A1 110.1 . . ?
N1A C6A H6A2 110.1 . . ?
C5A C6A H6A2 110.1 . . ?
H6A1 C6A H6A2 108.4 . . ?
N1A C7A C8A 107.70(15) . . ?
N1A C7A H7A1 110.2 . . ?
C8A C7A H7A1 110.2 . . ?
N1A C7A H7A2 110.2 . . ?
C8A C7A H7A2 110.2 . . ?
H7A1 C7A H7A2 108.5 . . ?
N4A C8A C7A 111.45(14) . . ?
N4A C8A H8A1 109.3 . . ?
C7A C8A H8A1 109.3 . . ?
N4A C8A H8A2 109.3 . . ?
C7A C8A H8A2 109.3 . . ?
H8A1 C8A H8A2 108.0 . . ?
C2B N1B C7B 109.21(15) . . ?
C2B N1B C6B 109.81(15) . . ?
C7B N1B C6B 110.28(13) . . ?
C2B N1B H1B 117.0(13) . . ?
C7B N1B H1B 103.8(13) . . ?
C6B N1B H1B 106.6(13) . . ?
N1B C2B C3B 106.71(14) . . ?
N1B C2B H2B1 110.4 . . ?
C3B C2B H2B1 110.4 . . ?
N1B C2B H2B2 110.4 . . ?
C3B C2B H2B2 110.4 . . ?
H2B1 C2B H2B2 108.6 . . ?
N4B C3B C2B 111.50(15) . . ?
N4B C3B H3B1 109.3 . . ?
C2B C3B H3B1 109.3 . . ?
N4B C3B H3B2 109.3 . . ?
C2B C3B H3B2 109.3 . . ?
H3B1 C3B H3B2 108.0 . . ?
C3B N4B C8B 108.36(14) . . ?
C3B N4B C5B 109.29(14) . . ?
C8B N4B C5B 108.54(14) . . ?
N4B C5B C6B 111.23(14) . . ?
N4B C5B H5B1 109.4 . . ?
C6B C5B H5B1 109.4 . . ?
N4B C5B H5B2 109.4 . . ?
C6B C5B H5B2 109.4 . . ?
H5B1 C5B H5B2 108.0 . . ?
N1B C6B C5B 107.53(14) . . ?
N1B C6B H6B1 110.2 . . ?
C5B C6B H6B1 110.2 . . ?
N1B C6B H6B2 110.2 . . ?
C5B C6B H6B2 110.2 . . ?
H6B1 C6B H6B2 108.5 . . ?
N1B C7B C8B 108.06(14) . . ?
N1B C7B H7B1 110.1 . . ?
C8B C7B H7B1 110.1 . . ?
N1B C7B H7B2 110.1 . . ?
C8B C7B H7B2 110.1 . . ?
H7B1 C7B H7B2 108.4 . . ?
N4B C8B C7B 110.59(14) . . ?
N4B C8B H8B1 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
N4B C8B H8B2 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 108.1 . . ?

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
O2 C1 C2 C11 -175.85(16) . . . . ?
O1 C1 C2 C11 3.4(2) . . . . ?
O2 C1 C2 C3 1.9(2) . . . . ?
O1 C1 C2 C3 -178.89(15) . . . . ?
C11 C2 C3 O3 -178.93(15) . . . . ?
C1 C2 C3 O3 3.3(2) . . . . ?
C11 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 C4 -176.79(15) . . . . ?
O3 C3 C4 C5 -179.22(15) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
O3 C3 C4 C12 -4.4(2) . . . . ?
C2 C3 C4 C12 175.65(15) . . . . ?
C3 C4 C5 C6 176.32(15) . . . . ?
C12 C4 C5 C6 1.7(2) . . . . ?
C3 C4 C5 C10 -2.3(2) . . . . ?
C12 C4 C5 C10 -176.96(15) . . . . ?
C4 C5 C6 C7 179.90(16) . . . . ?
C10 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 177.67(16) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C4 C5 C10 C9 -179.59(15) . . . . ?
C6 C5 C10 C9 1.7(2) . . . . ?
C4 C5 C10 C11 2.0(2) . . . . ?
C6 C5 C10 C11 -176.72(15) . . . . ?
C3 C2 C11 C10 -1.3(2) . . . . ?
C1 C2 C11 C10 176.41(15) . . . . ?
C9 C10 C11 C2 -178.52(16) . . . . ?
C5 C10 C11 C2 -0.1(2) . . . . ?
C3 C4 C12 C13 124.92(17) . . . . ?
C5 C4 C12 C13 -60.5(2) . . . . ?
C4 C12 C13 C14 124.81(16) . . . . ?
C4 C12 C13 C22 -60.2(2) . . . . ?
C22 C13 C14 O4 -178.89(14) . . . . ?
C12 C13 C14 O4 -3.7(2) . . . . ?
C22 C13 C14 C15 1.5(2) . . . . ?
C12 C13 C14 C15 176.68(14) . . . . ?
O4 C14 C15 C16 179.80(15) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
O4 C14 C15 C23 -1.3(2) . . . . ?
C13 C14 C15 C23 178.31(14) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C23 C15 C16 C17 -178.90(14) . . . . ?
C15 C16 C17 C18 -179.45(15) . . . . ?
C15 C16 C17 C22 -0.4(2) . . . . ?
C16 C17 C18 C19 177.31(15) . . . . ?
C22 C17 C18 C19 -1.7(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C14 C13 C22 C21 175.89(15) . . . . ?
C12 C13 C22 C21 0.9(2) . . . . ?
C14 C13 C22 C17 -1.9(2) . . . . ?
C12 C13 C22 C17 -176.81(14) . . . . ?
C20 C21 C22 C13 -179.05(16) . . . . ?
C20 C21 C22 C17 -1.2(2) . . . . ?
C16 C17 C22 C13 1.3(2) . . . . ?
C18 C17 C22 C13 -179.62(15) . . . . ?
C16 C17 C22 C21 -176.57(14) . . . . ?
C18 C17 C22 C21 2.5(2) . . . . ?
C16 C15 C23 O6 -0.7(2) . . . . ?
C14 C15 C23 O6 -179.66(15) . . . . ?
C16 C15 C23 O5 178.61(16) . . . . ?
C14 C15 C23 O5 -0.3(2) . . . . ?
C7A N1A C2A C3A 60.3(2) . . . . ?
C6A N1A C2A C3A -60.1(2) . . . . ?
N1A C2A C3A N4A 0.7(2) . . . . ?
C2A C3A N4A C5A 58.6(2) . . . . ?
C2A C3A N4A C8A -59.7(2) . . . . ?
C8A N4A C5A C6A 59.4(2) . . . . ?
C3A N4A C5A C6A -59.1(2) . . . . ?
C2A N1A C6A C5A 59.4(2) . . . . ?
C7A N1A C6A C5A -61.2(2) . . . . ?
N4A C5A C6A N1A 0.9(3) . . . . ?
C2A N1A C7A C8A -61.62(19) . . . . ?
C6A N1A C7A C8A 59.79(19) . . . . ?
C5A N4A C8A C7A -60.97(19) . . . . ?
C3A N4A C8A C7A 58.3(2) . . . . ?
N1A C7A C8A N4A 1.4(2) . . . . ?
C7B N1B C2B C3B 54.33(19) . . . . ?
C6B N1B C2B C3B -66.71(19) . . . . ?
N1B C2B C3B N4B 10.8(2) . . . . ?
C2B C3B N4B C8B -66.0(2) . . . . ?
C2B C3B N4B C5B 52.1(2) . . . . ?
C3B N4B C5B C6B -63.92(19) . . . . ?
C8B N4B C5B C6B 54.07(19) . . . . ?
C2B N1B C6B C5B 55.75(18) . . . . ?
C7B N1B C6B C5B -64.65(18) . . . . ?
N4B C5B C6B N1B 9.1(2) . . . . ?
C2B N1B C7B C8B -67.39(18) . . . . ?
C6B N1B C7B C8B 53.37(19) . . . . ?
C3B N4B C8B C7B 52.60(19) . . . . ?
C5B N4B C8B C7B -65.98(18) . . . . ?
N1B C7B C8B N4B 11.2(2) . . . . ?

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
O8 H8W1 O1 0.91(3) 1.79(3) 2.7003(18) 173(2) 4_576
N1A H1A O1 0.95(2) 1.71(2) 2.6573(19) 176(2) .
O3 H3 O2 0.92(3) 1.67(3) 2.5260(16) 154(2) .
N1B H1B O7 0.98(2) 1.71(2) 2.6684(19) 164(2) .
O7 H7W1 O6 0.91(3) 1.79(3) 2.6875(18) 170(3) .
O9 H9W2 O6 0.88(3) 1.97(3) 2.848(2) 175(2) 1_545
O4 H4 O5 0.95(2) 1.60(2) 2.5026(16) 157(2) .
O8 H8W2 O5 0.91(3) 1.94(3) 2.811(2) 160(2) .
O9 H9W1 O8 0.92(3) 1.92(3) 2.842(2) 174(2) .
O7 H7W2 O9 0.90(3) 1.92(3) 2.813(2) 171(3) 2

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.056


data_3.CIF
_database_code_depnum_ccdc_archive 'CCDC 898739'
#TrackingRef '13608_web_deposit_cif_file_0_DeliaHaynes_1346229442.submission.CIF'


_audit_update_record             
;
2012-08-28 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            \3
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O6, 2(C6 H13 N2), 2.7(H2 O)'
_chemical_formula_sum            'C35 H45.40 N4 O8.70'
_chemical_formula_weight         661.35

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           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.419(3)
_cell_length_b                   18.531(4)
_cell_length_c                   17.890(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.434(3)
_cell_angle_gamma                90.00
_cell_volume                     3195.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1412
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   'SADABS, 2009'

_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  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38459
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         28.89
_reflns_number_total             7865
_reflns_number_gt                6545
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)'
_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^)+(0.0493P)^2^+1.6007P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7865
_refine_ls_number_parameters     535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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 -0.35678(16) 0.37125(7) -0.22747(9) 0.0252(3) Uani 0.80 1 d P A 1
C1 C -0.3306(2) 0.40140(9) -0.15775(15) 0.0196(4) Uani 0.80 1 d P A 1
O2 O -0.3767(2) 0.37925(11) -0.11013(14) 0.0256(4) Uani 0.80 1 d P A 1
C2 C -0.24504(14) 0.46844(7) -0.12518(9) 0.0238(3) Uani 1 1 d . . .
O3 O -0.26088(11) 0.48158(5) 0.00320(7) 0.0270(2) Uani 1 1 d . . .
C3 C -0.21420(13) 0.50711(7) -0.04709(9) 0.0207(3) Uani 1 1 d . A .
H3 H -0.310(2) 0.4389(14) -0.0258(16) 0.066(7) Uiso 1 1 d . B 1
H9W2 H 0.163(3) 0.6377(15) 0.3130(18) 0.027(7) Uiso 0.70 1 d P C 1
H8W1 H -0.462(2) 0.4351(13) -0.3316(16) 0.057(7) Uiso 1 1 d . . .
H9W1 H 0.120(3) 0.6765(16) 0.254(2) 0.042(9) Uiso 0.70 1 d P D 1
O4 O 0.04739(9) 0.73882(5) 0.12867(6) 0.0218(2) Uani 1 1 d . . .
C4 C -0.13852(13) 0.57080(6) -0.02273(8) 0.0174(2) Uani 1 1 d . . .
H4 H 0.082(2) 0.7890(12) 0.1454(14) 0.053(6) Uiso 1 1 d . . .
H1A H -0.466(2) 0.2933(13) -0.1654(15) 0.058(6) Uiso 1 1 d . . .
H1B H 0.017(3) 1.0071(14) 0.1203(17) 0.042(7) Uiso 0.75 1 d P E 1
H8W2 H -0.507(2) 0.5029(13) -0.3653(14) 0.055(6) Uiso 1 1 d . . .
H7W1 H -0.247(2) 1.0086(14) 0.0785(15) 0.064(7) Uiso 1 1 d . . .
O5 O 0.07216(10) 0.87329(5) 0.14027(6) 0.0241(2) Uani 1 1 d . . .
C5 C -0.08415(12) 0.59519(7) -0.07377(8) 0.0171(2) Uani 1 1 d . A .
O6 O -0.11217(10) 0.94496(5) 0.07327(7) 0.0260(2) Uani 1 1 d . . .
C6 C 0.00376(13) 0.65665(7) -0.05007(8) 0.0197(2) Uani 1 1 d . . .
H6 H 0.0286 0.6828 0.0021 0.024 Uiso 1 1 calc R A .
O7 O -0.27517(13) 1.05010(6) 0.09282(8) 0.0364(3) Uani 1 1 d . . .
C7 C 0.05315(14) 0.67882(8) -0.10138(9) 0.0245(3) Uani 1 1 d . A .
H7 H 0.1124 0.7197 -0.0837 0.029 Uiso 1 1 calc R . .
O8 O -0.48855(11) 0.46012(6) -0.37898(8) 0.0300(2) Uani 1 1 d . . .
C8 C 0.01769(15) 0.64211(9) -0.17977(9) 0.0279(3) Uani 1 1 d . . .
H8 H 0.0500 0.6591 -0.2157 0.033 Uiso 1 1 calc R A .
O9 O 0.11439(16) 0.66921(9) 0.29215(11) 0.0258(3) Uani 0.70 1 d P F 1
C9 C -0.06331(14) 0.58201(8) -0.20355(9) 0.0259(3) Uani 1 1 d . A .
H9 H -0.0860 0.5567 -0.2559 0.031 Uiso 1 1 calc R . .
O10 O -0.4060(6) 0.3751(3) -0.2139(4) 0.0187(10) Uani 0.20 1 d P A 2
C10 C -0.11448(13) 0.55652(7) -0.15137(8) 0.0208(3) Uani 1 1 d . . .
O11 O -0.3713(10) 0.3786(5) -0.0778(5) 0.0239(16) Uani 0.20 1 d P A 2
C11 C -0.19540(13) 0.49361(7) -0.17480(9) 0.0237(3) Uani 1 1 d . A .
H11 H -0.2161 0.4679 -0.2265 0.028 Uiso 1 1 calc R . .
C12 C -0.11032(13) 0.61162(6) 0.05906(8) 0.0179(2) Uani 1 1 d . A .
H12A H -0.0087 0.6169 0.0997 0.021 Uiso 1 1 calc R . .
H12B H -0.1443 0.5822 0.0898 0.021 Uiso 1 1 calc R . .
C13 C -0.17631(13) 0.68611(6) 0.04148(8) 0.0164(2) Uani 1 1 d . . .
C14 C -0.09297(13) 0.74691(7) 0.07623(8) 0.0169(2) Uani 1 1 d . A .
C15 C -0.15061(13) 0.81814(6) 0.05717(8) 0.0165(2) Uani 1 1 d . . .
C16 C -0.29152(13) 0.82682(6) 0.00420(8) 0.0168(2) Uani 1 1 d . A .
H16 H -0.3294 0.8741 -0.0103 0.020 Uiso 1 1 calc R . .
C17 C -0.38157(13) 0.76660(6) -0.02921(8) 0.0163(2) Uani 1 1 d . . .
C18 C -0.52779(13) 0.77575(7) -0.07957(8) 0.0193(2) Uani 1 1 d . A .
H18 H -0.5660 0.8229 -0.0957 0.023 Uiso 1 1 calc R . .
C19 C -0.61439(14) 0.71713(7) -0.10522(9) 0.0228(3) Uani 1 1 d . . .
H19 H -0.7121 0.7237 -0.1387 0.027 Uiso 1 1 calc R A .
C20 C -0.55764(14) 0.64713(7) -0.08166(9) 0.0237(3) Uani 1 1 d . A .
H20 H -0.6179 0.6068 -0.0976 0.028 Uiso 1 1 calc R . .
C21 C -0.41731(14) 0.63613(7) -0.03631(9) 0.0203(3) Uani 1 1 d . . .
H21 H -0.3820 0.5883 -0.0233 0.024 Uiso 1 1 calc R A .
C22 C -0.32322(13) 0.69552(6) -0.00834(8) 0.0166(2) Uani 1 1 d . A .
C23 C -0.05736(13) 0.88314(7) 0.09311(8) 0.0184(2) Uani 1 1 d . A .
C24 C -0.3514(9) 0.3997(5) -0.1363(6) 0.0134(19) Uiso 0.20 1 d P A 2
N1A N -0.47448(13) 0.24269(6) -0.16630(8) 0.0258(3) Uani 1 1 d . . .
C2A C -0.4974(3) 0.21320(10) -0.24768(14) 0.0261(4) Uani 0.75 1 d P G 3
H2A1 H -0.4173 0.2239 -0.2530 0.031 Uiso 0.75 1 calc PR G 3
H2A2 H -0.5816 0.2348 -0.2990 0.031 Uiso 0.75 1 calc PR G 3
C3A C -0.51615(15) 0.12883(7) -0.24553(9) 0.0241(3) Uani 1 1 d . . .
H3A1 H -0.6150 0.1158 -0.2860 0.029 Uiso 1 1 calc R G 3
H3A2 H -0.4615 0.1036 -0.2657 0.029 Uiso 1 1 calc R G 3
N4A N -0.46869(11) 0.10645(6) -0.15462(7) 0.0195(2) Uani 1 1 d . G .
C5A C -0.56289(14) 0.13711(7) -0.13015(9) 0.0212(3) Uani 1 1 d . . .
H5A1 H -0.5269 0.1261 -0.0673 0.025 Uiso 1 1 calc R G .
H5A2 H -0.6557 0.1147 -0.1668 0.025 Uiso 1 1 calc R . .
C6A C -0.57563(18) 0.21943(8) -0.14412(11) 0.0326(3) Uani 1 1 d . G .
H6A1 H -0.6708 0.2322 -0.1928 0.039 Uiso 1 1 calc R . .
H6A2 H -0.5566 0.2439 -0.0895 0.039 Uiso 1 1 calc R . .
C7A C -0.3346(2) 0.21689(11) -0.08787(15) 0.0298(4) Uani 0.75 1 d P G 3
H7A1 H -0.2578 0.2392 -0.0901 0.036 Uiso 0.75 1 calc PR G 3
H7A2 H -0.3250 0.2308 -0.0314 0.036 Uiso 0.75 1 calc PR G 3
C8A C -0.32940(14) 0.13654(8) -0.09380(10) 0.0289(3) Uani 1 1 d . . .
H8A1 H -0.2679 0.1236 -0.1150 0.035 Uiso 1 1 calc R G 3
H8A2 H -0.2900 0.1153 -0.0342 0.035 Uiso 1 1 calc R G 3
N1B N 0.09137(17) 1.04441(8) 0.15181(12) 0.0181(3) Uani 0.75 1 d P H 1
C2B C 0.21564(18) 1.02520(10) 0.14837(12) 0.0229(4) Uani 0.75 1 d P H 1
H2B1 H 0.1894 1.0208 0.0861 0.027 Uiso 0.75 1 calc PR H 1
H2B2 H 0.2546 0.9785 0.1785 0.027 Uiso 0.75 1 calc PR H 1
C3B C 0.32362(18) 1.08566(10) 0.19533(12) 0.0233(4) Uani 0.75 1 d P H 1
H3B1 H 0.4120 1.0645 0.2433 0.028 Uiso 0.75 1 calc PR H 1
H3B2 H 0.3412 1.1090 0.1525 0.028 Uiso 0.75 1 calc PR H 1
N4B N 0.2764(3) 1.14023(13) 0.23284(17) 0.0184(5) Uani 0.75 1 d P H 1
C5B C 0.14838(19) 1.17302(9) 0.16127(12) 0.0251(4) Uani 0.75 1 d P H 1
H5B1 H 0.1682 1.1995 0.1212 0.030 Uiso 0.75 1 calc PR H 1
H5B2 H 0.1137 1.2082 0.1866 0.030 Uiso 0.75 1 calc PR H 1
C6B C 0.03540(18) 1.11568(9) 0.10777(11) 0.0200(3) Uani 0.75 1 d P H 1
H6B1 H -0.0500 1.1276 0.1067 0.024 Uiso 0.75 1 calc PR H 1
H6B2 H 0.0124 1.1141 0.0460 0.024 Uiso 0.75 1 calc PR H 1
C7B C 0.13131(18) 1.04772(9) 0.24666(11) 0.0198(3) Uani 0.75 1 d P H 1
H7B1 H 0.1643 0.9999 0.2751 0.024 Uiso 0.75 1 calc PR H 1
H7B2 H 0.0502 1.0617 0.2496 0.024 Uiso 0.75 1 calc PR H 1
C8B C 0.2480(2) 1.10434(10) 0.29481(12) 0.0253(4) Uani 0.75 1 d P H 1
H8B1 H 0.2203 1.1409 0.3229 0.030 Uiso 0.75 1 calc PR H 1
H8B2 H 0.3335 1.0804 0.3421 0.030 Uiso 0.75 1 calc PR H 1
N1C N 0.0754(6) 1.0428(3) 0.1735(4) 0.0192(15) Uiso 0.25 1 d P I 2
H1C H 0.0063 1.0079 0.1466 0.023 Uiso 0.25 1 calc PR I 2
C2C C 0.1200(6) 1.0628(3) 0.1112(4) 0.0261(11) Uiso 0.25 1 d P I 2
H2C1 H 0.0386 1.0771 0.0530 0.031 Uiso 0.25 1 calc PR I 2
H2C2 H 0.1657 1.0212 0.1023 0.031 Uiso 0.25 1 calc PR I 2
C3C C 0.2224(6) 1.1265(3) 0.1531(4) 0.0275(11) Uiso 0.25 1 d P I 2
H3C1 H 0.3050 1.1171 0.1500 0.033 Uiso 0.25 1 calc PR I 2
H3C2 H 0.1776 1.1712 0.1195 0.033 Uiso 0.25 1 calc PR I 2
N4C N 0.2655(10) 1.1360(5) 0.2469(6) 0.021(2) Uiso 0.25 1 d P I 2
C5C C 0.1394(6) 1.1611(3) 0.2456(4) 0.0238(11) Uiso 0.25 1 d P I 2
H5C1 H 0.1124 1.2097 0.2186 0.029 Uiso 0.25 1 calc PR I 2
H5C2 H 0.1613 1.1645 0.3071 0.029 Uiso 0.25 1 calc PR I 2
C6C C 0.0171(6) 1.1080(3) 0.1921(4) 0.0265(11) Uiso 0.25 1 d P I 2
H6C1 H -0.0239 1.0943 0.2268 0.032 Uiso 0.25 1 calc PR I 2
H6C2 H -0.0560 1.1306 0.1360 0.032 Uiso 0.25 1 calc PR I 2
C7C C 0.1927(6) 1.0129(3) 0.2567(4) 0.0234(10) Uiso 0.25 1 d P I 2
H7C1 H 0.2220 0.9660 0.2454 0.028 Uiso 0.25 1 calc PR I 2
H7C2 H 0.1652 1.0051 0.3000 0.028 Uiso 0.25 1 calc PR I 2
C8C C 0.3133(6) 1.0684(3) 0.2934(4) 0.0280(12) Uiso 0.25 1 d P I 2
H8C1 H 0.3521 1.0764 0.3573 0.034 Uiso 0.25 1 calc PR I 2
H8C2 H 0.3881 1.0489 0.2869 0.034 Uiso 0.25 1 calc PR I 2
C1D C -0.3329(6) 0.2221(3) -0.1265(5) 0.0273(13) Uiso 0.25 1 d P G 4
H1D1 H -0.2713 0.2535 -0.0753 0.033 Uiso 0.25 1 calc PR G 4
H1D2 H -0.3043 0.2246 -0.1697 0.033 Uiso 0.25 1 calc PR G 4
C2D C -0.5553(6) 0.2038(3) -0.2647(4) 0.0200(14) Uiso 0.25 1 d P G 4
H2D1 H -0.6571 0.2096 -0.2950 0.024 Uiso 0.25 1 calc PR G 4
H2D2 H -0.5247 0.2246 -0.3024 0.024 Uiso 0.25 1 calc PR G 4
H7W2 H -0.3455 1.0420 0.0942 0.031(5) 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 0.0307(8) 0.0152(6) 0.0229(7) -0.0050(5) 0.0097(6) -0.0022(5)
C1 0.0205(9) 0.0128(8) 0.0217(9) 0.0027(7) 0.0087(9) 0.0009(6)
O2 0.0334(8) 0.0183(7) 0.0259(11) -0.0019(9) 0.0163(10) -0.0090(6)
C2 0.0189(6) 0.0124(6) 0.0263(7) -0.0023(5) 0.0029(5) 0.0025(5)
O3 0.0317(5) 0.0148(4) 0.0387(6) 0.0019(4) 0.0217(5) -0.0023(4)
C3 0.0193(6) 0.0137(6) 0.0263(6) 0.0017(5) 0.0104(5) 0.0026(5)
O4 0.0196(4) 0.0186(4) 0.0215(5) -0.0023(3) 0.0072(4) 0.0010(3)
C4 0.0185(6) 0.0132(5) 0.0190(6) -0.0006(4) 0.0090(5) 0.0017(4)
O5 0.0215(5) 0.0196(5) 0.0299(5) -0.0029(4) 0.0131(4) -0.0026(4)
C5 0.0165(5) 0.0164(6) 0.0159(6) 0.0002(4) 0.0070(5) 0.0032(4)
O6 0.0253(5) 0.0149(4) 0.0302(5) -0.0034(4) 0.0099(4) -0.0014(4)
C6 0.0195(6) 0.0206(6) 0.0174(6) -0.0006(5) 0.0089(5) 0.0007(5)
O7 0.0491(7) 0.0236(5) 0.0485(7) -0.0030(5) 0.0342(6) -0.0036(5)
C7 0.0210(6) 0.0284(7) 0.0232(7) 0.0017(5) 0.0114(5) -0.0007(5)
O8 0.0311(5) 0.0173(5) 0.0331(6) -0.0057(4) 0.0115(5) -0.0004(4)
C8 0.0228(7) 0.0426(8) 0.0210(6) 0.0040(6) 0.0136(6) 0.0049(6)
O9 0.0290(8) 0.0278(8) 0.0244(8) 0.0041(6) 0.0168(7) -0.0021(6)
C9 0.0214(6) 0.0374(8) 0.0162(6) -0.0025(5) 0.0083(5) 0.0091(6)
O10 0.020(3) 0.017(2) 0.020(3) -0.0036(18) 0.012(2) -0.002(2)
C10 0.0165(6) 0.0227(6) 0.0173(6) -0.0024(5) 0.0053(5) 0.0059(5)
O11 0.038(3) 0.018(3) 0.023(4) 0.001(3) 0.021(4) -0.003(2)
C11 0.0208(6) 0.0195(6) 0.0192(6) -0.0052(5) 0.0032(5) 0.0065(5)
C12 0.0238(6) 0.0136(5) 0.0168(6) 0.0009(4) 0.0113(5) 0.0011(5)
C13 0.0231(6) 0.0148(5) 0.0140(5) 0.0003(4) 0.0117(5) 0.0009(5)
C14 0.0200(6) 0.0175(6) 0.0137(5) -0.0005(4) 0.0094(5) 0.0007(5)
C15 0.0227(6) 0.0149(6) 0.0139(5) -0.0011(4) 0.0112(5) -0.0013(5)
C16 0.0238(6) 0.0145(5) 0.0149(5) 0.0008(4) 0.0123(5) 0.0014(5)
C17 0.0219(6) 0.0173(6) 0.0131(5) -0.0004(4) 0.0117(5) -0.0004(5)
C18 0.0225(6) 0.0206(6) 0.0178(6) -0.0008(5) 0.0128(5) 0.0013(5)
C19 0.0206(6) 0.0269(7) 0.0243(6) -0.0038(5) 0.0142(5) -0.0018(5)
C20 0.0274(7) 0.0223(6) 0.0285(7) -0.0060(5) 0.0196(6) -0.0067(5)
C21 0.0263(6) 0.0166(6) 0.0230(6) -0.0021(5) 0.0165(5) -0.0026(5)
C22 0.0229(6) 0.0166(6) 0.0145(5) -0.0009(4) 0.0128(5) -0.0011(5)
C23 0.0238(6) 0.0174(6) 0.0162(6) -0.0026(4) 0.0123(5) -0.0024(5)
N1A 0.0373(7) 0.0127(5) 0.0360(7) -0.0023(4) 0.0255(6) -0.0051(5)
C2A 0.0461(14) 0.0187(9) 0.0230(9) 0.0024(7) 0.0248(10) 0.0001(9)
C3A 0.0329(7) 0.0215(6) 0.0189(6) -0.0029(5) 0.0146(6) -0.0021(5)
N4A 0.0238(5) 0.0150(5) 0.0217(5) 0.0025(4) 0.0135(5) 0.0004(4)
C5A 0.0257(6) 0.0178(6) 0.0241(6) 0.0043(5) 0.0160(6) 0.0017(5)
C6A 0.0532(10) 0.0208(7) 0.0438(9) 0.0109(6) 0.0394(8) 0.0105(6)
C7A 0.0260(10) 0.0356(11) 0.0280(10) -0.0109(8) 0.0147(8) -0.0132(8)
C8A 0.0203(6) 0.0349(8) 0.0267(7) 0.0050(6) 0.0096(6) 0.0018(6)
N1B 0.0199(8) 0.0159(8) 0.0189(8) -0.0033(6) 0.0109(7) -0.0018(5)
C2B 0.0232(8) 0.0210(8) 0.0274(9) -0.0073(7) 0.0155(7) -0.0012(7)
C3B 0.0218(8) 0.0237(9) 0.0297(9) -0.0053(7) 0.0174(8) -0.0025(7)
N4B 0.0239(10) 0.0160(9) 0.0179(10) -0.0013(7) 0.0128(9) -0.0034(6)
C5B 0.0259(9) 0.0164(8) 0.0274(9) 0.0002(7) 0.0105(8) 0.0000(7)
C6B 0.0209(8) 0.0203(8) 0.0180(8) 0.0010(6) 0.0098(7) 0.0021(6)
C7B 0.0210(8) 0.0202(8) 0.0195(8) 0.0011(6) 0.0117(7) -0.0019(7)
C8B 0.0302(9) 0.0299(9) 0.0186(8) -0.0042(7) 0.0149(8) -0.0105(8)

_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 C1 1.248(3) . ?
C1 O2 1.286(3) . ?
C1 C2 1.492(2) . ?
C2 C11 1.366(2) . ?
C2 C3 1.4358(19) . ?
C2 C24 1.696(11) . ?
O3 C3 1.3534(16) . ?
O3 H3 0.95(3) . ?
C3 C4 1.3877(17) . ?
O4 C14 1.3633(15) . ?
O4 H4 0.99(2) . ?
C4 C5 1.4254(17) . ?
C4 C12 1.5203(17) . ?
O5 C23 1.2626(16) . ?
C5 C6 1.4241(18) . ?
C5 C10 1.4299(17) . ?
O6 C23 1.2616(16) . ?
C6 C7 1.3730(18) . ?
C6 H6 0.9500 . ?
O7 H7W1 0.92(3) . ?
O7 H7W2 0.8307 . ?
C7 C8 1.409(2) . ?
C7 H7 0.9500 . ?
O8 H8W1 0.87(2) . ?
O8 H8W2 0.89(2) . ?
C8 C9 1.362(2) . ?
C8 H8 0.9500 . ?
O9 H9W2 0.75(3) . ?
O9 H9W1 0.72(3) . ?
C9 C10 1.422(2) . ?
C9 H9 0.9500 . ?
O10 C24 1.263(10) . ?
C10 C11 1.4046(19) . ?
O11 C24 1.248(11) . ?
O11 H3 1.38(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.5225(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3881(17) . ?
C13 C22 1.4267(18) . ?
C14 C15 1.4321(17) . ?
C15 C16 1.3702(18) . ?
C15 C23 1.5046(17) . ?
C16 C17 1.4146(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.4195(18) . ?
C17 C22 1.4323(17) . ?
C18 C19 1.3717(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.410(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3686(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.4280(17) . ?
C21 H21 0.9500 . ?
N1A C1D 1.425(6) . ?
N1A C2A 1.441(2) . ?
N1A C6A 1.4727(19) . ?
N1A C7A 1.531(3) . ?
N1A C2D 1.651(6) . ?
N1A H1A 0.94(2) . ?
C2A C3A 1.581(2) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C2D 1.444(6) . ?
C3A N4A 1.4716(17) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
N4A C8A 1.4726(18) . ?
N4A C5A 1.4753(16) . ?
C5A C6A 1.5400(19) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.496(3) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C1D 1.683(6) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
N1B C6B 1.494(2) . ?
N1B C2B 1.496(3) . ?
N1B C7B 1.504(2) . ?
N1B H1B 1.00(3) . ?
C2B C3B 1.540(2) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B N4B 1.467(3) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
N4B C5B 1.462(3) . ?
N4B C8B 1.470(3) . ?
C5B C6B 1.544(2) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B C8B 1.545(2) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
N1C C7C 1.476(8) . ?
N1C C2C 1.500(8) . ?
N1C C6C 1.501(8) . ?
N1C H1B 1.05(3) . ?
N1C H1C 0.9300 . ?
C2C C3C 1.543(8) . ?
C2C H2C1 0.9900 . ?
C2C H2C2 0.9900 . ?
C3C N4C 1.484(10) . ?
C3C H3C1 0.9900 . ?
C3C H3C2 0.9900 . ?
N4C C8C 1.440(11) . ?
N4C C5C 1.501(10) . ?
C5C C6C 1.549(8) . ?
C5C H5C1 0.9900 . ?
C5C H5C2 0.9900 . ?
C6C H6C1 0.9900 . ?
C6C H6C2 0.9900 . ?
C7C C8C 1.555(8) . ?
C7C H7C1 0.9900 . ?
C7C H7C2 0.9900 . ?
C8C H8C1 0.9900 . ?
C8C H8C2 0.9900 . ?
C1D H1D1 0.9900 . ?
C1D H1D2 0.9900 . ?
C2D H2D1 0.9900 . ?
C2D H2D2 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
O1 C1 O2 123.75(18) . . ?
O1 C1 C2 121.3(2) . . ?
O2 C1 C2 115.0(2) . . ?
C11 C2 C3 119.41(12) . . ?
C11 C2 C1 116.31(15) . . ?
C3 C2 C1 124.28(16) . . ?
C11 C2 C24 134.5(4) . . ?
C3 C2 C24 106.0(4) . . ?
C1 C2 C24 18.5(3) . . ?
C3 O3 H3 104.8(14) . . ?
O3 C3 C4 119.31(12) . . ?
O3 C3 C2 119.59(12) . . ?
C4 C3 C2 121.10(12) . . ?
C14 O4 H4 103.7(12) . . ?
C3 C4 C5 118.71(11) . . ?
C3 C4 C12 120.01(11) . . ?
C5 C4 C12 121.24(11) . . ?
C6 C5 C4 122.85(11) . . ?
C6 C5 C10 117.06(11) . . ?
C4 C5 C10 120.07(11) . . ?
C7 C6 C5 121.13(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
H7W1 O7 H7W2 110.2 . . ?
C6 C7 C8 121.29(13) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
H8W1 O8 H8W2 103(2) . . ?
C9 C8 C7 119.36(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
H9W2 O9 H9W1 101(3) . . ?
C8 C9 C10 121.07(12) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 121.07(12) . . ?
C11 C10 C5 118.93(12) . . ?
C9 C10 C5 120.00(12) . . ?
C24 O11 H3 93.2(12) . . ?
C2 C11 C10 121.68(12) . . ?
C2 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C4 C12 C13 115.24(10) . . ?
C4 C12 H12A 108.5 . . ?
C13 C12 H12A 108.5 . . ?
C4 C12 H12B 108.5 . . ?
C13 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C22 118.34(11) . . ?
C14 C13 C12 119.93(11) . . ?
C22 C13 C12 121.72(11) . . ?
O4 C14 C13 119.31(11) . . ?
O4 C14 C15 119.06(11) . . ?
C13 C14 C15 121.62(11) . . ?
C16 C15 C14 119.49(11) . . ?
C16 C15 C23 120.06(11) . . ?
C14 C15 C23 120.44(11) . . ?
C15 C16 C17 121.16(11) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 121.00(11) . . ?
C16 C17 C22 118.97(11) . . ?
C18 C17 C22 119.98(11) . . ?
C19 C18 C17 120.62(12) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.69(12) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 121.24(12) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.98(12) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C13 C22 C21 122.44(11) . . ?
C13 C22 C17 120.13(11) . . ?
C21 C22 C17 117.38(11) . . ?
O6 C23 O5 123.09(12) . . ?
O6 C23 C15 118.43(11) . . ?
O5 C23 C15 118.47(11) . . ?
O11 C24 O10 127.1(9) . . ?
O11 C24 C2 125.3(7) . . ?
O10 C24 C2 107.5(9) . . ?
C1D N1A C2A 86.9(3) . . ?
C1D N1A C6A 129.1(3) . . ?
C2A N1A C6A 114.66(15) . . ?
C1D N1A C7A 27.4(3) . . ?
C2A N1A C7A 110.01(15) . . ?
C6A N1A C7A 104.20(13) . . ?
C1D N1A C2D 104.6(4) . . ?
C2A N1A C2D 20.5(2) . . ?
C6A N1A C2D 95.1(2) . . ?
C7A N1A C2D 123.6(2) . . ?
C1D N1A H1A 100.6(14) . . ?
C2A N1A H1A 110.9(13) . . ?
C6A N1A H1A 111.8(13) . . ?
C7A N1A H1A 104.6(14) . . ?
C2D N1A H1A 116.5(14) . . ?
N1A C2A C3A 107.70(13) . . ?
N1A C2A H2A1 110.2 . . ?
C3A C2A H2A1 110.2 . . ?
N1A C2A H2A2 110.2 . . ?
C3A C2A H2A2 110.2 . . ?
H2A1 C2A H2A2 108.5 . . ?
C2D C3A N4A 114.7(3) . . ?
C2D C3A C2A 21.8(2) . . ?
N4A C3A C2A 109.33(11) . . ?
C2D C3A H3A1 88.5 . . ?
N4A C3A H3A1 109.8 . . ?
C2A C3A H3A1 109.8 . . ?
C2D C3A H3A2 123.0 . . ?
N4A C3A H3A2 109.8 . . ?
C2A C3A H3A2 109.8 . . ?
H3A1 C3A H3A2 108.3 . . ?
C3A N4A C8A 108.75(10) . . ?
C3A N4A C5A 108.93(10) . . ?
C8A N4A C5A 107.79(11) . . ?
N4A C5A C6A 110.73(10) . . ?
N4A C5A H5A1 109.5 . . ?
C6A C5A H5A1 109.5 . . ?
N4A C5A H5A2 109.5 . . ?
C6A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 108.1 . . ?
N1A C6A C5A 108.31(11) . . ?
N1A C6A H6A1 110.0 . . ?
C5A C6A H6A1 110.0 . . ?
N1A C6A H6A2 110.0 . . ?
C5A C6A H6A2 110.0 . . ?
H6A1 C6A H6A2 108.4 . . ?
C8A C7A N1A 107.90(13) . . ?
C8A C7A H7A1 110.1 . . ?
N1A C7A H7A1 110.1 . . ?
C8A C7A H7A2 110.1 . . ?
N1A C7A H7A2 110.1 . . ?
H7A1 C7A H7A2 108.4 . . ?
N4A C8A C7A 111.16(13) . . ?
N4A C8A C1D 106.6(2) . . ?
C7A C8A C1D 24.8(2) . . ?
N4A C8A H8A1 109.4 . . ?
C7A C8A H8A1 109.4 . . ?
C1D C8A H8A1 89.2 . . ?
N4A C8A H8A2 109.4 . . ?
C7A C8A H8A2 109.4 . . ?
C1D C8A H8A2 131.4 . . ?
H8A1 C8A H8A2 108.0 . . ?
C6B N1B C2B 109.60(16) . . ?
C6B N1B C7B 110.12(14) . . ?
C2B N1B C7B 109.62(14) . . ?
C6B N1B H1B 108.6(15) . . ?
C2B N1B H1B 110.4(15) . . ?
C7B N1B H1B 108.4(15) . . ?
N1B C2B C3B 107.71(13) . . ?
N1B C2B H2B1 110.2 . . ?
C3B C2B H2B1 110.2 . . ?
N1B C2B H2B2 110.2 . . ?
C3B C2B H2B2 110.2 . . ?
H2B1 C2B H2B2 108.5 . . ?
N4B C3B C2B 111.58(16) . . ?
N4B C3B H3B1 109.3 . . ?
C2B C3B H3B1 109.3 . . ?
N4B C3B H3B2 109.3 . . ?
C2B C3B H3B2 109.3 . . ?
H3B1 C3B H3B2 108.0 . . ?
C5B N4B C3B 109.03(19) . . ?
C5B N4B C8B 109.1(2) . . ?
C3B N4B C8B 108.48(19) . . ?
N4B C5B C6B 111.54(16) . . ?
N4B C5B H5B1 109.3 . . ?
C6B C5B H5B1 109.3 . . ?
N4B C5B H5B2 109.3 . . ?
C6B C5B H5B2 109.3 . . ?
H5B1 C5B H5B2 108.0 . . ?
N1B C6B C5B 107.60(14) . . ?
N1B C6B H6B1 110.2 . . ?
C5B C6B H6B1 110.2 . . ?
N1B C6B H6B2 110.2 . . ?
C5B C6B H6B2 110.2 . . ?
H6B1 C6B H6B2 108.5 . . ?
N1B C7B C8B 107.81(13) . . ?
N1B C7B H7B1 110.1 . . ?
C8B C7B H7B1 110.1 . . ?
N1B C7B H7B2 110.1 . . ?
C8B C7B H7B2 110.1 . . ?
H7B1 C7B H7B2 108.5 . . ?
N4B C8B C7B 111.08(16) . . ?
N4B C8B H8B1 109.4 . . ?
C7B C8B H8B1 109.4 . . ?
N4B C8B H8B2 109.4 . . ?
C7B C8B H8B2 109.4 . . ?
H8B1 C8B H8B2 108.0 . . ?
C7C N1C C2C 110.9(5) . . ?
C7C N1C C6C 110.4(5) . . ?
C2C N1C C6C 109.5(5) . . ?
C7C N1C H1B 117.9(15) . . ?
C2C N1C H1B 77.7(15) . . ?
C6C N1C H1B 124.4(15) . . ?
C7C N1C H1C 108.7 . . ?
C2C N1C H1C 108.7 . . ?
C6C N1C H1C 108.7 . . ?
H1B N1C H1C 31.2 . . ?
N1C C2C C3C 107.4(5) . . ?
N1C C2C H2C1 110.2 . . ?
C3C C2C H2C1 110.2 . . ?
N1C C2C H2C2 110.2 . . ?
C3C C2C H2C2 110.2 . . ?
H2C1 C2C H2C2 108.5 . . ?
N4C C3C C2C 110.2(5) . . ?
N4C C3C H3C1 109.6 . . ?
C2C C3C H3C1 109.6 . . ?
N4C C3C H3C2 109.6 . . ?
C2C C3C H3C2 109.6 . . ?
H3C1 C3C H3C2 108.1 . . ?
C8C N4C C3C 110.1(7) . . ?
C8C N4C C5C 109.9(6) . . ?
C3C N4C C5C 106.6(7) . . ?
N4C C5C C6C 110.7(6) . . ?
N4C C5C H5C1 109.5 . . ?
C6C C5C H5C1 109.5 . . ?
N4C C5C H5C2 109.5 . . ?
C6C C5C H5C2 109.5 . . ?
H5C1 C5C H5C2 108.1 . . ?
N1C C6C C5C 106.7(5) . . ?
N1C C6C H6C1 110.4 . . ?
C5C C6C H6C1 110.4 . . ?
N1C C6C H6C2 110.4 . . ?
C5C C6C H6C2 110.4 . . ?
H6C1 C6C H6C2 108.6 . . ?
N1C C7C C8C 107.2(5) . . ?
N1C C7C H7C1 110.3 . . ?
C8C C7C H7C1 110.3 . . ?
N1C C7C H7C2 110.3 . . ?
C8C C7C H7C2 110.3 . . ?
H7C1 C7C H7C2 108.5 . . ?
N4C C8C C7C 110.9(6) . . ?
N4C C8C H8C1 109.5 . . ?
C7C C8C H8C1 109.5 . . ?
N4C C8C H8C2 109.5 . . ?
C7C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 108.1 . . ?
N1A C1D C8A 103.6(4) . . ?
N1A C1D H1D1 111.0 . . ?
C8A C1D H1D1 111.0 . . ?
N1A C1D H1D2 111.0 . . ?
C8A C1D H1D2 111.0 . . ?
H1D1 C1D H1D2 109.0 . . ?
C3A C2D N1A 104.0(4) . . ?
C3A C2D H2D1 111.0 . . ?
N1A C2D H2D1 111.0 . . ?
C3A C2D H2D2 111.0 . . ?
N1A C2D H2D2 111.0 . . ?
H2D1 C2D H2D2 109.0 . . ?

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
O1 C1 C2 C11 -1.3(2) . . . . ?
O2 C1 C2 C11 -179.53(17) . . . . ?
O1 C1 C2 C3 178.10(15) . . . . ?
O2 C1 C2 C3 -0.1(2) . . . . ?
O1 C1 C2 C24 169.0(11) . . . . ?
O2 C1 C2 C24 -9.2(9) . . . . ?
C11 C2 C3 O3 -178.71(12) . . . . ?
C1 C2 C3 O3 1.9(2) . . . . ?
C24 C2 C3 O3 4.9(3) . . . . ?
C11 C2 C3 C4 2.03(19) . . . . ?
C1 C2 C3 C4 -177.36(13) . . . . ?
C24 C2 C3 C4 -174.4(3) . . . . ?
O3 C3 C4 C5 176.93(11) . . . . ?
C2 C3 C4 C5 -3.81(18) . . . . ?
O3 C3 C4 C12 -0.74(18) . . . . ?
C2 C3 C4 C12 178.52(11) . . . . ?
C3 C4 C5 C6 -174.92(12) . . . . ?
C12 C4 C5 C6 2.72(18) . . . . ?
C3 C4 C5 C10 3.55(18) . . . . ?
C12 C4 C5 C10 -178.81(11) . . . . ?
C4 C5 C6 C7 -179.45(12) . . . . ?
C10 C5 C6 C7 2.04(18) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 -2.3(2) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C8 C9 C10 C11 -178.53(13) . . . . ?
C8 C9 C10 C5 1.65(19) . . . . ?
C6 C5 C10 C11 177.03(11) . . . . ?
C4 C5 C10 C11 -1.53(18) . . . . ?
C6 C5 C10 C9 -3.16(17) . . . . ?
C4 C5 C10 C9 178.29(11) . . . . ?
C3 C2 C11 C10 0.09(19) . . . . ?
C1 C2 C11 C10 179.52(12) . . . . ?
C24 C2 C11 C10 175.2(4) . . . . ?
C9 C10 C11 C2 179.89(12) . . . . ?
C5 C10 C11 C2 -0.30(19) . . . . ?
C3 C4 C12 C13 -115.49(13) . . . . ?
C5 C4 C12 C13 66.90(15) . . . . ?
C4 C12 C13 C14 -117.55(12) . . . . ?
C4 C12 C13 C22 64.13(15) . . . . ?
C22 C13 C14 O4 175.91(10) . . . . ?
C12 C13 C14 O4 -2.46(17) . . . . ?
C22 C13 C14 C15 -5.15(17) . . . . ?
C12 C13 C14 C15 176.48(11) . . . . ?
O4 C14 C15 C16 179.70(10) . . . . ?
C13 C14 C15 C16 0.76(18) . . . . ?
O4 C14 C15 C23 1.16(17) . . . . ?
C13 C14 C15 C23 -177.78(11) . . . . ?
C14 C15 C16 C17 2.51(17) . . . . ?
C23 C15 C16 C17 -178.94(10) . . . . ?
C15 C16 C17 C18 176.12(11) . . . . ?
C15 C16 C17 C22 -1.23(17) . . . . ?
C16 C17 C18 C19 -174.34(11) . . . . ?
C22 C17 C18 C19 2.99(18) . . . . ?
C17 C18 C19 C20 -0.27(19) . . . . ?
C18 C19 C20 C21 -2.5(2) . . . . ?
C19 C20 C21 C22 2.4(2) . . . . ?
C14 C13 C22 C21 -171.20(11) . . . . ?
C12 C13 C22 C21 7.14(17) . . . . ?
C14 C13 C22 C17 6.36(16) . . . . ?
C12 C13 C22 C17 -175.30(10) . . . . ?
C20 C21 C22 C13 177.94(12) . . . . ?
C20 C21 C22 C17 0.32(18) . . . . ?
C16 C17 C22 C13 -3.27(16) . . . . ?
C18 C17 C22 C13 179.35(10) . . . . ?
C16 C17 C22 C21 174.41(11) . . . . ?
C18 C17 C22 C21 -2.97(16) . . . . ?
C16 C15 C23 O6 0.04(17) . . . . ?
C14 C15 C23 O6 178.57(11) . . . . ?
C16 C15 C23 O5 -178.61(11) . . . . ?
C14 C15 C23 O5 -0.08(17) . . . . ?
C11 C2 C24 O11 169.8(7) . . . . ?
C3 C2 C24 O11 -14.6(10) . . . . ?
C1 C2 C24 O11 157.6(17) . . . . ?
C11 C2 C24 O10 -10.5(8) . . . . ?
C3 C2 C24 O10 165.1(5) . . . . ?
C1 C2 C24 O10 -22.7(6) . . . . ?
C1D N1A C2A C3A 82.2(3) . . . . ?
C6A N1A C2A C3A -49.8(2) . . . . ?
C7A N1A C2A C3A 67.2(2) . . . . ?
C2D N1A C2A C3A -67.8(7) . . . . ?
N1A C2A C3A C2D 93.7(7) . . . . ?
N1A C2A C3A N4A -14.6(2) . . . . ?
C2D C3A N4A C8A -73.2(3) . . . . ?
C2A C3A N4A C8A -50.41(17) . . . . ?
C2D C3A N4A C5A 44.0(3) . . . . ?
C2A C3A N4A C5A 66.82(16) . . . . ?
C3A N4A C5A C6A -54.00(14) . . . . ?
C8A N4A C5A C6A 63.84(14) . . . . ?
C1D N1A C6A C5A -44.3(4) . . . . ?
C2A N1A C6A C5A 62.94(18) . . . . ?
C7A N1A C6A C5A -57.36(16) . . . . ?
C2D N1A C6A C5A 69.1(2) . . . . ?
N4A C5A C6A N1A -7.51(17) . . . . ?
C1D N1A C7A C8A -85.4(6) . . . . ?
C2A N1A C7A C8A -51.11(19) . . . . ?
C6A N1A C7A C8A 72.26(17) . . . . ?
C2D N1A C7A C8A -33.9(3) . . . . ?
C3A N4A C8A C7A 68.52(16) . . . . ?
C5A N4A C8A C7A -49.43(16) . . . . ?
C3A N4A C8A C1D 42.7(3) . . . . ?
C5A N4A C8A C1D -75.2(3) . . . . ?
N1A C7A C8A N4A -16.16(19) . . . . ?
N1A C7A C8A C1D 67.6(5) . . . . ?
C6B N1B C2B C3B 58.67(19) . . . . ?
C7B N1B C2B C3B -62.30(18) . . . . ?
N1B C2B C3B N4B 3.3(2) . . . . ?
C2B C3B N4B C5B -60.9(2) . . . . ?
C2B C3B N4B C8B 57.8(2) . . . . ?
C3B N4B C5B C6B 56.3(2) . . . . ?
C8B N4B C5B C6B -62.0(2) . . . . ?
C2B N1B C6B C5B -62.99(18) . . . . ?
C7B N1B C6B C5B 57.68(19) . . . . ?
N4B C5B C6B N1B 4.3(2) . . . . ?
C6B N1B C7B C8B -62.39(19) . . . . ?
C2B N1B C7B C8B 58.27(18) . . . . ?
C5B N4B C8B C7B 56.9(2) . . . . ?
C3B N4B C8B C7B -61.8(2) . . . . ?
N1B C7B C8B N4B 3.9(2) . . . . ?
C7C N1C C2C C3C -66.9(6) . . . . ?
C6C N1C C2C C3C 55.2(6) . . . . ?
N1C C2C C3C N4C 12.2(7) . . . . ?
C2C C3C N4C C8C 51.4(8) . . . . ?
C2C C3C N4C C5C -67.8(7) . . . . ?
C8C N4C C5C C6C -64.5(8) . . . . ?
C3C N4C C5C C6C 54.8(7) . . . . ?
C7C N1C C6C C5C 55.0(6) . . . . ?
C2C N1C C6C C5C -67.4(6) . . . . ?
N4C C5C C6C N1C 9.8(7) . . . . ?
C2C N1C C7C C8C 53.3(6) . . . . ?
C6C N1C C7C C8C -68.2(6) . . . . ?
C3C N4C C8C C7C -65.8(8) . . . . ?
C5C N4C C8C C7C 51.4(8) . . . . ?
N1C C7C C8C N4C 11.9(7) . . . . ?
C2A N1A C1D C8A -87.9(3) . . . . ?
C6A N1A C1D C8A 31.8(5) . . . . ?
C7A N1A C1D C8A 60.2(5) . . . . ?
C2D N1A C1D C8A -77.5(4) . . . . ?
N4A C8A C1D N1A 28.2(4) . . . . ?
C7A C8A C1D N1A -76.6(6) . . . . ?
N4A C3A C2D N1A 21.6(4) . . . . ?
C2A C3A C2D N1A -58.8(6) . . . . ?
C1D N1A C2D C3A 53.3(5) . . . . ?
C2A N1A C2D C3A 84.3(7) . . . . ?
C6A N1A C2D C3A -79.3(3) . . . . ?
C7A N1A C2D C3A 31.5(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
N1C H1C O6 0.93 1.73 2.640(6) 163.7 .
N1C H1C O5 0.93 2.63 3.193(6) 119.9 .
O7 H7W2 O8 0.83 1.93 2.7470(17) 166.0 4_576
O4 H4 O5 0.99(2) 1.57(2) 2.5038(14) 156(2) .
N1A H1A O2 0.94(2) 1.87(2) 2.731(2) 152(2) .
N1A H1A O10 0.94(2) 2.04(2) 2.841(5) 141.7(19) .
N1A H1A O11 0.94(2) 2.08(2) 2.869(9) 141.0(19) .
N1A H1A O1 0.94(2) 2.53(2) 3.2027(19) 129.0(17) .
N1B H1B O6 1.00(3) 1.70(3) 2.6962(19) 175(2) .
N1B H1B O5 1.00(3) 2.54(3) 3.1775(19) 121.6(18) .
O8 H8W2 N4A 0.89(2) 2.00(2) 2.8753(16) 170(2) 2_454
O7 H7W1 O6 0.92(3) 1.98(2) 2.8428(16) 155(2) .
O3 H3 O2 0.95(3) 1.69(2) 2.565(2) 153(2) .
O9 H9W2 O7 0.75(3) 2.19(3) 2.903(2) 158(3) 2_545
O8 H8W1 O1 0.87(2) 1.98(2) 2.8192(19) 164(2) .
O8 H8W1 O10 0.87(2) 2.15(2) 3.018(6) 177(2) .
O9 H9W1 O4 0.72(3) 2.25(3) 2.899(2) 149(3) .

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.044