# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


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#                 Cambridge Crystallographic Data Centre
#                                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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#  except for the purpose of generating routine backup copies 
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data_mo_dm11520_0m
_database_code_depnum_ccdc_archive 'CCDC 858690'
#TrackingRef 'mo_dm11520_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.42

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   P2(1)/c

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                   20.206(4)
_cell_length_b                   8.8525(16)
_cell_length_c                   22.032(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.898(3)
_cell_angle_gamma                90.00
_cell_volume                     3926.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4655
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(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-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26959
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.01
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7673
_reflns_number_gt                5255
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.1042P)^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       ?
_refine_ls_number_reflns         7673
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.003
_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 0.69549(8) 0.88448(18) 0.37831(8) 0.0205(4) Uani 1 1 d . . .
O2 O 0.50074(8) 0.67760(19) 0.32058(9) 0.0266(4) Uani 1 1 d . . .
O3 O 0.60828(10) 0.4826(2) 0.50212(10) 0.0400(5) Uani 1 1 d . . .
O4 O 0.69586(9) 0.5906(2) 0.46399(8) 0.0273(4) Uani 1 1 d . . .
O5 O 0.63311(10) 0.8568(2) 0.50806(8) 0.0304(5) Uani 1 1 d . . .
O6 O 0.56645(9) 0.95218(18) 0.43126(8) 0.0243(4) Uani 1 1 d . . .
O7 O 0.18979(8) 0.62306(17) 0.37472(7) 0.0196(4) Uani 1 1 d . . .
O8 O 0.00460(8) 0.82783(19) 0.29390(8) 0.0206(4) Uani 1 1 d . . .
O9 O 0.07991(10) 1.0420(2) 0.47794(9) 0.0345(5) Uani 1 1 d . . .
O10 O 0.17406(9) 0.9185(2) 0.46450(8) 0.0284(4) Uani 1 1 d . . .
O11 O 0.10940(10) 0.6539(2) 0.49499(8) 0.0286(4) Uani 1 1 d . . .
O12 O 0.05352(9) 0.55453(18) 0.41290(8) 0.0225(4) Uani 1 1 d . . .
N1 N 0.72353(10) 0.6560(2) 0.33876(9) 0.0184(4) Uani 1 1 d . . .
N2 N 0.56246(10) 0.7622(2) 0.32090(9) 0.0183(4) Uani 1 1 d . . .
N3 N 0.22563(10) 0.8579(2) 0.34753(10) 0.0207(5) Uani 1 1 d . . .
N4 N 0.06730(9) 0.7459(2) 0.30261(9) 0.0161(4) Uani 1 1 d . . .
C1 C 0.69277(12) 0.5157(3) 0.32731(11) 0.0193(5) Uani 1 1 d . . .
C2 C 0.72072(13) 0.3869(3) 0.30539(13) 0.0283(6) Uani 1 1 d . . .
H2 H 0.7658 0.3846 0.2964 0.034 Uiso 1 1 calc R . .
C3 C 0.68028(14) 0.2608(3) 0.29707(15) 0.0382(8) Uani 1 1 d . . .
H3 H 0.6983 0.1701 0.2823 0.046 Uiso 1 1 calc R . .
C4 C 0.61411(14) 0.2639(3) 0.30972(15) 0.0365(7) Uani 1 1 d . . .
H4 H 0.5873 0.1762 0.3033 0.044 Uiso 1 1 calc R . .
C5 C 0.58719(13) 0.3950(3) 0.33169(12) 0.0251(6) Uani 1 1 d . . .
H5 H 0.5419 0.3979 0.3403 0.030 Uiso 1 1 calc R . .
C6 C 0.62659(11) 0.5209(3) 0.34090(10) 0.0168(5) Uani 1 1 d . . .
C7 C 0.61236(12) 0.6791(3) 0.36247(11) 0.0167(5) Uani 1 1 d . . .
C8 C 0.68146(11) 0.7569(2) 0.36122(10) 0.0140(5) Uani 1 1 d . . .
C9 C 0.79491(13) 0.6779(3) 0.34254(14) 0.0313(7) Uani 1 1 d . . .
H9A H 0.8055 0.7814 0.3558 0.047 Uiso 1 1 calc R . .
H9B H 0.8111 0.6606 0.3024 0.047 Uiso 1 1 calc R . .
H9C H 0.8164 0.6064 0.3720 0.047 Uiso 1 1 calc R . .
C10 C 0.57918(12) 0.7663(3) 0.25863(11) 0.0203(5) Uani 1 1 d . . .
C11 C 0.61761(14) 0.8859(3) 0.24297(12) 0.0261(6) Uani 1 1 d . . .
H11 H 0.6326 0.9583 0.2729 0.031 Uiso 1 1 calc R . .
C12 C 0.63459(16) 0.9010(3) 0.18368(12) 0.0336(7) Uani 1 1 d . . .
H12 H 0.6615 0.9832 0.1731 0.040 Uiso 1 1 calc R . .
C13 C 0.61225(16) 0.7957(3) 0.13951(12) 0.0388(8) Uani 1 1 d . . .
H13 H 0.6232 0.8060 0.0986 0.047 Uiso 1 1 calc R . .
C14 C 0.57368(15) 0.6757(3) 0.15639(13) 0.0364(7) Uani 1 1 d . . .
H14 H 0.5584 0.6034 0.1265 0.044 Uiso 1 1 calc R . .
C15 C 0.55679(14) 0.6585(3) 0.21599(12) 0.0282(6) Uani 1 1 d . . .
H15 H 0.5307 0.5753 0.2271 0.034 Uiso 1 1 calc R . .
C16 C 0.47287(13) 0.7110(3) 0.37601(13) 0.0297(6) Uani 1 1 d . . .
H16A H 0.4272 0.6699 0.3748 0.036 Uiso 1 1 calc R . .
H16B H 0.4705 0.8218 0.3815 0.036 Uiso 1 1 calc R . .
C17 C 0.51568(12) 0.6411(3) 0.42911(13) 0.0257(6) Uani 1 1 d . . .
H17A H 0.5119 0.5298 0.4268 0.031 Uiso 1 1 calc R . .
H17B H 0.4988 0.6740 0.4679 0.031 Uiso 1 1 calc R . .
C18 C 0.58980(12) 0.6863(3) 0.42920(11) 0.0196(5) Uani 1 1 d . . .
C19 C 0.63096(13) 0.5737(3) 0.46969(11) 0.0220(5) Uani 1 1 d . . .
C20 C 0.73970(16) 0.4892(4) 0.49966(16) 0.0508(9) Uani 1 1 d . . .
H20A H 0.7372 0.5101 0.5431 0.076 Uiso 1 1 calc R . .
H20B H 0.7854 0.5042 0.4891 0.076 Uiso 1 1 calc R . .
H20C H 0.7262 0.3845 0.4910 0.076 Uiso 1 1 calc R . .
C21 C 0.60057(13) 0.8413(3) 0.46022(11) 0.0196(5) Uani 1 1 d . . .
C22 C 0.57808(16) 1.1000(3) 0.45806(13) 0.0345(7) Uani 1 1 d . . .
H22A H 0.5671 1.0983 0.5005 0.052 Uiso 1 1 calc R . .
H22B H 0.5501 1.1746 0.4352 0.052 Uiso 1 1 calc R . .
H22C H 0.6249 1.1273 0.4566 0.052 Uiso 1 1 calc R . .
C23 C 0.19667(12) 0.9999(3) 0.33449(11) 0.0198(5) Uani 1 1 d . . .
C24 C 0.22899(14) 1.1341(3) 0.32551(13) 0.0291(6) Uani 1 1 d . . .
H24 H 0.2760 1.1389 0.3267 0.035 Uiso 1 1 calc R . .
C25 C 0.18989(14) 1.2623(3) 0.31458(13) 0.0300(6) Uani 1 1 d . . .
H25 H 0.2108 1.3570 0.3095 0.036 Uiso 1 1 calc R . .
C26 C 0.12136(13) 1.2546(3) 0.31102(12) 0.0267(6) Uani 1 1 d . . .
H26 H 0.0958 1.3431 0.3020 0.032 Uiso 1 1 calc R . .
C27 C 0.08918(12) 1.1177(3) 0.32061(11) 0.0203(5) Uani 1 1 d . . .
H27 H 0.0421 1.1126 0.3183 0.024 Uiso 1 1 calc R . .
C28 C 0.12734(12) 0.9900(3) 0.33347(10) 0.0170(5) Uani 1 1 d . . .
C29 C 0.10962(11) 0.8296(2) 0.34994(10) 0.0139(5) Uani 1 1 d . . .
C30 C 0.17908(12) 0.7532(3) 0.35928(10) 0.0155(5) Uani 1 1 d . . .
C31 C 0.29656(13) 0.8369(3) 0.36271(14) 0.0315(7) Uani 1 1 d . . .
H31A H 0.3114 0.9017 0.3973 0.047 Uiso 1 1 calc R . .
H31B H 0.3207 0.8638 0.3275 0.047 Uiso 1 1 calc R . .
H31C H 0.3054 0.7310 0.3736 0.047 Uiso 1 1 calc R . .
C32 C 0.09267(12) 0.7425(3) 0.24308(10) 0.0170(5) Uani 1 1 d . . .
C33 C 0.07287(13) 0.8449(3) 0.19737(11) 0.0210(5) Uani 1 1 d . . .
H33 H 0.0438 0.9257 0.2052 0.025 Uiso 1 1 calc R . .
C34 C 0.09599(13) 0.8282(3) 0.14001(11) 0.0257(6) Uani 1 1 d . . .
H34 H 0.0816 0.8968 0.1084 0.031 Uiso 1 1 calc R . .
C35 C 0.13959(14) 0.7133(3) 0.12817(11) 0.0280(6) Uani 1 1 d . . .
H35 H 0.1552 0.7030 0.0889 0.034 Uiso 1 1 calc R . .
C36 C 0.16018(14) 0.6135(3) 0.17453(12) 0.0266(6) Uani 1 1 d . . .
H36 H 0.1907 0.5353 0.1671 0.032 Uiso 1 1 calc R . .
C37 C 0.13669(13) 0.6268(3) 0.23154(11) 0.0207(5) Uani 1 1 d . . .
H37 H 0.1506 0.5570 0.2628 0.025 Uiso 1 1 calc R . .
C38 C -0.03227(12) 0.7902(3) 0.34426(12) 0.0230(6) Uani 1 1 d . . .
H38A H -0.0337 0.6791 0.3492 0.028 Uiso 1 1 calc R . .
H38B H -0.0784 0.8275 0.3367 0.028 Uiso 1 1 calc R . .
C39 C 0.00037(12) 0.8614(3) 0.40123(12) 0.0219(6) Uani 1 1 d . . .
H39A H -0.0226 0.8269 0.4367 0.026 Uiso 1 1 calc R . .
H39B H -0.0046 0.9725 0.3983 0.026 Uiso 1 1 calc R . .
C40 C 0.07536(12) 0.8219(3) 0.41204(10) 0.0172(5) Uani 1 1 d . . .
C41 C 0.10875(13) 0.9400(3) 0.45629(11) 0.0213(5) Uani 1 1 d . . .
C42 C 0.21065(16) 1.0304(4) 0.50171(14) 0.0436(8) Uani 1 1 d . . .
H42A H 0.2090 1.1276 0.4803 0.065 Uiso 1 1 calc R . .
H42B H 0.2570 0.9982 0.5095 0.065 Uiso 1 1 calc R . .
H42C H 0.1908 1.0413 0.5405 0.065 Uiso 1 1 calc R . .
C43 C 0.08289(12) 0.6680(3) 0.44475(10) 0.0179(5) Uani 1 1 d . . .
C44 C 0.06270(14) 0.4079(3) 0.44211(12) 0.0284(6) Uani 1 1 d . . .
H44A H 0.1100 0.3817 0.4456 0.043 Uiso 1 1 calc R . .
H44B H 0.0377 0.3313 0.4176 0.043 Uiso 1 1 calc R . .
H44C H 0.0466 0.4118 0.4828 0.043 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 0.0231(9) 0.0145(9) 0.0237(9) -0.0023(7) 0.0012(7) -0.0038(7)
O2 0.0142(9) 0.0252(10) 0.0393(11) -0.0084(8) -0.0042(8) -0.0012(7)
O3 0.0429(13) 0.0338(12) 0.0446(13) 0.0200(10) 0.0109(10) -0.0023(10)
O4 0.0238(10) 0.0312(11) 0.0263(10) 0.0106(8) -0.0011(8) 0.0043(8)
O5 0.0443(12) 0.0254(10) 0.0209(10) -0.0001(7) -0.0007(9) -0.0019(9)
O6 0.0287(10) 0.0149(9) 0.0286(10) -0.0057(7) -0.0011(8) 0.0033(7)
O7 0.0252(10) 0.0147(9) 0.0185(9) 0.0029(6) 0.0005(7) 0.0031(7)
O8 0.0150(9) 0.0237(9) 0.0228(9) 0.0049(7) -0.0002(7) 0.0023(7)
O9 0.0427(12) 0.0300(11) 0.0322(11) -0.0147(8) 0.0125(9) -0.0050(9)
O10 0.0292(11) 0.0296(10) 0.0253(10) -0.0086(8) -0.0047(8) -0.0071(8)
O11 0.0422(12) 0.0253(10) 0.0179(10) 0.0012(7) 0.0000(8) -0.0027(8)
O12 0.0288(10) 0.0152(9) 0.0229(9) 0.0030(7) -0.0012(8) -0.0039(7)
N1 0.0152(10) 0.0149(10) 0.0256(11) -0.0014(8) 0.0044(9) -0.0021(8)
N2 0.0133(10) 0.0177(11) 0.0233(11) -0.0014(8) -0.0012(8) -0.0002(8)
N3 0.0155(11) 0.0158(11) 0.0305(12) 0.0034(8) -0.0003(9) 0.0017(8)
N4 0.0145(10) 0.0157(10) 0.0176(10) -0.0013(8) -0.0023(8) 0.0008(8)
C1 0.0173(13) 0.0183(13) 0.0219(13) -0.0012(9) 0.0003(10) -0.0033(10)
C2 0.0189(14) 0.0229(14) 0.0443(17) -0.0090(12) 0.0095(12) 0.0011(11)
C3 0.0272(16) 0.0242(15) 0.065(2) -0.0170(14) 0.0119(15) 0.0006(12)
C4 0.0224(15) 0.0175(14) 0.069(2) -0.0134(13) 0.0036(14) -0.0033(11)
C5 0.0169(13) 0.0208(13) 0.0379(15) -0.0050(11) 0.0036(11) -0.0016(10)
C6 0.0154(12) 0.0165(12) 0.0185(12) 0.0000(9) 0.0016(10) 0.0026(9)
C7 0.0140(12) 0.0136(12) 0.0222(12) -0.0004(9) -0.0005(10) -0.0005(9)
C8 0.0173(12) 0.0154(12) 0.0095(10) 0.0009(8) 0.0015(9) -0.0004(9)
C9 0.0173(14) 0.0280(15) 0.0499(18) -0.0088(13) 0.0093(13) -0.0078(11)
C10 0.0231(13) 0.0205(13) 0.0162(12) -0.0025(9) -0.0050(10) 0.0087(10)
C11 0.0382(16) 0.0159(13) 0.0236(13) -0.0002(10) -0.0016(12) 0.0085(11)
C12 0.0479(19) 0.0292(15) 0.0239(14) 0.0062(11) 0.0050(13) 0.0154(13)
C13 0.055(2) 0.0426(18) 0.0182(14) -0.0003(12) -0.0017(13) 0.0254(16)
C14 0.0428(18) 0.0403(18) 0.0233(14) -0.0140(12) -0.0129(13) 0.0199(14)
C15 0.0263(15) 0.0250(14) 0.0307(15) -0.0072(11) -0.0118(12) 0.0078(11)
C16 0.0172(13) 0.0242(14) 0.0481(18) -0.0072(12) 0.0056(12) 0.0002(11)
C17 0.0224(14) 0.0211(13) 0.0356(15) -0.0028(11) 0.0146(12) -0.0039(11)
C18 0.0170(12) 0.0176(13) 0.0245(13) -0.0004(10) 0.0030(10) -0.0013(10)
C19 0.0290(15) 0.0223(13) 0.0154(12) 0.0017(10) 0.0069(11) -0.0012(11)
C20 0.0407(19) 0.053(2) 0.056(2) 0.0271(17) -0.0104(16) 0.0119(16)
C21 0.0225(13) 0.0217(13) 0.0157(12) 0.0000(9) 0.0088(10) -0.0024(10)
C22 0.0459(18) 0.0208(14) 0.0360(16) -0.0102(11) -0.0013(14) 0.0031(13)
C23 0.0173(13) 0.0176(12) 0.0237(13) 0.0033(9) -0.0016(10) 0.0015(10)
C24 0.0210(14) 0.0257(15) 0.0408(16) 0.0079(12) 0.0037(12) -0.0029(11)
C25 0.0290(15) 0.0167(13) 0.0441(17) 0.0076(11) 0.0027(13) -0.0039(11)
C26 0.0276(15) 0.0161(13) 0.0363(15) 0.0054(11) 0.0019(12) 0.0028(11)
C27 0.0183(13) 0.0179(13) 0.0246(13) 0.0021(10) 0.0024(10) 0.0026(10)
C28 0.0185(12) 0.0150(12) 0.0175(12) -0.0008(9) 0.0013(10) -0.0007(9)
C29 0.0151(12) 0.0156(12) 0.0112(11) 0.0003(8) 0.0025(9) -0.0008(9)
C30 0.0171(12) 0.0183(12) 0.0114(11) -0.0010(9) 0.0019(9) 0.0012(9)
C31 0.0148(13) 0.0278(15) 0.0511(18) 0.0079(13) -0.0027(12) 0.0032(11)
C32 0.0192(13) 0.0144(12) 0.0170(12) -0.0016(9) -0.0012(10) -0.0041(9)
C33 0.0236(13) 0.0208(13) 0.0178(12) 0.0015(9) -0.0025(10) -0.0008(10)
C34 0.0309(15) 0.0288(15) 0.0167(12) 0.0057(10) -0.0023(11) -0.0059(12)
C35 0.0377(16) 0.0294(15) 0.0174(13) -0.0035(10) 0.0061(12) -0.0069(12)
C36 0.0367(16) 0.0193(13) 0.0246(13) -0.0044(10) 0.0080(12) 0.0006(11)
C37 0.0299(14) 0.0151(12) 0.0173(12) 0.0012(9) 0.0024(11) -0.0010(10)
C38 0.0156(12) 0.0245(14) 0.0293(14) 0.0028(10) 0.0037(11) -0.0022(10)
C39 0.0189(13) 0.0196(13) 0.0282(14) -0.0008(10) 0.0068(11) 0.0018(10)
C40 0.0204(13) 0.0171(12) 0.0146(11) -0.0007(9) 0.0033(10) -0.0005(10)
C41 0.0281(14) 0.0216(13) 0.0149(12) -0.0020(10) 0.0052(10) -0.0035(11)
C42 0.0456(19) 0.051(2) 0.0323(17) -0.0152(14) -0.0079(14) -0.0217(16)
C43 0.0205(13) 0.0191(13) 0.0145(12) -0.0005(9) 0.0033(10) 0.0004(10)
C44 0.0349(16) 0.0183(13) 0.0321(15) 0.0048(11) 0.0031(12) -0.0027(11)

_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 C8 1.216(3) . ?
O2 C16 1.419(3) . ?
O2 N2 1.454(3) . ?
O3 C19 1.195(3) . ?
O4 C19 1.336(3) . ?
O4 C20 1.445(3) . ?
O5 C21 1.202(3) . ?
O6 C21 1.331(3) . ?
O6 C22 1.447(3) . ?
O7 C30 1.215(3) . ?
O8 C38 1.428(3) . ?
O8 N4 1.458(2) . ?
O9 C41 1.196(3) . ?
O10 C41 1.330(3) . ?
O10 C42 1.448(3) . ?
O11 C43 1.194(3) . ?
O12 C43 1.335(3) . ?
O12 C44 1.454(3) . ?
N1 C8 1.355(3) . ?
N1 C1 1.402(3) . ?
N1 C9 1.451(3) . ?
N2 C10 1.441(3) . ?
N2 C7 1.497(3) . ?
N3 C30 1.361(3) . ?
N3 C23 1.406(3) . ?
N3 C31 1.456(3) . ?
N4 C32 1.449(3) . ?
N4 C29 1.488(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.514(3) . ?
C7 C8 1.559(3) . ?
C7 C18 1.577(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.374(4) . ?
C10 C15 1.388(3) . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.525(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.550(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.534(3) . ?
C18 C21 1.540(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.378(3) . ?
C23 C28 1.402(3) . ?
C24 C25 1.392(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.400(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.384(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.516(3) . ?
C29 C30 1.556(3) . ?
C29 C40 1.587(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.389(3) . ?
C32 C37 1.394(3) . ?
C33 C34 1.392(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.385(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.506(4) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.554(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C43 1.543(3) . ?
C40 C41 1.545(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 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
C16 O2 N2 106.95(17) . . ?
C19 O4 C20 116.1(2) . . ?
C21 O6 C22 114.4(2) . . ?
C38 O8 N4 106.68(16) . . ?
C41 O10 C42 115.6(2) . . ?
C43 O12 C44 113.88(19) . . ?
C8 N1 C1 111.5(2) . . ?
C8 N1 C9 122.8(2) . . ?
C1 N1 C9 123.5(2) . . ?
C10 N2 O2 106.18(18) . . ?
C10 N2 C7 113.23(18) . . ?
O2 N2 C7 106.38(17) . . ?
C30 N3 C23 111.4(2) . . ?
C30 N3 C31 123.5(2) . . ?
C23 N3 C31 123.1(2) . . ?
C32 N4 O8 105.20(16) . . ?
C32 N4 C29 114.72(17) . . ?
O8 N4 C29 106.59(16) . . ?
C2 C1 C6 122.1(2) . . ?
C2 C1 N1 127.4(2) . . ?
C6 C1 N1 110.5(2) . . ?
C1 C2 C3 117.3(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 132.3(2) . . ?
C1 C6 C7 108.0(2) . . ?
N2 C7 C6 113.51(19) . . ?
N2 C7 C8 109.22(18) . . ?
C6 C7 C8 102.04(18) . . ?
N2 C7 C18 108.49(18) . . ?
C6 C7 C18 114.09(19) . . ?
C8 C7 C18 109.20(18) . . ?
O1 C8 N1 126.0(2) . . ?
O1 C8 C7 126.2(2) . . ?
N1 C8 C7 107.80(18) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 121.2(2) . . ?
C11 C10 N2 116.2(2) . . ?
C15 C10 N2 122.6(2) . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C14 118.1(3) . . ?
C10 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
O2 C16 C17 109.6(2) . . ?
O2 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
O2 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 112.4(2) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C21 105.8(2) . . ?
C19 C18 C17 108.0(2) . . ?
C21 C18 C17 109.3(2) . . ?
C19 C18 C7 109.27(18) . . ?
C21 C18 C7 114.14(19) . . ?
C17 C18 C7 110.1(2) . . ?
O3 C19 O4 124.1(2) . . ?
O3 C19 C18 124.7(2) . . ?
O4 C19 C18 111.12(19) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 O6 124.0(2) . . ?
O5 C21 C18 122.5(2) . . ?
O6 C21 C18 113.4(2) . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 122.5(2) . . ?
C24 C23 N3 127.3(2) . . ?
C28 C23 N3 110.2(2) . . ?
C23 C24 C25 117.3(2) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C26 C25 C24 121.4(2) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 120.7(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 118.7(2) . . ?
C28 C27 H27 120.6 . . ?
C26 C27 H27 120.6 . . ?
C27 C28 C23 119.4(2) . . ?
C27 C28 C29 132.5(2) . . ?
C23 C28 C29 108.1(2) . . ?
N4 C29 C28 115.58(18) . . ?
N4 C29 C30 109.51(17) . . ?
C28 C29 C30 102.14(18) . . ?
N4 C29 C40 108.40(17) . . ?
C28 C29 C40 112.11(18) . . ?
C30 C29 C40 108.79(18) . . ?
O7 C30 N3 126.1(2) . . ?
O7 C30 C29 125.9(2) . . ?
N3 C30 C29 107.98(19) . . ?
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C37 119.8(2) . . ?
C33 C32 N4 122.7(2) . . ?
C37 C32 N4 117.5(2) . . ?
C32 C33 C34 119.4(2) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 121.2(2) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C36 119.0(2) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 H35 120.5 . . ?
C37 C36 C35 120.6(2) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C32 120.1(2) . . ?
C36 C37 H37 120.0 . . ?
C32 C37 H37 120.0 . . ?
O8 C38 C39 109.3(2) . . ?
O8 C38 H38A 109.8 . . ?
C39 C38 H38A 109.8 . . ?
O8 C38 H38B 109.8 . . ?
C39 C38 H38B 109.8 . . ?
H38A C38 H38B 108.3 . . ?
C38 C39 C40 112.7(2) . . ?
C38 C39 H39A 109.1 . . ?
C40 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
C40 C39 H39B 109.1 . . ?
H39A C39 H39B 107.8 . . ?
C43 C40 C41 106.40(19) . . ?
C43 C40 C39 109.07(19) . . ?
C41 C40 C39 108.17(19) . . ?
C43 C40 C29 114.09(18) . . ?
C41 C40 C29 108.41(18) . . ?
C39 C40 C29 110.47(19) . . ?
O9 C41 O10 124.4(2) . . ?
O9 C41 C40 124.2(2) . . ?
O10 C41 C40 111.3(2) . . ?
O10 C42 H42A 109.5 . . ?
O10 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O10 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O11 C43 O12 123.6(2) . . ?
O11 C43 C40 122.9(2) . . ?
O12 C43 C40 113.4(2) . . ?
O12 C44 H44A 109.5 . . ?
O12 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O12 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.170




data_cd212151
_database_code_depnum_ccdc_archive 'CCDC 880875'
#TrackingRef 'cd212151.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N2 O6'
_chemical_formula_weight         436.45

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7826(18)
_cell_length_b                   9.574(2)
_cell_length_c                   13.717(3)
_cell_angle_alpha                89.306(4)
_cell_angle_beta                 81.155(4)
_cell_angle_gamma                83.165(4)
_cell_volume                     1131.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2045
_cell_measurement_theta_min      2.599
_cell_measurement_theta_max      26.160

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6680
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4400
_reflns_number_gt                3333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0763P)^2^+0.1263P] 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       ?
_refine_ls_number_reflns         4400
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.74983(17) 0.90047(16) 0.44525(10) 0.0548(4) Uani 1 1 d . . .
O2 O 1.04378(14) 0.81811(13) 0.15442(9) 0.0388(3) Uani 1 1 d . . .
O3 O 0.57063(18) 0.6009(2) 0.20510(13) 0.0744(5) Uani 1 1 d . . .
O4 O 0.51057(15) 0.78325(16) 0.31104(11) 0.0521(4) Uani 1 1 d . . .
O5 O 0.95292(16) 0.61323(16) 0.38211(10) 0.0537(4) Uani 1 1 d . . .
O6 O 0.69957(16) 0.58234(15) 0.41556(10) 0.0512(4) Uani 1 1 d . . .
N1 N 0.64491(19) 1.06272(17) 0.34005(12) 0.0484(4) Uani 1 1 d . . .
N2 N 0.97692(16) 0.87239(15) 0.25315(10) 0.0345(3) Uani 1 1 d . . .
C1 C 0.7302(2) 0.9415(2) 0.36263(14) 0.0415(4) Uani 1 1 d . . .
C2 C 0.6394(2) 1.0730(2) 0.23746(15) 0.0460(5) Uani 1 1 d . . .
C3 C 0.5627(3) 1.1810(3) 0.1882(2) 0.0669(7) Uani 1 1 d . . .
H3 H 0.5052 1.2582 0.2221 0.080 Uiso 1 1 calc R . .
C4 C 0.5756(3) 1.1689(3) 0.0859(2) 0.0720(7) Uani 1 1 d . . .
H4 H 0.5251 1.2394 0.0511 0.086 Uiso 1 1 calc R . .
C5 C 0.6616(3) 1.0547(3) 0.03491(18) 0.0637(6) Uani 1 1 d . . .
H5 H 0.6689 1.0497 -0.0333 0.076 Uiso 1 1 calc R . .
C6 C 0.7376(2) 0.9467(2) 0.08546(14) 0.0483(5) Uani 1 1 d . . .
H6 H 0.7951 0.8699 0.0511 0.058 Uiso 1 1 calc R . .
C7 C 0.7264(2) 0.95503(19) 0.18791(13) 0.0380(4) Uani 1 1 d . . .
C8 C 0.8038(2) 0.86479(18) 0.26313(12) 0.0350(4) Uani 1 1 d . . .
C9 C 0.7800(2) 0.70351(19) 0.26543(13) 0.0370(4) Uani 1 1 d . . .
C10 C 0.8871(2) 0.62442(19) 0.17676(13) 0.0399(4) Uani 1 1 d . . .
H10A H 0.8919 0.5240 0.1884 0.048 Uiso 1 1 calc R . .
H10B H 0.8412 0.6440 0.1173 0.048 Uiso 1 1 calc R . .
C11 C 1.0530(2) 0.66573(18) 0.15978(13) 0.0383(4) Uani 1 1 d . . .
H11 H 1.1078 0.6314 0.2141 0.046 Uiso 1 1 calc R . .
C12 C 0.6095(2) 0.6870(2) 0.25646(14) 0.0441(5) Uani 1 1 d . . .
C13 C 0.3476(2) 0.7888(3) 0.3000(2) 0.0796(8) Uani 1 1 d . . .
H13A H 0.3367 0.8046 0.2320 0.119 Uiso 1 1 calc R . .
H13B H 0.2883 0.8642 0.3397 0.119 Uiso 1 1 calc R . .
H13C H 0.3103 0.7014 0.3209 0.119 Uiso 1 1 calc R . .
C14 C 0.8231(2) 0.63165(19) 0.36143(14) 0.0396(4) Uani 1 1 d . . .
C15 C 0.7307(3) 0.5077(3) 0.50487(17) 0.0646(6) Uani 1 1 d . . .
H15A H 0.8106 0.4306 0.4880 0.097 Uiso 1 1 calc R . .
H15B H 0.6378 0.4724 0.5366 0.097 Uiso 1 1 calc R . .
H15C H 0.7641 0.5709 0.5488 0.097 Uiso 1 1 calc R . .
C16 C 1.1432(2) 0.6111(2) 0.06270(15) 0.0469(5) Uani 1 1 d . . .
H16 H 1.1014 0.6356 0.0057 0.056 Uiso 1 1 calc R . .
C17 C 1.2774(3) 0.5309(2) 0.05323(18) 0.0605(6) Uani 1 1 d . . .
H17A H 1.3223 0.5045 0.1088 0.073 Uiso 1 1 calc R . .
H17B H 1.3271 0.5007 -0.0090 0.073 Uiso 1 1 calc R . .
C18 C 0.5678(3) 1.1684(3) 0.41317(19) 0.0792(8) Uani 1 1 d . . .
H18A H 0.5925 1.1414 0.4771 0.119 Uiso 1 1 calc R . .
H18B H 0.4575 1.1751 0.4146 0.119 Uiso 1 1 calc R . .
H18C H 0.6028 1.2579 0.3958 0.119 Uiso 1 1 calc R . .
C19 C 1.0179(2) 1.01487(18) 0.25799(13) 0.0358(4) Uani 1 1 d . . .
C20 C 1.0452(2) 1.0991(2) 0.17474(14) 0.0453(5) Uani 1 1 d . . .
H20 H 1.0340 1.0663 0.1130 0.054 Uiso 1 1 calc R . .
C21 C 1.0891(3) 1.2324(2) 0.18489(17) 0.0580(6) Uani 1 1 d . . .
H21 H 1.1093 1.2879 0.1294 0.070 Uiso 1 1 calc R . .
C22 C 1.1032(3) 1.2834(2) 0.27710(18) 0.0605(6) Uani 1 1 d . . .
H22 H 1.1313 1.3731 0.2835 0.073 Uiso 1 1 calc R . .
C23 C 1.0750(3) 1.1994(2) 0.35986(17) 0.0570(6) Uani 1 1 d . . .
H23 H 1.0831 1.2336 0.4218 0.068 Uiso 1 1 calc R . .
C24 C 1.0348(2) 1.0648(2) 0.35057(15) 0.0459(5) Uani 1 1 d . . .
H24 H 1.0191 1.0080 0.4058 0.055 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 0.0568(9) 0.0695(10) 0.0354(8) -0.0047(7) 0.0006(6) -0.0062(7)
O2 0.0398(7) 0.0353(7) 0.0379(7) -0.0081(5) 0.0026(5) -0.0008(5)
O3 0.0480(9) 0.0943(13) 0.0856(12) -0.0315(10) -0.0150(8) -0.0181(9)
O4 0.0297(7) 0.0603(9) 0.0642(9) -0.0026(7) -0.0051(6) 0.0004(6)
O5 0.0420(8) 0.0653(10) 0.0557(9) 0.0131(7) -0.0147(6) -0.0061(7)
O6 0.0472(8) 0.0580(9) 0.0504(8) 0.0161(7) -0.0090(6) -0.0136(7)
N1 0.0433(9) 0.0433(9) 0.0523(10) -0.0105(8) 0.0062(7) 0.0044(7)
N2 0.0322(8) 0.0340(8) 0.0354(8) -0.0077(6) -0.0004(6) -0.0014(6)
C1 0.0353(10) 0.0474(11) 0.0398(10) -0.0069(8) 0.0023(8) -0.0062(8)
C2 0.0365(10) 0.0415(11) 0.0559(12) 0.0010(9) 0.0003(9) 0.0018(8)
C3 0.0523(13) 0.0530(13) 0.0864(18) 0.0097(12) -0.0001(12) 0.0151(11)
C4 0.0593(15) 0.0678(16) 0.0841(18) 0.0302(14) -0.0120(13) 0.0098(12)
C5 0.0568(14) 0.0788(17) 0.0553(13) 0.0183(12) -0.0141(11) -0.0018(12)
C6 0.0444(11) 0.0560(12) 0.0435(11) 0.0025(9) -0.0069(9) -0.0015(9)
C7 0.0303(9) 0.0389(10) 0.0429(10) 0.0010(8) -0.0025(7) -0.0003(7)
C8 0.0314(9) 0.0374(10) 0.0346(9) -0.0042(7) -0.0032(7) 0.0005(7)
C9 0.0329(9) 0.0383(10) 0.0398(10) -0.0016(8) -0.0064(7) -0.0029(8)
C10 0.0409(10) 0.0355(9) 0.0437(10) -0.0063(8) -0.0076(8) -0.0033(8)
C11 0.0377(10) 0.0328(9) 0.0421(10) -0.0079(8) -0.0037(8) 0.0023(7)
C12 0.0381(10) 0.0489(11) 0.0465(11) 0.0025(9) -0.0091(8) -0.0068(9)
C13 0.0309(12) 0.111(2) 0.0954(19) 0.0045(17) -0.0138(12) 0.0030(13)
C14 0.0389(10) 0.0360(10) 0.0436(10) 0.0000(8) -0.0060(8) -0.0033(8)
C15 0.0727(16) 0.0675(15) 0.0572(13) 0.0214(12) -0.0140(12) -0.0207(13)
C16 0.0485(12) 0.0429(11) 0.0466(11) -0.0116(9) -0.0023(9) 0.0002(9)
C17 0.0499(13) 0.0566(13) 0.0674(14) -0.0173(11) 0.0095(11) 0.0023(10)
C18 0.0872(19) 0.0602(15) 0.0751(17) -0.0238(13) 0.0239(14) 0.0079(13)
C19 0.0318(9) 0.0324(9) 0.0420(10) -0.0034(7) -0.0045(7) 0.0007(7)
C20 0.0524(12) 0.0404(11) 0.0434(11) -0.0011(8) -0.0069(9) -0.0066(9)
C21 0.0729(15) 0.0410(11) 0.0619(14) 0.0082(10) -0.0130(11) -0.0112(11)
C22 0.0738(16) 0.0332(10) 0.0785(16) -0.0043(11) -0.0211(12) -0.0101(10)
C23 0.0669(14) 0.0479(12) 0.0594(13) -0.0153(11) -0.0195(11) -0.0063(11)
C24 0.0499(11) 0.0451(11) 0.0435(10) -0.0050(9) -0.0100(9) -0.0043(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 C1 1.225(2) . ?
O2 C11 1.453(2) . ?
O2 N2 1.4659(17) . ?
O3 C12 1.203(2) . ?
O4 C12 1.338(2) . ?
O4 C13 1.457(3) . ?
O5 C14 1.209(2) . ?
O6 C14 1.348(2) . ?
O6 C15 1.456(3) . ?
N1 C1 1.364(3) . ?
N1 C2 1.417(3) . ?
N1 C18 1.463(3) . ?
N2 C19 1.457(2) . ?
N2 C8 1.516(2) . ?
C1 C8 1.569(2) . ?
C2 C3 1.392(3) . ?
C2 C7 1.405(3) . ?
C3 C4 1.396(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.526(3) . ?
C8 C9 1.582(2) . ?
C9 C12 1.548(3) . ?
C9 C14 1.556(3) . ?
C9 C10 1.561(2) . ?
C10 C11 1.538(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.506(2) . ?
C11 H11 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.317(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.397(3) . ?
C19 C24 1.397(3) . ?
C20 C21 1.390(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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 O2 N2 106.71(12) . . ?
C12 O4 C13 116.52(18) . . ?
C14 O6 C15 115.36(16) . . ?
C1 N1 C2 111.70(15) . . ?
C1 N1 C18 123.94(19) . . ?
C2 N1 C18 124.36(19) . . ?
C19 N2 O2 106.49(12) . . ?
C19 N2 C8 113.87(13) . . ?
O2 N2 C8 106.25(12) . . ?
O1 C1 N1 126.69(17) . . ?
O1 C1 C8 125.61(18) . . ?
N1 C1 C8 107.67(16) . . ?
C3 C2 C7 122.4(2) . . ?
C3 C2 N1 127.59(19) . . ?
C7 C2 N1 110.04(17) . . ?
C2 C3 C4 117.3(2) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 118.78(18) . . ?
C6 C7 C8 132.83(16) . . ?
C2 C7 C8 108.13(15) . . ?
N2 C8 C7 113.14(14) . . ?
N2 C8 C1 106.02(13) . . ?
C7 C8 C1 101.93(14) . . ?
N2 C8 C9 107.01(13) . . ?
C7 C8 C9 116.35(14) . . ?
C1 C8 C9 111.96(14) . . ?
C12 C9 C14 109.83(14) . . ?
C12 C9 C10 108.23(14) . . ?
C14 C9 C10 107.19(14) . . ?
C12 C9 C8 109.84(14) . . ?
C14 C9 C8 111.62(14) . . ?
C10 C9 C8 110.04(14) . . ?
C11 C10 C9 113.49(14) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O2 C11 C16 105.98(15) . . ?
O2 C11 C10 108.43(14) . . ?
C16 C11 C10 112.12(15) . . ?
O2 C11 H11 110.1 . . ?
C16 C11 H11 110.1 . . ?
C10 C11 H11 110.1 . . ?
O3 C12 O4 124.16(18) . . ?
O3 C12 C9 124.40(18) . . ?
O4 C12 C9 111.42(16) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 123.72(17) . . ?
O5 C14 C9 124.59(16) . . ?
O6 C14 C9 111.51(15) . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C11 124.3(2) . . ?
C17 C16 H16 117.8 . . ?
C11 C16 H16 117.8 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 119.97(17) . . ?
C20 C19 N2 122.90(16) . . ?
C24 C19 N2 117.10(16) . . ?
C21 C20 C19 119.51(18) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.54(19) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.42(19) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 119.83(19) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?

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
C11 O2 N2 C19 160.10(13) . . . . ?
C11 O2 N2 C8 -78.17(15) . . . . ?
C2 N1 C1 O1 -176.42(18) . . . . ?
C18 N1 C1 O1 3.2(3) . . . . ?
C2 N1 C1 C8 5.2(2) . . . . ?
C18 N1 C1 C8 -175.21(19) . . . . ?
C1 N1 C2 C3 179.5(2) . . . . ?
C18 N1 C2 C3 0.0(3) . . . . ?
C1 N1 C2 C7 -0.9(2) . . . . ?
C18 N1 C2 C7 179.52(19) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
N1 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C5 C6 C7 C8 -173.9(2) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
N1 C2 C7 C6 -178.88(16) . . . . ?
C3 C2 C7 C8 175.63(19) . . . . ?
N1 C2 C7 C8 -4.0(2) . . . . ?
C19 N2 C8 C7 55.26(18) . . . . ?
O2 N2 C8 C7 -61.63(16) . . . . ?
C19 N2 C8 C1 -55.63(18) . . . . ?
O2 N2 C8 C1 -172.52(13) . . . . ?
C19 N2 C8 C9 -175.28(13) . . . . ?
O2 N2 C8 C9 67.83(15) . . . . ?
C6 C7 C8 N2 67.1(3) . . . . ?
C2 C7 C8 N2 -106.87(17) . . . . ?
C6 C7 C8 C1 -179.5(2) . . . . ?
C2 C7 C8 C1 6.53(19) . . . . ?
C6 C7 C8 C9 -57.5(3) . . . . ?
C2 C7 C8 C9 128.61(16) . . . . ?
O1 C1 C8 N2 -66.9(2) . . . . ?
N1 C1 C8 N2 111.52(16) . . . . ?
O1 C1 C8 C7 174.53(18) . . . . ?
N1 C1 C8 C7 -7.07(19) . . . . ?
O1 C1 C8 C9 49.5(2) . . . . ?
N1 C1 C8 C9 -132.12(16) . . . . ?
N2 C8 C9 C12 -169.80(13) . . . . ?
C7 C8 C9 C12 -42.19(19) . . . . ?
C1 C8 C9 C12 74.45(18) . . . . ?
N2 C8 C9 C14 68.14(17) . . . . ?
C7 C8 C9 C14 -164.26(14) . . . . ?
C1 C8 C9 C14 -47.62(19) . . . . ?
N2 C8 C9 C10 -50.74(17) . . . . ?
C7 C8 C9 C10 76.86(18) . . . . ?
C1 C8 C9 C10 -166.50(14) . . . . ?
C12 C9 C10 C11 163.81(15) . . . . ?
C14 C9 C10 C11 -77.79(18) . . . . ?
C8 C9 C10 C11 43.8(2) . . . . ?
N2 O2 C11 C16 -171.78(13) . . . . ?
N2 O2 C11 C10 67.67(16) . . . . ?
C9 C10 C11 O2 -51.7(2) . . . . ?
C9 C10 C11 C16 -168.37(16) . . . . ?
C13 O4 C12 O3 -5.1(3) . . . . ?
C13 O4 C12 C9 173.20(18) . . . . ?
C14 C9 C12 O3 -100.2(2) . . . . ?
C10 C9 C12 O3 16.5(3) . . . . ?
C8 C9 C12 O3 136.7(2) . . . . ?
C14 C9 C12 O4 81.49(19) . . . . ?
C10 C9 C12 O4 -161.80(16) . . . . ?
C8 C9 C12 O4 -41.6(2) . . . . ?
C15 O6 C14 O5 2.1(3) . . . . ?
C15 O6 C14 C9 177.41(17) . . . . ?
C12 C9 C14 O5 170.90(18) . . . . ?
C10 C9 C14 O5 53.5(2) . . . . ?
C8 C9 C14 O5 -67.0(2) . . . . ?
C12 C9 C14 O6 -4.3(2) . . . . ?
C10 C9 C14 O6 -121.68(16) . . . . ?
C8 C9 C14 O6 117.76(16) . . . . ?
O2 C11 C16 C17 117.9(2) . . . . ?
C10 C11 C16 C17 -124.0(2) . . . . ?
O2 N2 C19 C20 27.2(2) . . . . ?
C8 N2 C19 C20 -89.5(2) . . . . ?
O2 N2 C19 C24 -150.67(16) . . . . ?
C8 N2 C19 C24 92.57(19) . . . . ?
C24 C19 C20 C21 0.0(3) . . . . ?
N2 C19 C20 C21 -177.78(18) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
C22 C23 C24 C19 -2.0(3) . . . . ?
C20 C19 C24 C23 1.5(3) . . . . ?
N2 C19 C24 C23 179.49(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045