 
data_vm191b 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H22 N4 O4' 
_chemical_formula_weight          406.44 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    11.9493(9) 
_cell_length_b                    13.2285(9) 
_cell_length_c                    15.9117(11) 
_cell_angle_alpha                 103.066(4) 
_cell_angle_beta                  112.628(5) 
_cell_angle_gamma                 104.644(5) 
_cell_volume                      2093.8(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     4971 
_cell_measurement_theta_min       6.55 
_cell_measurement_theta_max       72.03 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.289 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              856 
_exptl_absorpt_coefficient_mu     0.745 
_exptl_absorpt_correction_type    multi-scan  
_exptl_absorpt_correction_T_min   0.9292 
_exptl_absorpt_correction_T_max   0.9637 
_exptl_absorpt_process_details    'CrystalClear (Rigaku/MSC Inc., 2005)'   
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      1.54180 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'micro-focus rotating anode' 
_diffrn_radiation_monochromator   'confocal' 
_diffrn_measurement_device_type   'Rigaku RAXIS Rapid' 
_diffrn_measurement_method        ω-scans 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             30281 
_diffrn_reflns_av_R_equivalents   0.0321 
_diffrn_reflns_av_sigmaI/netI     0.0245 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          6.55 
_diffrn_reflns_theta_max          72.03 
_reflns_number_total              7560 
_reflns_number_gt                 4971 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrystalClear (Rigaku/MSC Inc., 2005)'  
_computing_cell_refinement        'CrystalClear (Rigaku/MSC Inc., 2005)'  
_computing_data_reduction         'CrystalClear (Rigaku/MSC Inc., 2005)'  
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0696P)²+0.4137P] where P=(Fo²+2Fc²)/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          7560 
_refine_ls_number_parameters      550 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0810 
_refine_ls_R_factor_gt            0.0555 
_refine_ls_wR_factor_ref          0.1546 
_refine_ls_wR_factor_gt           0.1373 
_refine_ls_goodness_of_fit_ref    1.012 
_refine_ls_restrained_S_all       1.012 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.5924(2) 0.15372(15) 0.02221(16) 0.0663(5) Uani 1 1 d . . . 
C2 C 0.5825(2) 0.15151(17) 0.10633(16) 0.0734(6) Uani 1 1 d . . . 
C3 C 0.4624(3) 0.14160(19) 0.1039(2) 0.0853(7) Uani 1 1 d . . . 
H3 H 0.4528 0.1405 0.1591 0.102 Uiso 1 1 calc R . . 
C4 C 0.3583(3) 0.1335(2) 0.0226(2) 0.0886(7) Uani 1 1 d . . . 
H4 H 0.2789 0.1264 0.0226 0.106 Uiso 1 1 calc R . . 
C5 C 0.3710(3) 0.1357(2) -0.05926(19) 0.0900(7) Uani 1 1 d . . . 
H5 H 0.2994 0.1292 -0.1147 0.108 Uiso 1 1 calc R . . 
C6 C 0.4886(3) 0.14761(18) -0.06034(17) 0.0773(6) Uani 1 1 d . . . 
C7 C 0.6962(3) 0.1594(2) 0.19534(19) 0.1010(8) Uani 1 1 d . . . 
H7A H 0.7040 0.0877 0.1864 0.151 Uiso 1 1 calc R . . 
H7B H 0.6825 0.1815 0.2512 0.151 Uiso 1 1 calc R . . 
H7C H 0.7751 0.2140 0.2055 0.151 Uiso 1 1 calc R . . 
C8 C 0.5037(3) 0.1535(3) -0.14946(18) 0.1097(9) Uani 1 1 d . . . 
H8A H 0.4259 0.1563 -0.1966 0.165 Uiso 1 1 calc R . . 
H8B H 0.5173 0.0883 -0.1776 0.165 Uiso 1 1 calc R . . 
H8C H 0.5776 0.2195 -0.1308 0.165 Uiso 1 1 calc R . . 
N9 N 0.71096(18) 0.15955(13) 0.01826(13) 0.0721(5) Uani 1 1 d . . . 
H9 H 0.7199 0.0977 -0.0026 0.086 Uiso 1 1 calc R . . 
C10 C 0.8102(2) 0.25661(16) 0.04535(14) 0.0621(5) Uani 1 1 d . . . 
C11 C 0.9203(2) 0.26147(16) 0.02923(14) 0.0633(5) Uani 1 1 d . . . 
C12 C 1.0204(2) 0.36251(18) 0.06247(15) 0.0689(5) Uani 1 1 d . . . 
H12 H 1.0924 0.3642 0.0522 0.083 Uiso 1 1 calc R . . 
C13 C 1.0172(2) 0.46104(17) 0.11039(16) 0.0702(6) Uani 1 1 d . . . 
C14 C 0.9086(2) 0.46129(17) 0.12703(15) 0.0692(5) Uani 1 1 d . . . 
C15 C 0.8082(2) 0.35804(16) 0.09258(14) 0.0653(5) Uani 1 1 d . . . 
H15 H 0.7354 0.3566 0.1016 0.078 Uiso 1 1 calc R . . 
N16 N 0.9311(2) 0.16424(16) -0.02432(14) 0.0771(5) Uani 1 1 d . . . 
O17 O 0.84398(19) 0.07122(14) -0.05456(14) 0.1029(6) Uani 1 1 d . . . 
O18 O 1.02522(19) 0.17542(15) -0.03925(14) 0.1048(6) Uani 1 1 d . . . 
N19 N 1.1269(2) 0.56242(17) 0.13971(15) 0.0865(6) Uani 1 1 d . . . 
O20 O 1.2191(2) 0.55629(16) 0.12711(15) 0.1119(6) Uani 1 1 d . . . 
O21 O 1.12453(19) 0.65370(15) 0.17667(16) 0.1180(7) Uani 1 1 d . . . 
N22 N 0.9006(2) 0.55561(15) 0.17461(16) 0.0908(6) Uani 1 1 d . . . 
H22 H 0.9668 0.6175 0.1991 0.109 Uiso 1 1 calc R . . 
C23 C 0.7885(3) 0.55925(17) 0.1870(2) 0.0852(7) Uani 1 1 d . . . 
C24 C 0.7053(3) 0.5966(2) 0.1258(2) 0.1051(9) Uani 1 1 d . . . 
C25 C 0.5968(4) 0.6023(3) 0.1358(3) 0.1379(13) Uani 1 1 d . . . 
H25 H 0.5395 0.6264 0.0942 0.165 Uiso 1 1 calc R . . 
C26 C 0.5734(4) 0.5737(3) 0.2045(3) 0.1408(13) Uani 1 1 d . . . 
H26 H 0.5004 0.5790 0.2104 0.169 Uiso 1 1 calc R . . 
C27 C 0.6535(4) 0.5371(3) 0.2657(3) 0.1211(12) Uani 1 1 d . . . 
H27 H 0.6354 0.5185 0.3134 0.145 Uiso 1 1 calc R . . 
C28 C 0.7640(4) 0.5269(2) 0.2579(2) 0.1060(9) Uani 1 1 d . . . 
C29 C 0.7270(4) 0.6271(3) 0.0460(3) 0.1499(15) Uani 1 1 d . . . 
H29A H 0.8064 0.6920 0.0746 0.225 Uiso 1 1 calc R . . 
H29B H 0.6546 0.6433 0.0069 0.225 Uiso 1 1 calc R . . 
H29C H 0.7340 0.5656 0.0056 0.225 Uiso 1 1 calc R . . 
C30 C 0.8536(4) 0.4847(3) 0.3212(2) 0.1593(16) Uani 1 1 d . . . 
H30A H 0.8223 0.4046 0.2918 0.239 Uiso 1 1 calc R . . 
H30B H 0.8566 0.5045 0.3841 0.239 Uiso 1 1 calc R . . 
H30C H 0.9398 0.5175 0.3285 0.239 Uiso 1 1 calc R . . 
C51 C 0.1615(2) 0.30096(19) 0.32902(16) 0.0723(6) Uani 1 1 d . . . 
C52 C 0.1315(3) 0.2130(2) 0.24685(17) 0.0788(6) Uani 1 1 d . . . 
C53 C 0.2086(3) 0.2301(3) 0.20110(19) 0.0956(8) Uani 1 1 d . . . 
H53 H 0.1920 0.1719 0.1469 0.115 Uiso 1 1 calc R . . 
C54 C 0.3084(3) 0.3301(3) 0.2336(2) 0.1114(10) Uani 1 1 d . . . 
H54 H 0.3591 0.3395 0.2017 0.134 Uiso 1 1 calc R . . 
C55 C 0.3338(3) 0.4158(3) 0.3124(3) 0.1156(10) Uani 1 1 d . . . 
H55 H 0.4005 0.4843 0.3328 0.139 Uiso 1 1 calc R . . 
C56 C 0.2620(3) 0.4037(2) 0.3636(2) 0.0947(8) Uani 1 1 d . . . 
C57 C 0.0196(3) 0.1035(2) 0.2074(2) 0.1017(8) Uani 1 1 d . . . 
H57A H 0.0273 0.0745 0.2586 0.152 Uiso 1 1 calc R . . 
H57B H 0.0214 0.0511 0.1557 0.152 Uiso 1 1 calc R . . 
H57C H -0.0615 0.1146 0.1826 0.152 Uiso 1 1 calc R . . 
C58 C 0.2943(4) 0.4976(3) 0.4538(3) 0.1432(13) Uani 1 1 d . . . 
H58A H 0.2242 0.5245 0.4406 0.215 Uiso 1 1 calc R . . 
H58B H 0.3739 0.5576 0.4718 0.215 Uiso 1 1 calc R . . 
H58C H 0.3055 0.4704 0.5064 0.215 Uiso 1 1 calc R . . 
N59 N 0.08814(19) 0.28625(15) 0.38170(13) 0.0753(5) Uani 1 1 d . . . 
H59 H 0.0277 0.3130 0.3721 0.090 Uiso 1 1 calc R . . 
C60 C 0.1094(2) 0.23229(16) 0.44575(14) 0.0614(5) Uani 1 1 d . . . 
C61 C 0.0423(2) 0.22385(16) 0.50254(15) 0.0626(5) Uani 1 1 d . . . 
C62 C 0.0667(2) 0.16675(16) 0.56523(14) 0.0640(5) Uani 1 1 d . . . 
H62 H 0.0240 0.1644 0.6033 0.077 Uiso 1 1 calc R . . 
C63 C 0.15236(19) 0.11306(16) 0.57318(13) 0.0586(5) Uani 1 1 d . . . 
C64 C 0.22112(19) 0.11769(15) 0.51741(13) 0.0575(5) Uani 1 1 d . . . 
C65 C 0.1993(2) 0.18066(16) 0.45804(14) 0.0613(5) Uani 1 1 d . . . 
H65 H 0.2478 0.1887 0.4245 0.074 Uiso 1 1 calc R . . 
N66 N -0.05395(19) 0.27252(17) 0.49707(15) 0.0809(5) Uani 1 1 d . . . 
O67 O -0.08161(19) 0.32315(17) 0.44086(14) 0.1045(6) Uani 1 1 d . . . 
O68 O -0.10478(19) 0.26399(17) 0.55044(16) 0.1110(6) Uani 1 1 d . . . 
N69 N 0.16723(18) 0.05256(17) 0.63864(12) 0.0730(5) Uani 1 1 d . . . 
O70 O 0.23095(17) -0.00815(14) 0.63947(12) 0.0867(5) Uani 1 1 d . . . 
O71 O 0.11517(18) 0.06141(18) 0.69118(13) 0.1070(6) Uani 1 1 d . . . 
N72 N 0.30482(17) 0.06490(14) 0.52050(12) 0.0687(5) Uani 1 1 d . . . 
H72 H 0.3122 0.0218 0.5538 0.082 Uiso 1 1 calc R . . 
C73 C 0.3816(2) 0.07772(18) 0.47076(16) 0.0656(5) Uani 1 1 d . . . 
C74 C 0.5047(2) 0.1623(2) 0.51997(19) 0.0796(6) Uani 1 1 d . . . 
C75 C 0.5772(3) 0.1734(3) 0.4699(3) 0.1071(10) Uani 1 1 d . . . 
H75 H 0.6608 0.2287 0.5007 0.129 Uiso 1 1 calc R . . 
C76 C 0.5257(4) 0.1026(4) 0.3744(3) 0.1176(12) Uani 1 1 d . . . 
H76 H 0.5750 0.1107 0.3414 0.141 Uiso 1 1 calc R . . 
C77 C 0.4032(4) 0.0209(3) 0.3279(2) 0.1046(9) Uani 1 1 d . . . 
H77 H 0.3698 -0.0255 0.2634 0.126 Uiso 1 1 calc R . . 
C78 C 0.3288(3) 0.0061(2) 0.37475(17) 0.0778(6) Uani 1 1 d . . . 
C79 C 0.5566(3) 0.2392(2) 0.6231(2) 0.1150(9) Uani 1 1 d . . . 
H79A H 0.5012 0.2801 0.6252 0.172 Uiso 1 1 calc R . . 
H79B H 0.6438 0.2909 0.6459 0.172 Uiso 1 1 calc R . . 
H79C H 0.5580 0.1959 0.6642 0.172 Uiso 1 1 calc R . . 
C80 C 0.1950(3) -0.0855(2) 0.3242(2) 0.1058(9) Uani 1 1 d . . . 
H80A H 0.1723 -0.1224 0.2572 0.159 Uiso 1 1 calc R . . 
H80B H 0.1319 -0.0538 0.3267 0.159 Uiso 1 1 calc R . . 
H80C H 0.1953 -0.1389 0.3562 0.159 Uiso 1 1 calc R . . 
 
 
_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 
C1 C6 1.385(3) . ? 
C1 C2 1.394(3) . ? 
C1 N9 1.426(3) . ? 
C2 C3 1.393(3) . ? 
C2 C7 1.498(3) . ? 
C3 C4 1.365(4) . ? 
C4 C5 1.374(3) . ? 
C5 C6 1.381(3) . ? 
C6 C8 1.513(3) . ? 
N9 C10 1.352(2) . ? 
C10 C15 1.393(3) . ? 
C10 C11 1.423(3) . ? 
C11 C12 1.372(3) . ? 
C11 N16 1.439(3) . ? 
C12 C13 1.371(3) . ? 
C13 C14 1.422(3) . ? 
C13 N19 1.447(3) . ? 
C14 N22 1.352(3) . ? 
C14 C15 1.390(3) . ? 
N16 O18 1.217(2) . ? 
N16 O17 1.236(2) . ? 
N19 O20 1.212(2) . ? 
N19 O21 1.230(2) . ? 
N22 C23 1.437(3) . ? 
C23 C24 1.379(4) . ? 
C23 C28 1.397(4) . ? 
C24 C25 1.384(4) . ? 
C24 C29 1.508(4) . ? 
C25 C26 1.337(4) . ? 
C26 C27 1.352(5) . ? 
C27 C28 1.410(4) . ? 
C28 C30 1.483(5) . ? 
C51 C56 1.386(3) . ? 
C51 C52 1.390(3) . ? 
C51 N59 1.436(3) . ? 
C52 C53 1.384(3) . ? 
C52 C57 1.498(3) . ? 
C53 C54 1.363(4) . ? 
C54 C55 1.357(4) . ? 
C55 C56 1.397(4) . ? 
C56 C58 1.509(4) . ? 
N59 C60 1.354(2) . ? 
C60 C65 1.388(3) . ? 
C60 C61 1.425(3) . ? 
C61 C62 1.371(3) . ? 
C61 N66 1.438(3) . ? 
C62 C63 1.370(3) . ? 
C63 C64 1.423(2) . ? 
C63 N69 1.436(2) . ? 
C64 N72 1.350(2) . ? 
C64 C65 1.389(3) . ? 
N66 O68 1.228(2) . ? 
N66 O67 1.230(2) . ? 
N69 O71 1.222(2) . ? 
N69 O70 1.237(2) . ? 
N72 C73 1.427(2) . ? 
C73 C74 1.384(3) . ? 
C73 C78 1.390(3) . ? 
C74 C75 1.388(4) . ? 
C74 C79 1.502(4) . ? 
C75 C76 1.382(5) . ? 
C76 C77 1.365(4) . ? 
C77 C78 1.369(3) . ? 
C78 C80 1.504(4) . ? 
 
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 
C6 C1 C2 122.1(2) . . ? 
C6 C1 N9 117.79(19) . . ? 
C2 C1 N9 120.1(2) . . ? 
C3 C2 C1 117.1(2) . . ? 
C3 C2 C7 121.5(2) . . ? 
C1 C2 C7 121.4(2) . . ? 
C4 C3 C2 121.6(2) . . ? 
C3 C4 C5 120.0(2) . . ? 
C4 C5 C6 120.9(3) . . ? 
C5 C6 C1 118.3(2) . . ? 
C5 C6 C8 121.0(2) . . ? 
C1 C6 C8 120.7(2) . . ? 
C10 N9 C1 123.84(17) . . ? 
N9 C10 C15 119.82(19) . . ? 
N9 C10 C11 123.17(18) . . ? 
C15 C10 C11 117.00(18) . . ? 
C12 C11 C10 120.17(18) . . ? 
C12 C11 N16 116.86(19) . . ? 
C10 C11 N16 122.94(18) . . ? 
C13 C12 C11 121.7(2) . . ? 
C12 C13 C14 120.52(19) . . ? 
C12 C13 N19 116.6(2) . . ? 
C14 C13 N19 122.9(2) . . ? 
N22 C14 C15 120.0(2) . . ? 
N22 C14 C13 123.2(2) . . ? 
C15 C14 C13 116.81(19) . . ? 
C14 C15 C10 123.8(2) . . ? 
O18 N16 O17 121.50(19) . . ? 
O18 N16 C11 119.36(19) . . ? 
O17 N16 C11 119.14(19) . . ? 
O20 N19 O21 121.1(2) . . ? 
O20 N19 C13 119.7(2) . . ? 
O21 N19 C13 119.2(2) . . ? 
C14 N22 C23 124.29(19) . . ? 
C24 C23 C28 120.9(3) . . ? 
C24 C23 N22 117.2(2) . . ? 
C28 C23 N22 121.9(3) . . ? 
C23 C24 C25 119.1(3) . . ? 
C23 C24 C29 121.6(3) . . ? 
C25 C24 C29 119.3(3) . . ? 
C26 C25 C24 120.8(4) . . ? 
C25 C26 C27 121.5(4) . . ? 
C26 C27 C28 120.6(3) . . ? 
C23 C28 C27 117.2(3) . . ? 
C23 C28 C30 119.7(3) . . ? 
C27 C28 C30 123.1(3) . . ? 
C56 C51 C52 122.2(2) . . ? 
C56 C51 N59 117.9(2) . . ? 
C52 C51 N59 119.9(2) . . ? 
C53 C52 C51 117.5(2) . . ? 
C53 C52 C57 120.3(2) . . ? 
C51 C52 C57 122.1(2) . . ? 
C54 C53 C52 121.6(3) . . ? 
C55 C54 C53 119.9(3) . . ? 
C54 C55 C56 121.6(3) . . ? 
C51 C56 C55 117.1(3) . . ? 
C51 C56 C58 121.5(2) . . ? 
C55 C56 C58 121.4(3) . . ? 
C60 N59 C51 123.26(17) . . ? 
N59 C60 C65 120.22(17) . . ? 
N59 C60 C61 123.20(18) . . ? 
C65 C60 C61 116.57(17) . . ? 
C62 C61 C60 120.57(18) . . ? 
C62 C61 N66 116.64(18) . . ? 
C60 C61 N66 122.78(19) . . ? 
C63 C62 C61 121.56(18) . . ? 
C62 C63 C64 120.25(17) . . ? 
C62 C63 N69 116.96(17) . . ? 
C64 C63 N69 122.79(19) . . ? 
N72 C64 C65 119.94(17) . . ? 
N72 C64 C63 123.14(17) . . ? 
C65 C64 C63 116.92(18) . . ? 
C60 C65 C64 123.98(18) . . ? 
O68 N66 O67 121.7(2) . . ? 
O68 N66 C61 118.7(2) . . ? 
O67 N66 C61 119.62(19) . . ? 
O71 N69 O70 121.76(19) . . ? 
O71 N69 C63 119.0(2) . . ? 
O70 N69 C63 119.21(17) . . ? 
C64 N72 C73 122.66(16) . . ? 
C74 C73 C78 122.9(2) . . ? 
C74 C73 N72 118.4(2) . . ? 
C78 C73 N72 118.7(2) . . ? 
C73 C74 C75 117.3(3) . . ? 
C73 C74 C79 121.0(2) . . ? 
C75 C74 C79 121.7(3) . . ? 
C76 C75 C74 120.3(3) . . ? 
C77 C76 C75 120.8(3) . . ? 
C76 C77 C78 121.0(3) . . ? 
C77 C78 C73 117.8(3) . . ? 
C77 C78 C80 120.9(3) . . ? 
C73 C78 C80 121.2(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 
C6 C1 C2 C3 0.7(3) . . . . ? 
N9 C1 C2 C3 -177.69(18) . . . . ? 
C6 C1 C2 C7 -179.4(2) . . . . ? 
N9 C1 C2 C7 2.3(3) . . . . ? 
C1 C2 C3 C4 0.5(3) . . . . ? 
C7 C2 C3 C4 -179.5(2) . . . . ? 
C2 C3 C4 C5 -0.4(4) . . . . ? 
C3 C4 C5 C6 -0.9(4) . . . . ? 
C4 C5 C6 C1 2.0(3) . . . . ? 
C4 C5 C6 C8 -178.2(2) . . . . ? 
C2 C1 C6 C5 -1.9(3) . . . . ? 
N9 C1 C6 C5 176.50(19) . . . . ? 
C2 C1 C6 C8 178.3(2) . . . . ? 
N9 C1 C6 C8 -3.3(3) . . . . ? 
C6 C1 N9 C10 91.4(2) . . . . ? 
C2 C1 N9 C10 -90.2(2) . . . . ? 
C1 N9 C10 C15 9.3(3) . . . . ? 
C1 N9 C10 C11 -171.52(19) . . . . ? 
N9 C10 C11 C12 -177.09(19) . . . . ? 
C15 C10 C11 C12 2.1(3) . . . . ? 
N9 C10 C11 N16 5.1(3) . . . . ? 
C15 C10 C11 N16 -175.73(18) . . . . ? 
C10 C11 C12 C13 -1.0(3) . . . . ? 
N16 C11 C12 C13 176.97(19) . . . . ? 
C11 C12 C13 C14 -0.1(3) . . . . ? 
C11 C12 C13 N19 -178.45(19) . . . . ? 
C12 C13 C14 N22 179.4(2) . . . . ? 
N19 C13 C14 N22 -2.4(3) . . . . ? 
C12 C13 C14 C15 0.0(3) . . . . ? 
N19 C13 C14 C15 178.23(19) . . . . ? 
N22 C14 C15 C10 -178.1(2) . . . . ? 
C13 C14 C15 C10 1.3(3) . . . . ? 
N9 C10 C15 C14 176.92(19) . . . . ? 
C11 C10 C15 C14 -2.3(3) . . . . ? 
C12 C11 N16 O18 -1.3(3) . . . . ? 
C10 C11 N16 O18 176.5(2) . . . . ? 
C12 C11 N16 O17 179.0(2) . . . . ? 
C10 C11 N16 O17 -3.1(3) . . . . ? 
C12 C13 N19 O20 -4.8(3) . . . . ? 
C14 C13 N19 O20 176.9(2) . . . . ? 
C12 C13 N19 O21 174.9(2) . . . . ? 
C14 C13 N19 O21 -3.5(3) . . . . ? 
C15 C14 N22 C23 -4.8(4) . . . . ? 
C13 C14 N22 C23 175.8(2) . . . . ? 
C14 N22 C23 C24 -101.1(3) . . . . ? 
C14 N22 C23 C28 79.1(3) . . . . ? 
C28 C23 C24 C25 0.4(4) . . . . ? 
N22 C23 C24 C25 -179.5(3) . . . . ? 
C28 C23 C24 C29 -177.3(3) . . . . ? 
N22 C23 C24 C29 2.9(4) . . . . ? 
C23 C24 C25 C26 0.9(5) . . . . ? 
C29 C24 C25 C26 178.7(3) . . . . ? 
C24 C25 C26 C27 -0.7(6) . . . . ? 
C25 C26 C27 C28 -0.7(6) . . . . ? 
C24 C23 C28 C27 -1.7(4) . . . . ? 
N22 C23 C28 C27 178.1(2) . . . . ? 
C24 C23 C28 C30 178.6(3) . . . . ? 
N22 C23 C28 C30 -1.6(4) . . . . ? 
C26 C27 C28 C23 1.9(4) . . . . ? 
C26 C27 C28 C30 -178.4(3) . . . . ? 
C56 C51 C52 C53 1.8(3) . . . . ? 
N59 C51 C52 C53 -177.4(2) . . . . ? 
C56 C51 C52 C57 -177.7(2) . . . . ? 
N59 C51 C52 C57 3.2(3) . . . . ? 
C51 C52 C53 C54 -1.6(4) . . . . ? 
C57 C52 C53 C54 177.9(3) . . . . ? 
C52 C53 C54 C55 -0.1(5) . . . . ? 
C53 C54 C55 C56 1.7(5) . . . . ? 
C52 C51 C56 C55 -0.3(4) . . . . ? 
N59 C51 C56 C55 178.9(2) . . . . ? 
C52 C51 C56 C58 -179.1(3) . . . . ? 
N59 C51 C56 C58 0.1(4) . . . . ? 
C54 C55 C56 C51 -1.5(4) . . . . ? 
C54 C55 C56 C58 177.3(3) . . . . ? 
C56 C51 N59 C60 -100.1(3) . . . . ? 
C52 C51 N59 C60 79.2(3) . . . . ? 
C51 N59 C60 C65 -4.7(3) . . . . ? 
C51 N59 C60 C61 175.9(2) . . . . ? 
N59 C60 C61 C62 179.07(19) . . . . ? 
C65 C60 C61 C62 -0.3(3) . . . . ? 
N59 C60 C61 N66 -0.3(3) . . . . ? 
C65 C60 C61 N66 -179.62(19) . . . . ? 
C60 C61 C62 C63 -2.2(3) . . . . ? 
N66 C61 C62 C63 177.21(18) . . . . ? 
C61 C62 C63 C64 1.5(3) . . . . ? 
C61 C62 C63 N69 -177.94(18) . . . . ? 
C62 C63 C64 N72 -178.68(18) . . . . ? 
N69 C63 C64 N72 0.7(3) . . . . ? 
C62 C63 C64 C65 1.6(3) . . . . ? 
N69 C63 C64 C65 -179.01(17) . . . . ? 
N59 C60 C65 C64 -175.80(19) . . . . ? 
C61 C60 C65 C64 3.6(3) . . . . ? 
N72 C64 C65 C60 176.04(19) . . . . ? 
C63 C64 C65 C60 -4.2(3) . . . . ? 
C62 C61 N66 O68 2.6(3) . . . . ? 
C60 C61 N66 O68 -178.1(2) . . . . ? 
C62 C61 N66 O67 -178.8(2) . . . . ? 
C60 C61 N66 O67 0.6(3) . . . . ? 
C62 C63 N69 O71 -7.8(3) . . . . ? 
C64 C63 N69 O71 172.83(19) . . . . ? 
C62 C63 N69 O70 171.33(18) . . . . ? 
C64 C63 N69 O70 -8.1(3) . . . . ? 
C65 C64 N72 C73 5.2(3) . . . . ? 
C63 C64 N72 C73 -174.56(18) . . . . ? 
C64 N72 C73 C74 90.3(2) . . . . ? 
C64 N72 C73 C78 -88.6(2) . . . . ? 
C78 C73 C74 C75 -0.8(3) . . . . ? 
N72 C73 C74 C75 -179.72(19) . . . . ? 
C78 C73 C74 C79 178.7(2) . . . . ? 
N72 C73 C74 C79 -0.2(3) . . . . ? 
C73 C74 C75 C76 0.8(4) . . . . ? 
C79 C74 C75 C76 -178.8(3) . . . . ? 
C74 C75 C76 C77 0.0(4) . . . . ? 
C75 C76 C77 C78 -0.7(4) . . . . ? 
C76 C77 C78 C73 0.6(4) . . . . ? 
C76 C77 C78 C80 -178.7(3) . . . . ? 
C74 C73 C78 C77 0.1(3) . . . . ? 
N72 C73 C78 C77 179.03(19) . . . . ? 
C74 C73 C78 C80 179.4(2) . . . . ? 
N72 C73 C78 C80 -1.6(3) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.916 
_diffrn_reflns_theta_full              72.03 
_diffrn_measured_fraction_theta_full   0.916 
_refine_diff_density_max    0.275 
_refine_diff_density_min   -0.208 
_refine_diff_density_rms    0.048 
