# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N4 O4' _chemical_formula_sum 'C29.33 H25.33 N5.33 O5.33' _chemical_formula_weight 537.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _chemical_absolute_configuration rm _cell_length_a 7.5547(12) _cell_length_b 15.716(3) _cell_length_c 15.716 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1866.0(4) _cell_formula_units_Z 3 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.974 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 AXS area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16279 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4453 _reflns_number_gt 4160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.5(9) _refine_ls_number_reflns 4453 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 N1 N 0.00906(16) 0.68434(7) 0.17563(8) 0.0373(3) Uani 1 1 d . . . N2 N 0.07643(15) 0.87719(7) 0.05372(7) 0.0335(2) Uani 1 1 d . . . C3 C 0.27170(19) 0.98582(9) -0.04100(9) 0.0373(3) Uani 1 1 d . . . O1 O 0.22083(17) 0.71944(8) 0.07965(8) 0.0512(3) Uani 1 1 d . . . C5 C -0.3145(2) 0.69976(10) 0.42203(10) 0.0454(3) Uani 1 1 d . . . H5A H -0.2789 0.6516 0.4518 0.054 Uiso 1 1 calc R . . C6 C -0.27549(17) 0.71035(9) 0.33722(9) 0.0354(3) Uani 1 1 d . . . O2 O -0.40065(14) 0.77654(8) 0.13934(7) 0.0479(3) Uani 1 1 d . . . H2A H -0.4805 0.8084 0.1547 0.072 Uiso 1 1 calc R . . O3 O 0.27311(16) 0.88175(9) 0.16282(7) 0.0537(3) Uani 1 1 d . . . C9 C -0.12519(17) 0.84398(8) 0.17648(9) 0.0352(3) Uani 1 1 d . . . H9A H -0.1817 0.8984 0.1661 0.042 Uiso 1 1 calc R . . H9B H -0.0403 0.8509 0.2222 0.042 Uiso 1 1 calc R . . C10 C 0.02323(19) 0.90649(8) -0.02404(8) 0.0353(3) Uani 1 1 d . . . H10A H -0.0847 0.8868 -0.0445 0.042 Uiso 1 1 calc R . . N3 N -0.17666(17) 0.65525(7) 0.28445(8) 0.0380(3) Uani 1 1 d . . . C12 C -0.03255(17) 0.81287(8) 0.09624(8) 0.0325(3) Uani 1 1 d . . . H12A H -0.1250 0.7958 0.0560 0.039 Uiso 1 1 calc R . . C13 C 0.33682(18) 0.96076(9) 0.03753(10) 0.0385(3) Uani 1 1 d . . . O4 O 0.01346(18) 0.58057(8) 0.37042(8) 0.0566(3) Uani 1 1 d . . . C15 C 0.23170(19) 0.90486(9) 0.09190(9) 0.0383(3) Uani 1 1 d . . . C16 C -0.26319(16) 0.77749(8) 0.20046(8) 0.0323(3) Uani 1 1 d . . . C17 C 0.08062(19) 0.73367(8) 0.11460(8) 0.0363(3) Uani 1 1 d . . . N4 N 0.10858(17) 0.95866(8) -0.07127(7) 0.0390(3) Uani 1 1 d . . . H4A H 0.0671 0.9760 -0.1192 0.047 Uiso 1 1 calc R . . C19 C -0.42480(19) 0.84461(10) 0.33146(10) 0.0429(3) Uani 1 1 d . . . H19A H -0.4627 0.8924 0.3016 0.052 Uiso 1 1 calc R . . C20 C 0.3738(2) 1.03959(10) -0.09273(11) 0.0470(3) Uani 1 1 d . . . H20A H 0.3308 1.0572 -0.1453 0.056 Uiso 1 1 calc R . . C21 C -0.0235(2) 0.61253(9) 0.30302(10) 0.0399(3) Uani 1 1 d . . . C22 C -0.32822(17) 0.78189(9) 0.29149(8) 0.0339(3) Uani 1 1 d . . . C23 C 0.0964(2) 0.61678(9) 0.22484(9) 0.0391(3) Uani 1 1 d . . . H23A H 0.0919 0.5629 0.1936 0.047 Uiso 1 1 calc R . . C24 C 0.5039(2) 0.98904(11) 0.06493(13) 0.0510(4) Uani 1 1 d . . . H24A H 0.5473 0.9727 0.1178 0.061 Uiso 1 1 calc R . . C25 C -0.4086(2) 0.76381(12) 0.46073(10) 0.0503(4) Uani 1 1 d . . . H25A H -0.4357 0.7589 0.5183 0.060 Uiso 1 1 calc R . . C26 C -0.17618(17) 0.68828(8) 0.19803(8) 0.0330(3) Uani 1 1 d . . . H26A H -0.2445 0.6505 0.1609 0.040 Uiso 1 1 calc R . . C27 C -0.4643(2) 0.83506(11) 0.41707(11) 0.0503(4) Uani 1 1 d . . . H27A H -0.5287 0.8769 0.4452 0.060 Uiso 1 1 calc R . . C28 C 0.6026(2) 1.04103(12) 0.01284(14) 0.0594(4) Uani 1 1 d . . . H28A H 0.7138 1.0594 0.0303 0.071 Uiso 1 1 calc R . . C29 C 0.5366(2) 1.06599(11) -0.06550(13) 0.0556(4) Uani 1 1 d . . . H29A H 0.6042 1.1013 -0.1001 0.067 Uiso 1 1 calc R . . C14 C 0.2852(2) 0.63667(15) 0.25052(13) 0.0610(5) Uani 1 1 d . . . H14A H 0.3581 0.6399 0.2006 0.091 Uiso 1 1 calc R . . H14B H 0.3287 0.5926 0.2873 0.091 Uiso 1 1 calc R . . H14C H 0.2885 0.6902 0.2800 0.091 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 N1 0.0302(5) 0.0415(6) 0.0401(5) 0.0035(5) 0.0023(5) 0.0092(5) N2 0.0256(5) 0.0390(5) 0.0358(5) 0.0021(4) -0.0015(4) -0.0017(5) C3 0.0340(7) 0.0364(6) 0.0415(6) -0.0077(5) 0.0055(5) -0.0014(5) O1 0.0427(6) 0.0550(6) 0.0560(6) 0.0071(5) 0.0162(5) 0.0159(5) C5 0.0377(7) 0.0528(8) 0.0456(7) 0.0116(7) 0.0024(6) -0.0006(7) C6 0.0250(5) 0.0396(6) 0.0415(6) 0.0025(5) 0.0004(5) -0.0017(5) O2 0.0279(5) 0.0709(7) 0.0449(5) 0.0011(5) -0.0096(4) 0.0092(5) O3 0.0387(6) 0.0735(8) 0.0487(6) 0.0108(6) -0.0150(5) -0.0075(6) C9 0.0280(6) 0.0354(6) 0.0422(6) 0.0007(5) 0.0026(5) 0.0040(5) C10 0.0310(6) 0.0414(7) 0.0336(6) -0.0024(5) -0.0034(5) -0.0021(5) N3 0.0342(6) 0.0364(5) 0.0433(6) 0.0049(5) 0.0021(5) 0.0001(5) C12 0.0256(5) 0.0365(6) 0.0354(6) 0.0020(5) -0.0021(5) -0.0003(5) C13 0.0271(6) 0.0380(6) 0.0504(7) -0.0046(6) -0.0013(5) -0.0014(5) O4 0.0504(7) 0.0652(7) 0.0543(6) 0.0241(6) 0.0023(6) 0.0128(6) C15 0.0278(6) 0.0436(7) 0.0434(7) 0.0005(5) -0.0044(6) 0.0015(5) C16 0.0221(5) 0.0385(6) 0.0363(6) 0.0002(5) -0.0023(5) 0.0023(5) C17 0.0327(6) 0.0399(6) 0.0364(6) -0.0016(5) 0.0009(5) 0.0057(5) N4 0.0388(6) 0.0445(6) 0.0339(5) 0.0013(5) -0.0027(5) -0.0044(5) C19 0.0328(6) 0.0441(7) 0.0519(8) 0.0018(6) 0.0053(6) 0.0038(6) C20 0.0456(8) 0.0455(7) 0.0498(8) -0.0038(6) 0.0123(7) -0.0064(6) C21 0.0359(7) 0.0339(6) 0.0500(7) 0.0032(6) 0.0001(6) 0.0015(5) C22 0.0240(5) 0.0399(6) 0.0378(6) 0.0003(5) -0.0001(5) -0.0019(5) C23 0.0362(7) 0.0373(6) 0.0437(7) 0.0014(5) -0.0007(6) 0.0084(6) C24 0.0327(7) 0.0527(8) 0.0677(10) -0.0015(8) -0.0083(7) -0.0045(6) C25 0.0448(8) 0.0645(10) 0.0416(7) 0.0041(7) 0.0094(7) -0.0008(8) C26 0.0267(6) 0.0345(6) 0.0378(6) -0.0021(5) -0.0034(5) -0.0006(5) C27 0.0418(8) 0.0533(8) 0.0559(8) -0.0062(7) 0.0127(7) 0.0041(7) C28 0.0326(7) 0.0581(9) 0.0876(13) -0.0051(9) 0.0019(8) -0.0111(7) C29 0.0448(9) 0.0511(8) 0.0709(11) -0.0062(8) 0.0184(8) -0.0134(7) C14 0.0337(8) 0.0882(14) 0.0610(10) 0.0182(10) -0.0034(7) 0.0058(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 N1 C17 1.3466(18) . ? N1 C26 1.4443(17) . ? N1 C23 1.4701(17) . ? N2 C10 1.3665(16) . ? N2 C15 1.3875(18) . ? N2 C12 1.4650(16) . ? C3 C13 1.386(2) . ? C3 N4 1.3881(19) . ? C3 C20 1.403(2) . ? O1 C17 1.2139(18) . ? C5 C25 1.374(2) . ? C5 C6 1.375(2) . ? C6 C22 1.3926(18) . ? C6 N3 1.4125(18) . ? O2 C16 1.4147(15) . ? O3 C15 1.2133(18) . ? C9 C12 1.5227(18) . ? C9 C16 1.5235(18) . ? C10 N4 1.2802(18) . ? N3 C21 1.3689(19) . ? N3 C26 1.4540(18) . ? C12 C17 1.5375(17) . ? C13 C24 1.405(2) . ? C13 C15 1.460(2) . ? O4 C21 1.2052(18) . ? C16 C22 1.5143(17) . ? C16 C26 1.5489(18) . ? C19 C22 1.378(2) . ? C19 C27 1.386(2) . ? C20 C29 1.367(3) . ? C21 C23 1.528(2) . ? C23 C14 1.515(2) . ? C24 C28 1.376(3) . ? C25 C27 1.379(2) . ? C28 C29 1.385(3) . ? 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 C17 N1 C26 122.54(11) . . ? C17 N1 C23 127.60(12) . . ? C26 N1 C23 109.74(11) . . ? C10 N2 C15 121.99(12) . . ? C10 N2 C12 118.37(11) . . ? C15 N2 C12 119.61(11) . . ? C13 C3 N4 122.21(13) . . ? C13 C3 C20 119.47(14) . . ? N4 C3 C20 118.31(14) . . ? C25 C5 C6 116.83(14) . . ? C5 C6 C22 122.45(14) . . ? C5 C6 N3 127.47(13) . . ? C22 C6 N3 110.07(12) . . ? C12 C9 C16 107.41(11) . . ? N4 C10 N2 125.89(13) . . ? C21 N3 C6 128.47(13) . . ? C21 N3 C26 111.85(12) . . ? C6 N3 C26 109.33(11) . . ? N2 C12 C9 114.49(11) . . ? N2 C12 C17 109.37(10) . . ? C9 C12 C17 111.11(11) . . ? C3 C13 C24 120.12(15) . . ? C3 C13 C15 119.93(12) . . ? C24 C13 C15 119.95(15) . . ? O3 C15 N2 121.43(14) . . ? O3 C15 C13 125.27(14) . . ? N2 C15 C13 113.29(12) . . ? O2 C16 C22 113.82(11) . . ? O2 C16 C9 109.97(11) . . ? C22 C16 C9 115.11(11) . . ? O2 C16 C26 106.58(11) . . ? C22 C16 C26 101.67(10) . . ? C9 C16 C26 108.93(10) . . ? O1 C17 N1 124.51(13) . . ? O1 C17 C12 123.33(13) . . ? N1 C17 C12 112.12(11) . . ? C10 N4 C3 116.45(12) . . ? C22 C19 C27 118.62(14) . . ? C29 C20 C3 119.73(17) . . ? O4 C21 N3 126.00(14) . . ? O4 C21 C23 125.96(14) . . ? N3 C21 C23 107.96(12) . . ? C19 C22 C6 119.59(13) . . ? C19 C22 C16 129.44(12) . . ? C6 C22 C16 110.97(11) . . ? N1 C23 C14 114.45(14) . . ? N1 C23 C21 100.85(11) . . ? C14 C23 C21 110.69(13) . . ? C28 C24 C13 119.47(18) . . ? C5 C25 C27 122.16(15) . . ? N1 C26 N3 102.40(11) . . ? N1 C26 C16 117.13(11) . . ? N3 C26 C16 107.40(10) . . ? C25 C27 C19 120.34(15) . . ? C24 C28 C29 120.14(16) . . ? C20 C29 C28 121.06(16) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.231 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 791762' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_date 2013-12-05 _audit_creation_method ; Olex2 1.2 (compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720) ; _chemical_formula_moiety '0.5(C23 H23 N4 O5)' _chemical_formula_sum 'C11.5 H11.5 N2 O2.5' _chemical_formula_weight 217.73 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source _atom_type_scat_dispersion_source H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236 57.79970 0.0030380000826 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870 51.65120 0.215599998832 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390 32.90890 0.250800013542 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750 0.58260 -11.5290002823 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' 'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2' _space_group_crystal_system trigonal _space_group_IT_number 144 _space_group_name_H-M_alt 'P 31' _space_group_name_Hall 'P 31' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -y,x-y,z+1/3 3 -x+y,-x,z+2/3 _symmetry_Int_Tables_number 144 _cell_length_a 10.6073(15) _cell_length_b 10.6073(15) _cell_length_c 35.206(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 3430.5(12) _cell_formula_units_Z 12 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3659 _cell_measurement_theta_max 20.37 _cell_measurement_theta_min 2.22 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.2646 _exptl_crystal_density_meas . _exptl_crystal_F_000 1374.7182 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_unetI/netI 0.1016 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 21093 _diffrn_reflns_theta_full 24.9958 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.74 _diffrn_ambient_temperature 273.15 _diffrn_measured_fraction_theta_full 0.8412 _diffrn_measured_fraction_theta_max 0.8412 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _reflns_Friedel_coverage 0.683 _reflns_limit_h_max 10 _reflns_limit_h_min -10 _reflns_limit_k_max 10 _reflns_limit_k_min -10 _reflns_limit_l_max 41 _reflns_limit_l_min -33 _reflns_number_gt 4383 _reflns_number_total 6802 _reflns_threshold_expression I>=2u(I) _computing_cell_refinement 'SAINT v6.28A (Bruker, 2002)' _computing_data_reduction 'SAINT v6.28A (Bruker, 2002)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'olex2.refine (Bourhis et al., 2013)' _refine_diff_density_max 0.9742 _refine_diff_density_min -0.3643 _refine_diff_density_rms 0.0978 _refine_ls_abs_structure_details 'Flack, H. D. (1983). Acta Cryst. A39, 876-881.' _refine_ls_abs_structure_Flack -2.4(7) _refine_ls_d_res_high 0.8410 _refine_ls_d_res_low 11.7354 _refine_ls_goodness_of_fit_ref 0.9916 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 83 _refine_ls_number_parameters 564 _refine_ls_number_reflns 6802 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1316 _refine_ls_R_factor_gt 0.0973 _refine_ls_restrained_S_all 0.9916 _refine_ls_shift/su_max 0.1210 _refine_ls_shift/su_mean 0.0205 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1981P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2628 _refine_ls_wR_factor_ref 0.2887 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C12(H12), C22(H22), C25(H25), C16(H16), C19(H19), C24(H24) 2.b Secondary CH2 refined with riding coordinates: C26(H26a,H26b), C31(H31a,H31b) 2.c Me refined with riding coordinates: C57(H57a,H57b,H57c), C47(H47a,H47b,H47c), C58(H58a,H58b,H58c), C61(H61a,H61b, H61c) 2.d Aromatic/amide H refined with riding coordinates: N14(H14), C27(H27), N11(H11a), C38(H38), C40(H40), C43(H43), C45(H45), C55(H55), C56(H56), C60(H60), C62(H62), N4(H4), C28(H28), C35(H35), N1(H1a), C41(H41), C44(H44), C50(H50), C103(H103), C104(H104), C105(H105), C106(H106) 2.e Fitted hexagon refined as free rotating group: C101(C102,C103,C104,C105,C106) 2.f Tetrahedral OH refined with riding coordinates: O11(H11), O1(H1) ; 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_refinement_flags_posn O6 O -0.4341(5) -0.8603(5) -0.18656(16) 0.0609(13) Uani 1.000000 . O11 O -0.9121(5) -1.1224(5) -0.18438(16) 0.0619(14) Uani 1.000000 . H11 H -0.8490(5) -1.0376(5) -0.18810(16) 0.093(2) Uiso 1.000000 R N13 N -0.6001(6) -1.0895(5) -0.20059(17) 0.0517(15) Uani 1.000000 . C10 C -0.8479(7) -1.2003(7) -0.1699(2) 0.0453(15) Uani 1.000000 . C12 C -0.7488(7) -1.2110(6) -0.1992(2) 0.0499(17) Uani 1.000000 . H12 H -0.7925(7) -1.2191(6) -0.2242(2) 0.060(2) Uiso 1.000000 R N14 N -0.7569(6) -1.3479(6) -0.19107(19) 0.0551(15) Uani 1.000000 . H14 H -0.6911(6) -1.3709(6) -0.19542(19) 0.0662(18) Uiso 1.000000 R C15 C -0.5518(7) -0.9688(7) -0.1806(2) 0.0497(17) Uani 1.000000 . C17 C -0.9490(6) -1.3568(7) -0.1617(2) 0.0471(16) Uani 1.000000 . N12 N -0.5477(7) -0.8950(6) -0.1153(2) 0.0684(19) Uani 1.000000 . C20 C -0.8932(7) -1.4356(7) -0.1747(2) 0.0522(17) Uani 1.000000 . C22 C -0.5160(9) -1.0862(8) -0.2331(3) 0.070(2) Uani 1.000000 . H22 H -0.5590(9) -1.1873(8) -0.2417(3) 0.084(3) Uiso 1.000000 R O12 O -0.6614(9) -0.7744(8) -0.1049(2) 0.098(2) Uani 1.000000 . C25 C -0.6439(7) -0.9706(7) -0.1471(2) 0.0515(17) Uani 1.000000 . H25 H -0.6921(7) -0.9160(7) -0.1545(2) 0.062(2) Uiso 1.000000 R C26 C -0.7592(7) -1.1201(7) -0.1356(2) 0.0494(16) Uani 1.000000 . H26a H -0.8217(7) -1.1137(7) -0.1165(2) 0.0593(19) Uiso 1.000000 R H26b H -0.7145(7) -1.1724(7) -0.1247(2) 0.0593(19) Uiso 1.000000 R C27 C -1.0835(7) -1.4191(8) -0.1441(3) 0.064(2) Uani 1.000000 . H27 H -1.1237(7) -1.3642(8) -0.1354(3) 0.077(2) Uiso 1.000000 R O13 O -0.3572(8) -1.0915(8) -0.1887(4) 0.122(3) Uani 1.000000 . N11 N -0.3490(9) -0.8586(10) -0.0786(3) 0.103(3) Uani 1.000000 . H11a H -0.2795(9) -0.8744(10) -0.0726(3) 0.124(4) Uiso 1.000000 R C36 C -0.4577(9) -0.7137(9) -0.0651(2) 0.064(2) Uani 1.000000 . C38 C -1.0993(10) -1.6440(9) -0.1543(3) 0.078(3) Uani 1.000000 . H38 H -1.1559(10) -1.7448(9) -0.1524(3) 0.093(3) Uiso 1.000000 R C39 C -0.3665(11) -0.7585(11) -0.0607(3) 0.082(3) Uani 1.000000 . C40 C -0.9682(9) -1.5872(8) -0.1709(3) 0.071(2) Uani 1.000000 . H40 H -0.9298(9) -1.6444(8) -0.1791(3) 0.086(3) Uiso 1.000000 R C43 C -0.4413(9) -0.9330(13) -0.1058(3) 0.089(3) Uani 1.000000 . H43 H -0.4369(9) -1.0079(13) -0.1183(3) 0.107(4) Uiso 1.000000 R C45 C -1.1518(9) -1.5645(10) -0.1406(3) 0.080(3) Uani 1.000000 . H45 H -1.2405(9) -1.6111(10) -0.1279(3) 0.096(3) Uiso 1.000000 R C46 C -0.5666(10) -0.7933(10) -0.0970(3) 0.074(2) Uani 1.000000 . C23 C -0.3651(10) -1.0399(11) -0.2232(5) 0.109(5) Uani 1.000000 . O14 O -0.2668(10) -0.9785(10) -0.2420(3) 0.148(4) Uani 1.000000 . C55 C -0.4625(14) -0.6093(13) -0.0466(3) 0.110(4) Uani 1.000000 . H55 H -0.5347(14) -0.5861(13) -0.0513(3) 0.132(5) Uiso 1.000000 R C56 C -0.2641(16) -0.5735(17) -0.0149(3) 0.139(7) Uani 1.000000 . H56 H -0.1967(16) -0.5116(17) 0.0029(3) 0.167(8) Uiso 1.000000 R C57 C -0.5147(13) -1.0044(10) -0.2655(3) 0.101(4) Uani 1.000000 . H57a H -0.4551(13) -1.0110(10) -0.2850(3) 0.151(5) Uiso 1.000000 R H57b H -0.6122(13) -1.0429(10) -0.2748(3) 0.151(5) Uiso 1.000000 R H57c H -0.4760(13) -0.9043(10) -0.2585(3) 0.151(5) Uiso 1.000000 R C60 C -0.3706(15) -0.5455(19) -0.0234(4) 0.132(5) Uani 1.000000 . H60 H -0.3729(15) -0.4707(19) -0.0102(4) 0.158(6) Uiso 1.000000 R C62 C -0.2409(13) -0.6795(14) -0.0285(4) 0.114(4) Uani 1.000000 . H62 H -0.1700(13) -0.7018(14) -0.0212(4) 0.137(5) Uiso 1.000000 R O5 O -0.5633(5) -0.4256(6) -0.24874(15) 0.0591(13) Uani 1.000000 . O1 O -0.0883(5) -0.2092(5) -0.25104(15) 0.0581(13) Uani 1.000000 . H1 H -0.0392(5) -0.2017(5) -0.23226(15) 0.0872(19) Uiso 1.000000 R N3 N -0.3985(5) -0.4886(6) -0.23437(17) 0.0479(14) Uani 1.000000 . N4 N -0.2423(6) -0.5925(6) -0.2441(2) 0.0588(16) Uani 1.000000 . H4 H -0.3087(6) -0.6813(6) -0.2402(2) 0.071(2) Uiso 1.000000 R C8 C -0.1530(7) -0.3527(7) -0.2653(2) 0.0489(16) Uani 1.000000 . C9 C -0.0490(7) -0.4051(8) -0.2733(2) 0.0496(16) Uani 1.000000 . C11 C -0.4500(7) -0.4177(7) -0.2556(2) 0.0494(17) Uani 1.000000 . N2 N -0.4549(8) -0.3480(8) -0.3201(2) 0.0688(18) Uani 1.000000 . C16 C -0.2510(7) -0.4613(7) -0.2350(2) 0.0487(17) Uani 1.000000 . H16 H -0.2071(7) -0.4254(7) -0.2100(2) 0.058(2) Uiso 1.000000 R C19 C -0.3602(7) -0.3307(8) -0.2883(2) 0.0525(17) Uani 1.000000 . H19 H -0.3124(7) -0.2282(8) -0.2807(2) 0.063(2) Uiso 1.000000 R C21 C -0.1082(7) -0.5455(8) -0.2601(2) 0.0553(18) Uani 1.000000 . C24 C -0.4836(9) -0.5707(9) -0.2033(3) 0.071(2) Uani 1.000000 . H24 H -0.4403(9) -0.6278(9) -0.1941(3) 0.085(3) Uiso 1.000000 R C28 C 0.0822(8) -0.3393(9) -0.2915(3) 0.068(2) Uani 1.000000 . H28 H 0.1182(8) -0.2466(9) -0.3016(3) 0.081(3) Uiso 1.000000 R O3 O -0.6438(7) -0.7369(7) -0.2476(3) 0.104(3) Uani 1.000000 . O2 O -0.3381(9) -0.1102(9) -0.3304(2) 0.106(2) Uani 1.000000 . C31 C -0.2412(7) -0.3627(8) -0.2993(2) 0.0523(17) Uani 1.000000 . H31a H -0.1789(7) -0.2935(8) -0.3184(2) 0.063(2) Uiso 1.000000 R H31b H -0.2841(7) -0.4596(8) -0.3101(2) 0.063(2) Uiso 1.000000 R C35 C -0.0313(9) -0.6151(9) -0.2634(3) 0.068(2) Uani 1.000000 . H35 H -0.0681(9) -0.7080(9) -0.2533(3) 0.082(3) Uiso 1.000000 R N1 N -0.6520(9) -0.5100(10) -0.3570(4) 0.127(5) Uani 1.000000 . H1a H -0.7205(9) -0.5960(10) -0.3629(4) 0.153(6) Uiso 1.000000 R C41 C 0.0985(10) -0.5503(13) -0.2812(3) 0.084(3) Uani 1.000000 . H41 H 0.1489(10) -0.6003(13) -0.2845(3) 0.100(3) Uiso 1.000000 R C44 C 0.1579(9) -0.4059(12) -0.2947(3) 0.080(3) Uani 1.000000 . H44 H 0.2498(9) -0.3586(12) -0.3058(3) 0.096(3) Uiso 1.000000 R C47 C -0.4793(14) -0.4765(16) -0.1701(3) 0.110(4) Uani 1.000000 . H47a H -0.5388(14) -0.5377(16) -0.1498(3) 0.165(6) Uiso 1.000000 R H47b H -0.3808(14) -0.4183(16) -0.1614(3) 0.165(6) Uiso 1.000000 R H47c H -0.5154(14) -0.4140(16) -0.1782(3) 0.165(6) Uiso 1.000000 R O4 O -0.7368(9) -0.7088(13) -0.1926(4) 0.169(5) Uani 1.000000 . C50 C -0.5591(8) -0.4923(12) -0.3294(3) 0.082(3) Uani 1.000000 . H50 H -0.5628(8) -0.5713(12) -0.3169(3) 0.098(4) Uiso 1.000000 R C51 C -0.6354(11) -0.6761(13) -0.2136(4) 0.096(4) Uani 1.000000 . C54 C -0.4359(10) -0.2293(11) -0.3397(3) 0.071(2) Uani 1.000000 . C58 C -0.7880(13) -0.8426(14) -0.2627(6) 0.152(7) Uani 1.000000 . H58a H -0.7769(13) -0.8766(14) -0.2871(6) 0.228(10) Uiso 1.000000 R H58b H -0.8353(13) -0.9235(14) -0.2456(6) 0.228(10) Uiso 1.000000 R H58c H -0.8458(13) -0.7967(14) -0.2654(6) 0.228(10) Uiso 1.000000 R C61 C -0.2108(15) -1.0587(19) -0.1792(6) 0.160(7) Uani 1.000000 . H61a H -0.2109(15) -1.0974(19) -0.1545(6) 0.240(11) Uiso 1.000000 R H61b H -0.1776(15) -1.1018(19) -0.1978(6) 0.240(11) Uiso 1.000000 R H61c H -0.1471(15) -0.9551(19) -0.1790(6) 0.240(11) Uiso 1.000000 R C101 C -0.6394(8) -0.3975(7) -0.37507(19) 0.074(2) Uani 1.000000 . C102 C -0.5348(7) -0.2531(8) -0.36848(17) 0.077(2) Uani 1.000000 G C103 C -0.5372(9) -0.1427(7) -0.3892(2) 0.126(5) Uani 1.000000 G H103 H -0.4673(9) -0.0461(7) -0.3848(2) 0.151(6) Uiso 1.000000 R C104 C -0.6442(12) -0.1768(12) -0.4165(2) 0.157(7) Uani 1.000000 G H104 H -0.6459(12) -0.1030(12) -0.4303(2) 0.189(9) Uiso 1.000000 R C105 C -0.7488(9) -0.3213(14) -0.42307(19) 0.130(6) Uani 1.000000 G H105 H -0.8204(9) -0.3441(14) -0.44133(19) 0.156(7) Uiso 1.000000 R C106 C -0.7464(7) -0.4316(10) -0.4024(2) 0.139(5) Uani 1.000000 G H106 H -0.8164(7) -0.5282(10) -0.4068(2) 0.166(6) Uiso 1.000000 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O6 0.053(3) 0.038(2) 0.070(4) 0.007(2) 0.011(2) 0.006(2) O11 0.046(3) 0.048(3) 0.090(4) 0.022(2) -0.013(3) -0.005(3) N13 0.043(3) 0.031(3) 0.061(4) 0.003(2) 0.009(3) 0.005(3) C10 0.042(3) 0.042(3) 0.051(4) 0.019(3) 0.006(3) 0.006(3) C12 0.032(3) 0.038(3) 0.065(5) 0.006(3) 0.002(3) -0.000(3) N14 0.037(3) 0.048(3) 0.077(4) 0.018(3) 0.003(3) -0.006(3) C15 0.036(3) 0.038(4) 0.060(5) 0.007(3) -0.005(3) -0.004(3) C17 0.031(3) 0.046(4) 0.053(4) 0.011(3) 0.001(3) 0.000(3) N12 0.070(4) 0.040(3) 0.070(5) 0.009(3) 0.006(3) -0.013(3) C20 0.043(4) 0.045(4) 0.054(4) 0.011(3) -0.004(3) 0.002(3) C22 0.060(5) 0.038(4) 0.087(6) 0.005(3) 0.025(4) -0.011(4) O12 0.102(5) 0.104(5) 0.104(5) 0.064(4) -0.022(4) -0.040(4) C25 0.049(4) 0.041(3) 0.054(4) 0.014(3) -0.006(3) -0.011(3) C26 0.042(3) 0.048(4) 0.054(4) 0.019(3) 0.001(3) 0.003(3) C27 0.038(4) 0.063(5) 0.079(6) 0.015(3) 0.008(4) 0.014(4) O13 0.059(4) 0.075(5) 0.234(12) 0.034(4) 0.011(6) -0.009(6) N11 0.077(5) 0.097(6) 0.137(9) 0.044(5) 0.020(6) 0.050(6) C36 0.060(5) 0.061(5) 0.063(5) 0.023(4) 0.001(4) -0.002(4) C38 0.070(6) 0.044(4) 0.097(7) 0.012(4) 0.010(5) 0.018(4) C39 0.086(6) 0.089(6) 0.075(6) 0.047(6) 0.028(5) 0.005(5) C40 0.070(5) 0.031(4) 0.091(6) 0.009(4) 0.004(4) -0.001(4) C43 0.040(4) 0.139(9) 0.068(6) 0.029(5) -0.005(4) 0.039(6) C45 0.061(5) 0.064(5) 0.086(7) 0.009(4) 0.010(4) 0.008(5) C46 0.057(5) 0.065(5) 0.070(6) 0.009(4) 0.003(4) 0.004(4) C23 0.044(5) 0.049(5) 0.198(15) -0.004(4) 0.045(8) -0.034(7) O14 0.083(5) 0.125(6) 0.188(10) 0.016(5) 0.069(6) -0.024(6) C55 0.109(8) 0.108(8) 0.058(6) 0.013(7) -0.005(6) -0.035(6) C56 0.102(10) 0.138(12) 0.061(7) -0.028(9) -0.024(6) -0.028(8) C57 0.101(7) 0.063(6) 0.096(8) 0.009(5) 0.045(6) 0.014(5) C60 0.087(8) 0.194(16) 0.080(9) 0.044(9) -0.011(7) -0.001(9) C62 0.105(9) 0.105(8) 0.077(7) 0.011(7) 0.011(6) -0.015(7) O5 0.052(3) 0.077(3) 0.072(4) 0.050(3) 0.000(2) -0.001(3) O1 0.057(3) 0.056(3) 0.063(3) 0.029(2) -0.018(2) -0.011(2) N3 0.042(3) 0.055(3) 0.062(4) 0.035(3) 0.009(3) 0.014(3) N4 0.042(3) 0.046(3) 0.097(5) 0.028(3) 0.010(3) 0.006(3) C8 0.042(3) 0.050(4) 0.056(4) 0.024(3) 0.008(3) 0.008(3) C9 0.035(3) 0.055(4) 0.053(4) 0.018(3) 0.005(3) -0.005(3) C11 0.040(4) 0.049(4) 0.065(5) 0.026(3) -0.013(3) -0.017(3) N2 0.073(4) 0.103(5) 0.064(4) 0.069(4) 0.007(3) 0.008(4) C16 0.047(4) 0.055(4) 0.057(5) 0.035(3) 0.004(3) 0.003(3) C19 0.051(4) 0.064(4) 0.054(4) 0.037(3) -0.001(3) -0.001(3) C21 0.048(4) 0.072(5) 0.059(5) 0.040(4) 0.004(3) -0.004(4) C24 0.058(5) 0.090(6) 0.086(6) 0.054(5) 0.033(4) 0.034(5) C28 0.043(4) 0.065(5) 0.085(6) 0.019(4) 0.009(4) -0.011(4) O3 0.058(4) 0.061(4) 0.187(9) 0.026(3) 0.008(4) 0.012(5) O2 0.121(6) 0.084(5) 0.109(6) 0.048(5) -0.010(5) 0.018(4) C31 0.046(4) 0.055(4) 0.059(5) 0.027(3) 0.010(3) 0.011(3) C35 0.056(4) 0.064(5) 0.097(6) 0.040(4) -0.008(4) -0.001(4) N1 0.059(5) 0.093(6) 0.217(13) 0.028(5) 0.021(7) -0.073(8) C41 0.085(6) 0.140(9) 0.069(6) 0.088(7) 0.011(5) 0.006(6) C44 0.054(5) 0.109(7) 0.089(7) 0.049(5) 0.013(4) 0.001(6) C47 0.136(9) 0.190(12) 0.061(6) 0.125(10) 0.029(6) 0.022(7) O4 0.062(5) 0.218(10) 0.222(12) 0.067(6) 0.064(6) 0.105(9) C50 0.041(4) 0.120(8) 0.067(6) 0.028(5) -0.010(4) -0.042(5) C51 0.075(7) 0.093(7) 0.147(11) 0.061(6) 0.035(7) 0.057(8) C54 0.062(5) 0.087(6) 0.082(6) 0.050(5) -0.001(4) 0.005(5) C58 0.090(8) 0.077(7) 0.25(2) 0.010(6) 0.003(10) -0.001(9) C61 0.107(10) 0.143(12) 0.24(2) 0.070(9) -0.037(12) -0.046(13) C101 0.087(6) 0.073(6) 0.068(6) 0.045(5) 0.023(5) 0.013(4) C102 0.072(6) 0.104(7) 0.063(6) 0.049(5) 0.017(4) 0.003(5) C103 0.164(12) 0.157(12) 0.105(10) 0.117(11) 0.037(9) 0.037(8) C104 0.169(14) 0.31(2) 0.092(10) 0.193(17) -0.007(10) 0.033(12) C105 0.070(7) 0.243(18) 0.073(8) 0.075(9) -0.030(6) -0.054(10) C106 0.105(10) 0.183(15) 0.106(10) 0.056(10) 0.008(8) 0.020(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O6 C15 1.220(8) . O11 C10 1.403(8) . N13 C12 1.455(8) . N13 C15 1.319(9) . N13 C22 1.440(10) . C10 C12 1.516(10) . C10 C17 1.487(9) . C10 C26 1.507(10) . C12 N14 1.440(9) . N14 C20 1.393(9) . C15 C25 1.525(10) . C17 C20 1.325(10) . C17 C27 1.382(10) . N12 C25 1.457(10) . N12 C43 1.416(12) . N12 C46 1.354(12) . C20 C40 1.400(10) . C22 C23 1.462(16) . C22 C57 1.431(15) . O12 C46 1.154(11) . C25 C26 1.495(9) . C27 C45 1.342(12) . O13 C23 1.353(18) . O13 C61 1.450(15) . N11 C39 1.326(13) . N11 C43 1.314(14) . C36 C39 1.283(13) . C36 C46 1.527(13) . C36 C55 1.309(14) . C38 C40 1.342(13) . C38 C45 1.313(13) . C39 C62 1.624(17) . C23 O14 1.127(13) . C55 C60 1.189(16) . C56 C60 1.34(2) . C56 C62 1.35(2) . O5 C11 1.187(8) . O1 C8 1.412(8) . N3 C11 1.354(9) . N3 C16 1.442(8) . N3 C24 1.409(10) . N4 C16 1.474(8) . N4 C21 1.372(9) . C8 C9 1.489(9) . C8 C16 1.531(10) . C8 C31 1.492(10) . C9 C21 1.375(10) . C9 C28 1.365(10) . C11 C19 1.485(11) . N2 C19 1.452(10) . N2 C50 1.408(12) . N2 C54 1.359(11) . C19 C31 1.513(9) . C21 C35 1.351(10) . C24 C47 1.523(15) . C24 C51 1.475(15) . C28 C44 1.314(12) . O3 C51 1.340(16) . O3 C58 1.471(15) . O2 C54 1.212(11) . C35 C41 1.347(12) . N1 C50 1.328(15) . N1 C101 1.299(14) . C41 C44 1.417(14) . O4 C51 1.205(13) . C54 C102 1.389(11) . C101 C102 1.3900 . C101 C106 1.3900 . C102 C103 1.3900 . C103 C104 1.3900 . C104 C105 1.3900 . C105 C106 1.3900 . 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 C15 N13 C12 124.3(6) . . C22 N13 C12 115.6(6) . . C22 N13 C15 117.7(5) . . C12 C10 O11 110.9(6) . . C17 C10 O11 115.9(5) . . C17 C10 C12 100.9(5) . . C26 C10 O11 108.0(5) . . C26 C10 C12 109.0(5) . . C26 C10 C17 111.8(6) . . C10 C12 N13 116.2(6) . . N14 C12 N13 113.0(5) . . N14 C12 C10 104.3(5) . . C20 N14 C12 105.9(5) . . N13 C15 O6 122.8(6) . . C25 C15 O6 119.4(6) . . C25 C15 N13 117.7(5) . . C20 C17 C10 109.7(6) . . C27 C17 C10 128.1(7) . . C27 C17 C20 122.2(7) . . C43 N12 C25 117.6(8) . . C46 N12 C25 117.6(8) . . C46 N12 C43 124.8(8) . . C17 C20 N14 111.4(6) . . C40 C20 N14 127.7(7) . . C40 C20 C17 121.0(7) . . C23 C22 N13 112.3(9) . . C57 C22 N13 117.8(8) . . C57 C22 C23 108.0(10) . . N12 C25 C15 108.7(5) . . C26 C25 C15 113.7(5) . . C26 C25 N12 110.5(6) . . C25 C26 C10 109.2(6) . . C45 C27 C17 115.2(8) . . C61 O13 C23 112.6(12) . . C43 N11 C39 117.9(10) . . C46 C36 C39 112.8(9) . . C55 C36 C39 127.4(10) . . C55 C36 C46 119.8(10) . . C45 C38 C40 123.3(8) . . C36 C39 N11 132.2(11) . . C62 C39 N11 109.7(10) . . C62 C39 C36 118.0(10) . . C38 C40 C20 115.1(8) . . N11 C43 N12 117.5(11) . . C38 C45 C27 123.1(8) . . O12 C46 N12 120.9(9) . . C36 C46 N12 114.7(9) . . C36 C46 O12 124.4(9) . . O13 C23 C22 110.9(9) . . O14 C23 C22 126.5(18) . . O14 C23 O13 122.4(15) . . C60 C55 C36 117.2(16) . . C62 C56 C60 129.0(12) . . C56 C60 C55 124.7(18) . . C56 C62 C39 103.5(12) . . C16 N3 C11 125.3(5) . . C24 N3 C11 117.4(5) . . C24 N3 C16 115.6(6) . . C21 N4 C16 106.8(5) . . C9 C8 O1 114.7(5) . . C16 C8 O1 110.3(6) . . C16 C8 C9 101.6(5) . . C31 C8 O1 108.1(5) . . C31 C8 C9 112.1(6) . . C31 C8 C16 109.8(5) . . C21 C9 C8 108.6(6) . . C28 C9 C8 130.8(7) . . C28 C9 C21 120.5(7) . . N3 C11 O5 121.6(7) . . C19 C11 O5 120.9(6) . . C19 C11 N3 117.5(5) . . C50 N2 C19 115.8(7) . . C54 N2 C19 120.0(8) . . C54 N2 C50 124.1(8) . . N4 C16 N3 112.8(5) . . C8 C16 N3 115.0(5) . . C8 C16 N4 102.7(5) . . N2 C19 C11 109.3(6) . . C31 C19 C11 114.0(6) . . C31 C19 N2 112.1(6) . . C9 C21 N4 111.1(6) . . C35 C21 N4 129.5(7) . . C35 C21 C9 119.3(7) . . C47 C24 N3 113.0(8) . . C51 C24 N3 113.3(9) . . C51 C24 C47 110.5(9) . . C44 C28 C9 120.5(9) . . C58 O3 C51 118.9(11) . . C19 C31 C8 110.0(6) . . C41 C35 C21 120.2(8) . . C101 N1 C50 120.0(9) . . C44 C41 C35 119.8(7) . . C41 C44 C28 119.4(8) . . N1 C50 N2 116.6(11) . . O3 C51 C24 111.8(8) . . O4 C51 C24 123.0(15) . . O4 C51 O3 125.1(13) . . O2 C54 N2 118.8(9) . . C102 C54 N2 117.0(9) . . C102 C54 O2 124.2(9) . . C102 C101 N1 126.1 . . C106 C101 N1 113.9 . . C106 C101 C102 120.0 . . C101 C102 C54 115.9(7) . . C103 C102 C54 124.1(7) . . C103 C102 C101 120.0 . . C104 C103 C102 120.0 . . C105 C104 C103 120.0 . . C106 C105 C104 120.0 . . C105 C106 C101 120.0 . . _database_code_depnum_ccdc_archive 'CCDC 791763' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_y _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N4 O4' _chemical_formula_sum 'C44 H40 N8 O10' _chemical_formula_weight 840.84 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 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _chemical_absolute_configuration rm _cell_length_a 27.1139(17) _cell_length_b 8.5424(5) _cell_length_c 8.8326(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.562(6) _cell_angle_gamma 90.00 _cell_volume 2036.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'multiwire proportional' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13969 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.1479 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 32.83 _reflns_number_total 6100 _reflns_number_gt 2801 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0198P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(8) _refine_ls_number_reflns 6100 _refine_ls_number_parameters 360 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1265 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0589 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.767 _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 O4 O 0.13188(6) -1.13388(16) -0.45007(17) 0.0350(4) Uani 1 1 d . . . N2 N 0.15446(6) -1.07618(18) -0.06226(18) 0.0277(4) Uani 1 1 d . . . O2 O 0.11620(5) -0.88075(16) 0.05199(16) 0.0395(4) Uani 1 1 d . . . N3 N 0.08283(6) -0.74070(18) -0.21695(19) 0.0303(4) Uani 1 1 d . . . C13 C 0.15108(8) -0.8892(2) -0.3177(2) 0.0256(5) Uani 1 1 d . . . C12 C 0.10744(7) -0.8913(2) -0.2224(2) 0.0260(5) Uani 1 1 d . . . C8 C 0.16702(7) -1.0570(2) -0.3462(2) 0.0250(5) Uani 1 1 d . . . C7 C 0.16978(7) -1.1527(2) -0.1969(2) 0.0282(5) Uani 1 1 d . . . C4 C 0.21962(8) -1.0678(2) -0.3886(2) 0.0284(5) Uani 1 1 d . . . C3 C 0.25042(8) -1.1381(2) -0.2732(2) 0.0313(5) Uani 1 1 d . . . N1 N 0.22265(6) -1.18181(19) -0.1533(2) 0.0324(4) Uani 1 1 d . . . C14 C 0.03316(8) -0.7292(2) -0.2677(3) 0.0380(6) Uani 1 1 d . . . C11 C 0.12539(7) -0.9480(2) -0.0634(2) 0.0278(5) Uani 1 1 d . . . C9 C 0.23430(9) -1.1647(3) -0.0016(3) 0.0421(6) Uani 1 1 d . . . N4 N 0.09375(7) -0.47147(19) -0.1568(3) 0.0551(6) Uani 1 1 d . . . O1 O 0.27560(6) -1.1765(2) 0.06461(18) 0.0688(6) Uani 1 1 d . . . C2 C 0.30086(8) -1.1541(2) -0.2816(3) 0.0365(6) Uani 1 1 d . . . C5 C 0.23935(9) -1.0108(3) -0.5152(3) 0.0385(6) Uani 1 1 d . . . C15 C 0.01444(9) -0.5702(2) -0.2702(3) 0.0482(7) Uani 1 1 d . . . C10 C 0.18800(8) -1.1230(3) 0.0707(3) 0.0357(6) Uani 1 1 d . . . C1 C 0.31962(10) -1.0945(2) -0.4083(3) 0.0425(6) Uani 1 1 d . . . C17 C 0.10970(9) -0.6130(3) -0.1609(3) 0.0437(6) Uani 1 1 d . . . C6 C 0.28992(10) -1.0253(3) -0.5235(3) 0.0472(7) Uani 1 1 d . . . C16 C 0.04473(9) -0.4490(3) -0.2132(3) 0.0596(8) Uani 1 1 d . . . C22 C 0.16830(12) -1.2558(3) 0.1625(3) 0.0503(7) Uani 1 1 d . . . C18 C -0.03388(10) -0.5381(3) -0.3336(4) 0.0679(9) Uani 1 1 d . . . C21 C 0.02661(12) -0.2945(3) -0.2166(5) 0.0939(14) Uani 1 1 d . . . C19 C -0.05079(12) -0.3865(4) -0.3437(5) 0.0961(13) Uani 1 1 d . . . C20 C -0.02082(13) -0.2672(4) -0.2807(6) 0.1139(16) Uani 1 1 d . . . O5 O -0.09087(7) -0.91891(18) -0.3472(2) 0.0387(4) Uani 1 1 d . . . O3 O 0.00939(6) -0.84608(16) -0.30916(19) 0.0508(5) Uani 1 1 d . . . H1 H -0.0983(7) -0.917(2) -0.260(2) 0.031(7) Uiso 1 1 d . . . H2 H 0.1420(6) -0.8448(18) -0.4215(19) 0.014(4) Uiso 1 1 d . . . H3 H 0.1777(7) -0.831(2) -0.262(2) 0.027(5) Uiso 1 1 d . . . H4 H -0.0613(11) -0.889(4) -0.357(4) 0.093(12) Uiso 1 1 d . . . H5 H 0.3523(8) -1.103(2) -0.407(2) 0.029(6) Uiso 1 1 d . . . H6 H 0.1375(9) -1.224(3) 0.207(2) 0.052(7) Uiso 1 1 d . . . H7 H 0.1444(8) -0.627(2) -0.124(2) 0.038(6) Uiso 1 1 d . . . H8 H 0.3214(7) -1.208(2) -0.201(2) 0.031(6) Uiso 1 1 d . . . H9 H 0.0833(7) -0.9664(19) -0.2697(18) 0.023(5) Uiso 1 1 d . . . H10 H 0.1943(11) -1.282(3) 0.252(3) 0.090(10) Uiso 1 1 d . . . H11 H 0.1533(6) -1.248(2) -0.2096(18) 0.025(5) Uiso 1 1 d . . . H12 H 0.3026(8) -0.991(3) -0.616(2) 0.049(7) Uiso 1 1 d . . . H13 H 0.2187(7) -0.963(2) -0.591(2) 0.033(6) Uiso 1 1 d . . . H14 H 0.1944(7) -1.037(2) 0.132(2) 0.032(6) Uiso 1 1 d . . . H15 H 0.1598(9) -1.346(3) 0.094(3) 0.073(9) Uiso 1 1 d . . . H16 H 0.1210(10) -1.080(3) -0.518(3) 0.068(10) Uiso 1 1 d . . . H17 H -0.0545(8) -0.629(3) -0.379(2) 0.057(7) Uiso 1 1 d . . . H18 H -0.0288(12) -0.162(4) -0.288(3) 0.115(11) Uiso 1 1 d . . . H19 H -0.0864(12) -0.376(4) -0.393(4) 0.125(12) Uiso 1 1 d . . . H20 H 0.0478(11) -0.202(4) -0.164(3) 0.118(12) Uiso 1 1 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 O4 0.0378(9) 0.0271(8) 0.0369(9) -0.0027(7) -0.0127(8) -0.0002(7) N2 0.0294(10) 0.0224(8) 0.0302(10) 0.0029(8) -0.0023(8) 0.0021(8) O2 0.0446(10) 0.0377(8) 0.0369(9) -0.0012(7) 0.0076(8) 0.0028(8) N3 0.0226(10) 0.0202(8) 0.0468(11) -0.0014(8) -0.0037(9) -0.0006(8) C13 0.0253(11) 0.0215(10) 0.0282(11) 0.0021(10) -0.0072(10) -0.0001(9) C12 0.0212(11) 0.0165(10) 0.0389(13) -0.0020(9) -0.0045(10) -0.0003(9) C8 0.0231(11) 0.0247(10) 0.0259(11) 0.0010(9) -0.0053(9) 0.0014(9) C7 0.0258(12) 0.0211(10) 0.0364(12) 0.0020(10) -0.0030(10) -0.0019(9) C4 0.0303(12) 0.0213(10) 0.0329(12) -0.0079(9) -0.0005(10) -0.0021(9) C3 0.0295(12) 0.0207(11) 0.0427(13) -0.0042(10) -0.0011(11) -0.0002(9) N1 0.0242(10) 0.0348(10) 0.0367(11) 0.0080(8) -0.0048(9) 0.0052(8) C14 0.0235(12) 0.0337(13) 0.0566(16) 0.0058(11) 0.0024(12) 0.0048(11) C11 0.0213(12) 0.0266(11) 0.0356(13) 0.0049(10) 0.0028(10) -0.0063(9) C9 0.0353(15) 0.0451(14) 0.0434(14) 0.0177(12) -0.0093(12) 0.0023(12) N4 0.0353(12) 0.0230(10) 0.1049(18) -0.0071(11) -0.0032(12) -0.0013(9) O1 0.0344(10) 0.1134(15) 0.0548(11) 0.0239(11) -0.0148(9) 0.0035(11) C2 0.0293(13) 0.0297(12) 0.0497(15) -0.0036(12) -0.0003(12) 0.0046(10) C5 0.0439(17) 0.0354(12) 0.0357(14) 0.0004(11) 0.0026(13) 0.0005(12) C15 0.0307(14) 0.0267(12) 0.086(2) 0.0002(12) -0.0024(13) 0.0019(11) C10 0.0394(14) 0.0335(13) 0.0319(13) 0.0059(11) -0.0087(11) 0.0018(11) C1 0.0276(14) 0.0320(13) 0.0688(19) -0.0128(13) 0.0103(14) 0.0002(11) C17 0.0261(13) 0.0332(14) 0.0696(17) -0.0031(11) -0.0062(12) -0.0023(11) C6 0.0562(19) 0.0352(14) 0.0531(17) -0.0045(13) 0.0210(16) -0.0008(13) C16 0.0342(15) 0.0265(13) 0.118(2) 0.0024(14) 0.0080(16) 0.0050(11) C22 0.058(2) 0.0461(16) 0.0462(17) 0.0135(14) 0.0025(16) 0.0061(15) C18 0.0342(16) 0.0364(15) 0.131(3) 0.0079(16) -0.0018(17) 0.0080(13) C21 0.042(2) 0.0314(16) 0.207(4) -0.001(2) 0.005(2) 0.0019(13) C19 0.0403(18) 0.0471(18) 0.196(4) 0.015(2) -0.014(2) 0.0135(16) C20 0.061(2) 0.0289(17) 0.251(5) 0.012(2) 0.008(3) 0.0166(17) O5 0.0312(11) 0.0473(10) 0.0366(11) -0.0066(9) -0.0024(9) 0.0012(8) O3 0.0245(9) 0.0284(9) 0.0965(14) -0.0127(9) -0.0090(9) -0.0024(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 O4 C8 1.418(2) . ? N2 C11 1.349(2) . ? N2 C7 1.453(3) . ? N2 C10 1.469(2) . ? O2 C11 1.216(2) . ? N3 C17 1.377(3) . ? N3 C14 1.381(2) . ? N3 C12 1.452(2) . ? C13 C12 1.517(3) . ? C13 C8 1.525(3) . ? C12 C11 1.520(3) . ? C8 C4 1.512(3) . ? C8 C7 1.547(3) . ? C7 N1 1.469(2) . ? C4 C5 1.375(3) . ? C4 C3 1.390(3) . ? C3 C2 1.384(3) . ? C3 N1 1.408(3) . ? N1 C9 1.355(3) . ? C14 O3 1.225(2) . ? C14 C15 1.450(3) . ? C9 O1 1.216(2) . ? C9 C10 1.505(3) . ? N4 C17 1.286(3) . ? N4 C16 1.387(3) . ? C2 C1 1.371(3) . ? C5 C6 1.386(3) . ? C15 C16 1.385(3) . ? C15 C18 1.401(3) . ? C10 C22 1.521(3) . ? C1 C6 1.369(3) . ? C16 C21 1.408(3) . ? C18 C19 1.373(4) . ? C21 C20 1.374(4) . ? C19 C20 1.386(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 C11 N2 C7 124.93(16) . . ? C11 N2 C10 122.90(18) . . ? C7 N2 C10 109.13(16) . . ? C17 N3 C14 121.71(18) . . ? C17 N3 C12 119.03(17) . . ? C14 N3 C12 119.27(17) . . ? C12 C13 C8 109.24(16) . . ? N3 C12 C13 113.19(16) . . ? N3 C12 C11 110.98(17) . . ? C13 C12 C11 108.60(16) . . ? O4 C8 C4 113.70(16) . . ? O4 C8 C13 111.03(16) . . ? C4 C8 C13 112.82(16) . . ? O4 C8 C7 106.28(15) . . ? C4 C8 C7 102.10(15) . . ? C13 C8 C7 110.31(16) . . ? N2 C7 N1 102.17(15) . . ? N2 C7 C8 117.76(16) . . ? N1 C7 C8 106.14(17) . . ? C5 C4 C3 119.7(2) . . ? C5 C4 C8 129.07(18) . . ? C3 C4 C8 111.05(19) . . ? C2 C3 C4 122.0(2) . . ? C2 C3 N1 128.16(19) . . ? C4 C3 N1 109.82(18) . . ? C9 N1 C3 128.68(18) . . ? C9 N1 C7 111.65(19) . . ? C3 N1 C7 109.72(16) . . ? O3 C14 N3 120.48(19) . . ? O3 C14 C15 125.88(19) . . ? N3 C14 C15 113.61(19) . . ? O2 C11 N2 122.95(18) . . ? O2 C11 C12 123.41(18) . . ? N2 C11 C12 113.57(18) . . ? O1 C9 N1 125.6(2) . . ? O1 C9 C10 125.6(2) . . ? N1 C9 C10 108.73(19) . . ? C17 N4 C16 115.6(2) . . ? C1 C2 C3 117.0(2) . . ? C4 C5 C6 118.4(2) . . ? C16 C15 C18 119.8(2) . . ? C16 C15 C14 120.0(2) . . ? C18 C15 C14 120.1(2) . . ? N2 C10 C9 101.67(18) . . ? N2 C10 C22 114.02(19) . . ? C9 C10 C22 113.6(2) . . ? C6 C1 C2 121.9(2) . . ? N4 C17 N3 126.0(2) . . ? C1 C6 C5 120.9(3) . . ? C15 C16 N4 122.8(2) . . ? C15 C16 C21 120.0(2) . . ? N4 C16 C21 117.2(2) . . ? C19 C18 C15 120.2(3) . . ? C20 C21 C16 118.6(3) . . ? C18 C19 C20 119.2(3) . . ? C21 C20 C19 122.0(3) . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.209 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 791764'