# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # 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_cz9-2 #TrackingRef '19774_web_deposit_cif_file_0_ChenguangWang_1366793638.Polymorph red.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H82 N4 O2' _chemical_formula_weight 939.34 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 8.958(6) _cell_length_b 10.065(5) _cell_length_c 15.398(8) _cell_angle_alpha 100.358(17) _cell_angle_beta 100.19(2) _cell_angle_gamma 90.81(2) _cell_volume 1342.6(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8278 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.17 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9724 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13284 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6080 _reflns_number_gt 3089 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 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^)+(0.0815P)^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 6080 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1309 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _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 C1 C 0.4103(2) 0.40999(18) 0.29514(12) 0.0491(4) Uani 1 1 d . . . C2 C 0.3567(2) 0.47381(19) 0.22289(14) 0.0601(5) Uani 1 1 d . . . H2 H 0.2750 0.5297 0.2241 0.072 Uiso 1 1 calc R . . C3 C 0.4279(3) 0.4515(2) 0.15044(15) 0.0703(6) Uani 1 1 d . . . H3 H 0.3944 0.4929 0.1016 0.084 Uiso 1 1 calc R . . C4 C 0.5496(3) 0.3679(2) 0.14885(14) 0.0704(6) Uani 1 1 d . . . H4 H 0.5956 0.3538 0.0985 0.084 Uiso 1 1 calc R . . C5 C 0.6041(2) 0.3053(2) 0.21982(12) 0.0588(5) Uani 1 1 d . . . H5 H 0.6860 0.2499 0.2173 0.071 Uiso 1 1 calc R . . C6 C 0.5355(2) 0.32548(17) 0.29577(12) 0.0470(4) Uani 1 1 d . . . C7 C 0.55557(19) 0.27817(16) 0.38140(11) 0.0429(4) Uani 1 1 d . . . C8 C 0.65963(19) 0.19434(16) 0.42616(11) 0.0423(4) Uani 1 1 d . . . C9 C 0.63394(19) 0.16593(16) 0.50944(11) 0.0440(4) Uani 1 1 d . . . C10 C 0.5130(2) 0.22413(19) 0.54834(12) 0.0501(4) Uani 1 1 d . . . H10 H 0.4974 0.2045 0.6029 0.060 Uiso 1 1 calc R . . C11 C 0.4187(2) 0.30866(18) 0.50714(12) 0.0518(5) Uani 1 1 d . . . H11 H 0.3412 0.3483 0.5342 0.062 Uiso 1 1 calc R . . C12 C 0.4397(2) 0.33475(17) 0.42482(12) 0.0466(4) Uani 1 1 d . . . C13 C 0.7919(2) 0.14302(17) 0.39097(12) 0.0469(4) Uani 1 1 d . . . C14 C 0.8981(2) 0.07078(16) 0.44891(11) 0.0434(4) Uani 1 1 d . . . C15 C 0.86319(19) 0.04118(17) 0.52916(11) 0.0441(4) Uani 1 1 d . . . C16 C 1.0318(2) 0.03027(17) 0.42087(12) 0.0476(4) Uani 1 1 d . . . H16 H 1.0522 0.0511 0.3676 0.057 Uiso 1 1 calc R . . C17 C 0.2284(2) 0.49570(18) 0.39713(13) 0.0538(5) Uani 1 1 d . . . H17A H 0.2259 0.5753 0.3696 0.065 Uiso 1 1 calc R . . H17B H 0.2469 0.5262 0.4617 0.065 Uiso 1 1 calc R . . C18 C 0.0750(2) 0.42093(19) 0.36879(14) 0.0567(5) Uani 1 1 d . . . H18A H 0.0662 0.3577 0.4085 0.068 Uiso 1 1 calc R . . H18B H 0.0673 0.3694 0.3084 0.068 Uiso 1 1 calc R . . C19 C -0.0552(2) 0.5165(2) 0.37099(14) 0.0597(5) Uani 1 1 d . . . H19A H -0.1478 0.4653 0.3710 0.072 Uiso 1 1 calc R . . H19B H -0.0341 0.5829 0.4262 0.072 Uiso 1 1 calc R . . C20 C -0.0795(2) 0.5892(2) 0.29169(16) 0.0701(6) Uani 1 1 d . . . H20A H 0.0129 0.6418 0.2933 0.084 Uiso 1 1 calc R . . H20B H -0.0954 0.5218 0.2369 0.084 Uiso 1 1 calc R . . C21 C -0.2106(2) 0.6824(2) 0.28707(15) 0.0676(6) Uani 1 1 d . . . H21A H -0.1936 0.7533 0.3400 0.081 Uiso 1 1 calc R . . H21B H -0.3036 0.6317 0.2869 0.081 Uiso 1 1 calc R . . C22 C -0.2291(3) 0.7464(3) 0.20307(17) 0.0833(7) Uani 1 1 d . . . H22A H -0.1373 0.8004 0.2057 0.100 Uiso 1 1 calc R . . H22B H -0.2380 0.6745 0.1510 0.100 Uiso 1 1 calc R . . C23 C -0.3607(3) 0.8330(3) 0.18954(18) 0.0881(8) Uani 1 1 d . . . H23A H -0.3533 0.9047 0.2416 0.106 Uiso 1 1 calc R . . H23B H -0.4533 0.7791 0.1851 0.106 Uiso 1 1 calc R . . C24 C -0.3707(4) 0.8954(3) 0.10617(19) 0.1146(11) Uani 1 1 d . . . H24A H -0.2797 0.9494 0.1102 0.172 Uiso 1 1 calc R . . H24B H -0.4566 0.9514 0.1015 0.172 Uiso 1 1 calc R . . H24C H -0.3823 0.8250 0.0540 0.172 Uiso 1 1 calc R . . C25 C 0.6840(2) 0.02919(17) 0.63122(11) 0.0485(4) Uani 1 1 d . . . H25A H 0.7190 -0.0618 0.6298 0.058 Uiso 1 1 calc R . . H25B H 0.5740 0.0235 0.6226 0.058 Uiso 1 1 calc R . . C26 C 0.7452(2) 0.11306(18) 0.72276(12) 0.0559(5) Uani 1 1 d . . . H26A H 0.6890 0.1946 0.7313 0.067 Uiso 1 1 calc R . . H26B H 0.8509 0.1396 0.7261 0.067 Uiso 1 1 calc R . . C27 C 0.7320(3) 0.0337(2) 0.79757(13) 0.0625(5) Uani 1 1 d . . . H27A H 0.7360 0.0970 0.8535 0.075 Uiso 1 1 calc R . . H27B H 0.6339 -0.0151 0.7836 0.075 Uiso 1 1 calc R . . C28 C 0.8558(3) -0.0662(2) 0.81044(13) 0.0683(6) Uani 1 1 d . . . H28A H 0.8423 -0.1374 0.7577 0.082 Uiso 1 1 calc R . . H28B H 0.9536 -0.0201 0.8155 0.082 Uiso 1 1 calc R . . C29 C 0.8568(3) -0.1292(2) 0.89217(14) 0.0708(6) Uani 1 1 d . . . H29A H 0.7638 -0.1843 0.8838 0.085 Uiso 1 1 calc R . . H29B H 0.8576 -0.0578 0.9438 0.085 Uiso 1 1 calc R . . C30 C 0.9916(3) -0.2164(2) 0.91192(14) 0.0773(7) Uani 1 1 d . . . H30A H 0.9878 -0.2908 0.8617 0.093 Uiso 1 1 calc R . . H30B H 1.0847 -0.1627 0.9173 0.093 Uiso 1 1 calc R . . C31 C 0.9954(3) -0.2721(2) 0.99573(16) 0.0829(7) Uani 1 1 d . . . H31A H 0.9042 -0.3287 0.9895 0.100 Uiso 1 1 calc R . . H31B H 0.9953 -0.1979 1.0456 0.100 Uiso 1 1 calc R . . C32 C 1.1326(3) -0.3543(3) 1.01703(19) 0.0990(9) Uani 1 1 d . . . H32A H 1.1306 -0.4307 0.9694 0.148 Uiso 1 1 calc R . . H32B H 1.1309 -0.3852 1.0723 0.148 Uiso 1 1 calc R . . H32C H 1.2234 -0.2991 1.0229 0.148 Uiso 1 1 calc R . . N1 N 0.35414(17) 0.41566(15) 0.37324(10) 0.0516(4) Uani 1 1 d . . . N2 N 0.72892(17) 0.08231(14) 0.55593(9) 0.0474(4) Uani 1 1 d . . . O1 O 0.82028(16) 0.15954(16) 0.31817(9) 0.0714(4) Uani 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 C1 0.0402(10) 0.0501(10) 0.0567(10) 0.0123(9) 0.0051(8) 0.0072(8) C2 0.0493(12) 0.0594(11) 0.0735(13) 0.0233(10) 0.0038(10) 0.0164(10) C3 0.0619(15) 0.0833(15) 0.0717(13) 0.0364(12) 0.0051(11) 0.0176(12) C4 0.0626(14) 0.0928(15) 0.0650(12) 0.0343(12) 0.0155(10) 0.0189(12) C5 0.0494(12) 0.0706(12) 0.0618(11) 0.0237(10) 0.0116(9) 0.0177(10) C6 0.0366(10) 0.0476(9) 0.0569(10) 0.0139(8) 0.0039(8) 0.0072(8) C7 0.0326(9) 0.0425(9) 0.0529(9) 0.0078(8) 0.0065(7) 0.0048(7) C8 0.0337(9) 0.0418(9) 0.0511(9) 0.0078(8) 0.0072(7) 0.0062(7) C9 0.0331(9) 0.0459(9) 0.0538(9) 0.0103(8) 0.0086(7) 0.0073(8) C10 0.0378(10) 0.0611(11) 0.0540(10) 0.0119(9) 0.0137(8) 0.0123(9) C11 0.0365(10) 0.0598(11) 0.0597(10) 0.0069(9) 0.0140(8) 0.0156(9) C12 0.0358(10) 0.0456(9) 0.0581(10) 0.0106(8) 0.0061(8) 0.0103(8) C13 0.0377(10) 0.0507(10) 0.0555(10) 0.0136(8) 0.0121(8) 0.0108(8) C14 0.0361(9) 0.0463(9) 0.0508(9) 0.0131(8) 0.0114(7) 0.0104(8) C15 0.0344(10) 0.0472(9) 0.0539(9) 0.0117(8) 0.0136(7) 0.0093(8) C16 0.0432(11) 0.0532(10) 0.0516(9) 0.0163(8) 0.0150(8) 0.0135(8) C17 0.0431(11) 0.0506(10) 0.0654(11) 0.0078(9) 0.0056(9) 0.0149(9) C18 0.0439(12) 0.0544(11) 0.0701(12) 0.0111(10) 0.0059(9) 0.0083(9) C19 0.0403(11) 0.0663(12) 0.0741(12) 0.0153(11) 0.0113(9) 0.0121(9) C20 0.0461(13) 0.0875(15) 0.0859(14) 0.0323(13) 0.0188(11) 0.0212(11) C21 0.0499(13) 0.0743(13) 0.0833(14) 0.0251(12) 0.0130(10) 0.0166(11) C22 0.0565(15) 0.0992(17) 0.1073(18) 0.0437(16) 0.0235(13) 0.0256(13) C23 0.0720(17) 0.0987(18) 0.1033(18) 0.0387(16) 0.0199(14) 0.0275(15) C24 0.103(2) 0.150(3) 0.118(2) 0.076(2) 0.0371(19) 0.050(2) C25 0.0399(10) 0.0523(10) 0.0571(10) 0.0140(9) 0.0146(8) 0.0083(8) C26 0.0534(12) 0.0524(10) 0.0623(11) 0.0091(9) 0.0124(9) 0.0092(9) C27 0.0684(14) 0.0688(12) 0.0550(11) 0.0150(10) 0.0193(10) 0.0193(11) C28 0.0797(16) 0.0706(13) 0.0605(11) 0.0202(11) 0.0187(11) 0.0242(12) C29 0.0838(17) 0.0675(13) 0.0633(12) 0.0169(11) 0.0133(11) 0.0114(12) C30 0.098(2) 0.0702(13) 0.0658(12) 0.0179(12) 0.0137(12) 0.0224(13) C31 0.0863(19) 0.0803(15) 0.0851(15) 0.0299(14) 0.0078(13) 0.0145(14) C32 0.101(2) 0.0957(18) 0.1011(18) 0.0327(16) 0.0047(16) 0.0276(17) N1 0.0393(9) 0.0530(9) 0.0631(9) 0.0129(8) 0.0074(7) 0.0156(7) N2 0.0373(8) 0.0557(9) 0.0551(8) 0.0186(7) 0.0148(6) 0.0142(7) O1 0.0597(10) 0.1071(11) 0.0662(8) 0.0448(8) 0.0299(7) 0.0408(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 C1 N1 1.376(2) . ? C1 C2 1.399(3) . ? C1 C6 1.416(3) . ? C2 C3 1.367(3) . ? C2 H2 0.9300 . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 C6 1.400(3) . ? C5 H5 0.9300 . ? C6 C7 1.463(2) . ? C7 C12 1.405(3) . ? C7 C8 1.435(2) . ? C8 C9 1.419(2) . ? C8 C13 1.452(3) . ? C9 N2 1.402(2) . ? C9 C10 1.413(3) . ? C10 C11 1.366(2) . ? C10 H10 0.9300 . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 N1 1.384(2) . ? C13 O1 1.231(2) . ? C13 C14 1.477(2) . ? C14 C16 1.386(2) . ? C14 C15 1.407(2) . ? C15 N2 1.384(2) . ? C15 C16 1.398(2) 2_756 ? C16 C15 1.398(2) 2_756 ? C16 H16 0.9300 . ? C17 N1 1.455(2) . ? C17 C18 1.512(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.523(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.519(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.514(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.530(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.483(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.517(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N2 1.474(2) . ? C25 C26 1.512(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.535(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.519(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.506(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.523(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.492(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.511(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 127.76(18) . . ? N1 C1 C6 109.85(15) . . ? C2 C1 C6 122.38(18) . . ? C3 C2 C1 118.01(19) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 120.79(19) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 121.7(2) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C4 C5 C6 119.66(19) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 117.43(16) . . ? C5 C6 C7 136.59(17) . . ? C1 C6 C7 105.96(16) . . ? C12 C7 C8 118.42(16) . . ? C12 C7 C6 105.75(14) . . ? C8 C7 C6 135.83(17) . . ? C9 C8 C7 118.07(16) . . ? C9 C8 C13 119.56(14) . . ? C7 C8 C13 122.32(16) . . ? N2 C9 C10 118.43(15) . . ? N2 C9 C8 121.20(16) . . ? C10 C9 C8 120.36(14) . . ? C11 C10 C9 121.09(17) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 119.32(17) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 N1 127.08(17) . . ? C11 C12 C7 122.62(15) . . ? N1 C12 C7 110.30(16) . . ? O1 C13 C8 123.75(15) . . ? O1 C13 C14 119.82(17) . . ? C8 C13 C14 116.41(15) . . ? C16 C14 C15 120.89(14) . . ? C16 C14 C13 117.98(15) . . ? C15 C14 C13 121.11(16) . . ? N2 C15 C16 122.44(15) . 2_756 ? N2 C15 C14 120.02(14) . . ? C16 C15 C14 117.55(16) 2_756 . ? C14 C16 C15 121.56(16) . 2_756 ? C14 C16 H16 119.2 . . ? C15 C16 H16 119.2 2_756 . ? N1 C17 C18 114.15(16) . . ? N1 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? N1 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 112.17(16) . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18B 109.2 . . ? C19 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 112.56(18) . . ? C20 C19 H19A 109.1 . . ? C18 C19 H19A 109.1 . . ? C20 C19 H19B 109.1 . . ? C18 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C19 115.87(18) . . ? C21 C20 H20A 108.3 . . ? C19 C20 H20A 108.3 . . ? C21 C20 H20B 108.3 . . ? C19 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? C20 C21 C22 111.76(19) . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C21 115.8(2) . . ? C23 C22 H22A 108.3 . . ? C21 C22 H22A 108.3 . . ? C23 C22 H22B 108.3 . . ? C21 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24 113.2(2) . . ? C22 C23 H23A 108.9 . . ? C24 C23 H23A 108.9 . . ? C22 C23 H23B 108.9 . . ? C24 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 C26 114.34(15) . . ? N2 C25 H25A 108.7 . . ? C26 C25 H25A 108.7 . . ? N2 C25 H25B 108.7 . . ? C26 C25 H25B 108.7 . . ? H25A C25 H25B 107.6 . . ? C25 C26 C27 111.15(16) . . ? C25 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? C25 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C28 C27 C26 113.40(18) . . ? C28 C27 H27A 108.9 . . ? C26 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C26 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C29 C28 C27 113.42(19) . . ? C29 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C28 C29 C30 113.8(2) . . ? C28 C29 H29A 108.8 . . ? C30 C29 H29A 108.8 . . ? C28 C29 H29B 108.8 . . ? C30 C29 H29B 108.8 . . ? H29A C29 H29B 107.7 . . ? C31 C30 C29 113.1(2) . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30B 109.0 . . ? C29 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C30 C31 C32 113.0(2) . . ? C30 C31 H31A 109.0 . . ? C32 C31 H31A 109.0 . . ? C30 C31 H31B 109.0 . . ? C32 C31 H31B 109.0 . . ? H31A C31 H31B 107.8 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C1 N1 C12 108.11(15) . . ? C1 N1 C17 125.26(15) . . ? C12 N1 C17 126.62(16) . . ? C15 N2 C9 120.90(14) . . ? C15 N2 C25 118.15(13) . . ? C9 N2 C25 120.85(15) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.266 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 935852' ####################################################################### # # 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_cz9-6 #TrackingRef 'web_deposit_cif_file_1_ChenguangWang_1366793638.Polymorph black.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H82 N4 O2' _chemical_formula_weight 939.34 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 9.040(8) _cell_length_b 10.523(7) _cell_length_c 14.736(10) _cell_angle_alpha 75.89(2) _cell_angle_beta 89.97(3) _cell_angle_gamma 89.11(3) _cell_volume 1359.5(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5674 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 25 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9542 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10568 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_sigmaI/netI 0.1426 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4701 _reflns_number_gt 1454 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 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^)+(0.1125P)^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 4701 _refine_ls_number_parameters 316 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2425 _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.2817 _refine_ls_wR_factor_gt 0.2052 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.005 _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 1.1416(7) 0.2932(5) 0.1536(3) 0.0691(15) Uani 1 1 d . . . C2 C 1.2455(8) 0.1911(5) 0.1653(4) 0.0851(18) Uani 1 1 d . . . H2 H 1.2185 0.1045 0.1890 0.102 Uiso 1 1 calc R . . C3 C 1.3914(8) 0.2237(6) 0.1401(4) 0.0914(19) Uani 1 1 d . . . H3 H 1.4630 0.1575 0.1476 0.110 Uiso 1 1 calc R . . C4 C 1.4320(7) 0.3534(6) 0.1040(4) 0.0859(18) Uani 1 1 d . . . H4 H 1.5302 0.3726 0.0880 0.103 Uiso 1 1 calc R . . C5 C 1.3293(7) 0.4524(5) 0.0917(4) 0.0762(16) Uani 1 1 d . . . H5 H 1.3574 0.5386 0.0672 0.091 Uiso 1 1 calc R . . C6 C 1.1818(7) 0.4244(4) 0.1161(3) 0.0645(14) Uani 1 1 d . . . C7 C 1.0440(6) 0.4970(4) 0.1143(3) 0.0621(14) Uani 1 1 d . . . C8 C 1.0009(6) 0.6338(4) 0.0843(3) 0.0614(14) Uani 1 1 d . . . C9 C 0.8507(7) 0.6662(4) 0.0983(3) 0.0633(14) Uani 1 1 d . . . C10 C 0.7467(6) 0.5668(5) 0.1410(3) 0.0731(15) Uani 1 1 d . . . H10 H 0.6497 0.5900 0.1518 0.088 Uiso 1 1 calc R . . C11 C 0.7911(7) 0.4395(5) 0.1654(3) 0.0768(17) Uani 1 1 d . . . H11 H 0.7235 0.3750 0.1912 0.092 Uiso 1 1 calc R . . C12 C 0.9354(7) 0.4048(5) 0.1521(3) 0.0638(14) Uani 1 1 d . . . C13 C 1.1038(7) 0.7361(4) 0.0395(3) 0.0691(15) Uani 1 1 d . . . C14 C 1.0478(7) 0.8711(4) 0.0202(3) 0.0624(14) Uani 1 1 d . . . C15 C 0.8992(7) 0.8975(4) 0.0373(3) 0.0637(14) Uani 1 1 d . . . C16 C 0.8523(6) 1.0270(4) 0.0170(3) 0.0652(14) Uani 1 1 d . . . H16 H 0.7544 1.0475 0.0278 0.078 Uiso 1 1 calc R . . C17 C 0.9103(7) 0.1619(5) 0.2141(3) 0.0795(17) Uani 1 1 d . . . H17A H 0.9583 0.0887 0.1961 0.095 Uiso 1 1 calc R . . H17B H 0.8116 0.1721 0.1872 0.095 Uiso 1 1 calc R . . C18 C 0.8974(7) 0.1297(5) 0.3202(4) 0.0913(19) Uani 1 1 d . . . H18A H 0.8592 0.2058 0.3392 0.110 Uiso 1 1 calc R . . H18B H 0.9948 0.1087 0.3479 0.110 Uiso 1 1 calc R . . C19 C 0.7933(8) 0.0118(6) 0.3571(4) 0.106(2) Uani 1 1 d . . . H19A H 0.6954 0.0353 0.3308 0.128 Uiso 1 1 calc R . . H19B H 0.8291 -0.0620 0.3343 0.128 Uiso 1 1 calc R . . C20 C 0.7801(10) -0.0310(8) 0.4617(5) 0.157(4) Uani 1 1 d . . . H20A H 0.7407 0.0411 0.4852 0.188 Uiso 1 1 calc R . . H20B H 0.8775 -0.0538 0.4890 0.188 Uiso 1 1 calc R . . C21 C 0.6722(12) -0.1568(9) 0.4936(6) 0.189(5) Uani 1 1 d D . . H21A H 0.5731 -0.1303 0.4705 0.227 Uiso 1 1 calc R . . H21B H 0.7062 -0.2244 0.4636 0.227 Uiso 1 1 calc R . . C22 C 0.6646(15) -0.2102(13) 0.5887(8) 0.241(6) Uani 1 1 d D . . H22A H 0.6439 -0.1389 0.6182 0.289 Uiso 1 1 calc R . . H22B H 0.7624 -0.2443 0.6094 0.289 Uiso 1 1 calc R . . C23 C 0.554(2) -0.3187(18) 0.6282(9) 0.293(9) Uani 1 1 d D . . H23A H 0.6058 -0.3790 0.6791 0.352 Uiso 1 1 calc R . . H23B H 0.4766 -0.2775 0.6569 0.352 Uiso 1 1 calc R . . C24 C 0.477(3) -0.4027(19) 0.5750(13) 0.423(16) Uani 1 1 d D . . H24A H 0.4137 -0.4627 0.6166 0.634 Uiso 1 1 calc R . . H24B H 0.5487 -0.4512 0.5484 0.634 Uiso 1 1 calc R . . H24C H 0.4183 -0.3482 0.5258 0.634 Uiso 1 1 calc R . . C25 C 0.6418(6) 0.8223(5) 0.0842(4) 0.0738(15) Uani 1 1 d . . . H25A H 0.5858 0.7517 0.0700 0.089 Uiso 1 1 calc R . . H25B H 0.6151 0.9019 0.0378 0.089 Uiso 1 1 calc R . . C26 C 0.5928(7) 0.8386(5) 0.1793(4) 0.0891(18) Uani 1 1 d . . . H26A H 0.6268 0.9224 0.1868 0.107 Uiso 1 1 calc R . . H26B H 0.6405 0.7707 0.2273 0.107 Uiso 1 1 calc R . . C27 C 0.4248(8) 0.8319(7) 0.1953(5) 0.113(2) Uani 1 1 d . . . H27A H 0.3797 0.9048 0.1500 0.135 Uiso 1 1 calc R . . H27B H 0.3910 0.7523 0.1802 0.135 Uiso 1 1 calc R . . C28 C 0.3673(10) 0.8338(9) 0.2845(6) 0.153(3) Uani 1 1 d . . . H28A H 0.3889 0.9185 0.2961 0.183 Uiso 1 1 calc R . . H28B H 0.4212 0.7683 0.3310 0.183 Uiso 1 1 calc R . . C29 C 0.2005(10) 0.8095(9) 0.3015(6) 0.150(3) Uani 1 1 d . . . H29A H 0.1701 0.8509 0.3507 0.180 Uiso 1 1 calc R . . H29B H 0.1482 0.8546 0.2450 0.180 Uiso 1 1 calc R . . C30 C 0.1492(10) 0.6729(9) 0.3272(6) 0.137(3) Uani 1 1 d . . . H30A H 0.2060 0.6255 0.3809 0.165 Uiso 1 1 calc R . . H30B H 0.1713 0.6331 0.2758 0.165 Uiso 1 1 calc R . . C31 C -0.0134(10) 0.6545(9) 0.3502(6) 0.147(3) Uani 1 1 d . . . H31A H -0.0719 0.7016 0.2971 0.176 Uiso 1 1 calc R . . H31B H -0.0367 0.6912 0.4029 0.176 Uiso 1 1 calc R . . C32 C -0.0545(13) 0.5093(10) 0.3741(6) 0.198(5) Uani 1 1 d . . . H32A H -0.1580 0.5011 0.3884 0.297 Uiso 1 1 calc R . . H32B H 0.0022 0.4628 0.4273 0.297 Uiso 1 1 calc R . . H32C H -0.0333 0.4732 0.3216 0.297 Uiso 1 1 calc R . . N1 N 0.9938(5) 0.2815(4) 0.1743(3) 0.0717(13) Uani 1 1 d . . . N2 N 0.8000(5) 0.7946(4) 0.0730(3) 0.0672(12) Uani 1 1 d . . . O1 O 1.2334(5) 0.7159(3) 0.0174(3) 0.0937(13) Uani 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 C1 0.074(5) 0.069(3) 0.062(3) -0.012(3) 0.003(3) -0.005(3) C2 0.091(6) 0.070(3) 0.090(4) -0.012(3) -0.001(4) 0.001(4) C3 0.088(6) 0.086(4) 0.093(4) -0.007(3) -0.012(4) 0.009(4) C4 0.072(5) 0.085(4) 0.095(4) -0.012(3) -0.007(3) -0.007(3) C5 0.076(5) 0.067(3) 0.087(4) -0.020(3) -0.005(3) -0.008(3) C6 0.072(5) 0.059(3) 0.061(3) -0.012(2) 0.004(3) -0.014(3) C7 0.073(4) 0.062(3) 0.052(3) -0.013(2) 0.000(3) -0.011(3) C8 0.067(4) 0.060(3) 0.056(3) -0.011(2) -0.006(3) -0.013(3) C9 0.072(5) 0.059(3) 0.059(3) -0.012(2) -0.004(3) -0.013(3) C10 0.062(4) 0.069(3) 0.085(4) -0.012(3) 0.000(3) -0.013(3) C11 0.085(5) 0.062(3) 0.076(3) -0.002(3) -0.004(3) -0.022(3) C12 0.062(4) 0.064(3) 0.063(3) -0.010(2) -0.001(3) -0.006(3) C13 0.073(5) 0.056(3) 0.077(3) -0.014(3) 0.006(3) -0.010(3) C14 0.066(4) 0.058(3) 0.062(3) -0.014(2) -0.003(3) -0.005(3) C15 0.071(4) 0.058(3) 0.062(3) -0.014(2) -0.002(3) -0.007(3) C16 0.062(4) 0.060(3) 0.074(3) -0.014(2) 0.000(3) -0.012(3) C17 0.089(5) 0.062(3) 0.081(4) -0.005(3) -0.009(3) -0.010(3) C18 0.100(5) 0.078(3) 0.088(4) -0.004(3) -0.001(3) -0.021(3) C19 0.118(6) 0.087(4) 0.103(4) 0.002(3) 0.007(4) -0.029(4) C20 0.135(8) 0.188(8) 0.113(6) 0.033(5) 0.005(5) -0.060(6) C21 0.197(11) 0.190(9) 0.142(7) 0.037(7) 0.035(7) -0.040(8) C22 0.274(16) 0.263(14) 0.162(9) 0.000(9) 0.021(9) -0.115(12) C23 0.38(2) 0.30(2) 0.167(10) 0.002(12) 0.055(12) -0.148(17) C24 0.43(4) 0.29(2) 0.54(4) -0.08(2) 0.13(3) -0.05(2) C25 0.060(4) 0.067(3) 0.090(4) -0.010(3) 0.001(3) -0.010(3) C26 0.084(5) 0.087(4) 0.091(4) -0.013(3) 0.015(3) 0.002(3) C27 0.080(6) 0.140(6) 0.110(5) -0.017(4) 0.018(4) 0.017(4) C28 0.099(8) 0.197(8) 0.143(7) -0.004(6) 0.014(6) 0.008(6) C29 0.097(8) 0.165(8) 0.166(7) 0.004(6) 0.023(6) 0.003(6) C30 0.106(8) 0.161(7) 0.142(6) -0.033(6) -0.005(5) 0.001(6) C31 0.108(8) 0.194(9) 0.134(6) -0.027(6) 0.001(5) -0.032(6) C32 0.264(14) 0.215(10) 0.123(6) -0.047(7) -0.006(7) -0.117(10) N1 0.072(4) 0.055(2) 0.081(3) -0.004(2) 0.004(2) -0.010(2) N2 0.061(4) 0.063(3) 0.075(3) -0.009(2) 0.002(2) -0.011(2) O1 0.075(3) 0.067(2) 0.135(3) -0.016(2) 0.019(3) -0.005(2) _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 N1 1.372(6) . ? C1 C2 1.394(7) . ? C1 C6 1.410(6) . ? C2 C3 1.396(8) . ? C2 H2 0.9300 . ? C3 C4 1.394(7) . ? C3 H3 0.9300 . ? C4 C5 1.363(7) . ? C4 H4 0.9300 . ? C5 C6 1.399(7) . ? C5 H5 0.9300 . ? C6 C7 1.448(7) . ? C7 C12 1.408(7) . ? C7 C8 1.447(6) . ? C8 C9 1.422(7) . ? C8 C13 1.465(6) . ? C9 N2 1.382(6) . ? C9 C10 1.444(6) . ? C10 C11 1.354(7) . ? C10 H10 0.9300 . ? C11 C12 1.376(7) . ? C11 H11 0.9300 . ? C12 N1 1.357(6) . ? C13 O1 1.245(6) . ? C13 C14 1.461(7) . ? C14 C15 1.403(7) . ? C14 C16 1.417(6) 2_775 ? C15 C16 1.382(6) . ? C15 N2 1.416(6) . ? C16 C14 1.417(6) 2_775 ? C16 H16 0.9300 . ? C17 N1 1.472(6) . ? C17 C18 1.523(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.558(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.503(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.631(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.380(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.531(12) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.4993(13) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N2 1.472(6) . ? C25 C26 1.518(7) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.537(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.419(9) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.543(10) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.476(10) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.513(10) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.534(11) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 126.4(5) . . ? N1 C1 C6 112.3(5) . . ? C2 C1 C6 121.3(6) . . ? C1 C2 C3 117.6(5) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C4 C3 C2 121.3(6) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 120.6(6) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.0(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 119.1(5) . . ? C5 C6 C7 137.1(4) . . ? C1 C6 C7 103.7(5) . . ? C12 C7 C8 118.6(5) . . ? C12 C7 C6 106.7(4) . . ? C8 C7 C6 134.7(5) . . ? C9 C8 C7 117.0(4) . . ? C9 C8 C13 120.3(4) . . ? C7 C8 C13 122.7(5) . . ? N2 C9 C8 121.0(4) . . ? N2 C9 C10 117.7(5) . . ? C8 C9 C10 121.3(5) . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.5(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? N1 C12 C11 126.2(5) . . ? N1 C12 C7 110.9(5) . . ? C11 C12 C7 123.0(5) . . ? O1 C13 C14 118.7(5) . . ? O1 C13 C8 124.8(5) . . ? C14 C13 C8 116.5(5) . . ? C15 C14 C16 121.7(4) . 2_775 ? C15 C14 C13 120.4(5) . . ? C16 C14 C13 117.9(5) 2_775 . ? C16 C15 C14 117.9(4) . . ? C16 C15 N2 121.1(5) . . ? C14 C15 N2 121.0(4) . . ? C15 C16 C14 120.5(5) . 2_775 ? C15 C16 H16 119.8 . . ? C14 C16 H16 119.8 2_775 . ? N1 C17 C18 113.9(4) . . ? N1 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N1 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 C19 111.5(5) . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C20 C19 C18 115.0(6) . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? C18 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 C21 111.4(7) . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C20 115.3(9) . . ? C22 C21 H21A 108.5 . . ? C20 C21 H21A 108.5 . . ? C22 C21 H21B 108.5 . . ? C20 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 C23 120.3(10) . . ? C21 C22 H22A 107.3 . . ? C23 C22 H22A 107.3 . . ? C21 C22 H22B 107.3 . . ? C23 C22 H22B 107.3 . . ? H22A C22 H22B 106.9 . . ? C24 C23 C22 126.7(14) . . ? C24 C23 H23A 105.6 . . ? C22 C23 H23A 105.6 . . ? C24 C23 H23B 105.6 . . ? C22 C23 H23B 105.6 . . ? H23A C23 H23B 106.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 C26 117.0(5) . . ? N2 C25 H25A 108.0 . . ? C26 C25 H25A 108.0 . . ? N2 C25 H25B 108.0 . . ? C26 C25 H25B 108.0 . . ? H25A C25 H25B 107.3 . . ? C25 C26 C27 114.6(6) . . ? C25 C26 H26A 108.6 . . ? C27 C26 H26A 108.6 . . ? C25 C26 H26B 108.6 . . ? C27 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? C28 C27 C26 119.5(7) . . ? C28 C27 H27A 107.4 . . ? C26 C27 H27A 107.4 . . ? C28 C27 H27B 107.4 . . ? C26 C27 H27B 107.4 . . ? H27A C27 H27B 107.0 . . ? C27 C28 C29 118.0(8) . . ? C27 C28 H28A 107.8 . . ? C29 C28 H28A 107.8 . . ? C27 C28 H28B 107.8 . . ? C29 C28 H28B 107.8 . . ? H28A C28 H28B 107.2 . . ? C30 C29 C28 118.5(8) . . ? C30 C29 H29A 107.7 . . ? C28 C29 H29A 107.7 . . ? C30 C29 H29B 107.7 . . ? C28 C29 H29B 107.7 . . ? H29A C29 H29B 107.1 . . ? C29 C30 C31 116.2(7) . . ? C29 C30 H30A 108.2 . . ? C31 C30 H30A 108.2 . . ? C29 C30 H30B 108.2 . . ? C31 C30 H30B 108.2 . . ? H30A C30 H30B 107.4 . . ? C30 C31 C32 111.6(8) . . ? C30 C31 H31A 109.3 . . ? C32 C31 H31A 109.3 . . ? C30 C31 H31B 109.3 . . ? C32 C31 H31B 109.3 . . ? H31A C31 H31B 108.0 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C12 N1 C1 106.5(4) . . ? C12 N1 C17 125.0(5) . . ? C1 N1 C17 128.5(4) . . ? C9 N2 C15 120.3(5) . . ? C9 N2 C25 118.9(4) . . ? C15 N2 C25 120.8(4) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.310 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 935853'