# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_compound(R,R)-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H38 N4 O2' _chemical_formula_weight 606.74 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.5426(4) _cell_length_b 10.6326(6) _cell_length_c 12.1705(7) _cell_angle_alpha 77.018(2) _cell_angle_beta 74.588(2) _cell_angle_gamma 87.095(2) _cell_volume 795.30(8) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3080 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 29.99 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9906 _exptl_absorpt_correction_T_max 0.9937 _exptl_absorpt_process_details sadabs _exptl_special_details ; Absolute configurations have been fixed based on known configurations The starting porphyrin being chiral and enantiopure the space group is thus necessarly noncentrosymmetric ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8892 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.5 _reflns_number_total 6930 _reflns_number_gt 5725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The absolute configurations of C27 and C37 are known. ; _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^)+(0.0748P)^2^+0.1216P] 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(14) _refine_ls_number_reflns 6930 _refine_ls_number_parameters 419 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.8826(3) 0.19433(19) 0.41600(16) 0.0231(4) Uani 1 1 d . . . H1A H 0.7880 0.2560 0.4123 0.028 Uiso 1 1 calc R . . N2 N 0.5623(3) 0.26795(19) 0.29805(17) 0.0242(5) Uani 1 1 d . . . N3 N 0.4423(3) 0.49040(19) 0.41572(17) 0.0232(4) Uani 1 1 d . . . H3A H 0.5342 0.4274 0.4211 0.028 Uiso 1 1 calc R . . N4 N 0.7639(3) 0.41667(19) 0.53249(16) 0.0232(5) Uani 1 1 d . . . C1 C 1.0241(4) 0.1790(2) 0.4826(2) 0.0240(5) Uani 1 1 d . . . C2 C 1.1495(4) 0.0658(2) 0.4640(2) 0.0277(6) Uani 1 1 d . . . H2 H 1.2596 0.0324 0.4996 0.033 Uiso 1 1 calc R . . C3 C 1.0817(4) 0.0170(2) 0.3876(2) 0.0273(6) Uani 1 1 d . . . H3 H 1.1355 -0.0575 0.3591 0.033 Uiso 1 1 calc R . . C4 C 0.9128(4) 0.0973(2) 0.35585(19) 0.0238(5) Uani 1 1 d . . . C5 C 0.7959(4) 0.0808(2) 0.2796(2) 0.0238(5) Uani 1 1 d . . . C6 C 0.6340(4) 0.1630(2) 0.2514(2) 0.0257(6) Uani 1 1 d . . . C7 C 0.5231(4) 0.1530(3) 0.1671(2) 0.0279(6) Uani 1 1 d . . . H7 H 0.5442 0.0896 0.1213 0.034 Uiso 1 1 calc R . . C8 C 0.3816(4) 0.2512(2) 0.1648(2) 0.0291(6) Uani 1 1 d . . . H8 H 0.2848 0.2689 0.1174 0.035 Uiso 1 1 calc R . . C9 C 0.4060(4) 0.3232(2) 0.2473(2) 0.0247(5) Uani 1 1 d . . . C10 C 0.2889(4) 0.4316(2) 0.2703(2) 0.0253(5) Uani 1 1 d . . . H10 H 0.1841 0.4564 0.2287 0.030 Uiso 1 1 calc R . . C11 C 0.3052(4) 0.5082(2) 0.3460(2) 0.0240(5) Uani 1 1 d . . . C12 C 0.1799(4) 0.6207(2) 0.3640(2) 0.0270(6) Uani 1 1 d . . . H12 H 0.0718 0.6547 0.3271 0.032 Uiso 1 1 calc R . . C13 C 0.2450(4) 0.6691(2) 0.4435(2) 0.0256(5) Uani 1 1 d . . . H13 H 0.1909 0.7431 0.4727 0.031 Uiso 1 1 calc R . . C14 C 0.4120(4) 0.5867(2) 0.47527(19) 0.0217(5) Uani 1 1 d . . . C15 C 0.5263(4) 0.6040(2) 0.5532(2) 0.0228(5) Uani 1 1 d . . . C16 C 0.6888(4) 0.5203(2) 0.58074(19) 0.0217(5) Uani 1 1 d . . . C17 C 0.8008(4) 0.5298(3) 0.6667(2) 0.0280(6) Uani 1 1 d . . . H17 H 0.7781 0.5917 0.7140 0.034 Uiso 1 1 calc R . . C18 C 0.9439(4) 0.4334(3) 0.6665(2) 0.0294(6) Uani 1 1 d . . . H18 H 1.0412 0.4156 0.7136 0.035 Uiso 1 1 calc R . . C19 C 0.9227(4) 0.3627(2) 0.5825(2) 0.0254(5) Uani 1 1 d . . . C20 C 1.0420(4) 0.2557(2) 0.5587(2) 0.0264(5) Uani 1 1 d . . . H20 H 1.1487 0.2319 0.5991 0.032 Uiso 1 1 calc R . . C21 C 0.8400(4) -0.0337(2) 0.22396(19) 0.0248(5) Uani 1 1 d . . . C22 C 1.0233(4) -0.0436(3) 0.1364(2) 0.0289(6) Uani 1 1 d . . . H22 H 1.1339 0.0183 0.1177 0.035 Uiso 1 1 calc R . . C23 C 1.0477(4) -0.1413(3) 0.0761(2) 0.0303(6) Uani 1 1 d . . . H23 H 1.1739 -0.1455 0.0165 0.036 Uiso 1 1 calc R . . C24 C 0.8887(4) -0.2337(3) 0.1021(2) 0.0295(6) Uani 1 1 d . . . C25 C 0.7101(5) -0.2297(3) 0.1938(2) 0.0364(7) Uani 1 1 d . . . H25 H 0.6041 -0.2951 0.2161 0.044 Uiso 1 1 calc R . . C26 C 0.6870(4) -0.1299(3) 0.2529(2) 0.0317(6) Uani 1 1 d . . . H26 H 0.5634 -0.1275 0.3145 0.038 Uiso 1 1 calc R . . O1 O 0.9203(3) -0.32157(18) 0.03346(16) 0.0394(5) Uani 1 1 d . . . C27 C 0.7440(4) -0.4036(2) 0.0401(2) 0.0340(6) Uani 1 1 d . . . H27 H 0.6783 -0.4457 0.1236 0.041 Uiso 1 1 calc R . . C28 C 0.8364(5) -0.5053(3) -0.0269(2) 0.0394(6) Uani 1 1 d . . . H28A H 0.9086 -0.4627 -0.1083 0.047 Uiso 1 1 calc R . . H28B H 0.7199 -0.5596 -0.0295 0.047 Uiso 1 1 calc R . . C29 C 0.9930(5) -0.5908(3) 0.0264(3) 0.0471(7) Uani 1 1 d . . . H29A H 1.1217 -0.5410 0.0152 0.071 Uiso 1 1 calc R . . H29B H 1.0291 -0.6640 -0.0116 0.071 Uiso 1 1 calc R . . H29C H 0.9295 -0.6228 0.1101 0.071 Uiso 1 1 calc R . . C30 C 0.5768(6) -0.3258(3) -0.0122(3) 0.0568(8) Uani 1 1 d . . . H30A H 0.5289 -0.2548 0.0276 0.085 Uiso 1 1 calc R . . H30B H 0.4560 -0.3820 -0.0021 0.085 Uiso 1 1 calc R . . H30C H 0.6382 -0.2905 -0.0956 0.085 Uiso 1 1 calc R . . C31 C 0.4802(4) 0.7175(2) 0.6083(2) 0.0237(5) Uani 1 1 d . . . C32 C 0.6347(4) 0.8123(3) 0.5838(2) 0.0285(6) Uani 1 1 d . . . H32 H 0.7679 0.8040 0.5308 0.034 Uiso 1 1 calc R . . C33 C 0.5999(4) 0.9185(3) 0.6346(2) 0.0279(6) Uani 1 1 d . . . H33 H 0.7082 0.9818 0.6166 0.034 Uiso 1 1 calc R . . C34 C 0.4054(4) 0.9318(3) 0.7119(2) 0.0284(6) Uani 1 1 d . . . O2 O 0.3493(3) 1.03619(18) 0.76293(18) 0.0390(5) Uani 1 1 d . . . C35 C 0.2491(4) 0.8386(3) 0.7374(2) 0.0330(6) Uani 1 1 d . . . H35 H 0.1163 0.8471 0.7906 0.040 Uiso 1 1 calc R . . C36 C 0.2851(4) 0.7331(3) 0.6857(2) 0.0307(6) Uani 1 1 d . . . H36 H 0.1758 0.6705 0.7032 0.037 Uiso 1 1 calc R . . C37 C 0.5135(4) 1.1151(2) 0.7728(2) 0.0313(5) Uani 1 1 d . . . H37 H 0.6212 1.1388 0.6958 0.038 Uiso 1 1 calc R . . C38 C 0.6196(5) 1.0413(3) 0.8644(2) 0.0376(6) Uani 1 1 d . . . H38A H 0.5136 1.0241 0.9413 0.045 Uiso 1 1 calc R . . H38B H 0.6669 0.9570 0.8455 0.045 Uiso 1 1 calc R . . C39 C 0.8077(4) 1.1107(3) 0.8742(2) 0.0447(7) Uani 1 1 d . . . H39A H 0.9174 1.1236 0.7999 0.067 Uiso 1 1 calc R . . H39B H 0.8647 1.0588 0.9365 0.067 Uiso 1 1 calc R . . H39C H 0.7629 1.1946 0.8925 0.067 Uiso 1 1 calc R . . C40 C 0.4038(5) 1.2348(3) 0.8044(3) 0.0502(8) Uani 1 1 d . . . H40A H 0.3454 1.2812 0.7405 0.075 Uiso 1 1 calc R . . H40B H 0.5058 1.2905 0.8174 0.075 Uiso 1 1 calc R . . H40C H 0.2886 1.2105 0.8758 0.075 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 0.0233(10) 0.0210(10) 0.0263(10) -0.0069(8) -0.0076(8) 0.0033(8) N2 0.0243(10) 0.0224(11) 0.0280(10) -0.0077(8) -0.0089(9) 0.0018(9) N3 0.0264(11) 0.0193(10) 0.0274(10) -0.0082(8) -0.0111(8) 0.0025(8) N4 0.0252(11) 0.0216(11) 0.0246(9) -0.0073(8) -0.0082(8) 0.0024(8) C1 0.0237(12) 0.0225(12) 0.0247(11) -0.0031(9) -0.0065(9) 0.0021(10) C2 0.0273(13) 0.0247(13) 0.0308(12) -0.0053(10) -0.0091(11) 0.0063(10) C3 0.0305(13) 0.0221(12) 0.0304(12) -0.0084(10) -0.0088(11) 0.0073(11) C4 0.0234(12) 0.0240(13) 0.0232(11) -0.0065(10) -0.0039(9) 0.0013(10) C5 0.0248(12) 0.0193(12) 0.0273(11) -0.0088(9) -0.0042(10) 0.0012(10) C6 0.0276(13) 0.0261(13) 0.0246(11) -0.0087(10) -0.0063(10) 0.0008(11) C7 0.0333(14) 0.0261(13) 0.0289(12) -0.0124(10) -0.0109(11) 0.0027(11) C8 0.0377(15) 0.0251(13) 0.0310(12) -0.0090(11) -0.0182(11) 0.0033(11) C9 0.0278(13) 0.0241(12) 0.0237(11) -0.0049(9) -0.0092(10) -0.0009(10) C10 0.0261(12) 0.0259(12) 0.0280(12) -0.0068(10) -0.0136(10) 0.0015(10) C11 0.0236(12) 0.0237(12) 0.0264(11) -0.0056(10) -0.0099(10) 0.0036(10) C12 0.0265(13) 0.0274(13) 0.0294(12) -0.0070(10) -0.0118(10) 0.0070(11) C13 0.0271(13) 0.0208(12) 0.0281(12) -0.0060(10) -0.0060(10) 0.0047(10) C14 0.0240(12) 0.0149(11) 0.0261(11) -0.0047(9) -0.0068(10) 0.0020(9) C15 0.0236(12) 0.0227(12) 0.0225(10) -0.0060(9) -0.0053(9) -0.0021(10) C16 0.0241(12) 0.0194(12) 0.0243(11) -0.0068(9) -0.0086(9) -0.0026(10) C17 0.0333(14) 0.0271(13) 0.0295(12) -0.0102(10) -0.0148(11) 0.0002(11) C18 0.0309(14) 0.0330(14) 0.0302(12) -0.0113(11) -0.0149(11) 0.0024(11) C19 0.0275(13) 0.0262(13) 0.0264(11) -0.0081(10) -0.0114(10) -0.0021(10) C20 0.0266(12) 0.0267(13) 0.0287(12) -0.0068(10) -0.0120(10) 0.0025(10) C21 0.0299(13) 0.0211(12) 0.0241(11) -0.0086(9) -0.0061(10) 0.0035(10) C22 0.0272(13) 0.0268(13) 0.0339(12) -0.0104(10) -0.0066(11) -0.0027(10) C23 0.0246(12) 0.0343(14) 0.0334(12) -0.0158(10) -0.0033(10) 0.0024(11) C24 0.0338(13) 0.0238(12) 0.0322(11) -0.0127(10) -0.0060(10) 0.0029(10) C25 0.0380(16) 0.0254(14) 0.0405(14) -0.0120(12) 0.0040(12) -0.0074(12) C26 0.0332(14) 0.0259(13) 0.0320(12) -0.0114(11) 0.0033(11) -0.0028(11) O1 0.0413(11) 0.0333(10) 0.0446(10) -0.0242(8) 0.0009(8) -0.0032(8) C27 0.0374(14) 0.0238(12) 0.0427(13) -0.0137(10) -0.0077(11) -0.0024(10) C28 0.0509(16) 0.0348(13) 0.0408(13) -0.0176(11) -0.0192(12) 0.0061(12) C29 0.0537(18) 0.0383(15) 0.0551(16) -0.0171(13) -0.0203(14) 0.0114(13) C30 0.058(2) 0.0427(17) 0.079(2) -0.0158(16) -0.0324(18) 0.0114(15) C31 0.0248(12) 0.0218(12) 0.0274(12) -0.0083(10) -0.0092(10) -0.0003(10) C32 0.0250(13) 0.0282(13) 0.0317(12) -0.0132(10) -0.0006(10) -0.0006(11) C33 0.0264(13) 0.0241(13) 0.0345(12) -0.0133(10) -0.0043(11) -0.0005(10) C34 0.0273(12) 0.0279(13) 0.0322(11) -0.0140(10) -0.0054(10) 0.0009(10) O2 0.0276(9) 0.0371(10) 0.0589(11) -0.0337(9) -0.0034(8) 0.0000(8) C35 0.0259(13) 0.0370(15) 0.0371(12) -0.0204(11) 0.0009(11) -0.0033(11) C36 0.0254(13) 0.0343(14) 0.0342(13) -0.0156(11) -0.0031(11) -0.0060(11) C37 0.0301(13) 0.0283(12) 0.0408(12) -0.0180(10) -0.0099(10) 0.0010(10) C38 0.0456(15) 0.0342(13) 0.0350(11) -0.0079(10) -0.0133(11) 0.0000(11) C39 0.0389(15) 0.0589(18) 0.0365(12) -0.0048(12) -0.0150(11) 0.0013(13) C40 0.0418(16) 0.0416(16) 0.085(2) -0.0407(16) -0.0276(16) 0.0143(13) _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 C1 1.366(3) . ? N1 C4 1.371(3) . ? N1 H1A 0.8800 . ? N2 C6 1.371(3) . ? N2 C9 1.372(3) . ? N3 C14 1.360(3) . ? N3 C11 1.370(3) . ? N3 H3A 0.8800 . ? N4 C16 1.372(3) . ? N4 C19 1.378(3) . ? C1 C20 1.394(3) . ? C1 C2 1.448(3) . ? C2 C3 1.339(4) . ? C2 H2 0.9500 . ? C3 C4 1.443(3) . ? C3 H3 0.9500 . ? C4 C5 1.392(4) . ? C5 C6 1.403(3) . ? C5 C21 1.502(4) . ? C6 C7 1.429(4) . ? C7 C8 1.361(3) . ? C7 H7 0.9500 . ? C8 C9 1.437(3) . ? C8 H8 0.9500 . ? C9 C10 1.391(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.440(3) . ? C12 C13 1.360(4) . ? C12 H12 0.9500 . ? C13 C14 1.444(3) . ? C13 H13 0.9500 . ? C14 C15 1.401(3) . ? C15 C16 1.412(3) . ? C15 C31 1.488(4) . ? C16 C17 1.451(3) . ? C17 C18 1.352(4) . ? C17 H17 0.9500 . ? C18 C19 1.435(4) . ? C18 H18 0.9500 . ? C19 C20 1.388(3) . ? C20 H20 0.9500 . ? C21 C26 1.388(4) . ? C21 C22 1.394(3) . ? C22 C23 1.381(4) . ? C22 H22 0.9500 . ? C23 C24 1.391(4) . ? C23 H23 0.9500 . ? C24 O1 1.361(3) . ? C24 C25 1.392(4) . ? C25 C26 1.391(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1 C27 1.455(3) . ? C27 C28 1.507(4) . ? C27 C30 1.526(4) . ? C27 H27 1.0000 . ? C28 C29 1.514(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.391(4) . ? C31 C36 1.398(3) . ? C32 C33 1.387(4) . ? C32 H32 0.9500 . ? C33 C34 1.390(3) . ? C33 H33 0.9500 . ? C34 O2 1.378(3) . ? C34 C35 1.386(4) . ? O2 C37 1.442(3) . ? C35 C36 1.386(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C40 1.504(4) . ? C37 C38 1.517(3) . ? C37 H37 1.0000 . ? C38 C39 1.510(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 108.4(2) . . ? C1 N1 H1A 125.8 . . ? C4 N1 H1A 125.8 . . ? C6 N2 C9 107.2(2) . . ? C14 N3 C11 108.3(2) . . ? C14 N3 H3A 125.9 . . ? C11 N3 H3A 125.9 . . ? C16 N4 C19 107.1(2) . . ? N1 C1 C20 126.5(2) . . ? N1 C1 C2 108.2(2) . . ? C20 C1 C2 125.2(2) . . ? C3 C2 C1 107.3(2) . . ? C3 C2 H2 126.3 . . ? C1 C2 H2 126.3 . . ? C2 C3 C4 108.2(2) . . ? C2 C3 H3 125.9 . . ? C4 C3 H3 125.9 . . ? N1 C4 C5 124.8(2) . . ? N1 C4 C3 107.8(2) . . ? C5 C4 C3 127.3(2) . . ? C4 C5 C6 124.7(2) . . ? C4 C5 C21 119.0(2) . . ? C6 C5 C21 116.3(2) . . ? N2 C6 C5 125.1(2) . . ? N2 C6 C7 109.4(2) . . ? C5 C6 C7 125.5(2) . . ? C8 C7 C6 107.2(2) . . ? C8 C7 H7 126.4 . . ? C6 C7 H7 126.4 . . ? C7 C8 C9 107.2(2) . . ? C7 C8 H8 126.4 . . ? C9 C8 H8 126.4 . . ? N2 C9 C10 126.4(2) . . ? N2 C9 C8 109.0(2) . . ? C10 C9 C8 124.6(2) . . ? C11 C10 C9 128.4(2) . . ? C11 C10 H10 115.8 . . ? C9 C10 H10 115.8 . . ? N3 C11 C10 126.1(2) . . ? N3 C11 C12 108.6(2) . . ? C10 C11 C12 125.3(2) . . ? C13 C12 C11 107.3(2) . . ? C13 C12 H12 126.4 . . ? C11 C12 H12 126.4 . . ? C12 C13 C14 107.1(2) . . ? C12 C13 H13 126.4 . . ? C14 C13 H13 126.4 . . ? N3 C14 C15 125.5(2) . . ? N3 C14 C13 108.8(2) . . ? C15 C14 C13 125.7(2) . . ? C14 C15 C16 123.2(2) . . ? C14 C15 C31 119.2(2) . . ? C16 C15 C31 117.6(2) . . ? N4 C16 C15 125.9(2) . . ? N4 C16 C17 109.2(2) . . ? C15 C16 C17 124.9(2) . . ? C18 C17 C16 106.8(2) . . ? C18 C17 H17 126.6 . . ? C16 C17 H17 126.6 . . ? C17 C18 C19 107.9(2) . . ? C17 C18 H18 126.1 . . ? C19 C18 H18 126.1 . . ? N4 C19 C20 126.3(2) . . ? N4 C19 C18 109.1(2) . . ? C20 C19 C18 124.6(2) . . ? C19 C20 C1 127.8(2) . . ? C19 C20 H20 116.1 . . ? C1 C20 H20 116.1 . . ? C26 C21 C22 117.4(2) . . ? C26 C21 C5 119.7(2) . . ? C22 C21 C5 122.7(2) . . ? C23 C22 C21 121.5(3) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 120.4(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? O1 C24 C23 116.4(2) . . ? O1 C24 C25 124.7(2) . . ? C23 C24 C25 118.8(2) . . ? C26 C25 C24 119.9(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C21 C26 C25 121.7(2) . . ? C21 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C24 O1 C27 119.0(2) . . ? O1 C27 C28 106.4(2) . . ? O1 C27 C30 111.1(2) . . ? C28 C27 C30 110.7(2) . . ? O1 C27 H27 109.5 . . ? C28 C27 H27 109.5 . . ? C30 C27 H27 109.5 . . ? C27 C28 C29 112.7(2) . . ? C27 C28 H28A 109.1 . . ? C29 C28 H28A 109.1 . . ? C27 C28 H28B 109.1 . . ? C29 C28 H28B 109.1 . . ? H28A C28 H28B 107.8 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 C36 117.7(2) . . ? C32 C31 C15 119.9(2) . . ? C36 C31 C15 122.4(2) . . ? C33 C32 C31 121.9(2) . . ? C33 C32 H32 119.0 . . ? C31 C32 H32 119.0 . . ? C32 C33 C34 119.5(2) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? O2 C34 C35 115.8(2) . . ? O2 C34 C33 124.6(2) . . ? C35 C34 C33 119.5(2) . . ? C34 O2 C37 119.2(2) . . ? C34 C35 C36 120.5(2) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C35 C36 C31 120.9(2) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? O2 C37 C40 105.4(2) . . ? O2 C37 C38 109.7(2) . . ? C40 C37 C38 112.8(2) . . ? O2 C37 H37 109.6 . . ? C40 C37 H37 109.6 . . ? C38 C37 H37 109.6 . . ? C39 C38 C37 114.1(2) . . ? C39 C38 H38A 108.7 . . ? C37 C38 H38A 108.7 . . ? C39 C38 H38B 108.7 . . ? C37 C38 H38B 108.7 . . ? H38A C38 H38B 107.6 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.95 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.95 _refine_diff_density_max 0.330 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 942053' ####################################################################### # # 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_compound(S,S)-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H38 N4 O2' _chemical_formula_weight 606.74 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.5431(4) _cell_length_b 10.6318(6) _cell_length_c 12.1564(7) _cell_angle_alpha 76.976(3) _cell_angle_beta 74.585(3) _cell_angle_gamma 86.920(3) _cell_volume 794.25(8) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4207 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 29.30 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9906 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details sadabs _exptl_special_details ; Absolute configurations have been fixed based on known configurations The starting porphyrin being chiral and enantiopure the space group is thus necessarly noncentrosymmetric ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15915 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 29.89 _reflns_number_total 7128 _reflns_number_gt 5362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The absolute configurations of C27 and C37 are known ; _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^)+(0.0728P)^2^+0.2882P] 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 -0.9(18) _refine_ls_number_reflns 7128 _refine_ls_number_parameters 419 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.1178(4) 0.8057(2) 0.58397(19) 0.0231(6) Uani 1 1 d . . . H1A H 0.2123 0.7439 0.5875 0.028 Uiso 1 1 calc R . . N2 N 0.4390(4) 0.7317(2) 0.7015(2) 0.0249(6) Uani 1 1 d . . . N3 N 0.5579(4) 0.5091(2) 0.5843(2) 0.0241(6) Uani 1 1 d . . . H3A H 0.4658 0.5722 0.5791 0.029 Uiso 1 1 calc R . . N4 N 0.2358(4) 0.5833(2) 0.46758(19) 0.0241(6) Uani 1 1 d . . . C1 C -0.0242(4) 0.8217(3) 0.5180(2) 0.0253(7) Uani 1 1 d . . . C2 C -0.1489(5) 0.9350(3) 0.5367(3) 0.0292(7) Uani 1 1 d . . . H2 H -0.2594 0.9688 0.5014 0.035 Uiso 1 1 calc R . . C3 C -0.0798(5) 0.9834(3) 0.6129(2) 0.0266(7) Uani 1 1 d . . . H3 H -0.1328 1.0581 0.6415 0.032 Uiso 1 1 calc R . . C4 C 0.0879(5) 0.9031(3) 0.6440(2) 0.0231(7) Uani 1 1 d . . . C5 C 0.2051(5) 0.9195(3) 0.7204(3) 0.0250(7) Uani 1 1 d . . . C6 C 0.3672(5) 0.8371(3) 0.7485(2) 0.0261(7) Uani 1 1 d . . . C7 C 0.4789(5) 0.8465(3) 0.8329(3) 0.0293(7) Uani 1 1 d . . . H7 H 0.4586 0.9100 0.8786 0.035 Uiso 1 1 calc R . . C8 C 0.6188(5) 0.7480(3) 0.8353(3) 0.0302(8) Uani 1 1 d . . . H8 H 0.7155 0.7297 0.8828 0.036 Uiso 1 1 calc R . . C9 C 0.5941(5) 0.6761(3) 0.7525(2) 0.0246(7) Uani 1 1 d . . . C10 C 0.7123(5) 0.5678(3) 0.7297(2) 0.0272(7) Uani 1 1 d . . . H10 H 0.8178 0.5434 0.7710 0.033 Uiso 1 1 calc R . . C11 C 0.6949(5) 0.4910(3) 0.6542(2) 0.0246(7) Uani 1 1 d . . . C12 C 0.8207(5) 0.3791(3) 0.6366(3) 0.0277(7) Uani 1 1 d . . . H12 H 0.9291 0.3452 0.6734 0.033 Uiso 1 1 calc R . . C13 C 0.7549(5) 0.3305(3) 0.5566(2) 0.0267(7) Uani 1 1 d . . . H13 H 0.8087 0.2561 0.5276 0.032 Uiso 1 1 calc R . . C14 C 0.5886(5) 0.4130(3) 0.5244(2) 0.0232(7) Uani 1 1 d . . . C15 C 0.4737(5) 0.3961(3) 0.4466(2) 0.0222(6) Uani 1 1 d . . . C16 C 0.3105(5) 0.4796(3) 0.4195(2) 0.0225(7) Uani 1 1 d . . . C17 C 0.1985(5) 0.4701(3) 0.3336(3) 0.0289(7) Uani 1 1 d . . . H17 H 0.2215 0.4082 0.2862 0.035 Uiso 1 1 calc R . . C18 C 0.0555(5) 0.5662(3) 0.3339(3) 0.0302(7) Uani 1 1 d . . . H18 H -0.0421 0.5838 0.2869 0.036 Uiso 1 1 calc R . . C19 C 0.0767(5) 0.6373(3) 0.4180(2) 0.0262(7) Uani 1 1 d . . . C20 C -0.0418(5) 0.7446(3) 0.4418(2) 0.0271(7) Uani 1 1 d . . . H20 H -0.1483 0.7688 0.4012 0.033 Uiso 1 1 calc R . . C21 C 0.1601(5) 1.0329(3) 0.7765(2) 0.0259(7) Uani 1 1 d . . . C22 C -0.0247(5) 1.0438(3) 0.8632(3) 0.0310(7) Uani 1 1 d . . . H22 H -0.1361 0.9828 0.8812 0.037 Uiso 1 1 calc R . . C23 C -0.0485(5) 1.1423(3) 0.9233(3) 0.0338(8) Uani 1 1 d . . . H23 H -0.1746 1.1468 0.9829 0.041 Uiso 1 1 calc R . . C24 C 0.1093(5) 1.2340(3) 0.8974(3) 0.0326(8) Uani 1 1 d . . . C25 C 0.2893(6) 1.2299(4) 0.8063(3) 0.0377(8) Uani 1 1 d . . . H25 H 0.3952 1.2952 0.7842 0.045 Uiso 1 1 calc R . . C26 C 0.3124(5) 1.1293(3) 0.7481(3) 0.0325(8) Uani 1 1 d . . . H26 H 0.4367 1.1264 0.6869 0.039 Uiso 1 1 calc R . . O1 O 0.0785(4) 1.3225(2) 0.9660(2) 0.0448(6) Uani 1 1 d . . . C27 C 0.2546(6) 1.4036(3) 0.9595(3) 0.0393(8) Uani 1 1 d . . . H27 H 0.3206 1.4453 0.8759 0.047 Uiso 1 1 calc R . . C28 C 0.1644(6) 1.5060(3) 1.0263(3) 0.0443(8) Uani 1 1 d . . . H28A H 0.0925 1.4641 1.1080 0.053 Uiso 1 1 calc R . . H28B H 0.2815 1.5600 1.0281 0.053 Uiso 1 1 calc R . . C29 C 0.0083(7) 1.5910(4) 0.9722(3) 0.0528(10) Uani 1 1 d . . . H29A H -0.1200 1.5410 0.9834 0.079 Uiso 1 1 calc R . . H29B H 0.0723 1.6225 0.8884 0.079 Uiso 1 1 calc R . . H29C H -0.0286 1.6645 1.0099 0.079 Uiso 1 1 calc R . . C30 C 0.4222(7) 1.3263(4) 1.0126(4) 0.0630(11) Uani 1 1 d . . . H30A H 0.4770 1.2582 0.9702 0.094 Uiso 1 1 calc R . . H30B H 0.3585 1.2873 1.0950 0.094 Uiso 1 1 calc R . . H30C H 0.5386 1.3839 1.0065 0.094 Uiso 1 1 calc R . . C31 C 0.5188(5) 0.2817(3) 0.3920(2) 0.0237(7) Uani 1 1 d . . . C32 C 0.3656(5) 0.1875(3) 0.4170(3) 0.0304(7) Uani 1 1 d . . . H32 H 0.2329 0.1956 0.4706 0.036 Uiso 1 1 calc R . . C33 C 0.4005(5) 0.0811(3) 0.3657(3) 0.0290(7) Uani 1 1 d . . . H33 H 0.2925 0.0178 0.3840 0.035 Uiso 1 1 calc R . . C34 C 0.5933(5) 0.0681(3) 0.2881(3) 0.0301(7) Uani 1 1 d . . . O2 O 0.6511(4) -0.0364(2) 0.2371(2) 0.0429(6) Uani 1 1 d . . . C35 C 0.7499(5) 0.1613(3) 0.2625(3) 0.0351(8) Uani 1 1 d . . . H35 H 0.8828 0.1527 0.2093 0.042 Uiso 1 1 calc R . . C36 C 0.7135(5) 0.2664(3) 0.3139(3) 0.0320(7) Uani 1 1 d . . . H36 H 0.8221 0.3293 0.2960 0.038 Uiso 1 1 calc R . . C37 C 0.4856(5) -0.1148(3) 0.2265(3) 0.0360(7) Uani 1 1 d . . . H37 H 0.3775 -0.1382 0.3035 0.043 Uiso 1 1 calc R . . C38 C 0.3812(6) -0.0405(3) 0.1353(3) 0.0408(7) Uani 1 1 d . . . H38A H 0.4871 -0.0239 0.0584 0.049 Uiso 1 1 calc R . . H38B H 0.3349 0.0442 0.1541 0.049 Uiso 1 1 calc R . . C39 C 0.1926(5) -0.1090(4) 0.1260(3) 0.0487(9) Uani 1 1 d . . . H39A H 0.0844 -0.1229 0.2009 0.073 Uiso 1 1 calc R . . H39B H 0.2372 -0.1925 0.1063 0.073 Uiso 1 1 calc R . . H39C H 0.1336 -0.0562 0.0647 0.073 Uiso 1 1 calc R . . C40 C 0.5973(6) -0.2354(4) 0.1956(4) 0.0547(10) Uani 1 1 d . . . H40A H 0.6531 -0.2822 0.2605 0.082 Uiso 1 1 calc R . . H40B H 0.7145 -0.2113 0.1251 0.082 Uiso 1 1 calc R . . H40C H 0.4968 -0.2907 0.1811 0.082 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 0.0248(13) 0.0200(14) 0.0256(12) -0.0055(10) -0.0083(10) -0.0003(11) N2 0.0253(13) 0.0203(15) 0.0297(13) -0.0049(10) -0.0090(10) 0.0014(11) N3 0.0263(13) 0.0209(14) 0.0288(12) -0.0073(10) -0.0128(11) 0.0048(12) N4 0.0277(13) 0.0245(15) 0.0223(11) -0.0054(10) -0.0104(10) 0.0022(11) C1 0.0258(15) 0.0236(17) 0.0244(14) -0.0019(12) -0.0063(11) 0.0022(14) C2 0.0287(16) 0.0262(18) 0.0325(15) -0.0039(12) -0.0105(13) 0.0044(14) C3 0.0296(16) 0.0234(18) 0.0273(15) -0.0063(12) -0.0086(12) 0.0058(14) C4 0.0247(15) 0.0223(17) 0.0223(13) -0.0070(11) -0.0043(11) -0.0016(13) C5 0.0265(15) 0.0207(17) 0.0272(14) -0.0067(12) -0.0046(12) -0.0009(14) C6 0.0303(16) 0.0245(18) 0.0243(14) -0.0056(12) -0.0074(12) -0.0050(15) C7 0.0350(17) 0.0300(19) 0.0285(15) -0.0125(13) -0.0132(13) 0.0032(15) C8 0.0391(18) 0.0266(19) 0.0313(16) -0.0086(13) -0.0183(14) 0.0005(16) C9 0.0274(15) 0.0241(17) 0.0257(14) -0.0059(12) -0.0118(12) -0.0030(14) C10 0.0262(15) 0.0301(18) 0.0293(15) -0.0047(13) -0.0155(12) -0.0008(14) C11 0.0247(15) 0.0240(17) 0.0270(14) -0.0041(12) -0.0115(12) 0.0010(13) C12 0.0295(16) 0.0267(18) 0.0294(15) -0.0054(12) -0.0137(13) 0.0059(14) C13 0.0297(16) 0.0205(17) 0.0308(15) -0.0063(12) -0.0096(13) 0.0042(14) C14 0.0272(15) 0.0164(16) 0.0250(14) -0.0022(11) -0.0076(12) 0.0022(13) C15 0.0268(15) 0.0177(16) 0.0236(13) -0.0052(11) -0.0075(12) -0.0054(13) C16 0.0252(15) 0.0204(17) 0.0243(14) -0.0063(11) -0.0088(12) -0.0015(14) C17 0.0366(17) 0.0260(18) 0.0292(15) -0.0087(12) -0.0148(13) -0.0019(15) C18 0.0339(17) 0.032(2) 0.0317(15) -0.0108(13) -0.0182(13) 0.0007(16) C19 0.0293(16) 0.0260(17) 0.0265(14) -0.0050(12) -0.0126(13) -0.0033(14) C20 0.0287(15) 0.0273(17) 0.0275(14) -0.0049(12) -0.0124(12) 0.0024(14) C21 0.0306(17) 0.0228(17) 0.0245(14) -0.0050(12) -0.0081(13) 0.0020(14) C22 0.0303(16) 0.0275(18) 0.0356(16) -0.0104(13) -0.0058(13) -0.0030(15) C23 0.0285(15) 0.039(2) 0.0354(15) -0.0162(13) -0.0036(12) 0.0014(15) C24 0.0388(18) 0.0241(17) 0.0343(15) -0.0119(12) -0.0048(13) 0.0048(14) C25 0.0376(19) 0.029(2) 0.0414(18) -0.0126(15) 0.0039(15) -0.0094(17) C26 0.0351(18) 0.0269(19) 0.0339(16) -0.0139(13) 0.0005(14) -0.0023(16) O1 0.0480(14) 0.0384(14) 0.0462(13) -0.0229(11) 0.0034(10) -0.0058(12) C27 0.048(2) 0.0234(16) 0.0463(18) -0.0162(13) -0.0040(15) -0.0072(15) C28 0.059(2) 0.0383(19) 0.0426(16) -0.0146(14) -0.0204(15) 0.0038(17) C29 0.062(2) 0.040(2) 0.061(2) -0.0171(17) -0.0226(19) 0.0099(19) C30 0.071(3) 0.048(2) 0.078(3) -0.0113(19) -0.037(2) 0.011(2) C31 0.0272(16) 0.0204(17) 0.0278(15) -0.0092(12) -0.0109(12) -0.0011(14) C32 0.0284(16) 0.0294(19) 0.0308(15) -0.0095(13) -0.0004(13) -0.0037(15) C33 0.0306(17) 0.0221(17) 0.0359(16) -0.0116(13) -0.0062(13) -0.0042(14) C34 0.0295(15) 0.0301(18) 0.0334(15) -0.0138(13) -0.0070(12) -0.0001(14) O2 0.0340(12) 0.0394(14) 0.0632(15) -0.0360(12) -0.0054(10) -0.0017(11) C35 0.0277(16) 0.037(2) 0.0393(16) -0.0192(14) 0.0023(13) -0.0032(16) C36 0.0260(15) 0.036(2) 0.0344(16) -0.0133(14) -0.0024(13) -0.0072(15) C37 0.0361(17) 0.0300(18) 0.0468(17) -0.0187(13) -0.0109(13) 0.0007(14) C38 0.0515(19) 0.0389(19) 0.0349(14) -0.0066(13) -0.0170(13) -0.0014(16) C39 0.0421(18) 0.065(2) 0.0403(16) -0.0056(15) -0.0187(14) 0.0007(17) C40 0.052(2) 0.047(2) 0.084(3) -0.041(2) -0.031(2) 0.0161(19) _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 C1 1.362(4) . ? N1 C4 1.373(4) . ? N1 H1A 0.8800 . ? N2 C9 1.367(4) . ? N2 C6 1.375(4) . ? N3 C14 1.361(4) . ? N3 C11 1.369(4) . ? N3 H3A 0.8800 . ? N4 C16 1.371(4) . ? N4 C19 1.375(4) . ? C1 C20 1.397(4) . ? C1 C2 1.444(4) . ? C2 C3 1.339(4) . ? C2 H2 0.9500 . ? C3 C4 1.432(4) . ? C3 H3 0.9500 . ? C4 C5 1.395(4) . ? C5 C6 1.403(4) . ? C5 C21 1.494(4) . ? C6 C7 1.432(4) . ? C7 C8 1.354(4) . ? C7 H7 0.9500 . ? C8 C9 1.439(4) . ? C8 H8 0.9500 . ? C9 C10 1.391(4) . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 C12 1.433(4) . ? C12 C13 1.368(4) . ? C12 H12 0.9500 . ? C13 C14 1.441(4) . ? C13 H13 0.9500 . ? C14 C15 1.400(4) . ? C15 C16 1.410(4) . ? C15 C31 1.493(4) . ? C16 C17 1.449(4) . ? C17 C18 1.348(4) . ? C17 H17 0.9500 . ? C18 C19 1.439(4) . ? C18 H18 0.9500 . ? C19 C20 1.386(4) . ? C20 H20 0.9500 . ? C21 C26 1.389(5) . ? C21 C22 1.396(4) . ? C22 C23 1.385(5) . ? C22 H22 0.9500 . ? C23 C24 1.383(5) . ? C23 H23 0.9500 . ? C24 O1 1.366(4) . ? C24 C25 1.392(5) . ? C25 C26 1.391(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1 C27 1.450(4) . ? C27 C28 1.505(4) . ? C27 C30 1.528(5) . ? C27 H27 1.0000 . ? C28 C29 1.511(5) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.382(5) . ? C31 C36 1.398(4) . ? C32 C33 1.390(5) . ? C32 H32 0.9500 . ? C33 C34 1.381(4) . ? C33 H33 0.9500 . ? C34 O2 1.379(4) . ? C34 C35 1.389(5) . ? O2 C37 1.450(4) . ? C35 C36 1.379(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C38 1.507(4) . ? C37 C40 1.514(5) . ? C37 H37 1.0000 . ? C38 C39 1.509(5) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 108.0(2) . . ? C1 N1 H1A 126.0 . . ? C4 N1 H1A 126.0 . . ? C9 N2 C6 107.1(3) . . ? C14 N3 C11 108.3(2) . . ? C14 N3 H3A 125.8 . . ? C11 N3 H3A 125.8 . . ? C16 N4 C19 107.1(2) . . ? N1 C1 C20 125.9(3) . . ? N1 C1 C2 108.5(3) . . ? C20 C1 C2 125.6(3) . . ? C3 C2 C1 107.2(3) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 108.2(3) . . ? C2 C3 H3 125.9 . . ? C4 C3 H3 125.9 . . ? N1 C4 C5 124.9(3) . . ? N1 C4 C3 108.1(3) . . ? C5 C4 C3 127.0(3) . . ? C4 C5 C6 124.7(3) . . ? C4 C5 C21 119.0(3) . . ? C6 C5 C21 116.3(3) . . ? N2 C6 C5 125.0(3) . . ? N2 C6 C7 109.3(3) . . ? C5 C6 C7 125.6(3) . . ? C8 C7 C6 107.1(3) . . ? C8 C7 H7 126.4 . . ? C6 C7 H7 126.4 . . ? C7 C8 C9 107.3(3) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? N2 C9 C10 126.7(3) . . ? N2 C9 C8 109.1(3) . . ? C10 C9 C8 124.2(3) . . ? C9 C10 C11 128.0(3) . . ? C9 C10 H10 116.0 . . ? C11 C10 H10 116.0 . . ? N3 C11 C10 126.2(3) . . ? N3 C11 C12 108.9(3) . . ? C10 C11 C12 124.8(3) . . ? C13 C12 C11 106.9(3) . . ? C13 C12 H12 126.5 . . ? C11 C12 H12 126.5 . . ? C12 C13 C14 107.2(3) . . ? C12 C13 H13 126.4 . . ? C14 C13 H13 126.4 . . ? N3 C14 C15 125.4(3) . . ? N3 C14 C13 108.6(3) . . ? C15 C14 C13 126.0(3) . . ? C14 C15 C16 123.4(3) . . ? C14 C15 C31 119.1(3) . . ? C16 C15 C31 117.5(3) . . ? N4 C16 C15 125.9(3) . . ? N4 C16 C17 109.3(3) . . ? C15 C16 C17 124.8(3) . . ? C18 C17 C16 106.7(3) . . ? C18 C17 H17 126.6 . . ? C16 C17 H17 126.6 . . ? C17 C18 C19 108.0(3) . . ? C17 C18 H18 126.0 . . ? C19 C18 H18 126.0 . . ? N4 C19 C20 126.2(3) . . ? N4 C19 C18 108.9(3) . . ? C20 C19 C18 124.9(3) . . ? C19 C20 C1 128.2(3) . . ? C19 C20 H20 115.9 . . ? C1 C20 H20 115.9 . . ? C26 C21 C22 117.2(3) . . ? C26 C21 C5 119.7(3) . . ? C22 C21 C5 123.0(3) . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C24 C23 C22 120.8(3) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? O1 C24 C23 116.8(3) . . ? O1 C24 C25 124.0(3) . . ? C23 C24 C25 119.1(3) . . ? C26 C25 C24 119.3(3) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C21 122.3(3) . . ? C25 C26 H26 118.9 . . ? C21 C26 H26 118.9 . . ? C24 O1 C27 119.2(3) . . ? O1 C27 C28 106.9(3) . . ? O1 C27 C30 111.7(3) . . ? C28 C27 C30 109.9(3) . . ? O1 C27 H27 109.4 . . ? C28 C27 H27 109.4 . . ? C30 C27 H27 109.4 . . ? C29 C28 C27 112.0(3) . . ? C29 C28 H28A 109.2 . . ? C27 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C27 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C32 C31 C36 117.9(3) . . ? C32 C31 C15 120.2(3) . . ? C36 C31 C15 121.9(3) . . ? C31 C32 C33 121.8(3) . . ? C31 C32 H32 119.1 . . ? C33 C32 H32 119.1 . . ? C34 C33 C32 119.6(3) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 O2 124.9(3) . . ? C33 C34 C35 119.6(3) . . ? O2 C34 C35 115.4(3) . . ? C34 O2 C37 118.6(3) . . ? C36 C35 C34 120.4(3) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 120.9(3) . . ? C35 C36 H36 119.6 . . ? C31 C36 H36 119.6 . . ? O2 C37 C38 109.7(3) . . ? O2 C37 C40 104.7(3) . . ? C38 C37 C40 113.5(3) . . ? O2 C37 H37 109.6 . . ? C38 C37 H37 109.6 . . ? C40 C37 H37 109.6 . . ? C37 C38 C39 113.7(3) . . ? C37 C38 H38A 108.8 . . ? C39 C38 H38A 108.8 . . ? C37 C38 H38B 108.8 . . ? C39 C38 H38B 108.8 . . ? H38A C38 H38B 107.7 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.97 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.97 _refine_diff_density_max 0.403 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 942054' ####################################################################### # # 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_compound(R,R)-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H44 N6 O2' _chemical_formula_weight 760.91 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.6076(9) _cell_length_b 10.4384(16) _cell_length_c 14.810(2) _cell_angle_alpha 81.361(4) _cell_angle_beta 80.936(5) _cell_angle_gamma 76.921(5) _cell_volume 975.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1309 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 23.79 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9880 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details sadabs _exptl_special_details ; Absolute configurations have been fixed based on known configurations The starting porphyrin being chiral and enantiopure the space group is thus necessarly noncentrosymmetric ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12665 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.1266 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 30.19 _reflns_number_total 8796 _reflns_number_gt 4496 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. absolute configurations were determined based on known configurations ; _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^)+(0.0650P)^2^+0.0598P] 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 0(3) _refine_ls_number_reflns 8796 _refine_ls_number_parameters 527 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1556 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1755 _refine_ls_wR_factor_gt 0.1306 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 0.6670(9) 0.5615(5) 1.0207(4) 0.0232(13) Uani 1 1 d . . . H1A H 0.7656 0.5059 0.9907 0.028 Uiso 1 1 calc R . . N2 N 0.7390(8) 0.4655(5) 0.8364(4) 0.0222(14) Uani 1 1 d . . . N3 N 1.1544(8) 0.3242(5) 0.8744(4) 0.0193(13) Uani 1 1 d . . . H3A H 1.0525 0.3783 0.9040 0.023 Uiso 1 1 calc R . . N4 N 1.0894(9) 0.4121(5) 1.0522(3) 0.0219(13) Uani 1 1 d . . . C1 C 0.6712(11) 0.5888(6) 1.1062(5) 0.0245(17) Uani 1 1 d . . . C2 C 0.4781(11) 0.6815(6) 1.1307(5) 0.0264(17) Uani 1 1 d . . . H2 H 0.4355 0.7166 1.1879 0.032 Uiso 1 1 calc R . . C3 C 0.3688(10) 0.7092(6) 1.0573(4) 0.0186(14) Uani 1 1 d . . . H3 H 0.2375 0.7684 1.0524 0.022 Uiso 1 1 calc R . . C4 C 0.4935(12) 0.6301(6) 0.9879(4) 0.0250(16) Uani 1 1 d . . . C5 C 0.4348(10) 0.6283(6) 0.9002(5) 0.0197(15) Uani 1 1 d . . . C6 C 0.5464(10) 0.5503(6) 0.8316(5) 0.0234(16) Uani 1 1 d . . . C7 C 0.4904(11) 0.5515(7) 0.7444(5) 0.0266(17) Uani 1 1 d . . . H7 H 0.3656 0.6020 0.7222 0.032 Uiso 1 1 calc R . . C8 C 0.6439(12) 0.4684(6) 0.6964(5) 0.0256(17) Uani 1 1 d . . . H8 H 0.6435 0.4481 0.6360 0.031 Uiso 1 1 calc R . . C9 C 0.8074(12) 0.4167(7) 0.7541(5) 0.0245(17) Uani 1 1 d . . . C10 C 1.0039(10) 0.3361(6) 0.7305(4) 0.0189(15) Uani 1 1 d . . . C11 C 1.1658(10) 0.2920(6) 0.7858(4) 0.0196(16) Uani 1 1 d . . . C12 C 1.3593(11) 0.2010(7) 0.7616(5) 0.0260(16) Uani 1 1 d . . . H12 H 1.4035 0.1646 0.7050 0.031 Uiso 1 1 calc R . . C13 C 1.4656(13) 0.1775(7) 0.8351(5) 0.0342(19) Uani 1 1 d . . . H13 H 1.5999 0.1217 0.8390 0.041 Uiso 1 1 calc R . . C14 C 1.3409(10) 0.2514(6) 0.9065(5) 0.0192(15) Uani 1 1 d . . . C15 C 1.3982(12) 0.2512(6) 0.9926(5) 0.0238(16) Uani 1 1 d . . . C16 C 1.2834(11) 0.3282(6) 1.0591(4) 0.0222(16) Uani 1 1 d . . . C17 C 1.3387(12) 0.3284(7) 1.1515(5) 0.0257(17) Uani 1 1 d . . . H17 H 1.4651 0.2821 1.1743 0.031 Uiso 1 1 calc R . . C18 C 1.1776(12) 0.4061(7) 1.1978(5) 0.0283(17) Uani 1 1 d . . . H18 H 1.1674 0.4218 1.2601 0.034 Uiso 1 1 calc R . . C19 C 1.0247(10) 0.4608(6) 1.1366(5) 0.0198(15) Uani 1 1 d . . . C20 C 0.8307(12) 0.5428(6) 1.1627(5) 0.0255(17) Uani 1 1 d . . . C21 C 0.2432(10) 0.7277(6) 0.8739(4) 0.0194(15) Uani 1 1 d . . . C22 C 0.2409(12) 0.8620(7) 0.8613(5) 0.0295(18) Uani 1 1 d . . . H22 H 0.3587 0.8941 0.8704 0.035 Uiso 1 1 calc R . . C23 C 0.0600(11) 0.9493(7) 0.8345(5) 0.034(2) Uani 1 1 d . . . H23 H 0.0592 1.0414 0.8268 0.041 Uiso 1 1 calc R . . N5 N -0.1093(10) 0.9131(5) 0.8192(5) 0.0340(16) Uani 1 1 d . . . C24 C -0.1079(11) 0.7843(7) 0.8336(5) 0.0318(18) Uani 1 1 d . . . H24 H -0.2304 0.7557 0.8264 0.038 Uiso 1 1 calc R . . C25 C 0.0658(12) 0.6888(7) 0.8588(5) 0.0282(17) Uani 1 1 d . . . H25 H 0.0619 0.5974 0.8655 0.034 Uiso 1 1 calc R . . C26 C 1.0392(11) 0.2896(7) 0.6363(4) 0.0222(16) Uani 1 1 d . . . C27 C 1.1883(13) 0.3304(7) 0.5687(5) 0.036(2) Uani 1 1 d . . . H27 H 1.2650 0.3908 0.5817 0.044 Uiso 1 1 calc R . . C28 C 1.2304(12) 0.2862(7) 0.4821(5) 0.0323(19) Uani 1 1 d . . . H28 H 1.3380 0.3131 0.4379 0.039 Uiso 1 1 calc R . . C29 C 1.1136(14) 0.2029(8) 0.4616(5) 0.0351(19) Uani 1 1 d . . . C30 C 0.9585(12) 0.1647(7) 0.5289(5) 0.0320(18) Uani 1 1 d . . . H30 H 0.8760 0.1082 0.5153 0.038 Uiso 1 1 calc R . . C31 C 0.9236(12) 0.2072(7) 0.6135(5) 0.0334(19) Uani 1 1 d . . . H31 H 0.8170 0.1795 0.6580 0.040 Uiso 1 1 calc R . . O1 O 1.1724(8) 0.1590(5) 0.3770(3) 0.0359(12) Uani 1 1 d . . . C32 C 1.0579(13) 0.0716(8) 0.3498(5) 0.0367(19) Uani 1 1 d . . . H32 H 1.0229 0.0062 0.4034 0.044 Uiso 1 1 calc R . . C33 C 0.8598(13) 0.1535(8) 0.3156(5) 0.043(2) Uani 1 1 d . . . H33A H 0.7934 0.2197 0.3584 0.052 Uiso 1 1 calc R . . H33B H 0.8960 0.2021 0.2546 0.052 Uiso 1 1 calc R . . C34 C 0.7075(9) 0.0726(6) 0.3074(4) 0.0593(17) Uani 1 1 d . . . H34A H 0.7664 0.0135 0.2600 0.089 Uiso 1 1 calc R . . H34B H 0.5774 0.1310 0.2902 0.089 Uiso 1 1 calc R . . H34C H 0.6778 0.0197 0.3665 0.089 Uiso 1 1 calc R . . C35 C 1.2090(14) -0.0007(8) 0.2742(5) 0.049(2) Uani 1 1 d . . . H35A H 1.2605 0.0646 0.2267 0.074 Uiso 1 1 calc R . . H35B H 1.1348 -0.0531 0.2465 0.074 Uiso 1 1 calc R . . H35C H 1.3276 -0.0594 0.3015 0.074 Uiso 1 1 calc R . . C36 C 1.5912(12) 0.1550(7) 1.0178(5) 0.0253(17) Uani 1 1 d . . . C37 C 1.7681(12) 0.1940(7) 1.0340(5) 0.0296(18) Uani 1 1 d . . . H37 H 1.7730 0.2853 1.0271 0.036 Uiso 1 1 calc R . . C38 C 1.9361(11) 0.0992(7) 1.0601(5) 0.0307(18) Uani 1 1 d . . . H38 H 2.0543 0.1286 1.0718 0.037 Uiso 1 1 calc R . . N6 N 1.9457(10) -0.0315(6) 1.0702(4) 0.0321(16) Uani 1 1 d . . . C39 C 1.7717(13) -0.0692(7) 1.0559(5) 0.034(2) Uani 1 1 d . . . H39 H 1.7708 -0.1611 1.0642 0.041 Uiso 1 1 calc R . . C40 C 1.5975(12) 0.0178(6) 1.0300(5) 0.0278(18) Uani 1 1 d . . . H40 H 1.4800 -0.0142 1.0202 0.033 Uiso 1 1 calc R . . C41 C 0.7905(11) 0.5854(6) 1.2557(5) 0.0258(17) Uani 1 1 d . . . C42 C 0.9123(12) 0.6640(6) 1.2804(5) 0.0259(17) Uani 1 1 d . . . H42 H 1.0193 0.6914 1.2361 0.031 Uiso 1 1 calc R . . C43 C 0.8822(13) 0.7042(7) 1.3692(5) 0.0350(19) Uani 1 1 d . . . H43 H 0.9707 0.7554 1.3849 0.042 Uiso 1 1 calc R . . C44 C 0.7243(13) 0.6686(7) 1.4322(5) 0.0300(18) Uani 1 1 d . . . C45 C 0.6004(12) 0.5885(7) 1.4092(5) 0.0332(19) Uani 1 1 d . . . H45 H 0.4937 0.5613 1.4539 0.040 Uiso 1 1 calc R . . C46 C 0.6316(10) 0.5489(6) 1.3231(5) 0.0228(15) Uani 1 1 d . . . H46 H 0.5444 0.4959 1.3086 0.027 Uiso 1 1 calc R . . O2 O 0.6765(9) 0.7021(5) 1.5199(4) 0.0448(15) Uani 1 1 d . . . C47 C 0.7834(13) 0.7911(7) 1.5510(5) 0.0370(19) Uani 1 1 d . . . H47 H 0.8147 0.8583 1.4980 0.044 Uiso 1 1 calc R . . C48 C 0.6346(13) 0.8600(8) 1.6223(6) 0.042(2) Uani 1 1 d . . . H48A H 0.7049 0.9181 1.6480 0.050 Uiso 1 1 calc R . . H48B H 0.5944 0.7936 1.6731 0.050 Uiso 1 1 calc R . . C49 C 0.4370(9) 0.9434(6) 1.5853(4) 0.0543(16) Uani 1 1 d . . . H49A H 0.4720 1.0203 1.5443 0.081 Uiso 1 1 calc R . . H49B H 0.3333 0.9737 1.6368 0.081 Uiso 1 1 calc R . . H49C H 0.3790 0.8899 1.5511 0.081 Uiso 1 1 calc R . . C50 C 0.9906(14) 0.7158(8) 1.5845(6) 0.056(3) Uani 1 1 d . . . H50A H 0.9644 0.6424 1.6314 0.084 Uiso 1 1 calc R . . H50B H 1.0525 0.7761 1.6111 0.084 Uiso 1 1 calc R . . H50C H 1.0873 0.6807 1.5324 0.084 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 0.020(3) 0.019(3) 0.027(3) 0.001(2) -0.002(2) -0.001(2) N2 0.019(3) 0.019(3) 0.027(3) 0.002(2) -0.012(3) 0.001(2) N3 0.014(3) 0.020(3) 0.022(3) -0.010(2) -0.004(2) 0.006(2) N4 0.027(3) 0.019(3) 0.017(3) -0.007(2) 0.004(2) 0.001(2) C1 0.024(4) 0.020(3) 0.027(4) -0.002(3) 0.001(3) -0.002(3) C2 0.031(4) 0.024(3) 0.018(3) -0.001(3) 0.000(3) 0.005(3) C3 0.014(3) 0.020(3) 0.019(3) -0.010(2) 0.004(3) 0.003(2) C4 0.032(4) 0.021(3) 0.018(3) 0.001(3) -0.003(3) 0.001(3) C5 0.010(4) 0.018(3) 0.030(4) -0.003(3) -0.004(3) 0.000(3) C6 0.013(4) 0.019(3) 0.038(4) -0.008(3) -0.007(3) 0.004(3) C7 0.014(4) 0.028(4) 0.036(4) -0.001(3) -0.011(3) 0.001(3) C8 0.034(5) 0.022(3) 0.024(4) -0.003(3) -0.013(3) -0.007(3) C9 0.034(5) 0.020(3) 0.019(3) -0.003(3) -0.004(3) -0.004(3) C10 0.016(4) 0.024(3) 0.018(3) -0.003(3) -0.001(3) -0.009(3) C11 0.018(4) 0.019(3) 0.020(3) -0.003(3) -0.004(3) -0.001(3) C12 0.017(4) 0.029(4) 0.034(4) -0.014(3) -0.002(3) -0.005(3) C13 0.034(5) 0.026(3) 0.039(4) 0.004(3) -0.011(4) 0.000(3) C14 0.009(3) 0.018(3) 0.030(4) -0.005(3) -0.002(3) -0.001(3) C15 0.029(4) 0.017(3) 0.025(4) 0.002(3) -0.009(3) -0.003(3) C16 0.033(5) 0.020(3) 0.015(3) 0.005(3) -0.008(3) -0.011(3) C17 0.031(4) 0.028(4) 0.019(3) -0.001(3) -0.011(3) -0.005(3) C18 0.026(4) 0.032(4) 0.024(4) -0.007(3) -0.007(3) 0.004(3) C19 0.014(4) 0.020(3) 0.025(4) 0.000(3) -0.007(3) -0.002(3) C20 0.034(5) 0.017(3) 0.023(4) 0.001(3) -0.005(3) 0.000(3) C21 0.013(4) 0.019(3) 0.021(3) 0.006(2) -0.005(3) 0.004(3) C22 0.028(5) 0.027(4) 0.034(4) -0.004(3) -0.013(4) -0.001(3) C23 0.024(5) 0.025(4) 0.048(5) 0.002(3) -0.009(4) 0.004(3) N5 0.029(4) 0.020(3) 0.050(4) -0.001(3) -0.007(3) 0.002(3) C24 0.017(4) 0.032(4) 0.038(4) 0.011(3) 0.001(3) 0.000(3) C25 0.031(5) 0.023(3) 0.029(4) -0.001(3) -0.004(3) -0.004(3) C26 0.024(4) 0.028(3) 0.016(3) -0.012(3) -0.005(3) -0.001(3) C27 0.055(6) 0.029(4) 0.028(4) -0.006(3) -0.006(4) -0.014(4) C28 0.043(5) 0.037(4) 0.017(3) -0.007(3) 0.007(3) -0.015(4) C29 0.038(5) 0.034(4) 0.030(4) -0.004(3) 0.000(4) -0.004(3) C30 0.030(4) 0.039(4) 0.029(4) -0.007(3) 0.005(3) -0.014(3) C31 0.029(4) 0.032(4) 0.037(4) -0.010(3) 0.011(3) -0.008(3) O1 0.041(3) 0.048(3) 0.024(2) -0.016(2) 0.003(2) -0.017(2) C32 0.041(5) 0.045(4) 0.031(4) -0.011(3) -0.012(3) -0.016(3) C33 0.056(5) 0.050(4) 0.029(4) -0.005(3) -0.009(4) -0.018(4) C34 0.045(4) 0.074(4) 0.053(4) 0.003(3) -0.005(3) -0.008(3) C35 0.066(6) 0.050(4) 0.032(4) -0.026(3) 0.018(4) -0.014(4) C36 0.030(5) 0.027(3) 0.023(4) -0.008(3) -0.004(3) -0.010(3) C37 0.022(4) 0.023(3) 0.045(5) 0.004(3) -0.013(4) -0.006(3) C38 0.019(4) 0.039(4) 0.042(4) -0.012(3) -0.015(4) -0.010(3) N6 0.023(4) 0.040(4) 0.029(3) 0.001(3) -0.012(3) 0.006(3) C39 0.050(6) 0.017(3) 0.036(4) -0.006(3) -0.015(4) 0.003(3) C40 0.026(4) 0.017(3) 0.042(5) -0.004(3) -0.008(4) -0.004(3) C41 0.024(4) 0.020(3) 0.030(4) 0.005(3) -0.007(3) 0.000(3) C42 0.031(4) 0.031(4) 0.020(3) -0.008(3) -0.009(3) -0.008(3) C43 0.043(5) 0.036(4) 0.035(4) -0.013(3) -0.013(4) -0.016(4) C44 0.042(5) 0.033(4) 0.018(3) -0.011(3) -0.004(3) -0.007(3) C45 0.033(5) 0.033(4) 0.035(4) 0.000(3) -0.003(4) -0.014(4) C46 0.016(4) 0.029(4) 0.025(4) -0.004(3) -0.002(3) -0.008(3) O2 0.070(4) 0.040(3) 0.030(3) -0.011(2) 0.005(3) -0.027(3) C47 0.053(5) 0.026(3) 0.030(4) -0.004(3) 0.004(3) -0.008(3) C48 0.044(5) 0.039(3) 0.047(5) -0.007(3) -0.016(4) -0.008(3) C49 0.055(4) 0.046(3) 0.054(4) -0.015(3) -0.009(3) 0.014(3) C50 0.043(5) 0.053(5) 0.070(6) -0.004(4) -0.022(5) -0.001(4) _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 C4 1.327(8) . ? N1 C1 1.344(8) . ? N1 H1A 0.8800 . ? N2 C9 1.362(8) . ? N2 C6 1.381(8) . ? N3 C11 1.389(8) . ? N3 C14 1.405(7) . ? N3 H3A 0.8800 . ? N4 C16 1.388(8) . ? N4 C19 1.389(8) . ? C1 C20 1.404(9) . ? C1 C2 1.448(9) . ? C2 C3 1.359(8) . ? C2 H2 0.9500 . ? C3 C4 1.448(9) . ? C3 H3 0.9500 . ? C4 C5 1.418(9) . ? C5 C6 1.408(9) . ? C5 C21 1.506(8) . ? C6 C7 1.396(9) . ? C7 C8 1.358(10) . ? C7 H7 0.9500 . ? C8 C9 1.442(9) . ? C8 H8 0.9500 . ? C9 C10 1.402(9) . ? C10 C11 1.402(8) . ? C10 C26 1.513(9) . ? C11 C12 1.440(9) . ? C12 C13 1.349(9) . ? C12 H12 0.9500 . ? C13 C14 1.441(10) . ? C13 H13 0.9500 . ? C14 C15 1.386(9) . ? C15 C16 1.384(9) . ? C15 C36 1.494(10) . ? C16 C17 1.471(8) . ? C17 C18 1.345(10) . ? C17 H17 0.9500 . ? C18 C19 1.428(9) . ? C18 H18 0.9500 . ? C19 C20 1.404(9) . ? C20 C41 1.477(10) . ? C21 C22 1.383(9) . ? C21 C25 1.384(9) . ? C22 C23 1.401(9) . ? C22 H22 0.9500 . ? C23 N5 1.320(9) . ? C23 H23 0.9500 . ? N5 C24 1.327(8) . ? C24 C25 1.398(9) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C31 1.379(10) . ? C26 C27 1.380(10) . ? C27 C28 1.393(9) . ? C27 H27 0.9500 . ? C28 C29 1.379(11) . ? C28 H28 0.9500 . ? C29 O1 1.367(9) . ? C29 C30 1.395(11) . ? C30 C31 1.360(10) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? O1 C32 1.444(9) . ? C32 C33 1.508(10) . ? C32 C35 1.542(10) . ? C32 H32 1.0000 . ? C33 C34 1.481(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C37 1.387(9) . ? C36 C40 1.408(9) . ? C37 C38 1.372(9) . ? C37 H37 0.9500 . ? C38 N6 1.338(9) . ? C38 H38 0.9500 . ? N6 C39 1.353(9) . ? C39 C40 1.362(9) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C42 1.391(10) . ? C41 C46 1.407(9) . ? C42 C43 1.411(9) . ? C42 H42 0.9500 . ? C43 C44 1.364(11) . ? C43 H43 0.9500 . ? C44 O2 1.365(8) . ? C44 C45 1.404(11) . ? C45 C46 1.370(9) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? O2 C47 1.450(9) . ? C47 C48 1.477(11) . ? C47 C50 1.532(11) . ? C47 H47 1.0000 . ? C48 C49 1.527(8) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 110.6(6) . . ? C4 N1 H1A 124.7 . . ? C1 N1 H1A 124.7 . . ? C9 N2 C6 109.2(5) . . ? C11 N3 C14 105.0(5) . . ? C11 N3 H3A 127.5 . . ? C14 N3 H3A 127.5 . . ? C16 N4 C19 106.4(5) . . ? N1 C1 C20 128.6(6) . . ? N1 C1 C2 107.0(6) . . ? C20 C1 C2 124.4(6) . . ? C3 C2 C1 107.8(6) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? C2 C3 C4 105.8(6) . . ? C2 C3 H3 127.1 . . ? C4 C3 H3 127.1 . . ? N1 C4 C5 126.9(6) . . ? N1 C4 C3 108.8(6) . . ? C5 C4 C3 124.3(6) . . ? C6 C5 C4 126.7(6) . . ? C6 C5 C21 116.0(6) . . ? C4 C5 C21 117.1(6) . . ? N2 C6 C7 107.7(6) . . ? N2 C6 C5 125.7(6) . . ? C7 C6 C5 126.4(6) . . ? C8 C7 C6 108.7(6) . . ? C8 C7 H7 125.6 . . ? C6 C7 H7 125.6 . . ? C7 C8 C9 107.3(6) . . ? C7 C8 H8 126.4 . . ? C9 C8 H8 126.4 . . ? N2 C9 C10 125.6(6) . . ? N2 C9 C8 106.9(6) . . ? C10 C9 C8 127.4(6) . . ? C11 C10 C9 126.8(6) . . ? C11 C10 C26 117.5(6) . . ? C9 C10 C26 115.6(5) . . ? N3 C11 C10 124.1(6) . . ? N3 C11 C12 110.7(5) . . ? C10 C11 C12 125.1(6) . . ? C13 C12 C11 106.7(7) . . ? C13 C12 H12 126.7 . . ? C11 C12 H12 126.7 . . ? C12 C13 C14 108.4(7) . . ? C12 C13 H13 125.8 . . ? C14 C13 H13 125.8 . . ? C15 C14 N3 125.8(6) . . ? C15 C14 C13 125.1(6) . . ? N3 C14 C13 109.1(6) . . ? C16 C15 C14 124.8(6) . . ? C16 C15 C36 117.4(6) . . ? C14 C15 C36 117.6(6) . . ? C15 C16 N4 125.7(6) . . ? C15 C16 C17 126.0(6) . . ? N4 C16 C17 108.1(6) . . ? C18 C17 C16 107.5(6) . . ? C18 C17 H17 126.2 . . ? C16 C17 H17 126.2 . . ? C17 C18 C19 107.7(6) . . ? C17 C18 H18 126.1 . . ? C19 C18 H18 126.1 . . ? N4 C19 C20 126.1(6) . . ? N4 C19 C18 110.1(6) . . ? C20 C19 C18 123.6(6) . . ? C1 C20 C19 124.6(6) . . ? C1 C20 C41 117.1(6) . . ? C19 C20 C41 118.3(6) . . ? C22 C21 C25 117.4(6) . . ? C22 C21 C5 120.9(6) . . ? C25 C21 C5 121.7(6) . . ? C21 C22 C23 118.2(7) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? N5 C23 C22 124.9(7) . . ? N5 C23 H23 117.6 . . ? C22 C23 H23 117.6 . . ? C23 N5 C24 116.6(6) . . ? N5 C24 C25 123.0(7) . . ? N5 C24 H24 118.5 . . ? C25 C24 H24 118.5 . . ? C21 C25 C24 119.9(6) . . ? C21 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C31 C26 C27 117.2(7) . . ? C31 C26 C10 122.1(7) . . ? C27 C26 C10 120.6(6) . . ? C26 C27 C28 122.3(7) . . ? C26 C27 H27 118.8 . . ? C28 C27 H27 118.8 . . ? C29 C28 C27 119.1(8) . . ? C29 C28 H28 120.5 . . ? C27 C28 H28 120.5 . . ? O1 C29 C28 115.2(7) . . ? O1 C29 C30 126.1(8) . . ? C28 C29 C30 118.6(8) . . ? C31 C30 C29 121.1(8) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.4 . . ? C30 C31 C26 121.5(8) . . ? C30 C31 H31 119.2 . . ? C26 C31 H31 119.2 . . ? C29 O1 C32 118.8(7) . . ? O1 C32 C33 108.8(6) . . ? O1 C32 C35 105.0(7) . . ? C33 C32 C35 112.8(6) . . ? O1 C32 H32 110.0 . . ? C33 C32 H32 110.0 . . ? C35 C32 H32 110.0 . . ? C34 C33 C32 112.8(6) . . ? C34 C33 H33A 109.0 . . ? C32 C33 H33A 109.0 . . ? C34 C33 H33B 109.0 . . ? C32 C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 C40 116.5(6) . . ? C37 C36 C15 122.9(6) . . ? C40 C36 C15 120.5(6) . . ? C38 C37 C36 119.2(6) . . ? C38 C37 H37 120.4 . . ? C36 C37 H37 120.4 . . ? N6 C38 C37 124.9(7) . . ? N6 C38 H38 117.6 . . ? C37 C38 H38 117.6 . . ? C38 N6 C39 115.7(6) . . ? N6 C39 C40 123.4(7) . . ? N6 C39 H39 118.3 . . ? C40 C39 H39 118.3 . . ? C39 C40 C36 120.2(7) . . ? C39 C40 H40 119.9 . . ? C36 C40 H40 119.9 . . ? C42 C41 C46 117.0(7) . . ? C42 C41 C20 120.4(7) . . ? C46 C41 C20 122.6(7) . . ? C41 C42 C43 122.2(8) . . ? C41 C42 H42 118.9 . . ? C43 C42 H42 118.9 . . ? C44 C43 C42 119.0(7) . . ? C44 C43 H43 120.5 . . ? C42 C43 H43 120.5 . . ? O2 C44 C43 125.1(8) . . ? O2 C44 C45 115.1(7) . . ? C43 C44 C45 119.8(7) . . ? C46 C45 C44 120.8(8) . . ? C46 C45 H45 119.6 . . ? C44 C45 H45 119.6 . . ? C45 C46 C41 121.1(7) . . ? C45 C46 H46 119.4 . . ? C41 C46 H46 119.4 . . ? C44 O2 C47 120.9(7) . . ? O2 C47 C48 106.6(7) . . ? O2 C47 C50 111.0(6) . . ? C48 C47 C50 113.7(7) . . ? O2 C47 H47 108.4 . . ? C48 C47 H47 108.4 . . ? C50 C47 H47 108.4 . . ? C47 C48 C49 112.7(6) . . ? C47 C48 H48A 109.0 . . ? C49 C48 H48A 109.0 . . ? C47 C48 H48B 109.1 . . ? C49 C48 H48B 109.0 . . ? H48A C48 H48B 107.8 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.19 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.305 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 942055' ####################################################################### # # 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_compound(S,S)-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H44 N6 O2' _chemical_formula_weight 760.91 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.60010(10) _cell_length_b 10.4252(2) _cell_length_c 14.7935(2) _cell_angle_alpha 81.3670(10) _cell_angle_beta 80.8880(10) _cell_angle_gamma 76.8880(10) _cell_volume 971.93(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7162 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.30 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details sadabs _exptl_special_details ; crystals had low diffracting power, the diffrn_measured_fraction_theta_full is thus low Absolute configurations have been fixed based on known configurations The starting porphyrin being chiral and enantiopure the space group is thus necessarly noncentrosymmetric ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17081 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.31 _reflns_number_total 8316 _reflns_number_gt 7030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. absolute configurations were determined based on known configurations ; _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^)+(0.0363P)^2^+0.5856P] 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 -0.3(18) _refine_ls_number_reflns 8316 _refine_ls_number_parameters 527 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.003 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 0.1051(4) 0.5267(2) 0.56612(17) 0.0227(6) Uani 1 1 d . . . H1A H 0.1728 0.5069 0.6147 0.027 Uiso 1 1 calc R . . N2 N 0.0420(4) 0.6176(2) 0.74707(17) 0.0222(6) Uani 1 1 d . . . N3 N 0.4584(4) 0.4732(2) 0.78294(17) 0.0209(6) Uani 1 1 d . . . H3A H 0.3899 0.4910 0.7346 0.025 Uiso 1 1 calc R . . N4 N 0.5248(4) 0.3820(2) 0.60185(17) 0.0211(6) Uani 1 1 d . . . C1 C 0.1742(5) 0.4793(3) 0.4834(2) 0.0214(7) Uani 1 1 d . . . C2 C 0.0161(6) 0.5336(3) 0.4234(2) 0.0276(7) Uani 1 1 d . . . H2 H 0.0220 0.5163 0.3617 0.033 Uiso 1 1 calc R . . C3 C -0.1424(5) 0.6135(3) 0.4707(2) 0.0277(7) Uani 1 1 d . . . H3 H -0.2676 0.6627 0.4480 0.033 Uiso 1 1 calc R . . C4 C -0.0885(5) 0.6112(3) 0.5615(2) 0.0204(6) Uani 1 1 d . . . C5 C -0.2015(5) 0.6893(3) 0.6287(2) 0.0238(7) Uani 1 1 d . . . C6 C -0.1415(5) 0.6881(3) 0.7154(2) 0.0203(6) Uani 1 1 d . . . C7 C -0.2696(5) 0.7651(3) 0.7874(2) 0.0266(7) Uani 1 1 d . . . H7 H -0.4026 0.8227 0.7832 0.032 Uiso 1 1 calc R . . C8 C -0.1617(5) 0.7381(3) 0.8605(2) 0.0257(7) Uani 1 1 d . . . H8 H -0.2056 0.7724 0.9181 0.031 Uiso 1 1 calc R . . C9 C 0.0328(5) 0.6477(3) 0.8352(2) 0.0219(7) Uani 1 1 d . . . C10 C 0.1958(5) 0.6046(3) 0.8910(2) 0.0234(7) Uani 1 1 d . . . C11 C 0.3916(5) 0.5241(3) 0.8656(2) 0.0227(7) Uani 1 1 d . . . C12 C 0.5509(5) 0.4723(3) 0.9250(2) 0.0255(7) Uani 1 1 d . . . H12 H 0.5465 0.4915 0.9862 0.031 Uiso 1 1 calc R . . C13 C 0.7086(5) 0.3910(3) 0.8778(2) 0.0242(7) Uani 1 1 d . . . H13 H 0.8355 0.3431 0.8996 0.029 Uiso 1 1 calc R . . C14 C 0.6489(5) 0.3905(3) 0.7888(2) 0.0230(7) Uani 1 1 d . . . C15 C 0.7611(4) 0.3115(3) 0.7209(2) 0.0190(6) Uani 1 1 d . . . C16 C 0.7060(5) 0.3094(3) 0.6333(2) 0.0226(6) Uani 1 1 d . . . C17 C 0.8282(5) 0.2325(3) 0.5647(2) 0.0239(7) Uani 1 1 d . . . H17 H 0.9609 0.1747 0.5694 0.029 Uiso 1 1 calc R . . C18 C 0.7200(5) 0.2572(3) 0.4914(2) 0.0247(7) Uani 1 1 d . . . H18 H 0.7629 0.2196 0.4350 0.030 Uiso 1 1 calc R . . C19 C 0.5272(5) 0.3512(3) 0.5145(2) 0.0222(6) Uani 1 1 d . . . C20 C 0.3684(5) 0.3971(3) 0.4583(2) 0.0219(7) Uani 1 1 d . . . C21 C -0.3938(5) 0.7861(3) 0.6035(2) 0.0229(7) Uani 1 1 d . . . C22 C -0.3982(5) 0.9217(3) 0.5920(2) 0.0269(7) Uani 1 1 d . . . H22 H -0.2804 0.9537 0.6016 0.032 Uiso 1 1 calc R . . C23 C -0.5770(5) 1.0089(3) 0.5664(3) 0.0335(8) Uani 1 1 d . . . H23 H -0.5786 1.1012 0.5593 0.040 Uiso 1 1 calc R . . N5 N -0.7462(4) 0.9713(3) 0.5512(2) 0.0315(7) Uani 1 1 d . . . C24 C -0.7411(6) 0.8420(3) 0.5624(2) 0.0312(8) Uani 1 1 d . . . H24 H -0.8620 0.8131 0.5532 0.037 Uiso 1 1 calc R . . C25 C -0.5681(5) 0.7464(3) 0.5871(2) 0.0271(7) Uani 1 1 d . . . H25 H -0.5705 0.6548 0.5925 0.032 Uiso 1 1 calc R . . C26 C 0.1591(5) 0.6495(3) 0.9844(2) 0.0232(7) Uani 1 1 d . . . C27 C 0.2764(5) 0.7330(3) 1.0065(2) 0.0279(7) Uani 1 1 d . . . H27 H 0.3841 0.7596 0.9619 0.034 Uiso 1 1 calc R . . C28 C 0.2384(5) 0.7785(3) 1.0932(2) 0.0303(7) Uani 1 1 d . . . H28 H 0.3196 0.8359 1.1068 0.036 Uiso 1 1 calc R . . C29 C 0.0850(5) 0.7405(3) 1.1585(2) 0.0273(7) Uani 1 1 d . . . C30 C -0.0342(6) 0.6544(3) 1.1386(2) 0.0306(8) Uani 1 1 d . . . H30 H -0.1404 0.6272 1.1837 0.037 Uiso 1 1 calc R . . C31 C 0.0053(6) 0.6098(3) 1.0522(2) 0.0318(8) Uani 1 1 d . . . H31 H -0.0740 0.5510 1.0390 0.038 Uiso 1 1 calc R . . O1 O 0.0255(4) 0.7833(2) 1.24389(16) 0.0355(6) Uani 1 1 d . . . C32 C 0.1405(5) 0.8701(3) 1.2725(2) 0.0331(8) Uani 1 1 d . . . H32 H 0.1755 0.9357 1.2190 0.040 Uiso 1 1 calc R . . C33 C -0.0089(6) 0.9426(4) 1.3466(3) 0.0426(9) Uani 1 1 d . . . H33A H -0.1262 1.0023 1.3188 0.064 Uiso 1 1 calc R . . H33B H 0.0660 0.9944 1.3747 0.064 Uiso 1 1 calc R . . H33C H -0.0626 0.8780 1.3940 0.064 Uiso 1 1 calc R . . C34 C 0.3411(7) 0.7871(4) 1.3047(3) 0.0429(9) Uani 1 1 d . . . H34A H 0.4076 0.7231 1.2602 0.051 Uiso 1 1 calc R . . H34B H 0.3071 0.7358 1.3650 0.051 Uiso 1 1 calc R . . C35 C 0.4950(5) 0.8704(3) 1.3143(2) 0.0493(7) Uani 1 1 d . . . H35A H 0.5199 0.9271 1.2562 0.074 Uiso 1 1 calc R . . H35B H 0.6276 0.8122 1.3288 0.074 Uiso 1 1 calc R . . H35C H 0.4370 0.9260 1.3640 0.074 Uiso 1 1 calc R . . C36 C 0.9538(4) 0.2136(3) 0.7469(2) 0.0207(6) Uani 1 1 d . . . C37 C 1.1342(5) 0.2525(3) 0.7615(2) 0.0282(7) Uani 1 1 d . . . H37 H 1.1412 0.3436 0.7527 0.034 Uiso 1 1 calc R . . C38 C 1.3019(5) 0.1567(3) 0.7888(3) 0.0311(8) Uani 1 1 d . . . H38 H 1.4217 0.1857 0.7994 0.037 Uiso 1 1 calc R . . N6 N 1.3086(5) 0.0264(3) 0.8016(2) 0.0324(7) Uani 1 1 d . . . C39 C 1.1348(5) -0.0098(3) 0.7866(2) 0.0319(8) Uani 1 1 d . . . H39 H 1.1339 -0.1018 0.7948 0.038 Uiso 1 1 calc R . . C40 C 0.9571(5) 0.0779(3) 0.7601(2) 0.0286(7) Uani 1 1 d . . . H40 H 0.8388 0.0460 0.7510 0.034 Uiso 1 1 calc R . . C41 C 0.4080(5) 0.3539(3) 0.3634(2) 0.0247(7) Uani 1 1 d . . . C42 C 0.5637(5) 0.3908(3) 0.2979(2) 0.0270(7) Uani 1 1 d . . . H42 H 0.6507 0.4436 0.3129 0.032 Uiso 1 1 calc R . . C43 C 0.5950(6) 0.3523(3) 0.2107(3) 0.0331(8) Uani 1 1 d . . . H43 H 0.7028 0.3793 0.1664 0.040 Uiso 1 1 calc R . . C44 C 0.4727(6) 0.2753(3) 0.1867(2) 0.0315(8) Uani 1 1 d . . . C45 C 0.3109(6) 0.2389(3) 0.2513(2) 0.0338(8) Uani 1 1 d . . . H45 H 0.2210 0.1887 0.2355 0.041 Uiso 1 1 calc R . . C46 C 0.2836(6) 0.2775(3) 0.3393(2) 0.0316(8) Uani 1 1 d . . . H46 H 0.1764 0.2506 0.3840 0.038 Uiso 1 1 calc R . . O2 O 0.5224(4) 0.2397(2) 0.09968(16) 0.0385(6) Uani 1 1 d . . . C47 C 0.4121(6) 0.1510(3) 0.0705(2) 0.0347(8) Uani 1 1 d . . . H47 H 0.3795 0.0843 0.1238 0.042 Uiso 1 1 calc R . . C48 C 0.2089(7) 0.2264(4) 0.0347(3) 0.0480(10) Uani 1 1 d . . . H48A H 0.2398 0.2938 -0.0161 0.072 Uiso 1 1 calc R . . H48B H 0.1145 0.2694 0.0846 0.072 Uiso 1 1 calc R . . H48C H 0.1415 0.1644 0.0128 0.072 Uiso 1 1 calc R . . C49 C 0.5639(7) 0.0811(3) -0.0030(3) 0.0384(9) Uani 1 1 d . . . H49A H 0.6043 0.1479 -0.0535 0.046 Uiso 1 1 calc R . . H49B H 0.4933 0.0233 -0.0289 0.046 Uiso 1 1 calc R . . C50 C 0.7608(5) -0.0027(3) 0.0341(2) 0.0540(8) Uani 1 1 d . . . H50A H 0.7240 -0.0771 0.0776 0.081 Uiso 1 1 calc R . . H50B H 0.8231 0.0520 0.0657 0.081 Uiso 1 1 calc R . . H50C H 0.8618 -0.0369 -0.0172 0.081 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 0.0250(16) 0.0222(12) 0.0195(13) -0.0020(10) -0.0066(12) -0.0001(10) N2 0.0218(15) 0.0213(11) 0.0234(14) -0.0029(10) -0.0063(12) -0.0020(10) N3 0.0177(14) 0.0203(11) 0.0227(13) -0.0031(10) -0.0032(11) 0.0010(10) N4 0.0173(14) 0.0210(11) 0.0231(13) -0.0028(10) -0.0019(11) -0.0004(10) C1 0.0211(17) 0.0223(13) 0.0209(15) -0.0009(11) -0.0042(14) -0.0050(12) C2 0.034(2) 0.0270(15) 0.0211(15) -0.0053(12) -0.0046(15) -0.0021(14) C3 0.0265(18) 0.0259(15) 0.0298(18) 0.0013(12) -0.0133(16) 0.0000(13) C4 0.0172(16) 0.0201(13) 0.0244(16) -0.0017(11) -0.0053(14) -0.0037(11) C5 0.0276(18) 0.0183(12) 0.0260(16) -0.0014(11) -0.0041(14) -0.0065(12) C6 0.0137(15) 0.0197(13) 0.0255(15) -0.0052(11) 0.0000(13) 0.0005(11) C7 0.0219(17) 0.0241(14) 0.0298(17) -0.0047(12) -0.0006(14) 0.0027(12) C8 0.0234(17) 0.0280(14) 0.0223(15) -0.0062(11) -0.0020(14) 0.0032(12) C9 0.0214(17) 0.0211(13) 0.0220(15) -0.0061(11) -0.0019(13) -0.0006(12) C10 0.0241(18) 0.0233(14) 0.0235(16) 0.0001(12) -0.0065(14) -0.0061(12) C11 0.0252(18) 0.0206(13) 0.0222(15) -0.0042(11) -0.0043(14) -0.0027(12) C12 0.0214(17) 0.0299(15) 0.0253(16) -0.0020(12) -0.0106(14) -0.0013(12) C13 0.0209(17) 0.0269(14) 0.0244(16) -0.0062(12) -0.0040(14) -0.0012(12) C14 0.0239(18) 0.0189(13) 0.0250(16) -0.0006(11) -0.0047(14) -0.0023(12) C15 0.0089(14) 0.0196(12) 0.0265(16) -0.0016(11) -0.0024(13) 0.0004(10) C16 0.0223(17) 0.0205(13) 0.0245(16) -0.0009(11) -0.0029(13) -0.0049(11) C17 0.0182(16) 0.0255(14) 0.0253(16) -0.0056(12) -0.0012(14) 0.0011(12) C18 0.0220(17) 0.0237(13) 0.0275(16) -0.0088(11) 0.0018(14) -0.0026(12) C19 0.0216(17) 0.0194(13) 0.0247(16) -0.0012(11) -0.0018(14) -0.0043(12) C20 0.0235(17) 0.0189(13) 0.0221(15) -0.0072(11) 0.0011(14) -0.0016(11) C21 0.0259(18) 0.0194(13) 0.0206(15) -0.0046(11) -0.0004(13) 0.0008(12) C22 0.0221(18) 0.0242(14) 0.0343(18) -0.0054(13) -0.0045(15) -0.0027(12) C23 0.034(2) 0.0200(14) 0.043(2) -0.0046(13) -0.0094(17) 0.0032(13) N5 0.0218(15) 0.0308(13) 0.0374(16) -0.0012(12) -0.0072(13) 0.0041(11) C24 0.0227(19) 0.0381(17) 0.0343(19) -0.0010(14) -0.0066(15) -0.0095(14) C25 0.0225(18) 0.0247(14) 0.0336(18) 0.0000(12) -0.0071(15) -0.0041(12) C26 0.0206(17) 0.0244(14) 0.0218(16) -0.0041(12) -0.0011(13) 0.0013(12) C27 0.0280(19) 0.0342(16) 0.0239(16) -0.0066(12) -0.0027(15) -0.0095(13) C28 0.0284(18) 0.0370(15) 0.0292(16) -0.0123(12) -0.0024(14) -0.0098(12) C29 0.0272(18) 0.0332(14) 0.0232(16) -0.0084(11) -0.0079(14) -0.0034(12) C30 0.035(2) 0.0322(16) 0.0244(16) -0.0067(13) 0.0031(15) -0.0098(14) C31 0.040(2) 0.0309(16) 0.0274(17) -0.0052(13) -0.0035(17) -0.0123(15) O1 0.0405(14) 0.0469(12) 0.0249(11) -0.0149(9) 0.0005(10) -0.0176(10) C32 0.0314(18) 0.0408(16) 0.0312(17) -0.0122(13) -0.0053(14) -0.0098(13) C33 0.041(2) 0.0505(19) 0.0373(19) -0.0225(15) 0.0070(16) -0.0087(15) C34 0.052(2) 0.0450(18) 0.0325(17) -0.0048(14) -0.0117(17) -0.0076(16) C35 0.0413(16) 0.0634(18) 0.0420(15) 0.0042(13) -0.0072(13) -0.0142(13) C36 0.0124(16) 0.0255(14) 0.0228(15) -0.0009(11) -0.0027(13) -0.0020(11) C37 0.0233(18) 0.0237(14) 0.0361(19) 0.0002(13) -0.0018(15) -0.0057(13) C38 0.0160(17) 0.0360(17) 0.0371(19) -0.0010(14) -0.0046(15) 0.0019(13) N6 0.0267(16) 0.0332(14) 0.0317(15) -0.0020(12) -0.0056(13) 0.0055(12) C39 0.035(2) 0.0236(14) 0.0349(19) -0.0019(12) -0.0066(16) -0.0010(14) C40 0.0272(19) 0.0234(14) 0.0360(18) -0.0044(13) -0.0097(16) -0.0028(12) C41 0.0256(18) 0.0254(14) 0.0231(16) -0.0059(12) -0.0049(14) -0.0021(13) C42 0.0237(19) 0.0304(15) 0.0279(16) -0.0080(12) -0.0014(15) -0.0060(13) C43 0.034(2) 0.0398(18) 0.0252(16) -0.0024(14) 0.0020(16) -0.0122(15) C44 0.043(2) 0.0270(14) 0.0221(16) -0.0054(11) 0.0035(15) -0.0056(13) C45 0.040(2) 0.0345(16) 0.0309(17) -0.0116(13) -0.0005(16) -0.0144(14) C46 0.029(2) 0.0348(16) 0.0305(18) -0.0107(13) 0.0064(16) -0.0077(14) O2 0.0561(17) 0.0381(11) 0.0240(11) -0.0109(9) 0.0076(11) -0.0195(11) C47 0.052(2) 0.0282(13) 0.0255(16) -0.0066(11) 0.0001(15) -0.0128(13) C48 0.040(2) 0.051(2) 0.052(2) -0.0106(17) -0.0098(18) -0.0014(16) C49 0.054(2) 0.0343(14) 0.0296(16) -0.0092(12) -0.0127(16) -0.0066(14) C50 0.0528(19) 0.0525(17) 0.0534(17) -0.0205(14) -0.0097(15) 0.0071(14) _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 C1 1.361(4) . ? N1 C4 1.383(4) . ? N1 H1A 0.8800 . ? N2 C6 1.378(3) . ? N2 C9 1.375(4) . ? N3 C14 1.361(4) . ? N3 C11 1.374(4) . ? N3 H3A 0.8800 . ? N4 C19 1.374(4) . ? N4 C16 1.371(4) . ? C1 C20 1.401(4) . ? C1 C2 1.439(4) . ? C2 C3 1.351(5) . ? C2 H2 0.9500 . ? C3 C4 1.439(4) . ? C3 H3 0.9500 . ? C4 C5 1.393(4) . ? C5 C6 1.398(4) . ? C5 C21 1.491(4) . ? C6 C7 1.469(4) . ? C7 C8 1.348(4) . ? C7 H7 0.9500 . ? C8 C9 1.443(4) . ? C8 H8 0.9500 . ? C9 C10 1.411(4) . ? C10 C11 1.402(4) . ? C10 C26 1.492(4) . ? C11 C12 1.436(4) . ? C12 C13 1.356(5) . ? C12 H12 0.9500 . ? C13 C14 1.433(4) . ? C13 H13 0.9500 . ? C14 C15 1.405(4) . ? C15 C16 1.405(4) . ? C15 C36 1.502(4) . ? C16 C17 1.419(4) . ? C17 C18 1.353(4) . ? C17 H17 0.9500 . ? C18 C19 1.447(4) . ? C18 H18 0.9500 . ? C19 C20 1.396(4) . ? C20 C41 1.504(4) . ? C21 C25 1.374(4) . ? C21 C22 1.393(4) . ? C22 C23 1.384(4) . ? C22 H22 0.9500 . ? C23 N5 1.325(4) . ? C23 H23 0.9500 . ? N5 C24 1.327(4) . ? C24 C25 1.392(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.390(5) . ? C26 C31 1.396(5) . ? C27 C28 1.400(4) . ? C27 H27 0.9500 . ? C28 C29 1.368(5) . ? C28 H28 0.9500 . ? C29 O1 1.372(4) . ? C29 C30 1.408(5) . ? C30 C31 1.392(5) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? O1 C32 1.450(4) . ? C32 C34 1.512(5) . ? C32 C33 1.522(5) . ? C32 H32 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.513(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C37 1.399(4) . ? C36 C40 1.394(4) . ? C37 C38 1.381(4) . ? C37 H37 0.9500 . ? C38 N6 1.335(4) . ? C38 H38 0.9500 . ? N6 C39 1.345(5) . ? C39 C40 1.385(4) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C46 1.382(5) . ? C41 C42 1.377(5) . ? C42 C43 1.379(5) . ? C42 H42 0.9500 . ? C43 C44 1.375(5) . ? C43 H43 0.9500 . ? C44 O2 1.363(4) . ? C44 C45 1.396(5) . ? C45 C46 1.391(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? O2 C47 1.448(4) . ? C47 C49 1.509(5) . ? C47 C48 1.523(5) . ? C47 H47 1.0000 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C49 C50 1.523(5) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 109.0(2) . . ? C1 N1 H1A 125.5 . . ? C4 N1 H1A 125.5 . . ? C6 N2 C9 106.2(2) . . ? C14 N3 C11 108.1(2) . . ? C14 N3 H3A 125.9 . . ? C11 N3 H3A 125.9 . . ? C19 N4 C16 106.9(2) . . ? N1 C1 C20 126.7(3) . . ? N1 C1 C2 108.0(3) . . ? C20 C1 C2 125.2(3) . . ? C3 C2 C1 107.7(3) . . ? C3 C2 H2 126.2 . . ? C1 C2 H2 126.2 . . ? C2 C3 C4 108.1(3) . . ? C2 C3 H3 126.0 . . ? C4 C3 H3 126.0 . . ? C5 C4 N1 126.6(3) . . ? C5 C4 C3 126.0(3) . . ? N1 C4 C3 107.2(3) . . ? C4 C5 C6 124.7(3) . . ? C4 C5 C21 117.0(3) . . ? C6 C5 C21 118.2(3) . . ? N2 C6 C5 126.8(3) . . ? N2 C6 C7 109.4(3) . . ? C5 C6 C7 123.8(3) . . ? C8 C7 C6 106.7(3) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C7 C8 C9 107.3(3) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? N2 C9 C10 125.2(3) . . ? N2 C9 C8 110.4(3) . . ? C10 C9 C8 124.3(3) . . ? C9 C10 C11 125.4(3) . . ? C9 C10 C26 117.7(3) . . ? C11 C10 C26 116.9(3) . . ? N3 C11 C10 126.4(3) . . ? N3 C11 C12 108.3(3) . . ? C10 C11 C12 125.2(3) . . ? C13 C12 C11 107.4(3) . . ? C13 C12 H12 126.3 . . ? C11 C12 H12 126.3 . . ? C12 C13 C14 107.4(3) . . ? C12 C13 H13 126.3 . . ? C14 C13 H13 126.3 . . ? N3 C14 C15 125.2(3) . . ? N3 C14 C13 108.8(3) . . ? C15 C14 C13 125.9(3) . . ? C16 C15 C14 126.9(2) . . ? C16 C15 C36 116.6(3) . . ? C14 C15 C36 116.3(3) . . ? N4 C16 C15 124.5(3) . . ? N4 C16 C17 110.2(3) . . ? C15 C16 C17 125.4(3) . . ? C18 C17 C16 107.0(3) . . ? C18 C17 H17 126.5 . . ? C16 C17 H17 126.5 . . ? C17 C18 C19 107.6(3) . . ? C17 C18 H18 126.2 . . ? C19 C18 H18 126.2 . . ? N4 C19 C20 126.5(3) . . ? N4 C19 C18 108.4(3) . . ? C20 C19 C18 125.0(3) . . ? C19 C20 C1 125.2(3) . . ? C19 C20 C41 117.5(3) . . ? C1 C20 C41 117.3(3) . . ? C25 C21 C22 117.6(3) . . ? C25 C21 C5 122.2(3) . . ? C22 C21 C5 120.1(3) . . ? C23 C22 C21 118.8(3) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? N5 C23 C22 123.9(3) . . ? N5 C23 H23 118.0 . . ? C22 C23 H23 118.0 . . ? C23 N5 C24 116.9(3) . . ? N5 C24 C25 123.5(3) . . ? N5 C24 H24 118.2 . . ? C25 C24 H24 118.2 . . ? C21 C25 C24 119.2(3) . . ? C21 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C27 C26 C31 118.0(3) . . ? C27 C26 C10 120.9(3) . . ? C31 C26 C10 121.1(3) . . ? C28 C27 C26 121.1(3) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C29 C28 C27 120.3(3) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.9 . . ? O1 C29 C28 125.9(3) . . ? O1 C29 C30 114.2(3) . . ? C28 C29 C30 119.9(3) . . ? C31 C30 C29 119.3(3) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C30 C31 C26 121.4(3) . . ? C30 C31 H31 119.3 . . ? C26 C31 H31 119.3 . . ? C29 O1 C32 118.9(3) . . ? O1 C32 C34 108.7(3) . . ? O1 C32 C33 105.5(3) . . ? C34 C32 C33 114.4(3) . . ? O1 C32 H32 109.4 . . ? C34 C32 H32 109.4 . . ? C33 C32 H32 109.4 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 C35 112.4(3) . . ? C32 C34 H34A 109.1 . . ? C35 C34 H34A 109.1 . . ? C32 C34 H34B 109.1 . . ? C35 C34 H34B 109.1 . . ? H34A C34 H34B 107.9 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C37 C36 C40 116.9(3) . . ? C37 C36 C15 122.5(3) . . ? C40 C36 C15 120.5(3) . . ? C38 C37 C36 119.1(3) . . ? C38 C37 H37 120.5 . . ? C36 C37 H37 120.5 . . ? N6 C38 C37 125.0(3) . . ? N6 C38 H38 117.5 . . ? C37 C38 H38 117.5 . . ? C38 N6 C39 115.3(3) . . ? N6 C39 C40 124.5(3) . . ? N6 C39 H39 117.8 . . ? C40 C39 H39 117.8 . . ? C39 C40 C36 119.2(3) . . ? C39 C40 H40 120.4 . . ? C36 C40 H40 120.4 . . ? C46 C41 C42 118.2(3) . . ? C46 C41 C20 120.1(3) . . ? C42 C41 C20 121.7(3) . . ? C41 C42 C43 120.9(3) . . ? C41 C42 H42 119.6 . . ? C43 C42 H42 119.6 . . ? C44 C43 C42 121.1(4) . . ? C44 C43 H43 119.5 . . ? C42 C43 H43 119.5 . . ? C43 C44 O2 115.9(3) . . ? C43 C44 C45 119.1(3) . . ? O2 C44 C45 125.0(3) . . ? C46 C45 C44 118.9(3) . . ? C46 C45 H45 120.6 . . ? C44 C45 H45 120.6 . . ? C41 C46 C45 121.8(4) . . ? C41 C46 H46 119.1 . . ? C45 C46 H46 119.1 . . ? C44 O2 C47 119.8(3) . . ? O2 C47 C49 105.4(3) . . ? O2 C47 C48 111.4(3) . . ? C49 C47 C48 112.1(3) . . ? O2 C47 H47 109.3 . . ? C49 C47 H47 109.3 . . ? C48 C47 H47 109.3 . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C47 C49 C50 112.4(3) . . ? C47 C49 H49A 109.1 . . ? C50 C49 H49A 109.1 . . ? C47 C49 H49B 109.1 . . ? C50 C49 H49B 109.1 . . ? H49A C49 H49B 107.9 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.343 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 942056' ####################################################################### # # 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_compound _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H55 N7 O6 Zn' _chemical_formula_weight 951.41 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 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' _cell_length_a 34.3268(10) _cell_length_b 14.1957(3) _cell_length_c 21.8632(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.382(2) _cell_angle_gamma 90.00 _cell_volume 9851.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9575 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 23.61 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4000 _exptl_absorpt_coefficient_mu 0.555 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9517 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_process_details sadabs _exptl_special_details ; the crystals are of poor quality and collapse within few minutes at room temperture The corresponding retraints were used in the refinements EADP C97 C98 C99 C100 EADP C82 C83 C84 C85 EADP C47 C48 C49 C50 EADP C32 C33 C34 C35 DFIX 1.54 0.02 C32 C35 C32 C33 C33 C34 DFIX 1.54 0.02 C47 C48 C48 C49 C47 C50 DFIX 1.54 0.02 C82 C83 C83 C84 C82 C85 DFIX 1.54 0.02 C97 C98 C98 C99 C97 C100 DFIX 2.52 0.02 C33 C35 C48 C50 C83 C85 C98 C100 DFIX 3.02 0.02 C99 C100 the H of the 6 Methyl groups are disordered,the HFIX 123 command to calculate the corresponding H positions were used, thus leading to Large Non-Solvent H Uiso(max)/Uiso(min) ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26372 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0948 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 30.13 _reflns_number_total 26372 _reflns_number_gt 14269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1236P)^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 0.119(14) _refine_ls_number_reflns 26372 _refine_ls_number_parameters 981 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1356 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.2225 _refine_ls_wR_factor_gt 0.2011 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.001 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 Zn1 Zn 0.300143(14) 0.65307(3) 0.66741(2) 0.02950(14) Uani 1 1 d . . . N1 N 0.32892(11) 0.7269(3) 0.61486(19) 0.0322(9) Uani 1 1 d . . . N2 N 0.25454(12) 0.7584(3) 0.6429(2) 0.0384(10) Uani 1 1 d . . . N3 N 0.28079(11) 0.6105(3) 0.74145(18) 0.0292(9) Uani 1 1 d . . . N4 N 0.35565(12) 0.5807(3) 0.7137(2) 0.0358(10) Uani 1 1 d . . . C1 C 0.36491(17) 0.7074(4) 0.6098(3) 0.0418(13) Uani 1 1 d . . . C2 C 0.37107(19) 0.7633(5) 0.5584(3) 0.0526(16) Uani 1 1 d . . . H2 H 0.3943 0.7613 0.5448 0.063 Uiso 1 1 calc R . . C3 C 0.33676(15) 0.8184(4) 0.5344(2) 0.0357(12) Uani 1 1 d . . . H3 H 0.3308 0.8646 0.5006 0.043 Uiso 1 1 calc R . . C4 C 0.31201(16) 0.7941(4) 0.5687(2) 0.0387(12) Uani 1 1 d . . . C5 C 0.27075(17) 0.8398(4) 0.5580(3) 0.0380(12) Uani 1 1 d . . . C6 C 0.24554(17) 0.8213(3) 0.5940(3) 0.0361(12) Uani 1 1 d . . . C7 C 0.2081(2) 0.8715(4) 0.5855(3) 0.0577(17) Uani 1 1 d . . . H7 H 0.1952 0.9192 0.5538 0.069 Uiso 1 1 calc R . . C8 C 0.1950(2) 0.8383(4) 0.6305(3) 0.0554(17) Uani 1 1 d . . . H8 H 0.1706 0.8591 0.6371 0.066 Uiso 1 1 calc R . . C9 C 0.22310(17) 0.7660(4) 0.6680(3) 0.0453(14) Uani 1 1 d . . . C10 C 0.21971(15) 0.7160(4) 0.7206(3) 0.0379(12) Uani 1 1 d . . . C11 C 0.24792(14) 0.6430(5) 0.7555(2) 0.0389(12) Uani 1 1 d . . . C12 C 0.24493(18) 0.5954(5) 0.8105(3) 0.0539(16) Uani 1 1 d . . . H12 H 0.2240 0.6039 0.8287 0.065 Uiso 1 1 calc R . . C13 C 0.27804(16) 0.5354(4) 0.8319(3) 0.0459(14) Uani 1 1 d . . . H13 H 0.2856 0.4965 0.8701 0.055 Uiso 1 1 calc R . . C14 C 0.29975(15) 0.5399(4) 0.7877(2) 0.0412(13) Uani 1 1 d . . . C15 C 0.33634(15) 0.4924(4) 0.7950(3) 0.0395(13) Uani 1 1 d . . . C16 C 0.36327(15) 0.5144(3) 0.7616(2) 0.0350(11) Uani 1 1 d . . . C17 C 0.40433(16) 0.4689(4) 0.7758(3) 0.0455(13) Uani 1 1 d . . . H17 H 0.4167 0.4190 0.8059 0.055 Uiso 1 1 calc R . . C18 C 0.42042(16) 0.5144(4) 0.7361(2) 0.0457(14) Uani 1 1 d . . . H18 H 0.4474 0.5034 0.7348 0.055 Uiso 1 1 calc R . . C19 C 0.39056(16) 0.5811(4) 0.6968(3) 0.0405(13) Uani 1 1 d . . . C20 C 0.39669(15) 0.6413(5) 0.6485(2) 0.0429(12) Uani 1 1 d . . . C21 C 0.25679(19) 0.9112(4) 0.5043(3) 0.0375(13) Uani 1 1 d . . . C22 C 0.26253(19) 1.0108(4) 0.5209(3) 0.0537(16) Uani 1 1 d . . . H22 H 0.2760 1.0321 0.5652 0.064 Uiso 1 1 calc R . . H24 H 0.2083 0.9400 0.3470 0.064 Uiso 1 1 d R . . H23 H 0.2511 1.1367 0.4806 0.064 Uiso 1 1 d R . . C23 C 0.24766(17) 1.0703(3) 0.4699(2) 0.0372(12) Uani 1 1 d . . . N5 N 0.22803(12) 1.0502(3) 0.40721(19) 0.0320(9) Uani 1 1 d . . . C24 C 0.22236(18) 0.9574(4) 0.3920(3) 0.0386(13) Uani 1 1 d . . . C25 C 0.23732(18) 0.8869(4) 0.4404(3) 0.0439(14) Uani 1 1 d . . . H25 H 0.2337 0.8224 0.4281 0.053 Uiso 1 1 calc R . . C26 C 0.18283(18) 0.7366(4) 0.7384(3) 0.0470(14) Uani 1 1 d . . . C27 C 0.1508(2) 0.6768(7) 0.7254(6) 0.139(5) Uani 1 1 d . . . H27 H 0.1509 0.6215 0.7009 0.166 Uiso 1 1 calc R . . C28 C 0.1160(3) 0.6907(12) 0.7461(5) 0.145 Uani 1 1 d . . . H28 H 0.0956 0.6426 0.7401 0.174 Uiso 1 1 calc R . . C29 C 0.1133(3) 0.7684(8) 0.7726(5) 0.105(3) Uani 1 1 d . . . C30 C 0.1450(2) 0.8353(6) 0.7867(3) 0.080(3) Uani 1 1 d . . . H30 H 0.1432 0.8914 0.8091 0.096 Uiso 1 1 calc R . . C31 C 0.17959(19) 0.8219(6) 0.7686(3) 0.069(2) Uani 1 1 d . . . H31 H 0.2004 0.8694 0.7766 0.083 Uiso 1 1 calc R . . O1 O 0.0769(2) 0.7889(5) 0.7801(6) 0.175 Uani 1 1 d . . . C32 C 0.0700(5) 0.8741(13) 0.8156(11) 0.307(8) Uani 1 1 d D . . H32 H 0.0892 0.9280 0.8172 0.368 Uiso 1 1 calc R . . C33 C 0.0272(4) 0.9003(12) 0.7963(10) 0.307(8) Uani 1 1 d D . . H33A H 0.0224 0.9621 0.7736 0.368 Uiso 1 1 calc R . . H33B H 0.0200 0.9064 0.8360 0.368 Uiso 1 1 calc R . . C34 C -0.0005(4) 0.8270(13) 0.7506(10) 0.307(8) Uani 1 1 d D . . H34A H -0.0301 0.8458 0.7369 0.460 Uiso 0.50 1 calc PR . . H34B H 0.0038 0.7663 0.7736 0.460 Uiso 0.50 1 calc PR . . H34C H 0.0067 0.8212 0.7115 0.460 Uiso 0.50 1 calc PR . . H34D H 0.0171 0.7764 0.7444 0.460 Uiso 0.50 1 calc PR . . H34E H -0.0169 0.8559 0.7078 0.460 Uiso 0.50 1 calc PR . . H34F H -0.0197 0.8010 0.7699 0.460 Uiso 0.50 1 calc PR . . C35 C 0.0865(5) 0.8099(13) 0.8769(10) 0.307(8) Uani 1 1 d D . . H35A H 0.1163 0.7957 0.8876 0.460 Uiso 0.50 1 calc PR . . H35B H 0.0703 0.7511 0.8677 0.460 Uiso 0.50 1 calc PR . . H35C H 0.0834 0.8420 0.9145 0.460 Uiso 0.50 1 calc PR . . H35D H 0.0637 0.7969 0.8923 0.460 Uiso 0.50 1 calc PR . . H35E H 0.1097 0.8414 0.9122 0.460 Uiso 0.50 1 calc PR . . H35F H 0.0966 0.7505 0.8654 0.460 Uiso 0.50 1 calc PR . . C36 C 0.34826(15) 0.4144(5) 0.8462(3) 0.0462(15) Uani 1 1 d . . . C37 C 0.32294(17) 0.3440(4) 0.8397(3) 0.0424(13) Uani 1 1 d . . . H37 H 0.2976 0.3397 0.8016 0.051 Uiso 1 1 calc R . . C38 C 0.3332(2) 0.2706(4) 0.8911(3) 0.0560(16) Uani 1 1 d . . . H38 H 0.3147 0.2185 0.8852 0.067 Uiso 1 1 calc R . . N6 N 0.36681(17) 0.2758(4) 0.9439(3) 0.0641(15) Uani 1 1 d . . . C39 C 0.39372(19) 0.3536(5) 0.9497(3) 0.0560(16) Uani 1 1 d . . . H39 H 0.4191 0.3589 0.9877 0.067 Uiso 1 1 calc R . . C40 C 0.38438(17) 0.4190(5) 0.9034(3) 0.0526(16) Uani 1 1 d . . . H40 H 0.4030 0.4709 0.9095 0.063 Uiso 1 1 calc R . . C41 C 0.43563(18) 0.6394(5) 0.6395(2) 0.0590(17) Uani 1 1 d . . . C42 C 0.4503(3) 0.5631(5) 0.6173(5) 0.103(3) Uani 1 1 d . . . H42 H 0.4343 0.5066 0.6063 0.124 Uiso 1 1 calc R . . C43 C 0.4933(2) 0.5701(5) 0.6105(3) 0.071(2) Uani 1 1 d . . . H43 H 0.5063 0.5166 0.6001 0.085 Uiso 1 1 calc R . . C44 C 0.51105(19) 0.6529(5) 0.6197(3) 0.0710(17) Uani 1 1 d . . . C45 C 0.4979(2) 0.7314(5) 0.6417(4) 0.0712(18) Uani 1 1 d . . . H45 H 0.5142 0.7874 0.6500 0.085 Uiso 1 1 calc R . . C46 C 0.46077(19) 0.7293(6) 0.6522(3) 0.0701(18) Uani 1 1 d . . . H46 H 0.4511 0.7839 0.6673 0.084 Uiso 1 1 calc R . . O2 O 0.54876(14) 0.6672(3) 0.6072(3) 0.0870(14) Uani 1 1 d . . . C47 C 0.5729(2) 0.5875(6) 0.6033(5) 0.1014(14) Uani 1 1 d D . . H47 H 0.5536 0.5405 0.5723 0.122 Uiso 1 1 calc R . . C48 C 0.6011(2) 0.6284(5) 0.5712(5) 0.1014(14) Uani 1 1 d D . . H48A H 0.6181 0.6798 0.5995 0.122 Uiso 1 1 calc R . . H48B H 0.5833 0.6563 0.5281 0.122 Uiso 1 1 calc R . . C49 C 0.6314(2) 0.5551(6) 0.5598(5) 0.1014(14) Uani 1 1 d D . . H49A H 0.6560 0.5464 0.6009 0.152 Uiso 1 1 calc R . . H49B H 0.6405 0.5778 0.5250 0.152 Uiso 1 1 calc R . . H49C H 0.6166 0.4949 0.5462 0.152 Uiso 1 1 calc R . . C50 C 0.5944(2) 0.5416(6) 0.6689(4) 0.1014(14) Uani 1 1 d D . . H50A H 0.6142 0.5861 0.6994 0.152 Uiso 1 1 calc R . . H50B H 0.6097 0.4858 0.6638 0.152 Uiso 1 1 calc R . . H50C H 0.5733 0.5228 0.6867 0.152 Uiso 1 1 calc R . . Zn2 Zn 0.702328(14) 0.64859(3) 0.83170(2) 0.02667(13) Uani 1 1 d . . . N7 N 0.67247(11) 0.5774(3) 0.88415(18) 0.0291(9) Uani 1 1 d . . . N8 N 0.74403(12) 0.5381(3) 0.85185(17) 0.0324(9) Uani 1 1 d . . . N9 N 0.72181(12) 0.6884(3) 0.75717(19) 0.0345(10) Uani 1 1 d . . . N10 N 0.64772(12) 0.7285(3) 0.78490(18) 0.0299(9) Uani 1 1 d . . . C51 C 0.63402(14) 0.6050(4) 0.8905(2) 0.0308(11) Uani 1 1 d . . . C52 C 0.62795(14) 0.5470(4) 0.9390(2) 0.0357(12) Uani 1 1 d . . . H52 H 0.6043 0.5503 0.9513 0.043 Uiso 1 1 calc R . . C53 C 0.65948(19) 0.4884(4) 0.9645(3) 0.0499(15) Uani 1 1 d . . . H53 H 0.6631 0.4436 0.9985 0.060 Uiso 1 1 calc R . . C54 C 0.68940(14) 0.5062(3) 0.9287(2) 0.0299(11) Uani 1 1 d . . . C55 C 0.72390(16) 0.4591(4) 0.9369(2) 0.0314(11) Uani 1 1 d . . . C56 C 0.74957(17) 0.4693(4) 0.9002(3) 0.0361(12) Uani 1 1 d . . . C57 C 0.78602(18) 0.4131(4) 0.9057(3) 0.0521(15) Uani 1 1 d . . . H57 H 0.7973 0.3628 0.9359 0.063 Uiso 1 1 calc R . . C58 C 0.8012(2) 0.4437(5) 0.8612(3) 0.0629(19) Uani 1 1 d . . . H58 H 0.8245 0.4186 0.8532 0.075 Uiso 1 1 calc R . . C59 C 0.77472(16) 0.5237(4) 0.8272(3) 0.0396(12) Uani 1 1 d . . . C60 C 0.77969(16) 0.5749(4) 0.7763(2) 0.0431(14) Uani 1 1 d . . . C61 C 0.75374(13) 0.6490(4) 0.7428(2) 0.0306(10) Uani 1 1 d . . . C62 C 0.75595(16) 0.6953(4) 0.6849(2) 0.0407(12) Uani 1 1 d . . . H62 H 0.7751 0.6807 0.6644 0.049 Uiso 1 1 calc R . . C63 C 0.72598(16) 0.7627(4) 0.6656(3) 0.0400(12) Uani 1 1 d . . . H63 H 0.7205 0.8054 0.6298 0.048 Uiso 1 1 calc R . . C64 C 0.70376(14) 0.7568(3) 0.7105(2) 0.0275(10) Uani 1 1 d . . . C65 C 0.66830(15) 0.8118(3) 0.7032(2) 0.0290(11) Uani 1 1 d . . . C66 C 0.64218(14) 0.7993(3) 0.7388(2) 0.0294(11) Uani 1 1 d . . . C67 C 0.60673(15) 0.8537(4) 0.7336(3) 0.0382(12) Uani 1 1 d . . . H67 H 0.5967 0.9076 0.7064 0.046 Uiso 1 1 calc R . . C68 C 0.58960(16) 0.8160(4) 0.7737(3) 0.0461(14) Uani 1 1 d . . . H68 H 0.5653 0.8384 0.7798 0.055 Uiso 1 1 calc R . . C69 C 0.61487(14) 0.7343(4) 0.8066(2) 0.0323(11) Uani 1 1 d . . . C70 C 0.60846(13) 0.6778(3) 0.8526(2) 0.0306(12) Uani 1 1 d . . . C71 C 0.73926(16) 0.3802(4) 0.9890(2) 0.0350(13) Uani 1 1 d . . . C72 C 0.75824(17) 0.4091(4) 1.0570(2) 0.0384(13) Uani 1 1 d . . . H72 H 0.7622 0.4738 1.0688 0.046 Uiso 1 1 calc R . . C73 C 0.77033(17) 0.3403(4) 1.1037(3) 0.0392(13) Uani 1 1 d . . . H73 H 0.7822 0.3595 1.1487 0.047 Uiso 1 1 calc R . . N11 N 0.76699(12) 0.2497(3) 1.09173(19) 0.0340(10) Uani 1 1 d . . . C74 C 0.74943(18) 0.2219(4) 1.0274(3) 0.0475(14) Uani 1 1 d . . . H74 H 0.7470 0.1568 1.0164 0.057 Uiso 1 1 calc R . . C75 C 0.73486(18) 0.2905(4) 0.9774(3) 0.0476(15) Uani 1 1 d . . . H75 H 0.7211 0.2701 0.9329 0.057 Uiso 1 1 calc R . . C76 C 0.81517(16) 0.5507(4) 0.7554(3) 0.0432(13) Uani 1 1 d . . . C77 C 0.8467(2) 0.6160(5) 0.7636(3) 0.0609(17) Uani 1 1 d . . . H77 H 0.8441 0.6770 0.7796 0.073 Uiso 1 1 calc R . . C78 C 0.8822(2) 0.5958(5) 0.7494(4) 0.076(2) Uani 1 1 d . . . H78 H 0.9053 0.6382 0.7595 0.091 Uiso 1 1 calc R . . C79 C 0.8812(2) 0.5042(5) 0.7177(4) 0.078(2) Uani 1 1 d . . . C80 C 0.8492(2) 0.4437(5) 0.7055(3) 0.0613(17) Uani 1 1 d . . . H80 H 0.8488 0.3856 0.6838 0.074 Uiso 1 1 calc R . . C81 C 0.81672(18) 0.4680(5) 0.7255(3) 0.0503(14) Uani 1 1 d . . . H81 H 0.7944 0.4243 0.7179 0.060 Uiso 1 1 calc R . . O3 O 0.9124(2) 0.4719(5) 0.6963(4) 0.145(3) Uani 1 1 d . . . C82 C 0.9429(4) 0.5369(15) 0.6952(7) 0.223(4) Uani 1 1 d D . . H82 H 0.9350 0.6032 0.7011 0.268 Uiso 1 1 calc R . . C83 C 0.9832(4) 0.5033(15) 0.7539(7) 0.223(4) Uani 1 1 d D . . H83A H 0.9843 0.5340 0.7951 0.268 Uiso 1 1 calc R . . H83B H 0.9815 0.4344 0.7595 0.268 Uiso 1 1 calc R . . C84 C 1.0230(4) 0.5252(15) 0.7437(8) 0.223(4) Uani 1 1 d D . . H84A H 1.0470 0.4967 0.7793 0.335 Uiso 0.50 1 calc PR . . H84B H 1.0268 0.5936 0.7440 0.335 Uiso 0.50 1 calc PR . . H84C H 1.0212 0.4996 0.7010 0.335 Uiso 0.50 1 calc PR . . H84D H 1.0163 0.5633 0.7036 0.335 Uiso 0.50 1 calc PR . . H84E H 1.0365 0.4663 0.7389 0.335 Uiso 0.50 1 calc PR . . H84F H 1.0421 0.5604 0.7818 0.335 Uiso 0.50 1 calc PR . . C85 C 0.9484(4) 0.5214(14) 0.6252(6) 0.223(4) Uani 1 1 d D . . H85A H 0.9233 0.5443 0.5889 0.335 Uiso 0.50 1 calc PR . . H85B H 0.9523 0.4542 0.6189 0.335 Uiso 0.50 1 calc PR . . H85C H 0.9732 0.5565 0.6256 0.335 Uiso 0.50 1 calc PR . . H85D H 0.9759 0.4924 0.6334 0.335 Uiso 0.50 1 calc PR . . H85E H 0.9468 0.5824 0.6034 0.335 Uiso 0.50 1 calc PR . . H85F H 0.9260 0.4802 0.5966 0.335 Uiso 0.50 1 calc PR . . C86 C 0.65644(16) 0.8864(3) 0.6534(2) 0.0329(11) Uani 1 1 d . . . C87 C 0.68498(17) 0.9612(3) 0.6535(3) 0.0372(12) Uani 1 1 d . . . H87 H 0.7119 0.9656 0.6885 0.045 Uiso 1 1 calc R . . C88 C 0.67356(19) 1.0240(4) 0.6048(3) 0.0506(14) Uani 1 1 d . . . H88 H 0.6938 1.0696 0.6045 0.061 Uiso 1 1 calc R . . N12 N 0.63476(19) 1.0270(4) 0.5553(2) 0.0605(15) Uani 1 1 d . . . C89 C 0.60792(19) 0.9628(5) 0.5540(3) 0.0558(16) Uani 1 1 d . . . H89 H 0.5808 0.9650 0.5194 0.067 Uiso 1 1 calc R . . C90 C 0.61657(17) 0.8874(4) 0.6021(3) 0.0465(14) Uani 1 1 d . . . H90 H 0.5961 0.8406 0.5989 0.056 Uiso 1 1 calc R . . C91 C 0.56882(14) 0.7014(4) 0.8676(2) 0.0355(11) Uani 1 1 d . . . C92 C 0.57130(17) 0.7432(6) 0.9249(3) 0.077(2) Uani 1 1 d . . . H92 H 0.5982 0.7548 0.9585 0.093 Uiso 1 1 calc R . . C93 C 0.53564(18) 0.7694(5) 0.9357(3) 0.0643(17) Uani 1 1 d . . . H93 H 0.5379 0.8013 0.9751 0.077 Uiso 1 1 calc R . . C94 C 0.49805(18) 0.7490(5) 0.8897(3) 0.0586(17) Uani 1 1 d . . . C95 C 0.49409(18) 0.7080(6) 0.8322(3) 0.084(2) Uani 1 1 d . . . H95 H 0.4670 0.6975 0.7987 0.100 Uiso 1 1 calc R . . O4 O 0.46322(12) 0.7722(4) 0.9042(2) 0.0745(13) Uani 1 1 d . . . C96 C 0.53102(17) 0.6809(5) 0.8224(3) 0.0613(16) Uani 1 1 d . . . H96 H 0.5288 0.6478 0.7835 0.074 Uiso 1 1 calc R . . C97 C 0.4314(4) 0.8299(7) 0.8597(5) 0.1357(18) Uani 1 1 d D . . H97 H 0.4391 0.8486 0.8216 0.163 Uiso 1 1 calc R . . C98 C 0.3983(3) 0.7486(7) 0.8389(5) 0.1357(18) Uani 1 1 d D . . H98A H 0.3741 0.7674 0.7985 0.163 Uiso 1 1 calc R . . H98B H 0.4111 0.6917 0.8283 0.163 Uiso 1 1 calc R . . C99 C 0.3821(3) 0.7248(7) 0.8947(5) 0.1357(18) Uani 1 1 d D . . H99A H 0.3613 0.6738 0.8800 0.204 Uiso 0.50 1 calc PR . . H99B H 0.3689 0.7807 0.9048 0.204 Uiso 0.50 1 calc PR . . H99C H 0.4058 0.7048 0.9345 0.204 Uiso 0.50 1 calc PR . . H99D H 0.3960 0.7658 0.9329 0.204 Uiso 0.50 1 calc PR . . H99E H 0.3885 0.6588 0.9080 0.204 Uiso 0.50 1 calc PR . . H99F H 0.3516 0.7347 0.8784 0.204 Uiso 0.50 1 calc PR . . C100 C 0.4153(4) 0.9110(6) 0.8838(5) 0.1357(18) Uani 1 1 d D . . H10A H 0.4363 0.9616 0.8959 0.204 Uiso 0.50 1 calc PR . . H10B H 0.4096 0.8926 0.9228 0.204 Uiso 0.50 1 calc PR . . H10C H 0.3892 0.9332 0.8491 0.204 Uiso 0.50 1 calc PR . . H10D H 0.3871 0.8966 0.8826 0.204 Uiso 0.50 1 calc PR . . H10E H 0.4139 0.9657 0.8557 0.204 Uiso 0.50 1 calc PR . . H10F H 0.4342 0.9250 0.9294 0.204 Uiso 0.50 1 calc PR . . 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 Zn1 0.0365(3) 0.0262(3) 0.0298(3) 0.0013(3) 0.0170(2) 0.0009(3) N1 0.029(2) 0.036(2) 0.036(2) -0.002(2) 0.0172(19) -0.0029(19) N2 0.045(2) 0.039(3) 0.045(3) 0.005(2) 0.032(2) 0.008(2) N3 0.036(2) 0.028(2) 0.028(2) 0.0095(17) 0.0165(18) 0.0106(17) N4 0.040(2) 0.037(2) 0.036(2) 0.007(2) 0.021(2) 0.0036(19) C1 0.052(3) 0.037(3) 0.040(3) -0.010(3) 0.022(3) -0.008(3) C2 0.066(4) 0.065(4) 0.036(3) 0.006(3) 0.031(3) -0.014(3) C3 0.035(3) 0.036(3) 0.034(3) 0.012(2) 0.013(2) 0.002(2) C4 0.045(3) 0.039(3) 0.037(3) 0.008(3) 0.022(3) -0.001(3) C5 0.051(3) 0.031(3) 0.038(3) 0.005(2) 0.023(3) 0.011(2) C6 0.048(3) 0.025(3) 0.037(3) 0.005(2) 0.018(2) 0.010(2) C7 0.085(4) 0.038(3) 0.058(4) 0.010(3) 0.037(4) 0.015(3) C8 0.082(4) 0.049(3) 0.053(4) 0.024(3) 0.045(3) 0.029(3) C9 0.047(3) 0.048(3) 0.050(3) 0.003(3) 0.029(3) 0.015(3) C10 0.040(3) 0.028(3) 0.049(3) 0.003(2) 0.022(3) -0.001(2) C11 0.041(3) 0.047(3) 0.035(3) 0.017(3) 0.021(2) 0.007(3) C12 0.062(4) 0.067(4) 0.051(4) 0.015(3) 0.042(3) 0.019(3) C13 0.044(3) 0.065(4) 0.039(3) 0.020(3) 0.027(3) 0.003(3) C14 0.036(3) 0.056(3) 0.035(3) -0.001(3) 0.018(2) 0.007(3) C15 0.035(3) 0.044(3) 0.041(3) 0.011(3) 0.017(2) 0.000(2) C16 0.045(3) 0.030(3) 0.031(3) 0.003(2) 0.016(2) 0.004(2) C17 0.045(3) 0.060(4) 0.029(3) 0.002(2) 0.011(2) 0.005(3) C18 0.038(3) 0.065(4) 0.035(3) 0.012(3) 0.015(2) 0.017(3) C19 0.038(3) 0.051(3) 0.038(3) 0.001(3) 0.021(2) 0.009(2) C20 0.039(3) 0.059(3) 0.031(3) 0.010(3) 0.013(2) 0.000(3) C21 0.057(4) 0.019(2) 0.044(3) -0.009(2) 0.028(3) -0.004(2) C22 0.073(4) 0.036(3) 0.043(4) -0.002(3) 0.012(3) -0.012(3) C23 0.060(3) 0.021(2) 0.024(3) 0.002(2) 0.009(2) -0.006(2) N5 0.032(2) 0.034(2) 0.031(2) -0.0068(19) 0.0139(18) -0.0045(18) C24 0.059(3) 0.029(3) 0.036(3) 0.008(2) 0.027(3) -0.001(2) C25 0.064(4) 0.033(3) 0.044(3) 0.009(3) 0.031(3) 0.007(3) C26 0.064(4) 0.051(3) 0.043(3) 0.008(3) 0.040(3) 0.012(3) C27 0.080(5) 0.130(8) 0.259(13) -0.091(9) 0.124(7) -0.028(5) C28 0.097 0.245 0.120 0.000 0.072 0.000 C29 0.066(5) 0.136(8) 0.129(7) -0.047(7) 0.054(5) 0.017(5) C30 0.068(5) 0.110(6) 0.053(4) -0.029(4) 0.012(3) 0.048(5) C31 0.043(3) 0.101(6) 0.062(4) -0.011(4) 0.019(3) 0.020(3) O1 0.086 0.123 0.338 0.000 0.106 0.013 C32 0.170(9) 0.199(11) 0.61(3) -0.129(12) 0.220(14) 0.007(6) C33 0.170(9) 0.199(11) 0.61(3) -0.129(12) 0.220(14) 0.007(6) C34 0.170(9) 0.199(11) 0.61(3) -0.129(12) 0.220(14) 0.007(6) C35 0.170(9) 0.199(11) 0.61(3) -0.129(12) 0.220(14) 0.007(6) C36 0.028(3) 0.074(4) 0.036(3) 0.010(3) 0.011(2) 0.021(3) C37 0.041(3) 0.048(3) 0.037(3) 0.005(3) 0.014(2) -0.003(3) C38 0.086(4) 0.034(3) 0.066(4) 0.024(3) 0.049(4) 0.027(3) N6 0.065(3) 0.074(4) 0.050(3) 0.031(3) 0.018(3) 0.025(3) C39 0.055(4) 0.064(4) 0.051(4) 0.030(3) 0.022(3) 0.028(3) C40 0.046(3) 0.075(4) 0.041(3) 0.000(3) 0.021(3) -0.009(3) C41 0.063(3) 0.091(5) 0.031(3) 0.023(3) 0.027(3) 0.029(4) C42 0.135(7) 0.055(4) 0.179(9) 0.043(5) 0.126(7) 0.044(4) C43 0.111(6) 0.040(3) 0.074(5) -0.001(3) 0.050(4) 0.001(4) C44 0.057(3) 0.069(4) 0.080(4) -0.005(4) 0.019(3) 0.022(4) C45 0.068(4) 0.069(4) 0.091(5) -0.006(4) 0.046(4) -0.011(3) C46 0.055(4) 0.093(5) 0.066(4) 0.003(4) 0.027(3) -0.007(4) O2 0.076(3) 0.079(3) 0.127(4) -0.004(3) 0.063(3) 0.000(3) C47 0.085(3) 0.080(3) 0.163(4) -0.013(3) 0.073(3) 0.005(2) C48 0.085(3) 0.080(3) 0.163(4) -0.013(3) 0.073(3) 0.005(2) C49 0.085(3) 0.080(3) 0.163(4) -0.013(3) 0.073(3) 0.005(2) C50 0.085(3) 0.080(3) 0.163(4) -0.013(3) 0.073(3) 0.005(2) Zn2 0.0317(3) 0.0262(3) 0.0229(3) 0.0007(3) 0.0114(2) 0.0010(3) N7 0.042(2) 0.022(2) 0.024(2) 0.0024(18) 0.0136(18) 0.0045(18) N8 0.043(2) 0.030(2) 0.022(2) 0.0057(18) 0.0104(17) 0.0112(19) N9 0.046(2) 0.032(2) 0.029(2) 0.0012(18) 0.0179(19) -0.0039(18) N10 0.037(2) 0.030(2) 0.025(2) -0.0001(18) 0.0147(18) -0.0007(18) C51 0.024(2) 0.040(3) 0.028(3) 0.008(2) 0.010(2) 0.005(2) C52 0.027(2) 0.049(3) 0.037(3) 0.003(3) 0.020(2) 0.008(2) C53 0.071(4) 0.046(3) 0.040(3) 0.001(3) 0.029(3) -0.009(3) C54 0.038(3) 0.028(3) 0.027(3) -0.003(2) 0.015(2) -0.008(2) C55 0.043(3) 0.031(3) 0.019(2) 0.002(2) 0.010(2) -0.004(2) C56 0.048(3) 0.031(3) 0.032(3) 0.006(2) 0.018(2) 0.009(2) C57 0.061(3) 0.060(4) 0.046(3) 0.030(3) 0.032(3) 0.034(3) C58 0.064(4) 0.079(4) 0.045(3) 0.017(3) 0.020(3) 0.049(3) C59 0.053(3) 0.030(3) 0.040(3) 0.003(2) 0.022(3) 0.003(2) C60 0.042(3) 0.061(4) 0.026(3) 0.010(3) 0.013(2) 0.022(3) C61 0.039(2) 0.024(2) 0.032(2) -0.009(3) 0.0159(19) -0.001(3) C62 0.045(3) 0.043(3) 0.039(3) 0.006(2) 0.022(2) 0.000(2) C63 0.055(3) 0.033(3) 0.039(3) 0.010(2) 0.026(3) 0.003(2) C64 0.039(2) 0.016(2) 0.029(2) 0.010(2) 0.013(2) 0.0006(19) C65 0.046(3) 0.022(2) 0.020(2) -0.001(2) 0.015(2) 0.001(2) C66 0.037(2) 0.030(2) 0.025(2) 0.004(2) 0.015(2) 0.001(2) C67 0.044(3) 0.033(3) 0.037(3) 0.008(2) 0.015(2) 0.010(2) C68 0.043(3) 0.044(3) 0.057(3) 0.007(3) 0.025(3) 0.016(2) C69 0.031(2) 0.042(3) 0.024(2) 0.003(2) 0.010(2) 0.003(2) C70 0.025(2) 0.037(3) 0.034(3) 0.000(2) 0.016(2) -0.0002(19) C71 0.049(3) 0.035(3) 0.023(3) 0.012(2) 0.016(2) 0.010(2) C72 0.065(3) 0.025(3) 0.029(3) -0.008(2) 0.022(3) 0.005(2) C73 0.051(3) 0.035(3) 0.028(3) -0.011(2) 0.011(2) 0.007(2) N11 0.045(2) 0.026(2) 0.032(2) 0.0122(19) 0.0166(19) 0.0133(18) C74 0.065(4) 0.029(3) 0.039(3) -0.005(3) 0.008(3) 0.003(3) C75 0.069(4) 0.044(4) 0.021(3) 0.006(3) 0.007(3) 0.018(3) C76 0.035(3) 0.051(3) 0.044(3) 0.006(3) 0.015(2) 0.014(3) C77 0.072(4) 0.063(4) 0.063(4) 0.010(3) 0.043(3) 0.015(3) C78 0.070(4) 0.058(4) 0.131(6) -0.020(4) 0.073(4) -0.004(3) C79 0.076(4) 0.079(5) 0.115(6) -0.015(4) 0.077(4) 0.016(4) C80 0.072(4) 0.064(4) 0.062(4) -0.011(3) 0.041(3) 0.010(3) C81 0.056(3) 0.065(4) 0.034(3) 0.003(3) 0.021(3) 0.013(3) O3 0.125(5) 0.163(7) 0.193(7) -0.060(6) 0.114(5) -0.023(5) C82 0.174(7) 0.318(11) 0.202(9) 0.045(8) 0.099(6) -0.036(8) C83 0.174(7) 0.318(11) 0.202(9) 0.045(8) 0.099(6) -0.036(8) C84 0.174(7) 0.318(11) 0.202(9) 0.045(8) 0.099(6) -0.036(8) C85 0.174(7) 0.318(11) 0.202(9) 0.045(8) 0.099(6) -0.036(8) C86 0.054(3) 0.018(2) 0.039(3) 0.006(2) 0.032(3) 0.008(2) C87 0.052(3) 0.023(2) 0.044(3) 0.011(2) 0.027(2) 0.005(2) C88 0.065(4) 0.044(3) 0.058(4) 0.007(3) 0.040(3) 0.009(3) N12 0.104(4) 0.047(3) 0.045(3) 0.014(3) 0.045(3) 0.027(3) C89 0.054(3) 0.075(4) 0.034(3) 0.006(3) 0.011(3) 0.000(3) C90 0.053(3) 0.041(3) 0.037(3) 0.019(3) 0.007(3) 0.014(3) C91 0.028(2) 0.043(3) 0.035(3) 0.004(2) 0.012(2) 0.007(2) C92 0.036(3) 0.145(7) 0.055(4) -0.031(4) 0.022(3) -0.013(4) C93 0.054(3) 0.088(5) 0.061(4) -0.031(3) 0.033(3) -0.005(3) C94 0.049(3) 0.094(5) 0.045(3) -0.003(3) 0.032(3) 0.020(3) C95 0.035(3) 0.166(8) 0.048(4) -0.020(4) 0.013(3) -0.004(4) O4 0.049(2) 0.121(4) 0.060(2) 0.021(3) 0.0280(19) 0.032(2) C96 0.050(3) 0.091(5) 0.050(3) -0.029(3) 0.027(3) -0.005(3) C97 0.171(5) 0.124(4) 0.129(4) 0.001(3) 0.076(4) 0.023(4) C98 0.171(5) 0.124(4) 0.129(4) 0.001(3) 0.076(4) 0.023(4) C99 0.171(5) 0.124(4) 0.129(4) 0.001(3) 0.076(4) 0.023(4) C100 0.171(5) 0.124(4) 0.129(4) 0.001(3) 0.076(4) 0.023(4) _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 Zn1 N4 2.059(4) . ? Zn1 N3 2.061(4) . ? Zn1 N1 2.063(4) . ? Zn1 N2 2.082(4) . ? Zn1 N5 2.128(4) 4_546 ? N1 C1 1.311(6) . ? N1 C4 1.349(6) . ? N2 C6 1.336(6) . ? N2 C9 1.388(6) . ? N3 C11 1.358(6) . ? N3 C14 1.397(6) . ? N4 C16 1.357(6) . ? N4 C19 1.383(6) . ? C1 C20 1.444(8) . ? C1 C2 1.454(7) . ? C2 C3 1.343(8) . ? C2 H2 0.9500 . ? C3 C4 1.374(6) . ? C3 H3 0.9500 . ? C4 C5 1.493(7) . ? C5 C6 1.398(7) . ? C5 C21 1.486(8) . ? C6 C7 1.417(8) . ? C7 C8 1.317(8) . ? C7 H7 0.9500 . ? C8 C9 1.434(8) . ? C8 H8 0.9500 . ? C9 C10 1.393(7) . ? C10 C11 1.426(8) . ? C10 C26 1.488(7) . ? C11 C12 1.418(7) . ? C12 C13 1.354(8) . ? C12 H12 0.9500 . ? C13 C14 1.428(7) . ? C13 H13 0.9500 . ? C14 C15 1.381(7) . ? C15 C16 1.414(7) . ? C15 C36 1.516(8) . ? C16 C17 1.472(7) . ? C17 C18 1.358(7) . ? C17 H17 0.9500 . ? C18 C19 1.419(7) . ? C18 H18 0.9500 . ? C19 C20 1.434(7) . ? C20 C41 1.424(7) . ? C21 C25 1.343(8) . ? C21 C22 1.453(8) . ? C22 C23 1.336(7) . ? C22 H22 0.9500 . ? C23 N5 1.309(6) . ? C23 H23 0.9672 . ? N5 C24 1.355(7) . ? N5 Zn1 2.128(4) 4_556 ? C24 C25 1.404(7) . ? C24 H24 0.9486 . ? C25 H25 0.9500 . ? C26 C27 1.331(10) . ? C26 C31 1.403(9) . ? C27 C28 1.446(11) . ? C27 H27 0.9500 . ? C28 C29 1.266(16) . ? C28 H28 0.9500 . ? C29 O1 1.350(9) . ? C29 C30 1.388(12) . ? C30 C31 1.401(9) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? O1 C32 1.504(19) . ? C32 C33 1.417(14) . ? C32 C35 1.540(17) . ? C32 H32 1.0000 . ? C33 C34 1.504(15) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C34 H34D 0.9800 . ? C34 H34E 0.9800 . ? C34 H34F 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C35 H35D 0.9800 . ? C35 H35E 0.9800 . ? C35 H35F 0.9800 . ? C36 C37 1.297(8) . ? C36 C40 1.388(8) . ? C37 C38 1.473(8) . ? C37 H37 0.9500 . ? C38 N6 1.285(8) . ? C38 H38 0.9500 . ? N6 C39 1.415(8) . ? C39 C40 1.319(8) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? C41 C42 1.357(9) . ? C41 C46 1.506(10) . ? C42 C43 1.545(10) . ? C42 H42 0.9500 . ? C43 C44 1.303(9) . ? C43 H43 0.9500 . ? C44 C45 1.359(9) . ? C44 O2 1.435(7) . ? C45 C46 1.377(8) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? O2 C47 1.424(8) . ? C47 C50 1.490(10) . ? C47 C48 1.512(9) . ? C47 H47 1.0000 . ? C48 C49 1.556(9) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? Zn2 N8 2.055(4) . ? Zn2 N9 2.062(4) . ? Zn2 N7 2.069(4) . ? Zn2 N10 2.095(4) . ? Zn2 N11 2.152(4) 4_657 ? N7 C54 1.370(6) . ? N7 C51 1.433(6) . ? N8 C59 1.369(6) . ? N8 C56 1.398(6) . ? N9 C61 1.369(6) . ? N9 C64 1.374(6) . ? N10 C69 1.381(6) . ? N10 C66 1.384(6) . ? C51 C70 1.403(6) . ? C51 C52 1.420(7) . ? C52 C53 1.310(7) . ? C52 H52 0.9500 . ? C53 C54 1.531(7) . ? C53 H53 0.9500 . ? C54 C55 1.311(7) . ? C55 C56 1.406(7) . ? C55 C71 1.541(7) . ? C56 C57 1.450(7) . ? C57 C58 1.339(8) . ? C57 H57 0.9500 . ? C58 C59 1.467(8) . ? C58 H58 0.9500 . ? C59 C60 1.394(7) . ? C60 C61 1.392(8) . ? C60 C76 1.494(7) . ? C61 C62 1.454(7) . ? C62 C63 1.350(7) . ? C62 H62 0.9500 . ? C63 C64 1.457(7) . ? C63 H63 0.9500 . ? C64 C65 1.403(6) . ? C65 C66 1.405(6) . ? C65 C86 1.461(6) . ? C66 C67 1.408(7) . ? C67 C68 1.340(7) . ? C67 H67 0.9500 . ? C68 C69 1.462(7) . ? C68 H68 0.9500 . ? C69 C70 1.368(6) . ? C70 C91 1.553(6) . ? C71 C75 1.295(8) . ? C71 C72 1.437(7) . ? C72 C73 1.359(8) . ? C72 H72 0.9500 . ? C73 N11 1.309(7) . ? C73 H73 0.9500 . ? N11 C74 1.361(7) . ? N11 Zn2 2.152(4) 4_647 ? C74 C75 1.407(7) . ? C74 H74 0.9500 . ? C75 H75 0.9500 . ? C76 C81 1.354(8) . ? C76 C77 1.383(8) . ? C77 C78 1.399(8) . ? C77 H77 0.9500 . ? C78 C79 1.469(9) . ? C78 H78 0.9500 . ? C79 C80 1.338(9) . ? C79 O3 1.400(8) . ? C80 C81 1.388(8) . ? C80 H80 0.9500 . ? C81 H81 0.9500 . ? O3 C82 1.399(17) . ? C82 C83 1.562(14) . ? C82 C85 1.630(14) . ? C82 H82 1.0000 . ? C83 C84 1.497(14) . ? C83 H83A 0.9900 . ? C83 H83B 0.9900 . ? C84 H84A 0.9800 . ? C84 H84B 0.9800 . ? C84 H84C 0.9800 . ? C84 H84D 0.9800 . ? C84 H84E 0.9800 . ? C84 H84F 0.9800 . ? C85 H85A 0.9800 . ? C85 H85B 0.9800 . ? C85 H85C 0.9800 . ? C85 H85D 0.9800 . ? C85 H85E 0.9800 . ? C85 H85F 0.9800 . ? C86 C90 1.401(7) . ? C86 C87 1.445(7) . ? C87 C88 1.329(7) . ? C87 H87 0.9500 . ? C88 N12 1.360(8) . ? C88 H88 0.9500 . ? N12 C89 1.289(8) . ? C89 C90 1.449(8) . ? C89 H89 0.9500 . ? C90 H90 0.9500 . ? C91 C96 1.329(7) . ? C91 C92 1.361(8) . ? C92 C93 1.383(7) . ? C92 H92 0.9500 . ? C93 C94 1.331(8) . ? C93 H93 0.9500 . ? C94 C95 1.345(8) . ? C94 O4 1.389(6) . ? C95 C96 1.416(8) . ? C95 H95 0.9500 . ? O4 C97 1.414(11) . ? C96 H96 0.9500 . ? C97 C100 1.460(11) . ? C97 C98 1.562(12) . ? C97 H97 1.0000 . ? C98 C99 1.559(11) . ? C98 H98A 0.9900 . ? C98 H98B 0.9900 . ? C99 H99A 0.9800 . ? C99 H99B 0.9800 . ? C99 H99C 0.9800 . ? C99 H99D 0.9800 . ? C99 H99E 0.9800 . ? C99 H99F 0.9800 . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? C100 H10D 0.9800 . ? C100 H10E 0.9800 . ? C100 H10F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Zn1 N3 88.99(15) . . ? N4 Zn1 N1 88.71(16) . . ? N3 Zn1 N1 162.21(16) . . ? N4 Zn1 N2 161.60(17) . . ? N3 Zn1 N2 88.68(15) . . ? N1 Zn1 N2 87.96(16) . . ? N4 Zn1 N5 95.75(16) . 4_546 ? N3 Zn1 N5 102.27(16) . 4_546 ? N1 Zn1 N5 95.50(15) . 4_546 ? N2 Zn1 N5 102.58(15) . 4_546 ? C1 N1 C4 103.7(4) . . ? C1 N1 Zn1 127.3(4) . . ? C4 N1 Zn1 127.9(3) . . ? C6 N2 C9 106.7(4) . . ? C6 N2 Zn1 127.5(3) . . ? C9 N2 Zn1 125.1(3) . . ? C11 N3 C14 106.2(4) . . ? C11 N3 Zn1 128.5(3) . . ? C14 N3 Zn1 125.4(3) . . ? C16 N4 C19 106.1(4) . . ? C16 N4 Zn1 126.5(3) . . ? C19 N4 Zn1 126.9(3) . . ? N1 C1 C20 127.8(5) . . ? N1 C1 C2 111.7(5) . . ? C20 C1 C2 120.5(5) . . ? C3 C2 C1 104.8(5) . . ? C3 C2 H2 127.6 . . ? C1 C2 H2 127.6 . . ? C2 C3 C4 105.8(5) . . ? C2 C3 H3 127.1 . . ? C4 C3 H3 127.1 . . ? N1 C4 C3 114.0(4) . . ? N1 C4 C5 122.5(4) . . ? C3 C4 C5 123.5(5) . . ? C6 C5 C21 119.4(5) . . ? C6 C5 C4 125.7(5) . . ? C21 C5 C4 114.9(4) . . ? N2 C6 C5 124.9(5) . . ? N2 C6 C7 111.3(5) . . ? C5 C6 C7 123.7(5) . . ? C8 C7 C6 105.9(5) . . ? C8 C7 H7 127.1 . . ? C6 C7 H7 127.1 . . ? C7 C8 C9 109.6(5) . . ? C7 C8 H8 125.2 . . ? C9 C8 H8 125.2 . . ? N2 C9 C10 127.5(5) . . ? N2 C9 C8 106.6(5) . . ? C10 C9 C8 125.9(5) . . ? C9 C10 C11 124.0(5) . . ? C9 C10 C26 117.5(5) . . ? C11 C10 C26 118.4(4) . . ? N3 C11 C12 111.4(5) . . ? N3 C11 C10 125.4(4) . . ? C12 C11 C10 123.1(5) . . ? C13 C12 C11 105.7(5) . . ? C13 C12 H12 127.2 . . ? C11 C12 H12 127.2 . . ? C12 C13 C14 108.9(5) . . ? C12 C13 H13 125.5 . . ? C14 C13 H13 125.5 . . ? C15 C14 N3 125.9(4) . . ? C15 C14 C13 125.9(5) . . ? N3 C14 C13 107.6(4) . . ? C14 C15 C16 125.3(5) . . ? C14 C15 C36 114.8(4) . . ? C16 C15 C36 119.8(4) . . ? N4 C16 C15 125.4(4) . . ? N4 C16 C17 110.8(4) . . ? C15 C16 C17 123.8(5) . . ? C18 C17 C16 104.3(5) . . ? C18 C17 H17 127.9 . . ? C16 C17 H17 127.9 . . ? C17 C18 C19 109.2(5) . . ? C17 C18 H18 125.4 . . ? C19 C18 H18 125.4 . . ? N4 C19 C18 109.6(4) . . ? N4 C19 C20 125.8(5) . . ? C18 C19 C20 124.6(5) . . ? C41 C20 C19 119.9(5) . . ? C41 C20 C1 118.1(5) . . ? C19 C20 C1 121.9(4) . . ? C25 C21 C22 118.4(6) . . ? C25 C21 C5 122.0(5) . . ? C22 C21 C5 119.6(5) . . ? C23 C22 C21 115.8(5) . . ? C23 C22 H22 122.1 . . ? C21 C22 H22 122.1 . . ? N5 C23 C22 128.1(5) . . ? N5 C23 H23 115.7 . . ? C22 C23 H23 116.3 . . ? C23 N5 C24 116.0(4) . . ? C23 N5 Zn1 123.8(3) . 4_556 ? C24 N5 Zn1 119.9(3) . 4_556 ? N5 C24 C25 122.1(5) . . ? N5 C24 H24 118.4 . . ? C25 C24 H24 119.5 . . ? C21 C25 C24 119.7(5) . . ? C21 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C27 C26 C31 116.4(6) . . ? C27 C26 C10 122.2(6) . . ? C31 C26 C10 121.4(6) . . ? C26 C27 C28 124.1(9) . . ? C26 C27 H27 118.0 . . ? C28 C27 H27 118.0 . . ? C29 C28 C27 118.4(11) . . ? C29 C28 H28 120.8 . . ? C27 C28 H28 120.8 . . ? C28 C29 O1 118.4(10) . . ? C28 C29 C30 120.6(8) . . ? O1 C29 C30 120.6(8) . . ? C29 C30 C31 121.5(6) . . ? C29 C30 H30 119.3 . . ? C31 C30 H30 119.3 . . ? C30 C31 C26 118.6(7) . . ? C30 C31 H31 120.7 . . ? C26 C31 H31 120.7 . . ? C29 O1 C32 124.8(10) . . ? C33 C32 O1 114.1(15) . . ? C33 C32 C35 114.2(14) . . ? O1 C32 C35 84.0(12) . . ? C33 C32 H32 113.8 . . ? O1 C32 H32 113.8 . . ? C35 C32 H32 113.8 . . ? C32 C33 C34 109.7(13) . . ? C32 C33 H33A 109.7 . . ? C34 C33 H33A 109.7 . . ? C32 C33 H33B 109.7 . . ? C34 C33 H33B 109.7 . . ? H33A C33 H33B 108.2 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C34 H34D 109.5 . . ? H34A C34 H34D 141.1 . . ? H34B C34 H34D 56.3 . . ? H34C C34 H34D 56.3 . . ? C33 C34 H34E 109.5 . . ? H34A C34 H34E 56.3 . . ? H34B C34 H34E 141.1 . . ? H34C C34 H34E 56.3 . . ? H34D C34 H34E 109.5 . . ? C33 C34 H34F 109.5 . . ? H34A C34 H34F 56.3 . . ? H34B C34 H34F 56.3 . . ? H34C C34 H34F 141.1 . . ? H34D C34 H34F 109.5 . . ? H34E C34 H34F 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C35 H35D 109.5 . . ? H35A C35 H35D 141.1 . . ? H35B C35 H35D 56.3 . . ? H35C C35 H35D 56.3 . . ? C32 C35 H35E 109.5 . . ? H35A C35 H35E 56.3 . . ? H35B C35 H35E 141.1 . . ? H35C C35 H35E 56.3 . . ? H35D C35 H35E 109.5 . . ? C32 C35 H35F 109.5 . . ? H35A C35 H35F 56.3 . . ? H35B C35 H35F 56.3 . . ? H35C C35 H35F 141.1 . . ? H35D C35 H35F 109.5 . . ? H35E C35 H35F 109.5 . . ? C37 C36 C40 117.8(6) . . ? C37 C36 C15 120.1(5) . . ? C40 C36 C15 121.9(6) . . ? C36 C37 C38 120.4(5) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? N6 C38 C37 121.1(6) . . ? N6 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? C38 N6 C39 117.2(5) . . ? C40 C39 N6 121.4(6) . . ? C40 C39 H39 119.3 . . ? N6 C39 H39 119.3 . . ? C39 C40 C36 122.1(6) . . ? C39 C40 H40 119.0 . . ? C36 C40 H40 119.0 . . ? C42 C41 C20 124.0(7) . . ? C42 C41 C46 118.5(6) . . ? C20 C41 C46 117.4(6) . . ? C41 C42 C43 118.8(7) . . ? C41 C42 H42 120.6 . . ? C43 C42 H42 120.6 . . ? C44 C43 C42 116.8(6) . . ? C44 C43 H43 121.6 . . ? C42 C43 H43 121.6 . . ? C43 C44 C45 126.5(6) . . ? C43 C44 O2 120.0(6) . . ? C45 C44 O2 113.5(6) . . ? C44 C45 C46 119.7(7) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C45 C46 C41 119.3(6) . . ? C45 C46 H46 120.4 . . ? C41 C46 H46 120.4 . . ? C47 O2 C44 119.1(5) . . ? O2 C47 C50 112.0(7) . . ? O2 C47 C48 102.3(6) . . ? C50 C47 C48 116.5(7) . . ? O2 C47 H47 108.6 . . ? C50 C47 H47 108.6 . . ? C48 C47 H47 108.6 . . ? C47 C48 C49 113.7(6) . . ? C47 C48 H48A 108.8 . . ? C49 C48 H48A 108.8 . . ? C47 C48 H48B 108.8 . . ? C49 C48 H48B 108.8 . . ? H48A C48 H48B 107.7 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C50 H50A 109.5 . . ? C47 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C47 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? N8 Zn2 N9 88.26(15) . . ? N8 Zn2 N7 87.70(15) . . ? N9 Zn2 N7 161.80(16) . . ? N8 Zn2 N10 159.86(15) . . ? N9 Zn2 N10 87.99(15) . . ? N7 Zn2 N10 89.72(14) . . ? N8 Zn2 N11 104.35(15) . 4_657 ? N9 Zn2 N11 102.83(15) . 4_657 ? N7 Zn2 N11 95.37(15) . 4_657 ? N10 Zn2 N11 95.77(15) . 4_657 ? C54 N7 C51 106.9(4) . . ? C54 N7 Zn2 126.0(3) . . ? C51 N7 Zn2 126.0(3) . . ? C59 N8 C56 106.9(4) . . ? C59 N8 Zn2 127.4(3) . . ? C56 N8 Zn2 125.3(3) . . ? C61 N9 C64 107.0(4) . . ? C61 N9 Zn2 126.7(3) . . ? C64 N9 Zn2 126.2(3) . . ? C69 N10 C66 107.6(4) . . ? C69 N10 Zn2 124.1(3) . . ? C66 N10 Zn2 126.7(3) . . ? C70 C51 C52 129.2(4) . . ? C70 C51 N7 122.4(4) . . ? C52 C51 N7 108.4(4) . . ? C53 C52 C51 110.7(4) . . ? C53 C52 H52 124.6 . . ? C51 C52 H52 124.6 . . ? C52 C53 C54 106.5(5) . . ? C52 C53 H53 126.8 . . ? C54 C53 H53 126.8 . . ? C55 C54 N7 126.2(4) . . ? C55 C54 C53 126.3(5) . . ? N7 C54 C53 107.4(4) . . ? C54 C55 C56 126.8(5) . . ? C54 C55 C71 120.6(4) . . ? C56 C55 C71 112.6(4) . . ? N8 C56 C55 124.7(5) . . ? N8 C56 C57 108.1(4) . . ? C55 C56 C57 127.2(5) . . ? C58 C57 C56 108.9(5) . . ? C58 C57 H57 125.5 . . ? C56 C57 H57 125.5 . . ? C57 C58 C59 106.4(5) . . ? C57 C58 H58 126.8 . . ? C59 C58 H58 126.8 . . ? N8 C59 C60 125.7(5) . . ? N8 C59 C58 109.7(4) . . ? C60 C59 C58 124.6(5) . . ? C61 C60 C59 124.4(5) . . ? C61 C60 C76 116.5(5) . . ? C59 C60 C76 119.1(5) . . ? N9 C61 C60 126.6(4) . . ? N9 C61 C62 109.0(5) . . ? C60 C61 C62 124.3(4) . . ? C63 C62 C61 107.9(4) . . ? C63 C62 H62 126.0 . . ? C61 C62 H62 126.0 . . ? C62 C63 C64 106.3(4) . . ? C62 C63 H63 126.9 . . ? C64 C63 H63 126.9 . . ? N9 C64 C65 127.2(4) . . ? N9 C64 C63 109.7(4) . . ? C65 C64 C63 123.1(4) . . ? C64 C65 C66 125.2(4) . . ? C64 C65 C86 118.1(4) . . ? C66 C65 C86 116.7(4) . . ? N10 C66 C65 123.7(4) . . ? N10 C66 C67 109.4(4) . . ? C65 C66 C67 126.9(4) . . ? C68 C67 C66 108.0(4) . . ? C68 C67 H67 126.0 . . ? C66 C67 H67 126.0 . . ? C67 C68 C69 108.2(4) . . ? C67 C68 H68 125.9 . . ? C69 C68 H68 125.9 . . ? C70 C69 N10 126.7(4) . . ? C70 C69 C68 126.4(4) . . ? N10 C69 C68 106.7(4) . . ? C69 C70 C51 128.8(4) . . ? C69 C70 C91 115.4(4) . . ? C51 C70 C91 115.8(4) . . ? C75 C71 C72 117.1(5) . . ? C75 C71 C55 126.1(5) . . ? C72 C71 C55 116.7(4) . . ? C73 C72 C71 117.5(5) . . ? C73 C72 H72 121.3 . . ? C71 C72 H72 121.3 . . ? N11 C73 C72 125.2(5) . . ? N11 C73 H73 117.4 . . ? C72 C73 H73 117.4 . . ? C73 N11 C74 117.6(4) . . ? C73 N11 Zn2 121.3(4) . 4_647 ? C74 N11 Zn2 120.2(3) . 4_647 ? N11 C74 C75 119.2(5) . . ? N11 C74 H74 120.4 . . ? C75 C74 H74 120.4 . . ? C71 C75 C74 123.3(5) . . ? C71 C75 H75 118.4 . . ? C74 C75 H75 118.4 . . ? C81 C76 C77 118.1(5) . . ? C81 C76 C60 122.2(5) . . ? C77 C76 C60 119.6(5) . . ? C76 C77 C78 122.6(6) . . ? C76 C77 H77 118.7 . . ? C78 C77 H77 118.7 . . ? C77 C78 C79 114.9(6) . . ? C77 C78 H78 122.6 . . ? C79 C78 H78 122.6 . . ? C80 C79 O3 113.5(6) . . ? C80 C79 C78 122.1(5) . . ? O3 C79 C78 124.4(7) . . ? C79 C80 C81 118.4(6) . . ? C79 C80 H80 120.8 . . ? C81 C80 H80 120.8 . . ? C76 C81 C80 123.4(6) . . ? C76 C81 H81 118.3 . . ? C80 C81 H81 118.3 . . ? C79 O3 C82 117.4(10) . . ? O3 C82 C83 102.7(13) . . ? O3 C82 C85 106.4(13) . . ? C83 C82 C85 110.2(12) . . ? O3 C82 H82 112.3 . . ? C83 C82 H82 112.3 . . ? C85 C82 H82 112.3 . . ? C84 C83 C82 112.8(12) . . ? C84 C83 H83A 109.0 . . ? C82 C83 H83A 109.0 . . ? C84 C83 H83B 109.0 . . ? C82 C83 H83B 109.0 . . ? H83A C83 H83B 107.8 . . ? C83 C84 H84A 109.5 . . ? C83 C84 H84B 109.5 . . ? H84A C84 H84B 109.5 . . ? C83 C84 H84C 109.5 . . ? H84A C84 H84C 109.5 . . ? H84B C84 H84C 109.5 . . ? C83 C84 H84D 109.5 . . ? H84A C84 H84D 141.1 . . ? H84B C84 H84D 56.3 . . ? H84C C84 H84D 56.3 . . ? C83 C84 H84E 109.5 . . ? H84A C84 H84E 56.3 . . ? H84B C84 H84E 141.1 . . ? H84C C84 H84E 56.3 . . ? H84D C84 H84E 109.5 . . ? C83 C84 H84F 109.5 . . ? H84A C84 H84F 56.3 . . ? H84B C84 H84F 56.3 . . ? H84C C84 H84F 141.1 . . ? H84D C84 H84F 109.5 . . ? H84E C84 H84F 109.5 . . ? C82 C85 H85A 109.5 . . ? C82 C85 H85B 109.5 . . ? H85A C85 H85B 109.5 . . ? C82 C85 H85C 109.5 . . ? H85A C85 H85C 109.5 . . ? H85B C85 H85C 109.5 . . ? C82 C85 H85D 109.5 . . ? H85A C85 H85D 141.1 . . ? H85B C85 H85D 56.3 . . ? H85C C85 H85D 56.3 . . ? C82 C85 H85E 109.5 . . ? H85A C85 H85E 56.3 . . ? H85B C85 H85E 141.1 . . ? H85C C85 H85E 56.3 . . ? H85D C85 H85E 109.5 . . ? C82 C85 H85F 109.5 . . ? H85A C85 H85F 56.3 . . ? H85B C85 H85F 56.3 . . ? H85C C85 H85F 141.1 . . ? H85D C85 H85F 109.5 . . ? H85E C85 H85F 109.5 . . ? C90 C86 C87 116.7(4) . . ? C90 C86 C65 121.0(4) . . ? C87 C86 C65 122.4(5) . . ? C88 C87 C86 120.0(5) . . ? C88 C87 H87 120.0 . . ? C86 C87 H87 120.0 . . ? C87 C88 N12 124.0(6) . . ? C87 C88 H88 118.0 . . ? N12 C88 H88 118.0 . . ? C89 N12 C88 118.1(5) . . ? N12 C89 C90 124.0(5) . . ? N12 C89 H89 118.0 . . ? C90 C89 H89 118.0 . . ? C86 C90 C89 117.2(5) . . ? C86 C90 H90 121.4 . . ? C89 C90 H90 121.4 . . ? C96 C91 C92 118.7(5) . . ? C96 C91 C70 118.8(4) . . ? C92 C91 C70 122.4(4) . . ? C91 C92 C93 121.7(5) . . ? C91 C92 H92 119.2 . . ? C93 C92 H92 119.2 . . ? C94 C93 C92 118.6(5) . . ? C94 C93 H93 120.7 . . ? C92 C93 H93 120.7 . . ? C93 C94 C95 121.7(5) . . ? C93 C94 O4 116.5(5) . . ? C95 C94 O4 121.8(5) . . ? C94 C95 C96 118.7(5) . . ? C94 C95 H95 120.6 . . ? C96 C95 H95 120.6 . . ? C94 O4 C97 119.0(6) . . ? C91 C96 C95 120.4(5) . . ? C91 C96 H96 119.8 . . ? C95 C96 H96 119.8 . . ? O4 C97 C100 120.5(9) . . ? O4 C97 C98 93.3(8) . . ? C100 C97 C98 110.6(9) . . ? O4 C97 H97 110.4 . . ? C100 C97 H97 110.4 . . ? C98 C97 H97 110.4 . . ? C99 C98 C97 111.7(8) . . ? C99 C98 H98A 109.3 . . ? C97 C98 H98A 109.3 . . ? C99 C98 H98B 109.3 . . ? C97 C98 H98B 109.3 . . ? H98A C98 H98B 107.9 . . ? C98 C99 H99A 109.5 . . ? C98 C99 H99B 109.5 . . ? H99A C99 H99B 109.5 . . ? C98 C99 H99C 109.5 . . ? H99A C99 H99C 109.5 . . ? H99B C99 H99C 109.5 . . ? C98 C99 H99D 109.5 . . ? H99A C99 H99D 141.1 . . ? H99B C99 H99D 56.3 . . ? H99C C99 H99D 56.3 . . ? C98 C99 H99E 109.5 . . ? H99A C99 H99E 56.3 . . ? H99B C99 H99E 141.1 . . ? H99C C99 H99E 56.3 . . ? H99D C99 H99E 109.5 . . ? C98 C99 H99F 109.5 . . ? H99A C99 H99F 56.3 . . ? H99B C99 H99F 56.3 . . ? H99C C99 H99F 141.1 . . ? H99D C99 H99F 109.5 . . ? H99E C99 H99F 109.5 . . ? C97 C100 H10A 109.5 . . ? C97 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? C97 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? C97 C100 H10D 109.5 . . ? H10A C100 H10D 141.1 . . ? H10B C100 H10D 56.3 . . ? H10C C100 H10D 56.3 . . ? C97 C100 H10E 109.5 . . ? H10A C100 H10E 56.3 . . ? H10B C100 H10E 141.1 . . ? H10C C100 H10E 56.3 . . ? H10D C100 H10E 109.5 . . ? C97 C100 H10F 109.5 . . ? H10A C100 H10F 56.3 . . ? H10B C100 H10F 56.3 . . ? H10C C100 H10F 141.1 . . ? H10D C100 H10F 109.5 . . ? H10E C100 H10F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.13 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.901 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.089 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 -0.338 0.000 570 147 ' ' 2 0.500 0.162 0.000 570 147 ' ' 3 0.500 0.218 0.500 577 139 ' ' 4 0.189 0.185 0.045 18 2 ' ' 5 0.811 0.185 0.955 18 2 ' ' 6 0.000 0.718 0.500 577 139 ' ' 7 0.311 0.685 0.955 18 2 ' ' 8 0.689 0.685 0.045 18 2 ' ' _platon_squeeze_details ; Disordered solvent molecules (2 DMF, 6 H2O) were removed from the asymetric unit. However their contributions were included in the overall formula ; _database_code_depnum_ccdc_archive 'CCDC 942057' ####################################################################### # # 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_compound((S,S)-2-Zn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57 H45 Cl9 N6 O2 Zn' _chemical_formula_weight 1230.41 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.7983(11) _cell_length_b 19.3351(19) _cell_length_c 13.5576(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.192(4) _cell_angle_gamma 90.00 _cell_volume 2814.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5907 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 24.35 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.912 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8985 _exptl_absorpt_correction_T_max 0.9644 _exptl_absorpt_process_details sadabs _exptl_special_details ; Absolute configurations have been fixed based on known configurations The starting porphyrin being chiral and enantiopure the space group is thus necessarly noncentrosymmetric ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29124 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0992 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 29.95 _reflns_number_total 14889 _reflns_number_gt 8668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. DFIX 1.54 0.02 C52 C53 and DFIX 1.54 0.02 C34 C35 were used in order to fix Csp3-Csp3 distances to acceptable values ; _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^)+(0.1935P)^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 0.07(2) _refine_ls_number_reflns 14889 _refine_ls_number_parameters 608 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1532 _refine_ls_R_factor_gt 0.0951 _refine_ls_wR_factor_ref 0.3080 _refine_ls_wR_factor_gt 0.2630 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.003 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 Zn1 Zn 0.25189(8) 0.32607(6) 0.75085(6) 0.02479(18) Uani 1 1 d . . . N1 N 0.4135(6) 0.3837(3) 0.7539(4) 0.0229(13) Uani 1 1 d . . . N2 N 0.2060(6) 0.3736(3) 0.8765(4) 0.0262(13) Uani 1 1 d . . . N3 N 0.0905(6) 0.2690(3) 0.7457(4) 0.0260(14) Uani 1 1 d . . . N4 N 0.3026(6) 0.2749(3) 0.6260(4) 0.0236(9) Uani 1 1 d . . . C1 C 0.5011(7) 0.3808(4) 0.6872(5) 0.0264(16) Uani 1 1 d . . . C2 C 0.5912(8) 0.4364(4) 0.7107(6) 0.0310(17) Uani 1 1 d . . . H2 H 0.6606 0.4470 0.6759 0.037 Uiso 1 1 calc R . . C3 C 0.5573(7) 0.4702(4) 0.7916(6) 0.0303(16) Uani 1 1 d . . . H3 H 0.5994 0.5084 0.8241 0.036 Uiso 1 1 calc R . . C4 C 0.4459(8) 0.4377(4) 0.8190(6) 0.0258(17) Uani 1 1 d . . . C5 C 0.3789(7) 0.4580(4) 0.9001(5) 0.0282(17) Uani 1 1 d . . . C6 C 0.2693(7) 0.4281(4) 0.9261(6) 0.0266(16) Uani 1 1 d . . . C7 C 0.2020(9) 0.4518(5) 1.0085(6) 0.042(2) Uani 1 1 d . . . H7 H 0.2254 0.4880 1.0541 0.050 Uiso 1 1 calc R . . C8 C 0.1022(9) 0.4121(5) 1.0057(7) 0.043(2) Uani 1 1 d . . . H8 H 0.0417 0.4145 1.0516 0.051 Uiso 1 1 calc R . . C9 C 0.0981(8) 0.3653(4) 0.9243(6) 0.0318(17) Uani 1 1 d . . . C10 C 0.0025(6) 0.3171(4) 0.8936(5) 0.0283(17) Uani 1 1 d . . . C11 C 0.0048(7) 0.2695(3) 0.8117(5) 0.0259(17) Uani 1 1 d . . . C12 C -0.0862(8) 0.2143(4) 0.7916(6) 0.038(2) Uani 1 1 d . . . H12 H -0.1572 0.2053 0.8252 0.045 Uiso 1 1 calc R . . C13 C -0.0477(9) 0.1790(4) 0.7148(6) 0.042(2) Uani 1 1 d . . . H13 H -0.0849 0.1385 0.6850 0.051 Uiso 1 1 calc R . . C14 C 0.0612(8) 0.2144(4) 0.6862(6) 0.0284(17) Uani 1 1 d . . . C15 C 0.1270(8) 0.1924(4) 0.6087(6) 0.035(2) Uani 1 1 d . . . C16 C 0.2391(7) 0.2205(4) 0.5809(6) 0.0294(17) Uani 1 1 d . . . C17 C 0.3053(8) 0.1970(4) 0.5020(6) 0.038(2) Uani 1 1 d . . . H17 H 0.2802 0.1605 0.4574 0.046 Uiso 1 1 calc R . . C18 C 0.4129(8) 0.2364(4) 0.5010(6) 0.0306(17) Uani 1 1 d . . . H18 H 0.4764 0.2321 0.4581 0.037 Uiso 1 1 calc R . . C19 C 0.4052(7) 0.2865(3) 0.5818(5) 0.0236(9) Uani 1 1 d . . . C20 C 0.4979(7) 0.3350(4) 0.6099(5) 0.0258(15) Uani 1 1 d . . . C21 C 0.4298(8) 0.5140(4) 0.9558(6) 0.0266(16) Uani 1 1 d . . . C22 C 0.4771(8) 0.5620(4) 1.0031(7) 0.0338(18) Uani 1 1 d . . . C23 C 0.5314(7) 0.6214(4) 1.0556(5) 0.0256(16) Uani 1 1 d . . . C24 C 0.6485(9) 0.6465(5) 1.0368(7) 0.050(2) Uani 1 1 d . . . H24 H 0.6929 0.6234 0.9898 0.060 Uiso 1 1 calc R . . C25 C 0.6986(9) 0.7021(5) 1.0836(7) 0.040(2) Uani 1 1 d . . . H25 H 0.7764 0.7184 1.0663 0.048 Uiso 1 1 calc R . . N5 N 0.3558(6) 0.2367(3) 0.8451(5) 0.0287(14) Uani 1 1 d . . . C26 C 0.4662(7) 0.2111(3) 0.8240(6) 0.0281(16) Uani 1 1 d . . . H26 H 0.5040 0.2330 0.7722 0.034 Uiso 1 1 calc R . . C27 C 0.4697(7) 0.6551(3) 1.1286(5) 0.0284(15) Uani 1 1 d . . . H27 H 0.3900 0.6408 1.1445 0.034 Uiso 1 1 calc R . . C28 C -0.1083(7) 0.3139(4) 0.9500(5) 0.0325(19) Uani 1 1 d . . . C29 C -0.1029(8) 0.2913(5) 1.0451(6) 0.043(2) Uani 1 1 d . . . H29 H -0.0247 0.2792 1.0797 0.052 Uiso 1 1 calc R . . C30 C -0.2101(11) 0.2856(6) 1.0924(8) 0.065(3) Uani 1 1 d . . . H30 H -0.2031 0.2733 1.1606 0.078 Uiso 1 1 calc R . . C31 C -0.3248(8) 0.2972(5) 1.0437(7) 0.047(2) Uani 1 1 d . . . C32 C -0.3325(7) 0.3223(4) 0.9520(7) 0.0404(17) Uani 1 1 d . . . H32 H -0.4117 0.3348 0.9195 0.049 Uiso 1 1 calc R . . C33 C -0.2249(7) 0.3310(5) 0.9014(5) 0.0328(15) Uani 1 1 d . . . H33 H -0.2321 0.3482 0.8354 0.039 Uiso 1 1 calc R . . O1 O -0.4356(9) 0.2863(6) 1.0836(7) 0.0975(18) Uani 1 1 d . . . C34 C -0.4448(14) 0.2741(8) 1.1793(10) 0.0975(18) Uani 1 1 d D . . H34 H -0.3777 0.2981 1.2231 0.117 Uiso 1 1 calc R . . C35 C -0.4276(14) 0.1917(8) 1.1824(10) 0.0975(18) Uani 1 1 d D . . H35A H -0.5040 0.1700 1.1492 0.117 Uiso 1 1 calc R . . H35B H -0.3578 0.1792 1.1442 0.117 Uiso 1 1 calc R . . C36 C -0.4019(14) 0.1618(9) 1.2869(10) 0.0975(18) Uani 1 1 d . . . H36A H -0.3158 0.1449 1.2973 0.146 Uiso 1 1 calc R . . H36B H -0.4592 0.1234 1.2948 0.146 Uiso 1 1 calc R . . H36C H -0.4140 0.1978 1.3358 0.146 Uiso 1 1 calc R . . C37 C -0.5654(14) 0.2862(10) 1.2109(10) 0.0975(18) Uani 1 1 d . . . H37A H -0.6291 0.2641 1.1643 0.146 Uiso 1 1 calc R . . H37B H -0.5812 0.3361 1.2127 0.146 Uiso 1 1 calc R . . H37C H -0.5685 0.2666 1.2773 0.146 Uiso 1 1 calc R . . C38 C -0.0768(9) 0.6310(5) 0.4471(7) 0.042(2) Uani 1 1 d . . . C39 C -0.0363(9) 0.5830(4) 0.4933(6) 0.040(2) Uani 1 1 d . . . C40 C 0.0229(9) 0.5261(4) 0.5471(6) 0.036(2) Uani 1 1 d . . . C41 C -0.0400(9) 0.4776(5) 0.5928(7) 0.049(2) Uani 1 1 d . . . H41 H -0.1283 0.4794 0.5887 0.059 Uiso 1 1 calc R . . C42 C 0.0250(8) 0.4246(4) 0.6465(6) 0.0381(19) Uani 1 1 d . . . H42 H -0.0217 0.3913 0.6785 0.046 Uiso 1 1 calc R . . N6 N 0.1475(6) 0.4182(3) 0.6551(4) 0.0281(14) Uani 1 1 d . . . C43 C 0.2086(10) 0.4640(5) 0.6104(7) 0.048(2) Uani 1 1 d . . . H43 H 0.2969 0.4608 0.6159 0.058 Uiso 1 1 calc R . . C44 C 0.1492(9) 0.5192(5) 0.5530(9) 0.061(3) Uani 1 1 d . . . H44 H 0.1973 0.5508 0.5193 0.073 Uiso 1 1 calc R . . C45 C 0.6070(7) 0.3388(4) 0.5469(5) 0.0303(18) Uani 1 1 d . . . C46 C 0.7193(8) 0.3100(5) 0.5799(6) 0.047(2) Uani 1 1 d . . . H46 H 0.7304 0.2894 0.6439 0.056 Uiso 1 1 calc R . . C47 C 0.8210(9) 0.3101(5) 0.5200(7) 0.054(3) Uani 1 1 d . . . H47 H 0.8982 0.2887 0.5426 0.065 Uiso 1 1 calc R . . C48 C 0.8038(9) 0.3410(6) 0.4320(6) 0.050(2) Uani 1 1 d . . . C49 C 0.6929(9) 0.3720(5) 0.3955(6) 0.042(2) Uani 1 1 d . . . H49 H 0.6850 0.3945 0.3329 0.051 Uiso 1 1 calc R . . C50 C 0.5920(10) 0.3696(5) 0.4527(7) 0.051(2) Uani 1 1 d . . . H50 H 0.5139 0.3887 0.4277 0.061 Uiso 1 1 calc R . . O2 O 0.8989(9) 0.3468(6) 0.3657(6) 0.0924(17) Uani 1 1 d . . . C51 C 1.0105(13) 0.2921(9) 0.3771(10) 0.0924(17) Uani 1 1 d . . . H51 H 1.0419 0.2915 0.4492 0.111 Uiso 1 1 calc R . . C52 C 1.1068(12) 0.3152(9) 0.3292(9) 0.0924(17) Uani 1 1 d D . . H52A H 1.0714 0.3279 0.2612 0.111 Uiso 1 1 calc R . . H52B H 1.1623 0.2751 0.3226 0.111 Uiso 1 1 calc R . . C53 C 1.1886(13) 0.3744(8) 0.3678(9) 0.0924(17) Uani 1 1 d D . . H53A H 1.1387 0.4167 0.3679 0.139 Uiso 1 1 calc R . . H53B H 1.2553 0.3809 0.3249 0.139 Uiso 1 1 calc R . . H53C H 1.2252 0.3641 0.4355 0.139 Uiso 1 1 calc R . . C54 C 0.9606(13) 0.2206(9) 0.3534(10) 0.0924(17) Uani 1 1 d . . . H54A H 1.0123 0.1865 0.3922 0.139 Uiso 1 1 calc R . . H54B H 0.9622 0.2114 0.2825 0.139 Uiso 1 1 calc R . . H54C H 0.8747 0.2175 0.3702 0.139 Uiso 1 1 calc R . . C55 C 0.9787(15) 0.5709(8) 0.8748(10) 0.087(4) Uani 1 1 d . . . H55 H 0.9730 0.5217 0.8967 0.105 Uiso 1 1 calc R . . Cl1 Cl 0.8436(5) 0.5895(4) 0.8034(4) 0.150(2) Uani 1 1 d . . . Cl2 Cl 1.0035(6) 0.6216(3) 0.9825(4) 0.1250(17) Uani 1 1 d . . . Cl3 Cl 1.1109(4) 0.5773(2) 0.8114(3) 0.0999(11) Uani 1 1 d . . . C56 C 0.4634(10) 0.5760(5) 0.3893(8) 0.058(3) Uani 1 1 d . . . H56 H 0.5409 0.5990 0.3717 0.069 Uiso 1 1 calc R . . Cl4 Cl 0.3464(3) 0.63912(16) 0.3854(3) 0.0864(10) Uani 1 1 d . . . Cl5 Cl 0.4958(3) 0.54081(14) 0.5052(2) 0.0679(7) Uani 1 1 d . . . Cl6 Cl 0.4231(5) 0.51215(18) 0.3004(3) 0.1140(15) Uani 1 1 d . . . C57 C 0.836(2) 0.5103(13) 0.1935(17) 0.1554(14) Uani 1 1 d . . . H57 H 0.8193 0.4648 0.2246 0.187 Uiso 1 1 calc R . . Cl7 Cl 0.7393(5) 0.5481(4) 0.2622(5) 0.1554(14) Uani 1 1 d . . . Cl8 Cl 0.9867(6) 0.4986(3) 0.2208(5) 0.1554(14) Uani 1 1 d . . . Cl9 Cl 0.7753(6) 0.4772(3) 0.0747(5) 0.1554(14) 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 Zn1 0.0309(3) 0.0136(3) 0.0280(3) -0.0042(2) -0.0053(2) -0.0036(2) N1 0.033(3) 0.015(3) 0.019(3) 0.001(2) -0.006(3) 0.000(3) N2 0.034(3) 0.014(2) 0.027(3) 0.001(2) -0.013(2) -0.005(2) N3 0.032(3) 0.017(3) 0.028(3) -0.002(2) -0.006(3) -0.002(3) N4 0.032(2) 0.016(2) 0.023(2) -0.0047(18) -0.0014(17) -0.0019(19) C1 0.030(4) 0.024(4) 0.024(3) 0.007(3) -0.004(3) -0.006(3) C2 0.036(4) 0.023(4) 0.034(4) -0.003(3) 0.002(3) -0.002(3) C3 0.032(4) 0.021(3) 0.038(4) 0.001(3) 0.003(3) 0.000(3) C4 0.032(4) 0.014(3) 0.029(4) -0.004(3) -0.009(3) -0.005(3) C5 0.032(4) 0.019(3) 0.031(4) -0.008(3) -0.006(3) 0.002(3) C6 0.034(4) 0.012(3) 0.031(4) -0.004(3) -0.008(3) -0.003(3) C7 0.053(5) 0.032(4) 0.039(4) -0.013(4) 0.001(4) -0.010(4) C8 0.038(5) 0.046(5) 0.046(5) -0.004(4) 0.012(4) -0.001(4) C9 0.041(4) 0.020(3) 0.031(4) -0.004(3) -0.012(3) 0.001(3) C10 0.024(3) 0.024(4) 0.035(4) -0.001(3) -0.007(3) 0.000(3) C11 0.031(4) 0.010(3) 0.034(4) -0.005(3) -0.010(3) 0.001(3) C12 0.044(5) 0.026(4) 0.041(5) -0.003(4) -0.001(4) -0.023(4) C13 0.052(5) 0.028(4) 0.043(5) -0.005(4) -0.014(4) -0.027(4) C14 0.032(4) 0.018(3) 0.032(4) -0.006(3) -0.008(3) -0.003(3) C15 0.040(5) 0.022(4) 0.037(4) -0.003(3) -0.017(4) -0.015(3) C16 0.034(4) 0.017(3) 0.035(4) -0.004(3) -0.006(3) -0.002(3) C17 0.046(5) 0.031(4) 0.036(4) -0.017(3) -0.005(4) -0.010(4) C18 0.039(4) 0.021(3) 0.033(4) -0.015(3) 0.004(3) -0.003(3) C19 0.032(2) 0.016(2) 0.023(2) -0.0047(18) -0.0014(17) -0.0019(19) C20 0.035(4) 0.020(4) 0.022(3) 0.004(3) -0.002(3) 0.002(3) C21 0.039(4) 0.013(3) 0.028(3) -0.002(3) 0.004(3) -0.001(3) C22 0.036(4) 0.021(4) 0.045(4) -0.008(3) 0.006(4) -0.006(3) C23 0.032(4) 0.020(3) 0.024(4) -0.004(3) -0.002(3) -0.002(3) C24 0.046(5) 0.047(5) 0.056(5) -0.026(4) 0.005(4) -0.019(4) C25 0.037(4) 0.039(4) 0.044(5) -0.016(4) 0.008(4) -0.014(3) N5 0.026(3) 0.025(3) 0.034(3) 0.007(3) -0.001(3) 0.003(3) C26 0.039(4) 0.013(3) 0.032(4) 0.003(3) 0.001(3) 0.003(3) C27 0.036(4) 0.016(3) 0.033(3) -0.005(3) 0.001(3) -0.006(3) C28 0.033(4) 0.030(5) 0.033(4) 0.005(3) -0.006(3) -0.003(3) C29 0.035(4) 0.058(6) 0.036(4) 0.016(4) -0.001(4) 0.011(4) C30 0.077(8) 0.072(7) 0.046(5) 0.027(5) -0.003(5) -0.018(6) C31 0.031(4) 0.054(5) 0.057(5) 0.007(4) 0.006(4) 0.000(4) C32 0.028(4) 0.030(4) 0.064(5) -0.001(4) 0.008(3) 0.003(3) C33 0.031(4) 0.027(3) 0.039(4) 0.003(3) 0.002(3) -0.002(3) O1 0.085(4) 0.131(5) 0.079(3) 0.007(4) 0.021(3) -0.025(4) C34 0.085(4) 0.131(5) 0.079(3) 0.007(4) 0.021(3) -0.025(4) C35 0.085(4) 0.131(5) 0.079(3) 0.007(4) 0.021(3) -0.025(4) C36 0.085(4) 0.131(5) 0.079(3) 0.007(4) 0.021(3) -0.025(4) C37 0.085(4) 0.131(5) 0.079(3) 0.007(4) 0.021(3) -0.025(4) C38 0.043(5) 0.037(5) 0.046(5) 0.025(4) 0.004(4) 0.007(4) C39 0.059(6) 0.022(4) 0.035(4) 0.009(3) -0.009(4) 0.012(4) C40 0.052(5) 0.020(4) 0.035(4) 0.011(3) -0.001(4) 0.014(4) C41 0.047(5) 0.038(4) 0.063(6) 0.014(4) 0.004(4) 0.011(4) C42 0.033(4) 0.029(4) 0.052(5) 0.012(4) 0.001(4) 0.005(3) N6 0.044(4) 0.012(3) 0.027(3) 0.003(2) -0.005(3) 0.002(3) C43 0.053(5) 0.043(5) 0.047(5) 0.033(4) -0.001(4) 0.013(4) C44 0.039(5) 0.051(5) 0.097(8) 0.063(6) 0.026(5) 0.012(4) C45 0.038(4) 0.023(4) 0.029(3) -0.006(3) -0.001(3) -0.006(3) C46 0.044(5) 0.061(7) 0.033(4) 0.006(4) -0.004(3) 0.003(4) C47 0.043(5) 0.059(7) 0.059(6) 0.006(4) -0.001(4) 0.001(4) C48 0.046(5) 0.074(7) 0.031(4) -0.007(4) 0.009(3) -0.025(5) C49 0.061(6) 0.041(4) 0.028(4) 0.002(3) 0.018(4) 0.007(4) C50 0.069(7) 0.039(5) 0.041(5) 0.008(4) -0.009(5) 0.002(5) O2 0.079(4) 0.131(5) 0.068(3) 0.001(3) 0.008(3) -0.017(3) C51 0.079(4) 0.131(5) 0.068(3) 0.001(3) 0.008(3) -0.017(3) C52 0.079(4) 0.131(5) 0.068(3) 0.001(3) 0.008(3) -0.017(3) C53 0.079(4) 0.131(5) 0.068(3) 0.001(3) 0.008(3) -0.017(3) C54 0.079(4) 0.131(5) 0.068(3) 0.001(3) 0.008(3) -0.017(3) C55 0.124(12) 0.061(7) 0.082(9) -0.018(6) 0.032(8) 0.016(8) Cl1 0.099(3) 0.224(7) 0.131(4) -0.030(4) 0.032(3) -0.027(4) Cl2 0.154(4) 0.110(3) 0.117(3) -0.051(3) 0.040(3) -0.033(3) Cl3 0.095(3) 0.115(3) 0.089(2) 0.009(2) 0.0085(19) 0.001(2) C56 0.064(6) 0.033(5) 0.077(7) 0.001(5) 0.012(5) 0.013(4) Cl4 0.0545(15) 0.0642(17) 0.139(3) 0.0363(18) 0.0029(17) 0.0164(13) Cl5 0.0712(17) 0.0461(13) 0.0857(18) 0.0160(13) 0.0060(13) 0.0048(12) Cl6 0.167(4) 0.0573(17) 0.107(3) 0.0139(18) -0.034(3) -0.016(2) C57 0.153(3) 0.134(3) 0.172(3) -0.061(2) -0.016(2) 0.037(2) Cl7 0.153(3) 0.134(3) 0.172(3) -0.061(2) -0.016(2) 0.037(2) Cl8 0.153(3) 0.134(3) 0.172(3) -0.061(2) -0.016(2) 0.037(2) Cl9 0.153(3) 0.134(3) 0.172(3) -0.061(2) -0.016(2) 0.037(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 Zn1 N2 2.042(6) . ? Zn1 N3 2.057(6) . ? Zn1 N1 2.067(6) . ? Zn1 N4 2.084(6) . ? Zn1 N5 2.359(6) . ? Zn1 N6 2.411(6) . ? N1 C1 1.378(10) . ? N1 C4 1.388(9) . ? N2 C6 1.389(9) . ? N2 C9 1.402(11) . ? N3 C14 1.346(9) . ? N3 C11 1.355(10) . ? N4 C19 1.335(10) . ? N4 C16 1.364(9) . ? C1 C20 1.370(10) . ? C1 C2 1.462(10) . ? C2 C3 1.360(11) . ? C2 H2 0.9500 . ? C3 C4 1.441(11) . ? C3 H3 0.9500 . ? C4 C5 1.434(12) . ? C5 C6 1.396(11) . ? C5 C21 1.398(10) . ? C6 C7 1.471(12) . ? C7 C8 1.319(13) . ? C7 H7 0.9500 . ? C8 C9 1.424(12) . ? C8 H8 0.9500 . ? C9 C10 1.420(10) . ? C10 C11 1.445(10) . ? C10 C28 1.490(11) . ? C11 C12 1.455(10) . ? C12 C13 1.348(13) . ? C12 H12 0.9500 . ? C13 C14 1.449(12) . ? C13 H13 0.9500 . ? C14 C15 1.396(13) . ? C15 C16 1.414(12) . ? C15 C38 1.481(11) 2_546 ? C16 C17 1.424(12) . ? C17 C18 1.390(11) . ? C17 H17 0.9500 . ? C18 C19 1.472(9) . ? C18 H18 0.9500 . ? C19 C20 1.393(10) . ? C20 C45 1.529(11) . ? C21 C22 1.210(11) . ? C22 C23 1.442(11) . ? C23 C24 1.404(12) . ? C23 C27 1.410(11) . ? C24 C25 1.333(12) . ? C24 H24 0.9500 . ? C25 N5 1.361(11) 2_657 ? C25 H25 0.9500 . ? N5 C26 1.349(10) . ? N5 C25 1.361(11) 2_647 ? C26 C27 1.403(9) 2_647 ? C26 H26 0.9500 . ? C27 C26 1.403(9) 2_657 ? C27 H27 0.9500 . ? C28 C29 1.356(11) . ? C28 C33 1.396(10) . ? C29 C30 1.387(15) . ? C29 H29 0.9500 . ? C30 C31 1.359(14) . ? C30 H30 0.9500 . ? C31 C32 1.329(13) . ? C31 O1 1.381(13) . ? C32 C33 1.422(11) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O1 C34 1.333(16) . ? C34 C37 1.43(2) . ? C34 C35 1.604(16) . ? C34 H34 1.0000 . ? C35 C36 1.53(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C39 1.177(11) . ? C38 C15 1.481(11) 2_556 ? C39 C40 1.431(10) . ? C40 C41 1.347(13) . ? C40 C44 1.363(13) . ? C41 C42 1.402(11) . ? C41 H41 0.9500 . ? C42 N6 1.321(10) . ? C42 H42 0.9500 . ? N6 C43 1.294(11) . ? C43 C44 1.433(11) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.365(12) . ? C45 C50 1.402(12) . ? C46 C47 1.434(14) . ? C46 H46 0.9500 . ? C47 C48 1.330(13) . ? C47 H47 0.9500 . ? C48 C49 1.383(14) . ? C48 O2 1.439(13) . ? C49 C50 1.404(14) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? O2 C51 1.599(19) . ? C51 C52 1.359(18) . ? C51 C54 1.50(2) . ? C51 H51 1.0000 . ? C52 C53 1.505(15) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 Cl1 1.700(17) . ? C55 Cl3 1.748(16) . ? C55 Cl2 1.754(14) . ? C55 H55 1.0000 . ? C56 Cl5 1.714(11) . ? C56 Cl6 1.747(11) . ? C56 Cl4 1.753(10) . ? C56 H56 1.0000 . ? C57 Cl8 1.65(2) . ? C57 Cl7 1.64(2) . ? C57 Cl9 1.79(2) . ? C57 H57 1.0000 . ? 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 N2 Zn1 N3 89.4(2) . . ? N2 Zn1 N1 91.2(2) . . ? N3 Zn1 N1 179.2(3) . . ? N2 Zn1 N4 177.9(3) . . ? N3 Zn1 N4 90.8(2) . . ? N1 Zn1 N4 88.7(2) . . ? N2 Zn1 N5 91.3(2) . . ? N3 Zn1 N5 88.7(2) . . ? N1 Zn1 N5 91.9(2) . . ? N4 Zn1 N5 86.6(2) . . ? N2 Zn1 N6 88.6(2) . . ? N3 Zn1 N6 91.9(2) . . ? N1 Zn1 N6 87.6(2) . . ? N4 Zn1 N6 93.5(2) . . ? N5 Zn1 N6 179.4(3) . . ? C1 N1 C4 107.7(6) . . ? C1 N1 Zn1 127.1(4) . . ? C4 N1 Zn1 124.9(5) . . ? C6 N2 C9 104.6(6) . . ? C6 N2 Zn1 126.4(6) . . ? C9 N2 Zn1 128.5(4) . . ? C14 N3 C11 105.5(6) . . ? C14 N3 Zn1 125.8(6) . . ? C11 N3 Zn1 127.6(5) . . ? C19 N4 C16 109.3(6) . . ? C19 N4 Zn1 126.0(4) . . ? C16 N4 Zn1 124.5(5) . . ? C20 C1 N1 124.5(6) . . ? C20 C1 C2 127.1(7) . . ? N1 C1 C2 108.3(6) . . ? C3 C2 C1 107.4(7) . . ? C3 C2 H2 126.3 . . ? C1 C2 H2 126.3 . . ? C2 C3 C4 107.7(7) . . ? C2 C3 H3 126.2 . . ? C4 C3 H3 126.2 . . ? N1 C4 C5 125.4(7) . . ? N1 C4 C3 108.9(7) . . ? C5 C4 C3 125.7(7) . . ? C6 C5 C21 118.7(7) . . ? C6 C5 C4 126.3(7) . . ? C21 C5 C4 115.1(7) . . ? N2 C6 C5 125.3(7) . . ? N2 C6 C7 110.3(7) . . ? C5 C6 C7 124.4(7) . . ? C8 C7 C6 105.4(7) . . ? C8 C7 H7 127.3 . . ? C6 C7 H7 127.3 . . ? C7 C8 C9 110.4(8) . . ? C7 C8 H8 124.8 . . ? C9 C8 H8 124.8 . . ? N2 C9 C10 123.6(7) . . ? N2 C9 C8 109.2(7) . . ? C10 C9 C8 127.2(8) . . ? C9 C10 C11 124.9(7) . . ? C9 C10 C28 118.5(7) . . ? C11 C10 C28 116.7(6) . . ? N3 C11 C10 125.5(6) . . ? N3 C11 C12 111.5(6) . . ? C10 C11 C12 123.0(8) . . ? C13 C12 C11 105.0(8) . . ? C13 C12 H12 127.5 . . ? C11 C12 H12 127.5 . . ? C12 C13 C14 107.1(7) . . ? C12 C13 H13 126.5 . . ? C14 C13 H13 126.5 . . ? N3 C14 C15 125.7(7) . . ? N3 C14 C13 110.8(7) . . ? C15 C14 C13 123.4(7) . . ? C14 C15 C16 127.1(7) . . ? C14 C15 C38 116.2(8) . 2_546 ? C16 C15 C38 116.7(8) . 2_546 ? N4 C16 C15 125.5(8) . . ? N4 C16 C17 108.3(7) . . ? C15 C16 C17 126.2(7) . . ? C18 C17 C16 108.7(7) . . ? C18 C17 H17 125.7 . . ? C16 C17 H17 125.7 . . ? C17 C18 C19 103.9(7) . . ? C17 C18 H18 128.1 . . ? C19 C18 H18 128.1 . . ? N4 C19 C20 126.7(6) . . ? N4 C19 C18 109.8(6) . . ? C20 C19 C18 123.3(7) . . ? C1 C20 C19 127.0(7) . . ? C1 C20 C45 116.1(6) . . ? C19 C20 C45 117.0(6) . . ? C22 C21 C5 178.2(10) . . ? C21 C22 C23 177.2(9) . . ? C24 C23 C27 118.1(7) . . ? C24 C23 C22 120.8(8) . . ? C27 C23 C22 121.1(7) . . ? C25 C24 C23 121.4(9) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 N5 123.4(9) . 2_657 ? C24 C25 H25 118.3 . . ? N5 C25 H25 118.3 2_657 . ? C26 N5 C25 115.4(7) . 2_647 ? C26 N5 Zn1 122.3(5) . . ? C25 N5 Zn1 121.9(5) 2_647 . ? N5 C26 C27 126.2(7) . 2_647 ? N5 C26 H26 116.9 . . ? C27 C26 H26 116.9 2_647 . ? C26 C27 C23 115.5(7) 2_657 . ? C26 C27 H27 122.3 2_657 . ? C23 C27 H27 122.3 . . ? C29 C28 C33 118.0(8) . . ? C29 C28 C10 123.1(7) . . ? C33 C28 C10 118.7(6) . . ? C28 C29 C30 120.8(8) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C31 C30 C29 121.7(9) . . ? C31 C30 H30 119.2 . . ? C29 C30 H30 119.2 . . ? C32 C31 C30 118.5(9) . . ? C32 C31 O1 117.0(8) . . ? C30 C31 O1 124.6(9) . . ? C31 C32 C33 121.5(7) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C28 C33 C32 119.1(7) . . ? C28 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? C34 O1 C31 124.5(11) . . ? O1 C34 C37 115.3(13) . . ? O1 C34 C35 100.4(12) . . ? C37 C34 C35 105.1(13) . . ? O1 C34 H34 111.7 . . ? C37 C34 H34 111.8 . . ? C35 C34 H34 111.8 . . ? C36 C35 C34 114.1(13) . . ? C36 C35 H35A 108.7 . . ? C34 C35 H35A 108.7 . . ? C36 C35 H35B 108.7 . . ? C34 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 C38 C15 178.5(11) . 2_556 ? C38 C39 C40 175.2(11) . . ? C41 C40 C44 117.1(7) . . ? C41 C40 C39 123.3(9) . . ? C44 C40 C39 119.6(8) . . ? C40 C41 C42 119.9(9) . . ? C40 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? N6 C42 C41 123.7(8) . . ? N6 C42 H42 118.1 . . ? C41 C42 H42 118.1 . . ? C43 N6 C42 116.8(7) . . ? C43 N6 Zn1 121.7(6) . . ? C42 N6 Zn1 121.5(5) . . ? N6 C43 C44 122.9(9) . . ? N6 C43 H43 118.5 . . ? C44 C43 H43 118.5 . . ? C40 C44 C43 119.4(8) . . ? C40 C44 H44 120.3 . . ? C43 C44 H44 120.3 . . ? C46 C45 C50 118.8(8) . . ? C46 C45 C20 120.6(7) . . ? C50 C45 C20 120.6(7) . . ? C45 C46 C47 121.5(8) . . ? C45 C46 H46 119.3 . . ? C47 C46 H46 119.3 . . ? C48 C47 C46 117.9(9) . . ? C48 C47 H47 121.1 . . ? C46 C47 H47 121.1 . . ? C47 C48 C49 123.2(9) . . ? C47 C48 O2 123.7(10) . . ? C49 C48 O2 113.1(8) . . ? C48 C49 C50 118.8(8) . . ? C48 C49 H49 120.6 . . ? C50 C49 H49 120.6 . . ? C45 C50 C49 119.8(9) . . ? C45 C50 H50 120.1 . . ? C49 C50 H50 120.1 . . ? C48 O2 C51 118.0(9) . . ? C52 C51 C54 118.4(14) . . ? C52 C51 O2 110.1(13) . . ? C54 C51 O2 109.7(11) . . ? C52 C51 H51 105.9 . . ? C54 C51 H51 105.9 . . ? O2 C51 H51 105.9 . . ? C51 C52 C53 122.4(13) . . ? C51 C52 H52A 106.7 . . ? C53 C52 H52A 106.7 . . ? C51 C52 H52B 106.7 . . ? C53 C52 H52B 106.7 . . ? H52A C52 H52B 106.6 . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? Cl1 C55 Cl3 113.6(8) . . ? Cl1 C55 Cl2 113.6(8) . . ? Cl3 C55 Cl2 108.1(9) . . ? Cl1 C55 H55 107.0 . . ? Cl3 C55 H55 107.0 . . ? Cl2 C55 H55 107.0 . . ? Cl5 C56 Cl6 111.3(6) . . ? Cl5 C56 Cl4 112.3(6) . . ? Cl6 C56 Cl4 110.3(6) . . ? Cl5 C56 H56 107.6 . . ? Cl6 C56 H56 107.6 . . ? Cl4 C56 H56 107.6 . . ? Cl8 C57 Cl7 127.3(13) . . ? Cl8 C57 Cl9 114.1(12) . . ? Cl7 C57 Cl9 118.6(13) . . ? Cl8 C57 H57 90.0 . . ? Cl7 C57 H57 90.0 . . ? Cl9 C57 H57 90.0 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.029 _refine_diff_density_min -1.404 _refine_diff_density_rms 0.147 _database_code_depnum_ccdc_archive 'CCDC 942058' ####################################################################### # # 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_compound(R,R)-2-Zn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56.50 H44.50 Cl7.50 N6 O2 Zn' _chemical_formula_weight 1170.73 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.7272(4) _cell_length_b 19.2135(7) _cell_length_c 13.6582(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.605(2) _cell_angle_gamma 90.00 _cell_volume 2801.59(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6329 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 24.15 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1198 _exptl_absorpt_coefficient_mu 0.843 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9056 _exptl_absorpt_correction_T_max 0.9356 _exptl_absorpt_process_details sadabs _exptl_special_details ; The starting porphyrin being chiral the space group is thus necessarly noncentrosymmetric Absolute configurations have been fixed based on known configurations The crystal has a low diffracting power ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 38630 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 30.00 _reflns_number_total 14452 _reflns_number_gt 9458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. DFIX 1.54 0.02 C52 C53 wer used in order to fix Csp3-Csp3 to acceptable values ; _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^)+(0.1878P)^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 0.02(2) _refine_ls_number_reflns 14452 _refine_ls_number_parameters 632 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1317 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.2842 _refine_ls_wR_factor_gt 0.2441 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Zn1 Zn 0.74896(7) 0.67403(6) 0.24876(5) 0.02709(16) Uani 1 1 d . . . N1 N 0.5857(5) 0.6165(3) 0.2458(3) 0.0264(11) Uani 1 1 d . . . N2 N 0.7961(5) 0.6256(3) 0.1229(4) 0.0305(13) Uani 1 1 d . . . N3 N 0.9122(5) 0.7308(3) 0.2539(4) 0.0290(12) Uani 1 1 d . . . N4 N 0.6994(5) 0.7243(3) 0.3742(3) 0.0258(11) Uani 1 1 d . . . C1 C 0.4993(6) 0.6181(3) 0.3118(4) 0.0267(13) Uani 1 1 d . . . C2 C 0.4054(7) 0.5638(4) 0.2900(5) 0.0379(16) Uani 1 1 d . . . H2 H 0.3347 0.5540 0.3244 0.045 Uiso 1 1 calc R . . C3 C 0.4416(7) 0.5304(4) 0.2093(5) 0.0387(17) Uani 1 1 d . . . H3 H 0.3996 0.4921 0.1768 0.046 Uiso 1 1 calc R . . C4 C 0.5537(7) 0.5626(4) 0.1816(5) 0.0316(16) Uani 1 1 d . . . C5 C 0.6206(7) 0.5421(4) 0.1000(5) 0.0342(15) Uani 1 1 d . . . C6 C 0.7330(6) 0.5726(4) 0.0731(5) 0.0296(14) Uani 1 1 d . . . C7 C 0.7985(9) 0.5494(5) -0.0077(6) 0.053(2) Uani 1 1 d . . . H7 H 0.7725 0.5137 -0.0534 0.063 Uiso 1 1 calc R . . C8 C 0.9001(8) 0.5865(5) -0.0063(6) 0.0469(19) Uani 1 1 d . . . H8 H 0.9616 0.5830 -0.0516 0.056 Uiso 1 1 calc R . . C9 C 0.9032(6) 0.6349(3) 0.0776(4) 0.0297(14) Uani 1 1 d . . . C10 C 1.0000(6) 0.6835(3) 0.1054(4) 0.0279(14) Uani 1 1 d . . . C11 C 1.0000(6) 0.7284(4) 0.1875(5) 0.0321(15) Uani 1 1 d . . . C12 C 1.0876(7) 0.7835(4) 0.2090(6) 0.0407(18) Uani 1 1 d . . . H12 H 1.1583 0.7931 0.1744 0.049 Uiso 1 1 calc R . . C13 C 1.0533(8) 0.8196(4) 0.2866(6) 0.0454(19) Uani 1 1 d . . . H13 H 1.0928 0.8597 0.3160 0.054 Uiso 1 1 calc R . . C14 C 0.9438(8) 0.7844(4) 0.3155(5) 0.0357(17) Uani 1 1 d . . . C15 C 0.8769(8) 0.8068(4) 0.3929(5) 0.0371(17) Uani 1 1 d . . . C16 C 0.7644(8) 0.7786(4) 0.4196(5) 0.0358(17) Uani 1 1 d . . . C17 C 0.6957(8) 0.8026(4) 0.4998(5) 0.0414(17) Uani 1 1 d . . . H17 H 0.7197 0.8395 0.5441 0.050 Uiso 1 1 calc R . . C18 C 0.5890(7) 0.7621(4) 0.5002(5) 0.0385(17) Uani 1 1 d . . . H18 H 0.5257 0.7657 0.5439 0.046 Uiso 1 1 calc R . . C19 C 0.5938(7) 0.7133(3) 0.4202(5) 0.0346(16) Uani 1 1 d . . . C20 C 0.5004(7) 0.6658(4) 0.3919(4) 0.0327(15) Uani 1 1 d . . . C21 C 0.5677(8) 0.4870(4) 0.0436(5) 0.0378(18) Uani 1 1 d . . . C22 C 0.5241(8) 0.4380(4) -0.0039(6) 0.0403(18) Uani 1 1 d . . . C23 C 0.4662(8) 0.3798(4) -0.0545(5) 0.0360(17) Uani 1 1 d . . . C24 C 0.3475(8) 0.3561(5) -0.0382(7) 0.057(2) Uani 1 1 d . . . H24 H 0.2997 0.3798 0.0063 0.069 Uiso 1 1 calc R . . C25 C 0.3001(8) 0.2980(4) -0.0872(6) 0.048(2) Uani 1 1 d . . . H25 H 0.2221 0.2806 -0.0704 0.058 Uiso 1 1 calc R . . N5 N 0.6455(5) 0.7643(3) 0.1560(4) 0.0298(12) Uani 1 1 d . . . C26 C 0.5333(7) 0.7878(4) 0.1750(5) 0.0344(15) Uani 1 1 d . . . H26 H 0.4932 0.7645 0.2247 0.041 Uiso 1 1 calc R . . C27 C 0.5301(7) 0.3439(3) -0.1277(4) 0.0364(14) Uani 1 1 d . . . H27 H 0.6110 0.3577 -0.1430 0.044 Uiso 1 1 calc R . . C28 C 1.1087(6) 0.6852(4) 0.0491(5) 0.0342(16) Uani 1 1 d . . . C29 C 1.1054(8) 0.7087(5) -0.0468(6) 0.055(2) Uani 1 1 d . . . H29 H 1.0268 0.7194 -0.0817 0.066 Uiso 1 1 calc R . . C30 C 1.2116(9) 0.7169(6) -0.0925(7) 0.068(3) Uani 1 1 d . . . H30 H 1.2051 0.7339 -0.1581 0.082 Uiso 1 1 calc R . . C31 C 1.3286(8) 0.7013(5) -0.0460(7) 0.058(2) Uani 1 1 d . . . C32 C 1.3358(7) 0.6758(6) 0.0452(6) 0.0569(19) Uani 1 1 d . . . H32 H 1.4146 0.6618 0.0767 0.068 Uiso 1 1 calc R . . C33 C 1.2288(6) 0.6697(5) 0.0949(5) 0.0407(15) Uani 1 1 d . . . H33 H 1.2371 0.6546 0.1614 0.049 Uiso 1 1 calc R . . O1 O 1.4388(8) 0.7080(6) -0.0875(6) 0.1040(17) Uani 1 1 d . . . C34 C 1.4423(14) 0.7292(9) -0.1785(10) 0.1040(17) Uani 1 1 d . . . H34 H 1.3740 0.7071 -0.2231 0.125 Uiso 1 1 calc R . . C35 C 1.4326(13) 0.8106(8) -0.1829(10) 0.1040(17) Uani 1 1 d . . . H35A H 1.3637 0.8262 -0.1449 0.125 Uiso 1 1 calc R . . H35B H 1.5116 0.8312 -0.1521 0.125 Uiso 1 1 calc R . . C36 C 1.4077(13) 0.8373(9) -0.2917(9) 0.1040(17) Uani 1 1 d . . . H36A H 1.3240 0.8226 -0.3192 0.156 Uiso 1 1 calc R . . H36B H 1.4707 0.8177 -0.3312 0.156 Uiso 1 1 calc R . . H36C H 1.4127 0.8882 -0.2926 0.156 Uiso 1 1 calc R . . C37 C 1.5709(13) 0.7131(8) -0.2126(10) 0.1040(17) Uani 1 1 d . . . H37A H 1.6364 0.7332 -0.1659 0.156 Uiso 1 1 calc R . . H37B H 1.5764 0.7332 -0.2779 0.156 Uiso 1 1 calc R . . H37C H 1.5824 0.6626 -0.2156 0.156 Uiso 1 1 calc R . . C38 C 1.0733(9) 0.3672(5) 0.5498(6) 0.049(2) Uani 1 1 d . . . C39 C 1.0309(9) 0.4147(5) 0.5044(6) 0.054(2) Uani 1 1 d . . . C40 C 0.9737(8) 0.4719(4) 0.4483(6) 0.043(2) Uani 1 1 d . . . C41 C 1.0368(9) 0.5198(5) 0.4074(7) 0.061(2) Uani 1 1 d . . . H41 H 1.1258 0.5180 0.4139 0.073 Uiso 1 1 calc R . . C42 C 0.9747(9) 0.5745(5) 0.3532(7) 0.054(2) Uani 1 1 d . . . H42 H 1.0235 0.6082 0.3232 0.065 Uiso 1 1 calc R . . N6 N 0.8528(6) 0.5807(3) 0.3428(4) 0.0346(14) Uani 1 1 d . . . C43 C 0.7863(9) 0.5334(4) 0.3887(6) 0.049(2) Uani 1 1 d . . . H43 H 0.6978 0.5375 0.3856 0.059 Uiso 1 1 calc R . . C44 C 0.8479(9) 0.4772(5) 0.4418(7) 0.062(3) Uani 1 1 d . . . H44 H 0.8001 0.4434 0.4726 0.074 Uiso 1 1 calc R . . C45 C 0.3904(7) 0.6607(3) 0.4549(4) 0.0339(16) Uani 1 1 d . . . C46 C 0.2797(8) 0.6893(5) 0.4231(6) 0.053(2) Uani 1 1 d . . . H46 H 0.2700 0.7112 0.3604 0.063 Uiso 1 1 calc R . . C47 C 0.1773(8) 0.6876(6) 0.4808(7) 0.068(3) Uani 1 1 d . . . H47 H 0.0991 0.7075 0.4568 0.081 Uiso 1 1 calc R . . C48 C 0.1923(7) 0.6569(5) 0.5715(5) 0.050(2) Uani 1 1 d . . . C49 C 0.3071(9) 0.6291(5) 0.6060(6) 0.056(2) Uani 1 1 d . . . H49 H 0.3177 0.6085 0.6695 0.067 Uiso 1 1 calc R . . C50 C 0.4085(9) 0.6311(5) 0.5479(6) 0.051(2) Uani 1 1 d . . . H50 H 0.4878 0.6126 0.5720 0.061 Uiso 1 1 calc R . . O2 O 0.1011(8) 0.6506(7) 0.6358(6) 0.116(2) Uani 1 1 d . . . C51 C -0.0134(13) 0.7015(10) 0.6242(10) 0.116(2) Uani 1 1 d . . . H51 H -0.0451 0.7009 0.5529 0.139 Uiso 1 1 calc R . . C52 C -0.1080(12) 0.6778(10) 0.6734(9) 0.116(2) Uani 1 1 d D . . H52A H -0.1674 0.7165 0.6801 0.139 Uiso 1 1 calc R . . H52B H -0.0731 0.6644 0.7406 0.139 Uiso 1 1 calc R . . C53 C -0.1779(12) 0.6185(10) 0.6290(9) 0.116(2) Uani 1 1 d D . . H53A H -0.1347 0.5752 0.6495 0.174 Uiso 1 1 calc R . . H53B H -0.1834 0.6225 0.5572 0.174 Uiso 1 1 calc R . . H53C H -0.2624 0.6181 0.6505 0.174 Uiso 1 1 calc R . . C54 C 0.0253(13) 0.7742(11) 0.6477(9) 0.116(2) Uani 1 1 d . . . H54A H -0.0462 0.8054 0.6322 0.174 Uiso 1 1 calc R . . H54B H 0.0934 0.7874 0.6086 0.174 Uiso 1 1 calc R . . H54C H 0.0541 0.7779 0.7179 0.174 Uiso 1 1 calc R . . C55 C 0.0205(14) 0.4285(7) 0.1195(9) 0.098(4) Uani 1 1 d . . . H55 H 0.0257 0.4782 0.0989 0.117 Uiso 1 1 calc R . . Cl1 Cl 0.1552(5) 0.4103(4) 0.1894(4) 0.174(3) Uani 1 1 d . . . Cl2 Cl -0.0038(5) 0.3804(3) 0.0140(4) 0.1392(17) Uani 1 1 d . . . Cl3 Cl -0.1118(4) 0.4212(3) 0.1850(3) 0.1124(12) Uani 1 1 d . . . C56 C 0.5265(10) 0.4221(6) 0.6144(8) 0.073(3) Uani 1 1 d . . . H56 H 0.4486 0.3988 0.6325 0.088 Uiso 1 1 calc R . . Cl4 Cl 0.6511(3) 0.36113(18) 0.6155(3) 0.1087(12) Uani 1 1 d . . . Cl5 Cl 0.5011(3) 0.45915(14) 0.4958(2) 0.0782(7) Uani 1 1 d . . . Cl6 Cl 0.5740(6) 0.4877(2) 0.7000(3) 0.1474(19) Uani 1 1 d . . . C57 C 0.1691(19) 0.5008(16) 0.788(2) 0.110(11) Uani 0.50 1 d P . . H57 H 0.1736 0.5453 0.7503 0.133 Uiso 0.50 1 calc PR . . Cl7 Cl 0.2564(5) 0.4491(3) 0.7319(4) 0.0848(16) Uani 0.50 1 d P . . Cl8 Cl 0.0111(8) 0.4885(7) 0.7901(8) 0.180(6) Uani 0.50 1 d P . . Cl9 Cl 0.2299(8) 0.5255(4) 0.9124(8) 0.173(6) Uani 0.50 1 d P . . 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 Zn1 0.0303(3) 0.0194(2) 0.0297(2) -0.00416(18) -0.00668(18) -0.0036(2) N1 0.033(3) 0.018(2) 0.027(2) -0.0029(19) -0.006(2) -0.003(2) N2 0.038(3) 0.020(3) 0.031(2) -0.003(2) -0.010(2) -0.002(2) N3 0.034(3) 0.019(3) 0.031(2) 0.003(2) -0.014(2) 0.001(2) N4 0.030(3) 0.016(2) 0.029(2) 0.0003(19) -0.007(2) -0.001(2) C1 0.029(4) 0.019(3) 0.031(3) 0.006(2) -0.006(2) -0.006(3) C2 0.040(4) 0.036(4) 0.037(3) -0.004(3) 0.000(3) -0.007(3) C3 0.043(5) 0.029(3) 0.041(4) -0.008(3) -0.007(3) -0.007(3) C4 0.027(4) 0.026(3) 0.039(3) -0.005(3) -0.012(3) -0.007(3) C5 0.039(4) 0.027(3) 0.035(3) -0.006(3) -0.004(3) -0.008(3) C6 0.024(4) 0.028(3) 0.035(3) -0.007(3) -0.006(2) -0.003(3) C7 0.058(6) 0.048(5) 0.053(4) -0.021(4) 0.010(4) -0.024(4) C8 0.034(5) 0.057(5) 0.051(4) -0.009(4) 0.010(3) -0.005(4) C9 0.027(4) 0.028(3) 0.031(3) -0.004(2) -0.007(2) -0.002(3) C10 0.023(3) 0.023(3) 0.037(3) -0.004(3) -0.002(2) 0.001(3) C11 0.030(4) 0.028(3) 0.036(3) -0.002(3) -0.010(3) 0.001(3) C12 0.032(4) 0.034(4) 0.054(4) -0.001(3) -0.005(3) -0.016(3) C13 0.045(5) 0.038(4) 0.052(4) -0.005(3) 0.001(3) -0.021(4) C14 0.050(5) 0.020(3) 0.035(3) -0.002(3) -0.010(3) -0.006(3) C15 0.048(5) 0.024(3) 0.036(3) -0.008(3) -0.015(3) -0.012(3) C16 0.055(5) 0.020(3) 0.031(3) -0.005(2) -0.002(3) -0.002(3) C17 0.055(5) 0.034(4) 0.034(3) -0.015(3) 0.001(3) 0.000(3) C18 0.048(5) 0.029(3) 0.037(3) -0.018(3) 0.000(3) -0.001(3) C19 0.049(5) 0.021(3) 0.032(3) -0.001(2) -0.008(3) 0.001(3) C20 0.047(4) 0.026(3) 0.024(2) 0.007(3) -0.005(2) 0.002(3) C21 0.054(5) 0.022(3) 0.037(3) -0.010(3) 0.001(3) -0.007(3) C22 0.050(5) 0.030(4) 0.040(3) -0.018(3) 0.001(3) -0.003(3) C23 0.043(4) 0.027(3) 0.034(3) -0.010(3) -0.013(3) -0.002(3) C24 0.049(5) 0.052(5) 0.072(5) -0.040(4) 0.018(4) -0.024(4) C25 0.033(4) 0.051(5) 0.061(5) -0.029(4) 0.010(3) -0.009(3) N5 0.021(3) 0.030(3) 0.037(3) 0.006(2) -0.006(2) 0.011(2) C26 0.036(4) 0.028(3) 0.039(3) 0.012(2) 0.005(3) 0.008(3) C27 0.036(4) 0.034(3) 0.038(3) -0.011(2) 0.002(3) -0.010(3) C28 0.028(4) 0.034(4) 0.040(3) 0.005(3) -0.001(3) -0.005(3) C29 0.040(5) 0.073(6) 0.051(4) 0.026(4) 0.007(3) 0.016(4) C30 0.060(6) 0.096(8) 0.051(4) 0.020(5) 0.016(4) -0.013(6) C31 0.035(5) 0.072(6) 0.068(5) 0.005(4) 0.007(4) 0.000(4) C32 0.035(4) 0.057(5) 0.077(5) 0.009(5) -0.001(3) 0.006(4) C33 0.030(4) 0.042(3) 0.047(3) 0.006(3) -0.010(2) 0.000(3) O1 0.090(4) 0.124(4) 0.102(3) 0.017(3) 0.029(3) -0.010(3) C34 0.090(4) 0.124(4) 0.102(3) 0.017(3) 0.029(3) -0.010(3) C35 0.090(4) 0.124(4) 0.102(3) 0.017(3) 0.029(3) -0.010(3) C36 0.090(4) 0.124(4) 0.102(3) 0.017(3) 0.029(3) -0.010(3) C37 0.090(4) 0.124(4) 0.102(3) 0.017(3) 0.029(3) -0.010(3) C38 0.052(6) 0.045(5) 0.047(4) 0.018(3) -0.004(4) 0.017(4) C39 0.076(7) 0.046(5) 0.041(4) 0.007(3) 0.002(4) 0.025(4) C40 0.059(6) 0.034(4) 0.038(4) 0.013(3) 0.009(3) 0.025(4) C41 0.063(6) 0.058(5) 0.062(5) 0.024(4) 0.007(4) 0.024(4) C42 0.056(6) 0.038(4) 0.066(5) 0.026(4) -0.007(4) 0.000(4) N6 0.052(4) 0.021(3) 0.028(3) 0.005(2) -0.008(2) -0.002(3) C43 0.049(5) 0.038(4) 0.057(4) 0.028(3) -0.010(3) 0.008(3) C44 0.050(5) 0.058(5) 0.078(6) 0.053(5) 0.009(4) 0.019(4) C45 0.040(4) 0.026(4) 0.034(3) -0.002(3) -0.004(3) 0.001(3) C46 0.048(5) 0.066(6) 0.043(3) 0.006(3) -0.001(3) -0.001(4) C47 0.034(5) 0.093(9) 0.074(5) 0.016(5) -0.010(4) -0.004(5) C48 0.033(4) 0.074(6) 0.043(3) -0.003(3) 0.006(3) -0.014(4) C49 0.075(6) 0.052(5) 0.040(4) 0.005(3) 0.006(4) 0.000(4) C50 0.056(5) 0.053(4) 0.042(4) 0.004(3) -0.006(3) 0.005(4) O2 0.077(4) 0.195(7) 0.077(3) -0.008(4) 0.008(2) -0.033(4) C51 0.077(4) 0.195(7) 0.077(3) -0.008(4) 0.008(2) -0.033(4) C52 0.077(4) 0.195(7) 0.077(3) -0.008(4) 0.008(2) -0.033(4) C53 0.077(4) 0.195(7) 0.077(3) -0.008(4) 0.008(2) -0.033(4) C54 0.077(4) 0.195(7) 0.077(3) -0.008(4) 0.008(2) -0.033(4) C55 0.137(12) 0.078(8) 0.078(7) -0.017(6) 0.006(7) -0.038(8) Cl1 0.104(3) 0.258(7) 0.167(4) -0.044(5) 0.049(3) -0.047(4) Cl2 0.155(4) 0.132(4) 0.135(3) -0.068(3) 0.038(3) -0.022(3) Cl3 0.099(3) 0.146(3) 0.094(2) 0.003(2) 0.0207(17) 0.013(2) C56 0.073(7) 0.056(6) 0.090(7) 0.014(5) 0.005(5) -0.004(5) Cl4 0.0642(18) 0.0858(19) 0.175(3) 0.053(2) 0.0062(18) 0.0155(15) Cl5 0.0802(17) 0.0570(13) 0.0954(17) 0.0203(12) -0.0016(12) -0.0034(12) Cl6 0.230(5) 0.074(2) 0.125(3) 0.016(2) -0.052(3) -0.013(3) C57 0.047(12) 0.13(2) 0.15(2) -0.103(19) 0.011(12) -0.003(12) Cl7 0.080(4) 0.087(4) 0.093(3) 0.014(3) 0.040(3) 0.011(3) Cl8 0.096(5) 0.263(13) 0.184(9) -0.169(10) 0.032(5) -0.033(7) Cl9 0.140(6) 0.096(4) 0.255(10) -0.122(6) -0.130(7) 0.065(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N3 2.058(6) . ? Zn1 N2 2.061(5) . ? Zn1 N1 2.068(5) . ? Zn1 N4 2.081(5) . ? Zn1 N5 2.360(5) . ? Zn1 N6 2.415(6) . ? N1 C1 1.355(8) . ? N1 C4 1.378(8) . ? N2 C9 1.369(9) . ? N2 C6 1.367(8) . ? N3 C14 1.352(8) . ? N3 C11 1.372(9) . ? N4 C19 1.364(9) . ? N4 C16 1.370(9) . ? C1 C20 1.426(9) . ? C1 C2 1.460(9) . ? C2 C3 1.364(10) . ? C2 H2 0.9500 . ? C3 C4 1.435(11) . ? C3 H3 0.9500 . ? C4 C5 1.439(11) . ? C5 C21 1.397(10) . ? C5 C6 1.420(10) . ? C6 C7 1.435(11) . ? C7 C8 1.302(11) . ? C7 H7 0.9500 . ? C8 C9 1.474(10) . ? C8 H8 0.9500 . ? C9 C10 1.421(9) . ? C10 C11 1.414(9) . ? C10 C28 1.458(9) . ? C11 C12 1.427(10) . ? C12 C13 1.347(11) . ? C12 H12 0.9500 . ? C13 C14 1.443(11) . ? C13 H13 0.9500 . ? C14 C15 1.402(12) . ? C15 C16 1.403(11) . ? C15 C38 1.470(10) 2_756 ? C16 C17 1.455(10) . ? C17 C18 1.384(11) . ? C17 H17 0.9500 . ? C18 C19 1.443(9) . ? C18 H18 0.9500 . ? C19 C20 1.383(10) . ? C20 C45 1.530(10) . ? C21 C22 1.212(9) . ? C22 C23 1.425(10) . ? C23 C24 1.391(12) . ? C23 C27 1.441(10) . ? C24 C25 1.373(11) . ? C24 H24 0.9500 . ? C25 N5 1.323(10) 2_645 ? C25 H25 0.9500 . ? N5 C25 1.323(10) 2_655 ? N5 C26 1.334(9) . ? C26 C27 1.400(9) 2_655 ? C26 H26 0.9500 . ? C27 C26 1.400(9) 2_645 ? C27 H27 0.9500 . ? C28 C29 1.383(10) . ? C28 C33 1.407(9) . ? C29 C30 1.360(13) . ? C29 H29 0.9500 . ? C30 C31 1.383(13) . ? C30 H30 0.9500 . ? C31 C32 1.334(12) . ? C31 O1 1.366(12) . ? C32 C33 1.394(11) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O1 C34 1.312(15) . ? C34 C37 1.531(18) . ? C34 C35 1.57(2) . ? C34 H34 1.0000 . ? C35 C36 1.570(18) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C39 1.170(11) . ? C38 C15 1.470(10) 2_746 ? C39 C40 1.442(11) . ? C40 C41 1.301(13) . ? C40 C44 1.348(12) . ? C41 C42 1.414(11) . ? C41 H41 0.9500 . ? C42 N6 1.307(11) . ? C42 H42 0.9500 . ? N6 C43 1.347(10) . ? C43 C44 1.426(10) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.341(11) . ? C45 C50 1.388(10) . ? C46 C47 1.414(13) . ? C46 H46 0.9500 . ? C47 C48 1.368(12) . ? C47 H47 0.9500 . ? C48 C49 1.382(13) . ? C48 O2 1.383(11) . ? C49 C50 1.408(13) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? O2 C51 1.57(2) . ? C51 C52 1.350(18) . ? C51 C54 1.48(2) . ? C51 H51 1.0000 . ? C52 C53 1.462(15) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 Cl1 1.689(16) . ? C55 Cl2 1.709(12) . ? C55 Cl3 1.757(14) . ? C55 H55 1.0000 . ? C56 Cl6 1.760(12) . ? C56 Cl5 1.766(11) . ? C56 Cl4 1.777(12) . ? C56 H56 1.0000 . ? C57 Cl7 1.608(19) . ? C57 Cl8 1.71(2) . ? C57 Cl9 1.83(2) . ? C57 H57 1.0000 . ? 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 N3 Zn1 N2 89.5(2) . . ? N3 Zn1 N1 179.1(2) . . ? N2 Zn1 N1 91.1(2) . . ? N3 Zn1 N4 90.6(2) . . ? N2 Zn1 N4 178.9(2) . . ? N1 Zn1 N4 88.9(2) . . ? N3 Zn1 N5 89.0(2) . . ? N2 Zn1 N5 91.4(2) . . ? N1 Zn1 N5 91.7(2) . . ? N4 Zn1 N5 87.46(19) . . ? N3 Zn1 N6 91.7(2) . . ? N2 Zn1 N6 88.3(2) . . ? N1 Zn1 N6 87.6(2) . . ? N4 Zn1 N6 92.78(19) . . ? N5 Zn1 N6 179.3(2) . . ? C1 N1 C4 107.2(5) . . ? C1 N1 Zn1 127.4(4) . . ? C4 N1 Zn1 124.9(5) . . ? C9 N2 C6 105.6(5) . . ? C9 N2 Zn1 127.1(4) . . ? C6 N2 Zn1 127.0(5) . . ? C14 N3 C11 106.9(6) . . ? C14 N3 Zn1 125.9(5) . . ? C11 N3 Zn1 126.6(4) . . ? C19 N4 C16 108.6(5) . . ? C19 N4 Zn1 126.8(4) . . ? C16 N4 Zn1 124.5(5) . . ? N1 C1 C20 124.8(5) . . ? N1 C1 C2 110.5(5) . . ? C20 C1 C2 124.7(6) . . ? C3 C2 C1 104.9(6) . . ? C3 C2 H2 127.6 . . ? C1 C2 H2 127.6 . . ? C2 C3 C4 108.7(6) . . ? C2 C3 H3 125.6 . . ? C4 C3 H3 125.6 . . ? N1 C4 C3 108.7(6) . . ? N1 C4 C5 125.9(7) . . ? C3 C4 C5 125.5(6) . . ? C21 C5 C6 118.6(7) . . ? C21 C5 C4 115.3(7) . . ? C6 C5 C4 126.1(6) . . ? N2 C6 C5 124.7(6) . . ? N2 C6 C7 111.0(6) . . ? C5 C6 C7 124.2(6) . . ? C8 C7 C6 106.9(7) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C7 C8 C9 108.2(7) . . ? C7 C8 H8 125.9 . . ? C9 C8 H8 125.9 . . ? N2 C9 C10 126.1(6) . . ? N2 C9 C8 108.2(6) . . ? C10 C9 C8 125.7(6) . . ? C11 C10 C9 123.8(6) . . ? C11 C10 C28 117.8(6) . . ? C9 C10 C28 118.3(6) . . ? N3 C11 C10 126.7(6) . . ? N3 C11 C12 108.7(6) . . ? C10 C11 C12 124.4(7) . . ? C13 C12 C11 108.6(7) . . ? C13 C12 H12 125.7 . . ? C11 C12 H12 125.7 . . ? C12 C13 C14 105.5(7) . . ? C12 C13 H13 127.3 . . ? C14 C13 H13 127.3 . . ? N3 C14 C15 125.9(7) . . ? N3 C14 C13 110.4(7) . . ? C15 C14 C13 123.6(7) . . ? C14 C15 C16 126.5(6) . . ? C14 C15 C38 117.2(7) . 2_756 ? C16 C15 C38 116.3(7) . 2_756 ? N4 C16 C15 126.1(6) . . ? N4 C16 C17 108.0(7) . . ? C15 C16 C17 125.9(6) . . ? C18 C17 C16 107.7(6) . . ? C18 C17 H17 126.1 . . ? C16 C17 H17 126.1 . . ? C17 C18 C19 105.8(6) . . ? C17 C18 H18 127.1 . . ? C19 C18 H18 127.1 . . ? N4 C19 C20 125.8(6) . . ? N4 C19 C18 109.9(6) . . ? C20 C19 C18 124.2(7) . . ? C19 C20 C1 126.2(6) . . ? C19 C20 C45 117.5(6) . . ? C1 C20 C45 116.2(6) . . ? C22 C21 C5 178.2(9) . . ? C21 C22 C23 175.7(9) . . ? C24 C23 C22 122.8(7) . . ? C24 C23 C27 117.4(6) . . ? C22 C23 C27 119.8(7) . . ? C25 C24 C23 119.3(8) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? N5 C25 C24 125.1(8) 2_645 . ? N5 C25 H25 117.4 2_645 . ? C24 C25 H25 117.4 . . ? C25 N5 C26 116.3(6) 2_655 . ? C25 N5 Zn1 121.6(5) 2_655 . ? C26 N5 Zn1 122.0(4) . . ? N5 C26 C27 125.2(6) . 2_655 ? N5 C26 H26 117.4 . . ? C27 C26 H26 117.4 2_655 . ? C26 C27 C23 116.5(7) 2_645 . ? C26 C27 H27 121.7 2_645 . ? C23 C27 H27 121.7 . . ? C29 C28 C33 115.3(6) . . ? C29 C28 C10 124.0(6) . . ? C33 C28 C10 120.4(6) . . ? C30 C29 C28 121.8(8) . . ? C30 C29 H29 119.1 . . ? C28 C29 H29 119.1 . . ? C29 C30 C31 121.8(8) . . ? C29 C30 H30 119.1 . . ? C31 C30 H30 119.1 . . ? C32 C31 O1 116.7(8) . . ? C32 C31 C30 118.3(8) . . ? O1 C31 C30 125.0(9) . . ? C31 C32 C33 120.7(7) . . ? C31 C32 H32 119.6 . . ? C33 C32 H32 119.6 . . ? C32 C33 C28 121.8(6) . . ? C32 C33 H33 119.1 . . ? C28 C33 H33 119.1 . . ? C34 O1 C31 121.8(10) . . ? O1 C34 C37 109.5(12) . . ? O1 C34 C35 109.8(13) . . ? C37 C34 C35 104.4(11) . . ? O1 C34 H34 111.0 . . ? C37 C34 H34 111.0 . . ? C35 C34 H34 111.0 . . ? C36 C35 C34 111.5(13) . . ? C36 C35 H35A 109.3 . . ? C34 C35 H35A 109.3 . . ? C36 C35 H35B 109.3 . . ? C34 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 C38 C15 178.4(11) . 2_746 ? C38 C39 C40 177.6(12) . . ? C41 C40 C44 118.6(7) . . ? C41 C40 C39 123.7(8) . . ? C44 C40 C39 117.7(8) . . ? C40 C41 C42 120.8(9) . . ? C40 C41 H41 119.6 . . ? C42 C41 H41 119.6 . . ? N6 C42 C41 122.7(8) . . ? N6 C42 H42 118.7 . . ? C41 C42 H42 118.7 . . ? C42 N6 C43 117.3(6) . . ? C42 N6 Zn1 122.0(5) . . ? C43 N6 Zn1 120.7(5) . . ? N6 C43 C44 120.5(8) . . ? N6 C43 H43 119.8 . . ? C44 C43 H43 119.8 . . ? C40 C44 C43 120.1(8) . . ? C40 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C46 C45 C50 120.3(7) . . ? C46 C45 C20 119.9(6) . . ? C50 C45 C20 119.6(6) . . ? C45 C46 C47 121.4(8) . . ? C45 C46 H46 119.3 . . ? C47 C46 H46 119.3 . . ? C48 C47 C46 119.1(8) . . ? C48 C47 H47 120.5 . . ? C46 C47 H47 120.5 . . ? C47 C48 C49 119.9(8) . . ? C47 C48 O2 125.8(9) . . ? C49 C48 O2 114.3(8) . . ? C48 C49 C50 120.6(7) . . ? C48 C49 H49 119.7 . . ? C50 C49 H49 119.7 . . ? C45 C50 C49 118.7(8) . . ? C45 C50 H50 120.7 . . ? C49 C50 H50 120.7 . . ? C48 O2 C51 118.6(10) . . ? C52 C51 C54 114.7(15) . . ? C52 C51 O2 111.1(15) . . ? C54 C51 O2 111.5(11) . . ? C52 C51 H51 106.3 . . ? C54 C51 H51 106.3 . . ? O2 C51 H51 106.3 . . ? C51 C52 C53 115.8(13) . . ? C51 C52 H52A 108.3 . . ? C53 C52 H52A 108.3 . . ? C51 C52 H52B 108.3 . . ? C53 C52 H52B 108.3 . . ? H52A C52 H52B 107.4 . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? Cl1 C55 Cl2 114.6(9) . . ? Cl1 C55 Cl3 112.6(7) . . ? Cl2 C55 Cl3 108.8(7) . . ? Cl1 C55 H55 106.8 . . ? Cl2 C55 H55 106.8 . . ? Cl3 C55 H55 106.8 . . ? Cl6 C56 Cl5 109.2(6) . . ? Cl6 C56 Cl4 107.3(6) . . ? Cl5 C56 Cl4 108.8(6) . . ? Cl6 C56 H56 110.5 . . ? Cl5 C56 H56 110.5 . . ? Cl4 C56 H56 110.5 . . ? Cl7 C57 Cl8 123.1(13) . . ? Cl7 C57 Cl9 115.6(15) . . ? Cl8 C57 Cl9 106.4(14) . . ? Cl7 C57 H57 103.0 . . ? Cl8 C57 H57 103.0 . . ? Cl9 C57 H57 103.0 . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 1.573 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.140 _database_code_depnum_ccdc_archive 'CCDC 942059' ####################################################################### # # 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_compound(S,S)-2-Zn _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H42 N6 O2 Zn' _chemical_formula_weight 872.31 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9454(3) _cell_length_b 17.1422(6) _cell_length_c 11.7118(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.639(2) _cell_angle_gamma 90.00 _cell_volume 2166.44(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9943 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.37 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9296 _exptl_absorpt_correction_T_max 0.9580 _exptl_absorpt_process_details sadabs _exptl_special_details ; The starting porphyrin being chiral and enantiopure the space group is thus necessarly noncentrosymmetric ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50660 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.20 _reflns_number_total 12469 _reflns_number_gt 9771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.7292P] 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 0.013(11) _refine_ls_number_reflns 12469 _refine_ls_number_parameters 554 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Zn1 Zn 0.24714(3) 0.11164(4) 0.24449(3) 0.02022(7) Uani 1 1 d . . . N1 N 0.3522(2) 0.01561(17) 0.3077(2) 0.0204(6) Uani 1 1 d . . . N2 N 0.1959(2) 0.05636(17) 0.0874(2) 0.0193(5) Uani 1 1 d . . . N3 N 0.1398(2) 0.20667(16) 0.1812(2) 0.0197(5) Uani 1 1 d . . . N4 N 0.2979(2) 0.16722(17) 0.4014(2) 0.0213(6) Uani 1 1 d . . . C1 C 0.4131(3) 0.0057(2) 0.4189(3) 0.0222(7) Uani 1 1 d . . . C2 C 0.4638(3) -0.0727(2) 0.4308(3) 0.0301(8) Uani 1 1 d . . . H2 H 0.5090 -0.0953 0.4992 0.036 Uiso 1 1 calc R . . C3 C 0.4347(3) -0.1075(2) 0.3270(3) 0.0278(7) Uani 1 1 d . . . H3 H 0.4571 -0.1588 0.3079 0.033 Uiso 1 1 calc R . . C4 C 0.3636(3) -0.0527(2) 0.2501(3) 0.0204(6) Uani 1 1 d . . . C5 C 0.3120(3) -0.0666(2) 0.1337(3) 0.0226(7) Uani 1 1 d . . . C6 C 0.2335(3) -0.0163(2) 0.0584(3) 0.0201(6) Uani 1 1 d . . . C7 C 0.1843(3) -0.0321(2) -0.0621(3) 0.0249(7) Uani 1 1 d . . . H7 H 0.1947 -0.0786 -0.1035 0.030 Uiso 1 1 calc R . . C8 C 0.1205(3) 0.0323(2) -0.1043(3) 0.0237(7) Uani 1 1 d . . . H8 H 0.0778 0.0393 -0.1812 0.028 Uiso 1 1 calc R . . C9 C 0.1292(3) 0.0880(2) -0.0119(3) 0.0221(7) Uani 1 1 d . . . C10 C 0.0754(3) 0.1630(2) -0.0212(3) 0.0235(7) Uani 1 1 d . . . C11 C 0.0785(3) 0.2174(2) 0.0707(3) 0.0220(7) Uani 1 1 d . . . C12 C 0.0203(3) 0.2941(2) 0.0608(3) 0.0282(7) Uani 1 1 d . . . H12 H -0.0270 0.3164 -0.0067 0.034 Uiso 1 1 calc R . . C13 C 0.0469(3) 0.3275(2) 0.1674(3) 0.0290(7) Uani 1 1 d . . . H13 H 0.0200 0.3772 0.1894 0.035 Uiso 1 1 calc R . . C14 C 0.1241(3) 0.2728(2) 0.2407(3) 0.0232(7) Uani 1 1 d . . . C15 C 0.1789(3) 0.2887(2) 0.3572(3) 0.0211(6) Uani 1 1 d . . . C16 C 0.2626(3) 0.2398(2) 0.4302(3) 0.0212(6) Uani 1 1 d . . . C17 C 0.3183(3) 0.2582(2) 0.5477(3) 0.0249(7) Uani 1 1 d . . . H17 H 0.3097 0.3055 0.5879 0.030 Uiso 1 1 calc R . . C18 C 0.3852(3) 0.1948(2) 0.5894(3) 0.0268(7) Uani 1 1 d . . . H18 H 0.4325 0.1892 0.6647 0.032 Uiso 1 1 calc R . . C19 C 0.3711(3) 0.13723(19) 0.4975(3) 0.0193(7) Uani 1 1 d . . . C20 C 0.4225(3) 0.0606(2) 0.5087(3) 0.0218(7) Uani 1 1 d . . . C21 C 0.3485(3) -0.1375(2) 0.0816(3) 0.0249(7) Uani 1 1 d . . . C22 C 0.3852(3) -0.1910(2) 0.0340(3) 0.0285(7) Uani 1 1 d . . . C23 C 0.5504(3) 0.2583(2) 0.0342(3) 0.0256(7) Uani 1 1 d . . . C24 C 0.5338(3) 0.1789(2) 0.0153(3) 0.0342(8) Uani 1 1 d . . . H24 H 0.5699 0.1533 -0.0429 0.041 Uiso 1 1 calc R . . C25 C 0.4633(3) 0.1372(2) 0.0829(3) 0.0325(9) Uani 1 1 d . . . H25 H 0.4529 0.0828 0.0692 0.039 Uiso 1 1 calc R . . N5 N 0.4099(2) 0.16899(18) 0.1654(2) 0.0241(6) Uani 1 1 d . . . C26 C 0.4306(3) 0.2457(2) 0.1863(3) 0.0270(7) Uani 1 1 d . . . H26 H 0.3964 0.2690 0.2474 0.032 Uiso 1 1 calc R . . C27 C 0.4988(3) 0.2920(2) 0.1240(3) 0.0275(7) Uani 1 1 d . . . H27 H 0.5104 0.3459 0.1416 0.033 Uiso 1 1 calc R . . C28 C 0.0170(3) 0.1883(2) -0.1396(3) 0.0233(7) Uani 1 1 d . . . C29 C -0.1081(3) 0.2054(2) -0.1716(3) 0.0323(8) Uani 1 1 d . . . H29 H -0.1605 0.2027 -0.1147 0.039 Uiso 1 1 calc R . . C30 C -0.1589(3) 0.2262(3) -0.2834(3) 0.0352(9) Uani 1 1 d . . . H30 H -0.2451 0.2368 -0.3025 0.042 Uiso 1 1 calc R . . C31 C -0.0838(3) 0.2317(2) -0.3682(3) 0.0261(7) Uani 1 1 d . . . C32 C 0.0429(3) 0.2160(2) -0.3371(3) 0.0272(7) Uani 1 1 d . . . H32 H 0.0957 0.2203 -0.3935 0.033 Uiso 1 1 calc R . . C33 C 0.0913(3) 0.1945(2) -0.2263(3) 0.0252(7) Uani 1 1 d . . . H33 H 0.1774 0.1835 -0.2073 0.030 Uiso 1 1 calc R . . O1 O -0.1202(2) 0.2515(2) -0.48096(19) 0.0377(7) Uani 1 1 d . . . C34 C -0.2470(3) 0.2782(2) -0.5196(3) 0.0354(8) Uani 1 1 d . . . H34 H -0.2744 0.3104 -0.4573 0.042 Uiso 1 1 calc R . . C35 C -0.3351(4) 0.2105(3) -0.5490(4) 0.0602(13) Uani 1 1 d . . . H35A H -0.3354 0.1791 -0.4781 0.072 Uiso 1 1 calc R . . H35B H -0.4198 0.2315 -0.5729 0.072 Uiso 1 1 calc R . . C36 C -0.3064(4) 0.1585(3) -0.6413(5) 0.0762(15) Uani 1 1 d . . . H36A H -0.3058 0.1888 -0.7121 0.114 Uiso 1 1 calc R . . H36B H -0.3695 0.1175 -0.6561 0.114 Uiso 1 1 calc R . . H36C H -0.2248 0.1347 -0.6168 0.114 Uiso 1 1 calc R . . C37 C -0.2351(4) 0.3311(3) -0.6252(3) 0.0520(10) Uani 1 1 d . . . H37A H -0.1801 0.3750 -0.5996 0.078 Uiso 1 1 calc R . . H37B H -0.3172 0.3509 -0.6594 0.078 Uiso 1 1 calc R . . H37C H -0.2007 0.3007 -0.6832 0.078 Uiso 1 1 calc R . . C38 C 0.1400(3) 0.3578(2) 0.4098(3) 0.0238(7) Uani 1 1 d . . . C39 C -0.1010(3) -0.0890(3) 0.5395(3) 0.0300(8) Uani 1 1 d . . . C40 C -0.0423(3) -0.0377(2) 0.4680(3) 0.0257(7) Uani 1 1 d . . . C41 C -0.0206(4) 0.0407(2) 0.4907(3) 0.0353(9) Uani 1 1 d . . . H41 H -0.0476 0.0649 0.5551 0.042 Uiso 1 1 calc R . . C42 C 0.0416(3) 0.0836(2) 0.4174(3) 0.0355(9) Uani 1 1 d . . . H42 H 0.0542 0.1377 0.4325 0.043 Uiso 1 1 calc R . . N6 N 0.0846(2) 0.05302(18) 0.3269(2) 0.0254(6) Uani 1 1 d . . . C43 C 0.0620(3) -0.0220(2) 0.3050(3) 0.0269(7) Uani 1 1 d . . . H43 H 0.0907 -0.0446 0.2403 0.032 Uiso 1 1 calc R . . C44 C -0.0009(3) -0.0690(2) 0.3708(3) 0.0295(8) Uani 1 1 d . . . H44 H -0.0160 -0.1221 0.3504 0.035 Uiso 1 1 calc R . . C45 C 0.4820(3) 0.0374(2) 0.6270(3) 0.0238(7) Uani 1 1 d . . . C46 C 0.4115(3) 0.0302(2) 0.7146(3) 0.0292(8) Uani 1 1 d . . . H46 H 0.3249 0.0400 0.6977 0.035 Uiso 1 1 calc R . . C47 C 0.4641(3) 0.0091(2) 0.8251(3) 0.0316(8) Uani 1 1 d . . . H47 H 0.4138 0.0048 0.8835 0.038 Uiso 1 1 calc R . . C48 C 0.5911(3) -0.0059(2) 0.8523(3) 0.0327(8) Uani 1 1 d . . . C49 C 0.6630(3) -0.0017(3) 0.7670(3) 0.0409(10) Uani 1 1 d . . . H49 H 0.7487 -0.0140 0.7838 0.049 Uiso 1 1 calc R . . C50 C 0.6088(3) 0.0209(3) 0.6545(3) 0.0372(9) Uani 1 1 d . . . H50 H 0.6591 0.0251 0.5961 0.045 Uiso 1 1 calc R . . O2 O 0.6296(2) -0.02796(19) 0.9658(2) 0.0406(7) Uani 1 1 d . . . C51 C 0.7573(5) -0.0474(4) 1.0051(5) 0.0825(10) Uani 1 1 d . . . H51 H 0.7895 -0.0752 0.9412 0.099 Uiso 1 1 calc R . . C52 C 0.7599(5) -0.1033(4) 1.1059(4) 0.0825(10) Uani 1 1 d . . . H52A H 0.8464 -0.1193 1.1348 0.099 Uiso 1 1 calc R . . H52B H 0.7118 -0.1507 1.0791 0.099 Uiso 1 1 calc R . . C53 C 0.7053(4) -0.0656(4) 1.2041(4) 0.0825(10) Uani 1 1 d . . . H53A H 0.7425 -0.0140 1.2211 0.124 Uiso 1 1 calc R . . H53B H 0.7228 -0.0984 1.2734 0.124 Uiso 1 1 calc R . . H53C H 0.6154 -0.0601 1.1809 0.124 Uiso 1 1 calc R . . C54 C 0.8301(5) 0.0237(4) 1.0329(5) 0.0825(10) Uani 1 1 d . . . H54A H 0.8247 0.0561 0.9633 0.124 Uiso 1 1 calc R . . H54B H 0.9169 0.0098 1.0605 0.124 Uiso 1 1 calc R . . H54C H 0.7976 0.0527 1.0933 0.124 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 Zn1 0.02207(12) 0.01813(12) 0.02033(13) -0.00075(12) 0.00318(9) 0.00296(10) N1 0.0184(12) 0.0236(17) 0.0199(12) -0.0010(10) 0.0048(9) 0.0022(10) N2 0.0172(11) 0.0184(15) 0.0228(12) -0.0027(10) 0.0049(9) -0.0011(10) N3 0.0217(12) 0.0178(15) 0.0201(12) -0.0008(10) 0.0055(9) 0.0004(10) N4 0.0222(12) 0.0212(16) 0.0208(12) 0.0002(10) 0.0042(9) 0.0037(11) C1 0.0222(14) 0.0216(18) 0.0239(15) -0.0003(12) 0.0072(11) 0.0038(12) C2 0.0330(16) 0.031(2) 0.0252(16) 0.0038(14) 0.0023(12) 0.0094(14) C3 0.0296(15) 0.027(2) 0.0278(16) -0.0020(13) 0.0083(12) 0.0066(13) C4 0.0167(12) 0.0186(18) 0.0275(15) -0.0010(12) 0.0080(11) 0.0017(11) C5 0.0200(13) 0.0240(19) 0.0254(15) -0.0033(12) 0.0085(11) 0.0001(12) C6 0.0193(13) 0.0184(18) 0.0240(14) -0.0027(12) 0.0074(11) -0.0008(12) C7 0.0230(14) 0.0251(19) 0.0266(15) -0.0066(13) 0.0040(11) 0.0000(13) C8 0.0242(14) 0.0240(18) 0.0224(14) -0.0032(12) 0.0029(11) 0.0003(12) C9 0.0176(13) 0.028(2) 0.0203(14) 0.0006(11) 0.0026(10) -0.0017(11) C10 0.0236(15) 0.023(2) 0.0237(15) -0.0019(12) 0.0040(12) 0.0008(13) C11 0.0208(13) 0.0236(19) 0.0217(14) 0.0037(12) 0.0038(11) 0.0037(12) C12 0.0308(16) 0.0231(19) 0.0298(16) 0.0018(13) 0.0025(12) 0.0096(13) C13 0.0308(15) 0.0212(18) 0.0345(17) 0.0022(13) 0.0034(13) 0.0115(13) C14 0.0224(14) 0.0221(19) 0.0258(15) 0.0009(12) 0.0060(11) 0.0013(12) C15 0.0219(14) 0.0169(17) 0.0258(14) -0.0007(12) 0.0076(11) 0.0019(12) C16 0.0206(14) 0.0226(19) 0.0216(14) -0.0040(12) 0.0073(11) -0.0015(12) C17 0.0280(15) 0.0244(19) 0.0218(14) -0.0045(12) 0.0031(11) -0.0019(13) C18 0.0275(15) 0.029(2) 0.0233(15) -0.0038(13) 0.0026(11) -0.0013(13) C19 0.0197(13) 0.0204(18) 0.0178(13) -0.0010(10) 0.0034(10) 0.0020(11) C20 0.0165(14) 0.029(2) 0.0203(14) 0.0021(12) 0.0033(11) 0.0009(13) C21 0.0246(15) 0.025(2) 0.0254(15) -0.0026(13) 0.0043(12) 0.0026(13) C22 0.0312(16) 0.025(2) 0.0301(16) -0.0033(14) 0.0088(13) 0.0059(14) C23 0.0256(15) 0.024(2) 0.0276(16) 0.0039(13) 0.0047(12) -0.0024(13) C24 0.0410(19) 0.029(2) 0.0372(19) -0.0028(15) 0.0202(15) -0.0072(16) C25 0.0382(19) 0.024(2) 0.0405(19) -0.0048(14) 0.0214(15) -0.0088(15) N5 0.0214(13) 0.0244(17) 0.0272(13) 0.0045(11) 0.0060(10) -0.0015(11) C26 0.0243(15) 0.028(2) 0.0303(17) -0.0025(14) 0.0079(12) 0.0007(14) C27 0.0292(16) 0.020(2) 0.0342(18) 0.0024(14) 0.0079(13) -0.0034(14) C28 0.0270(15) 0.0200(18) 0.0213(14) -0.0014(12) -0.0008(11) 0.0021(13) C29 0.0264(16) 0.043(2) 0.0281(16) 0.0050(15) 0.0057(12) 0.0028(15) C30 0.0212(15) 0.052(3) 0.0314(17) 0.0050(16) 0.0003(12) 0.0041(15) C31 0.0309(16) 0.0264(19) 0.0213(14) -0.0006(12) 0.0052(11) -0.0002(13) C32 0.0252(14) 0.032(2) 0.0258(15) 0.0014(13) 0.0072(12) 0.0002(13) C33 0.0216(14) 0.026(2) 0.0284(16) -0.0006(13) 0.0053(11) -0.0005(13) O1 0.0302(12) 0.057(2) 0.0233(12) 0.0049(11) -0.0017(9) 0.0009(12) C34 0.0303(15) 0.0418(19) 0.0312(16) -0.0008(14) -0.0031(12) 0.0149(13) C35 0.0298(17) 0.085(3) 0.058(3) 0.021(2) -0.0154(17) -0.0193(19) C36 0.063(3) 0.056(3) 0.097(4) 0.006(3) -0.024(3) -0.002(2) C37 0.056(2) 0.041(2) 0.049(2) 0.0050(18) -0.0193(18) 0.0021(17) C38 0.0245(14) 0.0198(18) 0.0276(16) -0.0021(12) 0.0060(12) 0.0008(12) C39 0.0263(15) 0.034(2) 0.0297(17) 0.0013(15) 0.0052(13) -0.0029(14) C40 0.0202(14) 0.028(2) 0.0288(16) 0.0068(14) 0.0043(12) -0.0042(13) C41 0.0411(19) 0.029(2) 0.0414(19) -0.0039(16) 0.0245(15) -0.0080(16) C42 0.043(2) 0.021(2) 0.048(2) -0.0009(15) 0.0203(17) -0.0059(16) N6 0.0257(13) 0.0237(18) 0.0285(13) -0.0006(11) 0.0099(10) -0.0028(12) C43 0.0279(16) 0.027(2) 0.0270(16) -0.0004(13) 0.0072(12) -0.0047(14) C44 0.0320(17) 0.023(2) 0.0346(18) -0.0022(14) 0.0090(14) -0.0053(15) C45 0.0244(15) 0.0249(19) 0.0221(14) -0.0011(12) 0.0035(11) 0.0035(13) C46 0.0270(16) 0.036(2) 0.0229(15) 0.0000(14) 0.0007(12) 0.0029(15) C47 0.0321(17) 0.038(2) 0.0251(16) 0.0000(14) 0.0061(13) -0.0075(15) C48 0.0351(18) 0.033(2) 0.0264(16) 0.0066(14) -0.0040(13) -0.0032(15) C49 0.0295(17) 0.062(3) 0.0314(18) 0.0084(17) 0.0039(13) 0.0145(18) C50 0.0310(17) 0.058(3) 0.0236(16) 0.0035(16) 0.0069(13) 0.0120(17) O2 0.0349(13) 0.053(2) 0.0310(13) 0.0135(12) -0.0023(10) -0.0051(12) C51 0.0485(13) 0.131(3) 0.0618(16) 0.0422(17) -0.0089(11) -0.0073(14) C52 0.0485(13) 0.131(3) 0.0618(16) 0.0422(17) -0.0089(11) -0.0073(14) C53 0.0485(13) 0.131(3) 0.0618(16) 0.0422(17) -0.0089(11) -0.0073(14) C54 0.0485(13) 0.131(3) 0.0618(16) 0.0422(17) -0.0089(11) -0.0073(14) _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 Zn1 N4 2.062(3) . ? Zn1 N2 2.062(2) . ? Zn1 N3 2.071(3) . ? Zn1 N1 2.072(3) . ? Zn1 N5 2.356(3) . ? Zn1 N6 2.383(3) . ? N1 C4 1.368(4) . ? N1 C1 1.371(4) . ? N2 C6 1.372(4) . ? N2 C9 1.377(4) . ? N3 C14 1.356(4) . ? N3 C11 1.367(4) . ? N4 C16 1.362(4) . ? N4 C19 1.368(4) . ? C1 C20 1.402(5) . ? C1 C2 1.453(5) . ? C2 C3 1.344(5) . ? C2 H2 0.9500 . ? C3 C4 1.436(5) . ? C3 H3 0.9500 . ? C4 C5 1.406(4) . ? C5 C6 1.417(5) . ? C5 C21 1.446(5) . ? C6 C7 1.450(4) . ? C7 C8 1.355(5) . ? C7 H7 0.9500 . ? C8 C9 1.435(5) . ? C8 H8 0.9500 . ? C9 C10 1.410(5) . ? C10 C11 1.420(5) . ? C10 C28 1.491(4) . ? C11 C12 1.458(5) . ? C12 C13 1.360(5) . ? C12 H12 0.9500 . ? C13 C14 1.445(4) . ? C13 H13 0.9500 . ? C14 C15 1.423(4) . ? C15 C16 1.418(5) . ? C15 C38 1.431(5) . ? C16 C17 1.444(4) . ? C17 C18 1.354(5) . ? C17 H17 0.9500 . ? C18 C19 1.450(5) . ? C18 H18 0.9500 . ? C19 C20 1.426(5) . ? C20 C45 1.483(4) . ? C21 C22 1.178(5) . ? C22 C23 1.442(5) 2_645 ? C23 C24 1.386(5) . ? C23 C27 1.399(5) . ? C23 C22 1.442(5) 2_655 ? C24 C25 1.391(5) . ? C24 H24 0.9500 . ? C25 N5 1.328(4) . ? C25 H25 0.9500 . ? N5 C26 1.349(5) . ? C26 C27 1.380(5) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.389(4) . ? C28 C33 1.408(4) . ? C29 C30 1.381(5) . ? C29 H29 0.9500 . ? C30 C31 1.395(5) . ? C30 H30 0.9500 . ? C31 O1 1.357(4) . ? C31 C32 1.400(5) . ? C32 C33 1.368(4) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? O1 C34 1.459(4) . ? C34 C35 1.511(6) . ? C34 C37 1.557(5) . ? C34 H34 1.0000 . ? C35 C36 1.475(7) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C39 1.204(5) 2_556 ? C39 C38 1.205(5) 2_546 ? C39 C40 1.438(5) . ? C40 C41 1.384(5) . ? C40 C44 1.400(5) . ? C41 C42 1.392(5) . ? C41 H41 0.9500 . ? C42 N6 1.336(4) . ? C42 H42 0.9500 . ? N6 C43 1.327(5) . ? C43 C44 1.376(5) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.389(4) . ? C45 C50 1.399(5) . ? C46 C47 1.374(4) . ? C46 H46 0.9500 . ? C47 C48 1.397(5) . ? C47 H47 0.9500 . ? C48 C49 1.374(5) . ? C48 O2 1.378(4) . ? C49 C50 1.405(5) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? O2 C51 1.435(6) . ? C51 C54 1.461(9) . ? C51 C52 1.518(7) . ? C51 H51 1.0000 . ? C52 C53 1.526(8) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Zn1 N2 179.80(15) . . ? N4 Zn1 N3 90.43(11) . . ? N2 Zn1 N3 89.37(10) . . ? N4 Zn1 N1 89.89(10) . . ? N2 Zn1 N1 90.30(11) . . ? N3 Zn1 N1 179.17(13) . . ? N4 Zn1 N5 92.79(10) . . ? N2 Zn1 N5 87.22(10) . . ? N3 Zn1 N5 87.25(10) . . ? N1 Zn1 N5 93.50(10) . . ? N4 Zn1 N6 86.68(10) . . ? N2 Zn1 N6 93.31(10) . . ? N3 Zn1 N6 93.41(10) . . ? N1 Zn1 N6 85.84(10) . . ? N5 Zn1 N6 179.16(11) . . ? C4 N1 C1 107.0(3) . . ? C4 N1 Zn1 126.5(2) . . ? C1 N1 Zn1 126.2(2) . . ? C6 N2 C9 106.7(2) . . ? C6 N2 Zn1 126.1(2) . . ? C9 N2 Zn1 126.8(2) . . ? C14 N3 C11 106.8(3) . . ? C14 N3 Zn1 125.9(2) . . ? C11 N3 Zn1 127.1(2) . . ? C16 N4 C19 106.9(3) . . ? C16 N4 Zn1 126.7(2) . . ? C19 N4 Zn1 126.4(2) . . ? N1 C1 C20 126.4(3) . . ? N1 C1 C2 108.8(3) . . ? C20 C1 C2 124.8(3) . . ? C3 C2 C1 107.1(3) . . ? C3 C2 H2 126.4 . . ? C1 C2 H2 126.4 . . ? C2 C3 C4 107.4(3) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? N1 C4 C5 124.6(3) . . ? N1 C4 C3 109.6(3) . . ? C5 C4 C3 125.8(3) . . ? C4 C5 C6 127.1(3) . . ? C4 C5 C21 117.2(3) . . ? C6 C5 C21 115.5(3) . . ? N2 C6 C5 125.1(3) . . ? N2 C6 C7 109.4(3) . . ? C5 C6 C7 125.4(3) . . ? C8 C7 C6 106.7(3) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C7 C8 C9 107.6(3) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? N2 C9 C10 125.4(3) . . ? N2 C9 C8 109.5(3) . . ? C10 C9 C8 125.0(3) . . ? C9 C10 C11 125.7(3) . . ? C9 C10 C28 116.5(3) . . ? C11 C10 C28 117.7(3) . . ? N3 C11 C10 125.1(3) . . ? N3 C11 C12 109.6(3) . . ? C10 C11 C12 125.3(3) . . ? C13 C12 C11 106.5(3) . . ? C13 C12 H12 126.8 . . ? C11 C12 H12 126.8 . . ? C12 C13 C14 106.6(3) . . ? C12 C13 H13 126.7 . . ? C14 C13 H13 126.7 . . ? N3 C14 C15 125.8(3) . . ? N3 C14 C13 110.5(3) . . ? C15 C14 C13 123.7(3) . . ? C16 C15 C14 126.2(3) . . ? C16 C15 C38 116.0(3) . . ? C14 C15 C38 117.6(3) . . ? N4 C16 C15 124.9(3) . . ? N4 C16 C17 110.1(3) . . ? C15 C16 C17 124.9(3) . . ? C18 C17 C16 106.6(3) . . ? C18 C17 H17 126.7 . . ? C16 C17 H17 126.7 . . ? C17 C18 C19 107.2(3) . . ? C17 C18 H18 126.4 . . ? C19 C18 H18 126.4 . . ? N4 C19 C20 126.1(3) . . ? N4 C19 C18 109.2(3) . . ? C20 C19 C18 124.6(3) . . ? C1 C20 C19 124.8(3) . . ? C1 C20 C45 119.1(3) . . ? C19 C20 C45 116.0(3) . . ? C22 C21 C5 173.7(4) . . ? C21 C22 C23 165.6(4) . 2_645 ? C24 C23 C27 117.9(3) . . ? C24 C23 C22 124.5(3) . 2_655 ? C27 C23 C22 117.6(3) . 2_655 ? C23 C24 C25 118.9(3) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? N5 C25 C24 123.9(4) . . ? N5 C25 H25 118.1 . . ? C24 C25 H25 118.1 . . ? C25 N5 C26 116.8(3) . . ? C25 N5 Zn1 124.7(2) . . ? C26 N5 Zn1 116.8(2) . . ? N5 C26 C27 123.7(3) . . ? N5 C26 H26 118.2 . . ? C27 C26 H26 118.2 . . ? C26 C27 C23 118.8(3) . . ? C26 C27 H27 120.6 . . ? C23 C27 H27 120.6 . . ? C29 C28 C33 116.9(3) . . ? C29 C28 C10 124.2(3) . . ? C33 C28 C10 118.9(3) . . ? C30 C29 C28 122.2(3) . . ? C30 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C29 C30 C31 120.1(3) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? O1 C31 C30 126.7(3) . . ? O1 C31 C32 114.7(3) . . ? C30 C31 C32 118.6(3) . . ? C33 C32 C31 120.5(3) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C28 121.7(3) . . ? C32 C33 H33 119.1 . . ? C28 C33 H33 119.1 . . ? C31 O1 C34 119.3(3) . . ? O1 C34 C35 111.6(3) . . ? O1 C34 C37 103.2(3) . . ? C35 C34 C37 113.7(3) . . ? O1 C34 H34 109.4 . . ? C35 C34 H34 109.4 . . ? C37 C34 H34 109.4 . . ? C36 C35 C34 115.1(4) . . ? C36 C35 H35A 108.5 . . ? C34 C35 H35A 108.5 . . ? C36 C35 H35B 108.5 . . ? C34 C35 H35B 108.5 . . ? H35A C35 H35B 107.5 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C39 C38 C15 173.4(4) 2_556 . ? C38 C39 C40 168.4(4) 2_546 . ? C41 C40 C44 117.3(3) . . ? C41 C40 C39 124.1(3) . . ? C44 C40 C39 118.5(4) . . ? C40 C41 C42 118.7(3) . . ? C40 C41 H41 120.6 . . ? C42 C41 H41 120.6 . . ? N6 C42 C41 123.8(4) . . ? N6 C42 H42 118.1 . . ? C41 C42 H42 118.1 . . ? C43 N6 C42 117.0(3) . . ? C43 N6 Zn1 117.3(2) . . ? C42 N6 Zn1 122.8(2) . . ? N6 C43 C44 123.6(3) . . ? N6 C43 H43 118.2 . . ? C44 C43 H43 118.2 . . ? C43 C44 C40 119.5(4) . . ? C43 C44 H44 120.3 . . ? C40 C44 H44 120.3 . . ? C46 C45 C50 117.7(3) . . ? C46 C45 C20 120.1(3) . . ? C50 C45 C20 122.2(3) . . ? C47 C46 C45 121.5(3) . . ? C47 C46 H46 119.3 . . ? C45 C46 H46 119.3 . . ? C46 C47 C48 120.5(3) . . ? C46 C47 H47 119.8 . . ? C48 C47 H47 119.8 . . ? C49 C48 O2 126.6(3) . . ? C49 C48 C47 119.6(3) . . ? O2 C48 C47 113.7(3) . . ? C48 C49 C50 119.5(3) . . ? C48 C49 H49 120.2 . . ? C50 C49 H49 120.2 . . ? C45 C50 C49 121.2(3) . . ? C45 C50 H50 119.4 . . ? C49 C50 H50 119.4 . . ? C48 O2 C51 119.8(3) . . ? O2 C51 C54 110.1(6) . . ? O2 C51 C52 106.6(4) . . ? C54 C51 C52 114.5(5) . . ? O2 C51 H51 108.5 . . ? C54 C51 H51 108.5 . . ? C52 C51 H51 108.5 . . ? C51 C52 C53 111.1(5) . . ? C51 C52 H52A 109.4 . . ? C53 C52 H52A 109.4 . . ? C51 C52 H52B 109.4 . . ? C53 C52 H52B 109.4 . . ? H52A C52 H52B 108.0 . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C51 C54 H54A 109.5 . . ? C51 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C51 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.20 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.763 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 942060'