# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H78 Cu N8 O10, 4(Cl O4), 2(H2 O)' _chemical_formula_sum 'C48 H82 Cl4 Cu N8 O28' _chemical_formula_weight 1424.56 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.791(3) _cell_length_b 17.227(3) _cell_length_c 25.476(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.96(3) _cell_angle_gamma 90.00 _cell_volume 6351(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 56598 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 28.61 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2988 _exptl_absorpt_coefficient_mu 0.602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7139 _exptl_absorpt_correction_T_max 0.8400 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 56598 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.61 _reflns_number_total 8074 _reflns_number_gt 6433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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 largest residual peak was 2.41 A from H17B. ; _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^)+(0.1053P)^2^+42.1654P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8074 _refine_ls_number_parameters 422 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.2239 _refine_ls_wR_factor_gt 0.2100 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Cu1 Cu 0.5000 0.23937(3) 0.7500 0.02438(16) Uani 1 2 d S . . Cl2 Cl 0.14632(7) 0.15540(6) 0.65697(5) 0.0389(2) Uani 1 1 d . . . Cl1 Cl 0.28710(10) 0.31091(7) 0.88801(6) 0.0588(4) Uani 1 1 d . . . N1 N 0.47697(19) 0.32049(16) 0.69159(12) 0.0245(6) Uani 1 1 d . . . O15 O 0.3346(2) 0.24624(18) 0.75303(13) 0.0370(6) Uani 1 1 d D . . H15A H 0.311(4) 0.253(4) 0.7804(15) 0.07(2) Uiso 1 1 d D . . H15B H 0.291(3) 0.232(4) 0.7287(17) 0.08(2) Uiso 1 1 d D . . N3 N 0.4728(2) 0.15327(17) 0.69443(13) 0.0268(6) Uani 1 1 d . . . C5 C 0.4022(2) 0.3185(2) 0.65123(14) 0.0262(7) Uani 1 1 d . . . H5 H 0.3588 0.2777 0.6504 0.031 Uiso 1 1 calc R . . O1 O 0.7861(2) 0.0389(2) 0.64790(13) 0.0442(7) Uani 1 1 d . . . O2 O 0.6564(2) -0.04525(18) 0.69361(14) 0.0430(7) Uani 1 1 d . . . O3 O 0.5402(2) -0.1407(2) 0.49410(14) 0.0493(8) Uani 1 1 d . . . O12 O 0.1848(2) 0.07944(18) 0.66882(15) 0.0458(8) Uani 1 1 d . . . N2 N 0.3437(2) 0.5199(2) 0.54849(15) 0.0377(8) Uani 1 1 d . . . C2 C 0.5263(2) 0.4354(2) 0.65265(16) 0.0305(7) Uani 1 1 d . . . H2 H 0.5710 0.4754 0.6543 0.037 Uiso 1 1 calc R . . C12 C 0.5162(3) 0.0793(2) 0.62438(16) 0.0310(7) Uani 1 1 d . . . H12 H 0.5553 0.0731 0.5994 0.037 Uiso 1 1 calc R . . C13 C 0.4490(3) 0.0238(2) 0.62759(16) 0.0304(7) Uani 1 1 d . . . C14 C 0.3927(3) 0.0358(2) 0.66415(17) 0.0322(8) Uani 1 1 d . . . H14 H 0.3445 0.0003 0.6665 0.039 Uiso 1 1 calc R . . N4 N 0.5094(3) -0.1057(2) 0.60657(17) 0.0404(8) Uani 1 1 d . . . C15 C 0.4079(3) 0.1005(2) 0.69718(16) 0.0300(7) Uani 1 1 d . . . H15 H 0.3705 0.1075 0.7229 0.036 Uiso 1 1 calc R . . O4 O 0.7151(2) -0.0880(2) 0.48667(14) 0.0541(9) Uani 1 1 d . . . C3 C 0.4492(2) 0.4330(2) 0.61058(15) 0.0276(7) Uani 1 1 d . . . C1 C 0.5370(2) 0.3790(2) 0.69189(16) 0.0294(7) Uani 1 1 d . . . H1 H 0.5895 0.3817 0.7206 0.035 Uiso 1 1 calc R . . C4 C 0.3860(2) 0.3737(2) 0.61086(15) 0.0280(7) Uani 1 1 d . . . H4 H 0.3317 0.3709 0.5834 0.034 Uiso 1 1 calc R . . C6 C 0.4382(3) 0.4906(3) 0.56489(18) 0.0361(9) Uani 1 1 d . . . H6A H 0.4805 0.5349 0.5759 0.043 Uiso 1 1 calc R . . H6B H 0.4564 0.4653 0.5337 0.043 Uiso 1 1 calc R . . C11 C 0.5255(2) 0.1434(2) 0.65779(15) 0.0286(7) Uani 1 1 d . . . H11 H 0.5705 0.1815 0.6548 0.034 Uiso 1 1 calc R . . C9 C 0.8491(3) 0.0938(3) 0.6333(2) 0.0467(11) Uani 1 1 d . . . H9A H 0.9135 0.0782 0.6486 0.056 Uiso 1 1 calc R . . H9B H 0.8384 0.1459 0.6473 0.056 Uiso 1 1 calc R . . C16 C 0.4333(3) -0.0461(2) 0.59110(18) 0.0363(8) Uani 1 1 d . . . H16A H 0.4304 -0.0293 0.5536 0.044 Uiso 1 1 calc R . . H16B H 0.3732 -0.0702 0.5929 0.044 Uiso 1 1 calc R . . O6 O 0.2672(3) 0.3871(2) 0.86687(17) 0.0571(9) Uani 1 1 d . . . C18 C 0.6277(3) -0.1235(3) 0.6915(2) 0.0486(11) Uani 1 1 d . . . H18A H 0.6379 -0.1454 0.7282 0.058 Uiso 1 1 calc R . . H18B H 0.6640 -0.1545 0.6704 0.058 Uiso 1 1 calc R . . C19 C 0.7514(3) -0.0372(3) 0.71866(19) 0.0465(11) Uani 1 1 d . . . H19A H 0.7874 -0.0799 0.7070 0.056 Uiso 1 1 calc R . . H19B H 0.7583 -0.0406 0.7581 0.056 Uiso 1 1 calc R . . O10 O 0.2124(3) 0.2064(2) 0.6435(2) 0.0649(11) Uani 1 1 d . . . C17 C 0.5267(3) -0.1269(3) 0.6656(2) 0.0468(11) Uani 1 1 d . . . H17A H 0.4921 -0.0908 0.6844 0.056 Uiso 1 1 calc R . . H17B H 0.5032 -0.1800 0.6694 0.056 Uiso 1 1 calc R . . C23 C 0.6803(4) -0.1615(3) 0.46371(19) 0.0522(13) Uani 1 1 d . . . H23A H 0.7322 -0.1980 0.4646 0.063 Uiso 1 1 calc R . . H23B H 0.6485 -0.1540 0.4258 0.063 Uiso 1 1 calc R . . C8 C 0.3330(3) 0.5961(3) 0.5724(2) 0.0477(11) Uani 1 1 d . . . H8A H 0.2698 0.6157 0.5579 0.057 Uiso 1 1 calc R . . H8B H 0.3773 0.6330 0.5617 0.057 Uiso 1 1 calc R . . O8 O 0.2347(3) 0.2938(3) 0.92750(19) 0.0698(12) Uani 1 1 d . . . C21 C 0.4654(4) -0.1708(3) 0.5155(2) 0.0554(13) Uani 1 1 d . . . H21A H 0.4479 -0.2221 0.4991 0.067 Uiso 1 1 calc R . . H21B H 0.4115 -0.1359 0.5049 0.067 Uiso 1 1 calc R . . C24 C 0.7894(4) -0.0572(4) 0.4659(2) 0.0560(14) Uani 1 1 d . . . H24A H 0.7714 -0.0533 0.4263 0.067 Uiso 1 1 calc R . . H24B H 0.8437 -0.0920 0.4750 0.067 Uiso 1 1 calc R . . O5 O 0.3837(4) 0.3070(4) 0.9133(3) 0.120(3) Uani 1 1 d . . . C20 C 0.4853(4) -0.1794(3) 0.5743(2) 0.0526(12) Uani 1 1 d . . . H20A H 0.5373 -0.2163 0.5845 0.063 Uiso 1 1 calc R . . H20B H 0.4306 -0.2030 0.5847 0.063 Uiso 1 1 calc R . . C10 C 0.7876(3) 0.0383(3) 0.7044(2) 0.0491(11) Uani 1 1 d . . . H10A H 0.7490 0.0811 0.7135 0.059 Uiso 1 1 calc R . . H10B H 0.8516 0.0457 0.7248 0.059 Uiso 1 1 calc R . . C22 C 0.6144(4) -0.1941(3) 0.4949(3) 0.0559(13) Uani 1 1 d . . . H22A H 0.5897 -0.2442 0.4791 0.067 Uiso 1 1 calc R . . H22B H 0.6468 -0.2037 0.5324 0.067 Uiso 1 1 calc R . . O11 O 0.1191(7) 0.1861(3) 0.7022(3) 0.142(3) Uani 1 1 d . . . C7 C 0.3136(4) 0.5222(3) 0.4898(2) 0.0529(13) Uani 1 1 d . . . H7A H 0.3636 0.5448 0.4741 0.064 Uiso 1 1 calc R . . H7B H 0.2589 0.5564 0.4802 0.064 Uiso 1 1 calc R . . O7 O 0.2764(6) 0.2533(3) 0.8486(3) 0.121(3) Uani 1 1 d . . . O9 O 0.0697(4) 0.1503(3) 0.6155(3) 0.128(3) Uani 1 1 d . . . H9 H 0.563(3) -0.083(3) 0.5950(19) 0.032(12) Uiso 1 1 d . . . O13 O 0.6493(2) -0.0328(2) 0.57417(16) 0.0542(9) Uani 1 1 d D . . H13B H 0.674(4) -0.037(4) 0.5476(17) 0.08(2) Uiso 1 1 d D . . H13A H 0.686(4) -0.005(4) 0.596(2) 0.09(2) Uiso 1 1 d 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 Cu1 0.0258(3) 0.0176(3) 0.0286(3) 0.000 0.0028(2) 0.000 Cl2 0.0284(4) 0.0314(5) 0.0548(6) -0.0060(4) 0.0037(4) -0.0030(3) Cl1 0.0702(8) 0.0382(6) 0.0811(9) -0.0061(6) 0.0458(7) -0.0062(5) N1 0.0208(13) 0.0198(13) 0.0318(15) 0.0005(11) 0.0028(11) -0.0001(10) O15 0.0257(13) 0.0421(16) 0.0425(16) -0.0044(13) 0.0055(12) -0.0007(11) N3 0.0264(14) 0.0214(13) 0.0321(15) -0.0007(11) 0.0049(12) -0.0010(11) C5 0.0215(15) 0.0245(16) 0.0308(17) -0.0003(13) 0.0010(13) -0.0021(12) O1 0.0349(15) 0.0503(19) 0.0458(17) -0.0110(14) 0.0045(13) -0.0023(13) O2 0.0369(15) 0.0359(15) 0.0526(18) -0.0038(14) 0.0010(13) 0.0089(12) O3 0.0451(18) 0.0484(19) 0.0517(19) -0.0075(15) 0.0037(15) 0.0093(15) O12 0.0355(15) 0.0309(15) 0.069(2) 0.0008(14) 0.0058(15) -0.0010(12) N2 0.0320(17) 0.0398(19) 0.0385(18) 0.0112(15) 0.0011(14) 0.0070(14) C2 0.0214(15) 0.0272(17) 0.040(2) 0.0049(15) 0.0004(14) -0.0049(13) C12 0.0279(17) 0.0312(18) 0.0329(18) -0.0017(15) 0.0039(14) 0.0022(14) C13 0.0308(17) 0.0256(17) 0.0329(18) -0.0017(14) 0.0023(14) 0.0039(13) C14 0.0303(18) 0.0241(17) 0.041(2) -0.0029(15) 0.0046(15) -0.0029(13) N4 0.0346(18) 0.0304(17) 0.054(2) -0.0098(16) 0.0037(16) 0.0051(14) C15 0.0287(17) 0.0244(16) 0.0377(19) -0.0037(14) 0.0091(14) -0.0038(13) O4 0.0408(17) 0.073(2) 0.0463(19) -0.0173(17) 0.0046(14) 0.0047(17) C3 0.0207(15) 0.0287(17) 0.0329(17) 0.0041(14) 0.0042(13) 0.0022(12) C1 0.0244(16) 0.0236(16) 0.0372(19) 0.0031(14) -0.0003(14) -0.0027(13) C4 0.0205(15) 0.0298(17) 0.0315(17) 0.0004(14) 0.0006(13) 0.0005(13) C6 0.0273(18) 0.040(2) 0.041(2) 0.0146(17) 0.0069(15) 0.0000(15) C11 0.0268(16) 0.0260(17) 0.0332(18) 0.0004(14) 0.0069(14) 0.0002(13) C9 0.040(2) 0.034(2) 0.063(3) -0.002(2) 0.004(2) 0.0032(17) C16 0.0337(19) 0.0323(19) 0.040(2) -0.0081(16) 0.0013(16) 0.0045(15) O6 0.048(2) 0.053(2) 0.071(2) 0.0105(18) 0.0159(18) 0.0125(16) C18 0.048(3) 0.035(2) 0.059(3) 0.000(2) 0.002(2) 0.0110(19) C19 0.038(2) 0.056(3) 0.042(2) -0.007(2) 0.0014(18) 0.014(2) O10 0.0437(19) 0.0400(19) 0.114(4) 0.008(2) 0.023(2) -0.0102(15) C17 0.048(3) 0.034(2) 0.056(3) 0.009(2) 0.006(2) 0.0036(18) C23 0.061(3) 0.050(3) 0.039(2) -0.008(2) -0.003(2) 0.024(2) C8 0.039(2) 0.035(2) 0.065(3) 0.013(2) 0.001(2) 0.0078(18) O8 0.085(3) 0.060(2) 0.081(3) -0.006(2) 0.057(3) -0.010(2) C21 0.042(2) 0.054(3) 0.067(3) -0.020(3) 0.005(2) -0.001(2) C24 0.043(2) 0.089(4) 0.034(2) 0.002(2) 0.0017(19) 0.012(3) O5 0.065(3) 0.119(5) 0.184(7) 0.081(5) 0.042(4) 0.043(3) C20 0.047(3) 0.036(2) 0.075(4) -0.020(2) 0.013(2) 0.0001(19) C10 0.038(2) 0.061(3) 0.044(2) -0.019(2) 0.0008(19) 0.001(2) C22 0.053(3) 0.042(3) 0.072(4) -0.006(2) 0.012(3) 0.018(2) O11 0.283(10) 0.049(3) 0.139(6) -0.002(3) 0.148(7) 0.022(4) C7 0.042(2) 0.073(4) 0.042(2) 0.024(2) 0.004(2) 0.013(2) O7 0.188(7) 0.071(3) 0.144(5) -0.048(3) 0.127(6) -0.041(4) O9 0.071(3) 0.052(3) 0.210(7) 0.022(3) -0.091(4) -0.014(2) O13 0.0343(16) 0.075(3) 0.055(2) -0.0294(19) 0.0114(15) -0.0049(16) _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 Cu1 N1 2.018(3) . ? Cu1 N1 2.018(3) 2_656 ? Cu1 N3 2.032(3) . ? Cu1 N3 2.032(3) 2_656 ? Cl2 O9 1.382(4) . ? Cl2 O11 1.401(5) . ? Cl2 O10 1.409(4) . ? Cl2 O12 1.434(3) . ? Cl1 O7 1.397(5) . ? Cl1 O8 1.422(4) . ? Cl1 O6 1.426(4) . ? Cl1 O5 1.441(6) . ? N1 C1 1.343(4) . ? N1 C5 1.345(4) . ? O15 H15A 0.849(19) . ? O15 H15B 0.84(2) . ? N3 C15 1.334(5) . ? N3 C11 1.346(5) . ? C5 C4 1.384(5) . ? C5 H5 0.9500 . ? O1 C9 1.430(6) . ? O1 C10 1.434(6) . ? O2 C18 1.412(6) . ? O2 C19 1.424(5) . ? O3 C21 1.428(7) . ? O3 C22 1.428(6) . ? N2 C6 1.463(5) . ? N2 C7 1.469(6) . ? N2 C8 1.469(6) . ? C2 C1 1.379(5) . ? C2 C3 1.394(5) . ? C2 H2 0.9500 . ? C12 C11 1.383(5) . ? C12 C13 1.393(5) . ? C12 H12 0.9500 . ? C13 C14 1.388(6) . ? C13 C16 1.510(5) . ? C14 C15 1.387(5) . ? C14 H14 0.9500 . ? N4 C20 1.514(6) . ? N4 C16 1.514(5) . ? N4 C17 1.518(6) . ? N4 H9 0.98(5) . ? C15 H15 0.9500 . ? O4 C24 1.418(7) . ? O4 C23 1.443(6) . ? C3 C4 1.387(5) . ? C3 C6 1.512(5) . ? C1 H1 0.9500 . ? C4 H4 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 H11 0.9500 . ? C9 C8 1.520(7) 3_545 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C18 C17 1.504(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C10 1.479(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C23 C22 1.490(8) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C8 C9 1.520(7) 3_455 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C21 C20 1.473(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C24 C7 1.511(8) 3_545 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C7 C24 1.511(8) 3_455 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? O13 H13B 0.834(19) . ? O13 H13A 0.85(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 92.36(17) . 2_656 ? N1 Cu1 N3 90.74(12) . . ? N1 Cu1 N3 176.19(12) 2_656 . ? N1 Cu1 N3 176.19(12) . 2_656 ? N1 Cu1 N3 90.74(12) 2_656 2_656 ? N3 Cu1 N3 86.25(17) . 2_656 ? O9 Cl2 O11 108.8(5) . . ? O9 Cl2 O10 110.7(4) . . ? O11 Cl2 O10 107.3(4) . . ? O9 Cl2 O12 109.2(3) . . ? O11 Cl2 O12 109.9(3) . . ? O10 Cl2 O12 110.8(2) . . ? O7 Cl1 O8 111.3(3) . . ? O7 Cl1 O6 113.5(4) . . ? O8 Cl1 O6 111.0(3) . . ? O7 Cl1 O5 104.0(5) . . ? O8 Cl1 O5 108.0(4) . . ? O6 Cl1 O5 108.7(3) . . ? C1 N1 C5 117.5(3) . . ? C1 N1 Cu1 120.4(2) . . ? C5 N1 Cu1 122.2(2) . . ? H15A O15 H15B 106(4) . . ? C15 N3 C11 118.5(3) . . ? C15 N3 Cu1 120.1(3) . . ? C11 N3 Cu1 121.1(2) . . ? N1 C5 C4 122.6(3) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C9 O1 C10 113.1(4) . . ? C18 O2 C19 111.8(3) . . ? C21 O3 C22 114.5(4) . . ? C6 N2 C7 111.7(4) . . ? C6 N2 C8 111.6(4) . . ? C7 N2 C8 111.2(4) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C11 C12 C13 119.5(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 118.2(3) . . ? C14 C13 C16 119.6(4) . . ? C12 C13 C16 122.1(4) . . ? C15 C14 C13 118.8(4) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C20 N4 C16 110.4(3) . . ? C20 N4 C17 108.0(4) . . ? C16 N4 C17 112.6(4) . . ? C20 N4 H9 106(3) . . ? C16 N4 H9 105(3) . . ? C17 N4 H9 114(3) . . ? N3 C15 C14 123.0(4) . . ? N3 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C24 O4 C23 114.6(4) . . ? C4 C3 C2 117.5(3) . . ? C4 C3 C6 121.5(3) . . ? C2 C3 C6 120.9(3) . . ? N1 C1 C2 123.2(3) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N2 C6 C3 113.0(3) . . ? N2 C6 H6A 109.0 . . ? C3 C6 H6A 109.0 . . ? N2 C6 H6B 109.0 . . ? C3 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N3 C11 C12 122.0(3) . . ? N3 C11 H11 119.0 . . ? C12 C11 H11 119.0 . . ? O1 C9 C8 108.1(4) . 3_545 ? O1 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 3_545 . ? O1 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 3_545 . ? H9A C9 H9B 108.4 . . ? C13 C16 N4 111.7(3) . . ? C13 C16 H16A 109.3 . . ? N4 C16 H16A 109.3 . . ? C13 C16 H16B 109.3 . . ? N4 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? O2 C18 C17 108.5(4) . . ? O2 C18 H18A 110.0 . . ? C17 C18 H18A 110.0 . . ? O2 C18 H18B 110.0 . . ? C17 C18 H18B 110.0 . . ? H18A C18 H18B 108.4 . . ? O2 C19 C10 110.5(4) . . ? O2 C19 H19A 109.6 . . ? C10 C19 H19A 109.6 . . ? O2 C19 H19B 109.6 . . ? C10 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C18 C17 N4 111.9(4) . . ? C18 C17 H17A 109.2 . . ? N4 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? N4 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? O4 C23 C22 109.4(4) . . ? O4 C23 H23A 109.8 . . ? C22 C23 H23A 109.8 . . ? O4 C23 H23B 109.8 . . ? C22 C23 H23B 109.8 . . ? H23A C23 H23B 108.2 . . ? N2 C8 C9 113.1(4) . 3_455 ? N2 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 3_455 . ? N2 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 3_455 . ? H8A C8 H8B 107.8 . . ? O3 C21 C20 114.7(4) . . ? O3 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? O3 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? O4 C24 C7 109.0(4) . 3_545 ? O4 C24 H24A 109.9 . . ? C7 C24 H24A 109.9 3_545 . ? O4 C24 H24B 109.9 . . ? C7 C24 H24B 109.9 3_545 . ? H24A C24 H24B 108.3 . . ? C21 C20 N4 116.3(5) . . ? C21 C20 H20A 108.2 . . ? N4 C20 H20A 108.2 . . ? C21 C20 H20B 108.2 . . ? N4 C20 H20B 108.2 . . ? H20A C20 H20B 107.4 . . ? O1 C10 C19 108.8(4) . . ? O1 C10 H10A 109.9 . . ? C19 C10 H10A 109.9 . . ? O1 C10 H10B 109.9 . . ? C19 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? O3 C22 C23 109.5(4) . . ? O3 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? O3 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? N2 C7 C24 112.5(4) . 3_455 ? N2 C7 H7A 109.1 . . ? C24 C7 H7A 109.1 3_455 . ? N2 C7 H7B 109.1 . . ? C24 C7 H7B 109.1 3_455 . ? H7A C7 H7B 107.8 . . ? H13B O13 H13A 106(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H9 O13 0.98(5) 1.71(5) 2.693(6) 172(4) . O13 H13A O1 0.85(2) 1.92(3) 2.752(5) 167(7) . O13 H13B O4 0.834(19) 1.99(3) 2.779(5) 159(6) . O15 H15A O7 0.849(19) 1.91(2) 2.748(6) 168(6) . O15 H15B O10 0.84(2) 2.28(3) 3.072(6) 158(6) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.60 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.373 _refine_diff_density_min -1.773 _refine_diff_density_rms 0.126 _database_code_depnum_ccdc_archive 'CCDC 898006' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H74 Fe N10 O8 S2, 2(Cl O4), 2(H2 O)' _chemical_formula_sum 'C50 H78 Cl2 Fe N10 O18 S2' _chemical_formula_weight 1298.09 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' S S 0.1246 0.1234 '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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.231(3) _cell_length_b 16.882(3) _cell_length_c 26.121(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.73(3) _cell_angle_gamma 90.00 _cell_volume 6203(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 66154 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 30.81 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2736 _exptl_absorpt_coefficient_mu 0.472 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7650 _exptl_absorpt_correction_T_max 0.8338 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.710698 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 66154 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 30.81 _reflns_number_total 9290 _reflns_number_gt 7296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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 largest residual peak was 2.51 A from H20B. ; _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^)+(0.1427P)^2^+21.0754P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9290 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0825 _refine_ls_wR_factor_ref 0.2592 _refine_ls_wR_factor_gt 0.2426 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Fe1 Fe 0.5000 0.55816(3) 0.7500 0.02784(16) Uani 1 2 d S . . S1 S 0.76793(8) 0.63344(6) 0.67261(5) 0.0559(3) Uani 1 1 d . . . N5 N 0.63850(19) 0.56357(15) 0.72900(11) 0.0336(5) Uani 1 1 d . . . N1 N 0.45724(18) 0.65226(14) 0.69245(10) 0.0313(5) Uani 1 1 d . . . C15 C 0.3969(2) 0.34735(16) 0.61915(12) 0.0307(5) Uani 1 1 d . . . N3 N 0.45639(18) 0.46700(14) 0.69132(10) 0.0306(5) Uani 1 1 d . . . C13 C 0.5032(2) 0.45241(17) 0.65185(12) 0.0311(6) Uani 1 1 d . . . H13 H 0.5576 0.4835 0.6487 0.037 Uiso 1 1 calc R . . C3 C 0.4086(2) 0.76705(18) 0.61588(13) 0.0338(6) Uani 1 1 d . . . C1 C 0.3732(2) 0.64999(17) 0.66099(13) 0.0331(6) Uani 1 1 d . . . H1 H 0.3304 0.6081 0.6652 0.040 Uiso 1 1 calc R . . N4 N 0.4397(2) 0.24250(15) 0.55997(11) 0.0351(5) Uani 1 1 d . . . C22 C 0.6935(2) 0.59152(17) 0.70614(13) 0.0350(6) Uani 1 1 d . . . C16 C 0.3483(2) 0.36279(19) 0.66003(14) 0.0371(6) Uani 1 1 d . . . H16 H 0.2939 0.3323 0.6643 0.045 Uiso 1 1 calc R . . C18 C 0.3621(2) 0.28464(18) 0.57970(12) 0.0338(6) Uani 1 1 d . . . H18B H 0.3232 0.2458 0.5956 0.041 Uiso 1 1 calc R . . H18A H 0.3208 0.3098 0.5503 0.041 Uiso 1 1 calc R . . C6 C 0.3860(2) 0.82827(19) 0.57426(13) 0.0369(6) Uani 1 1 d . . . H6B H 0.3643 0.8007 0.5411 0.044 Uiso 1 1 calc R . . H6A H 0.4453 0.8568 0.5705 0.044 Uiso 1 1 calc R . . C17 C 0.3789(2) 0.42247(19) 0.69463(13) 0.0363(6) Uani 1 1 d . . . H17 H 0.3438 0.4327 0.7221 0.044 Uiso 1 1 calc R . . C2 C 0.3463(2) 0.70578(18) 0.62285(13) 0.0338(6) Uani 1 1 d . . . H2 H 0.2860 0.7024 0.6016 0.041 Uiso 1 1 calc R . . C4 C 0.4961(2) 0.76965(18) 0.64800(14) 0.0359(6) Uani 1 1 d . . . H4 H 0.5405 0.8105 0.6443 0.043 Uiso 1 1 calc R . . C14 C 0.4761(2) 0.39390(17) 0.61510(12) 0.0322(6) Uani 1 1 d . . . H14 H 0.5114 0.3858 0.5875 0.039 Uiso 1 1 calc R . . C19 C 0.4670(3) 0.1698(2) 0.58934(16) 0.0442(8) Uani 1 1 d . . . H19B H 0.5171 0.1425 0.5736 0.053 Uiso 1 1 calc R . . H19A H 0.4112 0.1341 0.5863 0.053 Uiso 1 1 calc R . . C5 C 0.5173(2) 0.71165(17) 0.68555(13) 0.0345(6) Uani 1 1 d . . . H5 H 0.5770 0.7139 0.7074 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.13292(8) 0.47509(6) 0.60048(7) 0.0708(4) Uani 1 1 d . . . O9 O 0.15935(17) 0.78425(15) 0.56051(11) 0.0378(5) Uani 1 1 d . . . O4 O 0.51392(16) 0.32689(15) 0.47912(9) 0.0383(5) Uani 1 1 d . . . O1 O 0.22346(18) 0.84851(16) 0.67083(10) 0.0451(6) Uani 1 1 d . . . O3 O 0.58930(19) 0.22872(15) 0.65104(10) 0.0431(5) Uani 1 1 d . . . N2 N 0.3117(2) 0.88839(16) 0.58294(12) 0.0378(6) Uani 1 1 d . . . C10 C 0.3083(3) 0.9467(2) 0.53846(18) 0.0479(9) Uani 1 1 d . . . H10A H 0.3661 0.9800 0.5444 0.057 Uiso 1 1 calc R . . H10B H 0.3097 0.9166 0.5061 0.057 Uiso 1 1 calc R . . C23 C 0.4193(2) 0.2965(2) 0.47156(14) 0.0437(8) Uani 1 1 d . . . H23A H 0.3999 0.2823 0.4347 0.052 Uiso 1 1 calc R . . H23B H 0.3749 0.3373 0.4809 0.052 Uiso 1 1 calc R . . C25 C 0.4154(3) 0.2250(2) 0.50467(14) 0.0418(7) Uani 1 1 d . . . H22A H 0.3506 0.2023 0.4980 0.050 Uiso 1 1 calc R . . H22B H 0.4601 0.1847 0.4950 0.050 Uiso 1 1 calc R . . C7 C 0.3316(3) 0.9316(2) 0.63384(18) 0.0497(9) Uani 1 1 d . . . H7B H 0.3988 0.9490 0.6390 0.060 Uiso 1 1 calc R . . H7A H 0.2916 0.9798 0.6314 0.060 Uiso 1 1 calc R . . O8 O 0.1826(3) 0.5442(3) 0.5941(2) 0.0935(14) Uani 1 1 d . . . C9 C 0.2109(3) 0.7918(3) 0.70948(14) 0.0501(9) Uani 1 1 d . . . H9B H 0.2260 0.8164 0.7442 0.060 Uiso 1 1 calc R . . H9A H 0.2552 0.7470 0.7078 0.060 Uiso 1 1 calc R . . C20 C 0.5026(3) 0.1835(2) 0.64548(16) 0.0468(8) Uani 1 1 d . . . H20A H 0.4541 0.2125 0.6615 0.056 Uiso 1 1 calc R . . H20B H 0.5144 0.1320 0.6635 0.056 Uiso 1 1 calc R . . C11 C 0.2225(3) 1.0001(2) 0.5310(2) 0.0568(11) Uani 1 1 d . . . H11B H 0.2208 1.0304 0.5633 0.068 Uiso 1 1 calc R . . H11A H 0.2289 1.0385 0.5032 0.068 Uiso 1 1 calc R . . C21 C 0.6120(3) 0.2620(2) 0.70197(15) 0.0483(8) Uani 1 1 d . . . H21B H 0.6050 0.2211 0.7283 0.058 Uiso 1 1 calc R . . H21A H 0.5678 0.3060 0.7062 0.058 Uiso 1 1 calc R . . C8 C 0.3146(3) 0.8857(3) 0.68087(17) 0.0544(10) Uani 1 1 d . . . H8A H 0.3647 0.8450 0.6893 0.065 Uiso 1 1 calc R . . H8B H 0.3172 0.9218 0.7109 0.065 Uiso 1 1 calc R . . O6 O 0.1671(4) 0.4088(3) 0.5777(2) 0.147(3) Uani 1 1 d . . . O5 O 0.1526(6) 0.4610(5) 0.6574(2) 0.164(3) Uani 1 1 d . . . O2 O 0.13527(19) 0.95866(16) 0.51811(11) 0.0470(6) Uani 1 1 d . . . C24 C 0.5210(2) 0.4002(2) 0.45273(13) 0.0399(7) Uani 1 1 d . . . H24A H 0.4755 0.4390 0.4634 0.048 Uiso 1 1 calc R . . H24B H 0.5052 0.3920 0.4149 0.048 Uiso 1 1 calc R . . C12 C 0.1207(3) 0.9312(2) 0.46590(15) 0.0426(7) Uani 1 1 d . . . H12A H 0.1668 0.8887 0.4617 0.051 Uiso 1 1 calc R . . H12B H 0.1308 0.9752 0.4422 0.051 Uiso 1 1 calc R . . O7 O 0.0377(3) 0.4857(3) 0.5849(4) 0.187(4) Uani 1 1 d . . . H9 H 0.250(3) 0.858(3) 0.5829(19) 0.055(13) Uiso 1 1 d . . . H25A H 0.141(4) 0.771(3) 0.589(2) 0.067(16) Uiso 1 1 d . . . H25B H 0.115(3) 0.799(3) 0.5377(18) 0.045(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0314(3) 0.0228(3) 0.0299(3) 0.000 0.0065(2) 0.000 S1 0.0689(7) 0.0374(4) 0.0709(7) -0.0073(4) 0.0409(5) -0.0162(4) N5 0.0352(12) 0.0302(11) 0.0360(13) 0.0011(9) 0.0075(10) -0.0007(9) N1 0.0326(11) 0.0258(10) 0.0350(13) -0.0006(9) 0.0041(9) -0.0004(9) C15 0.0339(13) 0.0259(12) 0.0325(14) -0.0013(10) 0.0055(11) -0.0004(10) N3 0.0355(12) 0.0251(10) 0.0318(12) 0.0008(9) 0.0069(10) -0.0001(9) C13 0.0351(14) 0.0265(12) 0.0325(14) 0.0016(10) 0.0079(11) -0.0028(10) C3 0.0350(14) 0.0299(13) 0.0367(15) 0.0033(11) 0.0054(11) 0.0055(11) C1 0.0322(13) 0.0290(12) 0.0390(16) -0.0005(11) 0.0078(11) 0.0005(10) N4 0.0392(13) 0.0304(12) 0.0370(14) -0.0057(10) 0.0095(11) -0.0013(10) C22 0.0407(15) 0.0257(12) 0.0399(16) -0.0052(11) 0.0104(12) -0.0040(11) C16 0.0360(15) 0.0352(14) 0.0414(17) -0.0050(12) 0.0102(12) -0.0077(11) C18 0.0356(14) 0.0322(13) 0.0348(15) -0.0063(11) 0.0089(11) -0.0037(11) C6 0.0395(15) 0.0323(14) 0.0389(16) 0.0052(12) 0.0062(12) 0.0078(12) C17 0.0391(15) 0.0337(14) 0.0383(16) -0.0060(12) 0.0132(12) -0.0040(12) C2 0.0321(13) 0.0311(13) 0.0376(15) -0.0020(11) 0.0033(11) 0.0033(10) C4 0.0330(14) 0.0274(13) 0.0469(18) 0.0037(11) 0.0047(12) 0.0011(10) C14 0.0376(14) 0.0299(13) 0.0304(14) -0.0003(10) 0.0098(11) -0.0011(11) C19 0.0506(19) 0.0290(14) 0.055(2) -0.0017(13) 0.0132(16) 0.0009(13) C5 0.0338(14) 0.0284(13) 0.0400(16) 0.0024(11) 0.0014(12) 0.0003(10) Cl1 0.0464(5) 0.0423(5) 0.1216(11) -0.0042(6) 0.0054(6) 0.0061(4) O9 0.0332(11) 0.0396(12) 0.0399(13) 0.0016(9) 0.0034(10) 0.0033(9) O4 0.0357(11) 0.0448(12) 0.0338(11) 0.0012(9) 0.0037(9) 0.0008(9) O1 0.0423(13) 0.0498(14) 0.0414(13) -0.0037(10) 0.0001(10) 0.0057(11) O3 0.0486(14) 0.0409(12) 0.0406(13) 0.0025(10) 0.0091(10) 0.0060(10) N2 0.0334(12) 0.0287(12) 0.0490(16) 0.0013(10) -0.0016(11) 0.0030(10) C10 0.0407(17) 0.0320(15) 0.067(2) 0.0132(15) -0.0050(16) -0.0012(12) C23 0.0369(16) 0.059(2) 0.0337(16) -0.0059(14) 0.0022(13) -0.0014(14) C25 0.0419(17) 0.0427(17) 0.0417(17) -0.0147(13) 0.0090(13) -0.0069(13) C7 0.0431(18) 0.0402(17) 0.064(2) -0.0163(16) 0.0018(16) -0.0011(14) O8 0.074(3) 0.083(3) 0.130(4) -0.033(3) 0.036(3) -0.033(2) C9 0.052(2) 0.063(2) 0.0348(17) -0.0049(15) 0.0036(15) 0.0204(18) C20 0.055(2) 0.0344(15) 0.052(2) 0.0086(14) 0.0135(16) 0.0030(14) C11 0.052(2) 0.0312(16) 0.078(3) -0.0003(17) -0.017(2) 0.0070(15) C21 0.057(2) 0.052(2) 0.0370(18) 0.0052(14) 0.0098(15) 0.0146(17) C8 0.0442(19) 0.065(3) 0.051(2) -0.0219(19) -0.0021(16) 0.0091(17) O6 0.141(5) 0.113(4) 0.155(5) -0.094(4) -0.079(4) 0.076(4) O5 0.210(8) 0.193(7) 0.090(4) 0.018(4) 0.023(4) 0.119(6) O2 0.0447(13) 0.0392(12) 0.0530(15) -0.0060(11) -0.0057(11) 0.0100(10) C24 0.0391(16) 0.0433(17) 0.0357(16) 0.0020(13) 0.0012(13) 0.0079(13) C12 0.0438(17) 0.0386(16) 0.0444(18) 0.0035(13) 0.0037(14) 0.0047(13) O7 0.050(2) 0.059(3) 0.427(13) 0.009(5) -0.044(4) -0.0093(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 Fe1 N5 2.127(3) . ? Fe1 N5 2.127(3) 2_656 ? Fe1 N3 2.194(3) . ? Fe1 N3 2.194(3) 2_656 ? Fe1 N1 2.208(3) 2_656 ? Fe1 N1 2.208(3) . ? S1 C22 1.635(3) . ? N5 C22 1.155(4) . ? N1 C1 1.345(4) . ? N1 C5 1.347(4) . ? C15 C16 1.383(4) . ? C15 C14 1.391(4) . ? C15 C18 1.508(4) . ? N3 C13 1.332(4) . ? N3 C17 1.348(4) . ? C13 C14 1.391(4) . ? C13 H13 0.9500 . ? C3 C4 1.392(4) . ? C3 C2 1.393(4) . ? C3 C6 1.499(4) . ? C1 C2 1.382(4) . ? C1 H1 0.9500 . ? N4 C25 1.463(4) . ? N4 C19 1.468(5) . ? N4 C18 1.471(4) . ? C16 C17 1.379(4) . ? C16 H16 0.9500 . ? C18 H18B 0.9900 . ? C18 H18A 0.9900 . ? C6 N2 1.507(4) . ? C6 H6B 0.9900 . ? C6 H6A 0.9900 . ? C17 H17 0.9500 . ? C2 H2 0.9500 . ? C4 C5 1.386(4) . ? C4 H4 0.9500 . ? C14 H14 0.9500 . ? C19 C20 1.495(6) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C5 H5 0.9500 . ? Cl1 O7 1.366(5) . ? Cl1 O6 1.388(4) . ? Cl1 O8 1.387(4) . ? Cl1 O5 1.490(6) . ? O9 H25A 0.85(6) . ? O9 H25B 0.84(5) . ? O4 C23 1.427(4) . ? O4 C24 1.427(4) . ? O1 C9 1.422(5) . ? O1 C8 1.429(5) . ? O3 C21 1.435(5) . ? O3 C20 1.439(5) . ? N2 C7 1.505(5) . ? N2 C10 1.518(5) . ? N2 H9 1.02(5) . ? C10 C11 1.506(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C23 C25 1.490(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C25 H22A 0.9900 . ? C25 H22B 0.9900 . ? C7 C8 1.503(7) . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C9 C21 1.479(6) 3_455 ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C11 O2 1.419(5) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C21 C9 1.479(6) 3_545 ? C21 H21B 0.9900 . ? C21 H21A 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O2 C12 1.425(5) . ? C24 C12 1.503(5) 3_545 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C12 C24 1.503(5) 3_455 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? 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 N5 Fe1 N5 175.08(14) . 2_656 ? N5 Fe1 N3 91.43(10) . . ? N5 Fe1 N3 92.03(10) 2_656 . ? N5 Fe1 N3 92.03(10) . 2_656 ? N5 Fe1 N3 91.43(10) 2_656 2_656 ? N3 Fe1 N3 90.92(13) . 2_656 ? N5 Fe1 N1 88.52(10) . 2_656 ? N5 Fe1 N1 87.93(10) 2_656 2_656 ? N3 Fe1 N1 178.53(9) . 2_656 ? N3 Fe1 N1 90.55(9) 2_656 2_656 ? N5 Fe1 N1 87.93(10) . . ? N5 Fe1 N1 88.52(10) 2_656 . ? N3 Fe1 N1 90.55(9) . . ? N3 Fe1 N1 178.53(9) 2_656 . ? N1 Fe1 N1 87.98(13) 2_656 . ? C22 N5 Fe1 151.4(3) . . ? C1 N1 C5 117.6(3) . . ? C1 N1 Fe1 121.5(2) . . ? C5 N1 Fe1 120.8(2) . . ? C16 C15 C14 117.3(3) . . ? C16 C15 C18 120.6(3) . . ? C14 C15 C18 122.1(3) . . ? C13 N3 C17 117.1(3) . . ? C13 N3 Fe1 123.3(2) . . ? C17 N3 Fe1 119.6(2) . . ? N3 C13 C14 123.2(3) . . ? N3 C13 H13 118.4 . . ? C14 C13 H13 118.4 . . ? C4 C3 C2 118.3(3) . . ? C4 C3 C6 119.3(3) . . ? C2 C3 C6 122.4(3) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C25 N4 C19 110.6(3) . . ? C25 N4 C18 111.5(3) . . ? C19 N4 C18 112.0(3) . . ? N5 C22 S1 177.7(3) . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? N4 C18 C15 113.1(3) . . ? N4 C18 H18B 109.0 . . ? C15 C18 H18B 109.0 . . ? N4 C18 H18A 109.0 . . ? C15 C18 H18A 109.0 . . ? H18B C18 H18A 107.8 . . ? C3 C6 N2 115.7(3) . . ? C3 C6 H6B 108.4 . . ? N2 C6 H6B 108.4 . . ? C3 C6 H6A 108.4 . . ? N2 C6 H6A 108.4 . . ? H6B C6 H6A 107.4 . . ? N3 C17 C16 123.1(3) . . ? N3 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C5 C4 C3 118.9(3) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C13 C14 C15 119.4(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? N4 C19 C20 114.0(3) . . ? N4 C19 H19B 108.8 . . ? C20 C19 H19B 108.8 . . ? N4 C19 H19A 108.8 . . ? C20 C19 H19A 108.8 . . ? H19B C19 H19A 107.7 . . ? N1 C5 C4 123.1(3) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.4 . . ? O7 Cl1 O6 112.0(4) . . ? O7 Cl1 O8 110.8(3) . . ? O6 Cl1 O8 114.1(4) . . ? O7 Cl1 O5 110.2(6) . . ? O6 Cl1 O5 105.9(4) . . ? O8 Cl1 O5 103.5(5) . . ? H25A O9 H25B 114(5) . . ? C23 O4 C24 112.3(3) . . ? C9 O1 C8 111.9(3) . . ? C21 O3 C20 111.7(3) . . ? C7 N2 C6 114.6(3) . . ? C7 N2 C10 110.0(3) . . ? C6 N2 C10 105.3(3) . . ? C7 N2 H9 107(3) . . ? C6 N2 H9 106(3) . . ? C10 N2 H9 114(3) . . ? C11 C10 N2 114.7(4) . . ? C11 C10 H10A 108.6 . . ? N2 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? N2 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O4 C23 C25 109.1(3) . . ? O4 C23 H23A 109.9 . . ? C25 C23 H23A 109.9 . . ? O4 C23 H23B 109.9 . . ? C25 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? N4 C25 C23 112.7(3) . . ? N4 C25 H22A 109.1 . . ? C23 C25 H22A 109.1 . . ? N4 C25 H22B 109.1 . . ? C23 C25 H22B 109.1 . . ? H22A C25 H22B 107.8 . . ? C8 C7 N2 116.1(3) . . ? C8 C7 H7B 108.3 . . ? N2 C7 H7B 108.3 . . ? C8 C7 H7A 108.3 . . ? N2 C7 H7A 108.3 . . ? H7B C7 H7A 107.4 . . ? O1 C9 C21 110.7(3) . 3_455 ? O1 C9 H9B 109.5 . . ? C21 C9 H9B 109.5 3_455 . ? O1 C9 H9A 109.5 . . ? C21 C9 H9A 109.5 3_455 . ? H9B C9 H9A 108.1 . . ? O3 C20 C19 109.8(3) . . ? O3 C20 H20A 109.7 . . ? C19 C20 H20A 109.7 . . ? O3 C20 H20B 109.7 . . ? C19 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? O2 C11 C10 113.5(3) . . ? O2 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? O2 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? H11B C11 H11A 107.7 . . ? O3 C21 C9 109.4(3) . 3_545 ? O3 C21 H21B 109.8 . . ? C9 C21 H21B 109.8 3_545 . ? O3 C21 H21A 109.8 . . ? C9 C21 H21A 109.8 3_545 . ? H21B C21 H21A 108.2 . . ? O1 C8 C7 109.3(3) . . ? O1 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O1 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? C11 O2 C12 112.5(3) . . ? O4 C24 C12 109.0(3) . 3_545 ? O4 C24 H24A 109.9 . . ? C12 C24 H24A 109.9 3_545 . ? O4 C24 H24B 109.9 . . ? C12 C24 H24B 109.9 3_545 . ? H24A C24 H24B 108.3 . . ? O2 C12 C24 109.1(3) . 3_455 ? O2 C12 H12A 109.9 . . ? C24 C12 H12A 109.9 3_455 . ? O2 C12 H12B 109.9 . . ? C24 C12 H12B 109.9 3_455 . ? H12A C12 H12B 108.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H9 O9 1.02(5) 1.82(5) 2.784(4) 156(4) . O9 H25A O3 0.85(6) 2.01(6) 2.860(4) 172(5) 3_455 O9 H25B O4 0.84(5) 1.99(5) 2.826(4) 175(4) 3_455 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 2.367 _refine_diff_density_min -1.398 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 898007' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H74 N10 Ni O8 S2, 2(Cl O4), 2(H2 O)' _chemical_formula_sum 'C50 H78 Cl2 N10 Ni O18 S2' _chemical_formula_weight 1300.95 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' S S 0.1246 0.1234 '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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.138(3) _cell_length_b 16.749(3) _cell_length_c 26.051(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.11(3) _cell_angle_gamma 90.00 _cell_volume 6091(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 33212 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 30.80 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2744 _exptl_absorpt_coefficient_mu 0.551 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7701 _exptl_absorpt_correction_T_max 0.8977 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 33212 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 30.80 _reflns_number_total 9365 _reflns_number_gt 6521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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^)+(0.1043P)^2^+10.9251P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9365 _refine_ls_number_parameters 396 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1017 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2120 _refine_ls_wR_factor_gt 0.1849 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.56027(3) 0.7500 0.02682(13) Uani 1 2 d S . . Cl1 Cl 0.13389(8) 0.47147(6) 0.60040(6) 0.0695(3) Uani 1 1 d . . . S1 S 0.77107(9) 0.63067(6) 0.67544(4) 0.0620(3) Uani 1 1 d . . . O1 O 0.23009(18) 0.85200(16) 0.67167(9) 0.0484(6) Uani 1 1 d . . . N1 N 0.6374(2) 0.56544(14) 0.73081(10) 0.0365(5) Uani 1 1 d . . . C1 C 0.6937(2) 0.59113(18) 0.70827(13) 0.0386(6) Uani 1 1 d . . . H9OB H 0.111(3) 0.793(2) 0.5395(16) 0.049(11) Uiso 1 1 d . . . H9OA H 0.142(4) 0.782(4) 0.589(2) 0.096(19) Uiso 1 1 d . . . O2 O 0.59494(18) 0.23013(14) 0.65359(9) 0.0458(5) Uani 1 1 d . . . N2 N 0.46044(18) 0.65044(14) 0.69375(9) 0.0309(5) Uani 1 1 d . . . C2 C 0.5209(2) 0.71044(17) 0.68725(12) 0.0343(6) Uani 1 1 d . . . H2 H 0.5806 0.7130 0.7098 0.041 Uiso 1 1 calc R . . O3 O 0.51314(16) 0.32571(14) 0.48010(8) 0.0388(5) Uani 1 1 d . . . N3 N 0.3158(2) 0.88913(15) 0.58254(10) 0.0381(5) Uani 1 1 d . . . H3N H 0.2565 0.8642 0.5809 0.046 Uiso 1 1 calc R . . C3 C 0.5002(2) 0.76836(17) 0.64942(12) 0.0357(6) Uani 1 1 d . . . H3 H 0.5452 0.8091 0.6456 0.043 Uiso 1 1 calc R . . O4 O 0.63712(18) 0.45950(14) 0.51786(10) 0.0458(5) Uani 1 1 d . . . N4 N 0.45845(17) 0.47099(13) 0.69374(9) 0.0286(4) Uani 1 1 d . . . C4 C 0.4117(2) 0.76580(17) 0.61692(11) 0.0347(6) Uani 1 1 d . . . O5 O 0.1913(3) 0.5382(2) 0.59728(18) 0.0894(12) Uani 1 1 d . A . N5 N 0.44137(19) 0.24256(15) 0.56269(10) 0.0355(5) Uani 1 1 d . . . C5 C 0.3489(2) 0.70463(17) 0.62411(11) 0.0332(5) Uani 1 1 d . . . H5 H 0.2877 0.7015 0.6030 0.040 Uiso 1 1 calc R . . O6 O 0.1682(3) 0.4020(3) 0.58128(18) 0.1189(19) Uani 1 1 d . A . C6 C 0.3761(2) 0.64852(17) 0.66223(11) 0.0329(5) Uani 1 1 d . . . H6 H 0.3328 0.6064 0.6663 0.039 Uiso 1 1 calc R . . C7 C 0.3892(2) 0.82732(18) 0.57442(12) 0.0374(6) Uani 1 1 d . . . H7A H 0.4493 0.8552 0.5704 0.045 Uiso 1 1 calc R . . H7B H 0.3664 0.7991 0.5414 0.045 Uiso 1 1 calc R . . C8 C 0.3374(3) 0.9341(2) 0.63297(15) 0.0509(8) Uani 1 1 d . . . H8A H 0.4052 0.9514 0.6376 0.061 Uiso 1 1 calc R . . H8B H 0.2973 0.9828 0.6301 0.061 Uiso 1 1 calc R . . O9 O 0.16131(18) 0.78497(14) 0.56163(10) 0.0404(5) Uiso 1 1 d . . . C9 C 0.3217(3) 0.8900(3) 0.68080(15) 0.0532(9) Uani 1 1 d . . . H9A H 0.3726 0.8495 0.6898 0.064 Uiso 1 1 calc R . . H9B H 0.3247 0.9277 0.7103 0.064 Uiso 1 1 calc R . . C10 C 0.2194(3) 0.7960(3) 0.71111(13) 0.0517(9) Uani 1 1 d . . . H10A H 0.2354 0.8217 0.7456 0.062 Uiso 1 1 calc R . . H10B H 0.2642 0.7509 0.7097 0.062 Uiso 1 1 calc R . . C11 C 0.3112(3) 0.9464(2) 0.53695(15) 0.0466(8) Uani 1 1 d . . . H11A H 0.3699 0.9797 0.5420 0.056 Uiso 1 1 calc R . . H11B H 0.3110 0.9150 0.5047 0.056 Uiso 1 1 calc R . . C12 C 0.2254(3) 1.0006(2) 0.52974(17) 0.0540(9) Uani 1 1 d . . . H12A H 0.2253 1.0319 0.5620 0.065 Uiso 1 1 calc R . . H12B H 0.2311 1.0387 0.5013 0.065 Uiso 1 1 calc R . . C13 C 0.5051(2) 0.45659(16) 0.65378(11) 0.0318(5) Uani 1 1 d . . . H13 H 0.5591 0.4887 0.6502 0.038 Uiso 1 1 calc R . . C14 C 0.4783(2) 0.39683(16) 0.61728(11) 0.0327(5) Uani 1 1 d . . . H14 H 0.5132 0.3889 0.5894 0.039 Uiso 1 1 calc R . . C15 C 0.3998(2) 0.34883(16) 0.62199(10) 0.0310(5) Uani 1 1 d . . . C16 C 0.3525(2) 0.36379(18) 0.66362(11) 0.0360(6) Uani 1 1 d . . . H16 H 0.2988 0.3321 0.6685 0.043 Uiso 1 1 calc R . . C17 C 0.3829(2) 0.42441(17) 0.69797(11) 0.0354(6) Uani 1 1 d . . . H17 H 0.3488 0.4337 0.7260 0.042 Uiso 1 1 calc R . . C18 C 0.3644(2) 0.28489(18) 0.58279(12) 0.0364(6) Uani 1 1 d . . . H18A H 0.3260 0.2458 0.5992 0.044 Uiso 1 1 calc R . . H18B H 0.3217 0.3097 0.5533 0.044 Uiso 1 1 calc R . . C19 C 0.4706(3) 0.16934(19) 0.59272(14) 0.0468(8) Uani 1 1 d . . . H19A H 0.5205 0.1418 0.5766 0.056 Uiso 1 1 calc R . . H19B H 0.4147 0.1332 0.5904 0.056 Uiso 1 1 calc R . . C20 C 0.5088(3) 0.1840(2) 0.64899(14) 0.0488(8) Uani 1 1 d . . . H20A H 0.4604 0.2130 0.6654 0.059 Uiso 1 1 calc R . . H20B H 0.5221 0.1324 0.6672 0.059 Uiso 1 1 calc R . . C21 C 0.6197(3) 0.2655(2) 0.70433(13) 0.0510(9) Uani 1 1 d . . . H21A H 0.6137 0.2251 0.7314 0.061 Uiso 1 1 calc R . . H21B H 0.5751 0.3099 0.7082 0.061 Uiso 1 1 calc R . . C22 C 0.4149(3) 0.2234(2) 0.50751(13) 0.0435(7) Uani 1 1 d . . . H22A H 0.3494 0.2007 0.5015 0.052 Uiso 1 1 calc R . . H22B H 0.4593 0.1822 0.4979 0.052 Uiso 1 1 calc R . . C23 C 0.4181(2) 0.2952(2) 0.47324(12) 0.0443(7) Uani 1 1 d . . . H23A H 0.3976 0.2801 0.4364 0.053 Uiso 1 1 calc R . . H23B H 0.3737 0.3367 0.4824 0.053 Uiso 1 1 calc R . . C24 C 0.5195(2) 0.3994(2) 0.45339(12) 0.0405(7) Uani 1 1 d . . . H24A H 0.4744 0.4387 0.4644 0.049 Uiso 1 1 calc R . . H24B H 0.5021 0.3911 0.4154 0.049 Uiso 1 1 calc R . . C25 C 0.6200(3) 0.4306(2) 0.46564(13) 0.0429(7) Uani 1 1 d . . . H25A H 0.6660 0.3875 0.4614 0.052 Uiso 1 1 calc R . . H25B H 0.6293 0.4743 0.4414 0.052 Uiso 1 1 calc R . . O7A O 0.1569(11) 0.4637(9) 0.6621(4) 0.146(7) Uani 0.50 1 d P A 1 O8A O 0.0373(6) 0.4863(5) 0.5927(4) 0.079(2) Uani 0.50 1 d P A 1 O7B O 0.1067(12) 0.4561(7) 0.6456(5) 0.140(7) Uani 0.50 1 d P A 2 O8B O 0.0507(6) 0.4843(5) 0.5542(6) 0.105(4) Uani 0.50 1 d P A 2 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 Ni1 0.0318(3) 0.0236(2) 0.0267(2) 0.000 0.00939(18) 0.000 Cl1 0.0500(5) 0.0440(5) 0.1154(10) -0.0079(5) 0.0159(6) 0.0025(4) S1 0.0794(7) 0.0439(5) 0.0759(7) -0.0131(4) 0.0532(6) -0.0202(5) O1 0.0463(13) 0.0578(15) 0.0415(12) -0.0006(10) 0.0079(10) 0.0107(11) N1 0.0479(14) 0.0300(11) 0.0338(11) 0.0013(9) 0.0136(10) -0.0008(10) C1 0.0426(16) 0.0298(13) 0.0451(16) -0.0066(12) 0.0126(13) -0.0044(12) O2 0.0546(14) 0.0457(13) 0.0401(11) 0.0037(10) 0.0172(10) 0.0091(11) N2 0.0361(12) 0.0273(10) 0.0304(10) 0.0001(8) 0.0081(9) 0.0005(9) C2 0.0343(14) 0.0305(12) 0.0388(14) -0.0015(11) 0.0078(11) -0.0003(11) O3 0.0387(11) 0.0449(12) 0.0338(10) 0.0018(9) 0.0090(8) 0.0011(9) N3 0.0377(13) 0.0313(11) 0.0450(13) -0.0003(10) 0.0061(11) 0.0033(10) C3 0.0365(14) 0.0307(13) 0.0415(15) -0.0002(11) 0.0112(12) -0.0010(11) O4 0.0487(13) 0.0382(11) 0.0489(13) -0.0049(10) 0.0025(11) 0.0062(10) N4 0.0331(11) 0.0262(10) 0.0280(10) 0.0014(8) 0.0095(9) 0.0008(9) C4 0.0399(15) 0.0304(13) 0.0360(13) 0.0024(10) 0.0130(11) 0.0055(11) O5 0.074(2) 0.089(2) 0.112(3) -0.027(2) 0.035(2) -0.038(2) N5 0.0409(13) 0.0319(11) 0.0363(12) -0.0059(9) 0.0142(10) -0.0009(10) C5 0.0326(13) 0.0338(13) 0.0342(13) -0.0015(10) 0.0080(11) 0.0046(11) O6 0.121(4) 0.099(3) 0.116(3) -0.065(3) -0.045(3) 0.053(3) C6 0.0350(14) 0.0297(12) 0.0356(13) -0.0026(10) 0.0104(11) 0.0009(11) C7 0.0428(16) 0.0324(13) 0.0387(14) 0.0033(11) 0.0117(12) 0.0062(12) C8 0.052(2) 0.0435(17) 0.057(2) -0.0167(15) 0.0084(16) 0.0012(15) C9 0.051(2) 0.061(2) 0.0469(18) -0.0178(16) 0.0054(15) 0.0102(17) C10 0.054(2) 0.068(2) 0.0353(15) -0.0023(15) 0.0112(14) 0.0207(18) C11 0.0443(17) 0.0348(15) 0.059(2) 0.0110(14) 0.0036(15) -0.0006(13) C12 0.052(2) 0.0328(15) 0.071(2) 0.0015(15) -0.0082(18) 0.0035(15) C13 0.0376(14) 0.0299(12) 0.0303(12) 0.0024(10) 0.0126(11) -0.0012(11) C14 0.0386(14) 0.0317(12) 0.0306(12) 0.0003(10) 0.0146(11) 0.0012(11) C15 0.0351(13) 0.0275(12) 0.0317(12) -0.0010(10) 0.0091(11) 0.0011(10) C16 0.0369(15) 0.0359(14) 0.0379(14) -0.0061(11) 0.0146(12) -0.0081(12) C17 0.0398(15) 0.0348(13) 0.0354(13) -0.0041(11) 0.0176(12) -0.0043(11) C18 0.0391(15) 0.0367(14) 0.0360(14) -0.0064(11) 0.0141(12) -0.0022(12) C19 0.057(2) 0.0313(14) 0.0564(19) -0.0023(13) 0.0219(16) 0.0012(14) C20 0.064(2) 0.0371(15) 0.0495(18) 0.0082(13) 0.0226(17) 0.0052(15) C21 0.059(2) 0.058(2) 0.0386(16) 0.0071(15) 0.0170(15) 0.0180(17) C22 0.0478(18) 0.0434(16) 0.0421(16) -0.0144(13) 0.0162(14) -0.0088(14) C23 0.0405(16) 0.060(2) 0.0342(14) -0.0063(14) 0.0096(12) -0.0014(15) C24 0.0415(16) 0.0425(16) 0.0375(14) 0.0023(12) 0.0063(12) 0.0081(13) C25 0.0474(18) 0.0410(16) 0.0408(15) 0.0015(13) 0.0084(13) 0.0045(14) O7A 0.178(13) 0.170(13) 0.072(6) -0.032(7) -0.037(7) 0.107(11) O8A 0.047(4) 0.069(4) 0.114(7) 0.002(5) -0.005(4) -0.008(3) O7B 0.226(16) 0.097(7) 0.129(10) -0.043(7) 0.126(11) -0.100(10) O8B 0.054(4) 0.063(5) 0.187(11) 0.008(7) -0.019(6) 0.000(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 Ni1 N1 2.083(3) . ? Ni1 N1 2.083(3) 2_656 ? Ni1 N4 2.111(2) . ? Ni1 N4 2.111(2) 2_656 ? Ni1 N2 2.117(2) 2_656 ? Ni1 N2 2.117(2) . ? Cl1 O7B 1.321(9) . ? Cl1 O8A 1.371(8) . ? Cl1 O6 1.383(4) . ? Cl1 O5 1.392(4) . ? Cl1 O8B 1.558(11) . ? Cl1 O7A 1.595(11) . ? S1 C1 1.632(3) . ? O1 C10 1.417(5) . ? O1 C9 1.429(5) . ? N1 C1 1.145(4) . ? O2 C20 1.431(5) . ? O2 C21 1.440(4) . ? N2 C6 1.337(4) . ? N2 C2 1.347(4) . ? C2 C3 1.381(4) . ? C2 H2 0.9500 . ? O3 C23 1.422(4) . ? O3 C24 1.427(4) . ? N3 C8 1.503(4) . ? N3 C7 1.505(4) . ? N3 C11 1.520(4) . ? N3 H3N 0.9300 . ? C3 C4 1.395(4) . ? C3 H3 0.9500 . ? O4 C12 1.416(5) 3_545 ? O4 C25 1.428(4) . ? N4 C13 1.340(3) . ? N4 C17 1.341(4) . ? C4 C5 1.388(4) . ? C4 C7 1.509(4) . ? N5 C22 1.462(4) . ? N5 C18 1.463(4) . ? N5 C19 1.478(4) . ? C5 C6 1.377(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.494(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O9 H9OB 0.85(4) . ? O9 H9OA 0.82(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C21 1.483(6) 3_455 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.503(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O4 1.416(5) 3_455 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.391(4) . ? C13 H13 0.9500 . ? C14 C15 1.391(4) . ? C14 H14 0.9500 . ? C15 C16 1.384(4) . ? C15 C18 1.509(4) . ? C16 C17 1.377(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.500(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C10 1.483(6) 3_545 ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.502(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.500(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 175.23(14) . 2_656 ? N1 Ni1 N4 91.74(10) . . ? N1 Ni1 N4 91.63(10) 2_656 . ? N1 Ni1 N4 91.63(9) . 2_656 ? N1 Ni1 N4 91.74(10) 2_656 2_656 ? N4 Ni1 N4 89.80(12) . 2_656 ? N1 Ni1 N2 88.98(10) . 2_656 ? N1 Ni1 N2 87.62(10) 2_656 2_656 ? N4 Ni1 N2 179.16(9) . 2_656 ? N4 Ni1 N2 90.62(9) 2_656 2_656 ? N1 Ni1 N2 87.62(10) . . ? N1 Ni1 N2 88.98(10) 2_656 . ? N4 Ni1 N2 90.62(9) . . ? N4 Ni1 N2 179.16(9) 2_656 . ? N2 Ni1 N2 88.98(13) 2_656 . ? O7B Cl1 O8A 75.1(9) . . ? O7B Cl1 O6 109.0(7) . . ? O8A Cl1 O6 119.8(4) . . ? O7B Cl1 O5 117.6(5) . . ? O8A Cl1 O5 115.0(4) . . ? O6 Cl1 O5 114.4(3) . . ? O7B Cl1 O8B 115.1(9) . . ? O8A Cl1 O8B 41.3(5) . . ? O6 Cl1 O8B 95.9(5) . . ? O5 Cl1 O8B 102.8(4) . . ? O7B Cl1 O7A 29.2(8) . . ? O8A Cl1 O7A 101.7(7) . . ? O6 Cl1 O7A 105.5(5) . . ? O5 Cl1 O7A 95.5(7) . . ? O8B Cl1 O7A 143.0(7) . . ? C10 O1 C9 111.9(3) . . ? C1 N1 Ni1 152.7(3) . . ? N1 C1 S1 177.8(3) . . ? C20 O2 C21 112.2(3) . . ? C6 N2 C2 117.5(2) . . ? C6 N2 Ni1 121.35(19) . . ? C2 N2 Ni1 121.1(2) . . ? N2 C2 C3 123.2(3) . . ? N2 C2 H2 118.4 . . ? C3 C2 H2 118.4 . . ? C23 O3 C24 112.4(3) . . ? C8 N3 C7 114.7(3) . . ? C8 N3 C11 110.1(3) . . ? C7 N3 C11 105.6(2) . . ? C8 N3 H3N 108.7 . . ? C7 N3 H3N 108.7 . . ? C11 N3 H3N 108.7 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C12 O4 C25 112.6(3) 3_545 . ? C13 N4 C17 117.1(2) . . ? C13 N4 Ni1 123.36(19) . . ? C17 N4 Ni1 119.52(18) . . ? C5 C4 C3 118.2(3) . . ? C5 C4 C7 122.5(3) . . ? C3 C4 C7 119.3(3) . . ? C22 N5 C18 111.7(3) . . ? C22 N5 C19 110.2(3) . . ? C18 N5 C19 112.0(2) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N2 C6 C5 123.1(3) . . ? N2 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? N3 C7 C4 115.9(2) . . ? N3 C7 H7A 108.3 . . ? C4 C7 H7A 108.3 . . ? N3 C7 H7B 108.3 . . ? C4 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C9 C8 N3 116.4(3) . . ? C9 C8 H8A 108.2 . . ? N3 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? N3 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? H9OB O9 H9OA 104(5) . . ? O1 C9 C8 109.4(3) . . ? O1 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? O1 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? O1 C10 C21 110.5(3) . 3_455 ? O1 C10 H10A 109.5 . . ? C21 C10 H10A 109.5 3_455 . ? O1 C10 H10B 109.5 . . ? C21 C10 H10B 109.5 3_455 . ? H10A C10 H10B 108.1 . . ? C12 C11 N3 114.3(3) . . ? C12 C11 H11A 108.7 . . ? N3 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? N3 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? O4 C12 C11 113.6(3) 3_455 . ? O4 C12 H12A 108.8 3_455 . ? C11 C12 H12A 108.8 . . ? O4 C12 H12B 108.8 3_455 . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? N4 C13 C14 123.1(3) . . ? N4 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C15 C14 C13 119.4(2) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 117.1(3) . . ? C16 C15 C18 120.6(3) . . ? C14 C15 C18 122.3(2) . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N4 C17 C16 123.2(3) . . ? N4 C17 H17 118.4 . . ? C16 C17 H17 118.4 . . ? N5 C18 C15 113.6(2) . . ? N5 C18 H18A 108.8 . . ? C15 C18 H18A 108.8 . . ? N5 C18 H18B 108.8 . . ? C15 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? N5 C19 C20 114.1(3) . . ? N5 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? N5 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? O2 C20 C19 109.9(3) . . ? O2 C20 H20A 109.7 . . ? C19 C20 H20A 109.7 . . ? O2 C20 H20B 109.7 . . ? C19 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? O2 C21 C10 109.8(3) . 3_545 ? O2 C21 H21A 109.7 . . ? C10 C21 H21A 109.7 3_545 . ? O2 C21 H21B 109.7 . . ? C10 C21 H21B 109.7 3_545 . ? H21A C21 H21B 108.2 . . ? N5 C22 C23 112.4(3) . . ? N5 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? N5 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? O3 C23 C22 109.2(3) . . ? O3 C23 H23A 109.8 . . ? C22 C23 H23A 109.8 . . ? O3 C23 H23B 109.8 . . ? C22 C23 H23B 109.8 . . ? H23A C23 H23B 108.3 . . ? O3 C24 C25 109.2(3) . . ? O3 C24 H24A 109.8 . . ? C25 C24 H24A 109.8 . . ? O3 C24 H24B 109.8 . . ? C25 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? O4 C25 C24 109.4(3) . . ? O4 C25 H25A 109.8 . . ? C24 C25 H25A 109.8 . . ? O4 C25 H25B 109.8 . . ? C24 C25 H25B 109.8 . . ? H25A C25 H25B 108.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O9 0.93 1.90 2.781(4) 156.9 . O9 H9OA O2 0.82(6) 2.08(6) 2.859(3) 159(6) 3_455 O9 H9OB O3 0.85(4) 1.98(4) 2.821(4) 168(4) 3_455 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.069 _refine_diff_density_min -0.845 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 898008' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H78 N8 Ni O10, 4(Cl O4), O, 3(H2 O)' _chemical_formula_sum 'C48 H84 Cl4 N8 Ni O30' _chemical_formula_weight 1453.74 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.576(4) _cell_length_b 14.207(3) _cell_length_c 25.869(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.43(3) _cell_angle_gamma 90.00 _cell_volume 6431(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 58514 _cell_measurement_theta_min 1.16 _cell_measurement_theta_max 28.60 _exptl_crystal_description plate _exptl_crystal_colour olive-green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3056 _exptl_absorpt_coefficient_mu 0.561 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 58514 _diffrn_reflns_av_R_equivalents 0.1551 _diffrn_reflns_av_sigmaI/netI 0.1167 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 28.60 _reflns_number_total 16085 _reflns_number_gt 8461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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^)+(0.0978P)^2^+20.7792P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16085 _refine_ls_number_parameters 833 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1746 _refine_ls_R_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.2742 _refine_ls_wR_factor_gt 0.2335 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.011 _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 Ni1 Ni 0.74690(4) 0.61139(5) 0.75723(3) 0.0322(9) Uani 1 1 d . . . Cl3 Cl 0.67793(10) 0.31860(13) 0.86843(7) 0.0506(9) Uani 1 1 d . . . Cl4 Cl 0.79558(10) 0.35816(12) 0.56509(7) 0.0499(9) Uani 1 1 d . . . Cl1 Cl 0.83193(10) 0.94005(12) 0.83345(7) 0.0459(9) Uani 1 1 d . . . Cl2 Cl 0.67326(9) 0.92912(11) 0.65328(7) 0.0459(9) Uani 1 1 d . . . O2 O 0.7416(3) 0.7595(3) 0.75756(17) 0.0414(13) Uani 1 1 d D . . N5 N 0.8256(3) 0.6063(4) 0.7005(2) 0.0362(14) Uani 1 1 d . . . N3 N 0.6563(3) 0.6111(3) 0.69837(19) 0.0338(13) Uani 1 1 d . . . N7 N 0.8404(3) 0.6180(4) 0.8145(2) 0.0371(14) Uani 1 1 d . . . O1 O 0.7470(3) 0.4639(3) 0.76019(18) 0.0438(13) Uani 1 1 d D . . N1 N 0.6659(3) 0.6088(4) 0.81263(19) 0.0345(13) Uani 1 1 d . . . C3 C 0.5554(3) 0.5983(4) 0.8844(2) 0.0372(15) Uani 1 1 d . . . O11 O 0.7880(3) 0.8591(3) 0.84812(19) 0.0462(14) Uani 1 1 d . . . C28 C 0.8687(4) 0.6599(4) 0.6207(2) 0.0381(16) Uani 1 1 d . . . H28 H 0.8625 0.7024 0.5922 0.046 Uiso 1 1 calc R . . C5 C 0.6685(3) 0.6657(4) 0.8540(2) 0.0356(15) Uani 1 1 d . . . H5 H 0.7089 0.7103 0.8587 0.043 Uiso 1 1 calc R . . C27 C 0.9275(4) 0.5947(4) 0.6238(3) 0.0416(17) Uani 1 1 d . . . C39 C 0.9727(4) 0.6216(4) 0.8845(3) 0.0414(16) Uani 1 1 d . . . O15 O 0.7278(3) 0.8535(4) 0.6647(2) 0.0568(16) Uani 1 1 d . . . C29 C 0.8189(3) 0.6633(4) 0.6588(2) 0.0356(15) Uani 1 1 d . . . H29 H 0.7783 0.7077 0.6555 0.043 Uiso 1 1 calc R . . O25 O 0.7315(4) 0.4005(5) 0.5850(3) 0.081(2) Uani 1 1 d . . . C15 C 0.5381(3) 0.6769(4) 0.6618(2) 0.0357(15) Uani 1 1 d . . . H15 H 0.5010 0.7255 0.6622 0.043 Uiso 1 1 calc R . . C18 C 0.6482(3) 0.5423(4) 0.6623(2) 0.0341(15) Uani 1 1 d . . . H18 H 0.6872 0.4961 0.6620 0.041 Uiso 1 1 calc R . . C4 C 0.6151(3) 0.6629(4) 0.8906(2) 0.0345(15) Uani 1 1 d . . . H4 H 0.6194 0.7047 0.9194 0.041 Uiso 1 1 calc R . . C2 C 0.5525(4) 0.5410(4) 0.8406(3) 0.0415(16) Uani 1 1 d . . . H2 H 0.5126 0.4961 0.8344 0.050 Uiso 1 1 calc R . . C14 C 0.6014(3) 0.6776(4) 0.6971(2) 0.0359(15) Uani 1 1 d . . . H14 H 0.6068 0.7273 0.7217 0.043 Uiso 1 1 calc R . . O13 O 0.8273(4) 1.0130(4) 0.8703(3) 0.079(2) Uani 1 1 d . . . C38 C 0.9566(4) 0.6919(5) 0.8475(3) 0.0445(17) Uani 1 1 d . . . H38 H 0.9907 0.7435 0.8460 0.053 Uiso 1 1 calc R . . O16 O 0.6002(3) 0.9019(4) 0.6665(3) 0.076(2) Uani 1 1 d . . . C40 C 0.9188(4) 0.5498(4) 0.8854(3) 0.0413(16) Uani 1 1 d . . . H40 H 0.9266 0.5001 0.9099 0.050 Uiso 1 1 calc R . . O18 O 0.7003(4) 1.0127(4) 0.6783(3) 0.083(2) Uani 1 1 d . . . C1 C 0.6069(4) 0.5491(4) 0.8062(3) 0.0432(17) Uani 1 1 d . . . H1 H 0.6025 0.5102 0.7762 0.052 Uiso 1 1 calc R . . C41 C 0.8543(4) 0.5511(4) 0.8507(3) 0.0408(16) Uani 1 1 d . . . H41 H 0.8178 0.5022 0.8526 0.049 Uiso 1 1 calc R . . C26 C 0.9338(4) 0.5370(5) 0.6668(3) 0.0489(19) Uani 1 1 d . . . H26 H 0.9730 0.4909 0.6706 0.059 Uiso 1 1 calc R . . O26 O 0.8371(4) 0.3038(5) 0.6046(2) 0.087(2) Uani 1 1 d . . . C25 C 0.8832(4) 0.5457(5) 0.7050(3) 0.0477(18) Uani 1 1 d . . . H25 H 0.8903 0.5071 0.7350 0.057 Uiso 1 1 calc R . . O17 O 0.6701(4) 0.9458(4) 0.5975(2) 0.0678(18) Uani 1 1 d . . . C17 C 0.5860(4) 0.5360(4) 0.6262(2) 0.0373(15) Uani 1 1 d . . . H17 H 0.5820 0.4856 0.6019 0.045 Uiso 1 1 calc R . . C37 C 0.8922(4) 0.6876(5) 0.8131(3) 0.0428(17) Uani 1 1 d . . . H37 H 0.8838 0.7354 0.7875 0.051 Uiso 1 1 calc R . . O12 O 0.9081(3) 0.9138(4) 0.8297(3) 0.079(2) Uani 1 1 d . . . O20 O 0.6551(6) 0.3319(7) 0.8157(3) 0.126(3) Uani 1 1 d . . . O14 O 0.7958(5) 0.9731(6) 0.7845(3) 0.094(2) Uani 1 1 d . . . O23 O 0.7721(4) 0.2990(5) 0.5221(2) 0.0745(19) Uani 1 1 d . . . O21 O 0.6124(5) 0.3254(5) 0.8939(4) 0.116(3) Uani 1 1 d . . . O22 O 0.7117(4) 0.2292(5) 0.8766(4) 0.118(4) Uani 1 1 d . . . N4 N 0.4029(3) 0.5286(4) 0.5929(2) 0.0382(14) Uani 1 1 d . . . N6 N 1.0018(4) 0.6700(4) 0.5570(2) 0.0498(17) Uani 1 1 d . . . N2 N 0.4671(3) 0.6728(3) 0.9431(2) 0.0374(14) Uani 1 1 d . . . C6 C 0.4990(4) 0.5850(4) 0.9244(3) 0.0388(16) Uani 1 1 d . . . H6A H 0.4564 0.5451 0.9091 0.047 Uiso 1 1 calc R . . H6B H 0.5246 0.5506 0.9545 0.047 Uiso 1 1 calc R . . C19 C 0.4608(4) 0.6045(5) 0.5849(2) 0.0395(15) Uani 1 1 d . . . H19A H 0.4793 0.5962 0.5502 0.047 Uiso 1 1 calc R . . H19B H 0.4352 0.6665 0.5853 0.047 Uiso 1 1 calc R . . C16 C 0.5282(4) 0.6043(4) 0.6251(2) 0.0371(15) Uani 1 1 d . . . C30 C 0.9785(4) 0.5811(5) 0.5803(3) 0.052(2) Uani 1 1 d . . . H30A H 1.0249 0.5464 0.5940 0.062 Uiso 1 1 calc R . . H30B H 0.9512 0.5419 0.5528 0.062 Uiso 1 1 calc R . . C42 C 1.0424(4) 0.6267(5) 0.9221(3) 0.0483(18) Uani 1 1 d . . . H42A H 1.0278 0.6144 0.9575 0.058 Uiso 1 1 calc R . . H42B H 1.0638 0.6911 0.9216 0.058 Uiso 1 1 calc R . . N8 N 1.1034(4) 0.5566(4) 0.9099(3) 0.067(2) Uani 1 1 d . . . H8 H 1.0860 0.4964 0.9166 0.080 Uiso 1 1 calc R . . C11 C 0.3896(4) 0.7069(5) 0.8594(3) 0.0450(17) Uani 1 1 d . . . H11A H 0.4056 0.6480 0.8430 0.054 Uiso 1 1 calc R . . H11B H 0.3373 0.7228 0.8443 0.054 Uiso 1 1 calc R . . C10 C 0.3910(4) 0.6941(5) 0.9177(3) 0.0420(16) Uani 1 1 d . . . H10A H 0.3718 0.7523 0.9330 0.050 Uiso 1 1 calc R . . H10B H 0.3557 0.6423 0.9248 0.050 Uiso 1 1 calc R . . C43 C 1.1198(5) 0.5616(6) 0.8502(4) 0.078(3) Uani 1 1 d . . . H43A H 1.0833 0.6059 0.8317 0.094 Uiso 1 1 calc R . . H43B H 1.1720 0.5865 0.8479 0.094 Uiso 1 1 calc R . . C31 C 0.9891(6) 0.6657(5) 0.4995(3) 0.070(3) Uani 1 1 d . . . H31A H 1.0227 0.7126 0.4848 0.084 Uiso 1 1 calc R . . H31B H 1.0046 0.6027 0.4879 0.084 Uiso 1 1 calc R . . O24 O 0.8425(4) 0.4300(6) 0.5476(3) 0.090(2) Uani 1 1 d . . . O19 O 0.7283(5) 0.3919(6) 0.8806(5) 0.142(4) Uani 1 1 d . . . O28 O 0.4875(3) 0.3812(3) 0.56551(17) 0.0417(13) Uani 1 1 d . . . O6 O 0.3180(3) 0.3732(3) 0.52688(17) 0.0442(13) Uani 1 1 d . . . O5 O 0.4668(3) 0.4258(3) 0.68369(18) 0.0449(13) Uani 1 1 d . . . O4 O 0.4414(3) 0.7817(3) 0.84998(18) 0.0449(13) Uani 1 1 d . . . O3 O 0.5701(3) 0.7697(3) 1.02054(17) 0.0439(13) Uani 1 1 d . . . O9 O 1.0373(4) 0.4443(4) 0.8198(3) 0.0715(19) Uani 1 1 d . . . O8 O 1.0372(3) 0.7887(4) 0.6444(2) 0.0557(15) Uani 1 1 d . . . C22 C 0.3381(4) 0.5401(5) 0.5503(3) 0.0413(16) Uani 1 1 d . . . H22A H 0.3082 0.5968 0.5576 0.050 Uiso 1 1 calc R . . H22B H 0.3599 0.5504 0.5169 0.050 Uiso 1 1 calc R . . O10 O 1.1568(4) 0.4627(5) 1.0104(2) 0.0698(18) Uani 1 1 d . . . O7 O 0.8856(4) 0.7729(4) 0.4931(2) 0.0675(18) Uani 1 1 d . . . C8 C 0.5393(4) 0.6797(5) 1.0303(3) 0.0468(18) Uani 1 1 d . . . H8A H 0.5337 0.6726 1.0678 0.056 Uiso 1 1 calc R . . H8B H 0.5741 0.6298 1.0199 0.056 Uiso 1 1 calc R . . C13 C 0.5136(5) 0.8442(5) 0.7864(3) 0.0500(19) Uani 1 1 d . . . H13A H 0.5531 0.7953 0.7943 0.060 Uiso 1 1 calc R . . H13B H 0.5126 0.8598 0.7490 0.060 Uiso 1 1 calc R . . C7 C 0.4621(4) 0.6701(5) 0.9995(3) 0.0447(17) Uani 1 1 d . . . H7A H 0.4385 0.6098 1.0086 0.054 Uiso 1 1 calc R . . H7B H 0.4285 0.7217 1.0092 0.054 Uiso 1 1 calc R . . C20 C 0.3746(4) 0.5323(5) 0.6465(3) 0.0426(16) Uani 1 1 d . . . H20A H 0.4007 0.5843 0.6665 0.051 Uiso 1 1 calc R . . H20B H 0.3191 0.5460 0.6429 0.051 Uiso 1 1 calc R . . C21 C 0.3882(4) 0.4433(6) 0.6756(3) 0.053(2) Uani 1 1 d . . . H21A H 0.3664 0.4479 0.7094 0.064 Uiso 1 1 calc R . . H21B H 0.3626 0.3908 0.6557 0.064 Uiso 1 1 calc R . . C23 C 0.2850(4) 0.4565(5) 0.5449(3) 0.0451(17) Uani 1 1 d . . . H23A H 0.2664 0.4435 0.5791 0.054 Uiso 1 1 calc R . . H23B H 0.2401 0.4732 0.5206 0.054 Uiso 1 1 calc R . . C12 C 0.4391(4) 0.8070(5) 0.7970(3) 0.0495(18) Uani 1 1 d . . . H12A H 0.3992 0.8553 0.7888 0.059 Uiso 1 1 calc R . . H12B H 0.4263 0.7512 0.7750 0.059 Uiso 1 1 calc R . . C32 C 0.9100(6) 0.6835(6) 0.4784(3) 0.067(2) Uani 1 1 d . . . H32A H 0.9063 0.6794 0.4400 0.081 Uiso 1 1 calc R . . H32B H 0.8761 0.6347 0.4912 0.081 Uiso 1 1 calc R . . C34 C 1.0785(4) 0.6973(6) 0.5752(4) 0.062(2) Uani 1 1 d . . . H34A H 1.0918 0.7553 0.5568 0.075 Uiso 1 1 calc R . . H34B H 1.1141 0.6472 0.5663 0.075 Uiso 1 1 calc R . . C35 C 1.0899(4) 0.7151(6) 0.6331(4) 0.066(2) Uani 1 1 d . . . H35A H 1.0794 0.6570 0.6524 0.079 Uiso 1 1 calc R . . H35B H 1.1432 0.7350 0.6434 0.079 Uiso 1 1 calc R . . C44 C 1.1134(6) 0.4732(8) 0.8255(5) 0.083(3) Uani 1 1 d . . . H44A H 1.1331 0.4775 0.7910 0.100 Uiso 1 1 calc R . . H44B H 1.1446 0.4263 0.8464 0.100 Uiso 1 1 calc R . . C46 C 1.1784(6) 0.5700(7) 0.9399(5) 0.081(3) Uani 1 1 d . . . H46A H 1.2150 0.5241 0.9276 0.097 Uiso 1 1 calc R . . H46B H 1.1974 0.6339 0.9328 0.097 Uiso 1 1 calc R . . C47 C 1.1769(8) 0.5593(8) 0.9933(4) 0.094(4) Uani 1 1 d . . . H47A H 1.1395 0.6044 1.0054 0.112 Uiso 1 1 calc R . . H47B H 1.2278 0.5761 1.0105 0.112 Uiso 1 1 calc R . . O29 O 0.8112(4) 0.3249(4) 0.7109(2) 0.0635(17) Uani 1 1 d D . . O30 O 1.0355(3) 0.3928(4) 0.9350(2) 0.0628(17) Uani 1 1 d . . . C9 C 0.6467(4) 0.7813(5) 1.0433(3) 0.0460(17) Uani 1 1 d . . . H9A H 0.6790 0.7296 1.0319 0.055 Uiso 1 1 calc R . . H9B H 0.6479 0.7788 1.0816 0.055 Uiso 1 1 calc R . . O27 O 0.7497(5) 0.1732(5) 0.7578(3) 0.094(2) Uani 1 1 d . . . C24 C 0.3228(4) 0.3739(5) 0.4730(3) 0.0466(18) Uani 1 1 d . . . H24A H 0.3571 0.4253 0.4637 0.056 Uiso 1 1 calc R . . H24B H 0.2716 0.3849 0.4546 0.056 Uiso 1 1 calc R . . C33 C 0.8165(5) 0.8035(7) 0.4661(3) 0.070(3) Uani 1 1 d . . . H33A H 0.7771 0.7540 0.4672 0.084 Uiso 1 1 calc R . . H33B H 0.8244 0.8156 0.4293 0.084 Uiso 1 1 calc R . . C48 C 1.2105(5) 0.3948(7) 1.0085(4) 0.076(3) Uani 1 1 d . . . H48A H 1.2592 0.4163 1.0272 0.091 Uiso 1 1 calc R . . H48B H 1.2195 0.3823 0.9719 0.091 Uiso 1 1 calc R . . C45 C 1.0249(7) 0.3590(8) 0.7912(4) 0.087(4) Uani 1 1 d . . . H45A H 1.0682 0.3153 0.7996 0.105 Uiso 1 1 calc R . . H45B H 1.0210 0.3722 0.7535 0.105 Uiso 1 1 calc R . . C36 C 1.0472(6) 0.8154(6) 0.6945(3) 0.080(3) Uani 1 1 d . . . H36A H 1.0896 0.8613 0.6996 0.096 Uiso 1 1 calc R . . H36B H 1.0603 0.7601 0.7169 0.096 Uiso 1 1 calc R . . H6 H 0.4293 0.4630 0.5862 0.040(18) Uiso 1 1 d R . . H29D H 0.8158 0.3025 0.6751 0.08(3) Uiso 1 1 d R . . H29C H 0.7806 0.2620 0.7248 0.11(4) Uiso 1 1 d RD . . H1C H 0.7528 0.4225 0.7368 0.08(3) Uiso 1 1 d R . . H2C H 0.7462 0.8011 0.7308 0.07(3) Uiso 1 1 d R . . H2D H 0.7281 0.8032 0.7899 0.11(4) Uiso 1 1 d RD . . H1D H 0.7358 0.4404 0.7916 0.05(2) Uiso 1 1 d RD . . H28D H 0.5049 0.3477 0.5899 0.04(2) Uiso 1 1 d R . . H30C H 1.0034 0.3611 0.9042 0.13(5) Uiso 1 1 d R . . H28C H 0.4675 0.3356 0.5464 0.06(3) Uiso 1 1 d R . . H30D H 1.0545 0.3392 0.9579 0.14(5) Uiso 1 1 d 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 Ni1 0.0316(9) 0.0279(9) 0.0378(9) 0.0020(3) 0.0068(3) 0.0005(3) Cl3 0.0517(12) 0.0505(13) 0.0505(13) 0.0109(8) 0.0090(7) -0.0115(8) Cl4 0.0539(13) 0.0443(12) 0.0529(13) -0.0026(7) 0.0125(8) 0.0055(7) Cl1 0.0463(12) 0.0405(12) 0.0522(13) -0.0024(7) 0.0117(7) -0.0090(7) Cl2 0.0438(12) 0.0338(11) 0.0592(13) 0.0047(7) 0.0004(7) 0.0043(6) O2 0.051(3) 0.030(2) 0.043(3) 0.0000(19) 0.0006(19) 0.0007(19) N5 0.036(3) 0.031(3) 0.043(3) 0.002(2) 0.009(2) 0.005(2) N3 0.035(3) 0.029(2) 0.038(3) 0.002(2) 0.009(2) 0.002(2) N7 0.034(3) 0.034(3) 0.044(3) 0.005(2) 0.004(2) 0.000(2) O1 0.055(3) 0.033(2) 0.045(3) 0.005(2) 0.015(2) 0.004(2) N1 0.036(3) 0.032(3) 0.036(3) 0.003(2) 0.006(2) 0.000(2) C3 0.041(3) 0.034(3) 0.038(3) 0.003(2) 0.011(3) 0.006(2) O11 0.045(3) 0.045(3) 0.050(3) -0.005(2) 0.010(2) -0.012(2) C28 0.044(3) 0.032(3) 0.040(3) 0.004(2) 0.010(3) -0.001(2) C5 0.034(3) 0.033(3) 0.039(3) -0.001(2) 0.003(2) -0.004(2) C27 0.042(3) 0.033(3) 0.051(4) 0.003(3) 0.013(3) -0.003(3) C39 0.043(3) 0.035(3) 0.046(4) -0.004(3) 0.007(3) 0.000(3) O15 0.062(3) 0.040(3) 0.070(4) 0.007(2) 0.015(3) 0.021(2) C29 0.039(3) 0.032(3) 0.037(3) -0.002(2) 0.005(2) 0.001(2) O25 0.083(4) 0.072(4) 0.095(5) -0.005(4) 0.039(4) 0.022(3) C15 0.037(3) 0.034(3) 0.037(3) -0.003(2) 0.003(2) 0.004(2) C18 0.030(3) 0.032(3) 0.040(3) 0.000(2) 0.005(2) 0.006(2) C4 0.034(3) 0.035(3) 0.035(3) -0.001(2) 0.003(2) 0.001(2) C2 0.042(3) 0.033(3) 0.050(4) -0.005(3) 0.012(3) -0.005(3) C14 0.037(3) 0.034(3) 0.038(3) -0.005(2) 0.011(2) 0.000(2) O13 0.078(4) 0.054(4) 0.111(5) -0.029(3) 0.040(4) -0.021(3) C38 0.039(3) 0.038(3) 0.056(4) 0.005(3) 0.002(3) -0.004(3) O16 0.059(3) 0.065(4) 0.108(5) 0.030(4) 0.030(3) 0.013(3) C40 0.044(4) 0.032(3) 0.049(4) 0.007(3) 0.010(3) 0.004(3) O18 0.087(5) 0.050(4) 0.108(5) -0.026(3) -0.023(4) 0.012(3) C1 0.051(4) 0.032(3) 0.048(4) -0.006(3) 0.017(3) -0.004(3) C41 0.041(3) 0.035(3) 0.047(4) 0.006(3) 0.009(3) 0.000(3) C26 0.043(4) 0.043(4) 0.065(5) 0.014(3) 0.024(3) 0.014(3) O26 0.123(6) 0.080(5) 0.056(4) -0.004(3) 0.002(4) 0.053(4) C25 0.047(4) 0.037(3) 0.061(4) 0.017(3) 0.015(3) 0.009(3) O17 0.078(4) 0.063(4) 0.062(4) 0.016(3) 0.003(3) 0.004(3) C17 0.048(4) 0.029(3) 0.036(3) -0.002(2) 0.010(3) -0.001(2) C37 0.042(3) 0.036(3) 0.050(4) 0.008(3) 0.006(3) -0.006(3) O12 0.045(3) 0.055(4) 0.139(6) -0.012(4) 0.026(3) -0.010(3) O20 0.196(10) 0.111(7) 0.064(5) -0.009(4) -0.014(5) 0.014(7) O14 0.120(6) 0.092(5) 0.069(4) 0.029(4) -0.001(4) -0.015(4) O23 0.096(5) 0.068(4) 0.058(4) -0.014(3) 0.000(3) 0.001(3) O21 0.146(7) 0.069(5) 0.152(8) -0.009(5) 0.105(6) -0.018(5) O22 0.063(4) 0.064(4) 0.224(10) 0.065(6) 0.004(5) 0.000(3) N4 0.038(3) 0.039(3) 0.039(3) -0.003(2) 0.004(2) 0.001(2) N6 0.060(4) 0.033(3) 0.060(4) 0.003(3) 0.026(3) -0.002(2) N2 0.043(3) 0.030(3) 0.040(3) 0.000(2) 0.008(2) 0.002(2) C6 0.044(3) 0.031(3) 0.044(4) 0.001(2) 0.015(3) -0.001(2) C19 0.041(3) 0.039(3) 0.039(3) -0.004(3) 0.004(3) 0.000(3) C16 0.042(3) 0.032(3) 0.038(3) -0.004(2) 0.008(2) -0.004(2) C30 0.064(5) 0.026(3) 0.069(5) 0.003(3) 0.028(4) 0.006(3) C42 0.047(4) 0.052(4) 0.045(4) -0.001(3) 0.004(3) -0.002(3) N8 0.043(3) 0.038(3) 0.115(6) 0.010(3) -0.020(4) -0.004(3) C11 0.041(3) 0.044(4) 0.049(4) 0.001(3) -0.001(3) -0.006(3) C10 0.040(3) 0.038(3) 0.048(4) -0.002(3) 0.007(3) -0.006(3) C43 0.065(5) 0.055(5) 0.124(9) 0.025(5) 0.054(6) 0.010(4) C31 0.121(8) 0.037(4) 0.060(5) 0.001(3) 0.048(5) -0.001(4) O24 0.066(4) 0.094(5) 0.111(6) 0.016(4) 0.006(4) -0.019(4) O19 0.099(6) 0.089(6) 0.230(12) 0.059(7) -0.032(7) -0.057(5) O28 0.049(3) 0.034(2) 0.041(3) 0.003(2) -0.0008(19) -0.002(2) O6 0.047(3) 0.046(3) 0.040(3) -0.001(2) 0.007(2) -0.004(2) O5 0.047(3) 0.044(3) 0.043(3) 0.007(2) 0.005(2) 0.003(2) O4 0.052(3) 0.038(2) 0.043(3) 0.0032(19) -0.002(2) -0.007(2) O3 0.048(3) 0.043(3) 0.040(3) 0.008(2) 0.002(2) -0.001(2) O9 0.072(4) 0.061(4) 0.087(4) 0.004(3) 0.040(3) 0.011(3) O8 0.058(3) 0.053(3) 0.054(3) 0.001(2) -0.003(2) 0.004(2) C22 0.040(3) 0.039(3) 0.044(4) 0.000(3) 0.000(3) 0.002(3) O10 0.071(4) 0.079(4) 0.058(4) 0.003(3) -0.003(3) -0.004(3) O7 0.100(5) 0.045(3) 0.054(3) -0.004(2) -0.013(3) -0.009(3) C8 0.060(4) 0.042(4) 0.038(4) 0.008(3) 0.003(3) 0.000(3) C13 0.071(5) 0.047(4) 0.033(3) -0.006(3) 0.010(3) 0.003(3) C7 0.056(4) 0.038(3) 0.042(4) 0.004(3) 0.016(3) -0.005(3) C20 0.042(3) 0.047(4) 0.039(3) 0.000(3) 0.008(3) 0.006(3) C21 0.049(4) 0.067(5) 0.046(4) 0.000(3) 0.014(3) 0.003(3) C23 0.044(4) 0.048(4) 0.044(4) -0.009(3) 0.006(3) -0.001(3) C12 0.061(4) 0.042(4) 0.044(4) -0.002(3) -0.005(3) -0.003(3) C32 0.106(7) 0.049(5) 0.046(4) -0.005(3) 0.008(4) -0.003(5) C34 0.055(4) 0.043(4) 0.093(7) 0.020(4) 0.030(4) 0.007(3) C35 0.043(4) 0.056(5) 0.098(7) 0.022(5) 0.003(4) 0.000(3) C44 0.074(6) 0.084(7) 0.097(8) 0.000(6) 0.033(6) 0.020(5) C46 0.065(6) 0.060(6) 0.113(9) 0.009(5) -0.013(6) 0.003(4) C47 0.123(9) 0.082(7) 0.078(7) -0.025(6) 0.021(6) -0.049(7) O29 0.089(4) 0.051(3) 0.050(3) -0.012(2) 0.005(3) 0.004(3) O30 0.074(4) 0.038(3) 0.071(4) 0.013(3) -0.021(3) -0.004(3) C9 0.051(4) 0.046(4) 0.040(4) 0.005(3) 0.004(3) 0.000(3) O27 0.141(7) 0.070(4) 0.071(4) 0.006(3) 0.005(4) -0.010(4) C24 0.052(4) 0.050(4) 0.037(3) -0.007(3) 0.001(3) 0.000(3) C33 0.067(5) 0.079(6) 0.060(5) 0.017(4) -0.013(4) -0.035(5) C48 0.055(5) 0.072(6) 0.100(7) -0.008(5) -0.001(5) 0.008(4) C45 0.134(10) 0.082(7) 0.047(5) 0.005(5) 0.017(5) 0.051(7) C36 0.107(8) 0.064(6) 0.065(6) 0.002(5) -0.012(5) -0.007(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 Ni1 O1 2.096(4) . ? Ni1 N3 2.097(5) . ? Ni1 O2 2.106(4) . ? Ni1 N7 2.109(5) . ? Ni1 N5 2.112(5) . ? Ni1 N1 2.113(5) . ? Cl3 O21 1.383(7) . ? Cl3 O19 1.385(8) . ? Cl3 O20 1.397(8) . ? Cl3 O22 1.410(7) . ? Cl4 O24 1.413(7) . ? Cl4 O25 1.417(6) . ? Cl4 O23 1.424(6) . ? Cl4 O26 1.425(6) . ? Cl1 O12 1.402(6) . ? Cl1 O13 1.415(6) . ? Cl1 O14 1.441(7) . ? Cl1 O11 1.455(5) . ? Cl2 O18 1.414(6) . ? Cl2 O16 1.413(6) . ? Cl2 O15 1.452(5) . ? Cl2 O17 1.459(6) . ? O2 H2C 0.9207 . ? O2 H2D 1.0858 . ? N5 C25 1.326(8) . ? N5 C29 1.344(8) . ? N3 C18 1.349(8) . ? N3 C14 1.349(7) . ? N7 C41 1.339(8) . ? N7 C37 1.347(8) . ? O1 H1C 0.8576 . ? O1 H1D 0.9169 . ? N1 C5 1.338(8) . ? N1 C1 1.338(8) . ? C3 C4 1.391(9) . ? C3 C2 1.394(9) . ? C3 C6 1.511(8) . ? C28 C29 1.380(8) . ? C28 C27 1.384(9) . ? C28 H28 0.9500 . ? C5 C4 1.397(8) . ? C5 H5 0.9500 . ? C27 C26 1.379(9) . ? C27 C30 1.516(9) . ? C39 C40 1.394(9) . ? C39 C38 1.393(9) . ? C39 C42 1.492(10) . ? C29 H29 0.9500 . ? C15 C14 1.370(8) . ? C15 C16 1.401(8) . ? C15 H15 0.9500 . ? C18 C17 1.373(9) . ? C18 H18 0.9500 . ? C4 H4 0.9500 . ? C2 C1 1.371(9) . ? C2 H2 0.9500 . ? C14 H14 0.9500 . ? C38 C37 1.373(9) . ? C38 H38 0.9500 . ? C40 C41 1.378(9) . ? C40 H40 0.9500 . ? C1 H1 0.9500 . ? C41 H41 0.9500 . ? C26 C25 1.395(9) . ? C26 H26 0.9500 . ? C25 H25 0.9500 . ? C17 C16 1.403(9) . ? C17 H17 0.9500 . ? C37 H37 0.9500 . ? N4 C19 1.509(8) . ? N4 C20 1.517(8) . ? N4 C22 1.517(8) . ? N4 H6 1.0625 . ? N6 C34 1.440(10) . ? N6 C30 1.474(8) . ? N6 C31 1.483(11) . ? N2 C10 1.466(8) . ? N2 C6 1.468(8) . ? N2 C7 1.469(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C19 C16 1.502(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C42 N8 1.519(10) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? N8 C46 1.477(11) . ? N8 C43 1.598(13) . ? N8 H8 0.9300 . ? C11 O4 1.434(8) . ? C11 C10 1.518(10) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C43 C44 1.408(14) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C31 C32 1.468(14) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? O28 H28D 0.8248 . ? O28 H28C 0.8684 . ? O6 C24 1.406(8) . ? O6 C23 1.416(8) . ? O5 C21 1.400(8) . ? O5 C13 1.419(8) 2_646 ? O4 C12 1.413(8) . ? O3 C8 1.421(8) . ? O3 C9 1.426(8) . ? O9 C44 1.393(12) . ? O9 C45 1.427(12) . ? O8 C36 1.346(10) . ? O8 C35 1.446(10) . ? C22 C23 1.508(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O10 C48 1.354(11) . ? O10 C47 1.495(12) . ? O7 C32 1.405(10) . ? O7 C33 1.410(10) . ? C8 C7 1.512(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C13 O5 1.419(8) 2_656 ? C13 C12 1.462(11) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C20 C21 1.479(10) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C34 C35 1.513(13) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C46 C47 1.393(15) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? O29 H29D 0.9900 . ? O29 H29C 1.1192 . ? O30 H30C 1.0350 . ? O30 H30D 1.0014 . ? C9 C24 1.495(10) 2_656 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C24 C9 1.495(10) 2_646 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C33 C48 1.549(14) 2_756 ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C48 C33 1.549(14) 2_746 ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C45 C36 1.488(15) 2_746 ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C36 C45 1.488(15) 2_756 ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? 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 O1 Ni1 N3 91.30(19) . . ? O1 Ni1 O2 176.47(18) . . ? N3 Ni1 O2 88.53(18) . . ? O1 Ni1 N7 91.2(2) . . ? N3 Ni1 N7 177.0(2) . . ? O2 Ni1 N7 89.11(19) . . ? O1 Ni1 N5 89.57(19) . . ? N3 Ni1 N5 89.85(19) . . ? O2 Ni1 N5 93.96(19) . . ? N7 Ni1 N5 88.4(2) . . ? O1 Ni1 N1 87.52(19) . . ? N3 Ni1 N1 88.77(19) . . ? O2 Ni1 N1 88.95(19) . . ? N7 Ni1 N1 93.1(2) . . ? N5 Ni1 N1 176.7(2) . . ? O21 Cl3 O19 112.5(7) . . ? O21 Cl3 O20 106.2(7) . . ? O19 Cl3 O20 103.8(7) . . ? O21 Cl3 O22 110.5(5) . . ? O19 Cl3 O22 113.1(5) . . ? O20 Cl3 O22 110.3(6) . . ? O24 Cl4 O25 108.6(5) . . ? O24 Cl4 O23 108.1(5) . . ? O25 Cl4 O23 110.7(4) . . ? O24 Cl4 O26 110.2(5) . . ? O25 Cl4 O26 109.9(4) . . ? O23 Cl4 O26 109.3(4) . . ? O12 Cl1 O13 110.9(4) . . ? O12 Cl1 O14 111.8(5) . . ? O13 Cl1 O14 107.8(5) . . ? O12 Cl1 O11 110.0(3) . . ? O13 Cl1 O11 109.7(3) . . ? O14 Cl1 O11 106.6(4) . . ? O18 Cl2 O16 113.1(5) . . ? O18 Cl2 O15 110.0(4) . . ? O16 Cl2 O15 110.2(3) . . ? O18 Cl2 O17 107.3(4) . . ? O16 Cl2 O17 109.5(4) . . ? O15 Cl2 O17 106.6(3) . . ? Ni1 O2 H2C 129.2 . . ? Ni1 O2 H2D 126.0 . . ? H2C O2 H2D 104.6 . . ? C25 N5 C29 118.1(5) . . ? C25 N5 Ni1 120.4(4) . . ? C29 N5 Ni1 121.5(4) . . ? C18 N3 C14 117.5(5) . . ? C18 N3 Ni1 121.8(4) . . ? C14 N3 Ni1 120.6(4) . . ? C41 N7 C37 117.5(5) . . ? C41 N7 Ni1 122.5(4) . . ? C37 N7 Ni1 119.8(4) . . ? Ni1 O1 H1C 131.3 . . ? Ni1 O1 H1D 113.5 . . ? H1C O1 H1D 115.1 . . ? C5 N1 C1 116.7(5) . . ? C5 N1 Ni1 123.9(4) . . ? C1 N1 Ni1 119.4(4) . . ? C4 C3 C2 116.7(5) . . ? C4 C3 C6 122.7(6) . . ? C2 C3 C6 120.5(6) . . ? C29 C28 C27 120.2(6) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? N1 C5 C4 123.5(5) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C26 C27 C28 116.5(6) . . ? C26 C27 C30 121.0(6) . . ? C28 C27 C30 122.3(6) . . ? C40 C39 C38 116.2(6) . . ? C40 C39 C42 122.8(6) . . ? C38 C39 C42 120.9(6) . . ? N5 C29 C28 122.5(6) . . ? N5 C29 H29 118.7 . . ? C28 C29 H29 118.7 . . ? C14 C15 C16 119.8(6) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? N3 C18 C17 122.9(5) . . ? N3 C18 H18 118.6 . . ? C17 C18 H18 118.6 . . ? C3 C4 C5 119.2(6) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C1 C2 C3 120.3(6) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? N3 C14 C15 123.1(6) . . ? N3 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C37 C38 C39 121.0(6) . . ? C37 C38 H38 119.5 . . ? C39 C38 H38 119.5 . . ? C41 C40 C39 119.9(6) . . ? C41 C40 H40 120.0 . . ? C39 C40 H40 120.0 . . ? N1 C1 C2 123.7(6) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? N7 C41 C40 123.2(6) . . ? N7 C41 H41 118.4 . . ? C40 C41 H41 118.4 . . ? C27 C26 C25 120.8(6) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? N5 C25 C26 121.8(6) . . ? N5 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C18 C17 C16 119.7(6) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N7 C37 C38 122.2(6) . . ? N7 C37 H37 118.9 . . ? C38 C37 H37 118.9 . . ? C19 N4 C20 112.6(5) . . ? C19 N4 C22 107.1(5) . . ? C20 N4 C22 111.8(5) . . ? C19 N4 H6 107.1 . . ? C20 N4 H6 111.5 . . ? C22 N4 H6 106.5 . . ? C34 N6 C30 112.6(6) . . ? C34 N6 C31 112.8(6) . . ? C30 N6 C31 110.7(6) . . ? C10 N2 C6 112.8(5) . . ? C10 N2 C7 108.2(5) . . ? C6 N2 C7 111.4(5) . . ? N2 C6 C3 114.5(5) . . ? N2 C6 H6A 108.6 . . ? C3 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C3 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C16 C19 N4 113.7(5) . . ? C16 C19 H19A 108.8 . . ? N4 C19 H19A 108.8 . . ? C16 C19 H19B 108.8 . . ? N4 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C15 C16 C17 117.0(6) . . ? C15 C16 C19 120.5(6) . . ? C17 C16 C19 122.4(5) . . ? N6 C30 C27 113.6(5) . . ? N6 C30 H30A 108.8 . . ? C27 C30 H30A 108.8 . . ? N6 C30 H30B 108.8 . . ? C27 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? C39 C42 N8 112.6(6) . . ? C39 C42 H42A 109.1 . . ? N8 C42 H42A 109.1 . . ? C39 C42 H42B 109.1 . . ? N8 C42 H42B 109.1 . . ? H42A C42 H42B 107.8 . . ? C46 N8 C42 114.8(7) . . ? C46 N8 C43 105.6(8) . . ? C42 N8 C43 111.6(6) . . ? C46 N8 H8 108.2 . . ? C42 N8 H8 108.2 . . ? C43 N8 H8 108.2 . . ? O4 C11 C10 107.9(5) . . ? O4 C11 H11A 110.1 . . ? C10 C11 H11A 110.1 . . ? O4 C11 H11B 110.1 . . ? C10 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? N2 C10 C11 113.4(5) . . ? N2 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? N2 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C44 C43 N8 112.7(8) . . ? C44 C43 H43A 109.1 . . ? N8 C43 H43A 109.1 . . ? C44 C43 H43B 109.1 . . ? N8 C43 H43B 109.1 . . ? H43A C43 H43B 107.8 . . ? C32 C31 N6 114.4(7) . . ? C32 C31 H31A 108.7 . . ? N6 C31 H31A 108.7 . . ? C32 C31 H31B 108.7 . . ? N6 C31 H31B 108.7 . . ? H31A C31 H31B 107.6 . . ? H28D O28 H28C 96.1 . . ? C24 O6 C23 112.7(5) . . ? C21 O5 C13 114.3(6) . 2_646 ? C12 O4 C11 113.1(5) . . ? C8 O3 C9 113.1(5) . . ? C44 O9 C45 113.8(8) . . ? C36 O8 C35 111.8(7) . . ? C23 C22 N4 113.5(5) . . ? C23 C22 H22A 108.9 . . ? N4 C22 H22A 108.9 . . ? C23 C22 H22B 108.9 . . ? N4 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C48 O10 C47 117.3(8) . . ? C32 O7 C33 114.5(7) . . ? O3 C8 C7 109.0(5) . . ? O3 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? O3 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O5 C13 C12 111.5(6) 2_656 . ? O5 C13 H13A 109.3 2_656 . ? C12 C13 H13A 109.3 . . ? O5 C13 H13B 109.3 2_656 . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N2 C7 C8 112.7(5) . . ? N2 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C21 C20 N4 112.6(5) . . ? C21 C20 H20A 109.1 . . ? N4 C20 H20A 109.1 . . ? C21 C20 H20B 109.1 . . ? N4 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? O5 C21 C20 109.8(6) . . ? O5 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? O5 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? O6 C23 C22 114.8(5) . . ? O6 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? O6 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.5 . . ? O4 C12 C13 109.4(6) . . ? O4 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? O4 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? O7 C32 C31 110.9(7) . . ? O7 C32 H32A 109.5 . . ? C31 C32 H32A 109.5 . . ? O7 C32 H32B 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 108.0 . . ? N6 C34 C35 113.7(6) . . ? N6 C34 H34A 108.8 . . ? C35 C34 H34A 108.8 . . ? N6 C34 H34B 108.8 . . ? C35 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? O8 C35 C34 107.1(6) . . ? O8 C35 H35A 110.3 . . ? C34 C35 H35A 110.3 . . ? O8 C35 H35B 110.3 . . ? C34 C35 H35B 110.3 . . ? H35A C35 H35B 108.6 . . ? O9 C44 C43 110.2(8) . . ? O9 C44 H44A 109.6 . . ? C43 C44 H44A 109.6 . . ? O9 C44 H44B 109.6 . . ? C43 C44 H44B 109.6 . . ? H44A C44 H44B 108.1 . . ? C47 C46 N8 114.1(10) . . ? C47 C46 H46A 108.7 . . ? N8 C46 H46A 108.7 . . ? C47 C46 H46B 108.7 . . ? N8 C46 H46B 108.7 . . ? H46A C46 H46B 107.6 . . ? C46 C47 O10 114.9(8) . . ? C46 C47 H47A 108.6 . . ? O10 C47 H47A 108.6 . . ? C46 C47 H47B 108.6 . . ? O10 C47 H47B 108.6 . . ? H47A C47 H47B 107.5 . . ? H29D O29 H29C 97.4 . . ? H30C O30 H30D 104.6 . . ? O3 C9 C24 109.6(6) . 2_656 ? O3 C9 H9A 109.8 . . ? C24 C9 H9A 109.8 2_656 . ? O3 C9 H9B 109.8 . . ? C24 C9 H9B 109.8 2_656 . ? H9A C9 H9B 108.2 . . ? O6 C24 C9 109.2(6) . 2_646 ? O6 C24 H24A 109.8 . . ? C9 C24 H24A 109.8 2_646 . ? O6 C24 H24B 109.8 . . ? C9 C24 H24B 109.8 2_646 . ? H24A C24 H24B 108.3 . . ? O7 C33 C48 109.4(7) . 2_756 ? O7 C33 H33A 109.8 . . ? C48 C33 H33A 109.8 2_756 . ? O7 C33 H33B 109.8 . . ? C48 C33 H33B 109.8 2_756 . ? H33A C33 H33B 108.2 . . ? O10 C48 C33 109.7(8) . 2_746 ? O10 C48 H48A 109.7 . . ? C33 C48 H48A 109.7 2_746 . ? O10 C48 H48B 109.7 . . ? C33 C48 H48B 109.7 2_746 . ? H48A C48 H48B 108.2 . . ? O9 C45 C36 108.5(7) . 2_746 ? O9 C45 H45A 110.0 . . ? C36 C45 H45A 110.0 2_746 . ? O9 C45 H45B 110.0 . . ? C36 C45 H45B 110.0 2_746 . ? H45A C45 H45B 108.4 . . ? O8 C36 C45 108.6(8) . 2_756 ? O8 C36 H36A 110.0 . . ? C45 C36 H36A 110.0 2_756 . ? O8 C36 H36B 110.0 . . ? C45 C36 H36B 110.0 2_756 . ? H36A C36 H36B 108.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 O30 0.93 1.81 2.723(8) 167.7 . N4 H6 O28 1.06 1.67 2.702(7) 162.4 . O1 H1D O20 0.92 2.22 2.939(12) 134.3 . O1 H1C O29 0.86 1.89 2.660(7) 149.3 . O29 H29C O27 1.12 1.64 2.745(9) 166.2 . O2 H2D O11 1.09 1.93 2.792(6) 133.9 . O2 H2C O15 0.92 1.86 2.739(7) 158.0 . O28 H28C O3 0.87 2.02 2.840(6) 156.1 2_646 O28 H28D O4 0.82 1.98 2.797(6) 171.6 2_646 O30 H30D O7 1.00 1.83 2.791(7) 159.7 2_746 O30 H30C O8 1.04 1.73 2.747(7) 167.9 2_746 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.705 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 898009' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H76 N8 O10 Zn, 4(Cl O4), O, 3(H2 O)' _chemical_formula_sum 'C48 H82 Cl4 N8 O30 Zn' _chemical_formula_weight 1458.39 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' Cl Cl 0.1484 0.1585 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.7217(5) _cell_length_b 14.2395(5) _cell_length_c 25.8471(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.9290(10) _cell_angle_gamma 90.00 _cell_volume 6487.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 55355 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 29.01 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3056 _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7417 _exptl_absorpt_correction_T_max 0.7851 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 Apex KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55355 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 29.01 _reflns_number_total 17125 _reflns_number_gt 14571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_cell_refinement 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_data_reduction 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0204P)^2^+19.7363P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 17125 _refine_ls_number_parameters 868 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.1534 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 0.25080(2) 0.11192(3) 0.240226(15) 0.01517(9) Uani 1 1 d . . . Cl1 Cl -0.20474(6) 0.14220(7) 0.56504(4) 0.0305(2) Uani 1 1 d . . . O1 O 0.25065(16) -0.03730(19) 0.23705(11) 0.0249(6) Uani 1 1 d D . . N1 N 0.33345(15) 0.1099(2) 0.18399(11) 0.0172(6) Uani 1 1 d . . . C1 C 0.33342(18) 0.1681(2) 0.14317(12) 0.0167(7) Uani 1 1 d . . . H1 H 0.2942 0.2137 0.1382 0.020 Uiso 1 1 calc R . . Cl2 Cl 0.32812(5) 0.42918(6) 0.34686(4) 0.02370(19) Uani 1 1 d . . . O2 O 0.25746(15) 0.26285(18) 0.24054(10) 0.0223(5) Uani 1 1 d D . . N2 N 0.53260(16) 0.1732(2) 0.05655(11) 0.0178(6) Uani 1 1 d . . . C2 C 0.38688(19) 0.1657(2) 0.10787(13) 0.0186(7) Uani 1 1 d . . . H2 H 0.3846 0.2096 0.0801 0.022 Uiso 1 1 calc R . . Cl3 Cl 0.16778(5) 0.44380(6) 0.16388(3) 0.02329(18) Uani 1 1 d . . . O3 O 0.43178(14) 0.27141(18) -0.02136(10) 0.0236(6) Uani 1 1 d . . . N3 N 0.34484(15) 0.1127(2) 0.30095(11) 0.0170(6) Uani 1 1 d . . . C3 C 0.44397(19) 0.0984(2) 0.11349(13) 0.0171(7) Uani 1 1 d . . . Cl4 Cl 0.32017(5) -0.18496(7) 0.13149(4) 0.0297(2) Uani 1 1 d . . . O4 O 0.55829(15) 0.2813(2) 0.15096(10) 0.0262(6) Uani 1 1 d . . . N4 N 0.59805(16) 0.0281(2) 0.40696(11) 0.0176(6) Uani 1 1 d . . . C4 C 0.4452(2) 0.0387(3) 0.15627(16) 0.0282(9) Uani 1 1 d . . . H4 H 0.4839 -0.0074 0.1622 0.034 Uiso 1 1 calc R . . N5 N 0.17308(15) 0.1073(2) 0.29890(11) 0.0175(6) Uani 1 1 d . . . C5 C 0.3901(2) 0.0469(3) 0.18994(16) 0.0265(8) Uani 1 1 d . . . H5 H 0.3923 0.0057 0.2190 0.032 Uiso 1 1 calc R . . O6 O 0.68050(14) -0.12687(18) 0.47444(9) 0.0217(5) Uani 1 1 d . . . N6 N 0.00400(17) 0.1721(2) 0.44422(12) 0.0232(6) Uani 1 1 d . . . C6 C 0.5005(2) 0.0854(3) 0.07423(14) 0.0220(7) Uani 1 1 d . . . H6A H 0.5425 0.0452 0.0898 0.026 Uiso 1 1 calc R . . H6B H 0.4753 0.0518 0.0436 0.026 Uiso 1 1 calc R . . O7 O -0.03311(16) 0.2881(2) 0.35590(11) 0.0330(7) Uani 1 1 d . . . N7 N 0.15505(16) 0.1210(2) 0.18147(11) 0.0199(6) Uani 1 1 d . . . C7 C 0.5384(2) 0.1726(3) 0.00043(14) 0.0222(7) Uani 1 1 d . . . H7A H 0.5626 0.1131 -0.0090 0.027 Uiso 1 1 calc R . . H7B H 0.5716 0.2249 -0.0083 0.027 Uiso 1 1 calc R . . O8 O -0.03874(17) -0.0534(2) 0.18139(12) 0.0359(7) Uani 1 1 d . . . N8 N -0.10884(18) 0.0588(2) 0.09218(14) 0.0283(7) Uani 1 1 d . . . C8 C 0.4629(2) 0.1820(3) -0.03130(14) 0.0274(8) Uani 1 1 d . . . H8A H 0.4693 0.1758 -0.0688 0.033 Uiso 1 1 calc R . . H8B H 0.4283 0.1317 -0.0218 0.033 Uiso 1 1 calc R . . O9 O -0.16053(17) -0.0326(2) -0.01209(11) 0.0357(7) Uani 1 1 d . . . C9 C 0.3554(2) 0.2813(3) -0.04463(14) 0.0262(8) Uani 1 1 d . . . H9A H 0.3236 0.2299 -0.0329 0.031 Uiso 1 1 calc R . . H9B H 0.3540 0.2779 -0.0830 0.031 Uiso 1 1 calc R . . O10 O -0.12036(18) -0.2245(2) -0.00619(11) 0.0364(7) Uani 1 1 d . . . C10 C 0.6081(2) 0.1928(3) 0.08389(14) 0.0236(8) Uani 1 1 d . . . H10A H 0.6284 0.2506 0.0691 0.028 Uiso 1 1 calc R . . H10B H 0.6426 0.1405 0.0774 0.028 Uiso 1 1 calc R . . O11 O -0.1672(3) 0.1985(3) 0.60548(14) 0.0747(15) Uani 1 1 d . . . C11 C 0.6080(2) 0.2053(3) 0.14134(15) 0.0273(8) Uani 1 1 d . . . H11A H 0.5906 0.1468 0.1571 0.033 Uiso 1 1 calc R . . H11B H 0.6600 0.2192 0.1572 0.033 Uiso 1 1 calc R . . O12 O -0.2662(2) 0.0930(3) 0.58382(17) 0.0694(13) Uani 1 1 d . . . C12 C 0.5583(3) 0.3058(4) 0.20365(16) 0.0478(14) Uani 1 1 d . . . H12A H 0.6000 0.3508 0.2133 0.057 Uiso 1 1 calc R . . H12B H 0.5678 0.2490 0.2254 0.057 Uiso 1 1 calc R . . O13 O -0.2320(2) 0.2020(3) 0.52295(14) 0.0593(11) Uani 1 1 d . . . C13 C 0.39909(19) 0.1784(3) 0.30202(14) 0.0193(7) Uani 1 1 d . . . H13 H 0.3933 0.2280 0.2774 0.023 Uiso 1 1 calc R . . O14 O -0.1544(2) 0.0762(3) 0.54635(18) 0.0745(13) Uani 1 1 d . . . C14 C 0.46325(19) 0.1771(3) 0.33749(14) 0.0211(7) Uani 1 1 d . . . H14 H 0.5003 0.2252 0.3371 0.025 Uiso 1 1 calc R . . O15 O 0.33241(18) 0.4451(2) 0.40231(11) 0.0388(7) Uani 1 1 d . . . C15 C 0.47302(19) 0.1048(3) 0.37359(13) 0.0190(7) Uani 1 1 d . . . O16 O 0.2989(2) 0.5119(2) 0.32149(14) 0.0521(10) Uani 1 1 d . . . C16 C 0.41652(19) 0.0367(2) 0.37292(13) 0.0194(7) Uani 1 1 d . . . H16 H 0.4210 -0.0137 0.3971 0.023 Uiso 1 1 calc R . . O17 O 0.40094(18) 0.4047(3) 0.33291(15) 0.0500(9) Uani 1 1 d . . . C17 C 0.35379(19) 0.0434(2) 0.33652(13) 0.0179(7) Uani 1 1 d . . . H17 H 0.3153 -0.0030 0.3366 0.022 Uiso 1 1 calc R . . O18 O 0.27654(16) 0.3518(2) 0.33472(11) 0.0315(7) Uani 1 1 d . . . C18 C 0.54082(19) 0.1042(3) 0.41405(14) 0.0218(7) Uani 1 1 d . . . H18A H 0.5665 0.1659 0.4135 0.026 Uiso 1 1 calc R . . H18B H 0.5227 0.0967 0.4488 0.026 Uiso 1 1 calc R . . O19 O 0.2044(2) 0.4760(3) 0.21322(14) 0.0625(11) Uani 1 1 d . . . C19 C 0.6274(2) 0.0300(3) 0.35441(13) 0.0253(8) Uani 1 1 d . . . H19A H 0.6047 0.0842 0.3345 0.030 Uiso 1 1 calc R . . H19B H 0.6831 0.0396 0.3592 0.030 Uiso 1 1 calc R . . O20 O 0.09217(17) 0.4172(3) 0.16935(17) 0.0552(10) Uani 1 1 d . . . O21 O 0.21021(15) 0.36246(19) 0.14957(10) 0.0258(6) Uani 1 1 d . . . C21 C 0.5118(3) -0.1530(3) 0.28595(15) 0.0373(10) Uani 1 1 d . . . H21A H 0.5517 -0.2019 0.2901 0.045 Uiso 1 1 calc R . . H21B H 0.5072 -0.1325 0.2492 0.045 Uiso 1 1 calc R . . O22 O 0.17121(19) 0.5153(2) 0.12590(14) 0.0466(9) Uani 1 1 d . . . C22 C 0.6612(2) 0.0394(3) 0.45042(14) 0.0214(7) Uani 1 1 d . . . H22A H 0.6909 0.0962 0.4438 0.026 Uiso 1 1 calc R . . H22B H 0.6387 0.0490 0.4835 0.026 Uiso 1 1 calc R . . O23 O 0.2670(2) -0.1128(3) 0.1290(2) 0.0964(19) Uani 1 1 d . . . C23 C 0.7140(2) -0.0435(3) 0.45626(15) 0.0240(8) Uani 1 1 d . . . H23A H 0.7325 -0.0568 0.4222 0.029 Uiso 1 1 calc R . . H23B H 0.7585 -0.0267 0.4808 0.029 Uiso 1 1 calc R . . O24 O 0.3597(4) -0.1794(4) 0.1807(2) 0.129(3) Uani 1 1 d . . . C24 C 0.6746(2) -0.1253(3) 0.52885(13) 0.0258(8) Uani 1 1 d . . . H24A H 0.6398 -0.0745 0.5373 0.031 Uiso 1 1 calc R . . H24B H 0.7250 -0.1135 0.5480 0.031 Uiso 1 1 calc R . . O25 O 0.2839(2) -0.2736(3) 0.1250(2) 0.0853(16) Uani 1 1 d . . . C25 C 0.1147(2) 0.0466(3) 0.29529(15) 0.0274(8) Uani 1 1 d . . . H25 H 0.1068 0.0077 0.2654 0.033 Uiso 1 1 calc R . . O26 O 0.3728(4) -0.1756(4) 0.0974(3) 0.136(3) Uani 1 1 d . . . C26 C 0.0658(2) 0.0386(3) 0.33338(16) 0.0299(9) Uani 1 1 d . . . H26 H 0.0260 -0.0063 0.3296 0.036 Uiso 1 1 calc R . . O27 O 0.2506(3) 0.6737(3) 0.24145(16) 0.0775(14) Uani 1 1 d . . . C27 C 0.07459(19) 0.0954(3) 0.37695(14) 0.0203(7) Uani 1 1 d . . . O28 O 0.1898(2) -0.1739(3) 0.28891(13) 0.0481(9) Uani 1 1 d D . . C28 C 0.13331(19) 0.1601(2) 0.37982(13) 0.0188(7) Uani 1 1 d . . . H28 H 0.1405 0.2024 0.4084 0.023 Uiso 1 1 calc R . . C29 C 0.18123(18) 0.1630(2) 0.34112(13) 0.0171(7) Uani 1 1 d . . . H29 H 0.2221 0.2064 0.3444 0.020 Uiso 1 1 calc R . . C30 C 0.0252(2) 0.0830(3) 0.42077(15) 0.0251(8) Uani 1 1 d . . . H30A H -0.0216 0.0492 0.4073 0.030 Uiso 1 1 calc R . . H30B H 0.0525 0.0434 0.4481 0.030 Uiso 1 1 calc R . . C31 C 0.0163(3) 0.1695(3) 0.50134(15) 0.0338(10) Uani 1 1 d . . . H31A H -0.0004 0.1078 0.5136 0.041 Uiso 1 1 calc R . . H31B H -0.0152 0.2185 0.5157 0.041 Uiso 1 1 calc R . . C32 C -0.0739(2) 0.2004(3) 0.42611(17) 0.0317(9) Uani 1 1 d . . . H32A H -0.0864 0.2584 0.4446 0.038 Uiso 1 1 calc R . . H32B H -0.1092 0.1506 0.4352 0.038 Uiso 1 1 calc R . . C33 C -0.0856(2) 0.2177(3) 0.36867(18) 0.0343(10) Uani 1 1 d . . . H33A H -0.0772 0.1589 0.3496 0.041 Uiso 1 1 calc R . . H33B H -0.1383 0.2390 0.3586 0.041 Uiso 1 1 calc R . . C34 C -0.0425(3) 0.3145(4) 0.30293(18) 0.0465(13) Uani 1 1 d . . . H34A H -0.0860 0.3580 0.2965 0.056 Uiso 1 1 calc R . . H34B H -0.0527 0.2583 0.2808 0.056 Uiso 1 1 calc R . . C35 C 0.1045(2) 0.1911(3) 0.18233(15) 0.0248(8) Uani 1 1 d . . . H35 H 0.1144 0.2393 0.2075 0.030 Uiso 1 1 calc R . . C36 C 0.0391(2) 0.1969(3) 0.14862(15) 0.0247(8) Uani 1 1 d . . . H36 H 0.0060 0.2492 0.1500 0.030 Uiso 1 1 calc R . . C37 C 0.0220(2) 0.1256(3) 0.11277(14) 0.0223(7) Uani 1 1 d . . . C38 C 0.0739(2) 0.0528(3) 0.11121(15) 0.0234(8) Uani 1 1 d . . . H38 H 0.0646 0.0030 0.0869 0.028 Uiso 1 1 calc R . . C39 C 0.1392(2) 0.0535(3) 0.14532(14) 0.0219(7) Uani 1 1 d . . . H39 H 0.1747 0.0040 0.1433 0.026 Uiso 1 1 calc R . . C40 C -0.0503(2) 0.1286(3) 0.07624(14) 0.0236(8) Uani 1 1 d . . . H40A H -0.0385 0.1139 0.0405 0.028 Uiso 1 1 calc R . . H40B H -0.0719 0.1927 0.0761 0.028 Uiso 1 1 calc R . . C41 C -0.1225(2) 0.0673(3) 0.14921(18) 0.0354(10) Uani 1 1 d . . . H41A H -0.0856 0.1122 0.1666 0.043 Uiso 1 1 calc R . . H41B H -0.1741 0.0927 0.1516 0.043 Uiso 1 1 calc R . . C42 C -0.1150(3) -0.0246(4) 0.17671(19) 0.0416(11) Uani 1 1 d . . . H42A H -0.1326 -0.0185 0.2117 0.050 Uiso 1 1 calc R . . H42B H -0.1470 -0.0722 0.1570 0.050 Uiso 1 1 calc R . . C43 C -0.0280(3) -0.1389(4) 0.20988(17) 0.0431(12) Uani 1 1 d . . . H43A H -0.0719 -0.1810 0.2010 0.052 Uiso 1 1 calc R . . H43B H -0.0245 -0.1256 0.2476 0.052 Uiso 1 1 calc R . . C44 C -0.1839(2) 0.0708(3) 0.06038(18) 0.0363(10) Uani 1 1 d . . . H44A H -0.2200 0.0248 0.0726 0.044 Uiso 1 1 calc R . . H44B H -0.2035 0.1343 0.0671 0.044 Uiso 1 1 calc R . . C45 C -0.1832(3) 0.0594(3) 0.00383(19) 0.0390(11) Uani 1 1 d . . . H45A H -0.2347 0.0729 -0.0133 0.047 Uiso 1 1 calc R . . H45B H -0.1482 0.1065 -0.0087 0.047 Uiso 1 1 calc R . . C46 C -0.2150(2) -0.1035(3) -0.00869(19) 0.0408(11) Uani 1 1 d . . . H46A H -0.2644 -0.0830 -0.0265 0.049 Uiso 1 1 calc R . . H46B H -0.2216 -0.1159 0.0283 0.049 Uiso 1 1 calc R . . C47 C -0.1890(2) -0.1925(3) -0.03401(15) 0.0346(10) Uani 1 1 d . . . H47A H -0.2286 -0.2416 -0.0337 0.042 Uiso 1 1 calc R . . H47B H -0.1808 -0.1796 -0.0706 0.042 Uiso 1 1 calc R . . C48 C -0.0980(3) -0.3151(3) -0.02169(16) 0.0380(11) Uani 1 1 d . . . H48A H -0.1040 -0.3199 -0.0601 0.046 Uiso 1 1 calc R . . H48B H -0.1303 -0.3636 -0.0076 0.046 Uiso 1 1 calc R . . O29 O 0.51259(15) -0.11873(19) 0.43448(10) 0.0220(5) Uani 1 1 d D . . O30 O -0.04443(18) -0.1052(2) 0.06693(13) 0.0383(8) Uani 1 1 d D . . H8N H -0.090(3) 0.003(4) 0.0842(19) 0.047(15) Uiso 1 1 d . . . O5 O 0.53556(17) -0.0772(2) 0.31686(11) 0.0378(8) Uani 1 1 d . . . C20 C 0.6109(3) -0.0557(4) 0.32418(19) 0.0455(12) Uani 1 1 d . . . H20A H 0.6301 -0.0484 0.2898 0.055 Uiso 1 1 calc R . . H20B H 0.6384 -0.1088 0.3422 0.055 Uiso 1 1 calc R . . H29A H 0.534(2) -0.161(3) 0.4567(15) 0.039(13) Uiso 1 1 d D . . H29B H 0.497(3) -0.149(3) 0.4059(14) 0.060(17) Uiso 1 1 d D . . H30C H -0.024(3) -0.140(4) 0.0927(17) 0.07(2) Uiso 1 1 d D . . H30D H -0.064(3) -0.143(3) 0.0418(16) 0.058(17) Uiso 1 1 d D . . H1B H 0.232(2) -0.079(3) 0.2576(14) 0.029(12) Uiso 1 1 d D . . H28B H 0.191(4) -0.173(5) 0.3232(8) 0.08(2) Uiso 1 1 d D . . H28A H 0.212(3) -0.226(3) 0.278(2) 0.08(2) Uiso 1 1 d D . . H1A H 0.270(3) -0.070(3) 0.2129(15) 0.049(15) Uiso 1 1 d D . . H4N H 0.575(2) -0.024(3) 0.4126(13) 0.007(9) Uiso 1 1 d . . . H2A H 0.265(3) 0.297(3) 0.2685(12) 0.039(13) Uiso 1 1 d D . . H2B H 0.242(3) 0.296(3) 0.2129(12) 0.041(14) Uiso 1 1 d 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 0.01301(17) 0.01418(19) 0.01876(18) -0.00081(15) 0.00373(14) -0.00033(15) Cl1 0.0322(5) 0.0270(5) 0.0331(5) 0.0006(4) 0.0074(4) -0.0053(4) O1 0.0327(14) 0.0137(13) 0.0307(14) -0.0039(11) 0.0144(12) -0.0013(11) N1 0.0147(13) 0.0157(14) 0.0215(14) -0.0014(12) 0.0031(11) -0.0013(11) C1 0.0132(14) 0.0187(17) 0.0175(15) -0.0019(13) -0.0013(12) 0.0029(13) Cl2 0.0213(4) 0.0182(4) 0.0307(4) -0.0041(4) -0.0016(3) -0.0051(3) O2 0.0297(14) 0.0154(13) 0.0205(12) -0.0001(10) -0.0033(11) 0.0011(11) N2 0.0161(13) 0.0182(15) 0.0200(13) -0.0020(12) 0.0054(11) -0.0002(11) C2 0.0201(16) 0.0176(17) 0.0179(15) 0.0021(13) 0.0002(13) -0.0013(13) Cl3 0.0233(4) 0.0215(4) 0.0264(4) 0.0027(3) 0.0088(3) 0.0065(3) O3 0.0261(13) 0.0213(14) 0.0225(12) -0.0067(11) -0.0020(10) 0.0039(11) N3 0.0159(13) 0.0153(14) 0.0203(13) 0.0027(11) 0.0048(11) 0.0003(11) C3 0.0165(15) 0.0133(16) 0.0223(16) -0.0014(13) 0.0055(13) -0.0003(12) Cl4 0.0294(5) 0.0336(5) 0.0267(4) -0.0068(4) 0.0057(4) 0.0107(4) O4 0.0295(14) 0.0280(15) 0.0203(12) -0.0032(11) -0.0008(11) 0.0099(12) N4 0.0141(13) 0.0181(15) 0.0202(14) 0.0024(12) -0.0003(11) -0.0046(11) C4 0.0251(19) 0.022(2) 0.040(2) 0.0108(17) 0.0140(17) 0.0118(15) N5 0.0151(13) 0.0162(14) 0.0218(14) -0.0031(12) 0.0047(11) -0.0013(11) C5 0.0260(19) 0.0210(19) 0.035(2) 0.0131(16) 0.0165(16) 0.0072(15) O6 0.0234(12) 0.0234(14) 0.0183(11) 0.0018(10) 0.0021(10) 0.0013(10) N6 0.0244(15) 0.0172(16) 0.0296(16) -0.0039(13) 0.0110(13) 0.0007(12) C6 0.0230(17) 0.0162(18) 0.0285(18) 0.0020(14) 0.0113(15) 0.0012(14) O7 0.0360(16) 0.0298(16) 0.0307(14) 0.0014(12) -0.0086(12) -0.0041(13) N7 0.0165(13) 0.0186(15) 0.0250(14) -0.0038(12) 0.0040(11) -0.0006(12) C7 0.0276(18) 0.0175(18) 0.0233(17) -0.0031(14) 0.0113(15) 0.0020(14) O8 0.0383(17) 0.0334(17) 0.0377(16) -0.0012(14) 0.0115(13) -0.0072(14) N8 0.0200(15) 0.0198(17) 0.044(2) -0.0009(15) -0.0021(14) -0.0004(13) C8 0.038(2) 0.024(2) 0.0201(17) -0.0059(15) 0.0002(16) 0.0027(17) O9 0.0356(16) 0.0372(18) 0.0333(15) 0.0024(13) -0.0015(13) -0.0052(14) C9 0.0269(19) 0.029(2) 0.0217(17) -0.0053(16) -0.0022(15) -0.0016(16) O10 0.0508(19) 0.0262(16) 0.0282(14) -0.0032(12) -0.0151(13) -0.0034(14) C10 0.0168(16) 0.024(2) 0.0309(19) -0.0032(16) 0.0060(14) 0.0040(14) O11 0.115(4) 0.070(3) 0.0361(19) 0.0075(19) -0.007(2) -0.059(3) C11 0.0230(18) 0.029(2) 0.0289(19) -0.0001(16) -0.0026(15) 0.0114(16) O12 0.070(3) 0.065(3) 0.079(3) -0.010(2) 0.036(2) -0.040(2) C12 0.063(3) 0.057(3) 0.0210(19) -0.003(2) -0.007(2) 0.033(3) O13 0.086(3) 0.046(2) 0.0425(19) 0.0077(17) -0.0088(19) 0.007(2) C13 0.0162(15) 0.0176(17) 0.0249(17) 0.0037(14) 0.0058(13) 0.0004(13) O14 0.053(2) 0.079(3) 0.093(3) -0.002(3) 0.015(2) 0.034(2) C14 0.0162(16) 0.0195(18) 0.0272(17) 0.0030(15) 0.0007(14) -0.0025(13) O15 0.0427(18) 0.0384(18) 0.0336(16) -0.0123(14) -0.0033(14) -0.0022(14) C15 0.0160(15) 0.0185(17) 0.0225(16) -0.0001(14) 0.0013(13) 0.0025(13) O16 0.058(2) 0.0328(19) 0.060(2) 0.0213(17) -0.0190(18) -0.0128(16) C16 0.0208(16) 0.0157(17) 0.0216(16) 0.0044(13) 0.0022(14) 0.0013(13) O17 0.0337(17) 0.049(2) 0.072(2) -0.0246(19) 0.0264(17) -0.0122(15) C17 0.0167(15) 0.0147(16) 0.0226(16) 0.0009(13) 0.0033(13) -0.0030(13) O18 0.0349(15) 0.0223(15) 0.0378(15) -0.0086(12) 0.0069(13) -0.0167(12) C18 0.0189(16) 0.0189(18) 0.0262(17) 0.0015(15) -0.0046(14) -0.0012(14) O19 0.084(3) 0.061(3) 0.042(2) -0.0211(19) 0.0029(19) 0.006(2) C19 0.0252(18) 0.033(2) 0.0177(16) 0.0045(15) 0.0030(14) -0.0067(16) O20 0.0227(15) 0.041(2) 0.105(3) 0.017(2) 0.0245(18) 0.0101(14) O21 0.0255(13) 0.0230(14) 0.0298(13) 0.0044(11) 0.0067(11) 0.0105(11) C21 0.051(3) 0.041(3) 0.0212(18) -0.0122(18) 0.0092(18) -0.012(2) O22 0.049(2) 0.0347(19) 0.060(2) 0.0230(16) 0.0268(17) 0.0219(15) C22 0.0189(16) 0.0216(18) 0.0226(17) 0.0018(14) -0.0036(14) -0.0046(14) O23 0.057(3) 0.050(3) 0.175(5) -0.041(3) -0.021(3) 0.036(2) C23 0.0175(16) 0.029(2) 0.0251(17) 0.0049(15) 0.0016(14) -0.0004(15) O24 0.206(7) 0.098(4) 0.066(3) 0.020(3) -0.067(4) -0.037(4) C24 0.0303(19) 0.029(2) 0.0172(16) 0.0036(15) -0.0021(14) -0.0041(16) O25 0.056(3) 0.042(2) 0.155(5) -0.043(3) -0.001(3) 0.002(2) C25 0.0238(18) 0.027(2) 0.032(2) -0.0138(17) 0.0084(16) -0.0089(16) O26 0.209(7) 0.066(4) 0.165(6) 0.016(4) 0.165(5) 0.027(4) C26 0.0221(18) 0.028(2) 0.042(2) -0.0141(18) 0.0159(17) -0.0108(16) O27 0.138(4) 0.040(2) 0.053(2) -0.0040(19) 0.003(3) 0.001(3) C27 0.0177(16) 0.0164(18) 0.0277(18) -0.0020(14) 0.0068(14) 0.0020(13) O28 0.079(3) 0.035(2) 0.0306(17) 0.0092(15) 0.0057(18) -0.0114(19) C28 0.0196(16) 0.0151(17) 0.0222(16) -0.0038(13) 0.0048(13) -0.0009(13) C29 0.0151(15) 0.0158(17) 0.0203(15) -0.0021(13) 0.0012(13) -0.0027(13) C30 0.0299(19) 0.0147(18) 0.034(2) -0.0024(15) 0.0182(16) -0.0027(15) C31 0.057(3) 0.022(2) 0.0279(19) 0.0011(16) 0.027(2) 0.0032(19) C32 0.0207(18) 0.027(2) 0.049(2) -0.0106(19) 0.0126(17) -0.0046(16) C33 0.0187(18) 0.033(2) 0.050(3) -0.010(2) -0.0023(18) -0.0053(17) C34 0.063(3) 0.034(3) 0.038(2) -0.003(2) -0.018(2) 0.002(2) C35 0.0236(18) 0.0193(19) 0.0312(19) -0.0071(15) 0.0019(15) -0.0015(15) C36 0.0178(16) 0.0201(19) 0.036(2) -0.0038(16) 0.0003(15) 0.0006(14) C37 0.0185(16) 0.0210(19) 0.0274(18) 0.0044(15) 0.0020(14) -0.0035(14) C38 0.0212(17) 0.0206(19) 0.0284(18) -0.0083(15) 0.0030(15) -0.0039(14) C39 0.0189(16) 0.0173(18) 0.0303(18) -0.0047(15) 0.0069(14) -0.0011(14) C40 0.0233(18) 0.0204(19) 0.0258(18) 0.0002(15) -0.0033(15) -0.0027(14) C41 0.032(2) 0.031(2) 0.047(3) -0.005(2) 0.0176(19) -0.0021(18) C42 0.037(2) 0.045(3) 0.045(3) 0.001(2) 0.014(2) -0.008(2) C43 0.063(3) 0.042(3) 0.024(2) 0.0000(19) 0.006(2) -0.011(2) C44 0.024(2) 0.026(2) 0.057(3) 0.000(2) -0.0036(19) 0.0004(17) C45 0.034(2) 0.029(2) 0.051(3) 0.009(2) -0.004(2) 0.0038(19) C46 0.029(2) 0.041(3) 0.050(3) 0.004(2) -0.005(2) -0.009(2) C47 0.034(2) 0.044(3) 0.0229(18) 0.0057(18) -0.0074(17) -0.015(2) C48 0.061(3) 0.028(2) 0.0247(19) -0.0051(17) 0.001(2) -0.009(2) O29 0.0244(13) 0.0176(13) 0.0228(12) 0.0046(11) -0.0027(11) -0.0008(11) O30 0.0424(18) 0.0227(16) 0.0443(18) -0.0089(14) -0.0219(15) 0.0046(13) O5 0.0409(17) 0.048(2) 0.0249(14) -0.0095(13) 0.0063(13) -0.0212(15) C20 0.033(2) 0.063(4) 0.043(3) -0.018(2) 0.016(2) -0.010(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 O1 2.126(3) . ? Zn1 O2 2.152(3) . ? Zn1 N5 2.152(3) . ? Zn1 N7 2.161(3) . ? Zn1 N1 2.167(3) . ? Zn1 N3 2.168(3) . ? Cl1 O14 1.415(4) . ? Cl1 O12 1.422(4) . ? Cl1 O11 1.426(4) . ? Cl1 O13 1.426(4) . ? O1 H1B 0.880(19) . ? O1 H1A 0.873(19) . ? N1 C1 1.341(4) . ? N1 C5 1.343(5) . ? C1 C2 1.382(5) . ? C1 H1 0.9500 . ? Cl2 O17 1.419(3) . ? Cl2 O16 1.420(3) . ? Cl2 O15 1.445(3) . ? Cl2 O18 1.446(3) . ? O2 H2A 0.875(19) . ? O2 H2B 0.877(19) . ? N2 C7 1.465(4) . ? N2 C6 1.466(5) . ? N2 C10 1.473(4) . ? C2 C3 1.390(5) . ? C2 H2 0.9500 . ? Cl3 O20 1.414(3) . ? Cl3 O22 1.419(3) . ? Cl3 O19 1.444(4) . ? Cl3 O21 1.449(3) . ? O3 C8 1.422(5) . ? O3 C9 1.430(4) . ? N3 C13 1.339(4) . ? N3 C17 1.347(4) . ? C3 C4 1.393(5) . ? C3 C6 1.509(5) . ? Cl4 O26 1.354(4) . ? Cl4 O24 1.389(4) . ? Cl4 O23 1.390(4) . ? Cl4 O25 1.419(4) . ? O4 C12 1.406(5) . ? O4 C11 1.433(4) . ? N4 C19 1.504(5) . ? N4 C18 1.508(5) . ? N4 C22 1.510(4) . ? N4 H4N 0.86(4) . ? C4 C5 1.379(5) . ? C4 H4 0.9500 . ? N5 C25 1.343(5) . ? N5 C29 1.345(4) . ? C5 H5 0.9500 . ? O6 C24 1.421(4) . ? O6 C23 1.428(5) . ? N6 C32 1.467(5) . ? N6 C31 1.470(5) . ? N6 C30 1.471(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? O7 C34 1.413(5) . ? O7 C33 1.430(5) . ? N7 C35 1.342(5) . ? N7 C39 1.350(4) . ? C7 C8 1.502(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? O8 C42 1.406(5) . ? O8 C43 1.425(6) . ? N8 C44 1.500(5) . ? N8 C41 1.523(6) . ? N8 C40 1.523(5) . ? N8 H8N 0.89(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O9 C46 1.406(5) . ? O9 C45 1.443(5) . ? C9 C24 1.504(5) 2_655 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? O10 C48 1.420(5) . ? O10 C47 1.423(5) . ? C10 C11 1.496(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C21 1.424(6) 2_655 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.385(5) . ? C13 H13 0.9500 . ? C14 C15 1.388(5) . ? C14 H14 0.9500 . ? C15 C16 1.393(5) . ? C15 C18 1.509(4) . ? C16 C17 1.384(5) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.463(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C21 O5 1.382(5) . ? C21 C12 1.424(6) 2_645 ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.504(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C9 1.504(5) 2_645 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.382(5) . ? C25 H25 0.9500 . ? C26 C27 1.383(5) . ? C26 H26 0.9500 . ? C27 C28 1.386(5) . ? C27 C30 1.512(5) . ? O28 H28B 0.88(2) . ? O28 H28A 0.89(2) . ? C28 C29 1.378(5) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C48 1.504(7) 2 ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.498(6) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C43 1.482(7) 2 ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.380(5) . ? C35 H35 0.9500 . ? C36 C37 1.386(5) . ? C36 H36 0.9500 . ? C37 C38 1.390(5) . ? C37 C40 1.512(5) . ? C38 C39 1.380(5) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.488(6) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C34 1.482(7) 2_545 ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 C45 1.472(7) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C47 1.519(7) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C31 1.504(7) 2_545 ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? O29 H29A 0.883(19) . ? O29 H29B 0.880(19) . ? O30 H30C 0.88(2) . ? O30 H30D 0.880(19) . ? O5 C20 1.363(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? 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 O1 Zn1 O2 176.17(11) . . ? O1 Zn1 N5 89.89(11) . . ? O2 Zn1 N5 93.84(11) . . ? O1 Zn1 N7 92.00(11) . . ? O2 Zn1 N7 88.94(11) . . ? N5 Zn1 N7 89.07(11) . . ? O1 Zn1 N1 87.67(11) . . ? O2 Zn1 N1 88.57(11) . . ? N5 Zn1 N1 176.33(11) . . ? N7 Zn1 N1 93.76(11) . . ? O1 Zn1 N3 91.77(11) . . ? O2 Zn1 N3 87.39(10) . . ? N5 Zn1 N3 89.43(10) . . ? N7 Zn1 N3 175.94(11) . . ? N1 Zn1 N3 87.90(10) . . ? O14 Cl1 O12 108.8(3) . . ? O14 Cl1 O11 111.1(3) . . ? O12 Cl1 O11 110.0(2) . . ? O14 Cl1 O13 108.2(3) . . ? O12 Cl1 O13 110.1(3) . . ? O11 Cl1 O13 108.6(2) . . ? Zn1 O1 H1B 130(3) . . ? Zn1 O1 H1A 124(4) . . ? H1B O1 H1A 106(4) . . ? C1 N1 C5 116.2(3) . . ? C1 N1 Zn1 125.0(2) . . ? C5 N1 Zn1 118.7(2) . . ? N1 C1 C2 124.0(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? O17 Cl2 O16 112.6(2) . . ? O17 Cl2 O15 109.5(2) . . ? O16 Cl2 O15 107.9(2) . . ? O17 Cl2 O18 109.21(19) . . ? O16 Cl2 O18 109.90(19) . . ? O15 Cl2 O18 107.59(18) . . ? Zn1 O2 H2A 125(3) . . ? Zn1 O2 H2B 121(3) . . ? H2A O2 H2B 112(4) . . ? C7 N2 C6 111.9(3) . . ? C7 N2 C10 108.8(3) . . ? C6 N2 C10 112.0(3) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? O20 Cl3 O22 111.7(2) . . ? O20 Cl3 O19 109.9(3) . . ? O22 Cl3 O19 109.6(2) . . ? O20 Cl3 O21 109.48(19) . . ? O22 Cl3 O21 109.63(18) . . ? O19 Cl3 O21 106.3(2) . . ? C8 O3 C9 112.3(3) . . ? C13 N3 C17 117.6(3) . . ? C13 N3 Zn1 121.0(2) . . ? C17 N3 Zn1 121.2(2) . . ? C2 C3 C4 117.1(3) . . ? C2 C3 C6 122.8(3) . . ? C4 C3 C6 120.1(3) . . ? O26 Cl4 O24 105.8(5) . . ? O26 Cl4 O23 113.9(4) . . ? O24 Cl4 O23 106.0(4) . . ? O26 Cl4 O25 110.2(3) . . ? O24 Cl4 O25 109.8(3) . . ? O23 Cl4 O25 110.8(3) . . ? C12 O4 C11 114.7(3) . . ? C19 N4 C18 113.4(3) . . ? C19 N4 C22 111.7(3) . . ? C18 N4 C22 106.9(3) . . ? C19 N4 H4N 112(2) . . ? C18 N4 H4N 105(2) . . ? C22 N4 H4N 107(2) . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C25 N5 C29 116.9(3) . . ? C25 N5 Zn1 121.0(2) . . ? C29 N5 Zn1 122.1(2) . . ? N1 C5 C4 123.7(3) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C24 O6 C23 112.9(3) . . ? C32 N6 C31 111.4(3) . . ? C32 N6 C30 112.1(3) . . ? C31 N6 C30 112.0(3) . . ? N2 C6 C3 114.2(3) . . ? N2 C6 H6A 108.7 . . ? C3 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C3 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C34 O7 C33 113.3(3) . . ? C35 N7 C39 116.7(3) . . ? C35 N7 Zn1 120.6(2) . . ? C39 N7 Zn1 122.4(2) . . ? N2 C7 C8 113.0(3) . . ? N2 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C42 O8 C43 111.7(4) . . ? C44 N8 C41 107.5(3) . . ? C44 N8 C40 111.6(3) . . ? C41 N8 C40 113.0(3) . . ? C44 N8 H8N 108(3) . . ? C41 N8 H8N 113(3) . . ? C40 N8 H8N 104(3) . . ? O3 C8 C7 108.8(3) . . ? O3 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? O3 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C46 O9 C45 114.9(4) . . ? O3 C9 C24 108.6(3) . 2_655 ? O3 C9 H9A 110.0 . . ? C24 C9 H9A 110.0 2_655 . ? O3 C9 H9B 110.0 . . ? C24 C9 H9B 110.0 2_655 . ? H9A C9 H9B 108.4 . . ? C48 O10 C47 113.4(3) . . ? N2 C10 C11 113.9(3) . . ? N2 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? N2 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? O4 C11 C10 109.0(3) . . ? O4 C11 H11A 109.9 . . ? C10 C11 H11A 109.9 . . ? O4 C11 H11B 109.9 . . ? C10 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O4 C12 C21 111.9(4) . 2_655 ? O4 C12 H12A 109.2 . . ? C21 C12 H12A 109.2 2_655 . ? O4 C12 H12B 109.2 . . ? C21 C12 H12B 109.2 2_655 . ? H12A C12 H12B 107.9 . . ? N3 C13 C14 122.9(3) . . ? N3 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 117.9(3) . . ? C14 C15 C18 120.3(3) . . ? C16 C15 C18 121.6(3) . . ? C17 C16 C15 119.1(3) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? N3 C17 C16 123.0(3) . . ? N3 C17 H17 118.5 . . ? C16 C17 H17 118.5 . . ? N4 C18 C15 114.7(3) . . ? N4 C18 H18A 108.6 . . ? C15 C18 H18A 108.6 . . ? N4 C18 H18B 108.6 . . ? C15 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C20 C19 N4 113.5(3) . . ? C20 C19 H19A 108.9 . . ? N4 C19 H19A 108.9 . . ? C20 C19 H19B 108.9 . . ? N4 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? O5 C21 C12 115.6(4) . 2_645 ? O5 C21 H21A 108.4 . . ? C12 C21 H21A 108.4 2_645 . ? O5 C21 H21B 108.4 . . ? C12 C21 H21B 108.4 2_645 . ? H21A C21 H21B 107.4 . . ? C23 C22 N4 113.4(3) . . ? C23 C22 H22A 108.9 . . ? N4 C22 H22A 108.9 . . ? C23 C22 H22B 108.9 . . ? N4 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? O6 C23 C22 114.2(3) . . ? O6 C23 H23A 108.7 . . ? C22 C23 H23A 108.7 . . ? O6 C23 H23B 108.7 . . ? C22 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? O6 C24 C9 108.6(3) . 2_645 ? O6 C24 H24A 110.0 . . ? C9 C24 H24A 110.0 2_645 . ? O6 C24 H24B 110.0 . . ? C9 C24 H24B 110.0 2_645 . ? H24A C24 H24B 108.3 . . ? N5 C25 C26 122.6(3) . . ? N5 C25 H25 118.7 . . ? C26 C25 H25 118.7 . . ? C25 C26 C27 120.4(3) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C28 117.0(3) . . ? C26 C27 C30 121.1(3) . . ? C28 C27 C30 121.8(3) . . ? H28B O28 H28A 111(6) . . ? C29 C28 C27 119.7(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? N5 C29 C28 123.3(3) . . ? N5 C29 H29 118.3 . . ? C28 C29 H29 118.3 . . ? N6 C30 C27 113.6(3) . . ? N6 C30 H30A 108.9 . . ? C27 C30 H30A 108.9 . . ? N6 C30 H30B 108.9 . . ? C27 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? N6 C31 C48 112.7(3) . 2 ? N6 C31 H31A 109.1 . . ? C48 C31 H31A 109.1 2 . ? N6 C31 H31B 109.1 . . ? C48 C31 H31B 109.1 2 . ? H31A C31 H31B 107.8 . . ? N6 C32 C33 113.0(3) . . ? N6 C32 H32A 109.0 . . ? C33 C32 H32A 109.0 . . ? N6 C32 H32B 109.0 . . ? C33 C32 H32B 109.0 . . ? H32A C32 H32B 107.8 . . ? O7 C33 C32 108.5(3) . . ? O7 C33 H33A 110.0 . . ? C32 C33 H33A 110.0 . . ? O7 C33 H33B 110.0 . . ? C32 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? O7 C34 C43 108.5(4) . 2 ? O7 C34 H34A 110.0 . . ? C43 C34 H34A 110.0 2 . ? O7 C34 H34B 110.0 . . ? C43 C34 H34B 110.0 2 . ? H34A C34 H34B 108.4 . . ? N7 C35 C36 123.6(3) . . ? N7 C35 H35 118.2 . . ? C36 C35 H35 118.2 . . ? C35 C36 C37 119.3(4) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C36 C37 C38 117.8(3) . . ? C36 C37 C40 120.7(3) . . ? C38 C37 C40 121.6(3) . . ? C39 C38 C37 119.3(3) . . ? C39 C38 H38 120.3 . . ? C37 C38 H38 120.3 . . ? N7 C39 C38 123.2(3) . . ? N7 C39 H39 118.4 . . ? C38 C39 H39 118.4 . . ? C37 C40 N8 111.7(3) . . ? C37 C40 H40A 109.3 . . ? N8 C40 H40A 109.3 . . ? C37 C40 H40B 109.3 . . ? N8 C40 H40B 109.3 . . ? H40A C40 H40B 107.9 . . ? C42 C41 N8 112.1(4) . . ? C42 C41 H41A 109.2 . . ? N8 C41 H41A 109.2 . . ? C42 C41 H41B 109.2 . . ? N8 C41 H41B 109.2 . . ? H41A C41 H41B 107.9 . . ? O8 C42 C41 109.6(4) . . ? O8 C42 H42A 109.8 . . ? C41 C42 H42A 109.8 . . ? O8 C42 H42B 109.8 . . ? C41 C42 H42B 109.8 . . ? H42A C42 H42B 108.2 . . ? O8 C43 C34 109.7(4) . 2_545 ? O8 C43 H43A 109.7 . . ? C34 C43 H43A 109.7 2_545 . ? O8 C43 H43B 109.7 . . ? C34 C43 H43B 109.7 2_545 . ? H43A C43 H43B 108.2 . . ? C45 C44 N8 115.7(4) . . ? C45 C44 H44A 108.4 . . ? N8 C44 H44A 108.4 . . ? C45 C44 H44B 108.4 . . ? N8 C44 H44B 108.4 . . ? H44A C44 H44B 107.4 . . ? O9 C45 C44 114.5(4) . . ? O9 C45 H45A 108.6 . . ? C44 C45 H45A 108.6 . . ? O9 C45 H45B 108.6 . . ? C44 C45 H45B 108.6 . . ? H45A C45 H45B 107.6 . . ? O9 C46 C47 109.4(4) . . ? O9 C46 H46A 109.8 . . ? C47 C46 H46A 109.8 . . ? O9 C46 H46B 109.8 . . ? C47 C46 H46B 109.8 . . ? H46A C46 H46B 108.2 . . ? O10 C47 C46 109.3(3) . . ? O10 C47 H47A 109.8 . . ? C46 C47 H47A 109.8 . . ? O10 C47 H47B 109.8 . . ? C46 C47 H47B 109.8 . . ? H47A C47 H47B 108.3 . . ? O10 C48 C31 108.7(3) . 2_545 ? O10 C48 H48A 109.9 . . ? C31 C48 H48A 109.9 2_545 . ? O10 C48 H48B 109.9 . . ? C31 C48 H48B 109.9 2_545 . ? H48A C48 H48B 108.3 . . ? H29A O29 H29B 107(5) . . ? H30C O30 H30D 108(5) . . ? C20 O5 C21 119.4(4) . . ? O5 C20 C19 113.7(4) . . ? O5 C20 H20A 108.8 . . ? C19 C20 H20A 108.8 . . ? O5 C20 H20B 108.8 . . ? C19 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B O28 0.880(19) 1.78(2) 2.654(4) 170(4) . O1 H1A O23 0.873(19) 2.25(3) 3.035(6) 150(4) . O2 H2A O18 0.875(19) 1.87(2) 2.734(4) 169(5) . O2 H2B O21 0.877(19) 1.92(2) 2.799(4) 176(5) . N8 H8N O30 0.89(5) 1.82(5) 2.709(5) 175(5) . O30 H30D O10 0.880(19) 1.91(2) 2.782(4) 170(5) . O30 H30C O7 0.88(2) 1.89(2) 2.758(4) 172(6) 2_545 N4 H4N O29 0.86(4) 1.87(4) 2.720(4) 167(3) . O29 H29A O3 0.883(19) 1.97(2) 2.829(3) 163(4) 2_645 O29 H29B O4 0.880(19) 1.95(2) 2.812(4) 168(5) 2_645 O28 H28A O27 0.89(2) 1.89(2) 2.766(6) 168(6) 1_545 O28 H28B O11 0.88(2) 1.97(3) 2.821(5) 162(6) 3_556 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.393 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 898010' ####################################################################### # # 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_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H36 N6 O4 S2 Zn' _chemical_formula_sum 'C26 H36 N6 O4 S2 Zn' _chemical_formula_weight 626.10 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' S S 0.1246 0.1234 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5947(3) _cell_length_b 10.3589(3) _cell_length_c 14.8323(4) _cell_angle_alpha 86.675(1) _cell_angle_beta 88.007(1) _cell_angle_gamma 85.200(1) _cell_volume 1465.88(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 22144 _cell_measurement_theta_min 1.38 _cell_measurement_theta_max 31.46 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6289 _exptl_absorpt_correction_T_max 0.6852 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 Apex KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22144 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 31.46 _reflns_number_total 7703 _reflns_number_gt 7458 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_cell_refinement 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_data_reduction 'Bruker Apex2 v2.0 (Bruker Axs 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed (Barbour, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0471P)^2^+0.8138P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7703 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.653172(18) 0.569691(17) 0.727033(12) 0.01621(6) Uani 1 1 d . . . S1 S 0.46765(6) 0.96521(5) 0.84434(4) 0.03694(12) Uani 1 1 d . . . O1 O 0.80924(12) 0.46797(11) 1.14100(8) 0.0207(2) Uani 1 1 d . . . N1 N 0.57718(16) 0.73549(15) 0.77144(11) 0.0254(3) Uani 1 1 d . . . C1 C 0.53187(17) 0.83128(17) 0.80175(12) 0.0226(3) Uani 1 1 d . . . S2 S 0.38318(4) 0.34640(4) 0.54179(3) 0.02236(9) Uani 1 1 d . . . O2 O 1.22249(12) 0.30596(11) 0.99061(8) 0.0202(2) Uani 1 1 d . . . N2 N 0.52349(16) 0.47509(15) 0.66567(10) 0.0251(3) Uani 1 1 d . . . C2 C 0.46497(16) 0.42141(15) 0.61321(11) 0.0173(3) Uani 1 1 d . . . O3 O 1.15367(12) 1.02743(11) 0.64569(8) 0.0213(2) Uani 1 1 d . . . N3 N 0.72837(13) 0.43949(12) 0.82481(9) 0.0156(2) Uani 1 1 d . . . C3 C 0.83387(17) 0.46712(15) 0.87608(10) 0.0177(3) Uani 1 1 d . . . H3 H 0.8718 0.5465 0.8654 0.021 Uiso 1 1 calc R . . O4 O 1.11534(13) 0.80702(11) 0.31389(9) 0.0233(2) Uani 1 1 d . . . N4 N 0.97811(14) 0.22902(12) 1.09640(9) 0.0162(2) Uani 1 1 d . . . C4 C 0.88811(17) 0.38252(15) 0.94389(10) 0.0178(3) Uani 1 1 d . . . H4 H 0.9626 0.4041 0.9769 0.021 Uiso 1 1 calc R . . N5 N 0.82889(14) 0.61326(12) 0.65571(9) 0.0156(2) Uani 1 1 d . . . C5 C 0.83028(16) 0.26490(14) 0.96229(10) 0.0150(3) Uani 1 1 d . . . N6 N 1.22399(15) 0.84079(12) 0.49707(9) 0.0179(3) Uani 1 1 d . . . C6 C 0.72170(16) 0.23537(15) 0.90901(11) 0.0182(3) Uani 1 1 d . . . H6 H 0.6809 0.1573 0.9192 0.022 Uiso 1 1 calc R . . C7 C 0.67530(16) 0.32348(15) 0.84080(11) 0.0184(3) Uani 1 1 d . . . H7 H 0.6046 0.3019 0.8045 0.022 Uiso 1 1 calc R . . C8 C 0.88717(17) 0.17039(14) 1.03633(11) 0.0190(3) Uani 1 1 d . . . H8A H 0.8095 0.1373 1.0716 0.023 Uiso 1 1 calc R . . H8B H 0.9393 0.0976 1.0091 0.023 Uiso 1 1 calc R . . C9 C 0.91141(18) 0.25347(15) 1.18481(11) 0.0197(3) Uani 1 1 d . . . H9A H 0.9769 0.2914 1.2218 0.024 Uiso 1 1 calc R . . H9B H 0.8892 0.1716 1.2146 0.024 Uiso 1 1 calc R . . C10 C 0.77922(18) 0.34309(16) 1.17806(12) 0.0221(3) Uani 1 1 d . . . H10A H 0.7140 0.3065 1.1401 0.027 Uiso 1 1 calc R . . H10B H 0.7355 0.3512 1.2377 0.027 Uiso 1 1 calc R . . C11 C 0.68262(18) 0.54252(17) 1.11925(14) 0.0271(4) Uani 1 1 d . . . H11A H 0.6172 0.5387 1.1705 0.032 Uiso 1 1 calc R . . H11B H 0.6409 0.5063 1.0687 0.032 Uiso 1 1 calc R . . C12 C 1.11811(17) 0.16329(15) 1.10192(11) 0.0192(3) Uani 1 1 d . . . H12A H 1.1105 0.0724 1.1192 0.023 Uiso 1 1 calc R . . H12B H 1.1678 0.2003 1.1487 0.023 Uiso 1 1 calc R . . C13 C 1.20192(18) 0.17381(15) 1.01396(12) 0.0218(3) Uani 1 1 d . . . H13A H 1.2918 0.1244 1.0201 0.026 Uiso 1 1 calc R . . H13B H 1.1526 0.1381 0.9664 0.026 Uiso 1 1 calc R . . C14 C 1.29070(19) 0.31838(18) 0.90487(12) 0.0259(3) Uiso 1 1 d . . . H14A H 1.2332 0.2874 0.8595 0.031 Uiso 1 1 calc R . . H14B H 1.3789 0.2653 0.9053 0.031 Uiso 1 1 calc R . . C15 C 0.83996(16) 0.73206(15) 0.61495(11) 0.0179(3) Uani 1 1 d . . . H15 H 0.7649 0.7943 0.6202 0.021 Uiso 1 1 calc R . . C16 C 0.95784(17) 0.76523(14) 0.56577(11) 0.0182(3) Uani 1 1 d . . . H16 H 0.9612 0.8480 0.5384 0.022 Uiso 1 1 calc R . . C17 C 1.07185(16) 0.67348(14) 0.55755(10) 0.0161(3) Uani 1 1 d . . . C18 C 1.06050(17) 0.55102(15) 0.60026(11) 0.0197(3) Uani 1 1 d . . . H18 H 1.1345 0.4874 0.5968 0.024 Uiso 1 1 calc R . . C19 C 0.93881(17) 0.52482(15) 0.64770(11) 0.0183(3) Uani 1 1 d . . . H19 H 0.9326 0.4425 0.6753 0.022 Uiso 1 1 calc R . . C20 C 1.20020(18) 0.70251(15) 0.50094(12) 0.0208(3) Uani 1 1 d . . . H20A H 1.2812 0.6526 0.5260 0.025 Uiso 1 1 calc R . . H20B H 1.1897 0.6757 0.4401 0.025 Uiso 1 1 calc R . . C21 C 1.30821(17) 0.86846(16) 0.57351(11) 0.0206(3) Uani 1 1 d . . . H21A H 1.4063 0.8489 0.5577 0.025 Uiso 1 1 calc R . . H21B H 1.2850 0.8114 0.6250 0.025 Uiso 1 1 calc R . . C22 C 1.28695(17) 1.00709(16) 0.60068(12) 0.0215(3) Uani 1 1 d . . . H22A H 1.3603 1.0246 0.6406 0.026 Uiso 1 1 calc R . . H22B H 1.2916 1.0658 0.5475 0.026 Uiso 1 1 calc R . . C23 C 1.14001(19) 1.14913(16) 0.68598(12) 0.0236(3) Uani 1 1 d . . . H23A H 1.1426 1.2184 0.6392 0.028 Uiso 1 1 calc R . . H23B H 1.2179 1.1549 0.7251 0.028 Uiso 1 1 calc R . . C24 C 1.28514(17) 0.88427(15) 0.40931(11) 0.0196(3) Uani 1 1 d . . . H24A H 1.3503 0.8155 0.3876 0.024 Uiso 1 1 calc R . . H24B H 1.3374 0.9587 0.4175 0.024 Uiso 1 1 calc R . . C25 C 1.17638(18) 0.92065(15) 0.33899(11) 0.0214(3) Uani 1 1 d . . . H25A H 1.1041 0.9815 0.3631 0.026 Uiso 1 1 calc R . . H25B H 1.2196 0.9624 0.2862 0.026 Uiso 1 1 calc R . . C26 C 0.99574(18) 0.83479(17) 0.25980(11) 0.0226(3) Uani 1 1 d . . . H26A H 0.9906 0.7650 0.2195 0.027 Uiso 1 1 calc R . . H26B H 1.0071 0.9138 0.2229 0.027 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 0.01478(9) 0.01730(9) 0.01667(10) 0.00093(7) -0.00085(7) -0.00307(6) S1 0.0315(2) 0.0260(2) 0.0541(3) -0.0154(2) -0.0020(2) 0.00218(18) O1 0.0201(5) 0.0160(5) 0.0254(6) 0.0029(4) 0.0046(5) -0.0022(4) N1 0.0205(7) 0.0236(7) 0.0317(8) -0.0022(6) 0.0010(6) -0.0008(5) C1 0.0170(7) 0.0231(8) 0.0280(8) 0.0000(6) -0.0017(6) -0.0042(6) S2 0.01909(18) 0.02190(19) 0.0271(2) -0.00683(16) -0.00166(16) -0.00342(14) O2 0.0230(6) 0.0143(5) 0.0229(6) 0.0010(4) 0.0055(5) -0.0026(4) N2 0.0232(7) 0.0312(8) 0.0216(7) 0.0009(6) -0.0020(6) -0.0082(6) C2 0.0143(6) 0.0182(7) 0.0187(7) 0.0037(5) 0.0019(5) -0.0012(5) O3 0.0209(5) 0.0181(5) 0.0253(6) -0.0070(4) 0.0063(5) -0.0028(4) N3 0.0158(6) 0.0164(6) 0.0147(6) -0.0011(5) 0.0013(5) -0.0023(4) C3 0.0230(7) 0.0143(6) 0.0168(7) -0.0014(5) 0.0000(6) -0.0067(5) O4 0.0274(6) 0.0167(5) 0.0259(6) -0.0041(5) -0.0013(5) 0.0003(4) N4 0.0173(6) 0.0151(6) 0.0164(6) 0.0006(5) -0.0023(5) -0.0026(5) C4 0.0221(7) 0.0158(7) 0.0164(7) -0.0020(5) -0.0032(6) -0.0059(5) N5 0.0169(6) 0.0144(6) 0.0159(6) 0.0001(5) -0.0015(5) -0.0037(4) C5 0.0170(6) 0.0136(6) 0.0147(6) -0.0019(5) 0.0012(5) -0.0018(5) N6 0.0227(6) 0.0136(6) 0.0174(6) -0.0007(5) 0.0046(5) -0.0035(5) C6 0.0175(7) 0.0154(6) 0.0225(7) -0.0009(6) -0.0009(6) -0.0052(5) C7 0.0151(6) 0.0193(7) 0.0214(7) -0.0008(6) -0.0020(6) -0.0049(5) C8 0.0235(7) 0.0121(6) 0.0217(7) 0.0012(5) -0.0046(6) -0.0040(5) C9 0.0238(7) 0.0178(7) 0.0173(7) 0.0024(6) 0.0006(6) -0.0034(6) C10 0.0238(8) 0.0187(7) 0.0234(8) 0.0036(6) 0.0065(6) -0.0048(6) C11 0.0199(8) 0.0238(8) 0.0354(10) 0.0070(7) 0.0108(7) 0.0006(6) C12 0.0197(7) 0.0150(6) 0.0223(7) 0.0047(6) -0.0020(6) -0.0009(5) C13 0.0237(8) 0.0139(7) 0.0267(8) 0.0015(6) 0.0043(6) 0.0003(6) C15 0.0175(7) 0.0151(6) 0.0208(7) 0.0003(5) -0.0009(6) -0.0001(5) C16 0.0217(7) 0.0128(6) 0.0195(7) 0.0019(5) 0.0017(6) -0.0016(5) C17 0.0200(7) 0.0143(6) 0.0143(6) -0.0025(5) 0.0024(5) -0.0028(5) C18 0.0223(7) 0.0138(6) 0.0222(7) -0.0001(6) 0.0048(6) 0.0003(5) C19 0.0223(7) 0.0133(6) 0.0194(7) 0.0006(5) 0.0016(6) -0.0030(5) C20 0.0255(8) 0.0137(7) 0.0225(8) -0.0020(6) 0.0100(6) -0.0021(6) C21 0.0207(7) 0.0198(7) 0.0206(7) -0.0010(6) 0.0024(6) 0.0016(6) C22 0.0199(7) 0.0215(7) 0.0235(8) -0.0055(6) 0.0044(6) -0.0034(6) C23 0.0256(8) 0.0199(7) 0.0259(8) -0.0074(6) 0.0035(7) -0.0035(6) C24 0.0209(7) 0.0167(7) 0.0206(7) 0.0009(6) 0.0064(6) -0.0025(6) C25 0.0273(8) 0.0149(7) 0.0218(7) 0.0006(6) 0.0019(6) -0.0027(6) C26 0.0270(8) 0.0223(7) 0.0184(7) -0.0040(6) 0.0014(6) 0.0002(6) _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 1.9295(15) . ? Zn1 N1 1.9502(16) . ? Zn1 N5 2.0281(13) . ? Zn1 N3 2.0313(13) . ? S1 C1 1.6233(18) . ? O1 C11 1.420(2) . ? O1 C10 1.4239(18) . ? N1 C1 1.158(2) . ? S2 C2 1.6116(17) . ? O2 C14 1.414(2) . ? O2 C13 1.4206(18) . ? N2 C2 1.167(2) . ? O3 C23 1.421(2) . ? O3 C22 1.4273(19) . ? N3 C7 1.3493(19) . ? N3 C3 1.346(2) . ? C3 C4 1.381(2) . ? C3 H3 0.9300 . ? O4 C26 1.423(2) . ? O4 C25 1.431(2) . ? N4 C12 1.457(2) . ? N4 C8 1.459(2) . ? N4 C9 1.465(2) . ? C4 C5 1.390(2) . ? C4 H4 0.9300 . ? N5 C19 1.345(2) . ? N5 C15 1.3499(19) . ? C5 C6 1.394(2) . ? C5 C8 1.513(2) . ? N6 C20 1.4668(19) . ? N6 C24 1.4712(19) . ? N6 C21 1.470(2) . ? C6 C7 1.382(2) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.510(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C14 1.505(2) 2_767 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.512(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C11 1.505(2) 2_767 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.381(2) . ? C15 H15 0.9300 . ? C16 C17 1.395(2) . ? C16 H16 0.9300 . ? C17 C18 1.395(2) . ? C17 C20 1.508(2) . ? C18 C19 1.380(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.510(2) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C26 1.509(2) 2_776 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.511(2) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C23 1.509(2) 2_776 ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? 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 N1 115.63(7) . . ? N2 Zn1 N5 116.30(6) . . ? N1 Zn1 N5 104.03(6) . . ? N2 Zn1 N3 103.45(6) . . ? N1 Zn1 N3 114.27(6) . . ? N5 Zn1 N3 102.77(5) . . ? C11 O1 C10 109.78(12) . . ? C1 N1 Zn1 176.88(15) . . ? N1 C1 S1 179.72(18) . . ? C14 O2 C13 110.48(13) . . ? C2 N2 Zn1 165.50(14) . . ? N2 C2 S2 179.30(15) . . ? C23 O3 C22 110.84(12) . . ? C7 N3 C3 117.81(13) . . ? C7 N3 Zn1 121.76(11) . . ? C3 N3 Zn1 120.43(10) . . ? N3 C3 C4 122.76(14) . . ? N3 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C26 O4 C25 113.46(13) . . ? C12 N4 C8 113.91(13) . . ? C12 N4 C9 113.50(13) . . ? C8 N4 C9 112.82(13) . . ? C3 C4 C5 119.38(14) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C19 N5 C15 117.64(13) . . ? C19 N5 Zn1 121.09(10) . . ? C15 N5 Zn1 121.27(11) . . ? C4 C5 C6 118.09(14) . . ? C4 C5 C8 120.60(14) . . ? C6 C5 C8 121.28(13) . . ? C20 N6 C24 112.09(13) . . ? C20 N6 C21 109.87(13) . . ? C24 N6 C21 112.67(13) . . ? C7 C6 C5 119.24(14) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N3 C7 C6 122.67(14) . . ? N3 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? N4 C8 C5 112.77(12) . . ? N4 C8 H8A 109.0 . . ? C5 C8 H8A 109.0 . . ? N4 C8 H8B 109.0 . . ? C5 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? N4 C9 C10 112.66(13) . . ? N4 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N4 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? O1 C10 C9 110.75(13) . . ? O1 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O1 C11 C14 110.72(14) . 2_767 ? O1 C11 H11A 109.5 . . ? C14 C11 H11A 109.5 2_767 . ? O1 C11 H11B 109.5 . . ? C14 C11 H11B 109.5 2_767 . ? H11A C11 H11B 108.1 . . ? N4 C12 C13 112.95(13) . . ? N4 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? N4 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? O2 C13 C12 109.85(13) . . ? O2 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? O2 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? O2 C14 C11 110.96(15) . 2_767 ? O2 C14 H14A 109.4 . . ? C11 C14 H14A 109.4 2_767 . ? O2 C14 H14B 109.4 . . ? C11 C14 H14B 109.4 2_767 . ? H14A C14 H14B 108.0 . . ? N5 C15 C16 122.90(14) . . ? N5 C15 H15 118.5 . . ? C16 C15 H15 118.5 . . ? C15 C16 C17 119.42(14) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 117.56(14) . . ? C18 C17 C20 120.83(14) . . ? C16 C17 C20 121.55(13) . . ? C19 C18 C17 119.67(14) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? N5 C19 C18 122.80(14) . . ? N5 C19 H19 118.6 . . ? C18 C19 H19 118.6 . . ? N6 C20 C17 112.15(13) . . ? N6 C20 H20A 109.2 . . ? C17 C20 H20A 109.2 . . ? N6 C20 H20B 109.2 . . ? C17 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? N6 C21 C22 113.94(13) . . ? N6 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? N6 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? O3 C22 C21 109.32(13) . . ? O3 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? O3 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? O3 C23 C26 110.64(14) . 2_776 ? O3 C23 H23A 109.5 . . ? C26 C23 H23A 109.5 2_776 . ? O3 C23 H23B 109.5 . . ? C26 C23 H23B 109.5 2_776 . ? H23A C23 H23B 108.1 . . ? N6 C24 C25 112.89(13) . . ? N6 C24 H24A 109.0 . . ? C25 C24 H24A 109.0 . . ? N6 C24 H24B 109.0 . . ? C25 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? O4 C25 C24 109.95(13) . . ? O4 C25 H25A 109.7 . . ? C24 C25 H25A 109.7 . . ? O4 C25 H25B 109.7 . . ? C24 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? O4 C26 C23 113.61(14) . 2_776 ? O4 C26 H26A 108.8 . . ? C23 C26 H26A 108.8 2_776 . ? O4 C26 H26B 108.8 . . ? C23 C26 H26B 108.8 2_776 . ? H26A C26 H26B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.791 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.803 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 898011' ####################################################################### # # 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_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H74 Fe N10 O8 S2, 2(Cl O4), 2(C4 H8 O), 2(H2 O)' _chemical_formula_sum 'C58 H94 Cl2 Fe N10 O20 S2' _chemical_formula_weight 1442.30 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' S S 0.1246 0.1234 '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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6015(3) _cell_length_b 23.5649(4) _cell_length_c 23.6458(5) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 7021.7(4) _cell_measurement_temperature 123.01(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9507 _cell_measurement_theta_min 2.6450 _cell_measurement_theta_max 66.4038 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3056.0 _exptl_absorpt_coefficient_mu 3.618 _cell_oxdiff_length_a 12.6018(4) _cell_oxdiff_length_b 23.5583(7) _cell_oxdiff_length_c 23.6520(9) _cell_oxdiff_angle_alpha 89.998(3) _cell_oxdiff_angle_beta 89.993(3) _cell_oxdiff_angle_gamma 90.008(3) _cell_oxdiff_volume 7021.7(4) _cell_oxdiff_measurement_reflns_used 9507 _exptl_absorpt_correction_T_min 0.44283 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 123.01(15) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_detector_area_resol_mean 10.3389 _diffrn_reflns_number 43461 _diffrn_reflns_av_R_equivalents 0.0809 _diffrn_reflns_av_sigmaI/netI 0.2001 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.6450 _diffrn_reflns_theta_max 66.4038 _reflns_number_total 6172 _reflns_number_gt 4928 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0422236000 _diffrn_orient_matrix_UB_12 -0.0141584000 _diffrn_orient_matrix_UB_13 0.0594811000 _diffrn_orient_matrix_UB_21 0.1146935000 _diffrn_orient_matrix_UB_22 -0.0067230000 _diffrn_orient_matrix_UB_23 0.0215174000 _diffrn_orient_matrix_UB_31 0.0027476000 _diffrn_orient_matrix_UB_32 0.0634876000 _diffrn_orient_matrix_UB_33 0.0155411000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 11.00 108.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 41.0046 57.0000 -120.0000 97 #__ type_ start__ end____ width___ exp.time_ 2 omega -35.00 52.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 41.0046 -38.0000 90.0000 87 #__ type_ start__ end____ width___ exp.time_ 3 omega 21.00 67.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -92.0000 -170.0000 46 #__ type_ start__ end____ width___ exp.time_ 4 omega 21.00 70.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -45.0000 -60.0000 49 #__ type_ start__ end____ width___ exp.time_ 5 omega 36.00 65.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -30.0000 -60.0000 29 #__ type_ start__ end____ width___ exp.time_ 6 omega 19.00 77.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -45.0000 -150.0000 58 #__ type_ start__ end____ width___ exp.time_ 7 omega 10.00 74.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -95.0000 -120.0000 64 #__ type_ start__ end____ width___ exp.time_ 8 omega 60.00 111.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 77.0000 -120.0000 51 #__ type_ start__ end____ width___ exp.time_ 9 omega 18.00 61.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -61.0000 -180.0000 43 #__ type_ start__ end____ width___ exp.time_ 10 omega 30.00 56.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -125.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 71.00 96.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -125.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 12 omega 30.00 69.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -30.0000 -30.0000 39 #__ type_ start__ end____ width___ exp.time_ 13 omega 17.00 60.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -30.0000 0.0000 43 #__ type_ start__ end____ width___ exp.time_ 14 omega 87.00 130.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 61.0000 -60.0000 43 #__ type_ start__ end____ width___ exp.time_ 15 omega 134.00 162.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 61.0000 -60.0000 28 #__ type_ start__ end____ width___ exp.time_ 16 omega 82.00 127.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -92.0000 -170.0000 45 #__ type_ start__ end____ width___ exp.time_ 17 omega 133.00 170.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 77.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 18 omega 33.00 65.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -95.0000 120.0000 32 #__ type_ start__ end____ width___ exp.time_ 19 omega 50.00 128.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -86.0000 92.0000 78 #__ type_ start__ end____ width___ exp.time_ 20 omega 78.00 104.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -61.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 21 omega 12.00 38.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 92.5000 -86.0000 92.0000 26 ; _diffrn_measurement_method '\w scans' _reflns_odcompleteness_completeness 98.48 _reflns_odcompleteness_theta 66.97 _reflns_odcompleteness_iscentric 1 _chemical_oxdiff_formula 'C20 H20 Fe N6 O6 S2 Cl1' _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0737P)^2^+3.4584P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6172 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Fe1 Fe 0.5000 0.0000 0.5000 0.02293(16) Uani 1 2 d S . . Cl1 Cl 0.31582(7) 0.15184(4) 0.26785(4) 0.0424(2) Uani 1 1 d . . . S1 S 0.56106(8) 0.13428(4) 0.65186(4) 0.0470(3) Uani 1 1 d . . . O3 O 0.78063(17) 0.27052(8) 0.44596(10) 0.0301(5) Uani 1 1 d . . . N4 N 0.57343(18) 0.06906(9) 0.44624(10) 0.0207(5) Uani 1 1 d . . . N1 N 0.34325(18) 0.03218(9) 0.47198(10) 0.0222(5) Uani 1 1 d . . . N5 N 0.49742(19) 0.05526(10) 0.57087(10) 0.0234(5) Uani 1 1 d . . . O2 O -0.12712(19) 0.12545(9) 0.54575(12) 0.0406(6) Uani 1 1 d . . . O1 O 0.1775(2) 0.20372(9) 0.45467(10) 0.0363(5) Uani 1 1 d . . . N3 N 0.6327(2) 0.26324(10) 0.34463(10) 0.0245(5) Uani 1 1 d . . . O4 O 0.46745(19) 0.35643(10) 0.34876(11) 0.0402(6) Uani 1 1 d . . . C1 C 0.3231(3) 0.03749(12) 0.41634(13) 0.0279(7) Uani 1 1 d . . . H1 H 0.3779 0.0282 0.3904 0.033 Uiso 1 1 calc R . . O5 O 0.2087(2) 0.13206(11) 0.27483(11) 0.0427(6) Uani 1 1 d . . . C25 C 0.5230(2) 0.08799(13) 0.60505(13) 0.0247(6) Uani 1 1 d . . . N2 N -0.0079(2) 0.13688(11) 0.43675(12) 0.0331(6) Uani 1 1 d . . . C5 C 0.2648(2) 0.04674(11) 0.50766(13) 0.0232(6) Uani 1 1 d . . . H5 H 0.2774 0.0439 0.5472 0.028 Uiso 1 1 calc R . . C20 C 0.5918(2) 0.16077(12) 0.37110(13) 0.0236(6) Uani 1 1 d . . . O6 O 0.3485(3) 0.14037(13) 0.21087(13) 0.0626(8) Uani 1 1 d . . . C4 C 0.1665(2) 0.06568(12) 0.48944(14) 0.0276(7) Uani 1 1 d . . . H4 H 0.1134 0.0757 0.5162 0.033 Uiso 1 1 calc R . . C8 C 0.1318(3) 0.20206(14) 0.39948(14) 0.0397(8) Uani 1 1 d . . . H8A H 0.1669 0.1724 0.3765 0.048 Uiso 1 1 calc R . . H8B H 0.1417 0.2391 0.3804 0.048 Uiso 1 1 calc R . . C14 C 0.8003(3) 0.29525(13) 0.39258(15) 0.0340(7) Uani 1 1 d . . . H14A H 0.8776 0.2989 0.3861 0.041 Uiso 1 1 calc R . . H14B H 0.7681 0.3335 0.3906 0.041 Uiso 1 1 calc R . . C2 C 0.2267(3) 0.05572(12) 0.39498(14) 0.0312(7) Uani 1 1 d . . . H2 H 0.2161 0.0584 0.3553 0.037 Uiso 1 1 calc R . . C23 C 0.5667(3) 0.12342(12) 0.46364(14) 0.0300(7) Uani 1 1 d . . . H23 H 0.5554 0.1303 0.5028 0.036 Uiso 1 1 calc R . . C16 C 0.6064(3) 0.30874(13) 0.30157(14) 0.0338(7) Uani 1 1 d . . . H16A H 0.6492 0.3429 0.3102 0.041 Uiso 1 1 calc R . . H16B H 0.6279 0.2951 0.2637 0.041 Uiso 1 1 calc R . . C3 C 0.1460(2) 0.06999(12) 0.43179(14) 0.0302(7) Uani 1 1 d . . . O7 O 0.3183(3) 0.21170(13) 0.27856(14) 0.0708(9) Uani 1 1 d . . . C21 C 0.6069(2) 0.10537(12) 0.35313(13) 0.0269(6) Uani 1 1 d . . . H21 H 0.6237 0.0976 0.3147 0.032 Uiso 1 1 calc R . . C22 C 0.5972(2) 0.06143(12) 0.39167(13) 0.0259(6) Uani 1 1 d . . . H22 H 0.6081 0.0238 0.3786 0.031 Uiso 1 1 calc R . . C6 C 0.0381(3) 0.08661(14) 0.40924(17) 0.0415(9) Uani 1 1 d . . . H6A H 0.0443 0.0941 0.3682 0.050 Uiso 1 1 calc R . . H6B H -0.0110 0.0542 0.4142 0.050 Uiso 1 1 calc R . . O8 O 0.3830(3) 0.12282(14) 0.30693(16) 0.0750(11) Uani 1 1 d . . . C24 C 0.5752(3) 0.16944(12) 0.42822(13) 0.0303(7) Uani 1 1 d . . . H24 H 0.5697 0.2069 0.4429 0.036 Uiso 1 1 calc R . . C19 C 0.5823(3) 0.20774(12) 0.32775(13) 0.0286(7) Uani 1 1 d . . . H19A H 0.6152 0.1947 0.2920 0.034 Uiso 1 1 calc R . . H19B H 0.5060 0.2145 0.3201 0.034 Uiso 1 1 calc R . . C17 C 0.4911(3) 0.32552(15) 0.29945(16) 0.0427(9) Uani 1 1 d . . . H17A H 0.4774 0.3491 0.2656 0.051 Uiso 1 1 calc R . . H17B H 0.4459 0.2912 0.2973 0.051 Uiso 1 1 calc R . . C15 C 0.7516(2) 0.25693(13) 0.34863(14) 0.0300(7) Uani 1 1 d . . . H15A H 0.7689 0.2170 0.3580 0.036 Uiso 1 1 calc R . . H15B H 0.7834 0.2656 0.3113 0.036 Uiso 1 1 calc R . . C10 C -0.1224(3) 0.13034(14) 0.44509(17) 0.0405(9) Uani 1 1 d . . . H10A H -0.1536 0.1130 0.4108 0.049 Uiso 1 1 calc R . . H10B H -0.1547 0.1683 0.4500 0.049 Uiso 1 1 calc R . . C11 C -0.1490(3) 0.09485(14) 0.49475(19) 0.0455(10) Uani 1 1 d . . . H11A H -0.2251 0.0844 0.4935 0.055 Uiso 1 1 calc R . . H11B H -0.1067 0.0595 0.4939 0.055 Uiso 1 1 calc R . . C7 C 0.0164(3) 0.18924(14) 0.40514(15) 0.0411(9) Uani 1 1 d . . . H7A H -0.0185 0.2216 0.4243 0.049 Uiso 1 1 calc R . . H7B H -0.0147 0.1861 0.3668 0.049 Uiso 1 1 calc R . . C13 C 0.8331(3) 0.29990(14) 0.49059(16) 0.0397(8) Uani 1 1 d . . . H13A H 0.8239 0.3413 0.4858 0.048 Uiso 1 1 calc R . . H13B H 0.9100 0.2913 0.4898 0.048 Uiso 1 1 calc R . . C9 C 0.2868(3) 0.21846(16) 0.45473(17) 0.0464(10) Uani 1 1 d . . . H9A H 0.2951 0.2600 0.4501 0.056 Uiso 1 1 calc R . . H9B H 0.3237 0.1994 0.4230 0.056 Uiso 1 1 calc R . . C18 C 0.3569(3) 0.36762(19) 0.35518(19) 0.0533(11) Uani 1 1 d . . . H18A H 0.3177 0.3316 0.3602 0.064 Uiso 1 1 calc R . . H18B H 0.3292 0.3869 0.3210 0.064 Uiso 1 1 calc R . . C12 C -0.1583(3) 0.09567(17) 0.5946(2) 0.0551(11) Uani 1 1 d . . . H12A H -0.1152 0.0608 0.5986 0.066 Uiso 1 1 calc R . . H12B H -0.2338 0.0845 0.5915 0.066 Uiso 1 1 calc R . . O10 O 0.05663(19) 0.19680(9) 0.55404(10) 0.0349(5) Uani 1 1 d . . . O9 O 0.2344(2) 0.06119(12) 0.65644(12) 0.0525(7) Uani 1 1 d . . . C26 C 0.1453(3) 0.02416(18) 0.65533(19) 0.0531(10) Uani 1 1 d . . . H26A H 0.1648 -0.0125 0.6376 0.064 Uiso 1 1 calc R . . H26B H 0.0869 0.0413 0.6332 0.064 Uiso 1 1 calc R . . C29 C 0.2860(4) 0.0567(2) 0.70926(19) 0.0608(12) Uani 1 1 d . . . H29A H 0.2919 0.0945 0.7273 0.073 Uiso 1 1 calc R . . H29B H 0.3582 0.0409 0.7044 0.073 Uiso 1 1 calc R . . C27 C 0.1116(4) 0.01515(19) 0.7148(2) 0.0676(13) Uani 1 1 d . . . H27A H 0.0767 -0.0221 0.7199 0.081 Uiso 1 1 calc R . . H27B H 0.0634 0.0456 0.7279 0.081 Uiso 1 1 calc R . . C28 C 0.2188(5) 0.0175(2) 0.7452(2) 0.0798(17) Uani 1 1 d . . . H28A H 0.2106 0.0328 0.7840 0.096 Uiso 1 1 calc R . . H28B H 0.2512 -0.0207 0.7475 0.096 Uiso 1 1 calc R . . H1A H 0.6023 0.2751 0.3799 0.041(10) Uiso 1 1 d R . . H3A H 0.0167 0.1672 0.5523 0.052(12) Uiso 1 1 d R . . H2A H 0.0920 0.1952 0.5177 0.074(15) Uiso 1 1 d 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 Fe1 0.0208(3) 0.0220(3) 0.0260(3) 0.0026(2) -0.0009(2) -0.0011(2) Cl1 0.0429(5) 0.0424(5) 0.0420(5) 0.0135(4) -0.0160(4) -0.0056(4) S1 0.0425(6) 0.0504(5) 0.0483(6) -0.0230(4) -0.0097(4) -0.0045(4) O3 0.0287(12) 0.0225(10) 0.0389(13) -0.0042(9) -0.0051(9) 0.0039(8) N4 0.0189(12) 0.0192(12) 0.0241(13) 0.0037(9) 0.0003(10) -0.0024(9) N1 0.0190(12) 0.0196(12) 0.0279(13) 0.0035(9) -0.0021(10) -0.0013(9) N5 0.0235(13) 0.0249(12) 0.0218(12) 0.0046(10) 0.0000(10) -0.0015(10) O2 0.0309(13) 0.0310(12) 0.0599(17) 0.0060(11) -0.0080(12) -0.0102(9) O1 0.0421(14) 0.0355(12) 0.0311(12) -0.0060(9) 0.0035(10) -0.0074(10) N3 0.0246(13) 0.0222(12) 0.0267(13) 0.0055(10) 0.0053(10) 0.0014(10) O4 0.0325(13) 0.0403(13) 0.0477(15) 0.0123(11) 0.0003(11) 0.0071(10) C1 0.0276(16) 0.0273(15) 0.0288(16) 0.0017(12) -0.0063(13) 0.0029(12) O5 0.0415(14) 0.0515(14) 0.0352(14) 0.0009(11) -0.0095(11) 0.0000(11) C25 0.0193(15) 0.0294(15) 0.0254(15) 0.0035(13) -0.0004(12) 0.0027(11) N2 0.0311(15) 0.0236(13) 0.0444(16) -0.0125(11) -0.0163(12) 0.0104(10) C5 0.0202(15) 0.0185(13) 0.0308(16) 0.0037(11) -0.0034(12) -0.0026(11) C20 0.0206(15) 0.0229(14) 0.0274(15) 0.0038(12) 0.0018(12) -0.0006(11) O6 0.065(2) 0.0668(18) 0.0557(19) 0.0181(15) 0.0172(15) 0.0128(15) C4 0.0231(16) 0.0180(14) 0.0416(18) -0.0045(12) -0.0031(13) 0.0007(11) C8 0.058(2) 0.0318(17) 0.0288(17) -0.0044(13) -0.0003(16) 0.0089(16) C14 0.0258(17) 0.0261(16) 0.050(2) 0.0029(14) 0.0030(15) 0.0037(12) C2 0.0339(18) 0.0259(15) 0.0337(17) -0.0040(12) -0.0124(14) 0.0054(13) C23 0.0388(19) 0.0252(15) 0.0260(16) 0.0004(12) 0.0055(14) -0.0034(13) C16 0.043(2) 0.0276(16) 0.0303(17) 0.0118(13) 0.0029(14) -0.0009(13) C3 0.0282(17) 0.0168(14) 0.0457(19) -0.0062(12) -0.0159(15) 0.0007(12) O7 0.101(3) 0.0514(17) 0.060(2) 0.0039(14) -0.0319(18) -0.0182(16) C21 0.0280(16) 0.0283(15) 0.0246(15) 0.0008(12) 0.0052(13) 0.0001(12) C22 0.0235(16) 0.0225(14) 0.0316(16) 0.0007(12) 0.0047(13) -0.0003(11) C6 0.0360(19) 0.0304(17) 0.058(2) -0.0207(16) -0.0241(17) 0.0147(14) O8 0.0561(19) 0.082(2) 0.086(2) 0.0483(19) -0.0414(18) -0.0206(16) C24 0.0438(19) 0.0199(14) 0.0272(16) -0.0004(12) 0.0057(14) -0.0023(12) C19 0.0334(17) 0.0240(15) 0.0283(16) 0.0040(12) -0.0024(13) -0.0017(12) C17 0.046(2) 0.0345(18) 0.047(2) 0.0169(16) -0.0111(17) 0.0038(15) C15 0.0246(16) 0.0290(15) 0.0363(17) 0.0032(13) 0.0082(14) 0.0029(12) C10 0.0307(19) 0.0286(17) 0.062(2) -0.0162(16) -0.0223(17) 0.0132(13) C11 0.0262(18) 0.0286(17) 0.082(3) -0.0108(18) -0.0194(18) -0.0029(13) C7 0.058(2) 0.0305(17) 0.0347(19) -0.0064(14) -0.0142(17) 0.0200(15) C13 0.0305(18) 0.0351(18) 0.053(2) -0.0191(15) -0.0105(16) 0.0079(14) C9 0.044(2) 0.048(2) 0.047(2) -0.0180(17) 0.0167(18) -0.0204(16) C18 0.032(2) 0.068(3) 0.059(3) 0.030(2) -0.0045(19) 0.0131(18) C12 0.036(2) 0.045(2) 0.084(3) 0.022(2) -0.009(2) -0.0204(17) O10 0.0367(13) 0.0348(12) 0.0333(13) -0.0059(9) 0.0009(10) -0.0163(10) O9 0.0559(18) 0.0562(15) 0.0454(16) -0.0021(12) -0.0065(13) -0.0164(13) C26 0.045(2) 0.049(2) 0.065(3) -0.0106(19) -0.004(2) -0.0094(17) C29 0.071(3) 0.062(3) 0.050(3) -0.007(2) -0.018(2) 0.006(2) C27 0.079(3) 0.044(2) 0.080(3) 0.001(2) 0.021(3) -0.002(2) C28 0.142(5) 0.045(2) 0.053(3) 0.004(2) -0.015(3) -0.010(3) _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 Fe1 N5 2.122(2) 5_656 ? Fe1 N5 2.122(2) . ? Fe1 N1 2.217(2) 5_656 ? Fe1 N1 2.217(2) . ? Fe1 N4 2.263(2) . ? Fe1 N4 2.263(2) 5_656 ? Cl1 O8 1.428(3) . ? Cl1 O6 1.434(3) . ? Cl1 O7 1.434(3) . ? Cl1 O5 1.438(3) . ? S1 C25 1.626(3) . ? O3 C14 1.412(4) . ? O3 C13 1.425(4) . ? N4 C22 1.337(4) . ? N4 C23 1.348(4) . ? N1 C5 1.344(4) . ? N1 C1 1.346(4) . ? N5 C25 1.163(4) . ? O2 C12 1.408(5) . ? O2 C11 1.432(5) . ? O1 C9 1.421(4) . ? O1 C8 1.427(4) . ? N3 C19 1.508(4) . ? N3 C15 1.509(4) . ? N3 C16 1.515(4) . ? N3 H1A 0.9592 . ? O4 C17 1.407(5) . ? O4 C18 1.426(5) . ? C1 C2 1.384(4) . ? C1 H1 0.9500 . ? N2 C10 1.464(5) . ? N2 C6 1.471(4) . ? N2 C7 1.475(5) . ? C5 C4 1.386(4) . ? C5 H5 0.9500 . ? C20 C24 1.382(4) . ? C20 C21 1.386(4) . ? C20 C19 1.513(4) . ? C4 C3 1.391(5) . ? C4 H4 0.9500 . ? C8 C7 1.492(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C14 C15 1.507(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C2 C3 1.380(5) . ? C2 H2 0.9500 . ? C23 C24 1.375(4) . ? C23 H23 0.9500 . ? C16 C17 1.507(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C3 C6 1.512(4) . ? C21 C22 1.385(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C24 H24 0.9500 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C10 C11 1.480(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C13 C9 1.483(6) 3_556 ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C9 C13 1.483(6) 3_456 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C18 C12 1.481(7) 3_556 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C12 C18 1.481(7) 3_456 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? O10 H3A 0.8616 . ? O10 H2A 0.9688 . ? O9 C29 1.412(5) . ? O9 C26 1.422(5) . ? C26 C27 1.485(7) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C29 C28 1.515(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C27 C28 1.531(8) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 N5 Fe1 N5 180.0 5_656 . ? N5 Fe1 N1 90.72(9) 5_656 5_656 ? N5 Fe1 N1 89.28(9) . 5_656 ? N5 Fe1 N1 89.28(9) 5_656 . ? N5 Fe1 N1 90.72(9) . . ? N1 Fe1 N1 180.00(12) 5_656 . ? N5 Fe1 N4 89.51(9) 5_656 . ? N5 Fe1 N4 90.49(9) . . ? N1 Fe1 N4 92.84(8) 5_656 . ? N1 Fe1 N4 87.16(8) . . ? N5 Fe1 N4 90.49(9) 5_656 5_656 ? N5 Fe1 N4 89.51(9) . 5_656 ? N1 Fe1 N4 87.16(8) 5_656 5_656 ? N1 Fe1 N4 92.84(8) . 5_656 ? N4 Fe1 N4 180.00(8) . 5_656 ? O8 Cl1 O6 110.3(2) . . ? O8 Cl1 O7 110.1(2) . . ? O6 Cl1 O7 110.19(19) . . ? O8 Cl1 O5 109.09(17) . . ? O6 Cl1 O5 108.43(18) . . ? O7 Cl1 O5 108.6(2) . . ? C14 O3 C13 112.3(3) . . ? C22 N4 C23 115.9(2) . . ? C22 N4 Fe1 122.49(18) . . ? C23 N4 Fe1 119.09(19) . . ? C5 N1 C1 116.8(3) . . ? C5 N1 Fe1 123.69(19) . . ? C1 N1 Fe1 119.5(2) . . ? C25 N5 Fe1 162.1(2) . . ? C12 O2 C11 112.7(3) . . ? C9 O1 C8 113.5(3) . . ? C19 N3 C15 110.5(2) . . ? C19 N3 C16 110.1(2) . . ? C15 N3 C16 109.2(2) . . ? C19 N3 H1A 108.4 . . ? C15 N3 H1A 111.8 . . ? C16 N3 H1A 106.9 . . ? C17 O4 C18 113.0(3) . . ? N1 C1 C2 123.5(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? N5 C25 S1 178.6(3) . . ? C10 N2 C6 111.3(3) . . ? C10 N2 C7 111.1(3) . . ? C6 N2 C7 111.6(3) . . ? N1 C5 C4 123.0(3) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C24 C20 C21 117.4(3) . . ? C24 C20 C19 122.8(3) . . ? C21 C20 C19 119.5(3) . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? O1 C8 C7 108.5(3) . . ? O1 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O1 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? O3 C14 C15 107.3(2) . . ? O3 C14 H14A 110.3 . . ? C15 C14 H14A 110.3 . . ? O3 C14 H14B 110.3 . . ? C15 C14 H14B 110.3 . . ? H14A C14 H14B 108.5 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? N4 C23 C24 124.0(3) . . ? N4 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C17 C16 N3 114.7(3) . . ? C17 C16 H16A 108.6 . . ? N3 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? N3 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C2 C3 C4 117.6(3) . . ? C2 C3 C6 120.2(3) . . ? C4 C3 C6 122.1(3) . . ? C20 C21 C22 119.4(3) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? N4 C22 C21 123.7(3) . . ? N4 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? N2 C6 C3 114.0(3) . . ? N2 C6 H6A 108.7 . . ? C3 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C3 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C23 C24 C20 119.4(3) . . ? C23 C24 H24 120.3 . . ? C20 C24 H24 120.3 . . ? N3 C19 C20 114.9(2) . . ? N3 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? N3 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? O4 C17 C16 108.2(3) . . ? O4 C17 H17A 110.1 . . ? C16 C17 H17A 110.1 . . ? O4 C17 H17B 110.1 . . ? C16 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? C14 C15 N3 112.9(2) . . ? C14 C15 H15A 109.0 . . ? N3 C15 H15A 109.0 . . ? C14 C15 H15B 109.0 . . ? N3 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? N2 C10 C11 113.0(3) . . ? N2 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N2 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? O2 C11 C10 109.9(3) . . ? O2 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? O2 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N2 C7 C8 114.7(3) . . ? N2 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? N2 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? O3 C13 C9 108.8(3) . 3_556 ? O3 C13 H13A 109.9 . . ? C9 C13 H13A 109.9 3_556 . ? O3 C13 H13B 109.9 . . ? C9 C13 H13B 109.9 3_556 . ? H13A C13 H13B 108.3 . . ? O1 C9 C13 108.1(3) . 3_456 ? O1 C9 H9A 110.1 . . ? C13 C9 H9A 110.1 3_456 . ? O1 C9 H9B 110.1 . . ? C13 C9 H9B 110.1 3_456 . ? H9A C9 H9B 108.4 . . ? O4 C18 C12 108.6(3) . 3_556 ? O4 C18 H18A 110.0 . . ? C12 C18 H18A 110.0 3_556 . ? O4 C18 H18B 110.0 . . ? C12 C18 H18B 110.0 3_556 . ? H18A C18 H18B 108.3 . . ? O2 C12 C18 109.3(3) . 3_456 ? O2 C12 H12A 109.8 . . ? C18 C12 H12A 109.8 3_456 . ? O2 C12 H12B 109.8 . . ? C18 C12 H12B 109.8 3_456 . ? H12A C12 H12B 108.3 . . ? H3A O10 H2A 101.2 . . ? C29 O9 C26 109.5(3) . . ? O9 C26 C27 107.2(4) . . ? O9 C26 H26A 110.3 . . ? C27 C26 H26A 110.3 . . ? O9 C26 H26B 110.3 . . ? C27 C26 H26B 110.3 . . ? H26A C26 H26B 108.5 . . ? O9 C29 C28 106.5(4) . . ? O9 C29 H29A 110.4 . . ? C28 C29 H29A 110.4 . . ? O9 C29 H29B 110.4 . . ? C28 C29 H29B 110.4 . . ? H29A C29 H29B 108.6 . . ? C26 C27 C28 100.8(4) . . ? C26 C27 H27A 111.6 . . ? C28 C27 H27A 111.6 . . ? C26 C27 H27B 111.6 . . ? C28 C27 H27B 111.6 . . ? H27A C27 H27B 109.4 . . ? C29 C28 C27 104.6(4) . . ? C29 C28 H28A 110.8 . . ? C27 C28 H28A 110.8 . . ? C29 C28 H28B 110.8 . . ? C27 C28 H28B 110.8 . . ? H28A C28 H28B 108.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.525 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 898012' ####################################################################### # # 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_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H72 Cu N9 O8 S, C N S' _chemical_formula_sum 'C50 H72 Cu N10 O8 S2' _chemical_formula_weight 1068.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 4' _symmetry_space_group_name_Hall 'P 4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z' '-x, -y, z' 'y, -x, z' _cell_length_a 16.366(2) _cell_length_b 16.366(2) _cell_length_c 10.158(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2720.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 47462 _cell_measurement_theta_min 1.24 _cell_measurement_theta_max 31.41 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1134 _exptl_absorpt_coefficient_mu 0.538 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.710698 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 47462 _diffrn_reflns_av_R_equivalents 0.2118 _diffrn_reflns_av_sigmaI/netI 0.1244 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 31.41 _reflns_number_total 8316 _reflns_number_gt 3812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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^)+(0.2000P)^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 0.47(5) _refine_ls_number_reflns 8316 _refine_ls_number_parameters 249 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.2808 _refine_ls_R_factor_gt 0.2050 _refine_ls_wR_factor_ref 0.5275 _refine_ls_wR_factor_gt 0.4817 _refine_ls_goodness_of_fit_ref 1.550 _refine_ls_restrained_S_all 1.554 _refine_ls_shift/su_max 0.069 _refine_ls_shift/su_mean 0.013 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 Cu1 Cu 0.5000 0.5000 0.3567(2) 0.0595(6) Uani 1 4 d S . . C6 C 0.3533(5) 0.3980(5) 0.3092(11) 0.068(2) Uani 1 1 d . . . H6 H 0.3826 0.3854 0.2311 0.082 Uiso 1 1 calc R . . C3 C 0.2677(8) 0.4341(7) 0.5326(13) 0.090(3) Uani 1 1 d . . . H3 H 0.2415 0.4452 0.6140 0.108 Uiso 1 1 calc R . . C5 C 0.2794(6) 0.3585(6) 0.3343(12) 0.075(3) Uani 1 1 d . . . H5 H 0.2619 0.3171 0.2751 0.090 Uiso 1 1 calc R . . C4 C 0.2327(8) 0.3759(7) 0.4364(14) 0.085(3) Uani 1 1 d . . . Cu2 Cu 0.0000 0.0000 -0.0040(8) 0.178(3) Uani 1 4 d S . . C23 C 0.2656(10) 0.1203(10) -0.0864(18) 0.131(5) Uani 1 1 d DU . . C21 C 0.1469(10) 0.1023(12) 0.061(2) 0.145(6) Uani 1 1 d DU . . H21 H 0.1184 0.1163 0.1388 0.174 Uiso 1 1 calc R . . N4 N 0.3738(8) 0.2442(8) -0.0260(14) 0.121(4) Uani 1 1 d D . . C20 C 0.3526(11) 0.1629(8) -0.1098(18) 0.144(8) Uani 1 1 d . . . H20A H 0.3567 0.1769 -0.2043 0.173 Uiso 1 1 calc R . . H20B H 0.3954 0.1218 -0.0910 0.173 Uiso 1 1 calc R . . N5 N 0.1111(11) 0.0441(13) -0.030(2) 0.171(7) Uani 1 1 d DU . . C25 C 0.1670(10) 0.0328(12) -0.136(2) 0.151(5) Uani 1 1 d DU . . H25 H 0.1501 -0.0070 -0.1978 0.182 Uiso 1 1 calc R . . C24 C 0.2338(12) 0.0649(9) -0.162(3) 0.172(8) Uani 1 1 d DU . . H24 H 0.2622 0.0486 -0.2394 0.206 Uiso 1 1 calc R . . O3 O 0.2118(12) 0.3243(12) -0.039(2) 0.190(6) Uiso 1 1 d D . . C15 C 0.2747(12) 0.3159(11) -0.153(3) 0.168(8) Uiso 1 1 d D . . H15A H 0.2599 0.2679 -0.2077 0.202 Uiso 1 1 calc R . . H15B H 0.2711 0.3650 -0.2102 0.202 Uiso 1 1 calc R . . C14 C 0.3575(12) 0.3068(14) -0.109(3) 0.160(8) Uiso 1 1 d D . . H14A H 0.3930 0.3008 -0.1869 0.192 Uiso 1 1 calc R . . H14B H 0.3736 0.3582 -0.0640 0.192 Uiso 1 1 calc R . . C13 C 0.4575(8) 0.2544(9) 0.0318(17) 0.108(4) Uiso 1 1 d D . . H13A H 0.4989 0.2519 -0.0392 0.129 Uiso 1 1 calc R . . H13B H 0.4617 0.3086 0.0746 0.129 Uiso 1 1 calc R . . N3 N 0.1332(7) 0.2698(7) 0.4037(14) 0.116(5) Uani 1 1 d D . . C7 C 0.1622(9) 0.3368(10) 0.481(2) 0.129(7) Uani 1 1 d . . . H7A H 0.1180 0.3779 0.4866 0.155 Uiso 1 1 calc R . . H7B H 0.1726 0.3167 0.5713 0.155 Uiso 1 1 calc R . . O1 O 0.2987(6) 0.1683(6) 0.3839(11) 0.116(3) Uiso 1 1 d . . . C9 C 0.2588(7) 0.1704(8) 0.4739(14) 0.090(3) Uiso 1 1 d . . . H9A H 0.2820 0.2134 0.5315 0.108 Uiso 1 1 calc R . . H9B H 0.2671 0.1179 0.5204 0.108 Uiso 1 1 calc R . . C8 C 0.1645(9) 0.1853(9) 0.4708(18) 0.108(4) Uiso 1 1 d . . . H8A H 0.1441 0.1837 0.5625 0.129 Uiso 1 1 calc R . . H8B H 0.1389 0.1391 0.4231 0.129 Uiso 1 1 calc R . . O2 O 0.4229(7) 0.2129(7) 0.2303(14) 0.126(4) Uiso 1 1 d . . . C12 C 0.4727(12) 0.1944(13) 0.1224(16) 0.144(6) Uiso 1 1 d . . . H12A H 0.5310 0.1944 0.1484 0.173 Uiso 1 1 calc R . . H12B H 0.4588 0.1400 0.0861 0.173 Uiso 1 1 calc R . . C22 C 0.2187(8) 0.1360(11) 0.0356(19) 0.129(5) Uani 1 1 d DU . . H22 H 0.2413 0.1721 0.0992 0.155 Uiso 1 1 calc R . . C10 C 0.3874(9) 0.1616(9) 0.4001(16) 0.113(5) Uiso 1 1 d . . . H10A H 0.4044 0.2137 0.4413 0.136 Uiso 1 1 calc R . . H10B H 0.3954 0.1190 0.4680 0.136 Uiso 1 1 calc R . . C11 C 0.4393(10) 0.1475(11) 0.3162(16) 0.126(5) Uiso 1 1 d . . . H11A H 0.4307 0.0939 0.2733 0.152 Uiso 1 1 calc R . . H11B H 0.4954 0.1503 0.3526 0.152 Uiso 1 1 calc R . . S3 S 0.5000 0.0000 0.6829(11) 0.145(3) Uani 1 2 d S A 2 C27 C 0.5000 0.0000 0.838(2) 0.110(6) Uani 1 2 d S A 2 N7 N 0.5000 0.0000 0.963(7) 0.36(4) Uani 1 2 d SU A 2 N2 N 0.3835(4) 0.4528(4) 0.3920(8) 0.065(2) Uani 1 1 d . . . S2 S 0.0000 0.0000 0.4946(6) 0.0740(14) Uani 1 4 d S . . S1 S 0.5000 0.5000 -0.1420(13) 0.146(3) Uani 1 4 d S . . C2 C 0.3430(5) 0.4726(6) 0.4969(11) 0.070(2) Uani 1 1 d . . . H2 H 0.3641 0.5144 0.5522 0.084 Uiso 1 1 calc R . . N1 N 0.5000 0.5000 0.156(2) 0.073(4) Uani 1 4 d SD . . C26 C 0.0000 0.0000 0.341(2) 0.081(5) Uani 1 4 d S . . N6 N 0.0000 0.0000 0.214(3) 0.190(19) Uani 1 4 d S . . C17 C 0.0784(18) 0.328(2) 0.020(4) 0.195(11) Uiso 1 1 d . . . H17A H 0.0572 0.3842 0.0328 0.234 Uiso 1 1 calc R . . H17B H 0.0325 0.2984 -0.0222 0.234 Uiso 1 1 calc R . . O4 O 0.0742(10) 0.3003(10) 0.1374(18) 0.165(6) Uiso 1 1 d D . . C1 C 0.5000 0.5000 0.039(3) 0.18(3) Uani 1 4 d SD . . C16 C 0.1358(13) 0.3416(17) -0.102(3) 0.179(10) Uiso 1 1 d D . . H16A H 0.1240 0.3028 -0.1743 0.215 Uiso 1 1 calc R . . H16B H 0.1333 0.3984 -0.1355 0.215 Uiso 1 1 calc R . . C19 C 0.0446(8) 0.2675(10) 0.3951(15) 0.118(5) Uiso 1 1 d D . . H19A H 0.0189 0.3026 0.4628 0.141 Uiso 1 1 calc R . . H19B H 0.0234 0.2111 0.4035 0.141 Uiso 1 1 calc R . . C18 C 0.0317(12) 0.2999(14) 0.2628(17) 0.147(6) Uiso 1 1 d D . . H18A H 0.0224 0.3588 0.2794 0.176 Uiso 1 1 calc R . . H18B H -0.0226 0.2778 0.2392 0.176 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 Cu1 0.0500(6) 0.0500(6) 0.0787(14) 0.000 0.000 0.000 C6 0.060(4) 0.061(4) 0.084(6) -0.014(4) 0.002(4) 0.002(3) C3 0.113(8) 0.077(6) 0.080(7) -0.027(5) -0.001(6) -0.001(6) C5 0.076(5) 0.065(4) 0.084(8) 0.009(5) 0.013(5) -0.015(4) C4 0.088(7) 0.071(6) 0.097(8) 0.004(5) -0.010(6) -0.012(5) Cu2 0.185(4) 0.185(4) 0.165(6) 0.000 0.000 0.000 C23 0.136(10) 0.133(10) 0.124(11) 0.074(8) 0.055(8) 0.068(8) C21 0.106(10) 0.188(18) 0.140(14) 0.055(10) 0.040(9) 0.019(9) N4 0.120(9) 0.106(8) 0.136(11) 0.046(8) 0.027(8) 0.028(6) C20 0.179(16) 0.075(7) 0.18(2) 0.011(9) 0.092(15) 0.028(8) N5 0.142(13) 0.22(2) 0.145(15) 0.033(12) 0.021(9) 0.015(10) C25 0.169(13) 0.151(12) 0.134(11) 0.083(9) 0.036(10) 0.040(9) C24 0.218(18) 0.077(7) 0.221(18) 0.050(9) 0.092(16) 0.014(9) N3 0.100(7) 0.092(6) 0.157(12) -0.037(7) 0.044(7) -0.046(5) C7 0.113(10) 0.107(10) 0.166(17) -0.036(10) 0.058(11) -0.030(8) C22 0.089(7) 0.161(12) 0.136(11) 0.075(8) 0.034(7) 0.048(7) S3 0.129(5) 0.137(5) 0.168(7) 0.000 0.000 0.035(4) C27 0.18(2) 0.079(9) 0.074(14) 0.000 0.000 0.004(10) N7 0.54(8) 0.21(4) 0.33(7) 0.000 0.000 0.06(4) N2 0.066(4) 0.052(3) 0.076(6) 0.000(3) -0.007(3) 0.003(3) S2 0.0634(16) 0.0634(16) 0.095(4) 0.000 0.000 0.000 S1 0.167(5) 0.167(5) 0.105(6) 0.000 0.000 0.000 C2 0.054(4) 0.064(5) 0.092(7) -0.002(4) 0.002(4) -0.005(3) N1 0.071(6) 0.071(6) 0.079(11) 0.000 0.000 0.000 C26 0.092(7) 0.092(7) 0.058(12) 0.000 0.000 0.000 N6 0.25(3) 0.25(3) 0.071(18) 0.000 0.000 0.000 C1 0.062(9) 0.062(9) 0.43(10) 0.000 0.000 0.000 _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 Cu1 N1 2.04(2) . ? Cu1 N2 2.089(7) . ? Cu1 N2 2.089(7) 3_665 ? Cu1 N2 2.089(7) 4_565 ? Cu1 N2 2.089(7) 2_655 ? C6 N2 1.324(12) . ? C6 C5 1.395(13) . ? C6 H6 0.9500 . ? C3 C2 1.431(16) . ? C3 C4 1.479(16) . ? C3 H3 0.9500 . ? C5 C4 1.320(17) . ? C5 H5 0.9500 . ? C4 C7 1.394(17) . ? Cu2 N5 1.974(19) 3 ? Cu2 N5 1.974(19) 4 ? Cu2 N5 1.974(19) . ? Cu2 N5 1.974(19) 2 ? Cu2 N6 2.22(4) . ? C23 C24 1.30(3) . ? C23 C22 1.48(2) . ? C23 C20 1.60(2) . ? C21 C22 1.32(2) . ? C21 N5 1.45(3) . ? C21 H21 0.9500 . ? N4 C14 1.35(2) . ? N4 C13 1.501(14) . ? N4 C20 1.62(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? N5 C25 1.42(3) . ? C25 C24 1.243(16) . ? C25 H25 0.9500 . ? C24 H24 0.9500 . ? O3 C16 1.430(17) . ? O3 C15 1.56(3) . ? C15 C14 1.438(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C13 C12 1.37(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N3 C7 1.430(17) . ? N3 C19 1.453(14) . ? N3 C8 1.63(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? O1 C9 1.124(15) . ? O1 C10 1.465(17) . ? C9 C8 1.563(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O2 C11 1.41(2) . ? O2 C12 1.40(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C22 H22 0.9500 . ? C10 C11 1.225(13) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? S3 C27 1.57(2) . ? C27 N7 1.28(7) . ? N2 C2 1.296(13) . ? S2 C26 1.56(3) . ? S1 C1 1.84(3) . ? C2 H2 0.9500 . ? N1 C1 1.19(2) . ? C26 N6 1.29(4) . ? C17 O4 1.28(4) . ? C17 C16 1.57(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? O4 C18 1.451(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C19 C18 1.460(13) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 99.9(2) . . ? N1 Cu1 N2 99.9(2) . 3_665 ? N2 Cu1 N2 160.3(5) . 3_665 ? N1 Cu1 N2 99.9(2) . 4_565 ? N2 Cu1 N2 88.32(8) . 4_565 ? N2 Cu1 N2 88.32(8) 3_665 4_565 ? N1 Cu1 N2 99.9(2) . 2_655 ? N2 Cu1 N2 88.32(8) . 2_655 ? N2 Cu1 N2 88.32(8) 3_665 2_655 ? N2 Cu1 N2 160.3(5) 4_565 2_655 ? N2 C6 C5 121.4(10) . . ? N2 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C2 C3 C4 116.8(11) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 121.6 . . ? C4 C5 C6 123.0(10) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C5 C4 C7 129.4(12) . . ? C5 C4 C3 115.7(11) . . ? C7 C4 C3 113.7(13) . . ? N5 Cu2 N5 88.96(18) 3 4 ? N5 Cu2 N5 164.5(14) 3 . ? N5 Cu2 N5 88.96(18) 4 . ? N5 Cu2 N5 88.96(18) 3 2 ? N5 Cu2 N5 164.5(14) 4 2 ? N5 Cu2 N5 88.96(18) . 2 ? N5 Cu2 N6 97.8(7) 3 . ? N5 Cu2 N6 97.8(7) 4 . ? N5 Cu2 N6 97.8(7) . . ? N5 Cu2 N6 97.8(7) 2 . ? C24 C23 C22 114(2) . . ? C24 C23 C20 124.9(15) . . ? C22 C23 C20 121(2) . . ? C22 C21 N5 121(2) . . ? C22 C21 H21 119.6 . . ? N5 C21 H21 119.6 . . ? C14 N4 C13 109.7(13) . . ? C14 N4 C20 104.8(16) . . ? C13 N4 C20 119.6(11) . . ? C23 C20 N4 118.1(13) . . ? C23 C20 H20A 107.8 . . ? N4 C20 H20A 107.8 . . ? C23 C20 H20B 107.8 . . ? N4 C20 H20B 107.8 . . ? H20A C20 H20B 107.1 . . ? C25 N5 C21 107.7(19) . . ? C25 N5 Cu2 130(2) . . ? C21 N5 Cu2 121.8(15) . . ? C24 C25 N5 133(3) . . ? C24 C25 H25 113.7 . . ? N5 C25 H25 113.7 . . ? C23 C24 C25 121(3) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C16 O3 C15 104.7(19) . . ? C14 C15 O3 113(2) . . ? C14 C15 H15A 108.9 . . ? O3 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? O3 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? N4 C14 C15 117.4(19) . . ? N4 C14 H14A 107.9 . . ? C15 C14 H14A 108.0 . . ? N4 C14 H14B 107.9 . . ? C15 C14 H14B 107.9 . . ? H14A C14 H14B 107.2 . . ? C12 C13 N4 110.4(13) . . ? C12 C13 H13A 109.6 . . ? N4 C13 H13A 109.6 . . ? C12 C13 H13B 109.6 . . ? N4 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C7 N3 C19 112.6(11) . . ? C7 N3 C8 108.5(15) . . ? C19 N3 C8 108.6(9) . . ? C4 C7 N3 116.7(13) . . ? C4 C7 H7A 108.1 . . ? N3 C7 H7A 108.1 . . ? C4 C7 H7B 108.1 . . ? N3 C7 H7B 108.2 . . ? H7A C7 H7B 107.3 . . ? C9 O1 C10 119.1(13) . . ? O1 C9 C8 124.2(13) . . ? O1 C9 H9A 106.3 . . ? C8 C9 H9A 106.3 . . ? O1 C9 H9B 106.3 . . ? C8 C9 H9B 106.3 . . ? H9A C9 H9B 106.4 . . ? C9 C8 N3 116.9(11) . . ? C9 C8 H8A 108.1 . . ? N3 C8 H8A 108.1 . . ? C9 C8 H8B 108.1 . . ? N3 C8 H8B 108.0 . . ? H8A C8 H8B 107.3 . . ? C11 O2 C12 102.1(12) . . ? C13 C12 O2 105.4(17) . . ? C13 C12 H12A 110.7 . . ? O2 C12 H12A 110.7 . . ? C13 C12 H12B 110.7 . . ? O2 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C21 C22 C23 123(2) . . ? C21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C11 C10 O1 128.6(17) . . ? C11 C10 H10A 105.1 . . ? O1 C10 H10A 105.2 . . ? C11 C10 H10B 105.2 . . ? O1 C10 H10B 105.2 . . ? H10A C10 H10B 105.9 . . ? C10 C11 O2 99.0(13) . . ? C10 C11 H11A 111.9 . . ? O2 C11 H11A 111.9 . . ? C10 C11 H11B 112.0 . . ? O2 C11 H11B 112.0 . . ? H11A C11 H11B 109.7 . . ? N7 C27 S3 180.000(14) . . ? C2 N2 C6 120.1(8) . . ? C2 N2 Cu1 121.0(6) . . ? C6 N2 Cu1 118.8(7) . . ? N2 C2 C3 122.5(9) . . ? N2 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C1 N1 Cu1 180.000(4) . . ? N6 C26 S2 180.000(2) . . ? C26 N6 Cu2 180.000(2) . . ? O4 C17 C16 145(3) . . ? O4 C17 H17A 100.7 . . ? C16 C17 H17A 100.6 . . ? O4 C17 H17B 100.7 . . ? C16 C17 H17B 100.7 . . ? H17A C17 H17B 104.4 . . ? C17 O4 C18 148(2) . . ? N1 C1 S1 180.000(4) . . ? O3 C16 C17 98(2) . . ? O3 C16 H16A 112.2 . . ? C17 C16 H16A 112.1 . . ? O3 C16 H16B 112.2 . . ? C17 C16 H16B 112.2 . . ? H16A C16 H16B 109.8 . . ? N3 C19 C18 100.9(14) . . ? N3 C19 H19A 111.6 . . ? C18 C19 H19A 111.6 . . ? N3 C19 H19B 111.6 . . ? C18 C19 H19B 111.6 . . ? H19A C19 H19B 109.4 . . ? C19 C18 O4 137.8(18) . . ? C19 C18 H18A 102.6 . . ? O4 C18 H18A 102.7 . . ? C19 C18 H18B 102.7 . . ? O4 C18 H18B 102.7 . . ? H18A C18 H18B 105.0 . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 31.41 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 1.438 _refine_diff_density_min -1.651 _refine_diff_density_rms 0.152 _database_code_depnum_ccdc_archive 'CCDC 898013'