# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Leonard Lindoy' _publ_contact_author_email lindoy@gmail.com _publ_section_title ; Comparative investigation of the interaction of Co(II), Ni(II) and Cu(II) with dibenzo-substituted macrocyclic ligands incorporating both symmetrically and unsymmetrically arranged N, O and S donors. Synthetic, X-ray and solution studies ; _publ_author_name L.Lindoy # Attachment '- newcombined_revised.CIF' data_nsncu _database_code_depnum_ccdc_archive 'CCDC 819258' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28.125 Cl2 Cu N3 O3.375 S' _chemical_formula_sum 'C20 H28.125 Cl2 Cu N3 O3.375 S' _chemical_formula_weight 531.08 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' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_international_tables_no 15 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 16.9284(17) _cell_length_b 16.2096(17) _cell_length_c 38.129(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.261(4) _cell_angle_gamma 90.00 _cell_volume 10418.5(18) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8568 _cell_measurement_theta_min 2.501 _cell_measurement_theta_max 21.96 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.0750 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4402 _exptl_absorpt_coefficient_mu 1.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23228 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 22.05 _reflns_number_total 6334 _reflns_number_gt 5150 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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. These crystals were very small and despite appearing (at least visually) to be of good quality they were poorly diffracting, with few reflections recorded above 1 resolution. This complex crystallises with two molecules in the asymmetric unit and the uncoordinated anions and solvent water molecules are disordered. The 4.75 water molecules were modelled over 14 positions and their hydrogen atoms could not be located in the difference Fourier map. In addition, the uncoordinated chloride ions were modelled over eight positions often with water molecules in close proximity. One of the coordinated chlorides (Cl(3)) was modelled over two (0.75 and 0.25 occupancy) positions. The phenyl ring of the Cu(1)-containing macrocycle appears to be disordered, however, as no satisfactoy model was found the ellipsoids were contrainted with EADP commands. Similar constraints were applied to the disordered chloride ions, acetonitrile and the anisotropically refined partial occupancy water molecules. The large amount of disordered solvent presumeably contributes to the poor diffraction. ; _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^)+(0.1583P)^2^+91.0995P] 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 6334 _refine_ls_number_parameters 559 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2465 _refine_ls_wR_factor_gt 0.2343 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 C1B C 0.2470(16) 0.3229(13) 0.2761(5) 0.043(3) Uani 0.40 1 d P A 1 H1B1 H 0.2766 0.2882 0.2942 0.051 Uiso 0.40 1 calc PR A 1 H1B2 H 0.1945 0.3379 0.2837 0.051 Uiso 0.40 1 calc PR A 1 C2B C 0.2959(14) 0.3998(14) 0.2652(6) 0.042(3) Uani 0.40 1 d P A 1 H2B1 H 0.3239 0.4259 0.2863 0.050 Uiso 0.40 1 calc PR A 1 H2B2 H 0.3357 0.3828 0.2492 0.050 Uiso 0.40 1 calc PR A 1 C1A C 0.2536(10) 0.3980(9) 0.2795(4) 0.043(3) Uani 0.60 1 d P A 2 H1A1 H 0.2870 0.4239 0.2992 0.051 Uiso 0.60 1 calc PR A 2 H1A2 H 0.2025 0.3808 0.2879 0.051 Uiso 0.60 1 calc PR A 2 C2A C 0.2940(9) 0.3289(9) 0.2646(4) 0.042(3) Uani 0.60 1 d P A 2 H2A1 H 0.3134 0.2906 0.2837 0.050 Uiso 0.60 1 calc PR A 2 H2A2 H 0.3407 0.3496 0.2534 0.050 Uiso 0.60 1 calc PR A 2 C3 C 0.1937(4) 0.5190(5) 0.2564(2) 0.0367(19) Uani 1 1 d . . . C4 C 0.1658(4) 0.5726(5) 0.2293(2) 0.0374(19) Uani 1 1 d . . . C5 C 0.1183(5) 0.6390(5) 0.2375(3) 0.054(3) Uani 1 1 d . . . H5 H 0.0985 0.6756 0.2193 0.065 Uiso 1 1 calc R A . C6 C 0.1000(6) 0.6523(7) 0.2708(4) 0.072(3) Uani 1 1 d . . . H6 H 0.0690 0.6991 0.2756 0.087 Uiso 1 1 calc R . . C7 C 0.1241(7) 0.6019(10) 0.2970(4) 0.082(4) Uani 1 1 d . . . H7 H 0.1092 0.6124 0.3200 0.098 Uiso 1 1 calc R A . C8 C 0.1712(6) 0.5336(7) 0.2911(2) 0.065(3) Uani 1 1 d . . . H8 H 0.1880 0.4973 0.3099 0.078 Uiso 1 1 calc R . . C9 C 0.1877(6) 0.5605(6) 0.1924(2) 0.053(2) Uani 1 1 d . . . H9A H 0.1702 0.6096 0.1783 0.064 Uiso 1 1 calc R A . H9B H 0.2462 0.5575 0.1930 0.064 Uiso 1 1 calc R . . C10 C 0.0658(5) 0.4893(6) 0.1681(3) 0.063(3) Uani 1 1 d . . . H10A H 0.0488 0.4542 0.1475 0.075 Uiso 1 1 calc R A . H10B H 0.0489 0.5465 0.1623 0.075 Uiso 1 1 calc R . . C11 C 0.0248(5) 0.4600(5) 0.1994(3) 0.054(2) Uani 1 1 d . A . H11A H -0.0307 0.4457 0.1913 0.065 Uiso 1 1 calc R . . H11B H 0.0236 0.5060 0.2164 0.065 Uiso 1 1 calc R . . C12 C 0.0270(5) 0.2889(5) 0.1957(2) 0.048(2) Uani 1 1 d . A . H12A H 0.0307 0.2379 0.2100 0.057 Uiso 1 1 calc R . . H12B H -0.0300 0.3011 0.1898 0.057 Uiso 1 1 calc R . . C13 C 0.0648(5) 0.2732(6) 0.1618(2) 0.056(2) Uani 1 1 d . . . H13A H 0.0490 0.2177 0.1529 0.067 Uiso 1 1 calc R . . H13B H 0.0440 0.3141 0.1439 0.067 Uiso 1 1 calc R . . C14 C 0.1919(6) 0.1977(6) 0.1774(2) 0.061(3) Uani 1 1 d . . . H14A H 0.1759 0.1544 0.1599 0.073 Uiso 1 1 calc R B 1 H14B H 0.2503 0.2040 0.1784 0.073 Uiso 1 1 calc R B 1 C15 C 0.1703(5) 0.1716(6) 0.2119(3) 0.0598(11) Uani 1 1 d . A 1 C16 C 0.1937(5) 0.2165(6) 0.2424(3) 0.0598(11) Uani 1 1 d . A 1 C17 C 0.1669(5) 0.1947(6) 0.2746(3) 0.0598(11) Uani 1 1 d . A 1 H17 H 0.1819 0.2276 0.2948 0.072 Uiso 1 1 calc R A 1 C18 C 0.1225(5) 0.1315(6) 0.2779(3) 0.0598(11) Uani 1 1 d . A 1 H18 H 0.1042 0.1195 0.3002 0.072 Uiso 1 1 calc R A 1 C19 C 0.1018(5) 0.0831(6) 0.2510(3) 0.0598(11) Uani 1 1 d . A 1 H19 H 0.0715 0.0351 0.2548 0.072 Uiso 1 1 calc R A 1 C20 C 0.1232(5) 0.0997(6) 0.2159(3) 0.0598(11) Uani 1 1 d . A 1 H20A H 0.1069 0.0647 0.1966 0.072 Uiso 0.60 1 calc PR A 1 C21 C 0.4799(5) 0.7056(5) 0.0711(2) 0.052(2) Uani 1 1 d . . . H21A H 0.4961 0.6855 0.0483 0.062 Uiso 1 1 calc R . . H21B H 0.5166 0.7500 0.0799 0.062 Uiso 1 1 calc R . . C22 C 0.3966(6) 0.7365(5) 0.0668(2) 0.056(2) Uani 1 1 d . . . H22A H 0.3808 0.7529 0.0902 0.067 Uiso 1 1 calc R . . H22B H 0.3943 0.7864 0.0518 0.067 Uiso 1 1 calc R . . C23 C 0.3247(5) 0.6728(5) 0.0131(2) 0.041(2) Uani 1 1 d . . . C24 C 0.2615(5) 0.6255(5) -0.0010(2) 0.046(2) Uani 1 1 d . . . C25 C 0.2460(6) 0.6233(6) -0.0378(3) 0.061(3) Uani 1 1 d . . . H25 H 0.2021 0.5929 -0.0483 0.074 Uiso 1 1 calc R . . C26 C 0.2956(8) 0.6661(7) -0.0589(3) 0.069(3) Uani 1 1 d . . . H26 H 0.2851 0.6640 -0.0838 0.083 Uiso 1 1 calc R . . C27 C 0.3581(7) 0.7103(6) -0.0447(3) 0.060(3) Uani 1 1 d . . . H27 H 0.3909 0.7387 -0.0596 0.072 Uiso 1 1 calc R . . C28 C 0.3748(6) 0.7146(5) -0.0087(2) 0.050(2) Uani 1 1 d . . . H28 H 0.4191 0.7452 0.0013 0.060 Uiso 1 1 calc R . . C29 C 0.2114(5) 0.5757(6) 0.0216(3) 0.061(3) Uani 1 1 d . . . H29A H 0.1895 0.6122 0.0391 0.073 Uiso 1 1 calc R . . H29B H 0.1664 0.5514 0.0067 0.073 Uiso 1 1 calc R . . C30 C 0.2832(6) 0.4461(5) 0.0161(3) 0.054(2) Uani 1 1 d . . . H30A H 0.2421 0.4406 -0.0040 0.065 Uiso 1 1 calc R . . H30B H 0.2873 0.3924 0.0285 0.065 Uiso 1 1 calc R . . C31 C 0.3609(5) 0.4647(5) 0.0021(2) 0.047(2) Uani 1 1 d . . . H31A H 0.3518 0.5055 -0.0171 0.056 Uiso 1 1 calc R . . H31B H 0.3808 0.4136 -0.0082 0.056 Uiso 1 1 calc R . . C32 C 0.4709(5) 0.4144(5) 0.0591(2) 0.052(2) Uani 1 1 d . . . H32A H 0.4690 0.3663 0.0431 0.062 Uiso 1 1 calc R . . H32B H 0.5268 0.4226 0.0685 0.062 Uiso 1 1 calc R . . C33 C 0.4223(6) 0.3952(5) 0.0895(3) 0.055(2) Uani 1 1 d . . . H33A H 0.3737 0.3652 0.0804 0.066 Uiso 1 1 calc R . . H33B H 0.4534 0.3586 0.1063 0.066 Uiso 1 1 calc R . . C34 C 0.4619(6) 0.5007(6) 0.1355(2) 0.054(2) Uani 1 1 d . . . H34A H 0.4413 0.5501 0.1469 0.065 Uiso 1 1 calc R . . H34B H 0.4709 0.4575 0.1538 0.065 Uiso 1 1 calc R . . C35 C 0.5398(5) 0.5221(5) 0.1224(2) 0.046(2) Uani 1 1 d . . . C36 C 0.5476(5) 0.5924(5) 0.1020(2) 0.0381(19) Uani 1 1 d . . . C37 C 0.6189(5) 0.6132(5) 0.0894(2) 0.047(2) Uani 1 1 d . . . H37 H 0.6234 0.6611 0.0753 0.057 Uiso 1 1 calc R . . C38 C 0.6843(6) 0.5620(6) 0.0978(2) 0.056(3) Uani 1 1 d . . . H38 H 0.7336 0.5746 0.0891 0.067 Uiso 1 1 calc R . . C39 C 0.6780(6) 0.4934(6) 0.1186(2) 0.054(2) Uani 1 1 d . . . H39 H 0.7230 0.4597 0.1249 0.064 Uiso 1 1 calc R . . C40 C 0.6067(6) 0.4744(6) 0.1302(2) 0.053(2) Uani 1 1 d . . . H40 H 0.6026 0.4263 0.1441 0.063 Uiso 1 1 calc R . . N1A N 0.2408(4) 0.4562(4) 0.2479(2) 0.0438(18) Uani 0.60 1 d P A 1 H1A H 0.2775 0.4879 0.2371 0.053 Uiso 0.60 1 calc PR A 1 N1B N 0.2408(4) 0.4562(4) 0.2479(2) 0.0438(18) Uani 0.40 1 d P A 2 H1B H 0.2899 0.4784 0.2439 0.053 Uiso 0.40 1 calc PR A 2 N2 N 0.1540(4) 0.4868(4) 0.17433(18) 0.0487(18) Uani 1 1 d . A . H2 H 0.1727 0.4869 0.1522 0.058 Uiso 1 1 calc R . . N3 N 0.1529(4) 0.2783(5) 0.16578(18) 0.055(2) Uani 1 1 d . A . H3 H 0.1685 0.2894 0.1435 0.066 Uiso 1 1 calc R . . N4 N 0.3391(4) 0.6755(4) 0.05107(16) 0.0407(16) Uani 1 1 d . G . H4 H 0.2909 0.6932 0.0583 0.049 Uiso 1 1 calc R . . N5 N 0.2579(4) 0.5089(5) 0.0402(2) 0.0528(19) Uani 1 1 d . G . H5A H 0.2240 0.4827 0.0545 0.063 Uiso 1 1 calc R . . N6 N 0.3996(4) 0.4706(4) 0.10810(17) 0.0456(17) Uani 1 1 d . G . H6A H 0.3572 0.4547 0.1205 0.055 Uiso 1 1 calc R . . O1 O 0.2419(4) 0.2837(4) 0.23828(18) 0.0636(18) Uani 1 1 d . . . O2 O 0.4805(3) 0.6391(3) 0.09622(14) 0.0453(14) Uani 1 1 d . G . S1 S 0.07107(11) 0.37225(13) 0.22164(5) 0.0407(6) Uani 1 1 d . . . S2 S 0.43800(12) 0.50443(12) 0.03416(5) 0.0402(5) Uani 1 1 d . G . Cl1 Cl 0.31929(11) 0.38532(13) 0.17612(5) 0.0460(6) Uani 1 1 d . . . Cl2A Cl 0.8550(7) 0.3557(6) 0.1499(3) 0.0537(13) Uani 0.25 1 d P C 1 Cl2B Cl 0.0392(8) 0.7471(7) 0.1523(3) 0.0537(13) Uani 0.25 1 d P D 2 Cl2C Cl 0.7188(6) 0.2747(5) 0.1458(2) 0.0537(13) Uani 0.25 1 d P E 3 Cl2D Cl 0.9628(6) 0.5616(5) 0.0605(2) 0.0537(13) Uani 0.25 1 d P F 4 Cl3A Cl 0.2750(2) 0.6012(2) 0.11797(8) 0.0492(8) Uani 0.75 1 d P G 1 Cl3B Cl 0.3002(7) 0.6391(7) 0.1222(3) 0.0492(8) Uani 0.25 1 d P G 2 Cl4A Cl 0.1718(5) 0.3757(5) 0.0922(2) 0.0548(14) Uani 0.35 1 d P H 4 Cl4B Cl 0.4940(7) 0.3711(8) 0.2157(3) 0.0548(14) Uani 0.25 1 d P I 2 Cl4C Cl 0.0910(5) 0.3643(6) 0.0451(2) 0.0548(14) Uani 0.25 1 d P J 3 Cl4D Cl 0.9016(10) 0.4719(12) 0.1042(5) 0.0548(14) Uani 0.15 1 d P K 1 O1W O 0.8662(8) 0.3839(8) 0.1411(3) 0.0504(17) Uani 0.50 1 d P L 2 O2W O 0.1463(8) 0.4044(9) 0.0938(3) 0.0504(17) Uani 0.50 1 d P M 2 O3W O 0.0522(11) 0.7654(11) 0.1650(4) 0.0504(17) Uani 0.50 1 d P N 3 O4W O 0.1959(9) 0.3514(9) 0.0894(4) 0.0504(17) Uani 0.50 1 d P O 3 O5W O 0.6092(7) 0.7633(7) 0.0020(3) 0.0504(17) Uani 0.50 1 d P P 3 O10W O 0.9879(14) 0.4429(15) 0.0409(7) 0.053(6) Uiso 0.25 1 d P Q 2 O6W O 0.071(2) 0.775(3) 0.1534(13) 0.091(14) Uiso 0.25 1 d P R 5 O7W O 0.9410(13) 0.6586(14) 0.1143(6) 0.049(6) Uiso 0.25 1 d P S 5 O8W O 0.0315(15) 0.4459(15) 0.0623(7) 0.058(6) Uiso 0.25 1 d P T 4 O9W O 0.4942(14) 0.3416(13) 0.2090(6) 0.030(6) Uiso 0.25 1 d P U 4 O11W O 0.002(2) 0.375(2) -0.0021(9) 0.092(10) Uiso 0.25 1 d P V 4 O13W O 0.0740(17) 0.5963(18) 0.0900(8) 0.073(8) Uiso 0.25 1 d P W 4 O14W O 0.8967(15) 0.4985(16) 0.0936(7) 0.051(7) Uiso 0.25 1 d P X 3 O15W O 0.0242(19) 0.6130(18) 0.0564(8) 0.079(8) Uiso 0.25 1 d P Y 3 Cu1 Cu 0.19615(5) 0.37794(5) 0.19872(2) 0.0315(3) Uani 1 1 d . A . Cu2 Cu 0.35679(6) 0.56099(6) 0.07574(2) 0.0396(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1B 0.058(8) 0.039(6) 0.031(7) 0.001(6) -0.001(6) 0.000(7) C2B 0.043(7) 0.050(7) 0.030(7) 0.004(7) -0.005(6) -0.002(8) C1A 0.058(8) 0.039(6) 0.031(7) 0.001(6) -0.001(6) 0.000(7) C2A 0.043(7) 0.050(7) 0.030(7) 0.004(7) -0.005(6) -0.002(8) C3 0.033(4) 0.031(5) 0.046(5) 0.000(4) 0.001(4) -0.012(4) C4 0.030(4) 0.039(5) 0.044(5) -0.003(4) 0.008(4) -0.012(4) C5 0.035(5) 0.038(5) 0.090(8) 0.000(5) 0.007(5) -0.009(4) C6 0.050(6) 0.063(7) 0.108(10) -0.053(7) 0.033(7) -0.021(5) C7 0.062(7) 0.117(11) 0.073(8) -0.060(8) 0.043(7) -0.054(8) C8 0.061(6) 0.090(8) 0.041(6) 0.009(5) -0.008(5) -0.052(6) C9 0.056(6) 0.059(6) 0.047(5) 0.002(4) 0.010(4) -0.020(4) C10 0.051(6) 0.050(6) 0.081(7) 0.001(5) -0.024(5) -0.006(5) C11 0.029(4) 0.043(5) 0.091(7) -0.014(5) 0.002(5) 0.002(4) C12 0.034(4) 0.040(5) 0.068(6) -0.005(4) 0.000(4) 0.004(4) C13 0.062(6) 0.051(6) 0.049(5) -0.011(4) -0.025(5) 0.014(5) C14 0.074(6) 0.064(6) 0.043(5) -0.001(5) 0.001(5) 0.037(5) C15 0.040(2) 0.057(3) 0.081(3) 0.015(2) 0.002(2) 0.0161(18) C16 0.040(2) 0.057(3) 0.081(3) 0.015(2) 0.002(2) 0.0161(18) C17 0.040(2) 0.057(3) 0.081(3) 0.015(2) 0.002(2) 0.0161(18) C18 0.040(2) 0.057(3) 0.081(3) 0.015(2) 0.002(2) 0.0161(18) C19 0.040(2) 0.057(3) 0.081(3) 0.015(2) 0.002(2) 0.0161(18) C20 0.040(2) 0.057(3) 0.081(3) 0.015(2) 0.002(2) 0.0161(18) C21 0.064(6) 0.036(5) 0.053(5) 0.002(4) -0.006(5) 0.003(4) C22 0.074(6) 0.041(5) 0.051(5) -0.008(4) -0.009(5) 0.012(5) C23 0.052(5) 0.036(5) 0.036(5) 0.005(4) 0.003(4) 0.030(4) C24 0.049(5) 0.043(5) 0.044(5) -0.006(4) -0.010(4) 0.021(4) C25 0.074(7) 0.051(6) 0.054(6) -0.007(5) -0.021(6) 0.029(5) C26 0.118(10) 0.055(6) 0.035(5) 0.006(5) 0.004(6) 0.052(7) C27 0.082(7) 0.052(6) 0.049(6) 0.014(5) 0.018(5) 0.036(6) C28 0.063(6) 0.047(5) 0.041(5) 0.011(4) 0.005(4) 0.023(4) C29 0.046(5) 0.065(6) 0.073(7) -0.005(5) 0.010(5) 0.014(5) C30 0.060(6) 0.043(5) 0.059(6) 0.003(4) 0.001(5) 0.002(4) C31 0.054(5) 0.045(5) 0.041(5) -0.007(4) 0.005(4) 0.011(4) C32 0.044(5) 0.048(5) 0.063(6) -0.018(5) -0.005(4) 0.019(4) C33 0.063(6) 0.035(5) 0.065(6) 0.017(4) -0.004(5) 0.003(4) C34 0.067(6) 0.070(6) 0.026(4) 0.014(4) 0.012(4) 0.017(5) C35 0.057(6) 0.056(6) 0.025(4) -0.005(4) -0.006(4) 0.017(5) C36 0.041(5) 0.042(5) 0.030(4) -0.003(4) -0.006(4) 0.006(4) C37 0.057(6) 0.046(5) 0.036(5) -0.010(4) -0.009(4) 0.002(4) C38 0.050(6) 0.073(7) 0.044(5) -0.022(5) -0.004(4) -0.004(5) C39 0.047(6) 0.059(6) 0.053(6) -0.016(5) -0.006(5) 0.010(5) C40 0.068(7) 0.046(5) 0.043(5) -0.003(4) -0.002(5) 0.017(5) N1A 0.029(3) 0.025(3) 0.073(5) 0.017(3) -0.018(3) -0.012(3) N1B 0.029(3) 0.025(3) 0.073(5) 0.017(3) -0.018(3) -0.012(3) N2 0.050(4) 0.062(5) 0.034(4) -0.004(3) 0.002(3) -0.009(4) N3 0.061(5) 0.071(5) 0.034(4) 0.002(4) 0.009(3) 0.035(4) N4 0.048(4) 0.043(4) 0.031(4) -0.005(3) 0.002(3) 0.020(3) N5 0.040(4) 0.059(5) 0.061(5) 0.015(4) 0.017(4) 0.006(4) N6 0.039(4) 0.061(5) 0.038(4) 0.018(3) 0.010(3) 0.003(3) O1 0.054(4) 0.046(4) 0.085(5) -0.015(3) -0.024(3) 0.007(3) O2 0.059(4) 0.038(3) 0.037(3) -0.004(3) -0.004(3) 0.010(3) S1 0.0281(10) 0.0530(13) 0.0419(12) -0.0080(10) 0.0079(9) -0.0002(9) S2 0.0433(12) 0.0436(12) 0.0362(11) -0.0075(9) 0.0174(9) 0.0006(9) Cl1 0.0323(11) 0.0630(14) 0.0448(12) 0.0079(10) 0.0154(9) 0.0012(9) Cl2A 0.070(3) 0.047(3) 0.044(3) 0.007(2) 0.003(2) 0.009(2) Cl2B 0.070(3) 0.047(3) 0.044(3) 0.007(2) 0.003(2) 0.009(2) Cl2C 0.070(3) 0.047(3) 0.044(3) 0.007(2) 0.003(2) 0.009(2) Cl2D 0.070(3) 0.047(3) 0.044(3) 0.007(2) 0.003(2) 0.009(2) Cl3A 0.061(2) 0.048(2) 0.0435(15) -0.0009(17) 0.0303(15) 0.0058(15) Cl3B 0.061(2) 0.048(2) 0.0435(15) -0.0009(17) 0.0303(15) 0.0058(15) Cl4A 0.057(3) 0.057(4) 0.051(3) 0.013(3) 0.009(2) -0.004(3) Cl4B 0.057(3) 0.057(4) 0.051(3) 0.013(3) 0.009(2) -0.004(3) Cl4C 0.057(3) 0.057(4) 0.051(3) 0.013(3) 0.009(2) -0.004(3) Cl4D 0.057(3) 0.057(4) 0.051(3) 0.013(3) 0.009(2) -0.004(3) O1W 0.059(4) 0.058(4) 0.036(3) 0.003(3) 0.009(3) 0.010(3) O2W 0.059(4) 0.058(4) 0.036(3) 0.003(3) 0.009(3) 0.010(3) O3W 0.059(4) 0.058(4) 0.036(3) 0.003(3) 0.009(3) 0.010(3) O4W 0.059(4) 0.058(4) 0.036(3) 0.003(3) 0.009(3) 0.010(3) O5W 0.059(4) 0.058(4) 0.036(3) 0.003(3) 0.009(3) 0.010(3) Cu1 0.0256(5) 0.0392(6) 0.0302(6) -0.0003(4) 0.0050(4) 0.0020(4) Cu2 0.0429(6) 0.0495(7) 0.0283(6) 0.0058(4) 0.0144(4) 0.0167(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 C1B O1 1.57(2) . ? C1B C2B 1.57(3) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B N1A 1.42(2) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C1A C2A 1.46(2) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A O1 1.468(15) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3 N1A 1.351(10) . ? C3 C4 1.396(11) . ? C3 C8 1.431(13) . ? C4 C5 1.397(12) . ? C4 C9 1.501(12) . ? C5 C6 1.353(15) . ? C5 H5 0.9500 . ? C6 C7 1.325(18) . ? C6 H6 0.9500 . ? C7 C8 1.394(17) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N2 1.467(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.490(11) . ? C10 C11 1.511(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 S1 1.799(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.516(13) . ? C12 S1 1.797(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N3 1.488(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.460(14) . ? C14 N3 1.513(11) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.397(14) . ? C15 C20 1.429(14) . ? C16 O1 1.378(12) . ? C16 C17 1.396(14) . ? C17 C18 1.284(13) . ? C17 H17 0.9500 . ? C18 C19 1.315(14) . ? C18 H18 0.9500 . ? C19 C20 1.442(14) . ? C19 H19 0.9500 . ? C20 H20A 0.9500 . ? C21 O2 1.443(10) . ? C21 C22 1.491(13) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N4 1.476(11) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.384(12) . ? C23 C28 1.414(12) . ? C23 N4 1.445(10) . ? C24 C25 1.404(13) . ? C24 C29 1.498(14) . ? C25 C26 1.399(16) . ? C25 H25 0.9500 . ? C26 C27 1.349(15) . ? C26 H26 0.9500 . ? C27 C28 1.377(13) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 N5 1.480(12) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 N5 1.461(12) . ? C30 C31 1.494(13) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 S2 1.821(9) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.512(13) . ? C32 S2 1.802(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N6 1.482(12) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.493(13) . ? C34 N6 1.496(11) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C40 1.380(12) . ? C35 C36 1.393(12) . ? C36 O2 1.366(10) . ? C36 C37 1.382(12) . ? C37 C38 1.397(13) . ? C37 H37 0.9500 . ? C38 C39 1.376(14) . ? C38 H38 0.9500 . ? C39 C40 1.358(13) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? N1A Cu1 2.333(7) . ? N1A H1A 0.9300 . ? N2 Cu1 2.090(7) . ? N2 H2 0.9300 . ? N3 Cu1 2.133(8) . ? N3 H3 0.9300 . ? N4 Cu2 2.089(6) . ? N4 H4 0.9300 . ? N5 Cu2 2.223(8) . ? N5 H5A 0.9300 . ? N6 Cu2 2.008(6) . ? N6 H6A 0.9300 . ? O1 Cu1 2.235(6) . ? O2 Cu2 2.510(6) . ? S1 Cu1 2.365(2) . ? S2 Cu2 2.376(2) . ? Cl1 Cu1 2.331(2) . ? Cl3A Cu2 2.312(3) . ? Cl3B Cu2 2.443(10) . ? 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 C1B C2B 93.6(15) . . ? O1 C1B H1B1 113.0 . . ? C2B C1B H1B1 113.0 . . ? O1 C1B H1B2 113.0 . . ? C2B C1B H1B2 113.0 . . ? H1B1 C1B H1B2 110.4 . . ? N1A C2B C1B 107.1(17) . . ? N1A C2B H2B1 110.3 . . ? C1B C2B H2B1 110.3 . . ? N1A C2B H2B2 110.3 . . ? C1B C2B H2B2 110.3 . . ? H2B1 C2B H2B2 108.6 . . ? C2A C1A H1A1 111.4 . . ? C2A C1A H1A2 111.4 . . ? H1A1 C1A H1A2 109.3 . . ? C1A C2A O1 112.1(11) . . ? C1A C2A H2A1 109.2 . . ? O1 C2A H2A1 109.2 . . ? C1A C2A H2A2 109.2 . . ? O1 C2A H2A2 109.2 . . ? H2A1 C2A H2A2 107.9 . . ? N1A C3 C4 117.3(7) . . ? N1A C3 C8 124.0(8) . . ? C4 C3 C8 118.7(8) . . ? C3 C4 C5 118.5(8) . . ? C3 C4 C9 121.1(8) . . ? C5 C4 C9 120.4(8) . . ? C6 C5 C4 121.2(10) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C7 C6 C5 121.8(11) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 120.7(10) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C3 119.0(10) . . ? C7 C8 H8 120.5 . . ? C3 C8 H8 120.5 . . ? N2 C9 C4 115.3(7) . . ? N2 C9 H9A 108.4 . . ? C4 C9 H9A 108.4 . . ? N2 C9 H9B 108.4 . . ? C4 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? N2 C10 C11 113.0(7) . . ? 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 . . ? C10 C11 S1 114.2(6) . . ? C10 C11 H11A 108.7 . . ? S1 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? S1 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 S1 114.1(6) . . ? C13 C12 H12A 108.7 . . ? S1 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? S1 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? N3 C13 C12 113.7(7) . . ? N3 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? N3 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C15 C14 N3 112.1(7) . . ? C15 C14 H14A 109.2 . . ? N3 C14 H14A 109.2 . . ? C15 C14 H14B 109.2 . . ? N3 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C20 117.1(10) . . ? C16 C15 C14 121.5(9) . . ? C20 C15 C14 121.4(10) . . ? O1 C16 C17 122.9(10) . . ? O1 C16 C15 116.4(9) . . ? C17 C16 C15 120.7(10) . . ? C18 C17 C16 122.0(11) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C19 121.0(11) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C20 122.9(10) . . ? C18 C19 H19 118.6 . . ? C20 C19 H19 118.6 . . ? C15 C20 C19 116.1(10) . . ? C15 C20 H20A 121.9 . . ? C19 C20 H20A 121.9 . . ? O2 C21 C22 105.8(8) . . ? O2 C21 H21A 110.6 . . ? C22 C21 H21A 110.6 . . ? O2 C21 H21B 110.6 . . ? C22 C21 H21B 110.6 . . ? H21A C21 H21B 108.7 . . ? N4 C22 C21 113.6(7) . . ? N4 C22 H22A 108.8 . . ? C21 C22 H22A 108.8 . . ? N4 C22 H22B 108.8 . . ? C21 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C24 C23 C28 121.4(8) . . ? C24 C23 N4 117.2(8) . . ? C28 C23 N4 121.3(8) . . ? C23 C24 C25 117.9(9) . . ? C23 C24 C29 122.3(8) . . ? C25 C24 C29 119.8(9) . . ? C26 C25 C24 119.7(10) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C27 C26 C25 121.5(9) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C26 C27 C28 120.6(10) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 118.9(9) . . ? C27 C28 H28 120.6 . . ? C23 C28 H28 120.6 . . ? N5 C29 C24 111.4(7) . . ? N5 C29 H29A 109.3 . . ? C24 C29 H29A 109.3 . . ? N5 C29 H29B 109.3 . . ? C24 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? N5 C30 C31 113.7(7) . . ? N5 C30 H30A 108.8 . . ? C31 C30 H30A 108.8 . . ? N5 C30 H30B 108.8 . . ? C31 C30 H30B 108.8 . . ? H30A C30 H30B 107.7 . . ? C30 C31 S2 115.7(6) . . ? C30 C31 H31A 108.4 . . ? S2 C31 H31A 108.4 . . ? C30 C31 H31B 108.4 . . ? S2 C31 H31B 108.4 . . ? H31A C31 H31B 107.4 . . ? C33 C32 S2 114.1(6) . . ? C33 C32 H32A 108.7 . . ? S2 C32 H32A 108.7 . . ? C33 C32 H32B 108.7 . . ? S2 C32 H32B 108.7 . . ? H32A C32 H32B 107.6 . . ? N6 C33 C32 112.3(7) . . ? N6 C33 H33A 109.1 . . ? C32 C33 H33A 109.1 . . ? N6 C33 H33B 109.1 . . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 107.9 . . ? C35 C34 N6 115.5(6) . . ? C35 C34 H34A 108.4 . . ? N6 C34 H34A 108.4 . . ? C35 C34 H34B 108.4 . . ? N6 C34 H34B 108.4 . . ? H34A C34 H34B 107.5 . . ? C40 C35 C36 117.4(9) . . ? C40 C35 C34 122.0(8) . . ? C36 C35 C34 120.6(7) . . ? O2 C36 C37 123.2(7) . . ? O2 C36 C35 115.1(7) . . ? C37 C36 C35 121.7(8) . . ? C36 C37 C38 118.3(8) . . ? C36 C37 H37 120.9 . . ? C38 C37 H37 120.9 . . ? C39 C38 C37 120.7(9) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C40 C39 C38 119.3(9) . . ? C40 C39 H39 120.4 . . ? C38 C39 H39 120.4 . . ? C39 C40 C35 122.6(9) . . ? C39 C40 H40 118.7 . . ? C35 C40 H40 118.7 . . ? C3 N1A C2B 138.5(12) . . ? C3 N1A Cu1 116.5(5) . . ? C2B N1A Cu1 100.0(10) . . ? C3 N1A H1A 97.1 . . ? C2B N1A H1A 97.1 . . ? Cu1 N1A H1A 97.1 . . ? C9 N2 C10 113.2(7) . . ? C9 N2 Cu1 112.1(5) . . ? C10 N2 Cu1 113.0(5) . . ? C9 N2 H2 105.9 . . ? C10 N2 H2 105.9 . . ? Cu1 N2 H2 105.9 . . ? C13 N3 C14 112.9(8) . . ? C13 N3 Cu1 112.9(5) . . ? C14 N3 Cu1 111.4(5) . . ? C13 N3 H3 106.4 . . ? C14 N3 H3 106.4 . . ? Cu1 N3 H3 106.4 . . ? C23 N4 C22 118.1(7) . . ? C23 N4 Cu2 115.4(5) . . ? C22 N4 Cu2 110.5(5) . . ? C23 N4 H4 103.6 . . ? C22 N4 H4 103.6 . . ? Cu2 N4 H4 103.6 . . ? C30 N5 C29 112.5(7) . . ? C30 N5 Cu2 113.6(5) . . ? C29 N5 Cu2 110.6(6) . . ? C30 N5 H5A 106.6 . . ? C29 N5 H5A 106.6 . . ? Cu2 N5 H5A 106.6 . . ? C33 N6 C34 114.0(7) . . ? C33 N6 Cu2 113.7(5) . . ? C34 N6 Cu2 112.5(5) . . ? C33 N6 H6A 105.2 . . ? C34 N6 H6A 105.2 . . ? Cu2 N6 H6A 105.2 . . ? C16 O1 C2A 129.9(9) . . ? C16 O1 C1B 101.5(11) . . ? C2A O1 C1B 36.2(9) . . ? C16 O1 Cu1 116.4(5) . . ? C2A O1 Cu1 105.6(7) . . ? C1B O1 Cu1 109.3(8) . . ? C36 O2 C21 118.5(7) . . ? C36 O2 Cu2 115.4(4) . . ? C21 O2 Cu2 102.4(4) . . ? C12 S1 C11 101.2(4) . . ? C12 S1 Cu1 99.6(3) . . ? C11 S1 Cu1 99.2(3) . . ? C32 S2 C31 103.6(4) . . ? C32 S2 Cu2 97.5(3) . . ? C31 S2 Cu2 99.3(3) . . ? N2 Cu1 N3 107.0(3) . . ? N2 Cu1 O1 163.9(3) . . ? N3 Cu1 O1 87.6(2) . . ? N2 Cu1 Cl1 94.2(2) . . ? N3 Cu1 Cl1 95.2(2) . . ? O1 Cu1 Cl1 91.05(19) . . ? N2 Cu1 N1A 88.3(2) . . ? N3 Cu1 N1A 162.5(3) . . ? O1 Cu1 N1A 76.3(2) . . ? Cl1 Cu1 N1A 91.96(18) . . ? N2 Cu1 S1 85.2(2) . . ? N3 Cu1 S1 85.3(2) . . ? O1 Cu1 S1 89.45(19) . . ? Cl1 Cu1 S1 179.29(9) . . ? N1A Cu1 S1 87.68(18) . . ? N6 Cu2 N4 162.5(3) . . ? N6 Cu2 N5 107.9(3) . . ? N4 Cu2 N5 89.6(3) . . ? N6 Cu2 Cl3A 89.1(2) . . ? N4 Cu2 Cl3A 89.57(19) . . ? N5 Cu2 Cl3A 93.8(2) . . ? N6 Cu2 S2 86.0(2) . . ? N4 Cu2 S2 96.33(18) . . ? N5 Cu2 S2 84.0(2) . . ? Cl3A Cu2 S2 173.69(10) . . ? N6 Cu2 Cl3B 94.4(3) . . ? N4 Cu2 Cl3B 79.4(3) . . ? N5 Cu2 Cl3B 108.4(3) . . ? Cl3A Cu2 Cl3B 18.0(2) . . ? S2 Cu2 Cl3B 166.7(3) . . ? N6 Cu2 O2 86.2(2) . . ? N4 Cu2 O2 76.9(2) . . ? N5 Cu2 O2 160.4(2) . . ? Cl3A Cu2 O2 100.20(16) . . ? S2 Cu2 O2 83.38(14) . . ? Cl3B Cu2 O2 83.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1B C2B N1A 80.2(17) . . . . ? N1A C3 C4 C5 -178.6(7) . . . . ? C8 C3 C4 C5 1.1(10) . . . . ? N1A C3 C4 C9 0.0(10) . . . . ? C8 C3 C4 C9 179.8(7) . . . . ? C3 C4 C5 C6 0.7(12) . . . . ? C9 C4 C5 C6 -178.0(8) . . . . ? C4 C5 C6 C7 -2.0(14) . . . . ? C5 C6 C7 C8 1.4(16) . . . . ? C6 C7 C8 C3 0.5(14) . . . . ? N1A C3 C8 C7 178.0(7) . . . . ? C4 C3 C8 C7 -1.7(11) . . . . ? C3 C4 C9 N2 68.0(10) . . . . ? C5 C4 C9 N2 -113.3(9) . . . . ? N2 C10 C11 S1 -40.1(10) . . . . ? S1 C12 C13 N3 41.7(9) . . . . ? N3 C14 C15 C16 -66.0(11) . . . . ? N3 C14 C15 C20 112.9(9) . . . . ? C20 C15 C16 O1 177.3(7) . . . . ? C14 C15 C16 O1 -3.7(12) . . . . ? C20 C15 C16 C17 -4.5(12) . . . . ? C14 C15 C16 C17 174.5(8) . . . . ? O1 C16 C17 C18 -179.5(8) . . . . ? C15 C16 C17 C18 2.5(13) . . . . ? C16 C17 C18 C19 1.7(13) . . . . ? C17 C18 C19 C20 -3.7(14) . . . . ? C16 C15 C20 C19 2.6(11) . . . . ? C14 C15 C20 C19 -176.4(8) . . . . ? C18 C19 C20 C15 1.4(12) . . . . ? O2 C21 C22 N4 -64.8(9) . . . . ? C28 C23 C24 C25 -3.0(11) . . . . ? N4 C23 C24 C25 179.0(7) . . . . ? C28 C23 C24 C29 175.4(7) . . . . ? N4 C23 C24 C29 -2.6(11) . . . . ? C23 C24 C25 C26 2.1(12) . . . . ? C29 C24 C25 C26 -176.4(8) . . . . ? C24 C25 C26 C27 -0.5(13) . . . . ? C25 C26 C27 C28 -0.1(13) . . . . ? C26 C27 C28 C23 -0.8(12) . . . . ? C24 C23 C28 C27 2.4(11) . . . . ? N4 C23 C28 C27 -179.7(7) . . . . ? C23 C24 C29 N5 -65.0(11) . . . . ? C25 C24 C29 N5 113.4(9) . . . . ? N5 C30 C31 S2 42.5(10) . . . . ? S2 C32 C33 N6 -39.6(9) . . . . ? N6 C34 C35 C40 -109.1(9) . . . . ? N6 C34 C35 C36 71.6(10) . . . . ? C40 C35 C36 O2 -177.6(7) . . . . ? C34 C35 C36 O2 1.7(11) . . . . ? C40 C35 C36 C37 1.2(12) . . . . ? C34 C35 C36 C37 -179.5(8) . . . . ? O2 C36 C37 C38 178.2(7) . . . . ? C35 C36 C37 C38 -0.5(12) . . . . ? C36 C37 C38 C39 -1.1(12) . . . . ? C37 C38 C39 C40 1.9(13) . . . . ? C38 C39 C40 C35 -1.2(13) . . . . ? C36 C35 C40 C39 -0.3(13) . . . . ? C34 C35 C40 C39 -179.6(8) . . . . ? C4 C3 N1A C2B 162.1(16) . . . . ? C8 C3 N1A C2B -18(2) . . . . ? C4 C3 N1A Cu1 -48.9(8) . . . . ? C8 C3 N1A Cu1 131.4(7) . . . . ? C1B C2B N1A C3 88(2) . . . . ? C1B C2B N1A Cu1 -64.3(16) . . . . ? C4 C9 N2 C10 65.0(10) . . . . ? C4 C9 N2 Cu1 -64.2(9) . . . . ? C11 C10 N2 C9 -84.4(9) . . . . ? C11 C10 N2 Cu1 44.3(9) . . . . ? C12 C13 N3 C14 86.3(9) . . . . ? C12 C13 N3 Cu1 -41.1(9) . . . . ? C15 C14 N3 C13 -61.9(10) . . . . ? C15 C14 N3 Cu1 66.2(9) . . . . ? C24 C23 N4 C22 -169.4(7) . . . . ? C28 C23 N4 C22 12.6(10) . . . . ? C24 C23 N4 Cu2 56.8(8) . . . . ? C28 C23 N4 Cu2 -121.1(7) . . . . ? C21 C22 N4 C23 -88.6(9) . . . . ? C21 C22 N4 Cu2 47.2(9) . . . . ? C31 C30 N5 C29 88.3(9) . . . . ? C31 C30 N5 Cu2 -38.2(9) . . . . ? C24 C29 N5 C30 -66.8(10) . . . . ? C24 C29 N5 Cu2 61.4(9) . . . . ? C32 C33 N6 C34 -84.2(9) . . . . ? C32 C33 N6 Cu2 46.5(9) . . . . ? C35 C34 N6 C33 59.4(10) . . . . ? C35 C34 N6 Cu2 -71.9(8) . . . . ? C17 C16 O1 C2A 21.1(14) . . . . ? C15 C16 O1 C2A -160.8(10) . . . . ? C17 C16 O1 C1B -4.2(13) . . . . ? C15 C16 O1 C1B 173.9(11) . . . . ? C17 C16 O1 Cu1 -122.7(7) . . . . ? C15 C16 O1 Cu1 55.4(9) . . . . ? C1A C2A O1 C16 -91.5(14) . . . . ? C1A C2A O1 C1B -46.2(16) . . . . ? C1A C2A O1 Cu1 55.2(13) . . . . ? C2B C1B O1 C16 -175.2(12) . . . . ? C2B C1B O1 C2A 38.6(14) . . . . ? C2B C1B O1 Cu1 -51.8(15) . . . . ? C37 C36 O2 C21 10.6(11) . . . . ? C35 C36 O2 C21 -170.6(7) . . . . ? C37 C36 O2 Cu2 132.5(7) . . . . ? C35 C36 O2 Cu2 -48.7(8) . . . . ? C22 C21 O2 C36 172.2(6) . . . . ? C22 C21 O2 Cu2 43.9(7) . . . . ? C13 C12 S1 C11 80.4(7) . . . . ? C13 C12 S1 Cu1 -21.1(6) . . . . ? C10 C11 S1 C12 -84.8(7) . . . . ? C10 C11 S1 Cu1 17.0(7) . . . . ? C33 C32 S2 C31 -86.0(7) . . . . ? C33 C32 S2 Cu2 15.5(7) . . . . ? C30 C31 S2 C32 75.9(7) . . . . ? C30 C31 S2 Cu2 -24.2(7) . . . . ? C9 N2 Cu1 N3 -173.1(5) . . . . ? C10 N2 Cu1 N3 57.5(7) . . . . ? C9 N2 Cu1 O1 32.3(12) . . . . ? C10 N2 Cu1 O1 -97.1(10) . . . . ? C9 N2 Cu1 Cl1 -76.3(5) . . . . ? C10 N2 Cu1 Cl1 154.3(6) . . . . ? C9 N2 Cu1 N1A 15.5(6) . . . . ? C10 N2 Cu1 N1A -113.8(6) . . . . ? C9 N2 Cu1 S1 103.3(5) . . . . ? C10 N2 Cu1 S1 -26.0(6) . . . . ? C13 N3 Cu1 N2 -62.2(6) . . . . ? C14 N3 Cu1 N2 169.6(6) . . . . ? C13 N3 Cu1 O1 111.0(6) . . . . ? C14 N3 Cu1 O1 -17.2(6) . . . . ? C13 N3 Cu1 Cl1 -158.2(6) . . . . ? C14 N3 Cu1 Cl1 73.6(6) . . . . ? C13 N3 Cu1 N1A 87.9(10) . . . . ? C14 N3 Cu1 N1A -40.2(11) . . . . ? C13 N3 Cu1 S1 21.3(6) . . . . ? C14 N3 Cu1 S1 -106.9(6) . . . . ? C16 O1 Cu1 N2 116.0(10) . . . . ? C2A O1 Cu1 N2 -35.9(13) . . . . ? C1B O1 Cu1 N2 1.9(15) . . . . ? C16 O1 Cu1 N3 -39.8(7) . . . . ? C2A O1 Cu1 N3 168.3(8) . . . . ? C1B O1 Cu1 N3 -153.9(11) . . . . ? C16 O1 Cu1 Cl1 -135.0(6) . . . . ? C2A O1 Cu1 Cl1 73.1(8) . . . . ? C1B O1 Cu1 Cl1 110.9(11) . . . . ? C16 O1 Cu1 N1A 133.3(7) . . . . ? C2A O1 Cu1 N1A -18.7(8) . . . . ? C1B O1 Cu1 N1A 19.1(11) . . . . ? C16 O1 Cu1 S1 45.5(6) . . . . ? C2A O1 Cu1 S1 -106.4(8) . . . . ? C1B O1 Cu1 S1 -68.6(11) . . . . ? C3 N1A Cu1 N2 38.3(6) . . . . ? C2B N1A Cu1 N2 -162.0(11) . . . . ? C3 N1A Cu1 N3 -113.3(8) . . . . ? C2B N1A Cu1 N3 46.5(15) . . . . ? C3 N1A Cu1 O1 -137.0(6) . . . . ? C2B N1A Cu1 O1 22.8(11) . . . . ? C3 N1A Cu1 Cl1 132.4(5) . . . . ? C2B N1A Cu1 Cl1 -67.8(11) . . . . ? C3 N1A Cu1 S1 -47.0(5) . . . . ? C2B N1A Cu1 S1 112.8(11) . . . . ? C12 S1 Cu1 N2 107.6(4) . . . . ? C11 S1 Cu1 N2 4.4(4) . . . . ? C12 S1 Cu1 N3 0.0(3) . . . . ? C11 S1 Cu1 N3 -103.1(4) . . . . ? C12 S1 Cu1 O1 -87.7(3) . . . . ? C11 S1 Cu1 O1 169.2(3) . . . . ? C12 S1 Cu1 Cl1 137(6) . . . . ? C11 S1 Cu1 Cl1 34(6) . . . . ? C12 S1 Cu1 N1A -163.9(3) . . . . ? C11 S1 Cu1 N1A 92.9(3) . . . . ? C33 N6 Cu2 N4 -127.0(9) . . . . ? C34 N6 Cu2 N4 4.5(12) . . . . ? C33 N6 Cu2 N5 53.8(6) . . . . ? C34 N6 Cu2 N5 -174.8(5) . . . . ? C33 N6 Cu2 Cl3A 147.5(6) . . . . ? C34 N6 Cu2 Cl3A -81.1(5) . . . . ? C33 N6 Cu2 S2 -28.6(6) . . . . ? C34 N6 Cu2 S2 102.8(5) . . . . ? C33 N6 Cu2 Cl3B 164.7(6) . . . . ? C34 N6 Cu2 Cl3B -63.8(6) . . . . ? C33 N6 Cu2 O2 -112.3(6) . . . . ? C34 N6 Cu2 O2 19.2(5) . . . . ? C23 N4 Cu2 N6 138.3(8) . . . . ? C22 N4 Cu2 N6 1.1(12) . . . . ? C23 N4 Cu2 N5 -42.4(6) . . . . ? C22 N4 Cu2 N5 -179.5(6) . . . . ? C23 N4 Cu2 Cl3A -136.2(5) . . . . ? C22 N4 Cu2 Cl3A 86.6(5) . . . . ? C23 N4 Cu2 S2 41.5(6) . . . . ? C22 N4 Cu2 S2 -95.6(5) . . . . ? C23 N4 Cu2 Cl3B -151.2(6) . . . . ? C22 N4 Cu2 Cl3B 71.6(6) . . . . ? C23 N4 Cu2 O2 123.2(6) . . . . ? C22 N4 Cu2 O2 -13.9(5) . . . . ? C30 N5 Cu2 N6 -66.0(6) . . . . ? C29 N5 Cu2 N6 166.5(6) . . . . ? C30 N5 Cu2 N4 114.2(6) . . . . ? C29 N5 Cu2 N4 -13.3(6) . . . . ? C30 N5 Cu2 Cl3A -156.2(6) . . . . ? C29 N5 Cu2 Cl3A 76.2(6) . . . . ? C30 N5 Cu2 S2 17.8(5) . . . . ? C29 N5 Cu2 S2 -109.7(6) . . . . ? C30 N5 Cu2 Cl3B -167.1(6) . . . . ? C29 N5 Cu2 Cl3B 65.4(6) . . . . ? C30 N5 Cu2 O2 68.1(9) . . . . ? C29 N5 Cu2 O2 -59.5(9) . . . . ? C32 S2 Cu2 N6 6.4(4) . . . . ? C31 S2 Cu2 N6 111.5(4) . . . . ? C32 S2 Cu2 N4 168.9(4) . . . . ? C31 S2 Cu2 N4 -85.9(3) . . . . ? C32 S2 Cu2 N5 -102.1(4) . . . . ? C31 S2 Cu2 N5 3.1(3) . . . . ? C32 S2 Cu2 Cl3A -32.0(11) . . . . ? C31 S2 Cu2 Cl3A 73.2(11) . . . . ? C32 S2 Cu2 Cl3B 98.4(12) . . . . ? C31 S2 Cu2 Cl3B -156.4(12) . . . . ? C32 S2 Cu2 O2 93.0(3) . . . . ? C31 S2 Cu2 O2 -161.9(3) . . . . ? C36 O2 Cu2 N6 36.6(5) . . . . ? C21 O2 Cu2 N6 166.8(5) . . . . ? C36 O2 Cu2 N4 -147.9(5) . . . . ? C21 O2 Cu2 N4 -17.7(5) . . . . ? C36 O2 Cu2 N5 -100.1(8) . . . . ? C21 O2 Cu2 N5 30.1(9) . . . . ? C36 O2 Cu2 Cl3A 125.0(5) . . . . ? C21 O2 Cu2 Cl3A -104.8(5) . . . . ? C36 O2 Cu2 S2 -49.8(5) . . . . ? C21 O2 Cu2 S2 80.4(5) . . . . ? C36 O2 Cu2 Cl3B 131.5(6) . . . . ? C21 O2 Cu2 Cl3B -98.3(5) . . . . ? 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 H2 Cl4A 0.93 2.91 3.650(11) 137.3 . N2 H2 Cl3A 0.93 2.92 3.614(8) 132.2 . N3 H3 O4W 0.93 2.38 3.288(16) 165.5 . N3 H3 Cl4A 0.93 2.41 3.260(11) 152.1 . N5 H5A O2W 0.93 2.44 3.366(16) 174.1 . N5 H5A Cl4A 0.93 2.47 3.353(10) 159.3 . N5 H5A O4W 0.93 2.58 3.390(17) 146.3 . N5 H5A Cl4C 0.93 2.96 3.688(11) 136.7 . N6 H6A Cl1 0.93 2.54 3.336(7) 144.5 . _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 22.05 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.273 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.138 data_nonnisad _database_code_depnum_ccdc_archive 'CCDC 819259' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20.25 H34.875 Cl2 N3.125 Ni O5.75' _chemical_formula_sum 'C20.25 H34.875 Cl2 N3.125 Ni O5.75' _chemical_formula_weight 543.75 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 P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.0787(8) _cell_length_b 18.0874(13) _cell_length_c 24.7617(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.238(2) _cell_angle_gamma 90.00 _cell_volume 5323.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9985 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.22 _exptl_crystal_description multi-face _exptl_crystal_colour green _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2290 _exptl_absorpt_coefficient_mu 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.693 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 42018 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 27.64 _reflns_number_total 12334 _reflns_number_gt 8470 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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. his molecule crystallises with two complexes in the asymmetric unit and there is a large amount of disordered solvent in the lattice. This was modelled as a quarter occupancy acetonitrile, two full occupancy water molecules, one three-quarter occupancy water molecule, six half-occupancy water molecules and eight quarter occupancy water molecules. Hydrogen atoms could not be located on the water molecules of half or lower occupancy and were not included in the model. In addition the lattice chloride anions are modelled each over two positions of 0.8 and 0.2 occupancy and were found in close proximity to disordered water molecules. The each disordered chloride was modelled with identical thermal parameters. The bond lengths in the acetontrile solvent molecule were restrained to N-C 1.00(1) and C-C 1.45(1) angstroms. The hydrogen water atoms were with bond length restraints of 0.870(1). ; _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^)+(0.1606P)^2^+8.3940P] 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 12334 _refine_ls_number_parameters 651 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0778 _refine_ls_wR_factor_ref 0.2631 _refine_ls_wR_factor_gt 0.2317 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3725(4) 0.9206(3) 0.09992(18) 0.0325(9) Uani 1 1 d . . . H1A H 0.3769 0.9753 0.1017 0.039 Uiso 1 1 calc R . . H1B H 0.4241 0.9001 0.1319 0.039 Uiso 1 1 calc R . . C2 C 0.2539(4) 0.8954(3) 0.10032(19) 0.0336(10) Uani 1 1 d . . . H2A H 0.2314 0.9094 0.1355 0.040 Uiso 1 1 calc R . . H2B H 0.2018 0.9198 0.0702 0.040 Uiso 1 1 calc R . . C3 C 0.2572(4) 0.7690(3) 0.14019(18) 0.0335(10) Uani 1 1 d . . . C4 C 0.2239(4) 0.6965(3) 0.1294(2) 0.0383(11) Uani 1 1 d . . . C5 C 0.2323(4) 0.6479(3) 0.1743(3) 0.0502(14) Uani 1 1 d . . . H5 H 0.2080 0.5981 0.1685 0.060 Uiso 1 1 calc R . . C6 C 0.2758(5) 0.6723(4) 0.2268(2) 0.0517(15) Uani 1 1 d . . . H6 H 0.2820 0.6388 0.2567 0.062 Uiso 1 1 calc R . . C7 C 0.3097(4) 0.7435(4) 0.2362(2) 0.0491(14) Uani 1 1 d . . . H7 H 0.3391 0.7592 0.2725 0.059 Uiso 1 1 calc R . . C8 C 0.3015(4) 0.7935(3) 0.1930(2) 0.0401(11) Uani 1 1 d . . . H8 H 0.3256 0.8432 0.1994 0.048 Uiso 1 1 calc R . . C9 C 0.1852(4) 0.6721(3) 0.0711(2) 0.0468(13) Uani 1 1 d . . . H9A H 0.1579 0.6204 0.0709 0.056 Uiso 1 1 calc R . . H9B H 0.1215 0.7035 0.0540 0.056 Uiso 1 1 calc R . . C10 C 0.3716(4) 0.6246(3) 0.0571(2) 0.0435(12) Uani 1 1 d . . . H10A H 0.4060 0.6088 0.0256 0.052 Uiso 1 1 calc R . . H10B H 0.3422 0.5800 0.0730 0.052 Uiso 1 1 calc R . . C11 C 0.4596(4) 0.6603(3) 0.0996(2) 0.0387(11) Uani 1 1 d . . . H11A H 0.4322 0.6623 0.1349 0.046 Uiso 1 1 calc R . . H11B H 0.5287 0.6298 0.1050 0.046 Uiso 1 1 calc R . . C12 C 0.5803(4) 0.7384(3) 0.05468(19) 0.0366(10) Uani 1 1 d . . . H12A H 0.6356 0.6995 0.0689 0.044 Uiso 1 1 calc R . . H12B H 0.6179 0.7870 0.0617 0.044 Uiso 1 1 calc R . . C13 C 0.5430(4) 0.7279(3) -0.00687(19) 0.0382(11) Uani 1 1 d . . . H13A H 0.6038 0.7440 -0.0263 0.046 Uiso 1 1 calc R . . H13B H 0.5277 0.6750 -0.0151 0.046 Uiso 1 1 calc R . . C14 C 0.4633(4) 0.8447(3) -0.04968(17) 0.0370(10) Uani 1 1 d . . . H14A H 0.3917 0.8719 -0.0609 0.044 Uiso 1 1 calc R . . H14B H 0.4968 0.8366 -0.0829 0.044 Uiso 1 1 calc R . . C15 C 0.5420(4) 0.8911(3) -0.00962(17) 0.0326(9) Uani 1 1 d . . . C16 C 0.5120(3) 0.9148(3) 0.03965(17) 0.0296(9) Uani 1 1 d . . . C17 C 0.5870(4) 0.9548(3) 0.07791(19) 0.0340(9) Uani 1 1 d . . . H17 H 0.5668 0.9699 0.1116 0.041 Uiso 1 1 calc R . . C18 C 0.6929(4) 0.9725(3) 0.0657(2) 0.0411(11) Uani 1 1 d . . . H18 H 0.7450 0.9998 0.0914 0.049 Uiso 1 1 calc R . . C19 C 0.7220(4) 0.9505(3) 0.0168(2) 0.0433(12) Uani 1 1 d . . . H19 H 0.7936 0.9631 0.0087 0.052 Uiso 1 1 calc R . . C20 C 0.6482(4) 0.9105(3) -0.0200(2) 0.0396(11) Uani 1 1 d . . . H20 H 0.6694 0.8956 -0.0535 0.047 Uiso 1 1 calc R . . C21 C 0.9377(5) 0.5900(3) 0.1630(2) 0.0498(13) Uani 1 1 d . . . H21A H 0.9951 0.5646 0.1902 0.060 Uiso 1 1 calc R . . H21B H 0.9539 0.5797 0.1259 0.060 Uiso 1 1 calc R . . C22 C 0.8220(5) 0.5616(3) 0.16731(19) 0.0425(12) Uani 1 1 d . . . H22A H 0.7647 0.5839 0.1383 0.051 Uiso 1 1 calc R . . H22B H 0.8190 0.5072 0.1629 0.051 Uiso 1 1 calc R . . C23 C 0.6935(4) 0.5604(3) 0.23455(18) 0.0342(10) Uani 1 1 d . . . C24 C 0.6700(4) 0.5814(3) 0.28537(18) 0.0363(10) Uani 1 1 d . . . C25 C 0.5657(4) 0.5616(3) 0.2981(2) 0.0431(12) Uani 1 1 d . . . H25 H 0.5485 0.5752 0.3327 0.052 Uiso 1 1 calc R . . C26 C 0.4870(5) 0.5226(3) 0.2615(3) 0.0511(13) Uani 1 1 d . . . H26 H 0.4170 0.5093 0.2711 0.061 Uiso 1 1 calc R . . C27 C 0.5111(5) 0.5035(3) 0.2110(3) 0.0519(13) Uani 1 1 d . . . H27 H 0.4567 0.4777 0.1854 0.062 Uiso 1 1 calc R . . C28 C 0.6150(4) 0.5217(3) 0.1973(2) 0.0410(11) Uani 1 1 d . . . H28 H 0.6319 0.5078 0.1627 0.049 Uiso 1 1 calc R . . C29 C 0.7502(4) 0.6267(3) 0.32463(18) 0.0409(11) Uani 1 1 d . . . H29A H 0.7206 0.6327 0.3592 0.049 Uiso 1 1 calc R . . H29B H 0.8233 0.6006 0.3334 0.049 Uiso 1 1 calc R . . C30 C 0.6635(4) 0.7442(3) 0.2848(2) 0.0442(12) Uani 1 1 d . . . H30A H 0.6792 0.7970 0.2931 0.053 Uiso 1 1 calc R . . H30B H 0.6060 0.7276 0.3061 0.053 Uiso 1 1 calc R . . C31 C 0.6177(4) 0.7355(3) 0.2240(2) 0.0411(11) Uani 1 1 d . . . H31A H 0.5795 0.6870 0.2175 0.049 Uiso 1 1 calc R . . H31B H 0.5614 0.7746 0.2121 0.049 Uiso 1 1 calc R . . C32 C 0.7301(4) 0.8139(3) 0.1749(2) 0.0419(11) Uani 1 1 d . . . H32A H 0.6598 0.8433 0.1694 0.050 Uiso 1 1 calc R . . H32B H 0.7568 0.8116 0.1394 0.050 Uiso 1 1 calc R . . C33 C 0.8182(4) 0.8520(3) 0.2170(3) 0.0472(12) Uani 1 1 d . . . H33A H 0.8450 0.8971 0.2007 0.057 Uiso 1 1 calc R . . H33B H 0.7845 0.8670 0.2489 0.057 Uiso 1 1 calc R . . C34 C 1.0061(5) 0.8098(4) 0.2006(4) 0.073(2) Uani 1 1 d . . . H34A H 1.0315 0.8619 0.2023 0.088 Uiso 1 1 calc R . . H34B H 1.0713 0.7788 0.2167 0.088 Uiso 1 1 calc R . . C35 C 0.9703(5) 0.7890(4) 0.1434(3) 0.0594(18) Uani 1 1 d . . . C36 C 0.9355(4) 0.7175(3) 0.1284(2) 0.0472(14) Uani 1 1 d . . . C37 C 0.8941(5) 0.6982(4) 0.0748(3) 0.0596(17) Uani 1 1 d . . . H37 H 0.8680 0.6494 0.0658 0.071 Uiso 1 1 calc R . . C38 C 0.8912(6) 0.7510(6) 0.0344(3) 0.084(3) Uani 1 1 d . . . H38 H 0.8630 0.7375 -0.0025 0.101 Uiso 1 1 calc R . . C39 C 0.9249(7) 0.8178(6) 0.0447(4) 0.093(3) Uani 1 1 d . . . H39 H 0.9226 0.8520 0.0154 0.112 Uiso 1 1 calc R . . C40 C 0.9666(6) 0.8412(4) 0.1007(5) 0.095(4) Uani 1 1 d . . . H40 H 0.9909 0.8906 0.1085 0.114 Uiso 1 1 calc R . . N1 N 0.2475(3) 0.8156(2) 0.09342(14) 0.0269(7) Uani 1 1 d . R . H1 H 0.1733 0.8083 0.0763 0.032 Uiso 1 1 calc R . . N2 N 0.2768(3) 0.6766(2) 0.03772(17) 0.0397(9) Uani 1 1 d . R . H2 H 0.2454 0.6623 0.0022 0.048 Uiso 1 1 calc R . . N3 N 0.4395(3) 0.7721(2) -0.02633(14) 0.0329(8) Uani 1 1 d . R . H3 H 0.3976 0.7454 -0.0550 0.039 Uiso 1 1 calc R . . N4 N 0.8007(3) 0.5824(2) 0.22183(14) 0.0326(8) Uani 1 1 d . . . H4 H 0.8522 0.5543 0.2457 0.039 Uiso 1 1 calc R . . N5 N 0.7679(3) 0.7007(2) 0.30166(17) 0.0401(9) Uani 1 1 d . . . H5A H 0.8124 0.7273 0.3295 0.048 Uiso 1 1 calc R . . N6 N 0.9149(4) 0.8013(3) 0.2353(2) 0.0519(12) Uani 1 1 d . . . H6A H 0.9464 0.8149 0.2710 0.062 Uiso 1 1 calc R . . O1 O 0.4036(3) 0.8940(2) 0.04872(13) 0.0373(7) Uani 1 1 d . R . O2 O 0.4861(2) 0.73475(18) 0.08356(12) 0.0312(7) Uani 1 1 d . R . O3 O 0.9422(3) 0.6684(2) 0.17309(16) 0.0528(10) Uani 1 1 d . . . O4 O 0.7069(3) 0.74018(19) 0.19187(13) 0.0359(7) Uani 1 1 d . . . O1W O 0.8185(3) 0.9286(3) -0.12997(16) 0.0534(11) Uani 1 1 d D . . H1O H 0.870(3) 0.951(4) -0.107(2) 0.080 Uiso 1 1 d D . . H2O H 0.753(2) 0.940(4) -0.123(3) 0.080 Uiso 1 1 d D . . O2W O 0.9903(4) 1.0341(3) 0.0494(2) 0.0705(13) Uani 1 1 d D . . H3O H 0.995(3) 1.000(2) 0.0746(15) 0.106 Uiso 1 1 d D . . H4O H 0.937(5) 1.065(3) 0.053(3) 0.106 Uiso 1 1 d D . . O3W O 0.6931(6) 0.5550(3) 0.0255(3) 0.069(2) Uani 0.75 1 d PD A 1 H5O H 0.720(8) 0.511(3) 0.033(4) 0.104 Uiso 0.75 1 d PD B 1 H6O H 0.726(9) 0.575(5) 0.001(4) 0.104 Uiso 0.75 1 d PD C 1 N1A N 0.4960(15) 0.4627(11) 0.0650(9) 0.060(5) Uiso 0.25 1 d PD D 2 C1A C 0.6399(16) 0.5411(13) 0.0371(9) 0.038(5) Uiso 0.25 1 d PD D 2 H1A1 H 0.6355 0.5904 0.0530 0.057 Uiso 0.25 1 calc PR D 2 H1A2 H 0.6298 0.5451 -0.0029 0.057 Uiso 0.25 1 calc PR D 2 H1A3 H 0.7137 0.5193 0.0513 0.057 Uiso 0.25 1 calc PR D 2 C2A C 0.5521(15) 0.4944(11) 0.0520(8) 0.044(4) Uiso 0.25 1 d PD D 2 O4WA O 0.4679(7) 0.7400(5) 0.3807(3) 0.058(2) Uani 0.50 1 d P E 1 O5WA O 0.2952(6) 0.9915(5) 0.2208(4) 0.055(2) Uani 0.50 1 d P F 1 O6W O 0.9938(8) 0.3860(6) 0.1509(4) 0.076(3) Uani 0.50 1 d P G 1 O7WA O 0.8066(12) 0.3998(7) 0.0702(4) 0.093(4) Uani 0.50 1 d P H 1 O8W O 0.2259(8) 0.4333(6) 0.1783(5) 0.089(4) Uani 0.50 1 d P I 1 O9W O 0.6137(7) 0.6909(7) -0.1623(4) 0.081(3) Uani 0.50 1 d P J 1 O10A O 0.7263(14) 0.7699(9) -0.1181(7) 0.050(4) Uiso 0.25 1 d P K 1 O10B O 0.7872(13) 0.7860(9) -0.1036(6) 0.044(3) Uiso 0.25 1 d P L 2 O7WB O 0.7493(16) 0.3954(10) 0.0788(7) 0.038(3) Uiso 0.25 1 d P M 2 O7WC O 0.7176(14) 0.3765(10) 0.0879(6) 0.042(4) Uiso 0.25 1 d P N 3 O5WB O 0.3465(16) 1.0339(12) 0.2190(8) 0.066(5) Uiso 0.25 1 d P O 2 O11W O 0.6578(15) 0.6251(11) -0.1045(7) 0.064(4) Uiso 0.25 1 d P P 2 O4WB O 0.487(2) 0.7838(15) 0.4070(11) 0.094(7) Uiso 0.25 1 d P Q 2 Cl1 Cl 0.18262(9) 0.82394(8) -0.03441(4) 0.0405(3) Uani 1 1 d . R 2 Cl2A Cl 0.3844(4) 0.6565(2) -0.12860(19) 0.0807(11) Uani 0.80 1 d P S 1 Cl2B Cl 0.414(2) 0.6737(11) -0.1341(10) 0.0807(11) Uani 0.20 1 d P T 2 Cl3 Cl 1.02021(18) 0.65260(15) 0.30071(10) 0.0945(7) Uani 1 1 d . . . Cl4A Cl 0.95177(14) 0.43231(11) 0.26429(8) 0.0506(4) Uani 0.80 1 d P U 1 Cl4B Cl 0.9589(6) 0.4676(5) 0.2812(3) 0.0506(4) Uani 0.20 1 d P V 2 Ni1 Ni 0.33977(4) 0.78265(3) 0.03228(2) 0.02837(18) Uani 1 1 d . . . Ni2 Ni 0.85731(5) 0.69287(4) 0.23849(3) 0.03701(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(2) 0.031(2) 0.032(2) 0.0001(18) 0.0107(17) 0.0020(18) C2 0.037(2) 0.029(2) 0.036(2) 0.0038(18) 0.0116(18) 0.0059(18) C3 0.0283(19) 0.038(3) 0.037(2) 0.0129(19) 0.0128(17) 0.0038(18) C4 0.028(2) 0.041(3) 0.048(3) 0.012(2) 0.0132(19) 0.0047(19) C5 0.037(2) 0.041(3) 0.077(4) 0.022(3) 0.022(3) 0.005(2) C6 0.045(3) 0.066(4) 0.049(3) 0.030(3) 0.020(2) 0.015(3) C7 0.043(3) 0.071(4) 0.037(2) 0.012(3) 0.015(2) 0.015(3) C8 0.035(2) 0.051(3) 0.037(2) 0.008(2) 0.0132(19) 0.006(2) C9 0.033(2) 0.039(3) 0.066(3) 0.009(3) 0.002(2) -0.002(2) C10 0.045(3) 0.031(3) 0.054(3) 0.000(2) 0.007(2) 0.008(2) C11 0.038(2) 0.033(3) 0.046(3) 0.012(2) 0.009(2) 0.012(2) C12 0.031(2) 0.039(3) 0.037(2) 0.005(2) -0.0004(18) 0.0081(19) C13 0.039(2) 0.039(3) 0.037(2) -0.004(2) 0.0075(19) 0.015(2) C14 0.041(2) 0.045(3) 0.0253(19) 0.0044(19) 0.0073(17) 0.009(2) C15 0.035(2) 0.031(2) 0.031(2) 0.0105(18) 0.0064(17) 0.0101(18) C16 0.0296(19) 0.030(2) 0.031(2) 0.0091(17) 0.0097(16) 0.0054(17) C17 0.037(2) 0.026(2) 0.039(2) 0.0026(18) 0.0062(18) 0.0022(18) C18 0.040(2) 0.026(3) 0.057(3) 0.005(2) 0.007(2) -0.004(2) C19 0.033(2) 0.034(3) 0.066(3) 0.016(2) 0.019(2) 0.004(2) C20 0.041(2) 0.037(3) 0.045(3) 0.016(2) 0.021(2) 0.012(2) C21 0.058(3) 0.045(3) 0.053(3) 0.010(3) 0.029(3) 0.015(3) C22 0.060(3) 0.040(3) 0.031(2) 0.006(2) 0.016(2) 0.007(2) C23 0.044(2) 0.027(2) 0.035(2) 0.0043(18) 0.0126(19) 0.0075(19) C24 0.047(2) 0.035(3) 0.029(2) 0.0057(18) 0.0094(18) 0.004(2) C25 0.048(3) 0.042(3) 0.044(3) 0.005(2) 0.020(2) 0.007(2) C26 0.043(3) 0.047(3) 0.067(4) 0.007(3) 0.019(3) 0.001(2) C27 0.053(3) 0.038(3) 0.062(3) -0.002(3) 0.002(3) -0.003(2) C28 0.054(3) 0.032(3) 0.037(2) 0.000(2) 0.009(2) 0.003(2) C29 0.043(2) 0.053(3) 0.027(2) 0.002(2) 0.0073(18) 0.004(2) C30 0.041(2) 0.039(3) 0.057(3) -0.010(2) 0.021(2) 0.004(2) C31 0.028(2) 0.035(3) 0.060(3) -0.002(2) 0.005(2) 0.0017(19) C32 0.037(2) 0.041(3) 0.049(3) 0.006(2) 0.011(2) 0.010(2) C33 0.039(2) 0.033(3) 0.069(3) 0.001(2) 0.010(2) 0.002(2) C34 0.034(3) 0.047(4) 0.140(7) 0.010(4) 0.020(4) -0.001(3) C35 0.036(3) 0.054(4) 0.095(5) 0.031(3) 0.030(3) 0.012(3) C36 0.035(2) 0.051(3) 0.061(3) 0.028(3) 0.025(2) 0.015(2) C37 0.046(3) 0.086(5) 0.054(3) 0.028(3) 0.030(3) 0.023(3) C38 0.062(4) 0.116(7) 0.087(5) 0.064(5) 0.045(4) 0.045(5) C39 0.070(5) 0.120(8) 0.103(7) 0.075(6) 0.054(5) 0.048(5) C40 0.052(4) 0.062(5) 0.189(10) 0.063(6) 0.072(5) 0.029(3) N1 0.0320(17) 0.0223(19) 0.0288(17) 0.0048(14) 0.0118(14) 0.0015(14) N2 0.038(2) 0.036(2) 0.042(2) -0.0040(18) -0.0028(17) 0.0035(17) N3 0.0330(18) 0.040(2) 0.0247(16) -0.0047(15) 0.0022(14) 0.0078(16) N4 0.041(2) 0.033(2) 0.0266(16) 0.0034(15) 0.0128(15) 0.0043(16) N5 0.040(2) 0.043(3) 0.037(2) -0.0115(18) 0.0040(17) -0.0011(18) N6 0.033(2) 0.044(3) 0.075(3) 0.000(2) 0.000(2) 0.0015(19) O1 0.0371(16) 0.041(2) 0.0359(16) -0.0015(14) 0.0125(13) -0.0009(14) O2 0.0323(14) 0.0312(17) 0.0294(14) 0.0000(12) 0.0034(12) 0.0106(13) O3 0.061(2) 0.046(2) 0.056(2) 0.0178(18) 0.0236(19) 0.0068(19) O4 0.0322(15) 0.0323(18) 0.0426(17) -0.0011(14) 0.0050(13) 0.0039(13) O1W 0.0334(17) 0.077(3) 0.053(2) -0.035(2) 0.0162(16) -0.0125(18) O2W 0.055(2) 0.045(3) 0.114(4) 0.014(3) 0.021(3) 0.010(2) O3W 0.096(5) 0.025(3) 0.069(4) -0.017(3) -0.031(4) 0.019(3) O4WA 0.060(5) 0.073(6) 0.038(4) -0.005(4) -0.003(3) 0.025(4) O5WA 0.033(3) 0.052(5) 0.082(6) -0.030(4) 0.013(4) 0.012(3) O6W 0.074(6) 0.078(7) 0.081(6) -0.024(5) 0.027(5) -0.043(5) O7WA 0.107(9) 0.127(11) 0.047(5) -0.041(6) 0.023(6) -0.064(8) O8W 0.058(5) 0.093(8) 0.123(9) -0.047(7) 0.037(6) -0.047(5) O9W 0.052(5) 0.112(9) 0.065(6) -0.028(6) -0.022(4) 0.014(5) Cl1 0.0337(5) 0.0517(8) 0.0339(5) 0.0067(5) -0.0001(4) 0.0111(5) Cl2A 0.105(3) 0.058(2) 0.0669(15) -0.0119(16) -0.0185(18) 0.0018(15) Cl2B 0.105(3) 0.058(2) 0.0669(15) -0.0119(16) -0.0185(18) 0.0018(15) Cl3 0.0769(12) 0.1082(18) 0.1011(15) 0.0057(13) 0.0233(11) 0.0044(12) Cl4A 0.0468(8) 0.0426(11) 0.0563(10) 0.0139(8) -0.0077(7) -0.0120(8) Cl4B 0.0468(8) 0.0426(11) 0.0563(10) 0.0139(8) -0.0077(7) -0.0120(8) Ni1 0.0283(3) 0.0300(3) 0.0258(3) 0.0011(2) 0.0019(2) 0.0076(2) Ni2 0.0312(3) 0.0396(4) 0.0399(3) 0.0021(3) 0.0056(2) 0.0061(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.467(5) . ? C1 C2 1.505(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.455(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.383(7) . ? C3 C8 1.395(7) . ? C3 N1 1.421(5) . ? C4 C5 1.406(7) . ? C4 C9 1.503(8) . ? C5 C6 1.385(9) . ? C5 H5 0.9500 . ? C6 C7 1.358(9) . ? C6 H6 0.9500 . ? C7 C8 1.390(7) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N2 1.496(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.494(6) . ? C10 C11 1.501(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.456(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O2 1.449(6) . ? C12 C13 1.522(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N3 1.490(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N3 1.484(7) . ? C14 C15 1.501(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C20 1.398(6) . ? C15 C16 1.400(6) . ? C16 C17 1.391(6) . ? C16 O1 1.419(5) . ? C17 C18 1.403(7) . ? C17 H17 0.9500 . ? C18 C19 1.379(8) . ? C18 H18 0.9500 . ? C19 C20 1.363(8) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 O3 1.438(7) . ? C21 C22 1.510(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N4 1.468(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C28 1.389(7) . ? C23 C24 1.391(6) . ? C23 N4 1.441(6) . ? C24 C25 1.399(7) . ? C24 C29 1.490(7) . ? C25 C26 1.383(8) . ? C25 H25 0.9500 . ? C26 C27 1.377(8) . ? C26 H26 0.9500 . ? C27 C28 1.397(8) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 N5 1.485(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 N5 1.481(7) . ? C30 C31 1.516(8) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O4 1.452(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 O4 1.441(6) . ? C32 C33 1.516(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N6 1.490(7) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.455(11) . ? C34 N6 1.521(9) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.389(9) . ? C35 C40 1.413(10) . ? C36 C37 1.379(9) . ? C36 O3 1.411(6) . ? C37 C38 1.378(9) . ? C37 H37 0.9500 . ? C38 C39 1.285(14) . ? C38 H38 0.9500 . ? C39 C40 1.452(14) . ? C39 H39 0.9500 . ? C40 H40 0.9500 . ? N1 Ni1 2.119(3) . ? N1 H1 0.9300 . ? N2 Ni1 2.077(4) . ? N2 H2 0.9300 . ? N3 Ni1 2.053(4) . ? N3 H3 0.9300 . ? N4 Ni2 2.128(4) . ? N4 H4 0.9300 . ? N5 Ni2 2.058(4) . ? N5 H5A 0.9300 . ? N6 Ni2 2.087(5) . ? N6 H6A 0.9300 . ? O1 Ni1 2.168(4) . ? O2 Ni1 2.166(3) . ? O3 Ni2 2.112(4) . ? O4 Ni2 2.149(3) . ? O1W H1O 0.8699(10) . ? O1W H2O 0.8699(10) . ? O2W H3O 0.8700(10) . ? O2W H4O 0.8700(10) . ? O3W H5O 0.8700(11) . ? O3W H6O 0.8700(11) . ? N1A C2A 0.984(8) . ? C1A C2A 1.453(8) . ? C1A H5O 1.13(7) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? Cl1 Ni1 2.4029(11) . ? Cl3 Ni2 2.387(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 O1 C1 C2 107.3(4) . . ? O1 C1 H1A 110.3 . . ? C2 C1 H1A 110.3 . . ? O1 C1 H1B 110.3 . . ? C2 C1 H1B 110.3 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C1 109.3(4) . . ? N1 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C8 122.2(4) . . ? C4 C3 N1 115.2(4) . . ? C8 C3 N1 122.6(5) . . ? C3 C4 C5 117.5(5) . . ? C3 C4 C9 119.7(4) . . ? C5 C4 C9 122.8(5) . . ? C6 C5 C4 120.3(6) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 121.0(5) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.5(5) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 118.5(5) . . ? C7 C8 H8 120.8 . . ? C3 C8 H8 120.8 . . ? N2 C9 C4 112.3(4) . . ? N2 C9 H9A 109.1 . . ? C4 C9 H9A 109.1 . . ? N2 C9 H9B 109.1 . . ? C4 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? N2 C10 C11 111.2(4) . . ? N2 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O2 C11 C10 111.7(4) . . ? O2 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? O2 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? O2 C12 C13 111.7(4) . . ? O2 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? O2 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? N3 C13 C12 109.8(4) . . ? N3 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? N3 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N3 C14 C15 112.4(3) . . ? N3 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? N3 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C20 C15 C16 118.1(4) . . ? C20 C15 C14 120.8(4) . . ? C16 C15 C14 121.0(4) . . ? C17 C16 C15 121.0(4) . . ? C17 C16 O1 122.5(4) . . ? C15 C16 O1 116.5(4) . . ? C16 C17 C18 118.7(4) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C19 C18 C17 120.5(5) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.1(5) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C15 121.5(5) . . ? C19 C20 H20 119.2 . . ? C15 C20 H20 119.2 . . ? O3 C21 C22 109.3(4) . . ? O3 C21 H21A 109.8 . . ? C22 C21 H21A 109.8 . . ? O3 C21 H21B 109.8 . . ? C22 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? N4 C22 C21 107.1(4) . . ? N4 C22 H22A 110.3 . . ? C21 C22 H22A 110.3 . . ? N4 C22 H22B 110.3 . . ? C21 C22 H22B 110.3 . . ? H22A C22 H22B 108.6 . . ? C28 C23 C24 120.8(5) . . ? C28 C23 N4 121.9(4) . . ? C24 C23 N4 117.3(4) . . ? C23 C24 C25 118.1(5) . . ? C23 C24 C29 121.8(4) . . ? C25 C24 C29 120.0(4) . . ? C26 C25 C24 121.6(5) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C27 C26 C25 119.4(5) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C28 120.3(5) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C23 C28 C27 119.7(5) . . ? C23 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? N5 C29 C24 111.5(4) . . ? N5 C29 H29A 109.3 . . ? C24 C29 H29A 109.3 . . ? N5 C29 H29B 109.3 . . ? C24 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? N5 C30 C31 111.5(4) . . ? N5 C30 H30A 109.3 . . ? C31 C30 H30A 109.3 . . ? N5 C30 H30B 109.3 . . ? C31 C30 H30B 109.3 . . ? H30A C30 H30B 108.0 . . ? O4 C31 C30 111.2(4) . . ? O4 C31 H31A 109.4 . . ? C30 C31 H31A 109.4 . . ? O4 C31 H31B 109.4 . . ? C30 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? O4 C32 C33 111.6(4) . . ? O4 C32 H32A 109.3 . . ? C33 C32 H32A 109.3 . . ? O4 C32 H32B 109.3 . . ? C33 C32 H32B 109.3 . . ? H32A C32 H32B 108.0 . . ? N6 C33 C32 110.3(4) . . ? N6 C33 H33A 109.6 . . ? C32 C33 H33A 109.6 . . ? N6 C33 H33B 109.6 . . ? C32 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C35 C34 N6 113.9(5) . . ? C35 C34 H34A 108.8 . . ? N6 C34 H34A 108.8 . . ? C35 C34 H34B 108.8 . . ? N6 C34 H34B 108.8 . . ? H34A C34 H34B 107.7 . . ? C36 C35 C40 117.0(8) . . ? C36 C35 C34 121.6(6) . . ? C40 C35 C34 121.4(8) . . ? C37 C36 C35 122.3(6) . . ? C37 C36 O3 123.8(6) . . ? C35 C36 O3 113.8(6) . . ? C38 C37 C36 118.7(8) . . ? C38 C37 H37 120.6 . . ? C36 C37 H37 120.6 . . ? C39 C38 C37 122.8(9) . . ? C39 C38 H38 118.6 . . ? C37 C38 H38 118.6 . . ? C38 C39 C40 120.5(7) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C35 C40 C39 118.7(8) . . ? C35 C40 H40 120.7 . . ? C39 C40 H40 120.7 . . ? C3 N1 C2 119.9(4) . . ? C3 N1 Ni1 115.9(3) . . ? C2 N1 Ni1 109.8(3) . . ? C3 N1 H1 102.8 . . ? C2 N1 H1 102.8 . . ? Ni1 N1 H1 102.8 . . ? C10 N2 C9 112.8(4) . . ? C10 N2 Ni1 109.5(3) . . ? C9 N2 Ni1 113.7(3) . . ? C10 N2 H2 106.8 . . ? C9 N2 H2 106.8 . . ? Ni1 N2 H2 106.8 . . ? C14 N3 C13 113.0(4) . . ? C14 N3 Ni1 111.9(3) . . ? C13 N3 Ni1 112.7(3) . . ? C14 N3 H3 106.2 . . ? C13 N3 H3 106.2 . . ? Ni1 N3 H3 106.2 . . ? C23 N4 C22 116.2(4) . . ? C23 N4 Ni2 119.2(3) . . ? C22 N4 Ni2 108.4(3) . . ? C23 N4 H4 103.6 . . ? C22 N4 H4 103.6 . . ? Ni2 N4 H4 103.6 . . ? C30 N5 C29 114.4(4) . . ? C30 N5 Ni2 111.0(3) . . ? C29 N5 Ni2 111.1(3) . . ? C30 N5 H5A 106.6 . . ? C29 N5 H5A 106.6 . . ? Ni2 N5 H5A 106.6 . . ? C33 N6 C34 111.9(5) . . ? C33 N6 Ni2 110.0(3) . . ? C34 N6 Ni2 113.2(4) . . ? C33 N6 H6A 107.1 . . ? C34 N6 H6A 107.1 . . ? Ni2 N6 H6A 107.1 . . ? C16 O1 C1 115.8(3) . . ? C16 O1 Ni1 121.6(3) . . ? C1 O1 Ni1 109.3(3) . . ? C12 O2 C11 114.0(3) . . ? C12 O2 Ni1 108.9(2) . . ? C11 O2 Ni1 109.5(2) . . ? C36 O3 C21 119.4(5) . . ? C36 O3 Ni2 120.1(3) . . ? C21 O3 Ni2 109.3(3) . . ? C32 O4 C31 114.6(4) . . ? C32 O4 Ni2 109.6(3) . . ? C31 O4 Ni2 108.7(3) . . ? H1O O1W H2O 110(6) . . ? H3O O2W H4O 110(5) . . ? H5O O3W H6O 109.2(12) . . ? C2A C1A H5O 115(4) . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? N1A C2A C1A 175(3) . . ? N3 Ni1 N2 103.17(17) . . ? N3 Ni1 N1 168.65(15) . . ? N2 Ni1 N1 88.19(15) . . ? N3 Ni1 O2 81.79(13) . . ? N2 Ni1 O2 82.10(14) . . ? N1 Ni1 O2 99.90(12) . . ? N3 Ni1 O1 89.15(14) . . ? N2 Ni1 O1 165.36(15) . . ? N1 Ni1 O1 79.59(13) . . ? O2 Ni1 O1 92.04(12) . . ? N3 Ni1 Cl1 91.94(10) . . ? N2 Ni1 Cl1 94.48(11) . . ? N1 Ni1 Cl1 87.25(10) . . ? O2 Ni1 Cl1 171.93(9) . . ? O1 Ni1 Cl1 92.95(9) . . ? N5 Ni2 N6 100.77(19) . . ? N5 Ni2 O3 171.62(17) . . ? N6 Ni2 O3 87.61(19) . . ? N5 Ni2 N4 91.03(15) . . ? N6 Ni2 N4 166.58(18) . . ? O3 Ni2 N4 80.65(15) . . ? N5 Ni2 O4 82.70(15) . . ? N6 Ni2 O4 82.01(15) . . ? O3 Ni2 O4 98.69(14) . . ? N4 Ni2 O4 93.30(14) . . ? N5 Ni2 Cl3 90.82(13) . . ? N6 Ni2 Cl3 93.97(14) . . ? O3 Ni2 Cl3 88.50(13) . . ? N4 Ni2 Cl3 92.20(12) . . ? O4 Ni2 Cl3 171.57(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 55.5(5) . . . . ? C8 C3 C4 C5 2.3(7) . . . . ? N1 C3 C4 C5 179.7(4) . . . . ? C8 C3 C4 C9 -175.3(4) . . . . ? N1 C3 C4 C9 2.2(6) . . . . ? C3 C4 C5 C6 -1.9(7) . . . . ? C9 C4 C5 C6 175.6(5) . . . . ? C4 C5 C6 C7 0.9(8) . . . . ? C5 C6 C7 C8 -0.1(8) . . . . ? C6 C7 C8 C3 0.4(7) . . . . ? C4 C3 C8 C7 -1.6(7) . . . . ? N1 C3 C8 C7 -178.8(4) . . . . ? C3 C4 C9 N2 64.1(6) . . . . ? C5 C4 C9 N2 -113.4(5) . . . . ? N2 C10 C11 O2 -45.2(6) . . . . ? O2 C12 C13 N3 44.0(6) . . . . ? N3 C14 C15 C20 116.0(5) . . . . ? N3 C14 C15 C16 -62.8(5) . . . . ? C20 C15 C16 C17 -1.8(6) . . . . ? C14 C15 C16 C17 177.0(4) . . . . ? C20 C15 C16 O1 179.9(4) . . . . ? C14 C15 C16 O1 -1.3(6) . . . . ? C15 C16 C17 C18 1.3(7) . . . . ? O1 C16 C17 C18 179.5(4) . . . . ? C16 C17 C18 C19 0.0(7) . . . . ? C17 C18 C19 C20 -0.7(7) . . . . ? C18 C19 C20 C15 0.2(7) . . . . ? C16 C15 C20 C19 1.0(7) . . . . ? C14 C15 C20 C19 -177.8(4) . . . . ? O3 C21 C22 N4 -56.2(5) . . . . ? C28 C23 C24 C25 0.7(7) . . . . ? N4 C23 C24 C25 179.0(4) . . . . ? C28 C23 C24 C29 -176.3(5) . . . . ? N4 C23 C24 C29 1.9(7) . . . . ? C23 C24 C25 C26 -0.3(8) . . . . ? C29 C24 C25 C26 176.8(5) . . . . ? C24 C25 C26 C27 -0.7(8) . . . . ? C25 C26 C27 C28 1.4(9) . . . . ? C24 C23 C28 C27 -0.1(7) . . . . ? N4 C23 C28 C27 -178.2(5) . . . . ? C26 C27 C28 C23 -1.0(8) . . . . ? C23 C24 C29 N5 62.9(6) . . . . ? C25 C24 C29 N5 -114.2(5) . . . . ? N5 C30 C31 O4 -43.9(6) . . . . ? O4 C32 C33 N6 46.2(6) . . . . ? N6 C34 C35 C36 -61.8(7) . . . . ? N6 C34 C35 C40 116.6(6) . . . . ? C40 C35 C36 C37 -3.0(8) . . . . ? C34 C35 C36 C37 175.4(5) . . . . ? C40 C35 C36 O3 179.6(4) . . . . ? C34 C35 C36 O3 -2.0(7) . . . . ? C35 C36 C37 C38 2.6(8) . . . . ? O3 C36 C37 C38 179.8(5) . . . . ? C36 C37 C38 C39 -0.4(9) . . . . ? C37 C38 C39 C40 -1.2(11) . . . . ? C36 C35 C40 C39 1.4(8) . . . . ? C34 C35 C40 C39 -177.1(6) . . . . ? C38 C39 C40 C35 0.6(10) . . . . ? C4 C3 N1 C2 165.3(4) . . . . ? C8 C3 N1 C2 -17.2(6) . . . . ? C4 C3 N1 Ni1 -59.0(4) . . . . ? C8 C3 N1 Ni1 118.5(4) . . . . ? C1 C2 N1 C3 95.6(4) . . . . ? C1 C2 N1 Ni1 -42.5(4) . . . . ? C11 C10 N2 C9 -89.9(5) . . . . ? C11 C10 N2 Ni1 37.8(5) . . . . ? C4 C9 N2 C10 65.0(6) . . . . ? C4 C9 N2 Ni1 -60.5(5) . . . . ? C15 C14 N3 C13 -57.3(5) . . . . ? C15 C14 N3 Ni1 71.1(4) . . . . ? C12 C13 N3 C14 96.9(5) . . . . ? C12 C13 N3 Ni1 -31.1(5) . . . . ? C28 C23 N4 C22 0.0(6) . . . . ? C24 C23 N4 C22 -178.2(4) . . . . ? C28 C23 N4 Ni2 132.7(4) . . . . ? C24 C23 N4 Ni2 -45.5(5) . . . . ? C21 C22 N4 C23 180.0(4) . . . . ? C21 C22 N4 Ni2 42.5(4) . . . . ? C31 C30 N5 C29 -95.6(5) . . . . ? C31 C30 N5 Ni2 31.0(5) . . . . ? C24 C29 N5 C30 56.6(5) . . . . ? C24 C29 N5 Ni2 -70.0(4) . . . . ? C32 C33 N6 C34 91.2(6) . . . . ? C32 C33 N6 Ni2 -35.6(6) . . . . ? C35 C34 N6 C33 -64.1(7) . . . . ? C35 C34 N6 Ni2 60.9(6) . . . . ? C17 C16 O1 C1 3.1(6) . . . . ? C15 C16 O1 C1 -178.6(4) . . . . ? C17 C16 O1 Ni1 -133.7(4) . . . . ? C15 C16 O1 Ni1 44.6(5) . . . . ? C2 C1 O1 C16 177.7(4) . . . . ? C2 C1 O1 Ni1 -40.5(4) . . . . ? C13 C12 O2 C11 87.8(5) . . . . ? C13 C12 O2 Ni1 -34.8(4) . . . . ? C10 C11 O2 C12 -92.9(4) . . . . ? C10 C11 O2 Ni1 29.2(4) . . . . ? C37 C36 O3 C21 18.8(7) . . . . ? C35 C36 O3 C21 -163.8(5) . . . . ? C37 C36 O3 Ni2 -121.0(5) . . . . ? C35 C36 O3 Ni2 56.4(5) . . . . ? C22 C21 O3 C36 -102.8(5) . . . . ? C22 C21 O3 Ni2 40.9(5) . . . . ? C33 C32 O4 C31 89.7(5) . . . . ? C33 C32 O4 Ni2 -32.9(5) . . . . ? C30 C31 O4 C32 -89.1(5) . . . . ? C30 C31 O4 Ni2 33.9(5) . . . . ? C14 N3 Ni1 N2 161.5(3) . . . . ? C13 N3 Ni1 N2 -69.9(3) . . . . ? C14 N3 Ni1 N1 -19.3(8) . . . . ? C13 N3 Ni1 N1 109.3(7) . . . . ? C14 N3 Ni1 O2 -118.7(3) . . . . ? C13 N3 Ni1 O2 9.9(3) . . . . ? C14 N3 Ni1 O1 -26.5(3) . . . . ? C13 N3 Ni1 O1 102.1(3) . . . . ? C14 N3 Ni1 Cl1 66.4(3) . . . . ? C13 N3 Ni1 Cl1 -165.0(3) . . . . ? C10 N2 Ni1 N3 62.8(3) . . . . ? C9 N2 Ni1 N3 -170.0(3) . . . . ? C10 N2 Ni1 N1 -117.0(3) . . . . ? C9 N2 Ni1 N1 10.1(3) . . . . ? C10 N2 Ni1 O2 -16.8(3) . . . . ? C9 N2 Ni1 O2 110.4(3) . . . . ? C10 N2 Ni1 O1 -83.9(6) . . . . ? C9 N2 Ni1 O1 43.3(7) . . . . ? C10 N2 Ni1 Cl1 155.9(3) . . . . ? C9 N2 Ni1 Cl1 -76.9(3) . . . . ? C3 N1 Ni1 N3 -132.0(6) . . . . ? C2 N1 Ni1 N3 8.0(8) . . . . ? C3 N1 Ni1 N2 47.3(3) . . . . ? C2 N1 Ni1 N2 -172.8(3) . . . . ? C3 N1 Ni1 O2 -34.3(3) . . . . ? C2 N1 Ni1 O2 105.6(3) . . . . ? C3 N1 Ni1 O1 -124.6(3) . . . . ? C2 N1 Ni1 O1 15.3(3) . . . . ? C3 N1 Ni1 Cl1 141.9(3) . . . . ? C2 N1 Ni1 Cl1 -78.2(3) . . . . ? C12 O2 Ni1 N3 13.9(3) . . . . ? C11 O2 Ni1 N3 -111.3(3) . . . . ? C12 O2 Ni1 N2 118.5(3) . . . . ? C11 O2 Ni1 N2 -6.7(3) . . . . ? C12 O2 Ni1 N1 -154.8(3) . . . . ? C11 O2 Ni1 N1 80.0(3) . . . . ? C12 O2 Ni1 O1 -75.0(3) . . . . ? C11 O2 Ni1 O1 159.8(3) . . . . ? C12 O2 Ni1 Cl1 53.2(8) . . . . ? C11 O2 Ni1 Cl1 -72.1(8) . . . . ? C16 O1 Ni1 N3 -27.7(3) . . . . ? C1 O1 Ni1 N3 -167.0(3) . . . . ? C16 O1 Ni1 N2 119.9(5) . . . . ? C1 O1 Ni1 N2 -19.3(7) . . . . ? C16 O1 Ni1 N1 153.7(3) . . . . ? C1 O1 Ni1 N1 14.5(3) . . . . ? C16 O1 Ni1 O2 54.0(3) . . . . ? C1 O1 Ni1 O2 -85.2(3) . . . . ? C16 O1 Ni1 Cl1 -119.6(3) . . . . ? C1 O1 Ni1 Cl1 101.1(3) . . . . ? C30 N5 Ni2 N6 70.7(4) . . . . ? C29 N5 Ni2 N6 -160.9(3) . . . . ? C30 N5 Ni2 O3 -109.8(11) . . . . ? C29 N5 Ni2 O3 18.6(12) . . . . ? C30 N5 Ni2 N4 -102.9(3) . . . . ? C29 N5 Ni2 N4 25.6(3) . . . . ? C30 N5 Ni2 O4 -9.7(3) . . . . ? C29 N5 Ni2 O4 118.7(3) . . . . ? C30 N5 Ni2 Cl3 164.9(3) . . . . ? C29 N5 Ni2 Cl3 -66.7(3) . . . . ? C33 N6 Ni2 N5 -66.9(4) . . . . ? C34 N6 Ni2 N5 167.1(4) . . . . ? C33 N6 Ni2 O3 113.2(4) . . . . ? C34 N6 Ni2 O3 -12.8(4) . . . . ? C33 N6 Ni2 N4 84.4(8) . . . . ? C34 N6 Ni2 N4 -41.7(9) . . . . ? C33 N6 Ni2 O4 14.1(4) . . . . ? C34 N6 Ni2 O4 -111.9(4) . . . . ? C33 N6 Ni2 Cl3 -158.5(4) . . . . ? C34 N6 Ni2 Cl3 75.5(4) . . . . ? C36 O3 Ni2 N5 137.1(10) . . . . ? C21 O3 Ni2 N5 -6.4(13) . . . . ? C36 O3 Ni2 N6 -43.4(4) . . . . ? C21 O3 Ni2 N6 173.1(4) . . . . ? C36 O3 Ni2 N4 130.1(4) . . . . ? C21 O3 Ni2 N4 -13.4(3) . . . . ? C36 O3 Ni2 O4 38.1(4) . . . . ? C21 O3 Ni2 O4 -105.3(4) . . . . ? C36 O3 Ni2 Cl3 -137.5(4) . . . . ? C21 O3 Ni2 Cl3 79.1(3) . . . . ? C23 N4 Ni2 N5 28.3(3) . . . . ? C22 N4 Ni2 N5 164.3(3) . . . . ? C23 N4 Ni2 N6 -123.5(6) . . . . ? C22 N4 Ni2 N6 12.5(8) . . . . ? C23 N4 Ni2 O3 -152.7(3) . . . . ? C22 N4 Ni2 O3 -16.8(3) . . . . ? C23 N4 Ni2 O4 -54.5(3) . . . . ? C22 N4 Ni2 O4 81.5(3) . . . . ? C23 N4 Ni2 Cl3 119.1(3) . . . . ? C22 N4 Ni2 Cl3 -104.9(3) . . . . ? C32 O4 Ni2 N5 112.4(3) . . . . ? C31 O4 Ni2 N5 -13.6(3) . . . . ? C32 O4 Ni2 N6 10.4(3) . . . . ? C31 O4 Ni2 N6 -115.6(3) . . . . ? C32 O4 Ni2 O3 -76.0(3) . . . . ? C31 O4 Ni2 O3 158.1(3) . . . . ? C32 O4 Ni2 N4 -157.0(3) . . . . ? C31 O4 Ni2 N4 77.0(3) . . . . ? C32 O4 Ni2 Cl3 72.3(8) . . . . ? C31 O4 Ni2 Cl3 -53.7(9) . . . . ? 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 H2 O7WA 0.93 2.11 3.018(9) 163.6 3_665 N2 H2 O7WB 0.93 2.27 3.129(17) 153.1 3_665 N2 H2 O7WC 0.93 2.46 3.269(16) 146.0 3_665 N3 H3 Cl2B 0.93 2.39 3.18(2) 142.7 . N3 H3 Cl2A 0.93 2.42 3.261(6) 151.1 . N3 H3 O7WC 0.93 2.66 3.482(18) 148.2 3_665 N4 H4 Cl4B 0.93 2.12 3.022(9) 163.4 . N4 H4 Cl4A 0.93 2.52 3.336(4) 147.3 . N5 H5A Cl2B 0.93 2.26 3.13(2) 154.9 4_676 N5 H5A Cl2A 0.93 2.44 3.282(6) 151.4 4_676 N6 H6A O9W 0.93 2.37 3.170(9) 143.5 4_676 N6 H6A Cl2B 0.93 2.46 3.27(2) 145.2 4_676 N6 H6A Cl2A 0.93 2.77 3.537(7) 140.4 4_676 O1W H1O O2W 0.8699(10) 2.02(3) 2.851(6) 159(7) 3_775 O2W H3O O1W 0.8700(10) 2.74(2) 2.851(6) 88.2(14) 3_775 O2W H4O Cl1 0.8700(10) 2.47(2) 3.289(5) 157(6) 3_675 O3W H5O O7WA 0.8700(11) 2.37(2) 3.232(16) 170(10) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.379 _refine_diff_density_min -1.396 _refine_diff_density_rms 0.137 data_lj206sad _database_code_depnum_ccdc_archive 'CCDC 819260' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 N3 O2' _chemical_formula_sum 'C20 H27 N3 O2' _chemical_formula_weight 341.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1852(10) _cell_length_b 10.0015(9) _cell_length_c 10.9234(8) _cell_angle_alpha 71.742(6) _cell_angle_beta 86.090(7) _cell_angle_gamma 73.961(8) _cell_volume 915.69(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1936 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 32.30 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 36808 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 33.07 _reflns_number_total 6910 _reflns_number_gt 5032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0734P)^2^+0.4525P] 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 6910 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1730 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.05943(15) 0.33353(14) 0.15190(12) 0.0199(2) Uani 1 1 d . . . C2 C 1.02067(16) 0.25388(15) 0.07870(12) 0.0212(2) Uani 1 1 d . . . C3 C 1.12683(18) 0.20591(17) -0.00710(13) 0.0268(3) Uani 1 1 d . . . H3 H 1.1023 0.1511 -0.0559 0.032 Uiso 1 1 calc R . . C4 C 1.26792(19) 0.23616(18) -0.02315(14) 0.0316(3) Uani 1 1 d . . . H4 H 1.3380 0.2034 -0.0825 0.038 Uiso 1 1 calc R . . C5 C 1.30352(18) 0.31496(17) 0.04939(14) 0.0292(3) Uani 1 1 d . . . H5 H 1.3992 0.3359 0.0397 0.035 Uiso 1 1 calc R . . C6 C 1.20050(17) 0.36411(16) 0.13668(14) 0.0251(3) Uani 1 1 d . . . H6 H 1.2263 0.4182 0.1855 0.030 Uiso 1 1 calc R . . C7 C 0.86848(16) 0.22176(16) 0.09250(13) 0.0246(3) Uani 1 1 d . . . H7A H 0.7876 0.3150 0.0727 0.029 Uiso 1 1 calc R . . H7B H 0.8588 0.1720 0.0293 0.029 Uiso 1 1 calc R . . C8 C 0.71756(17) 0.07030(17) 0.23103(15) 0.0271(3) Uani 1 1 d . . . H8A H 0.7242 0.0205 0.1647 0.033 Uiso 1 1 calc R . . H8B H 0.6229 0.1507 0.2150 0.033 Uiso 1 1 calc R . . C9 C 0.71479(17) -0.03721(16) 0.36363(16) 0.0287(3) Uani 1 1 d . . . H9A H 0.6304 -0.0823 0.3684 0.034 Uiso 1 1 calc R . . H9B H 0.8110 -0.1158 0.3816 0.034 Uiso 1 1 calc R . . C10 C 0.71586(18) -0.05323(15) 0.58479(16) 0.0281(3) Uani 1 1 d . . . H10A H 0.8145 -0.1282 0.5955 0.034 Uiso 1 1 calc R . . H10B H 0.6344 -0.1035 0.6079 0.034 Uiso 1 1 calc R . . C11 C 0.71145(16) 0.04045(15) 0.67067(15) 0.0250(3) Uani 1 1 d . . . H11A H 0.6175 0.1217 0.6520 0.030 Uiso 1 1 calc R . . H11B H 0.7102 -0.0190 0.7620 0.030 Uiso 1 1 calc R . . C12 C 0.84254(17) 0.19062(15) 0.73218(14) 0.0242(3) Uani 1 1 d . . . H12A H 0.9422 0.2122 0.7260 0.029 Uiso 1 1 calc R . . H12B H 0.8312 0.1336 0.8227 0.029 Uiso 1 1 calc R . . C13 C 0.71989(15) 0.33370(14) 0.70033(12) 0.0196(2) Uani 1 1 d . . . C14 C 0.72056(14) 0.44257(13) 0.58104(12) 0.0172(2) Uani 1 1 d . . . C15 C 0.61162(15) 0.57794(14) 0.55528(13) 0.0209(2) Uani 1 1 d . . . H15 H 0.6127 0.6518 0.4756 0.025 Uiso 1 1 calc R . . C16 C 0.50167(16) 0.60530(15) 0.64538(14) 0.0235(3) Uani 1 1 d . . . H16 H 0.4286 0.6976 0.6269 0.028 Uiso 1 1 calc R . . C17 C 0.49854(16) 0.49830(16) 0.76204(14) 0.0253(3) Uani 1 1 d . . . H17 H 0.4233 0.5164 0.8234 0.030 Uiso 1 1 calc R . . C18 C 0.60761(16) 0.36358(16) 0.78800(13) 0.0233(3) Uani 1 1 d . . . H18 H 0.6052 0.2902 0.8677 0.028 Uiso 1 1 calc R . . C19 C 0.84596(16) 0.52373(14) 0.37801(12) 0.0211(2) Uani 1 1 d . . . H19A H 0.8544 0.6107 0.3990 0.025 Uiso 1 1 calc R . . H19B H 0.7533 0.5527 0.3241 0.025 Uiso 1 1 calc R . . C20 C 0.98293(16) 0.47121(15) 0.30351(12) 0.0207(2) Uani 1 1 d . . . H20A H 1.0089 0.5563 0.2402 0.025 Uiso 1 1 calc R . . H20B H 1.0706 0.4168 0.3635 0.025 Uiso 1 1 calc R . . N1 N 0.84770(14) 0.12969(14) 0.22232(12) 0.0246(2) Uani 1 1 d . . . H1N H 0.837(2) 0.170(2) 0.281(2) 0.037 Uiso 1 1 d . . . N2 N 0.84291(13) 0.09995(13) 0.65016(12) 0.0209(2) Uani 1 1 d . . . H2N H 0.847(2) 0.133(2) 0.582(2) 0.031 Uiso 1 1 d . . . N3 N 0.83391(12) 0.41033(11) 0.49565(10) 0.01595(19) Uani 1 1 d . . . H3N H 0.8603 0.3272 0.4887 0.024 Uiso 1 1 d R . . O1 O 0.69528(12) 0.03976(11) 0.45498(11) 0.0274(2) Uani 1 1 d . . . O2 O 0.95259(12) 0.37751(12) 0.23698(10) 0.0267(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0237(6) 0.0176(6) 0.0161(5) -0.0019(4) 0.0009(4) -0.0058(5) C2 0.0240(6) 0.0209(6) 0.0157(5) -0.0029(4) -0.0021(4) -0.0035(5) C3 0.0327(7) 0.0281(7) 0.0171(5) -0.0064(5) 0.0009(5) -0.0049(6) C4 0.0324(8) 0.0346(8) 0.0219(6) -0.0055(6) 0.0081(5) -0.0053(6) C5 0.0274(7) 0.0285(7) 0.0268(7) -0.0007(5) 0.0060(5) -0.0101(6) C6 0.0268(7) 0.0231(6) 0.0243(6) -0.0031(5) 0.0035(5) -0.0102(5) C7 0.0265(7) 0.0277(7) 0.0196(6) -0.0076(5) -0.0045(5) -0.0059(5) C8 0.0230(7) 0.0265(7) 0.0375(8) -0.0156(6) 0.0000(5) -0.0088(5) C9 0.0248(7) 0.0202(6) 0.0451(8) -0.0141(6) 0.0048(6) -0.0086(5) C10 0.0293(7) 0.0143(6) 0.0385(8) -0.0034(5) -0.0059(6) -0.0060(5) C11 0.0233(6) 0.0180(6) 0.0319(7) -0.0040(5) 0.0014(5) -0.0071(5) C12 0.0262(7) 0.0189(6) 0.0247(6) -0.0062(5) -0.0087(5) 0.0001(5) C13 0.0199(6) 0.0172(6) 0.0214(5) -0.0062(4) -0.0035(4) -0.0036(4) C14 0.0175(5) 0.0152(5) 0.0207(5) -0.0072(4) -0.0009(4) -0.0050(4) C15 0.0232(6) 0.0143(5) 0.0248(6) -0.0053(5) -0.0016(5) -0.0046(5) C16 0.0214(6) 0.0182(6) 0.0312(7) -0.0102(5) 0.0002(5) -0.0027(5) C17 0.0224(6) 0.0262(7) 0.0290(7) -0.0124(5) 0.0032(5) -0.0055(5) C18 0.0254(6) 0.0229(6) 0.0213(6) -0.0058(5) 0.0003(5) -0.0074(5) C19 0.0253(6) 0.0173(6) 0.0193(5) -0.0033(4) 0.0006(5) -0.0061(5) C20 0.0246(6) 0.0199(6) 0.0206(5) -0.0066(5) 0.0010(5) -0.0102(5) N1 0.0242(6) 0.0234(6) 0.0259(6) -0.0034(5) -0.0043(4) -0.0094(5) N2 0.0228(5) 0.0170(5) 0.0224(5) -0.0050(4) -0.0003(4) -0.0055(4) N3 0.0188(5) 0.0102(4) 0.0180(4) -0.0038(3) 0.0023(4) -0.0035(4) O1 0.0314(5) 0.0132(4) 0.0353(5) -0.0054(4) -0.0062(4) -0.0033(4) O2 0.0294(5) 0.0307(5) 0.0271(5) -0.0148(4) 0.0045(4) -0.0133(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 C1 O2 1.3833(16) . ? C1 C6 1.399(2) . ? C1 C2 1.4126(18) . ? C2 C3 1.3993(19) . ? C2 C7 1.506(2) . ? C3 C4 1.398(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 C6 1.400(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.4619(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N1 1.4602(18) . ? C8 C9 1.513(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.4147(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O1 1.4228(19) . ? C10 C11 1.511(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N2 1.4625(18) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N2 1.4601(18) . ? C12 C13 1.5129(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.3944(19) . ? C13 C14 1.4131(18) . ? C14 N3 1.3888(16) . ? C14 C15 1.4016(18) . ? C15 C16 1.3943(19) . ? C15 H15 0.9500 . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.398(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N3 1.4445(16) . ? C19 C20 1.5113(19) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O2 1.4432(15) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? N1 H1N 0.84(2) . ? N2 H2N 0.71(2) . ? N3 H3N 0.8257 . ? 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 O2 C1 C6 123.12(12) . . ? O2 C1 C2 116.85(12) . . ? C6 C1 C2 120.03(12) . . ? C3 C2 C1 118.42(13) . . ? C3 C2 C7 120.84(12) . . ? C1 C2 C7 120.74(12) . . ? C4 C3 C2 121.96(13) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 118.68(13) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C5 C6 120.97(14) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 119.93(13) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N1 C7 C2 112.02(11) . . ? N1 C7 H7A 109.2 . . ? C2 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C2 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N1 C8 C9 109.75(12) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O1 C9 C8 108.06(11) . . ? O1 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O1 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O1 C10 C11 107.92(11) . . ? O1 C10 H10A 110.1 . . ? C11 C10 H10A 110.1 . . ? O1 C10 H10B 110.1 . . ? C11 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? N2 C11 C10 110.98(12) . . ? N2 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? N2 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N2 C12 C13 115.19(11) . . ? N2 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? N2 C12 H12B 108.5 . . ? C13 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C18 C13 C14 118.55(12) . . ? C18 C13 C12 121.53(12) . . ? C14 C13 C12 119.89(12) . . ? N3 C14 C15 123.02(11) . . ? N3 C14 C13 117.42(11) . . ? C15 C14 C13 119.53(12) . . ? C16 C15 C14 120.64(12) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.29(12) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.07(13) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C13 C18 C17 121.90(13) . . ? C13 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? N3 C19 C20 110.74(11) . . ? N3 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? O2 C20 C19 110.38(11) . . ? O2 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? O2 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C8 N1 C7 113.09(11) . . ? C8 N1 H1N 105.9(14) . . ? C7 N1 H1N 115.8(15) . . ? C12 N2 C11 112.41(12) . . ? C12 N2 H2N 116.7(17) . . ? C11 N2 H2N 106.9(17) . . ? C14 N3 C19 118.74(10) . . ? C14 N3 H3N 119.3 . . ? C19 N3 H3N 113.9 . . ? C9 O1 C10 113.36(11) . . ? C1 O2 C20 117.96(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 -179.15(12) . . . . ? C6 C1 C2 C3 0.68(19) . . . . ? O2 C1 C2 C7 1.01(18) . . . . ? C6 C1 C2 C7 -179.15(12) . . . . ? C1 C2 C3 C4 -0.8(2) . . . . ? C7 C2 C3 C4 179.01(13) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? O2 C1 C6 C5 179.46(13) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? C4 C5 C6 C1 0.2(2) . . . . ? C3 C2 C7 N1 117.00(14) . . . . ? C1 C2 C7 N1 -63.17(17) . . . . ? N1 C8 C9 O1 63.15(15) . . . . ? O1 C10 C11 N2 -67.49(15) . . . . ? N2 C12 C13 C18 117.02(14) . . . . ? N2 C12 C13 C14 -65.12(17) . . . . ? C18 C13 C14 N3 179.74(11) . . . . ? C12 C13 C14 N3 1.82(17) . . . . ? C18 C13 C14 C15 1.53(18) . . . . ? C12 C13 C14 C15 -176.39(11) . . . . ? N3 C14 C15 C16 -178.98(11) . . . . ? C13 C14 C15 C16 -0.87(18) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? C15 C16 C17 C18 0.4(2) . . . . ? C14 C13 C18 C17 -1.25(19) . . . . ? C12 C13 C18 C17 176.64(12) . . . . ? C16 C17 C18 C13 0.3(2) . . . . ? N3 C19 C20 O2 77.52(13) . . . . ? C9 C8 N1 C7 173.37(12) . . . . ? C2 C7 N1 C8 -167.21(12) . . . . ? C13 C12 N2 C11 -68.64(16) . . . . ? C10 C11 N2 C12 -179.75(11) . . . . ? C15 C14 N3 C19 3.65(17) . . . . ? C13 C14 N3 C19 -174.50(11) . . . . ? C20 C19 N3 C14 175.50(10) . . . . ? C8 C9 O1 C10 -170.18(12) . . . . ? C11 C10 O1 C9 173.04(12) . . . . ? C6 C1 O2 C20 6.18(19) . . . . ? C2 C1 O2 C20 -173.99(11) . . . . ? C19 C20 O2 C1 172.53(11) . . . . ? 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 N1 H1N O2 0.84(2) 2.49(2) 2.9472(16) 115.2(17) . N2 H2N O1 0.71(2) 2.56(2) 2.8976(16) 111.5(19) . N2 H2N N3 0.71(2) 2.60(2) 3.0143(16) 118.9(19) . N3 H3N N2 0.83 2.44 3.0143(16) 127.5 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.579 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.061 data_lj207sad _database_code_depnum_ccdc_archive 'CCDC 819261' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 N3 O S' _chemical_formula_sum 'C20 H27 N3 O S' _chemical_formula_weight 357.51 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9772(8) _cell_length_b 11.2223(8) _cell_length_c 11.6609(15) _cell_angle_alpha 116.367(8) _cell_angle_beta 110.079(9) _cell_angle_gamma 94.316(6) _cell_volume 951.70(20) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1324 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 32.68 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.110 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 45310 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 33.16 _reflns_number_total 7186 _reflns_number_gt 5719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0466P)^2^+0.3262P] 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 7186 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.06227(15) -0.11286(12) 0.81645(12) 0.0161(2) Uani 1 1 d . . . C2 C 0.96122(15) -0.24710(12) 0.70518(12) 0.0178(2) Uani 1 1 d . . . C3 C 1.02921(16) -0.35854(13) 0.67894(13) 0.0218(2) Uani 1 1 d . . . H3 H 0.9620 -0.4479 0.6038 0.026 Uiso 1 1 calc R . . C4 C 1.19318(17) -0.34323(13) 0.75961(14) 0.0238(3) Uani 1 1 d . . . H4 H 1.2371 -0.4208 0.7399 0.029 Uiso 1 1 calc R . . C5 C 1.29101(16) -0.21230(13) 0.86930(13) 0.0214(2) Uani 1 1 d . . . H5 H 1.4026 -0.2006 0.9255 0.026 Uiso 1 1 calc R . . C6 C 1.22742(15) -0.09785(12) 0.89786(12) 0.0185(2) Uani 1 1 d . . . H6 H 1.2962 -0.0090 0.9729 0.022 Uiso 1 1 calc R . . C7 C 0.78046(16) -0.26808(13) 0.62025(13) 0.0221(2) Uani 1 1 d . . . H7A H 0.7324 -0.3652 0.5423 0.027 Uiso 1 1 calc R . . H7B H 0.7220 -0.2517 0.6818 0.027 Uiso 1 1 calc R . . C8 C 0.79606(17) -0.21607(14) 0.44120(14) 0.0251(3) Uani 1 1 d . . . H8A H 0.7277 -0.3103 0.3643 0.030 Uiso 1 1 calc R . . H8B H 0.9132 -0.2168 0.4704 0.030 Uiso 1 1 calc R . . C9 C 0.76695(17) -0.11473(15) 0.38868(14) 0.0259(3) Uani 1 1 d . . . H9A H 0.8384 -0.0209 0.4637 0.031 Uiso 1 1 calc R . . H9B H 0.7929 -0.1423 0.3060 0.031 Uiso 1 1 calc R . . C10 C 0.54220(18) -0.04874(15) 0.27060(13) 0.0270(3) Uani 1 1 d . . . H10A H 0.4222 -0.0610 0.2418 0.032 Uiso 1 1 calc R . . H10B H 0.5602 -0.0942 0.1837 0.032 Uiso 1 1 calc R . . C11 C 0.62798(17) 0.10458(14) 0.35034(14) 0.0260(3) Uani 1 1 d . . . H11A H 0.7466 0.1175 0.3717 0.031 Uiso 1 1 calc R . . H11B H 0.5809 0.1449 0.2903 0.031 Uiso 1 1 calc R . . C12 C 0.71885(16) 0.31763(13) 0.57386(14) 0.0231(3) Uani 1 1 d . . . H12A H 0.6898 0.3716 0.5255 0.028 Uiso 1 1 calc R . . H12B H 0.8339 0.3139 0.5910 0.028 Uiso 1 1 calc R . . C13 C 0.70689(15) 0.38923(12) 0.71324(14) 0.0211(2) Uani 1 1 d . . . C14 C 0.78665(15) 0.36095(12) 0.82230(13) 0.0185(2) Uani 1 1 d . . . C15 C 0.76942(16) 0.42706(13) 0.94918(14) 0.0225(2) Uani 1 1 d . . . H15 H 0.8233 0.4084 1.0227 0.027 Uiso 1 1 calc R . . C16 C 0.67359(17) 0.52008(14) 0.96790(16) 0.0294(3) Uani 1 1 d . . . H16 H 0.6618 0.5640 1.0539 0.035 Uiso 1 1 calc R . . C17 C 0.59554(17) 0.54903(14) 0.86226(17) 0.0334(3) Uani 1 1 d . . . H17 H 0.5305 0.6127 0.8755 0.040 Uiso 1 1 calc R . . C18 C 0.61313(17) 0.48400(14) 0.73626(16) 0.0296(3) Uani 1 1 d . . . H18 H 0.5600 0.5047 0.6642 0.035 Uiso 1 1 calc R . . C19 C 0.98795(15) 0.23927(12) 0.95590(12) 0.0176(2) Uani 1 1 d . . . H19A H 1.0557 0.3330 1.0343 0.021 Uiso 1 1 calc R . . H19B H 0.8963 0.2119 0.9757 0.021 Uiso 1 1 calc R . . C20 C 1.09291(15) 0.13768(12) 0.94580(12) 0.0179(2) Uani 1 1 d . . . H20A H 1.1784 0.1604 0.9177 0.022 Uiso 1 1 calc R . . H20B H 1.1491 0.1459 1.0394 0.022 Uiso 1 1 calc R . . N1 N 0.75347(14) -0.17647(11) 0.56088(11) 0.0196(2) Uani 1 1 d . . . H1N H 0.629(2) 0.1288(17) 0.5248(18) 0.029 Uiso 1 1 d . . . N2 N 0.60882(13) 0.17661(11) 0.48219(11) 0.0205(2) Uani 1 1 d . . . H2N H 0.648(2) -0.1755(17) 0.5338(18) 0.031 Uiso 1 1 d . . . N3 N 0.99198(13) -0.00317(10) 0.84323(11) 0.0186(2) Uani 1 1 d . . . H3N H 0.911(2) -0.0138(17) 0.7701(18) 0.028 Uiso 1 1 d . . . O1 O 0.59785(11) -0.11563(10) 0.35034(9) 0.02342(19) Uani 1 1 d . . . S1 S 0.90584(4) 0.24073(3) 0.79086(3) 0.02002(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0190(6) 0.0157(5) 0.0154(5) 0.0092(4) 0.0072(4) 0.0056(4) C2 0.0188(6) 0.0163(5) 0.0177(5) 0.0092(4) 0.0062(4) 0.0042(4) C3 0.0269(7) 0.0154(5) 0.0213(5) 0.0083(5) 0.0095(5) 0.0057(5) C4 0.0300(7) 0.0210(6) 0.0257(6) 0.0133(5) 0.0137(5) 0.0143(5) C5 0.0206(6) 0.0268(6) 0.0203(5) 0.0142(5) 0.0083(5) 0.0108(5) C6 0.0192(6) 0.0189(5) 0.0169(5) 0.0095(4) 0.0065(4) 0.0054(4) C7 0.0192(6) 0.0187(6) 0.0235(6) 0.0099(5) 0.0052(5) 0.0024(5) C8 0.0245(7) 0.0267(6) 0.0227(6) 0.0110(5) 0.0100(5) 0.0097(5) C9 0.0220(6) 0.0327(7) 0.0273(6) 0.0169(6) 0.0121(5) 0.0084(5) C10 0.0276(7) 0.0340(7) 0.0170(5) 0.0141(5) 0.0053(5) 0.0079(6) C11 0.0288(7) 0.0338(7) 0.0234(6) 0.0196(6) 0.0125(5) 0.0085(6) C12 0.0205(6) 0.0241(6) 0.0262(6) 0.0173(5) 0.0059(5) 0.0023(5) C13 0.0158(6) 0.0159(5) 0.0275(6) 0.0117(5) 0.0043(5) 0.0012(4) C14 0.0164(6) 0.0139(5) 0.0241(5) 0.0094(5) 0.0075(5) 0.0037(4) C15 0.0220(6) 0.0180(6) 0.0271(6) 0.0094(5) 0.0126(5) 0.0058(5) C16 0.0211(7) 0.0202(6) 0.0378(7) 0.0057(6) 0.0147(6) 0.0052(5) C17 0.0190(7) 0.0191(6) 0.0469(9) 0.0084(6) 0.0081(6) 0.0084(5) C18 0.0191(6) 0.0209(6) 0.0385(7) 0.0150(6) 0.0012(6) 0.0047(5) C19 0.0216(6) 0.0154(5) 0.0161(5) 0.0078(4) 0.0082(4) 0.0061(4) C20 0.0199(6) 0.0154(5) 0.0155(5) 0.0072(4) 0.0051(4) 0.0045(4) N1 0.0171(5) 0.0205(5) 0.0182(4) 0.0091(4) 0.0049(4) 0.0065(4) N2 0.0199(5) 0.0229(5) 0.0209(5) 0.0138(4) 0.0076(4) 0.0038(4) N3 0.0186(5) 0.0146(5) 0.0167(4) 0.0067(4) 0.0026(4) 0.0047(4) O1 0.0190(4) 0.0282(5) 0.0222(4) 0.0144(4) 0.0057(4) 0.0044(4) S1 0.02601(17) 0.02013(15) 0.01803(14) 0.01092(12) 0.01067(12) 0.01208(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N3 1.3863(15) . ? C1 C6 1.4077(17) . ? C1 C2 1.4233(17) . ? C2 C3 1.3905(17) . ? C2 C7 1.5170(17) . ? C3 C4 1.3960(19) . ? C3 H3 0.9500 . ? C4 C5 1.3897(19) . ? C4 H4 0.9500 . ? C5 C6 1.3955(17) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.4662(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N1 1.4602(16) . ? C8 C9 1.5134(19) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.4255(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O1 1.4265(15) . ? C10 C11 1.519(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N2 1.4648(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N2 1.4696(17) . ? C12 C13 1.5072(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.3956(18) . ? C13 C14 1.4136(17) . ? C14 C15 1.4009(17) . ? C14 S1 1.7739(12) . ? C15 C16 1.3925(18) . ? C15 H15 0.9500 . ? C16 C17 1.382(2) . ? C16 H16 0.9500 . ? C17 C18 1.393(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.5233(16) . ? C19 S1 1.8174(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N3 1.4529(15) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? N1 H2N 0.889(18) . ? N2 H1N 0.870(17) . ? N3 H3N 0.861(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C1 C6 122.79(11) . . ? N3 C1 C2 118.46(11) . . ? C6 C1 C2 118.71(11) . . ? C3 C2 C1 119.10(11) . . ? C3 C2 C7 120.79(11) . . ? C1 C2 C7 120.08(10) . . ? C2 C3 C4 122.04(12) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 118.74(11) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 120.81(11) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 120.59(11) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C2 113.02(10) . . ? N1 C7 H7A 109.0 . . ? C2 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C9 109.76(11) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O1 C9 C8 107.61(10) . . ? O1 C9 H9A 110.2 . . ? C8 C9 H9A 110.2 . . ? O1 C9 H9B 110.2 . . ? C8 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? O1 C10 C11 113.66(10) . . ? O1 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? O1 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? N2 C11 C10 111.16(10) . . ? N2 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? N2 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N2 C12 C13 111.74(10) . . ? N2 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N2 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C14 118.38(12) . . ? C18 C13 C12 120.16(12) . . ? C14 C13 C12 121.45(11) . . ? C15 C14 C13 119.82(11) . . ? C15 C14 S1 122.63(9) . . ? C13 C14 S1 117.55(10) . . ? C16 C15 C14 120.21(13) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.51(14) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.42(13) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C13 121.66(13) . . ? C17 C18 H18 119.2 . . ? C13 C18 H18 119.2 . . ? C20 C19 S1 109.67(8) . . ? C20 C19 H19A 109.7 . . ? S1 C19 H19A 109.7 . . ? C20 C19 H19B 109.7 . . ? S1 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? N3 C20 C19 110.79(10) . . ? N3 C20 H20A 109.5 . . ? C19 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C8 N1 C7 113.52(10) . . ? C8 N1 H2N 109.0(11) . . ? C7 N1 H2N 109.2(11) . . ? C11 N2 C12 111.54(10) . . ? C11 N2 H1N 108.5(11) . . ? C12 N2 H1N 110.7(11) . . ? C1 N3 C20 120.67(10) . . ? C1 N3 H3N 113.9(11) . . ? C20 N3 H3N 116.0(11) . . ? C9 O1 C10 114.26(10) . . ? C14 S1 C19 102.86(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C3 -178.73(10) . . . . ? C6 C1 C2 C3 -1.03(16) . . . . ? N3 C1 C2 C7 -0.83(16) . . . . ? C6 C1 C2 C7 176.87(10) . . . . ? C1 C2 C3 C4 0.87(18) . . . . ? C7 C2 C3 C4 -177.01(11) . . . . ? C2 C3 C4 C5 -0.09(19) . . . . ? C3 C4 C5 C6 -0.53(18) . . . . ? C4 C5 C6 C1 0.34(17) . . . . ? N3 C1 C6 C5 178.03(10) . . . . ? C2 C1 C6 C5 0.44(16) . . . . ? C3 C2 C7 N1 -128.75(12) . . . . ? C1 C2 C7 N1 53.39(15) . . . . ? N1 C8 C9 O1 -58.40(14) . . . . ? O1 C10 C11 N2 -57.10(15) . . . . ? N2 C12 C13 C18 -100.57(13) . . . . ? N2 C12 C13 C14 78.22(14) . . . . ? C18 C13 C14 C15 0.37(18) . . . . ? C12 C13 C14 C15 -178.45(11) . . . . ? C18 C13 C14 S1 -179.73(9) . . . . ? C12 C13 C14 S1 1.46(15) . . . . ? C13 C14 C15 C16 0.22(18) . . . . ? S1 C14 C15 C16 -179.67(10) . . . . ? C14 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C18 0.2(2) . . . . ? C16 C17 C18 C13 0.5(2) . . . . ? C14 C13 C18 C17 -0.71(19) . . . . ? C12 C13 C18 C17 178.12(12) . . . . ? S1 C19 C20 N3 -66.44(11) . . . . ? C9 C8 N1 C7 -179.08(10) . . . . ? C2 C7 N1 C8 73.99(13) . . . . ? C10 C11 N2 C12 168.03(11) . . . . ? C13 C12 N2 C11 -176.63(10) . . . . ? C6 C1 N3 C20 8.63(16) . . . . ? C2 C1 N3 C20 -173.78(10) . . . . ? C19 C20 N3 C1 179.78(10) . . . . ? C8 C9 O1 C10 -167.04(10) . . . . ? C11 C10 O1 C9 -63.26(15) . . . . ? C15 C14 S1 C19 -1.50(12) . . . . ? C13 C14 S1 C19 178.60(9) . . . . ? C20 C19 S1 C14 179.09(8) . . . . ? 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 H1N O1 0.870(17) 2.506(16) 2.9151(15) 109.6(13) . N2 H1N S1 0.870(17) 2.857(17) 3.3770(12) 120.0(13) . N1 H2N N2 0.889(18) 2.250(18) 3.1156(16) 164.4(15) 2_656 N3 H3N N1 0.861(17) 2.138(17) 2.8377(16) 138.1(14) . N3 H3N S1 0.861(17) 2.763(16) 3.1530(10) 109.2(12) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 33.16 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.489 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.068 data_lj208sad _database_code_depnum_ccdc_archive 'CCDC 819262' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 N3 S2' _chemical_formula_sum 'C20 H27 N3 S2' _chemical_formula_weight 373.57 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' S S 0.1246 0.1234 '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' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4397(12) _cell_length_b 10.8410(14) _cell_length_c 11.552(2) _cell_angle_alpha 104.996(13) _cell_angle_beta 104.979(13) _cell_angle_gamma 111.385(9) _cell_volume 978.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2617 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.59 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.170 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 45395 _diffrn_reflns_av_R_equivalents 0.0872 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.33 _reflns_number_total 4854 _reflns_number_gt 4082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0353P)^2^+0.7706P] 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 4854 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6328(3) 0.5663(2) 0.3637(2) 0.0199(5) Uani 1 1 d . . . C2 C 0.5271(3) 0.5317(2) 0.2365(2) 0.0208(5) Uani 1 1 d . . . C3 C 0.5152(3) 0.4222(2) 0.1330(2) 0.0244(5) Uani 1 1 d . . . H3 H 0.4440 0.3982 0.0469 0.029 Uiso 1 1 calc R . . C4 C 0.6055(3) 0.3475(3) 0.1533(2) 0.0279(6) Uani 1 1 d . . . H4 H 0.5959 0.2732 0.0818 0.033 Uiso 1 1 calc R . . C5 C 0.7097(3) 0.3825(2) 0.2789(3) 0.0268(5) Uani 1 1 d . . . H5 H 0.7724 0.3325 0.2931 0.032 Uiso 1 1 calc R . . C6 C 0.7232(3) 0.4901(2) 0.3842(2) 0.0235(5) Uani 1 1 d . . . H6 H 0.7935 0.5121 0.4700 0.028 Uiso 1 1 calc R . . C7 C 0.4323(3) 0.6145(2) 0.2106(2) 0.0240(5) Uani 1 1 d . . . H7A H 0.3398 0.5577 0.1240 0.029 Uiso 1 1 calc R . . H7B H 0.3849 0.6297 0.2769 0.029 Uiso 1 1 calc R . . C8 C 0.4649(3) 0.8506(2) 0.2186(2) 0.0237(5) Uani 1 1 d . . . H8A H 0.4418 0.8707 0.2984 0.028 Uiso 1 1 calc R . . H8B H 0.3587 0.8037 0.1423 0.028 Uiso 1 1 calc R . . C9 C 0.5799(3) 0.9906(3) 0.2175(2) 0.0267(5) Uani 1 1 d . . . H9A H 0.5263 1.0541 0.2199 0.032 Uiso 1 1 calc R . . H9B H 0.5968 0.9698 0.1349 0.032 Uiso 1 1 calc R . . C10 C 0.7194(3) 1.1402(3) 0.4875(2) 0.0285(5) Uani 1 1 d . . . H10A H 0.6574 1.1942 0.4691 0.034 Uiso 1 1 calc R . . H10B H 0.6456 1.0534 0.4955 0.034 Uiso 1 1 calc R . . C11 C 0.8705(3) 1.2340(3) 0.6145(2) 0.0255(5) Uani 1 1 d . . . H11A H 0.9455 1.3194 0.6053 0.031 Uiso 1 1 calc R . . H11B H 0.8355 1.2682 0.6848 0.031 Uiso 1 1 calc R . . C12 C 1.0790(3) 1.2271(3) 0.7868(2) 0.0233(5) Uani 1 1 d . . . H12A H 1.1430 1.3309 0.8071 0.028 Uiso 1 1 calc R . . H12B H 1.1576 1.1865 0.7987 0.028 Uiso 1 1 calc R . . C13 C 0.9940(3) 1.2101(2) 0.8804(2) 0.0193(5) Uani 1 1 d . . . C14 C 0.8976(3) 1.0709(2) 0.8735(2) 0.0178(4) Uani 1 1 d . . . C15 C 0.8360(3) 1.0595(2) 0.9714(2) 0.0202(5) Uani 1 1 d . . . H15 H 0.7740 0.9673 0.9700 0.024 Uiso 1 1 calc R . . C16 C 0.8658(3) 1.1832(3) 1.0702(2) 0.0238(5) Uani 1 1 d . . . H16 H 0.8251 1.1739 1.1362 0.029 Uiso 1 1 calc R . . C17 C 0.9532(3) 1.3186(3) 1.0740(2) 0.0254(5) Uani 1 1 d . . . H17 H 0.9703 1.4020 1.1403 0.030 Uiso 1 1 calc R . . C18 C 1.0161(3) 1.3305(2) 0.9783(2) 0.0218(5) Uani 1 1 d . . . H18 H 1.0757 1.4234 0.9799 0.026 Uiso 1 1 calc R . . C19 C 0.7661(3) 0.8062(2) 0.7571(2) 0.0203(5) Uani 1 1 d . . . H19A H 0.6536 0.7949 0.7442 0.024 Uiso 1 1 calc R . . H19B H 0.8086 0.7895 0.8364 0.024 Uiso 1 1 calc R . . C20 C 0.7582(3) 0.6956(2) 0.6398(2) 0.0218(5) Uani 1 1 d . . . H20A H 0.7013 0.5976 0.6377 0.026 Uiso 1 1 calc R . . H20B H 0.8714 0.7152 0.6460 0.026 Uiso 1 1 calc R . . N1 N 0.5401(2) 0.7543(2) 0.2145(2) 0.0222(4) Uani 1 1 d . . . N2 N 0.9597(2) 1.1542(2) 0.6500(2) 0.0234(4) Uani 1 1 d . . . N3 N 0.8734(2) 0.9514(2) 0.7746(2) 0.0220(4) Uani 1 1 d . . . S1 S 0.78170(7) 1.08667(6) 0.35400(6) 0.02269(15) Uani 1 1 d . . . S2 S 0.64571(8) 0.70692(7) 0.49268(6) 0.02957(17) Uani 1 1 d . . . H1N H 1.014(4) 1.147(3) 0.602(3) 0.044 Uiso 1 1 d . . . H2N H 0.627(4) 0.793(3) 0.284(3) 0.044 Uiso 1 1 d . . . H3N H 0.873(4) 0.965(3) 0.706(3) 0.044 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 C1 0.0217(11) 0.0129(10) 0.0232(12) 0.0042(9) 0.0094(9) 0.0076(9) C2 0.0193(11) 0.0157(11) 0.0255(12) 0.0078(10) 0.0096(10) 0.0058(9) C3 0.0268(12) 0.0203(11) 0.0207(12) 0.0064(10) 0.0091(10) 0.0067(10) C4 0.0367(14) 0.0187(12) 0.0272(14) 0.0042(10) 0.0182(12) 0.0111(11) C5 0.0314(13) 0.0194(12) 0.0362(15) 0.0106(11) 0.0180(12) 0.0153(10) C6 0.0280(12) 0.0214(12) 0.0255(13) 0.0097(10) 0.0111(10) 0.0151(10) C7 0.0173(11) 0.0206(12) 0.0288(13) 0.0084(10) 0.0055(10) 0.0067(9) C8 0.0215(11) 0.0268(12) 0.0250(13) 0.0109(10) 0.0075(10) 0.0140(10) C9 0.0285(13) 0.0268(13) 0.0252(13) 0.0121(11) 0.0067(11) 0.0145(11) C10 0.0273(12) 0.0369(14) 0.0272(13) 0.0130(11) 0.0148(11) 0.0174(11) C11 0.0298(13) 0.0258(12) 0.0256(13) 0.0100(10) 0.0146(11) 0.0150(11) C12 0.0176(11) 0.0249(12) 0.0239(13) 0.0077(10) 0.0074(10) 0.0082(9) C13 0.0155(10) 0.0234(11) 0.0179(11) 0.0066(9) 0.0049(9) 0.0100(9) C14 0.0164(10) 0.0196(11) 0.0182(11) 0.0062(9) 0.0050(9) 0.0111(9) C15 0.0213(11) 0.0202(11) 0.0217(12) 0.0092(9) 0.0086(9) 0.0114(9) C16 0.0268(12) 0.0318(13) 0.0186(12) 0.0094(10) 0.0103(10) 0.0188(11) C17 0.0267(12) 0.0271(13) 0.0204(12) 0.0034(10) 0.0074(10) 0.0157(11) C18 0.0199(11) 0.0185(11) 0.0211(12) 0.0041(9) 0.0048(9) 0.0078(9) C19 0.0215(11) 0.0198(11) 0.0205(12) 0.0068(9) 0.0083(9) 0.0113(9) C20 0.0244(11) 0.0182(11) 0.0230(12) 0.0076(10) 0.0082(10) 0.0113(9) N1 0.0199(10) 0.0225(10) 0.0257(11) 0.0106(9) 0.0075(8) 0.0116(8) N2 0.0259(10) 0.0271(11) 0.0221(11) 0.0102(9) 0.0137(9) 0.0139(9) N3 0.0283(10) 0.0185(10) 0.0207(10) 0.0070(8) 0.0118(9) 0.0112(8) S1 0.0223(3) 0.0247(3) 0.0225(3) 0.0104(2) 0.0103(2) 0.0104(2) S2 0.0406(4) 0.0278(3) 0.0217(3) 0.0037(3) 0.0067(3) 0.0250(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 C1 C6 1.406(3) . ? C1 C2 1.407(3) . ? C1 S2 1.776(2) . ? C2 C3 1.397(3) . ? C2 C7 1.511(3) . ? C3 C4 1.392(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.466(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N1 1.459(3) . ? C8 C9 1.516(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 S1 1.830(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.519(4) . ? C10 S1 1.821(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N2 1.471(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N2 1.475(3) . ? C12 C13 1.513(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.394(3) . ? C13 C14 1.418(3) . ? C14 N3 1.385(3) . ? C14 C15 1.412(3) . ? C15 C16 1.395(3) . ? C15 H15 0.9500 . ? C16 C17 1.380(3) . ? C16 H16 0.9500 . ? C17 C18 1.396(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N3 1.453(3) . ? C19 C20 1.523(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 S2 1.817(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? N1 H2N 0.85(3) . ? N2 H1N 0.85(3) . ? N3 H3N 0.84(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.7(2) . . ? C6 C1 S2 122.76(18) . . ? C2 C1 S2 117.57(16) . . ? C3 C2 C1 118.9(2) . . ? C3 C2 C7 120.1(2) . . ? C1 C2 C7 121.0(2) . . ? C4 C3 C2 121.4(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.1(2) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N1 C7 C2 111.00(18) . . ? N1 C7 H7A 109.4 . . ? C2 C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C2 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N1 C8 C9 110.18(19) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 S1 113.57(17) . . ? C8 C9 H9A 108.9 . . ? S1 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? S1 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 S1 110.27(16) . . ? C11 C10 H10A 109.6 . . ? S1 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? S1 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N2 C11 C10 111.3(2) . . ? N2 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? N2 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N2 C12 C13 111.94(18) . . ? N2 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N2 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C18 C13 C14 119.2(2) . . ? C18 C13 C12 120.7(2) . . ? C14 C13 C12 120.1(2) . . ? N3 C14 C15 122.3(2) . . ? N3 C14 C13 119.0(2) . . ? C15 C14 C13 118.6(2) . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 121.3(2) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 118.6(2) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C13 C18 C17 121.9(2) . . ? C13 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? N3 C19 C20 110.58(18) . . ? N3 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C19 C20 S2 108.66(15) . . ? C19 C20 H20A 110.0 . . ? S2 C20 H20A 110.0 . . ? C19 C20 H20B 110.0 . . ? S2 C20 H20B 110.0 . . ? H20A C20 H20B 108.3 . . ? C8 N1 C7 112.88(18) . . ? C8 N1 H2N 108(2) . . ? C7 N1 H2N 106(2) . . ? C11 N2 C12 112.55(19) . . ? C11 N2 H1N 109(2) . . ? C12 N2 H1N 108(2) . . ? C14 N3 C19 121.41(19) . . ? C14 N3 H3N 113(2) . . ? C19 N3 H3N 116(2) . . ? C10 S1 C9 99.74(12) . . ? C1 S2 C20 104.43(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(3) . . . . ? S2 C1 C2 C3 179.56(17) . . . . ? C6 C1 C2 C7 -178.1(2) . . . . ? S2 C1 C2 C7 1.9(3) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C7 C2 C3 C4 177.7(2) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? S2 C1 C6 C5 -179.01(18) . . . . ? C3 C2 C7 N1 -100.3(2) . . . . ? C1 C2 C7 N1 77.3(3) . . . . ? N1 C8 C9 S1 -58.9(2) . . . . ? S1 C10 C11 N2 -63.2(2) . . . . ? N2 C12 C13 C18 -122.7(2) . . . . ? N2 C12 C13 C14 60.6(3) . . . . ? C18 C13 C14 N3 178.8(2) . . . . ? C12 C13 C14 N3 -4.5(3) . . . . ? C18 C13 C14 C15 -4.0(3) . . . . ? C12 C13 C14 C15 172.8(2) . . . . ? N3 C14 C15 C16 179.0(2) . . . . ? C13 C14 C15 C16 1.9(3) . . . . ? C14 C15 C16 C17 1.0(3) . . . . ? C15 C16 C17 C18 -1.7(3) . . . . ? C14 C13 C18 C17 3.4(3) . . . . ? C12 C13 C18 C17 -173.4(2) . . . . ? C16 C17 C18 C13 -0.5(3) . . . . ? N3 C19 C20 S2 -69.4(2) . . . . ? C9 C8 N1 C7 -177.9(2) . . . . ? C2 C7 N1 C8 -167.4(2) . . . . ? C10 C11 N2 C12 -164.93(19) . . . . ? C13 C12 N2 C11 75.5(2) . . . . ? C15 C14 N3 C19 7.4(3) . . . . ? C13 C14 N3 C19 -175.5(2) . . . . ? C20 C19 N3 C14 178.60(19) . . . . ? C11 C10 S1 C9 -175.68(18) . . . . ? C8 C9 S1 C10 -68.7(2) . . . . ? C6 C1 S2 C20 -10.9(2) . . . . ? C2 C1 S2 C20 169.16(17) . . . . ? C19 C20 S2 C1 -176.23(15) . . . . ? 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 N1 H2N S2 0.85(3) 2.78(3) 3.340(2) 124(2) . N3 H3N N2 0.84(3) 2.25(3) 2.917(3) 137(3) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.458 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.066 data_lj246sad _database_code_depnum_ccdc_archive 'CCDC 819263' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Cl2 N4 Ni O, 3(H2 O)' _chemical_formula_sum 'C20 H34 Cl2 N4 Ni O4' _chemical_formula_weight 524.12 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 C2/m _symmetry_space_group_name_Hall '-C 2y' _symmetry_Int_Tables_number 12 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 16.696(2) _cell_length_b 15.556(2) _cell_length_c 8.8940(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.522(2) _cell_angle_gamma 90.00 _cell_volume 2309.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8225 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.25 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6146 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 188 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.01 _diffrn_reflns_number 11490 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2854 _reflns_number_gt 2677 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0459P)^2^+3.0824P] 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 2854 _refine_ls_number_parameters 170 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.295 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8137(2) -0.0351(3) 0.4427(5) 0.0261(6) Uani 0.50 1 d P . 1 H1A H 0.8452 -0.0534 0.5321 0.031 Uiso 0.50 1 calc PR . 1 H1B H 0.8444 -0.0534 0.3536 0.031 Uiso 0.50 1 calc PRD . 1 C1A C 0.7978(2) -0.0443(3) 0.5250(5) 0.0261(6) Uani 0.50 1 d P . 2 H1A1 H 0.7954 -0.0635 0.6309 0.031 Uiso 0.50 1 calc PR . 2 H1A2 H 0.8500 -0.0635 0.4851 0.031 Uiso 0.50 1 calc PR . 2 C2 C 0.63551(12) -0.07987(15) 0.0809(2) 0.0276(4) Uani 1 1 d . . . H2A H 0.6759 -0.1263 0.0880 0.033 Uiso 1 1 calc R . . H2B H 0.6231 -0.0703 -0.0268 0.033 Uiso 1 1 calc R . . C3 C 0.55925(12) -0.10801(14) 0.1617(2) 0.0255(4) Uani 1 1 d . . . H3A H 0.5139 -0.0714 0.1287 0.031 Uiso 1 1 calc R . . H3B H 0.5465 -0.1682 0.1344 0.031 Uiso 1 1 calc R . . C4 C 0.59427(12) -0.18304(14) 0.3994(2) 0.0253(4) Uani 1 1 d . . . H4A H 0.5526 -0.2272 0.3810 0.030 Uiso 1 1 calc R . . H4B H 0.5991 -0.1744 0.5094 0.030 Uiso 1 1 calc R . . C5 C 0.67273(12) -0.21434(14) 0.3397(2) 0.0247(4) Uani 1 1 d . . . C6 C 0.74292(12) -0.16649(14) 0.3597(2) 0.0256(4) Uani 1 1 d . . . C7 C 0.81466(13) -0.19448(16) 0.2962(3) 0.0338(5) Uani 1 1 d . . . H7 H 0.8623 -0.1618 0.3096 0.041 Uiso 1 1 calc RD . . C8 C 0.81613(15) -0.26932(18) 0.2144(3) 0.0409(6) Uani 1 1 d . . . H8 H 0.8648 -0.2875 0.1698 0.049 Uiso 1 1 calc R . . C9 C 0.74806(15) -0.31829(17) 0.1962(3) 0.0394(6) Uani 1 1 d . . . H9 H 0.7501 -0.3710 0.1424 0.047 Uiso 1 1 calc R . . C10 C 0.67614(14) -0.29006(15) 0.2571(2) 0.0306(4) Uani 1 1 d . . . H10 H 0.6288 -0.3230 0.2419 0.037 Uiso 1 1 calc R . . N1 N 0.73574(10) -0.08884(11) 0.4425(2) 0.0277(3) Uani 0.50 1 d P . 1 O1 O 0.73574(10) -0.08884(11) 0.4425(2) 0.0277(3) Uani 0.50 1 d P . 2 N2 N 0.66937(14) 0.0000 0.1465(3) 0.0259(5) Uani 1 2 d S . . N3 N 0.56952(10) -0.10117(11) 0.32711(18) 0.0215(3) Uani 1 1 d . . . O1W O 1.0000 0.12020(19) 0.5000 0.0477(6) Uani 1 2 d SD . . O2W O 1.01104(18) 0.0000 0.2527(3) 0.0488(7) Uani 1 2 d SD . . O3W O 1.0000 0.8253(2) 0.0000 0.0785(12) Uani 1 2 d SD . . Cl1 Cl 0.60248(4) 0.0000 0.64196(7) 0.02104(15) Uani 1 2 d S . . Cl2 Cl 0.86373(5) 0.0000 0.01910(10) 0.0407(2) Uani 1 2 d S . . Ni1 Ni 0.645101(18) 0.0000 0.37932(4) 0.01778(12) Uani 1 2 d S . . H1N H 0.734(3) -0.096(3) 0.521(6) 0.021 Uiso 0.50 1 d P A 1 H2N H 0.718(2) 0.0000 0.129(4) 0.021 Uiso 1 2 d S . . H3N H 0.5217(15) -0.0857(17) 0.360(3) 0.021 Uiso 1 1 d . . . H1O H 0.9962(15) 0.0875(14) 0.5826(19) 0.021 Uiso 1 1 d D . . H2O H 0.9711(15) 0.0000 0.187(3) 0.021 Uiso 1 2 d SD . . H3O H 1.0564(12) 0.0000 0.204(3) 0.021 Uiso 1 2 d SD . . H4O H 0.9598(11) 0.8633(13) 0.004(3) 0.021 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 C1 0.0140(13) 0.0324(14) 0.0317(17) 0.0047(14) -0.0012(13) -0.0001(10) C1A 0.0140(13) 0.0324(14) 0.0317(17) 0.0047(14) -0.0012(13) -0.0001(10) C2 0.0237(9) 0.0422(12) 0.0169(9) -0.0057(8) 0.0026(7) 0.0085(9) C3 0.0216(9) 0.0334(11) 0.0213(9) -0.0075(8) -0.0016(7) 0.0029(8) C4 0.0232(9) 0.0275(10) 0.0253(9) -0.0007(8) 0.0035(7) -0.0014(8) C5 0.0227(9) 0.0269(10) 0.0246(9) 0.0007(8) 0.0024(7) 0.0044(8) C6 0.0231(9) 0.0278(10) 0.0259(10) 0.0020(8) 0.0003(7) 0.0057(8) C7 0.0226(10) 0.0412(13) 0.0375(12) 0.0057(10) 0.0037(9) 0.0063(9) C8 0.0340(12) 0.0483(14) 0.0408(13) 0.0000(11) 0.0124(10) 0.0180(11) C9 0.0427(14) 0.0377(13) 0.0380(13) -0.0098(10) 0.0090(10) 0.0118(11) C10 0.0320(11) 0.0301(11) 0.0297(10) -0.0024(9) 0.0027(8) 0.0030(9) N1 0.0209(7) 0.0250(8) 0.0371(9) -0.0033(7) -0.0052(7) 0.0020(6) O1 0.0209(7) 0.0250(8) 0.0371(9) -0.0033(7) -0.0052(7) 0.0020(6) N2 0.0145(11) 0.0454(15) 0.0180(11) 0.000 0.0042(8) 0.000 N3 0.0165(7) 0.0288(9) 0.0193(8) -0.0043(6) 0.0029(6) 0.0012(6) O1W 0.0422(14) 0.0428(15) 0.0581(18) 0.000 0.0052(13) 0.000 O2W 0.0419(15) 0.073(2) 0.0312(13) 0.000 0.0040(11) 0.000 O3W 0.083(3) 0.0456(19) 0.107(3) 0.000 -0.026(2) 0.000 Cl1 0.0163(3) 0.0311(3) 0.0157(3) 0.000 0.0031(2) 0.000 Cl2 0.0275(4) 0.0574(5) 0.0371(4) 0.000 0.0061(3) 0.000 Ni1 0.01265(18) 0.0251(2) 0.01564(18) 0.000 0.00257(12) 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 C1 C1 1.093(8) 6 ? C1 N1 1.547(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1A C1A 1.377(9) 6 ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2 N2 1.482(3) . ? C2 C3 1.531(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N3 1.484(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N3 1.484(3) . ? C4 C5 1.499(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.390(3) . ? C5 C6 1.398(3) . ? C6 C7 1.398(3) . ? C6 N1 1.420(3) . ? C7 C8 1.373(4) . ? C7 H7 0.9500 . ? C8 C9 1.376(4) . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N1 Ni1 2.1214(17) . ? N1 H1N 0.71(5) . ? N2 C2 1.482(3) 6 ? N2 Ni1 2.113(2) . ? N2 H2N 0.83(4) . ? N3 Ni1 2.0675(17) . ? N3 H3N 0.89(3) . ? O1W H1O 0.896(11) . ? O2W H2O 0.88(3) . ? O2W H3O 0.876(12) . ? O3W H4O 0.896(11) . ? Cl1 Ni1 2.4481(7) . ? Ni1 N3 2.0675(17) 6 ? Ni1 O1 2.1214(17) 6 ? Ni1 N1 2.1214(17) 6 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C1 N1 122.71(16) 6 . ? C1 C1 H1A 106.7 6 . ? N1 C1 H1A 106.7 . . ? C1 C1 H1B 106.7 6 . ? N1 C1 H1B 106.7 . . ? H1A C1 H1B 106.6 . . ? C1A C1A H1A1 107.6 6 . ? C1A C1A H1A2 107.6 6 . ? H1A1 C1A H1A2 107.1 . . ? C1A C1A H1N 127(2) 6 . ? H1A1 C1A H1N 78.7 . . ? H1A2 C1A H1N 121.0 . . ? N2 C2 C3 111.76(17) . . ? N2 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N3 C3 C2 110.82(16) . . ? N3 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N3 C4 C5 111.48(17) . . ? N3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C10 C5 C6 118.69(19) . . ? C10 C5 C4 120.18(19) . . ? C6 C5 C4 121.07(19) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 N1 116.37(18) . . ? C7 C6 N1 123.4(2) . . ? C8 C7 C6 119.8(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.9(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C10 119.6(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C5 C10 C9 120.8(2) . . ? C5 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C6 N1 C1 112.7(2) . . ? C6 N1 Ni1 118.68(13) . . ? C1 N1 Ni1 104.28(18) . . ? C6 N1 H1N 113(4) . . ? C1 N1 H1N 98(4) . . ? Ni1 N1 H1N 109(4) . . ? C2 N2 C2 113.9(2) . 6 ? C2 N2 Ni1 108.05(13) . . ? C2 N2 Ni1 108.05(13) 6 . ? C2 N2 H2N 107.2(12) . . ? C2 N2 H2N 107.2(12) 6 . ? Ni1 N2 H2N 113(2) . . ? C3 N3 C4 113.43(16) . . ? C3 N3 Ni1 110.01(13) . . ? C4 N3 Ni1 112.89(12) . . ? C3 N3 H3N 104.7(15) . . ? C4 N3 H3N 109.7(16) . . ? Ni1 N3 H3N 105.5(16) . . ? H2O O2W H3O 109(3) . . ? N3 Ni1 N3 99.15(10) . 6 ? N3 Ni1 N2 84.38(6) . . ? N3 Ni1 N2 84.38(6) 6 . ? N3 Ni1 O1 171.07(7) . 6 ? N3 Ni1 O1 89.78(7) 6 6 ? N2 Ni1 O1 96.71(7) . 6 ? N3 Ni1 N1 171.07(7) . 6 ? N3 Ni1 N1 89.78(7) 6 6 ? N2 Ni1 N1 96.71(7) . 6 ? O1 Ni1 N1 0.00(14) 6 6 ? N3 Ni1 N1 89.78(7) . . ? N3 Ni1 N1 171.07(7) 6 . ? N2 Ni1 N1 96.71(7) . . ? O1 Ni1 N1 81.30(9) 6 . ? N1 Ni1 N1 81.30(9) 6 . ? N3 Ni1 Cl1 91.85(5) . . ? N3 Ni1 Cl1 91.85(5) 6 . ? N2 Ni1 Cl1 174.15(7) . . ? O1 Ni1 Cl1 87.71(6) 6 . ? N1 Ni1 Cl1 87.71(6) 6 . ? N1 Ni1 Cl1 87.71(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N3 -44.2(2) . . . . ? N3 C4 C5 C10 -114.0(2) . . . . ? N3 C4 C5 C6 63.1(3) . . . . ? C10 C5 C6 C7 0.5(3) . . . . ? C4 C5 C6 C7 -176.5(2) . . . . ? C10 C5 C6 N1 178.80(19) . . . . ? C4 C5 C6 N1 1.7(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? N1 C6 C7 C8 -178.3(2) . . . . ? C6 C7 C8 C9 -1.2(4) . . . . ? C7 C8 C9 C10 2.2(4) . . . . ? C6 C5 C10 C9 0.5(3) . . . . ? C4 C5 C10 C9 177.6(2) . . . . ? C8 C9 C10 C5 -1.9(4) . . . . ? C5 C6 N1 C1 -173.2(2) . . . . ? C7 C6 N1 C1 5.0(3) . . . . ? C5 C6 N1 Ni1 -51.0(2) . . . . ? C7 C6 N1 Ni1 127.23(19) . . . . ? C1 C1 N1 C6 145.80(13) 6 . . . ? C1 C1 N1 Ni1 15.8(2) 6 . . . ? C3 C2 N2 C2 -87.2(2) . . . 6 ? C3 C2 N2 Ni1 32.8(2) . . . . ? C2 C3 N3 C4 -95.2(2) . . . . ? C2 C3 N3 Ni1 32.3(2) . . . . ? C5 C4 N3 C3 60.0(2) . . . . ? C5 C4 N3 Ni1 -65.97(18) . . . . ? C3 N3 Ni1 N3 71.95(14) . . . 6 ? C4 N3 Ni1 N3 -160.24(10) . . . 6 ? C3 N3 Ni1 N2 -11.41(13) . . . . ? C4 N3 Ni1 N2 116.40(13) . . . . ? C3 N3 Ni1 N1 -108.18(13) . . . . ? C4 N3 Ni1 N1 19.63(13) . . . . ? C3 N3 Ni1 Cl1 164.12(12) . . . . ? C4 N3 Ni1 Cl1 -68.07(12) . . . . ? C2 N2 Ni1 N3 -11.92(14) . . . . ? C2 N2 Ni1 N3 111.72(15) 6 . . . ? C2 N2 Ni1 N3 -111.72(15) . . . 6 ? C2 N2 Ni1 N3 11.92(14) 6 . . 6 ? C2 N2 Ni1 O1 159.17(14) . . . 6 ? C2 N2 Ni1 O1 -77.19(15) 6 . . 6 ? C2 N2 Ni1 N1 159.17(14) . . . 6 ? C2 N2 Ni1 N1 -77.19(15) 6 . . 6 ? C2 N2 Ni1 N1 77.19(15) . . . . ? C2 N2 Ni1 N1 -159.17(14) 6 . . . ? C6 N1 Ni1 N3 36.22(15) . . . . ? C1 N1 Ni1 N3 162.5(2) . . . . ? C6 N1 Ni1 N2 -48.09(16) . . . . ? C1 N1 Ni1 N2 78.2(2) . . . . ? C6 N1 Ni1 O1 -143.89(13) . . . 6 ? C1 N1 Ni1 O1 -17.6(2) . . . 6 ? C6 N1 Ni1 N1 -143.89(13) . . . 6 ? C1 N1 Ni1 N1 -17.6(2) . . . 6 ? C6 N1 Ni1 Cl1 128.07(15) . . . . ? C1 N1 Ni1 Cl1 -105.6(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 N2 H2N Cl2 0.83(4) 2.62(4) 3.447(3) 169(3) . N3 H3N Cl1 0.89(3) 2.46(3) 3.2884(18) 155(2) 5_656 O2W H2O Cl2 0.88(3) 2.32(3) 3.205(3) 178(3) . O2W H3O Cl2 0.876(12) 2.400(19) 3.210(3) 154(3) 5_755 O1W H1O O2W 0.896(11) 2.004(12) 2.894(3) 172(2) 5_756 O3W H4O Cl2 0.896(11) 2.667(12) 3.549(3) 168(2) 1_565 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.548 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.067 data_lj259sad _database_code_depnum_ccdc_archive 'CCDC 819264' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Cl2 Cu N4 O, C2 H3 N' _chemical_formula_sum 'C22 H31 Cl2 Cu N5 O' _chemical_formula_weight 515.96 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 21.9824(12) _cell_length_b 8.3281(4) _cell_length_c 26.8453(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.319(3) _cell_angle_gamma 90.00 _cell_volume 4874.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9956 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 29.87 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.180 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 1.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.738 _exptl_absorpt_correction_T_max 0.815 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 51326 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 30.03 _reflns_number_total 7111 _reflns_number_gt 5492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0355P)^2^+5.1593P] 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 7111 _refine_ls_number_parameters 293 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.57357(9) 0.5008(3) 0.70204(7) 0.0317(4) Uani 1 1 d . . . H1A H 0.5365 0.4851 0.7189 0.038 Uiso 1 1 calc R . . H1B H 0.6003 0.5810 0.7213 0.038 Uiso 1 1 calc R . . C2 C 0.60735(9) 0.3442(2) 0.69946(7) 0.0321(4) Uani 1 1 d . . . H2A H 0.6206 0.3064 0.7341 0.039 Uiso 1 1 calc R . . H2B H 0.5786 0.2633 0.6828 0.039 Uiso 1 1 calc R . . C3 C 0.72069(9) 0.3662(2) 0.69645(6) 0.0243(4) Uani 1 1 d . . . C4 C 0.73207(9) 0.4482(2) 0.74259(6) 0.0285(4) Uani 1 1 d . . . H4 H 0.6986 0.4925 0.7572 0.034 Uiso 1 1 calc R . . C5 C 0.79051(10) 0.4655(2) 0.76684(7) 0.0319(4) Uani 1 1 d . . . H5 H 0.7969 0.5234 0.7976 0.038 Uiso 1 1 calc R . . C6 C 0.84038(10) 0.4001(2) 0.74732(7) 0.0324(4) Uani 1 1 d . . . H6 H 0.8807 0.4120 0.7643 0.039 Uiso 1 1 calc R . . C7 C 0.82981(9) 0.3163(2) 0.70199(7) 0.0281(4) Uani 1 1 d . . . H7 H 0.8635 0.2680 0.6889 0.034 Uiso 1 1 calc R . . C8 C 0.77154(9) 0.3014(2) 0.67540(6) 0.0229(4) Uani 1 1 d . . . C9 C 0.76445(9) 0.2068(2) 0.62674(6) 0.0237(4) Uani 1 1 d . . . H9A H 0.7970 0.1240 0.6290 0.028 Uiso 1 1 calc R . . H9B H 0.7245 0.1502 0.6235 0.028 Uiso 1 1 calc R . . C10 C 0.82767(9) 0.3809(2) 0.57617(7) 0.0265(4) Uani 1 1 d . . . H10A H 0.8339 0.3903 0.5404 0.032 Uiso 1 1 calc R . . H10B H 0.8611 0.3136 0.5934 0.032 Uiso 1 1 calc R . . C11 C 0.83014(8) 0.5478(2) 0.60011(7) 0.0247(4) Uani 1 1 d . . . H11A H 0.8382 0.5379 0.6371 0.030 Uiso 1 1 calc R . . H11B H 0.8638 0.6109 0.5886 0.030 Uiso 1 1 calc R . . C12 C 0.75194(8) 0.7384(2) 0.62477(6) 0.0228(4) Uani 1 1 d . . . H12A H 0.7801 0.8313 0.6302 0.027 Uiso 1 1 calc R . . H12B H 0.7522 0.6802 0.6570 0.027 Uiso 1 1 calc R . . C13 C 0.68769(8) 0.7940(2) 0.60551(7) 0.0247(4) Uani 1 1 d . . . H13A H 0.6703 0.8553 0.6319 0.030 Uiso 1 1 calc R . . H13B H 0.6886 0.8648 0.5760 0.030 Uiso 1 1 calc R . . C14 C 0.58840(9) 0.6926(2) 0.56558(7) 0.0283(4) Uani 1 1 d . . . H14A H 0.5664 0.5934 0.5537 0.034 Uiso 1 1 calc R . . H14B H 0.5932 0.7594 0.5358 0.034 Uiso 1 1 calc R . . C15 C 0.55049(8) 0.7840(2) 0.59971(7) 0.0287(4) Uani 1 1 d . . . C16 C 0.53648(8) 0.7109(2) 0.64383(7) 0.0281(4) Uani 1 1 d . . . C17 C 0.50324(9) 0.7931(3) 0.67662(8) 0.0363(5) Uani 1 1 d . . . H17 H 0.4930 0.7417 0.7060 0.044 Uiso 1 1 calc R . . C18 C 0.48517(10) 0.9509(3) 0.66601(9) 0.0419(5) Uani 1 1 d . . . H18 H 0.4629 1.0076 0.6885 0.050 Uiso 1 1 calc R . . C19 C 0.49926(10) 1.0255(3) 0.62322(10) 0.0450(6) Uani 1 1 d . . . H19 H 0.4867 1.1332 0.6162 0.054 Uiso 1 1 calc R . . C20 C 0.53191(9) 0.9427(3) 0.59015(9) 0.0372(5) Uani 1 1 d . . . H20 H 0.5417 0.9949 0.5607 0.045 Uiso 1 1 calc R . . C21 C 0.42324(10) 0.4402(3) 0.62445(9) 0.0379(5) Uani 1 1 d . . . C22 C 0.44014(11) 0.4544(3) 0.57390(8) 0.0447(6) Uani 1 1 d . . . H22A H 0.4105 0.3955 0.5503 0.067 Uiso 1 1 calc R . . H22B H 0.4812 0.4093 0.5731 0.067 Uiso 1 1 calc R . . H22C H 0.4401 0.5679 0.5642 0.067 Uiso 1 1 calc R . . N1 N 0.66132(7) 0.3530(2) 0.67245(5) 0.0278(3) Uani 1 1 d D . . H1N H 0.6565(10) 0.307(3) 0.6423(4) 0.042 Uiso 1 1 d D . . N2 N 0.76751(7) 0.30331(17) 0.57997(5) 0.0209(3) Uani 1 1 d D . . H2N H 0.7618(9) 0.2297(18) 0.5558(5) 0.031 Uiso 1 1 d D . . N3 N 0.77119(7) 0.63049(17) 0.58583(5) 0.0190(3) Uani 1 1 d D . . H3N H 0.7739(9) 0.689(2) 0.5585(4) 0.029 Uiso 1 1 d D . . N4 N 0.64936(7) 0.65000(18) 0.59121(5) 0.0223(3) Uani 1 1 d D . . H4N H 0.6442(9) 0.597(2) 0.6191(4) 0.033 Uiso 1 1 d D . . N5 N 0.41004(10) 0.4282(3) 0.66393(8) 0.0528(5) Uani 1 1 d . . . O1 O 0.55652(6) 0.55547(17) 0.65112(5) 0.0289(3) Uani 1 1 d . . . Cl1 Cl 0.71181(2) 0.53759(5) 0.475307(14) 0.02378(9) Uani 1 1 d . . . Cl2 Cl 0.62389(2) 0.28969(6) 0.551389(16) 0.03101(11) Uani 1 1 d . . . Cu1 Cu 0.701973(9) 0.47489(2) 0.563872(7) 0.01901(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0306(10) 0.0450(12) 0.0208(9) 0.0022(8) 0.0076(8) 0.0002(9) C2 0.0391(11) 0.0351(11) 0.0239(9) 0.0042(8) 0.0107(8) -0.0054(9) C3 0.0365(10) 0.0192(8) 0.0178(8) 0.0034(6) 0.0054(7) 0.0016(7) C4 0.0428(11) 0.0253(9) 0.0178(8) -0.0002(6) 0.0057(8) 0.0078(8) C5 0.0505(13) 0.0250(9) 0.0188(8) -0.0002(7) -0.0004(8) 0.0050(9) C6 0.0393(11) 0.0316(10) 0.0241(9) 0.0024(7) -0.0050(8) -0.0007(9) C7 0.0353(11) 0.0258(9) 0.0231(9) 0.0036(7) 0.0036(8) 0.0024(8) C8 0.0365(10) 0.0158(8) 0.0171(8) 0.0017(6) 0.0062(7) 0.0003(7) C9 0.0364(10) 0.0162(8) 0.0198(8) -0.0001(6) 0.0082(7) 0.0002(7) C10 0.0292(10) 0.0248(9) 0.0268(9) 0.0010(7) 0.0076(8) 0.0018(7) C11 0.0246(9) 0.0229(9) 0.0264(9) 0.0018(7) 0.0026(7) -0.0031(7) C12 0.0274(9) 0.0222(8) 0.0194(8) -0.0046(6) 0.0053(7) -0.0059(7) C13 0.0270(9) 0.0225(9) 0.0262(9) -0.0056(7) 0.0093(7) -0.0036(7) C14 0.0301(10) 0.0330(10) 0.0215(9) 0.0014(7) 0.0021(7) -0.0069(8) C15 0.0201(9) 0.0342(10) 0.0314(10) -0.0011(8) 0.0024(8) -0.0043(8) C16 0.0194(9) 0.0367(11) 0.0280(9) -0.0036(8) 0.0023(7) -0.0025(8) C17 0.0243(10) 0.0530(14) 0.0320(10) -0.0055(9) 0.0053(8) -0.0011(9) C18 0.0260(11) 0.0490(14) 0.0511(14) -0.0140(11) 0.0065(10) 0.0033(9) C19 0.0312(11) 0.0386(12) 0.0645(16) -0.0049(11) 0.0034(11) 0.0034(10) C20 0.0282(10) 0.0377(12) 0.0453(12) 0.0039(9) 0.0033(9) -0.0022(9) C21 0.0278(11) 0.0370(12) 0.0480(13) -0.0057(9) 0.0013(10) -0.0039(9) C22 0.0361(12) 0.0571(15) 0.0397(12) 0.0006(10) -0.0004(10) -0.0094(11) N1 0.0323(9) 0.0344(9) 0.0178(7) 0.0002(6) 0.0072(7) 0.0029(7) N2 0.0313(8) 0.0172(7) 0.0151(7) -0.0013(5) 0.0064(6) -0.0022(6) N3 0.0232(7) 0.0187(7) 0.0158(6) 0.0007(5) 0.0046(6) -0.0025(6) N4 0.0236(7) 0.0239(7) 0.0203(7) -0.0004(6) 0.0071(6) -0.0049(6) N5 0.0444(12) 0.0645(14) 0.0514(13) -0.0072(11) 0.0131(10) -0.0094(10) O1 0.0278(7) 0.0385(8) 0.0212(6) 0.0020(5) 0.0058(5) -0.0011(6) Cl1 0.0367(2) 0.0214(2) 0.01415(18) 0.00001(14) 0.00649(16) -0.00376(17) Cl2 0.0381(3) 0.0309(2) 0.0245(2) -0.00373(17) 0.00558(19) -0.0163(2) Cu1 0.02447(12) 0.01825(10) 0.01487(10) -0.00113(7) 0.00472(8) -0.00498(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.444(2) . ? C1 C2 1.507(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.469(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.384(2) . ? C3 C4 1.409(2) . ? C3 C8 1.422(3) . ? C4 C5 1.372(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.397(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C9 1.516(2) . ? C9 N2 1.500(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.487(2) . ? C10 C11 1.529(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N3 1.474(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N3 1.480(2) . ? C12 C13 1.513(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.488(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.470(2) . ? C14 C15 1.519(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C20 1.398(3) . ? C15 C16 1.400(3) . ? C16 O1 1.374(2) . ? C16 C17 1.393(3) . ? C17 C18 1.392(3) . ? C17 H17 0.9500 . ? C18 C19 1.375(4) . ? C18 H18 0.9500 . ? C19 C20 1.393(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 N5 1.138(3) . ? C21 C22 1.457(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 H1N 0.890(14) . ? N2 Cu1 2.0361(15) . ? N2 H2N 0.889(13) . ? N3 Cu1 2.0281(14) . ? N3 H3N 0.889(13) . ? N4 Cu1 2.0540(15) . ? N4 H4N 0.889(13) . ? Cl1 Cu1 2.4705(4) . ? Cl2 Cu1 2.3003(5) . ? 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 C1 C2 107.42(15) . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? O1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C1 114.39(16) . . ? N1 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N1 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N1 C3 C4 119.91(17) . . ? N1 C3 C8 121.84(15) . . ? C4 C3 C8 118.24(17) . . ? C5 C4 C3 121.26(18) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 121.16(17) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C7 118.32(19) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C8 C7 C6 122.17(18) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C3 118.78(16) . . ? C7 C8 C9 118.41(16) . . ? C3 C8 C9 122.67(16) . . ? N2 C9 C8 115.59(14) . . ? N2 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? N2 C9 H9B 108.4 . . ? C8 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? N2 C10 C11 110.51(14) . . ? N2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C10 109.41(14) . . ? N3 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? N3 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? N3 C12 C13 106.43(13) . . ? N3 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? N3 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? N4 C13 C12 108.33(14) . . ? N4 C13 H13A 110.0 . . ? C12 C13 H13A 110.0 . . ? N4 C13 H13B 110.0 . . ? C12 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? N4 C14 C15 112.08(15) . . ? N4 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N4 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C20 C15 C16 118.39(19) . . ? C20 C15 C14 122.20(18) . . ? C16 C15 C14 119.30(18) . . ? O1 C16 C17 123.87(18) . . ? O1 C16 C15 115.40(16) . . ? C17 C16 C15 120.72(19) . . ? C18 C17 C16 119.6(2) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 120.6(2) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.8(2) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C15 120.9(2) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? N5 C21 C22 179.6(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 N1 C2 123.18(15) . . ? C3 N1 H1N 117.0(15) . . ? C2 N1 H1N 114.6(15) . . ? C10 N2 C9 115.20(14) . . ? C10 N2 Cu1 106.96(10) . . ? C9 N2 Cu1 116.61(11) . . ? C10 N2 H2N 107.1(14) . . ? C9 N2 H2N 103.0(14) . . ? Cu1 N2 H2N 107.3(13) . . ? C11 N3 C12 114.88(13) . . ? C11 N3 Cu1 112.27(10) . . ? C12 N3 Cu1 108.76(10) . . ? C11 N3 H3N 108.8(13) . . ? C12 N3 H3N 107.6(13) . . ? Cu1 N3 H3N 103.8(13) . . ? C14 N4 C13 112.26(14) . . ? C14 N4 Cu1 121.70(11) . . ? C13 N4 Cu1 109.78(11) . . ? C14 N4 H4N 107.9(14) . . ? C13 N4 H4N 108.2(14) . . ? Cu1 N4 H4N 95.0(14) . . ? C16 O1 C1 118.16(15) . . ? N3 Cu1 N2 84.40(6) . . ? N3 Cu1 N4 83.01(6) . . ? N2 Cu1 N4 146.91(6) . . ? N3 Cu1 Cl2 171.52(4) . . ? N2 Cu1 Cl2 93.15(4) . . ? N4 Cu1 Cl2 94.84(4) . . ? N3 Cu1 Cl1 89.44(4) . . ? N2 Cu1 Cl1 101.91(4) . . ? N4 Cu1 Cl1 108.43(4) . . ? Cl2 Cu1 Cl1 99.015(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 56.6(2) . . . . ? N1 C3 C4 C5 -178.90(17) . . . . ? C8 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C8 2.1(3) . . . . ? C6 C7 C8 C3 -3.5(3) . . . . ? C6 C7 C8 C9 -179.44(17) . . . . ? N1 C3 C8 C7 -178.83(16) . . . . ? C4 C3 C8 C7 2.4(2) . . . . ? N1 C3 C8 C9 -3.0(3) . . . . ? C4 C3 C8 C9 178.19(16) . . . . ? C7 C8 C9 N2 -92.9(2) . . . . ? C3 C8 C9 N2 91.3(2) . . . . ? N2 C10 C11 N3 -42.13(19) . . . . ? N3 C12 C13 N4 52.29(17) . . . . ? N4 C14 C15 C20 115.8(2) . . . . ? N4 C14 C15 C16 -60.4(2) . . . . ? C20 C15 C16 O1 -179.45(17) . . . . ? C14 C15 C16 O1 -3.1(2) . . . . ? C20 C15 C16 C17 1.9(3) . . . . ? C14 C15 C16 C17 178.25(17) . . . . ? O1 C16 C17 C18 179.75(18) . . . . ? C15 C16 C17 C18 -1.7(3) . . . . ? C16 C17 C18 C19 0.8(3) . . . . ? C17 C18 C19 C20 0.0(3) . . . . ? C18 C19 C20 C15 0.3(3) . . . . ? C16 C15 C20 C19 -1.2(3) . . . . ? C14 C15 C20 C19 -177.41(19) . . . . ? C4 C3 N1 C2 -31.6(3) . . . . ? C8 C3 N1 C2 149.69(17) . . . . ? C1 C2 N1 C3 99.5(2) . . . . ? C11 C10 N2 C9 -89.25(17) . . . . ? C11 C10 N2 Cu1 42.13(16) . . . . ? C8 C9 N2 C10 65.0(2) . . . . ? C8 C9 N2 Cu1 -61.64(18) . . . . ? C10 C11 N3 C12 146.14(15) . . . . ? C10 C11 N3 Cu1 21.18(16) . . . . ? C13 C12 N3 C11 -173.07(14) . . . . ? C13 C12 N3 Cu1 -46.29(15) . . . . ? C15 C14 N4 C13 -64.76(19) . . . . ? C15 C14 N4 Cu1 162.20(12) . . . . ? C12 C13 N4 C14 -172.11(14) . . . . ? C12 C13 N4 Cu1 -33.47(15) . . . . ? C17 C16 O1 C1 -33.2(3) . . . . ? C15 C16 O1 C1 148.17(16) . . . . ? C2 C1 O1 C16 -166.82(16) . . . . ? C11 N3 Cu1 N2 1.38(11) . . . . ? C12 N3 Cu1 N2 -126.89(11) . . . . ? C11 N3 Cu1 N4 150.71(11) . . . . ? C12 N3 Cu1 N4 22.45(11) . . . . ? C11 N3 Cu1 Cl1 -100.65(10) . . . . ? C12 N3 Cu1 Cl1 131.09(10) . . . . ? C10 N2 Cu1 N3 -23.93(10) . . . . ? C9 N2 Cu1 N3 106.65(12) . . . . ? C10 N2 Cu1 N4 -91.93(14) . . . . ? C9 N2 Cu1 N4 38.65(17) . . . . ? C10 N2 Cu1 Cl2 164.21(10) . . . . ? C9 N2 Cu1 Cl2 -65.20(11) . . . . ? C10 N2 Cu1 Cl1 64.31(10) . . . . ? C9 N2 Cu1 Cl1 -165.10(10) . . . . ? C14 N4 Cu1 N3 140.46(13) . . . . ? C13 N4 Cu1 N3 6.42(11) . . . . ? C14 N4 Cu1 N2 -151.15(12) . . . . ? C13 N4 Cu1 N2 74.81(15) . . . . ? C14 N4 Cu1 Cl2 -47.79(13) . . . . ? C13 N4 Cu1 Cl2 178.17(10) . . . . ? C14 N4 Cu1 Cl1 53.40(13) . . . . ? C13 N4 Cu1 Cl1 -80.64(11) . . . . ? 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 N1 H1N Cl2 0.890(14) 2.458(9) 3.2919(16) 156(2) . N2 H2N Cl1 0.889(13) 2.473(11) 3.2621(14) 148.1(18) 7_656 N3 H3N Cl1 0.889(13) 2.484(11) 3.2605(14) 146.1(17) 7_666 N4 H4N O1 0.889(13) 2.234(16) 2.8649(19) 127.6(17) . N4 H4N N1 0.889(13) 2.486(11) 3.286(2) 149.8(18) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.000 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.079 data_lj238sad _database_code_depnum_ccdc_archive 'CCDC 819265' #TrackingRef '- newcombined_revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H27 Cl2 Cu N3 O2, C2 H3 N ' _chemical_formula_sum 'C22 H30 Cl2 Cu N4 O2' _chemical_formula_weight 516.94 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.6290(6) _cell_length_b 9.9320(5) _cell_length_c 22.7210(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.271(5) _cell_angle_gamma 90.00 _cell_volume 2398.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5409 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 30.01 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 1.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6760 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26255 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.44 _reflns_number_total 5463 _reflns_number_gt 4938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0542P)^2^+0.4273P] 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 5463 _refine_ls_number_parameters 284 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.07023(16) 0.09934(16) 0.22829(7) 0.0202(3) Uani 1 1 d . . . H1A H 1.1434 0.0721 0.2527 0.024 Uiso 1 1 calc R . . H1B H 1.0161 0.0195 0.2219 0.024 Uiso 1 1 calc R . . C2 C 0.99690(16) 0.20956(17) 0.25881(7) 0.0194(3) Uani 1 1 d . . . H2A H 0.9821 0.1822 0.3001 0.023 Uiso 1 1 calc R . . H2B H 1.0489 0.2923 0.2596 0.023 Uiso 1 1 calc R . . C3 C 0.77116(15) 0.16265(16) 0.23847(7) 0.0189(3) Uani 1 1 d . . . C4 C 0.66208(15) 0.19272(16) 0.20492(7) 0.0191(3) Uani 1 1 d . . . C5 C 0.55212(17) 0.11974(19) 0.21485(8) 0.0278(4) Uani 1 1 d . . . H5 H 0.4787 0.1407 0.1927 0.033 Uiso 1 1 calc R . . C6 C 0.54717(19) 0.0169(2) 0.25642(9) 0.0385(5) Uani 1 1 d . . . H6 H 0.4714 -0.0316 0.2627 0.046 Uiso 1 1 calc R . . C7 C 0.65488(19) -0.0133(2) 0.28844(9) 0.0356(5) Uani 1 1 d . . . H7 H 0.6526 -0.0838 0.3167 0.043 Uiso 1 1 calc R . . C8 C 0.76619(17) 0.05767(18) 0.27997(8) 0.0258(4) Uani 1 1 d . . . H8 H 0.8390 0.0352 0.3023 0.031 Uiso 1 1 calc R . . C9 C 0.65925(15) 0.30215(16) 0.15860(7) 0.0187(3) Uani 1 1 d . . . H9A H 0.5714 0.3331 0.1533 0.022 Uiso 1 1 calc R . . H9B H 0.7095 0.3797 0.1728 0.022 Uiso 1 1 calc R . . C10 C 0.65169(16) 0.34008(18) 0.05247(7) 0.0227(3) Uani 1 1 d . . . H10A H 0.6660 0.4368 0.0607 0.027 Uiso 1 1 calc R . . H10B H 0.5598 0.3242 0.0514 0.027 Uiso 1 1 calc R . . C11 C 0.70769(16) 0.30457(19) -0.00668(8) 0.0246(4) Uani 1 1 d . . . H11A H 0.6979 0.2073 -0.0149 0.029 Uiso 1 1 calc R . . H11B H 0.6664 0.3564 -0.0386 0.029 Uiso 1 1 calc R . . C12 C 0.92203(17) 0.28239(18) -0.04442(7) 0.0204(3) Uani 1 1 d . . . H12A H 0.9124 0.3274 -0.0831 0.025 Uiso 1 1 calc R . . H12B H 0.9058 0.1849 -0.0494 0.025 Uiso 1 1 calc R . . C13 C 1.05179(16) 0.30648(16) -0.01915(7) 0.0189(3) Uani 1 1 d . . . H13A H 1.1161 0.2748 -0.0474 0.023 Uiso 1 1 calc R . . H13B H 1.0646 0.4041 -0.0128 0.023 Uiso 1 1 calc R . . C14 C 1.18841(16) 0.27254(16) 0.06778(8) 0.0189(3) Uani 1 1 d . . . H14A H 1.1708 0.3379 0.0996 0.023 Uiso 1 1 calc R . . H14B H 1.2447 0.3164 0.0390 0.023 Uiso 1 1 calc R . . C15 C 1.25286(15) 0.15012(16) 0.09332(7) 0.0185(3) Uani 1 1 d . . . C16 C 1.20733(15) 0.08682(16) 0.14423(7) 0.0184(3) Uani 1 1 d . . . C17 C 1.25871(16) -0.03548(17) 0.16325(8) 0.0218(3) Uani 1 1 d . . . H17 H 1.2242 -0.0807 0.1963 0.026 Uiso 1 1 calc R . . C18 C 1.36085(16) -0.09051(17) 0.13342(8) 0.0244(4) Uani 1 1 d . . . H18 H 1.3961 -0.1733 0.1464 0.029 Uiso 1 1 calc R . . C19 C 1.41151(16) -0.02556(19) 0.08489(8) 0.0253(4) Uani 1 1 d . . . H19 H 1.4831 -0.0616 0.0656 0.030 Uiso 1 1 calc R . . C20 C 1.35591(16) 0.09347(18) 0.06473(8) 0.0230(4) Uani 1 1 d . . . H20 H 1.3890 0.1367 0.0309 0.028 Uiso 1 1 calc R . . C21 C 0.64082(18) 0.7187(2) 0.10569(10) 0.0317(4) Uani 1 1 d . . . C22 C 0.7033(3) 0.7611(3) 0.15921(12) 0.0503(7) Uani 1 1 d . . . H22A H 0.7223 0.8575 0.1569 0.075 Uiso 1 1 calc R . . H22B H 0.7817 0.7104 0.1641 0.075 Uiso 1 1 calc R . . H22C H 0.6482 0.7442 0.1929 0.075 Uiso 1 1 calc R . . N1 N 0.87696(14) 0.24094(13) 0.23169(7) 0.0188(3) Uani 1 1 d D . . N2 N 0.70952(13) 0.25738(12) 0.10029(6) 0.0164(3) Uani 1 1 d . . . H2N H 0.6786 0.1707 0.0948 0.020 Uiso 1 1 calc R . . N3 N 1.06702(13) 0.23338(13) 0.03790(6) 0.0160(3) Uani 1 1 d . . . H3N H 1.0761 0.1431 0.0279 0.019 Uiso 1 1 calc R . . N4 N 0.59213(18) 0.68610(19) 0.06312(9) 0.0418(4) Uani 1 1 d . . . O1 O 1.11202(11) 0.15255(12) 0.17267(5) 0.0235(3) Uani 1 1 d . . . O2 O 0.83793(10) 0.33983(11) -0.00182(5) 0.0185(2) Uani 1 1 d . . . Cl1 Cl 0.94284(4) 0.44901(4) 0.127568(16) 0.01877(10) Uani 1 1 d . . . Cl2 Cl 0.87588(4) 0.01705(4) 0.07411(2) 0.02844(12) Uani 1 1 d . . . Cu1 Cu 0.901114(17) 0.245222(17) 0.083337(8) 0.01425(8) Uani 1 1 d . . . H1N H 0.8829(17) 0.2997(15) 0.2023(6) 0.017 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 C1 0.0212(8) 0.0201(8) 0.0192(8) 0.0048(6) 0.0024(6) 0.0013(6) C2 0.0202(8) 0.0199(7) 0.0181(8) 0.0006(6) -0.0016(6) -0.0009(7) C3 0.0199(8) 0.0213(8) 0.0157(8) -0.0022(6) 0.0053(6) -0.0009(6) C4 0.0206(8) 0.0214(8) 0.0155(8) -0.0007(6) 0.0036(6) -0.0001(6) C5 0.0202(8) 0.0399(10) 0.0232(9) 0.0042(8) 0.0005(7) -0.0057(7) C6 0.0296(10) 0.0532(13) 0.0328(11) 0.0152(9) -0.0008(8) -0.0180(9) C7 0.0364(11) 0.0426(11) 0.0278(10) 0.0152(9) 0.0002(8) -0.0134(9) C8 0.0253(9) 0.0317(9) 0.0203(8) 0.0058(7) -0.0003(7) -0.0025(7) C9 0.0178(8) 0.0197(8) 0.0188(8) -0.0011(6) 0.0030(6) 0.0040(6) C10 0.0188(8) 0.0280(8) 0.0215(9) 0.0047(7) -0.0011(7) 0.0034(7) C11 0.0203(8) 0.0344(10) 0.0190(8) 0.0020(7) -0.0038(7) -0.0028(7) C12 0.0269(9) 0.0210(7) 0.0135(8) -0.0002(6) 0.0022(7) 0.0013(7) C13 0.0241(8) 0.0176(8) 0.0151(8) 0.0032(6) 0.0044(6) 0.0020(6) C14 0.0182(8) 0.0191(7) 0.0196(8) 0.0030(6) 0.0017(7) -0.0005(6) C15 0.0165(7) 0.0196(7) 0.0195(8) -0.0016(6) -0.0008(6) 0.0015(6) C16 0.0161(7) 0.0190(7) 0.0202(8) -0.0007(6) 0.0004(6) 0.0011(6) C17 0.0216(8) 0.0207(8) 0.0231(8) 0.0021(7) -0.0018(7) 0.0018(7) C18 0.0243(9) 0.0206(8) 0.0282(9) -0.0034(7) -0.0051(7) 0.0062(7) C19 0.0205(8) 0.0282(9) 0.0273(9) -0.0067(7) 0.0004(7) 0.0082(7) C20 0.0205(8) 0.0266(8) 0.0219(8) -0.0012(7) 0.0014(7) 0.0013(7) C21 0.0245(9) 0.0281(9) 0.0425(13) 0.0085(9) 0.0062(9) 0.0097(8) C22 0.0437(14) 0.0692(18) 0.0380(14) 0.0128(11) -0.0041(11) -0.0045(11) N1 0.0180(7) 0.0198(7) 0.0187(7) 0.0055(5) 0.0006(6) -0.0006(5) N2 0.0181(7) 0.0154(6) 0.0157(7) -0.0001(5) 0.0012(6) 0.0000(5) N3 0.0193(7) 0.0134(6) 0.0152(7) 0.0010(5) 0.0021(6) 0.0017(5) N4 0.0373(10) 0.0391(10) 0.0490(12) -0.0026(9) -0.0002(9) 0.0091(8) O1 0.0247(6) 0.0231(6) 0.0227(6) 0.0077(5) 0.0072(5) 0.0077(5) O2 0.0192(6) 0.0205(5) 0.0159(6) -0.0011(4) 0.0002(4) 0.0007(5) Cl1 0.0248(2) 0.01400(18) 0.01748(19) -0.00129(14) 0.00154(15) -0.00277(14) Cl2 0.0317(2) 0.01233(19) 0.0414(3) -0.00199(16) 0.01299(19) -0.00095(16) Cu1 0.01655(12) 0.01193(12) 0.01428(12) -0.00027(6) 0.00195(8) 0.00062(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 C1 O1 1.4419(19) . ? C1 C2 1.514(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.447(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.376(2) . ? C3 C8 1.407(2) . ? C3 C4 1.416(2) . ? C4 C5 1.395(2) . ? C4 C9 1.513(2) . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C7 C8 1.391(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N2 1.498(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.492(2) . ? C10 C11 1.514(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.432(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O2 1.439(2) . ? C12 C13 1.510(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N3 1.494(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N3 1.506(2) . ? C14 C15 1.510(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C20 1.395(2) . ? C15 C16 1.405(2) . ? C16 O1 1.3699(19) . ? C16 C17 1.399(2) . ? C17 C18 1.394(2) . ? C17 H17 0.9500 . ? C18 C19 1.388(3) . ? C18 H18 0.9500 . ? C19 C20 1.398(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 N4 1.142(3) . ? C21 C22 1.445(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N1 H1N 0.889(14) . ? N2 Cu1 2.0779(14) . ? N2 H2N 0.9300 . ? N3 Cu1 2.0510(14) . ? N3 H3N 0.9300 . ? O2 Cu1 2.2506(11) . ? Cl1 Cu1 2.3019(4) . ? Cl2 Cu1 2.2915(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 107.33(13) . . ? O1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? O1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C1 114.52(14) . . ? N1 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N1 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N1 C3 C8 121.80(16) . . ? N1 C3 C4 119.19(15) . . ? C8 C3 C4 118.93(15) . . ? C5 C4 C3 119.19(15) . . ? C5 C4 C9 118.16(15) . . ? C3 C4 C9 122.64(14) . . ? C6 C5 C4 121.70(17) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C5 118.76(18) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 121.22(18) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C3 120.19(17) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? N2 C9 C4 113.32(13) . . ? N2 C9 H9A 108.9 . . ? C4 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C4 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? N2 C10 C11 110.84(14) . . ? N2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O2 C11 C10 104.99(13) . . ? O2 C11 H11A 110.7 . . ? C10 C11 H11A 110.7 . . ? O2 C11 H11B 110.7 . . ? C10 C11 H11B 110.7 . . ? H11A C11 H11B 108.8 . . ? O2 C12 C13 104.52(13) . . ? O2 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? O2 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? N3 C13 C12 110.35(13) . . ? N3 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? N3 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? N3 C14 C15 110.57(13) . . ? N3 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C20 C15 C16 118.52(15) . . ? C20 C15 C14 120.12(15) . . ? C16 C15 C14 121.29(14) . . ? O1 C16 C17 123.80(15) . . ? O1 C16 C15 115.70(14) . . ? C17 C16 C15 120.49(15) . . ? C18 C17 C16 119.59(16) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 120.65(16) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C20 119.22(15) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C15 C20 C19 121.36(16) . . ? C15 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? N4 C21 C22 179.3(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 N1 C2 123.31(14) . . ? C3 N1 H1N 121.0(12) . . ? C2 N1 H1N 113.3(12) . . ? C10 N2 C9 109.46(12) . . ? C10 N2 Cu1 107.32(10) . . ? C9 N2 Cu1 122.34(10) . . ? C10 N2 H2N 105.5 . . ? C9 N2 H2N 105.5 . . ? Cu1 N2 H2N 105.5 . . ? C13 N3 C14 110.77(12) . . ? C13 N3 Cu1 108.61(10) . . ? C14 N3 Cu1 119.67(11) . . ? C13 N3 H3N 105.6 . . ? C14 N3 H3N 105.6 . . ? Cu1 N3 H3N 105.6 . . ? C16 O1 C1 118.06(12) . . ? C11 O2 C12 117.05(13) . . ? C11 O2 Cu1 104.40(9) . . ? C12 O2 Cu1 103.24(9) . . ? N3 Cu1 N2 160.45(6) . . ? N3 Cu1 O2 81.08(5) . . ? N2 Cu1 O2 81.16(5) . . ? N3 Cu1 Cl2 89.87(4) . . ? N2 Cu1 Cl2 87.71(4) . . ? O2 Cu1 Cl2 107.45(3) . . ? N3 Cu1 Cl1 96.08(4) . . ? N2 Cu1 Cl1 93.15(4) . . ? O2 Cu1 Cl1 93.69(3) . . ? Cl2 Cu1 Cl1 158.703(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 69.69(17) . . . . ? N1 C3 C4 C5 -175.36(16) . . . . ? C8 C3 C4 C5 1.5(2) . . . . ? N1 C3 C4 C9 4.2(2) . . . . ? C8 C3 C4 C9 -178.93(15) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C9 C4 C5 C6 179.60(18) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? C6 C7 C8 C3 0.2(3) . . . . ? N1 C3 C8 C7 175.56(17) . . . . ? C4 C3 C8 C7 -1.2(3) . . . . ? C5 C4 C9 N2 -97.43(18) . . . . ? C3 C4 C9 N2 82.99(19) . . . . ? N2 C10 C11 O2 -63.10(17) . . . . ? O2 C12 C13 N3 62.92(16) . . . . ? N3 C14 C15 C20 103.03(18) . . . . ? N3 C14 C15 C16 -73.70(19) . . . . ? C20 C15 C16 O1 175.41(15) . . . . ? C14 C15 C16 O1 -7.8(2) . . . . ? C20 C15 C16 C17 -4.5(2) . . . . ? C14 C15 C16 C17 172.26(15) . . . . ? O1 C16 C17 C18 -176.02(15) . . . . ? C15 C16 C17 C18 3.9(3) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? C17 C18 C19 C20 -2.4(3) . . . . ? C16 C15 C20 C19 1.7(3) . . . . ? C14 C15 C20 C19 -175.13(16) . . . . ? C18 C19 C20 C15 1.8(3) . . . . ? C8 C3 N1 C2 10.4(2) . . . . ? C4 C3 N1 C2 -172.81(15) . . . . ? C1 C2 N1 C3 77.7(2) . . . . ? C11 C10 N2 C9 175.75(14) . . . . ? C11 C10 N2 Cu1 40.96(15) . . . . ? C4 C9 N2 C10 153.77(14) . . . . ? C4 C9 N2 Cu1 -79.54(15) . . . . ? C12 C13 N3 C14 -171.75(13) . . . . ? C12 C13 N3 Cu1 -38.41(15) . . . . ? C15 C14 N3 C13 -137.67(14) . . . . ? C15 C14 N3 Cu1 94.82(14) . . . . ? C17 C16 O1 C1 6.0(2) . . . . ? C15 C16 O1 C1 -173.90(14) . . . . ? C2 C1 O1 C16 162.67(13) . . . . ? C10 C11 O2 C12 162.42(13) . . . . ? C10 C11 O2 Cu1 49.05(14) . . . . ? C13 C12 O2 C11 -165.55(13) . . . . ? C13 C12 O2 Cu1 -51.53(13) . . . . ? C13 N3 Cu1 N2 31.5(2) . . . . ? C14 N3 Cu1 N2 160.01(13) . . . . ? C13 N3 Cu1 O2 6.59(9) . . . . ? C14 N3 Cu1 O2 135.09(11) . . . . ? C13 N3 Cu1 Cl2 114.29(9) . . . . ? C14 N3 Cu1 Cl2 -117.22(10) . . . . ? C13 N3 Cu1 Cl1 -86.20(10) . . . . ? C14 N3 Cu1 Cl1 42.30(11) . . . . ? C10 N2 Cu1 N3 -34.5(2) . . . . ? C9 N2 Cu1 N3 -162.09(14) . . . . ? C10 N2 Cu1 O2 -9.54(10) . . . . ? C9 N2 Cu1 O2 -137.18(11) . . . . ? C10 N2 Cu1 Cl2 -117.60(10) . . . . ? C9 N2 Cu1 Cl2 114.77(11) . . . . ? C10 N2 Cu1 Cl1 83.70(10) . . . . ? C9 N2 Cu1 Cl1 -43.93(11) . . . . ? C11 O2 Cu1 N3 148.86(10) . . . . ? C12 O2 Cu1 N3 25.99(9) . . . . ? C11 O2 Cu1 N2 -22.94(10) . . . . ? C12 O2 Cu1 N2 -145.81(10) . . . . ? C11 O2 Cu1 Cl2 61.83(10) . . . . ? C12 O2 Cu1 Cl2 -61.04(9) . . . . ? C11 O2 Cu1 Cl1 -115.55(9) . . . . ? C12 O2 Cu1 Cl1 121.57(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.609 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.243