# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email cfclover@163.com _publ_contact_author_name 'Yakun Gu' _publ_author_name X.Li data_100511a_0m _database_code_depnum_ccdc_archive 'CCDC 778758' #TrackingRef '778758.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Cl2 Cu N6' _chemical_formula_weight 326.68 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.5366(4) _cell_length_b 9.4270(4) _cell_length_c 8.9888(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.744(3) _cell_angle_gamma 90.00 _cell_volume 634.21(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1663 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 28.25 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 2.130 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5490 _exptl_absorpt_correction_T_max 0.6516 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3816 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 28.45 _reflns_number_total 1580 _reflns_number_gt 1362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.2107P] 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 1580 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.7274(3) 0.7007(2) 0.0975(2) 0.0263(4) Uani 1 1 d . . . H1 H 0.6321 0.6482 0.0510 0.032 Uiso 1 1 calc R . . C2 C 0.9831(3) 0.7719(3) 0.1813(3) 0.0460(7) Uani 1 1 d . . . H2 H 1.1068 0.7757 0.2031 0.055 Uiso 1 1 calc R . . C3 C 0.5494(3) 0.9002(2) 0.1906(2) 0.0281(4) Uani 1 1 d . . . H3A H 0.5588 0.9368 0.2921 0.034 Uiso 1 1 calc R . . H3B H 0.4478 0.8364 0.1772 0.034 Uiso 1 1 calc R . . C4 C 0.5167(3) 1.0226(2) 0.0816(2) 0.0334(5) Uani 1 1 d . . . H4A H 0.6196 1.0852 0.0940 0.040 Uiso 1 1 calc R . . H4B H 0.4143 1.0762 0.1064 0.040 Uiso 1 1 calc R . . Cl1 Cl 1.26352(6) 0.62060(5) -0.00675(6) 0.02922(14) Uani 1 1 d . . . Cu1 Cu 1.0000 0.5000 0.0000 0.02474(12) Uani 1 2 d S . . N1 N 0.8981(2) 0.66590(19) 0.09958(19) 0.0280(4) Uani 1 1 d . . . N2 N 0.7121(2) 0.82048(18) 0.17081(18) 0.0253(4) Uani 1 1 d . . . N3 N 0.8770(2) 0.8687(2) 0.2272(2) 0.0449(5) 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 0.0218(9) 0.0257(10) 0.0315(10) -0.0041(8) 0.0038(7) -0.0001(8) C2 0.0225(10) 0.0522(16) 0.0630(16) -0.0311(13) 0.0040(10) -0.0011(10) C3 0.0264(10) 0.0298(11) 0.0293(10) -0.0049(8) 0.0081(8) 0.0056(8) C4 0.0390(12) 0.0278(12) 0.0327(11) -0.0069(9) 0.0017(9) 0.0084(9) Cl1 0.0206(2) 0.0259(3) 0.0421(3) -0.0003(2) 0.00804(18) -0.00341(18) Cu1 0.01739(18) 0.0223(2) 0.0357(2) -0.00733(14) 0.00837(13) -0.00171(12) N1 0.0207(8) 0.0276(9) 0.0363(9) -0.0086(7) 0.0052(7) 0.0000(7) N2 0.0201(8) 0.0258(9) 0.0302(8) -0.0039(7) 0.0038(6) 0.0013(6) N3 0.0257(9) 0.0469(13) 0.0620(13) -0.0308(10) 0.0051(9) -0.0021(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 N2 1.319(3) . ? C1 N1 1.325(2) . ? C1 H1 0.9300 . ? C2 N3 1.311(3) . ? C2 N1 1.356(3) . ? C2 H2 0.9300 . ? C3 N2 1.467(2) . ? C3 C4 1.515(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.520(4) 3_675 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? Cl1 Cu1 2.2954(5) . ? Cu1 N1 1.9997(17) . ? Cu1 N1 1.9997(17) 3_765 ? Cu1 Cl1 2.2954(5) 3_765 ? N2 N3 1.364(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 N2 C1 N1 110.27(17) . . ? N2 C1 H1 124.9 . . ? N1 C1 H1 124.9 . . ? N3 C2 N1 114.59(19) . . ? N3 C2 H2 122.7 . . ? N1 C2 H2 122.7 . . ? N2 C3 C4 112.75(17) . . ? N2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C4 114.0(2) . 3_675 ? C3 C4 H4A 108.8 . . ? C4 C4 H4A 108.8 3_675 . ? C3 C4 H4B 108.8 . . ? C4 C4 H4B 108.8 3_675 . ? H4A C4 H4B 107.7 . . ? N1 Cu1 N1 180.00(9) . 3_765 ? N1 Cu1 Cl1 89.80(5) . 3_765 ? N1 Cu1 Cl1 90.20(5) 3_765 3_765 ? N1 Cu1 Cl1 90.20(5) . . ? N1 Cu1 Cl1 89.80(5) 3_765 . ? Cl1 Cu1 Cl1 180.0 3_765 . ? C1 N1 C2 102.80(17) . . ? C1 N1 Cu1 127.61(14) . . ? C2 N1 Cu1 129.56(14) . . ? C1 N2 N3 109.95(16) . . ? C1 N2 C3 128.52(17) . . ? N3 N2 C3 121.50(17) . . ? C2 N3 N2 102.38(17) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.372 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.078 # Attachment 'test_0m.cif' data_test_0m _database_code_depnum_ccdc_archive 'CCDC 780207' #TrackingRef 'test_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 N20 Ni O6' _chemical_formula_weight 759.44 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' Ni Ni 0.3393 1.1124 '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 Trigonal _symmetry_space_group_name_H-M P-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' _cell_length_a 10.9001(7) _cell_length_b 10.9001(7) _cell_length_c 8.1598(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 839.60(12) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1926 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 24.93 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.650 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7950 _exptl_absorpt_correction_T_max 0.8920 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5493 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 29.73 _reflns_number_total 1583 _reflns_number_gt 1397 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.2193P] 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 1583 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.09479(13) 0.22806(14) 0.21911(17) 0.0434(3) Uani 1 1 d . . . H1 H 0.0030 0.1855 0.1779 0.052 Uiso 1 1 calc R . . C2 C 0.26852(12) 0.26681(12) 0.36486(15) 0.0357(3) Uani 1 1 d . . . H2 H 0.3269 0.2612 0.4441 0.043 Uiso 1 1 calc R . . C3 C 0.45355(15) 0.48989(15) 0.23256(18) 0.0514(4) Uani 1 1 d . . . H3A H 0.5106 0.4956 0.3267 0.062 Uiso 1 1 calc R . . H3B H 0.4467 0.5752 0.2306 0.062 Uiso 1 1 calc R . . C4 C 0.52717(14) 0.48358(15) 0.07774(17) 0.0488(4) Uani 1 1 d . . . H4A H 0.5154 0.3896 0.0682 0.059 Uiso 1 1 calc R . . H4B H 0.6278 0.5504 0.0877 0.059 Uiso 1 1 calc R . . N1 N 0.13064(9) 0.17583(9) 0.34947(11) 0.0296(2) Uani 1 1 d . . . N2 N 0.20000(12) 0.34389(13) 0.15509(16) 0.0525(3) Uani 1 1 d . . . N3 N 0.31078(11) 0.36635(11) 0.25157(13) 0.0389(3) Uani 1 1 d . . . N4 N 0.6667 0.3333 0.4514(3) 0.0540(6) Uani 1 3 d S . . Ni1 Ni 0.0000 0.0000 0.5000 0.02321(8) Uani 1 6 d S . . O1 O 0.75150(14) 0.29028(15) 0.4520(2) 0.0923(5) 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 0.0342(5) 0.0459(6) 0.0475(7) 0.0166(5) 0.0053(5) 0.0180(5) C2 0.0337(5) 0.0317(5) 0.0340(6) 0.0028(4) 0.0021(5) 0.0105(4) C3 0.0451(7) 0.0354(6) 0.0465(7) 0.0015(6) 0.0109(6) -0.0004(6) C4 0.0375(6) 0.0431(7) 0.0507(8) 0.0079(6) 0.0119(6) 0.0088(5) N1 0.0289(4) 0.0257(4) 0.0326(5) 0.0040(3) 0.0045(4) 0.0124(3) N2 0.0433(5) 0.0530(6) 0.0569(7) 0.0258(5) 0.0093(5) 0.0207(5) N3 0.0361(5) 0.0319(5) 0.0386(5) 0.0050(4) 0.0092(4) 0.0095(4) N4 0.0562(8) 0.0562(8) 0.0496(12) 0.000 0.000 0.0281(4) Ni1 0.02184(10) 0.02184(10) 0.02594(16) 0.000 0.000 0.01092(5) O1 0.0755(7) 0.0841(8) 0.1344(13) -0.0018(8) -0.0115(9) 0.0528(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 N2 1.3169(16) . ? C1 N1 1.3531(16) . ? C1 H1 0.9300 . ? C2 N3 1.3206(16) . ? C2 N1 1.3295(14) . ? C2 H2 0.9300 . ? C3 N3 1.4709(15) . ? C3 C4 1.517(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.517(3) 4_665 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N1 Ni1 2.1167(9) . ? N2 N3 1.3573(16) . ? N4 O1 1.2285(14) . ? N4 O1 1.2285(14) 3_665 ? N4 O1 1.2285(14) 2_655 ? Ni1 N1 2.1167(9) 5_556 ? Ni1 N1 2.1167(9) 6_556 ? Ni1 N1 2.1167(9) 4_556 ? Ni1 N1 2.1167(9) 2 ? Ni1 N1 2.1167(9) 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 N2 C1 N1 114.77(11) . . ? N2 C1 H1 122.6 . . ? N1 C1 H1 122.6 . . ? N3 C2 N1 110.27(11) . . ? N3 C2 H2 124.9 . . ? N1 C2 H2 124.9 . . ? N3 C3 C4 112.83(11) . . ? N3 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N3 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C3 C4 C4 114.09(17) . 4_665 ? C3 C4 H4A 108.7 . . ? C4 C4 H4A 108.7 4_665 . ? C3 C4 H4B 108.7 . . ? C4 C4 H4B 108.7 4_665 . ? H4A C4 H4B 107.6 . . ? C2 N1 C1 102.53(9) . . ? C2 N1 Ni1 128.20(8) . . ? C1 N1 Ni1 129.20(7) . . ? C1 N2 N3 102.27(11) . . ? C2 N3 N2 110.15(10) . . ? C2 N3 C3 126.92(12) . . ? N2 N3 C3 122.86(11) . . ? O1 N4 O1 119.998(3) . 3_665 ? O1 N4 O1 119.998(3) . 2_655 ? O1 N4 O1 119.998(3) 3_665 2_655 ? N1 Ni1 N1 89.71(4) 5_556 6_556 ? N1 Ni1 N1 89.71(4) 5_556 4_556 ? N1 Ni1 N1 89.71(4) 6_556 4_556 ? N1 Ni1 N1 180.00(3) 5_556 2 ? N1 Ni1 N1 90.29(4) 6_556 2 ? N1 Ni1 N1 90.29(4) 4_556 2 ? N1 Ni1 N1 90.29(4) 5_556 . ? N1 Ni1 N1 90.29(4) 6_556 . ? N1 Ni1 N1 180.00(4) 4_556 . ? N1 Ni1 N1 89.71(4) 2 . ? N1 Ni1 N1 90.29(4) 5_556 3 ? N1 Ni1 N1 180.0 6_556 3 ? N1 Ni1 N1 90.29(4) 4_556 3 ? N1 Ni1 N1 89.71(4) 2 3 ? N1 Ni1 N1 89.71(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 N3 C3 C4 C4 75.3(2) . . . 4_665 ? N3 C2 N1 C1 0.31(14) . . . . ? N3 C2 N1 Ni1 -176.96(8) . . . . ? N2 C1 N1 C2 -0.36(16) . . . . ? N2 C1 N1 Ni1 176.87(10) . . . . ? N1 C1 N2 N3 0.27(17) . . . . ? N1 C2 N3 N2 -0.17(16) . . . . ? N1 C2 N3 C3 176.72(12) . . . . ? C1 N2 N3 C2 -0.06(15) . . . . ? C1 N2 N3 C3 -177.09(13) . . . . ? C4 C3 N3 C2 113.00(16) . . . . ? C4 C3 N3 N2 -70.48(19) . . . . ? C2 N1 Ni1 N1 0.06(11) . . . 5_556 ? C1 N1 Ni1 N1 -176.50(11) . . . 5_556 ? C2 N1 Ni1 N1 89.77(12) . . . 6_556 ? C1 N1 Ni1 N1 -86.79(10) . . . 6_556 ? C2 N1 Ni1 N1 -179.77(14) . . . 4_556 ? C1 N1 Ni1 N1 3.67(9) . . . 4_556 ? C2 N1 Ni1 N1 -179.94(11) . . . 2 ? C1 N1 Ni1 N1 3.50(11) . . . 2 ? C2 N1 Ni1 N1 -90.23(12) . . . 3 ? C1 N1 Ni1 N1 93.21(10) . . . 3 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.73 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.233 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.049 # Attachment '100525a_0m.cif' #============================================================================== data_100525a_0m _database_code_depnum_ccdc_archive 'CCDC 787792' #TrackingRef '100525a_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 Co N14 O2 S2' _chemical_formula_weight 591.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 8.96520(10) _cell_length_b 9.6841(2) _cell_length_c 15.5712(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.7830(10) _cell_angle_gamma 90.00 _cell_volume 1351.76(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 610 _exptl_absorpt_coefficient_mu 0.834 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7157 _exptl_absorpt_correction_T_max 0.8851 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7317 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.69 _reflns_number_total 3147 _reflns_number_gt 2345 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1249P)^2^+1.3128P] 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 SHELXL _refine_ls_extinction_coef 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3147 _refine_ls_number_parameters 181 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.2118 _refine_ls_wR_factor_gt 0.1922 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.044 _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 0.7872(4) 0.2497(4) 1.0548(2) 0.0429(8) Uani 1 1 d . . . H1 H 0.8639 0.3055 1.0758 0.052 Uiso 1 1 calc R . . C2 C 0.6655(4) 0.0885(4) 0.9988(3) 0.0487(9) Uani 1 1 d . . . H2 H 0.6432 0.0059 0.9711 0.058 Uiso 1 1 calc R . . C3 C 0.5700(5) 0.3969(4) 1.0997(3) 0.0529(10) Uani 1 1 d . . . H3A H 0.6449 0.4624 1.1193 0.063 Uiso 1 1 calc R . . H3B H 0.5162 0.3648 1.1495 0.063 Uiso 1 1 calc R . . C4 C 0.4623(5) 0.4686(5) 1.0384(3) 0.0552(10) Uani 1 1 d . . . H4A H 0.3884 0.4024 1.0185 0.066 Uiso 1 1 calc R . . H4B H 0.4105 0.5408 1.0692 0.066 Uiso 1 1 calc R . . C5 C 1.4491(10) 0.2653(14) 0.7243(6) 0.068(2) Uani 0.503(9) 1 d PD . 1 H5B H 1.4964 0.2270 0.6739 0.081 Uiso 0.503(9) 1 calc PR . 1 H5A H 1.4389 0.3630 0.7118 0.081 Uiso 0.503(9) 1 calc PR . 1 C5A C 1.4578(10) 0.1666(14) 0.7236(6) 0.068(2) Uani 0.497(9) 1 d PD . 2 H5A2 H 1.4535 0.0704 0.7064 0.081 Uiso 0.497(9) 1 calc PR . 2 H5A1 H 1.5086 0.2134 0.6773 0.081 Uiso 0.497(9) 1 calc PR . 2 C6 C 1.2922(6) 0.2161(7) 0.7125(3) 0.0720(14) Uani 1 1 d D . . H6B H 1.2394 0.2785 0.6740 0.086 Uiso 1 1 calc R . 1 H6A H 1.2930 0.1255 0.6859 0.086 Uiso 1 1 calc R . 1 C7 C 1.1515(5) 0.0998(5) 0.8312(3) 0.0536(10) Uani 1 1 d . . . H7 H 1.1488 0.0111 0.8083 0.064 Uiso 1 1 calc R . . C8 C 1.1260(6) 0.2715(5) 0.9095(4) 0.0701(14) Uani 1 1 d . . . H8 H 1.0986 0.3264 0.9557 0.084 Uiso 1 1 calc R . . C9 C 1.1649(6) 0.1701(6) 1.1485(3) 0.0769(16) Uani 1 1 d . . . Co1 Co 1.0000 0.0000 1.0000 0.0370(3) Uani 1 2 d S . . N1 N 0.8062(3) 0.1290(3) 1.0165(2) 0.0416(7) Uani 1 1 d . . . N2 N 0.6436(3) 0.2795(3) 1.0589(2) 0.0429(7) Uani 1 1 d . . . N3 N 0.5623(4) 0.1753(4) 1.0239(2) 0.0534(8) Uani 1 1 d . . . N4 N 1.2126(4) 0.2082(4) 0.7935(2) 0.0597(9) Uani 1 1 d . . . N5 N 1.1969(6) 0.3201(4) 0.8440(3) 0.0821(14) Uani 1 1 d . . . N6 N 1.0952(4) 0.1356(3) 0.9056(2) 0.0476(8) Uani 1 1 d . . . N7 N 1.1082(4) 0.1115(4) 1.0977(2) 0.0524(8) Uani 1 1 d . . . S1 S 1.2461(17) 0.2514(16) 1.2289(12) 0.128(4) Uani 0.50 1 d PU A 1 S1A S 1.2937(17) 0.2060(16) 1.2272(12) 0.128(4) Uani 0.50 1 d P A 2 O1 O 0.0721(13) 0.4730(10) 0.1313(7) 0.0875(17) Uani 0.412(7) 1 d P B 1 O2 O 1.1744(9) 0.3483(8) 1.2003(5) 0.0875(17) Uani 0.588(7) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0407(19) 0.0400(19) 0.0480(19) -0.0001(15) -0.0004(14) -0.0031(14) C2 0.0376(19) 0.044(2) 0.065(2) -0.0095(17) 0.0028(16) -0.0006(15) C3 0.060(2) 0.048(2) 0.051(2) -0.0039(17) 0.0026(18) 0.0153(18) C4 0.052(2) 0.053(2) 0.061(3) 0.0019(19) 0.0065(19) 0.0175(18) C5 0.063(4) 0.091(6) 0.050(3) -0.004(5) 0.017(2) -0.010(5) C5A 0.063(4) 0.091(6) 0.050(3) -0.004(5) 0.017(2) -0.010(5) C6 0.062(3) 0.110(4) 0.044(2) 0.014(2) 0.0022(19) -0.021(3) C7 0.050(2) 0.057(2) 0.054(2) -0.0018(18) 0.0051(17) -0.0073(18) C8 0.080(3) 0.050(3) 0.081(3) -0.003(2) 0.030(3) -0.009(2) C9 0.075(3) 0.112(4) 0.045(2) -0.012(3) 0.011(2) -0.046(3) Co1 0.0314(4) 0.0378(4) 0.0417(4) -0.0035(3) 0.0026(3) -0.0006(2) N1 0.0372(15) 0.0395(16) 0.0482(16) -0.0009(13) 0.0026(12) 0.0004(12) N2 0.0423(17) 0.0391(16) 0.0474(17) -0.0004(13) -0.0010(13) 0.0065(13) N3 0.0382(17) 0.053(2) 0.069(2) -0.0118(17) -0.0016(15) 0.0026(14) N4 0.052(2) 0.074(2) 0.053(2) 0.0103(18) 0.0049(16) -0.0098(18) N5 0.103(4) 0.058(2) 0.086(3) 0.008(2) 0.035(3) -0.018(2) N6 0.0424(17) 0.0469(18) 0.0538(18) 0.0022(14) 0.0071(14) -0.0017(13) N7 0.0457(18) 0.055(2) 0.056(2) -0.0126(16) -0.0014(15) -0.0024(15) S1 0.154(8) 0.159(8) 0.0717(13) -0.021(5) -0.011(5) -0.075(6) S1A 0.154(8) 0.159(8) 0.0717(13) -0.021(5) -0.011(5) -0.075(6) O1 0.091(4) 0.079(4) 0.093(4) -0.033(3) 0.011(3) -0.013(3) O2 0.091(4) 0.079(4) 0.093(4) -0.033(3) 0.011(3) -0.013(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 N2 1.322(5) . ? C1 N1 1.325(5) . ? C1 H1 0.9300 . ? C2 N3 1.313(5) . ? C2 N1 1.346(5) . ? C2 H2 0.9300 . ? C3 N2 1.464(5) . ? C3 C4 1.517(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.510(9) 3_667 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.207(19) 2_856 ? C5 C6 1.494(10) . ? C5 H5B 0.9700 . ? C5 H5A 0.9700 . ? C5A C5A 1.110(19) 2_856 ? C5A C6 1.568(11) . ? C5A H5A2 0.9700 . ? C5A H5A1 0.9700 . ? C6 N4 1.460(6) . ? C6 H6B 0.9700 . ? C6 H6A 0.9700 . ? C7 N6 1.317(5) . ? C7 N4 1.325(6) . ? C7 H7 0.9300 . ? C8 N5 1.297(6) . ? C8 N6 1.345(5) . ? C8 H8 0.9300 . ? C9 N7 1.093(5) . ? C9 S1 1.640(18) . ? C9 S1A 1.708(18) . ? C9 O2 1.906(8) . ? Co1 N7 2.093(3) 3_757 ? Co1 N7 2.093(3) . ? Co1 N6 2.156(3) 3_757 ? Co1 N6 2.156(3) . ? Co1 N1 2.158(3) . ? Co1 N1 2.158(3) 3_757 ? N2 N3 1.355(4) . ? N4 N5 1.347(6) . ? S1A O2 1.790(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 N2 C1 N1 110.2(3) . . ? N2 C1 H1 124.9 . . ? N1 C1 H1 124.9 . . ? N3 C2 N1 114.5(3) . . ? N3 C2 H2 122.7 . . ? N1 C2 H2 122.7 . . ? N2 C3 C4 111.6(3) . . ? N2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C4 C4 C3 113.3(5) 3_667 . ? C4 C4 H4A 108.9 3_667 . ? C3 C4 H4A 108.9 . . ? C4 C4 H4B 108.9 3_667 . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C5 C5 C6 141.7(10) 2_856 . ? C5 C5 H5B 101.6 2_856 . ? C6 C5 H5B 101.6 . . ? C5 C5 H5A 101.6 2_856 . ? C6 C5 H5A 101.6 . . ? H5B C5 H5A 104.6 . . ? C5A C5A C6 135.8(11) 2_856 . ? C5A C5A H5A2 103.2 2_856 . ? C6 C5A H5A2 103.2 . . ? C5A C5A H5A1 103.2 2_856 . ? C6 C5A H5A1 103.2 . . ? H5A2 C5A H5A1 105.2 . . ? N4 C6 C5 112.4(5) . . ? N4 C6 C5A 111.2(5) . . ? C5 C6 C5A 36.4(5) . . ? N4 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? C5A C6 H6B 135.4 . . ? N4 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C5A C6 H6A 75.9 . . ? H6B C6 H6A 107.9 . . ? N6 C7 N4 110.2(4) . . ? N6 C7 H7 124.9 . . ? N4 C7 H7 124.9 . . ? N5 C8 N6 114.9(5) . . ? N5 C8 H8 122.5 . . ? N6 C8 H8 122.5 . . ? N7 C9 S1 176.6(8) . . ? N7 C9 S1A 158.1(8) . . ? S1 C9 S1A 21.0(9) . . ? N7 C9 O2 142.6(6) . . ? S1 C9 O2 39.3(6) . . ? S1A C9 O2 59.1(5) . . ? N7 Co1 N7 180.000(1) 3_757 . ? N7 Co1 N6 89.86(13) 3_757 3_757 ? N7 Co1 N6 90.14(13) . 3_757 ? N7 Co1 N6 90.14(13) 3_757 . ? N7 Co1 N6 89.86(13) . . ? N6 Co1 N6 180.000(1) 3_757 . ? N7 Co1 N1 91.12(12) 3_757 . ? N7 Co1 N1 88.88(12) . . ? N6 Co1 N1 86.83(11) 3_757 . ? N6 Co1 N1 93.17(11) . . ? N7 Co1 N1 88.88(12) 3_757 3_757 ? N7 Co1 N1 91.12(12) . 3_757 ? N6 Co1 N1 93.17(11) 3_757 3_757 ? N6 Co1 N1 86.83(11) . 3_757 ? N1 Co1 N1 180.00(16) . 3_757 ? C1 N1 C2 102.9(3) . . ? C1 N1 Co1 132.3(3) . . ? C2 N1 Co1 124.1(2) . . ? C1 N2 N3 109.7(3) . . ? C1 N2 C3 129.4(3) . . ? N3 N2 C3 120.7(3) . . ? C2 N3 N2 102.7(3) . . ? C7 N4 N5 109.4(4) . . ? C7 N4 C6 129.3(4) . . ? N5 N4 C6 121.2(4) . . ? C8 N5 N4 102.9(4) . . ? C7 N6 C8 102.5(4) . . ? C7 N6 Co1 126.8(3) . . ? C8 N6 Co1 130.4(3) . . ? C9 N7 Co1 179.7(4) . . ? C9 S1A O2 66.0(7) . . ? S1A O2 C9 54.9(6) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.69 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.532 _refine_diff_density_min -1.049 _refine_diff_density_rms 0.101 # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 792564' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H18 N6 Ni O7 S' _chemical_formula_weight 401.05 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' Ni Ni 0.3393 1.1124 '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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 8.506(2) _cell_length_b 17.003(4) _cell_length_c 10.491(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1517.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1256 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 23.57 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.463 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8214 _exptl_absorpt_correction_T_max 0.8675 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7031 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1465 _reflns_number_gt 1177 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w1/[\s^2^(Fo^2^)+(0.0920P)^2^+0.2251P] 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 1465 _refine_ls_number_parameters 123 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.069 _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 0.0794(5) 0.5938(3) 0.0636(4) 0.0214(10) Uani 1 1 d . . . H1 H 0.0375 0.5860 -0.0194 0.026 Uiso 1 1 calc R . . C2 C 0.1939(5) 0.6470(2) 0.2189(4) 0.0181(9) Uani 1 1 d . . . H2 H 0.2492 0.6825 0.2726 0.022 Uiso 1 1 calc R . . C3 C 0.1532(5) 0.5389(3) 0.3792(4) 0.0185(9) Uani 1 1 d . . . H3A H 0.2115 0.5737 0.4381 0.022 Uiso 1 1 calc R . . H3B H 0.2137 0.4895 0.3700 0.022 Uiso 1 1 calc R . . C4 C -0.0077(5) 0.5205(2) 0.4354(4) 0.0197(9) Uani 1 1 d . . . H4A H -0.0668 0.4863 0.3760 0.024 Uiso 1 1 calc R . . H4B H -0.0677 0.5700 0.4460 0.024 Uiso 1 1 calc R . . N1 N 0.1596(4) 0.6604(2) 0.0980(3) 0.0166(8) Uani 1 1 d . . . N2 N 0.0655(5) 0.5418(2) 0.1551(3) 0.0240(9) Uani 1 1 d . . . N3 N 0.1400(4) 0.5770(2) 0.2551(3) 0.0169(8) Uani 1 1 d . . . Ni1 Ni 0.22205(8) 0.7500 -0.02479(6) 0.0134(3) Uani 1 2 d S . . O1 O 0.0023(5) 0.7500 -0.1064(4) 0.0246(10) Uani 1 2 d SD . . H1A H -0.084(4) 0.7500 -0.066(5) 0.037 Uiso 1 2 d SD . . H1B H -0.009(7) 0.728(5) -0.179(4) 0.037 Uiso 0.50 1 d PD . . O2 O 0.2760(4) 0.66139(18) -0.1574(3) 0.0196(7) Uani 1 1 d D . . H2A H 0.3738(16) 0.654(3) -0.171(4) 0.029 Uiso 1 1 d D . . H2B H 0.228(4) 0.668(3) -0.228(2) 0.029 Uiso 1 1 d D . . O3 O 0.4561(5) 0.7500 0.0345(4) 0.0184(9) Uani 1 2 d S . . O4 O 0.5918(4) 0.6794(2) -0.1317(3) 0.0291(8) Uani 1 1 d . . . O5 O 0.7397(5) 0.7500 0.0284(4) 0.0344(13) Uani 1 2 d S . . S1 S 0.59579(16) 0.7500 -0.04897(13) 0.0164(4) Uani 1 2 d S . . 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 0.023(2) 0.029(2) 0.012(2) 0.0043(18) -0.0023(17) -0.0061(19) C2 0.026(2) 0.017(2) 0.012(2) -0.0011(16) 0.0026(17) -0.0017(18) C3 0.023(2) 0.021(2) 0.011(2) 0.0049(17) 0.0015(17) 0.0001(18) C4 0.025(2) 0.021(2) 0.013(2) 0.0064(18) 0.0025(17) 0.0008(19) N1 0.0195(18) 0.0198(19) 0.0104(17) 0.0011(14) -0.0010(14) -0.0001(15) N2 0.032(2) 0.026(2) 0.0143(19) -0.0007(16) -0.0007(16) -0.0110(17) N3 0.0261(19) 0.0169(19) 0.0077(16) 0.0016(13) 0.0025(15) 0.0004(14) Ni1 0.0149(4) 0.0175(4) 0.0077(4) 0.000 0.0005(3) 0.000 O1 0.015(2) 0.048(3) 0.011(2) 0.000 0.0006(16) 0.000 O2 0.0220(16) 0.0243(16) 0.0125(15) -0.0015(12) -0.0032(12) 0.0019(14) O3 0.013(2) 0.023(2) 0.019(2) 0.000 0.0017(17) 0.000 O4 0.0270(18) 0.0308(19) 0.0294(17) -0.0128(15) 0.0129(14) -0.0057(14) O5 0.018(2) 0.078(4) 0.008(2) 0.000 0.0008(17) 0.000 S1 0.0147(8) 0.0252(8) 0.0093(7) 0.000 0.0011(5) 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 N2 1.311(5) . ? C1 N1 1.371(5) . ? C1 H1 0.9500 . ? C2 N1 1.321(5) . ? C2 N3 1.332(5) . ? C2 H2 0.9500 . ? C3 N3 1.458(5) . ? C3 C4 1.523(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C4 1.529(8) 5_566 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N1 Ni1 2.065(3) . ? N2 N3 1.364(5) . ? Ni1 O1 2.056(4) . ? Ni1 N1 2.065(3) 7_575 ? Ni1 O3 2.086(4) . ? Ni1 O2 2.102(3) . ? Ni1 O2 2.102(3) 7_575 ? O1 H1A 0.853(10) . ? O1 H1B 0.848(10) . ? O2 H2A 0.853(10) . ? O2 H2B 0.848(10) . ? O3 S1 1.476(4) . ? O4 S1 1.481(3) . ? O5 S1 1.468(5) . ? S1 O4 1.481(3) 7_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 114.1(4) . . ? N2 C1 H1 122.9 . . ? N1 C1 H1 122.9 . . ? N1 C2 N3 110.6(4) . . ? N1 C2 H2 124.7 . . ? N3 C2 H2 124.7 . . ? N3 C3 C4 111.6(3) . . ? N3 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? N3 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C4 111.1(4) . 5_566 ? C3 C4 H4A 109.4 . . ? C4 C4 H4A 109.4 5_566 . ? C3 C4 H4B 109.4 . . ? C4 C4 H4B 109.4 5_566 . ? H4A C4 H4B 108.0 . . ? C2 N1 C1 102.8(3) . . ? C2 N1 Ni1 132.0(3) . . ? C1 N1 Ni1 125.0(3) . . ? C1 N2 N3 103.1(3) . . ? C2 N3 N2 109.4(3) . . ? C2 N3 C3 128.7(4) . . ? N2 N3 C3 121.9(3) . . ? O1 Ni1 N1 91.48(12) . 7_575 ? O1 Ni1 N1 91.48(12) . . ? N1 Ni1 N1 95.11(19) 7_575 . ? O1 Ni1 O3 172.74(16) . . ? N1 Ni1 O3 93.41(12) 7_575 . ? N1 Ni1 O3 93.41(12) . . ? O1 Ni1 O2 85.56(12) . . ? N1 Ni1 O2 176.64(12) 7_575 . ? N1 Ni1 O2 86.58(13) . . ? O3 Ni1 O2 89.38(11) . . ? O1 Ni1 O2 85.56(12) . 7_575 ? N1 Ni1 O2 86.58(13) 7_575 7_575 ? N1 Ni1 O2 176.64(12) . 7_575 ? O3 Ni1 O2 89.38(11) . 7_575 ? O2 Ni1 O2 91.59(17) . 7_575 ? Ni1 O1 H1A 125(4) . . ? Ni1 O1 H1B 119(5) . . ? H1A O1 H1B 110(3) . . ? Ni1 O2 H2A 115(3) . . ? Ni1 O2 H2B 112(3) . . ? H2A O2 H2B 110(2) . . ? S1 O3 Ni1 126.2(2) . . ? O5 S1 O3 110.0(2) . . ? O5 S1 O4 110.05(17) . . ? O3 S1 O4 109.24(15) . . ? O5 S1 O4 110.05(17) . 7_575 ? O3 S1 O4 109.24(15) . 7_575 ? O4 S1 O4 108.2(3) . 7_575 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.483 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.146 # Attachment '792565.cif' data_100713b_0m _database_code_depnum_ccdc_archive 'CCDC 792565' #TrackingRef '792565.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 Br2 Cu N12' _chemical_formula_weight 607.83 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.7348(5) _cell_length_b 17.2121(12) _cell_length_c 8.7343(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.8490(10) _cell_angle_gamma 90.00 _cell_volume 1063.53(12) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 1839 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 26.86 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 4.817 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2012 _exptl_absorpt_correction_T_max 0.4776 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6160 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.61 _reflns_number_total 2435 _reflns_number_gt 1914 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+0.3171P] 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 2435 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0634 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 -0.0337(4) 0.32957(16) 0.4016(4) 0.0293(6) Uani 1 1 d . . . H1 H -0.1422 0.3239 0.4219 0.035 Uiso 1 1 calc R . . C2 C 0.2060(4) 0.38011(16) 0.3845(3) 0.0286(6) Uani 1 1 d . . . H2 H 0.2999 0.4146 0.3874 0.034 Uiso 1 1 calc R . . C3 C 0.3098(4) 0.26512(18) 0.2679(4) 0.0381(8) Uani 1 1 d . . . H3A H 0.3607 0.3018 0.2126 0.046 Uiso 1 1 calc R . . H3B H 0.2319 0.2283 0.1843 0.046 Uiso 1 1 calc R . . C4 C 0.4717(4) 0.22176(16) 0.3998(3) 0.0287(6) Uani 1 1 d . . . H4A H 0.4225 0.1858 0.4580 0.034 Uiso 1 1 calc R . . H4B H 0.5541 0.2583 0.4811 0.034 Uiso 1 1 calc R . . C5 C 0.5840(4) 0.17713(16) 0.3202(3) 0.0271(6) Uani 1 1 d . . . H5A H 0.5015 0.1400 0.2406 0.032 Uiso 1 1 calc R . . H5B H 0.6296 0.2131 0.2594 0.032 Uiso 1 1 calc R . . C6 C 0.7491(4) 0.13482(18) 0.4484(3) 0.0330(7) Uani 1 1 d . . . H6A H 0.8229 0.1709 0.5358 0.040 Uiso 1 1 calc R . . H6B H 0.7027 0.0944 0.4993 0.040 Uiso 1 1 calc R . . C7 C 1.1194(4) 0.06036(16) 0.3628(4) 0.0293(6) Uani 1 1 d . . . H7 H 1.2455 0.0477 0.3914 0.035 Uiso 1 1 calc R . . C8 C 0.8280(4) 0.07507(16) 0.2215(3) 0.0264(6) Uani 1 1 d . . . H8 H 0.7073 0.0756 0.1360 0.032 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.5000 0.5000 0.02607(13) Uani 1 2 d S . . N1 N 0.0661(3) 0.39678(12) 0.4306(3) 0.0236(5) Uani 1 1 d . . . N2 N 0.0356(3) 0.27329(13) 0.3426(3) 0.0345(6) Uani 1 1 d . . . N3 N 0.1912(3) 0.30704(13) 0.3337(3) 0.0277(5) Uani 1 1 d . . . N4 N 0.8709(3) 0.09992(12) 0.3752(3) 0.0243(5) Uani 1 1 d . . . N5 N 1.0587(3) 0.09040(14) 0.4691(3) 0.0314(5) Uani 1 1 d . . . N6 N 0.9822(3) 0.04916(12) 0.2063(3) 0.0246(5) Uani 1 1 d . . . Br1 Br 0.40867(4) 0.538209(18) 0.70339(4) 0.03400(10) 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 0.0284(15) 0.0248(15) 0.0399(17) 0.0030(12) 0.0192(13) 0.0025(11) C2 0.0296(15) 0.0299(16) 0.0307(15) -0.0010(12) 0.0167(12) -0.0003(12) C3 0.0450(18) 0.046(2) 0.0284(16) -0.0015(14) 0.0202(14) 0.0214(14) C4 0.0286(15) 0.0325(16) 0.0282(15) -0.0028(12) 0.0149(12) 0.0076(12) C5 0.0287(14) 0.0301(16) 0.0239(14) -0.0048(12) 0.0123(12) 0.0048(11) C6 0.0392(17) 0.0419(18) 0.0239(14) 0.0010(13) 0.0189(13) 0.0146(13) C7 0.0249(14) 0.0272(16) 0.0387(16) -0.0019(12) 0.0157(13) 0.0021(11) C8 0.0271(14) 0.0302(16) 0.0245(14) -0.0007(12) 0.0133(11) 0.0036(12) Cu1 0.0392(3) 0.0171(2) 0.0352(3) 0.0029(2) 0.0288(2) 0.0030(2) N1 0.0233(11) 0.0229(12) 0.0296(12) 0.0014(9) 0.0158(10) 0.0030(9) N2 0.0360(14) 0.0252(13) 0.0435(15) 0.0009(11) 0.0174(12) 0.0046(11) N3 0.0306(13) 0.0296(14) 0.0247(12) -0.0003(10) 0.0129(10) 0.0102(10) N4 0.0264(12) 0.0250(13) 0.0254(12) 0.0004(9) 0.0147(10) 0.0058(9) N5 0.0285(13) 0.0341(14) 0.0296(13) -0.0040(10) 0.0098(10) 0.0047(10) N6 0.0253(11) 0.0223(12) 0.0333(13) -0.0011(9) 0.0192(10) 0.0003(9) Br1 0.02426(15) 0.0455(2) 0.03515(17) 0.00452(13) 0.01500(12) 0.00064(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 N2 1.309(3) . ? C1 N1 1.357(3) . ? C1 H1 0.9300 . ? C2 N3 1.323(3) . ? C2 N1 1.329(3) . ? C2 H2 0.9300 . ? C3 N3 1.455(3) . ? C3 C4 1.512(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.522(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.503(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N4 1.464(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N5 1.305(3) . ? C7 N6 1.363(4) . ? C7 H7 0.9300 . ? C8 N4 1.317(3) . ? C8 N6 1.330(3) . ? C8 H8 0.9300 . ? Cu1 N1 2.009(2) . ? Cu1 N1 2.009(2) 3_566 ? Cu1 N6 2.045(2) 4_466 ? Cu1 N6 2.045(2) 2_655 ? Cu1 Br1 3.0065(3) . ? N2 N3 1.367(3) . ? N4 N5 1.359(3) . ? N6 Cu1 2.045(2) 2_645 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 114.3(2) . . ? N2 C1 H1 122.8 . . ? N1 C1 H1 122.8 . . ? N3 C2 N1 109.6(2) . . ? N3 C2 H2 125.2 . . ? N1 C2 H2 125.2 . . ? N3 C3 C4 113.8(2) . . ? N3 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? N3 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 110.6(2) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 112.0(2) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N4 C6 C5 112.1(2) . . ? N4 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? N4 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N5 C7 N6 114.3(2) . . ? N5 C7 H7 122.8 . . ? N6 C7 H7 122.8 . . ? N4 C8 N6 110.1(2) . . ? N4 C8 H8 124.9 . . ? N6 C8 H8 124.9 . . ? N1 Cu1 N1 180.0 . 3_566 ? N1 Cu1 N6 90.92(8) . 4_466 ? N1 Cu1 N6 89.08(8) 3_566 4_466 ? N1 Cu1 N6 89.08(8) . 2_655 ? N1 Cu1 N6 90.92(8) 3_566 2_655 ? N6 Cu1 N6 180.0 4_466 2_655 ? N1 Cu1 Br1 92.10(6) . . ? N1 Cu1 Br1 87.90(6) 3_566 . ? N6 Cu1 Br1 89.94(6) 4_466 . ? N6 Cu1 Br1 90.06(6) 2_655 . ? C2 N1 C1 103.3(2) . . ? C2 N1 Cu1 128.31(18) . . ? C1 N1 Cu1 127.98(17) . . ? C1 N2 N3 102.6(2) . . ? C2 N3 N2 110.1(2) . . ? C2 N3 C3 128.4(3) . . ? N2 N3 C3 121.4(2) . . ? C8 N4 N5 110.1(2) . . ? C8 N4 C6 129.6(2) . . ? N5 N4 C6 120.3(2) . . ? C7 N5 N4 102.9(2) . . ? C8 N6 C7 102.6(2) . . ? C8 N6 Cu1 127.54(19) . 2_645 ? C7 N6 Cu1 129.77(17) . 2_645 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.491 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.081 # Attachment 'BO872.cif' data_bo872 _database_code_depnum_ccdc_archive 'CCDC 807514' #TrackingRef 'BO872.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C72 H108 Cl6 N54 Ni3 O24' _chemical_formula_weight 2502.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 18.787(2) _cell_length_b 18.787(2) _cell_length_c 25.170(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7693.2(16) _cell_formula_units_Z 3 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 7360 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 27.48 _exptl_crystal_description Chunk _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3888 _exptl_absorpt_coefficient_mu 0.800 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.8251 _exptl_absorpt_correction_T_max 0.8894 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24493 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3919 _reflns_number_gt 3407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w1/[\s^2^(Fo^2^)+(0.0631P)^2^+26.6800P] 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 3919 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.3333 0.6667 0.005710(16) 0.00827(12) Uani 1 3 d S . . Ni2 Ni 0.0000 0.0000 0.0000 0.01161(15) Uani 1 6 d S . . N1 N 0.26340(10) 0.56283(10) 0.05512(7) 0.0115(3) Uani 1 1 d . . . N2 N 0.20992(11) 0.44260(11) 0.09301(7) 0.0142(4) Uani 1 1 d . . . N3 N 0.18618(12) 0.48635(12) 0.12390(7) 0.0185(4) Uani 1 1 d . . . N4 N 0.14594(11) 0.22934(11) 0.26250(7) 0.0140(4) Uani 1 1 d . . . N5 N 0.17389(13) 0.18638(12) 0.23476(8) 0.0206(4) Uani 1 1 d . . . N6 N 0.07366(10) 0.10358(10) 0.29129(7) 0.0111(3) Uani 1 1 d . . . N7 N 0.08621(11) -0.00761(11) 0.04945(7) 0.0152(4) Uani 1 1 d . . . N8 N 0.20077(11) 0.03649(12) 0.09285(8) 0.0170(4) Uani 1 1 d . . . N9 N 0.14283(12) -0.02351(12) 0.12417(8) 0.0223(4) Uani 1 1 d . . . C1 C 0.25475(13) 0.48807(13) 0.05279(8) 0.0133(4) Uani 1 1 d . . . H1 H 0.2776 0.4700 0.0259 0.016 Uiso 1 1 calc R . . C2 C 0.21995(13) 0.55815(13) 0.09971(8) 0.0151(4) Uani 1 1 d . . . H2 H 0.2145 0.6029 0.1123 0.018 Uiso 1 1 calc R . . C3 C 0.17973(15) 0.35494(13) 0.10212(9) 0.0176(4) Uani 1 1 d . . . H3A H 0.1993 0.3339 0.0729 0.021 Uiso 1 1 calc R . . H3B H 0.1189 0.3251 0.1008 0.021 Uiso 1 1 calc R . . C4 C 0.20662(14) 0.33592(13) 0.15479(9) 0.0164(4) Uani 1 1 d . . . H4A H 0.2658 0.3753 0.1603 0.020 Uiso 1 1 calc R . . H4B H 0.1995 0.2801 0.1531 0.020 Uiso 1 1 calc R . . C5 C 0.15834(14) 0.34062(13) 0.20215(8) 0.0163(4) Uani 1 1 d . . . H5A H 0.1675 0.3972 0.2045 0.020 Uiso 1 1 calc R . . H5B H 0.0990 0.3032 0.1956 0.020 Uiso 1 1 calc R . . C6 C 0.18093(14) 0.31828(13) 0.25517(9) 0.0171(4) Uani 1 1 d . . . H6A H 0.2415 0.3455 0.2578 0.021 Uiso 1 1 calc R . . H6B H 0.1614 0.3397 0.2842 0.021 Uiso 1 1 calc R . . C7 C 0.08700(13) 0.17986(13) 0.29565(8) 0.0135(4) Uani 1 1 d . . . H7 H 0.0584 0.1965 0.3191 0.016 Uiso 1 1 calc R . . C8 C 0.12837(14) 0.11126(14) 0.25319(9) 0.0181(5) Uani 1 1 d . . . H8 H 0.1333 0.0661 0.2409 0.022 Uiso 1 1 calc R . . C9 C 0.16672(13) 0.04548(14) 0.04933(9) 0.0171(4) Uani 1 1 d . . . H9 H 0.1955 0.0842 0.0220 0.021 Uiso 1 1 calc R . . C10 C 0.07511(14) -0.04878(14) 0.09620(9) 0.0193(5) Uani 1 1 d . . . H10 H 0.0231 -0.0919 0.1076 0.023 Uiso 1 1 calc R . . C11 C 0.28567(13) 0.08586(15) 0.11106(9) 0.0198(5) Uani 1 1 d . . . H11A H 0.3208 0.1202 0.0815 0.024 Uiso 1 1 calc R . . H11B H 0.3064 0.0493 0.1229 0.024 Uiso 1 1 calc R . . C12 C 0.28958(13) 0.14030(14) 0.15657(9) 0.0180(5) Uani 1 1 d . . . H12A H 0.2541 0.1056 0.1859 0.022 Uiso 1 1 calc R . . H12B H 0.2683 0.1763 0.1446 0.022 Uiso 1 1 calc R . . Cl1 Cl 0.33476(4) 0.30430(4) 0.02968(2) 0.02280(15) Uani 1 1 d . . . O1 O 0.34011(15) 0.38260(14) 0.02725(11) 0.0554(7) Uani 1 1 d . . . O2 O 0.25237(13) 0.23939(13) 0.03638(12) 0.0534(7) Uani 1 1 d . . . O3 O 0.3738(2) 0.29515(19) -0.01536(13) 0.0933(13) Uani 1 1 d . . . O4 O 0.38126(18) 0.30525(17) 0.07399(13) 0.0825(11) 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 Ni1 0.00844(15) 0.00844(15) 0.0079(2) 0.000 0.000 0.00422(8) Ni2 0.0102(2) 0.0102(2) 0.0144(3) 0.000 0.000 0.00510(10) N1 0.0102(8) 0.0110(8) 0.0114(8) 0.0008(6) -0.0001(6) 0.0040(7) N2 0.0161(9) 0.0124(9) 0.0132(8) 0.0015(7) 0.0022(7) 0.0064(7) N3 0.0222(10) 0.0178(9) 0.0181(9) 0.0047(7) 0.0071(7) 0.0120(8) N4 0.0163(9) 0.0119(8) 0.0128(8) 0.0026(6) 0.0011(7) 0.0064(7) N5 0.0242(10) 0.0177(10) 0.0231(10) 0.0054(8) 0.0105(8) 0.0129(8) N6 0.0108(8) 0.0112(8) 0.0107(8) 0.0015(6) 0.0004(6) 0.0050(7) N7 0.0128(9) 0.0154(9) 0.0194(9) -0.0015(7) -0.0015(7) 0.0086(7) N8 0.0137(9) 0.0165(9) 0.0213(9) -0.0032(7) -0.0031(7) 0.0080(8) N9 0.0198(10) 0.0187(10) 0.0269(10) 0.0034(8) -0.0048(8) 0.0085(8) C1 0.0155(10) 0.0134(10) 0.0107(9) 0.0011(7) 0.0013(7) 0.0069(8) C2 0.0164(10) 0.0144(10) 0.0150(10) 0.0032(8) 0.0038(8) 0.0082(9) C3 0.0228(11) 0.0100(10) 0.0169(10) 0.0019(8) 0.0021(8) 0.0058(9) C4 0.0177(11) 0.0135(10) 0.0177(11) 0.0038(8) 0.0030(8) 0.0076(9) C5 0.0189(11) 0.0129(10) 0.0162(10) 0.0031(8) 0.0017(8) 0.0073(9) C6 0.0220(11) 0.0095(10) 0.0152(10) 0.0016(8) 0.0006(8) 0.0044(9) C7 0.0151(10) 0.0137(10) 0.0108(9) 0.0004(7) 0.0007(7) 0.0066(8) C8 0.0225(11) 0.0150(10) 0.0188(11) 0.0041(8) 0.0076(9) 0.0109(9) C9 0.0150(10) 0.0194(11) 0.0184(10) -0.0019(8) -0.0004(8) 0.0097(9) C10 0.0173(11) 0.0139(10) 0.0254(12) 0.0033(9) -0.0036(9) 0.0068(9) C11 0.0114(10) 0.0248(12) 0.0224(11) -0.0067(9) -0.0042(8) 0.0084(9) C12 0.0128(11) 0.0222(11) 0.0183(11) -0.0039(8) -0.0026(8) 0.0082(9) Cl1 0.0247(3) 0.0226(3) 0.0222(3) -0.0027(2) -0.0002(2) 0.0126(2) O1 0.0431(13) 0.0297(12) 0.096(2) 0.0117(12) 0.0258(13) 0.0203(11) O2 0.0249(11) 0.0292(11) 0.095(2) 0.0010(12) -0.0131(12) 0.0052(9) O3 0.136(3) 0.0628(19) 0.081(2) -0.0091(16) 0.057(2) 0.049(2) O4 0.0632(18) 0.0543(17) 0.082(2) 0.0262(15) -0.0410(16) -0.0065(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N6 2.1103(17) 7_554 ? Ni1 N6 2.1104(17) 8_554 ? Ni1 N6 2.1104(17) 9_554 ? Ni1 N1 2.1249(17) 2_665 ? Ni1 N1 2.1249(17) 3_565 ? Ni1 N1 2.1249(17) . ? Ni2 N7 2.1033(18) 2 ? Ni2 N7 2.1033(18) 11 ? Ni2 N7 2.1034(18) 10 ? Ni2 N7 2.1034(18) . ? Ni2 N7 2.1034(18) 12 ? Ni2 N7 2.1034(18) 3 ? N1 C1 1.332(3) . ? N1 C2 1.364(3) . ? N2 C1 1.321(3) . ? N2 N3 1.359(3) . ? N2 C3 1.467(3) . ? N3 C2 1.318(3) . ? N4 C7 1.326(3) . ? N4 N5 1.356(3) . ? N4 C6 1.470(3) . ? N5 C8 1.316(3) . ? N6 C7 1.330(3) . ? N6 C8 1.360(3) . ? N6 Ni1 2.1103(17) 4_445 ? N7 C9 1.332(3) . ? N7 C10 1.366(3) . ? N8 C9 1.321(3) . ? N8 N9 1.360(3) . ? N8 C11 1.461(3) . ? N9 C10 1.317(3) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C4 1.523(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.527(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.522(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.513(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C12 1.521(4) 13 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? Cl1 O3 1.407(3) . ? Cl1 O4 1.411(3) . ? Cl1 O2 1.423(2) . ? Cl1 O1 1.425(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 N6 Ni1 N6 90.77(7) 7_554 8_554 ? N6 Ni1 N6 90.77(7) 7_554 9_554 ? N6 Ni1 N6 90.77(7) 8_554 9_554 ? N6 Ni1 N1 88.65(7) 7_554 2_665 ? N6 Ni1 N1 177.77(6) 8_554 2_665 ? N6 Ni1 N1 91.39(6) 9_554 2_665 ? N6 Ni1 N1 91.39(6) 7_554 3_565 ? N6 Ni1 N1 88.66(7) 8_554 3_565 ? N6 Ni1 N1 177.77(6) 9_554 3_565 ? N1 Ni1 N1 89.20(7) 2_665 3_565 ? N6 Ni1 N1 177.77(6) 7_554 . ? N6 Ni1 N1 91.39(6) 8_554 . ? N6 Ni1 N1 88.65(7) 9_554 . ? N1 Ni1 N1 89.21(7) 2_665 . ? N1 Ni1 N1 89.21(7) 3_565 . ? N7 Ni2 N7 180.0 2 11 ? N7 Ni2 N7 91.45(7) 2 10 ? N7 Ni2 N7 88.55(7) 11 10 ? N7 Ni2 N7 88.55(7) 2 . ? N7 Ni2 N7 91.45(7) 11 . ? N7 Ni2 N7 180.0 10 . ? N7 Ni2 N7 91.45(7) 2 12 ? N7 Ni2 N7 88.55(7) 11 12 ? N7 Ni2 N7 88.55(7) 10 12 ? N7 Ni2 N7 91.45(7) . 12 ? N7 Ni2 N7 88.55(7) 2 3 ? N7 Ni2 N7 91.45(7) 11 3 ? N7 Ni2 N7 91.45(7) 10 3 ? N7 Ni2 N7 88.55(7) . 3 ? N7 Ni2 N7 180.00(8) 12 3 ? C1 N1 C2 102.40(17) . . ? C1 N1 Ni1 129.46(14) . . ? C2 N1 Ni1 128.02(14) . . ? C1 N2 N3 110.09(17) . . ? C1 N2 C3 127.54(18) . . ? N3 N2 C3 122.01(17) . . ? C2 N3 N2 102.65(17) . . ? C7 N4 N5 110.06(17) . . ? C7 N4 C6 128.19(18) . . ? N5 N4 C6 121.73(18) . . ? C8 N5 N4 102.67(18) . . ? C7 N6 C8 102.63(17) . . ? C7 N6 Ni1 129.04(14) . 4_445 ? C8 N6 Ni1 127.73(14) . 4_445 ? C9 N7 C10 102.75(18) . . ? C9 N7 Ni2 124.92(15) . . ? C10 N7 Ni2 130.07(15) . . ? C9 N8 N9 110.39(18) . . ? C9 N8 C11 128.6(2) . . ? N9 N8 C11 120.77(19) . . ? C10 N9 N8 102.57(19) . . ? N2 C1 N1 110.50(18) . . ? N2 C1 H1 124.8 . . ? N1 C1 H1 124.8 . . ? N3 C2 N1 114.36(19) . . ? N3 C2 H2 122.8 . . ? N1 C2 H2 122.8 . . ? N2 C3 C4 114.33(18) . . ? N2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? N2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 112.92(18) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 114.40(19) . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N4 C6 C5 113.31(18) . . ? N4 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? N4 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N4 C7 N6 110.18(18) . . ? N4 C7 H7 124.9 . . ? N6 C7 H7 124.9 . . ? N5 C8 N6 114.45(19) . . ? N5 C8 H8 122.8 . . ? N6 C8 H8 122.8 . . ? N8 C9 N7 110.1(2) . . ? N8 C9 H9 125.0 . . ? N7 C9 H9 125.0 . . ? N9 C10 N7 114.2(2) . . ? N9 C10 H10 122.9 . . ? N7 C10 H10 122.9 . . ? N8 C11 C12 109.58(18) . . ? N8 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N8 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C12 111.4(2) . 13 ? C11 C12 H12A 109.4 . . ? C12 C12 H12A 109.4 13 . ? C11 C12 H12B 109.4 . . ? C12 C12 H12B 109.4 13 . ? H12A C12 H12B 108.0 . . ? O3 Cl1 O4 106.3(2) . . ? O3 Cl1 O2 113.64(19) . . ? O4 Cl1 O2 108.57(16) . . ? O3 Cl1 O1 108.65(18) . . ? O4 Cl1 O1 107.29(18) . . ? O2 Cl1 O1 112.03(14) . . ? 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 N6 Ni1 N1 C1 -70.6(18) 7_554 . . . ? N6 Ni1 N1 C1 95.09(18) 8_554 . . . ? N6 Ni1 N1 C1 4.36(18) 9_554 . . . ? N1 Ni1 N1 C1 -87.1(2) 2_665 . . . ? N1 Ni1 N1 C1 -176.27(18) 3_565 . . . ? N6 Ni1 N1 C2 104.7(17) 7_554 . . . ? N6 Ni1 N1 C2 -89.57(18) 8_554 . . . ? N6 Ni1 N1 C2 179.69(18) 9_554 . . . ? N1 Ni1 N1 C2 88.28(14) 2_665 . . . ? N1 Ni1 N1 C2 -0.93(18) 3_565 . . . ? C1 N2 N3 C2 -0.5(2) . . . . ? C3 N2 N3 C2 -174.15(19) . . . . ? C7 N4 N5 C8 0.4(2) . . . . ? C6 N4 N5 C8 179.10(19) . . . . ? N7 Ni2 N7 C9 -76.8(2) 2 . . . ? N7 Ni2 N7 C9 103.2(2) 11 . . . ? N7 Ni2 N7 C9 94(2) 10 . . . ? N7 Ni2 N7 C9 14.65(17) 12 . . . ? N7 Ni2 N7 C9 -165.36(17) 3 . . . ? N7 Ni2 N7 C10 83.10(16) 2 . . . ? N7 Ni2 N7 C10 -96.90(16) 11 . . . ? N7 Ni2 N7 C10 -106(2) 10 . . . ? N7 Ni2 N7 C10 174.51(19) 12 . . . ? N7 Ni2 N7 C10 -5.49(19) 3 . . . ? C9 N8 N9 C10 0.9(2) . . . . ? C11 N8 N9 C10 175.5(2) . . . . ? N3 N2 C1 N1 0.5(2) . . . . ? C3 N2 C1 N1 173.70(19) . . . . ? C2 N1 C1 N2 -0.2(2) . . . . ? Ni1 N1 C1 N2 175.99(14) . . . . ? N2 N3 C2 N1 0.3(2) . . . . ? C1 N1 C2 N3 -0.1(2) . . . . ? Ni1 N1 C2 N3 -176.39(15) . . . . ? C1 N2 C3 C4 122.5(2) . . . . ? N3 N2 C3 C4 -65.0(3) . . . . ? N2 C3 C4 C5 76.5(2) . . . . ? C3 C4 C5 C6 177.43(18) . . . . ? C7 N4 C6 C5 -110.3(2) . . . . ? N5 N4 C6 C5 71.2(3) . . . . ? C4 C5 C6 N4 -76.9(2) . . . . ? N5 N4 C7 N6 -0.1(2) . . . . ? C6 N4 C7 N6 -178.67(19) . . . . ? C8 N6 C7 N4 -0.3(2) . . . . ? Ni1 N6 C7 N4 171.29(14) 4_445 . . . ? N4 N5 C8 N6 -0.6(3) . . . . ? C7 N6 C8 N5 0.6(3) . . . . ? Ni1 N6 C8 N5 -171.15(15) 4_445 . . . ? N9 N8 C9 N7 -0.5(3) . . . . ? C11 N8 C9 N7 -174.6(2) . . . . ? C10 N7 C9 N8 -0.1(2) . . . . ? Ni2 N7 C9 N8 164.24(14) . . . . ? N8 N9 C10 N7 -1.0(3) . . . . ? C9 N7 C10 N9 0.7(3) . . . . ? Ni2 N7 C10 N9 -162.45(16) . . . . ? C9 N8 C11 C12 105.4(3) . . . . ? N9 N8 C11 C12 -68.1(3) . . . . ? N8 C11 C12 C12 -179.9(2) . . . 13 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.004 _refine_diff_density_min -0.770 _refine_diff_density_rms 0.085 data_1 _database_code_depnum_ccdc_archive 'CCDC 819014' #TrackingRef '101004b_0m.cif' #============================================================================== # 1. SUBMISSION DETAILS _pub1_contact_author # Name and address of author for correspondence ; Yakun Gu Department of Chemistry Capital Normal University Beijing 100048 P. R. China ; #============================================================================== _audit_creation_method SHELXL-97 _chemical_formula_moiety '2(C4 H9 Co0.5 N3 O3.5 S0.5)' _chemical_formula_sum 'C8 H18 Co N6 O7 S' _chemical_formula_weight 401.27 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z' 4 'x+1/2, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z' 8 '-x-1/2, y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.5182(11) _cell_length_b 17.061(2) _cell_length_c 10.5318(14) _cell_measurement_reflns_used 1262 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 23.947 _cell_measurement_theta_min 2.273 _cell_volume 1530.6(4) _exptl_absorpt_coefficient_mu 1.304 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.799256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0541 before and 0.0445 after correction. The Ratio of minimum to maximum transmission is 0.799256. The \l/2 correction factor is 0.0015 ; _exptl_crystal_F_000 828 _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_special_details ? _diffrn_ambient_temperature 150.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8798 _diffrn_reflns_theta_full 27.59 _diffrn_reflns_theta_max 27.59 _diffrn_reflns_theta_min 2.27 _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1444 _reflns_number_total 1831 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.34A (Bruker, 200?)' _computing_molecular_graphics ; _computing_publication_material ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.676 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.091 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0359 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 123 _refine_ls_number_reflns 1831 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.0855 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.6308P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.1946(3) 0.35416(15) 0.7215(2) 0.0168(5) Uani 1 1 d . . . H1 H 0.2499 0.3188 0.7751 0.020 Uiso 1 1 calc R . . C2 C 0.0815(3) 0.40715(15) 0.5660(2) 0.0194(5) Uani 1 1 d . . . H2 H 0.0410 0.4152 0.4830 0.023 Uiso 1 1 calc R . . C3 C 0.1526(3) 0.46209(15) 0.8804(2) 0.0180(5) Uani 1 1 d . . . H3B H 0.2119 0.5117 0.8713 0.022 Uiso 1 1 calc R . . H3A H 0.2112 0.4278 0.9395 0.022 Uiso 1 1 calc R . . C4 C -0.0078(3) 0.47950(15) 0.9356(2) 0.0194(6) Uani 1 1 d . . . H4A H -0.0669 0.4300 0.9461 0.023 Uiso 1 1 calc R . . H4B H -0.0672 0.5135 0.8764 0.023 Uiso 1 1 calc R . . Co1 Co 0.22460(5) 0.2500 0.47554(4) 0.01203(14) Uani 1 2 d S . . N1 N 0.1598(2) 0.34096(11) 0.60031(18) 0.0152(4) Uani 1 1 d . . . N2 N 0.1410(2) 0.42385(12) 0.75693(18) 0.0155(4) Uani 1 1 d . . . N3 N 0.0666(3) 0.45898(13) 0.6571(2) 0.0219(5) Uani 1 1 d . . . O1 O 0.4607(3) 0.2500 0.5351(2) 0.0165(5) Uani 1 2 d S . . O2 O 0.5947(2) 0.32014(11) 0.36882(19) 0.0283(5) Uani 1 1 d . . . O3 O 0.7424(3) 0.2500 0.5261(2) 0.0318(7) Uani 1 2 d S . . O4 O 0.2793(2) 0.33958(11) 0.34072(16) 0.0181(4) Uani 1 1 d D . . H4C H 0.236(3) 0.3344(17) 0.2698(19) 0.027 Uiso 1 1 d D . . H4D H 0.3787(19) 0.3420(17) 0.334(2) 0.027 Uiso 1 1 d D . . O5 O 0.0046(3) 0.2500 0.3921(2) 0.0246(6) Uani 1 2 d SD . . H5A H -0.002(5) 0.228(3) 0.322(3) 0.037 Uiso 0.50 1 d PD . . H5B H -0.079(3) 0.2500 0.433(3) 0.037 Uiso 1 2 d SD . . S1 S 0.59895(9) 0.2500 0.45043(8) 0.0148(2) Uani 1 2 d S . . 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 0.0211(13) 0.0167(13) 0.0127(12) 0.0011(10) 0.0019(10) 0.0034(10) C2 0.0230(13) 0.0234(14) 0.0118(12) -0.0003(11) -0.0007(10) 0.0058(11) C3 0.0214(13) 0.0184(13) 0.0142(12) -0.0075(10) 0.0022(10) 0.0008(10) C4 0.0208(13) 0.0224(14) 0.0150(13) -0.0061(11) 0.0011(10) 0.0014(11) Co1 0.0118(2) 0.0140(3) 0.0102(2) 0.000 0.00062(18) 0.000 N1 0.0178(11) 0.0159(11) 0.0119(10) -0.0006(8) 0.0018(8) 0.0012(8) N2 0.0211(11) 0.0149(11) 0.0103(10) -0.0009(8) 0.0011(8) 0.0020(8) N3 0.0282(12) 0.0216(12) 0.0159(11) -0.0011(9) -0.0004(9) 0.0077(10) O1 0.0131(12) 0.0241(14) 0.0124(12) 0.000 0.0012(9) 0.000 O2 0.0249(10) 0.0278(11) 0.0324(11) 0.0128(9) 0.0122(8) 0.0043(8) O3 0.0117(13) 0.070(2) 0.0136(13) 0.000 -0.0023(10) 0.000 O4 0.0190(9) 0.0211(10) 0.0142(9) 0.0021(7) -0.0020(7) -0.0016(8) O5 0.0133(13) 0.0468(18) 0.0137(13) 0.000 -0.0013(10) 0.000 S1 0.0112(4) 0.0217(5) 0.0114(4) 0.000 0.0005(3) 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 H1 0.9500 . ? C1 N1 1.330(3) . ? C1 N2 1.327(3) . ? C2 H2 0.9500 . ? C2 N1 1.360(3) . ? C2 N3 1.311(3) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C3 C4 1.514(3) . ? C3 N2 1.458(3) . ? C4 C4 1.533(5) 5_567 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? Co1 N1 2.107(2) 7_565 ? Co1 N1 2.107(2) . ? Co1 O1 2.107(2) . ? Co1 O4 2.1375(18) . ? Co1 O4 2.1375(18) 7_565 ? Co1 O5 2.070(2) . ? N2 N3 1.366(3) . ? O1 S1 1.477(2) . ? O2 S1 1.4738(19) . ? O3 S1 1.459(2) . ? O4 H4C 0.837(16) . ? O4 H4D 0.850(16) . ? O5 H5A 0.829(18) . ? O5 H5B 0.835(18) . ? S1 O2 1.4738(19) 7_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 102.9(2) . . ? C1 N1 Co1 131.69(17) . . ? C1 N2 C3 128.9(2) . . ? C1 N2 N3 109.68(19) . . ? C2 N1 Co1 125.06(16) . . ? C2 N3 N2 102.8(2) . . ? C3 C4 C4 110.5(3) . 5_567 ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H3B C3 H3A 108.0 . . ? C4 C3 H3B 109.3 . . ? C4 C3 H3A 109.3 . . ? C4 C4 H4A 109.5 5_567 . ? C4 C4 H4B 109.5 5_567 . ? H4A C4 H4B 108.1 . . ? Co1 O4 H4C 115(2) . . ? Co1 O4 H4D 108(2) . . ? Co1 O5 H5A 116(3) . . ? Co1 O5 H5B 123(3) . . ? N1 C1 H1 124.9 . . ? N1 C2 H2 122.8 . . ? N1 Co1 N1 94.87(11) . 7_565 ? N1 Co1 O4 176.35(7) . 7_565 ? N1 Co1 O4 176.35(7) 7_565 . ? N1 Co1 O4 86.83(7) . . ? N1 Co1 O4 86.83(7) 7_565 7_565 ? N2 C1 H1 124.9 . . ? N2 C1 N1 110.2(2) . . ? N2 C3 H3B 109.3 . . ? N2 C3 H3A 109.3 . . ? N2 C3 C4 111.6(2) . . ? N3 C2 H2 122.8 . . ? N3 C2 N1 114.4(2) . . ? N3 N2 C3 121.4(2) . . ? O1 Co1 N1 93.68(7) . 7_565 ? O1 Co1 N1 93.68(7) . . ? O1 Co1 O4 89.42(7) . . ? O1 Co1 O4 89.42(7) . 7_565 ? O2 S1 O1 109.42(9) . . ? O2 S1 O1 109.42(9) 7_565 . ? O2 S1 O2 108.57(17) 7_565 . ? O3 S1 O1 109.76(14) . . ? O3 S1 O2 109.83(10) . . ? O3 S1 O2 109.83(10) . 7_565 ? O4 Co1 O4 91.29(10) 7_565 . ? H4C O4 H4D 112(2) . . ? O5 Co1 N1 91.59(7) . 7_565 ? O5 Co1 N1 91.59(7) . . ? O5 Co1 O1 172.20(10) . . ? O5 Co1 O4 85.13(7) . 7_565 ? O5 Co1 O4 85.13(7) . . ? H5A O5 H5B 114(3) . . ? S1 O1 Co1 125.52(14) . . ? # Attachment '100613a_0m.cif' #============================================================================== data_100613a_0m _database_code_depnum_ccdc_archive 'CCDC 819015' #TrackingRef '100613a_0m.cif' #TrackingRef '100613a_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H28 Cl2 Cu N12 O10' _chemical_formula_weight 682.76 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 orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 13.1073(9) _cell_length_b 17.5935(13) _cell_length_c 25.4796(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5875.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3536 _exptl_absorpt_coefficient_mu 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.706 _exptl_absorpt_correction_T_max 0.742 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7488 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1451 _reflns_number_gt 1214 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+8.0686P] 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 1451 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 Cu1 Cu 0.6250 0.6250 0.6250 0.0342(2) Uani 1 4 d S . . Cl1 Cl 0.8750 0.3750 0.63245(4) 0.0559(3) Uani 1 2 d S . . N1 N 0.73366(15) 0.62944(11) 0.68081(8) 0.0411(5) Uani 1 1 d . . . N2 N 0.8691(2) 0.59949(16) 0.72926(15) 0.0766(9) Uani 1 1 d . . . N3 N 0.83081(17) 0.66661(13) 0.74440(8) 0.0485(5) Uani 1 1 d . . . O1 O 0.9361(11) 0.4478(6) 0.6268(5) 0.102(4) Uani 0.384(13) 1 d P . 1 O2 O 0.8750 0.3750 0.6856(3) 0.146(6) Uani 0.77(3) 2 d SP . 1 O3 O 0.9323(9) 0.3260(7) 0.6017(5) 0.063(3) Uani 0.384(13) 1 d P . 1 O4 O 0.7829(9) 0.3925(10) 0.6111(7) 0.115(9) Uani 0.384(13) 1 d P . 1 O1' O 0.7877(15) 0.3750(12) 0.6615(10) 0.138(18) Uani 0.23(3) 1 d P . 2 O2' O 0.885(3) 0.3087(15) 0.6026(11) 0.110(15) Uani 0.23(3) 1 d P . 2 O5 O 0.6250 0.48729(15) 0.6250 0.0575(7) Uani 1 2 d S . . H5 H 0.6766 0.4590 0.6199 0.069 Uiso 1 1 d R . . C1 C 0.8089(2) 0.57971(17) 0.69109(15) 0.0737(10) Uani 1 1 d . . . H1 H 0.8172 0.5347 0.6724 0.088 Uiso 1 1 calc R . . C2 C 0.75021(17) 0.68349(14) 0.71572(9) 0.0410(5) Uani 1 1 d . . . H2 H 0.7108 0.7271 0.7195 0.049 Uiso 1 1 calc R . . C3 C 0.8790(2) 0.7116(2) 0.78585(11) 0.0619(8) Uani 1 1 d . . . H3B H 0.9122 0.6776 0.8105 0.074 Uiso 1 1 calc R . . H3A H 0.8268 0.7395 0.8048 0.074 Uiso 1 1 calc R . . C4 C 0.9568(2) 0.76702(19) 0.76465(12) 0.0671(8) Uani 1 1 d . . . H4A H 0.9221 0.8025 0.7417 0.081 Uiso 1 1 calc R . . H4B H 0.9842 0.7959 0.7938 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0215(3) 0.0409(3) 0.0403(3) 0.000 0.000 0.000 Cl1 0.0486(6) 0.0636(6) 0.0555(6) 0.000 0.000 0.0189(4) N1 0.0302(10) 0.0417(11) 0.0515(12) -0.0016(9) -0.0069(9) -0.0004(8) N2 0.0612(17) 0.0556(15) 0.113(2) -0.0071(17) -0.0452(17) 0.0098(13) N3 0.0404(12) 0.0546(14) 0.0504(12) 0.0027(10) -0.0102(10) -0.0107(11) O1 0.091(8) 0.098(7) 0.118(8) -0.021(6) 0.034(6) -0.038(7) O2 0.187(18) 0.187(8) 0.064(4) 0.000 0.000 -0.034(8) O3 0.032(6) 0.068(7) 0.088(6) -0.026(5) -0.005(6) 0.014(4) O4 0.040(6) 0.148(14) 0.157(19) -0.063(14) -0.019(8) 0.032(7) O1' 0.097(16) 0.17(2) 0.15(4) 0.050(17) 0.06(2) -0.017(13) O2' 0.11(3) 0.105(16) 0.114(19) -0.051(15) -0.05(2) 0.02(2) O5 0.0405(14) 0.0402(14) 0.092(2) 0.000 0.0038(13) 0.000 C1 0.0616(18) 0.0506(17) 0.109(3) -0.0203(17) -0.0439(19) 0.0155(15) C2 0.0352(12) 0.0462(13) 0.0416(12) 0.0006(10) 0.0007(10) -0.0019(11) C3 0.0589(18) 0.081(2) 0.0462(15) -0.0040(14) -0.0095(13) -0.0214(15) C4 0.0620(18) 0.075(2) 0.0645(18) -0.0148(16) -0.0120(15) -0.0195(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.014(2) . ? Cu1 N1 2.0141(19) 11 ? Cu1 N1 2.014(2) 8 ? Cu1 N1 2.0141(19) 14 ? Cu1 O5 2.423(3) . ? Cu1 O5 2.423(3) 14 ? Cl1 O2 1.355(7) . ? Cl1 O4 1.360(11) 2_655 ? Cl1 O4 1.360(11) . ? Cl1 O1' 1.362(15) 2_655 ? Cl1 O1' 1.362(15) . ? Cl1 O3 1.387(9) . ? Cl1 O3 1.387(9) 2_655 ? Cl1 O2' 1.40(2) . ? Cl1 O2' 1.40(2) 2_655 ? Cl1 O1 1.518(9) 2_655 ? Cl1 O1 1.518(9) . ? N1 C2 1.320(3) . ? N1 C1 1.344(3) . ? N2 C1 1.300(4) . ? N2 N3 1.340(4) . ? N3 C2 1.318(3) . ? N3 C3 1.463(3) . ? O1 O4 1.688(19) 2_655 ? O1 O3 1.731(18) 2_655 ? O3 O4 0.758(19) 2_655 ? O3 O1 1.731(18) 2_655 ? O4 O3 0.758(19) 2_655 ? O4 O1 1.688(19) 2_655 ? O5 H5 0.8500 . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.511(4) . ? C3 H3B 0.9700 . ? C3 H3A 0.9700 . ? C4 C4 1.483(6) 21_766 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 175.55(11) . 11 ? N1 Cu1 N1 90.00(12) . 8 ? N1 Cu1 N1 90.18(12) 11 8 ? N1 Cu1 N1 90.18(12) . 14 ? N1 Cu1 N1 90.00(12) 11 14 ? N1 Cu1 N1 175.55(11) 8 14 ? N1 Cu1 O5 92.22(5) . . ? N1 Cu1 O5 92.22(5) 11 . ? N1 Cu1 O5 87.78(5) 8 . ? N1 Cu1 O5 87.78(5) 14 . ? N1 Cu1 O5 87.78(5) . 14 ? N1 Cu1 O5 87.78(5) 11 14 ? N1 Cu1 O5 92.22(5) 8 14 ? N1 Cu1 O5 92.22(5) 14 14 ? O5 Cu1 O5 180.0 . 14 ? O2 Cl1 O4 113.5(7) . 2_655 ? O2 Cl1 O4 113.5(7) . . ? O4 Cl1 O4 132.9(15) 2_655 . ? O2 Cl1 O1' 57.1(12) . 2_655 ? O4 Cl1 O1' 58.0(12) 2_655 2_655 ? O4 Cl1 O1' 164.3(10) . 2_655 ? O2 Cl1 O1' 57.1(12) . . ? O4 Cl1 O1' 164.3(10) 2_655 . ? O4 Cl1 O1' 58.0(12) . . ? O1' Cl1 O1' 114(2) 2_655 . ? O2 Cl1 O3 124.4(5) . . ? O4 Cl1 O3 32.0(8) 2_655 . ? O4 Cl1 O3 113.3(8) . . ? O1' Cl1 O3 81.5(9) 2_655 . ? O1' Cl1 O3 139.6(11) . . ? O2 Cl1 O3 124.4(5) . 2_655 ? O4 Cl1 O3 113.3(8) 2_655 2_655 ? O4 Cl1 O3 32.0(8) . 2_655 ? O1' Cl1 O3 139.6(11) 2_655 2_655 ? O1' Cl1 O3 81.5(9) . 2_655 ? O3 Cl1 O3 111.1(10) . 2_655 ? O2 Cl1 O2' 122.9(13) . . ? O4 Cl1 O2' 60.6(14) 2_655 . ? O4 Cl1 O2' 93.2(10) . . ? O1' Cl1 O2' 102.4(12) 2_655 . ? O1' Cl1 O2' 112.0(19) . . ? O3 Cl1 O2' 28.7(11) . . ? O3 Cl1 O2' 105.2(9) 2_655 . ? O2 Cl1 O2' 122.9(13) . 2_655 ? O4 Cl1 O2' 93.2(10) 2_655 2_655 ? O4 Cl1 O2' 60.6(14) . 2_655 ? O1' Cl1 O2' 112.0(19) 2_655 2_655 ? O1' Cl1 O2' 102.4(12) . 2_655 ? O3 Cl1 O2' 105.2(9) . 2_655 ? O3 Cl1 O2' 28.7(11) 2_655 2_655 ? O2' Cl1 O2' 114(3) . 2_655 ? O2 Cl1 O1 95.5(5) . 2_655 ? O4 Cl1 O1 103.9(9) 2_655 2_655 ? O4 Cl1 O1 71.6(8) . 2_655 ? O1' Cl1 O1 119.6(10) 2_655 2_655 ? O1' Cl1 O1 67.0(11) . 2_655 ? O3 Cl1 O1 73.0(9) . 2_655 ? O3 Cl1 O1 100.7(7) 2_655 2_655 ? O2' Cl1 O1 45.1(17) . 2_655 ? O2' Cl1 O1 127.0(17) 2_655 2_655 ? O2 Cl1 O1 95.5(5) . . ? O4 Cl1 O1 71.6(8) 2_655 . ? O4 Cl1 O1 103.9(9) . . ? O1' Cl1 O1 67.0(11) 2_655 . ? O1' Cl1 O1 119.6(10) . . ? O3 Cl1 O1 100.7(7) . . ? O3 Cl1 O1 73.0(9) 2_655 . ? O2' Cl1 O1 127.0(17) . . ? O2' Cl1 O1 45.1(17) 2_655 . ? O1 Cl1 O1 169.1(9) 2_655 . ? C2 N1 C1 102.5(2) . . ? C2 N1 Cu1 128.31(17) . . ? C1 N1 Cu1 129.14(19) . . ? C1 N2 N3 103.0(2) . . ? C2 N3 N2 109.8(2) . . ? C2 N3 C3 128.6(3) . . ? N2 N3 C3 121.5(2) . . ? Cl1 O1 O4 49.8(5) . 2_655 ? Cl1 O1 O3 50.0(6) . 2_655 ? O4 O1 O3 84.3(8) 2_655 2_655 ? O4 O3 Cl1 72.0(13) 2_655 . ? O4 O3 O1 126.8(16) 2_655 2_655 ? Cl1 O3 O1 57.0(6) . 2_655 ? O3 O4 Cl1 76.0(11) 2_655 . ? O3 O4 O1 128.3(14) 2_655 2_655 ? Cl1 O4 O1 58.5(6) . 2_655 ? Cu1 O5 H5 125.8 . . ? N2 C1 N1 114.6(3) . . ? N2 C1 H1 122.7 . . ? N1 C1 H1 122.7 . . ? N3 C2 N1 110.1(2) . . ? N3 C2 H2 125.0 . . ? N1 C2 H2 125.0 . . ? N3 C3 C4 112.5(2) . . ? N3 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? N3 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? H3B C3 H3A 107.8 . . ? C4 C4 C3 115.8(4) 21_766 . ? C4 C4 H4A 108.3 21_766 . ? C3 C4 H4A 108.3 . . ? C4 C4 H4B 108.3 21_766 . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.481 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.055 # Attachment '100629b_0m.cif' #============================================================================== data_100629b_0m _database_code_depnum_ccdc_archive 'CCDC 819016' #TrackingRef '100629b_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C8H12CuN3O4 _chemical_formula_sum 'C8 H12 Cu N3 O4' _chemical_formula_weight 277.76 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' 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 8.4528(17) _cell_length_b 8.9701(18) _cell_length_c 15.530(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.559(3) _cell_angle_gamma 90.00 _cell_volume 1139.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.066 _cell_measurement_theta_max 0.187 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method ? _exptl_crystal_F_000 714 _exptl_absorpt_coefficient_mu 1.919 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.410 _exptl_absorpt_correction_T_max 25.020 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5380 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2019 _reflns_number_gt 1599 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+0.4216P] 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 2019 _refine_ls_number_parameters 165 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.04700(5) 0.37778(5) 0.46679(2) 0.03748(17) Uani 1 1 d . . . N1 N 0.1326(4) 0.1988(3) 0.3976(2) 0.0430(7) Uani 1 1 d . . . N2 N 0.2130(4) 0.0999(4) 0.2886(2) 0.0581(10) Uani 1 1 d D . . N3 N 0.2093(6) -0.0135(4) 0.3452(3) 0.0739(12) Uani 1 1 d . . . O1 O -0.1567(3) 0.2864(3) 0.48009(17) 0.0504(7) Uani 1 1 d . . . O2 O -0.2338(3) 0.4921(3) 0.53725(18) 0.0504(7) Uani 1 1 d . . . O3 O 0.1534(3) 0.3258(3) 0.59045(17) 0.0537(7) Uani 1 1 d . . . O4 O -0.0791(3) 0.4645(3) 0.35344(15) 0.0471(7) Uani 1 1 d . . . C1 C 0.1675(5) 0.2233(5) 0.3200(3) 0.0486(10) Uani 1 1 d . . . H1 H 0.1605 0.3155 0.2920 0.058 Uiso 1 1 calc R . . C2 C 0.1625(6) 0.0531(5) 0.4097(3) 0.0599(12) Uani 1 1 d . . . H2 H 0.1509 0.0027 0.4601 0.072 Uiso 1 1 calc R . . C3 C 0.2504(18) 0.066(4) 0.2035(10) 0.065(5) Uani 0.50 1 d PD . . H3A H 0.2324 0.1543 0.1659 0.078 Uiso 0.50 1 d PR . . H3B H 0.1789 -0.0121 0.1730 0.078 Uiso 0.50 1 d PR . . C4 C 0.4280(9) 0.0175(10) 0.2203(5) 0.0496(19) Uani 0.50 1 d PD . . H4A H 0.4434 -0.0756 0.2531 0.060 Uiso 0.50 1 d PR . . H4B H 0.4553 0.0011 0.1640 0.060 Uiso 0.50 1 d PR . . C5 C 0.5385(12) 0.1349(11) 0.2726(7) 0.062(3) Uani 0.50 1 d PD . . H5A H 0.5118 0.1504 0.3292 0.074 Uiso 0.50 1 d PR . . H5B H 0.5217 0.2283 0.2401 0.074 Uiso 0.50 1 d PR . . C6 C 0.7170(15) 0.088(4) 0.2888(8) 0.088(11) Uani 0.50 1 d PD . . H6A H 0.7819 0.1481 0.3366 0.105 Uiso 0.50 1 d PR . . H6B H 0.7267 -0.0152 0.3089 0.105 Uiso 0.50 1 d PR . . C7 C -0.2561(4) 0.3615(5) 0.5105(2) 0.0425(9) Uani 1 1 d . . . C8 C -0.4141(5) 0.2884(5) 0.5137(3) 0.0587(11) Uani 1 1 d . . . H8A H -0.4171 0.2747 0.5746 0.088 Uiso 1 1 calc R . . H8B H -0.4225 0.1933 0.4846 0.088 Uiso 1 1 calc R . . H8C H -0.5038 0.3505 0.4840 0.088 Uiso 1 1 calc R . . C9 C 0.1512(5) 0.4129(5) 0.6535(2) 0.0479(10) Uani 1 1 d . . . C10 C 0.2439(7) 0.3637(6) 0.7448(3) 0.0798(16) Uani 1 1 d . . . H10A H 0.2222 0.4313 0.7884 0.120 Uiso 1 1 calc R . . H10B H 0.3589 0.3635 0.7482 0.120 Uiso 1 1 calc R . . H10C H 0.2099 0.2651 0.7561 0.120 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0433(3) 0.0358(3) 0.0343(2) -0.0007(2) 0.01150(18) 0.0094(2) N1 0.0478(18) 0.0384(19) 0.0475(18) -0.0020(15) 0.0208(15) 0.0106(15) N2 0.071(2) 0.067(3) 0.0475(18) 0.0150(19) 0.0360(17) 0.0325(19) N3 0.123(3) 0.053(2) 0.063(2) 0.012(2) 0.054(2) 0.040(2) O1 0.0535(16) 0.0477(16) 0.0554(16) -0.0047(14) 0.0235(13) 0.0008(13) O2 0.0466(16) 0.0458(17) 0.0627(17) -0.0010(14) 0.0210(13) 0.0024(13) O3 0.0721(19) 0.0477(17) 0.0393(14) 0.0035(13) 0.0101(13) 0.0229(14) O4 0.0587(17) 0.0450(16) 0.0366(14) 0.0015(12) 0.0104(12) 0.0154(13) C1 0.053(2) 0.040(2) 0.057(2) 0.0110(19) 0.021(2) 0.0101(19) C2 0.085(3) 0.047(3) 0.062(3) 0.017(2) 0.046(2) 0.024(2) C3 0.046(6) 0.110(13) 0.045(8) 0.004(9) 0.024(5) 0.027(8) C4 0.057(5) 0.048(5) 0.051(5) -0.007(4) 0.027(4) -0.004(4) C5 0.073(11) 0.058(6) 0.070(9) -0.020(5) 0.047(7) -0.023(6) C6 0.095(13) 0.14(2) 0.038(8) -0.037(11) 0.041(8) -0.072(17) C7 0.043(2) 0.046(3) 0.0369(18) 0.0064(19) 0.0075(15) 0.0037(19) C8 0.048(2) 0.058(3) 0.069(3) 0.004(2) 0.014(2) -0.002(2) C9 0.052(2) 0.055(3) 0.037(2) 0.0099(19) 0.0119(17) 0.011(2) C10 0.107(4) 0.084(4) 0.043(2) 0.012(3) 0.008(2) 0.040(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 Cu1 O3 1.961(3) . ? Cu1 O1 1.964(3) . ? Cu1 O4 1.974(2) . ? Cu1 O2 1.977(3) 3_566 ? Cu1 N1 2.156(3) . ? Cu1 Cu1 2.6297(9) 3_566 ? N1 C1 1.328(4) . ? N1 C2 1.335(5) . ? N2 C1 1.305(5) . ? N2 N3 1.350(5) . ? N2 C3 1.466(14) . ? N2 C6 1.472(7) 2_655 ? N3 C2 1.311(5) . ? O1 C7 1.258(4) . ? O2 C7 1.242(5) . ? O2 Cu1 1.977(3) 3_566 ? O3 C9 1.257(4) . ? O4 C9 1.248(4) 3_566 ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C6 0.33(5) 2_655 ? C3 C4 1.522(10) . ? C3 C5 1.83(3) 2_655 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.089(10) 2_655 ? C4 C4 1.330(15) 2_655 ? C4 C6 1.35(2) 2_655 ? C4 C5 1.504(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 0.829(16) 2_655 ? C5 C4 1.089(10) 2_655 ? C5 C6 1.526(10) . ? C5 C3 1.83(3) 2_655 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C3 0.33(5) 2_655 ? C6 C4 1.35(2) 2_655 ? C6 N2 1.472(7) 2_655 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.500(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O4 1.248(4) 3_566 ? C9 C10 1.503(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O1 89.78(12) . . ? O3 Cu1 O4 168.18(10) . . ? O1 Cu1 O4 88.11(11) . . ? O3 Cu1 O2 89.89(12) . 3_566 ? O1 Cu1 O2 167.92(11) . 3_566 ? O4 Cu1 O2 89.75(12) . 3_566 ? O3 Cu1 N1 100.52(11) . . ? O1 Cu1 N1 98.90(12) . . ? O4 Cu1 N1 91.30(11) . . ? O2 Cu1 N1 93.03(12) 3_566 . ? O3 Cu1 Cu1 85.61(8) . 3_566 ? O1 Cu1 Cu1 86.99(8) . 3_566 ? O4 Cu1 Cu1 82.67(7) . 3_566 ? O2 Cu1 Cu1 80.95(8) 3_566 3_566 ? N1 Cu1 Cu1 171.46(9) . 3_566 ? C1 N1 C2 102.3(3) . . ? C1 N1 Cu1 120.5(3) . . ? C2 N1 Cu1 137.2(3) . . ? C1 N2 N3 109.8(3) . . ? C1 N2 C3 131.4(15) . . ? N3 N2 C3 118.5(16) . . ? C1 N2 C6 125.9(13) . 2_655 ? N3 N2 C6 123.7(13) . 2_655 ? C3 N2 C6 12.9(19) . 2_655 ? C2 N3 N2 102.4(3) . . ? C7 O1 Cu1 120.1(3) . . ? C7 O2 Cu1 127.0(2) . 3_566 ? C9 O3 Cu1 121.5(2) . . ? C9 O4 Cu1 124.5(2) 3_566 . ? N2 C1 N1 110.6(3) . . ? N2 C1 H1 124.7 . . ? N1 C1 H1 124.7 . . ? N3 C2 N1 114.9(4) . . ? N3 C2 H2 122.6 . . ? N1 C2 H2 122.6 . . ? C6 C3 N2 85(4) 2_655 . ? C6 C3 C4 54(8) 2_655 . ? N2 C3 C4 109.3(10) . . ? C6 C3 C5 19(6) 2_655 2_655 ? N2 C3 C5 99.6(13) . 2_655 ? C4 C3 C5 36.4(6) . 2_655 ? C6 C3 H3A 74.9 2_655 . ? N2 C3 H3A 109.8 . . ? C4 C3 H3A 109.7 . . ? C5 C3 H3A 81.2 2_655 . ? C6 C3 H3B 162.3 2_655 . ? N2 C3 H3B 109.8 . . ? C4 C3 H3B 110.0 . . ? C5 C3 H3B 142.9 2_655 . ? H3A C3 H3B 108.2 . . ? C5 C4 C4 76.1(6) 2_655 2_655 ? C5 C4 C6 76.5(13) 2_655 2_655 ? C4 C4 C6 136.1(10) 2_655 2_655 ? C5 C4 C5 32.6(7) 2_655 . ? C4 C4 C5 44.7(4) 2_655 . ? C6 C4 C5 98.9(14) 2_655 . ? C5 C4 C3 87.6(18) 2_655 . ? C4 C4 C3 144.2(11) 2_655 . ? C6 C4 C3 11(3) 2_655 . ? C5 C4 C3 110.1(13) . . ? C5 C4 H4A 141.5 2_655 . ? C4 C4 H4A 69.9 2_655 . ? C6 C4 H4A 117.0 2_655 . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 97.1 2_655 . ? C4 C4 H4B 104.0 2_655 . ? C6 C4 H4B 113.0 2_655 . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C5 C5 C4 102.4(7) 2_655 2_655 ? C5 C5 C4 45.0(5) 2_655 . ? C4 C5 C4 59.2(8) 2_655 . ? C5 C5 C6 132(2) 2_655 . ? C4 C5 C6 59.6(13) 2_655 . ? C4 C5 C6 110.4(11) . . ? C5 C5 C3 134(2) 2_655 2_655 ? C4 C5 C3 56.0(13) 2_655 2_655 ? C4 C5 C3 108.4(14) . 2_655 ? C6 C5 C3 4.1(18) . 2_655 ? C5 C5 H5A 117.1 2_655 . ? C4 C5 H5A 99.2 2_655 . ? C4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? C3 C5 H5A 107.5 2_655 . ? C5 C5 H5B 65.1 2_655 . ? C4 C5 H5B 152.6 2_655 . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.6 . . ? C3 C5 H5B 113.7 2_655 . ? H5A C5 H5B 108.1 . . ? C3 C6 C4 115(10) 2_655 2_655 ? C3 C6 N2 83(3) 2_655 2_655 ? C4 C6 N2 119.2(14) 2_655 2_655 ? C3 C6 C5 156(8) 2_655 . ? C4 C6 C5 43.9(5) 2_655 . ? N2 C6 C5 115.3(11) 2_655 . ? C3 C6 H6A 77.7 2_655 . ? C4 C6 H6A 131.6 2_655 . ? N2 C6 H6A 108.5 2_655 . ? C5 C6 H6A 108.4 . . ? C3 C6 H6B 48.9 2_655 . ? C4 C6 H6B 66.0 2_655 . ? N2 C6 H6B 108.4 2_655 . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? O2 C7 O1 124.8(4) . . ? O2 C7 C8 117.6(4) . . ? O1 C7 C8 117.6(4) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O4 C9 O3 125.6(3) 3_566 . ? O4 C9 C10 117.9(4) 3_566 . ? O3 C9 C10 116.5(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.326 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.062 # Attachment '795368.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 823004' #TrackingRef '795368.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Co N9 O5' _chemical_formula_weight 529.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9762(7) _cell_length_b 11.3964(8) _cell_length_c 12.7958(14) _cell_angle_alpha 107.1730(10) _cell_angle_beta 103.271(2) _cell_angle_gamma 104.5450(10) _cell_volume 1143.39(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2045 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.804 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7662 _exptl_absorpt_correction_T_max 0.9027 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5785 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4107 _reflns_number_gt 3404 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.8510P] 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 4107 _refine_ls_number_parameters 356 _refine_ls_number_restraints 167 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.048 _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 0.2978(3) 0.1801(3) 0.9734(3) 0.0306(7) Uani 1 1 d . A . H1 H 0.2839 0.2534 1.0241 0.037 Uiso 1 1 calc R . . C2 C 0.2710(4) -0.0084(3) 0.8708(3) 0.0330(7) Uani 1 1 d . . . H2 H 0.2288 -0.1009 0.8331 0.040 Uiso 1 1 calc R . . C3 C 0.5259(7) 0.2986(6) 0.9128(5) 0.0268(13) Uani 0.537(5) 1 d PDU A 1 H3A H 0.6353 0.2904 0.9270 0.032 Uiso 0.537(5) 1 calc PR A 1 H3B H 0.5359 0.3801 0.9740 0.032 Uiso 0.537(5) 1 calc PR A 1 C4 C 0.4764(7) 0.3134(6) 0.7962(5) 0.0271(13) Uani 0.537(5) 1 d PDU A 1 H4A H 0.3793 0.3407 0.7877 0.032 Uiso 0.537(5) 1 calc PR A 1 H4B H 0.4474 0.2282 0.7328 0.032 Uiso 0.537(5) 1 calc PR A 1 C5 C 0.6160(6) 0.4151(5) 0.7875(5) 0.0289(12) Uani 0.537(5) 1 d PDU A 1 H5A H 0.6458 0.4988 0.8530 0.035 Uiso 0.537(5) 1 calc PR A 1 H5B H 0.7120 0.3864 0.7964 0.035 Uiso 0.537(5) 1 calc PR A 1 C6 C 0.5795(7) 0.4393(7) 0.6756(5) 0.0322(11) Uani 0.537(5) 1 d PDU A 1 H6A H 0.6743 0.5057 0.6751 0.039 Uiso 0.537(5) 1 calc PR A 1 H6B H 0.5484 0.3577 0.6077 0.039 Uiso 0.537(5) 1 calc PR A 1 C3' C 0.5679(8) 0.2969(7) 0.9660(6) 0.0322(17) Uani 0.463(5) 1 d PDU A 2 H3'1 H 0.6595 0.2646 0.9606 0.039 Uiso 0.463(5) 1 calc PR A 2 H3'2 H 0.5915 0.3529 1.0476 0.039 Uiso 0.463(5) 1 calc PR A 2 C4' C 0.5466(8) 0.3747(6) 0.8884(5) 0.0296(14) Uani 0.463(5) 1 d PDU A 2 H4'1 H 0.4487 0.3992 0.8907 0.036 Uiso 0.463(5) 1 calc PR A 2 H4'2 H 0.6416 0.4568 0.9219 0.036 Uiso 0.463(5) 1 calc PR A 2 C5' C 0.5294(9) 0.3073(6) 0.7628(5) 0.0264(14) Uani 0.463(5) 1 d PDU A 2 H5'1 H 0.4181 0.2422 0.7219 0.032 Uiso 0.463(5) 1 calc PR A 2 H5'2 H 0.6075 0.2597 0.7592 0.032 Uiso 0.463(5) 1 calc PR A 2 C6' C 0.5600(9) 0.4030(7) 0.6990(7) 0.0322(11) Uani 0.463(5) 1 d PDU A 2 H6'A H 0.5616 0.3511 0.6223 0.039 Uiso 0.463(5) 1 calc PR A 2 H6'B H 0.6718 0.4663 0.7422 0.039 Uiso 0.463(5) 1 calc PR A 2 C7 C 0.3174(4) 0.4513(3) 0.5889(3) 0.0362(7) Uani 1 1 d . A . H7 H 0.2851 0.3788 0.5182 0.043 Uiso 1 1 calc R . . C8 C 0.3305(5) 0.6172(3) 0.7203(3) 0.0544(11) Uani 1 1 d . A . H8 H 0.3040 0.6889 0.7615 0.065 Uiso 1 1 calc R . . C9 C 0.2926(3) 0.0437(3) 1.2073(2) 0.0223(6) Uani 1 1 d . . . H9 H 0.3105 -0.0294 1.1597 0.027 Uiso 1 1 calc R . . C10 C 0.2005(4) 0.1916(3) 1.2694(2) 0.0281(6) Uani 1 1 d . . . H10 H 0.1346 0.2452 1.2717 0.034 Uiso 1 1 calc R . . C11 C 0.5078(3) 0.0904(3) 1.3936(2) 0.0264(6) Uani 1 1 d . . . H11A H 0.5909 0.1749 1.4492 0.032 Uiso 1 1 calc R . . H11B H 0.5619 0.0409 1.3472 0.032 Uiso 1 1 calc R . . C12 C 0.4351(3) 0.0131(3) 1.4599(2) 0.0268(6) Uani 1 1 d . . . H12A H 0.3806 0.0626 1.5059 0.032 Uiso 1 1 calc R . . H12B H 0.3518 -0.0712 1.4041 0.032 Uiso 1 1 calc R . . C13 C 0.0477(3) -0.2739(2) 0.9329(2) 0.0200(6) Uani 1 1 d . . . C14 C 0.0240(3) -0.3908(2) 0.9689(2) 0.0162(5) Uani 1 1 d . . . C15 C 0.0447(4) -0.5033(3) 0.9034(2) 0.0267(6) Uani 1 1 d . . . H15 H 0.0763 -0.5058 0.8371 0.032 Uiso 1 1 calc R . . C16 C -0.0196(3) -0.3881(2) 1.0659(2) 0.0214(6) Uani 1 1 d . . . H16 H -0.0326 -0.3115 1.1120 0.026 Uiso 1 1 calc R . . C17 C -0.0620(3) 0.2458(3) 0.5409(2) 0.0268(6) Uani 1 1 d . A . C18 C -0.0296(3) 0.1185(2) 0.5196(2) 0.0224(6) Uani 1 1 d . . . C19 C -0.0001(4) 0.0711(3) 0.6081(2) 0.0270(6) Uani 1 1 d . . . H19 H 0.0001 0.1194 0.6827 0.032 Uiso 1 1 calc R . . C20 C 0.0289(4) -0.0458(3) 0.5883(2) 0.0287(6) Uani 1 1 d . . . H20 H 0.0488 -0.0768 0.6496 0.034 Uiso 1 1 calc R . . Co1 Co 0.0000 0.0000 1.0000 0.01453(13) Uani 1 2 d S . . Co2 Co 0.0000 0.5000 0.5000 0.03599(18) Uani 1 2 d S . . N1 N 0.2029(3) 0.0576(2) 0.94026(18) 0.0202(5) Uani 1 1 d . . . N2 N 0.4153(3) 0.1867(2) 0.9260(2) 0.0304(6) Uani 1 1 d D . . N3 N 0.4010(3) 0.0651(2) 0.8590(2) 0.0334(6) Uani 1 1 d . A . N4 N 0.4491(3) 0.4847(3) 0.6767(2) 0.0457(8) Uani 1 1 d D . . N5 N 0.2355(4) 0.5319(2) 0.6117(2) 0.0396(7) Uani 1 1 d . . . N6 N 0.4607(4) 0.5935(3) 0.7636(3) 0.0678(11) Uani 1 1 d . A . N7 N 0.1763(3) 0.0891(2) 1.17307(17) 0.0194(5) Uani 1 1 d . . . N8 N 0.3809(3) 0.1144(2) 1.31733(18) 0.0224(5) Uani 1 1 d . . . N9 N 0.3225(3) 0.2109(2) 1.3595(2) 0.0317(6) Uani 1 1 d . . . O1 O 0.0302(2) -0.17543(16) 0.99881(15) 0.0206(4) Uani 1 1 d . . . O2 O 0.0826(3) -0.28288(18) 0.84303(17) 0.0325(5) Uani 1 1 d . . . O3 O -0.0514(3) 0.29729(18) 0.46677(17) 0.0327(5) Uani 1 1 d . . . O4 O -0.0980(3) 0.29084(19) 0.62965(18) 0.0375(5) Uani 1 1 d . . . O6 O -0.0941(3) 0.5229(2) 0.63666(19) 0.0401(6) Uani 1 1 d D . . H6C H -0.036(4) 0.580(2) 0.704(2) 0.060 Uiso 1 1 d D . . H6D H -0.105(4) 0.4471(19) 0.641(3) 0.060 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 0.0288(16) 0.0213(14) 0.0357(17) 0.0009(13) 0.0169(13) 0.0048(12) C2 0.0417(18) 0.0203(14) 0.0460(18) 0.0128(13) 0.0272(15) 0.0132(13) C3 0.022(3) 0.027(3) 0.031(3) 0.013(3) 0.010(2) 0.003(2) C4 0.021(3) 0.028(3) 0.033(3) 0.015(2) 0.010(2) 0.005(2) C5 0.019(2) 0.030(2) 0.040(3) 0.020(2) 0.010(2) 0.0062(19) C6 0.0241(17) 0.041(2) 0.033(2) 0.0119(16) 0.0240(16) 0.0027(17) C3' 0.026(3) 0.039(3) 0.027(3) 0.017(3) 0.005(3) 0.001(3) C4' 0.029(3) 0.031(3) 0.028(3) 0.014(2) 0.009(2) 0.007(2) C5' 0.029(3) 0.030(3) 0.026(3) 0.013(2) 0.011(2) 0.013(2) C6' 0.0241(17) 0.041(2) 0.033(2) 0.0119(16) 0.0240(16) 0.0027(17) C7 0.0454(19) 0.0257(16) 0.0331(17) 0.0023(13) 0.0208(15) 0.0083(14) C8 0.059(3) 0.0274(18) 0.066(3) -0.0046(17) 0.044(2) 0.0023(17) C9 0.0257(14) 0.0211(13) 0.0197(14) 0.0055(11) 0.0071(11) 0.0102(11) C10 0.0453(18) 0.0241(14) 0.0202(14) 0.0078(12) 0.0116(13) 0.0204(13) C11 0.0236(14) 0.0335(16) 0.0200(14) 0.0082(12) 0.0044(11) 0.0110(12) C12 0.0236(14) 0.0350(16) 0.0218(14) 0.0115(13) 0.0050(12) 0.0113(12) C13 0.0214(13) 0.0142(13) 0.0255(14) 0.0095(11) 0.0075(11) 0.0056(10) C14 0.0157(12) 0.0134(12) 0.0200(13) 0.0066(10) 0.0046(10) 0.0064(10) C15 0.0464(18) 0.0210(14) 0.0263(15) 0.0136(12) 0.0215(13) 0.0197(13) C16 0.0319(15) 0.0138(12) 0.0226(14) 0.0069(11) 0.0105(12) 0.0130(11) C17 0.0296(15) 0.0185(14) 0.0328(16) 0.0091(12) 0.0110(13) 0.0088(12) C18 0.0218(14) 0.0164(13) 0.0291(15) 0.0094(11) 0.0092(11) 0.0049(11) C19 0.0378(16) 0.0226(14) 0.0213(14) 0.0067(12) 0.0107(12) 0.0125(13) C20 0.0405(17) 0.0246(15) 0.0266(15) 0.0138(12) 0.0113(13) 0.0151(13) Co1 0.0215(3) 0.0106(2) 0.0160(3) 0.00696(19) 0.0088(2) 0.00809(19) Co2 0.0662(4) 0.0254(3) 0.0413(4) 0.0212(3) 0.0374(3) 0.0280(3) N1 0.0239(12) 0.0199(11) 0.0202(11) 0.0091(9) 0.0106(9) 0.0083(9) N2 0.0272(13) 0.0218(12) 0.0406(15) 0.0070(11) 0.0178(11) 0.0054(10) N3 0.0392(15) 0.0256(13) 0.0454(16) 0.0144(12) 0.0270(13) 0.0145(11) N4 0.0292(15) 0.0404(16) 0.0436(16) -0.0134(13) 0.0199(13) 0.0002(12) N5 0.0623(19) 0.0247(13) 0.0443(16) 0.0132(12) 0.0353(14) 0.0190(13) N6 0.0382(18) 0.056(2) 0.065(2) -0.0297(17) 0.0280(17) -0.0043(16) N7 0.0247(12) 0.0172(11) 0.0183(11) 0.0067(9) 0.0076(9) 0.0098(9) N8 0.0267(12) 0.0226(12) 0.0191(11) 0.0076(10) 0.0068(10) 0.0111(10) N9 0.0484(16) 0.0247(13) 0.0207(12) 0.0040(10) 0.0074(11) 0.0194(12) O1 0.0298(10) 0.0130(9) 0.0237(10) 0.0096(8) 0.0096(8) 0.0111(8) O2 0.0605(14) 0.0219(10) 0.0358(12) 0.0183(9) 0.0333(11) 0.0231(10) O3 0.0545(14) 0.0257(11) 0.0359(11) 0.0201(9) 0.0259(10) 0.0228(10) O4 0.0638(15) 0.0231(10) 0.0401(12) 0.0151(9) 0.0318(11) 0.0212(10) O6 0.0738(17) 0.0267(11) 0.0440(13) 0.0206(10) 0.0408(13) 0.0288(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 N1 1.319(3) . ? C1 N2 1.329(4) . ? C1 H1 0.9500 . ? C2 N3 1.323(4) . ? C2 N1 1.347(4) . ? C2 H2 0.9500 . ? C3 N2 1.486(5) . ? C3 C4 1.527(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.529(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.516(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N4 1.395(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C3' N2 1.466(6) . ? C3' C4' 1.524(7) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.515(7) . ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C5' C6' 1.552(7) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' N4 1.560(7) . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C7 N4 1.310(4) . ? C7 N5 1.323(4) . ? C7 H7 0.9500 . ? C8 N6 1.302(5) . ? C8 N5 1.357(5) . ? C8 H8 0.9500 . ? C9 N7 1.321(3) . ? C9 N8 1.326(3) . ? C9 H9 0.9500 . ? C10 N9 1.314(4) . ? C10 N7 1.353(3) . ? C10 H10 0.9500 . ? C11 N8 1.458(3) . ? C11 C12 1.526(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C12 1.519(5) 2_658 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O2 1.242(3) . ? C13 O1 1.260(3) . ? C13 C14 1.515(3) . ? C14 C16 1.380(4) . ? C14 C15 1.392(4) . ? C15 C16 1.386(4) 2_547 ? C15 H15 0.9500 . ? C16 C15 1.386(4) 2_547 ? C16 H16 0.9500 . ? C17 O4 1.250(3) . ? C17 O3 1.263(3) . ? C17 C18 1.510(4) . ? C18 C20 1.387(4) 2_556 ? C18 C19 1.393(4) . ? C19 C20 1.382(4) . ? C19 H19 0.9500 . ? C20 C18 1.387(4) 2_556 ? C20 H20 0.9500 . ? Co1 O1 2.0801(16) 2_557 ? Co1 O1 2.0801(16) . ? Co1 N1 2.161(2) 2_557 ? Co1 N1 2.161(2) . ? Co1 N7 2.167(2) . ? Co1 N7 2.167(2) 2_557 ? Co2 O6 2.088(2) . ? Co2 O6 2.088(2) 2_566 ? Co2 O3 2.1273(18) 2_566 ? Co2 O3 2.1273(18) . ? Co2 N5 2.136(3) 2_566 ? Co2 N5 2.136(3) . ? N2 N3 1.353(3) . ? N4 N6 1.361(4) . ? N8 N9 1.359(3) . ? O6 H6C 0.858(18) . ? O6 H6D 0.862(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 110.6(2) . . ? N1 C1 H1 124.7 . . ? N2 C1 H1 124.7 . . ? N3 C2 N1 115.1(3) . . ? N3 C2 H2 122.5 . . ? N1 C2 H2 122.5 . . ? N2 C3 C4 116.7(4) . . ? N2 C3 H3A 108.1 . . ? C4 C3 H3A 108.1 . . ? N2 C3 H3B 108.1 . . ? C4 C3 H3B 108.1 . . ? H3A C3 H3B 107.3 . . ? C3 C4 C5 110.4(4) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 115.0(5) . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5B 108.5 . . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? N4 C6 C5 102.7(4) . . ? N4 C6 H6A 111.2 . . ? C5 C6 H6A 111.2 . . ? N4 C6 H6B 111.2 . . ? C5 C6 H6B 111.2 . . ? H6A C6 H6B 109.1 . . ? N2 C3' C4' 107.4(5) . . ? N2 C3' H3'1 110.2 . . ? C4' C3' H3'1 110.2 . . ? N2 C3' H3'2 110.2 . . ? C4' C3' H3'2 110.2 . . ? H3'1 C3' H3'2 108.5 . . ? C5' C4' C3' 116.5(6) . . ? C5' C4' H4'1 108.2 . . ? C3' C4' H4'1 108.2 . . ? C5' C4' H4'2 108.2 . . ? C3' C4' H4'2 108.2 . . ? H4'1 C4' H4'2 107.3 . . ? C4' C5' C6' 113.4(6) . . ? C4' C5' H5'1 108.9 . . ? C6' C5' H5'1 108.9 . . ? C4' C5' H5'2 108.9 . . ? C6' C5' H5'2 108.9 . . ? H5'1 C5' H5'2 107.7 . . ? C5' C6' N4 123.3(5) . . ? C5' C6' H6'A 106.5 . . ? N4 C6' H6'A 106.5 . . ? C5' C6' H6'B 106.5 . . ? N4 C6' H6'B 106.5 . . ? H6'A C6' H6'B 106.5 . . ? N4 C7 N5 111.0(3) . . ? N4 C7 H7 124.5 . . ? N5 C7 H7 124.5 . . ? N6 C8 N5 115.0(3) . . ? N6 C8 H8 122.5 . . ? N5 C8 H8 122.5 . . ? N7 C9 N8 110.5(2) . . ? N7 C9 H9 124.8 . . ? N8 C9 H9 124.8 . . ? N9 C10 N7 114.5(2) . . ? N9 C10 H10 122.7 . . ? N7 C10 H10 122.7 . . ? N8 C11 C12 110.5(2) . . ? N8 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N8 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C12 C12 C11 111.5(3) 2_658 . ? C12 C12 H12A 109.3 2_658 . ? C11 C12 H12A 109.3 . . ? C12 C12 H12B 109.3 2_658 . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? O2 C13 O1 126.1(2) . . ? O2 C13 C14 118.2(2) . . ? O1 C13 C14 115.8(2) . . ? C16 C14 C15 119.0(2) . . ? C16 C14 C13 120.8(2) . . ? C15 C14 C13 120.2(2) . . ? C16 C15 C14 120.7(2) 2_547 . ? C16 C15 H15 119.7 2_547 . ? C14 C15 H15 119.7 . . ? C14 C16 C15 120.4(2) . 2_547 ? C14 C16 H16 119.8 . . ? C15 C16 H16 119.8 2_547 . ? O4 C17 O3 125.6(3) . . ? O4 C17 C18 117.5(2) . . ? O3 C17 C18 116.9(2) . . ? C20 C18 C19 118.4(2) 2_556 . ? C20 C18 C17 121.0(2) 2_556 . ? C19 C18 C17 120.6(2) . . ? C20 C19 C18 120.5(3) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C18 121.1(3) . 2_556 ? C19 C20 H20 119.5 . . ? C18 C20 H20 119.5 2_556 . ? O1 Co1 O1 180.000(1) 2_557 . ? O1 Co1 N1 94.23(7) 2_557 2_557 ? O1 Co1 N1 85.77(7) . 2_557 ? O1 Co1 N1 85.77(7) 2_557 . ? O1 Co1 N1 94.23(7) . . ? N1 Co1 N1 180.000(1) 2_557 . ? O1 Co1 N7 93.43(7) 2_557 . ? O1 Co1 N7 86.57(7) . . ? N1 Co1 N7 93.46(8) 2_557 . ? N1 Co1 N7 86.54(8) . . ? O1 Co1 N7 86.57(7) 2_557 2_557 ? O1 Co1 N7 93.43(7) . 2_557 ? N1 Co1 N7 86.54(8) 2_557 2_557 ? N1 Co1 N7 93.46(8) . 2_557 ? N7 Co1 N7 180.0 . 2_557 ? O6 Co2 O6 180.000(1) . 2_566 ? O6 Co2 O3 88.87(8) . 2_566 ? O6 Co2 O3 91.13(8) 2_566 2_566 ? O6 Co2 O3 91.13(8) . . ? O6 Co2 O3 88.87(8) 2_566 . ? O3 Co2 O3 180.0 2_566 . ? O6 Co2 N5 88.45(10) . 2_566 ? O6 Co2 N5 91.55(10) 2_566 2_566 ? O3 Co2 N5 87.18(9) 2_566 2_566 ? O3 Co2 N5 92.82(9) . 2_566 ? O6 Co2 N5 91.55(10) . . ? O6 Co2 N5 88.45(10) 2_566 . ? O3 Co2 N5 92.82(9) 2_566 . ? O3 Co2 N5 87.18(9) . . ? N5 Co2 N5 180.000(1) 2_566 . ? C1 N1 C2 102.5(2) . . ? C1 N1 Co1 123.39(18) . . ? C2 N1 Co1 134.04(18) . . ? C1 N2 N3 109.8(2) . . ? C1 N2 C3' 126.2(4) . . ? N3 N2 C3' 121.2(4) . . ? C1 N2 C3 131.2(3) . . ? N3 N2 C3 117.2(3) . . ? C3' N2 C3 27.7(3) . . ? C2 N3 N2 102.0(2) . . ? C7 N4 N6 109.7(3) . . ? C7 N4 C6 126.6(4) . . ? N6 N4 C6 122.1(4) . . ? C7 N4 C6' 128.3(4) . . ? N6 N4 C6' 120.5(4) . . ? C6 N4 C6' 22.3(3) . . ? C7 N5 C8 101.9(3) . . ? C7 N5 Co2 123.1(2) . . ? C8 N5 Co2 134.6(2) . . ? C8 N6 N4 102.3(3) . . ? C9 N7 C10 102.8(2) . . ? C9 N7 Co1 122.83(17) . . ? C10 N7 Co1 134.33(18) . . ? C9 N8 N9 109.6(2) . . ? C9 N8 C11 129.0(2) . . ? N9 N8 C11 120.9(2) . . ? C10 N9 N8 102.6(2) . . ? C13 O1 Co1 139.94(16) . . ? C17 O3 Co2 124.89(18) . . ? Co2 O6 H6C 120(3) . . ? Co2 O6 H6D 99(2) . . ? H6C O6 H6D 107(2) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.378 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.062