# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_si210312_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 N4 S' _chemical_formula_weight 216.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.5026(2) _cell_length_b 19.8758(4) _cell_length_c 9.4612(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.0530(10) _cell_angle_gamma 90.00 _cell_volume 1963.99(7) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5678 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 30.56 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9293 _exptl_absorpt_correction_T_max 0.9824 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source Microfocus _diffrn_radiation_monochromator 'Quazar Mo multilayer optic' _diffrn_measurement_device_type 'APEX-II CCD-detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16440 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 30.06 _reflns_number_total 2877 _reflns_number_gt 2397 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2012.2-0' _computing_cell_refinement 'SAINT V8.18C (Bruker AXS Inc.)' _computing_data_reduction "'SAINT V8.18C (Bruker AXS Inc.)" _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0657P)^2^+1.2674P] 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 2877 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 S1 S 0.74072(4) 0.577667(18) 0.80675(4) 0.03232(13) Uani 1 1 d . . . C1 C 0.79382(15) 0.50594(7) 0.73255(18) 0.0326(3) Uani 1 1 d . . . H1 H 0.7749 0.4618 0.7629 0.039 Uiso 1 1 calc R . . C2 C 0.86603(14) 0.51926(7) 0.62542(16) 0.0297(3) Uani 1 1 d . . . H2 H 0.9037 0.4854 0.5725 0.036 Uiso 1 1 calc R . . C3 C 0.87948(13) 0.58921(7) 0.60057(15) 0.0256(3) Uani 1 1 d . . . H3 H 0.9270 0.6074 0.5295 0.031 Uiso 1 1 calc R . . C4 C 0.81539(12) 0.62763(7) 0.69170(14) 0.0220(3) Uani 1 1 d . . . C5 C 0.80647(12) 0.70036(6) 0.70021(13) 0.0207(2) Uani 1 1 d . . . N1 N 0.72729(11) 0.72681(6) 0.78890(12) 0.0240(2) Uani 1 1 d . . . C6 C 0.71969(13) 0.79399(7) 0.79945(15) 0.0266(3) Uani 1 1 d . . . H6 H 0.6626 0.8105 0.8628 0.032 Uiso 1 1 calc R . . N2 N 0.78245(11) 0.84067(6) 0.73183(13) 0.0254(2) Uani 1 1 d . . . C7 C 0.85890(12) 0.81279(6) 0.64459(14) 0.0210(2) Uani 1 1 d . . . C8 C 0.87618(12) 0.74389(6) 0.62234(13) 0.0203(2) Uani 1 1 d . . . N3 N 0.96451(11) 0.73349(6) 0.52490(12) 0.0242(2) Uani 1 1 d . . . C9 C 0.99754(13) 0.79470(7) 0.49201(15) 0.0254(3) Uani 1 1 d . . . H9 H 1.0580 0.8036 0.4265 0.030 Uiso 1 1 calc R . . N4 N 0.93783(11) 0.84473(6) 0.55972(12) 0.0234(2) Uani 1 1 d . . . C10 C 0.95836(15) 0.91658(7) 0.54693(17) 0.0299(3) Uani 1 1 d . . . H10A H 0.8859 0.9410 0.5798 0.045 Uiso 1 1 calc R . . H10C H 0.9656 0.9279 0.4473 0.045 Uiso 1 1 calc R . . H10B H 1.0374 0.9294 0.6050 0.045 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 S1 0.0420(2) 0.02265(19) 0.0350(2) 0.00598(13) 0.01701(16) 0.00063(13) C1 0.0384(8) 0.0200(6) 0.0399(8) 0.0051(6) 0.0065(6) 0.0006(5) C2 0.0332(7) 0.0208(6) 0.0353(7) -0.0024(5) 0.0047(6) 0.0033(5) C3 0.0281(6) 0.0211(6) 0.0283(6) 0.0009(5) 0.0065(5) 0.0005(5) C4 0.0233(6) 0.0196(6) 0.0235(6) 0.0027(4) 0.0041(5) 0.0004(4) C5 0.0213(5) 0.0198(6) 0.0210(6) 0.0004(4) 0.0030(4) 0.0002(4) N1 0.0248(5) 0.0217(5) 0.0271(5) 0.0001(4) 0.0098(4) -0.0001(4) C6 0.0285(6) 0.0224(6) 0.0308(7) -0.0020(5) 0.0123(5) 0.0002(5) N2 0.0259(5) 0.0216(5) 0.0300(6) -0.0021(4) 0.0088(5) -0.0008(4) C7 0.0201(5) 0.0205(6) 0.0228(6) 0.0001(4) 0.0045(5) -0.0019(4) C8 0.0202(5) 0.0201(6) 0.0211(5) 0.0000(4) 0.0048(4) 0.0012(4) N3 0.0248(5) 0.0238(5) 0.0255(5) 0.0008(4) 0.0097(4) 0.0016(4) C9 0.0253(6) 0.0262(6) 0.0262(6) 0.0018(5) 0.0097(5) 0.0003(5) N4 0.0233(5) 0.0203(5) 0.0275(5) 0.0024(4) 0.0074(4) -0.0021(4) C10 0.0323(7) 0.0210(6) 0.0375(8) 0.0033(5) 0.0085(6) -0.0052(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.7085(16) . ? S1 C4 1.7222(13) . ? C1 C2 1.355(2) . ? C1 H1 0.9500 . ? C2 C3 1.4197(18) . ? C2 H2 0.9500 . ? C3 C4 1.3790(19) . ? C3 H3 0.9500 . ? C4 C5 1.4514(18) . ? C5 N1 1.3488(16) . ? C5 C8 1.3932(17) . ? N1 C6 1.3421(18) . ? C6 N2 1.3391(18) . ? C6 H6 0.9500 . ? N2 C7 1.3315(17) . ? C7 N4 1.3694(16) . ? C7 C8 1.4003(17) . ? C8 N3 1.3906(16) . ? N3 C9 1.3116(18) . ? C9 N4 1.3701(18) . ? C9 H9 0.9500 . ? N4 C10 1.4513(17) . ? C10 H10A 0.9800 . ? C10 H10C 0.9800 . ? C10 H10B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 91.79(7) . . ? C2 C1 S1 112.16(11) . . ? C2 C1 H1 123.9 . . ? S1 C1 H1 123.9 . . ? C1 C2 C3 112.87(13) . . ? C1 C2 H2 123.6 . . ? C3 C2 H2 123.6 . . ? C4 C3 C2 112.03(13) . . ? C4 C3 H3 124.0 . . ? C2 C3 H3 124.0 . . ? C3 C4 C5 128.66(12) . . ? C3 C4 S1 111.15(10) . . ? C5 C4 S1 120.19(10) . . ? N1 C5 C8 118.67(12) . . ? N1 C5 C4 118.06(12) . . ? C8 C5 C4 123.27(12) . . ? C6 N1 C5 118.65(11) . . ? N2 C6 N1 128.14(13) . . ? N2 C6 H6 115.9 . . ? N1 C6 H6 115.9 . . ? C7 N2 C6 111.55(12) . . ? N2 C7 N4 127.77(12) . . ? N2 C7 C8 126.61(12) . . ? N4 C7 C8 105.61(11) . . ? N3 C8 C5 133.06(12) . . ? N3 C8 C7 110.56(11) . . ? C5 C8 C7 116.37(11) . . ? C9 N3 C8 103.35(11) . . ? N3 C9 N4 114.63(12) . . ? N3 C9 H9 122.7 . . ? N4 C9 H9 122.7 . . ? C7 N4 C9 105.84(11) . . ? C7 N4 C10 127.56(12) . . ? C9 N4 C10 126.57(12) . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? 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 C4 S1 C1 C2 0.40(13) . . . . ? S1 C1 C2 C3 -0.26(18) . . . . ? C1 C2 C3 C4 -0.07(19) . . . . ? C2 C3 C4 C5 179.79(13) . . . . ? C2 C3 C4 S1 0.37(15) . . . . ? C1 S1 C4 C3 -0.44(11) . . . . ? C1 S1 C4 C5 -179.91(11) . . . . ? C3 C4 C5 N1 173.40(13) . . . . ? S1 C4 C5 N1 -7.22(16) . . . . ? C3 C4 C5 C8 -7.1(2) . . . . ? S1 C4 C5 C8 172.27(10) . . . . ? C8 C5 N1 C6 -0.56(18) . . . . ? C4 C5 N1 C6 178.96(12) . . . . ? C5 N1 C6 N2 -0.2(2) . . . . ? N1 C6 N2 C7 0.6(2) . . . . ? C6 N2 C7 N4 -179.42(13) . . . . ? C6 N2 C7 C8 -0.3(2) . . . . ? N1 C5 C8 N3 179.49(13) . . . . ? C4 C5 C8 N3 0.0(2) . . . . ? N1 C5 C8 C7 0.77(17) . . . . ? C4 C5 C8 C7 -178.72(12) . . . . ? N2 C7 C8 N3 -179.32(12) . . . . ? N4 C7 C8 N3 -0.07(15) . . . . ? N2 C7 C8 C5 -0.3(2) . . . . ? N4 C7 C8 C5 178.93(11) . . . . ? C5 C8 N3 C9 -178.64(14) . . . . ? C7 C8 N3 C9 0.13(15) . . . . ? C8 N3 C9 N4 -0.15(16) . . . . ? N2 C7 N4 C9 179.22(13) . . . . ? C8 C7 N4 C9 -0.02(14) . . . . ? N2 C7 N4 C10 1.2(2) . . . . ? C8 C7 N4 C10 -178.03(13) . . . . ? N3 C9 N4 C7 0.11(16) . . . . ? N3 C9 N4 C10 178.14(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.401 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 945795' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 N4 O' _chemical_formula_weight 200.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 7.4259(2) _cell_length_b 17.6396(5) _cell_length_c 6.8688(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.245(2) _cell_angle_gamma 90.00 _cell_volume 890.44(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5173 _cell_measurement_theta_min 2.3092 _cell_measurement_theta_max 30.0314 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9597 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source Microfocus _diffrn_radiation_monochromator 'Quazar Mo multilayer optic' _diffrn_measurement_device_type 'APEX-II CCD-detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 15422 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 30.08 _reflns_number_total 2620 _reflns_number_gt 2226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2012.2-0' _computing_cell_refinement 'SAINT V8.18C (Bruker AXS Inc.)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0623P)^2^+0.3594P] 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 2620 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.19315(14) 0.68724(6) 0.38994(16) 0.0156(2) Uani 1 1 d . . . N1 N 0.04694(13) 0.73008(5) 0.32191(15) 0.0184(2) Uani 1 1 d . . . C2 C 0.06367(16) 0.80580(6) 0.33410(18) 0.0200(2) Uani 1 1 d . . . H2 H -0.0431 0.8338 0.2874 0.024 Uiso 1 1 calc R . . N2 N 0.20935(13) 0.84716(5) 0.40260(15) 0.0189(2) Uani 1 1 d . . . C3 C 0.35093(14) 0.80321(6) 0.46796(16) 0.0158(2) Uani 1 1 d . . . N3 N 0.52209(13) 0.82570(5) 0.54694(14) 0.0183(2) Uani 1 1 d . . . C31 C 0.58696(18) 0.90315(7) 0.5746(2) 0.0271(3) Uani 1 1 d . . . H31A H 0.7058 0.9033 0.6578 0.041 Uiso 1 1 calc R . . H33A H 0.5001 0.9328 0.6381 0.041 Uiso 1 1 calc R . . H32A H 0.5988 0.9256 0.4465 0.041 Uiso 1 1 calc R . . C4 C 0.61918(16) 0.76066(7) 0.59052(18) 0.0206(2) Uani 1 1 d . . . H4 H 0.7437 0.7608 0.6471 0.025 Uiso 1 1 calc R . . N4 N 0.52665(13) 0.69764(6) 0.54792(15) 0.0197(2) Uani 1 1 d . . . C5 C 0.35467(14) 0.72361(6) 0.46915(16) 0.0155(2) Uani 1 1 d . . . C6 C 0.17896(14) 0.60550(6) 0.37448(16) 0.0167(2) Uani 1 1 d . . . C7 C 0.29228(16) 0.54903(6) 0.44986(19) 0.0216(2) Uani 1 1 d . . . H7 H 0.4049 0.5548 0.5336 0.026 Uiso 1 1 calc R . . C8 C 0.20973(17) 0.47948(7) 0.37928(19) 0.0233(3) Uani 1 1 d . . . H8 H 0.2561 0.4298 0.4060 0.028 Uiso 1 1 calc R . . C9 C 0.05194(17) 0.49868(6) 0.26642(18) 0.0224(2) Uani 1 1 d . . . H9 H -0.0317 0.4634 0.1994 0.027 Uiso 1 1 calc R . . O1 O 0.02883(11) 0.57553(5) 0.26151(12) 0.0202(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0146(5) 0.0149(5) 0.0171(5) 0.0006(4) 0.0011(4) 0.0008(4) N1 0.0153(4) 0.0163(4) 0.0222(5) 0.0009(3) -0.0017(4) 0.0013(3) C2 0.0160(5) 0.0170(5) 0.0256(6) 0.0015(4) -0.0023(4) 0.0031(4) N2 0.0184(5) 0.0151(4) 0.0223(5) 0.0006(3) -0.0004(4) 0.0015(3) C3 0.0149(5) 0.0155(5) 0.0164(5) 0.0000(4) 0.0003(4) -0.0013(4) N3 0.0157(5) 0.0176(5) 0.0207(5) -0.0003(3) -0.0011(3) -0.0026(3) C31 0.0236(6) 0.0193(5) 0.0374(7) -0.0022(5) 0.0008(5) -0.0077(4) C4 0.0152(5) 0.0221(5) 0.0232(6) 0.0014(4) -0.0012(4) 0.0000(4) N4 0.0143(4) 0.0195(5) 0.0238(5) 0.0015(4) -0.0022(4) 0.0023(3) C5 0.0137(5) 0.0149(5) 0.0174(5) 0.0011(4) 0.0003(4) 0.0011(4) C6 0.0147(5) 0.0154(5) 0.0196(5) -0.0005(4) 0.0006(4) -0.0012(4) C7 0.0184(5) 0.0166(5) 0.0284(6) -0.0013(4) -0.0009(4) 0.0013(4) C8 0.0239(6) 0.0148(5) 0.0308(6) -0.0010(4) 0.0022(5) 0.0009(4) C9 0.0237(6) 0.0152(5) 0.0276(6) -0.0020(4) 0.0017(4) -0.0029(4) O1 0.0191(4) 0.0153(4) 0.0246(4) -0.0001(3) -0.0027(3) -0.0020(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 N1 1.3500(13) . ? C1 C5 1.3997(15) . ? C1 C6 1.4486(15) . ? N1 C2 1.3429(14) . ? C2 N2 1.3334(15) . ? C2 H2 0.9500 . ? N2 C3 1.3313(14) . ? C3 N3 1.3673(14) . ? C3 C5 1.4044(14) . ? N3 C4 1.3652(15) . ? N3 C31 1.4521(15) . ? C31 H31A 0.9800 . ? C31 H33A 0.9800 . ? C31 H32A 0.9800 . ? C4 N4 1.3176(15) . ? C4 H4 0.9500 . ? N4 C5 1.3912(14) . ? C6 C7 1.3578(15) . ? C6 O1 1.3699(13) . ? C7 C8 1.4250(16) . ? C7 H7 0.9500 . ? C8 C9 1.3521(17) . ? C8 H8 0.9500 . ? C9 O1 1.3661(13) . ? C9 H9 0.9500 . ? 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 C5 118.67(10) . . ? N1 C1 C6 119.04(10) . . ? C5 C1 C6 122.27(10) . . ? C2 N1 C1 118.20(10) . . ? N2 C2 N1 129.00(10) . . ? N2 C2 H2 115.5 . . ? N1 C2 H2 115.5 . . ? C3 N2 C2 111.22(10) . . ? N2 C3 N3 127.52(10) . . ? N2 C3 C5 126.74(10) . . ? N3 C3 C5 105.74(9) . . ? C4 N3 C3 105.95(9) . . ? C4 N3 C31 127.39(10) . . ? C3 N3 C31 126.65(10) . . ? N3 C31 H31A 109.5 . . ? N3 C31 H33A 109.5 . . ? H31A C31 H33A 109.5 . . ? N3 C31 H32A 109.5 . . ? H31A C31 H32A 109.5 . . ? H33A C31 H32A 109.5 . . ? N4 C4 N3 114.72(10) . . ? N4 C4 H4 122.6 . . ? N3 C4 H4 122.6 . . ? C4 N4 C5 103.24(9) . . ? N4 C5 C1 133.47(10) . . ? N4 C5 C3 110.35(9) . . ? C1 C5 C3 116.16(9) . . ? C7 C6 O1 110.02(10) . . ? C7 C6 C1 131.90(10) . . ? O1 C6 C1 118.06(9) . . ? C6 C7 C8 106.80(11) . . ? C6 C7 H7 126.6 . . ? C8 C7 H7 126.6 . . ? C9 C8 C7 105.93(10) . . ? C9 C8 H8 127.0 . . ? C7 C8 H8 127.0 . . ? C8 C9 O1 110.99(10) . . ? C8 C9 H9 124.5 . . ? O1 C9 H9 124.5 . . ? C9 O1 C6 106.25(9) . . ? 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 C5 C1 N1 C2 -0.16(15) . . . . ? C6 C1 N1 C2 -178.77(10) . . . . ? C1 N1 C2 N2 1.41(19) . . . . ? N1 C2 N2 C3 -1.20(18) . . . . ? C2 N2 C3 N3 179.61(11) . . . . ? C2 N2 C3 C5 -0.20(16) . . . . ? N2 C3 N3 C4 -179.64(11) . . . . ? C5 C3 N3 C4 0.20(12) . . . . ? N2 C3 N3 C31 -0.72(19) . . . . ? C5 C3 N3 C31 179.12(11) . . . . ? C3 N3 C4 N4 -0.28(14) . . . . ? C31 N3 C4 N4 -179.19(12) . . . . ? N3 C4 N4 C5 0.23(14) . . . . ? C4 N4 C5 C1 178.11(12) . . . . ? C4 N4 C5 C3 -0.08(12) . . . . ? N1 C1 C5 N4 -179.09(11) . . . . ? C6 C1 C5 N4 -0.53(19) . . . . ? N1 C1 C5 C3 -0.98(15) . . . . ? C6 C1 C5 C3 177.58(10) . . . . ? N2 C3 C5 N4 179.76(11) . . . . ? N3 C3 C5 N4 -0.08(12) . . . . ? N2 C3 C5 C1 1.22(16) . . . . ? N3 C3 C5 C1 -178.62(9) . . . . ? N1 C1 C6 C7 -170.67(12) . . . . ? C5 C1 C6 C7 10.77(19) . . . . ? N1 C1 C6 O1 11.07(15) . . . . ? C5 C1 C6 O1 -167.48(10) . . . . ? O1 C6 C7 C8 0.46(13) . . . . ? C1 C6 C7 C8 -177.90(12) . . . . ? C6 C7 C8 C9 -0.14(14) . . . . ? C7 C8 C9 O1 -0.24(14) . . . . ? C8 C9 O1 C6 0.52(13) . . . . ? C7 C6 O1 C9 -0.61(13) . . . . ? C1 C6 O1 C9 178.01(10) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.398 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 945796' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_is230413_0m_03 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Ag N6 O3 S' _chemical_formula_weight 427.20 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.652(3) _cell_length_b 7.2312(9) _cell_length_c 18.795(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.954(3) _cell_angle_gamma 90.00 _cell_volume 3067.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9893 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 1.474 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7471 _exptl_absorpt_correction_T_max 0.9571 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source Microfocus _diffrn_radiation_monochromator 'Venture Mo multilayer optic' _diffrn_measurement_device_type 'Photon 100 CMOS-detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16656 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.95 _reflns_number_total 3675 _reflns_number_gt 3071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^)+(0.1165P)^2^+2.5144P] 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 3675 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Ag1 Ag 0.863499(13) 0.95887(5) 0.193127(15) 0.02890(16) Uani 1 1 d . . . N1 N 0.87283(14) 0.7759(5) 0.29321(18) 0.0256(7) Uani 1 1 d . . . C1 C 0.91182(17) 0.8017(5) 0.3482(2) 0.0279(8) Uani 1 1 d . . . H1 H 0.9505 0.8481 0.3436 0.033 Uiso 1 1 calc R . . N2 N 0.89237(14) 0.7570(5) 0.41200(17) 0.0261(7) Uani 1 1 d . . . C21 C 0.9241(2) 0.7672(7) 0.4829(2) 0.0384(11) Uani 1 1 d . . . H21A H 0.9651 0.8065 0.4786 0.058 Uiso 1 1 calc R . . H21B H 0.9241 0.6452 0.5056 0.058 Uiso 1 1 calc R . . H21C H 0.9045 0.8567 0.5122 0.058 Uiso 1 1 calc R . . C2 C 0.83489(17) 0.7006(5) 0.3977(2) 0.0243(8) Uani 1 1 d . . . C3 C 0.82320(16) 0.7112(5) 0.32350(18) 0.0190(7) Uani 1 1 d . . . N3 N 0.79691(15) 0.6499(5) 0.44431(16) 0.0264(7) Uani 1 1 d . . . C4 C 0.74404(18) 0.6084(6) 0.4121(2) 0.0262(8) Uani 1 1 d . . . H4 H 0.7143 0.5760 0.4425 0.031 Uiso 1 1 calc R . . N4 N 0.72742(14) 0.6068(4) 0.34102(16) 0.0214(6) Uani 1 1 d . . . C5 C 0.76747(16) 0.6572(5) 0.29558(19) 0.0203(7) Uani 1 1 d . . . C6 C 0.75115(17) 0.6493(5) 0.21874(19) 0.0223(7) Uani 1 1 d . . . C7 C 0.78992(15) 0.5977(4) 0.16399(17) 0.0157(6) Uani 1 1 d . . . H7 H 0.8305 0.5645 0.1721 0.019 Uiso 1 1 calc R . . C8 C 0.7569(2) 0.6056(7) 0.0969(2) 0.0402(11) Uani 1 1 d . . . H8 H 0.7734 0.5732 0.0538 0.048 Uiso 1 1 calc R . . C9 C 0.7006(3) 0.6620(7) 0.0982(2) 0.0421(12) Uani 1 1 d . . . H9 H 0.6740 0.6761 0.0566 0.051 Uiso 1 1 calc R . . S1A S 0.68228(5) 0.70544(15) 0.18164(6) 0.0338(3) Uani 1 1 d . . . N5 N 0.91426(16) 0.7681(6) 0.0669(2) 0.0388(9) Uani 1 1 d . . . O51 O 0.86903(14) 0.8627(5) 0.06547(17) 0.0380(7) Uani 1 1 d . . . O52 O 0.92941(19) 0.7004(8) 0.0103(2) 0.0754(15) Uani 1 1 d . . . O53 O 0.94349(19) 0.7412(8) 0.1242(2) 0.0750(15) Uani 1 1 d . . . N10 N 0.9370(2) 1.1788(9) 0.1817(3) 0.0671(16) Uani 1 1 d . . . C10 C 0.9754(2) 1.2630(8) 0.1647(3) 0.0434(11) Uani 1 1 d . . . C11 C 1.0242(2) 1.3715(8) 0.1423(3) 0.0484(13) Uani 1 1 d . . . H11A H 1.0086 1.4803 0.1159 0.073 Uiso 1 1 calc R . . H11B H 1.0474 1.2963 0.1115 0.073 Uiso 1 1 calc R . . H11C H 1.0495 1.4113 0.1844 0.073 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 Ag1 0.0254(2) 0.0358(2) 0.0262(2) 0.00461(11) 0.00597(14) -0.00037(11) N1 0.0198(15) 0.0259(16) 0.0316(16) 0.0012(14) 0.0049(13) 0.0006(13) C1 0.0213(17) 0.0277(18) 0.035(2) 0.0018(17) 0.0022(16) 0.0027(15) N2 0.0226(15) 0.0301(16) 0.0252(15) 0.0013(14) -0.0004(13) 0.0010(13) C21 0.029(2) 0.052(3) 0.032(2) -0.010(2) -0.0076(18) 0.004(2) C2 0.0281(19) 0.0203(16) 0.0239(17) -0.0034(15) -0.0008(15) 0.0038(15) C3 0.0196(16) 0.0197(16) 0.0182(15) 0.0003(13) 0.0041(13) 0.0009(13) N3 0.0288(17) 0.0322(17) 0.0184(14) -0.0008(13) 0.0040(13) -0.0005(14) C4 0.0289(19) 0.0293(19) 0.0216(17) 0.0002(16) 0.0093(15) -0.0003(17) N4 0.0224(15) 0.0220(14) 0.0204(14) 0.0000(12) 0.0049(12) 0.0004(12) C5 0.0231(17) 0.0159(15) 0.0222(16) 0.0008(13) 0.0042(14) -0.0007(13) C6 0.0256(17) 0.0216(17) 0.0196(16) 0.0011(14) 0.0010(14) -0.0044(14) C7 0.0233(16) 0.0116(13) 0.0125(14) -0.0027(12) 0.0030(12) -0.0075(13) C8 0.060(3) 0.041(2) 0.0199(19) -0.0029(18) 0.007(2) -0.022(2) C9 0.060(3) 0.038(2) 0.026(2) 0.0090(19) -0.011(2) -0.020(2) S1A 0.0358(6) 0.0314(5) 0.0330(5) 0.0044(4) -0.0034(4) -0.0037(4) N5 0.0249(17) 0.047(2) 0.045(2) -0.0080(19) 0.0083(17) 0.0031(17) O51 0.0300(15) 0.0480(19) 0.0364(16) -0.0022(15) 0.0044(13) 0.0093(15) O52 0.052(3) 0.102(4) 0.076(3) -0.043(3) 0.032(2) 0.003(3) O53 0.044(2) 0.117(4) 0.062(2) 0.002(3) -0.011(2) 0.028(3) N10 0.063(3) 0.089(4) 0.049(3) 0.005(3) 0.003(2) -0.047(3) C10 0.048(3) 0.050(3) 0.032(2) 0.002(2) 0.000(2) -0.012(2) C11 0.036(2) 0.056(3) 0.054(3) 0.015(3) 0.012(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.294(3) . ? Ag1 N10 2.326(5) . ? Ag1 N4 2.360(3) 4_655 ? Ag1 O51 2.511(3) . ? N1 C1 1.314(5) . ? N1 C3 1.385(5) . ? C1 N2 1.351(5) . ? C1 H1 0.9500 . ? N2 C2 1.369(5) . ? N2 C21 1.461(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C2 N3 1.331(5) . ? C2 C3 1.400(5) . ? C3 C5 1.381(5) . ? N3 C4 1.329(5) . ? C4 N4 1.356(5) . ? C4 H4 0.9500 . ? N4 C5 1.349(5) . ? N4 Ag1 2.360(3) 4_645 ? C5 C6 1.461(5) . ? C6 C7 1.458(5) . ? C6 S1A 1.702(4) . ? C7 C8 1.410(5) . ? C7 H7 0.9500 . ? C8 C9 1.341(8) . ? C8 H8 0.9500 . ? C9 S1A 1.686(5) . ? C9 H9 0.9500 . ? N5 O51 1.230(5) . ? N5 O53 1.230(5) . ? N5 O52 1.246(5) . ? N10 C10 1.129(7) . ? C10 C11 1.448(7) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 N10 117.00(16) . . ? N1 Ag1 N4 120.05(11) . 4_655 ? N10 Ag1 N4 106.25(19) . 4_655 ? N1 Ag1 O51 127.94(11) . . ? N10 Ag1 O51 90.34(15) . . ? N4 Ag1 O51 88.85(10) 4_655 . ? C1 N1 C3 103.8(3) . . ? C1 N1 Ag1 124.9(3) . . ? C3 N1 Ag1 120.8(2) . . ? N1 C1 N2 114.6(4) . . ? N1 C1 H1 122.7 . . ? N2 C1 H1 122.7 . . ? C1 N2 C2 106.0(3) . . ? C1 N2 C21 128.7(4) . . ? C2 N2 C21 125.4(4) . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C2 N2 127.7(3) . . ? N3 C2 C3 126.4(4) . . ? N2 C2 C3 105.9(3) . . ? C5 C3 N1 133.4(3) . . ? C5 C3 C2 116.8(3) . . ? N1 C3 C2 109.7(3) . . ? C4 N3 C2 111.8(3) . . ? N3 C4 N4 127.8(4) . . ? N3 C4 H4 116.1 . . ? N4 C4 H4 116.1 . . ? C5 N4 C4 118.5(3) . . ? C5 N4 Ag1 124.7(2) . 4_645 ? C4 N4 Ag1 115.7(3) . 4_645 ? N4 C5 C3 118.6(3) . . ? N4 C5 C6 119.3(3) . . ? C3 C5 C6 122.1(3) . . ? C7 C6 C5 126.3(3) . . ? C7 C6 S1A 111.0(2) . . ? C5 C6 S1A 122.7(3) . . ? C8 C7 C6 108.4(4) . . ? C8 C7 H7 125.8 . . ? C6 C7 H7 125.8 . . ? C9 C8 C7 115.4(4) . . ? C9 C8 H8 122.3 . . ? C7 C8 H8 122.3 . . ? C8 C9 S1A 112.6(3) . . ? C8 C9 H9 123.7 . . ? S1A C9 H9 123.7 . . ? C9 S1A C6 92.6(2) . . ? O51 N5 O53 119.4(4) . . ? O51 N5 O52 119.4(4) . . ? O53 N5 O52 121.2(5) . . ? N5 O51 Ag1 104.1(3) . . ? C10 N10 Ag1 165.7(5) . . ? N10 C10 C11 179.4(6) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N10 Ag1 N1 C1 9.3(4) . . . . ? N4 Ag1 N1 C1 -121.9(3) 4_655 . . . ? O51 Ag1 N1 C1 123.2(3) . . . . ? N10 Ag1 N1 C3 148.1(3) . . . . ? N4 Ag1 N1 C3 17.0(3) 4_655 . . . ? O51 Ag1 N1 C3 -98.0(3) . . . . ? C3 N1 C1 N2 0.9(5) . . . . ? Ag1 N1 C1 N2 145.3(3) . . . . ? N1 C1 N2 C2 -1.4(5) . . . . ? N1 C1 N2 C21 179.4(4) . . . . ? C1 N2 C2 N3 -177.2(4) . . . . ? C21 N2 C2 N3 2.0(7) . . . . ? C1 N2 C2 C3 1.3(4) . . . . ? C21 N2 C2 C3 -179.5(4) . . . . ? C1 N1 C3 C5 -179.6(4) . . . . ? Ag1 N1 C3 C5 34.1(6) . . . . ? C1 N1 C3 C2 0.0(4) . . . . ? Ag1 N1 C3 C2 -146.2(3) . . . . ? N3 C2 C3 C5 -2.6(6) . . . . ? N2 C2 C3 C5 178.9(3) . . . . ? N3 C2 C3 N1 177.7(4) . . . . ? N2 C2 C3 N1 -0.8(4) . . . . ? N2 C2 N3 C4 178.1(4) . . . . ? C3 C2 N3 C4 -0.1(6) . . . . ? C2 N3 C4 N4 2.6(6) . . . . ? N3 C4 N4 C5 -2.0(6) . . . . ? N3 C4 N4 Ag1 166.3(3) . . . 4_645 ? C4 N4 C5 C3 -1.1(5) . . . . ? Ag1 N4 C5 C3 -168.2(3) 4_645 . . . ? C4 N4 C5 C6 177.6(3) . . . . ? Ag1 N4 C5 C6 10.4(5) 4_645 . . . ? N1 C3 C5 N4 -177.3(4) . . . . ? C2 C3 C5 N4 3.0(5) . . . . ? N1 C3 C5 C6 4.1(6) . . . . ? C2 C3 C5 C6 -175.5(3) . . . . ? N4 C5 C6 C7 -143.8(4) . . . . ? C3 C5 C6 C7 34.8(5) . . . . ? N4 C5 C6 S1A 37.4(5) . . . . ? C3 C5 C6 S1A -144.0(3) . . . . ? C5 C6 C7 C8 179.3(4) . . . . ? S1A C6 C7 C8 -1.8(4) . . . . ? C6 C7 C8 C9 2.1(5) . . . . ? C7 C8 C9 S1A -1.5(6) . . . . ? C8 C9 S1A C6 0.3(4) . . . . ? C7 C6 S1A C9 0.9(3) . . . . ? C5 C6 S1A C9 179.8(3) . . . . ? O53 N5 O51 Ag1 1.0(5) . . . . ? O52 N5 O51 Ag1 -179.5(4) . . . . ? N1 Ag1 O51 N5 -48.6(3) . . . . ? N10 Ag1 O51 N5 76.8(3) . . . . ? N4 Ag1 O51 N5 -176.9(3) 4_655 . . . ? N1 Ag1 N10 C10 112(2) . . . . ? N4 Ag1 N10 C10 -110(2) 4_655 . . . ? O51 Ag1 N10 C10 -22(2) . . . . ? Ag1 N10 C10 C11 72(83) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.606 _refine_diff_density_min -1.257 _refine_diff_density_rms 0.220 _database_code_depnum_ccdc_archive 'CCDC 945797' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_is130812_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Cl4 Cu2 N8 O4' _chemical_formula_weight 705.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5949(13) _cell_length_b 10.8315(7) _cell_length_c 15.5754(10) _cell_angle_alpha 90.00 _cell_angle_beta 126.1040(10) _cell_angle_gamma 90.00 _cell_volume 2534.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9925 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 30.08 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 2.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6585 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source Microfocus _diffrn_radiation_monochromator 'Venture Mo multilayer optic' _diffrn_measurement_device_type 'Photon 100 CMOS-detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29480 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.12 _reflns_number_total 3710 _reflns_number_gt 3466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'SAINT V8.18C (Bruker AXS Inc.)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+3.9758P] 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 3710 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.050115(13) 0.628043(17) 0.096699(15) 0.01700(6) Uani 1 1 d . . . Cl2 Cl -0.06935(3) 0.68597(4) 0.09273(3) 0.02367(9) Uani 1 1 d . . . O1 O 0.12357(9) 0.62111(12) 0.25605(10) 0.0227(2) Uani 1 1 d . . . H1A H 0.0983(18) 0.642(2) 0.277(2) 0.035(7) Uiso 1 1 d . . . H1B H 0.1444(18) 0.558(3) 0.279(2) 0.043(7) Uiso 1 1 d . . . N1 N 0.16508(9) 0.62036(12) 0.11200(11) 0.0194(3) Uani 1 1 d . . . C1 C 0.19483(11) 0.51558(16) 0.10118(13) 0.0221(3) Uani 1 1 d . . . H1 H 0.1673 0.4380 0.0921 0.026 Uiso 1 1 calc R . . N2 N 0.26855(9) 0.52978(14) 0.10431(11) 0.0227(3) Uani 1 1 d . . . C2 C 0.28925(11) 0.65289(16) 0.11962(12) 0.0213(3) Uani 1 1 d . . . N3 N 0.35728(10) 0.70661(15) 0.12736(12) 0.0261(3) Uani 1 1 d . . . C3 C 0.35812(12) 0.82830(18) 0.14205(14) 0.0281(4) Uani 1 1 d . . . H3 H 0.4059 0.8729 0.1504 0.034 Uiso 1 1 calc R . . N4 N 0.30007(10) 0.89429(14) 0.14638(12) 0.0253(3) Uani 1 1 d . . . C4 C 0.23009(11) 0.83763(15) 0.13582(12) 0.0219(3) Uani 1 1 d . . . C5 C 0.22395(10) 0.70944(15) 0.12414(12) 0.0197(3) Uani 1 1 d . . . C6 C 0.16624(12) 0.91504(15) 0.13502(13) 0.0232(3) Uani 1 1 d . . . C7 C 0.15746(13) 1.03956(17) 0.13626(14) 0.0291(4) Uani 1 1 d . . . H7 H 0.1953 1.1004 0.1384 0.035 Uiso 1 1 calc R . . C8 C 0.08103(13) 1.06111(16) 0.13372(14) 0.0299(4) Uani 1 1 d . . . H8 H 0.0578 1.1390 0.1341 0.036 Uiso 1 1 calc R . . C9 C 0.04801(13) 0.94955(17) 0.13067(15) 0.0292(4) Uani 1 1 d . . . H9 H -0.0035 0.9361 0.1285 0.035 Uiso 1 1 calc R . . O2 O 0.09919(9) 0.85780(11) 0.13122(11) 0.0264(3) Uani 1 1 d . . . C10 C 0.31591(13) 0.43080(19) 0.09219(16) 0.0318(4) Uani 1 1 d . . . H10B H 0.3726 0.4141 0.1610 0.048 Uiso 1 1 calc R . . H10C H 0.3274 0.4564 0.0409 0.048 Uiso 1 1 calc R . . H10A H 0.2794 0.3558 0.0665 0.048 Uiso 1 1 calc R . . Cl1 Cl -0.02715(3) 0.62327(3) -0.08417(3) 0.01883(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02049(11) 0.01572(10) 0.01935(10) 0.00026(6) 0.01427(8) 0.00164(6) Cl2 0.02524(19) 0.02683(19) 0.02538(18) 0.00009(14) 0.01848(16) 0.00517(14) O1 0.0274(6) 0.0235(6) 0.0222(6) 0.0033(4) 0.0174(5) 0.0080(5) N1 0.0188(6) 0.0211(6) 0.0207(6) -0.0019(5) 0.0129(5) -0.0026(5) C1 0.0206(7) 0.0246(8) 0.0235(7) -0.0023(6) 0.0143(6) -0.0004(6) N2 0.0205(6) 0.0276(7) 0.0227(6) -0.0016(5) 0.0142(6) 0.0012(5) C2 0.0195(7) 0.0288(8) 0.0169(6) -0.0004(6) 0.0114(6) 0.0008(6) N3 0.0242(7) 0.0349(8) 0.0239(7) -0.0005(6) 0.0169(6) -0.0028(6) C3 0.0282(8) 0.0351(9) 0.0235(8) -0.0023(7) 0.0167(7) -0.0091(7) N4 0.0298(7) 0.0255(7) 0.0218(6) -0.0031(5) 0.0159(6) -0.0097(6) C4 0.0259(8) 0.0228(7) 0.0176(7) -0.0009(5) 0.0132(6) -0.0044(6) C5 0.0204(7) 0.0227(7) 0.0177(6) -0.0008(5) 0.0121(6) -0.0023(6) C6 0.0290(8) 0.0201(7) 0.0195(7) -0.0008(6) 0.0137(6) -0.0013(6) C7 0.0373(10) 0.0204(8) 0.0242(8) -0.0008(6) 0.0151(7) -0.0030(7) C8 0.0378(10) 0.0184(8) 0.0249(8) -0.0011(6) 0.0137(8) 0.0068(7) C9 0.0315(9) 0.0229(8) 0.0329(9) -0.0018(7) 0.0188(8) 0.0045(7) O2 0.0320(7) 0.0164(5) 0.0341(7) -0.0004(5) 0.0213(6) 0.0019(5) C10 0.0304(9) 0.0348(10) 0.0370(9) -0.0034(8) 0.0236(8) 0.0077(7) Cl1 0.02415(18) 0.01559(16) 0.01981(16) 0.00175(11) 0.01464(14) 0.00035(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 Cu1 N1 2.0083(14) . ? Cu1 O1 2.0091(13) . ? Cu1 Cl2 2.2739(4) . ? Cu1 Cl1 2.2876(4) . ? Cu1 Cl1 2.7445(4) 5_565 ? O1 H1A 0.75(3) . ? O1 H1B 0.76(3) . ? N1 C1 1.316(2) . ? N1 C5 1.386(2) . ? C1 N2 1.351(2) . ? C1 H1 0.9500 . ? N2 C2 1.369(2) . ? N2 C10 1.468(2) . ? C2 N3 1.332(2) . ? C2 C5 1.398(2) . ? N3 C3 1.336(2) . ? C3 N4 1.329(2) . ? C3 H3 0.9500 . ? N4 C4 1.358(2) . ? C4 C5 1.396(2) . ? C4 C6 1.447(2) . ? C6 C7 1.360(2) . ? C6 O2 1.362(2) . ? C7 C8 1.418(3) . ? C7 H7 0.9500 . ? C8 C9 1.344(3) . ? C8 H8 0.9500 . ? C9 O2 1.373(2) . ? C9 H9 0.9500 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10A 0.9800 . ? Cl1 Cu1 2.7445(4) 5_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 N1 Cu1 O1 87.17(5) . . ? N1 Cu1 Cl2 165.74(4) . . ? O1 Cu1 Cl2 89.20(4) . . ? N1 Cu1 Cl1 89.85(4) . . ? O1 Cu1 Cl1 175.54(4) . . ? Cl2 Cu1 Cl1 94.486(15) . . ? N1 Cu1 Cl1 94.45(4) . 5_565 ? O1 Cu1 Cl1 90.85(4) . 5_565 ? Cl2 Cu1 Cl1 99.387(15) . 5_565 ? Cl1 Cu1 Cl1 86.075(13) . 5_565 ? Cu1 O1 H1A 113(2) . . ? Cu1 O1 H1B 114(2) . . ? H1A O1 H1B 110(3) . . ? C1 N1 C5 105.07(13) . . ? C1 N1 Cu1 121.25(11) . . ? C5 N1 Cu1 133.42(11) . . ? N1 C1 N2 113.02(15) . . ? N1 C1 H1 123.5 . . ? N2 C1 H1 123.5 . . ? C1 N2 C2 106.99(14) . . ? C1 N2 C10 125.77(16) . . ? C2 N2 C10 127.23(15) . . ? N3 C2 N2 126.57(15) . . ? N3 C2 C5 127.65(16) . . ? N2 C2 C5 105.78(14) . . ? C2 N3 C3 111.17(15) . . ? N4 C3 N3 127.68(16) . . ? N4 C3 H3 116.2 . . ? N3 C3 H3 116.2 . . ? C3 N4 C4 119.98(15) . . ? N4 C4 C5 117.64(16) . . ? N4 C4 C6 117.50(15) . . ? C5 C4 C6 124.84(15) . . ? N1 C5 C4 135.02(15) . . ? N1 C5 C2 109.13(14) . . ? C4 C5 C2 115.81(15) . . ? C7 C6 O2 109.72(16) . . ? C7 C6 C4 132.77(17) . . ? O2 C6 C4 117.51(14) . . ? C6 C7 C8 106.84(17) . . ? C6 C7 H7 126.6 . . ? C8 C7 H7 126.6 . . ? C9 C8 C7 106.43(16) . . ? C9 C8 H8 126.8 . . ? C7 C8 H8 126.8 . . ? C8 C9 O2 110.50(17) . . ? C8 C9 H9 124.8 . . ? O2 C9 H9 124.8 . . ? C6 O2 C9 106.52(14) . . ? N2 C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? Cu1 Cl1 Cu1 93.927(13) . 5_565 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N1 C1 98.12(13) . . . . ? Cl2 Cu1 N1 C1 173.54(12) . . . . ? Cl1 Cu1 N1 C1 -78.57(13) . . . . ? Cl1 Cu1 N1 C1 7.48(13) 5_565 . . . ? O1 Cu1 N1 C5 -88.74(15) . . . . ? Cl2 Cu1 N1 C5 -13.3(3) . . . . ? Cl1 Cu1 N1 C5 94.58(14) . . . . ? Cl1 Cu1 N1 C5 -179.37(14) 5_565 . . . ? C5 N1 C1 N2 -0.61(19) . . . . ? Cu1 N1 C1 N2 174.23(11) . . . . ? N1 C1 N2 C2 0.77(19) . . . . ? N1 C1 N2 C10 -178.60(16) . . . . ? C1 N2 C2 N3 -179.95(16) . . . . ? C10 N2 C2 N3 -0.6(3) . . . . ? C1 N2 C2 C5 -0.58(17) . . . . ? C10 N2 C2 C5 178.78(16) . . . . ? N2 C2 N3 C3 179.94(16) . . . . ? C5 C2 N3 C3 0.7(2) . . . . ? C2 N3 C3 N4 -1.7(3) . . . . ? N3 C3 N4 C4 0.4(3) . . . . ? C3 N4 C4 C5 2.1(2) . . . . ? C3 N4 C4 C6 -176.50(15) . . . . ? C1 N1 C5 C4 177.75(18) . . . . ? Cu1 N1 C5 C4 3.8(3) . . . . ? C1 N1 C5 C2 0.22(18) . . . . ? Cu1 N1 C5 C2 -173.71(11) . . . . ? N4 C4 C5 N1 179.73(16) . . . . ? C6 C4 C5 N1 -1.8(3) . . . . ? N4 C4 C5 C2 -2.9(2) . . . . ? C6 C4 C5 C2 175.62(15) . . . . ? N3 C2 C5 N1 179.59(15) . . . . ? N2 C2 C5 N1 0.23(18) . . . . ? N3 C2 C5 C4 1.5(2) . . . . ? N2 C2 C5 C4 -177.83(14) . . . . ? N4 C4 C6 C7 4.9(3) . . . . ? C5 C4 C6 C7 -173.62(18) . . . . ? N4 C4 C6 O2 -175.93(14) . . . . ? C5 C4 C6 O2 5.6(2) . . . . ? O2 C6 C7 C8 0.3(2) . . . . ? C4 C6 C7 C8 179.60(17) . . . . ? C6 C7 C8 C9 -0.2(2) . . . . ? C7 C8 C9 O2 0.1(2) . . . . ? C7 C6 O2 C9 -0.32(19) . . . . ? C4 C6 O2 C9 -179.70(14) . . . . ? C8 C9 O2 C6 0.2(2) . . . . ? N1 Cu1 Cl1 Cu1 94.47(4) . . . 5_565 ? O1 Cu1 Cl1 Cu1 46.5(5) . . . 5_565 ? Cl2 Cu1 Cl1 Cu1 -99.127(16) . . . 5_565 ? Cl1 Cu1 Cl1 Cu1 0.0 5_565 . . 5_565 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.12 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.701 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 945798'