# 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_ndb_a _database_code_depnum_ccdc_archive 'CCDC 852730' #TrackingRef 'ndb_a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Cl Cu N3 O2' _chemical_formula_weight 369.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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 7.2500(7) _cell_length_b 9.4099(9) _cell_length_c 11.1819(10) _cell_angle_alpha 85.320(6) _cell_angle_beta 86.289(5) _cell_angle_gamma 81.042(5) _cell_volume 749.98(12) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2445 _cell_measurement_theta_min 3.97 _cell_measurement_theta_max 60.78 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 3.786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7033 _exptl_absorpt_correction_T_max 0.9281 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER GADDS D8 Discover' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12160 _diffrn_reflns_av_R_equivalents 0.1001 _diffrn_reflns_av_sigmaI/netI 0.0921 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.97 _diffrn_reflns_theta_max 59.98 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _reflns_number_total 2131 _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'FRAMBO (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) ; _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _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^)+(0.0514P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2131 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1030 _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 Cu1 Cu 0.70855(9) 0.93224(7) 0.82111(6) 0.0134(2) Uani 1 1 d . . . Cl1 Cl 0.63099(16) 0.80548(12) 0.67669(10) 0.0181(3) Uani 1 1 d . . . C1 C 0.6484(6) 1.1682(5) 0.6201(4) 0.0161(12) Uani 1 1 d . . . H1 H 0.6438 1.0944 0.5677 0.019 Uiso 1 1 calc R . . C2 C 0.6362(6) 1.3088(5) 0.5731(4) 0.0171(12) Uani 1 1 d . . . H2 H 0.6246 1.3315 0.4893 0.021 Uiso 1 1 calc R . . C3 C 0.6412(6) 1.4166(5) 0.6488(4) 0.0178(12) Uani 1 1 d . . . H3 H 0.6333 1.5142 0.6178 0.021 Uiso 1 1 calc R . . C4 C 0.6579(6) 1.3804(5) 0.7708(4) 0.0139(12) Uani 1 1 d . . . H4 H 0.6605 1.4534 0.8243 0.017 Uiso 1 1 calc R . . C5 C 0.6708(6) 1.2377(5) 0.8139(4) 0.0104(11) Uani 1 1 d . . . C6 C 0.6966(6) 1.1859(5) 0.9409(4) 0.0107(11) Uani 1 1 d . . . C7 C 0.6957(6) 1.2849(5) 1.0375(4) 0.0170(12) Uani 1 1 d . . . H7A H 0.6468 1.2412 1.1131 0.026 Uiso 1 1 calc R . . H7B H 0.6162 1.3765 1.0163 0.026 Uiso 1 1 calc R . . H7C H 0.8235 1.3026 1.0469 0.026 Uiso 1 1 calc R . . C8 C 0.7654(6) 0.8321(5) 1.0516(4) 0.0138(12) Uani 1 1 d . . . C9 C 0.8113(6) 0.7291(5) 1.1577(4) 0.0114(11) Uani 1 1 d . . . C10 C 0.7935(6) 0.7704(5) 1.2752(4) 0.0135(11) Uani 1 1 d . . . H10 H 0.7493 0.8680 1.2904 0.016 Uiso 1 1 calc R . . C11 C 0.8400(6) 0.6699(5) 1.3698(4) 0.0166(12) Uani 1 1 d . . . H11 H 0.8287 0.6992 1.4496 0.020 Uiso 1 1 calc R . . C12 C 0.9030(7) 0.5271(5) 1.3491(4) 0.0201(12) Uani 1 1 d . . . H12 H 0.9344 0.4587 1.4147 0.024 Uiso 1 1 calc R . . C13 C 0.9203(7) 0.4837(5) 1.2329(4) 0.0180(12) Uani 1 1 d . . . H13 H 0.9640 0.3858 1.2184 0.022 Uiso 1 1 calc R . . C14 C 0.8731(6) 0.5847(5) 1.1378(4) 0.0145(12) Uani 1 1 d . . . H14 H 0.8830 0.5549 1.0582 0.017 Uiso 1 1 calc R . . C15 C 1.0987(7) 0.8972(5) 0.6551(4) 0.0206(13) Uani 1 1 d . . . H15A H 1.2332 0.8628 0.6577 0.031 Uiso 1 1 calc R . . H15B H 1.0784 0.9910 0.6091 0.031 Uiso 1 1 calc R . . H15C H 1.0388 0.8278 0.6164 0.031 Uiso 1 1 calc R . . N1 N 0.6665(5) 1.1318(4) 0.7382(3) 0.0115(9) Uani 1 1 d . . . N2 N 0.7195(5) 1.0470(4) 0.9571(3) 0.0102(9) Uani 1 1 d . . . N3 N 0.7553(5) 0.9730(4) 1.0676(3) 0.0118(9) Uani 1 1 d . . . O1 O 0.7414(4) 0.7789(3) 0.9535(3) 0.0146(8) Uani 1 1 d . . . O2 O 1.0192(4) 0.9118(3) 0.7750(3) 0.0174(8) Uani 1 1 d . . . H2A H 1.1015 0.9294 0.8203 0.026 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0197(5) 0.0111(4) 0.0108(4) -0.0022(3) -0.0027(3) -0.0047(3) Cl1 0.0254(8) 0.0162(7) 0.0150(7) -0.0060(5) -0.0052(5) -0.0063(5) C1 0.015(3) 0.016(3) 0.018(3) -0.004(2) -0.005(2) 0.000(2) C2 0.020(3) 0.016(3) 0.013(3) 0.010(2) -0.004(2) -0.002(2) C3 0.017(3) 0.014(3) 0.022(3) 0.002(2) -0.003(2) -0.001(2) C4 0.014(3) 0.018(3) 0.010(3) -0.004(2) 0.004(2) -0.004(2) C5 0.005(3) 0.018(3) 0.009(3) -0.004(2) -0.0007(19) -0.002(2) C6 0.010(3) 0.007(3) 0.015(3) -0.005(2) 0.002(2) -0.0001(19) C7 0.019(3) 0.014(3) 0.018(3) -0.003(2) -0.004(2) -0.004(2) C8 0.007(3) 0.016(3) 0.018(3) -0.002(2) 0.001(2) -0.003(2) C9 0.013(3) 0.010(3) 0.012(3) 0.001(2) 0.001(2) -0.004(2) C10 0.016(3) 0.014(3) 0.011(3) -0.003(2) -0.001(2) -0.005(2) C11 0.022(3) 0.025(3) 0.005(3) -0.005(2) -0.002(2) -0.008(2) C12 0.031(3) 0.018(3) 0.013(3) 0.003(2) -0.005(2) -0.009(2) C13 0.027(3) 0.006(3) 0.022(3) -0.001(2) -0.002(2) -0.005(2) C14 0.012(3) 0.019(3) 0.013(3) -0.006(2) 0.002(2) -0.003(2) C15 0.024(3) 0.025(3) 0.016(3) -0.010(2) -0.001(2) -0.009(2) N1 0.010(2) 0.014(2) 0.009(2) -0.0007(18) -0.0016(17) 0.0026(17) N2 0.010(2) 0.015(2) 0.006(2) -0.0007(18) 0.0002(16) -0.0053(17) N3 0.014(2) 0.010(2) 0.011(2) -0.0032(18) -0.0013(17) -0.0006(17) O1 0.025(2) 0.0114(19) 0.0089(19) -0.0020(15) -0.0046(14) -0.0043(14) O2 0.020(2) 0.022(2) 0.012(2) -0.0014(15) -0.0053(15) -0.0041(15) _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 N2 1.948(4) . ? Cu1 O1 1.980(3) . ? Cu1 N1 2.013(4) . ? Cu1 Cl1 2.2333(13) . ? Cu1 O2 2.260(3) . ? C1 N1 1.346(6) . ? C1 C2 1.376(6) . ? C1 H1 0.9500 . ? C2 C3 1.378(6) . ? C2 H2 0.9500 . ? C3 C4 1.387(6) . ? C3 H3 0.9500 . ? C4 C5 1.381(6) . ? C4 H4 0.9500 . ? C5 N1 1.364(6) . ? C5 C6 1.477(6) . ? C6 N2 1.291(5) . ? C6 C7 1.482(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O1 1.275(5) . ? C8 N3 1.343(6) . ? C8 C9 1.490(6) . ? C9 C10 1.393(6) . ? C9 C14 1.394(6) . ? C10 C11 1.382(6) . ? C10 H10 0.9500 . ? C11 C12 1.384(6) . ? C11 H11 0.9500 . ? C12 C13 1.386(7) . ? C12 H12 0.9500 . ? C13 C14 1.389(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O2 1.434(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N2 N3 1.387(5) . ? O2 H2A 0.8501 . ? 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 Cu1 O1 79.30(14) . . ? N2 Cu1 N1 79.98(16) . . ? O1 Cu1 N1 159.11(15) . . ? N2 Cu1 Cl1 167.74(11) . . ? O1 Cu1 Cl1 99.82(10) . . ? N1 Cu1 Cl1 99.87(11) . . ? N2 Cu1 O2 93.73(13) . . ? O1 Cu1 O2 92.80(12) . . ? N1 Cu1 O2 91.14(13) . . ? Cl1 Cu1 O2 98.52(9) . . ? N1 C1 C2 122.0(5) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C1 C2 C3 119.3(5) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 119.1(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.5(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 120.9(4) . . ? N1 C5 C6 114.8(4) . . ? C4 C5 C6 124.3(4) . . ? N2 C6 C5 112.6(4) . . ? N2 C6 C7 124.7(4) . . ? C5 C6 C7 122.8(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 N3 125.8(4) . . ? O1 C8 C9 117.3(4) . . ? N3 C8 C9 116.9(4) . . ? C10 C9 C14 118.8(4) . . ? C10 C9 C8 123.0(4) . . ? C14 C9 C8 118.2(4) . . ? C11 C10 C9 120.3(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.5(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 119.4(5) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C9 120.9(5) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 N1 C5 119.1(4) . . ? C1 N1 Cu1 127.7(3) . . ? C5 N1 Cu1 113.0(3) . . ? C6 N2 N3 123.2(4) . . ? C6 N2 Cu1 119.6(3) . . ? N3 N2 Cu1 117.2(3) . . ? C8 N3 N2 106.8(4) . . ? C8 O1 Cu1 110.6(3) . . ? C15 O2 Cu1 122.9(3) . . ? C15 O2 H2A 109.8 . . ? Cu1 O2 H2A 126.0 . . ? 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 N1 C1 C2 C3 -0.5(7) . . . . ? C1 C2 C3 C4 -0.1(7) . . . . ? C2 C3 C4 C5 0.5(6) . . . . ? C3 C4 C5 N1 -0.3(6) . . . . ? C3 C4 C5 C6 177.5(4) . . . . ? N1 C5 C6 N2 3.0(5) . . . . ? C4 C5 C6 N2 -174.8(4) . . . . ? N1 C5 C6 C7 -177.0(4) . . . . ? C4 C5 C6 C7 5.2(7) . . . . ? O1 C8 C9 C10 -162.8(4) . . . . ? N3 C8 C9 C10 17.9(6) . . . . ? O1 C8 C9 C14 16.6(6) . . . . ? N3 C8 C9 C14 -162.7(4) . . . . ? C14 C9 C10 C11 1.2(6) . . . . ? C8 C9 C10 C11 -179.4(4) . . . . ? C9 C10 C11 C12 -0.6(7) . . . . ? C10 C11 C12 C13 0.1(7) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C9 0.9(7) . . . . ? C10 C9 C14 C13 -1.4(7) . . . . ? C8 C9 C14 C13 179.2(4) . . . . ? C2 C1 N1 C5 0.8(6) . . . . ? C2 C1 N1 Cu1 -174.2(3) . . . . ? C4 C5 N1 C1 -0.4(6) . . . . ? C6 C5 N1 C1 -178.3(4) . . . . ? C4 C5 N1 Cu1 175.3(3) . . . . ? C6 C5 N1 Cu1 -2.6(4) . . . . ? N2 Cu1 N1 C1 176.5(4) . . . . ? O1 Cu1 N1 C1 -176.2(4) . . . . ? Cl1 Cu1 N1 C1 -16.0(4) . . . . ? O2 Cu1 N1 C1 82.9(4) . . . . ? N2 Cu1 N1 C5 1.2(3) . . . . ? O1 Cu1 N1 C5 8.5(6) . . . . ? Cl1 Cu1 N1 C5 168.8(3) . . . . ? O2 Cu1 N1 C5 -92.4(3) . . . . ? C5 C6 N2 N3 176.8(4) . . . . ? C7 C6 N2 N3 -3.2(6) . . . . ? C5 C6 N2 Cu1 -2.1(5) . . . . ? C7 C6 N2 Cu1 177.9(3) . . . . ? O1 Cu1 N2 C6 -176.8(3) . . . . ? N1 Cu1 N2 C6 0.6(3) . . . . ? Cl1 Cu1 N2 C6 -89.8(6) . . . . ? O2 Cu1 N2 C6 91.1(3) . . . . ? O1 Cu1 N2 N3 4.3(3) . . . . ? N1 Cu1 N2 N3 -178.3(3) . . . . ? Cl1 Cu1 N2 N3 91.3(6) . . . . ? O2 Cu1 N2 N3 -87.9(3) . . . . ? O1 C8 N3 N2 -1.7(6) . . . . ? C9 C8 N3 N2 177.5(3) . . . . ? C6 N2 N3 C8 178.3(4) . . . . ? Cu1 N2 N3 C8 -2.9(4) . . . . ? N3 C8 O1 Cu1 5.1(5) . . . . ? C9 C8 O1 Cu1 -174.1(3) . . . . ? N2 Cu1 O1 C8 -4.7(3) . . . . ? N1 Cu1 O1 C8 -12.0(5) . . . . ? Cl1 Cu1 O1 C8 -172.3(3) . . . . ? O2 Cu1 O1 C8 88.6(3) . . . . ? N2 Cu1 O2 C15 -150.4(3) . . . . ? O1 Cu1 O2 C15 130.1(3) . . . . ? N1 Cu1 O2 C15 -70.4(3) . . . . ? Cl1 Cu1 O2 C15 29.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 59.98 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.620 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.119 data_new_a _database_code_depnum_ccdc_archive 'CCDC 852731' #TrackingRef '- 2-CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Cl Cu N3 O2 S' _chemical_formula_weight 375.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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 7.1463(7) _cell_length_b 11.4225(11) _cell_length_c 18.1483(18) _cell_angle_alpha 90.00 _cell_angle_beta 99.366(7) _cell_angle_gamma 90.00 _cell_volume 1461.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 944 _cell_measurement_theta_min 4.59 _cell_measurement_theta_max 61.45 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 5.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7125 _exptl_absorpt_correction_T_max 0.8597 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER GADDS D8 Discover' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32062 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 59.98 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _reflns_number_total 2146 _reflns_number_gt 1805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'FRAMBO (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) ; _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _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^)+(0.0526P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2146 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.21190(6) 0.68906(3) 1.03936(2) 0.01408(16) Uani 1 1 d . . . Cl1 Cl 0.13709(11) 0.83805(6) 1.10809(4) 0.0210(2) Uani 1 1 d . . . S1 S 0.38810(12) 0.39112(7) 1.23247(4) 0.0228(2) Uani 1 1 d . . . C1 C 0.1998(4) 0.5595(2) 0.90714(16) 0.0129(6) Uani 1 1 d . . . C2 C 0.1714(4) 0.6822(2) 0.88175(16) 0.0128(6) Uani 1 1 d . . . C3 C 0.1382(4) 0.8746(3) 0.91854(16) 0.0167(7) Uani 1 1 d . . . H3A H 0.1277 0.9297 0.9569 0.020 Uiso 1 1 calc R . . C4 C 0.1294(4) 0.9144(3) 0.84603(17) 0.0187(7) Uani 1 1 d . . . H4A H 0.1133 0.9954 0.8350 0.022 Uiso 1 1 calc R . . C5 C 0.1443(4) 0.8347(3) 0.78983(17) 0.0183(7) Uani 1 1 d . . . H5A H 0.1424 0.8603 0.7399 0.022 Uiso 1 1 calc R . . C6 C 0.1620(4) 0.7170(3) 0.80773(16) 0.0159(7) Uani 1 1 d . . . H6A H 0.1676 0.6604 0.7698 0.019 Uiso 1 1 calc R . . C7 C 0.2061(4) 0.4606(3) 0.85472(16) 0.0194(7) Uani 1 1 d . . . H7A H 0.1396 0.3931 0.8715 0.029 Uiso 1 1 calc R . . H7B H 0.3384 0.4396 0.8534 0.029 Uiso 1 1 calc R . . H7C H 0.1444 0.4838 0.8046 0.029 Uiso 1 1 calc R . . C8 C 0.2721(4) 0.4650(2) 1.08848(16) 0.0136(7) Uani 1 1 d . . . C9 C 0.3148(4) 0.3657(3) 1.13918(16) 0.0159(7) Uani 1 1 d . . . C10 C 0.3082(4) 0.2438(2) 1.12288(15) 0.0093(6) Uani 1 1 d . . . H10A H 0.2730 0.2107 1.0746 0.011 Uiso 1 1 calc R . . C11 C 0.3622(4) 0.1792(3) 1.18981(18) 0.0213(7) Uani 1 1 d . . . H11A H 0.3641 0.0961 1.1912 0.026 Uiso 1 1 calc R . . C12 C 0.4107(4) 0.2461(3) 1.25150(18) 0.0220(7) Uani 1 1 d . . . H12A H 0.4526 0.2152 1.3000 0.026 Uiso 1 1 calc R . . C13 C 0.5970(5) 0.8473(3) 1.05302(19) 0.0275(8) Uani 1 1 d . . . H13A H 0.7358 0.8453 1.0648 0.041 Uiso 1 1 calc R . . H13B H 0.5462 0.8893 1.0925 0.041 Uiso 1 1 calc R . . H13C H 0.5585 0.8875 1.0053 0.041 Uiso 1 1 calc R . . N1 N 0.2214(3) 0.54995(19) 0.97889(13) 0.0124(5) Uani 1 1 d . . . N3 N 0.2590(3) 0.44375(19) 1.01525(13) 0.0140(5) Uani 1 1 d . . . N2 N 0.1610(3) 0.7616(2) 0.93663(13) 0.0132(5) Uani 1 1 d . . . O1 O 0.2540(3) 0.56581(16) 1.11777(10) 0.0162(5) Uani 1 1 d . . . O2 O 0.5255(3) 0.73094(16) 1.04786(11) 0.0183(5) Uani 1 1 d . . . H2O H 0.5979 0.6820 1.0312 0.027 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0190(3) 0.0134(3) 0.0103(3) -0.00055(17) 0.00349(18) 0.00329(17) Cl1 0.0296(5) 0.0191(4) 0.0152(4) -0.0028(3) 0.0065(3) 0.0084(3) S1 0.0311(5) 0.0213(4) 0.0159(4) 0.0028(3) 0.0032(3) -0.0022(3) C1 0.0096(16) 0.0152(15) 0.0141(17) -0.0004(12) 0.0026(12) 0.0002(11) C2 0.0086(16) 0.0163(16) 0.0132(16) -0.0004(12) 0.0012(11) -0.0003(11) C3 0.0175(17) 0.0153(16) 0.0168(18) -0.0015(13) 0.0017(13) 0.0015(12) C4 0.0185(18) 0.0160(16) 0.0212(18) 0.0034(14) 0.0024(13) 0.0022(12) C5 0.0173(17) 0.0237(17) 0.0142(17) 0.0049(13) 0.0032(12) 0.0032(13) C6 0.0141(16) 0.0199(17) 0.0134(16) -0.0021(13) 0.0019(12) 0.0007(12) C7 0.0243(18) 0.0186(16) 0.0157(17) -0.0018(13) 0.0047(13) -0.0006(13) C8 0.0101(16) 0.0152(16) 0.0165(17) 0.0002(13) 0.0051(12) 0.0007(11) C9 0.0138(17) 0.0207(16) 0.0150(17) 0.0013(13) 0.0076(12) 0.0001(12) C10 0.0066(15) 0.0120(14) 0.0099(15) 0.0030(12) 0.0031(11) -0.0037(11) C11 0.0220(19) 0.0129(16) 0.030(2) 0.0048(14) 0.0074(14) 0.0009(13) C12 0.0209(19) 0.0240(18) 0.0211(18) 0.0105(14) 0.0031(13) -0.0032(14) C13 0.027(2) 0.0236(18) 0.033(2) -0.0082(16) 0.0089(15) -0.0056(15) N1 0.0121(14) 0.0121(13) 0.0130(14) 0.0026(10) 0.0023(10) -0.0002(10) N3 0.0184(14) 0.0111(13) 0.0127(14) 0.0025(10) 0.0031(10) 0.0018(10) N2 0.0119(14) 0.0148(13) 0.0133(13) -0.0009(11) 0.0028(10) 0.0015(10) O1 0.0225(12) 0.0145(11) 0.0122(11) -0.0021(8) 0.0043(9) 0.0034(8) O2 0.0165(12) 0.0111(10) 0.0279(13) -0.0019(9) 0.0059(9) 0.0023(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 Cu1 N1 1.939(2) . ? Cu1 O1 1.9896(19) . ? Cu1 N3 2.019(2) . ? Cu1 Cl1 2.2259(8) . ? Cu1 O2 2.272(2) . ? S1 C12 1.694(3) . ? S1 C9 1.714(3) . ? C1 N1 1.291(4) . ? C1 C2 1.479(4) . ? C1 C7 1.482(4) . ? C2 N2 1.358(4) . ? C2 C6 1.392(4) . ? C3 N2 1.335(4) . ? C3 C4 1.384(4) . ? C3 H3A 0.9500 . ? C4 C5 1.384(4) . ? C4 H4A 0.9500 . ? C5 C6 1.384(4) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O1 1.284(3) . ? C8 N3 1.339(4) . ? C8 C9 1.461(4) . ? C9 C10 1.422(4) . ? C10 C11 1.420(4) . ? C10 H10A 0.9500 . ? C11 C12 1.353(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 O2 1.422(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 N3 1.386(3) . ? O2 H2O 0.8500 . ? 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 79.03(9) . . ? N1 Cu1 N2 80.29(9) . . ? O1 Cu1 N2 159.19(9) . . ? N1 Cu1 Cl1 167.85(7) . . ? O1 Cu1 Cl1 99.35(6) . . ? N2 Cu1 Cl1 100.37(7) . . ? N1 Cu1 O2 94.94(9) . . ? O1 Cu1 O2 93.88(8) . . ? N2 Cu1 O2 90.20(9) . . ? Cl1 Cu1 O2 97.19(6) . . ? C12 S1 C9 92.24(15) . . ? N1 C1 C2 112.5(2) . . ? N1 C1 C7 124.9(3) . . ? C2 C1 C7 122.6(3) . . ? N2 C2 C6 121.2(3) . . ? N2 C2 C1 115.2(2) . . ? C6 C2 C1 123.6(3) . . ? N2 C3 C4 122.5(3) . . ? N2 C3 H3A 118.8 . . ? C4 C3 H3A 118.8 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 118.8(3) . . ? C6 C5 H5A 120.6 . . ? C4 C5 H5A 120.6 . . ? C5 C6 C2 119.5(3) . . ? C5 C6 H6A 120.3 . . ? C2 C6 H6A 120.3 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 N3 125.3(3) . . ? O1 C8 C9 117.4(2) . . ? N3 C8 C9 117.2(2) . . ? C10 C9 C8 129.2(3) . . ? C10 C9 S1 111.5(2) . . ? C8 C9 S1 119.3(2) . . ? C11 C10 C9 109.6(3) . . ? C11 C10 H10A 125.2 . . ? C9 C10 H10A 125.2 . . ? C12 C11 C10 114.3(3) . . ? C12 C11 H11A 122.9 . . ? C10 C11 H11A 122.9 . . ? C11 C12 S1 112.4(2) . . ? C11 C12 H12A 123.8 . . ? S1 C12 H12A 123.8 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 N1 N3 122.5(2) . . ? C1 N1 Cu1 119.48(19) . . ? N3 N1 Cu1 118.01(17) . . ? C8 N3 N1 106.9(2) . . ? C3 N2 C2 119.0(2) . . ? C3 N2 Cu1 128.4(2) . . ? C2 N2 Cu1 112.33(18) . . ? C8 O1 Cu1 110.63(17) . . ? C13 O2 Cu1 122.79(17) . . ? C13 O2 H2O 113.8 . . ? Cu1 O2 H2O 119.2 . . ? 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 N1 C1 C2 N2 -3.9(4) . . . . ? C7 C1 C2 N2 177.3(3) . . . . ? N1 C1 C2 C6 174.0(3) . . . . ? C7 C1 C2 C6 -4.9(4) . . . . ? N2 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C6 1.9(5) . . . . ? C4 C5 C6 C2 -2.4(4) . . . . ? N2 C2 C6 C5 0.9(4) . . . . ? C1 C2 C6 C5 -176.9(3) . . . . ? O1 C8 C9 C10 167.3(3) . . . . ? N3 C8 C9 C10 -14.1(4) . . . . ? O1 C8 C9 S1 -13.9(4) . . . . ? N3 C8 C9 S1 164.7(2) . . . . ? C12 S1 C9 C10 -0.1(2) . . . . ? C12 S1 C9 C8 -179.1(2) . . . . ? C8 C9 C10 C11 179.8(3) . . . . ? S1 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C12 -1.6(4) . . . . ? C10 C11 C12 S1 1.5(4) . . . . ? C9 S1 C12 C11 -0.8(3) . . . . ? C2 C1 N1 N3 -176.9(2) . . . . ? C7 C1 N1 N3 2.0(4) . . . . ? C2 C1 N1 Cu1 0.5(3) . . . . ? C7 C1 N1 Cu1 179.3(2) . . . . ? O1 Cu1 N1 C1 179.5(2) . . . . ? N2 Cu1 N1 C1 1.8(2) . . . . ? Cl1 Cu1 N1 C1 96.0(4) . . . . ? O2 Cu1 N1 C1 -87.5(2) . . . . ? O1 Cu1 N1 N3 -3.08(18) . . . . ? N2 Cu1 N1 N3 179.3(2) . . . . ? Cl1 Cu1 N1 N3 -86.5(4) . . . . ? O2 Cu1 N1 N3 89.92(19) . . . . ? O1 C8 N3 N1 -0.5(4) . . . . ? C9 C8 N3 N1 -179.0(2) . . . . ? C1 N1 N3 C8 -179.8(2) . . . . ? Cu1 N1 N3 C8 2.8(3) . . . . ? C4 C3 N2 C2 -1.6(4) . . . . ? C4 C3 N2 Cu1 171.1(2) . . . . ? C6 C2 N2 C3 1.1(4) . . . . ? C1 C2 N2 C3 179.0(2) . . . . ? C6 C2 N2 Cu1 -172.7(2) . . . . ? C1 C2 N2 Cu1 5.2(3) . . . . ? N1 Cu1 N2 C3 -177.0(2) . . . . ? O1 Cu1 N2 C3 176.5(2) . . . . ? Cl1 Cu1 N2 C3 15.4(2) . . . . ? O2 Cu1 N2 C3 -82.0(2) . . . . ? N1 Cu1 N2 C2 -3.85(19) . . . . ? O1 Cu1 N2 C2 -10.4(4) . . . . ? Cl1 Cu1 N2 C2 -171.53(18) . . . . ? O2 Cu1 N2 C2 91.12(19) . . . . ? N3 C8 O1 Cu1 -1.9(3) . . . . ? C9 C8 O1 Cu1 176.60(19) . . . . ? N1 Cu1 O1 C8 2.52(18) . . . . ? N2 Cu1 O1 C8 9.1(4) . . . . ? Cl1 Cu1 O1 C8 170.29(17) . . . . ? O2 Cu1 O1 C8 -91.76(18) . . . . ? N1 Cu1 O2 C13 148.2(2) . . . . ? O1 Cu1 O2 C13 -132.5(2) . . . . ? N2 Cu1 O2 C13 67.9(2) . . . . ? Cl1 Cu1 O2 C13 -32.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 59.98 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.322 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.096