# 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_cu-h2ca-43 _audit_creation_date 2013-02-06T16:26:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C16 H8 Cl2 Cu1 N2 O4' _chemical_formula_sum 'C16 H8 Cl2 Cu N2 O4' _chemical_formula_weight 426.68 _chemical_absolute_configuration unk #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.2428(5) _cell_length_b 17.3184(17) _cell_length_c 8.4028(17) _cell_angle_alpha 90 _cell_angle_beta 93.638(11) _cell_angle_gamma 90 _cell_volume 761.41(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 957 _cell_measurement_theta_min 5.1035 _cell_measurement_theta_max 64.6662 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 5.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.39997 _exptl_absorpt_correction_T_max 1 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Xcalibur, Ruby, Nova' _diffrn_measurement_method 'CCD, \w scans' _diffrn_reflns_number 2113 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 64.76 _diffrn_reflns_theta_full 64.76 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1441 _reflns_number_gt 1125 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0200P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1441 _refine_ls_number_parameters 223 _refine_ls_number_restraints 13 _refine_ls_R_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.2589 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(12) _refine_diff_density_max 1.021 _refine_diff_density_min -1.566 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cu1 Cu 0.3617(5) 0.8057(2) 0.0930(5) 0.0546(10) Uani 1 d . . . Cl1 Cl -0.0625(12) 0.6214(4) -0.2682(9) 0.072(2) Uani 1 d . . . Cl2 Cl -0.3558(12) 0.9685(4) -0.1192(11) 0.075(2) Uani 1 d . . . O1 O 0.087(2) 0.8730(9) 0.0144(19) 0.047(4) Uani 1 d . . . O2 O 0.202(3) 0.7316(9) -0.059(2) 0.051(5) Uani 1 d . . . O3 O -0.512(3) 0.7100(11) -0.417(2) 0.069(6) Uani 1 d . . . O4 O -0.635(3) 0.8574(12) -0.338(2) 0.077(6) Uani 1 d . . . C1 C -0.070(5) 0.8417(16) -0.088(4) 0.059(8) Uani 1 d . . . C2 C 0.008(4) 0.7572(14) -0.125(3) 0.039(5) Uani 1 d . . . C3 C -0.151(4) 0.7152(13) -0.230(3) 0.049(6) Uani 1 d . . . C4 C -0.368(4) 0.7466(18) -0.318(4) 0.062(8) Uani 1 d . . . C5 C -0.446(5) 0.8297(17) -0.280(4) 0.072(9) Uani 1 d . . . C6 C -0.281(4) 0.8679(15) -0.155(3) 0.054(7) Uani 1 d . . . N1 N 0.538(3) 0.8769(12) 0.252(3) 0.055(6) Uani 1 d . . . N2 N 0.629(3) 0.7327(12) 0.180(2) 0.046(5) Uani 1 d . . . C7 C 0.458(4) 0.9497(15) 0.279(4) 0.063(8) Uani 1 d . . . H7 H 0.3069 0.968 0.2291 0.075 Uiso 1 calc R . . C8 C 0.603(5) 0.9963(17) 0.381(4) 0.074(9) Uani 1 d . . . H8 H 0.5579 1.0475 0.3961 0.089 Uiso 1 calc R . . C9 C 0.823(3) 0.9650(12) 0.462(2) 0.056(7) Uani 1 d . . . H9 H 0.9195 0.994 0.5368 0.067 Uiso 1 calc R . . C10 C 0.889(3) 0.8915(12) 0.429(2) 0.060(7) Uani 1 d R . . H10 H 1.0383 0.8706 0.4763 0.072 Uiso 1 d R . . C11 C 0.734(4) 0.8468(14) 0.324(3) 0.047(6) Uani 1 d . . . C12 C 0.806(4) 0.7667(13) 0.288(3) 0.038(5) Uani 1 d U . . C13 C 1.003(4) 0.7250(14) 0.358(3) 0.046(6) Uani 1 d U . . H13 H 1.1087 0.7467 0.4395 0.056 Uiso 1 calc R . . C14 C 1.047(5) 0.6498(18) 0.307(4) 0.081(10) Uani 1 d . . . H14 H 1.1894 0.6223 0.347 0.097 Uiso 1 calc R . . C15 C 0.866(4) 0.6157(15) 0.193(3) 0.053(6) Uani 1 d . . . H15 H 0.8822 0.5645 0.1613 0.063 Uiso 1 calc R . . C16 C 0.661(4) 0.6619(16) 0.128(3) 0.061(7) Uani 1 d . . . H16 H 0.5486 0.6421 0.0475 0.073 Uiso 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 0.0342(14) 0.0391(17) 0.088(3) -0.001(2) -0.0187(15) 0.0013(16) Cl1 0.065(4) 0.053(4) 0.095(5) -0.018(4) -0.012(4) -0.009(3) Cl2 0.049(3) 0.052(4) 0.121(7) 0.021(4) -0.006(4) 0.011(3) O1 0.031(7) 0.044(9) 0.066(11) -0.017(9) 0.003(8) -0.011(7) O2 0.031(8) 0.041(8) 0.077(12) -0.026(9) -0.026(8) 0.005(7) O3 0.060(10) 0.080(14) 0.062(12) 0.001(10) -0.035(10) -0.025(10) O4 0.047(10) 0.090(15) 0.088(14) -0.004(12) -0.032(10) 0.002(10) C1 0.037(12) 0.051(15) 0.09(2) -0.005(15) 0.016(14) -0.004(11) C2 0.031(11) 0.048(14) 0.038(12) -0.006(11) 0.012(11) -0.012(10) C3 0.048(12) 0.042(15) 0.054(16) -0.014(11) -0.009(12) -0.015(10) C4 0.028(11) 0.08(2) 0.08(2) 0.014(17) 0.001(14) -0.006(12) C5 0.025(11) 0.07(2) 0.12(3) 0.011(18) 0.012(14) -0.010(12) C6 0.026(10) 0.050(14) 0.086(18) 0.016(14) 0.006(12) 0.012(10) N1 0.029(9) 0.038(11) 0.097(17) -0.015(12) 0.004(10) -0.004(9) N2 0.040(10) 0.041(11) 0.055(13) -0.008(10) 0.002(10) 0.002(9) C7 0.029(11) 0.050(16) 0.11(2) 0.010(16) 0.018(13) 0.004(12) C8 0.053(15) 0.046(15) 0.12(3) -0.004(17) 0.001(17) -0.003(13) C9 0.054(14) 0.058(16) 0.058(17) -0.023(14) 0.014(13) -0.017(12) C10 0.036(12) 0.068(18) 0.075(19) 0.015(15) -0.002(13) -0.013(12) C11 0.027(11) 0.050(14) 0.068(16) -0.004(13) 0.021(12) 0.002(10) C12 0.027(8) 0.041(8) 0.044(9) 0.006(8) -0.008(7) -0.001(7) C13 0.047(9) 0.048(9) 0.041(9) -0.010(8) -0.018(8) -0.001(8) C14 0.046(12) 0.07(2) 0.13(3) 0.04(2) 0.015(16) 0.011(14) C15 0.049(12) 0.057(16) 0.050(14) 0.015(12) -0.017(11) 0.002(11) C16 0.051(13) 0.066(19) 0.064(17) 0.001(14) -0.014(13) -0.011(12) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O1 1.935(16) . ? Cu1 O2 1.958(14) . ? Cu1 N2 1.99(2) . ? Cu1 N1 2.00(2) . ? Cl1 C3 1.73(2) . ? Cl2 C6 1.82(3) . ? O1 C1 1.27(3) . ? O2 C2 1.21(3) . ? O3 C4 1.26(3) . ? O4 C5 1.18(3) . ? C1 C6 1.29(3) . ? C1 C2 1.56(3) . ? C2 C3 1.38(3) . ? C3 C4 1.42(3) . ? C4 C5 1.54(4) . ? C5 C6 1.47(4) . ? N1 C11 1.28(3) . ? N1 C7 1.35(3) . ? N2 C16 1.32(3) . ? N2 C12 1.39(3) . ? C7 C8 1.37(4) . ? C7 H7 0.93 . ? C8 C9 1.41(3) . ? C8 H8 0.93 . ? C9 C10 1.3531 . ? C9 H9 0.93 . ? C10 C11 1.39(3) . ? C10 H10 0.93 . ? C11 C12 1.47(3) . ? C12 C13 1.37(3) . ? C13 C14 1.39(4) . ? C13 H13 0.93 . ? C14 C15 1.44(4) . ? C14 H14 0.93 . ? C15 C16 1.42(3) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O2 83.9(6) . . ? O1 Cu1 N2 176.5(8) . . ? O2 Cu1 N2 94.9(7) . . ? O1 Cu1 N1 99.1(7) . . ? O2 Cu1 N1 177.0(8) . . ? N2 Cu1 N1 82.1(8) . . ? C1 O1 Cu1 114.1(16) . . ? C2 O2 Cu1 111.8(15) . . ? O1 C1 C6 130(3) . . ? O1 C1 C2 112(2) . . ? C6 C1 C2 118(3) . . ? O2 C2 C3 124(2) . . ? O2 C2 C1 118(2) . . ? C3 C2 C1 118(2) . . ? C2 C3 C4 124(2) . . ? C2 C3 Cl1 117.0(19) . . ? C4 C3 Cl1 118.6(19) . . ? O3 C4 C3 125(3) . . ? O3 C4 C5 117(2) . . ? C3 C4 C5 118(3) . . ? O4 C5 C6 124(3) . . ? O4 C5 C4 122(3) . . ? C6 C5 C4 115(2) . . ? C1 C6 C5 127(3) . . ? C1 C6 Cl2 117(2) . . ? C5 C6 Cl2 115.1(17) . . ? C11 N1 C7 123(2) . . ? C11 N1 Cu1 113.1(17) . . ? C7 N1 Cu1 123.7(18) . . ? C16 N2 C12 121(2) . . ? C16 N2 Cu1 124.6(17) . . ? C12 N2 Cu1 113.3(16) . . ? N1 C7 C8 119(2) . . ? N1 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C7 C8 C9 119(2) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C10 C9 C8 118.3(15) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C11 120.5(13) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.7 . . ? N1 C11 C10 120(2) . . ? N1 C11 C12 120(2) . . ? C10 C11 C12 121(2) . . ? C13 C12 N2 121(2) . . ? C13 C12 C11 127(2) . . ? N2 C12 C11 112(2) . . ? C12 C13 C14 120(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C15 118(2) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 119(2) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N2 C16 C15 120(2) . . ? N2 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? 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 O2 Cu1 O1 C1 2.6(19) . . . . ? N2 Cu1 O1 C1 -68(14) . . . . ? N1 Cu1 O1 C1 -177.2(18) . . . . ? O1 Cu1 O2 C2 -3.3(18) . . . . ? N2 Cu1 O2 C2 173.5(18) . . . . ? N1 Cu1 O2 C2 173(17) . . . . ? Cu1 O1 C1 C6 175(3) . . . . ? Cu1 O1 C1 C2 -2(3) . . . . ? Cu1 O2 C2 C3 -176(2) . . . . ? Cu1 O2 C2 C1 3(3) . . . . ? O1 C1 C2 O2 -1(3) . . . . ? C6 C1 C2 O2 -178(3) . . . . ? O1 C1 C2 C3 178(2) . . . . ? C6 C1 C2 C3 1(4) . . . . ? O2 C2 C3 C4 -175(3) . . . . ? C1 C2 C3 C4 6(4) . . . . ? O2 C2 C3 Cl1 0(4) . . . . ? C1 C2 C3 Cl1 -179.5(19) . . . . ? C2 C3 C4 O3 178(3) . . . . ? Cl1 C3 C4 O3 4(4) . . . . ? C2 C3 C4 C5 -7(4) . . . . ? Cl1 C3 C4 C5 179(2) . . . . ? O3 C4 C5 O4 2(5) . . . . ? C3 C4 C5 O4 -173(3) . . . . ? O3 C4 C5 C6 176(2) . . . . ? C3 C4 C5 C6 1(4) . . . . ? O1 C1 C6 C5 176(3) . . . . ? C2 C1 C6 C5 -8(4) . . . . ? O1 C1 C6 Cl2 7(4) . . . . ? C2 C1 C6 Cl2 -176.3(18) . . . . ? O4 C5 C6 C1 -179(3) . . . . ? C4 C5 C6 C1 7(4) . . . . ? O4 C5 C6 Cl2 -10(4) . . . . ? C4 C5 C6 Cl2 176(2) . . . . ? O1 Cu1 N1 C11 -179.8(18) . . . . ? O2 Cu1 N1 C11 4(19) . . . . ? N2 Cu1 N1 C11 3(2) . . . . ? O1 Cu1 N1 C7 0(2) . . . . ? O2 Cu1 N1 C7 -176(16) . . . . ? N2 Cu1 N1 C7 -177(2) . . . . ? O1 Cu1 N2 C16 74(14) . . . . ? O2 Cu1 N2 C16 4(2) . . . . ? N1 Cu1 N2 C16 -176(2) . . . . ? O1 Cu1 N2 C12 -115(13) . . . . ? O2 Cu1 N2 C12 174.4(17) . . . . ? N1 Cu1 N2 C12 -5.6(18) . . . . ? C11 N1 C7 C8 5(4) . . . . ? Cu1 N1 C7 C8 -175(2) . . . . ? N1 C7 C8 C9 -4(4) . . . . ? C7 C8 C9 C10 4(3) . . . . ? C8 C9 C10 C11 -4.0(18) . . . . ? C7 N1 C11 C10 -5(4) . . . . ? Cu1 N1 C11 C10 174.7(17) . . . . ? C7 N1 C11 C12 179(2) . . . . ? Cu1 N1 C11 C12 -1(3) . . . . ? C9 C10 C11 N1 5(3) . . . . ? C9 C10 C11 C12 -179.9(16) . . . . ? C16 N2 C12 C13 -8(4) . . . . ? Cu1 N2 C12 C13 -179.4(19) . . . . ? C16 N2 C12 C11 178(2) . . . . ? Cu1 N2 C12 C11 6(3) . . . . ? N1 C11 C12 C13 -178(3) . . . . ? C10 C11 C12 C13 7(4) . . . . ? N1 C11 C12 N2 -4(3) . . . . ? C10 C11 C12 N2 -179(2) . . . . ? N2 C12 C13 C14 8(4) . . . . ? C11 C12 C13 C14 -179(2) . . . . ? C12 C13 C14 C15 -6(4) . . . . ? C13 C14 C15 C16 4(4) . . . . ? C12 N2 C16 C15 7(4) . . . . ? Cu1 N2 C16 C15 176.6(17) . . . . ? C14 C15 C16 N2 -5(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 947424' ####################################################################### # # 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_cu-h2ca-44 _audit_creation_date 2013-02-06T16:37:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C16 H8 Cl2 Cu1 N2 O4' _chemical_formula_sum 'C16 H8 Cl2 Cu N2 O4' _chemical_formula_weight 426.68 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' 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 25.0006(6) _cell_length_b 7.4597(2) _cell_length_c 17.2095(4) _cell_angle_alpha 90 _cell_angle_beta 104.509(3) _cell_angle_gamma 90 _cell_volume 3107.16(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3000 _cell_measurement_theta_min 3.6494 _cell_measurement_theta_max 65.0105 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 5.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.48072 _exptl_absorpt_correction_T_max 1 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Xcalibur, Ruby, Nova' _diffrn_measurement_method 'CCD, \w scans' _diffrn_reflns_number 4763 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 65.11 _diffrn_reflns_theta_full 65.11 _diffrn_measured_fraction_theta_max 0.95 _diffrn_measured_fraction_theta_full 0.95 _reflns_number_total 2430 _reflns_number_gt 2129 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0681P)^2^+0.9230P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00027(6) _refine_ls_number_reflns 2430 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.036 _refine_ls_wR_factor_ref 0.1057 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.811 _refine_diff_density_min -0.624 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cu1 Cu 0.449360(15) 0.21822(6) 0.97837(2) 0.0354(2) Uani 1 d . . . Cl1 Cl 0.62579(3) 0.18853(11) 1.18032(4) 0.0451(2) Uani 1 d . . . Cl2 Cl 0.56650(3) 0.52044(11) 0.82954(5) 0.0476(2) Uani 1 d . . . O1 O 0.49305(8) 0.3384(3) 0.91701(12) 0.0410(5) Uani 1 d . . . O2 O 0.51834(8) 0.1869(3) 1.05687(12) 0.0413(5) Uani 1 d . . . O3 O 0.70338(8) 0.3575(3) 1.09398(14) 0.0519(6) Uani 1 d . . . O4 O 0.67803(9) 0.4981(3) 0.94419(15) 0.0527(6) Uani 1 d . . . C1 C 0.54395(11) 0.3524(4) 0.95504(17) 0.0311(6) Uani 1 d . . . C2 C 0.55885(11) 0.2662(4) 1.03752(18) 0.0318(6) Uani 1 d . . . C3 C 0.61119(12) 0.2770(4) 1.08418(18) 0.0323(6) Uani 1 d . . . C4 C 0.65535(11) 0.3523(4) 1.05627(18) 0.0353(7) Uani 1 d . . . C5 C 0.64038(11) 0.4360(4) 0.96977(19) 0.0363(7) Uani 1 d . . . C6 C 0.58371(11) 0.4338(4) 0.92588(17) 0.0337(6) Uani 1 d . . . N1 N 0.40291(9) 0.1055(3) 1.04014(14) 0.0326(5) Uani 1 d . . . N2 N 0.37856(9) 0.2464(3) 0.89918(14) 0.0317(5) Uani 1 d . . . C7 C 0.42064(12) 0.0401(4) 1.11479(18) 0.0382(7) Uani 1 d . . . H7 H 0.4581 0.0452 1.1403 0.046 Uiso 1 calc R . . C8 C 0.38464(13) -0.0341(4) 1.15435(19) 0.0420(7) Uani 1 d . . . H8 H 0.3976 -0.08 1.2059 0.05 Uiso 1 calc R . . C9 C 0.32937(13) -0.0397(4) 1.1170(2) 0.0456(8) Uani 1 d . . . H9 H 0.3045 -0.0885 1.1434 0.055 Uiso 1 calc R . . C10 C 0.31068(12) 0.0275(4) 1.0399(2) 0.0415(7) Uani 1 d . . . H10 H 0.2733 0.0244 1.0138 0.05 Uiso 1 calc R . . C11 C 0.34848(11) 0.0990(3) 1.00265(17) 0.0314(6) Uani 1 d . . . C12 C 0.33476(11) 0.1770(4) 0.92108(18) 0.0325(6) Uani 1 d . . . C13 C 0.28234(13) 0.1803(4) 0.8694(2) 0.0441(8) Uani 1 d . . . H13 H 0.2524 0.1311 0.8847 0.053 Uiso 1 calc R . . C14 C 0.27558(13) 0.2580(5) 0.7949(2) 0.0493(8) Uani 1 d . . . H14 H 0.2408 0.2607 0.7592 0.059 Uiso 1 calc R . . C15 C 0.31988(13) 0.3309(4) 0.77360(19) 0.0431(8) Uani 1 d . . . H15 H 0.3155 0.3846 0.7236 0.052 Uiso 1 calc R . . C16 C 0.37116(13) 0.3244(4) 0.82667(18) 0.0384(7) Uani 1 d . . . H16 H 0.4013 0.3748 0.8122 0.046 Uiso 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 0.0197(3) 0.0555(3) 0.0302(3) 0.00093(18) 0.00479(19) -0.01040(17) Cl1 0.0350(4) 0.0586(5) 0.0371(5) 0.0057(3) 0.0005(3) -0.0031(3) Cl2 0.0513(5) 0.0620(5) 0.0337(4) 0.0024(3) 0.0183(4) -0.0073(4) O1 0.0232(10) 0.0675(13) 0.0307(11) 0.0059(10) 0.0039(9) -0.0118(9) O2 0.0235(10) 0.0675(13) 0.0317(11) 0.0074(10) 0.0047(9) -0.0143(9) O3 0.0211(10) 0.0766(15) 0.0554(15) -0.0037(12) 0.0050(10) -0.0082(10) O4 0.0309(11) 0.0741(15) 0.0593(16) 0.0025(12) 0.0228(11) -0.0150(11) C1 0.0264(14) 0.0397(14) 0.0288(15) -0.0039(11) 0.0099(12) -0.0051(11) C2 0.0243(13) 0.0415(14) 0.0313(15) -0.0055(12) 0.0104(12) -0.0052(11) C3 0.0264(14) 0.0395(14) 0.0305(16) -0.0023(11) 0.0058(12) -0.0039(11) C4 0.0240(14) 0.0428(15) 0.0403(17) -0.0129(13) 0.0102(13) -0.0031(12) C5 0.0274(14) 0.0404(14) 0.0457(18) -0.0093(13) 0.0179(13) -0.0070(12) C6 0.0312(14) 0.0428(15) 0.0300(15) -0.0037(12) 0.0129(12) -0.0050(12) N1 0.0231(11) 0.0423(12) 0.0323(13) -0.0058(10) 0.0068(10) -0.0071(10) N2 0.0236(11) 0.0452(12) 0.0265(13) -0.0072(10) 0.0068(10) -0.0053(10) C7 0.0314(14) 0.0475(16) 0.0349(17) -0.0022(13) 0.0068(13) -0.0038(12) C8 0.0460(17) 0.0474(16) 0.0365(18) 0.0017(13) 0.0174(15) -0.0044(14) C9 0.0412(17) 0.0523(17) 0.051(2) 0.0035(15) 0.0252(16) -0.0058(14) C10 0.0261(13) 0.0496(16) 0.051(2) -0.0042(14) 0.0145(14) -0.0071(13) C11 0.0245(13) 0.0367(14) 0.0348(16) -0.0070(12) 0.0106(12) -0.0054(11) C12 0.0213(13) 0.0413(14) 0.0348(16) -0.0102(12) 0.0066(12) -0.0036(11) C13 0.0253(15) 0.0576(18) 0.048(2) -0.0081(15) 0.0065(14) -0.0048(13) C14 0.0325(17) 0.069(2) 0.0399(19) -0.0071(16) -0.0031(15) 0.0024(15) C15 0.0408(17) 0.0538(17) 0.0312(17) -0.0036(13) 0.0026(14) 0.0065(14) C16 0.0364(16) 0.0487(16) 0.0322(17) -0.0058(13) 0.0124(14) -0.0049(13) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O2 1.920(2) . ? Cu1 O1 1.921(2) . ? Cu1 N1 1.951(2) . ? Cu1 N2 1.956(2) . ? Cl1 C3 1.733(3) . ? Cl2 C6 1.730(3) . ? O1 C1 1.281(3) . ? O2 C2 1.286(3) . ? O3 C4 1.214(4) . ? O4 C5 1.225(3) . ? C1 C6 1.363(4) . ? C1 C2 1.517(4) . ? C2 C3 1.356(4) . ? C3 C4 1.425(4) . ? C4 C5 1.571(4) . ? C5 C6 1.429(4) . ? N1 C7 1.341(4) . ? N1 C11 1.353(3) . ? N2 C16 1.347(4) . ? N2 C12 1.348(4) . ? C7 C8 1.374(4) . ? C7 H7 0.93 . ? C8 C9 1.371(5) . ? C8 H8 0.93 . ? C9 C10 1.387(5) . ? C9 H9 0.93 . ? C10 C11 1.375(4) . ? C10 H10 0.93 . ? C11 C12 1.478(4) . ? C12 C13 1.387(4) . ? C13 C14 1.379(5) . ? C13 H13 0.93 . ? C14 C15 1.364(5) . ? C14 H14 0.93 . ? C15 C16 1.376(4) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O1 84.80(8) . . ? O2 Cu1 N1 96.69(9) . . ? O1 Cu1 N1 177.49(10) . . ? O2 Cu1 N2 178.99(9) . . ? O1 Cu1 N2 96.13(9) . . ? N1 Cu1 N2 82.40(10) . . ? C1 O1 Cu1 112.72(18) . . ? C2 O2 Cu1 112.86(18) . . ? O1 C1 C6 124.8(3) . . ? O1 C1 C2 115.0(2) . . ? C6 C1 C2 120.2(2) . . ? O2 C2 C3 125.4(3) . . ? O2 C2 C1 114.4(2) . . ? C3 C2 C1 120.2(2) . . ? C2 C3 C4 122.6(3) . . ? C2 C3 Cl1 118.9(2) . . ? C4 C3 Cl1 118.5(2) . . ? O3 C4 C3 125.3(3) . . ? O3 C4 C5 117.6(3) . . ? C3 C4 C5 117.1(2) . . ? O4 C5 C6 124.3(3) . . ? O4 C5 C4 117.9(3) . . ? C6 C5 C4 117.8(2) . . ? C1 C6 C5 121.9(3) . . ? C1 C6 Cl2 119.3(2) . . ? C5 C6 Cl2 118.5(2) . . ? C7 N1 C11 119.7(2) . . ? C7 N1 Cu1 125.42(19) . . ? C11 N1 Cu1 114.86(19) . . ? C16 N2 C12 119.5(3) . . ? C16 N2 Cu1 125.6(2) . . ? C12 N2 Cu1 114.88(19) . . ? N1 C7 C8 121.4(3) . . ? N1 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 119.7(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 118.7(3) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? N1 C11 C10 121.2(3) . . ? N1 C11 C12 113.9(2) . . ? C10 C11 C12 124.9(3) . . ? N2 C12 C13 121.2(3) . . ? N2 C12 C11 113.9(2) . . ? C13 C12 C11 124.9(3) . . ? C14 C13 C12 118.6(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N2 C16 C15 121.3(3) . . ? N2 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 O1 C1 -3.8(2) . . . . ? N1 Cu1 O1 C1 123(2) . . . . ? N2 Cu1 O1 C1 176.6(2) . . . . ? O1 Cu1 O2 C2 4.7(2) . . . . ? N1 Cu1 O2 C2 -173.2(2) . . . . ? N2 Cu1 O2 C2 161(6) . . . . ? Cu1 O1 C1 C6 -179.1(2) . . . . ? Cu1 O1 C1 C2 2.3(3) . . . . ? Cu1 O2 C2 C3 175.1(2) . . . . ? Cu1 O2 C2 C1 -4.6(3) . . . . ? O1 C1 C2 O2 1.6(4) . . . . ? C6 C1 C2 O2 -177.1(3) . . . . ? O1 C1 C2 C3 -178.1(3) . . . . ? C6 C1 C2 C3 3.2(4) . . . . ? O2 C2 C3 C4 174.0(3) . . . . ? C1 C2 C3 C4 -6.3(4) . . . . ? O2 C2 C3 Cl1 -3.5(4) . . . . ? C1 C2 C3 Cl1 176.2(2) . . . . ? C2 C3 C4 O3 -176.2(3) . . . . ? Cl1 C3 C4 O3 1.4(4) . . . . ? C2 C3 C4 C5 4.1(4) . . . . ? Cl1 C3 C4 C5 -178.38(19) . . . . ? O3 C4 C5 O4 1.7(4) . . . . ? C3 C4 C5 O4 -178.5(3) . . . . ? O3 C4 C5 C6 -178.7(3) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? O1 C1 C6 C5 -176.4(3) . . . . ? C2 C1 C6 C5 2.1(4) . . . . ? O1 C1 C6 Cl2 -2.1(4) . . . . ? C2 C1 C6 Cl2 176.5(2) . . . . ? O4 C5 C6 C1 175.6(3) . . . . ? C4 C5 C6 C1 -4.1(4) . . . . ? O4 C5 C6 Cl2 1.1(4) . . . . ? C4 C5 C6 Cl2 -178.5(2) . . . . ? O2 Cu1 N1 C7 2.2(2) . . . . ? O1 Cu1 N1 C7 -124(2) . . . . ? N2 Cu1 N1 C7 -178.3(2) . . . . ? O2 Cu1 N1 C11 -179.22(19) . . . . ? O1 Cu1 N1 C11 54(2) . . . . ? N2 Cu1 N1 C11 0.34(19) . . . . ? O2 Cu1 N2 C16 -154(6) . . . . ? O1 Cu1 N2 C16 1.7(2) . . . . ? N1 Cu1 N2 C16 179.7(2) . . . . ? O2 Cu1 N2 C12 24(6) . . . . ? O1 Cu1 N2 C12 -179.5(2) . . . . ? N1 Cu1 N2 C12 -1.6(2) . . . . ? C11 N1 C7 C8 0.2(4) . . . . ? Cu1 N1 C7 C8 178.7(2) . . . . ? N1 C7 C8 C9 -0.7(5) . . . . ? C7 C8 C9 C10 0.7(5) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C7 N1 C11 C10 0.4(4) . . . . ? Cu1 N1 C11 C10 -178.3(2) . . . . ? C7 N1 C11 C12 179.5(2) . . . . ? Cu1 N1 C11 C12 0.8(3) . . . . ? C9 C10 C11 N1 -0.4(4) . . . . ? C9 C10 C11 C12 -179.4(3) . . . . ? C16 N2 C12 C13 1.7(4) . . . . ? Cu1 N2 C12 C13 -177.1(2) . . . . ? C16 N2 C12 C11 -178.8(2) . . . . ? Cu1 N2 C12 C11 2.4(3) . . . . ? N1 C11 C12 N2 -2.1(3) . . . . ? C10 C11 C12 N2 177.0(3) . . . . ? N1 C11 C12 C13 177.4(3) . . . . ? C10 C11 C12 C13 -3.5(5) . . . . ? N2 C12 C13 C14 -0.6(5) . . . . ? C11 C12 C13 C14 179.9(3) . . . . ? C12 C13 C14 C15 -0.5(5) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C12 N2 C16 C15 -1.6(4) . . . . ? Cu1 N2 C16 C15 177.1(2) . . . . ? C14 C15 C16 N2 0.4(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 947425' ####################################################################### # # 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_cu-h2caq-46 _audit_creation_date 2013-02-07T13:15:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C17 H14 Cl2 Cu1 N2 O6' _chemical_formula_sum 'C17 H14 Cl2 Cu N2 O6' _chemical_formula_weight 476.74 #------------------ UNIT CELL INFORMATION -----------------------------------# _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 9.6513(2) _cell_length_b 13.2880(3) _cell_length_c 14.3512(5) _cell_angle_alpha 90 _cell_angle_beta 98.049(2) _cell_angle_gamma 90 _cell_volume 1822.36(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3706 _cell_measurement_theta_min 3.1074 _cell_measurement_theta_max 75.8647 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 4.754 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70484 _exptl_absorpt_correction_T_max 1 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Xcalibur, Ruby, Nova' _diffrn_measurement_method 'CCD, \w scans' _diffrn_reflns_number 9435 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.56 _diffrn_reflns_theta_max 76.05 _diffrn_reflns_theta_full 76.05 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _reflns_number_total 3760 _reflns_number_gt 3261 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0841P)^2^+0.5404P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3760 _refine_ls_number_parameters 277 _refine_ls_number_restraints 9 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1352 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _refine_ls_shift/su_max 0 _refine_diff_density_max 1.465 _refine_diff_density_min -0.422 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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' 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' N N 0.0311 0.018 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cu1 Cu 0.10466(4) 0.64136(3) 0.11613(3) 0.03816(15) Uani 1 d . . . Cl1 Cl -0.19320(7) 0.35032(5) 0.14492(6) 0.04807(19) Uani 1 d . . . Cl2 Cl 0.43171(8) 0.37090(6) 0.05527(8) 0.0647(3) Uani 1 d . . . O1 O 0.23435(19) 0.53934(14) 0.08036(14) 0.0421(4) Uani 1 d . . . O2 O -0.02112(19) 0.52821(13) 0.11984(15) 0.0424(4) Uani 1 d . . . O3 O -0.0009(2) 0.17596(15) 0.11770(16) 0.0495(5) Uani 1 d . . . O4 O 0.2655(2) 0.18674(16) 0.08360(17) 0.0554(5) Uani 1 d . . . C1 C 0.1878(3) 0.45091(19) 0.08697(18) 0.0375(5) Uani 1 d . . . C2 C 0.0380(3) 0.44416(19) 0.10911(18) 0.0370(5) Uani 1 d . . . C3 C -0.0241(3) 0.35213(19) 0.1164(2) 0.0395(5) Uani 1 d . . . C4 C 0.0483(3) 0.2605(2) 0.10859(18) 0.0400(5) Uani 1 d . . . C5 C 0.2023(3) 0.2668(2) 0.08791(19) 0.0403(5) Uani 1 d . . . C6 C 0.2598(3) 0.36333(19) 0.0778(2) 0.0402(6) Uani 1 d . . . N1 N -0.0411(2) 0.74240(16) 0.13300(16) 0.0393(5) Uani 1 d . . . N2 N 0.2071(2) 0.76416(17) 0.08725(16) 0.0399(5) Uani 1 d . . . C7 C -0.1669(3) 0.7205(2) 0.1561(2) 0.0462(6) Uani 1 d . . . H7 H -0.192 0.6534 0.1617 0.055 Uiso 1 calc R . . C8 C -0.2612(3) 0.7953(2) 0.1719(2) 0.0494(6) Uani 1 d . . . H8 H -0.3487 0.7792 0.1878 0.059 Uiso 1 calc R . . C9 C -0.2203(3) 0.8962(2) 0.1630(2) 0.0517(7) Uani 1 d . . . H9 H -0.2807 0.9484 0.1732 0.062 Uiso 1 calc R . . C10 C -0.0912(3) 0.9166(2) 0.1394(2) 0.0489(6) Uani 1 d . . . H10 H -0.0627 0.983 0.1338 0.059 Uiso 1 calc R . . C11 C -0.0028(3) 0.8384(2) 0.12373(18) 0.0387(5) Uani 1 d . . . C12 C 0.1380(3) 0.85138(19) 0.09540(19) 0.0388(5) Uani 1 d . . . C13 C 0.1959(3) 0.9430(2) 0.0758(2) 0.0488(6) Uani 1 d . . . H13 H 0.1485 1.0029 0.0829 0.059 Uiso 1 calc R . . C14 C 0.3257(3) 0.9435(2) 0.0453(3) 0.0569(8) Uani 1 d . . . H14 H 0.3653 1.0041 0.0301 0.068 Uiso 1 calc R . . C15 C 0.3960(3) 0.8552(2) 0.0374(3) 0.0549(8) Uani 1 d . . . H15 H 0.4841 0.855 0.0182 0.066 Uiso 1 calc R . . C16 C 0.3330(3) 0.7657(2) 0.0589(2) 0.0462(6) Uani 1 d . . . H16 H 0.3798 0.7053 0.0534 0.055 Uiso 1 calc R . . O5 O 0.2040(2) 0.62310(16) 0.26719(16) 0.0502(5) Uani 1 d D . . H5A H 0.291(2) 0.647(3) 0.282(3) 0.069(13) Uiso 1 d D . . H5B H 0.154(4) 0.650(3) 0.309(2) 0.074(13) Uiso 1 d D . . H6A H 0.446(4) 0.171(4) 0.177(3) 0.099(17) Uiso 1 d D . . O6 O 0.5091(4) 0.1417(4) 0.2121(4) 0.134(2) Uani 1 d D . . C17 C 0.4607(6) 0.0637(5) 0.2630(4) 0.0927(14) Uani 1 d D . . H17A H 0.360(2) 0.055(6) 0.256(6) 0.21(4) Uiso 1 d D . . H17B H 0.485(8) 0.082(6) 0.328(2) 0.19(4) Uiso 1 d D . . H17C H 0.494(8) -0.005(3) 0.264(6) 0.21(4) Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0386(2) 0.0196(2) 0.0572(3) -0.00066(14) 0.00993(17) 0.00024(12) Cl1 0.0406(3) 0.0370(4) 0.0675(4) 0.0030(3) 0.0108(3) -0.0031(2) Cl2 0.0467(4) 0.0472(4) 0.1050(7) -0.0120(4) 0.0277(4) 0.0018(3) O1 0.0435(9) 0.0255(9) 0.0589(11) -0.0046(8) 0.0127(8) -0.0020(7) O2 0.0392(8) 0.0219(8) 0.0665(12) -0.0018(8) 0.0083(8) 0.0007(7) O3 0.0587(11) 0.0252(9) 0.0656(13) 0.0009(9) 0.0124(9) -0.0042(8) O4 0.0565(12) 0.0278(10) 0.0816(15) -0.0017(10) 0.0083(10) 0.0094(8) C1 0.0414(12) 0.0286(12) 0.0424(12) -0.0004(10) 0.0056(9) 0.0004(9) C2 0.0388(11) 0.0264(12) 0.0449(12) -0.0008(9) 0.0029(9) 0.0042(9) C3 0.0378(12) 0.0292(13) 0.0510(14) 0.0005(10) 0.0040(10) 0.0001(9) C4 0.0470(13) 0.0291(12) 0.0427(13) 0.0018(10) 0.0023(10) -0.0018(10) C5 0.0437(13) 0.0287(12) 0.0474(13) -0.0026(10) 0.0020(10) 0.0048(10) C6 0.0373(12) 0.0307(13) 0.0537(15) -0.0033(10) 0.0099(10) 0.0026(9) N1 0.0414(10) 0.0247(10) 0.0511(12) -0.0009(9) 0.0044(9) 0.0023(8) N2 0.0443(11) 0.0257(10) 0.0500(12) 0.0018(9) 0.0078(9) -0.0019(8) C7 0.0447(13) 0.0327(13) 0.0616(16) 0.0024(12) 0.0084(11) 0.0012(10) C8 0.0434(13) 0.0454(16) 0.0600(16) -0.0015(13) 0.0088(12) 0.0044(11) C9 0.0496(15) 0.0455(17) 0.0594(17) -0.0090(13) 0.0049(12) 0.0185(13) C10 0.0571(16) 0.0302(13) 0.0584(16) -0.0022(12) 0.0047(12) 0.0038(11) C11 0.0438(13) 0.0267(11) 0.0441(13) 0.0001(10) 0.0008(10) 0.0004(10) C12 0.0436(13) 0.0279(12) 0.0440(13) 0.0002(9) 0.0027(10) -0.0019(9) C13 0.0558(15) 0.0257(13) 0.0640(17) 0.0044(12) 0.0057(13) -0.0031(11) C14 0.0641(18) 0.0340(15) 0.073(2) 0.0098(14) 0.0100(15) -0.0119(13) C15 0.0451(15) 0.0513(19) 0.0695(19) 0.0044(14) 0.0122(14) -0.0044(12) C16 0.0443(13) 0.0337(14) 0.0619(17) 0.0010(12) 0.0115(12) 0.0000(10) O5 0.0569(12) 0.0393(10) 0.0550(11) -0.0039(9) 0.0102(9) 0.0026(9) O6 0.0592(18) 0.196(5) 0.142(4) 0.084(3) -0.007(2) 0.012(2) C17 0.079(3) 0.106(4) 0.092(3) 0.001(3) 0.007(2) 0.010(3) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O2 1.9378(18) . ? Cu1 O1 1.9616(19) . ? Cu1 N2 1.981(2) . ? Cu1 N1 1.984(2) . ? Cu1 O5 2.257(2) . ? Cl1 C3 1.737(3) . ? Cl2 C6 1.737(3) . ? O1 C1 1.266(3) . ? O2 C2 1.273(3) . ? O3 C4 1.234(3) . ? O4 C5 1.232(3) . ? C1 C6 1.371(4) . ? C1 C2 1.525(3) . ? C2 C3 1.373(4) . ? C3 C4 1.416(4) . ? C4 C5 1.558(4) . ? C5 C6 1.413(4) . ? N1 C7 1.335(4) . ? N1 C11 1.340(3) . ? N2 C16 1.335(4) . ? N2 C12 1.350(3) . ? C7 C8 1.388(4) . ? C7 H7 0.93 . ? C8 C9 1.409(5) . ? C8 H8 0.93 . ? C9 C10 1.363(4) . ? C9 H9 0.93 . ? C10 C11 1.383(4) . ? C10 H10 0.93 . ? C11 C12 1.482(4) . ? C12 C13 1.385(4) . ? C13 C14 1.384(5) . ? C13 H13 0.93 . ? C14 C15 1.368(5) . ? C14 H14 0.93 . ? C15 C16 1.389(4) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? O5 H5A 0.897(19) . ? O5 H5B 0.897(19) . ? O6 C17 1.387(7) . ? O6 H6A 0.833(19) . ? C17 H17A 0.974(19) . ? C17 H17B 0.961(19) . ? C17 H17C 0.96(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 O2 Cu1 O1 84.04(8) . . ? O2 Cu1 N2 167.82(9) . . ? O1 Cu1 N2 99.16(9) . . ? O2 Cu1 N1 93.68(9) . . ? O1 Cu1 N1 171.50(9) . . ? N2 Cu1 N1 81.44(9) . . ? O2 Cu1 O5 94.22(9) . . ? O1 Cu1 O5 88.64(8) . . ? N2 Cu1 O5 97.59(9) . . ? N1 Cu1 O5 99.70(9) . . ? C1 O1 Cu1 112.05(16) . . ? C2 O2 Cu1 112.59(17) . . ? O1 C1 C6 126.2(2) . . ? O1 C1 C2 115.3(2) . . ? C6 C1 C2 118.6(2) . . ? O2 C2 C3 124.4(2) . . ? O2 C2 C1 115.3(2) . . ? C3 C2 C1 120.3(2) . . ? C2 C3 C4 122.3(3) . . ? C2 C3 Cl1 117.7(2) . . ? C4 C3 Cl1 119.8(2) . . ? O3 C4 C3 124.9(3) . . ? O3 C4 C5 117.4(2) . . ? C3 C4 C5 117.7(2) . . ? O4 C5 C6 125.1(3) . . ? O4 C5 C4 117.1(2) . . ? C6 C5 C4 117.8(2) . . ? C1 C6 C5 123.3(3) . . ? C1 C6 Cl2 118.6(2) . . ? C5 C6 Cl2 118.1(2) . . ? C7 N1 C11 120.4(2) . . ? C7 N1 Cu1 124.60(18) . . ? C11 N1 Cu1 114.98(18) . . ? C16 N2 C12 119.6(2) . . ? C16 N2 Cu1 125.37(19) . . ? C12 N2 Cu1 114.96(18) . . ? N1 C7 C8 121.7(3) . . ? N1 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C9 117.9(3) . . ? C7 C8 H8 121 . . ? C9 C8 H8 121 . . ? C10 C9 C8 119.3(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N1 C11 C10 121.0(3) . . ? N1 C11 C12 114.4(2) . . ? C10 C11 C12 124.6(3) . . ? N2 C12 C13 121.3(3) . . ? N2 C12 C11 114.0(2) . . ? C13 C12 C11 124.7(3) . . ? C14 C13 C12 118.5(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 118.6(3) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? N2 C16 C15 121.8(3) . . ? N2 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? Cu1 O5 H5A 116(3) . . ? Cu1 O5 H5B 114(3) . . ? H5A O5 H5B 106(4) . . ? C17 O6 H6A 113(4) . . ? O6 C17 H17A 116(5) . . ? O6 C17 H17B 105(5) . . ? H17A C17 H17B 103(4) . . ? O6 C17 H17C 125(5) . . ? H17A C17 H17C 103(4) . . ? H17B C17 H17C 101(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 O1 C1 -7.80(18) . . . . ? N2 Cu1 O1 C1 -175.94(18) . . . . ? N1 Cu1 O1 C1 -82.6(6) . . . . ? O5 Cu1 O1 C1 86.59(19) . . . . ? O1 Cu1 O2 C2 7.17(18) . . . . ? N2 Cu1 O2 C2 113.1(4) . . . . ? N1 Cu1 O2 C2 178.95(19) . . . . ? O5 Cu1 O2 C2 -81.02(19) . . . . ? Cu1 O1 C1 C6 -171.8(2) . . . . ? Cu1 O1 C1 C2 6.9(3) . . . . ? Cu1 O2 C2 C3 174.5(2) . . . . ? Cu1 O2 C2 C1 -5.4(3) . . . . ? O1 C1 C2 O2 -1.1(3) . . . . ? C6 C1 C2 O2 177.7(2) . . . . ? O1 C1 C2 C3 179.0(2) . . . . ? C6 C1 C2 C3 -2.2(4) . . . . ? O2 C2 C3 C4 -176.7(2) . . . . ? C1 C2 C3 C4 3.1(4) . . . . ? O2 C2 C3 Cl1 -1.6(4) . . . . ? C1 C2 C3 Cl1 178.32(19) . . . . ? C2 C3 C4 O3 177.5(3) . . . . ? Cl1 C3 C4 O3 2.4(4) . . . . ? C2 C3 C4 C5 -1.9(4) . . . . ? Cl1 C3 C4 C5 -176.97(19) . . . . ? O3 C4 C5 O4 -1.2(4) . . . . ? C3 C4 C5 O4 178.2(3) . . . . ? O3 C4 C5 C6 -179.7(3) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? O1 C1 C6 C5 178.7(3) . . . . ? C2 C1 C6 C5 0.0(4) . . . . ? O1 C1 C6 Cl2 0.1(4) . . . . ? C2 C1 C6 Cl2 -178.55(19) . . . . ? O4 C5 C6 C1 -177.2(3) . . . . ? C4 C5 C6 C1 1.2(4) . . . . ? O4 C5 C6 Cl2 1.4(4) . . . . ? C4 C5 C6 Cl2 179.73(19) . . . . ? O2 Cu1 N1 C7 10.5(2) . . . . ? O1 Cu1 N1 C7 84.6(6) . . . . ? N2 Cu1 N1 C7 179.3(2) . . . . ? O5 Cu1 N1 C7 -84.4(2) . . . . ? O2 Cu1 N1 C11 -172.47(19) . . . . ? O1 Cu1 N1 C11 -98.4(6) . . . . ? N2 Cu1 N1 C11 -3.70(19) . . . . ? O5 Cu1 N1 C11 92.6(2) . . . . ? O2 Cu1 N2 C16 -108.8(4) . . . . ? O1 Cu1 N2 C16 -4.4(2) . . . . ? N1 Cu1 N2 C16 -175.8(2) . . . . ? O5 Cu1 N2 C16 85.4(2) . . . . ? O2 Cu1 N2 C12 69.3(5) . . . . ? O1 Cu1 N2 C12 173.66(19) . . . . ? N1 Cu1 N2 C12 2.24(19) . . . . ? O5 Cu1 N2 C12 -96.50(19) . . . . ? C11 N1 C7 C8 -0.5(4) . . . . ? Cu1 N1 C7 C8 176.4(2) . . . . ? N1 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C8 C9 C10 C11 0.5(5) . . . . ? C7 N1 C11 C10 1.2(4) . . . . ? Cu1 N1 C11 C10 -176.0(2) . . . . ? C7 N1 C11 C12 -178.4(2) . . . . ? Cu1 N1 C11 C12 4.4(3) . . . . ? C9 C10 C11 N1 -1.2(4) . . . . ? C9 C10 C11 C12 178.4(3) . . . . ? C16 N2 C12 C13 -0.6(4) . . . . ? Cu1 N2 C12 C13 -178.8(2) . . . . ? C16 N2 C12 C11 177.6(2) . . . . ? Cu1 N2 C12 C11 -0.6(3) . . . . ? N1 C11 C12 N2 -2.5(3) . . . . ? C10 C11 C12 N2 177.9(3) . . . . ? N1 C11 C12 C13 175.7(3) . . . . ? C10 C11 C12 C13 -3.9(4) . . . . ? N2 C12 C13 C14 1.4(4) . . . . ? C11 C12 C13 C14 -176.7(3) . . . . ? C12 C13 C14 C15 -1.7(5) . . . . ? C13 C14 C15 C16 1.2(5) . . . . ? C12 N2 C16 C15 0.1(4) . . . . ? Cu1 N2 C16 C15 178.1(2) . . . . ? C14 C15 C16 N2 -0.4(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 947426' ####################################################################### # # 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_cu-h2ca-42-3 _audit_creation_date 2013-02-06T15:13:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C31 H22 Cl2 Cu1 N5 O5' _chemical_formula_sum 'C31 H22 Cl2 Cu1 N5 O5' _chemical_formula_weight 678.99 #------------------ UNIT CELL INFORMATION -----------------------------------# _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 9.5497(7) _cell_length_b 13.1060(10) _cell_length_c 13.2621(10) _cell_angle_alpha 105.921(7) _cell_angle_beta 107.693(7) _cell_angle_gamma 99.079(6) _cell_volume 1467.06(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4019 _cell_measurement_theta_min 3.6322 _cell_measurement_theta_max 65.4689 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 3.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6184 _exptl_absorpt_correction_T_max 1 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Xcalibur, Ruby, Nova' _diffrn_measurement_method 'CCD, \w scans' _diffrn_reflns_number 8610 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 65.57 _diffrn_reflns_theta_full 65.57 _diffrn_measured_fraction_theta_max 0.95 _diffrn_measured_fraction_theta_full 0.95 _reflns_number_total 4814 _reflns_number_gt 3601 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.1469P)^2^+0.0086P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4814 _refine_ls_number_parameters 405 _refine_ls_number_restraints 3 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.2433 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0 _refine_diff_density_max 1.018 _refine_diff_density_min -0.721 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly O5 O -0.5073(5) 0.3550(4) 0.4453(5) 0.0920(13) Uani 1 d D . . C19 C 0.7058(7) 1.0001(6) 0.4141(6) 0.095(2) Uani 1 d . . . H19 H 0.8024 1.0482 0.4426 0.114 Uiso 1 calc R . . H5B H -0.422(8) 0.405(6) 0.449(10) 0.20(5) Uiso 1 d D . . H5A H -0.547(10) 0.398(6) 0.494(7) 0.16(4) Uiso 1 d D . . Cu1 Cu 0.17733(7) 0.76150(5) 0.25358(6) 0.0561(3) Uani 1 d . . . Cl1 Cl -0.40172(12) 0.57064(11) 0.15998(13) 0.0738(4) Uani 1 d . . . Cl2 Cl 0.17220(17) 0.72135(15) 0.61402(13) 0.0870(5) Uani 1 d . . . O1 O 0.1563(3) 0.7578(3) 0.3991(3) 0.0630(9) Uani 1 d . . . O2 O -0.0838(3) 0.6902(3) 0.2076(3) 0.0637(9) Uani 1 d . . . N1 N 0.2080(4) 0.6101(3) 0.2144(3) 0.0558(10) Uani 1 d . . . N3 N 0.4211(5) 0.8577(3) 0.3294(4) 0.0659(11) Uani 1 d . . . N2 N 0.1611(4) 0.7350(3) 0.0885(4) 0.0588(10) Uani 1 d . . . O3 O -0.3853(4) 0.5323(4) 0.3738(5) 0.1019(15) Uani 1 d . . . C2 C -0.1051(5) 0.6657(4) 0.2881(4) 0.0517(11) Uani 1 d . . . N4 N 0.1624(5) 0.9183(3) 0.2836(4) 0.0670(11) Uani 1 d . . . C1 C 0.0323(5) 0.7046(4) 0.3993(4) 0.0538(11) Uani 1 d . . . C4 C -0.2630(5) 0.5815(4) 0.3748(5) 0.0677(14) Uani 1 d . . . C11 C 0.1940(4) 0.5630(4) 0.1050(4) 0.0534(11) Uani 1 d . . . C7 C 0.2356(5) 0.5532(4) 0.2843(4) 0.0581(11) Uani 1 d . . . H7 H 0.2473 0.5861 0.3591 0.07 Uiso 1 calc R . . C13 C 0.1569(5) 0.6002(5) -0.0761(4) 0.0635(13) Uani 1 d . . . H13 H 0.163 0.5299 -0.1111 0.076 Uiso 1 calc R . . C16 C 0.1416(6) 0.8035(5) 0.0311(5) 0.0704(14) Uani 1 d . . . H16 H 0.1353 0.8733 0.0673 0.084 Uiso 1 calc R . . C22 C 0.2912(6) 0.9990(4) 0.3220(5) 0.0677(14) Uani 1 d . . . C12 C 0.1701(4) 0.6340(4) 0.0354(4) 0.0547(11) Uani 1 d . . . O4 O -0.1402(5) 0.5930(4) 0.5644(4) 0.1014(15) Uani 1 d . . . C5 C -0.1242(6) 0.6172(5) 0.4847(5) 0.0691(14) Uani 1 d . . . C15 C 0.1299(6) 0.7758(6) -0.0807(6) 0.0804(17) Uani 1 d . . . H15 H 0.1191 0.8265 -0.1178 0.097 Uiso 1 calc R . . C6 C 0.0164(5) 0.6795(4) 0.4894(5) 0.0644(13) Uani 1 d . . . C18 C 0.6896(7) 0.8912(6) 0.3930(6) 0.0900(19) Uani 1 d . . . H18 H 0.7748 0.8636 0.4064 0.108 Uiso 1 calc R . . C8 C 0.2471(5) 0.4471(5) 0.2484(5) 0.0691(14) Uani 1 d . . . H8 H 0.2673 0.4091 0.2987 0.083 Uiso 1 calc R . . C10 C 0.2032(5) 0.4566(4) 0.0658(5) 0.0589(12) Uani 1 d . . . H10 H 0.1924 0.4244 -0.0089 0.071 Uiso 1 calc R . . C14 C 0.1349(6) 0.6717(6) -0.1347(6) 0.0802(17) Uani 1 d . . . H14 H 0.1234 0.6497 -0.2103 0.096 Uiso 1 calc R . . C21 C 0.4354(6) 0.9657(4) 0.3489(4) 0.0676(14) Uani 1 d . . . C3 C -0.2439(5) 0.6086(4) 0.2834(5) 0.0591(12) Uani 1 d . . . C23 C 0.2834(9) 1.1069(5) 0.3369(6) 0.0879(19) Uani 1 d . . . H23 H 0.3723 1.1627 0.3619 0.105 Uiso 1 calc R . . C20 C 0.5789(7) 1.0391(5) 0.3931(5) 0.0833(18) Uani 1 d . . . H20 H 0.5886 1.1141 0.4084 0.1 Uiso 1 calc R . . C9 C 0.2289(5) 0.3980(4) 0.1393(5) 0.0646(13) Uani 1 d . . . H9 H 0.2336 0.3255 0.1138 0.077 Uiso 1 calc R . . C24 C 0.1463(10) 1.1312(6) 0.3149(7) 0.101(2) Uani 1 d . . . H24 H 0.1413 1.2035 0.3252 0.122 Uiso 1 calc R . . C25 C 0.0152(9) 1.0483(6) 0.2775(7) 0.095(2) Uani 1 d . . . H25 H -0.0794 1.0634 0.2635 0.114 Uiso 1 calc R . . C17 C 0.5437(6) 0.8208(5) 0.3508(5) 0.0775(16) Uani 1 d . . . H17 H 0.5327 0.746 0.3375 0.093 Uiso 1 calc R . . C26 C 0.0282(7) 0.9430(5) 0.2613(6) 0.0820(17) Uani 1 d . . . H26 H -0.0602 0.8861 0.2337 0.098 Uiso 1 calc R . . C27 C 0.4983(7) 0.2306(6) 0.1272(7) 0.092(2) Uani 1 d . . . H27 H 0.5141 0.2802 0.1975 0.11 Uiso 1 calc R . . C31 C 0.4902(5) 0.0564(5) 0.0086(5) 0.0692(14) Uani 1 d . . . C28 C 0.4609(7) 0.2617(6) 0.0352(8) 0.097(2) Uani 1 d . . . H28 H 0.4507 0.3324 0.0422 0.116 Uiso 1 calc R . . N5 N 0.5134(6) 0.1232(5) 0.1167(6) 0.1035(18) Uani 1 d . . . C30 C 0.4526(7) 0.0896(5) -0.0800(6) 0.0774(15) Uani 1 d . . . H30 H 0.4365 0.0416 -0.1512 0.093 Uiso 1 calc R . . C29 C 0.4383(9) 0.1893(7) -0.0674(8) 0.107(2) Uani 1 d . . . H29 H 0.4121 0.2114 -0.13 0.129 Uiso 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 O5 0.089(3) 0.074(3) 0.112(4) 0.035(3) 0.041(3) 0.005(2) C19 0.080(4) 0.096(5) 0.077(4) 0.008(4) 0.031(3) -0.030(3) Cu1 0.0565(4) 0.0505(5) 0.0608(5) 0.0198(4) 0.0270(3) -0.0001(3) Cl1 0.0534(6) 0.0705(8) 0.0874(10) 0.0244(7) 0.0208(6) 0.0038(5) Cl2 0.0818(8) 0.1091(12) 0.0657(9) 0.0381(9) 0.0235(7) 0.0057(8) O1 0.0551(16) 0.0581(19) 0.066(2) 0.0170(17) 0.0238(15) -0.0065(14) O2 0.0591(16) 0.066(2) 0.063(2) 0.0240(17) 0.0258(16) -0.0008(14) N1 0.0464(17) 0.063(2) 0.053(2) 0.019(2) 0.0195(16) -0.0007(16) N3 0.069(2) 0.051(2) 0.067(3) 0.011(2) 0.030(2) -0.0040(18) N2 0.0550(19) 0.060(2) 0.068(3) 0.035(2) 0.0256(18) 0.0022(16) O3 0.065(2) 0.129(4) 0.130(4) 0.068(3) 0.052(2) 0.000(2) C2 0.056(2) 0.045(2) 0.056(3) 0.017(2) 0.030(2) 0.0029(18) N4 0.078(2) 0.056(2) 0.073(3) 0.022(2) 0.043(2) 0.0072(19) C1 0.057(2) 0.052(3) 0.058(3) 0.023(2) 0.030(2) 0.0039(19) C4 0.060(3) 0.068(3) 0.090(4) 0.039(3) 0.042(3) 0.010(2) C11 0.0369(18) 0.059(3) 0.060(3) 0.021(2) 0.0176(18) -0.0006(17) C7 0.059(2) 0.061(3) 0.056(3) 0.029(2) 0.020(2) 0.007(2) C13 0.061(2) 0.080(3) 0.049(3) 0.017(3) 0.029(2) 0.009(2) C16 0.076(3) 0.067(3) 0.075(4) 0.035(3) 0.032(3) 0.008(2) C22 0.090(3) 0.049(3) 0.060(3) 0.012(2) 0.037(3) -0.002(2) C12 0.0401(18) 0.054(3) 0.068(3) 0.020(2) 0.0242(19) 0.0004(17) O4 0.105(3) 0.127(4) 0.093(3) 0.059(3) 0.056(3) 0.009(3) C5 0.076(3) 0.072(3) 0.074(4) 0.033(3) 0.045(3) 0.010(2) C15 0.081(3) 0.095(5) 0.084(4) 0.056(4) 0.036(3) 0.017(3) C6 0.064(3) 0.064(3) 0.069(3) 0.027(3) 0.031(2) 0.007(2) C18 0.068(3) 0.101(5) 0.077(4) 0.010(4) 0.026(3) -0.004(3) C8 0.060(2) 0.077(4) 0.085(4) 0.047(3) 0.030(3) 0.017(2) C10 0.052(2) 0.059(3) 0.064(3) 0.016(2) 0.028(2) 0.0077(19) C14 0.072(3) 0.111(5) 0.072(4) 0.049(4) 0.034(3) 0.014(3) C21 0.077(3) 0.057(3) 0.055(3) 0.008(2) 0.031(2) -0.013(2) C3 0.053(2) 0.052(3) 0.073(3) 0.020(2) 0.030(2) 0.0042(19) C23 0.124(5) 0.051(3) 0.089(5) 0.021(3) 0.051(4) 0.003(3) C20 0.088(4) 0.069(4) 0.073(4) 0.013(3) 0.035(3) -0.022(3) C9 0.053(2) 0.062(3) 0.083(4) 0.027(3) 0.031(2) 0.010(2) C24 0.153(7) 0.067(4) 0.102(6) 0.038(4) 0.060(5) 0.034(4) C25 0.121(5) 0.083(4) 0.116(6) 0.055(4) 0.064(5) 0.044(4) C17 0.068(3) 0.071(3) 0.082(4) 0.013(3) 0.033(3) 0.001(3) C26 0.090(4) 0.077(4) 0.104(5) 0.046(4) 0.054(4) 0.026(3) C27 0.081(4) 0.081(4) 0.098(5) 0.008(4) 0.032(4) 0.019(3) C31 0.062(3) 0.066(3) 0.080(4) 0.024(3) 0.031(3) 0.010(2) C28 0.085(4) 0.077(4) 0.141(7) 0.045(5) 0.052(4) 0.022(3) N5 0.091(3) 0.096(4) 0.116(5) 0.023(4) 0.043(3) 0.017(3) C30 0.107(4) 0.068(4) 0.075(4) 0.038(3) 0.042(3) 0.030(3) C29 0.126(6) 0.101(6) 0.119(7) 0.056(5) 0.058(5) 0.039(4) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 O5 H5B 0.94(2) . ? O5 H5A 0.95(2) . ? C19 C18 1.350(10) . ? C19 C20 1.370(11) . ? C19 H19 0.93 . ? Cu1 N1 2.000(4) . ? Cu1 O1 2.013(4) . ? Cu1 N4 2.020(4) . ? Cu1 N2 2.073(4) . ? Cu1 N3 2.230(4) . ? Cu1 O2 2.344(3) . ? Cl1 C3 1.736(5) . ? Cl2 C6 1.731(6) . ? O1 C1 1.277(5) . ? O2 C2 1.257(6) . ? N1 C7 1.333(6) . ? N1 C11 1.367(6) . ? N3 C17 1.318(7) . ? N3 C21 1.343(7) . ? N2 C16 1.327(7) . ? N2 C12 1.347(6) . ? O3 C4 1.236(6) . ? C2 C3 1.391(6) . ? C2 C1 1.535(7) . ? N4 C26 1.337(8) . ? N4 C22 1.343(6) . ? C1 C6 1.367(7) . ? C4 C3 1.407(7) . ? C4 C5 1.534(8) . ? C11 C10 1.376(7) . ? C11 C12 1.477(7) . ? C7 C8 1.375(8) . ? C7 H7 0.93 . ? C13 C14 1.374(8) . ? C13 C12 1.383(7) . ? C13 H13 0.93 . ? C16 C15 1.390(9) . ? C16 H16 0.93 . ? C22 C23 1.391(8) . ? C22 C21 1.480(9) . ? O4 C5 1.228(7) . ? C5 C6 1.431(7) . ? C15 C14 1.372(9) . ? C15 H15 0.93 . ? C18 C17 1.394(8) . ? C18 H18 0.93 . ? C8 C9 1.357(8) . ? C8 H8 0.93 . ? C10 C9 1.387(8) . ? C10 H10 0.93 . ? C14 H14 0.93 . ? C21 C20 1.391(7) . ? C23 C24 1.361(11) . ? C23 H23 0.93 . ? C20 H20 0.93 . ? C9 H9 0.93 . ? C24 C25 1.375(11) . ? C24 H24 0.93 . ? C25 C26 1.370(9) . ? C25 H25 0.93 . ? C17 H17 0.93 . ? C26 H26 0.93 . ? C27 C28 1.355(10) . ? C27 N5 1.411(10) . ? C27 H27 0.93 . ? C31 C30 1.331(8) . ? C31 N5 1.389(8) . ? C31 C31 1.484(12) 2_655 ? C28 C29 1.358(11) . ? C28 H28 0.93 . ? C30 C29 1.306(10) . ? C30 H30 0.93 . ? C29 H29 0.93 . ? 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 H5B O5 H5A 105(4) . . ? C18 C19 C20 119.5(5) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? N1 Cu1 O1 92.63(15) . . ? N1 Cu1 N4 173.35(15) . . ? O1 Cu1 N4 93.03(16) . . ? N1 Cu1 N2 80.59(16) . . ? O1 Cu1 N2 167.75(13) . . ? N4 Cu1 N2 94.44(18) . . ? N1 Cu1 N3 98.60(15) . . ? O1 Cu1 N3 96.23(15) . . ? N4 Cu1 N3 77.32(17) . . ? N2 Cu1 N3 94.88(15) . . ? N1 Cu1 O2 91.23(13) . . ? O1 Cu1 O2 74.84(12) . . ? N4 Cu1 O2 93.61(15) . . ? N2 Cu1 O2 94.99(13) . . ? N3 Cu1 O2 167.08(15) . . ? C1 O1 Cu1 120.6(3) . . ? C2 O2 Cu1 109.6(3) . . ? C7 N1 C11 119.4(4) . . ? C7 N1 Cu1 125.5(3) . . ? C11 N1 Cu1 115.0(3) . . ? C17 N3 C21 119.9(4) . . ? C17 N3 Cu1 128.3(4) . . ? C21 N3 Cu1 111.7(4) . . ? C16 N2 C12 118.1(5) . . ? C16 N2 Cu1 128.2(4) . . ? C12 N2 Cu1 113.7(3) . . ? O2 C2 C3 124.5(5) . . ? O2 C2 C1 116.9(3) . . ? C3 C2 C1 118.5(4) . . ? C26 N4 C22 119.5(5) . . ? C26 N4 Cu1 121.9(4) . . ? C22 N4 Cu1 118.5(4) . . ? O1 C1 C6 124.6(5) . . ? O1 C1 C2 115.9(4) . . ? C6 C1 C2 119.5(4) . . ? O3 C4 C3 124.4(6) . . ? O3 C4 C5 117.2(5) . . ? C3 C4 C5 118.4(4) . . ? N1 C11 C10 120.6(5) . . ? N1 C11 C12 115.5(4) . . ? C10 C11 C12 123.9(5) . . ? N1 C7 C8 121.6(5) . . ? N1 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C14 C13 C12 119.1(5) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? N2 C16 C15 123.1(6) . . ? N2 C16 H16 118.4 . . ? C15 C16 H16 118.4 . . ? N4 C22 C23 119.7(6) . . ? N4 C22 C21 116.3(5) . . ? C23 C22 C21 124.0(5) . . ? N2 C12 C13 122.0(5) . . ? N2 C12 C11 115.0(4) . . ? C13 C12 C11 123.0(5) . . ? O4 C5 C6 123.5(6) . . ? O4 C5 C4 118.5(5) . . ? C6 C5 C4 117.9(5) . . ? C14 C15 C16 118.2(6) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? C1 C6 C5 122.6(5) . . ? C1 C6 Cl2 119.5(3) . . ? C5 C6 Cl2 117.9(4) . . ? C19 C18 C17 119.2(7) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C9 C8 C7 119.7(5) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C11 C10 C9 119.1(5) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C15 C14 C13 119.4(6) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? N3 C21 C20 120.4(6) . . ? N3 C21 C22 115.8(4) . . ? C20 C21 C22 123.7(5) . . ? C2 C3 C4 122.9(5) . . ? C2 C3 Cl1 118.6(4) . . ? C4 C3 Cl1 118.4(3) . . ? C24 C23 C22 120.3(6) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C19 C20 C21 119.4(6) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C8 C9 C10 119.6(5) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C23 C24 C25 119.6(6) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 118.1(7) . . ? C26 C25 H25 121 . . ? C24 C25 H25 121 . . ? N3 C17 C18 121.6(6) . . ? N3 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? N4 C26 C25 122.8(6) . . ? N4 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? C28 C27 N5 120.1(7) . . ? C28 C27 H27 119.9 . . ? N5 C27 H27 119.9 . . ? C30 C31 N5 122.8(6) . . ? C30 C31 C31 118.6(7) . 2_655 ? N5 C31 C31 118.5(7) . 2_655 ? C27 C28 C29 119.9(7) . . ? C27 C28 H28 120 . . ? C29 C28 H28 120 . . ? C31 N5 C27 115.3(7) . . ? C29 C30 C31 120.2(7) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C29 C28 121.6(8) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 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 Cu1 O1 C1 -77.7(4) . . . . ? N4 Cu1 O1 C1 105.8(4) . . . . ? N2 Cu1 O1 C1 -21.7(9) . . . . ? N3 Cu1 O1 C1 -176.6(4) . . . . ? O2 Cu1 O1 C1 12.9(3) . . . . ? N1 Cu1 O2 C2 80.3(3) . . . . ? O1 Cu1 O2 C2 -12.1(3) . . . . ? N4 Cu1 O2 C2 -104.3(3) . . . . ? N2 Cu1 O2 C2 160.9(3) . . . . ? N3 Cu1 O2 C2 -59.4(8) . . . . ? O1 Cu1 N1 C7 -12.3(3) . . . . ? N4 Cu1 N1 C7 136.0(14) . . . . ? N2 Cu1 N1 C7 177.9(3) . . . . ? N3 Cu1 N1 C7 84.4(4) . . . . ? O2 Cu1 N1 C7 -87.2(3) . . . . ? O1 Cu1 N1 C11 165.7(3) . . . . ? N4 Cu1 N1 C11 -46.0(16) . . . . ? N2 Cu1 N1 C11 -4.1(3) . . . . ? N3 Cu1 N1 C11 -97.6(3) . . . . ? O2 Cu1 N1 C11 90.8(3) . . . . ? N1 Cu1 N3 C17 -6.4(5) . . . . ? O1 Cu1 N3 C17 87.3(5) . . . . ? N4 Cu1 N3 C17 179.0(5) . . . . ? N2 Cu1 N3 C17 -87.6(5) . . . . ? O2 Cu1 N3 C17 132.8(6) . . . . ? N1 Cu1 N3 C21 170.6(4) . . . . ? O1 Cu1 N3 C21 -95.8(4) . . . . ? N4 Cu1 N3 C21 -4.1(4) . . . . ? N2 Cu1 N3 C21 89.4(4) . . . . ? O2 Cu1 N3 C21 -50.3(9) . . . . ? N1 Cu1 N2 C16 -177.9(4) . . . . ? O1 Cu1 N2 C16 125.1(7) . . . . ? N4 Cu1 N2 C16 -2.3(4) . . . . ? N3 Cu1 N2 C16 -79.9(4) . . . . ? O2 Cu1 N2 C16 91.7(4) . . . . ? N1 Cu1 N2 C12 3.1(3) . . . . ? O1 Cu1 N2 C12 -53.9(8) . . . . ? N4 Cu1 N2 C12 178.7(3) . . . . ? N3 Cu1 N2 C12 101.0(3) . . . . ? O2 Cu1 N2 C12 -87.3(3) . . . . ? Cu1 O2 C2 C3 -171.4(4) . . . . ? Cu1 O2 C2 C1 10.2(5) . . . . ? N1 Cu1 N4 C26 129.4(14) . . . . ? O1 Cu1 N4 C26 -82.3(5) . . . . ? N2 Cu1 N4 C26 88.0(5) . . . . ? N3 Cu1 N4 C26 -178.0(5) . . . . ? O2 Cu1 N4 C26 -7.3(5) . . . . ? N1 Cu1 N4 C22 -47.5(17) . . . . ? O1 Cu1 N4 C22 100.9(4) . . . . ? N2 Cu1 N4 C22 -88.9(4) . . . . ? N3 Cu1 N4 C22 5.2(4) . . . . ? O2 Cu1 N4 C22 175.8(4) . . . . ? Cu1 O1 C1 C6 166.7(4) . . . . ? Cu1 O1 C1 C2 -11.9(5) . . . . ? O2 C2 C1 O1 -0.6(6) . . . . ? C3 C2 C1 O1 -179.2(4) . . . . ? O2 C2 C1 C6 -179.3(4) . . . . ? C3 C2 C1 C6 2.1(7) . . . . ? C7 N1 C11 C10 2.1(6) . . . . ? Cu1 N1 C11 C10 -176.0(3) . . . . ? C7 N1 C11 C12 -177.5(3) . . . . ? Cu1 N1 C11 C12 4.4(4) . . . . ? C11 N1 C7 C8 -1.4(6) . . . . ? Cu1 N1 C7 C8 176.5(3) . . . . ? C12 N2 C16 C15 0.0(7) . . . . ? Cu1 N2 C16 C15 -179.0(4) . . . . ? C26 N4 C22 C23 -0.8(9) . . . . ? Cu1 N4 C22 C23 176.1(4) . . . . ? C26 N4 C22 C21 177.6(5) . . . . ? Cu1 N4 C22 C21 -5.4(6) . . . . ? C16 N2 C12 C13 -1.1(6) . . . . ? Cu1 N2 C12 C13 178.0(3) . . . . ? C16 N2 C12 C11 179.2(4) . . . . ? Cu1 N2 C12 C11 -1.7(4) . . . . ? C14 C13 C12 N2 0.3(6) . . . . ? C14 C13 C12 C11 -180.0(4) . . . . ? N1 C11 C12 N2 -1.7(5) . . . . ? C10 C11 C12 N2 178.7(4) . . . . ? N1 C11 C12 C13 178.6(4) . . . . ? C10 C11 C12 C13 -1.0(6) . . . . ? O3 C4 C5 O4 1.8(8) . . . . ? C3 C4 C5 O4 -179.5(5) . . . . ? O3 C4 C5 C6 -176.6(5) . . . . ? C3 C4 C5 C6 2.1(8) . . . . ? N2 C16 C15 C14 1.8(8) . . . . ? O1 C1 C6 C5 -178.3(5) . . . . ? C2 C1 C6 C5 0.3(7) . . . . ? O1 C1 C6 Cl2 0.3(7) . . . . ? C2 C1 C6 Cl2 178.9(3) . . . . ? O4 C5 C6 C1 179.3(6) . . . . ? C4 C5 C6 C1 -2.3(8) . . . . ? O4 C5 C6 Cl2 0.7(8) . . . . ? C4 C5 C6 Cl2 179.1(4) . . . . ? C20 C19 C18 C17 -0.3(10) . . . . ? N1 C7 C8 C9 -0.6(7) . . . . ? N1 C11 C10 C9 -0.8(6) . . . . ? C12 C11 C10 C9 178.8(4) . . . . ? C16 C15 C14 C13 -2.5(8) . . . . ? C12 C13 C14 C15 1.5(7) . . . . ? C17 N3 C21 C20 -0.9(8) . . . . ? Cu1 N3 C21 C20 -178.1(4) . . . . ? C17 N3 C21 C22 179.8(5) . . . . ? Cu1 N3 C21 C22 2.6(6) . . . . ? N4 C22 C21 N3 1.5(7) . . . . ? C23 C22 C21 N3 179.8(5) . . . . ? N4 C22 C21 C20 -177.7(5) . . . . ? C23 C22 C21 C20 0.6(9) . . . . ? O2 C2 C3 C4 179.3(5) . . . . ? C1 C2 C3 C4 -2.3(7) . . . . ? O2 C2 C3 Cl1 -1.8(7) . . . . ? C1 C2 C3 Cl1 176.7(3) . . . . ? O3 C4 C3 C2 178.9(5) . . . . ? C5 C4 C3 C2 0.2(7) . . . . ? O3 C4 C3 Cl1 -0.1(8) . . . . ? C5 C4 C3 Cl1 -178.8(4) . . . . ? N4 C22 C23 C24 1.4(10) . . . . ? C21 C22 C23 C24 -176.9(6) . . . . ? C18 C19 C20 C21 -0.9(10) . . . . ? N3 C21 C20 C19 1.6(9) . . . . ? C22 C21 C20 C19 -179.2(6) . . . . ? C7 C8 C9 C10 1.9(7) . . . . ? C11 C10 C9 C8 -1.2(6) . . . . ? C22 C23 C24 C25 -0.3(12) . . . . ? C23 C24 C25 C26 -1.4(12) . . . . ? C21 N3 C17 C18 -0.4(9) . . . . ? Cu1 N3 C17 C18 176.3(4) . . . . ? C19 C18 C17 N3 1.0(10) . . . . ? C22 N4 C26 C25 -0.9(10) . . . . ? Cu1 N4 C26 C25 -177.8(5) . . . . ? C24 C25 C26 N4 2.0(11) . . . . ? N5 C27 C28 C29 -0.2(10) . . . . ? C30 C31 N5 C27 -1.6(8) . . . . ? C31 C31 N5 C27 177.7(5) 2_655 . . . ? C28 C27 N5 C31 1.1(8) . . . . ? N5 C31 C30 C29 1.1(9) . . . . ? C31 C31 C30 C29 -178.3(6) 2_655 . . . ? C31 C30 C29 C28 0.0(11) . . . . ? C27 C28 C29 C30 -0.4(11) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 947427' ####################################################################### # # 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_cu-h2ca-42-2 _audit_creation_date 2013-02-11T16:25:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C31 H24 Cl2 Cu1 N5 O6' _chemical_formula_sum 'C31 H24 Cl2 Cu N5 O6 S0' _chemical_formula_weight 696.99 #------------------ UNIT CELL INFORMATION -----------------------------------# _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 10.2366(9) _cell_length_b 13.1074(9) _cell_length_c 13.4361(12) _cell_angle_alpha 63.309(8) _cell_angle_beta 68.186(8) _cell_angle_gamma 81.456(7) _cell_volume 1495.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3623 _cell_measurement_theta_min 3.7723 _cell_measurement_theta_max 75.8476 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 3.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.67665 _exptl_absorpt_correction_T_max 1 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Xcalibur, Ruby, Nova' _diffrn_measurement_method 'CCD, \w scans' _diffrn_reflns_number 14124 _diffrn_reflns_av_R_equivalents 0.0923 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 76.04 _diffrn_reflns_theta_full 76.04 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 6111 _reflns_number_gt 4537 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.1000P)^2^+8.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6111 _refine_ls_number_parameters 417 _refine_ls_number_restraints 14 _refine_ls_R_factor_gt 0.102 _refine_ls_wR_factor_ref 0.2627 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.887 _refine_ls_shift/su_max 0.002 _refine_diff_density_max 1.508 _refine_diff_density_min -0.783 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Cu1 Cu 0.75445(8) 0.23414(7) 0.25120(8) 0.0494(3) Uani 1 d . . . Cl1 Cl 1.0092(2) -0.12941(19) 0.41319(17) 0.0788(5) Uani 1 d . . . Cl2 Cl 1.09141(18) 0.18732(15) -0.12776(15) 0.0656(4) Uani 1 d . . . O1 O 0.8860(4) 0.2123(4) 0.0864(4) 0.0587(11) Uani 1 d . . . O2 O 0.8482(5) 0.0764(4) 0.3117(4) 0.0605(11) Uani 1 d . . . O3 O 1.2254(6) -0.1465(5) 0.2004(5) 0.0806(15) Uani 1 d D . . O4 O 1.2572(5) -0.0150(5) -0.0284(5) 0.0742(14) Uani 1 d . . . C1 C 0.9667(6) 0.1269(5) 0.1068(6) 0.0503(13) Uani 1 d . . . C2 C 0.9468(6) 0.0495(5) 0.2365(6) 0.0506(13) Uani 1 d . . . C3 C 1.0331(6) -0.0422(6) 0.2660(6) 0.0573(14) Uani 1 d . . . C4 C 1.1440(6) -0.0672(6) 0.1779(6) 0.0580(15) Uani 1 d . . . C5 C 1.1624(6) 0.0084(6) 0.0462(6) 0.0564(14) Uani 1 d . . . C6 C 1.0717(6) 0.1020(5) 0.0204(6) 0.0534(13) Uani 1 d . . . N1 N 0.9192(5) 0.3182(4) 0.2338(4) 0.0483(10) Uani 1 d . . . N2 N 0.7050(5) 0.4051(4) 0.1573(5) 0.0518(11) Uani 1 d . . . C7 C 1.0200(7) 0.2674(6) 0.2768(6) 0.0601(15) Uani 1 d . . . H7 H 1.0175 0.1883 0.3187 0.072 Uiso 1 calc R . . C8 C 1.1301(8) 0.3305(7) 0.2604(7) 0.0697(18) Uani 1 d . . . H8 H 1.199 0.2939 0.2934 0.084 Uiso 1 calc R . . C9 C 1.1370(8) 0.4458(7) 0.1959(8) 0.078(2) Uani 1 d . . . H9 H 1.2127 0.4883 0.1812 0.093 Uiso 1 calc R . . C10 C 1.0304(8) 0.4985(6) 0.1529(7) 0.0637(16) Uani 1 d . . . H10 H 1.0312 0.5775 0.1108 0.076 Uiso 1 calc R . . C11 C 0.9224(6) 0.4324(5) 0.1732(5) 0.0496(12) Uani 1 d . . . C12 C 0.8005(6) 0.4821(5) 0.1322(5) 0.0510(13) Uani 1 d . . . C13 C 0.7828(9) 0.5986(6) 0.0767(7) 0.0706(19) Uani 1 d . . . H13 H 0.8515 0.6501 0.0573 0.085 Uiso 1 calc R . . C14 C 0.6611(10) 0.6367(7) 0.0506(8) 0.078(2) Uani 1 d . . . H14 H 0.6446 0.7145 0.0164 0.093 Uiso 1 calc R . . C15 C 0.5658(9) 0.5594(7) 0.0756(7) 0.074(2) Uani 1 d . . . H15 H 0.484 0.5837 0.0576 0.089 Uiso 1 calc R . . C16 C 0.5912(7) 0.4440(7) 0.1280(7) 0.0655(17) Uani 1 d . . . H16 H 0.526 0.3917 0.1432 0.079 Uiso 1 calc R . . N3 N 0.6291(5) 0.2128(4) 0.4297(5) 0.0514(11) Uani 1 d . . . N4 N 0.5751(5) 0.1649(4) 0.2756(5) 0.0510(11) Uani 1 d . . . C17 C 0.6635(8) 0.2370(6) 0.5034(7) 0.0643(16) Uani 1 d . . . H17 H 0.7517 0.2697 0.4767 0.077 Uiso 1 calc R . . C18 C 0.5751(9) 0.2159(7) 0.6165(7) 0.0726(19) Uani 1 d . . . H18 H 0.6034 0.233 0.6657 0.087 Uiso 1 calc R . . C19 C 0.4421(9) 0.1684(7) 0.6562(7) 0.075(2) Uani 1 d . . . H19 H 0.3796 0.1536 0.7323 0.09 Uiso 1 calc R . . C20 C 0.4046(7) 0.1438(6) 0.5810(6) 0.0661(17) Uani 1 d . . . H20 H 0.3158 0.113 0.6056 0.079 Uiso 1 calc R . . C21 C 0.4999(6) 0.1651(5) 0.4682(5) 0.0513(13) Uani 1 d . . . C22 C 0.4714(6) 0.1380(5) 0.3828(5) 0.0498(13) Uani 1 d . . . C23 C 0.3479(6) 0.0855(6) 0.4083(6) 0.0601(15) Uani 1 d . . . H23 H 0.2779 0.0645 0.4826 0.072 Uiso 1 calc R . . C24 C 0.3295(7) 0.0645(6) 0.3222(7) 0.0664(18) Uani 1 d . . . H24 H 0.2455 0.0319 0.337 0.08 Uiso 1 calc R . . C25 C 0.4359(8) 0.0920(6) 0.2148(7) 0.0679(17) Uani 1 d . . . H25 H 0.426 0.0776 0.1561 0.082 Uiso 1 calc R . . C26 C 0.5570(7) 0.1412(6) 0.1961(6) 0.0622(16) Uani 1 d . . . H26 H 0.63 0.1586 0.1238 0.075 Uiso 1 calc R . . N5 N 0.3138(14) 0.4553(10) 0.5934(9) 0.126(4) Uani 1 d . . . C27 C 0.1925(15) 0.4314(12) 0.5827(13) 0.124(4) Uani 1 d . . . H27 H 0.1112 0.4056 0.6492 0.149 Uiso 1 calc R . . C28 C 0.1915(17) 0.4452(17) 0.4774(15) 0.155(6) Uani 1 d . . . H28 H 0.1125 0.4307 0.4669 0.186 Uiso 1 calc R . . C29 C 0.321(3) 0.483(2) 0.385(2) 0.193(8) Uani 1 d U . . H29 H 0.3253 0.4936 0.3109 0.232 Uiso 1 calc R . . C30 C 0.4380(15) 0.5068(15) 0.3915(11) 0.141(6) Uani 1 d . . . H30 H 0.5185 0.5349 0.3246 0.17 Uiso 1 calc R . . C31 C 0.4356(11) 0.4890(8) 0.4947(9) 0.089(3) Uani 1 d . . . O5 O 1.5245(7) -0.1346(7) 0.0664(8) 0.110(2) Uani 1 d D . . H5B H 1.4358 -0.1125 0.107 0.17 Uiso 1 d D . . H5A H 1.586(4) -0.074(6) 0.045(11) 0.2 Uiso 1 d D . . O6 O 0.2532(6) 0.6955(5) 0.0924(6) 0.0780(15) Uani 1 d D . . H6A H 0.205(12) 0.741(8) 0.040(8) 0.14(5) Uiso 1 d D . . H6B H 0.241(8) 0.732(6) 0.142(5) 0.06(2) Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0372(4) 0.0504(5) 0.0558(5) -0.0217(4) -0.0122(3) 0.0005(3) Cl1 0.0621(10) 0.0938(13) 0.0670(10) -0.0238(9) -0.0234(8) 0.0069(9) Cl2 0.0620(9) 0.0674(9) 0.0614(9) -0.0264(7) -0.0151(7) -0.0024(7) O1 0.045(2) 0.056(2) 0.079(3) -0.034(2) -0.022(2) 0.0098(18) O2 0.047(2) 0.064(3) 0.065(3) -0.034(2) -0.0036(19) -0.0014(19) O3 0.065(3) 0.090(4) 0.088(4) -0.040(3) -0.037(3) 0.034(3) O4 0.054(3) 0.085(3) 0.082(3) -0.051(3) -0.008(2) 0.013(2) C1 0.038(3) 0.051(3) 0.068(4) -0.032(3) -0.016(2) 0.000(2) C2 0.037(3) 0.055(3) 0.065(4) -0.033(3) -0.014(2) -0.001(2) C3 0.043(3) 0.069(4) 0.064(4) -0.031(3) -0.019(3) 0.002(3) C4 0.043(3) 0.066(4) 0.076(4) -0.040(3) -0.023(3) 0.010(3) C5 0.040(3) 0.064(4) 0.071(4) -0.040(3) -0.012(3) 0.000(3) C6 0.040(3) 0.058(3) 0.066(4) -0.032(3) -0.015(3) 0.002(2) N1 0.040(2) 0.051(3) 0.052(3) -0.019(2) -0.0162(19) -0.0016(19) N2 0.044(2) 0.049(2) 0.059(3) -0.022(2) -0.018(2) 0.007(2) C7 0.055(3) 0.054(3) 0.067(4) -0.020(3) -0.025(3) 0.003(3) C8 0.057(4) 0.070(4) 0.089(5) -0.029(4) -0.040(4) 0.005(3) C9 0.058(4) 0.079(5) 0.105(6) -0.039(4) -0.034(4) -0.010(3) C10 0.063(4) 0.050(3) 0.078(4) -0.023(3) -0.028(3) -0.002(3) C11 0.050(3) 0.046(3) 0.053(3) -0.022(2) -0.014(2) -0.004(2) C12 0.053(3) 0.046(3) 0.055(3) -0.024(2) -0.018(3) 0.003(2) C13 0.084(5) 0.051(3) 0.087(5) -0.025(3) -0.047(4) 0.004(3) C14 0.095(6) 0.055(4) 0.089(5) -0.028(4) -0.051(5) 0.023(4) C15 0.068(4) 0.073(5) 0.082(5) -0.030(4) -0.037(4) 0.019(4) C16 0.049(3) 0.074(4) 0.076(4) -0.033(4) -0.026(3) 0.007(3) N3 0.043(2) 0.051(3) 0.058(3) -0.024(2) -0.015(2) 0.005(2) N4 0.036(2) 0.052(3) 0.056(3) -0.018(2) -0.011(2) -0.0008(19) C17 0.063(4) 0.060(4) 0.078(5) -0.034(3) -0.031(3) 0.009(3) C18 0.083(5) 0.081(5) 0.068(4) -0.042(4) -0.035(4) 0.020(4) C19 0.070(5) 0.081(5) 0.062(4) -0.033(4) -0.011(3) 0.012(4) C20 0.047(3) 0.075(4) 0.061(4) -0.024(3) -0.010(3) 0.006(3) C21 0.040(3) 0.046(3) 0.055(3) -0.017(2) -0.012(2) 0.006(2) C22 0.037(3) 0.043(3) 0.055(3) -0.015(2) -0.010(2) 0.004(2) C23 0.042(3) 0.059(3) 0.066(4) -0.019(3) -0.015(3) 0.002(3) C24 0.046(3) 0.061(4) 0.086(5) -0.022(3) -0.026(3) -0.004(3) C25 0.064(4) 0.070(4) 0.079(5) -0.034(4) -0.033(4) 0.004(3) C26 0.055(4) 0.065(4) 0.062(4) -0.028(3) -0.013(3) -0.001(3) N5 0.155(10) 0.125(8) 0.091(6) -0.047(6) -0.043(7) 0.030(7) C27 0.102(9) 0.135(11) 0.125(10) -0.052(8) -0.039(8) 0.023(8) C28 0.110(10) 0.25(2) 0.142(13) -0.118(14) -0.034(9) -0.001(11) C29 0.197(12) 0.236(12) 0.169(11) -0.093(8) -0.081(9) 0.009(9) C30 0.109(9) 0.250(19) 0.086(7) -0.092(10) -0.026(7) -0.010(10) C31 0.112(7) 0.075(5) 0.083(6) -0.039(4) -0.040(5) 0.028(5) O5 0.065(4) 0.127(6) 0.152(7) -0.085(6) -0.023(4) 0.014(4) O6 0.074(3) 0.061(3) 0.103(4) -0.034(3) -0.039(3) 0.009(2) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 N4 2.020(5) . ? Cu1 N1 2.034(5) . ? Cu1 O2 2.082(5) . ? Cu1 N2 2.113(5) . ? Cu1 N3 2.167(5) . ? Cu1 O1 2.244(5) . ? Cl1 C3 1.723(7) . ? Cl2 C6 1.738(7) . ? O1 C1 1.276(7) . ? O2 C2 1.274(7) . ? O3 C4 1.230(8) . ? O4 C5 1.227(8) . ? C1 C6 1.385(8) . ? C1 C2 1.522(9) . ? C2 C3 1.378(9) . ? C3 C4 1.427(9) . ? C4 C5 1.544(10) . ? C5 C6 1.417(9) . ? N1 C7 1.317(8) . ? N1 C11 1.343(8) . ? N2 C16 1.326(8) . ? N2 C12 1.353(8) . ? C7 C8 1.390(10) . ? C7 H7 0.93 . ? C8 C9 1.360(11) . ? C8 H8 0.93 . ? C9 C10 1.374(10) . ? C9 H9 0.93 . ? C10 C11 1.377(9) . ? C10 H10 0.93 . ? C11 C12 1.494(9) . ? C12 C13 1.384(9) . ? C13 C14 1.381(11) . ? C13 H13 0.93 . ? C14 C15 1.355(12) . ? C14 H14 0.93 . ? C15 C16 1.383(11) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? N3 C17 1.333(9) . ? N3 C21 1.362(8) . ? N4 C26 1.317(9) . ? N4 C22 1.358(8) . ? C17 C18 1.371(11) . ? C17 H17 0.93 . ? C18 C19 1.394(12) . ? C18 H18 0.93 . ? C19 C20 1.374(12) . ? C19 H19 0.93 . ? C20 C21 1.389(9) . ? C20 H20 0.93 . ? C21 C22 1.474(9) . ? C22 C23 1.384(9) . ? C23 C24 1.384(10) . ? C23 H23 0.93 . ? C24 C25 1.371(11) . ? C24 H24 0.93 . ? C25 C26 1.371(10) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? N5 C31 1.384(15) . ? N5 C27 1.396(17) . ? C27 C28 1.347(19) . ? C27 H27 0.93 . ? C28 C29 1.40(3) . ? C28 H28 0.93 . ? C29 C30 1.32(2) . ? C29 H29 0.93 . ? C30 C31 1.290(14) . ? C30 H30 0.93 . ? C31 C31 1.46(2) 2_666 ? O5 H5B 0.950(6) . ? O5 H5A 0.955(10) . ? O6 H6A 0.94(2) . ? O6 H6B 0.95(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 N4 Cu1 N1 172.7(2) . . ? N4 Cu1 O2 93.52(19) . . ? N1 Cu1 O2 92.23(19) . . ? N4 Cu1 N2 95.6(2) . . ? N1 Cu1 N2 79.5(2) . . ? O2 Cu1 N2 166.64(18) . . ? N4 Cu1 N3 79.0(2) . . ? N1 Cu1 N3 96.3(2) . . ? O2 Cu1 N3 92.65(18) . . ? N2 Cu1 N3 98.64(19) . . ? N4 Cu1 O1 96.40(19) . . ? N1 Cu1 O1 89.35(18) . . ? O2 Cu1 O1 75.15(17) . . ? N2 Cu1 O1 94.12(18) . . ? N3 Cu1 O1 166.79(18) . . ? C1 O1 Cu1 112.6(4) . . ? C2 O2 Cu1 118.6(4) . . ? O1 C1 C6 125.0(6) . . ? O1 C1 C2 116.5(5) . . ? C6 C1 C2 118.5(5) . . ? O2 C2 C3 124.3(6) . . ? O2 C2 C1 115.5(5) . . ? C3 C2 C1 120.2(5) . . ? C2 C3 C4 121.9(6) . . ? C2 C3 Cl1 119.8(5) . . ? C4 C3 Cl1 118.3(5) . . ? O3 C4 C3 124.0(7) . . ? O3 C4 C5 117.6(6) . . ? C3 C4 C5 118.4(6) . . ? O4 C5 C6 125.0(7) . . ? O4 C5 C4 117.5(6) . . ? C6 C5 C4 117.5(5) . . ? C1 C6 C5 123.5(6) . . ? C1 C6 Cl2 118.8(5) . . ? C5 C6 Cl2 117.7(5) . . ? C7 N1 C11 119.8(5) . . ? C7 N1 Cu1 124.1(4) . . ? C11 N1 Cu1 116.1(4) . . ? C16 N2 C12 118.1(6) . . ? C16 N2 Cu1 128.3(5) . . ? C12 N2 Cu1 113.4(4) . . ? N1 C7 C8 120.9(6) . . ? N1 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 119.9(7) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 119.0(7) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 118.9(6) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? N1 C11 C10 121.5(6) . . ? N1 C11 C12 115.7(5) . . ? C10 C11 C12 122.7(6) . . ? N2 C12 C13 122.1(6) . . ? N2 C12 C11 115.2(5) . . ? C13 C12 C11 122.7(6) . . ? C14 C13 C12 118.6(7) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 119.2(7) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 119.6(7) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? N2 C16 C15 122.4(7) . . ? N2 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C17 N3 C21 118.7(6) . . ? C17 N3 Cu1 129.0(5) . . ? C21 N3 Cu1 112.4(4) . . ? C26 N4 C22 119.6(5) . . ? C26 N4 Cu1 123.7(4) . . ? C22 N4 Cu1 116.6(4) . . ? N3 C17 C18 123.2(7) . . ? N3 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C17 C18 C19 118.6(7) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C18 C19 C20 118.9(7) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C21 119.8(7) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? N3 C21 C20 120.9(6) . . ? N3 C21 C22 115.3(5) . . ? C20 C21 C22 123.8(6) . . ? N4 C22 C23 120.1(6) . . ? N4 C22 C21 116.7(5) . . ? C23 C22 C21 123.3(6) . . ? C22 C23 C24 119.3(6) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 119.5(6) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 118.3(7) . . ? C24 C25 H25 120.8 . . ? C26 C25 H25 120.8 . . ? N4 C26 C25 123.1(7) . . ? N4 C26 H26 118.4 . . ? C25 C26 H26 118.4 . . ? C31 N5 C27 118.8(11) . . ? C28 C27 N5 121.0(14) . . ? C28 C27 H27 119.5 . . ? N5 C27 H27 119.5 . . ? C27 C28 C29 113.5(16) . . ? C27 C28 H28 123.3 . . ? C29 C28 H28 123.3 . . ? C30 C29 C28 127.4(19) . . ? C30 C29 H29 116.3 . . ? C28 C29 H29 116.3 . . ? C31 C30 C29 117.0(16) . . ? C31 C30 H30 121.5 . . ? C29 C30 H30 121.5 . . ? C30 C31 N5 122.1(12) . . ? C30 C31 C31 118.3(13) . 2_666 ? N5 C31 C31 119.5(12) . 2_666 ? H5B O5 H5A 103(2) . . ? H6A O6 H6B 105(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 N4 Cu1 O1 C1 -101.5(4) . . . . ? N1 Cu1 O1 C1 83.0(4) . . . . ? O2 Cu1 O1 C1 -9.5(4) . . . . ? N2 Cu1 O1 C1 162.4(4) . . . . ? N3 Cu1 O1 C1 -32.6(10) . . . . ? N4 Cu1 O2 C2 107.0(5) . . . . ? N1 Cu1 O2 C2 -77.5(5) . . . . ? N2 Cu1 O2 C2 -26.1(11) . . . . ? N3 Cu1 O2 C2 -173.9(4) . . . . ? O1 Cu1 O2 C2 11.3(4) . . . . ? Cu1 O1 C1 C6 -171.2(5) . . . . ? Cu1 O1 C1 C2 7.1(6) . . . . ? Cu1 O2 C2 C3 168.5(5) . . . . ? Cu1 O2 C2 C1 -11.2(7) . . . . ? O1 C1 C2 O2 2.0(8) . . . . ? C6 C1 C2 O2 -179.6(5) . . . . ? O1 C1 C2 C3 -177.7(5) . . . . ? C6 C1 C2 C3 0.7(8) . . . . ? O2 C2 C3 C4 -178.8(6) . . . . ? C1 C2 C3 C4 0.9(9) . . . . ? O2 C2 C3 Cl1 0.5(9) . . . . ? C1 C2 C3 Cl1 -179.8(4) . . . . ? C2 C3 C4 O3 178.2(7) . . . . ? Cl1 C3 C4 O3 -1.1(10) . . . . ? C2 C3 C4 C5 -2.7(9) . . . . ? Cl1 C3 C4 C5 178.0(5) . . . . ? O3 C4 C5 O4 0.0(10) . . . . ? C3 C4 C5 O4 -179.2(6) . . . . ? O3 C4 C5 C6 -177.9(6) . . . . ? C3 C4 C5 C6 3.0(9) . . . . ? O1 C1 C6 C5 177.9(6) . . . . ? C2 C1 C6 C5 -0.3(9) . . . . ? O1 C1 C6 Cl2 -3.8(8) . . . . ? C2 C1 C6 Cl2 178.0(4) . . . . ? O4 C5 C6 C1 -179.2(6) . . . . ? C4 C5 C6 C1 -1.5(9) . . . . ? O4 C5 C6 Cl2 2.5(9) . . . . ? C4 C5 C6 Cl2 -179.8(4) . . . . ? N4 Cu1 N1 C7 130.5(15) . . . . ? O2 Cu1 N1 C7 -11.8(5) . . . . ? N2 Cu1 N1 C7 178.8(6) . . . . ? N3 Cu1 N1 C7 81.1(5) . . . . ? O1 Cu1 N1 C7 -86.9(5) . . . . ? N4 Cu1 N1 C11 -50.1(18) . . . . ? O2 Cu1 N1 C11 167.6(4) . . . . ? N2 Cu1 N1 C11 -1.8(4) . . . . ? N3 Cu1 N1 C11 -99.5(4) . . . . ? O1 Cu1 N1 C11 92.5(4) . . . . ? N4 Cu1 N2 C16 -0.6(6) . . . . ? N1 Cu1 N2 C16 -175.2(6) . . . . ? O2 Cu1 N2 C16 132.2(8) . . . . ? N3 Cu1 N2 C16 -80.3(6) . . . . ? O1 Cu1 N2 C16 96.2(6) . . . . ? N4 Cu1 N2 C12 174.9(4) . . . . ? N1 Cu1 N2 C12 0.3(4) . . . . ? O2 Cu1 N2 C12 -52.2(11) . . . . ? N3 Cu1 N2 C12 95.2(4) . . . . ? O1 Cu1 N2 C12 -88.2(4) . . . . ? C11 N1 C7 C8 0.0(10) . . . . ? Cu1 N1 C7 C8 179.4(5) . . . . ? N1 C7 C8 C9 -2.1(12) . . . . ? C7 C8 C9 C10 3.2(13) . . . . ? C8 C9 C10 C11 -2.1(13) . . . . ? C7 N1 C11 C10 1.0(9) . . . . ? Cu1 N1 C11 C10 -178.4(5) . . . . ? C7 N1 C11 C12 -177.7(6) . . . . ? Cu1 N1 C11 C12 2.9(7) . . . . ? C9 C10 C11 N1 0.0(11) . . . . ? C9 C10 C11 C12 178.6(7) . . . . ? C16 N2 C12 C13 -0.5(10) . . . . ? Cu1 N2 C12 C13 -176.6(6) . . . . ? C16 N2 C12 C11 177.1(6) . . . . ? Cu1 N2 C12 C11 1.0(7) . . . . ? N1 C11 C12 N2 -2.6(8) . . . . ? C10 C11 C12 N2 178.7(6) . . . . ? N1 C11 C12 C13 175.0(6) . . . . ? C10 C11 C12 C13 -3.7(10) . . . . ? N2 C12 C13 C14 2.6(11) . . . . ? C11 C12 C13 C14 -174.8(7) . . . . ? C12 C13 C14 C15 -2.7(13) . . . . ? C13 C14 C15 C16 0.9(13) . . . . ? C12 N2 C16 C15 -1.5(11) . . . . ? Cu1 N2 C16 C15 173.9(6) . . . . ? C14 C15 C16 N2 1.3(12) . . . . ? N4 Cu1 N3 C17 178.8(6) . . . . ? N1 Cu1 N3 C17 -6.8(6) . . . . ? O2 Cu1 N3 C17 85.7(5) . . . . ? N2 Cu1 N3 C17 -87.1(6) . . . . ? O1 Cu1 N3 C17 108.0(9) . . . . ? N4 Cu1 N3 C21 0.6(4) . . . . ? N1 Cu1 N3 C21 175.0(4) . . . . ? O2 Cu1 N3 C21 -92.5(4) . . . . ? N2 Cu1 N3 C21 94.7(4) . . . . ? O1 Cu1 N3 C21 -70.2(9) . . . . ? N1 Cu1 N4 C26 131.3(15) . . . . ? O2 Cu1 N4 C26 -86.4(5) . . . . ? N2 Cu1 N4 C26 83.9(5) . . . . ? N3 Cu1 N4 C26 -178.4(6) . . . . ? O1 Cu1 N4 C26 -10.9(5) . . . . ? N1 Cu1 N4 C22 -51.5(18) . . . . ? O2 Cu1 N4 C22 90.8(4) . . . . ? N2 Cu1 N4 C22 -98.9(4) . . . . ? N3 Cu1 N4 C22 -1.2(4) . . . . ? O1 Cu1 N4 C22 166.3(4) . . . . ? C21 N3 C17 C18 0.2(10) . . . . ? Cu1 N3 C17 C18 -177.9(5) . . . . ? N3 C17 C18 C19 -0.9(11) . . . . ? C17 C18 C19 C20 0.4(12) . . . . ? C18 C19 C20 C21 0.9(11) . . . . ? C17 N3 C21 C20 1.1(9) . . . . ? Cu1 N3 C21 C20 179.5(5) . . . . ? C17 N3 C21 C22 -178.4(5) . . . . ? Cu1 N3 C21 C22 0.1(6) . . . . ? C19 C20 C21 N3 -1.6(10) . . . . ? C19 C20 C21 C22 177.8(6) . . . . ? C26 N4 C22 C23 0.2(9) . . . . ? Cu1 N4 C22 C23 -177.1(4) . . . . ? C26 N4 C22 C21 178.9(5) . . . . ? Cu1 N4 C22 C21 1.6(6) . . . . ? N3 C21 C22 N4 -1.1(7) . . . . ? C20 C21 C22 N4 179.5(6) . . . . ? N3 C21 C22 C23 177.6(5) . . . . ? C20 C21 C22 C23 -1.8(9) . . . . ? N4 C22 C23 C24 -2.2(9) . . . . ? C21 C22 C23 C24 179.2(6) . . . . ? C22 C23 C24 C25 2.5(10) . . . . ? C23 C24 C25 C26 -0.9(11) . . . . ? C22 N4 C26 C25 1.5(10) . . . . ? Cu1 N4 C26 C25 178.6(5) . . . . ? C24 C25 C26 N4 -1.1(11) . . . . ? C31 N5 C27 C28 -3(2) . . . . ? N5 C27 C28 C29 1(3) . . . . ? C27 C28 C29 C30 0(4) . . . . ? C28 C29 C30 C31 3(4) . . . . ? C29 C30 C31 N5 -5(2) . . . . ? C29 C30 C31 C31 178.3(17) . . . 2_666 ? C27 N5 C31 C30 5.1(18) . . . . ? C27 N5 C31 C31 -178.1(11) . . . 2_666 ? _database_code_depnum_ccdc_archive 'CCDC 947428'