# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1935 data_General #============================================================================== _audit_creation_date '1999-01-05' _audit_creation_method 'by teXsan for Windows v1.0' _audit_update_record ; ? ; #============================================================================== # SUBMISSION DETAILS _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_contact_author_name ' ENTER CONTACT NAME HERE' _publ_contact_author_address ; ENTER ADDRESS ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER ANY FOOTNOTES TO TITLE ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1997-1998). teXsan for Windows version 1.03. Single Crystal Structure Analysis Software. Version 1.04. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #============================================================================== data_x553 #(1)_____________________ #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows (MSC, 1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan for Windows (MSC, 1997)' _computing_publication_material 'teXsan for Windows (MSC, 1997)' #------------------------------------------------------------------------------ _cell_length_a 26.754(3) _cell_length_b 8.466(3) _cell_length_c 16.334(3) _cell_angle_alpha 90 _cell_angle_beta 100.94(1) _cell_angle_gamma 90 _cell_volume 3632(1) _cell_formula_units_Z 8 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 29.6 _cell_measurement_theta_max 30.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' +x, +y, +z' ' -x, +y,1/2-z' ' -x, +y,1/2-z' ' -x, -y, -z' ' -x, -y, -z' ' +x, -y,1/2+z' ' +x, -y,1/2+z' '1/2+x,1/2+y, +z' '1/2+x,1/2+y, +z' '1/2-x,1/2+y,1/2-z' '1/2-x,1/2+y,1/2-z' '1/2-x,1/2-y, -z' '1/2-x,1/2-y, -z' '1/2+x,1/2-y,1/2+z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irregular' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 454.24 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H10 Cl2 Cu2 N7 O ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1800.00 _exptl_absorpt_coefficient_mu 5.709 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.635 _exptl_special_details ; The scan width was (1.57+0.14tan\q)\% with an \w scan speed of 8\% per minute (up to 6 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.80 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 7 -1 -2 4 -2 1 5 -1 2 _diffrn_reflns_number 3004 _reflns_number_total 2930 _reflns_number_gt 2301 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.05504 _diffrn_reflns_av_sigmaI/netI 0.051 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 60.09 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.02035 _diffrn_orient_matrix_UB_12 -0.04798 _diffrn_orient_matrix_UB_13 0.05170 _diffrn_orient_matrix_UB_21 -0.02208 _diffrn_orient_matrix_UB_22 -0.09617 _diffrn_orient_matrix_UB_23 -0.00857 _diffrn_orient_matrix_UB_31 0.02340 _diffrn_orient_matrix_UB_32 -0.04901 _diffrn_orient_matrix_UB_33 -0.03379 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 88 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 80 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 56 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Cu 0 16 -2.019 0.589 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Cl 0 16 0.348 0.702 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Cu(1) 0.69451(2) 0.52125(8) 0.68977(3) 0.0370(2) 1.000 . Uani d ? Cu(2) 0.55304(2) 0.49454(8) 0.59044(4) 0.0353(2) 1.000 . Uani d ? Cl(1) 0.73315(5) 0.7197(2) 0.76832(7) 0.0628(4) 1.000 . Uani d ? Cl(2) 0.64410(4) 0.4559(1) 0.78126(6) 0.0434(3) 1.000 . Uani d ? Cl(3) 0.60527(4) 0.6950(1) 0.57506(8) 0.0491(4) 1.000 . Uani d ? Cl(4) 0.48396(4) 0.6484(1) 0.57686(7) 0.0488(3) 1.000 . Uani d ? O(1) 0.6132(1) 0.8481(5) 0.7806(2) 0.093(2) 1.000 . Uani d ? N(1) 0.7398(1) 0.5434(4) 0.6036(2) 0.034(1) 1.000 . Uani d ? N(2) 0.6597(1) 0.3738(4) 0.6017(2) 0.0276(9) 1.000 . Uani d ? N(3) 0.6446(1) 0.3526(5) 0.4575(2) 0.054(1) 1.000 . Uani d ? N(4) 0.6075(1) 0.3344(4) 0.5978(2) 0.0272(9) 1.000 . Uani d ? N(5) 0.6324(1) 0.0915(4) 0.6603(2) 0.055(1) 1.000 . Uani d ? N(6) 0.5169(1) 0.3055(4) 0.6302(2) 0.035(1) 1.000 . Uani d ? N(7) 0.4730(1) 0.0173(5) 0.6491(2) 0.063(1) 1.000 . Uani d ? C(1) 0.7828(2) 0.6225(6) 0.6096(3) 0.055(2) 1.000 . Uani d ? C(2) 0.8095(2) 0.6253(8) 0.5435(3) 0.077(2) 1.000 . Uani d ? C(3) 0.7915(2) 0.5475(8) 0.4730(3) 0.067(2) 1.000 . Uani d ? C(4) 0.7477(2) 0.4682(7) 0.4669(2) 0.055(2) 1.000 . Uani d ? C(5) 0.7215(1) 0.4676(5) 0.5314(2) 0.033(1) 1.000 . Uani d ? C(6) 0.6715(1) 0.3915(5) 0.5298(2) 0.035(1) 1.000 . Uani d ? C(7) 0.5988(1) 0.1978(5) 0.6300(2) 0.032(1) 1.000 . Uani d ? C(8) 0.5442(1) 0.1706(5) 0.6335(2) 0.030(1) 1.000 . Uani d ? C(9) 0.5227(2) 0.0271(5) 0.6398(3) 0.046(1) 1.000 . Uani d ? C(10) 0.4478(2) 0.1530(6) 0.6507(3) 0.047(1) 1.000 . Uani d ? C(11) 0.4689(2) 0.2960(6) 0.6385(3) 0.044(1) 1.000 . Uani d ? H(1) 0.7960 0.6769 0.6601 0.066 1.000 . Uiso c ? H(2) 0.8407 0.6840 0.5503 0.087 1.000 . Uiso c ? H(3) 0.8087 0.5470 0.4271 0.093 1.000 . Uiso c ? H(4) 0.7341 0.4125 0.4173 0.066 1.000 . Uiso c ? H(5) 0.6511 0.2986 0.3988 0.034 1.000 . Uiso c ? H(6) 0.6234 0.3281 0.4545 0.034 1.000 . Uiso c ? H(7) 0.6620 0.0977 0.6458 0.034 1.000 . Uiso c ? H(8) 0.6242 -0.0021 0.6928 0.034 1.000 . Uiso c ? H(9) 0.5423 -0.0659 0.6385 0.055 1.000 . Uiso c ? H(10) 0.4140 0.1491 0.6608 0.058 1.000 . Uiso c ? H(11) 0.4486 0.3894 0.6352 0.052 1.000 . Uiso c ? H(12) 0.5771 0.7927 0.7612 0.034 1.000 . Uiso c ? H(13) 0.6384 0.8253 0.8304 0.103 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu(1) 0.0330(3) 0.0475(4) 0.0319(3) -0.0117(3) 0.0094(3) -0.0053(3) Cu(2) 0.0250(3) 0.0338(3) 0.0469(4) -0.0011(3) 0.0059(3) 0.0061(3) Cl(1) 0.0651(8) 0.070(1) 0.0540(7) -0.0313(7) 0.0139(6) -0.0237(7) Cl(2) 0.0456(6) 0.0545(8) 0.0346(6) -0.0063(6) 0.0191(5) -0.0057(5) Cl(3) 0.0379(6) 0.0374(7) 0.0756(8) -0.0053(5) 0.0200(6) 0.0075(6) Cl(4) 0.0319(6) 0.0388(7) 0.0747(8) 0.0039(5) 0.0078(6) -0.0018(6) O(1) 0.117(3) 0.076(3) 0.080(3) 0.015(3) 0.000(2) 0.024(2) N(1) 0.026(2) 0.039(2) 0.037(2) -0.002(2) 0.009(2) 0.005(2) N(2) 0.021(2) 0.031(2) 0.031(2) -0.003(2) 0.005(1) 0.001(2) N(3) 0.038(2) 0.101(4) 0.025(2) -0.020(2) 0.008(2) -0.018(2) N(4) 0.017(2) 0.034(2) 0.030(2) -0.006(2) 0.004(1) 0.003(2) N(5) 0.036(2) 0.037(2) 0.099(3) 0.001(2) 0.033(2) 0.021(2) N(6) 0.026(2) 0.039(2) 0.038(2) -0.004(2) 0.005(2) 0.005(2) N(7) 0.046(2) 0.063(3) 0.084(3) -0.008(2) 0.024(2) 0.005(3) C(1) 0.030(2) 0.073(4) 0.058(3) -0.019(3) 0.003(2) 0.009(3) C(2) 0.023(3) 0.129(6) 0.082(4) -0.007(3) 0.015(3) 0.054(4) C(3) 0.023(2) 0.146(6) 0.033(3) 0.001(3) 0.010(2) 0.017(3) C(4) 0.042(3) 0.091(4) 0.032(2) 0.002(3) 0.007(2) 0.002(3) C(5) 0.022(2) 0.053(3) 0.025(2) 0.003(2) 0.006(2) 0.005(2) C(6) 0.032(2) 0.047(3) 0.025(2) 0.002(2) 0.003(2) -0.000(2) C(7) 0.024(2) 0.034(2) 0.040(2) 0.001(2) 0.009(2) 0.001(2) C(8) 0.028(2) 0.031(2) 0.034(2) -0.003(2) 0.010(2) -0.001(2) C(9) 0.038(3) 0.040(3) 0.062(3) 0.002(2) 0.018(2) 0.007(2) C(10) 0.033(3) 0.049(3) 0.063(3) -0.004(2) 0.017(2) 0.009(3) C(11) 0.028(2) 0.049(3) 0.056(3) -0.001(2) 0.014(2) 0.010(2) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.000000122(5) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2301 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_all 0.0390 _refine_ls_wR_factor_ref 0.0390 _refine_ls_goodness_of_fit_all 3.224 _refine_ls_goodness_of_fit_ref 3.490 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0001 _refine_diff_density_min -0.61 _refine_diff_density_max 0.70 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu(1) Cl(1) 2.243(2) . . ? Cu(1) Cl(2) 2.263(2) . . ? Cu(1) N(1) 2.032(6) . . ? Cu(1) N(2) 1.996(6) . . ? Cu(2) Cl(3) 2.243(2) . . ? Cu(2) Cl(4) 2.238(2) . . ? Cu(2) N(4) 1.977(6) . . ? Cu(2) N(6) 2.039(6) . . ? O(1) H(12) 1.07 . . no O(1) H(13) 0.97 . . no N(1) C(1) 1.319(9) . . ? N(1) C(5) 1.351(8) . . ? N(2) N(4) 1.426(7) . . ? N(2) C(6) 1.282(8) . . ? N(3) C(6) 1.304(8) . . ? N(3) H(5) 1.10 . . no N(3) H(6) 0.60 . . no N(4) C(7) 1.309(9) . . ? N(5) C(7) 1.301(9) . . ? N(5) H(7) 0.87 . . no N(5) H(8) 1.00 . . no N(6) C(8) 1.351(9) . . ? N(6) C(11) 1.319(9) . . ? N(7) C(9) 1.368(9) . . ? N(7) C(10) 1.34(1) . . ? C(1) C(2) 1.40(1) . . ? C(1) H(1) 0.95 . . no C(2) C(3) 1.34(1) . . ? C(2) H(2) 0.96 . . no C(3) C(4) 1.34(1) . . ? C(3) H(3) 0.95 . . no C(4) C(5) 1.372(9) . . ? C(4) H(4) 0.95 . . no C(5) C(6) 1.479(9) . . ? C(7) C(8) 1.491(9) . . ? C(8) C(9) 1.36(1) . . ? C(9) H(9) 0.95 . . no C(10) C(11) 1.37(1) . . ? C(10) H(10) 0.95 . . no C(11) H(11) 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl(1) Cu(1) Cl(2) 94.19(8) . . . ? Cl(1) Cu(1) N(1) 93.2(2) . . . ? Cl(1) Cu(1) N(2) 169.0(2) . . . ? Cl(2) Cu(1) N(1) 171.1(2) . . . ? Cl(2) Cu(1) N(2) 93.9(2) . . . ? N(1) Cu(1) N(2) 79.4(2) . . . ? Cl(3) Cu(2) Cl(4) 93.94(9) . . . ? Cl(3) Cu(2) N(4) 93.3(2) . . . ? Cl(3) Cu(2) N(6) 166.7(2) . . . ? Cl(4) Cu(2) N(4) 172.1(2) . . . ? Cl(4) Cu(2) N(6) 93.2(2) . . . ? N(4) Cu(2) N(6) 80.3(2) . . . ? H(12) O(1) H(13) 127.3 . . . no Cu(1) N(1) C(1) 128.4(6) . . . ? Cu(1) N(1) C(5) 113.3(4) . . . ? C(1) N(1) C(5) 118.2(7) . . . ? Cu(1) N(2) N(4) 119.9(4) . . . ? Cu(1) N(2) C(6) 115.1(5) . . . ? N(4) N(2) C(6) 113.4(6) . . . ? C(6) N(3) H(5) 137.7 . . . no C(6) N(3) H(6) 121.0 . . . no H(5) N(3) H(6) 95.1 . . . no Cu(2) N(4) N(2) 123.1(4) . . . ? Cu(2) N(4) C(7) 116.5(5) . . . ? N(2) N(4) C(7) 115.8(6) . . . ? C(7) N(5) H(7) 117.0 . . . no C(7) N(5) H(8) 122.9 . . . no H(7) N(5) H(8) 119.6 . . . no Cu(2) N(6) C(8) 112.9(5) . . . ? Cu(2) N(6) C(11) 127.6(6) . . . ? C(8) N(6) C(11) 118.4(7) . . . ? C(9) N(7) C(10) 117.1(8) . . . ? N(1) C(1) C(2) 121.1(9) . . . ? N(1) C(1) H(1) 119.1 . . . no C(2) C(1) H(1) 119.9 . . . no C(1) C(2) C(3) 120.1(9) . . . ? C(1) C(2) H(2) 118.6 . . . no C(3) C(2) H(2) 121.3 . . . no C(2) C(3) C(4) 118.6(8) . . . ? C(2) C(3) H(3) 122.2 . . . no C(4) C(3) H(3) 119.1 . . . no C(3) C(4) C(5) 120.9(8) . . . ? C(3) C(4) H(4) 120.0 . . . no C(5) C(4) H(4) 119.1 . . . no N(1) C(5) C(4) 121.0(7) . . . ? N(1) C(5) C(6) 113.5(6) . . . ? C(4) C(5) C(6) 125.4(7) . . . ? N(2) C(6) N(3) 127.6(7) . . . ? N(2) C(6) C(5) 114.4(6) . . . ? N(3) C(6) C(5) 117.9(7) . . . ? N(4) C(7) N(5) 127.0(7) . . . ? N(4) C(7) C(8) 113.6(7) . . . ? N(5) C(7) C(8) 119.3(7) . . . ? N(6) C(8) C(7) 113.3(7) . . . ? N(6) C(8) C(9) 121.7(7) . . . ? C(7) C(8) C(9) 125.0(7) . . . ? N(7) C(9) C(8) 119.8(8) . . . ? N(7) C(9) H(9) 120.3 . . . no C(8) C(9) H(9) 119.9 . . . no N(7) C(10) C(11) 122.4(7) . . . ? N(7) C(10) H(10) 118.4 . . . no C(11) C(10) H(10) 119.2 . . . no N(6) C(11) C(10) 120.3(8) . . . ? N(6) C(11) H(11) 119.9 . . . no C(10) C(11) H(11) 119.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cu(1) Cl(1) 3.198(3) . 6_646 no Cu(2) Cl(4) 2.981(2) . 3_666 no Cl(1) O(1) 3.429(8) . . no Cl(1) N(1) 3.440(6) . 6_656 no Cl(1) N(2) 3.481(6) . 6_656 no Cl(1) C(4) 3.567(8) . 4_565 no Cl(2) N(3) 3.301(7) . 4_565 no Cl(2) O(1) 3.421(8) . . no Cl(3) O(1) 3.568(7) . . no Cl(3) C(2) 3.597(9) . 7_666 no Cl(4) N(7) 3.370(9) . 1_565 no Cl(4) N(3) 3.378(6) . 3_666 no Cl(4) N(4) 3.391(6) . 3_666 no Cl(4) N(6) 3.401(6) . 3_666 no Cl(4) C(9) 3.464(9) . 1_565 no O(1) N(5) 2.959(9) . 1_565 no O(1) N(7) 3.11(1) . 2_666 no O(1) N(3) 3.319(8) . 4_565 no O(1) C(10) 3.36(1) . 2_666 no O(1) C(9) 3.37(1) . 1_565 no N(5) C(3) 3.46(1) . 7_656 no N(7) N(7) 3.34(1) . 2_656 no N(7) C(9) 3.43(1) . 2_656 no C(1) C(3) 3.54(1) . 7_666 no C(8) C(10) 3.49(1) . 2_656 no C(9) C(10) 3.53(1) . 2_656 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Cu(1) N(1) C(1) C(2) . . . . 180.0(7) no Cu(1) N(1) C(5) C(4) . . . . -179.0(7) no Cu(1) N(1) C(5) C(6) . . . . 2.6(8) no Cu(1) N(2) N(4) Cu(2) . . . . 54.8(6) no Cu(1) N(2) N(4) C(7) . . . . -100.4(6) no Cu(1) N(2) C(6) N(3) . . . . -155.7(8) no Cu(1) N(2) C(6) C(5) . . . . 23.3(9) no Cu(2) N(4) N(2) C(6) . . . . -86.6(7) no Cu(2) N(4) C(7) N(5) . . . . -161.2(7) no Cu(2) N(4) C(7) C(8) . . . . 16.3(8) no Cu(2) N(6) C(8) C(7) . . . . 15.6(8) no Cu(2) N(6) C(8) C(9) . . . . -164.8(6) no Cu(2) N(6) C(11) C(10) . . . . 167.6(6) no Cl(1) Cu(1) N(1) C(1) . . . . 14.1(7) no Cl(1) Cu(1) N(1) C(5) . . . . -164.7(5) no Cl(1) Cu(1) N(2) N(4) . . . . -108.8(9) no Cl(1) Cu(1) N(2) C(6) . . . . 32(1) no Cl(2) Cu(1) N(1) C(1) . . . . -132(1) no Cl(2) Cu(1) N(1) C(5) . . . . 49(1) no Cl(2) Cu(1) N(2) N(4) . . . . 28.1(5) no Cl(2) Cu(1) N(2) C(6) . . . . 168.9(5) no Cl(3) Cu(2) N(4) N(2) . . . . 6.9(5) no Cl(3) Cu(2) N(4) C(7) . . . . 161.9(5) no Cl(3) Cu(2) N(6) C(8) . . . . -68(1) no Cl(3) Cu(2) N(6) C(11) . . . . 124.3(8) no Cl(4) Cu(2) N(4) N(2) . . . . 165(1) no Cl(4) Cu(2) N(4) C(7) . . . . -40(2) no Cl(4) Cu(2) N(6) C(8) . . . . 169.7(5) no Cl(4) Cu(2) N(6) C(11) . . . . 2.0(7) no N(1) Cu(1) N(2) N(4) . . . . -157.8(5) no N(1) Cu(1) N(2) C(6) . . . . -17.1(5) no N(1) C(1) C(2) C(3) . . . . 0(2) no N(1) C(5) C(4) C(3) . . . . -2(2) no N(1) C(5) C(6) N(2) . . . . -17(1) no N(1) C(5) C(6) N(3) . . . . 162.1(7) no N(2) Cu(1) N(1) C(1) . . . . -174.3(8) no N(2) Cu(1) N(1) C(5) . . . . 6.9(5) no N(2) N(4) Cu(2) N(6) . . . . -161.3(5) no N(2) N(4) C(7) N(5) . . . . -4(1) no N(2) N(4) C(7) C(8) . . . . 173.1(6) no N(2) C(6) C(5) C(4) . . . . 164.7(9) no N(3) C(6) N(2) N(4) . . . . -12(1) no N(3) C(6) C(5) C(4) . . . . -16(1) no N(4) Cu(2) N(6) C(8) . . . . -5.9(5) no N(4) Cu(2) N(6) C(11) . . . . -173.6(7) no N(4) N(2) C(6) C(5) . . . . 166.6(6) no N(4) C(7) C(8) N(6) . . . . -21.1(9) no N(4) C(7) C(8) C(9) . . . . 159.3(8) no N(5) C(7) C(8) N(6) . . . . 156.6(7) no N(5) C(7) C(8) C(9) . . . . -23(1) no N(6) Cu(2) N(4) C(7) . . . . -6.4(5) no N(6) C(8) C(9) N(7) . . . . -5(1) no N(6) C(11) C(10) N(7) . . . . -5(1) no N(7) C(9) C(8) C(7) . . . . 174.8(7) no C(1) N(1) C(5) C(4) . . . . 2(1) no C(1) N(1) C(5) C(6) . . . . -176.3(7) no C(1) C(2) C(3) C(4) . . . . 0(2) no C(2) C(1) N(1) C(5) . . . . -1(1) no C(2) C(3) C(4) C(5) . . . . 0(2) no C(3) C(4) C(5) C(6) . . . . 176.5(9) no C(6) N(2) N(4) C(7) . . . . 118.3(8) no C(7) C(8) N(6) C(11) . . . . -175.5(7) no C(8) N(6) C(11) C(10) . . . . 1(1) no C(8) C(9) N(7) C(10) . . . . 1(1) no C(9) N(7) C(10) C(11) . . . . 4(1) no C(9) C(8) N(6) C(11) . . . . 4(1) no #------------------------------------------------------------------------------ #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== #===END data__x552 #(2) #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows (MSC, 1997)' _computing_structure_solution ; SHELX97 (Sheldrick, 1997) ; _computing_structure_refinement 'teXsan for Windows (MSC, 1997)' _computing_publication_material 'teXsan for Windows (MSC, 1997)' #------------------------------------------------------------------------------ _cell_length_a 27.260(4) _cell_length_b 8.688(8) _cell_length_c 16.644(5) _cell_angle_alpha 90 _cell_angle_beta 100.45(2) _cell_angle_gamma 90 _cell_volume 3876(3) _cell_formula_units_Z 8 _cell_measurement_temperature 299.2 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 7.1 _cell_measurement_theta_max 13.7 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' +x, +y, +z' ' -x, +y,1/2-z' ' -x, +y,1/2-z' ' -x, -y, -z' ' -x, -y, -z' ' +x, -y,1/2+z' ' +x, -y,1/2+z' '1/2+x,1/2+y, +z' '1/2+x,1/2+y, +z' '1/2-x,1/2+y,1/2-z' '1/2-x,1/2+y,1/2-z' '1/2-x,1/2-y, -z' '1/2-x,1/2-y, -z' '1/2+x,1/2-y,1/2+z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'irregular' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 2.419 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 705.98 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H13 Br4 Cu2 N7 O ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 2672.00 _exptl_absorpt_coefficient_mu 10.481 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.606 _exptl_special_details ; The scan width was (1.10+0.35tan\q)\% with an \w scan speed of 4\% per minute (up to 7 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 299.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.69 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -9 1 1 -7 1 3 -6 0 4 _diffrn_reflns_number 4873 _reflns_number_total 4773 _reflns_number_gt 2318 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.05490 _diffrn_reflns_av_sigmaI/netI 0.136 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00510 _diffrn_orient_matrix_UB_12 0.09700 _diffrn_orient_matrix_UB_13 0.02976 _diffrn_orient_matrix_UB_21 -0.00674 _diffrn_orient_matrix_UB_22 0.05703 _diffrn_orient_matrix_UB_23 -0.05305 _diffrn_orient_matrix_UB_31 -0.03633 _diffrn_orient_matrix_UB_32 -0.02421 _diffrn_orient_matrix_UB_33 -0.00571 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 88 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 104 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 56 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Cu 0 16 0.263 1.266 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Br 0 32 -0.374 2.456 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(1) 0.26970(4) -0.2332(1) 0.23177(6) 0.0562(3) 1.000 . Uani d ? Br(2) 0.35957(4) 0.0449(1) 0.21528(6) 0.0414(3) 1.000 . Uani d ? Br(3) 0.39251(3) -0.2006(1) 0.42800(6) 0.0436(3) 1.000 . Uani d ? Br(4) 0.51625(3) -0.1556(1) 0.41903(7) 0.0477(3) 1.000 . Uani d ? Cu(1) 0.30792(4) -0.0232(1) 0.31235(6) 0.0327(3) 1.000 . Uani d ? Cu(2) 0.44578(4) 0.0087(1) 0.40871(6) 0.0324(3) 1.000 . Uani d ? O(1) 0.3911(3) 0.357(1) 0.7169(5) 0.098(4) 1.000 . Uani d ? N(1) 0.2622(2) -0.0416(8) 0.3954(4) 0.031(2) 1.000 . Uani d ? N(2) 0.3540(2) 0.161(1) 0.5386(4) 0.046(2) 1.000 . Uani d ? N(3) 0.3410(2) 0.1263(7) 0.3958(4) 0.021(2) 1.000 . Uani d ? N(4) 0.3916(2) 0.1656(8) 0.3999(4) 0.027(2) 1.000 . Uani d ? N(5) 0.3667(3) 0.4016(9) 0.3387(5) 0.046(3) 1.000 . Uani d ? N(6) 0.5238(3) 0.474(1) 0.3484(5) 0.057(3) 1.000 . Uani d ? N(7) 0.4808(2) 0.1924(9) 0.3709(4) 0.035(2) 1.000 . Uani d ? C(1) 0.2195(3) -0.117(1) 0.3898(5) 0.046(3) 1.000 . Uani d ? C(2) 0.1933(3) -0.122(2) 0.4512(7) 0.069(4) 1.000 . Uani d ? C(3) 0.2099(3) -0.042(2) 0.5223(6) 0.069(4) 1.000 . Uani d ? C(4) 0.2539(3) 0.038(1) 0.5302(5) 0.051(3) 1.000 . Uani d ? C(5) 0.2788(3) 0.036(1) 0.4642(5) 0.031(2) 1.000 . Uani d ? C(6) 0.3279(3) 0.112(1) 0.4679(5) 0.029(2) 1.000 . Uani d ? C(7) 0.4004(3) 0.299(1) 0.3688(5) 0.028(2) 1.000 . Uani d ? C(8) 0.4534(3) 0.326(1) 0.3641(5) 0.029(2) 1.000 . Uani d ? C(9) 0.4742(3) 0.466(1) 0.3562(6) 0.049(3) 1.000 . Uani d ? C(10) 0.5494(3) 0.345(1) 0.3509(6) 0.046(3) 1.000 . Uani d ? C(11) 0.5287(3) 0.206(1) 0.3636(5) 0.039(3) 1.000 . Uani d ? H(1) 0.2069 -0.1705 0.3406 0.059 1.000 . Uiso c ? H(2) 0.1630 -0.1839 0.4452 0.087 1.000 . Uiso c ? H(3) 0.1901 -0.0405 0.5636 0.081 1.000 . Uiso c ? H(4) 0.2658 0.0915 0.5790 0.065 1.000 . Uiso c ? H(5) 0.4553 0.5563 0.3574 0.059 1.000 . Uiso c ? H(6) 0.5837 0.3496 0.3453 0.055 1.000 . Uiso c ? H(7) 0.5489 0.1141 0.3679 0.048 1.000 . Uiso c ? H(8) 0.3427 0.1467 0.5904 0.054 1.000 . Uiso c ? H(9) 0.3863 0.2109 0.5423 0.054 1.000 . Uiso c ? H(10) 0.3313 0.3866 0.3380 0.052 1.000 . Uiso c ? H(11) 0.3753 0.4998 0.3156 0.052 1.000 . Uiso c ? H(12) 0.3688 0.4578 0.6768 0.114 1.000 . Uiso c ? H(13) 0.4152 0.4648 0.7668 0.114 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0558(7) 0.0677(8) 0.0462(6) -0.0315(6) 0.0124(5) -0.0199(6) Br(2) 0.0434(5) 0.0540(7) 0.0321(5) -0.0103(5) 0.0210(4) -0.0055(5) Br(3) 0.0335(5) 0.0366(6) 0.0635(7) -0.0046(5) 0.0161(4) 0.0096(5) Br(4) 0.0292(5) 0.0412(6) 0.0725(7) 0.0045(5) 0.0086(5) -0.0033(6) Cu(1) 0.0275(5) 0.0472(8) 0.0250(5) -0.0134(5) 0.0087(4) -0.0049(5) Cu(2) 0.0201(5) 0.0370(7) 0.0403(7) -0.0024(5) 0.0062(5) 0.0041(5) O(1) 0.123(8) 0.077(7) 0.090(7) -0.023(6) 0.013(6) -0.022(5) N(1) 0.028(4) 0.039(5) 0.029(4) -0.001(4) 0.009(3) 0.005(4) N(2) 0.025(4) 0.083(7) 0.030(4) -0.020(4) 0.004(3) -0.015(4) N(3) 0.016(3) 0.023(4) 0.024(4) -0.007(3) 0.001(3) 0.006(3) N(4) 0.010(3) 0.048(5) 0.024(4) -0.008(3) 0.006(3) -0.000(3) N(5) 0.031(4) 0.035(5) 0.078(6) 0.003(4) 0.027(4) 0.016(4) N(6) 0.042(5) 0.059(6) 0.075(7) -0.019(5) 0.022(5) -0.003(5) N(7) 0.026(4) 0.038(5) 0.040(4) -0.006(4) 0.005(3) -0.004(4) C(1) 0.028(5) 0.072(8) 0.039(6) -0.024(5) 0.005(4) 0.014(5) C(2) 0.027(5) 0.12(1) 0.067(8) -0.018(6) 0.019(5) 0.021(8) C(3) 0.026(5) 0.13(1) 0.053(7) -0.006(7) 0.027(5) 0.016(8) C(4) 0.038(5) 0.085(9) 0.030(5) -0.007(6) 0.007(4) -0.009(6) C(5) 0.021(4) 0.044(6) 0.029(5) 0.003(4) 0.010(4) 0.010(4) C(6) 0.024(4) 0.038(6) 0.026(5) -0.003(4) 0.004(4) 0.004(4) C(7) 0.020(4) 0.029(5) 0.038(5) -0.008(4) 0.012(4) -0.004(4) C(8) 0.036(5) 0.023(5) 0.032(5) -0.007(4) 0.013(4) -0.004(4) C(9) 0.038(6) 0.043(7) 0.072(7) -0.005(5) 0.028(5) -0.009(6) C(10) 0.030(5) 0.050(7) 0.063(7) -0.005(5) 0.020(5) 0.007(6) C(11) 0.024(4) 0.055(7) 0.040(6) -0.006(5) 0.012(4) -0.001(5) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00013|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2318 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1612 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_all 0.0580 _refine_ls_wR_factor_ref 0.0480 _refine_ls_goodness_of_fit_all 1.230 _refine_ls_goodness_of_fit_ref 1.440 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -0.90 _refine_diff_density_max 1.36 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br(1) Cu(1) 2.389(2) . . ? Br(2) Cu(1) 2.401(2) . . ? Br(3) Cu(2) 2.384(2) . . ? Br(4) Cu(2) 2.374(2) . . ? Cu(1) N(1) 2.028(8) . . ? Cu(1) N(3) 1.994(7) . . ? Cu(2) N(4) 1.996(8) . . ? Cu(2) N(7) 2.018(9) . . ? O(1) H(12) 1.19 . . no O(1) H(13) 1.34 . . no N(1) C(1) 1.32(1) . . ? N(1) C(5) 1.33(1) . . ? N(2) C(6) 1.33(1) . . ? N(2) H(8) 0.97 . . no N(2) H(9) 0.97 . . no N(3) N(4) 1.411(9) . . ? N(3) C(6) 1.32(1) . . ? N(4) C(7) 1.31(1) . . ? N(5) C(7) 1.31(1) . . ? N(5) H(10) 0.97 . . no N(5) H(11) 0.98 . . no N(6) C(9) 1.38(1) . . ? N(6) C(10) 1.32(1) . . ? N(7) C(8) 1.37(1) . . ? N(7) C(11) 1.34(1) . . ? C(1) C(2) 1.35(1) . . ? C(1) H(1) 0.95 . . no C(2) C(3) 1.38(2) . . ? C(2) H(2) 0.97 . . no C(3) C(4) 1.37(2) . . ? C(3) H(3) 0.95 . . no C(4) C(5) 1.39(1) . . ? C(4) H(4) 0.94 . . no C(5) C(6) 1.49(1) . . ? C(7) C(8) 1.48(1) . . ? C(8) C(9) 1.36(1) . . ? C(9) H(5) 0.94 . . no C(10) C(11) 1.36(2) . . ? C(10) H(6) 0.96 . . no C(11) H(7) 0.97 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br(1) Cu(1) Br(2) 93.42(6) . . . ? Br(1) Cu(1) N(1) 93.6(2) . . . ? Br(1) Cu(1) N(3) 170.0(2) . . . ? Br(2) Cu(1) N(1) 170.2(3) . . . ? Br(2) Cu(1) N(3) 93.6(2) . . . ? N(1) Cu(1) N(3) 80.3(3) . . . ? Br(3) Cu(2) Br(4) 92.10(8) . . . ? Br(3) Cu(2) N(4) 94.0(2) . . . ? Br(3) Cu(2) N(7) 168.2(2) . . . ? Br(4) Cu(2) N(4) 173.8(2) . . . ? Br(4) Cu(2) N(7) 94.3(2) . . . ? N(4) Cu(2) N(7) 79.8(3) . . . ? H(12) O(1) H(13) 88.9 . . . no Cu(1) N(1) C(1) 129.1(7) . . . ? Cu(1) N(1) C(5) 113.1(6) . . . ? C(1) N(1) C(5) 117.8(9) . . . ? C(6) N(2) H(8) 122.6 . . . no C(6) N(2) H(9) 122.1 . . . no H(8) N(2) H(9) 115.3 . . . no Cu(1) N(3) N(4) 120.4(6) . . . ? Cu(1) N(3) C(6) 114.3(6) . . . ? N(4) N(3) C(6) 113.8(7) . . . ? Cu(2) N(4) N(3) 122.8(6) . . . ? Cu(2) N(4) C(7) 116.5(6) . . . ? N(3) N(4) C(7) 116.3(8) . . . ? C(7) N(5) H(10) 122.5 . . . no C(7) N(5) H(11) 122.8 . . . no H(10) N(5) H(11) 114.8 . . . no C(9) N(6) C(10) 119(1) . . . ? Cu(2) N(7) C(8) 114.3(6) . . . ? Cu(2) N(7) C(11) 128.6(8) . . . ? C(8) N(7) C(11) 116.2(9) . . . ? N(1) C(1) C(2) 123(1) . . . ? N(1) C(1) H(1) 118.8 . . . no C(2) C(1) H(1) 118.4 . . . no C(1) C(2) C(3) 120(1) . . . ? C(1) C(2) H(2) 119.7 . . . no C(3) C(2) H(2) 120.6 . . . no C(2) C(3) C(4) 119(1) . . . ? C(2) C(3) H(3) 119.1 . . . no C(4) C(3) H(3) 121.7 . . . no C(3) C(4) C(5) 117(1) . . . ? C(3) C(4) H(4) 119.5 . . . no C(5) C(4) H(4) 123.2 . . . no N(1) C(5) C(4) 123(1) . . . ? N(1) C(5) C(6) 115.0(8) . . . ? C(4) C(5) C(6) 122(1) . . . ? N(2) C(6) N(3) 125.9(9) . . . ? N(2) C(6) C(5) 120.9(9) . . . ? N(3) C(6) C(5) 113.2(8) . . . ? N(4) C(7) N(5) 126.0(9) . . . ? N(4) C(7) C(8) 114.3(9) . . . ? N(5) C(7) C(8) 119.6(9) . . . ? N(7) C(8) C(7) 112.6(9) . . . ? N(7) C(8) C(9) 122.3(9) . . . ? C(7) C(8) C(9) 125(1) . . . ? N(6) C(9) C(8) 119(1) . . . ? N(6) C(9) H(5) 120.8 . . . no C(8) C(9) H(5) 120.3 . . . no N(6) C(10) C(11) 122(1) . . . ? N(6) C(10) H(6) 119.1 . . . no C(11) C(10) H(6) 119.3 . . . no N(7) C(11) C(10) 122(1) . . . ? N(7) C(11) H(7) 118.0 . . . no C(10) C(11) H(7) 119.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br(1) Cu(1) 3.286(3) . 6_545 no Br(1) N(1) 3.428(9) . 6_545 no Br(1) O(1) 3.53(1) . 4_554 no Br(1) N(3) 3.575(7) . 6_545 no Br(2) N(2) 3.421(9) . 4_554 no Br(2) O(1) 3.60(1) . 4_554 no Br(4) Cu(2) 3.138(2) . 3_656 no Br(4) N(6) 3.45(1) . 1_545 no Br(4) N(2) 3.479(8) . 3_656 no Br(4) N(7) 3.497(8) . 3_656 no Br(4) N(4) 3.557(7) . 3_656 no Br(4) C(9) 3.57(1) . 1_545 no O(1) N(5) 3.07(1) . 4_565 no O(1) N(6) 3.10(1) . 3_666 no O(1) C(9) 3.31(2) . 4_565 no O(1) C(10) 3.35(2) . 3_666 no O(1) N(2) 3.41(1) . . no N(5) C(3) 3.60(1) . 7_556 no N(6) N(6) 3.30(2) . 2_655 no N(6) C(9) 3.42(2) . 2_655 no C(8) C(10) 3.57(2) . 2_655 no C(9) C(10) 3.55(2) . 2_655 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Br(1) Cu(1) N(1) C(1) . . . . -15(1) no Br(1) Cu(1) N(1) C(5) . . . . 165.1(7) no Br(1) Cu(1) N(3) N(4) . . . . 104(1) no Br(1) Cu(1) N(3) C(6) . . . . -37(2) no Br(2) Cu(1) N(1) C(1) . . . . 121(1) no Br(2) Cu(1) N(1) C(5) . . . . -59(2) no Br(2) Cu(1) N(3) N(4) . . . . -29.9(6) no Br(2) Cu(1) N(3) C(6) . . . . -170.9(6) no Br(3) Cu(2) N(4) N(3) . . . . -7.9(6) no Br(3) Cu(2) N(4) C(7) . . . . -163.7(7) no Br(3) Cu(2) N(7) C(8) . . . . 63(2) no Br(3) Cu(2) N(7) C(11) . . . . -128(1) no Br(4) Cu(2) N(4) N(3) . . . . 179(2) no Br(4) Cu(2) N(4) C(7) . . . . 23(3) no Br(4) Cu(2) N(7) C(8) . . . . -174.1(7) no Br(4) Cu(2) N(7) C(11) . . . . -4.9(9) no Cu(1) N(1) C(1) C(2) . . . . 178(1) no Cu(1) N(1) C(5) C(4) . . . . -179.1(9) no Cu(1) N(1) C(5) C(6) . . . . -3(1) no Cu(1) N(3) N(4) Cu(2) . . . . -53.3(8) no Cu(1) N(3) N(4) C(7) . . . . 102.5(9) no Cu(1) N(3) C(6) N(2) . . . . 158.0(9) no Cu(1) N(3) C(6) C(5) . . . . -23(1) no Cu(2) N(4) N(3) C(6) . . . . 87.9(9) no Cu(2) N(4) C(7) N(5) . . . . 161.6(9) no Cu(2) N(4) C(7) C(8) . . . . -15(1) no Cu(2) N(7) C(8) C(7) . . . . -12(1) no Cu(2) N(7) C(8) C(9) . . . . 166.0(9) no Cu(2) N(7) C(11) C(10) . . . . -168.3(9) no N(1) Cu(1) N(3) N(4) . . . . 157.8(7) no N(1) Cu(1) N(3) C(6) . . . . 16.8(7) no N(1) C(1) C(2) C(3) . . . . 2(2) no N(1) C(5) C(4) C(3) . . . . -1(2) no N(1) C(5) C(6) N(2) . . . . -164(1) no N(1) C(5) C(6) N(3) . . . . 17(1) no N(2) C(6) N(3) N(4) . . . . 14(2) no N(2) C(6) C(5) C(4) . . . . 13(2) no N(3) Cu(1) N(1) C(1) . . . . 173(1) no N(3) Cu(1) N(1) C(5) . . . . -6.9(7) no N(3) N(4) Cu(2) N(7) . . . . 162.0(7) no N(3) N(4) C(7) N(5) . . . . 4(2) no N(3) N(4) C(7) C(8) . . . . -172.0(8) no N(3) C(6) C(5) C(4) . . . . -167(1) no N(4) Cu(2) N(7) C(8) . . . . 4.1(7) no N(4) Cu(2) N(7) C(11) . . . . 173.2(9) no N(4) N(3) C(6) C(5) . . . . -166.3(8) no N(4) C(7) C(8) N(7) . . . . 18(1) no N(4) C(7) C(8) C(9) . . . . -161(1) no N(5) C(7) C(8) N(7) . . . . -158.9(9) no N(5) C(7) C(8) C(9) . . . . 23(2) no N(6) C(9) C(8) N(7) . . . . 5(2) no N(6) C(9) C(8) C(7) . . . . -177(1) no N(6) C(10) C(11) N(7) . . . . 3(2) no N(7) Cu(2) N(4) C(7) . . . . 6.3(7) no C(1) N(1) C(5) C(4) . . . . 1(2) no C(1) N(1) C(5) C(6) . . . . 178(1) no C(1) C(2) C(3) C(4) . . . . -2(2) no C(2) C(1) N(1) C(5) . . . . -2(2) no C(2) C(3) C(4) C(5) . . . . 1(2) no C(3) C(4) C(5) C(6) . . . . -177(1) no C(6) N(3) N(4) C(7) . . . . -116.3(9) no C(7) C(8) N(7) C(11) . . . . 177.1(8) no C(8) N(7) C(11) C(10) . . . . 1(2) no C(8) C(9) N(6) C(10) . . . . -2(2) no C(9) N(6) C(10) C(11) . . . . -2(2) no C(9) C(8) N(7) C(11) . . . . -5(2) no #------------------------------------------------------------------------------ #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== #===END data_sw6am #(3) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl4 Cu2 N6' _chemical_formula_weight 509.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.1727(4) _cell_length_b 8.3275(2) _cell_length_c 15.2603(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.0370(10) _cell_angle_gamma 90.00 _cell_volume 1732.46(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 930 _cell_measurement_theta_min 15.75 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.952 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 3.079 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3915 _exptl_absorpt_correction_T_max 0.7276 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10460 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.31 _reflns_number_total 2425 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+1.6971P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2425 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0185 _refine_ls_wR_factor_ref 0.0475 _refine_ls_wR_factor_gt 0.0464 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.132463(11) 0.338326(19) 0.406141(11) 0.01278(5) Uani 1 1 d . . . Cl1 Cl 0.17989(2) 0.45666(4) 0.30130(2) 0.01969(8) Uani 1 1 d . . . Cl2 Cl 0.26098(2) 0.44773(4) 0.53798(2) 0.01631(7) Uani 1 1 d . . . N1 N 0.05552(8) 0.28739(14) 0.48179(8) 0.0152(2) Uani 1 1 d . . . N2 N -0.12582(9) 0.07763(15) 0.27424(9) 0.0174(2) Uani 1 1 d . . . N3 N 0.01463(8) 0.22900(14) 0.30078(7) 0.0127(2) Uani 1 1 d . . . H2A H -0.1626(16) 0.054(3) 0.2979(16) 0.034(6) Uiso 1 1 d . . . H2B H -0.1405(14) 0.067(2) 0.2148(16) 0.028(5) Uiso 1 1 d . . . C1 C 0.07725(11) 0.33504(19) 0.57295(10) 0.0216(3) Uani 1 1 d . . . H1 H 0.1352(14) 0.390(2) 0.6061(14) 0.026(5) Uiso 1 1 d . . . C2 C 0.01371(12) 0.3089(2) 0.61538(11) 0.0235(3) Uani 1 1 d . . . H2 H 0.0317(18) 0.355(3) 0.6792(18) 0.051(7) Uiso 1 1 d . . . C3 C -0.07393(11) 0.23027(19) 0.56262(10) 0.0220(3) Uani 1 1 d . . . H3 H -0.1181(15) 0.215(3) 0.5903(14) 0.032(5) Uiso 1 1 d . . . C4 C -0.09576(11) 0.17558(17) 0.46873(10) 0.0185(3) Uani 1 1 d . . . H4 H -0.1515(14) 0.119(2) 0.4339(14) 0.023(5) Uiso 1 1 d . . . C5 C -0.02949(9) 0.20723(16) 0.43084(9) 0.0138(2) Uani 1 1 d . . . C6 C -0.04895(9) 0.16735(15) 0.32883(9) 0.0134(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00932(8) 0.01922(9) 0.00906(8) 0.00041(6) 0.00335(6) -0.00265(5) Cl1 0.01643(15) 0.02883(17) 0.01293(14) 0.00303(12) 0.00565(12) -0.00698(12) Cl2 0.01328(14) 0.02084(15) 0.01218(13) 0.00041(11) 0.00319(11) -0.00484(11) N1 0.0129(5) 0.0214(5) 0.0115(5) -0.0011(4) 0.0055(4) -0.0029(4) N2 0.0160(5) 0.0248(6) 0.0120(5) -0.0027(4) 0.0068(4) -0.0066(4) N3 0.0099(5) 0.0199(5) 0.0072(5) -0.0007(4) 0.0026(4) -0.0010(4) C1 0.0193(7) 0.0322(8) 0.0141(6) -0.0057(5) 0.0080(5) -0.0089(6) C2 0.0262(7) 0.0328(8) 0.0156(6) -0.0070(6) 0.0129(6) -0.0102(6) C3 0.0244(7) 0.0283(7) 0.0194(7) -0.0049(6) 0.0151(6) -0.0087(6) C4 0.0176(6) 0.0238(7) 0.0156(6) -0.0036(5) 0.0086(5) -0.0076(5) C5 0.0132(6) 0.0165(6) 0.0114(5) -0.0004(4) 0.0052(5) -0.0010(5) C6 0.0115(5) 0.0166(6) 0.0114(5) 0.0002(4) 0.0044(5) 0.0007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.0145(11) . ? Cu1 N3 2.0216(11) . ? Cu1 Cl1 2.2493(3) . ? Cu1 Cl2 2.2883(3) . ? N1 C1 1.3413(17) . ? N1 C5 1.3540(16) . ? N2 C6 1.3265(17) . ? N3 C6 1.3192(16) . ? N3 N3 1.412(2) 2 ? C1 C2 1.3943(19) . ? C2 C3 1.380(2) . ? C3 C4 1.3976(19) . ? C4 C5 1.3875(18) . ? C5 C6 1.4890(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 80.11(4) . . ? N1 Cu1 Cl1 161.20(4) . . ? N3 Cu1 Cl1 94.53(3) . . ? N1 Cu1 Cl2 93.70(3) . . ? N3 Cu1 Cl2 173.42(3) . . ? Cl1 Cu1 Cl2 92.047(12) . . ? C1 N1 C5 118.67(11) . . ? C1 N1 Cu1 126.28(9) . . ? C5 N1 Cu1 114.86(8) . . ? C6 N3 N3 115.70(12) . 2 ? C6 N3 Cu1 115.76(8) . . ? N3 N3 Cu1 127.95(9) 2 . ? N1 C1 C2 122.02(13) . . ? C3 C2 C1 119.26(13) . . ? C2 C3 C4 119.12(13) . . ? C5 C4 C3 118.45(13) . . ? N1 C5 C4 122.44(12) . . ? N1 C5 C6 114.33(11) . . ? C4 C5 C6 123.08(12) . . ? N3 C6 N2 125.59(12) . . ? N3 C6 C5 114.51(11) . . ? N2 C6 C5 119.90(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C1 -173.23(13) . . . . ? Cl1 Cu1 N1 C1 -98.49(15) . . . . ? Cl2 Cu1 N1 C1 9.03(12) . . . . ? N3 Cu1 N1 C5 1.65(9) . . . . ? Cl1 Cu1 N1 C5 76.39(15) . . . . ? Cl2 Cu1 N1 C5 -176.09(9) . . . . ? N1 Cu1 N3 C6 -5.21(9) . . . . ? Cl1 Cu1 N3 C6 -167.03(9) . . . . ? Cl2 Cu1 N3 C6 14.8(4) . . . . ? N1 Cu1 N3 N3 165.55(9) . . . 2 ? Cl1 Cu1 N3 N3 3.72(8) . . . 2 ? Cl2 Cu1 N3 N3 -174.4(2) . . . 2 ? C5 N1 C1 C2 -2.0(2) . . . . ? Cu1 N1 C1 C2 172.70(12) . . . . ? N1 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? C2 C3 C4 C5 -2.1(2) . . . . ? C1 N1 C5 C4 1.4(2) . . . . ? Cu1 N1 C5 C4 -173.94(11) . . . . ? C1 N1 C5 C6 176.98(12) . . . . ? Cu1 N1 C5 C6 1.69(14) . . . . ? C3 C4 C5 N1 0.7(2) . . . . ? C3 C4 C5 C6 -174.57(13) . . . . ? N3 N3 C6 N2 14.98(17) 2 . . . ? Cu1 N3 C6 N2 -173.10(11) . . . . ? N3 N3 C6 C5 -164.43(9) 2 . . . ? Cu1 N3 C6 C5 7.49(14) . . . . ? N1 C5 C6 N3 -6.05(17) . . . . ? C4 C5 C6 N3 169.54(13) . . . . ? N1 C5 C6 N2 174.50(12) . . . . ? C4 C5 C6 N2 -9.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.459 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.064 #===END