data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Susan Herringer' _publ_contact_author_address ;Department of Chemistry Clark University 950 Main Street Worcester, MA 01610 ; _publ_contact_author_email snherringer@gmail.com _publ_contact_author_phone 508-793-7116 _publ_contact_author_fax 508-793-8861 loop_ _publ_author_name _publ_author_address S.N.Herringer ;Department of Chemistry Clark University 950 Main Street Worcester, MA 01610 ; M.M.Turnbull ;Department of Chemistry Clark University 950 Main Street Worcester, MA 01610 ; C.P.Landee ;Department of Physics Clark University 950 Main Street Worcester, MA 01610 ; J.L.Wikaira ;Department of Chemistry University of Canterbury Private Bag 4800 Christchurch New Zealand ; data_snhm _database_code_depnum_ccdc_archive 'CCDC 787860' #TrackingRef '2043_web_deposit_cif_file_0_SusanHerringer_1281041344.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-bromo-3-methylpyridine)dichlorocopper (II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Br2 Cl2 Cu N2' _chemical_formula_weight 478.50 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2720(4) _cell_length_b 11.8897(5) _cell_length_c 15.1439(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.758(2) _cell_angle_gamma 90.00 _cell_volume 1614.41(12) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 9118 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 33.54 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.969 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 6.621 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1771 _exptl_absorpt_correction_T_max 0.2884 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 67159 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 33.82 _reflns_number_total 6445 _reflns_number_gt 5093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0444P)^2^+5.3669P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6445 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1188 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br13 Br 0.49920(4) 0.66149(3) 0.22517(3) 0.03056(10) Uani 1 1 d . . . Cu1 Cu 0.23495(4) 0.80456(3) 0.10566(3) 0.01759(9) Uani 1 1 d . . . Br3 Br -0.08922(4) 0.85673(3) -0.03416(3) 0.02962(9) Uani 1 1 d . . . Cl2 Cl 0.15885(9) 0.92285(7) 0.19979(6) 0.02605(16) Uani 1 1 d . . . Cl1 Cl 0.28471(10) 0.73588(7) -0.02110(6) 0.02764(17) Uani 1 1 d . . . N1 N 0.0595(3) 0.7005(2) 0.0900(2) 0.0205(5) Uani 1 1 d . . . C6 C 0.0807(3) 0.5967(2) 0.1428(2) 0.0165(5) Uani 1 1 d . . . H6 H 0.1688 0.5831 0.1897 0.020 Uiso 1 1 calc R . . N11 N 0.4427(3) 0.8669(2) 0.1421(2) 0.0198(5) Uani 1 1 d . . . C12 C 0.5564(3) 0.8009(3) 0.1840(2) 0.0200(5) Uani 1 1 d . . . C13 C 0.7066(3) 0.8289(3) 0.1977(2) 0.0208(6) Uani 1 1 d . . . C15 C 0.6177(4) 1.0040(3) 0.1208(3) 0.0266(7) Uani 1 1 d . . . H15 H 0.6372 1.0755 0.0984 0.032 Uiso 1 1 calc R . . C2 C -0.0713(4) 0.7191(3) 0.0308(2) 0.0219(6) Uani 1 1 d . . . C16 C 0.4734(4) 0.9684(3) 0.1124(3) 0.0252(6) Uani 1 1 d . . . H16 H 0.3933 1.0171 0.0849 0.030 Uiso 1 1 calc R . . C17 C 0.8301(4) 0.7533(3) 0.2464(2) 0.0280(7) Uani 1 1 d . . . H17A H 0.8298 0.7482 0.3109 0.034 Uiso 1 1 calc R . . H17B H 0.9258 0.7840 0.2413 0.034 Uiso 1 1 calc R . . H17C H 0.8157 0.6783 0.2188 0.034 Uiso 1 1 calc R . . C3 C -0.1906(4) 0.6436(3) 0.0135(3) 0.0271(7) Uani 1 1 d . . . C14 C 0.7344(4) 0.9328(3) 0.1629(2) 0.0241(6) Uani 1 1 d . . . H14 H 0.8344 0.9555 0.1680 0.029 Uiso 1 1 calc R . . C5 C -0.0300(5) 0.5215(3) 0.1221(3) 0.0334(8) Uani 1 1 d . . . H5 H -0.0151 0.4502 0.1512 0.040 Uiso 1 1 calc R . . C4 C -0.1656(5) 0.5428(3) 0.0601(3) 0.0356(9) Uani 1 1 d . . . H4 H -0.2419 0.4874 0.0495 0.043 Uiso 1 1 calc R . . C7 C -0.3367(5) 0.6688(5) -0.0545(3) 0.0467(11) Uani 1 1 d . . . H7A H -0.3787 0.7384 -0.0370 0.056 Uiso 1 1 calc R . . H7B H -0.4064 0.6066 -0.0551 0.056 Uiso 1 1 calc R . . H7C H -0.3199 0.6776 -0.1154 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br13 0.02252(15) 0.02548(17) 0.0432(2) 0.01590(15) 0.00759(14) -0.00097(12) Cu1 0.01559(15) 0.01324(16) 0.02533(19) -0.00043(13) 0.00775(13) -0.00209(12) Br3 0.02785(17) 0.02799(17) 0.03248(19) 0.00756(14) 0.00673(14) 0.00482(13) Cl2 0.0213(3) 0.0243(4) 0.0346(4) -0.0098(3) 0.0109(3) -0.0034(3) Cl1 0.0361(4) 0.0197(3) 0.0332(4) -0.0047(3) 0.0200(3) -0.0080(3) N1 0.0202(11) 0.0160(11) 0.0268(13) 0.0009(10) 0.0085(10) -0.0028(9) C6 0.0099(10) 0.0079(10) 0.0319(15) -0.0071(10) 0.0058(10) 0.0009(8) N11 0.0173(11) 0.0160(11) 0.0273(13) 0.0014(10) 0.0077(10) -0.0019(8) C12 0.0177(12) 0.0191(13) 0.0246(14) 0.0016(11) 0.0082(11) -0.0010(10) C13 0.0176(12) 0.0245(14) 0.0214(14) -0.0031(11) 0.0070(11) -0.0036(10) C15 0.0286(15) 0.0193(14) 0.0325(18) 0.0006(13) 0.0090(13) -0.0082(12) C2 0.0220(13) 0.0201(14) 0.0245(15) -0.0032(11) 0.0080(11) -0.0021(10) C16 0.0246(14) 0.0156(13) 0.0353(18) 0.0027(12) 0.0075(13) -0.0029(11) C17 0.0185(13) 0.0399(19) 0.0248(16) 0.0021(14) 0.0041(12) 0.0027(13) C3 0.0228(14) 0.0270(16) 0.0328(18) -0.0100(14) 0.0092(13) -0.0087(12) C14 0.0214(13) 0.0263(15) 0.0261(16) -0.0034(12) 0.0088(12) -0.0088(11) C5 0.040(2) 0.0155(14) 0.051(2) 0.0018(14) 0.0219(18) -0.0047(13) C4 0.0351(19) 0.0265(17) 0.049(2) -0.0111(16) 0.0182(17) -0.0130(15) C7 0.0297(19) 0.065(3) 0.042(2) -0.007(2) 0.0020(18) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br13 C12 1.893(3) . ? Cu1 N11 2.006(3) . ? Cu1 N1 2.009(3) . ? Cu1 Cl1 2.2395(9) . ? Cu1 Cl2 2.2407(9) . ? Br3 C2 1.895(3) . ? Cl2 Cl1 5.9187(13) 3_575 ? Cl1 Cl2 5.9187(13) 3_575 ? N1 C2 1.330(4) . ? N1 C6 1.457(4) . ? C6 C5 1.336(4) . ? C6 H6 0.9500 . ? N11 C12 1.337(4) . ? N11 C16 1.344(4) . ? C12 C13 1.396(4) . ? C13 C14 1.393(5) . ? C13 C17 1.493(5) . ? C15 C16 1.378(5) . ? C15 C14 1.394(5) . ? C15 H15 0.9500 . ? C2 C3 1.397(4) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C3 C4 1.380(6) . ? C3 C7 1.508(6) . ? C14 H14 0.9500 . ? C5 C4 1.388(6) . ? C5 H5 0.9500 . ? C4 H4 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cu1 N1 162.17(11) . . ? N11 Cu1 Cl1 88.69(8) . . ? N1 Cu1 Cl1 90.66(8) . . ? N11 Cu1 Cl2 91.68(8) . . ? N1 Cu1 Cl2 94.88(8) . . ? Cl1 Cu1 Cl2 160.25(4) . . ? Cu1 Cl2 Cl1 115.73(3) . 3_575 ? Cu1 Cl1 Cl2 82.59(3) . 3_575 ? C2 N1 C6 118.9(3) . . ? C2 N1 Cu1 123.3(2) . . ? C6 N1 Cu1 117.7(2) . . ? C5 C6 N1 116.7(3) . . ? C5 C6 H6 121.6 . . ? N1 C6 H6 121.6 . . ? C12 N11 C16 118.5(3) . . ? C12 N11 Cu1 120.0(2) . . ? C16 N11 Cu1 120.7(2) . . ? N11 C12 C13 124.5(3) . . ? N11 C12 Br13 114.7(2) . . ? C13 C12 Br13 120.8(2) . . ? C14 C13 C12 115.4(3) . . ? C14 C13 C17 121.9(3) . . ? C12 C13 C17 122.7(3) . . ? C16 C15 C14 118.6(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N1 C2 C3 124.2(3) . . ? N1 C2 Br3 116.0(2) . . ? C3 C2 Br3 119.8(3) . . ? N11 C16 C15 121.9(3) . . ? N11 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C3 C2 116.1(3) . . ? C4 C3 C7 121.7(4) . . ? C2 C3 C7 122.1(4) . . ? C13 C14 C15 121.0(3) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C6 C5 C4 123.1(4) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 Cu1 Cl2 Cl1 114.02(8) . . . 3_575 ? N1 Cu1 Cl2 Cl1 -82.57(9) . . . 3_575 ? Cl1 Cu1 Cl2 Cl1 23.22(12) . . . 3_575 ? N11 Cu1 Cl1 Cl2 -112.31(8) . . . 3_575 ? N1 Cu1 Cl1 Cl2 85.51(8) . . . 3_575 ? Cl2 Cu1 Cl1 Cl2 -20.98(11) . . . 3_575 ? N11 Cu1 N1 C2 -165.9(3) . . . . ? Cl1 Cu1 N1 C2 -78.2(3) . . . . ? Cl2 Cu1 N1 C2 82.8(3) . . . . ? N11 Cu1 N1 C6 10.6(5) . . . . ? Cl1 Cu1 N1 C6 98.4(2) . . . . ? Cl2 Cu1 N1 C6 -100.6(2) . . . . ? C2 N1 C6 C5 5.9(4) . . . . ? Cu1 N1 C6 C5 -170.8(3) . . . . ? N1 Cu1 N11 C12 5.0(5) . . . . ? Cl1 Cu1 N11 C12 -83.1(3) . . . . ? Cl2 Cu1 N11 C12 116.7(3) . . . . ? N1 Cu1 N11 C16 174.5(3) . . . . ? Cl1 Cu1 N11 C16 86.4(3) . . . . ? Cl2 Cu1 N11 C16 -73.8(3) . . . . ? C16 N11 C12 C13 -1.6(5) . . . . ? Cu1 N11 C12 C13 168.1(3) . . . . ? C16 N11 C12 Br13 178.6(3) . . . . ? Cu1 N11 C12 Br13 -11.7(3) . . . . ? N11 C12 C13 C14 -0.9(5) . . . . ? Br13 C12 C13 C14 178.9(2) . . . . ? N11 C12 C13 C17 178.9(3) . . . . ? Br13 C12 C13 C17 -1.3(5) . . . . ? C6 N1 C2 C3 -1.9(5) . . . . ? Cu1 N1 C2 C3 174.6(3) . . . . ? C6 N1 C2 Br3 179.5(2) . . . . ? Cu1 N1 C2 Br3 -4.0(4) . . . . ? C12 N11 C16 C15 2.7(5) . . . . ? Cu1 N11 C16 C15 -166.9(3) . . . . ? C14 C15 C16 N11 -1.3(6) . . . . ? N1 C2 C3 C4 -1.9(5) . . . . ? Br3 C2 C3 C4 176.6(3) . . . . ? N1 C2 C3 C7 -179.9(4) . . . . ? Br3 C2 C3 C7 -1.4(5) . . . . ? C12 C13 C14 C15 2.3(5) . . . . ? C17 C13 C14 C15 -177.5(3) . . . . ? C16 C15 C14 C13 -1.4(5) . . . . ? N1 C6 C5 C4 -6.2(5) . . . . ? C2 C3 C4 C5 1.9(6) . . . . ? C7 C3 C4 C5 179.8(4) . . . . ? C6 C5 C4 C3 2.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 33.82 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.015 _refine_diff_density_min -1.251 _refine_diff_density_rms 0.162 # Attachment '2044_web_deposit_cif_file_1_SusanHerringer_1281041344.cif' data_snhlr_2 _database_code_depnum_ccdc_archive 'CCDC 787861' #TrackingRef '2044_web_deposit_cif_file_1_SusanHerringer_1281041344.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-chloro-3-methylpyridine)dibromocopper (II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Br2 Cl2 Cu N2' _chemical_formula_weight 478.50 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0949(2) _cell_length_b 7.4718(3) _cell_length_c 9.5654(5) _cell_angle_alpha 104.579(3) _cell_angle_beta 91.809(3) _cell_angle_gamma 112.825(2) _cell_volume 384.47(3) _cell_formula_units_Z 1 _cell_measurement_temperature 111(2) _cell_measurement_reflns_used 6443 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 34.30 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.81 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 231 _exptl_absorpt_coefficient_mu 6.950 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0708 _exptl_absorpt_correction_T_max 0.4220 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 111(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10335 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2322 _reflns_number_gt 2143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0239P)^2^+0.2165P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2322 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0200 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0490 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.01604(7) Uani 1 2 d S . . Br1 Br 0.39523(3) 0.77079(3) 0.627307(17) 0.02235(6) Uani 1 1 d . . . Cl2 Cl 0.82343(7) 0.53803(7) 0.76416(5) 0.02566(9) Uani 1 1 d . . . N1 N 0.3760(2) 0.3553(2) 0.64752(14) 0.0181(3) Uani 1 1 d . . . C2 C 0.5290(3) 0.3716(2) 0.75760(17) 0.0185(3) Uani 1 1 d . . . C6 C 0.1406(3) 0.2325(3) 0.63540(19) 0.0220(3) Uani 1 1 d . . . H6 H 0.0317 0.2224 0.5603 0.026 Uiso 1 1 calc R . . C3 C 0.4646(3) 0.2666(3) 0.86165(18) 0.0225(3) Uani 1 1 d . . . C4 C 0.2235(4) 0.1392(3) 0.8457(2) 0.0288(4) Uani 1 1 d . . . H4 H 0.1705 0.0641 0.9114 0.035 Uiso 1 1 calc R . . C5 C 0.0601(3) 0.1216(3) 0.7339(2) 0.0287(4) Uani 1 1 d . . . H5 H -0.1017 0.0364 0.7249 0.034 Uiso 1 1 calc R . . C7 C 0.6472(4) 0.2879(3) 0.9807(2) 0.0320(4) Uani 1 1 d . . . H7A H 0.5662 0.2240 1.0509 0.038 Uiso 1 1 calc R . . H7B H 0.7427 0.4290 1.0279 0.038 Uiso 1 1 calc R . . H7C H 0.7495 0.2242 0.9395 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01784(13) 0.01909(13) 0.01360(11) 0.00453(9) 0.00272(9) 0.01013(11) Br1 0.02692(10) 0.02261(9) 0.02177(8) 0.00508(6) 0.00708(6) 0.01507(7) Cl2 0.01806(18) 0.0310(2) 0.02618(19) 0.00847(16) -0.00037(14) 0.00827(16) N1 0.0186(6) 0.0200(6) 0.0177(6) 0.0041(5) 0.0035(5) 0.0106(5) C2 0.0195(7) 0.0197(7) 0.0182(6) 0.0047(6) 0.0041(5) 0.0103(6) C6 0.0182(7) 0.0211(8) 0.0250(8) 0.0018(6) 0.0050(6) 0.0091(6) C3 0.0337(9) 0.0228(8) 0.0184(7) 0.0067(6) 0.0091(6) 0.0185(7) C4 0.0388(10) 0.0239(9) 0.0297(9) 0.0112(7) 0.0172(8) 0.0159(8) C5 0.0226(8) 0.0233(9) 0.0355(9) 0.0041(7) 0.0112(7) 0.0068(7) C7 0.0465(12) 0.0397(11) 0.0225(8) 0.0126(8) 0.0063(7) 0.0283(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9830(14) 2_666 ? Cu1 N1 1.9830(14) . ? Cu1 Br1 2.40735(18) 2_666 ? Cu1 Br1 2.40735(18) . ? Cu1 Br1 5.0123(3) 1_655 ? Br1 Cl2 3.6899(5) 1_455 ? Br1 Br1 4.5053(4) 2_676 ? Br1 Cu1 5.0123(3) 1_455 ? Cl2 C2 1.7298(17) . ? Cl2 Br1 3.6899(5) 1_655 ? N1 C2 1.334(2) . ? N1 C6 1.352(2) . ? C2 C3 1.392(2) . ? C6 C5 1.387(3) . ? C6 H6 0.9300 . ? C3 C4 1.384(3) . ? C3 C7 1.501(3) . ? C4 C5 1.383(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 2_666 . ? N1 Cu1 Br1 89.88(4) 2_666 2_666 ? N1 Cu1 Br1 90.12(4) . 2_666 ? N1 Cu1 Br1 90.12(4) 2_666 . ? N1 Cu1 Br1 89.88(4) . . ? Br1 Cu1 Br1 180.0 2_666 . ? N1 Cu1 Br1 76.54(4) 2_666 1_655 ? N1 Cu1 Br1 103.46(4) . 1_655 ? Br1 Cu1 Br1 75.042(6) 2_666 1_655 ? Br1 Cu1 Br1 104.958(6) . 1_655 ? Cu1 Br1 Cl2 107.235(10) . 1_455 ? Cu1 Br1 Br1 106.538(7) . 2_676 ? Cl2 Br1 Br1 129.702(9) 1_455 2_676 ? Cu1 Br1 Cu1 104.958(6) . 1_455 ? Cl2 Br1 Cu1 37.112(7) 1_455 1_455 ? Br1 Br1 Cu1 98.253(5) 2_676 1_455 ? C2 Cl2 Br1 157.37(6) . 1_655 ? C2 N1 C6 119.00(14) . . ? C2 N1 Cu1 119.51(11) . . ? C6 N1 Cu1 121.41(11) . . ? N1 C2 C3 124.41(16) . . ? N1 C2 Cl2 114.68(12) . . ? C3 C2 Cl2 120.91(13) . . ? N1 C6 C5 120.57(17) . . ? N1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C4 C3 C2 115.59(16) . . ? C4 C3 C7 122.68(16) . . ? C2 C3 C7 121.72(17) . . ? C5 C4 C3 121.28(17) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.13(17) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 Br1 Cl2 142.52(4) 2_666 . . 1_455 ? N1 Cu1 Br1 Cl2 -37.48(4) . . . 1_455 ? Br1 Cu1 Br1 Cl2 49(100) 2_666 . . 1_455 ? Br1 Cu1 Br1 Cl2 -141.384(7) 1_655 . . 1_455 ? N1 Cu1 Br1 Br1 0.36(4) 2_666 . . 2_676 ? N1 Cu1 Br1 Br1 -179.64(4) . . . 2_676 ? Br1 Cu1 Br1 Br1 -93(100) 2_666 . . 2_676 ? Br1 Cu1 Br1 Br1 76.449(8) 1_655 . . 2_676 ? N1 Cu1 Br1 Cu1 103.91(4) 2_666 . . 1_455 ? N1 Cu1 Br1 Cu1 -76.09(4) . . . 1_455 ? Br1 Cu1 Br1 Cu1 10(100) 2_666 . . 1_455 ? Br1 Cu1 Br1 Cu1 180.0 1_655 . . 1_455 ? N1 Cu1 N1 C2 -157(100) 2_666 . . . ? Br1 Cu1 N1 C2 82.58(12) 2_666 . . . ? Br1 Cu1 N1 C2 -97.42(12) . . . . ? Br1 Cu1 N1 C2 7.94(13) 1_655 . . . ? N1 Cu1 N1 C6 26(100) 2_666 . . . ? Br1 Cu1 N1 C6 -94.27(12) 2_666 . . . ? Br1 Cu1 N1 C6 85.73(12) . . . . ? Br1 Cu1 N1 C6 -168.91(12) 1_655 . . . ? C6 N1 C2 C3 1.3(2) . . . . ? Cu1 N1 C2 C3 -175.60(13) . . . . ? C6 N1 C2 Cl2 -178.40(12) . . . . ? Cu1 N1 C2 Cl2 4.68(17) . . . . ? Br1 Cl2 C2 N1 -50.1(2) 1_655 . . . ? Br1 Cl2 C2 C3 130.21(13) 1_655 . . . ? C2 N1 C6 C5 -1.4(2) . . . . ? Cu1 N1 C6 C5 175.43(13) . . . . ? N1 C2 C3 C4 -0.2(2) . . . . ? Cl2 C2 C3 C4 179.48(13) . . . . ? N1 C2 C3 C7 178.39(16) . . . . ? Cl2 C2 C3 C7 -1.9(2) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C7 C3 C4 C5 -179.36(17) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? N1 C6 C5 C4 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.670 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.079 # Attachment '2045_web_deposit_cif_file_2_SusanHerringer_1281041344.cif' data_snhi _database_code_depnum_ccdc_archive 'CCDC 787862' #TrackingRef '2045_web_deposit_cif_file_2_SusanHerringer_1281041344.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-chloro-3-methylpyridine)dichlorocopper (II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl4 Cu N2' _chemical_formula_weight 389.58 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5063(4) _cell_length_b 8.6802(4) _cell_length_c 11.7102(5) _cell_angle_alpha 83.729(2) _cell_angle_beta 70.284(2) _cell_angle_gamma 67.255(2) _cell_volume 750.43(6) _cell_formula_units_Z 2 _cell_measurement_temperature 165(2) _cell_measurement_reflns_used 9995 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.91 _exptl_crystal_size_mid 0.62 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 2.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5753 _exptl_absorpt_correction_T_max 0.7469 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 165(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19480 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 29.94 _reflns_number_total 4307 _reflns_number_gt 3955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0250P)^2^+0.3338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4307 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.86146(2) 0.122425(18) 0.177137(15) 0.01746(5) Uani 1 1 d . . . Cl1 Cl 1.09781(4) -0.12151(4) 0.11357(3) 0.02251(7) Uani 1 1 d . . . Cl2 Cl 0.63126(4) 0.37098(4) 0.21762(3) 0.02339(7) Uani 1 1 d . . . Cl3 Cl 0.79009(5) -0.11653(5) 0.40555(3) 0.02651(8) Uani 1 1 d . . . Cl13 Cl 0.95488(5) 0.23332(5) 0.38573(3) 0.02864(8) Uani 1 1 d . . . N11 N 1.02995(14) 0.24210(13) 0.15160(10) 0.0176(2) Uani 1 1 d . . . N1 N 0.68096(14) 0.01043(13) 0.22123(10) 0.0168(2) Uani 1 1 d . . . C2 C 0.66343(17) -0.09513(16) 0.31222(12) 0.0177(2) Uani 1 1 d . . . C13 C 1.15148(17) 0.39851(16) 0.23192(13) 0.0196(2) Uani 1 1 d . . . C12 C 1.05366(17) 0.29774(16) 0.24371(12) 0.0182(2) Uani 1 1 d . . . C14 C 1.23210(18) 0.43725(16) 0.11403(13) 0.0211(3) Uani 1 1 d . . . H14 H 1.2998 0.5037 0.1004 0.025 Uiso 1 1 calc R . . C3 C 0.54778(18) -0.18186(16) 0.33771(12) 0.0195(2) Uani 1 1 d . . . C6 C 0.57474(17) 0.04135(16) 0.15163(12) 0.0188(2) Uani 1 1 d . . . H6 H 0.5837 0.1163 0.0889 0.023 Uiso 1 1 calc R . . C5 C 0.45315(18) -0.03496(17) 0.17083(13) 0.0206(2) Uani 1 1 d . . . H5 H 0.3802 -0.0111 0.1223 0.025 Uiso 1 1 calc R . . C15 C 1.21269(18) 0.37790(17) 0.01644(13) 0.0216(3) Uani 1 1 d . . . H15 H 1.2685 0.4023 -0.0626 0.026 Uiso 1 1 calc R . . C16 C 1.10924(18) 0.28205(16) 0.03854(12) 0.0198(2) Uani 1 1 d . . . H16 H 1.0939 0.2439 -0.0266 0.024 Uiso 1 1 calc R . . C4 C 0.44129(18) -0.14788(17) 0.26365(13) 0.0213(3) Uani 1 1 d . . . H4 H 0.3611 -0.2015 0.2764 0.026 Uiso 1 1 calc R . . C17 C 1.1685(2) 0.4616(2) 0.33921(14) 0.0289(3) Uani 1 1 d . . . H17A H 1.2318 0.5364 0.3128 0.035 Uiso 1 1 calc R . . H17B H 1.2339 0.3691 0.3792 0.035 Uiso 1 1 calc R . . H17C H 1.0507 0.5198 0.3946 0.035 Uiso 1 1 calc R . . C7 C 0.5389(2) -0.30351(19) 0.43851(14) 0.0283(3) Uani 1 1 d . . . H7A H 0.4585 -0.3558 0.4374 0.034 Uiso 1 1 calc R . . H7B H 0.4958 -0.2455 0.5149 0.034 Uiso 1 1 calc R . . H7C H 0.6569 -0.3872 0.4279 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01438(8) 0.01607(8) 0.02414(9) 0.00331(6) -0.00722(6) -0.00786(6) Cl1 0.01774(15) 0.01722(13) 0.03443(18) 0.00216(12) -0.01073(13) -0.00686(11) Cl2 0.01709(15) 0.01841(14) 0.03096(17) 0.00223(12) -0.00433(12) -0.00611(11) Cl3 0.03216(18) 0.02967(16) 0.02749(17) 0.01012(13) -0.01894(14) -0.01624(14) Cl13 0.02776(18) 0.0411(2) 0.02163(16) 0.00664(14) -0.00669(13) -0.02024(15) N11 0.0143(5) 0.0162(5) 0.0225(5) 0.0011(4) -0.0057(4) -0.0062(4) N1 0.0141(5) 0.0165(5) 0.0206(5) 0.0031(4) -0.0066(4) -0.0065(4) C2 0.0172(6) 0.0177(5) 0.0192(6) 0.0021(4) -0.0071(5) -0.0069(4) C13 0.0142(5) 0.0182(5) 0.0255(6) -0.0031(5) -0.0058(5) -0.0047(4) C12 0.0146(5) 0.0191(5) 0.0197(6) 0.0016(4) -0.0043(5) -0.0064(4) C14 0.0162(6) 0.0156(5) 0.0309(7) 0.0013(5) -0.0058(5) -0.0070(5) C3 0.0198(6) 0.0188(5) 0.0192(6) 0.0016(4) -0.0030(5) -0.0097(5) C6 0.0163(6) 0.0195(5) 0.0205(6) 0.0034(5) -0.0070(5) -0.0063(5) C5 0.0155(6) 0.0246(6) 0.0226(6) 0.0000(5) -0.0075(5) -0.0069(5) C15 0.0195(6) 0.0197(6) 0.0230(6) 0.0039(5) -0.0045(5) -0.0075(5) C16 0.0183(6) 0.0196(6) 0.0210(6) 0.0008(5) -0.0062(5) -0.0066(5) C4 0.0175(6) 0.0232(6) 0.0250(7) -0.0007(5) -0.0040(5) -0.0114(5) C17 0.0239(7) 0.0362(8) 0.0298(8) -0.0090(6) -0.0061(6) -0.0143(6) C7 0.0338(8) 0.0273(7) 0.0262(7) 0.0096(6) -0.0074(6) -0.0181(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N11 2.0042(10) . ? Cu1 N1 2.0196(10) . ? Cu1 Cl2 2.2459(4) . ? Cu1 Cl1 2.2632(4) . ? Cl1 Cu1 3.3040(4) 2_755 ? Cl3 C2 1.7277(13) . ? Cl13 C12 1.7326(13) . ? N11 C12 1.3316(17) . ? N11 C16 1.3440(17) . ? N1 C2 1.3351(16) . ? N1 C6 1.3469(17) . ? C2 C3 1.3961(17) . ? C13 C14 1.3883(19) . ? C13 C12 1.3912(17) . ? C13 C17 1.4945(19) . ? C14 C15 1.386(2) . ? C14 H14 0.9300 . ? C3 C4 1.3883(19) . ? C3 C7 1.4977(19) . ? C6 C5 1.3782(17) . ? C6 H6 0.9300 . ? C5 C4 1.3864(19) . ? C5 H5 0.9300 . ? C15 C16 1.3780(18) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C4 H4 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cu1 N1 173.97(4) . . ? N11 Cu1 Cl2 88.57(3) . . ? N1 Cu1 Cl2 88.81(3) . . ? N11 Cu1 Cl1 90.50(3) . . ? N1 Cu1 Cl1 92.71(3) . . ? Cl2 Cu1 Cl1 173.426(15) . . ? Cu1 Cl1 Cu1 100.400(12) . 2_755 ? C12 N11 C16 118.18(11) . . ? C12 N11 Cu1 122.26(9) . . ? C16 N11 Cu1 119.25(9) . . ? C2 N1 C6 118.07(11) . . ? C2 N1 Cu1 124.50(9) . . ? C6 N1 Cu1 117.41(9) . . ? N1 C2 C3 124.67(12) . . ? N1 C2 Cl3 115.81(9) . . ? C3 C2 Cl3 119.48(10) . . ? C14 C13 C12 115.75(12) . . ? C14 C13 C17 122.03(12) . . ? C12 C13 C17 122.23(13) . . ? N11 C12 C13 124.68(12) . . ? N11 C12 Cl13 115.22(9) . . ? C13 C12 Cl13 120.09(10) . . ? C15 C14 C13 120.67(12) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C4 C3 C2 115.66(12) . . ? C4 C3 C7 122.15(12) . . ? C2 C3 C7 122.19(13) . . ? N1 C6 C5 121.83(12) . . ? N1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C5 C4 118.99(12) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C16 C15 C14 118.83(13) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N11 C16 C15 121.86(13) . . ? N11 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C5 C4 C3 120.72(12) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 Cu1 Cl1 Cu1 -93.66(3) . . . 2_755 ? N1 Cu1 Cl1 Cu1 91.45(3) . . . 2_755 ? Cl2 Cu1 Cl1 Cu1 -11.82(11) . . . 2_755 ? N1 Cu1 N11 C12 13.8(5) . . . . ? Cl2 Cu1 N11 C12 78.13(10) . . . . ? Cl1 Cu1 N11 C12 -108.38(10) . . . . ? N1 Cu1 N11 C16 -159.8(4) . . . . ? Cl2 Cu1 N11 C16 -95.41(10) . . . . ? Cl1 Cu1 N11 C16 78.08(10) . . . . ? N11 Cu1 N1 C2 -53.9(4) . . . . ? Cl2 Cu1 N1 C2 -118.26(10) . . . . ? Cl1 Cu1 N1 C2 68.14(10) . . . . ? N11 Cu1 N1 C6 128.0(4) . . . . ? Cl2 Cu1 N1 C6 63.64(9) . . . . ? Cl1 Cu1 N1 C6 -109.96(9) . . . . ? C6 N1 C2 C3 2.8(2) . . . . ? Cu1 N1 C2 C3 -175.25(10) . . . . ? C6 N1 C2 Cl3 -174.94(10) . . . . ? Cu1 N1 C2 Cl3 6.97(15) . . . . ? C16 N11 C12 C13 1.7(2) . . . . ? Cu1 N11 C12 C13 -171.90(10) . . . . ? C16 N11 C12 Cl13 -177.39(10) . . . . ? Cu1 N11 C12 Cl13 9.01(14) . . . . ? C14 C13 C12 N11 -1.8(2) . . . . ? C17 C13 C12 N11 178.01(13) . . . . ? C14 C13 C12 Cl13 177.22(10) . . . . ? C17 C13 C12 Cl13 -2.94(19) . . . . ? C12 C13 C14 C15 0.35(19) . . . . ? C17 C13 C14 C15 -179.50(13) . . . . ? N1 C2 C3 C4 -2.4(2) . . . . ? Cl3 C2 C3 C4 175.35(10) . . . . ? N1 C2 C3 C7 177.73(13) . . . . ? Cl3 C2 C3 C7 -4.56(19) . . . . ? C2 N1 C6 C5 -1.25(19) . . . . ? Cu1 N1 C6 C5 176.98(10) . . . . ? N1 C6 C5 C4 -0.6(2) . . . . ? C13 C14 C15 C16 1.1(2) . . . . ? C12 N11 C16 C15 -0.05(19) . . . . ? Cu1 N11 C16 C15 173.76(10) . . . . ? C14 C15 C16 N11 -1.3(2) . . . . ? C6 C5 C4 C3 1.1(2) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C7 C3 C4 C5 -179.79(13) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.94 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.447 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.066 # Attachment '2046_web_deposit_cif_file_3_SusanHerringer_1281041344.cif' data_snhc _database_code_depnum_ccdc_archive 'CCDC 787863' #TrackingRef '2046_web_deposit_cif_file_3_SusanHerringer_1281041344.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-bromo-3-methylpyridine)dibromocopper (II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Br4 Cu N2' _chemical_formula_weight 567.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2440(2) _cell_length_b 7.4588(3) _cell_length_c 9.5897(4) _cell_angle_alpha 104.777(2) _cell_angle_beta 90.043(2) _cell_angle_gamma 114.151(2) _cell_volume 391.24(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6170 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 30.00 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 267 _exptl_absorpt_coefficient_mu 11.595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1004 _exptl_absorpt_correction_T_max 0.2936 _exptl_absorpt_process_details 'via SADABS' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9966 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2270 _reflns_number_gt 2105 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0166P)^2^+0.5302P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2270 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0214 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0454 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.0000 0.5000 0.01466(7) Uani 1 2 d S . . Br1 Br 0.41397(4) 0.27905(3) 0.63431(2) 0.01982(6) Uani 1 1 d . . . N1 N 0.3802(3) -0.1458(3) 0.64915(18) 0.0162(3) Uani 1 1 d . . . C2 C 0.5319(4) -0.1271(3) 0.7558(2) 0.0163(4) Uani 1 1 d . . . Br2 Br 0.84955(4) 0.05327(3) 0.75217(2) 0.02063(6) Uani 1 1 d . . . C3 C 0.4700(4) -0.2307(3) 0.8622(2) 0.0192(4) Uani 1 1 d . . . C4 C 0.2318(4) -0.3604(3) 0.8517(2) 0.0233(4) Uani 1 1 d . . . H4 H 0.1788 -0.4363 0.9205 0.028 Uiso 1 1 calc R . . C5 C 0.0704(4) -0.3813(4) 0.7431(3) 0.0243(4) Uani 1 1 d . . . H5 H -0.0922 -0.4695 0.7380 0.029 Uiso 1 1 calc R . . C6 C 0.1476(4) -0.2728(3) 0.6424(2) 0.0190(4) Uani 1 1 d . . . H6 H 0.0374 -0.2869 0.5674 0.023 Uiso 1 1 calc R . . C7 C 0.6490(5) -0.2086(4) 0.9775(2) 0.0266(5) Uani 1 1 d . . . H7A H 0.5675 -0.2758 1.0498 0.032 Uiso 1 1 calc R . . H7B H 0.7453 -0.0630 1.0248 0.032 Uiso 1 1 calc R . . H7C H 0.7511 -0.2724 0.9331 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01590(16) 0.01806(17) 0.01221(15) 0.00469(12) 0.00315(12) 0.00905(13) Br1 0.02367(11) 0.02046(11) 0.01863(10) 0.00500(8) 0.00673(7) 0.01281(8) N1 0.0165(8) 0.0183(8) 0.0155(7) 0.0040(6) 0.0039(6) 0.0095(7) C2 0.0167(9) 0.0180(9) 0.0159(8) 0.0044(7) 0.0038(7) 0.0091(8) Br2 0.01553(10) 0.02436(11) 0.02188(10) 0.00826(8) 0.00015(7) 0.00730(8) C3 0.0276(11) 0.0195(10) 0.0151(9) 0.0057(8) 0.0061(8) 0.0139(9) C4 0.0304(12) 0.0197(10) 0.0234(10) 0.0081(8) 0.0113(9) 0.0128(9) C5 0.0201(10) 0.0192(10) 0.0294(11) 0.0042(9) 0.0101(9) 0.0057(8) C6 0.0180(10) 0.0185(10) 0.0187(9) -0.0001(8) 0.0041(7) 0.0091(8) C7 0.0382(14) 0.0333(13) 0.0185(10) 0.0103(9) 0.0054(9) 0.0233(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9793(17) 2_656 ? Cu1 N1 1.9793(17) . ? Cu1 Br1 2.4141(2) . ? Cu1 Br1 2.4141(2) 2_656 ? Br1 Br2 3.5572(3) 1_455 ? Br1 Cu1 5.2403(3) 1_455 ? N1 C2 1.334(3) . ? N1 C6 1.361(3) . ? C2 C3 1.396(3) . ? C2 Br2 1.893(2) . ? Br2 Br1 3.5572(3) 1_655 ? C3 C4 1.390(3) . ? C3 C7 1.500(3) . ? C4 C5 1.382(3) . ? C5 C6 1.379(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 2_656 . ? N1 Cu1 Br1 89.73(5) 2_656 . ? N1 Cu1 Br1 90.27(5) . . ? N1 Cu1 Br1 90.27(5) 2_656 2_656 ? N1 Cu1 Br1 89.73(5) . 2_656 ? Br1 Cu1 Br1 180.0 . 2_656 ? Cu1 Br1 Br2 106.450(8) . 1_455 ? Cu1 Br1 Cu1 103.016(7) . 1_455 ? Br2 Br1 Cu1 34.964(4) 1_455 1_455 ? C2 N1 C6 118.76(18) . . ? C2 N1 Cu1 119.45(14) . . ? C6 N1 Cu1 121.72(14) . . ? N1 C2 C3 124.6(2) . . ? N1 C2 Br2 114.44(15) . . ? C3 C2 Br2 120.99(16) . . ? C2 Br2 Br1 161.64(6) . 1_655 ? C4 C3 C2 115.3(2) . . ? C4 C3 C7 122.3(2) . . ? C2 C3 C7 122.4(2) . . ? C5 C4 C3 121.4(2) . . ? C6 C5 C4 119.3(2) . . ? N1 C6 C5 120.7(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 Br1 Br2 137.05(5) 2_656 . . 1_455 ? N1 Cu1 Br1 Br2 -42.95(5) . . . 1_455 ? Br1 Cu1 Br1 Br2 -164(100) 2_656 . . 1_455 ? N1 Cu1 Br1 Cu1 101.02(5) 2_656 . . 1_455 ? N1 Cu1 Br1 Cu1 -78.98(5) . . . 1_455 ? Br1 Cu1 Br1 Cu1 160(100) 2_656 . . 1_455 ? N1 Cu1 N1 C2 -117(100) 2_656 . . . ? Br1 Cu1 N1 C2 -95.30(15) . . . . ? Br1 Cu1 N1 C2 84.70(15) 2_656 . . . ? N1 Cu1 N1 C6 66(100) 2_656 . . . ? Br1 Cu1 N1 C6 87.80(15) . . . . ? Br1 Cu1 N1 C6 -92.20(15) 2_656 . . . ? C6 N1 C2 C3 0.6(3) . . . . ? Cu1 N1 C2 C3 -176.44(16) . . . . ? C6 N1 C2 Br2 179.75(14) . . . . ? Cu1 N1 C2 Br2 2.8(2) . . . . ? N1 C2 Br2 Br1 -59.0(3) . . . 1_655 ? C3 C2 Br2 Br1 120.22(19) . . . 1_655 ? N1 C2 C3 C4 -0.1(3) . . . . ? Br2 C2 C3 C4 -179.20(15) . . . . ? N1 C2 C3 C7 178.2(2) . . . . ? Br2 C2 C3 C7 -0.9(3) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C7 C3 C4 C5 -178.9(2) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C2 N1 C6 C5 -0.4(3) . . . . ? Cu1 N1 C6 C5 176.48(16) . . . . ? C4 C5 C6 N1 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.641 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.092 data_snhlr_1 _database_code_depnum_ccdc_archive 'CCDC 802934' #TrackingRef '3328_web_deposit_cif_file_0_SusanN.Herringer_1291229550.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-chloro-3-methylpyridine)dibromocopper (II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Br2 Cl2 Cu N2' _chemical_formula_weight 478.50 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6644(2) _cell_length_b 8.9944(2) _cell_length_c 11.9792(3) _cell_angle_alpha 80.2350(10) _cell_angle_beta 69.8130(10) _cell_angle_gamma 64.1000(10) _cell_volume 788.00(3) _cell_formula_units_Z 2 _cell_measurement_temperature 111(2) _cell_measurement_reflns_used 9911 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 30.36 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.017 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 6.782 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2131 _exptl_absorpt_correction_T_max 0.3169 _exptl_absorpt_process_details 'via SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 111(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21224 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 30.43 _reflns_number_total 4686 _reflns_number_gt 4109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0395P)^2^+0.1919P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4686 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.39099(3) 0.13932(2) 0.37674(2) 0.02104(6) Uani 1 1 d . . . Br2 Br 0.89226(3) -0.38725(2) 0.28700(2) 0.02281(6) Uani 1 1 d . . . Cu1 Cu 0.64647(3) -0.11943(3) 0.31457(2) 0.01681(7) Uani 1 1 d . . . Cl1 Cl 0.71945(8) 0.11251(7) 0.08509(5) 0.02623(12) Uani 1 1 d . . . Cl2 Cl 0.55804(8) -0.21832(8) 0.11131(5) 0.02968(13) Uani 1 1 d . . . N11 N 0.4799(2) -0.2294(2) 0.34139(16) 0.0174(3) Uani 1 1 d . . . N1 N 0.8214(2) -0.0129(2) 0.27334(16) 0.0171(3) Uani 1 1 d . . . C4 C 1.0420(3) 0.1497(3) 0.2366(2) 0.0216(4) Uani 1 1 d . . . H4 H 1.1154 0.2049 0.2258 0.026 Uiso 1 1 calc R . . C6 C 0.9205(3) -0.0420(2) 0.34636(19) 0.0192(4) Uani 1 1 d . . . H6 H 0.9131 -0.1168 0.4097 0.023 Uiso 1 1 calc R . . C15 C 0.2996(3) -0.3607(2) 0.4765(2) 0.0199(4) Uani 1 1 d . . . H15 H 0.2418 -0.3831 0.5545 0.024 Uiso 1 1 calc R . . C12 C 0.4610(3) -0.2828(2) 0.25170(19) 0.0182(4) Uani 1 1 d . . . C13 C 0.3693(3) -0.3827(2) 0.2654(2) 0.0185(4) Uani 1 1 d . . . C2 C 0.8369(3) 0.0931(2) 0.18169(19) 0.0179(4) Uani 1 1 d . . . C5 C 1.0329(3) 0.0367(3) 0.3293(2) 0.0202(4) Uani 1 1 d . . . H5 H 1.1017 0.0137 0.3799 0.024 Uiso 1 1 calc R . . C3 C 0.9424(3) 0.1821(2) 0.15879(19) 0.0195(4) Uani 1 1 d . . . C14 C 0.2872(3) -0.4200(2) 0.3818(2) 0.0195(4) Uani 1 1 d . . . H14 H 0.2234 -0.4853 0.3964 0.023 Uiso 1 1 calc R . . C16 C 0.3998(3) -0.2676(2) 0.45285(19) 0.0194(4) Uani 1 1 d . . . H16 H 0.4118 -0.2306 0.5161 0.023 Uiso 1 1 calc R . . C17 C 0.3605(3) -0.4461(3) 0.1612(2) 0.0275(5) Uani 1 1 d . . . H17A H 0.3179 -0.5321 0.1875 0.041 Uiso 1 1 calc R . . H17B H 0.4784 -0.4893 0.1044 0.041 Uiso 1 1 calc R . . H17C H 0.2796 -0.3575 0.1249 0.041 Uiso 1 1 calc R . . C7 C 0.9486(4) 0.3046(3) 0.0577(2) 0.0290(5) Uani 1 1 d . . . H7A H 1.0229 0.3570 0.0603 0.043 Uiso 1 1 calc R . . H7B H 0.8289 0.3866 0.0642 0.043 Uiso 1 1 calc R . . H7C H 0.9981 0.2487 -0.0162 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01861(11) 0.01554(10) 0.03005(13) -0.00017(7) -0.00861(9) -0.00718(8) Br2 0.01731(11) 0.01701(10) 0.03134(13) 0.00011(8) -0.00497(9) -0.00668(8) Cu1 0.01510(13) 0.01444(12) 0.02306(14) 0.00167(9) -0.00650(10) -0.00818(9) Cl1 0.0329(3) 0.0297(3) 0.0255(3) 0.0074(2) -0.0168(2) -0.0180(2) Cl2 0.0321(3) 0.0424(3) 0.0206(3) 0.0055(2) -0.0058(2) -0.0245(3) N11 0.0151(8) 0.0143(7) 0.0231(9) -0.0001(6) -0.0055(7) -0.0067(6) N1 0.0160(8) 0.0148(7) 0.0210(9) 0.0020(6) -0.0055(7) -0.0079(6) C4 0.0174(10) 0.0218(9) 0.0268(11) -0.0033(8) -0.0024(8) -0.0116(8) C6 0.0169(10) 0.0184(9) 0.0209(10) 0.0017(7) -0.0057(8) -0.0069(7) C15 0.0212(10) 0.0175(9) 0.0201(10) 0.0005(7) -0.0047(8) -0.0087(8) C12 0.0165(10) 0.0185(9) 0.0184(10) 0.0013(7) -0.0040(8) -0.0077(7) C13 0.0166(10) 0.0162(9) 0.0231(10) -0.0023(7) -0.0068(8) -0.0059(7) C2 0.0178(10) 0.0175(8) 0.0191(10) 0.0006(7) -0.0063(8) -0.0076(7) C5 0.0173(10) 0.0218(9) 0.0228(11) -0.0011(7) -0.0078(8) -0.0078(8) C3 0.0200(10) 0.0176(9) 0.0212(10) 0.0018(7) -0.0039(8) -0.0105(8) C14 0.0168(10) 0.0140(8) 0.0283(11) 0.0000(7) -0.0073(8) -0.0067(7) C16 0.0198(10) 0.0195(9) 0.0194(10) -0.0009(7) -0.0063(8) -0.0083(8) C17 0.0260(12) 0.0348(12) 0.0268(12) -0.0074(9) -0.0065(10) -0.0157(10) C7 0.0347(13) 0.0291(11) 0.0282(12) 0.0095(9) -0.0102(10) -0.0205(10) _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 Br1 Cu1 2.4126(3) . ? Br1 Cu1 3.5789(4) 2_656 ? Br2 Cu1 2.3979(3) . ? Cu1 N11 1.9963(17) . ? Cu1 N1 2.0126(17) . ? Cu1 Br1 3.5789(4) 2_656 ? Cl1 C2 1.730(2) . ? Cl2 C12 1.729(2) . ? N11 C12 1.333(3) . ? N11 C16 1.340(3) . ? N1 C2 1.337(3) . ? N1 C6 1.348(3) . ? C4 C5 1.378(3) . ? C4 C3 1.393(3) . ? C6 C5 1.381(3) . ? C15 C16 1.386(3) . ? C15 C14 1.386(3) . ? C12 C13 1.396(3) . ? C13 C14 1.388(3) . ? C13 C17 1.495(3) . ? C2 C3 1.394(3) . ? C3 C7 1.496(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu1 Br1 Cu1 99.520(9) . 2_656 ? N11 Cu1 N1 175.30(7) . . ? N11 Cu1 Br2 88.49(5) . . ? N1 Cu1 Br2 90.10(5) . . ? N11 Cu1 Br1 89.92(5) . . ? N1 Cu1 Br1 92.19(5) . . ? Br2 Cu1 Br1 170.589(14) . . ? N11 Cu1 Br1 93.38(5) . 2_656 ? N1 Cu1 Br1 91.11(5) . 2_656 ? Br2 Cu1 Br1 90.353(10) . 2_656 ? Br1 Cu1 Br1 80.480(9) . 2_656 ? C12 N11 C16 118.45(18) . . ? C12 N11 Cu1 122.00(14) . . ? C16 N11 Cu1 119.13(14) . . ? C2 N1 C6 118.02(17) . . ? C2 N1 Cu1 123.67(14) . . ? C6 N1 Cu1 118.18(14) . . ? C5 C4 C3 120.69(19) . . ? N1 C6 C5 121.59(19) . . ? C16 C15 C14 118.8(2) . . ? N11 C12 C13 124.38(19) . . ? N11 C12 Cl2 115.39(15) . . ? C13 C12 Cl2 120.23(17) . . ? C14 C13 C12 115.91(19) . . ? C14 C13 C17 122.04(19) . . ? C12 C13 C17 122.1(2) . . ? N1 C2 C3 124.75(19) . . ? N1 C2 Cl1 115.57(16) . . ? C3 C2 Cl1 119.65(16) . . ? C4 C5 C6 119.3(2) . . ? C4 C3 C2 115.57(19) . . ? C4 C3 C7 121.96(19) . . ? C2 C3 C7 122.5(2) . . ? C15 C14 C13 120.62(19) . . ? N11 C16 C15 121.8(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 Cu1 Br1 Cu1 N11 93.44(5) 2_656 . . . ? Cu1 Br1 Cu1 N1 -90.75(5) 2_656 . . . ? Cu1 Br1 Cu1 Br2 13.21(7) 2_656 . . . ? Cu1 Br1 Cu1 Br1 0.0 2_656 . . 2_656 ? N1 Cu1 N11 C12 -6.0(9) . . . . ? Br2 Cu1 N11 C12 -78.52(15) . . . . ? Br1 Cu1 N11 C12 110.76(15) . . . . ? Br1 Cu1 N11 C12 -168.78(15) 2_656 . . . ? N1 Cu1 N11 C16 166.4(7) . . . . ? Br2 Cu1 N11 C16 93.84(15) . . . . ? Br1 Cu1 N11 C16 -76.89(15) . . . . ? Br1 Cu1 N11 C16 3.57(15) 2_656 . . . ? N11 Cu1 N1 C2 47.4(9) . . . . ? Br2 Cu1 N1 C2 119.82(16) . . . . ? Br1 Cu1 N1 C2 -69.31(16) . . . . ? Br1 Cu1 N1 C2 -149.83(16) 2_656 . . . ? N11 Cu1 N1 C6 -136.9(8) . . . . ? Br2 Cu1 N1 C6 -64.47(15) . . . . ? Br1 Cu1 N1 C6 106.40(15) . . . . ? Br1 Cu1 N1 C6 25.89(15) 2_656 . . . ? C2 N1 C6 C5 1.1(3) . . . . ? Cu1 N1 C6 C5 -174.83(16) . . . . ? C16 N11 C12 C13 -2.9(3) . . . . ? Cu1 N11 C12 C13 169.53(16) . . . . ? C16 N11 C12 Cl2 176.54(15) . . . . ? Cu1 N11 C12 Cl2 -11.1(2) . . . . ? N11 C12 C13 C14 3.0(3) . . . . ? Cl2 C12 C13 C14 -176.40(15) . . . . ? N11 C12 C13 C17 -176.8(2) . . . . ? Cl2 C12 C13 C17 3.8(3) . . . . ? C6 N1 C2 C3 -3.0(3) . . . . ? Cu1 N1 C2 C3 172.71(17) . . . . ? C6 N1 C2 Cl1 175.19(15) . . . . ? Cu1 N1 C2 Cl1 -9.1(2) . . . . ? C3 C4 C5 C6 -1.5(3) . . . . ? N1 C6 C5 C4 1.0(3) . . . . ? C5 C4 C3 C2 -0.2(3) . . . . ? C5 C4 C3 C7 179.7(2) . . . . ? N1 C2 C3 C4 2.5(3) . . . . ? Cl1 C2 C3 C4 -175.60(16) . . . . ? N1 C2 C3 C7 -177.3(2) . . . . ? Cl1 C2 C3 C7 4.5(3) . . . . ? C16 C15 C14 C13 -1.9(3) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C17 C13 C14 C15 179.3(2) . . . . ? C12 N11 C16 C15 0.2(3) . . . . ? Cu1 N11 C16 C15 -172.41(16) . . . . ? C14 C15 C16 N11 2.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.43 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.804 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.139