#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/01/55/7015525.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7015525 loop_ _publ_author_name 'Brotherton, Wendy S.' 'Guha, Pampa M.' 'Phan, Hoa' 'Clark, Ronald J.' 'Shatruk, Michael' 'Zhu, Lei' _publ_section_title ; Tridentate complexes of 2,6-bis(4-substituted-1,2,3-triazol-1-ylmethyl)pyridine and its organic azide precursors: an application of the copper(II) acetate-accelerated azide-alkyne cycloaddition. ; _journal_issue 14 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 3655 _journal_page_last 3665 _journal_volume 40 _journal_year 2011 _chemical_formula_moiety 'C12 H12 Cl4 Cu2 N8' _chemical_formula_sum 'C12 H12 Cl4 Cu2 N8' _chemical_formula_weight 537.18 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 68.0600(10) _cell_angle_beta 71.7100(10) _cell_angle_gamma 89.3780(10) _cell_formula_units_Z 1 _cell_length_a 6.8184(3) _cell_length_b 8.0206(3) _cell_length_c 9.7388(3) _cell_measurement_reflns_used 5967 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 33.06 _cell_measurement_theta_min 2.39 _cell_volume 465.63(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6699 _diffrn_reflns_theta_full 28.25 _diffrn_reflns_theta_max 28.25 _diffrn_reflns_theta_min 2.39 _exptl_absorpt_coefficient_mu 2.872 _exptl_absorpt_correction_T_max 0.563 _exptl_absorpt_correction_T_min 0.457 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 266 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.279 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.085 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 2.709 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2249 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 2.709 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0210 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.0504 _reflns_number_gt 2171 _reflns_number_total 2249 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0dt01702g.txt _[local]_cod_data_source_block zhu37 _[local]_cod_cif_authors_sg_H-M P-1 _[local]_cod_cif_authors_sg_Hall -P1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 7015525 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.79596(3) 0.08118(3) 0.43876(2) 0.01678(7) Uani 1 1 d . . . N1 N 0.7650(2) 0.14757(19) 0.22496(16) 0.0168(3) Uani 1 1 d . . . N2 N 0.6936(2) -0.16228(19) 0.45064(16) 0.0211(3) Uani 1 1 d . . . N3 N 0.6593(2) -0.3104(2) 0.56641(17) 0.0194(3) Uani 1 1 d . . . N4 N 0.6255(3) -0.4349(2) 0.67614(18) 0.0270(4) Uani 1 1 d . . . C1 C 0.7881(3) 0.3196(2) 0.1184(2) 0.0229(4) Uani 1 1 d . . . H1 H 0.8067 0.4168 0.1482 0.027 Uiso 1 1 calc R . . C2 C 0.7858(3) 0.3588(3) -0.0307(2) 0.0262(4) Uani 1 1 d . . . H2 H 0.8010 0.4810 -0.1021 0.031 Uiso 1 1 calc R . . C3 C 0.7609(3) 0.2182(3) -0.0760(2) 0.0246(4) Uani 1 1 d . . . H3 H 0.7599 0.2422 -0.1790 0.030 Uiso 1 1 calc R . . C4 C 0.7374(3) 0.0425(2) 0.0316(2) 0.0222(4) Uani 1 1 d . . . H4 H 0.7218 -0.0564 0.0031 0.027 Uiso 1 1 calc R . . C5 C 0.7367(3) 0.0115(2) 0.1817(2) 0.0175(3) Uani 1 1 d . . . C6 C 0.7041(3) -0.1778(2) 0.30229(19) 0.0220(4) Uani 1 1 d . . . H6A H 0.5731 -0.2431 0.3149 0.026 Uiso 1 1 calc R . . H6B H 0.8208 -0.2448 0.2703 0.026 Uiso 1 1 calc R . . Cl1 Cl 0.82604(7) 0.36269(6) 0.42883(5) 0.02384(11) Uani 1 1 d . . . Cl2 Cl 0.79679(7) -0.04836(6) 0.68895(5) 0.02113(11) 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 0.01959(13) 0.01670(12) 0.01639(12) -0.00723(9) -0.00809(9) 0.00158(9) N1 0.0156(8) 0.0179(7) 0.0168(7) -0.0057(6) -0.0064(6) 0.0007(6) N2 0.0316(9) 0.0151(8) 0.0149(7) -0.0028(6) -0.0092(7) -0.0025(7) N3 0.0195(8) 0.0206(8) 0.0218(8) -0.0107(7) -0.0089(7) 0.0028(6) N4 0.0349(10) 0.0216(9) 0.0237(8) -0.0047(7) -0.0137(8) 0.0025(7) C1 0.0237(10) 0.0205(10) 0.0244(10) -0.0070(8) -0.0100(8) -0.0003(8) C2 0.0308(11) 0.0218(10) 0.0207(9) -0.0002(8) -0.0114(8) 0.0012(8) C3 0.0244(10) 0.0319(11) 0.0180(9) -0.0081(8) -0.0094(8) 0.0036(8) C4 0.0230(10) 0.0274(10) 0.0195(9) -0.0120(8) -0.0083(8) 0.0037(8) C5 0.0143(9) 0.0208(9) 0.0179(8) -0.0083(7) -0.0051(7) 0.0026(7) C6 0.0288(11) 0.0214(9) 0.0173(9) -0.0096(8) -0.0069(8) 0.0014(8) Cl1 0.0286(3) 0.0193(2) 0.0281(2) -0.01271(19) -0.0111(2) 0.00330(19) Cl2 0.0222(2) 0.0275(2) 0.0163(2) -0.01043(18) -0.00764(18) 0.00451(18) 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' 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 N2 77.98(5) . . ? N1 Cu1 Cl1 96.94(4) . . ? N2 Cu1 Cl1 165.46(5) . . ? N1 Cu1 Cl2 168.33(4) . . ? N2 Cu1 Cl2 90.52(4) . . ? Cl1 Cu1 Cl2 93.770(17) . . ? N1 Cu1 Cl2 88.91(4) . 2_756 ? N2 Cu1 Cl2 93.69(5) . 2_756 ? Cl1 Cu1 Cl2 99.879(17) . 2_756 ? Cl2 Cu1 Cl2 93.801(15) . 2_756 ? C5 N1 C1 118.04(14) . . ? C5 N1 Cu1 117.51(11) . . ? C1 N1 Cu1 124.21(11) . . ? N3 N2 C6 114.82(14) . . ? N3 N2 Cu1 126.00(10) . . ? C6 N2 Cu1 117.71(11) . . ? N4 N3 N2 174.81(16) . . ? N1 C1 C2 122.57(16) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.26(17) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 118.59(16) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 119.47(16) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 122.03(16) . . ? N1 C5 C6 117.48(14) . . ? C4 C5 C6 120.49(15) . . ? N2 C6 C5 106.63(13) . . ? N2 C6 H6A 110.4 . . ? C5 C6 H6A 110.4 . . ? N2 C6 H6B 110.4 . . ? C5 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? Cu1 Cl2 Cu1 86.199(15) . 2_756 ? 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 2.0270(13) . ? Cu1 N2 2.0305(14) . ? Cu1 Cl1 2.2325(4) . ? Cu1 Cl2 2.2656(4) . ? Cu1 Cl2 2.7181(5) 2_756 ? N1 C5 1.344(2) . ? N1 C1 1.355(2) . ? N2 N3 1.256(2) . ? N2 C6 1.476(2) . ? N3 N4 1.116(2) . ? C1 C2 1.372(2) . ? C1 H1 0.9500 . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.381(2) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C6 1.498(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? Cl2 Cu1 2.7181(5) 2_756 ? 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 N2 Cu1 N1 C5 -12.31(12) . . . . ? Cl1 Cu1 N1 C5 -178.48(12) . . . . ? Cl2 Cu1 N1 C5 -21.9(3) . . . . ? Cl2 Cu1 N1 C5 81.70(12) 2_756 . . . ? N2 Cu1 N1 C1 173.40(15) . . . . ? Cl1 Cu1 N1 C1 7.22(14) . . . . ? Cl2 Cu1 N1 C1 163.78(15) . . . . ? Cl2 Cu1 N1 C1 -92.60(14) 2_756 . . . ? N1 Cu1 N2 N3 -179.18(16) . . . . ? Cl1 Cu1 N2 N3 -108.37(18) . . . . ? Cl2 Cu1 N2 N3 -1.12(15) . . . . ? Cl2 Cu1 N2 N3 92.72(15) 2_756 . . . ? N1 Cu1 N2 C6 15.43(12) . . . . ? Cl1 Cu1 N2 C6 86.2(2) . . . . ? Cl2 Cu1 N2 C6 -166.50(12) . . . . ? Cl2 Cu1 N2 C6 -72.66(13) 2_756 . . . ? C5 N1 C1 C2 -0.7(3) . . . . ? Cu1 N1 C1 C2 173.59(13) . . . . ? N1 C1 C2 C3 -0.6(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C1 N1 C5 C4 2.1(2) . . . . ? Cu1 N1 C5 C4 -172.55(13) . . . . ? C1 N1 C5 C6 -177.97(15) . . . . ? Cu1 N1 C5 C6 7.4(2) . . . . ? C3 C4 C5 N1 -2.2(3) . . . . ? C3 C4 C5 C6 177.87(16) . . . . ? N3 N2 C6 C5 177.66(14) . . . . ? Cu1 N2 C6 C5 -15.34(19) . . . . ? N1 C5 C6 N2 4.9(2) . . . . ? C4 C5 C6 N2 -175.13(15) . . . . ? N1 Cu1 Cl2 Cu1 103.1(2) . . . 2_756 ? N2 Cu1 Cl2 Cu1 93.73(4) . . . 2_756 ? Cl1 Cu1 Cl2 Cu1 -100.177(16) . . . 2_756 ? Cl2 Cu1 Cl2 Cu1 0.0 2_756 . . 2_756 ? _journal_paper_doi 10.1039/c0dt01702g