#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/01/55/7015534.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_7015534 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 'C7 H7 Cl2 Cu N7' _chemical_formula_sum 'C7 H7 Cl2 Cu N7' _chemical_formula_weight 323.64 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 119.04 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.1972(7) _cell_length_b 12.5443(6) _cell_length_c 14.1168(10) _cell_measurement_reflns_used 6298 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.81 _cell_measurement_theta_min 2.23 _cell_volume 2352.9(2) _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 12958 _diffrn_reflns_theta_full 27.10 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_min 2.23 _exptl_absorpt_coefficient_mu 2.298 _exptl_absorpt_correction_T_max 0.8028 _exptl_absorpt_correction_T_min 0.6961 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular, _exptl_crystal_F_000 1288 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.330 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2598 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.974 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0209 _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^)+(0.0284P)^2^+3.1320P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.0553 _reflns_number_gt 2366 _reflns_number_total 2598 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0dt01702g.txt _[local]_cod_data_source_block zhu67 _[local]_cod_cif_authors_sg_H-M C2/c _[local]_cod_cif_authors_sg_Hall -C2yc _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_original_cell_volume 2352.8(2) _cod_database_code 7015534 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' 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 0.145958(14) 0.814045(15) 0.119086(17) 0.01996(7) Uani 1 1 d . . . Cl1 Cl 0.22811(3) 0.81906(3) 0.31643(4) 0.02947(11) Uani 1 1 d . . . Cl2 Cl 0.21291(3) 0.95118(3) 0.07753(4) 0.02629(10) Uani 1 1 d . . . C1 C -0.07327(13) 0.80924(14) 0.06051(17) 0.0293(4) Uani 1 1 d . . . H1A H -0.1270 0.8119 -0.0161 0.035 Uiso 1 1 calc R . . H1B H -0.1028 0.8295 0.1069 0.035 Uiso 1 1 calc R . . C2 C -0.02939(12) 0.69876(13) 0.08881(14) 0.0235(3) Uani 1 1 d . . . C3 C 0.11222(12) 0.59247(13) 0.13328(13) 0.0220(3) Uani 1 1 d . . . C4 C 0.06291(14) 0.50221(14) 0.13978(14) 0.0270(4) Uani 1 1 d . . . H4 H 0.0956 0.4348 0.1574 0.032 Uiso 1 1 calc R . . C5 C -0.03568(14) 0.51290(15) 0.11980(15) 0.0290(4) Uani 1 1 d . . . H5 H -0.0711 0.4522 0.1239 0.035 Uiso 1 1 calc R . . C6 C -0.08281(13) 0.61176(15) 0.09381(14) 0.0279(4) Uani 1 1 d . . . H6 H -0.1503 0.6194 0.0798 0.033 Uiso 1 1 calc R . . C7 C 0.22002(13) 0.59154(13) 0.15557(16) 0.0269(4) Uani 1 1 d . . . H7A H 0.2668 0.5850 0.2343 0.032 Uiso 1 1 calc R . . H7B H 0.2315 0.5309 0.1180 0.032 Uiso 1 1 calc R . . N1 N 0.23611(11) 0.69424(11) 0.11399(13) 0.0235(3) Uani 1 1 d . . . N2 N 0.32443(11) 0.71428(11) 0.13454(12) 0.0251(3) Uani 1 1 d . . . N3 N 0.39866(12) 0.74177(14) 0.14572(16) 0.0403(4) Uani 1 1 d . . . N4 N 0.06645(10) 0.68767(10) 0.10863(12) 0.0210(3) Uani 1 1 d . . . N5 N 0.00964(11) 0.88368(12) 0.07840(13) 0.0285(3) Uani 1 1 d . . . N6 N 0.01333(11) 0.97099(13) 0.12290(13) 0.0308(3) Uani 1 1 d . . . N7 N 0.02633(15) 1.05182(16) 0.16090(17) 0.0519(5) 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 0.01742(11) 0.01533(11) 0.02931(12) 0.00073(8) 0.01305(9) 0.00009(7) Cl1 0.0334(2) 0.0282(2) 0.0267(2) -0.00298(16) 0.01452(19) -0.00642(17) Cl2 0.0240(2) 0.02006(19) 0.0378(2) 0.00338(16) 0.01728(18) -0.00179(15) C1 0.0184(8) 0.0281(9) 0.0428(11) 0.0038(8) 0.0158(8) 0.0003(7) C2 0.0186(8) 0.0260(9) 0.0244(8) -0.0003(7) 0.0093(7) -0.0023(6) C3 0.0217(8) 0.0206(8) 0.0224(8) -0.0011(6) 0.0097(7) -0.0020(6) C4 0.0312(9) 0.0198(8) 0.0287(9) 0.0011(7) 0.0135(8) -0.0030(7) C5 0.0293(9) 0.0276(9) 0.0299(9) 0.0002(7) 0.0142(8) -0.0102(7) C6 0.0210(8) 0.0322(9) 0.0300(9) 0.0019(7) 0.0121(7) -0.0044(7) C7 0.0235(9) 0.0176(8) 0.0393(10) 0.0045(7) 0.0151(8) 0.0015(6) N1 0.0198(7) 0.0196(7) 0.0343(8) 0.0024(6) 0.0156(6) 0.0022(5) N2 0.0240(8) 0.0196(7) 0.0305(8) 0.0034(6) 0.0121(6) 0.0037(6) N3 0.0244(8) 0.0328(9) 0.0616(12) 0.0122(8) 0.0193(8) 0.0034(7) N4 0.0189(7) 0.0192(7) 0.0246(7) 0.0001(5) 0.0104(6) -0.0012(5) N5 0.0218(7) 0.0208(7) 0.0458(9) 0.0001(6) 0.0187(7) 0.0020(6) N6 0.0241(8) 0.0316(9) 0.0350(9) -0.0013(7) 0.0130(7) 0.0063(6) N7 0.0395(11) 0.0448(12) 0.0630(13) -0.0211(10) 0.0181(10) 0.0065(8) 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 N4 Cu1 N5 79.71(6) . . ? N4 Cu1 N1 78.63(6) . . ? N5 Cu1 N1 153.86(6) . . ? N4 Cu1 Cl2 162.78(5) . . ? N5 Cu1 Cl2 97.23(4) . . ? N1 Cu1 Cl2 99.12(4) . . ? N4 Cu1 Cl1 93.56(4) . . ? N5 Cu1 Cl1 101.29(5) . . ? N1 Cu1 Cl1 94.50(5) . . ? Cl2 Cu1 Cl1 103.648(17) . . ? N5 C1 C2 107.64(14) . . ? N5 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? N5 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N4 C2 C6 120.61(16) . . ? N4 C2 C1 116.37(14) . . ? C6 C2 C1 123.02(15) . . ? N4 C3 C4 121.08(15) . . ? N4 C3 C7 115.76(14) . . ? C4 C3 C7 123.14(15) . . ? C3 C4 C5 118.18(17) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 120.43(16) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C2 C6 C5 118.55(16) . . ? C2 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? N1 C7 C3 106.32(13) . . ? N1 C7 H7A 110.5 . . ? C3 C7 H7A 110.5 . . ? N1 C7 H7B 110.5 . . ? C3 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? N2 N1 C7 116.49(14) . . ? N2 N1 Cu1 120.12(11) . . ? C7 N1 Cu1 112.32(10) . . ? N3 N2 N1 172.26(18) . . ? C3 N4 C2 121.15(14) . . ? C3 N4 Cu1 118.62(11) . . ? C2 N4 Cu1 119.81(11) . . ? N6 N5 C1 117.55(15) . . ? N6 N5 Cu1 116.00(12) . . ? C1 N5 Cu1 115.85(11) . . ? N7 N6 N5 171.5(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.9549(13) . ? Cu1 N5 2.0565(14) . ? Cu1 N1 2.0582(14) . ? Cu1 Cl2 2.2177(4) . ? Cu1 Cl1 2.4386(5) . ? C1 N5 1.488(2) . ? C1 C2 1.505(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N4 1.350(2) . ? C2 C6 1.382(2) . ? C3 N4 1.340(2) . ? C3 C4 1.385(2) . ? C3 C7 1.511(2) . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.484(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N1 N2 1.253(2) . ? N2 N3 1.115(2) . ? N5 N6 1.250(2) . ? N6 N7 1.119(2) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 C2 N4 -8.5(2) . . . . ? N5 C1 C2 C6 172.11(17) . . . . ? N4 C3 C4 C5 0.1(3) . . . . ? C7 C3 C4 C5 178.64(16) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? N4 C2 C6 C5 0.1(3) . . . . ? C1 C2 C6 C5 179.46(17) . . . . ? C4 C5 C6 C2 -0.3(3) . . . . ? N4 C3 C7 N1 -15.3(2) . . . . ? C4 C3 C7 N1 166.16(16) . . . . ? C3 C7 N1 N2 172.95(15) . . . . ? C3 C7 N1 Cu1 28.80(17) . . . . ? N4 Cu1 N1 N2 -168.93(15) . . . . ? N5 Cu1 N1 N2 156.50(14) . . . . ? Cl2 Cu1 N1 N2 28.42(14) . . . . ? Cl1 Cu1 N1 N2 -76.20(13) . . . . ? N4 Cu1 N1 C7 -26.24(12) . . . . ? N5 Cu1 N1 C7 -60.8(2) . . . . ? Cl2 Cu1 N1 C7 171.11(11) . . . . ? Cl1 Cu1 N1 C7 66.50(12) . . . . ? C4 C3 N4 C2 -0.3(3) . . . . ? C7 C3 N4 C2 -178.93(15) . . . . ? C4 C3 N4 Cu1 172.28(13) . . . . ? C7 C3 N4 Cu1 -6.3(2) . . . . ? C6 C2 N4 C3 0.2(3) . . . . ? C1 C2 N4 C3 -179.21(16) . . . . ? C6 C2 N4 Cu1 -172.30(13) . . . . ? C1 C2 N4 Cu1 8.3(2) . . . . ? N5 Cu1 N4 C3 -176.52(14) . . . . ? N1 Cu1 N4 C3 18.20(13) . . . . ? Cl2 Cu1 N4 C3 102.30(17) . . . . ? Cl1 Cu1 N4 C3 -75.68(13) . . . . ? N5 Cu1 N4 C2 -3.83(13) . . . . ? N1 Cu1 N4 C2 -169.11(14) . . . . ? Cl2 Cu1 N4 C2 -85.01(19) . . . . ? Cl1 Cu1 N4 C2 97.01(13) . . . . ? C2 C1 N5 N6 -137.91(17) . . . . ? C2 C1 N5 Cu1 5.45(19) . . . . ? N4 Cu1 N5 N6 142.53(15) . . . . ? N1 Cu1 N5 N6 176.96(13) . . . . ? Cl2 Cu1 N5 N6 -54.62(14) . . . . ? Cl1 Cu1 N5 N6 50.92(14) . . . . ? N4 Cu1 N5 C1 -1.40(13) . . . . ? N1 Cu1 N5 C1 33.0(2) . . . . ? Cl2 Cu1 N5 C1 161.45(13) . . . . ? Cl1 Cu1 N5 C1 -93.01(13) . . . . ? _journal_paper_doi 10.1039/c0dt01702g