#------------------------------------------------------------------------------ #$Date: 2011-06-21 23:03:58 +0300 (Tue, 21 Jun 2011) $ #$Revision: 21182 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7015533.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_7015533 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 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 108.7560(10) _cell_angle_beta 94.2700(10) _cell_angle_gamma 107.2860(10) _cell_formula_units_Z 2 _cell_length_a 7.1364(4) _cell_length_b 9.0635(5) _cell_length_c 10.3618(5) _cell_measurement_reflns_used 5977 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 32.94 _cell_measurement_theta_min 2.52 _cell_volume 595.15(6) _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 0.731 _diffrn_measured_fraction_theta_max 0.731 _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 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8719 _diffrn_reflns_theta_full 33.14 _diffrn_reflns_theta_max 33.14 _diffrn_reflns_theta_min 2.11 _exptl_absorpt_coefficient_mu 2.271 _exptl_absorpt_correction_T_max 0.8217 _exptl_absorpt_correction_T_min 0.6349 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_description flat _exptl_crystal_F_000 322 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.418 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 3312 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0247 _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^)+(0.0264P)^2^+0.3109P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.0593 _reflns_number_gt 2909 _reflns_number_total 3312 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0dt01702g.txt _[local]_cod_data_source_block zhu41 _[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_original_cell_volume 595.15(5) _cod_database_code 7015533 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 0.69485(3) 0.70098(2) 0.76787(2) 0.02191(6) Uani 1 1 d . . . Cl1 Cl 0.63224(6) 0.78401(5) 0.99709(4) 0.02595(9) Uani 1 1 d . . . Cl2 Cl 0.55426(7) 0.83200(6) 0.66570(5) 0.03144(10) Uani 1 1 d . . . C1 C 0.7319(2) 0.3889(2) 0.75957(16) 0.0223(3) Uani 1 1 d . . . C2 C 0.8245(3) 0.2831(2) 0.78059(18) 0.0280(4) Uani 1 1 d . . . H2 H 0.7512 0.1688 0.7571 0.034 Uiso 1 1 calc R . . C3 C 1.0276(3) 0.3468(2) 0.83690(19) 0.0294(4) Uani 1 1 d . . . H3 H 1.0941 0.2765 0.8540 0.035 Uiso 1 1 calc R . . C4 C 1.1326(2) 0.5129(2) 0.86796(18) 0.0267(4) Uani 1 1 d . . . H4 H 1.2714 0.5578 0.9061 0.032 Uiso 1 1 calc R . . C5 C 1.0317(2) 0.6124(2) 0.84246(17) 0.0227(3) Uani 1 1 d . . . C6 C 0.5124(2) 0.3317(2) 0.70269(19) 0.0259(3) Uani 1 1 d . . . H6A H 0.4738 0.2297 0.6189 0.031 Uiso 1 1 calc R . . H6B H 0.4337 0.3075 0.7727 0.031 Uiso 1 1 calc R . . C7 C 1.1318(2) 0.7945(2) 0.8715(2) 0.0289(4) Uani 1 1 d . . . H7A H 1.1588 0.8580 0.9725 0.035 Uiso 1 1 calc R . . H7B H 1.2603 0.8137 0.8384 0.035 Uiso 1 1 calc R . . N1 N 0.83405(19) 0.55095(17) 0.79115(14) 0.0206(3) Uani 1 1 d . . . N2 N 0.9951(2) 0.84853(19) 0.79761(16) 0.0282(3) Uani 1 1 d . . . N3 N 1.0664(2) 0.91944(19) 0.71858(16) 0.0295(3) Uani 1 1 d . . . N4 N 1.1138(3) 0.9854(2) 0.6456(2) 0.0462(5) Uani 1 1 d . . . N5 N 0.4751(2) 0.46695(18) 0.66765(16) 0.0261(3) Uani 1 1 d . . . N6 N 0.3092(2) 0.43165(19) 0.59428(15) 0.0271(3) Uani 1 1 d . . . N7 N 0.1658(2) 0.4140(2) 0.52922(18) 0.0389(4) 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 0.02046(9) 0.02071(11) 0.02424(11) 0.00895(8) 0.00389(8) 0.00571(8) Cl1 0.02513(18) 0.0274(2) 0.02278(19) 0.00676(16) 0.00432(15) 0.00795(16) Cl2 0.0364(2) 0.0303(2) 0.0327(2) 0.01490(19) 0.00507(18) 0.01504(19) C1 0.0235(7) 0.0217(8) 0.0198(8) 0.0068(6) 0.0055(6) 0.0055(7) C2 0.0332(9) 0.0212(8) 0.0282(9) 0.0074(7) 0.0072(7) 0.0087(7) C3 0.0328(8) 0.0333(10) 0.0287(9) 0.0118(8) 0.0100(7) 0.0190(8) C4 0.0212(7) 0.0343(10) 0.0259(8) 0.0104(7) 0.0074(6) 0.0109(7) C5 0.0190(6) 0.0259(9) 0.0214(8) 0.0085(7) 0.0056(6) 0.0048(6) C6 0.0232(7) 0.0233(9) 0.0283(9) 0.0114(7) 0.0018(6) 0.0025(7) C7 0.0213(7) 0.0287(9) 0.0342(10) 0.0145(8) 0.0002(7) 0.0027(7) N1 0.0190(6) 0.0203(7) 0.0210(7) 0.0070(5) 0.0045(5) 0.0048(5) N2 0.0208(6) 0.0264(8) 0.0362(8) 0.0161(7) 0.0040(6) 0.0015(6) N3 0.0256(7) 0.0245(8) 0.0322(8) 0.0097(6) 0.0015(6) 0.0012(6) N4 0.0432(10) 0.0474(11) 0.0457(11) 0.0277(9) 0.0056(8) 0.0007(9) N5 0.0201(6) 0.0243(7) 0.0301(8) 0.0093(6) 0.0000(5) 0.0038(6) N6 0.0245(7) 0.0288(8) 0.0261(7) 0.0090(6) 0.0066(6) 0.0072(6) N7 0.0290(8) 0.0483(11) 0.0343(9) 0.0107(8) -0.0008(7) 0.0123(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 N1 Cu1 N5 77.64(6) . . ? N1 Cu1 N2 78.48(6) . . ? N5 Cu1 N2 146.78(6) . . ? N1 Cu1 Cl2 159.62(4) . . ? N5 Cu1 Cl2 95.59(4) . . ? N2 Cu1 Cl2 98.86(4) . . ? N1 Cu1 Cl1 95.96(4) . . ? N5 Cu1 Cl1 103.72(4) . . ? N2 Cu1 Cl1 101.42(5) . . ? Cl2 Cu1 Cl1 104.345(18) . . ? N1 C1 C2 121.40(15) . . ? N1 C1 C6 116.38(15) . . ? C2 C1 C6 122.22(15) . . ? C1 C2 C3 118.65(16) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.81(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 118.80(16) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 121.15(15) . . ? N1 C5 C7 115.70(15) . . ? C4 C5 C7 123.14(15) . . ? N5 C6 C1 106.87(13) . . ? N5 C6 H6A 110.3 . . ? C1 C6 H6A 110.3 . . ? N5 C6 H6B 110.3 . . ? C1 C6 H6B 110.3 . . ? H6A C6 H6B 108.6 . . ? N2 C7 C5 107.67(13) . . ? N2 C7 H7A 110.2 . . ? C5 C7 H7A 110.2 . . ? N2 C7 H7B 110.2 . . ? C5 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C5 N1 C1 120.15(14) . . ? C5 N1 Cu1 119.44(11) . . ? C1 N1 Cu1 120.38(11) . . ? N3 N2 C7 116.26(14) . . ? N3 N2 Cu1 124.85(12) . . ? C7 N2 Cu1 112.10(10) . . ? N4 N3 N2 173.5(2) . . ? N6 N5 C6 116.40(14) . . ? N6 N5 Cu1 128.20(12) . . ? C6 N5 Cu1 114.95(10) . . ? N7 N6 N5 173.94(19) . . ? 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 1.9677(14) . ? Cu1 N5 2.0978(15) . ? Cu1 N2 2.0997(14) . ? Cu1 Cl2 2.2127(5) . ? Cu1 Cl1 2.3697(5) . ? C1 N1 1.347(2) . ? C1 C2 1.377(2) . ? C1 C6 1.501(2) . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 N1 1.347(2) . ? C5 C7 1.507(2) . ? C6 N5 1.474(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N2 1.480(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N2 N3 1.244(2) . ? N3 N4 1.119(2) . ? N5 N6 1.252(2) . ? N6 N7 1.121(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 C1 C2 C3 0.6(2) . . . . ? C6 C1 C2 C3 -178.44(16) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 N1 1.4(2) . . . . ? C3 C4 C5 C7 -179.60(16) . . . . ? N1 C1 C6 N5 12.3(2) . . . . ? C2 C1 C6 N5 -168.60(15) . . . . ? N1 C5 C7 N2 -16.2(2) . . . . ? C4 C5 C7 N2 164.81(15) . . . . ? C4 C5 N1 C1 -2.1(2) . . . . ? C7 C5 N1 C1 178.86(14) . . . . ? C4 C5 N1 Cu1 176.17(12) . . . . ? C7 C5 N1 Cu1 -2.87(19) . . . . ? C2 C1 N1 C5 1.1(2) . . . . ? C6 C1 N1 C5 -179.85(14) . . . . ? C2 C1 N1 Cu1 -177.19(12) . . . . ? C6 C1 N1 Cu1 1.90(19) . . . . ? N5 Cu1 N1 C5 171.10(13) . . . . ? N2 Cu1 N1 C5 14.36(12) . . . . ? Cl2 Cu1 N1 C5 98.79(16) . . . . ? Cl1 Cu1 N1 C5 -86.12(11) . . . . ? N5 Cu1 N1 C1 -10.64(12) . . . . ? N2 Cu1 N1 C1 -167.38(13) . . . . ? Cl2 Cu1 N1 C1 -82.95(16) . . . . ? Cl1 Cu1 N1 C1 92.14(12) . . . . ? C5 C7 N2 N3 -126.07(16) . . . . ? C5 C7 N2 Cu1 26.56(17) . . . . ? N1 Cu1 N2 N3 127.05(16) . . . . ? N5 Cu1 N2 N3 82.30(18) . . . . ? Cl2 Cu1 N2 N3 -32.41(16) . . . . ? Cl1 Cu1 N2 N3 -139.11(15) . . . . ? N1 Cu1 N2 C7 -22.80(12) . . . . ? N5 Cu1 N2 C7 -67.56(16) . . . . ? Cl2 Cu1 N2 C7 177.74(11) . . . . ? Cl1 Cu1 N2 C7 71.04(12) . . . . ? C1 C6 N5 N6 166.64(14) . . . . ? C1 C6 N5 Cu1 -20.42(17) . . . . ? N1 Cu1 N5 N6 -170.52(15) . . . . ? N2 Cu1 N5 N6 -125.59(15) . . . . ? Cl2 Cu1 N5 N6 -10.00(15) . . . . ? Cl1 Cu1 N5 N6 96.27(14) . . . . ? N1 Cu1 N5 C6 17.53(11) . . . . ? N2 Cu1 N5 C6 62.47(16) . . . . ? Cl2 Cu1 N5 C6 178.06(11) . . . . ? Cl1 Cu1 N5 C6 -75.68(12) . . . . ?