#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/01/55/7015535.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_7015535 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 H9 Cu N9 O7' _chemical_formula_sum 'C7 H9 Cu N9 O7' _chemical_formula_weight 394.77 _chemical_name_systematic ; ? ; _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 15.5617(12) _cell_length_b 11.3047(9) _cell_length_c 7.9984(6) _cell_measurement_reflns_used 6109 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.59 _cell_measurement_theta_min 2.23 _cell_volume 1407.08(19) _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 16297 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.23 _exptl_absorpt_coefficient_mu 1.612 _exptl_absorpt_correction_T_max 0.9237 _exptl_absorpt_correction_T_min 0.7387 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_description flat _exptl_crystal_F_000 796 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.317 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1611 _refine_ls_number_restraints 36 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0233 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.8582P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.0651 _reflns_number_gt 1440 _reflns_number_total 1611 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c0dt01702g.txt _[local]_cod_data_source_block zhu68 _[local]_cod_cif_authors_sg_H-M Pbcn _[local]_cod_cif_authors_sg_Hall -P2n2ab _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 7015535 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, 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 0.5000 0.15484(2) 0.2500 0.01807(10) Uani 1 2 d S . . C1 C 0.36389(10) 0.30996(13) 0.1016(2) 0.0208(3) Uani 1 1 d . A . H1A H 0.3087 0.3242 0.1599 0.025 Uiso 1 1 calc R . . H1B H 0.3567 0.3306 -0.0179 0.025 Uiso 1 1 calc R . . C2 C 0.43413(9) 0.38393(13) 0.17860(19) 0.0190(3) Uani 1 1 d . . . C3 C 0.43238(10) 0.50672(14) 0.1771(2) 0.0251(3) Uani 1 1 d . . . H3 H 0.3858 0.5480 0.1271 0.030 Uiso 1 1 calc R . . C4 C 0.5000 0.5678(2) 0.2500 0.0272(5) Uani 1 2 d S . . H4 H 0.5000 0.6519 0.2500 0.033 Uiso 1 2 calc SR . . N1 N 0.5000 0.32559(16) 0.2500 0.0176(4) Uani 1 2 d S . . N2 N 0.38951(8) 0.18406(11) 0.11873(17) 0.0214(3) Uani 1 1 d . . . N3 N 0.3291(6) 0.1132(8) 0.142(3) 0.037(3) Uani 0.37(2) 1 d PU A 1 N4 N 0.2795(4) 0.0430(6) 0.152(4) 0.081(7) Uani 0.37(2) 1 d PU A 1 N3A N 0.3348(3) 0.1104(5) 0.0689(10) 0.0267(10) Uani 0.63(2) 1 d PU A 2 N4A N 0.2917(3) 0.0371(3) 0.0287(13) 0.0516(19) Uani 0.63(2) 1 d PU A 2 N5 N 0.63162(8) 0.20740(12) -0.06754(17) 0.0227(3) Uani 1 1 d . A . O1 O 0.56912(9) 0.14439(13) -0.01556(17) 0.0407(4) Uani 1 1 d . . . O2 O 0.64816(10) 0.20928(13) -0.21769(15) 0.0390(3) Uani 1 1 d . . . O3 O 0.67321(8) 0.26601(12) 0.03452(16) 0.0354(3) Uani 1 1 d . . . O4 O 0.5000 -0.01269(17) 0.2500 0.0414(5) Uani 1 2 d S . . H4O H 0.4812(17) -0.051(2) 0.180(3) 0.050 Uiso 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 0.01919(16) 0.01403(15) 0.02099(16) 0.000 -0.00429(9) 0.000 C1 0.0192(7) 0.0176(7) 0.0257(8) 0.0025(6) -0.0031(6) 0.0011(6) C2 0.0172(7) 0.0196(7) 0.0203(7) 0.0013(6) 0.0014(6) 0.0014(5) C3 0.0221(7) 0.0204(7) 0.0329(9) 0.0030(6) -0.0019(6) 0.0032(6) C4 0.0266(12) 0.0168(10) 0.0382(14) 0.000 0.0013(9) 0.000 N1 0.0168(9) 0.0170(8) 0.0191(9) 0.000 0.0015(6) 0.000 N2 0.0167(6) 0.0178(6) 0.0296(7) -0.0013(5) -0.0042(5) -0.0010(5) N3 0.019(3) 0.022(3) 0.072(8) 0.003(4) -0.014(4) 0.0041(19) N4 0.019(3) 0.024(3) 0.20(2) 0.020(5) -0.019(5) -0.003(2) N3A 0.0185(14) 0.0193(14) 0.042(3) 0.0040(18) -0.0076(18) 0.0012(10) N4A 0.0305(18) 0.0228(14) 0.102(5) 0.0022(19) -0.026(2) -0.0026(12) N5 0.0202(6) 0.0242(7) 0.0237(7) 0.0005(5) 0.0011(5) 0.0021(5) O1 0.0341(7) 0.0562(9) 0.0318(7) -0.0182(6) 0.0124(6) -0.0248(6) O2 0.0514(9) 0.0444(8) 0.0211(6) 0.0033(5) 0.0061(6) -0.0009(7) O3 0.0320(7) 0.0408(7) 0.0334(7) -0.0078(6) 0.0006(5) -0.0145(6) O4 0.0640(14) 0.0153(8) 0.0449(12) 0.000 -0.0329(10) 0.000 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' O O 0.0106 0.0060 '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 O4 Cu1 N1 180.0 . . ? O4 Cu1 N2 99.31(4) . . ? N1 Cu1 N2 80.69(4) . . ? O4 Cu1 N2 99.31(4) . 3_655 ? N1 Cu1 N2 80.69(4) . 3_655 ? N2 Cu1 N2 161.38(7) . 3_655 ? O4 Cu1 O1 87.16(3) . 3_655 ? N1 Cu1 O1 92.84(3) . 3_655 ? N2 Cu1 O1 94.95(5) . 3_655 ? N2 Cu1 O1 85.97(5) 3_655 3_655 ? O4 Cu1 O1 87.16(3) . . ? N1 Cu1 O1 92.84(3) . . ? N2 Cu1 O1 85.97(5) . . ? N2 Cu1 O1 94.95(5) 3_655 . ? O1 Cu1 O1 174.32(7) 3_655 . ? N2 C1 C2 107.41(12) . . ? N2 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? N2 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C3 120.57(15) . . ? N1 C2 C1 116.98(13) . . ? C3 C2 C1 122.45(13) . . ? C4 C3 C2 118.64(15) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C3 120.3(2) . 3_655 ? C3 C4 H4 119.9 . . ? C3 C4 H4 119.9 3_655 . ? C2 N1 C2 121.32(19) 3_655 . ? C2 N1 Cu1 119.34(9) 3_655 . ? C2 N1 Cu1 119.34(9) . . ? N3 N2 C1 115.3(4) . . ? N3A N2 C1 115.1(3) . . ? N3 N2 Cu1 117.0(6) . . ? N3A N2 Cu1 128.8(3) . . ? C1 N2 Cu1 115.39(9) . . ? N4 N3 N2 173.3(10) . . ? N4A N3A N2 173.5(5) . . ? O2 N5 O3 121.83(15) . . ? O2 N5 O1 119.22(14) . . ? O3 N5 O1 118.95(13) . . ? N5 O1 Cu1 127.37(10) . . ? Cu1 O4 H4O 124.2(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 O4 1.8939(19) . ? Cu1 N1 1.9303(19) . ? Cu1 N2 2.0415(13) . ? Cu1 N2 2.0415(13) 3_655 ? Cu1 O1 2.3838(13) 3_655 ? Cu1 O1 2.3838(13) . ? C1 N2 1.4845(19) . ? C1 C2 1.508(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.3460(17) . ? C2 C3 1.388(2) . ? C3 C4 1.3874(19) . ? C3 H3 0.9500 . ? C4 C3 1.3874(19) 3_655 ? C4 H4 0.9500 . ? N1 C2 1.3460(17) 3_655 ? N2 N3 1.248(10) . ? N2 N3A 1.256(6) . ? N3 N4 1.111(11) . ? N3A N4A 1.113(6) . ? N5 O2 1.2285(18) . ? N5 O3 1.2346(18) . ? N5 O1 1.2753(18) . ? O4 H4O 0.76(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 N2 C1 C2 N1 -2.83(17) . . . . ? N2 C1 C2 C3 177.04(14) . . . . ? N1 C2 C3 C4 0.2(2) . . . . ? C1 C2 C3 C4 -179.63(13) . . . . ? C2 C3 C4 C3 -0.11(11) . . . 3_655 ? C3 C2 N1 C2 -0.12(11) . . . 3_655 ? C1 C2 N1 C2 179.75(15) . . . 3_655 ? C3 C2 N1 Cu1 179.88(11) . . . . ? C1 C2 N1 Cu1 -0.25(15) . . . . ? N2 Cu1 N1 C2 -177.72(8) . . . 3_655 ? N2 Cu1 N1 C2 2.28(8) 3_655 . . 3_655 ? O1 Cu1 N1 C2 87.73(8) 3_655 . . 3_655 ? O1 Cu1 N1 C2 -92.27(8) . . . 3_655 ? N2 Cu1 N1 C2 2.28(8) . . . . ? N2 Cu1 N1 C2 -177.72(8) 3_655 . . . ? O1 Cu1 N1 C2 -92.27(8) 3_655 . . . ? O1 Cu1 N1 C2 87.73(8) . . . . ? C2 C1 N2 N3 145.8(10) . . . . ? C2 C1 N2 N3A 176.0(4) . . . . ? C2 C1 N2 Cu1 4.53(15) . . . . ? O4 Cu1 N2 N3 35.5(9) . . . . ? N1 Cu1 N2 N3 -144.5(9) . . . . ? N2 Cu1 N2 N3 -144.5(9) 3_655 . . . ? O1 Cu1 N2 N3 -52.4(9) 3_655 . . . ? O1 Cu1 N2 N3 122.0(9) . . . . ? O4 Cu1 N2 N3A 6.1(5) . . . . ? N1 Cu1 N2 N3A -173.9(5) . . . . ? N2 Cu1 N2 N3A -173.9(5) 3_655 . . . ? O1 Cu1 N2 N3A -81.8(5) 3_655 . . . ? O1 Cu1 N2 N3A 92.5(5) . . . . ? O4 Cu1 N2 C1 176.11(10) . . . . ? N1 Cu1 N2 C1 -3.89(10) . . . . ? N2 Cu1 N2 C1 -3.89(10) 3_655 . . . ? O1 Cu1 N2 C1 88.19(11) 3_655 . . . ? O1 Cu1 N2 C1 -97.43(11) . . . . ? O2 N5 O1 Cu1 -164.54(12) . . . . ? O3 N5 O1 Cu1 14.6(2) . . . . ? N1 Cu1 O1 N5 42.14(14) . . . . ? N2 Cu1 O1 N5 122.59(15) . . . . ? N2 Cu1 O1 N5 -38.75(15) 3_655 . . . ? _journal_paper_doi 10.1039/c0dt01702g