#------------------------------------------------------------------------------ #$Date: 2019-05-18 05:07:56 +0300 (Sat, 18 May 2019) $ #$Revision: 215296 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/00/7700025.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_7700025 loop_ _publ_author_name 'GUILLOU, Amaury' 'Lima, Lu\'is M. P.' 'Esteban, David' 'Delgado, Rita' 'Platas-Iglesias, Carlos' 'Patinec, Veronique' 'Tripier, Raphael' _publ_section_title ; Endo- versus Exocyclic Coordination in Copper Complexes with Methylthiazolylcarboxylate Tacn Derivatives ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/C9DT01366K _journal_year 2019 _chemical_formula_moiety 'C8 H4 Cu N2 O4 S2, 4(H2 O)' _chemical_formula_sum 'C8 H12 Cu N2 O8 S2' _chemical_formula_weight 391.86 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2018-05-04T20:45:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2019-03-07 deposited with the CCDC. 2019-05-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.069(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.9681(4) _cell_length_b 7.6471(3) _cell_length_c 9.1380(5) _cell_measurement_reflns_used 2047 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 28.752 _cell_measurement_theta_min 4.11 _cell_volume 692.66(5) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) ; _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) MERCURY (Bruno et al., 2002) ; _computing_publication_material ; WinGX (Farrugia, 1999) PLATON (Spek, 1990-2003) enCIFer (Allen et al., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SIR-92 (Altomare et al., 1992)' _diffrn_ambient_temperature 297(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.3622 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0069007 _diffrn_orient_matrix_UB_12 0.0618237 _diffrn_orient_matrix_UB_13 -0.0565909 _diffrn_orient_matrix_UB_21 0.0708915 _diffrn_orient_matrix_UB_22 -0.0128659 _diffrn_orient_matrix_UB_23 0.0084827 _diffrn_orient_matrix_UB_31 -0.0071736 _diffrn_orient_matrix_UB_32 -0.0678807 _diffrn_orient_matrix_UB_33 -0.0530994 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0425 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 4250 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 3.48 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.918 _exptl_absorpt_correction_T_max 0.9626 _exptl_absorpt_correction_T_min 0.4372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET) (compiled Aug 4 2014,14:34:23) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light blue' _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'hexagonal plate // (100), edges {011}, {01-1}' _exptl_crystal_F_000 398 _exptl_crystal_recrystallization_method 'from solution in water at room temperature,by slow evaporation of solvent' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.413 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.07 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1416 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0336 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.2929P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.0886 _reflns_number_gt 1218 _reflns_number_total 1416 _reflns_threshold_expression >2\s(I) _cod_data_source_file c9dt01366k2.cif _cod_data_source_block cu-tha3-a_297k _cod_original_sg_symbol_Hall -P2ybc _cod_original_sg_symbol_H-M P21/c _cod_database_code 7700025 _iucr_refine_instruction_details ; TITL Cu-tha3-a_297K in P2(1)/c CELL 0.71073 9.9681 7.6471 9.1380 90.000 96.069 90.000 ZERR 2.00 0.0004 0.0003 0.0005 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S CU UNIT 16 24 4 16 4 2 MERG 2 OMIT 1 1 0 SHEL 13 0.8 DFIX 0.85 O3 H3V O3 H3W O4 H4V O4 H4W DANG 1.34 H3V H3W H4V H4W EQIV $1 x+1, y, z EQIV $2 -x+1, -y+1, -z EQIV $3 -x+1, y+1/2, -z+1/2 HTAB O3 O4_$1 HTAB O3 O4_$2 HTAB O4 O2_$3 HTAB O4 O3_$3 FMAP 2 PLAN 25 SIZE 0.02 0.08 0.14 ACTA BOND $H L.S. 4 TEMP 24.00 WGHT 0.036400 0.292900 FVAR 1.41020 MOLE 1 C1 1 0.242180 0.282280 -0.072053 11.00000 0.03803 0.03997 = 0.04195 0.00535 -0.00178 -0.00032 AFIX 43 H1 2 0.196351 0.360033 -0.137776 11.00000 -1.20000 AFIX 0 C2 1 0.318494 0.045205 0.089645 11.00000 0.03990 0.03870 = 0.04094 0.00539 -0.00374 -0.00560 AFIX 43 H2 2 0.332548 -0.054831 0.147097 11.00000 -1.20000 AFIX 0 C3 1 0.407874 0.176705 0.084775 11.00000 0.03278 0.03458 = 0.03039 0.00044 0.00044 -0.00045 C4 1 0.546292 0.199052 0.162307 11.00000 0.03119 0.03571 = 0.03362 -0.00320 0.00101 0.00071 N1 3 0.363656 0.312179 -0.007634 11.00000 0.03055 0.03293 = 0.03674 0.00141 -0.00060 -0.00055 O1 4 0.610846 0.329931 0.119487 11.00000 0.03150 0.03495 = 0.04218 0.00171 -0.00139 -0.00270 O2 4 0.590659 0.094866 0.259629 11.00000 0.03750 0.05084 = 0.04383 0.01467 -0.00508 -0.00095 S1 5 0.176152 0.088501 -0.024483 11.00000 0.03650 0.04818 = 0.05024 0.00624 -0.00650 -0.01026 CU1 6 0.500000 0.500000 0.000000 10.50000 0.03290 0.02996 = 0.04614 0.00426 -0.00234 -0.00218 MOLE 2 O3 4 0.957902 0.376455 0.170502 11.00000 0.06920 0.07037 = 0.05464 0.00424 -0.00751 -0.01952 H3V 2 1.015936 0.452989 0.168399 11.00000 0.14661 H3W 2 0.919540 0.350610 0.090808 11.00000 0.06208 MOLE 3 O4 4 0.137439 0.650493 0.131114 11.00000 0.04079 0.06337 = 0.05061 -0.00575 -0.00326 -0.00091 H4V 2 0.214605 0.623196 0.159854 11.00000 0.09066 H4W 2 0.109378 0.720722 0.192518 11.00000 0.14342 HKLF 4 REM Cu-tha3-a_297K in P2(1)/c REM R1 = 0.0336 for 1218 Fo > 4sig(Fo) and 0.0418 for all 1416 data REM 113 parameters refined using 6 restraints END WGHT 0.0358 0.2876 REM Highest difference peak 0.413, deepest hole -0.311, 1-sigma level 0.070 Q1 1 0.2214 0.1900 -0.0497 11.00000 0.05 0.41 Q2 1 0.5518 0.3733 0.0223 11.00000 0.05 0.40 Q3 1 0.4304 0.3836 -0.0055 11.00000 0.05 0.38 Q4 1 0.5673 0.4206 0.0960 11.00000 0.05 0.36 Q5 1 0.2507 0.0778 0.0583 11.00000 0.05 0.28 Q6 1 0.3980 0.2357 0.0258 11.00000 0.05 0.27 Q7 1 0.6451 0.1663 0.2637 11.00000 0.05 0.26 Q8 1 0.3169 0.2976 -0.0382 11.00000 0.05 0.25 Q9 1 0.4768 0.1874 0.1315 11.00000 0.05 0.25 Q10 1 0.1601 -0.0858 -0.0287 11.00000 0.05 0.24 Q11 1 0.3749 0.1024 0.0720 11.00000 0.05 0.23 Q12 1 0.6136 0.0639 0.2001 11.00000 0.05 0.23 Q13 1 0.2464 0.0307 -0.0015 11.00000 0.05 0.22 Q14 1 0.1429 -0.0549 -0.0829 11.00000 0.05 0.22 Q15 1 0.9642 0.2869 0.2312 11.00000 0.05 0.21 Q16 1 0.6477 0.2941 0.0432 11.00000 0.05 0.20 Q17 1 0.3356 0.0029 0.0746 11.00000 0.05 0.20 Q18 1 0.1009 0.0133 -0.0349 11.00000 0.05 0.19 Q19 1 0.0581 0.5749 0.1272 11.00000 0.05 0.19 Q20 1 0.2939 -0.1126 0.2605 11.00000 0.05 0.18 Q21 1 0.5633 0.1674 0.2302 11.00000 0.05 0.17 Q22 1 0.5590 0.5273 -0.1117 11.00000 0.05 0.17 Q23 1 0.6627 0.3460 0.1540 11.00000 0.05 0.16 Q24 1 0.9204 0.2217 0.0408 11.00000 0.05 0.16 Q25 1 0.9410 0.3834 0.1263 11.00000 0.05 0.16 ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 0.2422(3) 0.2823(4) -0.0721(3) 0.0404(6) Uani 1 1 d . H1 H 0.1964 0.36 -0.1378 0.048 Uiso 1 1 calc R C2 C 0.3185(3) 0.0452(4) 0.0896(3) 0.0404(7) Uani 1 1 d . H2 H 0.3325 -0.0548 0.1471 0.049 Uiso 1 1 calc R C3 C 0.4079(3) 0.1767(3) 0.0848(3) 0.0328(6) Uani 1 1 d . C4 C 0.5463(3) 0.1991(3) 0.1623(3) 0.0337(6) Uani 1 1 d . N1 N 0.3637(2) 0.3122(3) -0.0076(2) 0.0337(5) Uani 1 1 d . O1 O 0.61085(19) 0.3299(2) 0.1195(2) 0.0366(4) Uani 1 1 d . O2 O 0.5907(2) 0.0949(3) 0.2596(2) 0.0447(5) Uani 1 1 d . S1 S 0.17615(8) 0.08850(10) -0.02448(9) 0.0458(2) Uani 1 1 d . Cu1 Cu 0.5 0.5 0 0.03680(18) Uani 1 2 d S O3 O 0.9579(3) 0.3765(4) 0.1705(3) 0.0657(7) Uani 1 1 d D H3V H 1.016(5) 0.453(6) 0.168(6) 0.15(3) Uiso 1 1 d D H3W H 0.920(3) 0.351(4) 0.091(3) 0.062(12) Uiso 1 1 d D O4 O 0.1374(3) 0.6505(3) 0.1311(3) 0.0522(6) Uani 1 1 d D H4V H 0.215(2) 0.623(5) 0.160(5) 0.091(15) Uiso 1 1 d D H4W H 0.109(5) 0.721(6) 0.193(5) 0.14(2) Uiso 1 1 d 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 C1 0.0380(16) 0.0400(15) 0.0419(16) 0.0054(12) -0.0018(12) -0.0003(13) C2 0.0399(17) 0.0387(14) 0.0409(16) 0.0054(12) -0.0037(13) -0.0056(13) C3 0.0328(14) 0.0346(13) 0.0304(13) 0.0004(10) 0.0004(11) -0.0005(12) C4 0.0312(14) 0.0357(14) 0.0336(14) -0.0032(11) 0.0010(11) 0.0007(12) N1 0.0305(12) 0.0329(11) 0.0367(12) 0.0014(9) -0.0006(9) -0.0006(10) O1 0.0315(10) 0.0350(10) 0.0422(11) 0.0017(8) -0.0014(8) -0.0027(9) O2 0.0375(12) 0.0508(12) 0.0438(12) 0.0147(9) -0.0051(9) -0.0009(10) S1 0.0365(4) 0.0482(4) 0.0502(5) 0.0062(3) -0.0065(3) -0.0103(4) Cu1 0.0329(3) 0.0300(3) 0.0461(3) 0.00426(19) -0.0023(2) -0.0022(2) O3 0.0692(18) 0.0704(17) 0.0546(17) 0.0042(13) -0.0075(13) -0.0195(15) O4 0.0408(13) 0.0634(14) 0.0506(14) -0.0057(11) -0.0033(11) -0.0009(12) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 1 -1 0.045 1 0 -1 0.035 0 1 -1 0.05 1 -1 -1 0.06 0 0 -1 0.04 0 -1 -1 0.06 -1 0 -1 0.03 -1 -1 -1 0.05 1 1 0 0.055 1 0 0 0.015 1 -1 0 0.065 -1 1 0 0.05 -1 0 0 0.005 -1 -1 0 0.055 1 1 1 0.055 1 0 1 0.035 0 1 1 0.06 0 0 1 0.04 -1 1 1 0.05 0 -1 1 0.06 -1 0 1 0.03 -1 -1 1 0.05 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 N1 C1 S1 113.7(2) . . N1 C1 H1 123.1 . . S1 C1 H1 123.1 . . C3 C2 S1 110.2(2) . . C3 C2 H2 124.9 . . S1 C2 H2 124.9 . . C2 C3 N1 114.3(2) . . C2 C3 C4 130.6(2) . . N1 C3 C4 115.1(2) . . O2 C4 O1 124.9(2) . . O2 C4 C3 120.6(2) . . O1 C4 C3 114.6(2) . . C1 N1 C3 111.4(2) . . C1 N1 Cu1 138.05(19) . . C3 N1 Cu1 110.53(17) . . C4 O1 Cu1 114.76(16) . . C1 S1 C2 90.35(14) . . O1 Cu1 O1 180 3_665 . O1 Cu1 N1 83.25(8) 3_665 3_665 O1 Cu1 N1 96.75(8) . 3_665 O1 Cu1 N1 96.75(8) 3_665 . O1 Cu1 N1 83.25(8) . . N1 Cu1 N1 180 3_665 . H3V O3 H3W 115(4) . . H4V O4 H4W 108(4) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N1 1.309(3) . C1 S1 1.697(3) . C1 H1 0.93 . C2 C3 1.347(4) . C2 S1 1.702(3) . C2 H2 0.93 . C3 N1 1.379(3) . C3 C4 1.493(4) . C4 O2 1.240(3) . C4 O1 1.274(3) . N1 Cu1 1.974(2) . O1 Cu1 1.9620(18) . Cu1 O1 1.9620(18) 3_665 Cu1 N1 1.974(2) 3_665 O3 H3V 0.825(19) . O3 H3W 0.810(18) . O4 H4V 0.813(19) . O4 H4W 0.845(19) . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3V O4 0.825(19) 1.99(2) 2.804(4) 170(6) 1_655 O3 H3W O4 0.810(18) 2.05(2) 2.826(4) 161(3) 3_665 O4 H4V O2 0.813(19) 2.01(2) 2.820(3) 171(4) 2_655 O4 H4W O3 0.845(19) 1.901(19) 2.746(4) 179(5) 2_655