#------------------------------------------------------------------------------ #$Date: 2018-08-10 03:38:16 +0300 (Fri, 10 Aug 2018) $ #$Revision: 209538 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/76/7057638.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_7057638 loop_ _publ_author_name 'Kersen, \"Ulo' 'Wojtczak, Andrzej' 'Bie\'nko, Alina' 'Jezierska, Julia' _publ_section_title ; The effects of protonated heterocyclic cations on structural and magnetic properties of tetrachlorocuprate(II) anions; X-ray, magnetochemical and EPR studies ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C8NJ03155J _journal_year 2018 _chemical_formula_moiety '2(C6 H8 Cl N2), Cl4 Cu, 2(H2 O)' _chemical_formula_sum 'C12 H20 Cl6 Cu N4 O2' _chemical_formula_weight 528.56 _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary patterson _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014 _audit_update_record ; 2017-01-30 deposited with the CCDC. 2018-08-09 downloaded from the CCDC. ; _cell_angle_alpha 94.831(6) _cell_angle_beta 90.917(7) _cell_angle_gamma 91.361(6) _cell_formula_units_Z 1 _cell_length_a 7.1563(6) _cell_length_b 8.0445(5) _cell_length_c 9.1508(8) _cell_measurement_reflns_used 1932 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.2406 _cell_measurement_theta_min 2.2277 _cell_volume 524.70(7) _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_publication_material 'CIFTAB (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.2564 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.885 _diffrn_measurement_device_type 'Oxford Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_unetI/netI 0.0336 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.885 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3419 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.885 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 28.370 _diffrn_reflns_theta_min 2.234 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.819 _exptl_absorpt_correction_T_max 0.817 _exptl_absorpt_correction_T_min 0.464 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'Oxford Diffraction CrysAlis' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.673 _exptl_crystal_description plate _exptl_crystal_F_000 267 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.516 _exptl_crystal_size_mid 0.417 _exptl_crystal_size_min 0.111 _refine_diff_density_max 0.370 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 115 _refine_ls_number_reflns 2329 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0355 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0902 _refine_ls_wR_factor_ref 0.0949 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1865 _reflns_number_total 2329 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8nj03155j2.cif _cod_data_source_block e1153a _cod_database_code 7057638 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.454 _shelx_estimated_absorpt_t_max 0.824 _shelxl_version_number 2014-3 _shelx_res_file ; TITL e1153a in P-1 REM P-1 (#2 in standard setting) CELL 0.71073 7.156268 8.044546 9.150777 94.8307 90.9170 91.3613 ZERR 1.00 0.000647 0.000492 0.000766 0.0060 0.0071 0.0062 LATT 1 SFAC C H N O Cl Cu UNIT 12.00 20.00 4.00 2.00 6.00 1.00 TEMP 20 SIZE 0.5159 0.4172 0.1105 L.S. 10 BOND $H FMAP 2 PLAN 5 OMIT -3 HTAB HTAB N1 O1W EQIV $1 -x+1, -y+2, -z HTAB N31 Cl2_$1 EQIV $2 x, y+1, z HTAB N31 Cl2_$2 HTAB C4 Cl1_$1 EQIV $3 -x, -y+1, -z HTAB C6 O1W_$3 EQIV $4 x-1, y, z HTAB O1W Cl1_$4 EQIV $5 -x+1, -y+1, -z-1 HTAB O1W Cl1_$5 HTAB O1W Cl2 CONF ACTA 50 WGHT 0.050010 FVAR 7.63215 CU1 6 0.500000 0.500000 -0.500000 10.50000 0.03845 0.02827 = 0.03439 0.00273 0.00192 -0.00251 CL1 5 0.758881 0.666683 -0.498194 11.00000 0.05633 0.05739 = 0.04756 -0.00488 0.00840 -0.02417 CL2 5 0.497856 0.524894 -0.250686 11.00000 0.06402 0.06120 = 0.03501 0.00490 0.00109 -0.01591 N1 3 0.177680 0.802154 -0.053424 11.00000 0.03632 0.03986 = 0.02712 -0.00201 -0.00351 -0.00312 AFIX 3 H1N 2 0.132400 0.723714 -0.122835 11.00000 -1.20000 AFIX 0 C2 1 0.231060 0.948817 -0.097483 11.00000 0.03140 0.04906 = 0.02484 0.00760 0.00079 0.00154 CL21 5 0.234013 0.968710 -0.280958 11.00000 0.06439 0.08807 = 0.02545 0.01456 0.00221 0.00179 C3 1 0.280454 1.083434 0.004013 11.00000 0.03065 0.03762 = 0.03601 0.00554 0.00419 -0.00003 N31 3 0.327287 1.235274 -0.038763 11.00000 0.06757 0.04406 = 0.05294 0.01545 0.00412 -0.01102 AFIX 3 H1N3 2 0.381987 1.316074 0.037117 11.00000 -1.20000 H2N3 2 0.340687 1.254874 -0.137883 11.00000 -1.20000 AFIX 0 C4 1 0.277570 1.049739 0.150589 11.00000 0.03772 0.03854 = 0.02910 -0.00186 0.00088 -0.00043 AFIX 43 H4A 2 0.311087 1.134825 0.221999 11.00000 -1.20000 AFIX 0 C5 1 0.226879 0.894832 0.194446 11.00000 0.03503 0.04062 = 0.02592 0.00356 0.00055 0.00185 C51 1 0.228273 0.862542 0.353044 11.00000 0.06630 0.05647 = 0.02806 0.00762 0.00136 0.00583 AFIX 33 H51A 2 0.268408 0.962120 0.411417 11.00000 -1.20000 H51B 2 0.104648 0.830265 0.380724 11.00000 -1.20000 H51C 2 0.312658 0.774516 0.368789 11.00000 -1.20000 AFIX 0 C6 1 0.174151 0.770945 0.087389 11.00000 0.04253 0.03533 = 0.03115 0.00580 0.00026 -0.00474 AFIX 43 H6A 2 0.136312 0.666137 0.113231 11.00000 -1.20000 AFIX 0 O1W 4 0.029832 0.556719 -0.238522 11.00000 0.05120 0.05702 = 0.04057 -0.00996 -0.00214 -0.00526 AFIX 3 H1W1 2 -0.059788 0.561310 -0.290602 11.00000 -1.20000 H2W1 2 0.114912 0.484308 -0.271502 11.00000 -1.20000 AFIX 0 HKLF 4 REM e1153a in P-1 REM R1 = 0.0355 for 1865 Fo > 4sig(Fo) and 0.0483 for all 2329 data REM 115 parameters refined using 0 restraints END WGHT 0.0501 0.0000 REM Instructions for potential hydrogen bonds HTAB N1 O1W HTAB N31 Cl2_$1 HTAB N31 Cl2_$2 HTAB C4 Cl1_$1 HTAB C6 O1W_$3 HTAB O1W Cl1_$4 HTAB O1W Cl1_$5 HTAB O1W Cl2 REM Highest difference peak 0.370, deepest hole -0.366, 1-sigma level 0.069 Q1 1 0.3552 0.8711 0.3932 11.00000 0.05 0.37 Q2 1 0.4589 0.6050 -0.2834 11.00000 0.05 0.33 Q3 1 0.7740 0.5691 -0.4883 11.00000 0.05 0.33 Q4 1 0.2176 1.0674 -0.2735 11.00000 0.05 0.30 Q5 1 0.1856 0.7592 0.3621 11.00000 0.05 0.27 ; _shelx_res_checksum 56283 loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy Cu1 Cu 0.5000 0.5000 -0.5000 0.03374(15) Uani 1 2 d S . P Cl1 Cl 0.75888(11) 0.66668(10) -0.49819(8) 0.0546(2) Uani 1 1 d . . . Cl2 Cl 0.49786(11) 0.52489(10) -0.25069(7) 0.0536(2) Uani 1 1 d . . . N1 N 0.1777(3) 0.8022(3) -0.0534(2) 0.0348(5) Uani 1 1 d . . . H1N H 0.1324 0.7237 -0.1228 0.042 Uiso 1 1 d R U . C2 C 0.2311(3) 0.9488(3) -0.0975(3) 0.0348(6) Uani 1 1 d . . . Cl21 Cl 0.23401(11) 0.96871(11) -0.28096(7) 0.0587(2) Uani 1 1 d . . . C3 C 0.2805(3) 1.0834(3) 0.0040(3) 0.0346(6) Uani 1 1 d . . . N31 N 0.3273(4) 1.2353(3) -0.0388(3) 0.0544(7) Uani 1 1 d . . . H1N3 H 0.3820 1.3161 0.0371 0.065 Uiso 1 1 d R U . H2N3 H 0.3407 1.2549 -0.1379 0.065 Uiso 1 1 d R U . C4 C 0.2776(3) 1.0497(3) 0.1506(3) 0.0354(6) Uani 1 1 d . . . H4A H 0.3111 1.1348 0.2220 0.042 Uiso 1 1 calc R U . C5 C 0.2269(3) 0.8948(3) 0.1944(3) 0.0338(5) Uani 1 1 d . . . C51 C 0.2283(5) 0.8625(4) 0.3530(3) 0.0500(7) Uani 1 1 d . . . H51A H 0.2684 0.9621 0.4114 0.060 Uiso 1 1 calc R U . H51B H 0.1046 0.8303 0.3807 0.060 Uiso 1 1 calc R U . H51C H 0.3127 0.7745 0.3688 0.060 Uiso 1 1 calc R U . C6 C 0.1742(4) 0.7709(3) 0.0874(3) 0.0363(6) Uani 1 1 d . . . H6A H 0.1363 0.6661 0.1132 0.044 Uiso 1 1 calc R U . O1W O 0.0298(3) 0.5567(3) -0.2385(2) 0.0505(5) Uani 1 1 d . . . H1W1 H -0.0598 0.5613 -0.2906 0.061 Uiso 1 1 d R U . H2W1 H 0.1149 0.4843 -0.2715 0.061 Uiso 1 1 d R U . 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 0.0384(3) 0.0283(2) 0.0344(2) 0.00273(18) 0.00192(18) -0.00251(18) Cl1 0.0563(5) 0.0574(5) 0.0476(4) -0.0049(3) 0.0084(3) -0.0242(4) Cl2 0.0640(5) 0.0612(5) 0.0350(3) 0.0049(3) 0.0011(3) -0.0159(4) N1 0.0363(11) 0.0399(12) 0.0271(10) -0.0020(9) -0.0035(9) -0.0031(9) C2 0.0314(13) 0.0491(16) 0.0248(11) 0.0076(11) 0.0008(10) 0.0015(11) Cl21 0.0644(5) 0.0881(6) 0.0254(3) 0.0146(3) 0.0022(3) 0.0018(4) C3 0.0306(13) 0.0376(14) 0.0360(13) 0.0055(11) 0.0042(10) 0.0000(10) N31 0.0676(17) 0.0441(14) 0.0529(14) 0.0154(12) 0.0041(13) -0.0110(12) C4 0.0377(14) 0.0385(14) 0.0291(12) -0.0019(11) 0.0009(10) -0.0004(11) C5 0.0350(13) 0.0406(14) 0.0259(11) 0.0036(11) 0.0006(10) 0.0019(11) C51 0.066(2) 0.0565(19) 0.0281(12) 0.0076(13) 0.0014(13) 0.0058(15) C6 0.0425(15) 0.0353(14) 0.0312(12) 0.0058(11) 0.0003(11) -0.0047(11) O1W 0.0512(12) 0.0570(13) 0.0406(10) -0.0100(9) -0.0021(9) -0.0053(9) 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' 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 Cl1 Cu1 Cl1 180.0 2_664 . Cl1 Cu1 Cl2 90.62(3) 2_664 2_664 Cl1 Cu1 Cl2 89.38(3) . 2_664 Cl1 Cu1 Cl2 89.38(3) 2_664 . Cl1 Cu1 Cl2 90.62(3) . . Cl2 Cu1 Cl2 180.00(4) 2_664 . C2 N1 C6 123.1(2) . . C2 N1 H1N 117.4 . . C6 N1 H1N 119.3 . . N1 C2 C3 121.0(2) . . N1 C2 Cl21 117.83(19) . . C3 C2 Cl21 121.1(2) . . N31 C3 C4 122.7(2) . . N31 C3 C2 121.8(2) . . C4 C3 C2 115.5(2) . . C3 N31 H1N3 116.3 . . C3 N31 H2N3 122.4 . . H1N3 N31 H2N3 119.1 . . C5 C4 C3 122.7(2) . . C5 C4 H4A 118.7 . . C3 C4 H4A 118.7 . . C6 C5 C4 117.9(2) . . C6 C5 C51 120.9(2) . . C4 C5 C51 121.1(2) . . C5 C51 H51A 109.5 . . C5 C51 H51B 109.5 . . H51A C51 H51B 109.5 . . C5 C51 H51C 109.5 . . H51A C51 H51C 109.5 . . H51B C51 H51C 109.5 . . N1 C6 C5 119.7(2) . . N1 C6 H6A 120.2 . . C5 C6 H6A 120.2 . . H1W1 O1W H2W1 114.9 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 Cl1 2.2600(7) 2_664 Cu1 Cl1 2.2600(7) . Cu1 Cl2 2.2736(7) 2_664 Cu1 Cl2 2.2737(7) . N1 C2 1.328(3) . N1 C6 1.334(3) . N1 H1N 0.9071 . C2 C3 1.401(4) . C2 Cl21 1.700(2) . C3 N31 1.350(3) . C3 C4 1.391(3) . N31 H1N3 0.9803 . N31 H2N3 0.9396 . C4 C5 1.383(4) . C4 H4A 0.9300 . C5 C6 1.379(4) . C5 C51 1.496(3) . C51 H51A 0.9600 . C51 H51B 0.9600 . C51 H51C 0.9600 . C6 H6A 0.9300 . O1W H1W1 0.7963 . O1W H2W1 0.8912 . 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 N1 H1N O1W 0.91 1.78 2.677(3) 172.1 . N31 H1N3 Cl2 0.98 2.38 3.350(3) 169.7 2_675 N31 H2N3 Cl2 0.94 2.71 3.374(2) 128.2 1_565 C4 H4A Cl1 0.93 2.93 3.771(3) 151.1 2_675 C6 H6A O1W 0.93 2.50 3.389(3) 161.1 2_565 O1W H1W1 Cl1 0.80 2.50 3.237(2) 154.2 1_455 O1W H2W1 Cl1 0.89 2.53 3.292(2) 143.5 2_664 O1W H2W1 Cl2 0.89 2.75 3.368(2) 127.2 . 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 C6 N1 C2 C3 -2.6(4) C6 N1 C2 Cl21 178.37(19) N1 C2 C3 N31 -177.1(3) Cl21 C2 C3 N31 1.9(3) N1 C2 C3 C4 2.8(4) Cl21 C2 C3 C4 -178.21(19) N31 C3 C4 C5 179.0(3) C2 C3 C4 C5 -0.9(4) C3 C4 C5 C6 -1.2(4) C3 C4 C5 C51 179.1(3) C2 N1 C6 C5 0.3(4) C4 C5 C6 N1 1.6(4) C51 C5 C6 N1 -178.7(2)