#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:55:05 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235460 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/63/7236378.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_7236378
loop_
_publ_author_name
'Wei, Mei-Jie'
'Fu, Jia-Qi'
'Wang, Yi-Di'
'Gu, Jing-Yang'
'Liu, Bai-Ling'
'Zang, Hong-Ying'
'Zhou, En-Long'
'Shao, Kui-Zhan'
'Su, Zhong-Min'
_publ_section_title
;
 Changes of coordination modes of Cu-based coordination complexes as
 tuneable proton-conducting solid electrolytes
;
_journal_issue                   3
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              1085
_journal_paper_doi               10.1039/C6TA08581D
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C19 H13 Cl Cu N4 O7 S2'
_chemical_formula_weight         572.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-09-11 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 104.136(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   9.688(5)
_cell_length_b                   13.529(5)
_cell_length_c                   15.760(5)
_cell_measurement_reflns_used    2792
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0563
_cell_measurement_theta_min      2.2505
_cell_volume                     2003.1(14)
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.077
_diffrn_reflns_theta_min         2.010
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.489
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4 Bruker AXS Madison WI USA'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       block
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0453P)²+1.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2797
_reflns_number_total             3557
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ta08581d2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7236378
_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   0.616
_shelx_estimated_absorpt_t_max   0.735
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
C1 C 0.4143(4) -0.0348(3) 0.3251(2) 0.0237(8) Uani 1 1 d
C2 C 0.4146(4) -0.1372(3) 0.3178(2) 0.0263(8) Uani 1 1 d
C3 C 0.5205(4) -0.1914(3) 0.3711(2) 0.0246(8) Uani 1 1 d
C4 C 0.6270(3) -0.1415(2) 0.4317(2) 0.0196(7) Uani 1 1 d
C5 C 0.7448(3) -0.1853(2) 0.4932(2) 0.0205(7) Uani 1 1 d
C6 C 0.8446(3) -0.1315(2) 0.5515(2) 0.0225(7) Uani 1 1 d
C7 C 0.8402(3) -0.0263(2) 0.5562(2) 0.0217(7) Uani 1 1 d
C8 C 0.9370(4) 0.0343(3) 0.6142(2) 0.0320(9) Uani 1 1 d
C9 C 0.9177(4) 0.1342(3) 0.6103(3) 0.0366(10) Uani 1 1 d
C10 C 0.8014(4) 0.1741(3) 0.5497(2) 0.0311(9) Uani 1 1 d
C11 C 0.7263(3) 0.0192(2) 0.4968(2) 0.0193(7) Uani 1 1 d
C12 C 0.6211(3) -0.0381(2) 0.4355(2) 0.0182(7) Uani 1 1 d
C13 C 0.8966(3) -0.2901(2) 0.5735(2) 0.0215(7) Uani 1 1 d
C14 C 0.9733(3) -0.3810(2) 0.6079(2) 0.0223(7) Uani 1 1 d
C15 C 0.9084(3) -0.4750(2) 0.6082(2) 0.0208(7) Uani 1 1 d
C16 C 0.9913(4) -0.5550(2) 0.6450(2) 0.0227(8) Uani 1 1 d
C17 C 1.1372(3) -0.5436(2) 0.6810(2) 0.0217(7) Uani 1 1 d
C18 C 1.2009(4) -0.4531(3) 0.6780(2) 0.0293(9) Uani 1 1 d
C19 C 1.1183(4) -0.3730(3) 0.6416(2) 0.0280(8) Uani 1 1 d
N1 N 0.5147(3) 0.01461(19) 0.38213(16) 0.0197(6) Uani 1 1 d
N2 N 0.7074(3) 0.11807(19) 0.49422(17) 0.0202(6) Uani 1 1 d
N3 N 0.7796(3) -0.2827(2) 0.50831(18) 0.0229(7) Uani 1 1 d
N4 N 0.9393(3) -0.19867(19) 0.60106(18) 0.0238(7) Uani 1 1 d
O6 O 1.3850(3) -0.62541(19) 0.74272(18) 0.0389(7) Uani 1 1 d
O4 O 1.1884(3) -0.72910(18) 0.67435(18) 0.0418(7) Uani 1 1 d
O7W O 0.5540(3) 0.3011(2) 0.4313(2) 0.0472(9) Uani 1 1 d
O5 O 1.2039(3) -0.6565(2) 0.81583(18) 0.0526(8) Uani 1 1 d
O1 O 0.6588(3) -0.43948(17) 0.63037(16) 0.0331(6) Uani 1 1 d
O2 O 0.6783(3) -0.46116(18) 0.48113(15) 0.0344(6) Uani 1 1 d
O3 O 0.7019(2) -0.60244(16) 0.57663(16) 0.0307(6) Uani 1 1 d
S2 S 1.23428(9) -0.64801(6) 0.73166(5) 0.0216(2) Uani 1 1 d
S1 S 0.71981(9) -0.49653(6) 0.57114(5) 0.0236(2) Uani 1 1 d
Cu1 Cu 0.53983(4) 0.16198(3) 0.39612(3) 0.02200(13) Uani 1 1 d
Cl1 Cl 0.33978(10) 0.19651(7) 0.29771(6) 0.0390(3) Uani 1 1 d
H1 H 0.348(4) -0.001(2) 0.292(2) 0.019(9) Uiso 1 1 d
H2 H 0.343(4) -0.168(3) 0.273(2) 0.032(10) Uiso 1 1 d
H3 H 0.521(4) -0.259(3) 0.366(2) 0.029(10) Uiso 1 1 d
H3A H 0.730(4) -0.335(3) 0.486(3) 0.040(12) Uiso 1 1 d
H8 H 1.005(5) 0.004(3) 0.658(3) 0.063(14) Uiso 1 1 d
H9 H 0.977(5) 0.184(3) 0.653(3) 0.066(14) Uiso 1 1 d
H10 H 0.785(3) 0.242(3) 0.546(2) 0.019(9) Uiso 1 1 d
H16 H 0.949(4) -0.617(3) 0.646(2) 0.029(10) Uiso 1 1 d
H18 H 1.295(4) -0.442(3) 0.697(2) 0.037(11) Uiso 1 1 d
H19 H 1.160(3) -0.315(2) 0.641(2) 0.016(8) Uiso 1 1 d
H7B H 0.596(4) 0.329(3) 0.477(3) 0.042(13) Uiso 1 1 d
H7A H 0.493(5) 0.336(3) 0.410(3) 0.047(14) Uiso 1 1 d
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'
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'
Cl Cl 0.1484 0.1585 '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_3
N1 C1 C2 122.7(3) .
N1 C1 H1 117(2) .
C2 C1 H1 120(2) .
C3 C2 C1 120.0(3) .
C3 C2 H2 121(2) .
C1 C2 H2 119(2) .
C2 C3 C4 118.6(3) .
C2 C3 H3 120(2) .
C4 C3 H3 121(2) .
C3 C4 C12 118.7(3) .
C3 C4 C5 126.6(3) .
C12 C4 C5 114.7(3) .
N3 C5 C6 107.0(3) .
N3 C5 C4 129.7(3) .
C6 C5 C4 123.3(3) .
C5 C6 N4 106.9(3) .
C5 C6 C7 122.7(3) .
N4 C6 C7 130.4(3) .
C8 C7 C11 118.0(3) .
C8 C7 C6 126.4(3) .
C11 C7 C6 115.5(3) .
C9 C8 C7 119.3(3) .
C9 C8 H8 122(3) .
C7 C8 H8 118(3) .
C8 C9 C10 119.5(3) .
C8 C9 H9 125(3) .
C10 C9 H9 115(3) .
N2 C10 C9 122.5(3) .
N2 C10 H10 116(2) .
C9 C10 H10 122(2) .
N2 C11 C7 122.2(3) .
N2 C11 C12 116.3(3) .
C7 C11 C12 121.5(3) .
N1 C12 C4 121.9(3) .
N1 C12 C11 115.8(3) .
C4 C12 C11 122.3(3) .
N3 C13 N4 108.4(3) .
N3 C13 C14 127.2(3) .
N4 C13 C14 124.3(3) .
C19 C14 C15 118.7(3) .
C19 C14 C13 116.8(3) .
C15 C14 C13 124.5(3) .
C16 C15 C14 119.2(3) .
C16 C15 S1 116.6(3) .
C14 C15 S1 124.0(2) .
C15 C16 C17 120.6(3) .
C15 C16 H16 120(2) .
C17 C16 H16 120(2) .
C18 C17 C16 120.1(3) .
C18 C17 S2 122.0(3) .
C16 C17 S2 117.9(3) .
C17 C18 C19 119.4(3) .
C17 C18 H18 124(2) .
C19 C18 H18 116(2) .
C14 C19 C18 121.9(3) .
C14 C19 H19 120(2) .
C18 C19 H19 119(2) .
C1 N1 C12 118.1(3) .
C1 N1 Cu1 128.3(2) .
C12 N1 Cu1 113.4(2) .
C10 N2 C11 118.6(3) .
C10 N2 Cu1 128.4(2) .
C11 N2 Cu1 112.9(2) .
C13 N3 C5 109.5(3) .
C13 N3 H3A 121(3) .
C5 N3 H3A 128(3) .
C13 N4 C6 108.2(3) .
Cu1 O7W H7B 132(3) .
Cu1 O7W H7A 119(3) .
H7B O7W H7A 105(4) .
S2 O5 Cu1 148.50(19) 4_656
O4 S2 O5 115.04(19) .
O4 S2 O6 112.69(17) .
O5 S2 O6 109.41(18) .
O4 S2 C17 106.22(15) .
O5 S2 C17 105.93(16) .
O6 S2 C17 106.96(16) .
O1 S1 O3 114.58(16) .
O1 S1 O2 113.22(15) .
O3 S1 O2 111.98(14) .
O1 S1 C15 104.29(15) .
O3 S1 C15 105.52(14) .
O2 S1 C15 106.26(15) .
O7W Cu1 N1 168.80(13) .
O7W Cu1 N2 94.45(12) .
N1 Cu1 N2 81.21(10) .
O7W Cu1 Cl1 89.11(10) .
N1 Cu1 Cl1 94.03(8) .
N2 Cu1 Cl1 172.26(8) .
O7W Cu1 O5 100.36(13) 4
N1 Cu1 O5 89.39(11) 4
N2 Cu1 O5 82.90(12) 4
Cl1 Cu1 O5 103.25(9) 4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.332(4) .
C1 C2 1.390(5) .
C1 H1 0.85(3) .
C2 C3 1.370(5) .
C2 H2 0.95(4) .
C3 C4 1.397(4) .
C3 H3 0.92(4) .
C4 C12 1.402(4) .
C4 C5 1.432(4) .
C5 N3 1.366(4) .
C5 C6 1.370(4) .
C6 N4 1.389(4) .
C6 C7 1.426(4) .
C7 C8 1.402(5) .
C7 C11 1.403(4) .
C8 C9 1.363(5) .
C8 H8 0.93(4) .
C9 C10 1.396(5) .
C9 H9 1.02(5) .
C10 N2 1.334(4) .
C10 H10 0.93(3) .
C11 N2 1.350(4) .
C11 C12 1.446(4) .
C12 N1 1.362(4) .
C13 N3 1.335(4) .
C13 N4 1.342(4) .
C13 C14 1.470(4) .
C14 C19 1.379(5) .
C14 C15 1.419(5) .
C15 C16 1.387(4) .
C15 S1 1.801(3) .
C16 C17 1.397(5) .
C16 H16 0.93(4) .
C17 C18 1.378(5) .
C17 S2 1.775(3) .
C18 C19 1.386(5) .
C18 H18 0.90(4) .
C19 H19 0.88(3) .
N1 Cu1 2.014(3) .
N2 Cu1 2.038(3) .
N3 H3A 0.88(4) .
O6 S2 1.460(3) .
O4 S2 1.422(3) .
O7W Cu1 1.958(3) .
O7W H7B 0.83(4) .
O7W H7A 0.77(4) .
O5 S2 1.432(3) .
O5 Cu1 2.261(3) 4_656
O1 S1 1.445(3) .
O2 S1 1.458(2) .
O3 S1 1.448(2) .
Cu1 Cl1 2.2163(12) .
Cu1 O5 2.261(3) 4
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
N1 C1 C2 C3 0.6(6) .
C1 C2 C3 C4 -0.4(5) .
C2 C3 C4 C12 0.0(5) .
C2 C3 C4 C5 179.3(3) .
C3 C4 C5 N3 -1.2(6) .
C12 C4 C5 N3 178.1(3) .
C3 C4 C5 C6 -179.3(4) .
C12 C4 C5 C6 0.1(5) .
N3 C5 C6 N4 0.3(4) .
C4 C5 C6 N4 178.7(3) .
N3 C5 C6 C7 -178.5(3) .
C4 C5 C6 C7 -0.1(6) .
C5 C6 C7 C8 179.5(4) .
N4 C6 C7 C8 1.0(6) .
C5 C6 C7 C11 -0.1(5) .
N4 C6 C7 C11 -178.6(3) .
C11 C7 C8 C9 -0.4(6) .
C6 C7 C8 C9 -179.9(4) .
C7 C8 C9 C10 0.8(6) .
C8 C9 C10 N2 -0.4(7) .
C8 C7 C11 N2 -0.3(5) .
C6 C7 C11 N2 179.2(3) .
C8 C7 C11 C12 -179.4(3) .
C6 C7 C11 C12 0.2(5) .
C3 C4 C12 N1 0.2(5) .
C5 C4 C12 N1 -179.1(3) .
C3 C4 C12 C11 179.5(3) .
C5 C4 C12 C11 0.1(5) .
N2 C11 C12 N1 -0.1(4) .
C7 C11 C12 N1 179.0(3) .
N2 C11 C12 C4 -179.3(3) .
C7 C11 C12 C4 -0.2(5) .
N3 C13 C14 C19 149.2(4) .
N4 C13 C14 C19 -27.1(5) .
N3 C13 C14 C15 -30.6(6) .
N4 C13 C14 C15 153.1(3) .
C19 C14 C15 C16 2.2(5) .
C13 C14 C15 C16 -178.0(3) .
C19 C14 C15 S1 177.2(3) .
C13 C14 C15 S1 -3.0(5) .
C14 C15 C16 C17 -0.2(5) .
S1 C15 C16 C17 -175.6(3) .
C15 C16 C17 C18 -1.9(5) .
C15 C16 C17 S2 176.9(3) .
C16 C17 C18 C19 2.0(6) .
S2 C17 C18 C19 -176.7(3) .
C15 C14 C19 C18 -2.1(6) .
C13 C14 C19 C18 178.1(3) .
C17 C18 C19 C14 0.0(6) .
C2 C1 N1 C12 -0.3(5) .
C2 C1 N1 Cu1 175.1(3) .
C4 C12 N1 C1 -0.1(5) .
C11 C12 N1 C1 -179.3(3) .
C4 C12 N1 Cu1 -176.2(3) .
C11 C12 N1 Cu1 4.5(4) .
C9 C10 N2 C11 -0.3(6) .
C9 C10 N2 Cu1 -175.4(3) .
C7 C11 N2 C10 0.7(5) .
C12 C11 N2 C10 179.8(3) .
C7 C11 N2 Cu1 176.5(3) .
C12 C11 N2 Cu1 -4.4(4) .
N4 C13 N3 C5 -0.3(4) .
C14 C13 N3 C5 -177.1(3) .
C6 C5 N3 C13 0.0(4) .
C4 C5 N3 C13 -178.3(3) .
N3 C13 N4 C6 0.5(4) .
C14 C13 N4 C6 177.4(3) .
C5 C6 N4 C13 -0.5(4) .
C7 C6 N4 C13 178.2(4) .
Cu1 O5 S2 O4 -67.2(4) 4_656
Cu1 O5 S2 O6 164.8(3) 4_656
Cu1 O5 S2 C17 49.8(4) 4_656
C18 C17 S2 O4 -136.4(3) .
C16 C17 S2 O4 44.8(3) .
C18 C17 S2 O5 100.8(3) .
C16 C17 S2 O5 -78.0(3) .
C18 C17 S2 O6 -15.8(4) .
C16 C17 S2 O6 165.4(3) .
C16 C15 S1 O1 111.9(3) .
C14 C15 S1 O1 -63.2(3) .
C16 C15 S1 O3 -9.2(3) .
C14 C15 S1 O3 175.7(3) .
C16 C15 S1 O2 -128.2(3) .
C14 C15 S1 O2 56.7(3) .
