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#$Date: 2023-12-22 15:56:34 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/32/7233260.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_7233260
loop_
_publ_author_name
'Wei, Mei-Jie'
'Gao, Ying'
'Li, Ke'
'Li, Bo'
'Fu, Jia-Qi'
'Zang, Hong-Ying'
'Shao, Kui-Zhan'
'Su, Zhong-Min'
_publ_section_title
;
 Supramolecular hydrogen-bonded organic networks through acid--base pairs
 as efficient proton-conducting electrolytes
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              4996
_journal_paper_doi               10.1039/C9CE00762H
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C8 H22 N12 O8 P0 S2'
_chemical_formula_weight         478.49
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-11-27 deposited with the CCDC.    2019-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                93.919(5)
_cell_angle_beta                 98.389(5)
_cell_angle_gamma                108.883(5)
_cell_formula_units_Z            1
_cell_length_a                   6.206(5)
_cell_length_b                   7.228(5)
_cell_length_c                   11.882(5)
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.00
_cell_volume                     495.1(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.986
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3749
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_min         1.746
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4 Bruker AXS Madison WI USA'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       flake
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0471
_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)+(0.0944P)²+0.0336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2046
_reflns_number_total             2488
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00762h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7233260--7233261.cif.'
_cod_database_code               7233260
_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   0.912
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2014-3
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
S1 S 0.13641(9) 0.62250(7) 0.85292(4) 0.02829(19) Uani 1 1 d
O2 O 0.0859(3) 0.5130(3) 0.73934(13) 0.0413(4) Uani 1 1 d
O3 O 0.0466(3) 0.7843(3) 0.85458(17) 0.0469(5) Uani 1 1 d
N2 N -0.4417(3) 0.1680(3) 0.69490(15) 0.0310(4) Uani 1 1 d
O1 O 0.3803(3) 0.6864(3) 0.90339(15) 0.0460(5) Uani 1 1 d
N6 N -0.3366(3) 0.3170(3) 0.53214(15) 0.0297(4) Uani 1 1 d
N5 N -0.0846(4) 0.2166(3) 0.44191(18) 0.0363(5) Uani 1 1 d
N4 N -0.1853(3) 0.0667(2) 0.59884(15) 0.0308(4) Uani 1 1 d
C3 C -0.2048(4) 0.2004(3) 0.52635(17) 0.0277(4) Uani 1 1 d
C4 C -0.0182(4) 0.4545(3) 0.93885(18) 0.0352(5) Uani 1 1 d
C2 C -0.3075(4) 0.0540(3) 0.68215(18) 0.0294(4) Uani 1 1 d
O1W O 0.3467(4) 1.1680(3) 0.87839(18) 0.0501(5) Uani 1 1 d
N3 N -0.3051(4) -0.0721(3) 0.75767(19) 0.0423(5) Uani 1 1 d
N1 N -0.5777(4) 0.4103(4) 0.6350(2) 0.0452(5) Uani 1 1 d
C1 C -0.4505(4) 0.2999(3) 0.61875(18) 0.0306(4) Uani 1 1 d
H4B H -0.184(5) 0.417(4) 0.898(3) 0.045(7) Uiso 1 1 d
H4A H 0.032(6) 0.354(5) 0.930(3) 0.070(11) Uiso 1 1 d
H3B H -0.402(6) -0.088(4) 0.805(3) 0.051(8) Uiso 1 1 d
H1B H -0.589(6) 0.508(5) 0.587(3) 0.057(9) Uiso 1 1 d
H3A H -0.213(5) -0.131(4) 0.756(2) 0.041(8) Uiso 1 1 d
H5A H -0.007(5) 0.146(4) 0.438(2) 0.033(7) Uiso 1 1 d
H1A H -0.645(5) 0.400(4) 0.688(3) 0.039(7) Uiso 1 1 d
H5B H -0.098(6) 0.289(5) 0.396(3) 0.055(9) Uiso 1 1 d
H1C H 0.233(7) 1.069(6) 0.884(3) 0.077(12) Uiso 1 1 d
H1D H 0.420(7) 1.194(6) 0.944(4) 0.071(12) 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'
P P 0.1023 0.0942 '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'
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
O3 S1 O1 111.90(12) .
O3 S1 O2 112.34(11) .
O1 S1 O2 112.68(11) .
O3 S1 C4 106.18(12) .
O1 S1 C4 107.81(12) .
O2 S1 C4 105.39(11) .
C2 N2 C1 118.79(17) .
C1 N6 C3 115.69(18) .
C3 N5 H5A 117.5(19) .
C3 N5 H5B 119(2) .
H5A N5 H5B 123(3) .
C2 N4 C3 115.12(18) .
N5 C3 N6 117.29(19) .
N5 C3 N4 116.6(2) .
N6 C3 N4 126.09(18) .
C4 C4 S1 112.1(2) 2_567
C4 C4 H4B 112.9(16) 2_567
S1 C4 H4B 102.8(16) .
C4 C4 H4A 115(2) 2_567
S1 C4 H4A 103(2) .
H4B C4 H4A 110(3) .
N4 C2 N3 121.0(2) .
N4 C2 N2 122.38(19) .
N3 C2 N2 116.64(19) .
H1C O1W H1D 102(4) .
C2 N3 H3B 118(2) .
C2 N3 H3A 118(2) .
H3B N3 H3A 124(3) .
C1 N1 H1B 122.3(19) .
C1 N1 H1A 121(2) .
H1B N1 H1A 117(3) .
N1 C1 N6 120.9(2) .
N1 C1 N2 117.2(2) .
N6 C1 N2 121.88(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4493(19) .
S1 O1 1.452(2) .
S1 O2 1.4547(17) .
S1 C4 1.772(2) .
N2 C2 1.364(3) .
N2 C1 1.366(3) .
N6 C1 1.322(3) .
N6 C3 1.356(3) .
N5 C3 1.324(3) .
N5 H5A 0.81(3) .
N5 H5B 0.79(4) .
N4 C2 1.323(3) .
N4 C3 1.360(3) .
C4 C4 1.508(4) 2_567
C4 H4B 1.01(3) .
C4 H4A 0.89(4) .
C2 N3 1.324(3) .
O1W H1C 0.84(4) .
O1W H1D 0.82(4) .
N3 H3B 0.87(3) .
N3 H3A 0.81(3) .
N1 C1 1.315(3) .
N1 H1B 0.95(4) .
N1 H1A 0.80(3) .
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_4
C1 N6 C3 N5 -178.7(2) .
C1 N6 C3 N4 1.8(3) .
C2 N4 C3 N5 -180.0(2) .
C2 N4 C3 N6 -0.5(3) .
O3 S1 C4 C4 -61.3(3) 2_567
O1 S1 C4 C4 58.8(3) 2_567
O2 S1 C4 C4 179.4(3) 2_567
C3 N4 C2 N3 179.3(2) .
C3 N4 C2 N2 -0.5(3) .
C1 N2 C2 N4 0.1(3) .
C1 N2 C2 N3 -179.7(2) .
C3 N6 C1 N1 177.8(2) .
C3 N6 C1 N2 -2.2(3) .
C2 N2 C1 N1 -178.6(2) .
C2 N2 C1 N6 1.4(3) .
