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#$Date: 2022-06-13 10:51:02 +0300 (Mon, 13 Jun 2022) $
#$Revision: 275987 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105392.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_8105392
loop_
_publ_author_name
'Chen, Xiao-Miao'
'Liu, Zheng-Jun'
'Cheng, Jing-Song'
'Zhao, Rong-Fei'
'Qin, Lan'
_publ_section_title
;
 Crystal structure of 3-((3-nitrophenyl)sulfonamido)propanoic acid ---
 4,4′-bipyridine (1/1), C19H18N4O6S
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1109
_journal_page_last               1111
_journal_paper_doi               10.1515/ncrs-2020-0190
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C9 H10 N2 O6 S, C10 H8 N2'
_chemical_formula_sum            'C19 H18 N4 O6 S'
_chemical_formula_weight         430.43
_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
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 97.398(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.343(4)
_cell_length_b                   7.367(3)
_cell_length_c                   31.532(14)
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.61
_cell_volume                     1921.9(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9298
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.302
_diffrn_source_current           30.0
_diffrn_source_power             1.44
_diffrn_source_voltage           48.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.9343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0420
_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/[σ²(Fo²)+(0.0618P)²+0.2244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2569
_reflns_number_total             3372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0190_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1921.8(14)
_cod_database_code               8105392
_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_max   0.964
_shelx_estimated_absorpt_t_min   0.934
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4A), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15),
 C16(H16), C17(H17), C19(H19)
;
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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.77366(6) 0.04750(8) 0.66439(2) 0.04207(19) Uani 1 1 d . . . . .
O1 O 1.1862(2) 0.4214(3) 0.60436(5) 0.0626(5) Uani 1 1 d . . . . .
O2 O 0.9970(2) 0.4060(3) 0.54952(6) 0.0787(6) Uani 1 1 d . . . . .
O3 O 0.63382(18) 0.1455(2) 0.67080(5) 0.0594(5) Uani 1 1 d . . . . .
O4 O 0.75810(18) -0.1214(2) 0.64291(5) 0.0525(4) Uani 1 1 d . . . . .
O5 O 1.0997(3) -0.4700(3) 0.74676(7) 0.0811(6) Uani 1 1 d . . . . .
O6 O 1.2458(2) -0.3503(3) 0.79975(6) 0.0699(5) Uani 1 1 d . . . . .
N1 N 0.8796(2) 0.0477(3) 0.39833(6) 0.0563(5) Uani 1 1 d . . . . .
N2 N 0.3723(2) 0.3264(3) 0.54736(6) 0.0507(5) Uani 1 1 d . . . . .
N3 N 1.1397(2) -0.3428(3) 0.76985(6) 0.0535(5) Uani 1 1 d . . . . .
N4 N 0.8818(2) 0.1731(3) 0.63859(5) 0.0434(5) Uani 1 1 d . . . . .
C1 C 0.9365(3) 0.1019(4) 0.43682(8) 0.0568(7) Uani 1 1 d . . . . .
H1A H 1.047867 0.098111 0.444539 0.068 Uiso 1 1 calc R U . . .
C2 C 0.8439(3) 0.1636(3) 0.46652(7) 0.0505(6) Uani 1 1 d . . . . .
H2 H 0.891998 0.200824 0.493350 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6797(2) 0.1698(3) 0.45631(6) 0.0389(5) Uani 1 1 d . . . . .
C4 C 0.6202(3) 0.1195(3) 0.41567(7) 0.0529(6) Uani 1 1 d . . . . .
H4A H 0.509697 0.125984 0.406676 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7221(3) 0.0600(4) 0.38829(8) 0.0625(7) Uani 1 1 d . . . . .
H5 H 0.677773 0.025984 0.360869 0.075 Uiso 1 1 calc R U . . .
C6 C 0.5732(2) 0.2249(3) 0.48772(7) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.6236(3) 0.2233(3) 0.53093(7) 0.0478(6) Uani 1 1 d . . . . .
H7 H 0.728597 0.187618 0.540971 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5221(3) 0.2731(3) 0.55904(8) 0.0525(6) Uani 1 1 d . . . . .
H8 H 0.560129 0.269434 0.588075 0.063 Uiso 1 1 calc R U . . .
C9 C 0.3216(3) 0.3299(3) 0.50611(8) 0.0502(6) Uani 1 1 d . . . . .
H9 H 0.216515 0.368457 0.497190 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4160(3) 0.2795(3) 0.47563(7) 0.0472(6) Uani 1 1 d . . . . .
H10 H 0.374036 0.282188 0.446849 0.057 Uiso 1 1 calc R U . . .
C11 C 1.0373(3) 0.4323(3) 0.58653(8) 0.0489(6) Uani 1 1 d . . . . .
C12 C 0.9215(3) 0.4835(3) 0.61636(8) 0.0544(6) Uani 1 1 d . . . . .
H12A H 0.813658 0.487489 0.600651 0.065 Uiso 1 1 calc R U . . .
H12B H 0.947653 0.604583 0.627177 0.065 Uiso 1 1 calc R U . . .
C13 C 0.9209(3) 0.3576(3) 0.65322(7) 0.0534(6) Uani 1 1 d . . . . .
H13A H 1.026371 0.358728 0.670247 0.064 Uiso 1 1 calc R U . . .
H13B H 0.841980 0.398511 0.671170 0.064 Uiso 1 1 calc R U . . .
C14 C 0.8822(2) 0.0093(3) 0.71510(6) 0.0387(5) Uani 1 1 d . . . . .
C15 C 0.8844(3) 0.1381(3) 0.74662(7) 0.0536(6) Uani 1 1 d . . . . .
H15 H 0.824476 0.244177 0.741619 0.064 Uiso 1 1 calc R U . . .
C16 C 0.9748(3) 0.1101(4) 0.78531(8) 0.0622(7) Uani 1 1 d . . . . .
H16 H 0.977005 0.198283 0.806472 0.075 Uiso 1 1 calc R U . . .
C17 C 1.0619(3) -0.0459(4) 0.79335(7) 0.0538(6) Uani 1 1 d . . . . .
H17 H 1.124269 -0.065302 0.819601 0.065 Uiso 1 1 calc R U . . .
C18 C 1.0544(2) -0.1722(3) 0.76157(7) 0.0414(5) Uani 1 1 d . . . . .
C19 C 0.9670(2) -0.1482(3) 0.72244(6) 0.0397(5) Uani 1 1 d . . . . .
H19 H 0.965133 -0.236698 0.701349 0.048 Uiso 1 1 calc R U . . .
H1 H 1.259(4) 0.382(4) 0.5824(11) 0.107(11) Uiso 1 1 d . . . . .
H4 H 0.957(3) 0.109(3) 0.6299(7) 0.050(7) 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'
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
O3 S1 O4 119.53(11) . .
O3 S1 N4 108.10(11) . .
O3 S1 C14 106.92(10) . .
O4 S1 N4 106.88(10) . .
O4 S1 C14 107.44(10) . .
N4 S1 C14 107.43(10) . .
C11 O1 H1 110.0(18) . .
C1 N1 C5 115.7(2) . .
C9 N2 C8 117.1(2) . .
O5 N3 O6 123.5(2) . .
O5 N3 C18 118.23(19) . .
O6 N3 C18 118.2(2) . .
S1 N4 H4 109.1(16) . .
C13 N4 S1 119.98(16) . .
C13 N4 H4 118.2(17) . .
N1 C1 H1A 117.7 . .
N1 C1 C2 124.6(2) . .
C2 C1 H1A 117.7 . .
C1 C2 H2 120.4 . .
C1 C2 C3 119.2(2) . .
C3 C2 H2 120.4 . .
C2 C3 C6 121.7(2) . .
C4 C3 C2 116.4(2) . .
C4 C3 C6 121.9(2) . .
C3 C4 H4A 119.9 . .
C5 C4 C3 120.1(2) . .
C5 C4 H4A 119.9 . .
N1 C5 C4 123.8(2) . .
N1 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
C7 C6 C3 122.12(19) . .
C7 C6 C10 115.8(2) . .
C10 C6 C3 122.1(2) . .
C6 C7 H7 119.7 . .
C8 C7 C6 120.7(2) . .
C8 C7 H7 119.7 . .
N2 C8 C7 123.3(2) . .
N2 C8 H8 118.3 . .
C7 C8 H8 118.3 . .
N2 C9 H9 118.4 . .
N2 C9 C10 123.2(2) . .
C10 C9 H9 118.4 . .
C6 C10 H10 120.1 . .
C9 C10 C6 119.9(2) . .
C9 C10 H10 120.1 . .
O1 C11 C12 114.0(2) . .
O2 C11 O1 123.4(2) . .
O2 C11 C12 122.6(2) . .
C11 C12 H12A 108.8 . .
C11 C12 H12B 108.8 . .
C11 C12 C13 113.9(2) . .
H12A C12 H12B 107.7 . .
C13 C12 H12A 108.8 . .
C13 C12 H12B 108.8 . .
N4 C13 C12 110.90(19) . .
N4 C13 H13A 109.5 . .
N4 C13 H13B 109.5 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 108.0 . .
C15 C14 S1 120.37(18) . .
C19 C14 S1 119.12(16) . .
C19 C14 C15 120.5(2) . .
C14 C15 H15 120.1 . .
C16 C15 C14 119.8(2) . .
C16 C15 H15 120.1 . .
C15 C16 H16 119.6 . .
C15 C16 C17 120.9(2) . .
C17 C16 H16 119.6 . .
C16 C17 H17 121.2 . .
C18 C17 C16 117.7(2) . .
C18 C17 H17 121.2 . .
C17 C18 N3 118.9(2) . .
C19 C18 N3 117.9(2) . .
C19 C18 C17 123.1(2) . .
C14 C19 H19 121.0 . .
C18 C19 C14 118.0(2) . .
C18 C19 H19 121.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4083(17) .
S1 O4 1.4147(17) .
S1 N4 1.588(2) .
S1 C14 1.756(2) .
O1 C11 1.298(3) .
O1 H1 1.02(3) .
O2 C11 1.188(3) .
O5 N3 1.207(3) .
O6 N3 1.208(2) .
N1 C1 1.307(3) .
N1 C5 1.315(3) .
N2 C8 1.317(3) .
N2 C9 1.315(3) .
N3 C18 1.451(3) .
N4 C13 1.458(3) .
N4 H4 0.86(2) .
C1 H1A 0.9300 .
C1 C2 1.366(3) .
C2 H2 0.9300 .
C2 C3 1.367(3) .
C3 C4 1.365(3) .
C3 C6 1.470(3) .
C4 H4A 0.9300 .
C4 C5 1.360(3) .
C5 H5 0.9300 .
C6 C7 1.373(3) .
C6 C10 1.378(3) .
C7 H7 0.9300 .
C7 C8 1.353(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C9 C10 1.370(3) .
C10 H10 0.9300 .
C11 C12 1.481(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.487(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.372(3) .
C14 C19 1.363(3) .
C15 H15 0.9300 .
C15 C16 1.365(3) .
C16 H16 0.9300 .
C16 C17 1.366(4) .
C17 H17 0.9300 .
C17 C18 1.363(3) .
C18 C19 1.361(3) .
C19 H19 0.9300 .
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
_geom_hbond_publ_flag
O1 H1 N2 1.02(3) 1.60(3) 2.617(3) 178(3) 1_655 yes
N4 H4 N1 0.86(2) 2.07(2) 2.926(3) 173(2) 3_756 yes
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
S1 N4 C13 C12 -142.82(18) . . . .
S1 C14 C15 C16 -177.2(2) . . . .
S1 C14 C19 C18 177.92(16) . . . .
O1 C11 C12 C13 -58.0(3) . . . .
O2 C11 C12 C13 122.9(3) . . . .
O3 S1 N4 C13 50.6(2) . . . .
O3 S1 C14 C15 -35.6(2) . . . .
O3 S1 C14 C19 145.81(17) . . . .
O4 S1 N4 C13 -179.51(17) . . . .
O4 S1 C14 C15 -165.02(19) . . . .
O4 S1 C14 C19 16.4(2) . . . .
O5 N3 C18 C17 160.7(2) . . . .
O5 N3 C18 C19 -17.7(3) . . . .
O6 N3 C18 C17 -18.6(3) . . . .
O6 N3 C18 C19 163.0(2) . . . .
N1 C1 C2 C3 0.4(4) . . . .
N2 C9 C10 C6 -1.2(4) . . . .
N3 C18 C19 C14 177.76(18) . . . .
N4 S1 C14 C15 80.3(2) . . . .
N4 S1 C14 C19 -98.34(18) . . . .
C1 N1 C5 C4 -1.8(4) . . . .
C1 C2 C3 C4 -2.6(4) . . . .
C1 C2 C3 C6 176.4(2) . . . .
C2 C3 C4 C5 2.6(4) . . . .
C2 C3 C6 C7 -18.8(3) . . . .
C2 C3 C6 C10 161.9(2) . . . .
C3 C4 C5 N1 -0.4(4) . . . .
C3 C6 C7 C8 -179.3(2) . . . .
C3 C6 C10 C9 -179.9(2) . . . .
C4 C3 C6 C7 160.1(2) . . . .
C4 C3 C6 C10 -19.2(3) . . . .
C5 N1 C1 C2 1.8(4) . . . .
C6 C3 C4 C5 -176.4(2) . . . .
C6 C7 C8 N2 -0.5(4) . . . .
C7 C6 C10 C9 0.8(3) . . . .
C8 N2 C9 C10 0.7(4) . . . .
C9 N2 C8 C7 0.1(4) . . . .
C10 C6 C7 C8 0.0(3) . . . .
C11 C12 C13 N4 -58.6(3) . . . .
C14 S1 N4 C13 -64.4(2) . . . .
C14 C15 C16 C17 -0.8(4) . . . .
C15 C14 C19 C18 -0.7(3) . . . .
C15 C16 C17 C18 -0.4(4) . . . .
C16 C17 C18 N3 -177.2(2) . . . .
C16 C17 C18 C19 1.1(4) . . . .
C17 C18 C19 C14 -0.6(3) . . . .
C19 C14 C15 C16 1.4(4) . . . .
