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#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/19/4131987.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_4131987
loop_
_publ_author_name
'Karak, Suvendu'
'Kumar, Sushil'
'Pachfule, Pradip'
'Banerjee, Rahul'
_publ_section_title
;
 Porosity Prediction through Hydrogen Bonding in Covalent Organic
 Frameworks.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5138
_journal_page_last               5145
_journal_paper_doi               10.1021/jacs.7b13558
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety
'C6 H7 Cl2 N2, 0.5(C6 H8 Cl2 N2), 2(C6 H5 O3 S)'
_chemical_formula_sum            'C21 H21 Cl3 N3 O6 S2'
_chemical_formula_weight         581.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                95.045(5)
_cell_angle_beta                 109.245(5)
_cell_angle_gamma                102.571(5)
_cell_formula_units_Z            2
_cell_length_a                   10.1766(6)
_cell_length_b                   10.7552(7)
_cell_length_c                   12.5205(8)
_cell_measurement_reflns_used    4373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.20
_cell_volume                     1243.69(15)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Supernova (Mo) X-ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.176
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crysalispro
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0394
_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)+(0.0420P)²+0.4161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3640
_reflns_number_total             4373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b13558_si_004.cif
_cod_data_source_block           BSA-Pa-Cl2
_cod_original_cell_volume        1243.69(14)
_cod_database_code               4131987
_shelx_shelxl_version_number     2016/4
_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   0.893
_shelx_estimated_absorpt_t_max   0.908
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
C1 C 0.0436(3) 0.1677(2) 0.8145(2) 0.0366(6) Uani 1 1 d . .
C2 C -0.0250(4) 0.1045(3) 0.8797(3) 0.0699(9) Uani 1 1 d . .
H2 H -0.062315 0.015123 0.862193 0.084 Uiso 1 1 calc R U
C3 C -0.0380(5) 0.1746(5) 0.9710(3) 0.0973(14) Uani 1 1 d . .
H3 H -0.084170 0.132305 1.015630 0.117 Uiso 1 1 calc R U
C4 C 0.0164(5) 0.3063(4) 0.9969(3) 0.0874(13) Uani 1 1 d . .
H4 H 0.009934 0.352896 1.060357 0.105 Uiso 1 1 calc R U
C5 C 0.0789(4) 0.3675(3) 0.9304(3) 0.0803(11) Uani 1 1 d . .
H5 H 0.113281 0.457092 0.946839 0.096 Uiso 1 1 calc R U
C6 C 0.0933(4) 0.2991(3) 0.8374(3) 0.0612(8) Uani 1 1 d . .
H6 H 0.136172 0.342346 0.791330 0.073 Uiso 1 1 calc R U
C7 C 0.7068(3) 0.3364(3) 0.1894(2) 0.0415(6) Uani 1 1 d . .
C8 C 0.5906(3) 0.3877(4) 0.1528(3) 0.0683(9) Uani 1 1 d . .
H8 H 0.587629 0.461853 0.195105 0.082 Uiso 1 1 calc R U
C9 C 0.4787(4) 0.3271(6) 0.0524(4) 0.1116(18) Uani 1 1 d . .
H9 H 0.398991 0.360467 0.026928 0.134 Uiso 1 1 calc R U
C10 C 0.4830(6) 0.2196(7) -0.0099(4) 0.129(3) Uani 1 1 d . .
H10 H 0.407069 0.180535 -0.078232 0.155 Uiso 1 1 calc R U
C11 C 0.5981(6) 0.1684(5) 0.0269(4) 0.1130(19) Uani 1 1 d . .
H11 H 0.599985 0.094234 -0.016135 0.136 Uiso 1 1 calc R U
C12 C 0.7120(4) 0.2259(3) 0.1278(3) 0.0694(9) Uani 1 1 d . .
H12 H 0.790447 0.190957 0.153644 0.083 Uiso 1 1 calc R U
C13 C 0.6032(2) 0.3431(2) 0.5601(2) 0.0373(6) Uani 1 1 d . .
C14 C 0.5301(3) 0.3254(2) 0.6360(2) 0.0384(6) Uani 1 1 d . .
C15 C 0.3832(2) 0.3095(2) 0.6017(2) 0.0364(6) Uani 1 1 d . .
H15 H 0.337340 0.298396 0.654564 0.044 Uiso 1 1 calc R U
C16 C 0.3050(2) 0.3100(2) 0.4891(2) 0.0319(5) Uani 1 1 d . .
C17 C 0.3751(2) 0.3260(2) 0.4117(2) 0.0333(5) Uani 1 1 d . .
C18 C 0.5215(3) 0.3431(2) 0.4463(2) 0.0384(6) Uani 1 1 d . .
H18 H 0.566757 0.354807 0.393044 0.046 Uiso 1 1 calc R U
C19 C 0.6189(2) 0.0348(2) 0.46930(19) 0.0281(5) Uani 1 1 d . .
C20 C 0.4826(2) 0.0224(2) 0.38998(19) 0.0305(5) Uani 1 1 d . .
C21 C 0.3631(2) -0.0129(2) 0.4208(2) 0.0308(5) Uani 1 1 d . .
N1 N 0.1500(2) 0.2952(2) 0.4526(2) 0.0370(5) Uani 1 1 d D .
N2 N 0.7486(3) 0.3556(3) 0.5941(3) 0.0566(7) Uani 1 1 d . .
N3 N 0.7440(2) 0.0730(2) 0.4362(2) 0.0342(5) Uani 1 1 d . .
O1 O -0.0307(2) -0.04823(18) 0.67627(19) 0.0650(6) Uani 1 1 d . .
O2 O 0.0167(2) 0.14687(19) 0.60080(15) 0.0536(5) Uani 1 1 d . .
O3 O 0.21351(18) 0.0836(2) 0.72930(16) 0.0571(5) Uani 1 1 d . .
O4 O 0.98096(18) 0.42707(18) 0.29518(16) 0.0504(5) Uani 1 1 d . .
O5 O 0.84484(19) 0.31211(17) 0.39621(15) 0.0503(5) Uani 1 1 d . .
O6 O 0.8219(2) 0.52341(18) 0.36110(17) 0.0618(6) Uani 1 1 d . .
S1 S 0.06309(6) 0.08004(6) 0.69723(5) 0.03582(17) Uani 1 1 d . .
S2 S 0.84966(6) 0.40649(6) 0.31972(5) 0.03400(16) Uani 1 1 d . .
CL1 Cl 0.27675(8) 0.32415(7) 0.26898(6) 0.0537(2) Uani 1 1 d . .
CL2 Cl 0.62672(8) 0.32327(8) 0.77836(6) 0.0646(2) Uani 1 1 d . .
CL3 Cl 0.46240(7) 0.05199(7) 0.25346(5) 0.04804(19) Uani 1 1 d . .
H1A H 0.116(3) 0.342(3) 0.402(2) 0.076(11) Uiso 1 1 d D .
H1B H 0.133(4) 0.319(3) 0.512(3) 0.073(11) Uiso 1 1 d . .
H1C H 0.102(3) 0.216(3) 0.422(2) 0.052(9) Uiso 1 1 d . .
H2A H 0.789(4) 0.376(3) 0.544(3) 0.068(11) Uiso 1 1 d . .
H2B H 0.792(4) 0.378(3) 0.664(3) 0.064(11) Uiso 1 1 d . .
H3A H 0.747(3) 0.153(3) 0.417(3) 0.072(10) Uiso 1 1 d . .
H3B H 0.737(3) 0.017(3) 0.379(2) 0.044(8) Uiso 1 1 d . .
H3C H 0.827(3) 0.087(2) 0.499(2) 0.045(8) Uiso 1 1 d . .
H21 H 0.272(3) -0.023(2) 0.3684(19) 0.031(6) 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'
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_1
C6 C1 C2 120.3(3) .
C6 C1 S1 119.4(2) .
C2 C1 S1 120.3(2) .
C1 C2 C3 119.3(3) .
C1 C2 H2 120.4 .
C3 C2 H2 120.4 .
C4 C3 C2 120.6(4) .
C4 C3 H3 119.7 .
C2 C3 H3 119.7 .
C5 C4 C3 119.6(3) .
C5 C4 H4 120.2 .
C3 C4 H4 120.2 .
C4 C5 C6 121.0(3) .
C4 C5 H5 119.5 .
C6 C5 H5 119.5 .
C1 C6 C5 119.1(3) .
C1 C6 H6 120.4 .
C5 C6 H6 120.4 .
C8 C7 C12 121.2(3) .
C8 C7 S2 120.5(2) .
C12 C7 S2 118.3(2) .
C7 C8 C9 118.7(4) .
C7 C8 H8 120.7 .
C9 C8 H8 120.7 .
C10 C9 C8 120.9(5) .
C10 C9 H9 119.5 .
C8 C9 H9 119.5 .
C9 C10 C11 120.3(4) .
C9 C10 H10 119.8 .
C11 C10 H10 119.8 .
C10 C11 C12 120.4(5) .
C10 C11 H11 119.8 .
C12 C11 H11 119.8 .
C7 C12 C11 118.5(4) .
C7 C12 H12 120.7 .
C11 C12 H12 120.7 .
N2 C13 C14 121.8(3) .
N2 C13 C18 121.1(3) .
C14 C13 C18 117.1(2) .
C15 C14 C13 122.0(2) .
C15 C14 CL2 119.0(2) .
C13 C14 CL2 118.92(19) .
C16 C15 C14 119.8(2) .
C16 C15 H15 120.1 .
C14 C15 H15 120.1 .
C15 C16 C17 119.3(2) .
C15 C16 N1 120.0(2) .
C17 C16 N1 120.7(2) .
C18 C17 C16 120.9(2) .
C18 C17 CL1 119.56(19) .
C16 C17 CL1 119.59(18) .
C17 C18 C13 120.9(2) .
C17 C18 H18 119.5 .
C13 C18 H18 119.5 .
C21 C19 C20 120.6(2) 2_656
C21 C19 N3 119.9(2) 2_656
C20 C19 N3 119.5(2) .
C21 C20 C19 119.9(2) .
C21 C20 CL3 120.10(17) .
C19 C20 CL3 119.97(18) .
C19 C21 C20 119.4(2) 2_656
C19 C21 H21 120.0(15) 2_656
C20 C21 H21 120.5(15) .
C16 N1 H1A 115(2) .
C16 N1 H1B 106(2) .
H1A N1 H1B 106(3) .
C16 N1 H1C 111.3(19) .
H1A N1 H1C 106(3) .
H1B N1 H1C 111(3) .
C13 N2 H2A 117(2) .
C13 N2 H2B 114(2) .
H2A N2 H2B 122(3) .
C19 N3 H3A 107(2) .
C19 N3 H3B 109.8(18) .
H3A N3 H3B 111(3) .
C19 N3 H3C 110.0(17) .
H3A N3 H3C 104(2) .
H3B N3 H3C 115(2) .
O3 S1 O1 113.95(13) .
O3 S1 O2 111.41(12) .
O1 S1 O2 111.41(12) .
O3 S1 C1 107.03(11) .
O1 S1 C1 106.33(12) .
O2 S1 C1 106.19(12) .
O6 S2 O4 113.97(13) .
O6 S2 O5 111.76(13) .
O4 S2 O5 111.14(11) .
O6 S2 C7 106.59(13) .
O4 S2 C7 106.86(12) .
O5 S2 C7 105.96(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.363(4) .
C1 C2 1.372(4) .
C1 S1 1.764(2) .
C2 C3 1.373(5) .
C2 H2 0.9300 .
C3 C4 1.370(6) .
C3 H3 0.9300 .
C4 C5 1.340(6) .
C4 H4 0.9300 .
C5 C6 1.388(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.372(4) .
C7 C12 1.379(4) .
C7 S2 1.757(2) .
C8 C9 1.375(5) .
C8 H8 0.9300 .
C9 C10 1.354(8) .
C9 H9 0.9300 .
C10 C11 1.363(8) .
C10 H10 0.9300 .
C11 C12 1.381(5) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 N2 1.370(3) .
C13 C14 1.389(4) .
C13 C18 1.393(3) .
C14 C15 1.378(3) .
C14 CL2 1.733(2) .
C15 C16 1.372(3) .
C15 H15 0.9300 .
C16 C17 1.382(3) .
C16 N1 1.458(3) .
C17 C18 1.372(3) .
C17 CL1 1.732(2) .
C18 H18 0.9300 .
C19 C21 1.375(3) 2_656
C19 C20 1.385(3) .
C19 N3 1.453(3) .
C20 C21 1.380(3) .
C20 CL3 1.720(2) .
C21 C19 1.375(3) 2_656
C21 H21 0.92(2) .
N1 H1A 0.876(18) .
N1 H1B 0.85(4) .
N1 H1C 0.86(3) .
N2 H2A 0.88(3) .
N2 H2B 0.82(3) .
N3 H3A 0.91(3) .
N3 H3B 0.87(3) .
N3 H3C 0.92(3) .
O1 S1 1.4427(19) .
O2 S1 1.4567(19) .
O3 S1 1.4397(18) .
O4 S2 1.4431(18) .
O5 S2 1.4596(18) .
O6 S2 1.437(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -2.5(5) . .
S1 C1 C2 C3 179.5(3) . .
C1 C2 C3 C4 0.2(6) . .
C2 C3 C4 C5 2.0(7) . .
C3 C4 C5 C6 -1.9(6) . .
C2 C1 C6 C5 2.7(5) . .
S1 C1 C6 C5 -179.4(3) . .
C4 C5 C6 C1 -0.5(6) . .
C12 C7 C8 C9 -0.5(5) . .
S2 C7 C8 C9 -177.7(3) . .
C7 C8 C9 C10 -0.5(6) . .
C8 C9 C10 C11 0.9(7) . .
C9 C10 C11 C12 -0.4(7) . .
C8 C7 C12 C11 1.0(5) . .
S2 C7 C12 C11 178.2(3) . .
C10 C11 C12 C7 -0.5(6) . .
N2 C13 C14 C15 -178.3(2) . .
C18 C13 C14 C15 -0.5(4) . .
N2 C13 C14 CL2 1.6(3) . .
C18 C13 C14 CL2 179.46(17) . .
C13 C14 C15 C16 0.4(4) . .
CL2 C14 C15 C16 -179.53(18) . .
C14 C15 C16 C17 0.3(3) . .
C14 C15 C16 N1 -179.1(2) . .
C15 C16 C17 C18 -0.9(3) . .
N1 C16 C17 C18 178.4(2) . .
C15 C16 C17 CL1 178.97(17) . .
N1 C16 C17 CL1 -1.7(3) . .
C16 C17 C18 C13 0.9(4) . .
CL1 C17 C18 C13 -179.04(18) . .
N2 C13 C18 C17 177.7(2) . .
C14 C13 C18 C17 -0.1(3) . .
C21 C19 C20 C21 -0.4(4) 2_656 .
N3 C19 C20 C21 -179.5(2) . .
C21 C19 C20 CL3 179.24(17) 2_656 .
N3 C19 C20 CL3 0.1(3) . .
C19 C20 C21 C19 0.4(4) . 2_656
CL3 C20 C21 C19 -179.24(17) . 2_656
C6 C1 S1 O3 72.7(3) . .
C2 C1 S1 O3 -109.4(3) . .
C6 C1 S1 O1 -165.2(2) . .
C2 C1 S1 O1 12.8(3) . .
C6 C1 S1 O2 -46.4(3) . .
C2 C1 S1 O2 131.5(2) . .
C8 C7 S2 O6 -6.6(3) . .
C12 C7 S2 O6 176.1(2) . .
C8 C7 S2 O4 -128.8(2) . .
C12 C7 S2 O4 53.9(2) . .
C8 C7 S2 O5 112.6(2) . .
C12 C7 S2 O5 -64.7(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168335285
