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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/4/13/19/4131974.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_4131974
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         'C12 H14 N2 O2, 2(C6 H4 N O5 S)'
_chemical_formula_sum            'C24 H22 N4 O12 S2'
_chemical_formula_weight         622.57
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.742(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9855(9)
_cell_length_b                   7.3929(5)
_cell_length_c                   13.8095(8)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.01
_cell_volume                     1302.49(15)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4741
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.003
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crysalispro
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0437
_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)+(0.0521P)²+0.9522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2003
_reflns_number_total             2292
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b13558_si_002.cif
_cod_data_source_block           NBSA-BD-(OH)2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4131974
_shelx_shelxl_version_number     2016/6
_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   0.936
_shelx_estimated_absorpt_t_max   0.946
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
C1 C 0.31916(18) 0.3673(3) 0.51710(17) 0.0308(5) Uani 1 1 d . .
C2 C 0.2227(2) 0.3947(4) 0.54267(19) 0.0444(7) Uani 1 1 d . .
H2 H 0.213128 0.371482 0.606607 0.053 Uiso 1 1 calc R U
C3 C 0.1406(2) 0.4566(4) 0.4728(2) 0.0488(7) Uani 1 1 d . .
H3 H 0.074977 0.474855 0.489012 0.059 Uiso 1 1 calc R U
C4 C 0.1562(2) 0.4909(4) 0.3792(2) 0.0402(6) Uani 1 1 d . .
C5 C 0.2508(2) 0.4633(5) 0.3526(2) 0.0533(8) Uani 1 1 d . .
H5 H 0.259710 0.486397 0.288456 0.064 Uiso 1 1 calc R U
C6 C 0.3329(2) 0.4007(4) 0.42195(19) 0.0455(7) Uani 1 1 d . .
H6 H 0.397838 0.380670 0.404768 0.055 Uiso 1 1 calc R U
C7 C 0.73528(16) 0.1373(3) 0.44302(16) 0.0266(5) Uani 1 1 d . .
C8 C 0.77438(18) 0.0689(3) 0.53516(17) 0.0316(5) Uani 1 1 d . .
H8 H 0.731302 0.056809 0.581556 0.038 Uiso 1 1 calc R U
C9 C 0.87917(18) 0.0181(4) 0.55798(17) 0.0326(5) Uani 1 1 d . .
H9 H 0.906244 -0.025904 0.620650 0.039 Uiso 1 1 calc R U
C10 C 0.94423(16) 0.0316(3) 0.48916(16) 0.0267(5) Uani 1 1 d . .
C11 C 0.90274(18) 0.1069(4) 0.39778(17) 0.0372(6) Uani 1 1 d . .
H11 H 0.945401 0.120833 0.351159 0.045 Uiso 1 1 calc R U
C12 C 0.79867(18) 0.1616(4) 0.37510(16) 0.0335(6) Uani 1 1 d . .
N1 N 0.0692(2) 0.5669(4) 0.3070(2) 0.0548(7) Uani 1 1 d . .
N2 N 0.62386(15) 0.1804(3) 0.41184(17) 0.0282(5) Uani 1 1 d . .
O1 O 0.08508(19) 0.6018(4) 0.22461(19) 0.0818(8) Uani 1 1 d . .
O2 O -0.01477(18) 0.5917(4) 0.33207(18) 0.0749(8) Uani 1 1 d . .
O3 O 0.39029(14) 0.1742(2) 0.67225(12) 0.0378(4) Uani 1 1 d . .
O4 O 0.50534(15) 0.2296(3) 0.55905(13) 0.0517(6) Uani 1 1 d . .
O5 O 0.46041(13) 0.4724(2) 0.66195(13) 0.0398(4) Uani 1 1 d . .
O6 O 0.75472(15) 0.2420(4) 0.28916(13) 0.0554(6) Uani 1 1 d D .
S1 S 0.42822(4) 0.30653(8) 0.60942(4) 0.0298(2) Uani 1 1 d . .
H2A H 0.613(2) 0.284(4) 0.381(2) 0.044(8) Uiso 1 1 d . .
H2B H 0.593(2) 0.095(4) 0.373(2) 0.040(8) Uiso 1 1 d . .
H2C H 0.589(2) 0.187(4) 0.459(2) 0.034(7) Uiso 1 1 d . .
H6A H 0.802(2) 0.266(5) 0.248(2) 0.070(10) Uiso 1 1 d 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_3
C2 C1 C6 120.1(2) .
C2 C1 S1 119.61(18) .
C6 C1 S1 120.07(19) .
C3 C2 C1 119.4(2) .
C4 C3 C2 119.5(2) .
C5 C4 C3 121.8(2) .
C5 C4 N1 119.4(3) .
C3 C4 N1 118.7(3) .
C4 C5 C6 118.9(3) .
C5 C6 C1 120.2(2) .
C12 C7 C8 121.1(2) .
C12 C7 N2 117.2(2) .
C8 C7 N2 121.7(2) .
C7 C8 C9 119.1(2) .
C10 C9 C8 121.4(2) .
C9 C10 C11 117.8(2) .
C9 C10 C10 122.0(3) 3_756
C11 C10 C10 120.1(2) 3_756
C12 C11 C10 121.1(2) .
O6 C12 C7 116.6(2) .
O6 C12 C11 124.0(2) .
C7 C12 C11 119.4(2) .
O2 N1 O1 123.3(3) .
O2 N1 C4 118.7(3) .
O1 N1 C4 118.0(3) .
O4 S1 O5 114.56(12) .
O4 S1 O3 111.49(12) .
O5 S1 O3 111.71(10) .
O4 S1 C1 106.65(11) .
O5 S1 C1 105.22(11) .
O3 S1 C1 106.56(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.379(3) .
C1 C6 1.381(3) .
C1 S1 1.778(2) .
C2 C3 1.376(4) .
C3 C4 1.368(4) .
C4 C5 1.363(4) .
C4 N1 1.472(3) .
C5 C6 1.374(4) .
C7 C12 1.370(3) .
C7 C8 1.375(3) .
C7 N2 1.466(3) .
C8 C9 1.390(3) .
C9 C10 1.388(3) .
C10 C11 1.393(3) .
C10 C10 1.498(4) 3_756
C11 C12 1.389(3) .
C12 O6 1.355(3) .
N1 O2 1.217(3) .
N1 O1 1.221(4) .
O3 S1 1.4534(18) .
O4 S1 1.4387(18) .
O5 S1 1.4464(19) .
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 -0.4(4) . .
S1 C1 C2 C3 174.5(2) . .
C1 C2 C3 C4 -0.4(5) . .
C2 C3 C4 C5 0.9(5) . .
C2 C3 C4 N1 -176.5(3) . .
C3 C4 C5 C6 -0.6(5) . .
N1 C4 C5 C6 176.9(3) . .
C4 C5 C6 C1 -0.3(5) . .
C2 C1 C6 C5 0.8(5) . .
S1 C1 C6 C5 -174.2(2) . .
C12 C7 C8 C9 -2.3(4) . .
N2 C7 C8 C9 175.3(2) . .
C7 C8 C9 C10 -1.3(4) . .
C8 C9 C10 C11 3.4(4) . .
C8 C9 C10 C10 -176.8(3) . 3_756
C9 C10 C11 C12 -2.0(4) . .
C10 C10 C11 C12 178.1(3) 3_756 .
C8 C7 C12 O6 -175.3(2) . .
N2 C7 C12 O6 7.1(4) . .
C8 C7 C12 C11 3.6(4) . .
N2 C7 C12 C11 -174.0(2) . .
C10 C11 C12 O6 177.4(3) . .
C10 C11 C12 C7 -1.5(4) . .
C5 C4 N1 O2 -179.6(3) . .
C3 C4 N1 O2 -2.1(4) . .
C5 C4 N1 O1 0.4(4) . .
C3 C4 N1 O1 177.9(3) . .
C2 C1 S1 O4 161.1(2) . .
C6 C1 S1 O4 -24.0(3) . .
C2 C1 S1 O5 -76.8(2) . .
C6 C1 S1 O5 98.1(2) . .
C2 C1 S1 O3 41.9(2) . .
C6 C1 S1 O3 -143.1(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168335273
