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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/4/13/19/4131971.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_4131971
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         'C14 H18 N2 O2, 2(C6 H4 N O5 S)'
_chemical_formula_sum            'C26 H26 N4 O12 S2'
_chemical_formula_weight         650.63
_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-2016/6
_cell_angle_alpha                98.012(7)
_cell_angle_beta                 94.549(8)
_cell_angle_gamma                97.848(7)
_cell_formula_units_Z            1
_cell_length_a                   6.0303(6)
_cell_length_b                   9.7210(8)
_cell_length_c                   12.4638(12)
_cell_measurement_reflns_used    2507
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.35
_cell_volume                     713.12(12)
_computing_structure_refinement  'SHELXL-2016/6 (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  0.0501
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4711
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crysalispro
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0528
_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)+(0.0645P)²+0.3184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2118
_reflns_number_total             2507
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b13558_si_002.cif
_cod_data_source_block           NBSA-BD-(OMe)2
_cod_database_code               4131971
_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   0.938
_shelx_estimated_absorpt_t_max   0.950
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 0.1861(4) 0.5461(3) 0.8276(2) 0.0379(6) Uani 1 1 d . .
C2 C 0.3795(5) 0.4853(3) 0.8317(2) 0.0477(7) Uani 1 1 d . .
H2 H 0.474548 0.497485 0.895886 0.057 Uiso 1 1 calc R U
C3 C 0.4287(5) 0.4062(3) 0.7389(2) 0.0448(7) Uani 1 1 d . .
H3 H 0.558972 0.364895 0.739514 0.054 Uiso 1 1 calc R U
C4 C 0.2843(4) 0.3882(2) 0.6443(2) 0.0347(6) Uani 1 1 d . .
C5 C 0.0924(4) 0.4509(3) 0.6418(2) 0.0390(6) Uani 1 1 d . .
H5 H -0.003258 0.438933 0.577865 0.047 Uiso 1 1 calc R U
C6 C 0.0428(5) 0.5315(3) 0.7349(2) 0.0401(6) Uani 1 1 d . .
H6 H -0.085393 0.574926 0.734244 0.048 Uiso 1 1 calc R U
C7 C 0.8115(4) 0.0004(3) 0.2087(2) 0.0386(6) Uani 1 1 d . .
C8 C 0.7288(4) -0.0366(3) 0.1012(2) 0.0400(6) Uani 1 1 d . .
H8 H 0.795088 -0.100282 0.056113 0.048 Uiso 1 1 calc R U
C9 C 0.5456(4) 0.0204(2) 0.05837(19) 0.0350(6) Uani 1 1 d . .
C10 C 0.4515(5) 0.1153(3) 0.1282(2) 0.0438(7) Uani 1 1 d . .
H10 H 0.332332 0.156135 0.101173 0.053 Uiso 1 1 calc R U
C11 C 0.5314(5) 0.1503(3) 0.2372(2) 0.0415(6) Uani 1 1 d . .
H11 H 0.464698 0.212705 0.283216 0.050 Uiso 1 1 calc R U
C12 C 0.7097(4) 0.0921(2) 0.27681(19) 0.0344(6) Uani 1 1 d . .
C13 C 1.0862(5) -0.1546(3) 0.2010(3) 0.0547(8) Uani 1 1 d . .
H13A H 1.210602 -0.175572 0.245699 0.082 Uiso 1 1 calc R U
H13B H 0.974581 -0.236744 0.182681 0.082 Uiso 1 1 calc R U
H13C H 1.138062 -0.125836 0.135545 0.082 Uiso 1 1 calc R U
N1 N 0.1302(4) 0.6284(2) 0.92752(19) 0.0498(6) Uani 1 1 d . .
N2 N 0.7962(4) 0.1229(3) 0.39144(18) 0.0401(5) Uani 1 1 d D .
O1 O -0.0324(4) 0.6886(3) 0.92156(19) 0.0793(8) Uani 1 1 d . .
O2 O 0.2480(5) 0.6317(3) 1.01146(17) 0.0816(8) Uani 1 1 d . .
O3 O 0.5782(4) 0.3032(3) 0.5228(2) 0.0914(10) Uani 1 1 d . .
O4 O 0.2568(6) 0.1382(2) 0.5428(2) 0.0940(10) Uani 1 1 d . .
O5 O 0.2141(4) 0.3134(2) 0.43527(16) 0.0594(6) Uani 1 1 d . .
O6 O 0.9912(4) -0.0449(2) 0.25862(15) 0.0590(6) Uani 1 1 d . .
S1 S 0.34148(11) 0.27756(6) 0.52678(5) 0.0398(2) Uani 1 1 d . .
H2A H 0.708(5) 0.174(3) 0.431(2) 0.037(7) Uiso 1 1 d . .
H2B H 0.946(4) 0.163(3) 0.404(3) 0.076(11) Uiso 1 1 d D .
H2C H 0.795(7) 0.045(4) 0.425(3) 0.098(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'
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
C6 C1 C2 122.6(2) .
C6 C1 N1 118.7(2) .
C2 C1 N1 118.7(2) .
C3 C2 C1 118.5(2) .
C3 C2 H2 120.7 .
C1 C2 H2 120.7 .
C2 C3 C4 120.0(2) .
C2 C3 H3 120.0 .
C4 C3 H3 120.0 .
C5 C4 C3 120.6(2) .
C5 C4 S1 119.85(19) .
C3 C4 S1 119.54(19) .
C4 C5 C6 119.8(2) .
C4 C5 H5 120.1 .
C6 C5 H5 120.1 .
C1 C6 C5 118.6(2) .
C1 C6 H6 120.7 .
C5 C6 H6 120.7 .
O6 C7 C8 126.2(2) .
O6 C7 C12 114.0(2) .
C8 C7 C12 119.8(2) .
C7 C8 C9 120.9(2) .
C7 C8 H8 119.6 .
C9 C8 H8 119.6 .
C10 C9 C8 117.8(2) .
C10 C9 C9 121.2(3) 2_655
C8 C9 C9 121.0(3) 2_655
C11 C10 C9 121.4(2) .
C11 C10 H10 119.3 .
C9 C10 H10 119.3 .
C12 C11 C10 119.4(2) .
C12 C11 H11 120.3 .
C10 C11 H11 120.3 .
C11 C12 C7 120.7(2) .
C11 C12 N2 121.5(2) .
C7 C12 N2 117.9(2) .
O6 C13 H13A 109.5 .
O6 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
O6 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
O2 N1 O1 123.4(2) .
O2 N1 C1 118.4(2) .
O1 N1 C1 118.2(2) .
C12 N2 H2A 111.3(16) .
C12 N2 H2B 114(2) .
H2A N2 H2B 111(3) .
C12 N2 H2C 114(3) .
H2A N2 H2C 103(3) .
H2B N2 H2C 102(3) .
C7 O6 C13 118.5(2) .
O3 S1 O4 114.33(19) .
O3 S1 O5 113.94(17) .
O4 S1 O5 109.50(16) .
O3 S1 C4 106.20(12) .
O4 S1 C4 105.20(14) .
O5 S1 C4 106.96(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.366(3) .
C1 C2 1.378(4) .
C1 N1 1.472(3) .
C2 C3 1.373(4) .
C2 H2 0.9300 .
C3 C4 1.384(3) .
C3 H3 0.9300 .
C4 C5 1.380(4) .
C4 S1 1.779(3) .
C5 C6 1.383(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 O6 1.362(3) .
C7 C8 1.374(4) .
C7 C12 1.383(3) .
C8 C9 1.403(3) .
C8 H8 0.9300 .
C9 C10 1.388(4) .
C9 C9 1.493(5) 2_655
C10 C11 1.385(3) .
C10 H10 0.9300 .
C11 C12 1.370(3) .
C11 H11 0.9300 .
C12 N2 1.457(3) .
C13 O6 1.414(3) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
N1 O2 1.211(3) .
N1 O1 1.211(3) .
N2 H2A 0.90(3) .
N2 H2B 0.925(19) .
N2 H2C 0.92(4) .
O3 S1 1.421(2) .
O4 S1 1.427(2) .
O5 S1 1.4343(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) . .
N1 C1 C2 C3 178.7(3) . .
C1 C2 C3 C4 -0.6(4) . .
C2 C3 C4 C5 1.1(4) . .
C2 C3 C4 S1 -176.5(2) . .
C3 C4 C5 C6 -0.6(4) . .
S1 C4 C5 C6 176.98(19) . .
C2 C1 C6 C5 1.0(4) . .
N1 C1 C6 C5 -178.2(2) . .
C4 C5 C6 C1 -0.4(4) . .
O6 C7 C8 C9 -178.2(3) . .
C12 C7 C8 C9 1.8(4) . .
C7 C8 C9 C10 0.1(4) . .
C7 C8 C9 C9 -179.6(3) . 2_655
C8 C9 C10 C11 -1.6(4) . .
C9 C9 C10 C11 178.1(3) 2_655 .
C9 C10 C11 C12 1.2(4) . .
C10 C11 C12 C7 0.7(4) . .
C10 C11 C12 N2 -178.4(2) . .
O6 C7 C12 C11 177.8(2) . .
C8 C7 C12 C11 -2.2(4) . .
O6 C7 C12 N2 -3.1(3) . .
C8 C7 C12 N2 177.0(2) . .
C6 C1 N1 O2 174.2(3) . .
C2 C1 N1 O2 -5.0(4) . .
C6 C1 N1 O1 -5.3(4) . .
C2 C1 N1 O1 175.5(3) . .
C8 C7 O6 C13 -9.4(4) . .
C12 C7 O6 C13 170.7(2) . .
C5 C4 S1 O3 142.8(2) . .
C3 C4 S1 O3 -39.6(3) . .
C5 C4 S1 O4 -95.6(3) . .
C3 C4 S1 O4 82.0(3) . .
C5 C4 S1 O5 20.8(3) . .
C3 C4 S1 O5 -161.6(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168335270
