#------------------------------------------------------------------------------
#$Date: 2022-03-18 12:32:04 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273808 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/13/1551362.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_1551362
loop_
_publ_author_name
'Xiaoyan Wang'
'Linjiang Chen'
'Samantha Y. Chong'
'Marc A. Little'
'Yongzhen Wu'
'Wei-Hong Zhu'
'Rob Clowes'
'Yong Yan'
'Martijn A. Zwijnenburg'
'Reiner Sebastian Sprick'
'Andrew I. Cooper'
_publ_section_title
;
 Sulfone-containing covalent organic frameworks for photocatalytic
 hydrogen evolution from water
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              1180
_journal_page_last               1189
_journal_paper_doi               10.1038/s41557-018-0141-5
_journal_volume                  10
_journal_year                    2018
_chemical_formula_moiety         'C12 H10 N2 O2 S'
_chemical_formula_sum            'C12 H10 N2 O2 S'
_chemical_formula_weight         246.78
_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
_cell_angle_alpha                97.595(4)
_cell_angle_beta                 100.424(4)
_cell_angle_gamma                90.636(4)
_cell_formula_units_Z            4
_cell_length_a                   7.4654(4)
_cell_length_b                   8.3783(4)
_cell_length_c                   17.0551(8)
_cell_measurement_reflns_used    6073
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.314
_cell_measurement_theta_min      1.198
_cell_volume                     1039.27(9)
_computing_cell_refinement
'DIALS 2theta refinement, DIALS 1.8.1-g1afca60c-release-hotfix1'
_computing_data_collection       'Diamond Light Source, I19, GUI'
_computing_data_reduction
'XIA2 0.5.474-gb1e580cd-dials-1.8 (Winter, G., 2010)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            PILATUS_2M_S_N_24_0107_Diamond
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       "'Fixed χ 3-circle diffractometer"
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_av_unetI/netI     0.1064
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13950
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         25.849
_diffrn_reflns_theta_min         2.376
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.991434307221
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CCP4 7.0.046: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       plate
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0789
_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)+(0.0920P)²+1.7113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2109
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3782
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            41557_2018_141_MOESM16_ESM.cif
_cod_data_source_block           Sulfone_Diamine_100K
_cod_depositor_comments
;

2022-03-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H21 N4 O4 S2'
_cod_original_formula_weight         493.57
_cod_original_formula_moiety         '2(C12 H10 N2 O2 S)'
_cod_original_formula_units_Z            2
_cod_database_code               1551362
_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   0.999
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C11-N2 \\sim N2-C9
 with sigma of 0.01
 C1-N1 \\sim N1-C3
 with sigma of 0.01
 C13-N3 \\sim N3-C15
 with sigma of 0.01
 C24-N4 \\sim N4-C22
 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C1(H1), C11(H11), C9(H9), C8(H8), C13(H13), C15(H15),
 C16(H16), C21(H21), C22(H22), C24(H24)
3.b Fitted hexagon refined as free rotating group:
 C6(C5,C4,C3,C2,C1), C12(C11,C10,C9,C8,C7), C18(C13,C14,C15,C16,C17), C19(C20,
 C21,C22,C23,C24)
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63594(10) 0.28703(9) 0.40757(5) 0.0283(3) Uani 1 1 d . . . . .
S2 S 0.77777(11) 0.29305(9) 0.90684(5) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.4452(3) 0.2399(3) 0.38284(14) 0.0334(5) Uani 1 1 d . . . . .
O2 O 0.7594(3) 0.1946(3) 0.36372(14) 0.0324(5) Uani 1 1 d . . . . .
O3 O 0.9412(3) 0.2474(3) 0.87605(14) 0.0340(5) Uani 1 1 d . . . . .
O4 O 0.6126(3) 0.2023(3) 0.86573(14) 0.0337(5) Uani 1 1 d . . . . .
N1 N 0.8046(4) 0.0676(4) 0.68331(19) 0.0358(7) Uani 1 1 d D . . . .
N2 N 0.6751(5) 0.8268(4) 0.2891(2) 0.0373(7) Uani 1 1 d D . . . .
N3 N 0.6309(5) 0.8409(4) 0.7998(2) 0.0400(7) Uani 1 1 d D . . . .
N4 N 0.8693(5) 0.0602(4) 1.1804(2) 0.0396(7) Uani 1 1 d D . . . .
C6 C 0.7080(3) 0.2956(2) 0.51027(9) 0.0293(7) Uani 1 1 d . . . . .
C5 C 0.7838(3) 0.44642(19) 0.54499(11) 0.0295(7) Uani 1 1 d G . . . .
C4 C 0.8638(3) 0.47221(18) 0.62601(11) 0.0308(7) Uani 1 1 d G . . . .
H4 H 0.9155 0.5753 0.6497 0.037 Uiso 1 1 calc R . . . .
C3 C 0.8680(3) 0.3472(2) 0.67231(9) 0.0321(7) Uani 1 1 d DG . . . .
H3 H 0.9226 0.3648 0.7277 0.039 Uiso 1 1 calc R . . . .
C2 C 0.7922(3) 0.19638(19) 0.63759(11) 0.0309(7) Uani 1 1 d G . . . .
C1 C 0.7123(3) 0.17059(18) 0.55657(11) 0.0293(7) Uani 1 1 d DG . . . .
H1 H 0.6605 0.0675 0.5328 0.035 Uiso 1 1 calc R . . . .
C12 C 0.6745(3) 0.49062(17) 0.40845(12) 0.0309(7) Uani 1 1 d . . . . .
C11 C 0.6427(3) 0.5783(2) 0.34390(9) 0.0307(7) Uani 1 1 d DG . . . .
H11 H 0.5799 0.5287 0.2929 0.037 Uiso 1 1 calc R . . . .
C10 C 0.7025(3) 0.7387(2) 0.35402(10) 0.0323(7) Uani 1 1 d G . . . .
C9 C 0.7943(3) 0.81132(17) 0.42871(12) 0.0327(7) Uani 1 1 d DG . . . .
H9 H 0.8352 0.9209 0.4356 0.039 Uiso 1 1 calc R . . . .
C8 C 0.8262(3) 0.7236(2) 0.49326(9) 0.0305(7) Uani 1 1 d G . . . .
H8 H 0.8889 0.7732 0.5443 0.037 Uiso 1 1 calc R . . . .
C7 C 0.7663(3) 0.5632(2) 0.48314(10) 0.0297(7) Uani 1 1 d G . . . .
C18 C 0.7409(3) 0.49681(17) 0.91181(11) 0.0293(7) Uani 1 1 d . . . . .
C13 C 0.7087(3) 0.5878(2) 0.84851(9) 0.0306(7) Uani 1 1 d DG . . . .
H13 H 0.7213 0.5413 0.7960 0.037 Uiso 1 1 calc R . . . .
C14 C 0.6579(3) 0.7467(2) 0.86207(10) 0.0330(7) Uani 1 1 d G . . . .
C15 C 0.6394(3) 0.81471(17) 0.93893(12) 0.0313(7) Uani 1 1 d DG . . . .
H15 H 0.6047 0.9234 0.9482 0.038 Uiso 1 1 calc R . . . .
C16 C 0.6716(3) 0.7237(2) 1.00224(9) 0.0307(7) Uani 1 1 d G . . . .
H16 H 0.6589 0.7702 1.0548 0.037 Uiso 1 1 calc R . . . .
C17 C 0.7223(3) 0.5648(2) 0.98868(10) 0.0288(7) Uani 1 1 d G . . . .
C19 C 0.8035(3) 0.2957(2) 1.01021(8) 0.0294(7) Uani 1 1 d . . . . .
C20 C 0.7662(3) 0.44544(19) 1.04836(11) 0.0293(7) Uani 1 1 d G . . . .
C21 C 0.7684(3) 0.46790(18) 1.13075(11) 0.0306(7) Uani 1 1 d G . . . .
H21 H 0.7429 0.5702 1.1568 0.037 Uiso 1 1 calc R . . . .
C22 C 0.8078(3) 0.3406(2) 1.17499(8) 0.0324(7) Uani 1 1 d DG . . . .
H22 H 0.8093 0.3560 1.2313 0.039 Uiso 1 1 calc R . . . .
C23 C 0.8451(3) 0.1909(2) 1.13684(11) 0.0325(7) Uani 1 1 d G . . . .
C24 C 0.8430(3) 0.16845(18) 1.05445(11) 0.0309(7) Uani 1 1 d DG . . . .
H24 H 0.8684 0.0661 1.0284 0.037 Uiso 1 1 calc R . . . .
H2A H 0.701(6) 0.926(6) 0.302(3) 0.046(12) Uiso 1 1 d . . . . .
H4A H 0.883(6) 0.079(5) 1.234(3) 0.038(11) Uiso 1 1 d . . . . .
H1A H 0.831(6) 0.086(5) 0.737(3) 0.038(10) Uiso 1 1 d . . . . .
H3A H 0.596(7) 0.939(6) 0.810(3) 0.055(13) Uiso 1 1 d . . . . .
H1B H 0.738(5) -0.014(5) 0.666(2) 0.029(10) Uiso 1 1 d . . . . .
H3B H 0.617(6) 0.808(5) 0.748(3) 0.044(11) Uiso 1 1 d . . . . .
H4B H 0.919(6) -0.012(6) 1.161(3) 0.049(13) Uiso 1 1 d . . . . .
H2B H 0.606(6) 0.796(5) 0.247(3) 0.035(11) 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 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0100 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1190 0.1170 '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
O1 S1 O2 115.44(14) . .
O1 S1 C6 112.16(12) . .
O1 S1 C12 112.18(12) . .
O2 S1 C6 110.92(12) . .
O2 S1 C12 110.40(12) . .
C12 S1 C6 93.73(10) . .
O3 S2 O4 115.00(14) . .
O3 S2 C18 113.08(13) . .
O3 S2 C19 112.92(13) . .
O4 S2 C18 109.69(12) . .
O4 S2 C19 110.68(13) . .
C18 S2 C19 93.48(9) . .
C2 N1 H1A 121(3) . .
C2 N1 H1B 119(3) . .
H1A N1 H1B 112(4) . .
C10 N2 H2A 114(3) . .
C10 N2 H2B 123(3) . .
H2A N2 H2B 119(4) . .
C14 N3 H3A 118(3) . .
C14 N3 H3B 127(3) . .
H3A N3 H3B 113(4) . .
C23 N4 H4A 119(3) . .
C23 N4 H4B 115(4) . .
H4A N4 H4B 119(4) . .
C5 C6 S1 111.73(11) . .
C5 C6 C1 120.0 . .
C1 C6 S1 127.99(11) . .
C6 C5 C7 110.93(14) . .
C4 C5 C6 120.0 . .
C4 C5 C7 129.06(14) . .
C5 C4 H4 120.0 . .
C5 C4 C3 120.0 . .
C3 C4 H4 120.0 . .
C4 C3 H3 120.0 . .
C2 C3 C4 120.0 . .
C2 C3 H3 120.0 . .
C3 C2 N1 120.05(17) . .
C3 C2 C1 120.0 . .
C1 C2 N1 119.87(17) . .
C6 C1 H1 120.0 . .
C2 C1 C6 120.0 . .
C2 C1 H1 120.0 . .
C11 C12 S1 128.00(11) . .
C11 C12 C7 120.0 . .
C7 C12 S1 111.62(11) . .
C12 C11 H11 120.0 . .
C10 C11 C12 120.0 . .
C10 C11 H11 120.0 . .
C11 C10 N2 120.44(18) . .
C11 C10 C9 120.0 . .
C9 C10 N2 119.54(18) . .
C10 C9 H9 120.0 . .
C8 C9 C10 120.0 . .
C8 C9 H9 120.0 . .
C9 C8 H8 120.0 . .
C9 C8 C7 120.0 . .
C7 C8 H8 120.0 . .
C12 C7 C5 111.16(14) . .
C8 C7 C5 128.83(14) . .
C8 C7 C12 120.0 . .
C13 C18 S2 127.73(11) . .
C13 C18 C17 120.0 . .
C17 C18 S2 111.81(11) . .
C18 C13 H13 120.0 . .
C14 C13 C18 120.0 . .
C14 C13 H13 120.0 . .
C13 C14 N3 120.62(17) . .
C13 C14 C15 120.0 . .
C15 C14 N3 119.35(17) . .
C14 C15 H15 120.0 . .
C16 C15 C14 120.0 . .
C16 C15 H15 120.0 . .
C15 C16 H16 120.0 . .
C17 C16 C15 120.0 . .
C17 C16 H16 120.0 . .
C18 C17 C20 111.15(13) . .
C16 C17 C18 120.0 . .
C16 C17 C20 128.85(13) . .
C20 C19 S2 111.68(11) . .
C20 C19 C24 120.0 . .
C24 C19 S2 128.17(11) . .
C19 C20 C17 111.16(13) . .
C19 C20 C21 120.0 . .
C21 C20 C17 128.82(13) . .
C20 C21 H21 120.0 . .
C20 C21 C22 120.0 . .
C22 C21 H21 120.0 . .
C21 C22 H22 120.0 . .
C23 C22 C21 120.0 . .
C23 C22 H22 120.0 . .
C22 C23 N4 119.56(18) . .
C22 C23 C24 120.0 . .
C24 C23 N4 120.22(18) . .
C19 C24 H24 120.0 . .
C23 C24 C19 120.0 . .
C23 C24 H24 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.445(2) .
S1 O2 1.456(2) .
S1 C6 1.7285(16) .
S1 C12 1.7244(15) .
S2 O3 1.449(2) .
S2 O4 1.454(3) .
S2 C18 1.7257(15) .
S2 C19 1.7356(16) .
N1 C2 1.407(3) .
N1 H1A 0.90(4) .
N1 H1B 0.83(4) .
N2 C10 1.397(3) .
N2 H2A 0.84(5) .
N2 H2B 0.81(4) .
N3 C14 1.392(3) .
N3 H3A 0.87(5) .
N3 H3B 0.87(5) .
N4 C23 1.399(3) .
N4 H4A 0.88(4) .
N4 H4B 0.77(5) .
C6 C5 1.3900 .
C6 C1 1.3900 .
C5 C4 1.3900 .
C5 C7 1.5211(19) .
C4 H4 0.9500 .
C4 C3 1.3900 .
C3 H3 0.9500 .
C3 C2 1.3900 .
C2 C1 1.3900 .
C1 H1 0.9500 .
C12 C11 1.3900 .
C12 C7 1.3900 .
C11 H11 0.9500 .
C11 C10 1.3900 .
C10 C9 1.3900 .
C9 H9 0.9500 .
C9 C8 1.3900 .
C8 H8 0.9500 .
C8 C7 1.3900 .
C18 C13 1.3900 .
C18 C17 1.3900 .
C13 H13 0.9500 .
C13 C14 1.3900 .
C14 C15 1.3900 .
C15 H15 0.9500 .
C15 C16 1.3900 .
C16 H16 0.9500 .
C16 C17 1.3900 .
C17 C20 1.5163(19) .
C19 C20 1.3900 .
C19 C24 1.3900 .
C20 C21 1.3900 .
C21 H21 0.9500 .
C21 C22 1.3900 .
C22 H22 0.9500 .
C22 C23 1.3900 .
C23 C24 1.3900 .
C24 H24 0.9500 .
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
N2 H2A O2 0.84(5) 2.35(5) 3.185(4) 168(4) 1_565
N3 H3A O4 0.87(5) 2.28(5) 3.102(4) 158(4) 1_565
N1 H1B O1 0.83(4) 2.30(4) 3.123(4) 179(4) 2_656
N3 H3B O1 0.87(5) 2.18(5) 3.046(4) 170(4) 2_666
N4 H4B O3 0.77(5) 2.31(5) 3.080(4) 170(5) 2_757
N2 H2B O4 0.81(4) 2.29(4) 3.067(4) 161(4) 2_666
