#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/18/1551857.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1551857
loop_
_publ_author_name
'Bolla, Geetha'
'Nangia, Ashwini'
_publ_section_title
;
 Supramolecular synthon hierarchy in sulfonamide cocrystals with
 syn-amides and N-oxides
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252519005037
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C6 H7 N O2, C17 H14 F3 N3 O2 S'
_chemical_formula_sum            'C23 H21 F3 N4 O4 S'
_chemical_formula_weight         506.50
_chemical_melting_point          385
_chemical_name_common            CELOMeHP
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                105.897(2)
_cell_angle_beta                 102.702(2)
_cell_angle_gamma                101.930(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6112(9)
_cell_length_b                   11.3462(14)
_cell_length_c                   15.1063(18)
_cell_measurement_reflns_used    4970
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.80
_cell_volume                     1173.4(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.630 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12619
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         1.466
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0614
_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)+(0.0938P)²+0.7405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4107
_reflns_number_total             4786
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {bb8c8d3e-c7ea-483e-bbec-55bdcdd3e535}
_cod_data_source_file            lq5020.cif
_cod_data_source_block           CELOMeHP
_cod_database_code               1551857
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C13(H13), C2(H2), C10(H10), C17(H17), C20(H20), C6(H6),
 C7(H7), C22(H22), C9(H9), C21(H21)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O3 O 0.1645(2) 0.64705(17) 0.01167(14) 0.0524(5) Uani 1 1 d .
S1 S 0.22117(8) 0.01466(6) 0.14159(4) 0.0414(2) Uani 1 1 d .
O4 O 0.5274(3) 0.77673(19) 0.08248(15) 0.0587(5) Uani 1 1 d .
C15 C 0.4578(3) 0.1093(2) 0.18939(17) 0.0375(5) Uani 1 1 d .
O1 O 0.1119(3) 0.09814(18) 0.12063(15) 0.0581(5) Uani 1 1 d .
O2 O 0.1827(3) -0.0470(2) 0.20785(14) 0.0607(5) Uani 1 1 d .
N3 N 0.2083(3) -0.0845(2) 0.04065(18) 0.0487(6) Uani 1 1 d .
N4 N 0.2176(3) 0.4866(2) 0.06694(17) 0.0489(5) Uani 1 1 d .
N2 N 0.9724(3) 0.3909(2) 0.31167(15) 0.0443(5) Uani 1 1 d .
C18 C 0.2768(3) 0.6008(2) 0.05476(18) 0.0423(5) Uani 1 1 d .
N1 N 0.9751(3) 0.4904(2) 0.27857(17) 0.0496(5) Uani 1 1 d .
C12 C 0.8041(3) 0.2869(2) 0.27094(17) 0.0394(5) Uani 1 1 d .
C3 C 1.1250(3) 0.4147(2) 0.38871(19) 0.0461(6) Uani 1 1 d .
C14 C 0.5494(4) 0.1559(2) 0.13146(17) 0.0430(5) Uani 1 1 d .
H14 H 0.493654 0.127661 0.065243 0.052 Uiso 1 1 calc R
C16 C 0.5414(3) 0.1479(3) 0.28807(18) 0.0453(6) Uani 1 1 d .
H16 H 0.480864 0.113467 0.326325 0.054 Uiso 1 1 calc R
C13 C 0.7243(4) 0.2445(2) 0.17201(18) 0.0434(5) Uani 1 1 d .
H13 H 0.787732 0.275430 0.133301 0.052 Uiso 1 1 calc R
C2 C 1.2313(4) 0.5371(3) 0.4050(2) 0.0549(7) Uani 1 1 d .
H2 H 1.344759 0.582737 0.452246 0.066 Uiso 1 1 calc R
C19 C 0.4763(4) 0.6623(2) 0.09500(18) 0.0463(6) Uani 1 1 d .
C10 C 1.2253(4) 0.3623(3) 0.5364(2) 0.0581(7) Uani 1 1 d .
H10 H 1.239445 0.446361 0.572468 0.070 Uiso 1 1 calc R
C1 C 1.1325(4) 0.5776(3) 0.3358(2) 0.0524(7) Uani 1 1 d .
F2 F 1.3114(4) 0.7121(2) 0.27650(19) 0.0996(8) Uani 1 1 d .
C5 C 1.1629(3) 0.3233(2) 0.43679(18) 0.0448(6) Uani 1 1 d .
C17 C 0.7150(3) 0.2378(3) 0.32897(18) 0.0467(6) Uani 1 1 d .
H17 H 0.771618 0.265090 0.395075 0.056 Uiso 1 1 calc R
C20 C 0.5900(4) 0.6057(3) 0.1398(2) 0.0556(7) Uani 1 1 d .
H20 H 0.718601 0.645231 0.164197 0.067 Uiso 1 1 calc R
C6 C 1.1442(4) 0.1975(3) 0.3852(2) 0.0512(6) Uani 1 1 d .
H6 H 1.103050 0.169253 0.318252 0.061 Uiso 1 1 calc R
C7 C 1.1861(4) 0.1140(3) 0.4321(2) 0.0552(7) Uani 1 1 d .
H7 H 1.173033 0.030158 0.396109 0.066 Uiso 1 1 calc R
F3 F 1.2693(5) 0.7964(2) 0.4060(2) 0.1237(10) Uani 1 1 d .
C22 C 0.3301(4) 0.4309(3) 0.1140(2) 0.0603(8) Uani 1 1 d .
H22 H 0.278929 0.353550 0.121302 0.072 Uiso 1 1 calc R
C8 C 1.2471(4) 0.1519(3) 0.5315(2) 0.0563(7) Uani 1 1 d .
F1 F 1.0436(4) 0.7340(3) 0.2812(3) 0.1764(19) Uani 1 1 d .
C9 C 1.2664(5) 0.2782(3) 0.5824(2) 0.0638(8) Uani 1 1 d .
H9 H 1.308303 0.306500 0.649372 0.077 Uiso 1 1 calc R
C4 C 1.1831(4) 0.7023(3) 0.3206(3) 0.0658(8) Uani 1 1 d .
C21 C 0.5154(5) 0.4878(3) 0.1498(2) 0.0646(8) Uani 1 1 d .
H21 H 0.594004 0.449479 0.181001 0.077 Uiso 1 1 calc R
C11 C 1.2900(5) 0.0601(4) 0.5824(3) 0.0775(10) Uani 1 1 d .
H11A H 1.174810 0.001828 0.578035 0.116 Uiso 1 1 calc GR
H11B H 1.357467 0.106680 0.648860 0.116 Uiso 1 1 calc GR
H11C H 1.365351 0.013023 0.552825 0.116 Uiso 1 1 calc GR
C23 C 0.7226(4) 0.8464(3) 0.1218(3) 0.0739(10) Uani 1 1 d .
H23A H 0.762141 0.859658 0.189498 0.111 Uiso 1 1 calc GR
H23B H 0.741448 0.927541 0.111854 0.111 Uiso 1 1 calc GR
H23C H 0.794950 0.798547 0.090252 0.111 Uiso 1 1 calc GR
H3A H 0.138(5) -0.081(3) -0.003(3) 0.063(10) Uiso 1 1 d .
H3B H 0.219(5) -0.157(3) 0.044(2) 0.065(10) Uiso 1 1 d .
H4 H 0.094(5) 0.448(3) 0.044(2) 0.063(9) 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'
F F 0.0171 0.0103 '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
O1 S1 C15 106.35(11)
O1 S1 N3 106.79(13)
O2 S1 C15 107.10(11)
O2 S1 O1 118.08(14)
O2 S1 N3 112.17(13)
N3 S1 C15 105.52(12)
C19 O4 C23 116.7(2)
C14 C15 S1 120.29(18)
C14 C15 C16 120.7(2)
C16 C15 S1 118.53(19)
C18 N4 C22 124.9(2)
N1 N2 C12 116.3(2)
N1 N2 C3 113.0(2)
C3 N2 C12 130.1(2)
O3 C18 N4 121.4(2)
O3 C18 C19 123.7(2)
N4 C18 C19 114.9(2)
C1 N1 N2 103.6(2)
C13 C12 N2 117.8(2)
C17 C12 N2 121.0(2)
C17 C12 C13 121.0(2)
N2 C3 C2 105.1(2)
N2 C3 C5 125.1(2)
C2 C3 C5 129.8(2)
C15 C14 C13 119.8(2)
C17 C16 C15 119.5(2)
C14 C13 C12 119.3(2)
C3 C2 C1 105.3(2)
O4 C19 C18 112.5(2)
C20 C19 O4 127.0(2)
C20 C19 C18 120.4(2)
C9 C10 C5 120.7(3)
N1 C1 C2 113.0(2)
N1 C1 C4 118.9(3)
C2 C1 C4 128.1(3)
C10 C5 C3 120.1(2)
C10 C5 C6 118.2(3)
C6 C5 C3 121.7(2)
C16 C17 C12 119.5(2)
C19 C20 C21 120.6(3)
C7 C6 C5 120.6(3)
C6 C7 C8 121.6(3)
C21 C22 N4 119.7(3)
C7 C8 C9 117.3(3)
C7 C8 C11 121.4(3)
C9 C8 C11 121.3(3)
C10 C9 C8 121.6(3)
F2 C4 C1 113.3(3)
F2 C4 F3 101.7(3)
F3 C4 C1 109.9(3)
F1 C4 C1 114.2(3)
F1 C4 F2 111.1(4)
F1 C4 F3 105.6(4)
C22 C21 C20 119.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C18 1.248(3)
S1 C15 1.767(2)
S1 O1 1.436(2)
S1 O2 1.416(2)
S1 N3 1.596(2)
O4 C19 1.353(3)
O4 C23 1.433(3)
C15 C14 1.379(3)
C15 C16 1.389(3)
N4 C18 1.357(3)
N4 C22 1.357(3)
N2 N1 1.353(3)
N2 C12 1.429(3)
N2 C3 1.371(3)
C18 C19 1.444(3)
N1 C1 1.322(3)
C12 C13 1.386(3)
C12 C17 1.382(3)
C3 C2 1.379(4)
C3 C5 1.459(4)
C14 C13 1.381(3)
C16 C17 1.381(3)
C2 C1 1.388(4)
C19 C20 1.353(4)
C10 C5 1.386(4)
C10 C9 1.373(4)
C1 C4 1.481(4)
F2 C4 1.301(4)
C5 C6 1.387(4)
C20 C21 1.403(4)
C6 C7 1.376(4)
C7 C8 1.383(4)
F3 C4 1.349(4)
C22 C21 1.340(4)
C8 C9 1.388(5)
C8 C11 1.500(4)
F1 C4 1.268(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168303057
