#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:38:38 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296339 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/37/7133765.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_7133765
loop_
_publ_author_name
'Hanna, Fergal E.'
'Hunter, Christopher A.'
_publ_section_title
;
 Polarisation effects on the H-bond acceptor properties of sulfonamides.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11750
_journal_page_last               11753
_journal_paper_doi               10.1039/d4cc03530e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H26 N4 O5 S'
_chemical_formula_sum            'C21 H26 N4 O5 S'
_chemical_formula_weight         446.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2024-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.787(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6438(2)
_cell_length_b                   35.5926(12)
_cell_length_c                   11.0653(4)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.54
_cell_measurement_theta_min      5.48
_cell_volume                     2211.44(13)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40491
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.552
_diffrn_reflns_theta_max         66.552
_diffrn_reflns_theta_min         5.482
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0379P)²+0.7977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             3896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03530e2.cif
_cod_data_source_block           CH_B1_0070
_cod_depositor_comments          'Adding full bibliography for 7133765.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7133765
_cambridge_user_name             'Fergal Hanna'
_cambridge_user_crsid            feh27
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             FHBK4-62
_cambridge_data_id               CH_B1_0070
_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   0.694
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.98727(6) 0.41977(2) 0.38839(4) 0.03242(12) Uani 1 1 d . . . . .
O1 O 0.45256(18) 0.30719(3) 0.25810(9) 0.0329(2) Uani 1 1 d . . . . .
O11 O 1.0731(2) 0.42091(3) 0.27079(11) 0.0421(3) Uani 1 1 d . . . . .
O12 O 1.1551(2) 0.42041(3) 0.49436(12) 0.0457(3) Uani 1 1 d . . . . .
O21 O 0.4342(3) 0.32089(4) 0.86087(11) 0.0613(4) Uani 1 1 d . . . . .
O22 O 0.1929(3) 0.29375(5) 0.72555(13) 0.0691(4) Uani 1 1 d . . . . .
N1 N 0.8260(2) 0.38182(3) 0.38516(13) 0.0323(3) Uani 1 1 d . . . . .
H1 H 0.790(3) 0.3733(5) 0.3132(18) 0.041(5) Uiso 1 1 d . . . . .
N2 N 0.3631(3) 0.31410(4) 0.75494(12) 0.0424(3) Uani 1 1 d . . . . .
N3 N 0.7430(2) 0.34078(3) 0.17158(11) 0.0299(3) Uani 1 1 d . . . . .
N4 N 0.9221(3) 0.21993(4) -0.09217(13) 0.0469(4) Uani 1 1 d . . . . .
C1 C 0.7115(3) 0.36556(4) 0.47912(13) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.8030(3) 0.36911(5) 0.60069(14) 0.0371(4) Uani 1 1 d . . . . .
H2A H 0.944364 0.383192 0.621069 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6896(3) 0.35232(5) 0.69134(14) 0.0383(4) Uani 1 1 d . . . . .
H3A H 0.750195 0.354968 0.774154 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4866(3) 0.33164(4) 0.65936(14) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.3931(3) 0.32748(4) 0.54010(14) 0.0315(3) Uani 1 1 d . . . . .
H5A H 0.252977 0.312968 0.521130 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5034(2) 0.34449(4) 0.44768(13) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.3840(3) 0.34084(4) 0.32006(13) 0.0312(3) Uani 1 1 d . . . . .
H7A H 0.209200 0.340653 0.322910 0.037 Uiso 1 1 calc R U . . .
H7B H 0.424113 0.363111 0.272562 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6219(2) 0.30937(4) 0.18105(12) 0.0279(3) Uani 1 1 d . . . . .
C9 C 0.6583(3) 0.27693(4) 0.11412(13) 0.0318(3) Uani 1 1 d . . . . .
H9A H 0.565914 0.254924 0.122115 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8333(3) 0.27814(4) 0.03627(13) 0.0323(3) Uani 1 1 d . . . . .
C16 C 0.9651(3) 0.31106(5) 0.02476(13) 0.0357(4) Uani 1 1 d . . . . .
H16A H 1.086733 0.312333 -0.028547 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9119(3) 0.34127(4) 0.09325(14) 0.0343(3) Uani 1 1 d . . . . .
H17A H 0.998421 0.363885 0.085367 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8810(3) 0.24548(5) -0.03512(14) 0.0375(4) Uani 1 1 d . . . . .
C19 C 0.7873(3) 0.45759(4) 0.40163(14) 0.0334(3) Uani 1 1 d . . . . .
H19A H 0.692115 0.452362 0.470145 0.040 Uiso 1 1 calc R U . . .
H19B H 0.880803 0.480686 0.421706 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6185(3) 0.46484(4) 0.28850(14) 0.0316(3) Uani 1 1 d . . . . .
H20A H 0.519044 0.442290 0.269499 0.038 Uiso 1 1 calc R U . . .
H20B H 0.711704 0.469657 0.218925 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4582(3) 0.49849(4) 0.30623(14) 0.0337(3) Uani 1 1 d . . . . .
H21A H 0.365302 0.493425 0.375735 0.040 Uiso 1 1 calc R U . . .
H21B H 0.559013 0.520801 0.326758 0.040 Uiso 1 1 calc R U . . .
C22 C 0.2873(3) 0.50726(4) 0.19500(14) 0.0339(3) Uani 1 1 d . . . . .
H22A H 0.184420 0.485114 0.175418 0.041 Uiso 1 1 calc R U . . .
H22B H 0.380096 0.511835 0.125118 0.041 Uiso 1 1 calc R U . . .
C23 C 0.1303(3) 0.54133(4) 0.21192(15) 0.0360(3) Uani 1 1 d . . . . .
H23A H 0.045948 0.537429 0.285135 0.043 Uiso 1 1 calc R U . . .
H23B H 0.233146 0.563748 0.226359 0.043 Uiso 1 1 calc R U . . .
C24 C -0.0526(3) 0.54901(4) 0.10420(15) 0.0366(4) Uani 1 1 d . . . . .
H24A H 0.031904 0.552850 0.030996 0.044 Uiso 1 1 calc R U . . .
H24B H -0.155415 0.526595 0.089875 0.044 Uiso 1 1 calc R U . . .
C25 C -0.2094(3) 0.58298(5) 0.12045(16) 0.0421(4) Uani 1 1 d . . . . .
H25A H -0.288121 0.579798 0.195785 0.051 Uiso 1 1 calc R U . . .
H25B H -0.107838 0.605679 0.130272 0.051 Uiso 1 1 calc R U . . .
C26 C -0.3985(3) 0.58896(5) 0.01468(17) 0.0481(4) Uani 1 1 d . . . . .
H26A H -0.491223 0.611495 0.029269 0.072 Uiso 1 1 calc R U . . .
H26B H -0.504549 0.567096 0.006776 0.072 Uiso 1 1 calc R U . . .
H26C H -0.321985 0.592131 -0.060322 0.072 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
O12 S1 O11 119.13(7) . . ?
O12 S1 N1 110.72(7) . . ?
O11 S1 N1 104.07(7) . . ?
O12 S1 C19 107.12(7) . . ?
O11 S1 C19 109.24(7) . . ?
N1 S1 C19 105.84(7) . . ?
C8 O1 C7 119.47(11) . . ?
C1 N1 S1 128.65(11) . . ?
C1 N1 H1 117.3(12) . . ?
S1 N1 H1 113.2(12) . . ?
O22 N2 O21 123.06(14) . . ?
O22 N2 C4 118.67(14) . . ?
O21 N2 C4 118.27(15) . . ?
C8 N3 C17 117.80(13) . . ?
C2 C1 N1 121.52(14) . . ?
C2 C1 C6 120.30(13) . . ?
N1 C1 C6 118.16(13) . . ?
C3 C2 C1 120.49(15) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 118.66(15) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 122.09(14) . . ?
C3 C4 N2 119.11(14) . . ?
C5 C4 N2 118.80(14) . . ?
C4 C5 C6 120.08(14) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 118.38(13) . . ?
C5 C6 C7 117.44(13) . . ?
C1 C6 C7 124.10(13) . . ?
O1 C7 C6 113.46(12) . . ?
O1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N3 C8 O1 120.38(13) . . ?
N3 C8 C9 123.51(13) . . ?
O1 C8 C9 116.10(13) . . ?
C15 C9 C8 117.35(14) . . ?
C15 C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C15 C16 120.32(14) . . ?
C9 C15 C18 120.13(14) . . ?
C16 C15 C18 119.54(14) . . ?
C17 C16 C15 117.35(14) . . ?
C17 C16 H16A 121.3 . . ?
C15 C16 H16A 121.3 . . ?
N3 C17 C16 123.66(14) . . ?
N3 C17 H17A 118.2 . . ?
C16 C17 H17A 118.2 . . ?
N4 C18 C15 178.85(19) . . ?
C20 C19 S1 114.41(10) . . ?
C20 C19 H19A 108.7 . . ?
S1 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
S1 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 111.03(12) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 113.19(12) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 C23 113.18(13) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 113.81(13) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 114.05(13) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 113.14(15) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O12 1.4313(12) . ?
S1 O11 1.4342(12) . ?
S1 N1 1.6270(12) . ?
S1 C19 1.7721(15) . ?
O1 C8 1.3453(17) . ?
O1 C7 1.4518(17) . ?
O21 N2 1.2242(19) . ?
O22 N2 1.221(2) . ?
N1 C1 1.4034(19) . ?
N1 H1 0.86(2) . ?
N2 C4 1.4636(19) . ?
N3 C8 1.3201(18) . ?
N3 C17 1.3516(19) . ?
N4 C18 1.144(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.407(2) . ?
C2 C3 1.379(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.378(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.379(2) . ?
C5 C6 1.389(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.508(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.398(2) . ?
C9 C15 1.375(2) . ?
C9 H9A 0.9500 . ?
C15 C16 1.401(2) . ?
C15 C18 1.446(2) . ?
C16 C17 1.366(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C19 C20 1.517(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.525(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.525(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.520(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.518(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
