#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:02:52 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160261.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_7160261
loop_
_publ_author_name
'Chang, Meng-Yang'
'Lin, Chun-Yi'
_publ_section_title
;
 One-pot synthesis of symmetrical bis-sulfonyl 2,6-diarylpyridines
 via BiCl₃-catalyzed and
 K₂S₂O₈-mediated domino annulation of
 β-ketosulfones and N,N-dimethylacetamide.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              844
_journal_page_last               853
_journal_paper_doi               10.1039/d4ob01681e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C31 H23 F2 N O4 S2'
_chemical_formula_sum            'C31 H23 F2 N O4 S2'
_chemical_formula_weight         575.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-09-09 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1425(3)
_cell_length_b                   13.6754(3)
_cell_length_c                   18.9825(4)
_cell_measurement_reflns_used    14800
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      26.9960
_cell_measurement_theta_min      1.8940
_cell_volume                     3042.65(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  38.00   0.50   13.20    --   10.60 -82.00  60.00  234
  2  ω    -15.00 100.00   0.50   13.20    --   10.60  77.00 -60.00  230
  3  ω    -79.00  36.00   0.50   13.20    --   10.60 -77.00   0.00  230
  4  ω    -79.00  41.00   0.50   13.20    --   10.60 -57.00 120.00  240
  5  ω    -79.00  41.00   0.50   13.20    --   10.60 -57.00  60.00  240
  6  ω    -79.00  38.00   0.50   13.20    --   10.60 -82.00 -90.00  234
  7  ω   -100.00  10.00   0.50   13.20    --  -10.90 -82.00  30.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0159513000
_diffrn_orient_matrix_UB_12      -0.0168890000
_diffrn_orient_matrix_UB_13      0.0365875000
_diffrn_orient_matrix_UB_21      0.0319454000
_diffrn_orient_matrix_UB_22      -0.0383291000
_diffrn_orient_matrix_UB_23      -0.0103008000
_diffrn_orient_matrix_UB_31      0.0488599000
_diffrn_orient_matrix_UB_32      0.0305967000
_diffrn_orient_matrix_UB_33      0.0072891000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19630
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.858
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0363
_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)+(0.0440P)²+4.3156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2467
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01681e2.cif
_cod_data_source_block           k11110-myc-e(ycm927)_auto-mask
_cod_depositor_comments
'Adding full bibliography for 7160261--7160263.cif.'
_cod_database_code               7160261
_shelx_shelxl_version_number     2018/3
_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   0.978
_shelx_estimated_absorpt_t_min   0.967
_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. Uiso/Uaniso restraints and constraints
S1 \\sim O1 \\sim O2 \\sim F1: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.775
_oxdiff_exptl_absorpt_empirical_full_min 0.563
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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 0.56729(3) 0.47632(3) 0.38348(2) 0.02185(14) Uani 1 1 d . U . . .
F1 F 0.29061(11) 0.86751(12) 0.30219(11) 0.0847(6) Uani 1 1 d . . . . .
O1 O 0.45315(10) 0.47611(9) 0.39213(7) 0.0280(3) Uani 1 1 d . U . . .
O2 O 0.62287(10) 0.38356(9) 0.38268(7) 0.0294(3) Uani 1 1 d . U . . .
N1 N 0.750000 0.69701(14) 0.500000 0.0214(4) Uani 1 2 d S T P . .
C1 C 0.66006(13) 0.64811(12) 0.45924(8) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.56180(14) 0.70839(12) 0.42004(9) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.45196(15) 0.68820(13) 0.42514(10) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.439808 0.636514 0.455687 0.033 Uiso 1 1 calc R U . . .
C4 C 0.36034(16) 0.74255(15) 0.38622(12) 0.0389(5) Uani 1 1 d . . . . .
H4 H 0.285174 0.729318 0.389773 0.047 Uiso 1 1 calc R U . . .
C5 C 0.38088(17) 0.81595(17) 0.34244(15) 0.0518(6) Uani 1 1 d . . . . .
C6 C 0.48795(18) 0.84054(18) 0.33741(15) 0.0570(7) Uani 1 1 d . . . . .
H6 H 0.499155 0.893215 0.307401 0.068 Uiso 1 1 calc R U . . .
C7 C 0.57893(16) 0.78654(15) 0.37722(12) 0.0397(5) Uani 1 1 d . . . . .
H7 H 0.654163 0.802894 0.375376 0.048 Uiso 1 1 calc R U . . .
C8 C 0.66251(13) 0.54582(12) 0.45361(8) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.750000 0.49438(17) 0.500000 0.0203(5) Uani 1 2 d S T P . .
H9 H 0.749998 0.424917 0.500003 0.024 Uiso 1 2 calc R U P . .
C10 C 0.57051(14) 0.54283(13) 0.30470(9) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.67494(15) 0.55486(14) 0.28873(10) 0.0295(4) Uani 1 1 d . . . . .
H11 H 0.742059 0.525807 0.318624 0.035 Uiso 1 1 calc R U . . .
C12 C 0.67927(17) 0.60983(16) 0.22858(11) 0.0367(5) Uani 1 1 d . . . . .
H12 H 0.750398 0.618693 0.217339 0.044 Uiso 1 1 calc R U . . .
C13 C 0.58160(17) 0.65267(15) 0.18395(10) 0.0364(5) Uani 1 1 d . . . . .
C14 C 0.47854(17) 0.63844(16) 0.20119(10) 0.0364(5) Uani 1 1 d . . . . .
H14 H 0.411066 0.666515 0.170944 0.044 Uiso 1 1 calc R U . . .
C15 C 0.47191(15) 0.58418(14) 0.26158(9) 0.0296(4) Uani 1 1 d . . . . .
H15 H 0.400983 0.575558 0.273136 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5877(2) 0.7135(2) 0.11873(13) 0.0556(7) Uani 1 1 d . . . . .
H16A H 0.510439 0.732588 0.091581 0.083 Uiso 1 1 calc R U . . .
H16B H 0.623153 0.675124 0.086963 0.083 Uiso 1 1 calc R U . . .
H16C H 0.633299 0.772230 0.135286 0.083 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 0.0033 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'
F F 0.0171 0.0103 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.93(8) . . ?
O1 S1 C8 111.75(7) . . ?
O1 S1 C10 109.53(8) . . ?
O2 S1 C8 105.20(7) . . ?
O2 S1 C10 109.40(8) . . ?
C10 S1 C8 101.77(8) . . ?
C1 N1 C1 120.1(2) . 2_656 ?
N1 C1 C2 116.12(15) . . ?
N1 C1 C8 120.72(15) . . ?
C8 C1 C2 123.15(14) . . ?
C3 C2 C1 121.08(15) . . ?
C3 C2 C7 119.08(16) . . ?
C7 C2 C1 119.85(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.63(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.10(18) . . ?
C5 C4 H4 120.9 . . ?
F1 C5 C4 118.33(18) . . ?
F1 C5 C6 118.32(19) . . ?
C4 C5 C6 123.34(19) . . ?
C5 C6 H6 121.0 . . ?
C5 C6 C7 118.00(19) . . ?
C7 C6 H6 121.0 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.74(18) . . ?
C6 C7 H7 119.6 . . ?
C1 C8 S1 124.26(12) . . ?
C9 C8 S1 116.29(14) . . ?
C9 C8 C1 119.12(15) . . ?
C8 C9 C8 118.8(2) . 2_656 ?
C8 C9 H9 120.6 . . ?
C8 C9 H9 120.6 2_656 . ?
C11 C10 S1 118.11(13) . . ?
C15 C10 S1 120.44(13) . . ?
C15 C10 C11 121.42(16) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.67(16) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.45(17) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C16 120.95(18) . . ?
C14 C13 C12 118.31(17) . . ?
C14 C13 C16 120.74(18) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.42(17) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 118.72(17) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 O1 1.4375(12) . ?
S1 O2 1.4388(13) . ?
S1 C8 1.7911(16) . ?
S1 C10 1.7596(17) . ?
F1 C5 1.358(2) . ?
N1 C1 1.3405(19) . ?
N1 C1 1.3406(19) 2_656 ?
C1 C2 1.481(2) . ?
C1 C8 1.404(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(3) . ?
C5 C6 1.370(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 C15 1.382(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 C14 1.387(3) . ?
C13 C16 1.509(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C8 C9 C8 168.46(13) . . . 2_656 ?
S1 C10 C11 C12 -177.69(15) . . . . ?
S1 C10 C15 C14 178.12(15) . . . . ?
F1 C5 C6 C7 -178.6(3) . . . . ?
O1 S1 C8 C1 -70.54(15) . . . . ?
O1 S1 C8 C9 116.04(11) . . . . ?
O1 S1 C10 C11 177.32(13) . . . . ?
O1 S1 C10 C15 -0.72(17) . . . . ?
O2 S1 C8 C1 160.33(14) . . . . ?
O2 S1 C8 C9 -13.08(13) . . . . ?
O2 S1 C10 C11 -52.01(16) . . . . ?
O2 S1 C10 C15 129.95(15) . . . . ?
N1 C1 C2 C3 -128.96(16) . . . . ?
N1 C1 C2 C7 51.1(2) . . . . ?
N1 C1 C8 S1 -162.20(10) . . . . ?
N1 C1 C8 C9 11.0(2) . . . . ?
C1 N1 C1 C2 176.05(15) 2_656 . . . ?
C1 N1 C1 C8 -5.52(11) 2_656 . . . ?
C1 C2 C3 C4 -177.57(17) . . . . ?
C1 C2 C7 C6 176.8(2) . . . . ?
C1 C8 C9 C8 -5.32(10) . . . 2_656 ?
C2 C1 C8 S1 16.1(2) . . . . ?
C2 C1 C8 C9 -170.65(13) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C2 C7 C6 -3.2(3) . . . . ?
C3 C4 C5 F1 177.8(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C4 C5 C6 C7 1.8(4) . . . . ?
C5 C6 C7 C2 1.2(4) . . . . ?
C7 C2 C3 C4 2.3(3) . . . . ?
C8 S1 C10 C11 58.92(15) . . . . ?
C8 S1 C10 C15 -119.12(15) . . . . ?
C8 C1 C2 C3 52.7(2) . . . . ?
C8 C1 C2 C7 -127.3(2) . . . . ?
C10 S1 C8 C1 46.25(16) . . . . ?
C10 S1 C8 C9 -127.17(11) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C11 C12 C13 C16 179.4(2) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C15 C10 C11 C12 0.3(3) . . . . ?
C16 C13 C14 C15 -178.9(2) . . . . ?
