#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:07:13 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299114 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160312.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_7160312
loop_
_publ_author_name
'Chang, Meng-Yang'
'Lin, Chun-Yi'
_publ_section_title
;
 Construction of diaryl oxacyclic sulfones via
 Bi(OTf)₃-catalyzed intramolecular cyclocondensation of
 1,3-diaroylsulfones.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1662
_journal_page_last               1672
_journal_paper_doi               10.1039/d4ob01916d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H10 Br2 O3 S'
_chemical_formula_sum            'C16 H10 Br2 O3 S'
_chemical_formula_weight         442.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.652(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4471(3)
_cell_length_b                   10.9120(4)
_cell_length_c                   17.0111(6)
_cell_measurement_reflns_used    7663
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.1880
_cell_measurement_theta_min      2.2200
_cell_volume                     1535.68(10)
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 100.00   0.50    3.90    --   10.60  19.00 120.00  358
  2  ω    -15.00 100.00   0.50    3.90    --   10.60  77.00 120.00  230
  3  ω    -79.00  36.00   0.50    3.90    --   10.60 -77.00 150.00  230
  4  ω    -79.00  41.00   0.50    3.90    --   10.60 -57.00  30.00  240
  5  ω    -17.00  86.00   0.50    3.90    --   10.60  57.00  90.00  206
  6  ω     23.00  78.00   0.50    3.90    --  -10.90  82.00  30.00  110
;
_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      -0.0249913000
_diffrn_orient_matrix_UB_12      -0.0082335000
_diffrn_orient_matrix_UB_13      -0.0420015000
_diffrn_orient_matrix_UB_21      -0.0231676000
_diffrn_orient_matrix_UB_22      -0.0610727000
_diffrn_orient_matrix_UB_23      0.0063739000
_diffrn_orient_matrix_UB_31      -0.0787960000
_diffrn_orient_matrix_UB_32      0.0205967000
_diffrn_orient_matrix_UB_33      0.0020890000
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17704
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.125
_diffrn_reflns_theta_min         2.231
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10807
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.603
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0432
_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)+(0.0332P)²+5.1047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2639
_reflns_number_total             3230
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01916d2.cif
_cod_data_source_block           k11212-myc-f(ynp1020)_auto
_cod_depositor_comments
'Adding full bibliography for 7160310--7160313.cif.'
_cod_database_code               7160312
_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   0.410
_shelx_estimated_absorpt_t_min   0.220
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H2), C15(H16), C1(H8), C9(H4), C3(H10), C4(H11), C2(H9), C12(H19),
 C14(H17), C13(H18)
;
_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 5.727
_oxdiff_exptl_absorpt_empirical_full_min 0.499
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br20 Br 0.08141(6) 0.74282(5) 0.72110(3) 0.03484(16) Uani 1 1 d . . . . .
Br13 Br 0.41712(6) 0.92869(5) 0.39072(3) 0.03753(16) Uani 1 1 d . . . . .
S1 S 0.60356(12) 0.65606(10) 0.59721(6) 0.0192(2) Uani 1 1 d . . . . .
O6 O 0.3271(3) 0.8307(3) 0.61844(15) 0.0162(6) Uani 1 1 d . . . . .
O24 O 0.6051(4) 0.5241(3) 0.60275(18) 0.0274(7) Uani 1 1 d . . . . .
O23 O 0.7484(3) 0.7109(3) 0.58104(18) 0.0268(7) Uani 1 1 d . . . . .
C14 C 0.3993(5) 0.8476(4) 0.7595(2) 0.0179(8) Uani 1 1 d . . . . .
C7 C 0.1932(5) 0.8351(4) 0.4837(2) 0.0157(8) Uani 1 1 d . . . . .
C2 C 0.4383(5) 0.7048(4) 0.5276(2) 0.0189(9) Uani 1 1 d . . . . .
H2 H 0.423369 0.672331 0.474821 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2115(5) 0.8998(4) 0.4153(2) 0.0194(9) Uani 1 1 d . . . . .
C1 C 0.3298(5) 0.7855(4) 0.5432(2) 0.0170(8) Uani 1 1 d . . . . .
C5 C 0.4341(5) 0.7915(4) 0.6851(2) 0.0174(9) Uani 1 1 d . . . . .
C16 C 0.2168(5) 0.8976(4) 0.8482(2) 0.0236(9) Uani 1 1 d . . . . .
H16 H 0.112485 0.893523 0.860922 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2473(5) 0.8395(4) 0.7806(2) 0.0195(9) Uani 1 1 d . . . . .
C8 C 0.0366(5) 0.8189(4) 0.4972(2) 0.0196(9) Uani 1 1 d . . . . .
H8 H 0.021536 0.776469 0.543856 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5586(5) 0.7165(4) 0.6838(2) 0.0191(9) Uani 1 1 d . . . . .
H4 H 0.626372 0.695296 0.733575 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0756(5) 0.9288(4) 0.3772(3) 0.0266(10) Uani 1 1 d . . . . .
H10 H -0.166878 0.960730 0.341040 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0792(6) 0.9479(4) 0.3629(3) 0.0251(10) Uani 1 1 d . . . . .
H11 H 0.093871 0.993649 0.317410 0.030 Uiso 1 1 calc R U . . .
C9 C -0.0966(5) 0.8633(4) 0.4441(3) 0.0234(9) Uani 1 1 d . . . . .
H9 H -0.202243 0.849026 0.453372 0.028 Uiso 1 1 calc R U . . .
C19 C 0.5230(5) 0.9097(4) 0.8116(2) 0.0236(9) Uani 1 1 d . . . . .
H19 H 0.628488 0.912628 0.800104 0.028 Uiso 1 1 calc R U . . .
C17 C 0.3399(6) 0.9615(4) 0.8970(3) 0.0301(11) Uani 1 1 d . . . . .
H17 H 0.319210 1.002280 0.943188 0.036 Uiso 1 1 calc R U . . .
C18 C 0.4926(6) 0.9670(4) 0.8795(3) 0.0284(10) Uani 1 1 d . . . . .
H18 H 0.576584 1.010003 0.914207 0.034 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'
Br Br -0.2901 2.4595 '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
O24 S1 C2 110.4(2) . . ?
O24 S1 C4 109.06(19) . . ?
O23 S1 O24 115.56(19) . . ?
O23 S1 C2 110.04(19) . . ?
O23 S1 C4 110.3(2) . . ?
C2 S1 C4 100.4(2) . . ?
C5 O6 C1 121.7(3) . . ?
C15 C14 C5 122.6(4) . . ?
C19 C14 C5 119.2(4) . . ?
C19 C14 C15 118.2(4) . . ?
C12 C7 C1 123.7(4) . . ?
C12 C7 C8 117.9(4) . . ?
C8 C7 C1 118.4(4) . . ?
S1 C2 H2 117.9 . . ?
C1 C2 S1 124.1(3) . . ?
C1 C2 H2 117.9 . . ?
C7 C12 Br13 122.0(3) . . ?
C11 C12 Br13 116.9(3) . . ?
C11 C12 C7 121.1(4) . . ?
O6 C1 C7 110.4(3) . . ?
C2 C1 O6 124.2(4) . . ?
C2 C1 C7 125.4(4) . . ?
O6 C5 C14 111.4(3) . . ?
C4 C5 O6 124.7(4) . . ?
C4 C5 C14 123.8(4) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C17 C16 C15 119.2(4) . . ?
C14 C15 Br20 121.2(3) . . ?
C16 C15 Br20 117.5(3) . . ?
C16 C15 C14 121.2(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(4) . . ?
C9 C8 H8 119.3 . . ?
S1 C4 H4 118.1 . . ?
C5 C4 S1 123.9(3) . . ?
C5 C4 H4 118.1 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(4) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C8 C9 C10 119.7(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.0 . . ?
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
Br20 C15 1.878(4) . ?
Br13 C12 1.893(4) . ?
S1 O24 1.442(3) . ?
S1 O23 1.437(3) . ?
S1 C2 1.722(4) . ?
S1 C4 1.725(4) . ?
O6 C1 1.376(5) . ?
O6 C5 1.368(5) . ?
C14 C5 1.488(6) . ?
C14 C15 1.404(6) . ?
C14 C19 1.401(6) . ?
C7 C12 1.396(6) . ?
C7 C1 1.475(6) . ?
C7 C8 1.399(6) . ?
C2 H2 0.9500 . ?
C2 C1 1.335(6) . ?
C12 C11 1.385(6) . ?
C5 C4 1.336(6) . ?
C16 H16 0.9500 . ?
C16 C15 1.382(6) . ?
C16 C17 1.381(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(6) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.393(6) . ?
C10 C9 1.384(6) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.383(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(7) . ?
C18 H18 0.9500 . ?
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
Br13 C12 C11 C10 179.4(3) . . . . ?
S1 C2 C1 O6 -6.7(6) . . . . ?
S1 C2 C1 C7 175.8(3) . . . . ?
O6 C5 C4 S1 -0.5(6) . . . . ?
O24 S1 C2 C1 125.1(4) . . . . ?
O24 S1 C4 C5 -122.7(4) . . . . ?
O23 S1 C2 C1 -106.1(4) . . . . ?
O23 S1 C4 C5 109.3(4) . . . . ?
C14 C5 C4 S1 -177.4(3) . . . . ?
C14 C19 C18 C17 0.9(7) . . . . ?
C7 C12 C11 C10 -1.8(6) . . . . ?
C7 C8 C9 C10 -2.1(6) . . . . ?
C2 S1 C4 C5 -6.7(4) . . . . ?
C12 C7 C1 O6 123.1(4) . . . . ?
C12 C7 C1 C2 -59.1(6) . . . . ?
C12 C7 C8 C9 1.1(6) . . . . ?
C1 O6 C5 C14 -176.1(3) . . . . ?
C1 O6 C5 C4 6.6(6) . . . . ?
C1 C7 C12 Br13 1.0(6) . . . . ?
C1 C7 C12 C11 -177.8(4) . . . . ?
C1 C7 C8 C9 179.8(4) . . . . ?
C5 O6 C1 C7 175.0(3) . . . . ?
C5 O6 C1 C2 -2.8(6) . . . . ?
C5 C14 C15 Br20 6.4(6) . . . . ?
C5 C14 C15 C16 -176.9(4) . . . . ?
C5 C14 C19 C18 177.4(4) . . . . ?
C16 C17 C18 C19 1.2(7) . . . . ?
C15 C14 C5 O6 54.8(5) . . . . ?
C15 C14 C5 C4 -127.9(5) . . . . ?
C15 C14 C19 C18 -3.4(6) . . . . ?
C15 C16 C17 C18 -0.7(7) . . . . ?
C8 C7 C12 Br13 179.6(3) . . . . ?
C8 C7 C12 C11 0.8(6) . . . . ?
C8 C7 C1 O6 -55.5(5) . . . . ?
C8 C7 C1 C2 122.4(5) . . . . ?
C4 S1 C2 C1 10.1(4) . . . . ?
C11 C10 C9 C8 1.1(6) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C19 C14 C5 O6 -126.0(4) . . . . ?
C19 C14 C5 C4 51.3(6) . . . . ?
C19 C14 C15 Br20 -172.8(3) . . . . ?
C19 C14 C15 C16 3.9(6) . . . . ?
C17 C16 C15 Br20 174.9(3) . . . . ?
C17 C16 C15 C14 -1.9(6) . . . . ?
