#------------------------------------------------------------------------------
#$Date: 2023-09-05 05:00:07 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/97/1569776.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_1569776
loop_
_publ_author_name
'Schollmeyer, Dieter'
'Detert, Heiner'
_publ_section_title
;
 (Z)-4,5-Di-bromo-3,3,6,6-tetra-methyl-2,3,6,7-tetra-hydro-thiepine-1,1-dione.
;
_journal_coeditor_code           BT4132
_journal_issue                   'Pt 1'
_journal_name_full               IUCrData
_journal_page_first              x230042
_journal_paper_doi               10.1107/S2414314623000421
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C10 H16 Br2 O2 S'
_chemical_formula_moiety         'C10 H16 Br2 O2 S'
_chemical_formula_sum            'C10 H16 Br2 O2 S'
_chemical_formula_weight         360.11
_chemical_name_systematic
;
(Z)-4,5-Dibromo-3,3,6,6-tetramethyl-2,3,6,7-tetrahydrothiepine-1,1-dione
;
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                94.804(6)
_cell_angle_beta                 102.448(5)
_cell_angle_gamma                99.356(5)
_cell_formula_units_Z            2
_cell_length_a                   5.9685(4)
_cell_length_b                   8.9642(6)
_cell_length_c                   12.4927(9)
_cell_measurement_reflns_used    18448
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.69
_cell_volume                     639.09(8)
_computing_cell_refinement
;
X-Area Recipe 1.36.0.0 (Stoe & Cie, 2019)
;
_computing_data_collection
;
X-Area WinXpose 2.0.22.0 (Stoe & Cie, 2019)
;
_computing_data_reduction
;
X-Area Integrate 1.77.0.0 (Stoe & Cie, 2019)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8129
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_min         2.693
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    6.485
_exptl_absorpt_correction_T_max  0.5530
_exptl_absorpt_correction_T_min  0.0884
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(XRED; Stoe et al., 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.277
_refine_diff_density_min         -0.894
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0362
_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)+(0.0307P)²+1.4492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                2686
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4132.cif
_cod_data_source_block           I
_cod_database_code               1569776
_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   0.098
_shelx_estimated_absorpt_t_max   0.625
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.15368(7) 0.46873(4) 0.40230(3) 0.03826(12) Uani d 1 . .
Br Br2 0.21628(8) 0.13145(5) 0.44057(3) 0.04584(13) Uani d 1 . .
C C1 0.2846(5) 0.3563(4) 0.3004(2) 0.0251(6) Uani d 1 . .
C C2 0.2791(5) 0.2074(4) 0.3085(3) 0.0265(6) Uani d 1 . .
C C3 0.3191(6) 0.0802(4) 0.2281(3) 0.0281(7) Uani d 1 . .
C C4 0.2643(5) 0.1158(4) 0.1074(3) 0.0266(6) Uani d 1 . .
H H4A 0.115877 0.154728 0.094409 0.032 Uiso calc 1 . .
H H4B 0.235588 0.018273 0.058883 0.032 Uiso calc 1 . .
S S5 0.46965(15) 0.24522(9) 0.06328(7) 0.02945(18) Uani d 1 . .
C C6 0.5605(5) 0.3987(3) 0.1695(3) 0.0254(6) Uani d 1 . .
H H6A 0.674923 0.368072 0.229620 0.031 Uiso calc 1 . .
H H6B 0.645465 0.484410 0.140356 0.031 Uiso calc 1 . .
C C7 0.3767(5) 0.4610(3) 0.2221(3) 0.0226(6) Uani d 1 . .
C C8 0.5636(6) 0.0428(5) 0.2667(4) 0.0401(9) Uani d 1 . .
H H8A 0.586667 -0.036909 0.213729 0.060 Uiso calc 1 . .
H H8B 0.578609 0.006994 0.339500 0.060 Uiso calc 1 . .
H H8C 0.681643 0.134537 0.271694 0.060 Uiso calc 1 . .
C C9 0.1385(7) -0.0676(4) 0.2226(4) 0.0396(8) Uani d 1 . .
H H9A 0.155064 -0.144330 0.165629 0.059 Uiso calc 1 . .
H H9B -0.019675 -0.045063 0.204374 0.059 Uiso calc 1 . .
H H9C 0.165983 -0.106587 0.294348 0.059 Uiso calc 1 . .
O O10 0.6724(5) 0.1800(3) 0.0569(3) 0.0434(7) Uani d 1 . .
O O11 0.3486(5) 0.2945(3) -0.0361(2) 0.0416(6) Uani d 1 . .
C C12 0.1749(6) 0.4981(4) 0.1357(3) 0.0300(7) Uani d 1 . .
H H12A 0.238109 0.561693 0.085059 0.045 Uiso calc 1 . .
H H12B 0.078319 0.553061 0.172897 0.045 Uiso calc 1 . .
H H12C 0.079307 0.403256 0.093870 0.045 Uiso calc 1 . .
C C13 0.5228(6) 0.6125(4) 0.2895(3) 0.0315(7) Uani d 1 . .
H H13A 0.593338 0.675014 0.240333 0.047 Uiso calc 1 . .
H H13B 0.646160 0.589899 0.348092 0.047 Uiso calc 1 . .
H H13C 0.420881 0.668146 0.322457 0.047 Uiso calc 1 . .
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'
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C7 . . 132.0(3) ?
C2 C1 Br1 . . 117.5(2) ?
C7 C1 Br1 . . 110.4(2) ?
C1 C2 C3 . . 130.6(3) ?
C1 C2 Br2 . . 118.0(2) ?
C3 C2 Br2 . . 111.4(2) ?
C8 C3 C2 . . 110.8(3) ?
C8 C3 C4 . . 113.7(3) ?
C2 C3 C4 . . 112.0(3) ?
C8 C3 C9 . . 107.6(3) ?
C2 C3 C9 . . 110.2(3) ?
C4 C3 C9 . . 102.1(3) ?
C3 C4 S5 . . 119.1(2) ?
C3 C4 H4A . . 107.5 ?
S5 C4 H4A . . 107.5 ?
C3 C4 H4B . . 107.5 ?
S5 C4 H4B . . 107.5 ?
H4A C4 H4B . . 107.0 ?
O11 S5 O10 . . 116.84(18) ?
O11 S5 C4 . . 107.11(16) ?
O10 S5 C4 . . 110.42(17) ?
O11 S5 C6 . . 109.96(16) ?
O10 S5 C6 . . 106.90(16) ?
C4 S5 C6 . . 105.01(15) ?
C7 C6 S5 . . 119.5(2) ?
C7 C6 H6A . . 107.4 ?
S5 C6 H6A . . 107.4 ?
C7 C6 H6B . . 107.4 ?
S5 C6 H6B . . 107.4 ?
H6A C6 H6B . . 107.0 ?
C1 C7 C12 . . 111.0(3) ?
C1 C7 C6 . . 112.8(2) ?
C12 C7 C6 . . 112.6(3) ?
C1 C7 C13 . . 109.7(3) ?
C12 C7 C13 . . 108.7(3) ?
C6 C7 C13 . . 101.5(2) ?
C3 C8 H8A . . 109.5 ?
C3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C3 C9 H9A . . 109.5 ?
C3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C7 C13 H13A . . 109.5 ?
C7 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C7 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.927(3) ?
Br2 C2 . 1.923(3) ?
C1 C2 . 1.343(5) ?
C1 C7 . 1.536(4) ?
C2 C3 . 1.538(5) ?
C3 C8 . 1.535(5) ?
C3 C4 . 1.543(5) ?
C3 C9 . 1.552(5) ?
C4 S5 . 1.758(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
S5 O11 . 1.438(3) ?
S5 O10 . 1.441(3) ?
S5 C6 . 1.758(3) ?
C6 C7 . 1.547(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C12 . 1.536(4) ?
C7 C13 . 1.556(4) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C1 C2 C3 . . . . -13.7(6) ?
Br1 C1 C2 C3 . . . . 165.7(3) ?
C7 C1 C2 Br2 . . . . 165.3(3) ?
Br1 C1 C2 Br2 . . . . -15.3(3) ?
C1 C2 C3 C8 . . . . 102.4(4) ?
Br2 C2 C3 C8 . . . . -76.6(3) ?
C1 C2 C3 C4 . . . . -25.7(5) ?
Br2 C2 C3 C4 . . . . 155.3(2) ?
C1 C2 C3 C9 . . . . -138.6(4) ?
Br2 C2 C3 C9 . . . . 42.4(3) ?
C8 C3 C4 S5 . . . . -48.3(4) ?
C2 C3 C4 S5 . . . . 78.3(3) ?
C9 C3 C4 S5 . . . . -163.9(2) ?
C3 C4 S5 O11 . . . . -161.6(2) ?
C3 C4 S5 O10 . . . . 70.2(3) ?
C3 C4 S5 C6 . . . . -44.7(3) ?
O11 S5 C6 C7 . . . . 71.3(3) ?
O10 S5 C6 C7 . . . . -161.0(3) ?
C4 S5 C6 C7 . . . . -43.7(3) ?
C2 C1 C7 C12 . . . . 105.5(4) ?
Br1 C1 C7 C12 . . . . -73.9(3) ?
C2 C1 C7 C6 . . . . -21.9(5) ?
Br1 C1 C7 C6 . . . . 158.6(2) ?
C2 C1 C7 C13 . . . . -134.3(4) ?
Br1 C1 C7 C13 . . . . 46.3(3) ?
S5 C6 C7 C1 . . . . 74.8(3) ?
S5 C6 C7 C12 . . . . -51.8(3) ?
S5 C6 C7 C13 . . . . -167.8(2) ?
