#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227069.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_2227069
loop_
_publ_author_name
'Jin, Guojun'
'Lu, Yinghui'
_publ_section_title
;
 5,8-Dibromo-15,18-dimethoxy-2,11-dithia[3.3]paracyclophane
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2144
_journal_paper_doi               10.1107/S1600536810029053
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H18 Br2 O2 S2'
_chemical_formula_moiety         'C18 H18 Br2 O2 S2'
_chemical_formula_sum            'C18 H18 Br2 O2 S2'
_chemical_formula_weight         490.26
_chemical_name_systematic
;
1²,1⁵-dibromo-5²,5⁵-dimethoxy-2,7-dithia-1,5(1,4)-dibenzenaoctaphane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9576(8)
_cell_length_b                   16.2291(14)
_cell_length_c                   13.0251(11)
_cell_measurement_reflns_used    3885
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.51
_cell_volume                     1843.2(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_av_sigmaI/netI    0.0953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12800
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    4.633
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.004
_refine_diff_density_min         -1.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0592
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0753P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                2812
_reflns_number_total             4475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            si2274.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227069
_cod_database_fobs_code          2227069
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.56512(6) 0.00221(3) 0.68306(4) 0.0672(2) Uani d . 1 . .
Br Br2 1.04343(6) 0.17844(3) 0.44267(4) 0.05796(19) Uani d . 1 . .
C C1 0.9651(5) 0.0721(2) 0.6001(3) 0.0383(9) Uani d . 1 . .
C C2 0.8556(5) 0.0352(2) 0.6428(3) 0.0414(9) Uani d . 1 . .
H H2 0.8858 -0.0067 0.6919 0.050 Uiso calc R 1 . .
C C3 0.7037(5) 0.0569(2) 0.6166(3) 0.0421(9) Uani d . 1 . .
C C4 0.6510(5) 0.1210(2) 0.5448(3) 0.0426(9) Uani d . 1 . .
C C5 0.7568(5) 0.1535(2) 0.4937(3) 0.0419(9) Uani d . 1 . .
H H5 0.7248 0.1924 0.4408 0.050 Uiso calc R 1 . .
C C6 0.9099(5) 0.1296(2) 0.5193(3) 0.0386(9) Uani d . 1 . .
C C7 1.1351(5) 0.0552(3) 0.6408(3) 0.0478(10) Uani d . 1 . .
H H7A 1.1921 0.1026 0.6250 0.057 Uiso calc R 1 . .
H H7B 1.1630 0.0085 0.6027 0.057 Uiso calc R 1 . .
C C8 1.2053(5) 0.1368(3) 0.8357(3) 0.0603(13) Uani d . 1 . .
H H8A 1.2330 0.1323 0.9120 0.072 Uiso calc R 1 . .
H H8B 1.2865 0.1669 0.8140 0.072 Uiso calc R 1 . .
C C9 1.0584(5) 0.1853(3) 0.8039(3) 0.0483(11) Uani d . 1 . .
C C10 0.9312(5) 0.1636(3) 0.8413(3) 0.0466(10) Uani d . 1 . .
C C11 0.7901(5) 0.1997(3) 0.7979(3) 0.0461(10) Uani d . 1 . .
H H11 0.7041 0.1842 0.8220 0.055 Uiso calc R 1 . .
C C12 0.7759(5) 0.2590(3) 0.7186(3) 0.0423(9) Uani d . 1 . .
C C13 0.9054(5) 0.2850(3) 0.6891(3) 0.0447(10) Uani d . 1 . .
C C14 1.0460(5) 0.2476(3) 0.7292(3) 0.0480(10) Uani d . 1 . .
H H14 1.1321 0.2642 0.7061 0.058 Uiso calc R 1 . .
C C15 0.6193(5) 0.2917(3) 0.6623(4) 0.0519(11) Uani d . 1 . .
H H15A 0.6279 0.3141 0.5948 0.062 Uiso calc R 1 . .
H H15B 0.5928 0.3368 0.7035 0.062 Uiso calc R 1 . .
C C16 0.4926(5) 0.1575(3) 0.5276(4) 0.0531(11) Uani d . 1 . .
H H16A 0.4179 0.1132 0.5143 0.064 Uiso calc R 1 . .
H H16B 0.4745 0.1922 0.4654 0.064 Uiso calc R 1 . .
C C17 0.8336(7) 0.0803(4) 0.9594(4) 0.0767(16) Uani d . 1 . .
H H17A 0.7924 0.1276 0.9874 0.115 Uiso calc R 1 . .
H H17B 0.8688 0.0411 1.0149 0.115 Uiso calc R 1 . .
H H17C 0.7553 0.0555 0.9054 0.115 Uiso calc R 1 . .
C C18 1.0126(6) 0.3817(3) 0.5888(4) 0.0703(14) Uani d . 1 . .
H H18A 1.0703 0.4095 0.6503 0.106 Uiso calc R 1 . .
H H18B 0.9807 0.4208 0.5328 0.106 Uiso calc R 1 . .
H H18C 1.0756 0.3402 0.5673 0.106 Uiso calc R 1 . .
O O1 0.9536(4) 0.1039(2) 0.9173(2) 0.0666(9) Uani d . 1 . .
O O2 0.8860(4) 0.34533(19) 0.6119(2) 0.0584(8) Uani d . 1 . .
S S1 1.19297(14) 0.03433(8) 0.77929(9) 0.0601(3) Uani d . 1 . .
S S2 0.46307(13) 0.21831(8) 0.63885(10) 0.0559(3) Uani d . 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 C6 . . 115.5(4) ?
C2 C1 C7 . . 122.2(4) ?
C6 C1 C7 . . 122.2(4) ?
C3 C2 C1 . . 123.3(4) ?
C3 C2 H2 . . 118.4 ?
C1 C2 H2 . . 118.4 ?
C2 C3 C4 . . 121.2(4) ?
C2 C3 Br1 . . 119.0(3) ?
C4 C3 Br1 . . 119.8(3) ?
C5 C4 C3 . . 116.1(4) ?
C5 C4 C16 . . 120.4(4) ?
C3 C4 C16 . . 123.4(4) ?
C4 C5 C6 . . 121.7(4) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 121.5(4) ?
C5 C6 Br2 . . 117.6(3) ?
C1 C6 Br2 . . 120.9(3) ?
C1 C7 S1 . . 114.9(3) ?
C1 C7 H7A . . 108.5 ?
S1 C7 H7A . . 108.5 ?
C1 C7 H7B . . 108.5 ?
S1 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C9 C8 S1 . . 113.5(3) ?
C9 C8 H8A . . 108.9 ?
S1 C8 H8A . . 108.9 ?
C9 C8 H8B . . 108.9 ?
S1 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.7 ?
C10 C9 C14 . . 119.4(4) ?
C10 C9 C8 . . 120.5(4) ?
C14 C9 C8 . . 119.8(4) ?
O1 C10 C9 . . 116.0(4) ?
O1 C10 C11 . . 124.2(4) ?
C9 C10 C11 . . 119.7(4) ?
C10 C11 C12 . . 120.7(4) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C13 C12 C11 . . 118.7(4) ?
C13 C12 C15 . . 120.3(4) ?
C11 C12 C15 . . 120.9(4) ?
C12 C13 O2 . . 116.6(4) ?
C12 C13 C14 . . 120.9(4) ?
O2 C13 C14 . . 122.3(4) ?
C13 C14 C9 . . 120.1(4) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
C12 C15 S2 . . 116.4(3) ?
C12 C15 H15A . . 108.2 ?
S2 C15 H15A . . 108.2 ?
C12 C15 H15B . . 108.2 ?
S2 C15 H15B . . 108.2 ?
H15A C15 H15B . . 107.3 ?
C4 C16 S2 . . 113.5(3) ?
C4 C16 H16A . . 108.9 ?
S2 C16 H16A . . 108.9 ?
C4 C16 H16B . . 108.9 ?
S2 C16 H16B . . 108.9 ?
H16A C16 H16B . . 107.7 ?
O1 C17 H17A . . 109.5 ?
O1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O2 C18 H18A . . 109.5 ?
O2 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O2 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C10 O1 C17 . . 119.3(4) ?
C18 O2 C13 . . 119.4(4) ?
C7 S1 C8 . . 102.2(2) ?
C15 S2 C16 . . 104.1(2) ?
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 C3 . 1.889(4) ?
Br2 C6 . 1.898(4) ?
C1 C2 . 1.372(6) ?
C1 C6 . 1.408(5) ?
C1 C7 . 1.518(6) ?
C2 C3 . 1.371(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.407(5) ?
C4 C5 . 1.382(6) ?
C4 C16 . 1.506(6) ?
C5 C6 . 1.390(6) ?
C5 H5 . 0.9300 ?
C7 S1 . 1.792(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.508(6) ?
C8 S1 . 1.812(5) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.384(6) ?
C9 C14 . 1.389(6) ?
C10 O1 . 1.368(5) ?
C10 C11 . 1.390(6) ?
C11 C12 . 1.397(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.369(6) ?
C12 C15 . 1.521(6) ?
C13 O2 . 1.386(5) ?
C13 C14 . 1.388(6) ?
C14 H14 . 0.9300 ?
C15 S2 . 1.809(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 S2 . 1.822(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 O1 . 1.369(6) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 O2 . 1.372(6) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
C6 C1 C2 C3 . . . . -5.6(6) ?
C7 C1 C2 C3 . . . . 171.5(4) ?
C1 C2 C3 C4 . . . . -1.6(6) ?
C1 C2 C3 Br1 . . . . -179.0(3) ?
C2 C3 C4 C5 . . . . 7.4(6) ?
Br1 C3 C4 C5 . . . . -175.2(3) ?
C2 C3 C4 C16 . . . . -168.8(4) ?
Br1 C3 C4 C16 . . . . 8.6(5) ?
C3 C4 C5 C6 . . . . -6.0(6) ?
C16 C4 C5 C6 . . . . 170.4(4) ?
C4 C5 C6 C1 . . . . -1.2(6) ?
C4 C5 C6 Br2 . . . . 179.7(3) ?
C2 C1 C6 C5 . . . . 7.0(5) ?
C7 C1 C6 C5 . . . . -170.2(4) ?
C2 C1 C6 Br2 . . . . -174.0(3) ?
C7 C1 C6 Br2 . . . . 8.8(5) ?
C2 C1 C7 S1 . . . . -32.5(5) ?
C6 C1 C7 S1 . . . . 144.4(3) ?
S1 C8 C9 C10 . . . . 69.9(5) ?
S1 C8 C9 C14 . . . . -104.4(4) ?
C14 C9 C10 O1 . . . . -177.8(4) ?
C8 C9 C10 O1 . . . . 7.9(6) ?
C14 C9 C10 C11 . . . . 5.1(6) ?
C8 C9 C10 C11 . . . . -169.2(4) ?
O1 C10 C11 C12 . . . . -178.4(4) ?
C9 C10 C11 C12 . . . . -1.5(6) ?
C10 C11 C12 C13 . . . . -4.2(6) ?
C10 C11 C12 C15 . . . . 173.1(4) ?
C11 C12 C13 O2 . . . . -178.4(4) ?
C15 C12 C13 O2 . . . . 4.2(5) ?
C11 C12 C13 C14 . . . . 6.4(6) ?
C15 C12 C13 C14 . . . . -171.0(4) ?
C12 C13 C14 C9 . . . . -2.8(6) ?
O2 C13 C14 C9 . . . . -177.7(3) ?
C10 C9 C14 C13 . . . . -3.0(6) ?
C8 C9 C14 C13 . . . . 171.4(4) ?
C13 C12 C15 S2 . . . . 141.2(3) ?
C11 C12 C15 S2 . . . . -36.0(5) ?
C5 C4 C16 S2 . . . . -105.9(4) ?
C3 C4 C16 S2 . . . . 70.2(5) ?
C9 C10 O1 C17 . . . . 178.9(4) ?
C11 C10 O1 C17 . . . . -4.1(7) ?
C12 C13 O2 C18 . . . . 171.4(4) ?
C14 C13 O2 C18 . . . . -13.5(6) ?
C1 C7 S1 C8 . . . . -80.3(4) ?
C9 C8 S1 C7 . . . . 56.6(4) ?
C12 C15 S2 C16 . . . . -76.7(4) ?
C4 C16 S2 C15 . . . . 53.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745627
2 PubChem 12415624
