#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:49:47 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/47/7234794.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_7234794
loop_
_publ_author_name
'Chongboriboon, Nucharee'
'Samakun, Kodchakorn'
'Inprasit, Thitirat'
'Kielar, Filip'
'Dungkaew, Winya'
'Wong, Lawrence W.-Y.'
'Sung, Herman H.-Y.'
'Ninković, Dragan B.'
'Zarić, Snežana D.'
'Chainok, Kittipong'
_publ_section_title
;
 Two-dimensional halogen-bonded organic frameworks based on the
 tetrabromobenzene-1,4-dicarboxylic acid building molecule
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              24
_journal_page_last               34
_journal_paper_doi               10.1039/C9CE01140D
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C8 H2 Br4 O4, 2(C2 H6 O S)'
_chemical_formula_sum            'C12 H14 Br4 O6 S2'
_chemical_formula_weight         637.99
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-18 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.24933(17)
_cell_length_b                   25.7601(6)
_cell_length_c                   8.66218(18)
_cell_measurement_reflns_used    3078
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.500
_cell_measurement_theta_min      5.388
_cell_volume                     2063.88(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10378
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.473
_diffrn_reflns_theta_min         5.388
_exptl_absorpt_coefficient_mu    11.639
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    2.053
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.713
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0453
_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)+(0.0378P)²+19.5076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1809
_reflns_number_total             1901
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01140d2.cif
_cod_data_source_block           4lt
_cod_depositor_comments
;Adding full bibliography for 7234791--7234798.cif.

 Adding full bibliography for 7234791--7234798.cif.
;
_cod_database_code               7234794
_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   0.184
_shelx_estimated_absorpt_t_min   0.152
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.82 with sigma of 0.01
3.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
Br1 Br 0.97147(6) 0.31523(2) 0.27940(6) 0.01516(19) Uani 1 1 d .
Br2 Br 0.52371(6) 0.31534(2) 0.71941(6) 0.01654(19) Uani 1 1 d .
S1 S 0.70934(14) 0.51505(5) 0.54164(14) 0.0180(3) Uani 1 1 d .
O1 O 0.8296(4) 0.38396(13) 0.5974(4) 0.0156(7) Uani 1 1 d D
O2 O 0.6660(4) 0.38577(13) 0.4071(4) 0.0166(8) Uani 1 1 d .
O3 O 0.8237(4) 0.48094(14) 0.6176(5) 0.0252(9) Uani 1 1 d .
C1 C 0.7445(4) 0.36284(18) 0.4987(5) 0.0102(9) Uani 1 1 d .
C2 C 0.7480(4) 0.30398(19) 0.5000(5) 0.0085(9) Uani 1 1 d .
C3 C 0.8428(5) 0.27702(17) 0.4056(5) 0.0103(9) Uani 1 1 d .
C4 C 0.6524(5) 0.27687(18) 0.5937(5) 0.0114(9) Uani 1 1 d .
C5 C 0.8013(8) 0.5740(2) 0.4973(8) 0.0358(15) Uani 1 1 d .
H5A H 0.840228 0.589149 0.592403 0.054 Uiso 1 1 calc GR
H5B H 0.733545 0.598462 0.449614 0.054 Uiso 1 1 calc GR
H5C H 0.880712 0.566815 0.425512 0.054 Uiso 1 1 calc GR
C6 C 0.6012(6) 0.5387(2) 0.6968(7) 0.0246(12) Uani 1 1 d .
H6A H 0.547868 0.509796 0.743337 0.037 Uiso 1 1 calc GR
H6B H 0.532766 0.564551 0.657560 0.037 Uiso 1 1 calc GR
H6C H 0.663671 0.554727 0.774781 0.037 Uiso 1 1 calc GR
H1 H 0.824(12) 0.4158(5) 0.600(12) 0.09(3) Uiso 1 1 d D
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'
Br Br -0.6763 1.2805 '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
O3 S1 C5 104.7(3) . .
O3 S1 C6 105.1(3) . .
C6 S1 C5 98.0(3) . .
C1 O1 H1 114(8) . .
O1 C1 C2 113.9(4) . .
O2 C1 O1 126.1(5) . .
O2 C1 C2 119.9(4) . .
C3 C2 C1 120.7(4) . .
C3 C2 C4 119.7(4) . .
C4 C2 C1 119.6(4) . .
C2 C3 Br1 118.6(3) . .
C2 C3 C3 120.1(3) . 7_565
C3 C3 Br1 121.35(14) 7_565 .
C2 C4 Br2 118.2(3) . .
C4 C4 Br2 121.55(14) 7_565 .
C4 C4 C2 120.2(3) 7_565 .
S1 C5 H5A 109.5 . .
S1 C5 H5B 109.5 . .
S1 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
S1 C6 H6A 109.5 . .
S1 C6 H6B 109.5 . .
S1 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.892(4) .
Br2 C4 1.893(5) .
S1 O3 1.524(4) .
S1 C5 1.782(6) .
S1 C6 1.782(6) .
O1 C1 1.284(6) .
O1 H1 0.821(10) .
O2 C1 1.227(6) .
C1 C2 1.516(7) .
C2 C3 1.386(6) .
C2 C4 1.388(7) .
C3 C3 1.392(9) 7_565
C4 C4 1.385(9) 7_565
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6B O2 0.98 2.31 3.272(6) 167.3 5_666 yes
O1 H1 O3 0.821(10) 1.686(15) 2.505(5) 175(11) . yes
