#------------------------------------------------------------------------------
#$Date: 2022-11-10 04:47:41 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022698.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_2022698
loop_
_publ_author_name
'De Silva, Viraj'
'Magueres, Pierre Le'
'Averkiev, Boris B.'
'Aakeröy, Christer B.'
_publ_section_title
;
 Competition between chalcogen and halogen bonding assessed through
 isostructural species
;
_journal_coeditor_code           BS3004
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322962201052X
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C8 H4 Br I N2 S'
_chemical_formula_moiety         'C8 H4 Br I N2 S'
_chemical_formula_sum            'C8 H4 Br I N2 S'
_chemical_formula_weight         367.00
_chemical_name_systematic
;
2-Bromo-5-(4-iodophenyl)-1,3,4-thiadiazole
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
OLEX2
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9919(2)
_cell_length_b                   6.99450(10)
_cell_length_c                   26.4076(4)
_cell_measurement_reflns_used    5134
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6430
_cell_measurement_theta_min      3.3330
_cell_volume                     2030.29(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(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 0.984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Custom diffractometer with a HyPix-Arc 150° detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7258
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.701
_diffrn_reflns_theta_min         3.347
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    30.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.401
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.669
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0210
_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)+(0.0219P)²+2.6464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0517
_reflns_number_gt                1802
_reflns_number_total             1920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bs3004sup1.cif
_cod_data_source_block           T4
_cod_database_code               2022698
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
C C1 0.6729(3) 0.3732(4) 0.40837(11) 0.0202(6) Uani d 1 . .
C C2 0.5551(3) 0.4009(4) 0.38896(11) 0.0228(7) Uani d 1 . .
H H2 0.487684 0.378054 0.409375 0.027 Uiso calc 1 . .
C C3 0.5392(3) 0.4619(5) 0.33964(11) 0.0252(7) Uani d 1 . .
H H3 0.461242 0.482985 0.327092 0.030 Uiso calc 1 . .
C C4 0.6391(3) 0.4915(5) 0.30907(11) 0.0245(7) Uani d 1 . .
C C5 0.7571(3) 0.4651(5) 0.32710(11) 0.0232(6) Uani d 1 . .
H H5 0.823891 0.487009 0.306263 0.028 Uiso calc 1 . .
C C6 0.7730(3) 0.4053(4) 0.37681(12) 0.0217(6) Uani d 1 . .
H H6 0.851192 0.386382 0.389268 0.026 Uiso calc 1 . .
C C7 0.6931(3) 0.3097(5) 0.46055(11) 0.0205(6) Uani d 1 . .
N N8 0.8022(2) 0.2851(4) 0.47936(9) 0.0229(6) Uani d 1 . .
N N9 0.8006(2) 0.2255(4) 0.52908(9) 0.0236(6) Uani d 1 . .
C C10 0.6900(3) 0.2081(5) 0.54533(11) 0.0225(6) Uani d 1 . .
S S11 0.57681(6) 0.25939(12) 0.50282(3) 0.02332(17) Uani d 1 . .
Br Br12 0.65699(3) 0.13399(5) 0.61220(2) 0.02781(10) Uani d 1 . .
I I13 0.61471(2) 0.58780(3) 0.23455(2) 0.03153(9) 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 0.0181 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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0038
0 0 -1 0.0078
0 -1 0 0.0231
0 1 0 0.0251
-3 0 2 0.0133
3 0 -2 0.0213
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 . . 121.6(3) ?
C6 C1 C2 . . 119.0(3) ?
C6 C1 C7 . . 119.4(3) ?
C1 C2 H2 . . 119.9 ?
C3 C2 C1 . . 120.2(3) ?
C3 C2 H2 . . 119.9 ?
C2 C3 H3 . . 120.1 ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C3 C4 C5 . . 121.4(3) ?
C3 C4 I13 . . 119.7(2) ?
C5 C4 I13 . . 118.8(2) ?
C4 C5 H5 . . 120.7 ?
C6 C5 C4 . . 118.7(3) ?
C6 C5 H5 . . 120.7 ?
C1 C6 H6 . . 119.6 ?
C5 C6 C1 . . 120.9(3) ?
C5 C6 H6 . . 119.6 ?
C1 C7 S11 . . 123.8(2) ?
N8 C7 C1 . . 122.4(3) ?
N8 C7 S11 . . 113.9(2) ?
C7 N8 N9 . . 113.0(2) ?
C10 N9 N8 . . 110.8(2) ?
N9 C10 S11 . . 116.4(2) ?
N9 C10 Br12 . . 121.3(2) ?
S11 C10 Br12 . . 122.26(17) ?
C10 S11 C7 . . 85.92(14) ?
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
C1 C2 . 1.407(4) ?
C1 C6 . 1.398(4) ?
C1 C7 . 1.465(4) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.382(4) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.379(4) ?
C4 C5 . 1.394(4) ?
C4 I13 . 2.097(3) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.388(4) ?
C6 H6 . 0.9300 ?
C7 N8 . 1.309(4) ?
C7 S11 . 1.733(3) ?
N8 N9 . 1.378(3) ?
N9 C10 . 1.295(4) ?
C10 S11 . 1.714(3) ?
C10 Br12 . 1.876(3) ?
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
C1 C2 C3 C4 . . . . 1.5(5) ?
C1 C7 N8 N9 . . . . 179.9(3) ?
C1 C7 S11 C10 . . . . -179.7(3) ?
C2 C1 C6 C5 . . . . 0.5(5) ?
C2 C1 C7 N8 . . . . -179.3(3) ?
C2 C1 C7 S11 . . . . 1.0(4) ?
C2 C3 C4 C5 . . . . -1.4(5) ?
C2 C3 C4 I13 . . . . -179.2(2) ?
C3 C4 C5 C6 . . . . 0.8(5) ?
C4 C5 C6 C1 . . . . -0.4(5) ?
C6 C1 C2 C3 . . . . -1.0(5) ?
C6 C1 C7 N8 . . . . 1.3(5) ?
C6 C1 C7 S11 . . . . -178.3(2) ?
C7 C1 C2 C3 . . . . 179.6(3) ?
C7 C1 C6 C5 . . . . 179.8(3) ?
C7 N8 N9 C10 . . . . 0.0(4) ?
N8 C7 S11 C10 . . . . 0.6(3) ?
N8 N9 C10 S11 . . . . 0.5(4) ?
N8 N9 C10 Br12 . . . . -178.7(2) ?
N9 C10 S11 C7 . . . . -0.6(3) ?
S11 C7 N8 N9 . . . . -0.5(4) ?
Br12 C10 S11 C7 . . . . 178.6(2) ?
I13 C4 C5 C6 . . . . 178.6(2) ?

_cod_database_fobs_code 2022698
