#------------------------------------------------------------------------------
#$Date: 2022-11-10 04:47:41 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279171 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022697.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_2022697
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 Se'
_chemical_formula_moiety         'C8 H4 Br I N2 Se'
_chemical_formula_sum            'C8 H4 Br I N2 Se'
_chemical_formula_weight         413.90
_chemical_name_systematic
;
2-Bromo-5-(4-iodophenyl)-1,3,4-selenadiazole
;
_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 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1735(4)
_cell_length_b                   7.1222(2)
_cell_length_c                   26.1875(8)
_cell_measurement_reflns_used    7358
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      33.0220
_cell_measurement_theta_min      2.3610
_cell_volume                     2084.00(11)
_computing_cell_refinement
;
CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro 1.171.40.84a (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      100.00(10)
_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 1.000
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12091
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    10.355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    2.638
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.003
_refine_diff_density_min         -1.013
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0296
_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)+(0.0300P)²+10.0022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                1815
_reflns_number_total             2055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bs3004sup1.cif
_cod_data_source_block           T3
_cod_database_code               2022697
_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   0.147
_shelx_estimated_absorpt_t_max   0.575
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 0.6730(4) 0.6139(6) 0.59069(17) 0.0149(9) Uani d 1 . .
C C2 0.5578(4) 0.5876(7) 0.61022(17) 0.0196(10) Uani d 1 . .
H H2 0.4902 0.6141 0.5894 0.023 Uiso calc 1 . .
C C3 0.5414(5) 0.5230(7) 0.65978(18) 0.0226(10) Uani d 1 . .
H H3 0.4630 0.5045 0.6729 0.027 Uiso calc 1 . .
C C4 0.6408(5) 0.4859(6) 0.68987(16) 0.0195(10) Uani d 1 . .
C C5 0.7557(5) 0.5112(6) 0.67115(17) 0.0213(10) Uani d 1 . .
H H5 0.8227 0.4847 0.6923 0.026 Uiso calc 1 . .
C C6 0.7731(4) 0.5751(6) 0.62163(17) 0.0176(10) Uani d 1 . .
H H6 0.8518 0.5925 0.6087 0.021 Uiso calc 1 . .
C C7 0.6914(4) 0.6814(6) 0.53853(16) 0.0122(9) Uani d 1 . .
N N8 0.7974(3) 0.7053(5) 0.51957(14) 0.0171(8) Uani d 1 . .
N N9 0.8006(3) 0.7683(5) 0.46942(14) 0.0184(8) Uani d 1 . .
C C10 0.6957(4) 0.7927(6) 0.45060(17) 0.0151(9) Uani d 1 . .
Se Se11 0.56664(4) 0.74266(7) 0.49341(2) 0.01587(12) Uani d 1 . .
Br Br12 0.67471(4) 0.87353(7) 0.38316(2) 0.02129(13) Uani d 1 . .
I I13 0.61637(4) 0.38409(5) 0.76407(2) 0.03129(12) 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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 . . 119.6(4) ?
C2 C1 C7 . . 121.0(4) ?
C6 C1 C7 . . 119.4(4) ?
C1 C2 H2 . . 119.7 ?
C3 C2 C1 . . 120.5(5) ?
C3 C2 H2 . . 119.7 ?
C2 C3 H3 . . 120.4 ?
C4 C3 C2 . . 119.2(5) ?
C4 C3 H3 . . 120.4 ?
C3 C4 I13 . . 119.3(3) ?
C5 C4 C3 . . 121.1(4) ?
C5 C4 I13 . . 119.6(4) ?
C4 C5 H5 . . 119.9 ?
C4 C5 C6 . . 120.2(4) ?
C6 C5 H5 . . 119.9 ?
C1 C6 H6 . . 120.3 ?
C5 C6 C1 . . 119.4(4) ?
C5 C6 H6 . . 120.3 ?
C1 C7 Se11 . . 124.0(3) ?
N8 C7 C1 . . 122.0(4) ?
N8 C7 Se11 . . 114.0(3) ?
C7 N8 N9 . . 115.4(4) ?
C10 N9 N8 . . 112.5(4) ?
N9 C10 Se11 . . 116.8(3) ?
N9 C10 Br12 . . 121.2(3) ?
Se11 C10 Br12 . . 122.0(2) ?
C10 Se11 C7 . . 81.29(19) ?
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 . 1.398(7) ?
C1 C6 . 1.408(6) ?
C1 C7 . 1.462(6) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.389(7) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.387(7) ?
C4 C5 . 1.386(7) ?
C4 I13 . 2.092(4) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.388(6) ?
C6 H6 . 0.9500 ?
C7 N8 . 1.295(6) ?
C7 Se11 . 1.879(4) ?
N8 N9 . 1.388(5) ?
N9 C10 . 1.284(6) ?
C10 Se11 . 1.861(5) ?
C10 Br12 . 1.872(4) ?
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 . . . . 0.4(7) ?
C1 C7 N8 N9 . . . . 179.4(4) ?
C1 C7 Se11 C10 . . . . -179.4(4) ?
C2 C1 C6 C5 . . . . 0.0(7) ?
C2 C1 C7 N8 . . . . -179.5(4) ?
C2 C1 C7 Se11 . . . . 1.1(6) ?
C2 C3 C4 C5 . . . . -0.4(7) ?
C2 C3 C4 I13 . . . . -178.9(3) ?
C3 C4 C5 C6 . . . . 0.2(7) ?
C4 C5 C6 C1 . . . . 0.0(7) ?
C6 C1 C2 C3 . . . . -0.2(7) ?
C6 C1 C7 N8 . . . . 0.6(6) ?
C6 C1 C7 Se11 . . . . -178.9(3) ?
C7 C1 C2 C3 . . . . 179.8(4) ?
C7 C1 C6 C5 . . . . 180.0(4) ?
C7 N8 N9 C10 . . . . 0.3(6) ?
N8 C7 Se11 C10 . . . . 1.1(3) ?
N8 N9 C10 Se11 . . . . 0.7(5) ?
N8 N9 C10 Br12 . . . . -179.0(3) ?
N9 C10 Se11 C7 . . . . -1.0(4) ?
Se11 C7 N8 N9 . . . . -1.1(5) ?
Br12 C10 Se11 C7 . . . . 178.7(3) ?
I13 C4 C5 C6 . . . . 178.7(3) ?

_cod_database_fobs_code 2022697
