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#$Date: 2022-02-04 05:20:17 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244027.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_2244027
loop_
_publ_author_name
'Luz, Eduardo Q.'
'Santana, Francielli S.'
'Silverio, Gabriel L.'
'Tullio, Suelen C. M. C.'
'Iodice, Bianca'
'Prola, Liziê D. T.'
'Barbosa, Ronilson V.'
'Rampon, Daniel S.'
_publ_section_title
;
 Crystal structures of
 3-halo-2-organochalcogenylbenzo[b]chalcogenophenes
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022000962
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C14 H9 Br Se2'
_chemical_formula_moiety         'C14 H9 Br Se2'
_chemical_formula_structural     C14H9BrSe2
_chemical_formula_sum            'C14 H9 Br Se2'
_chemical_formula_weight         415.04
_chemical_name_systematic
;
3-Bromo-2-(phenylselanyl)benzo[b]selenophene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.398(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3864(11)
_cell_length_b                   13.6816(11)
_cell_length_c                   8.0982(6)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.94
_cell_volume                     1363.82(19)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            43875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    8.326
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.898
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0345
_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)+(0.0201P)²+2.3843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                2208
_reflns_number_total             2976
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jy2015sup1.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244027
_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.27259(4) 0.68913(3) -0.08792(6) 0.06404(14) Uani d 1 . .
C C2 0.2358(3) 0.5151(2) 0.0834(5) 0.0433(8) Uani d 1 . .
C C3 0.2903(3) 0.5551(3) -0.0323(5) 0.0451(8) Uani d 1 . .
C C4 0.3618(3) 0.4929(3) -0.1127(4) 0.0465(9) Uani d 1 . .
C C5 0.4294(3) 0.5160(4) -0.2330(5) 0.0632(12) Uani d 1 . .
H H5 0.431618 0.579335 -0.274038 0.076 Uiso calc 1 . .
C C6 0.4933(4) 0.4437(5) -0.2911(5) 0.0795(16) Uani d 1 . .
H H6 0.540102 0.459228 -0.369395 0.095 Uiso calc 1 . .
C C7 0.4887(4) 0.3486(5) -0.2344(6) 0.0819(16) Uani d 1 . .
H H7 0.531156 0.300749 -0.277171 0.098 Uiso calc 1 . .
C C8 0.4225(4) 0.3237(4) -0.1160(6) 0.0700(13) Uani d 1 . .
H H8 0.419621 0.259777 -0.077799 0.084 Uiso calc 1 . .
C C9 0.3605(3) 0.3961(3) -0.0552(5) 0.0496(9) Uani d 1 . .
Se Se1 0.26699(4) 0.38117(3) 0.11070(6) 0.05761(13) Uani d 1 . .
Se Se10 0.13853(4) 0.58065(3) 0.21047(6) 0.06282(15) Uani d 1 . .
C C11 0.1055(3) 0.4715(2) 0.3458(4) 0.0422(8) Uani d 1 . .
C C12 0.1734(4) 0.4475(3) 0.4854(5) 0.0616(11) Uani d 1 . .
H H12 0.236377 0.483315 0.515093 0.074 Uiso calc 1 . .
C C13 0.1472(5) 0.3698(4) 0.5807(6) 0.0723(14) Uani d 1 . .
H H13 0.193489 0.352550 0.674522 0.087 Uiso calc 1 . .
C C14 0.0552(4) 0.3181(3) 0.5402(6) 0.0653(13) Uani d 1 . .
H H14 0.038533 0.265737 0.606089 0.078 Uiso calc 1 . .
C C15 -0.0132(4) 0.3424(3) 0.4031(6) 0.0611(11) Uani d 1 . .
H H15 -0.076485 0.306615 0.375672 0.073 Uiso calc 1 . .
C C16 0.0109(3) 0.4202(3) 0.3041(5) 0.0475(9) Uani d 1 . .
H H16 -0.036003 0.437373 0.210910 0.057 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'
Se Se -0.0929 2.2259 '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
C3 C2 Se1 . . 111.6(3) ?
C3 C2 Se10 . . 126.2(3) ?
Se1 C2 Se10 . . 122.15(18) ?
C2 C3 C4 . . 117.5(3) ?
C2 C3 Br1 . . 120.7(3) ?
C4 C3 Br1 . . 121.8(3) ?
C5 C4 C9 . . 118.4(4) ?
C5 C4 C3 . . 129.3(4) ?
C9 C4 C3 . . 112.3(3) ?
C6 C5 C4 . . 119.3(5) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C7 . . 120.9(5) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 121.0(5) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 C9 . . 118.1(5) ?
C7 C8 H8 . . 120.9 ?
C9 C8 H8 . . 120.9 ?
C8 C9 C4 . . 122.2(4) ?
C8 C9 Se1 . . 126.1(4) ?
C4 C9 Se1 . . 111.7(3) ?
C9 Se1 C2 . . 86.85(16) ?
C2 Se10 C11 . . 97.51(14) ?
C12 C11 C16 . . 120.5(4) ?
C12 C11 Se10 . . 120.4(3) ?
C16 C11 Se10 . . 119.1(3) ?
C11 C12 C13 . . 119.2(4) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C14 C13 C12 . . 121.0(4) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 C15 . . 120.1(4) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.4(4) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C11 C16 C15 . . 118.9(4) ?
C11 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
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 C3 . 1.895(4) ?
C2 C3 . 1.333(5) ?
C2 Se1 . 1.881(3) ?
C2 Se10 . 1.894(3) ?
C3 C4 . 1.435(5) ?
C4 C5 . 1.391(5) ?
C4 C9 . 1.404(6) ?
C5 C6 . 1.381(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.383(8) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.372(7) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.378(6) ?
C8 H8 . 0.9300 ?
C9 Se1 . 1.881(4) ?
Se10 C11 . 1.923(3) ?
C11 C12 . 1.372(5) ?
C11 C16 . 1.375(5) ?
C12 C13 . 1.374(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.350(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.361(6) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.385(5) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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
Se1 C2 C3 C4 . . . . -0.7(5) ?
Se10 C2 C3 C4 . . . . 178.9(3) ?
Se1 C2 C3 Br1 . . . . 179.03(19) ?
Se10 C2 C3 Br1 . . . . -1.4(5) ?
C2 C3 C4 C5 . . . . -178.2(4) ?
Br1 C3 C4 C5 . . . . 2.1(6) ?
C2 C3 C4 C9 . . . . 1.1(5) ?
Br1 C3 C4 C9 . . . . -178.6(3) ?
C9 C4 C5 C6 . . . . -0.4(6) ?
C3 C4 C5 C6 . . . . 178.8(4) ?
C4 C5 C6 C7 . . . . 1.7(7) ?
C5 C6 C7 C8 . . . . -1.6(8) ?
C6 C7 C8 C9 . . . . 0.1(7) ?
C7 C8 C9 C4 . . . . 1.2(6) ?
C7 C8 C9 Se1 . . . . -178.2(3) ?
C5 C4 C9 C8 . . . . -1.0(6) ?
C3 C4 C9 C8 . . . . 179.6(4) ?
C5 C4 C9 Se1 . . . . 178.4(3) ?
C3 C4 C9 Se1 . . . . -0.9(4) ?
C8 C9 Se1 C2 . . . . 179.9(4) ?
C4 C9 Se1 C2 . . . . 0.5(3) ?
C3 C2 Se1 C9 . . . . 0.1(3) ?
Se10 C2 Se1 C9 . . . . -179.5(2) ?
C3 C2 Se10 C11 . . . . -177.6(4) ?
Se1 C2 Se10 C11 . . . . 1.9(3) ?
C16 C11 C12 C13 . . . . 1.7(6) ?
Se10 C11 C12 C13 . . . . 179.3(3) ?
C11 C12 C13 C14 . . . . -1.0(7) ?
C12 C13 C14 C15 . . . . 0.1(7) ?
C13 C14 C15 C16 . . . . 0.0(7) ?
C12 C11 C16 C15 . . . . -1.5(6) ?
Se10 C11 C16 C15 . . . . -179.2(3) ?
C14 C15 C16 C11 . . . . 0.7(6) ?

_cod_database_fobs_code 2244027
