#------------------------------------------------------------------------------
#$Date: 2021-07-28 08:23:42 +0300 (Wed, 28 Jul 2021) $
#$Revision: 267783 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108852.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_2108852
loop_
_publ_author_name
'Bujak, Maciej'
'Podsiadło, Marcin'
'Katrusiak, Andrzej'
_publ_section_title
;
 Properties and interactions -- melting point of tribromobenzene isomers
;
_journal_coeditor_code           LO5092
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520621006399
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C6 H3 Br3'
_chemical_formula_sum            'C6 H3 Br3'
_chemical_formula_weight         314.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            48
_cell_length_a                   29.313(2)
_cell_length_b                   78.645(4)
_cell_length_c                   3.9320(2)
_cell_measurement_reflns_used    5134
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      3.09
_cell_volume                     9064.5(9)
_computing_cell_refinement
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2020)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_unetI/netI     0.1169
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       97
_diffrn_reflns_limit_k_min       -82
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            19208
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    15.924
_exptl_absorpt_correction_T_max  0.375
_exptl_absorpt_correction_T_min  0.042
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             6912
_exptl_crystal_size_max          0.93
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.179
_refine_diff_density_min         -1.717
_refine_diff_density_rms         0.281
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4368
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3365
_reflns_number_total             4368
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5092sup1.cif
_cod_data_source_block           124TBB_100K
_cod_database_code               2108852
_shelx_shelxl_version_number     2014/7
_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   0.024
_shelx_estimated_absorpt_t_max   0.402
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br11 Br 0.07364(7) 0.00227(2) 0.8783(6) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.1255(6) 0.0158(2) 0.830(5) 0.016(4) Uani 1 1 d . U . . .
Br12 Br 0.17899(7) -0.01151(2) 1.0908(6) 0.0265(5) Uani 1 1 d . . . . .
C12 C 0.1686(7) 0.0109(2) 0.929(5) 0.016(4) Uani 1 1 d . U . . .
C13 C 0.2060(7) 0.0215(2) 0.897(5) 0.023(4) Uani 1 1 d . U . . .
H13 H 0.2349 0.0180 0.9664 0.028 Uiso 1 1 calc R U . . .
Br14 Br 0.25167(7) 0.05160(2) 0.7012(6) 0.0271(5) Uani 1 1 d . . . . .
C14 C 0.1992(7) 0.0375(2) 0.759(5) 0.021(4) Uani 1 1 d . U . . .
C15 C 0.1580(6) 0.0430(2) 0.655(5) 0.017(4) Uani 1 1 d . U . . .
H15 H 0.1549 0.0539 0.5646 0.021 Uiso 1 1 calc R U . . .
C16 C 0.1194(7) 0.0323(2) 0.683(5) 0.018(4) Uani 1 1 d . U . . .
H16 H 0.0909 0.0359 0.6084 0.022 Uiso 1 1 calc R U . . .
Br21 Br 0.18472(7) 0.08497(2) 0.1248(5) 0.0229(5) Uani 1 1 d . . . . .
C21 C 0.1358(7) 0.0989(2) 0.262(5) 0.017(4) Uani 1 1 d . U . . .
Br22 Br 0.07519(7) 0.07272(2) 0.0359(5) 0.0244(5) Uani 1 1 d . . . . .
C22 C 0.0899(7) 0.0943(2) 0.215(5) 0.019(4) Uani 1 1 d . U . . .
C23 C 0.0555(7) 0.1052(2) 0.309(5) 0.018(4) Uani 1 1 d . U . . .
H23 H 0.0252 0.1021 0.2718 0.021 Uiso 1 1 calc R U . . .
Br24 Br 0.01803(7) 0.13522(2) 0.5908(5) 0.0225(5) Uani 1 1 d . . . . .
C24 C 0.0652(6) 0.1205(2) 0.456(5) 0.016(4) Uani 1 1 d . U . . .
C25 C 0.1111(7) 0.1255(2) 0.503(5) 0.024(4) Uani 1 1 d . U . . .
H25 H 0.1180 0.1359 0.6024 0.029 Uiso 1 1 calc R U . . .
C26 C 0.1452(7) 0.1148(2) 0.399(5) 0.020(4) Uani 1 1 d . U . . .
H26 H 0.1754 0.1182 0.4215 0.024 Uiso 1 1 calc R U . . .
Br31 Br 0.33716(7) 0.08135(2) 0.3904(6) 0.0243(5) Uani 1 1 d . . . . .
C31 C 0.3841(6) 0.0677(2) 0.200(5) 0.016(4) Uani 1 1 d . U . . .
Br32 Br 0.44409(7) 0.09620(2) 0.2874(5) 0.0237(5) Uani 1 1 d . . . . .
C32 C 0.4269(6) 0.0739(2) 0.158(5) 0.017(4) Uani 1 1 d . U . . .
C33 C 0.4623(7) 0.0635(2) 0.017(5) 0.026(5) Uani 1 1 d . U . . .
H33 H 0.4916 0.0676 -0.0189 0.031 Uiso 1 1 calc R U . . .
Br34 Br 0.49705(7) 0.03286(2) -0.2465(5) 0.0249(5) Uani 1 1 d . . . . .
C34 C 0.4501(6) 0.0469(2) -0.064(5) 0.017(4) Uani 1 1 d . U . . .
C35 C 0.4073(7) 0.0404(2) -0.025(5) 0.020(4) Uani 1 1 d . U . . .
H35 H 0.4005 0.0294 -0.0890 0.024 Uiso 1 1 calc R U . . .
C36 C 0.3736(7) 0.0512(2) 0.116(5) 0.021(4) Uani 1 1 d . U . . .
H36 H 0.3443 0.0472 0.1526 0.025 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_publ_flag
C12 C11 C16 118.9(16) . . ?
C12 C11 Br11 123.9(13) . . ?
C16 C11 Br11 117.2(14) . . ?
C11 C12 C13 122.1(16) . . ?
C11 C12 Br12 120.2(13) . . ?
C13 C12 Br12 117.6(14) . . ?
C12 C13 C14 118.0(18) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C15 C14 C13 122.7(18) . . ?
C15 C14 Br14 120.0(14) . . ?
C13 C14 Br14 117.2(15) . . ?
C14 C15 C16 120.0(17) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 118.2(17) . . ?
C15 C16 H16 120.9 . . ?
C11 C16 H16 120.9 . . ?
C26 C21 C22 118.3(17) . . ?
C26 C21 Br21 118.9(14) . . ?
C22 C21 Br21 122.7(14) . . ?
C23 C22 C21 120.4(17) . . ?
C23 C22 Br22 119.4(15) . . ?
C21 C22 Br22 120.1(14) . . ?
C24 C23 C22 120.6(18) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 120.1(17) . . ?
C23 C24 Br24 120.6(14) . . ?
C25 C24 Br24 119.3(14) . . ?
C26 C25 C24 118.8(18) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C21 121.7(18) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C32 C31 C36 121.0(17) . . ?
C32 C31 Br31 121.1(14) . . ?
C36 C31 Br31 117.9(14) . . ?
C31 C32 C33 121.0(17) . . ?
C31 C32 Br32 123.0(14) . . ?
C33 C32 Br32 116.1(14) . . ?
C34 C33 C32 116.0(18) . . ?
C34 C33 H33 122.0 . . ?
C32 C33 H33 122.0 . . ?
C35 C34 C33 124.2(18) . . ?
C35 C34 Br34 119.3(13) . . ?
C33 C34 Br34 116.5(14) . . ?
C34 C35 C36 117.5(17) . . ?
C34 C35 H35 121.3 . . ?
C36 C35 H35 121.3 . . ?
C31 C36 C35 120.4(18) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br11 C11 1.866(17) . ?
C11 C12 1.38(2) . ?
C11 C16 1.43(2) . ?
Br12 C12 1.896(17) . ?
C12 C13 1.38(2) . ?
C13 C14 1.39(2) . ?
C13 H13 0.9300 . ?
Br14 C14 1.908(18) . ?
C14 C15 1.35(2) . ?
C15 C16 1.42(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Br21 C21 1.883(18) . ?
C21 C26 1.39(2) . ?
C21 C22 1.40(2) . ?
Br22 C22 1.884(18) . ?
C22 C23 1.38(2) . ?
C23 C24 1.37(2) . ?
C23 H23 0.9300 . ?
Br24 C24 1.882(18) . ?
C24 C25 1.41(3) . ?
C25 C26 1.37(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
Br31 C31 1.898(18) . ?
C31 C32 1.36(2) . ?
C31 C36 1.37(2) . ?
Br32 C32 1.896(17) . ?
C32 C33 1.43(2) . ?
C33 C34 1.39(2) . ?
C33 H33 0.9300 . ?
Br34 C34 1.906(18) . ?
C34 C35 1.36(2) . ?
C35 C36 1.42(2) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
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
C13 H13 Br12 0.93 2.97 3.66(2) 133 10_554
C33 H33 Br22 0.93 3.04 3.88(2) 152 9_554
C35 H35 Br12 0.93 3.00 3.723(19) 136 10_553
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 1(3) . . . . ?
Br11 C11 C12 C13 -178.2(15) . . . . ?
C16 C11 C12 Br12 -174.9(13) . . . . ?
Br11 C11 C12 Br12 6(2) . . . . ?
C11 C12 C13 C14 0(3) . . . . ?
Br12 C12 C13 C14 176.0(14) . . . . ?
C12 C13 C14 C15 0(3) . . . . ?
C12 C13 C14 Br14 -177.7(15) . . . . ?
C13 C14 C15 C16 0(3) . . . . ?
Br14 C14 C15 C16 177.1(13) . . . . ?
C14 C15 C16 C11 1(3) . . . . ?
C12 C11 C16 C15 -2(3) . . . . ?
Br11 C11 C16 C15 177.8(13) . . . . ?
C26 C21 C22 C23 -1(3) . . . . ?
Br21 C21 C22 C23 -177.7(14) . . . . ?
C26 C21 C22 Br22 -179.0(13) . . . . ?
Br21 C21 C22 Br22 5(2) . . . . ?
C21 C22 C23 C24 -1(3) . . . . ?
Br22 C22 C23 C24 176.5(14) . . . . ?
C22 C23 C24 C25 2(3) . . . . ?
C22 C23 C24 Br24 -179.0(14) . . . . ?
C23 C24 C25 C26 0(3) . . . . ?
Br24 C24 C25 C26 -179.1(15) . . . . ?
C24 C25 C26 C21 -3(3) . . . . ?
C22 C21 C26 C25 3(3) . . . . ?
Br21 C21 C26 C25 179.8(16) . . . . ?
C36 C31 C32 C33 2(3) . . . . ?
Br31 C31 C32 C33 179.6(15) . . . . ?
C36 C31 C32 Br32 -177.3(14) . . . . ?
Br31 C31 C32 Br32 1(2) . . . . ?
C31 C32 C33 C34 -2(3) . . . . ?
Br32 C32 C33 C34 177.4(14) . . . . ?
C32 C33 C34 C35 2(3) . . . . ?
C32 C33 C34 Br34 -179.1(14) . . . . ?
C33 C34 C35 C36 -2(3) . . . . ?
Br34 C34 C35 C36 179.0(14) . . . . ?
C32 C31 C36 C35 -2(3) . . . . ?
Br31 C31 C36 C35 -179.8(14) . . . . ?
C34 C35 C36 C31 2(3) . . . . ?

_cod_database_fobs_code 2108852
