#------------------------------------------------------------------------------
#$Date: 2021-07-28 08:23:42 +0300 (Wed, 28 Jul 2021) $
#$Revision: 267783 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108851.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_2108851
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                   29.383(2)
_cell_length_b                   79.163(4)
_cell_length_c                   3.9713(3)
_cell_measurement_reflns_used    4227
_cell_measurement_temperature    200.0(1)
_cell_measurement_theta_max      24.17
_cell_measurement_theta_min      3.77
_cell_volume                     9237.4(10)
_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      200.0(1)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.998
_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  0.1155
_diffrn_reflns_av_unetI/netI     0.1243
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       -83
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            19496
_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         25.998
_diffrn_reflns_theta_min         2.773
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    15.626
_exptl_absorpt_correction_T_max  0.388
_exptl_absorpt_correction_T_min  0.040
_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    2.716
_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         1.753
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.217
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.42(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4444
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0621
_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)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2801
_reflns_number_total             4444
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lo5092sup1.cif
_cod_data_source_block           124TBB_200K
_cod_database_code               2108851
_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   0.408
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 0.07378(8) 0.00241(3) 0.8770(7) 0.0489(7) Uani 1 1 d . . . . .
C11 C 0.1255(7) 0.0158(2) 0.836(6) 0.037(5) Uani 1 1 d . U . . .
Br12 Br 0.17889(8) -0.01126(2) 1.0872(7) 0.0497(7) Uani 1 1 d . . . . .
C12 C 0.1677(7) 0.0108(2) 0.931(4) 0.026(4) Uani 1 1 d . U . . .
C13 C 0.2053(7) 0.0215(2) 0.896(6) 0.042(5) Uani 1 1 d . U . . .
H13 H 0.2341 0.0180 0.9625 0.051 Uiso 1 1 calc R U . . .
Br14 Br 0.25112(8) 0.05143(3) 0.7025(7) 0.0526(7) Uani 1 1 d . . . . .
C14 C 0.1988(8) 0.0375(2) 0.762(6) 0.045(6) Uani 1 1 d . U . . .
C15 C 0.1569(7) 0.0425(2) 0.652(6) 0.041(5) Uani 1 1 d . U . . .
H15 H 0.1535 0.0530 0.5488 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1195(7) 0.0321(2) 0.692(5) 0.039(5) Uani 1 1 d . U . . .
H16 H 0.0907 0.0357 0.6257 0.047 Uiso 1 1 calc R U . . .
Br21 Br 0.18420(8) 0.08511(2) 0.1299(6) 0.0459(6) Uani 1 1 d . . . . .
C21 C 0.1358(7) 0.0993(2) 0.261(5) 0.032(4) Uani 1 1 d . U . . .
Br22 Br 0.07490(8) 0.07302(3) 0.0375(6) 0.0461(6) Uani 1 1 d . . . . .
C22 C 0.0889(7) 0.0944(2) 0.218(5) 0.029(4) Uani 1 1 d . U . . .
C23 C 0.0558(7) 0.1054(2) 0.310(5) 0.031(4) Uani 1 1 d . U . . .
H23 H 0.0256 0.1025 0.2731 0.037 Uiso 1 1 calc R U . . .
Br24 Br 0.01798(8) 0.13502(3) 0.5871(6) 0.0437(6) Uani 1 1 d . . . . .
C24 C 0.0655(7) 0.1207(2) 0.454(5) 0.036(5) Uani 1 1 d . U . . .
C25 C 0.1097(7) 0.1255(2) 0.500(5) 0.038(5) Uani 1 1 d . U . . .
H25 H 0.1165 0.1360 0.5949 0.046 Uiso 1 1 calc R U . . .
C26 C 0.1444(7) 0.1145(2) 0.403(5) 0.040(5) Uani 1 1 d . U . . .
H26 H 0.1745 0.1178 0.4359 0.048 Uiso 1 1 calc R U . . .
Br31 Br 0.33683(8) 0.08126(3) 0.3870(7) 0.0460(6) Uani 1 1 d . . . . .
C31 C 0.3840(7) 0.0674(2) 0.205(5) 0.032(5) Uani 1 1 d . U . . .
Br32 Br 0.44345(8) 0.09601(2) 0.2855(6) 0.0458(6) Uani 1 1 d . . . . .
C32 C 0.4261(6) 0.0739(2) 0.166(5) 0.029(4) Uani 1 1 d . U . . .
C33 C 0.4616(7) 0.0636(2) 0.021(5) 0.040(5) Uani 1 1 d . U . . .
H33 H 0.4907 0.0678 -0.0170 0.049 Uiso 1 1 calc R U . . .
Br34 Br 0.49663(8) 0.03306(3) -0.2411(6) 0.0460(6) Uani 1 1 d . . . . .
C34 C 0.4501(7) 0.0471(2) -0.058(5) 0.032(4) Uani 1 1 d . U . . .
C35 C 0.4075(7) 0.0407(2) -0.021(5) 0.037(5) Uani 1 1 d . U . . .
H35 H 0.4007 0.0297 -0.0859 0.045 Uiso 1 1 calc R U . . .
C36 C 0.3746(7) 0.0511(2) 0.116(5) 0.041(5) Uani 1 1 d . U . . .
H36 H 0.3453 0.0470 0.1479 0.049 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 119.5(18) . . ?
C12 C11 Br11 123.7(15) . . ?
C16 C11 Br11 116.8(15) . . ?
C11 C12 C13 121.1(17) . . ?
C11 C12 Br12 121.6(15) . . ?
C13 C12 Br12 117.1(15) . . ?
C14 C13 C12 118.8(19) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 120.9(19) . . ?
C15 C14 Br14 121.2(16) . . ?
C13 C14 Br14 117.7(16) . . ?
C14 C15 C16 120.3(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.3(19) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C26 C21 C22 118.0(18) . . ?
C26 C21 Br21 120.3(15) . . ?
C22 C21 Br21 121.7(14) . . ?
C23 C22 C21 118.6(17) . . ?
C23 C22 Br22 121.6(16) . . ?
C21 C22 Br22 119.8(14) . . ?
C22 C23 C24 122.2(19) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C25 C24 C23 120.1(19) . . ?
C25 C24 Br24 120.0(15) . . ?
C23 C24 Br24 119.9(15) . . ?
C24 C25 C26 118.8(19) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C21 C26 C25 122.2(19) . . ?
C21 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C32 C31 C36 121.0(19) . . ?
C32 C31 Br31 119.5(14) . . ?
C36 C31 Br31 119.4(15) . . ?
C31 C32 C33 119.6(17) . . ?
C31 C32 Br32 124.9(15) . . ?
C33 C32 Br32 115.5(14) . . ?
C34 C33 C32 116.6(19) . . ?
C34 C33 H33 121.7 . . ?
C32 C33 H33 121.7 . . ?
C35 C34 C33 123.7(18) . . ?
C35 C34 Br34 118.7(14) . . ?
C33 C34 Br34 117.5(15) . . ?
C34 C35 C36 117.4(18) . . ?
C34 C35 H35 121.3 . . ?
C36 C35 H35 121.3 . . ?
C31 C36 C35 121.6(19) . . ?
C31 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
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 1.861(19) . ?
C11 C12 1.36(3) . ?
C11 C16 1.42(2) . ?
Br12 C12 1.882(17) . ?
C12 C13 1.40(3) . ?
C13 C14 1.39(2) . ?
C13 H13 0.9300 . ?
Br14 C14 1.91(2) . ?
C14 C15 1.36(3) . ?
C15 C16 1.38(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Br21 C21 1.887(19) . ?
C21 C26 1.35(2) . ?
C21 C22 1.44(3) . ?
Br22 C22 1.882(17) . ?
C22 C23 1.35(2) . ?
C23 C24 1.37(2) . ?
C23 H23 0.9300 . ?
Br24 C24 1.875(19) . ?
C24 C25 1.37(3) . ?
C25 C26 1.40(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
Br31 C31 1.908(19) . ?
C31 C32 1.35(2) . ?
C31 C36 1.37(2) . ?
Br32 C32 1.885(17) . ?
C32 C33 1.44(2) . ?
C33 C34 1.38(2) . ?
C33 H33 0.9300 . ?
Br34 C34 1.910(18) . ?
C34 C35 1.36(3) . ?
C35 C36 1.38(3) . ?
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 3.01 3.71(2) 133 10_554
C33 H33 Br22 0.93 3.07 3.92(2) 152 9_554
C35 H35 Br12 0.93 3.05 3.78(2) 137 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 2(3) . . . . ?
Br11 C11 C12 C13 -179.5(15) . . . . ?
C16 C11 C12 Br12 -174.5(15) . . . . ?
Br11 C11 C12 Br12 4(3) . . . . ?
C11 C12 C13 C14 0(3) . . . . ?
Br12 C12 C13 C14 176.0(16) . . . . ?
C12 C13 C14 C15 -3(3) . . . . ?
C12 C13 C14 Br14 -177.7(15) . . . . ?
C13 C14 C15 C16 4(4) . . . . ?
Br14 C14 C15 C16 179.0(16) . . . . ?
C14 C15 C16 C11 -3(3) . . . . ?
C12 C11 C16 C15 0(3) . . . . ?
Br11 C11 C16 C15 -179.1(16) . . . . ?
C26 C21 C22 C23 2(3) . . . . ?
Br21 C21 C22 C23 -178.3(14) . . . . ?
C26 C21 C22 Br22 -177.8(14) . . . . ?
Br21 C21 C22 Br22 2(2) . . . . ?
C21 C22 C23 C24 -3(3) . . . . ?
Br22 C22 C23 C24 177.3(15) . . . . ?
C22 C23 C24 C25 2(3) . . . . ?
C22 C23 C24 Br24 -178.1(15) . . . . ?
C23 C24 C25 C26 -1(3) . . . . ?
Br24 C24 C25 C26 179.3(16) . . . . ?
C22 C21 C26 C25 -1(3) . . . . ?
Br21 C21 C26 C25 179.3(17) . . . . ?
C24 C25 C26 C21 1(3) . . . . ?
C36 C31 C32 C33 1(3) . . . . ?
Br31 C31 C32 C33 -178.5(15) . . . . ?
C36 C31 C32 Br32 -179.1(16) . . . . ?
Br31 C31 C32 Br32 1(3) . . . . ?
C31 C32 C33 C34 -2(3) . . . . ?
Br32 C32 C33 C34 177.9(15) . . . . ?
C32 C33 C34 C35 3(3) . . . . ?
C32 C33 C34 Br34 -178.7(14) . . . . ?
C33 C34 C35 C36 -3(3) . . . . ?
Br34 C34 C35 C36 179.3(15) . . . . ?
C32 C31 C36 C35 -1(3) . . . . ?
Br31 C31 C36 C35 179.1(16) . . . . ?
C34 C35 C36 C31 1(3) . . . . ?

_cod_database_fobs_code 2108851
