#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/54/2015456.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_2015456
loop_
_publ_author_name
'Kirsop, Peter'
'Storey, John M. D.'
'Harrison, William T. A.'
_publ_section_title
;
 2-Bromo-1,3-bis(bromomethyl)benzene, with Z' = 1.5:
 whole-molecule disorder of one of the two independent molecules
;
_journal_coeditor_code           SK3024
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o376
_journal_page_last               o378
_journal_paper_doi               10.1107/S0108270106017707
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H7 Br3'
_chemical_formula_moiety         'C8 H7 Br3'
_chemical_formula_sum            'C8 H7 Br3'
_chemical_formula_weight         342.87
_chemical_name_systematic
;
2-Bromo-1,3-bis(bromomethyl)benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.971(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   9.1114(4)
_cell_length_b                   22.6016(10)
_cell_length_c                   7.5004(3)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1432.40(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
HKL Denzo (Otwinowski & Minor, 1997) and Scalepack, and SORTAV
(Blessing, 1995)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14563
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    12.607
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.889
_refine_diff_density_min         -2.785
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3266
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1847P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2286
_refine_ls_wR_factor_ref         0.2534
_reflns_number_gt                2406
_reflns_number_total             3266
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3024.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015456
_cod_database_fobs_code          2015456
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8454(10) 0.6929(4) 0.7788(10) 0.0206(17) Uani d U 1 . .
C C2 0.7173(10) 0.7232(4) 0.7914(10) 0.0178(15) Uani d U 1 . .
C C3 0.7214(11) 0.7863(4) 0.7936(11) 0.0195(17) Uani d U 1 . .
H H3 0.6339 0.8081 0.7986 0.023 Uiso calc R 1 . .
C C4 0.8526(11) 0.8155(4) 0.7887(11) 0.0236(19) Uani d . 1 . .
H H4 0.8553 0.8575 0.7923 0.028 Uiso calc R 1 . .
C C5 0.9812(11) 0.7846(4) 0.7786(11) 0.0215(18) Uani d . 1 . .
H H5 1.0693 0.8058 0.7728 0.026 Uiso calc R 1 . .
C C6 0.9828(10) 0.7233(4) 0.7768(10) 0.0198(17) Uani d . 1 . .
C C7 0.5713(11) 0.6931(4) 0.7972(11) 0.0237(18) Uani d U 1 . .
H H7A 0.5170 0.7201 0.8566 0.028 Uiso calc R 1 . .
H H7B 0.6031 0.6573 0.8786 0.028 Uiso calc R 1 . .
C C8 1.1180(12) 0.6912(4) 0.7647(12) 0.029(2) Uani d . 1 . .
H H8A 1.1779 0.7178 0.7118 0.034 Uiso calc R 1 . .
H H8B 1.0790 0.6575 0.6748 0.034 Uiso calc R 1 . .
Br Br1 0.83970(12) 0.60963(4) 0.76676(13) 0.0314(3) Uani d . 1 . .
Br Br2 0.42421(11) 0.67059(4) 0.54093(12) 0.0251(3) Uani d . 1 . .
Br Br3 1.26224(12) 0.66087(4) 1.01763(12) 0.0271(3) Uani d . 1 . .
C C11 1.0313(14) 0.5093(6) 0.4755(12) 0.027(4) Uiso d PG 0.50 A -1
C C12 1.1455(11) 0.5068(5) 0.6607(14) 0.018(3) Uiso d PG 0.50 A -1
C C13 1.1082(14) 0.4830(6) 0.8093(11) 0.028(3) Uiso d PG 0.50 A -1
H H13 1.1862 0.4813 0.9358 0.034 Uiso calc PR 0.50 A -1
C C14 0.9567(17) 0.4616(6) 0.7728(16) 0.028(3) Uiso d PG 0.50 A -1
H H14 0.9312 0.4453 0.8744 0.034 Uiso calc PR 0.50 A -1
C C15 0.8425(12) 0.4640(6) 0.5877(19) 0.038(5) Uiso d PG 0.50 A -1
H H15 0.7390 0.4493 0.5627 0.045 Uiso calc PR 0.50 A -1
C C16 0.8798(12) 0.4878(6) 0.4391(13) 0.029(4) Uiso d PG 0.50 A -1
C C17 1.314(2) 0.5274(7) 0.719(2) 0.021(3) Uiso d P 0.50 A -1
H H17A 1.3514 0.5434 0.8514 0.026 Uiso calc PR 0.50 A -1
H H17B 1.3198 0.5596 0.6322 0.026 Uiso calc PR 0.50 A -1
C C18 0.756(3) 0.4905(10) 0.240(3) 0.042(5) Uiso d P 0.50 A -1
H H18A 0.6996 0.4522 0.2101 0.051 Uiso calc PR 0.50 A -1
H H18B 0.8091 0.4962 0.1473 0.051 Uiso calc PR 0.50 A -1
Br Br11 1.0902(3) 0.54495(9) 0.2818(3) 0.0364(6) Uani d P 0.50 A -1
Br Br12 1.4532(3) 0.46312(11) 0.7090(4) 0.0479(6) Uani d P 0.50 A -1
Br Br13 0.6022(3) 0.55394(10) 0.2047(4) 0.0465(6) Uani d P 0.50 A -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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 121.6(8)
C2 C1 Br1 119.2(6)
C6 C1 Br1 119.1(7)
C1 C2 C3 118.4(8)
C1 C2 C7 123.5(8)
C3 C2 C7 118.0(8)
C4 C3 C2 119.8(8)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 121.1(9)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 121.1(8)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C1 117.8(8)
C5 C6 C8 120.6(8)
C1 C6 C8 121.5(8)
C2 C7 Br2 112.1(5)
C2 C7 H7A 109.2
Br2 C7 H7A 109.2
C2 C7 H7B 109.2
Br2 C7 H7B 109.2
H7A C7 H7B 107.9
C6 C8 Br3 112.6(6)
C6 C8 H8A 109.1
Br3 C8 H8A 109.1
C6 C8 H8B 109.1
Br3 C8 H8B 109.1
H8A C8 H8B 107.8
C12 C11 C16 120.0
C12 C11 Br11 117.3(6)
C16 C11 Br11 122.7(6)
C13 C12 C11 120.0
C13 C12 C17 114.6(10)
C11 C12 C17 125.4(10)
C12 C13 C14 120.0
C12 C13 H13 120.0
C14 C13 H13 120.0
C13 C14 C15 120.0
C13 C14 H14 120.0
C15 C14 H14 120.0
C16 C15 C14 120.0
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C11 120.0
C15 C16 C18 119.8(13)
C11 C16 C18 120.2(13)
C12 C17 Br12 111.5(11)
C12 C17 H17A 109.3
Br12 C17 H17A 109.3
C12 C17 H17B 109.3
Br12 C17 H17B 109.3
H17A C17 H17B 108.0
C16 C18 Br13 113.5(14)
C16 C18 H18A 108.9
Br13 C18 H18A 108.9
C16 C18 H18B 108.9
Br13 C18 H18B 108.9
H18A C18 H18B 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(12)
C1 C6 1.432(12)
C1 Br1 1.884(9)
C2 C3 1.426(12)
C2 C7 1.510(13)
C3 C4 1.379(12)
C3 H3 0.9500
C4 C5 1.390(13)
C4 H4 0.9500
C5 C6 1.386(12)
C5 H5 0.9500
C6 C8 1.462(13)
C7 Br2 1.955(9)
C7 H7A 0.9900
C7 H7B 0.9900
C8 Br3 1.982(9)
C8 H8A 0.9900
C8 H8B 0.9900
C11 C12 1.3900
C11 C16 1.3900
C11 Br11 1.907(8)
C12 C13 1.3900
C12 C17 1.51(2)
C13 C14 1.3900
C13 H13 0.9500
C14 C15 1.3900
C14 H14 0.9500
C15 C16 1.3900
C15 H15 0.9500
C16 C18 1.50(2)
C17 Br12 1.945(17)
C17 H17A 0.9900
C17 H17B 0.9900
C18 Br13 1.95(2)
C18 H18A 0.9900
C18 H18B 0.9900
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
C6 C1 C2 C3 2.8(11)
Br1 C1 C2 C3 -177.9(5)
C6 C1 C2 C7 -179.0(7)
Br1 C1 C2 C7 0.4(10)
C1 C2 C3 C4 -1.7(11)
C7 C2 C3 C4 179.9(7)
C2 C3 C4 C5 1.0(11)
C3 C4 C5 C6 -1.2(11)
C4 C5 C6 C1 2.2(11)
C4 C5 C6 C8 179.5(7)
C2 C1 C6 C5 -3.0(11)
Br1 C1 C6 C5 177.6(5)
C2 C1 C6 C8 179.6(7)
Br1 C1 C6 C8 0.3(10)
C1 C2 C7 Br2 -81.2(9)
C3 C2 C7 Br2 97.0(7)
C5 C6 C8 Br3 100.6(8)
C1 C6 C8 Br3 -82.1(9)
C16 C11 C12 C13 0.0
Br11 C11 C12 C13 178.0(10)
C16 C11 C12 C17 178.7(13)
Br11 C11 C12 C17 -3.2(13)
C11 C12 C13 C14 0.0
C17 C12 C13 C14 -178.9(12)
C12 C13 C14 C15 0.0
C13 C14 C15 C16 0.0
C14 C15 C16 C11 0.0
C14 C15 C16 C18 -179.8(15)
C12 C11 C16 C15 0.0
Br11 C11 C16 C15 -177.9(11)
C12 C11 C16 C18 179.8(15)
Br11 C11 C16 C18 1.9(14)
C13 C12 C17 Br12 86.4(11)
C11 C12 C17 Br12 -92.4(12)
C15 C16 C18 Br13 76.6(16)
C11 C16 C18 Br13 -103.2(14)
