#------------------------------------------------------------------------------
#$Date: 2018-04-30 20:04:28 +0300 (Mon, 30 Apr 2018) $
#$Revision: 207575 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549344.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_1549344
loop_
_publ_author_name
'Peloquin, Andrew J.'
'Godman, Nicholas P.'
'Allison, Bruce D.'
'Balaich, Gary J.'
'Iacono, Scott T.'
_publ_section_title
;
 1,3-Bis(4-bromophenyl)propane
;
_journal_coeditor_code           BV4016
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x180563
_journal_paper_doi               10.1107/S2414314618005631
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C15 H14 Br2'
_chemical_formula_moiety         'C15 H14 Br2'
_chemical_formula_sum            'C15 H14 Br2'
_chemical_formula_weight         354.08
_chemical_name_common            1,3-di(4-bromophenyl)propane
_chemical_name_systematic
;
1,3-Bis(4-bromophenyl)propane
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 101.808(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4526(13)
_cell_length_b                   5.8441(10)
_cell_length_c                   16.278(3)
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.6708
_cell_measurement_theta_min      2.5566
_cell_volume                     694.0(2)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et
al.,
2008)
;
_computing_publication_material
;
SHELXL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'Omega Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14936
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    5.816
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat prism'
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.353
_refine_ls_abs_structure_details
;
Flack x determined using 1492 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.019(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.376
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0231
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0548
_reflns_number_gt                3421
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bv4016sup1.cif
_cod_data_source_block           I
_cod_database_code               1549344
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
Br Br1 0.72512(6) 0.64324(6) 0.32150(2) 0.02990(11) Uani d 1
Br Br2 0.07038(4) 0.07332(6) 0.93844(2) 0.01940(9) Uani d 1
C C1 0.7965(5) 0.8018(7) 0.7041(2) 0.0203(7) Uani d 1
H H1A 0.773435 0.961347 0.714801 0.024 Uiso calc 1
H H1B 0.91894 0.764318 0.734497 0.024 Uiso calc 1
C C2 0.6578(4) 0.6530(7) 0.73599(18) 0.0185(6) Uani d 1
H H2A 0.688304 0.493461 0.72972 0.022 Uiso calc 1
H H2B 0.53722 0.679954 0.701533 0.022 Uiso calc 1
C C3 0.6507(5) 0.6981(6) 0.8280(2) 0.0186(7) Uani d 1
H H3A 0.770709 0.669457 0.862731 0.022 Uiso calc 1
H H3B 0.620835 0.857725 0.834565 0.022 Uiso calc 1
C C4 0.7860(5) 0.7678(6) 0.6108(2) 0.0172(7) Uani d 1
C C5 0.6973(5) 0.9269(6) 0.5527(2) 0.0194(7) Uani d 1
H H5 0.649793 1.05945 0.571618 0.023 Uiso calc 1
C C6 0.6785(5) 0.8907(6) 0.4664(2) 0.0205(7) Uani d 1
H H6 0.619388 0.997936 0.42798 0.025 Uiso calc 1
C C7 0.7494(5) 0.6922(6) 0.43923(19) 0.0191(7) Uani d 1
C C8 0.8384(5) 0.5303(6) 0.4947(2) 0.0203(8) Uani d 1
H H8 0.885231 0.397812 0.475442 0.024 Uiso calc 1
C C9 0.8562(4) 0.5710(7) 0.5808(2) 0.0193(6) Uani d 1
H H9 0.916431 0.463847 0.618886 0.023 Uiso calc 1
C C10 0.5111(4) 0.5499(6) 0.85791(18) 0.0157(6) Uani d 1
C C11 0.5604(5) 0.3371(6) 0.8952(2) 0.0165(7) Uani d 1
H H11 0.68188 0.289513 0.903494 0.02 Uiso calc 1
C C12 0.4309(4) 0.1948(6) 0.92003(19) 0.0162(7) Uani d 1
H H12 0.465409 0.054546 0.945371 0.019 Uiso calc 1
C C13 0.2489(4) 0.2666(6) 0.90622(19) 0.0154(6) Uani d 1
C C14 0.1967(5) 0.4775(6) 0.8701(2) 0.0192(7) Uani d 1
H H14 0.075257 0.525136 0.862057 0.023 Uiso calc 1
C C15 0.3282(4) 0.6167(6) 0.84615(19) 0.0195(7) Uani d 1
H H15 0.293275 0.757895 0.821671 0.023 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'
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
C4 C1 C2 111.5(3)
C4 C1 H1A 109.3
C2 C1 H1A 109.3
C4 C1 H1B 109.3
C2 C1 H1B 109.3
H1A C1 H1B 108.0
C1 C2 C3 113.4(3)
C1 C2 H2A 108.9
C3 C2 H2A 108.9
C1 C2 H2B 108.9
C3 C2 H2B 108.9
H2A C2 H2B 107.7
C10 C3 C2 112.4(3)
C10 C3 H3A 109.1
C2 C3 H3A 109.1
C10 C3 H3B 109.1
C2 C3 H3B 109.1
H3A C3 H3B 107.9
C9 C4 C5 118.3(3)
C9 C4 C1 120.9(3)
C5 C4 C1 120.8(3)
C4 C5 C6 121.1(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C7 C6 C5 118.8(3)
C7 C6 H6 120.6
C5 C6 H6 120.6
C8 C7 C6 121.9(3)
C8 C7 Br1 119.2(3)
C6 C7 Br1 118.8(3)
C7 C8 C9 118.2(3)
C7 C8 H8 120.9
C9 C8 H8 120.9
C4 C9 C8 121.7(3)
C4 C9 H9 119.1
C8 C9 H9 119.1
C15 C10 C11 118.1(3)
C15 C10 C3 121.0(3)
C11 C10 C3 120.8(3)
C12 C11 C10 121.3(3)
C12 C11 H11 119.4
C10 C11 H11 119.4
C13 C12 C11 118.8(3)
C13 C12 H12 120.6
C11 C12 H12 120.6
C14 C13 C12 121.0(3)
C14 C13 Br2 119.6(3)
C12 C13 Br2 119.4(2)
C13 C14 C15 119.1(3)
C13 C14 H14 120.4
C15 C14 H14 120.4
C14 C15 C10 121.6(3)
C14 C15 H15 119.2
C10 C15 H15 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C7 1.909(3)
Br2 C13 1.899(3)
C1 C4 1.519(4)
C1 C2 1.521(5)
C1 H1A 0.97
C1 H1B 0.97
C2 C3 1.532(4)
C2 H2A 0.97
C2 H2B 0.97
C3 C10 1.509(5)
C3 H3A 0.97
C3 H3B 0.97
C4 C9 1.392(5)
C4 C5 1.393(5)
C5 C6 1.399(5)
C5 H5 0.93
C6 C7 1.384(5)
C6 H6 0.93
C7 C8 1.380(5)
C8 C9 1.400(5)
C8 H8 0.93
C9 H9 0.93
C10 C15 1.392(4)
C10 C11 1.400(5)
C11 C12 1.395(5)
C11 H11 0.93
C12 C13 1.393(4)
C12 H12 0.93
C13 C14 1.387(5)
C14 C15 1.390(5)
C14 H14 0.93
C15 H15 0.93

_cod_database_fobs_code 1549344
