#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/23/2012341.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_2012341
loop_
_publ_author_name
'Eriksson, Johan'
'Eriksson, Lars'
_publ_section_title
;
 2,2',6,6'-Tetrachloro-4,4'-propane-2,2-diyldiphenol,
 2,2',6-tribromo-4,4'-propane-2,2-diyldiphenol and
 2,2',6,6'-tetrabromo-4,4'-propane-2,2-diyldiphenol
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1308
_journal_page_last               1312
_journal_paper_doi               10.1107/S0108270101012112
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C15 H13 Br3 O2'
_chemical_formula_sum            'C15 H13 Br3 O2'
_chemical_formula_weight         464.98
_chemical_name_common            'Tribromo bisphenol A'
_chemical_name_systematic
;
3,3',5'-Tribromo-4,4'-dihydroxy-diphenyl-dimethyl-methane
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.545(3)
_cell_length_b                   30.971(4)
_cell_length_c                   10.0335(19)
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.65
_cell_volume                     6073.6(17)
_computing_cell_refinement       'CELL (Stoe, 1997)'
_computing_data_collection       'EXPOSE (Stoe, 1997)'
_computing_data_reduction        'INTEGRATE (Stoe, 1997)'
_computing_molecular_graphics    'DIAMOND (Bergerhoff, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.0
_diffrn_measured_fraction_theta_full .992
_diffrn_measured_fraction_theta_max .992
_diffrn_measurement_device_type  'Stoe IPDS area-detector'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .066
_diffrn_reflns_av_sigmaI/netI    .034
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10060
_diffrn_reflns_theta_full        25.89
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    7.968
_exptl_absorpt_correction_T_max  .167
_exptl_absorpt_correction_T_min  .086
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED; Stoe, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.034
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3584
_exptl_crystal_size_max          .31
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .22
_refine_diff_density_max         1.50
_refine_diff_density_min         -.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1559
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          .028
_refine_ls_R_factor_gt           .026
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.04P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .063
_reflns_number_gt                1500
_reflns_number_total             1559
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1139.cif
_cod_data_source_block           II
_cod_original_cell_volume        6073.6(16)
_cod_database_code               2012341
_cod_database_fobs_code          2012341
loop_
_symmetry_equiv_pos_as_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_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
_atom_site_type_symbol
Br1 .04130(3) .251655(17) .20723(6) .01990(14) Uani d . 1 . . Br
Br2 .36051(3) .238662(17) -.14632(5) .02046(14) Uani d . 1 . . Br
Br3 .26465(4) .400527(18) -.32651(5) .02824(16) Uani d . 1 . . Br
O1 .3320(2) .31433(13) -.3416(4) .0237(9) Uani d . 1 . . O
H1 .3586 .2938 -.3424 .036 Uiso calc R 1 . . H
O2 .0917(2) .24357(14) .5008(4) .0245(9) Uani d . 1 . . O
H2 .0524 .2436 .4722 .037 Uiso calc R 1 . . H
C1 .2617(3) .35635(16) .1956(5) .0138(11) Uani d . 1 . . C
C2 .2242(3) .39992(16) .2086(6) .0178(12) Uani d . 1 . . C
H2A .1791 .3975 .1714 .027 Uiso calc R 1 . . H
H2B .2493 .4218 .1616 .027 Uiso calc R 1 . . H
H2C .2209 .4077 .3010 .027 Uiso calc R 1 . . H
C3 .3334(3) .3616(2) .2562(6) .0219(12) Uani d . 1 . . C
H3A .3297 .3746 .3427 .033 Uiso calc R 1 . . H
H3B .3607 .3796 .1993 .033 Uiso calc R 1 . . H
H3C .3546 .3337 .2644 .033 Uiso calc R 1 . . H
C4 .2189(3) .32320(16) .2718(5) .0120(10) Uani d . 1 . . C
C5 .1617(3) .30387(15) .2131(5) .0118(9) Uani d . 1 . . C
H5 .1521 .3088 .1236 .014 Uiso calc R 1 . . H
C6 .1194(3) .27745(17) .2879(5) .0134(10) Uani d . 1 . . C
C7 .1320(3) .26925(17) .4211(6) .0157(11) Uani d . 1 . . C
C8 .1889(3) .28782(18) .4793(6) .0189(11) Uani d . 1 . . C
H8 .1986 .2825 .5686 .023 Uiso calc R 1 . . H
C9 .2314(3) .31417(17) .4056(5) .0158(11) Uani d . 1 . . C
H9 .2695 .3263 .4464 .019 Uiso calc R 1 . . H
C10 .2724(3) .34332(16) .0512(5) .0110(10) Uani d . 1 . . C
C11 .2603(3) .37152(16) -.0552(6) .0162(11) Uani d . 1 . . C
H11 .2390 .3979 -.0391 .019 Uiso calc R 1 . . H
C12 .2795(3) .36073(17) -.1853(5) .0155(11) Uani d . 1 . . C
C13 .3108(3) .32183(18) -.2145(5) .0142(10) Uani d . 1 . . C
C14 .3197(3) .29320(16) -.1094(5) .0135(10) Uani d . 1 . . C
C15 .3013(3) .30340(17) .0206(5) .0140(10) Uani d . 1 . . C
H15 .3083 .2833 .0882 .017 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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_publ_flag
C13 O1 H1 109.5 ?
C7 O2 H2 109.5 ?
C10 C1 C4 112.0(4) yes
C10 C1 C3 106.2(4) yes
C4 C1 C3 111.8(5) yes
C10 C1 C2 112.3(4) yes
C4 C1 C2 106.6(4) yes
C3 C1 C2 107.9(5) yes
C1 C2 H2A 109.5 ?
C1 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
C1 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
C1 C3 H3A 109.5 ?
C1 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C1 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
C9 C4 C5 117.4(5) yes
C9 C4 C1 121.4(5) yes
C5 C4 C1 121.0(5) yes
C6 C5 C4 120.2(5) ?
C6 C5 H5 119.9 ?
C4 C5 H5 119.9 ?
C7 C6 C5 121.7(5) ?
C7 C6 Br1 118.5(4) ?
C5 C6 Br1 119.8(4) ?
O2 C7 C8 117.1(5) yes
O2 C7 C6 124.4(5) yes
C8 C7 C6 118.5(5) ?
C9 C8 C7 120.2(5) ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.9 ?
C8 C9 C4 122.1(5) ?
C8 C9 H9 119.0 ?
C4 C9 H9 119.0 ?
C15 C10 C11 117.1(5) yes
C15 C10 C1 120.1(4) yes
C11 C10 C1 122.6(5) yes
C12 C11 C10 121.1(5) ?
C12 C11 H11 119.4 ?
C10 C11 H11 119.4 ?
C13 C12 C11 121.7(5) ?
C13 C12 Br3 118.3(4) ?
C11 C12 Br3 120.0(4) ?
O1 C13 C12 118.8(5) yes
O1 C13 C14 124.4(5) yes
C12 C13 C14 116.8(5) ?
C13 C14 C15 122.4(5) ?
C13 C14 Br2 118.1(4) ?
C15 C14 Br2 119.5(4) ?
C14 C15 C10 120.8(5) ?
C14 C15 H15 119.6 ?
C10 C15 H15 119.6 ?
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 C6 . 1.903(5) yes
Br2 C14 . 1.905(5) yes
Br3 C12 . 1.900(5) yes
O1 C13 . 1.361(7) ?
O1 H1 . .8200 ?
O2 C7 . 1.376(7) ?
O2 H2 . .8200 ?
C1 C10 . 1.520(7) yes
C1 C4 . 1.528(7) yes
C1 C3 . 1.537(7) yes
C1 C2 . 1.541(7) yes
C2 H2A . .9600 ?
C2 H2B . .9600 ?
C2 H2C . .9600 ?
C3 H3A . .9600 ?
C3 H3B . .9600 ?
C3 H3C . .9600 ?
C4 C9 . 1.393(7) ?
C4 C5 . 1.398(7) ?
C5 C6 . 1.385(7) ?
C5 H5 . .9300 ?
C6 C7 . 1.382(7) ?
C7 C8 . 1.381(8) ?
C8 C9 . 1.380(8) ?
C8 H8 . .9300 ?
C9 H9 . .9300 ?
C10 C15 . 1.393(7) ?
C10 C11 . 1.400(7) ?
C11 C12 . 1.398(8) ?
C11 H11 . .9300 ?
C12 C13 . 1.383(8) ?
C13 C14 . 1.388(7) ?
C14 C15 . 1.390(7) ?
C15 H15 . .9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 14_554 .82 2.18 2.818(5) 134 yes
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_publ_flag
C10 C1 C4 C9 144.8(5) yes
C3 C1 C4 C9 25.8(7) yes
C2 C1 C4 C9 -92.0(6) yes
C10 C1 C4 C5 -41.3(6) yes
C3 C1 C4 C5 -160.4(5) yes
C2 C1 C4 C5 81.8(6) yes
C9 C4 C5 C6 1.0(7) yes
C1 C4 C5 C6 -173.1(5) yes
C4 C5 C6 C7 -.2(8) ?
C4 C5 C6 Br1 179.6(4) ?
C5 C6 C7 O2 179.5(5) ?
Br1 C6 C7 O2 -.2(7) ?
C5 C6 C7 C8 -.5(8) ?
Br1 C6 C7 C8 179.7(4) ?
O2 C7 C8 C9 -179.6(5) ?
C6 C7 C8 C9 .5(8) ?
C7 C8 C9 C4 .3(9) ?
C5 C4 C9 C8 -1.0(8) ?
C1 C4 C9 C8 173.0(5) ?
C4 C1 C10 C15 -55.7(7) ?
C3 C1 C10 C15 66.7(6) ?
C2 C1 C10 C15 -175.6(5) ?
C4 C1 C10 C11 130.4(5) ?
C3 C1 C10 C11 -107.3(6) ?
C2 C1 C10 C11 10.4(7) ?
C15 C10 C11 C12 -3.1(8) yes
C1 C10 C11 C12 171.1(5) yes
C10 C11 C12 C13 .4(9) ?
C10 C11 C12 Br3 -178.1(4) ?
C11 C12 C13 O1 -176.1(5) ?
Br3 C12 C13 O1 2.4(7) ?
C11 C12 C13 C14 2.6(8) ?
Br3 C12 C13 C14 -178.8(4) ?
O1 C13 C14 C15 175.6(5) ?
C12 C13 C14 C15 -3.0(8) ?
O1 C13 C14 Br2 -2.9(7) ?
C12 C13 C14 Br2 178.4(4) ?
C13 C14 C15 C10 .4(8) ?
Br2 C14 C15 C10 178.9(4) ?
C11 C10 C15 C14 2.7(8) ?
C1 C10 C15 C14 -171.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 72955
