#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/79/2217984.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_2217984
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Babitha, K. S.'
'Fuess, Hartmut'
_publ_section_title
;
 4-Bromophenyl benzoate
;
_journal_coeditor_code           OM2221
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o771
_journal_paper_doi               10.1107/S1600536808008167
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H9 Br O2'
_chemical_formula_moiety         'C13 H9 Br O2'
_chemical_formula_sum            'C13 H9 Br O2'
_chemical_formula_weight         277.11
_chemical_name_systematic
;
4-Bromophenyl benzoate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7480(10)
_cell_length_b                   5.5946(7)
_cell_length_c                   26.814(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      23.43
_cell_measurement_theta_min      9.92
_cell_volume                     1162.3(3)
_computing_cell_refinement       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_collection       'CAD-4-PC Software (Enraf--Nonius, 1996)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1987)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1986
_diffrn_reflns_theta_full        66.93
_diffrn_reflns_theta_max         66.93
_diffrn_reflns_theta_min         3.30
_diffrn_standards_decay_%        2.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.674
_exptl_absorpt_correction_T_max  0.6849
_exptl_absorpt_correction_T_min  0.2415
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.044
_refine_diff_density_min         -1.324
_refine_ls_abs_structure_details 'Flack (1983), with 375 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1442
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1268P)²+0.565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1894
_reflns_number_gt                1252
_reflns_number_total             1442
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2221.cif
_cod_data_source_block           I
_cod_database_code               2217984
_cod_database_fobs_code          2217984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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_refinement_flags
_atom_site_occupancy
Br Br1 0.29159(16) 0.2659(2) -0.12742(8) 0.0950(5) Uani d . 1
O O1 0.4692(6) 0.1882(9) 0.0901(2) 0.0581(13) Uani d . 1
O O2 0.3231(11) 0.5195(14) 0.1104(3) 0.107(3) Uani d . 1
C C1 0.4260(8) 0.2190(10) 0.0403(3) 0.0463(14) Uani d . 1
C C2 0.4854(8) 0.4121(12) 0.0127(3) 0.0544(16) Uani d . 1
H H2 0.5500 0.5321 0.0278 0.065 Uiso calc R 1
C C3 0.4478(8) 0.4229(12) -0.0367(3) 0.0560(17) Uani d . 1
H H3 0.4888 0.5492 -0.0559 0.067 Uiso calc R 1
C C4 0.3474(11) 0.2440(12) -0.0586(3) 0.0559(17) Uani d . 1
C C5 0.2920(9) 0.0437(12) -0.0313(3) 0.0589(18) Uani d . 1
H H5 0.2301 -0.0794 -0.0462 0.071 Uiso calc R 1
C C6 0.3332(9) 0.0389(13) 0.0176(3) 0.0583(17) Uani d . 1
H H6 0.2977 -0.0908 0.0368 0.070 Uiso calc R 1
C C7 0.4106(9) 0.3510(14) 0.1226(3) 0.0577(17) Uani d . 1
C C8 0.4601(9) 0.2976(12) 0.1748(3) 0.0521(15) Uani d . 1
C C9 0.5527(8) 0.0900(13) 0.1879(3) 0.0585(17) Uani d . 1
H H9 0.5846 -0.0209 0.1638 0.070 Uiso calc R 1
C C10 0.5943(10) 0.0558(13) 0.2368(4) 0.0644(19) Uani d . 1
H H10 0.6544 -0.0820 0.2454 0.077 Uiso calc R 1
C C11 0.5530(10) 0.2107(14) 0.2731(4) 0.0627(19) Uani d . 1
H H11 0.5834 0.1803 0.3060 0.075 Uiso calc R 1
C C12 0.4636(9) 0.4180(14) 0.2604(3) 0.0602(17) Uani d . 1
H H12 0.4353 0.5284 0.2851 0.072 Uiso calc R 1
C C13 0.4164(9) 0.4607(13) 0.2112(3) 0.0585(16) Uani d . 1
H H13 0.3558 0.5985 0.2029 0.070 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.1056(8) 0.1322(9) 0.0472(6) 0.0167(6) -0.0058(7) -0.0056(7)
O1 0.053(2) 0.064(3) 0.058(3) 0.008(2) -0.003(2) -0.011(3)
O2 0.145(6) 0.117(5) 0.059(4) 0.089(5) 0.005(4) 0.001(4)
C1 0.044(3) 0.047(3) 0.049(4) 0.003(2) -0.001(3) -0.003(3)
C2 0.046(3) 0.052(3) 0.066(5) -0.007(3) 0.004(3) -0.009(3)
C3 0.055(3) 0.052(3) 0.061(5) 0.007(3) 0.011(3) 0.005(3)
C4 0.058(4) 0.067(4) 0.042(4) 0.006(3) 0.005(4) -0.006(3)
C5 0.062(4) 0.049(3) 0.066(5) -0.004(3) -0.005(4) -0.006(3)
C6 0.054(3) 0.058(4) 0.063(5) -0.012(3) 0.002(4) 0.010(4)
C7 0.050(3) 0.068(4) 0.055(4) 0.019(3) 0.004(3) 0.002(4)
C8 0.051(3) 0.055(3) 0.050(4) -0.005(3) 0.006(3) -0.001(3)
C9 0.053(3) 0.062(3) 0.061(4) 0.017(3) -0.004(3) -0.010(4)
C10 0.057(3) 0.062(4) 0.074(5) 0.007(3) -0.008(4) 0.015(4)
C11 0.056(3) 0.082(5) 0.050(5) -0.001(3) -0.002(3) 0.003(4)
C12 0.064(4) 0.065(4) 0.052(4) -0.007(3) 0.005(4) -0.002(4)
C13 0.056(3) 0.059(4) 0.060(4) 0.010(3) -0.003(3) 0.001(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 O1 C1 117.4(5)
C6 C1 C2 120.4(8)
C6 C1 O1 117.3(6)
C2 C1 O1 122.0(6)
C3 C2 C1 118.9(6)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 119.9(7)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 121.4(8)
C3 C4 Br1 119.3(6)
C5 C4 Br1 119.2(6)
C6 C5 C4 116.7(7)
C6 C5 H5 121.6
C4 C5 H5 121.6
C5 C6 C1 122.4(7)
C5 C6 H6 118.8
C1 C6 H6 118.8
O2 C7 O1 123.0(8)
O2 C7 C8 124.1(7)
O1 C7 C8 112.9(6)
C13 C8 C9 119.5(8)
C13 C8 C7 118.2(6)
C9 C8 C7 122.2(7)
C10 C9 C8 118.4(7)
C10 C9 H9 120.8
C8 C9 H9 120.8
C11 C10 C9 123.4(7)
C11 C10 H10 118.3
C9 C10 H10 118.3
C10 C11 C12 118.7(8)
C10 C11 H11 120.7
C12 C11 H11 120.7
C13 C12 C11 120.4(8)
C13 C12 H12 119.8
C11 C12 H12 119.8
C8 C13 C12 119.6(7)
C8 C13 H13 120.2
C12 C13 H13 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.899(9)
O1 C7 1.340(10)
O1 C1 1.388(10)
O2 C7 1.206(9)
C1 C6 1.379(10)
C1 C2 1.388(10)
C2 C3 1.356(12)
C2 H2 0.9300
C3 C4 1.398(11)
C3 H3 0.9300
C4 C5 1.406(11)
C5 C6 1.351(12)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.481(12)
C8 C13 1.379(11)
C8 C9 1.410(10)
C9 C10 1.364(12)
C9 H9 0.9300
C10 C11 1.342(12)
C10 H10 0.9300
C11 C12 1.392(11)
C11 H11 0.9300
C12 C13 1.390(12)
C12 H12 0.9300
C13 H13 0.9300
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
C7 O1 C1 C6 -120.1(7)
C7 O1 C1 C2 65.4(9)
C6 C1 C2 C3 1.3(10)
O1 C1 C2 C3 175.6(6)
C1 C2 C3 C4 1.4(10)
C2 C3 C4 C5 -3.8(10)
C2 C3 C4 Br1 178.5(5)
C3 C4 C5 C6 3.2(10)
Br1 C4 C5 C6 -179.1(6)
C4 C5 C6 C1 -0.5(11)
C2 C1 C6 C5 -1.8(11)
O1 C1 C6 C5 -176.4(7)
C1 O1 C7 O2 0.2(12)
C1 O1 C7 C8 178.5(6)
O2 C7 C8 C13 -5.8(12)
O1 C7 C8 C13 175.9(6)
O2 C7 C8 C9 175.6(9)
O1 C7 C8 C9 -2.7(10)
C13 C8 C9 C10 0.9(10)
C7 C8 C9 C10 179.5(7)
C8 C9 C10 C11 -0.6(12)
C9 C10 C11 C12 -0.3(12)
C10 C11 C12 C13 0.9(11)
C9 C8 C13 C12 -0.3(11)
C7 C8 C13 C12 -178.9(7)
C11 C12 C13 C8 -0.6(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 232530
