#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230785.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_2230785
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
'Garudachari, B.'
'Isloor, Arun M.'
'Satyanarayan, M. N.'
_publ_section_title
;
 2-(4-Bromophenyl)-2-oxoethyl 2-methoxybenzoate
;
_journal_coeditor_code           LH5263
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1724
_journal_paper_doi               10.1107/S1600536811023002
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H13 Br O4'
_chemical_formula_moiety         'C16 H13 Br O4'
_chemical_formula_sum            'C16 H13 Br O4'
_chemical_formula_weight         349.17
_chemical_name_systematic
;
2-(4-Bromophenyl)-2-oxoethyl 2-methoxybenzoate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8424(5)
_cell_length_b                   14.6799(9)
_cell_length_c                   25.7677(14)
_cell_measurement_reflns_used    3938
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.78
_cell_volume                     2966.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19358
_diffrn_reflns_theta_full        31.04
_diffrn_reflns_theta_max         31.04
_diffrn_reflns_theta_min         2.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.784
_exptl_absorpt_correction_T_max  0.7330
_exptl_absorpt_correction_T_min  0.3057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.543
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0368
_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)+(0.0329P)²+1.2401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                2916
_reflns_number_total             4731
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5263.cif
_cod_data_source_block           I
_cod_database_code               2230785
_cod_database_fobs_code          2230785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.19995(4) 0.063553(17) 0.603716(11) 0.07024(11) Uani d . 1 1 . .
O O1 0.4583(2) 0.13020(14) 0.46925(7) 0.0717(5) Uani d . 1 1 . .
O O2 0.4899(2) 0.19606(9) 0.37415(6) 0.0579(4) Uani d . 1 1 . .
O O3 0.4628(2) 0.04790(10) 0.35626(6) 0.0604(4) Uani d . 1 1 . .
O O4 0.19571(19) 0.00663(10) 0.29651(6) 0.0544(4) Uani d . 1 1 . .
C C1 0.9183(3) 0.14467(14) 0.47702(8) 0.0488(5) Uani d . 1 1 . .
H H1A 0.9406 0.1695 0.4445 0.059 Uiso calc R 1 1 . .
C C2 1.0517(3) 0.12695(15) 0.51036(8) 0.0517(5) Uani d . 1 1 . .
H H2A 1.1635 0.1396 0.5007 0.062 Uiso calc R 1 1 . .
C C3 1.0158(3) 0.09006(13) 0.55825(8) 0.0487(5) Uani d . 1 1 . .
C C4 0.8516(3) 0.07055(14) 0.57344(8) 0.0538(5) Uani d . 1 1 . .
H H4A 0.8302 0.0457 0.6060 0.065 Uiso calc R 1 1 . .
C C5 0.7199(3) 0.08825(15) 0.53991(8) 0.0504(5) Uani d . 1 1 . .
H H5A 0.6087 0.0749 0.5498 0.060 Uiso calc R 1 1 . .
C C6 0.7504(3) 0.12584(13) 0.49133(7) 0.0428(4) Uani d . 1 1 . .
C C7 0.6034(3) 0.14284(14) 0.45588(8) 0.0470(4) Uani d . 1 1 . .
C C8 0.6423(3) 0.17663(14) 0.40202(8) 0.0496(5) Uani d . 1 1 . .
H H8A 0.7113 0.2313 0.4042 0.059 Uiso calc R 1 1 . .
H H8B 0.7073 0.1308 0.3835 0.059 Uiso calc R 1 1 . .
C C9 0.4043(3) 0.12319(13) 0.35557(7) 0.0444(4) Uani d . 1 1 . .
C C10 0.2356(3) 0.15108(13) 0.33476(7) 0.0420(4) Uani d . 1 1 . .
C C11 0.1753(3) 0.23898(15) 0.34381(8) 0.0540(5) Uani d . 1 1 . .
H H11A 0.2411 0.2790 0.3633 0.065 Uiso calc R 1 1 . .
C C12 0.0207(3) 0.26793(17) 0.32457(9) 0.0654(6) Uani d . 1 1 . .
H H12A -0.0176 0.3268 0.3311 0.078 Uiso calc R 1 1 . .
C C13 -0.0762(3) 0.20873(18) 0.29561(9) 0.0643(6) Uani d . 1 1 . .
H H13A -0.1803 0.2280 0.2823 0.077 Uiso calc R 1 1 . .
C C14 -0.0216(3) 0.12187(16) 0.28619(8) 0.0551(5) Uani d . 1 1 . .
H H14A -0.0894 0.0827 0.2668 0.066 Uiso calc R 1 1 . .
C C15 0.1337(3) 0.09149(13) 0.30522(7) 0.0442(4) Uani d . 1 1 . .
C C16 0.0967(4) -0.05475(17) 0.26574(11) 0.0735(7) Uani d . 1 1 . .
H H16A 0.1556 -0.1118 0.2627 0.110 Uiso calc R 1 1 . .
H H16B 0.0799 -0.0292 0.2318 0.110 Uiso calc R 1 1 . .
H H16C -0.0120 -0.0644 0.2820 0.110 Uiso calc R 1 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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O2 C8 . . 115.94(15) ?
C15 O4 C16 . . 118.42(17) ?
C2 C1 C6 . . 120.95(19) ?
C2 C1 H1A . . 119.5 ?
C6 C1 H1A . . 119.5 ?
C3 C2 C1 . . 118.55(19) ?
C3 C2 H2A . . 120.7 ?
C1 C2 H2A . . 120.7 ?
C4 C3 C2 . . 121.9(2) ?
C4 C3 Br1 . . 119.56(16) ?
C2 C3 Br1 . . 118.56(17) ?
C5 C4 C3 . . 119.1(2) ?
C5 C4 H4A . . 120.5 ?
C3 C4 H4A . . 120.5 ?
C4 C5 C6 . . 120.9(2) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C5 C6 C1 . . 118.64(19) ?
C5 C6 C7 . . 119.04(18) ?
C1 C6 C7 . . 122.30(18) ?
O1 C7 C6 . . 121.99(19) ?
O1 C7 C8 . . 120.4(2) ?
C6 C7 C8 . . 117.61(18) ?
O2 C8 C7 . . 111.19(18) ?
O2 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
O2 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
O3 C9 O2 . . 122.39(19) ?
O3 C9 C10 . . 126.97(18) ?
O2 C9 C10 . . 110.63(16) ?
C11 C10 C15 . . 118.24(19) ?
C11 C10 C9 . . 119.80(18) ?
C15 C10 C9 . . 121.96(17) ?
C12 C11 C10 . . 121.6(2) ?
C12 C11 H11A . . 119.2 ?
C10 C11 H11A . . 119.2 ?
C13 C12 C11 . . 119.2(2) ?
C13 C12 H12A . . 120.4 ?
C11 C12 H12A . . 120.4 ?
C14 C13 C12 . . 120.8(2) ?
C14 C13 H13A . . 119.6 ?
C12 C13 H13A . . 119.6 ?
C13 C14 C15 . . 120.8(2) ?
C13 C14 H14A . . 119.6 ?
C15 C14 H14A . . 119.6 ?
O4 C15 C14 . . 123.50(19) ?
O4 C15 C10 . . 117.17(17) ?
C14 C15 C10 . . 119.32(19) ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 C3 . 1.900(2) ?
O1 C7 . 1.203(3) ?
O2 C9 . 1.351(2) ?
O2 C8 . 1.423(2) ?
O3 C9 . 1.197(2) ?
O4 C15 . 1.356(2) ?
O4 C16 . 1.430(3) ?
C1 C2 . 1.378(3) ?
C1 C6 . 1.395(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.377(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.376(3) ?
C4 C5 . 1.371(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.389(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.492(3) ?
C7 C8 . 1.505(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.485(3) ?
C10 C11 . 1.394(3) ?
C10 C15 . 1.408(3) ?
C11 C12 . 1.377(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.375(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.367(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.386(3) ?
C14 H14A . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
C2 H2A O1 1_655 0.93 2.45 3.360(3) 165 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.1(3) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C1 C2 C3 Br1 . . . . 178.86(15) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
Br1 C3 C4 C5 . . . . -178.69(15) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C5 C6 C7 . . . . 179.23(18) ?
C2 C1 C6 C5 . . . . -0.4(3) ?
C2 C1 C6 C7 . . . . -179.03(19) ?
C5 C6 C7 O1 . . . . 4.6(3) ?
C1 C6 C7 O1 . . . . -176.7(2) ?
C5 C6 C7 C8 . . . . -175.25(18) ?
C1 C6 C7 C8 . . . . 3.4(3) ?
C9 O2 C8 C7 . . . . -76.7(2) ?
O1 C7 C8 O2 . . . . 4.4(3) ?
C6 C7 C8 O2 . . . . -175.70(16) ?
C8 O2 C9 O3 . . . . -9.5(3) ?
C8 O2 C9 C10 . . . . 171.08(17) ?
O3 C9 C10 C11 . . . . 170.4(2) ?
O2 C9 C10 C11 . . . . -10.3(3) ?
O3 C9 C10 C15 . . . . -10.5(3) ?
O2 C9 C10 C15 . . . . 168.90(17) ?
C15 C10 C11 C12 . . . . -0.2(3) ?
C9 C10 C11 C12 . . . . 179.0(2) ?
C10 C11 C12 C13 . . . . -0.2(3) ?
C11 C12 C13 C14 . . . . 0.5(4) ?
C12 C13 C14 C15 . . . . -0.6(4) ?
C16 O4 C15 C14 . . . . 0.5(3) ?
C16 O4 C15 C10 . . . . -178.7(2) ?
C13 C14 C15 O4 . . . . -179.0(2) ?
C13 C14 C15 C10 . . . . 0.2(3) ?
C11 C10 C15 O4 . . . . 179.39(17) ?
C9 C10 C15 O4 . . . . 0.2(3) ?
C11 C10 C15 C14 . . . . 0.1(3) ?
C9 C10 C15 C14 . . . . -179.03(18) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1760877
