#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221719.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_2221719
loop_
_publ_author_name
'Chen, Lei'
'Xu, Qing-Bing'
'Song, Guang-Liang'
'Zhu, Hong-Jun'
_publ_section_title
;
 2-Bromo-1-mesitylethanone
;
_journal_coeditor_code           HK2660
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1083
_journal_paper_doi               10.1107/S1600536809012276
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H13 Br O'
_chemical_formula_moiety         'C11 H13 Br O'
_chemical_formula_sum            'C11 H13 Br O'
_chemical_formula_weight         241.12
_chemical_name_systematic
;
2-bromo-1-mesitylethanone
;
_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                   15.379(3)
_cell_length_b                   8.2820(17)
_cell_length_c                   17.374(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     2212.9(8)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0990
_diffrn_reflns_av_sigmaI/netI    0.1434
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3509
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.676
_exptl_absorpt_correction_T_max  0.7101
_exptl_absorpt_correction_T_min  0.5268
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1981
_refine_ls_R_factor_gt           0.0637
_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)+(0.022P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                805
_reflns_number_total             2002
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2660.cif
_cod_data_source_block           I
_cod_database_code               2221719
_cod_database_fobs_code          2221719
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_disorder_assembly
_atom_site_disorder_group
Br Br 0.22106(4) 0.01688(8) 0.59900(4) 0.0758(3) Uani d . 1 . .
O O 0.1783(3) -0.1396(5) 0.7510(3) 0.0853(16) Uani d . 1 . .
C C1 -0.0250(4) 0.1475(7) 0.8818(4) 0.0557(19) Uani d . 1 . .
H H1A -0.0852 0.1583 0.8816 0.067 Uiso calc R 1 . .
C C2 0.0138(4) 0.0860(6) 0.8160(4) 0.0461(16) Uani d . 1 . .
C C3 0.1038(4) 0.0675(6) 0.8208(4) 0.0458(17) Uani d . 1 . .
C C4 0.1509(4) 0.1135(7) 0.8840(4) 0.0462(17) Uani d . 1 . .
C C5 0.1083(4) 0.1744(7) 0.9464(4) 0.0540(18) Uani d . 1 . .
H H5A 0.1400 0.2040 0.9898 0.065 Uiso calc R 1 . .
C C6 0.0180(5) 0.1932(7) 0.9465(4) 0.062(2) Uani d . 1 . .
C C7 -0.0290(3) 0.2598(7) 1.0151(4) 0.079(2) Uani d . 1 . .
H H7A -0.0903 0.2624 1.0048 0.119 Uiso calc R 1 . .
H H7B -0.0088 0.3672 1.0255 0.119 Uiso calc R 1 . .
H H7C -0.0181 0.1924 1.0590 0.119 Uiso calc R 1 . .
C C8 -0.0388(3) 0.0364(6) 0.7488(3) 0.0630(18) Uani d . 1 . .
H H8A -0.0989 0.0601 0.7583 0.094 Uiso calc R 1 . .
H H8B -0.0319 -0.0774 0.7403 0.094 Uiso calc R 1 . .
H H8C -0.0196 0.0944 0.7040 0.094 Uiso calc R 1 . .
C C9 0.2492(3) 0.0917(7) 0.8895(3) 0.068(2) Uani d . 1 . .
H H9A 0.2692 0.1304 0.9385 0.101 Uiso calc R 1 . .
H H9B 0.2769 0.1517 0.8491 0.101 Uiso calc R 1 . .
H H9C 0.2633 -0.0207 0.8843 0.101 Uiso calc R 1 . .
C C10 0.1514(4) -0.0002(8) 0.7513(3) 0.0459(15) Uani d . 1 . .
C C11 0.1681(3) 0.1137(7) 0.6882(3) 0.0592(19) Uani d . 1 . .
H H11A 0.2057 0.1991 0.7069 0.071 Uiso calc R 1 . .
H H11B 0.1135 0.1628 0.6729 0.071 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
Br 0.0835(6) 0.0705(5) 0.0734(5) -0.0009(5) 0.0146(4) -0.0066(5)
O 0.111(4) 0.057(3) 0.088(4) 0.040(3) 0.016(3) 0.015(3)
C1 0.033(4) 0.044(4) 0.090(6) 0.000(3) 0.021(4) 0.011(4)
C2 0.037(5) 0.036(4) 0.065(5) 0.002(3) 0.000(4) -0.005(4)
C3 0.044(5) 0.030(4) 0.064(5) -0.002(3) 0.011(4) -0.009(3)
C4 0.026(4) 0.041(4) 0.072(6) -0.004(3) 0.005(4) 0.001(4)
C5 0.047(5) 0.050(4) 0.065(5) -0.008(4) -0.004(4) 0.002(4)
C6 0.087(7) 0.039(4) 0.059(6) -0.005(5) 0.016(5) 0.002(4)
C7 0.075(6) 0.084(5) 0.079(7) 0.015(4) 0.011(5) 0.009(5)
C8 0.049(4) 0.054(4) 0.085(5) 0.000(4) -0.021(4) 0.002(4)
C9 0.048(5) 0.080(5) 0.075(5) -0.016(3) -0.015(4) 0.014(4)
C10 0.038(4) 0.038(4) 0.061(4) -0.005(4) -0.016(3) 0.010(5)
C11 0.042(4) 0.065(5) 0.070(5) 0.002(3) 0.003(4) 0.003(4)
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
C6 C1 C2 . . 125.2(6) ?
C6 C1 H1A . . 117.4 ?
C2 C1 H1A . . 117.4 ?
C1 C2 C3 . . 114.7(6) ?
C1 C2 C8 . . 121.2(6) ?
C3 C2 C8 . . 124.0(6) ?
C4 C3 C2 . . 122.8(6) ?
C4 C3 C10 . . 119.0(6) ?
C2 C3 C10 . . 118.1(6) ?
C5 C4 C3 . . 119.1(6) ?
C5 C4 C9 . . 118.0(6) ?
C3 C4 C9 . . 122.8(6) ?
C4 C5 C6 . . 121.3(6) ?
C4 C5 H5A . . 119.4 ?
C6 C5 H5A . . 119.4 ?
C1 C6 C5 . . 116.8(7) ?
C1 C6 C7 . . 121.8(7) ?
C5 C6 C7 . . 121.4(8) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C2 C8 H8A . . 109.5 ?
C2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C4 C9 H9A . . 109.5 ?
C4 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C4 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O C10 C11 . . 122.8(6) ?
O C10 C3 . . 120.9(5) ?
C11 C10 C3 . . 116.1(6) ?
C10 C11 Br . . 114.0(4) ?
C10 C11 H11A . . 108.7 ?
Br C11 H11A . . 108.7 ?
C10 C11 H11B . . 108.7 ?
Br C11 H11B . . 108.7 ?
H11A C11 H11B . . 107.6 ?
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
Br C11 . 1.925(6) ?
O C10 . 1.226(6) ?
C1 C6 . 1.358(9) ?
C1 C2 . 1.387(8) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.396(7) ?
C2 C8 . 1.479(7) ?
C3 C4 . 1.369(8) ?
C3 C10 . 1.519(8) ?
C4 C5 . 1.364(7) ?
C4 C9 . 1.526(7) ?
C5 C6 . 1.399(7) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.499(8) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.470(7) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
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
C9 H9B O 8_665 0.96 2.52 3.462(7) 166 yes
C11 H11A O 8_665 0.97 2.36 3.308(7) 167 yes
C7 H7C Cg1 5_566 0.96 2.94 3.722(3) 140 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 . . . . 2.1(9) ?
C6 C1 C2 C8 . . . . 178.8(6) ?
C1 C2 C3 C4 . . . . -3.0(8) ?
C8 C2 C3 C4 . . . . -179.6(6) ?
C1 C2 C3 C10 . . . . 179.6(5) ?
C8 C2 C3 C10 . . . . 3.0(8) ?
C2 C3 C4 C5 . . . . 2.6(9) ?
C10 C3 C4 C5 . . . . 180.0(5) ?
C2 C3 C4 C9 . . . . 179.4(5) ?
C10 C3 C4 C9 . . . . -3.3(8) ?
C3 C4 C5 C6 . . . . -1.2(9) ?
C9 C4 C5 C6 . . . . -178.0(5) ?
C2 C1 C6 C5 . . . . -0.8(10) ?
C2 C1 C6 C7 . . . . 179.6(6) ?
C4 C5 C6 C1 . . . . 0.2(9) ?
C4 C5 C6 C7 . . . . 179.9(6) ?
C4 C3 C10 O . . . . 77.5(8) ?
C2 C3 C10 O . . . . -105.0(7) ?
C4 C3 C10 C11 . . . . -98.3(6) ?
C2 C3 C10 C11 . . . . 79.2(7) ?
O C10 C11 Br . . . . 8.5(8) ?
C3 C10 C11 Br . . . . -175.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 190253
