#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221719.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_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       \w/2\q
_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 <i>et al.</i>,  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/[\s^2^(Fo^2^)+(0.022P)^2^] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_[local]_cod_data_source_file    hk2660.cif
_[local]_cod_data_source_block   I
_cod_database_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
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
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_distance
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
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)