#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/42/2014254.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_2014254
loop_
_publ_author_name
'Britton, Doyle'
'Brennessel, William W.'
_publ_section_title
;
 p-Chloro-, p-bromo- and two polymorphs of
 p-iodoacetophenone
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o552
_journal_page_last               o556
_journal_paper_doi               10.1107/S0108270104013824
_journal_volume                  60
_journal_year                    2004
_chemical_formula_sum            'C8 H7 Br O'
_chemical_formula_weight         199.05
_chemical_name_systematic
;
  4-bromoacetophenone
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXTL plus manual additions'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.635(5)
_cell_length_b                   6.9554(17)
_cell_length_c                   5.9035(15)
_cell_measurement_reflns_used    2078
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.2
_cell_volume                     760.5(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Siemens SMART area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.038
_diffrn_reflns_av_sigmaI/netI    0.051
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3840
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.328
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.39
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS including thin plate correction; Sheldrick, 1996; Blessing,
1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.75
_refine_diff_density_min         -0.27
_refine_ls_abs_structure_details
;
  Flack(1983),
  849 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.004(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.036P)²] where
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.074
_refine_ls_wR_factor_ref         0.077
_reflns_number_gt                1569
_reflns_number_total             1691
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1158.cif
_cod_data_source_block           BrM
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured ' was changed to
'?' - the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2014254
_cod_database_fobs_code          2014254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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 0.5000 0.27942(5) 0.5000 0.04028(13) Uani d . 1 . . Br
O1 0.8276(2) 0.1930(5) 0.0907(6) 0.0486(8) Uani d . 1 . . O
C1 0.7401(2) 0.2382(4) 0.3424(7) 0.0266(7) Uani d . 1 . . C
C2 0.6834(2) 0.1785(6) 0.1811(7) 0.0284(9) Uani d . 1 . . C
H2 0.6941 0.1297 0.0384 0.034 Uiso calc R 1 . . H
C3 0.6124(2) 0.1895(5) 0.2261(6) 0.0292(8) Uani d . 1 . . C
H3 0.5746 0.1480 0.1157 0.035 Uiso calc R 1 . . H
C4 0.5969(2) 0.2617(5) 0.4340(7) 0.0282(8) Uani d . 1 . . C
C5 0.6516(2) 0.3221(5) 0.5979(6) 0.0271(7) Uani d . 1 . . C
H5 0.6402 0.3728 0.7390 0.033 Uiso calc R 1 . . H
C6 0.7226(2) 0.3078(5) 0.5534(6) 0.0282(8) Uani d . 1 . . C
H6 0.7602 0.3454 0.6668 0.034 Uiso calc R 1 . . H
C7 0.8153(3) 0.2291(7) 0.2851(8) 0.0341(9) Uani d . 1 . . C
C8 0.8756(3) 0.2688(6) 0.4701(9) 0.0439(10) Uani d . 1 . . C
H8A 0.9221 0.2574 0.4079 0.066 Uiso calc R 1 . . H
H8B 0.8737 0.1757 0.5938 0.066 Uiso calc R 1 . . H
H8C 0.8705 0.3992 0.5291 0.066 Uiso calc R 1 . . H
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 0.03165(19) 0.0465(2) 0.0438(2) 0.0034(4) 0.00901(13) 0.0015(5)
O1 0.0398(19) 0.071(2) 0.0368(16) -0.0005(16) 0.0133(14) -0.0054(14)
C1 0.036(2) 0.0173(16) 0.0269(16) -0.0001(12) 0.0042(15) 0.0007(12)
C2 0.040(2) 0.023(2) 0.0228(18) 0.0000(17) 0.0047(14) 0.0003(15)
C3 0.035(2) 0.026(2) 0.0261(17) -0.0029(14) -0.0015(14) -0.0036(12)
C4 0.0271(19) 0.0241(18) 0.0342(19) 0.0020(13) 0.0074(15) 0.0050(13)
C5 0.037(2) 0.0214(18) 0.0234(16) 0.0033(13) 0.0041(14) -0.0021(12)
C6 0.037(2) 0.0221(19) 0.0257(18) -0.0018(13) 0.0031(15) -0.0010(12)
C7 0.038(2) 0.030(2) 0.035(2) 0.002(2) 0.0076(18) 0.0011(19)
C8 0.031(2) 0.056(3) 0.046(3) -0.0022(18) 0.0067(19) -0.0032(18)
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
C2 C1 C6 118.1(4)
C2 C1 C7 119.6(4)
C6 C1 C7 122.4(4)
C3 C2 C1 121.3(4)
C3 C2 H2 119.4
C1 C2 H2 119.4
C4 C3 C2 119.3(4)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 121.1(4)
C3 C4 Br1 120.3(3)
C5 C4 Br1 118.7(3)
C6 C5 C4 119.4(3)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C6 C1 120.9(4)
C5 C6 H6 119.5
C1 C6 H6 119.5
O1 C7 C1 120.4(4)
O1 C7 C8 121.1(5)
C1 C7 C8 118.5(4)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 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 C4 . 1.892(4) ?
O1 C7 . 1.221(6) ?
C1 C2 . 1.405(6) ?
C1 C6 . 1.408(5) ?
C1 C7 . 1.478(7) ?
C2 C3 . 1.379(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.386(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.390(6) ?
C5 C6 . 1.382(5) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.504(7) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7186
