#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/05/2210542.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_2210542
loop_
_publ_author_name
'Jeannie Bee-Jan Teh'
'P. S. Patil'
'Hoong-Kun Fun'
'Ibrahim Abdul Razak'
'S. M. Dharmaprakash'
_publ_section_title
;
 3-(4-Bromophenyl)-1-(2,4-dichlorophenyl)prop-2-en-1-one
;
_journal_coeditor_code           CI2160
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4380
_journal_page_last               o4381
_journal_paper_doi               10.1107/S1600536806035951
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H9 Br Cl2 O'
_chemical_formula_moiety         'C15 H9 Br Cl2 O'
_chemical_formula_sum            'C15 H9 Br Cl2 O'
_chemical_formula_weight         356.03
_chemical_name_systematic
;
3-(4-Bromophenyl)-1-(2,4-dichlorophenyl) prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 94.9230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.9039(3)
_cell_length_b                   3.84740(10)
_cell_length_c                   13.9069(2)
_cell_measurement_reflns_used    5935
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      38.84
_cell_measurement_theta_min      0.82
_cell_volume                     1327.58(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Brucker SMART APEX2 CCD area-detector
;
_diffrn_measurement_method       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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42784
_diffrn_reflns_theta_full        38.84
_diffrn_reflns_theta_max         38.84
_diffrn_reflns_theta_min         0.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.485
_exptl_absorpt_correction_T_max  0.7376
_exptl_absorpt_correction_T_min  0.5518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.574
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         7604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0298
_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)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                5633
_reflns_number_total             7604
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2160.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210542
_cod_database_fobs_code          2210542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.450297(6) 0.20900(4) 0.418371(10) 0.01889(4) Uani d . 1
Cl Cl1 0.153167(14) -0.19917(9) 0.09487(2) 0.01663(6) Uani d . 1
Cl Cl2 -0.002537(12) 0.39293(9) -0.13853(2) 0.01669(6) Uani d . 1
O O1 0.24920(4) -0.2145(3) -0.13899(8) 0.0214(2) Uani d . 1
C C1 0.13438(5) -0.0020(3) -0.01572(9) 0.0134(2) Uani d . 1
C C2 0.08074(5) 0.1009(4) -0.03212(9) 0.0138(2) Uani d . 1
H H2A 0.0568 0.0680 0.0148 0.017 Uiso calc R 1
C C3 0.06392(5) 0.2528(3) -0.11960(10) 0.0135(2) Uani d . 1
C C4 0.09838(5) 0.2964(4) -0.19196(10) 0.0155(2) Uani d . 1
H H4A 0.0862 0.3961 -0.2507 0.019 Uiso calc R 1
C C5 0.15163(5) 0.1874(4) -0.17442(10) 0.0150(2) Uani d . 1
H H5A 0.1750 0.2124 -0.2226 0.018 Uiso calc R 1
C C6 0.17083(5) 0.0404(4) -0.08564(9) 0.0139(2) Uani d . 1
C C7 0.22943(5) -0.0626(4) -0.07318(10) 0.0155(2) Uani d . 1
C C8 0.26055(5) 0.0397(4) 0.01707(10) 0.0165(2) Uani d . 1
H H8A 0.2453 0.1939 0.0584 0.020 Uiso calc R 1
C C9 0.31027(5) -0.0826(4) 0.04166(10) 0.0154(2) Uani d . 1
H H9A 0.3252 -0.2293 -0.0021 0.018 Uiso calc R 1
C C10 0.34309(5) -0.0044(4) 0.13164(9) 0.0143(2) Uani d . 1
C C11 0.39747(5) -0.1066(4) 0.14139(10) 0.0151(2) Uani d . 1
H H11A 0.4121 -0.2184 0.0904 0.018 Uiso calc R 1
C C12 0.42964(5) -0.0427(4) 0.22617(10) 0.0157(2) Uani d . 1
H H12A 0.4657 -0.1088 0.2321 0.019 Uiso calc R 1
C C13 0.40699(5) 0.1216(4) 0.30193(9) 0.0149(2) Uani d . 1
C C14 0.35325(6) 0.2229(4) 0.29487(11) 0.0171(2) Uani d . 1
H H14A 0.3387 0.3310 0.3465 0.021 Uiso calc R 1
C C15 0.32171(5) 0.1604(4) 0.20979(10) 0.0173(2) Uani d . 1
H H15A 0.2858 0.2288 0.2044 0.021 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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 121.63(12)
C2 C1 Cl1 116.70(10)
C6 C1 Cl1 121.63(10)
C3 C2 C1 118.57(12)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
C2 C3 C4 122.00(12)
C2 C3 Cl2 118.50(10)
C4 C3 Cl2 119.50(11)
C3 C4 C5 118.40(13)
C3 C4 H4A 120.8
C5 C4 H4A 120.8
C4 C5 C6 121.51(12)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
C1 C6 C5 117.85(11)
C1 C6 C7 124.76(12)
C5 C6 C7 117.38(11)
O1 C7 C8 123.30(12)
O1 C7 C6 119.15(12)
C8 C7 C6 117.50(11)
C9 C8 C7 122.09(13)
C9 C8 H8A 119.0
C7 C8 H8A 119.0
C8 C9 C10 125.49(13)
C8 C9 H9A 117.3
C10 C9 H9A 117.3
C15 C10 C11 118.59(12)
C15 C10 C9 122.24(12)
C11 C10 C9 119.14(12)
C12 C11 C10 120.86(12)
C12 C11 H11A 119.6
C10 C11 H11A 119.6
C13 C12 C11 118.82(12)
C13 C12 H12A 120.6
C11 C12 H12A 120.6
C12 C13 C14 121.70(12)
C12 C13 Br1 119.34(10)
C14 C13 Br1 118.96(10)
C15 C14 C13 118.97(13)
C15 C14 H14A 120.5
C13 C14 H14A 120.5
C14 C15 C10 121.06(12)
C14 C15 H15A 119.5
C10 C15 H15A 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.8971(13)
Cl1 C1 1.7424(13)
Cl2 C3 1.7390(13)
O1 C7 1.2244(17)
C1 C2 1.3932(18)
C1 C6 1.3955(17)
C2 C3 1.3819(19)
C2 H2A 0.93
C3 C4 1.3878(19)
C4 C5 1.3923(19)
C4 H4A 0.93
C5 C6 1.4040(19)
C5 H5A 0.93
C6 C7 1.5078(18)
C7 C8 1.4711(19)
C8 C9 1.3411(18)
C8 H8A 0.93
C9 C10 1.4659(18)
C9 H9A 0.93
C10 C15 1.4020(19)
C10 C11 1.4055(18)
C11 C12 1.3893(18)
C11 H11A 0.93
C12 C13 1.3890(19)
C12 H12A 0.93
C13 C14 1.3893(19)
C14 C15 1.384(2)
C14 H14A 0.93
C15 H15A 0.93
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 -0.9(2)
Cl1 C1 C2 C3 -178.88(10)
C1 C2 C3 C4 1.8(2)
C1 C2 C3 Cl2 -178.08(10)
C2 C3 C4 C5 -1.0(2)
Cl2 C3 C4 C5 178.94(10)
C3 C4 C5 C6 -0.8(2)
C2 C1 C6 C5 -0.8(2)
Cl1 C1 C6 C5 177.09(10)
C2 C1 C6 C7 179.71(13)
Cl1 C1 C6 C7 -2.43(19)
C4 C5 C6 C1 1.6(2)
C4 C5 C6 C7 -178.79(13)
C1 C6 C7 O1 135.83(15)
C5 C6 C7 O1 -43.69(19)
C1 C6 C7 C8 -46.69(19)
C5 C6 C7 C8 133.79(13)
O1 C7 C8 C9 -12.9(2)
C6 C7 C8 C9 169.75(13)
C7 C8 C9 C10 -177.55(13)
C8 C9 C10 C15 11.7(2)
C8 C9 C10 C11 -170.24(14)
C15 C10 C11 C12 -0.7(2)
C9 C10 C11 C12 -178.85(13)
C10 C11 C12 C13 0.6(2)
C11 C12 C13 C14 0.0(2)
C11 C12 C13 Br1 179.75(10)
C12 C13 C14 C15 -0.5(2)
Br1 C13 C14 C15 179.74(11)
C13 C14 C15 C10 0.4(2)
C11 C10 C15 C14 0.2(2)
C9 C10 C15 C14 178.27(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655058
