#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/21/2212165.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_2212165
loop_
_publ_author_name
'Hoong-Kun Fun'
'Suchada Chantrapromma'
'Shyamaprosad Goswami'
'Subrata Jana'
_publ_section_title
;
 [3-Benzoyl-2,4-bis(3-bromophenyl)cyclobutyl](phenyl)methanone
;
_journal_coeditor_code           FL2096
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1069
_journal_page_last               o1070
_journal_paper_doi               10.1107/S1600536807004217
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C30 H22 Br2 O2'
_chemical_formula_moiety         'C30 H22 Br2 O2'
_chemical_formula_sum            'C30 H22 Br2 O2'
_chemical_formula_weight         574.28
_chemical_melting_point          337.5(5)
_chemical_name_common
;
3-Benzoyl-2,4-bis(3-bromophenyl)cyclobutyl phenyl ketone
;
_chemical_name_systematic
;
[3-Benzoyl-2,4-bis(3-bromophenyl)cyclobutyl](phenyl)methanone
;
_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                 102.9880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.78130(10)
_cell_length_b                   14.6794(2)
_cell_length_c                   14.2828(2)
_cell_measurement_reflns_used    3429
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.78
_cell_volume                     1181.11(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18746
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.458
_exptl_absorpt_correction_T_max  0.7369
_exptl_absorpt_correction_T_min  0.3003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.349
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0261P)²+0.7106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0615
_reflns_number_gt                2869
_reflns_number_total             3429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2096.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:

'_chemical_melting_point' value '337-338' was changed to '337.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '337-338' was changed to '337.5(5)' -
the average value was taken and precision was
estimated.

'_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               2212165
_cod_database_fobs_code          2212165
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 Br1A 0.95743(3) 0.677394(12) 0.090265(11) 0.02250(6) Uani d . 1
O O1 1.46944(19) 0.58511(9) 0.58587(8) 0.0194(2) Uani d . 1
C C1 1.0989(3) 0.61914(11) 0.75297(11) 0.0161(3) Uani d . 1
H H1 0.9565 0.6359 0.7104 0.024(5) Uiso d R 1
C C2 1.1158(3) 0.62929(12) 0.85149(12) 0.0199(3) Uani d . 1
H H2 0.9925 0.6547 0.8728 0.017(5) Uiso d R 1
C C3 1.3218(3) 0.60353(13) 0.91637(12) 0.0221(4) Uani d . 1
H H3 1.3315 0.6099 0.9819 0.030(6) Uiso d R 1
C C4 1.5126(3) 0.56867(12) 0.88346(12) 0.0205(3) Uani d . 1
H H4 1.6516 0.5506 0.9263 0.025(5) Uiso d R 1
C C5 1.4993(3) 0.56172(11) 0.78581(12) 0.0169(3) Uani d . 1
H H5 1.6252 0.5400 0.7630 0.016(5) Uiso d R 1
C C6 1.2925(3) 0.58670(10) 0.71972(11) 0.0137(3) Uani d . 1
C C7 1.2873(3) 0.57827(10) 0.61493(11) 0.0139(3) Uani d . 1
C C8 1.0498(3) 0.55832(10) 0.54807(10) 0.0124(3) Uani d . 1
H H8 0.9455 0.6015 0.5581 0.013(4) Uiso d R 1
C C9 1.0544(3) 0.54013(11) 0.44219(10) 0.0124(3) Uani d . 1
H H9 1.2145 0.5363 0.4339 0.012(4) Uiso d R 1
C C10 0.9128(3) 0.60158(10) 0.36589(11) 0.0131(3) Uani d . 1
C C11 0.9880(3) 0.61289(10) 0.28015(11) 0.0137(3) Uani d . 1
H H11 1.1279 0.5846 0.2724 0.012(4) Uiso d R 1
C C12 0.8518(3) 0.66377(11) 0.20650(11) 0.0155(3) Uani d . 1
C C13 0.6432(3) 0.70614(11) 0.21493(12) 0.0176(3) Uani d . 1
H H13 0.5599 0.7401 0.1639 0.027(6) Uiso d R 1
C C14 0.5706(3) 0.69579(11) 0.30056(12) 0.0180(3) Uani d . 1
H H14 0.4260 0.7247 0.3077 0.018(5) Uiso d R 1
C C15 0.7020(3) 0.64359(11) 0.37522(11) 0.0158(3) Uani d . 1
H H15 0.6477 0.6377 0.4286 0.013(4) Uiso d 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'
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 . . 119.99(15) ?
C6 C1 H1 . . 121.5 ?
C2 C1 H1 . . 118.5 ?
C3 C2 C1 . . 119.95(16) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 119.7 ?
C2 C3 C4 . . 120.12(15) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 120.3 ?
C5 C4 C3 . . 119.97(15) ?
C5 C4 H4 . . 119.0 ?
C3 C4 H4 . . 121.0 ?
C4 C5 C6 . . 120.50(15) ?
C4 C5 H5 . . 120.9 ?
C6 C5 H5 . . 118.6 ?
C1 C6 C5 . . 119.39(14) ?
C1 C6 C7 . . 122.14(14) ?
C5 C6 C7 . . 118.47(14) ?
O1 C7 C6 . . 120.59(14) ?
O1 C7 C8 . . 122.08(14) ?
C6 C7 C8 . . 117.30(13) y
C7 C8 C9 . . 116.02(12) y
C7 C8 C9 . 3_766 115.46(12) ?
C9 C8 C9 . 3_766 91.09(11) ?
C7 C8 H8 . . 107.8 ?
C9 C8 H8 . . 115.7 ?
C9 C8 H8 3_766 . 110.1 ?
C10 C9 C8 . . 118.63(13) ?
C10 C9 C8 . 3_766 117.01(12) ?
C8 C9 C8 . 3_766 88.91(11) ?
C10 C9 H9 . . 109.1 ?
C8 C9 H9 . . 111.2 ?
C8 C9 H9 3_766 . 110.7 ?
C11 C10 C15 . . 118.69(14) ?
C11 C10 C9 . . 118.63(13) ?
C15 C10 C9 . . 122.58(14) ?
C12 C11 C10 . . 119.62(14) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 119.8 ?
C11 C12 C13 . . 122.29(15) ?
C11 C12 Br1A . . 118.72(12) ?
C13 C12 Br1A . . 118.98(12) ?
C12 C13 C14 . . 117.95(15) ?
C12 C13 H13 . . 118.9 ?
C14 C13 H13 . . 123.1 ?
C13 C14 C15 . . 120.97(15) ?
C13 C14 H14 . . 119.1 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C10 . . 120.46(15) ?
C14 C15 H15 . . 118.2 ?
C10 C15 H15 . . 121.4 ?
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
Br1A C12 . 1.9039(16) y
O1 C7 . 1.2199(19) y
C1 C6 . 1.394(2) ?
C1 C2 . 1.396(2) ?
C1 H1 . 0.9397 ?
C2 C3 . 1.387(2) ?
C2 H2 . 0.9148 ?
C3 C4 . 1.390(3) ?
C3 H3 . 0.9295 ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.9324 ?
C5 C6 . 1.396(2) ?
C5 H5 . 0.9188 ?
C6 C7 . 1.495(2) ?
C7 C8 . 1.514(2) y
C8 C9 . 1.542(2) y
C8 C9 3_766 1.584(2) ?
C8 H8 . 0.9083 ?
C9 C10 . 1.507(2) ?
C9 C8 3_766 1.584(2) ?
C9 H9 . 0.9607 ?
C10 C11 . 1.398(2) ?
C10 C15 . 1.399(2) ?
C11 C12 . 1.383(2) ?
C11 H11 . 0.9377 ?
C12 C13 . 1.386(2) ?
C13 C14 . 1.388(2) ?
C13 H13 . 0.9237 ?
C14 C15 . 1.392(2) ?
C14 H14 . 0.9632 ?
C15 H15 . 0.8912 ?
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 H9 O1 3_866 0.96 2.6128 3.408(2) 140 y
C2 H2 Cg3 4_565 0.93 3.1862 3.7323(19) 120 n
C14 H14 Cg2 4_464 0.96 2.7499 3.4655(18) 132 n
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_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . -2.7(3) ?
C1 C2 C3 C4 . . 0.8(3) ?
C2 C3 C4 C5 . . 1.6(3) ?
C3 C4 C5 C6 . . -2.1(3) ?
C2 C1 C6 C5 . . 2.2(2) ?
C2 C1 C6 C7 . . -177.37(15) ?
C4 C5 C6 C1 . . 0.2(2) ?
C4 C5 C6 C7 . . 179.77(15) ?
C1 C6 C7 O1 . . 151.02(16) ?
C5 C6 C7 O1 . . -28.5(2) y
C1 C6 C7 C8 . . -30.7(2) y
C5 C6 C7 C8 . . 149.72(15) ?
O1 C7 C8 C9 . . 4.3(2) ?
C6 C7 C8 C9 . . -173.86(13) ?
O1 C7 C8 C9 . 3_766 109.17(17) ?
C6 C7 C8 C9 . 3_766 -69.03(17) ?
C7 C8 C9 C10 . . -120.33(15) ?
C9 C8 C9 C10 3_766 . 120.48(15) ?
C7 C8 C9 C8 . 3_766 119.19(15) ?
C9 C8 C9 C8 3_766 3_766 0.0 ?
C8 C9 C10 C11 . . 152.96(14) ?
C8 C9 C10 C11 3_766 . -102.33(16) ?
C8 C9 C10 C15 . . -30.8(2) y
C8 C9 C10 C15 3_766 . 73.96(19) ?
C15 C10 C11 C12 . . -1.0(2) ?
C9 C10 C11 C12 . . 175.47(14) ?
C10 C11 C12 C13 . . 1.3(2) ?
C10 C11 C12 Br1A . . -179.60(11) ?
C11 C12 C13 C14 . . -0.5(2) ?
Br1A C12 C13 C14 . . -179.55(12) ?
C12 C13 C14 C15 . . -0.7(2) ?
C13 C14 C15 C10 . . 1.0(2) ?
C11 C10 C15 C14 . . -0.2(2) ?
C9 C10 C15 C14 . . -176.48(15) ?
