#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/27/2222726.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_2222726
loop_
_publ_author_name
'Zhou, Yi-Xin'
'Wang, Jian-Qiang'
'Du, Ren-Jun'
'Tang, Jian-Guo'
'Guo, Cheng'
_publ_section_title
;
 4-Bromo-2-(4-fluorobenzylidene)indan-1-one
;
_journal_coeditor_code           HK2723
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1936
_journal_paper_doi               10.1107/S1600536809025781
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H10 Br F O'
_chemical_formula_moiety         'C16 H10 Br F O'
_chemical_formula_sum            'C16 H10 Br F O'
_chemical_formula_weight         317.15
_chemical_name_systematic
;
4-Bromo-2-(4-fluorobenzylidene)indan-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.45(3)
_cell_angle_beta                 96.80(3)
_cell_angle_gamma                111.72(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3580(15)
_cell_length_b                   7.4630(15)
_cell_length_c                   13.140(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     642.2(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2518
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.200
_exptl_absorpt_correction_T_max  0.8564
_exptl_absorpt_correction_T_min  0.7403
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.354
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0588
_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)+(0.067P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                1351
_reflns_number_total             2319
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2723.cif
_cod_data_source_block           I
_cod_database_code               2222726
_cod_database_fobs_code          2222726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.47010(11) 0.25337(12) 0.59830(5) 0.0759(3) Uani d . 1 . .
O O 0.2276(6) 0.2064(7) 1.0423(3) 0.0688(12) Uani d . 1 . .
F F 0.8344(6) 0.2939(6) 1.4682(2) 0.0883(12) Uani d . 1 . .
C C1 0.7931(11) 0.2919(9) 1.3633(4) 0.0618(17) Uani d . 1 . .
C C2 0.6046(11) 0.2666(9) 1.3199(4) 0.0657(18) Uani d . 1 . .
H H2A 0.5071 0.2516 1.3604 0.079 Uiso calc R 1 . .
C C3 0.5620(9) 0.2638(9) 1.2136(4) 0.0558(16) Uani d . 1 . .
H H3A 0.4348 0.2475 1.1823 0.067 Uiso calc R 1 . .
C C4 0.7092(9) 0.2854(8) 1.1535(4) 0.0483(14) Uani d . 1 . .
C C5 0.8976(9) 0.3109(9) 1.2025(4) 0.0586(16) Uani d . 1 . .
H H5A 0.9979 0.3272 1.1639 0.070 Uiso calc R 1 . .
C C6 0.9387(10) 0.3124(9) 1.3084(5) 0.0678(18) Uani d . 1 . .
H H6A 1.0648 0.3273 1.3407 0.081 Uiso calc R 1 . .
C C7 0.6811(9) 0.2884(8) 1.0409(4) 0.0543(15) Uani d . 1 . .
H H7A 0.7986 0.3146 1.0156 0.065 Uiso calc R 1 . .
C C8 0.5240(8) 0.2619(8) 0.9659(4) 0.0467(14) Uani d . 1 . .
C C9 0.3131(9) 0.2200(8) 0.9680(4) 0.0497(15) Uani d . 1 . .
C C10 0.2123(9) 0.1972(8) 0.8595(4) 0.0449(13) Uani d . 1 . .
C C11 0.0132(10) 0.1497(9) 0.8219(4) 0.0621(17) Uani d . 1 . .
H H11A -0.0777 0.1254 0.8663 0.075 Uiso calc R 1 . .
C C12 -0.0493(10) 0.1387(9) 0.7156(4) 0.0642(17) Uani d . 1 . .
H H12A -0.1827 0.1093 0.6886 0.077 Uiso calc R 1 . .
C C13 0.0868(10) 0.1714(9) 0.6507(4) 0.0607(17) Uani d . 1 . .
H H13A 0.0442 0.1646 0.5800 0.073 Uiso calc R 1 . .
C C14 0.2830(10) 0.2135(8) 0.6883(4) 0.0510(15) Uani d . 1 . .
C C15 0.3494(9) 0.2285(8) 0.7946(4) 0.0474(14) Uani d . 1 . .
C C16 0.5512(8) 0.2711(9) 0.8538(4) 0.0515(15) Uani d . 1 . .
H H16A 0.6460 0.4025 0.8538 0.062 Uiso calc R 1 . .
H H16B 0.5987 0.1720 0.8228 0.062 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'
F F 0.0171 0.0103 '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 . . 123.3(5) ?
C6 C1 F . . 118.5(6) ?
C2 C1 F . . 118.1(6) ?
C1 C2 C3 . . 118.3(6) ?
C1 C2 H2A . . 120.9 ?
C3 C2 H2A . . 120.9 ?
C2 C3 C4 . . 120.3(6) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
C5 C4 C3 . . 118.4(5) ?
C5 C4 C7 . . 116.8(5) ?
C3 C4 C7 . . 124.7(5) ?
C4 C5 C6 . . 120.9(6) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C1 C6 C5 . . 118.7(6) ?
C1 C6 H6A . . 120.7 ?
C5 C6 H6A . . 120.7 ?
C8 C7 C4 . . 134.8(5) ?
C8 C7 H7A . . 112.6 ?
C4 C7 H7A . . 112.6 ?
C7 C8 C9 . . 132.6(5) ?
C7 C8 C16 . . 119.9(5) ?
C9 C8 C16 . . 107.5(4) ?
O C9 C8 . . 129.6(5) ?
O C9 C10 . . 123.4(5) ?
C8 C9 C10 . . 107.1(4) ?
C11 C10 C15 . . 122.0(5) ?
C11 C10 C9 . . 128.3(5) ?
C15 C10 C9 . . 109.7(5) ?
C10 C11 C12 . . 118.4(6) ?
C10 C11 H11A . . 120.8 ?
C12 C11 H11A . . 120.8 ?
C13 C12 C11 . . 119.9(6) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C14 C13 C12 . . 121.2(5) ?
C14 C13 H13A . . 119.4 ?
C12 C13 H13A . . 119.4 ?
C13 C14 C15 . . 119.9(5) ?
C13 C14 Br . . 121.3(4) ?
C15 C14 Br . . 118.8(5) ?
C10 C15 C14 . . 118.5(5) ?
C10 C15 C16 . . 111.1(4) ?
C14 C15 C16 . . 130.3(5) ?
C15 C16 C8 . . 104.5(4) ?
C15 C16 H16A . . 110.8 ?
C8 C16 H16A . . 110.8 ?
C15 C16 H16B . . 110.8 ?
C8 C16 H16B . . 110.8 ?
H16A C16 H16B . . 108.9 ?
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 C14 . 1.898(6) ?
O C9 . 1.224(6) ?
F C1 . 1.371(6) ?
C1 C6 . 1.341(9) ?
C1 C2 . 1.365(8) ?
C2 C3 . 1.389(7) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.395(8) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.385(7) ?
C4 C7 . 1.476(7) ?
C5 C6 . 1.385(7) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C8 . 1.352(7) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.470(8) ?
C8 C16 . 1.521(7) ?
C9 C10 . 1.473(7) ?
C10 C11 . 1.375(8) ?
C10 C15 . 1.382(7) ?
C11 C12 . 1.394(7) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.376(8) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.364(8) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.393(7) ?
C15 C16 . 1.480(7) ?
C16 H16A . 0.9700 ?
C16 H16B . 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
C3 H3A O . 0.93 2.14 2.972(8) 149.00
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 . . . . -0.6(10) ?
F C1 C2 C3 . . . . -179.8(5) ?
C1 C2 C3 C4 . . . . 0.3(9) ?
C2 C3 C4 C5 . . . . -0.5(9) ?
C2 C3 C4 C7 . . . . -178.8(5) ?
C3 C4 C5 C6 . . . . 0.8(9) ?
C7 C4 C5 C6 . . . . 179.3(5) ?
C2 C1 C6 C5 . . . . 1.0(10) ?
F C1 C6 C5 . . . . -179.9(5) ?
C4 C5 C6 C1 . . . . -1.1(10) ?
C5 C4 C7 C8 . . . . 176.9(6) ?
C3 C4 C7 C8 . . . . -4.8(11) ?
C4 C7 C8 C9 . . . . 0.7(12) ?
C4 C7 C8 C16 . . . . -178.4(6) ?
C7 C8 C9 O . . . . 3.4(11) ?
C16 C8 C9 O . . . . -177.5(6) ?
C7 C8 C9 C10 . . . . -177.3(6) ?
C16 C8 C9 C10 . . . . 1.9(6) ?
O C9 C10 C11 . . . . -3.3(10) ?
C8 C9 C10 C11 . . . . 177.4(6) ?
O C9 C10 C15 . . . . 177.6(5) ?
C8 C9 C10 C15 . . . . -1.8(6) ?
C15 C10 C11 C12 . . . . -1.8(9) ?
C9 C10 C11 C12 . . . . 179.1(5) ?
C10 C11 C12 C13 . . . . 1.2(9) ?
C11 C12 C13 C14 . . . . 0.4(10) ?
C12 C13 C14 C15 . . . . -1.4(9) ?
C12 C13 C14 Br . . . . 178.7(5) ?
C11 C10 C15 C14 . . . . 0.8(9) ?
C9 C10 C15 C14 . . . . 180.0(5) ?
C11 C10 C15 C16 . . . . -178.2(5) ?
C9 C10 C15 C16 . . . . 0.9(7) ?
C13 C14 C15 C10 . . . . 0.9(8) ?
Br C14 C15 C10 . . . . -179.3(4) ?
C13 C14 C15 C16 . . . . 179.7(6) ?
Br C14 C15 C16 . . . . -0.5(8) ?
C10 C15 C16 C8 . . . . 0.2(6) ?
C14 C15 C16 C8 . . . . -178.7(5) ?
C7 C8 C16 C15 . . . . 178.0(5) ?
C9 C8 C16 C15 . . . . -1.3(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742767
