#------------------------------------------------------------------------------
#$Date: 2021-06-09 08:19:05 +0300 (Wed, 09 Jun 2021) $
#$Revision: 266286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243849.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_2243849
loop_
_publ_author_name
'Brown, Loren C.'
'Balaich, Gary J.'
_publ_section_title
;
 Crystal structure of 1,2-bis(3,5-difluorophenyl)ethane-1,2-dione
;
_journal_coeditor_code           YK2148
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              700
_journal_page_last               702
_journal_paper_doi               10.1107/S2056989021005363
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C14 H6 F4 O2'
_chemical_formula_moiety         'C14 H6 F4 O2'
_chemical_formula_sum            'C14 H6 F4 O2'
_chemical_formula_weight         282.19
_chemical_name_systematic
;
1,2-Bis(3,5-difluorophenyl)ethane-1,2-dione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0588(2)
_cell_length_b                   7.4008(2)
_cell_length_c                   21.5265(4)
_cell_measurement_reflns_used    7273
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      27.0370
_cell_measurement_theta_min      1.8890
_cell_volume                     1124.56(5)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13347
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.111
_diffrn_reflns_theta_min         1.892
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0435P)²+0.4818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                1014
_reflns_number_total             1202
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2148sup1.cif
_cod_data_source_block           I
_cod_database_code               2243849
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 1.04484(11) 0.64342(12) 0.45793(3) 0.0274(2) Uani d 1 . .
F F2 0.41188(11) 0.52722(13) 0.40758(4) 0.0298(2) Uani d 1 . .
O O1 0.78193(13) 0.28658(13) 0.22568(4) 0.0236(3) Uani d 1 . .
C C1 0.97690(19) 0.50922(17) 0.36170(6) 0.0183(3) Uani d 1 . .
H H1 1.1050 0.5083 0.3516 0.022 Uiso calc 1 . .
C C2 0.91452(19) 0.57731(18) 0.41774(6) 0.0196(3) Uani d 1 . .
C C3 0.72718(19) 0.58412(18) 0.43505(6) 0.0200(3) Uani d 1 . .
H H3 0.6896 0.6293 0.4734 0.024 Uiso calc 1 . .
C C4 0.59783(19) 0.51991(19) 0.39216(6) 0.0200(3) Uani d 1 . .
C C5 0.64773(18) 0.44830(18) 0.33558(6) 0.0190(3) Uani d 1 . .
H H5 0.5563 0.4056 0.3081 0.023 Uiso calc 1 . .
C C6 0.84090(18) 0.44170(17) 0.32055(6) 0.0167(3) Uani d 1 . .
C C7 0.89509(18) 0.36177(17) 0.25965(6) 0.0174(3) Uani d 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'
F F 0.0171 0.0103 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 5 0.0463
-1 -1 5 0.0776
2 0 -5 0.0608
0 2 -5 0.1145
1 5 -2 0.1305
-2 -5 -1 0.1215
1 0 5 0.0476
0 -4 -5 0.1259
0 0 1 0.0411
1 -1 -5 0.0687
-1 0 0 0.0710
5 1 5 0.0646
-1 -1 1 0.0993
-1 0 -5 0.0592
-1 -2 -5 0.1011
0 0 -1 0.0562
0 -3 -29 0.0650
2 1 -29 0.0567
3 -2 -28 0.0555
10 0 7 0.0604
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
C2 C1 H1 . . 121.1 ?
C2 C1 C6 . . 117.73(12) ?
C6 C1 H1 . . 121.1 ?
F1 C2 C1 . . 118.28(11) ?
F1 C2 C3 . . 117.84(11) ?
C3 C2 C1 . . 123.87(13) ?
C2 C3 H3 . . 121.9 ?
C2 C3 C4 . . 116.21(12) ?
C4 C3 H3 . . 121.9 ?
F2 C4 C3 . . 117.54(12) ?
F2 C4 C5 . . 118.74(12) ?
C5 C4 C3 . . 123.72(13) ?
C4 C5 H5 . . 121.1 ?
C4 C5 C6 . . 117.85(12) ?
C6 C5 H5 . . 121.1 ?
C1 C6 C5 . . 120.59(12) ?
C1 C6 C7 . . 121.56(12) ?
C5 C6 C7 . . 117.84(11) ?
O1 C7 C6 . . 122.83(12) ?
O1 C7 C7 . 3_755 117.99(12) ?
C6 C7 C7 . 3_755 119.05(12) ?
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
F1 C2 . 1.3543(15) ?
F2 C4 . 1.3550(15) ?
O1 C7 . 1.2176(16) ?
C1 H1 . 0.9300 ?
C1 C2 . 1.3796(18) ?
C1 C6 . 1.3985(18) ?
C2 C3 . 1.3748(19) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.3827(19) ?
C4 C5 . 1.3741(19) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.4023(18) ?
C6 C7 . 1.4882(17) ?
C7 C7 3_755 1.538(3) ?
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
C1 H1 F2 1_655 0.93 2.48 3.2281(16) 137 yes
C3 H3 F1 4_466 0.93 2.46 3.3211(15) 154 yes
C5 H5 O1 3_655 0.93 2.65 3.517(2) 156 yes

_cod_database_fobs_code 2243849
