#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/87/2238734.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_2238734
loop_
_publ_author_name
'Manoj Kumar, K.E.'
'Palakshamurthy, B. S.'
'Suchetan, P. A.'
'Madan Kumar, S.'
'Lokanath, N.K.'
'Sreenivasa, S.'
_publ_section_title
;
 1-(3,5-Difluorophenyl)-4,4,4-trifluorobutane-1,3-dione
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1705
_journal_paper_doi               10.1107/S1600536813028535
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H5 F5 O2'
_chemical_formula_moiety         'C10 H5 F5 O2'
_chemical_formula_sum            'C10 H5 F5 O2'
_chemical_formula_weight         252.14
_chemical_melting_point          393
_chemical_name_systematic
;
1-(3,5-Difluorophenyl)-4,4,4-trifluorobutane-1,3-dione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 112.49(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.393(4)
_cell_length_b                   13.433(5)
_cell_length_c                   12.877(5)
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      0.0
_cell_volume                     1980.7(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and 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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5651
_diffrn_reflns_theta_full        24.60
_diffrn_reflns_theta_max         24.60
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 2
_diffrn_standards_number         1234
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.466
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1433P)²+2.2069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2389
_reflns_number_gt                1246
_reflns_number_total             1604
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7151.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2238734
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'
'-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_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_symmetry_multiplicity
C C1 0.0373(3) 0.3441(3) 0.4970(3) 0.0558(9) Uani d . 1 1
H H1 0.0691 0.4058 0.4923 0.067 Uiso calc R 1 1
C C2 -0.0308(3) 0.3323(3) 0.5594(3) 0.0624(10) Uani d . 1 1
C C3 -0.0787(4) 0.2426(3) 0.5705(3) 0.0684(11) Uani d . 1 1
H H3 -0.1238 0.2360 0.6135 0.082 Uiso calc R 1 1
C C4 -0.0565(4) 0.1636(3) 0.5147(4) 0.0649(10) Uani d . 1 1
C C5 0.0106(3) 0.1700(3) 0.4506(3) 0.0574(9) Uani d . 1 1
H H5 0.0242 0.1143 0.4144 0.069 Uiso calc R 1 1
C C6 0.0574(3) 0.2624(2) 0.4416(3) 0.0474(8) Uani d . 1 1
C C7 0.1298(3) 0.2699(2) 0.3734(3) 0.0476(8) Uani d . 1 1
C C8 0.1640(3) 0.3603(3) 0.3419(3) 0.0511(8) Uani d . 1 1
H H8A 0.0937 0.3983 0.3019 0.061 Uiso calc R 1 1
H H8B 0.2077 0.3967 0.4101 0.061 Uiso calc R 1 1
C C9 0.2304(3) 0.3596(3) 0.2760(3) 0.0515(9) Uani d . 1 1
C C10 0.2656(3) 0.4562(3) 0.2375(3) 0.0624(10) Uani d . 1 1
F F1 -0.0500(3) 0.4121(2) 0.6129(3) 0.1000(11) Uani d . 1 1
F F2 -0.1027(3) 0.0740(2) 0.5224(3) 0.1010(11) Uani d . 1 1
F F3 0.2245(3) 0.4627(2) 0.1272(2) 0.0913(9) Uani d . 1 1
F F4 0.3807(2) 0.4629(2) 0.2695(3) 0.0989(10) Uani d . 1 1
F F5 0.2306(3) 0.5370(2) 0.2748(3) 0.1110(13) Uani d . 1 1
O O1 0.1598(2) 0.18650(19) 0.3425(2) 0.0671(8) Uani d . 1 1
O O2 0.2645(2) 0.2827(2) 0.2411(2) 0.0666(8) Uani d . 1 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.8(3)
C2 C1 H1 120.6
C6 C1 H1 120.6
F1 C2 C3 118.5(3)
F1 C2 C1 118.4(4)
C3 C2 C1 123.1(4)
C4 C3 C2 116.4(3)
C4 C3 H3 121.8
C2 C3 H3 121.8
F2 C4 C3 118.5(3)
F2 C4 C5 117.9(4)
C3 C4 C5 123.7(4)
C4 C5 C6 118.0(4)
C4 C5 H5 121.0
C6 C5 H5 121.0
C1 C6 C5 120.0(3)
C1 C6 C7 121.5(3)
C5 C6 C7 118.4(3)
O1 C7 C8 120.7(3)
O1 C7 C6 115.8(3)
C8 C7 C6 123.5(3)
C9 C8 C7 119.2(3)
C9 C8 H8A 107.5
C7 C8 H8A 107.5
C9 C8 H8B 107.5
C7 C8 H8B 107.5
H8A C8 H8B 107.0
O2 C9 C8 125.5(3)
O2 C9 C10 114.0(3)
C8 C9 C10 120.5(3)
F3 C10 F5 106.9(4)
F3 C10 F4 104.9(3)
F5 C10 F4 107.1(3)
F3 C10 C9 111.8(3)
F5 C10 C9 114.1(3)
F4 C10 C9 111.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.379(5)
C1 C6 1.383(5)
C1 H1 0.9300
C2 F1 1.344(5)
C2 C3 1.374(6)
C3 C4 1.367(6)
C3 H3 0.9300
C4 F2 1.353(5)
C4 C5 1.381(5)
C5 C6 1.393(5)
C5 H5 0.9300
C6 C7 1.479(5)
C7 O1 1.290(4)
C7 C8 1.396(5)
C8 C9 1.389(5)
C8 H8A 0.9700
C8 H8B 0.9700
C9 O2 1.262(4)
C9 C10 1.512(5)
C10 F3 1.316(5)
C10 F5 1.327(5)
C10 F4 1.328(4)
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 H3 O2 8_456 0.93 2.53 3.462(5) 177
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 F1 -179.9(3)
C6 C1 C2 C3 0.8(6)
F1 C2 C3 C4 -179.9(4)
C1 C2 C3 C4 -0.6(6)
C2 C3 C4 F2 -179.5(4)
C2 C3 C4 C5 0.4(6)
F2 C4 C5 C6 179.4(3)
C3 C4 C5 C6 -0.5(6)
C2 C1 C6 C5 -0.9(5)
C2 C1 C6 C7 -179.9(3)
C4 C5 C6 C1 0.7(5)
C4 C5 C6 C7 179.8(3)
C1 C6 C7 O1 168.0(3)
C5 C6 C7 O1 -11.0(5)
C1 C6 C7 C8 -12.7(5)
C5 C6 C7 C8 168.3(3)
O1 C7 C8 C9 0.4(5)
C6 C7 C8 C9 -178.9(3)
C7 C8 C9 O2 -0.3(6)
C7 C8 C9 C10 178.1(3)
O2 C9 C10 F3 59.0(4)
C8 C9 C10 F3 -119.5(4)
O2 C9 C10 F5 -179.5(3)
C8 C9 C10 F5 1.9(5)
O2 C9 C10 F4 -58.1(4)
C8 C9 C10 F4 123.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 80198629
