#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225934.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_2225934
loop_
_publ_author_name
'Jiang, Chengxi'
'Feng, Zhiguo'
'Song, Bo'
'Li, Xiaoxia'
'Li, Xiaokun'
_publ_section_title
;
 (2E,6E)-2,6-Bis(2,5-difluorobenzylidene)cyclohexanone
;
_journal_coeditor_code           NG2751
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1009
_journal_paper_doi               10.1107/S1600536810011499
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H14 F4 O'
_chemical_formula_moiety         'C20 H14 F4 O'
_chemical_formula_sum            'C20 H14 F4 O'
_chemical_formula_weight         346.31
_chemical_name_systematic
;
(2E,6E)-2,6-Bis(2,5-difluorobenzylidene)cyclohexanone
;
_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                 111.756(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.824(2)
_cell_length_b                   6.3128(8)
_cell_length_c                   17.097(2)
_cell_measurement_reflns_used    1858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3
_cell_measurement_theta_min      2.4
_cell_volume                     1586.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8935
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.238
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0557
_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)+(0.0820P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                2018
_reflns_number_total             3425
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2751.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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225934
_cod_database_fobs_code          2225934
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.40753(15) 0.4774(3) 1.14644(10) 0.1192(7) Uani d . 1 . .
F F2 0.42662(12) 1.2350(2) 1.00801(10) 0.0934(5) Uani d . 1 . .
F F3 0.00929(10) 0.5237(2) 0.36811(8) 0.0809(5) Uani d . 1 . .
F F4 0.16575(11) 1.2677(2) 0.49902(9) 0.0839(5) Uani d . 1 . .
O O1 0.17234(12) 1.1232(3) 0.76698(9) 0.0796(6) Uani d . 1 . .
C C1 0.20606(14) 0.9520(4) 0.76181(12) 0.0520(6) Uani d . 1 . .
C C2 0.26784(13) 0.8418(3) 0.83949(12) 0.0466(5) Uani d . 1 . .
C C3 0.29758(14) 0.9609(4) 0.90938(13) 0.0556(6) Uani d . 1 . .
H H3 0.2766 1.0999 0.9033 0.067 Uiso calc R 1 . .
C C4 0.35876(14) 0.9001(4) 0.99398(12) 0.0528(6) Uani d . 1 . .
C C5 0.35519(16) 0.7068(4) 1.03101(14) 0.0633(6) Uani d . 1 . .
H H5 0.3125 0.6053 1.0019 0.076 Uiso calc R 1 . .
C C6 0.4149(2) 0.6673(5) 1.11059(15) 0.0760(8) Uani d . 1 . .
C C7 0.47922(18) 0.8090(6) 1.15698(15) 0.0836(9) Uani d . 1 . .
H H7 0.5196 0.7755 1.2108 0.100 Uiso calc R 1 . .
C C8 0.48225(18) 1.0026(5) 1.12152(16) 0.0794(8) Uani d . 1 . .
H H8 0.5247 1.1039 1.1512 0.095 Uiso calc R 1 . .
C C9 0.42230(17) 1.0439(4) 1.04241(14) 0.0654(7) Uani d . 1 . .
C C10 0.18662(13) 0.8503(3) 0.67808(12) 0.0466(5) Uani d . 1 . .
C C11 0.14905(14) 0.9764(3) 0.61179(13) 0.0517(6) Uani d . 1 . .
H H11 0.1403 1.1160 0.6244 0.062 Uiso calc R 1 . .
C C12 0.11951(13) 0.9273(3) 0.52187(12) 0.0470(5) Uani d . 1 . .
C C13 0.07950(14) 0.7364(3) 0.48623(12) 0.0503(5) Uani d . 1 . .
H H13 0.0731 0.6275 0.5202 0.060 Uiso calc R 1 . .
C C14 0.04988(14) 0.7102(4) 0.40128(13) 0.0556(6) Uani d . 1 . .
C C15 0.05733(15) 0.8634(4) 0.34722(14) 0.0614(7) Uani d . 1 . .
H H15 0.0367 0.8396 0.2895 0.074 Uiso calc R 1 . .
C C16 0.09649(17) 1.0538(4) 0.38151(14) 0.0629(7) Uani d . 1 . .
H H16 0.1025 1.1624 0.3472 0.076 Uiso calc R 1 . .
C C17 0.12608(15) 1.0796(3) 0.46646(14) 0.0562(6) Uani d . 1 . .
C C18 0.29633(15) 0.6182(3) 0.83255(12) 0.0528(6) Uani d . 1 . .
H H18A 0.2525 0.5215 0.8405 0.063 Uiso calc R 1 . .
H H18B 0.3549 0.5916 0.8769 0.063 Uiso calc R 1 . .
C C19 0.30317(15) 0.5754(4) 0.74764(12) 0.0541(6) Uani d . 1 . .
H H19A 0.3514 0.6616 0.7421 0.065 Uiso calc R 1 . .
H H19B 0.3188 0.4279 0.7446 0.065 Uiso calc R 1 . .
C C20 0.21500(14) 0.6242(3) 0.67610(12) 0.0523(6) Uani d . 1 . .
H H20A 0.2220 0.5968 0.6230 0.063 Uiso calc R 1 . .
H H20B 0.1677 0.5313 0.6796 0.063 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'
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
O1 C1 C10 . . 120.60(18) ?
O1 C1 C2 . . 120.36(18) ?
C10 C1 C2 . . 119.03(19) ?
C3 C2 C1 . . 115.35(19) ?
C3 C2 C18 . . 125.57(18) ?
C1 C2 C18 . . 118.93(17) ?
C2 C3 C4 . . 128.3(2) ?
C2 C3 H3 . . 115.9 ?
C4 C3 H3 . . 115.9 ?
C9 C4 C5 . . 116.7(2) ?
C9 C4 C3 . . 119.3(2) ?
C5 C4 C3 . . 124.0(2) ?
C6 C5 C4 . . 119.1(2) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C7 . . 123.5(3) ?
C5 C6 F1 . . 117.7(3) ?
C7 C6 F1 . . 118.8(2) ?
C6 C7 C8 . . 117.8(2) ?
C6 C7 H7 . . 121.1 ?
C8 C7 H7 . . 121.1 ?
C9 C8 C7 . . 119.0(3) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
F2 C9 C8 . . 118.3(2) ?
F2 C9 C4 . . 117.9(2) ?
C8 C9 C4 . . 123.8(3) ?
C11 C10 C1 . . 115.29(19) ?
C11 C10 C20 . . 126.35(18) ?
C1 C10 C20 . . 118.28(17) ?
C10 C11 C12 . . 129.4(2) ?
C10 C11 H11 . . 115.3 ?
C12 C11 H11 . . 115.3 ?
C17 C12 C13 . . 116.12(19) ?
C17 C12 C11 . . 119.8(2) ?
C13 C12 C11 . . 124.00(19) ?
C14 C13 C12 . . 119.5(2) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
F3 C14 C13 . . 118.2(2) ?
F3 C14 C15 . . 118.3(2) ?
C13 C14 C15 . . 123.5(2) ?
C14 C15 C16 . . 117.7(2) ?
C14 C15 H15 . . 121.2 ?
C16 C15 H15 . . 121.2 ?
C17 C16 C15 . . 118.7(2) ?
C17 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
C16 C17 F4 . . 117.7(2) ?
C16 C17 C12 . . 124.4(2) ?
F4 C17 C12 . . 117.9(2) ?
C2 C18 C19 . . 111.88(17) ?
C2 C18 H18A . . 109.2 ?
C19 C18 H18A . . 109.2 ?
C2 C18 H18B . . 109.2 ?
C19 C18 H18B . . 109.2 ?
H18A C18 H18B . . 107.9 ?
C20 C19 C18 . . 111.50(18) ?
C20 C19 H19A . . 109.3 ?
C18 C19 H19A . . 109.3 ?
C20 C19 H19B . . 109.3 ?
C18 C19 H19B . . 109.3 ?
H19A C19 H19B . . 108.0 ?
C10 C20 C19 . . 111.77(17) ?
C10 C20 H20A . . 109.3 ?
C19 C20 H20A . . 109.3 ?
C10 C20 H20B . . 109.3 ?
C19 C20 H20B . . 109.3 ?
H20A C20 H20B . . 107.9 ?
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
F1 C6 . 1.371(3) ?
F2 C9 . 1.355(3) ?
F3 C14 . 1.360(2) ?
F4 C17 . 1.362(2) ?
O1 C1 . 1.223(2) ?
C1 C10 . 1.493(3) ?
C1 C2 . 1.497(3) ?
C2 C3 . 1.341(3) ?
C2 C18 . 1.500(3) ?
C3 C4 . 1.462(3) ?
C3 H3 . 0.9300 ?
C4 C9 . 1.380(3) ?
C4 C5 . 1.386(3) ?
C5 C6 . 1.361(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.366(4) ?
C7 C8 . 1.373(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.359(3) ?
C8 H8 . 0.9300 ?
C10 C11 . 1.331(3) ?
C10 C20 . 1.500(3) ?
C11 C12 . 1.465(3) ?
C11 H11 . 0.9300 ?
C12 C17 . 1.381(3) ?
C12 C13 . 1.392(3) ?
C13 C14 . 1.361(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.372(3) ?
C15 C16 . 1.380(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.361(3) ?
C16 H16 . 0.9300 ?
C18 C19 . 1.519(3) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.508(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9700 ?
C20 H20B . 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
_geom_hbond_publ_flag
C16 H16 O1 4_585 0.93 2.46 3.343(3) 158.3 no
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
O1 C1 C2 C3 . . . . -13.6(3) ?
C10 C1 C2 C3 . . . . 166.2(2) ?
O1 C1 C2 C18 . . . . 170.6(2) ?
C10 C1 C2 C18 . . . . -9.7(3) ?
C1 C2 C3 C4 . . . . -179.3(2) ?
C18 C2 C3 C4 . . . . -3.8(4) ?
C2 C3 C4 C9 . . . . 141.8(2) ?
C2 C3 C4 C5 . . . . -40.8(4) ?
C9 C4 C5 C6 . . . . -1.8(3) ?
C3 C4 C5 C6 . . . . -179.3(2) ?
C4 C5 C6 C7 . . . . 0.1(4) ?
C4 C5 C6 F1 . . . . 177.8(2) ?
C5 C6 C7 C8 . . . . 1.1(4) ?
F1 C6 C7 C8 . . . . -176.6(2) ?
C6 C7 C8 C9 . . . . -0.5(4) ?
C7 C8 C9 F2 . . . . -179.5(2) ?
C7 C8 C9 C4 . . . . -1.4(4) ?
C5 C4 C9 F2 . . . . -179.4(2) ?
C3 C4 C9 F2 . . . . -1.7(3) ?
C5 C4 C9 C8 . . . . 2.5(4) ?
C3 C4 C9 C8 . . . . -179.8(2) ?
O1 C1 C10 C11 . . . . 14.5(3) ?
C2 C1 C10 C11 . . . . -165.28(19) ?
O1 C1 C10 C20 . . . . -168.7(2) ?
C2 C1 C10 C20 . . . . 11.5(3) ?
C1 C10 C11 C12 . . . . -178.3(2) ?
C20 C10 C11 C12 . . . . 5.2(4) ?
C10 C11 C12 C17 . . . . -146.9(2) ?
C10 C11 C12 C13 . . . . 36.8(4) ?
C17 C12 C13 C14 . . . . 0.1(3) ?
C11 C12 C13 C14 . . . . 176.5(2) ?
C12 C13 C14 F3 . . . . -178.60(18) ?
C12 C13 C14 C15 . . . . 0.2(3) ?
F3 C14 C15 C16 . . . . 178.34(19) ?
C13 C14 C15 C16 . . . . -0.5(4) ?
C14 C15 C16 C17 . . . . 0.5(4) ?
C15 C16 C17 F4 . . . . 179.0(2) ?
C15 C16 C17 C12 . . . . -0.2(4) ?
C13 C12 C17 C16 . . . . 0.0(3) ?
C11 C12 C17 C16 . . . . -176.6(2) ?
C13 C12 C17 F4 . . . . -179.30(18) ?
C11 C12 C17 F4 . . . . 4.1(3) ?
C3 C2 C18 C19 . . . . -143.7(2) ?
C1 C2 C18 C19 . . . . 31.7(3) ?
C2 C18 C19 C20 . . . . -56.2(3) ?
C11 C10 C20 C19 . . . . 140.9(2) ?
C1 C10 C20 C19 . . . . -35.6(3) ?
C18 C19 C20 C10 . . . . 58.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24668762
