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#$Date: 2023-02-08 12:06:32 +0200 (Wed, 08 Feb 2023) $
#$Revision: 280822 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106721.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106721
loop_
_publ_author_name
'Zhang, Wenxin'
'Qiu, Chenyu'
'Li, Shanshan'
'Zhou, Lina'
'Hu, Mengwei'
'Chen, Xiaojing'
'Yu, Bin'
'Hong, Yan'
'Liu, Zhiguo'
'Xia, Qinqin'
_publ_section_title
;
 Crystal structure of
 2,5-bis((E)-2-(trifluoromethyl)benzylidene)cyclopentan-1-one, C21H14F6O
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              921
_journal_page_last               922
_journal_paper_doi               10.1515/ncrs-2017-0080
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C21 H14 F6 O'
_chemical_formula_weight         396.32
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                83.25(3)
_cell_angle_beta                 89.18(3)
_cell_angle_gamma                73.79(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8470(16)
_cell_length_b                   7.9390(16)
_cell_length_c                   14.993(3)
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.974
_cell_measurement_theta_min      0.961
_cell_volume                     890.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius CAD4'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3150
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3150
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1659
_refine_ls_R_factor_gt           0.0636
_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)+(0.0301P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1298
_reflns_number_total             3150
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0080_suppl.cif
_cod_data_source_block           b
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8106721
_publcif_funding_html
;
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.3518(3) 0.1788(3) 0.12515(15) 0.0671(8) Uani 1 1 d . . .
F1 F 0.2333(4) -0.1261(4) 0.51161(16) 0.1268(12) Uani 1 1 d . . .
C1 C 0.2977(5) -0.2847(5) 0.3855(3) 0.0588(11) Uani 1 1 d . . .
F2 F 0.1382(4) 0.0185(3) 0.38446(16) 0.0995(9) Uani 1 1 d . . .
C2 C 0.2981(6) -0.4343(6) 0.4439(3) 0.0852(14) Uani 1 1 d . . .
H2A H 0.2831 -0.4267 0.5051 0.102 Uiso 1 1 calc R . .
F3 F 0.4119(4) -0.0540(3) 0.41798(16) 0.0978(9) Uani 1 1 d . . .
C3 C 0.3207(6) -0.5934(6) 0.4112(3) 0.0956(16) Uani 1 1 d . . .
H3A H 0.3198 -0.6932 0.4503 0.115 Uiso 1 1 calc R . .
F4 F 0.0923(5) 0.7135(4) -0.21608(18) 0.1480(14) Uani 1 1 d . . .
C4 C 0.3442(6) -0.6054(6) 0.3227(3) 0.0887(15) Uani 1 1 d . . .
H4A H 0.3614 -0.7137 0.3008 0.106 Uiso 1 1 calc R . .
F5 F 0.3074(4) 0.5680(4) -0.12766(19) 0.1099(10) Uani 1 1 d . . .
C5 C 0.3425(6) -0.4567(6) 0.2647(3) 0.0771(13) Uani 1 1 d . . .
H5A H 0.3568 -0.4666 0.2037 0.093 Uiso 1 1 calc R . .
F6 F 0.0446(4) 0.5745(3) -0.09335(18) 0.1072(9) Uani 1 1 d . . .
C6 C 0.3202(5) -0.2930(5) 0.2941(3) 0.0612(11) Uani 1 1 d . . .
C7 C 0.2711(7) -0.1148(7) 0.4241(3) 0.0746(13) Uani 1 1 d . . .
C8 C 0.3224(5) -0.1373(5) 0.2300(3) 0.0609(11) Uani 1 1 d . . .
H8A H 0.3457 -0.0451 0.2560 0.073 Uiso 1 1 calc R . .
C9 C 0.2966(5) -0.1071(5) 0.1416(3) 0.0573(11) Uani 1 1 d . . .
C10 C 0.2523(5) -0.2174(5) 0.0759(2) 0.0708(12) Uani 1 1 d . . .
H10A H 0.1384 -0.2389 0.0893 0.085 Uiso 1 1 calc R . .
H10B H 0.3421 -0.3302 0.0784 0.085 Uiso 1 1 calc R . .
C11 C 0.2460(5) -0.1119(5) -0.0179(2) 0.0659(11) Uani 1 1 d . . .
H11A H 0.3397 -0.1740 -0.0549 0.079 Uiso 1 1 calc R . .
H11B H 0.1327 -0.0962 -0.0477 0.079 Uiso 1 1 calc R . .
C12 C 0.2704(5) 0.0626(5) -0.0040(2) 0.0596(11) Uani 1 1 d . . .
C13 C 0.3126(5) 0.0609(5) 0.0919(2) 0.0542(10) Uani 1 1 d . . .
C14 C 0.2613(5) 0.2052(5) -0.0631(2) 0.0576(11) Uani 1 1 d . . .
H14A H 0.2824 0.3005 -0.0392 0.069 Uiso 1 1 calc R . .
C15 C 0.2229(5) 0.2331(5) -0.1600(2) 0.0591(11) Uani 1 1 d . . .
C16 C 0.2400(5) 0.0915(5) -0.2090(3) 0.0710(12) Uani 1 1 d . . .
H16A H 0.2774 -0.0230 -0.1798 0.085 Uiso 1 1 calc R . .
C17 C 0.2023(6) 0.1174(7) -0.3013(3) 0.0861(14) Uani 1 1 d . . .
H17A H 0.2120 0.0207 -0.3325 0.103 Uiso 1 1 calc R . .
C18 C 0.1514(6) 0.2838(7) -0.3455(3) 0.0898(16) Uani 1 1 d . . .
H18A H 0.1281 0.3011 -0.4070 0.108 Uiso 1 1 calc R . .
C19 C 0.1347(6) 0.4255(6) -0.2989(3) 0.0817(14) Uani 1 1 d . . .
H19A H 0.0989 0.5393 -0.3290 0.098 Uiso 1 1 calc R . .
C20 C 0.1705(5) 0.4016(6) -0.2071(3) 0.0654(12) Uani 1 1 d U . .
C21 C 0.1536(8) 0.5632(7) -0.1621(4) 0.0916(15) Uani 1 1 d U . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 121.0(4) . .
C6 C1 C7 121.0(4) . .
C2 C1 C7 118.0(4) . .
C3 C2 C1 119.9(4) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C4 C3 C2 120.3(4) . .
C4 C3 H3A 119.9 . .
C2 C3 H3A 119.9 . .
C3 C4 C5 119.8(4) . .
C3 C4 H4A 120.1 . .
C5 C4 H4A 120.1 . .
C4 C5 C6 122.4(4) . .
C4 C5 H5A 118.8 . .
C6 C5 H5A 118.8 . .
C5 C6 C1 116.6(4) . .
C5 C6 C8 120.7(4) . .
C1 C6 C8 122.6(4) . .
F3 C7 F1 105.2(4) . .
F3 C7 F2 104.8(4) . .
F1 C7 F2 105.2(4) . .
F3 C7 C1 113.4(4) . .
F1 C7 C1 113.2(4) . .
F2 C7 C1 114.1(4) . .
C9 C8 C6 130.7(4) . .
C9 C8 H8A 114.6 . .
C6 C8 H8A 114.6 . .
C8 C9 C13 120.0(4) . .
C8 C9 C10 131.3(4) . .
C13 C9 C10 108.7(3) . .
C9 C10 C11 106.5(3) . .
C9 C10 H10A 110.4 . .
C11 C10 H10A 110.4 . .
C9 C10 H10B 110.4 . .
C11 C10 H10B 110.4 . .
H10A C10 H10B 108.6 . .
C12 C11 C10 106.9(3) . .
C12 C11 H11A 110.3 . .
C10 C11 H11A 110.3 . .
C12 C11 H11B 110.3 . .
C10 C11 H11B 110.3 . .
H11A C11 H11B 108.6 . .
C14 C12 C13 121.1(4) . .
C14 C12 C11 130.0(3) . .
C13 C12 C11 108.9(3) . .
O C13 C12 125.8(4) . .
O C13 C9 125.6(3) . .
C12 C13 C9 108.6(3) . .
C12 C14 C15 129.5(4) . .
C12 C14 H14A 115.2 . .
C15 C14 H14A 115.2 . .
C16 C15 C20 117.1(4) . .
C16 C15 C14 121.1(4) . .
C20 C15 C14 121.7(4) . .
C15 C16 C17 121.4(4) . .
C15 C16 H16A 119.3 . .
C17 C16 H16A 119.3 . .
C18 C17 C16 120.1(4) . .
C18 C17 H17A 119.9 . .
C16 C17 H17A 119.9 . .
C17 C18 C19 119.6(4) . .
C17 C18 H18A 120.2 . .
C19 C18 H18A 120.2 . .
C18 C19 C20 120.8(4) . .
C18 C19 H19A 119.6 . .
C20 C19 H19A 119.6 . .
C19 C20 C15 120.9(4) . .
C19 C20 C21 117.2(4) . .
C15 C20 C21 121.9(4) . .
F6 C21 F5 104.9(5) . .
F6 C21 F4 105.6(4) . .
F5 C21 F4 106.6(5) . .
F6 C21 C20 112.8(4) . .
F5 C21 C20 112.5(5) . .
F4 C21 C20 113.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O C13 1.222(4) .
F1 C7 1.340(4) .
C1 C6 1.387(5) .
C1 C2 1.389(5) .
C1 C7 1.490(5) .
F2 C7 1.347(5) .
C2 C3 1.372(5) .
C2 H2A 0.9300 .
F3 C7 1.321(5) .
C3 C4 1.348(5) .
C3 H3A 0.9300 .
F4 C21 1.331(5) .
C4 C5 1.379(5) .
C4 H4A 0.9300 .
F5 C21 1.331(6) .
C5 C6 1.385(5) .
C5 H5A 0.9300 .
F6 C21 1.326(5) .
C6 C8 1.478(5) .
C8 C9 1.327(4) .
C8 H8A 0.9300 .
C9 C13 1.485(5) .
C9 C10 1.497(4) .
C10 C11 1.544(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.489(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C14 1.339(5) .
C12 C13 1.477(4) .
C14 C15 1.466(5) .
C14 H14A 0.9300 .
C15 C16 1.388(5) .
C15 C20 1.392(5) .
C16 C17 1.399(5) .
C16 H16A 0.9300 .
C17 C18 1.360(6) .
C17 H17A 0.9300 .
C18 C19 1.368(5) .
C18 H18A 0.9300 .
C19 C20 1.389(5) .
C19 H19A 0.9300 .
C20 C21 1.491(6) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.1(7) . . . .
C7 C1 C2 C3 179.5(4) . . . .
C1 C2 C3 C4 0.6(8) . . . .
C2 C3 C4 C5 -1.1(8) . . . .
C3 C4 C5 C6 1.1(7) . . . .
C4 C5 C6 C1 -0.6(7) . . . .
C4 C5 C6 C8 178.9(4) . . . .
C2 C1 C6 C5 0.1(6) . . . .
C7 C1 C6 C5 -179.5(4) . . . .
C2 C1 C6 C8 -179.3(4) . . . .
C7 C1 C6 C8 1.1(6) . . . .
C6 C1 C7 F3 -66.8(5) . . . .
C2 C1 C7 F3 113.6(5) . . . .
C6 C1 C7 F1 173.5(4) . . . .
C2 C1 C7 F1 -6.1(6) . . . .
C6 C1 C7 F2 53.1(6) . . . .
C2 C1 C7 F2 -126.5(4) . . . .
C5 C6 C8 C9 20.2(7) . . . .
C1 C6 C8 C9 -160.4(4) . . . .
C6 C8 C9 C13 -177.8(4) . . . .
C6 C8 C9 C10 1.6(7) . . . .
C8 C9 C10 C11 -178.1(4) . . . .
C13 C9 C10 C11 1.4(4) . . . .
C9 C10 C11 C12 -5.0(4) . . . .
C10 C11 C12 C14 -174.1(4) . . . .
C10 C11 C12 C13 6.7(4) . . . .
C14 C12 C13 O -4.2(6) . . . .
C11 C12 C13 O 175.0(4) . . . .
C14 C12 C13 C9 174.8(4) . . . .
C11 C12 C13 C9 -6.0(4) . . . .
C8 C9 C13 O 1.4(6) . . . .
C10 C9 C13 O -178.2(4) . . . .
C8 C9 C13 C12 -177.7(4) . . . .
C10 C9 C13 C12 2.8(4) . . . .
C13 C12 C14 C15 179.6(4) . . . .
C11 C12 C14 C15 0.5(7) . . . .
C12 C14 C15 C16 -19.1(7) . . . .
C12 C14 C15 C20 161.9(4) . . . .
C20 C15 C16 C17 -1.4(6) . . . .
C14 C15 C16 C17 179.5(4) . . . .
C15 C16 C17 C18 1.5(7) . . . .
C16 C17 C18 C19 -1.0(7) . . . .
C17 C18 C19 C20 0.6(7) . . . .
C18 C19 C20 C15 -0.5(7) . . . .
C18 C19 C20 C21 178.4(5) . . . .
C16 C15 C20 C19 0.9(6) . . . .
C14 C15 C20 C19 180.0(4) . . . .
C16 C15 C20 C21 -177.9(4) . . . .
C14 C15 C20 C21 1.2(6) . . . .
C19 C20 C21 F6 125.1(5) . . . .
C15 C20 C21 F6 -56.1(7) . . . .
C19 C20 C21 F5 -116.6(5) . . . .
C15 C20 C21 F5 62.3(6) . . . .
C19 C20 C21 F4 4.8(7) . . . .
C15 C20 C21 F4 -176.3(4) . . . .
