#------------------------------------------------------------------------------
#$Date: 2022-03-07 11:35:06 +0200 (Mon, 07 Mar 2022) $
#$Revision: 273493 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104665.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_8104665
loop_
_publ_author_name
'Meng, Qing-Guo'
'Zhao, Sheng-Nan'
'Sun, Zhong-Hao'
'Shan, Guang-Zhi'
'Meng, Qing-Guo'
_publ_section_title
;
 Crystal structure of
 (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one,
 C19H14F4O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1059
_journal_page_last               1061
_journal_paper_doi               10.1515/ncrs-2021-0209
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C19 H14 F4 O2'
_chemical_formula_sum            'C19 H14 F4 O2'
_chemical_formula_weight         350.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.150(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8614(10)
_cell_length_b                   7.9148(6)
_cell_length_c                   16.7999(16)
_cell_measurement_reflns_used    2754
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.5080
_cell_measurement_theta_min      2.8380
_cell_volume                     1557.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6570
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0446
_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)+(0.0536P)²+0.2573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2362
_reflns_number_total             2891
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0209_suppl.cif
_cod_data_source_block           XF-1-7
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104665
_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.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28309(15) 0.5351(2) 0.78121(11) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.27811(15) 0.5544(2) 0.86916(11) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.36931(15) 0.6621(2) 0.91647(11) 0.0284(4) Uani 1 1 d . . . . .
H3A H 0.367680 0.648498 0.973661 0.034 Uiso 1 1 calc R U . . .
H3B H 0.354869 0.779988 0.902764 0.034 Uiso 1 1 calc R U . . .
C4 C 0.48686(16) 0.6116(3) 0.89791(11) 0.0327(5) Uani 1 1 d . . . . .
H4A H 0.543716 0.689546 0.924611 0.039 Uiso 1 1 calc R U . . .
H4B H 0.505830 0.499491 0.919318 0.039 Uiso 1 1 calc R U . . .
C5 C 0.59270(16) 0.6416(2) 0.77932(12) 0.0323(5) Uani 1 1 d . . . . .
H5 H 0.658930 0.662887 0.815598 0.039 Uiso 1 1 calc R U . . .
C6 C 0.59774(17) 0.6400(2) 0.69787(12) 0.0322(5) Uani 1 1 d . . . . .
H6 H 0.666504 0.657909 0.679216 0.039 Uiso 1 1 calc R U . . .
C7 C 0.49842(17) 0.6113(2) 0.64475(11) 0.0287(4) Uani 1 1 d . . . . .
C8 C 0.39622(16) 0.5805(2) 0.67011(11) 0.0269(4) Uani 1 1 d . . . . .
H8 H 0.330568 0.560696 0.633021 0.032 Uiso 1 1 calc R U . . .
C9 C 0.39252(15) 0.5795(2) 0.75310(11) 0.0236(4) Uani 1 1 d . . . . .
C10 C 0.49092(15) 0.6120(2) 0.80877(11) 0.0262(4) Uani 1 1 d . . . . .
C11 C 0.19726(15) 0.4668(2) 0.89900(11) 0.0255(4) Uani 1 1 d . . . . .
H11 H 0.151055 0.397381 0.862845 0.031 Uiso 1 1 calc R U . . .
C12 C 0.17339(14) 0.4679(2) 0.98250(11) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.14704(14) 0.3193(2) 1.02263(11) 0.0222(4) Uani 1 1 d . . . . .
C14 C 0.12003(14) 0.3241(2) 1.09972(11) 0.0236(4) Uani 1 1 d . . . . .
H14 H 0.103418 0.224366 1.124732 0.028 Uiso 1 1 calc R U . . .
C15 C 0.11756(14) 0.4778(2) 1.14019(11) 0.0239(4) Uani 1 1 d . . . . .
C16 C 0.14380(15) 0.6255(2) 1.10272(11) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.143609 0.728480 1.129337 0.031 Uiso 1 1 calc R U . . .
C17 C 0.17037(15) 0.6187(2) 1.02523(11) 0.0268(4) Uani 1 1 d . . . . .
H17 H 0.186882 0.719063 1.000702 0.032 Uiso 1 1 calc R U . . .
C18 C 0.0905(2) 0.6203(2) 1.26099(12) 0.0370(5) Uani 1 1 d . . . . .
H18A H 0.166907 0.663892 1.271356 0.056 Uiso 1 1 calc R U . . .
H18B H 0.064546 0.597491 1.311225 0.056 Uiso 1 1 calc R U . . .
H18C H 0.041027 0.701959 1.231018 0.056 Uiso 1 1 calc R U . . .
C19 C 0.15198(15) 0.1506(2) 0.98292(11) 0.0268(4) Uani 1 1 d . . . . .
F1 F 0.50222(10) 0.61374(15) 0.56421(7) 0.0421(3) Uani 1 1 d . . . . .
F2 F 0.25497(9) 0.11891(13) 0.96276(8) 0.0411(3) Uani 1 1 d . . . . .
F3 F 0.07742(10) 0.13620(13) 0.91407(7) 0.0377(3) Uani 1 1 d . . . . .
F4 F 0.12968(10) 0.02243(12) 1.02984(7) 0.0356(3) Uani 1 1 d . . . . .
O1 O 0.20172(11) 0.48343(16) 0.73312(8) 0.0323(3) Uani 1 1 d . . . . .
O2 O 0.08882(11) 0.46776(15) 1.21546(8) 0.0307(3) Uani 1 1 d . . . . .
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
O1 C1 C9 120.21(16) . .
O1 C1 C2 122.29(16) . .
C9 C1 C2 117.50(15) . .
C11 C2 C1 117.30(16) . .
C11 C2 C3 126.33(17) . .
C1 C2 C3 116.26(15) . .
C2 C3 C4 110.31(15) . .
C2 C3 H3A 109.6 . .
C4 C3 H3A 109.6 . .
C2 C3 H3B 109.6 . .
C4 C3 H3B 109.6 . .
H3A C3 H3B 108.1 . .
C10 C4 C3 112.11(16) . .
C10 C4 H4A 109.2 . .
C3 C4 H4A 109.2 . .
C10 C4 H4B 109.2 . .
C3 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C6 C5 C10 121.79(18) . .
C6 C5 H5 119.1 . .
C10 C5 H5 119.1 . .
C7 C6 C5 118.44(17) . .
C7 C6 H6 120.8 . .
C5 C6 H6 120.8 . .
F1 C7 C8 118.86(17) . .
F1 C7 C6 118.76(16) . .
C8 C7 C6 122.38(18) . .
C7 C8 C9 118.67(17) . .
C7 C8 H8 120.7 . .
C9 C8 H8 120.7 . .
C10 C9 C8 120.61(17) . .
C10 C9 C1 120.47(16) . .
C8 C9 C1 118.85(16) . .
C5 C10 C9 118.09(17) . .
C5 C10 C4 121.28(17) . .
C9 C10 C4 120.62(16) . .
C2 C11 C12 127.46(17) . .
C2 C11 H11 116.3 . .
C12 C11 H11 116.3 . .
C17 C12 C13 116.09(16) . .
C17 C12 C11 121.27(16) . .
C13 C12 C11 122.57(16) . .
C14 C13 C12 121.66(16) . .
C14 C13 C19 118.20(15) . .
C12 C13 C19 120.10(16) . .
C13 C14 C15 120.38(16) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
O2 C15 C16 125.29(16) . .
O2 C15 C14 115.38(15) . .
C16 C15 C14 119.33(16) . .
C15 C16 C17 119.61(16) . .
C15 C16 H16 120.2 . .
C17 C16 H16 120.2 . .
C16 C17 C12 122.92(16) . .
C16 C17 H17 118.5 . .
C12 C17 H17 118.5 . .
O2 C18 H18A 109.5 . .
O2 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
O2 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
F4 C19 F2 106.28(14) . .
F4 C19 F3 106.15(14) . .
F2 C19 F3 105.52(14) . .
F4 C19 C13 112.86(15) . .
F2 C19 C13 112.38(14) . .
F3 C19 C13 113.06(14) . .
C15 O2 C18 117.62(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.226(2) .
C1 C9 1.492(2) .
C1 C2 1.496(2) .
C2 C11 1.343(2) .
C2 C3 1.502(2) .
C3 C4 1.530(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C10 1.506(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.379(3) .
C5 C10 1.395(3) .
C5 H5 0.9300 .
C6 C7 1.379(3) .
C6 H6 0.9300 .
C7 F1 1.361(2) .
C7 C8 1.369(3) .
C8 C9 1.402(2) .
C8 H8 0.9300 .
C9 C10 1.398(3) .
C11 C12 1.475(2) .
C11 H11 0.9300 .
C12 C17 1.396(2) .
C12 C13 1.415(2) .
C13 C14 1.383(2) .
C13 C19 1.498(2) .
C14 C15 1.396(2) .
C14 H14 0.9300 .
C15 O2 1.363(2) .
C15 C16 1.386(2) .
C16 C17 1.388(2) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 O2 1.427(2) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 F4 1.337(2) .
C19 F2 1.342(2) .
C19 F3 1.345(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C18 H18B F3 0.96 2.52 3.299(2) 138.4 4_566 yes
C14 H14 O1 0.93 2.59 3.346(2) 138.8 4_566 yes
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
O1 C1 C2 C11 20.2(2) . . . .
C9 C1 C2 C11 -159.10(15) . . . .
O1 C1 C2 C3 -163.54(17) . . . .
C9 C1 C2 C3 17.2(2) . . . .
C11 C2 C3 C4 127.83(19) . . . .
C1 C2 C3 C4 -48.1(2) . . . .
C2 C3 C4 C10 53.1(2) . . . .
C10 C5 C6 C7 1.2(3) . . . .
C5 C6 C7 F1 178.41(15) . . . .
C5 C6 C7 C8 -1.6(3) . . . .
F1 C7 C8 C9 -179.50(15) . . . .
C6 C7 C8 C9 0.5(3) . . . .
C7 C8 C9 C10 1.0(3) . . . .
C7 C8 C9 C1 -176.12(15) . . . .
O1 C1 C9 C10 -169.57(16) . . . .
C2 C1 C9 C10 9.7(2) . . . .
O1 C1 C9 C8 7.6(2) . . . .
C2 C1 C9 C8 -173.13(15) . . . .
C6 C5 C10 C9 0.3(3) . . . .
C6 C5 C10 C4 179.11(17) . . . .
C8 C9 C10 C5 -1.4(2) . . . .
C1 C9 C10 C5 175.71(15) . . . .
C8 C9 C10 C4 179.76(16) . . . .
C1 C9 C10 C4 -3.1(2) . . . .
C3 C4 C10 C5 152.32(17) . . . .
C3 C4 C10 C9 -28.9(2) . . . .
C1 C2 C11 C12 -178.32(16) . . . .
C3 C2 C11 C12 5.8(3) . . . .
C2 C11 C12 C17 44.1(3) . . . .
C2 C11 C12 C13 -138.93(19) . . . .
C17 C12 C13 C14 -0.1(2) . . . .
C11 C12 C13 C14 -177.14(16) . . . .
C17 C12 C13 C19 -177.86(16) . . . .
C11 C12 C13 C19 5.1(3) . . . .
C12 C13 C14 C15 0.3(3) . . . .
C19 C13 C14 C15 178.15(15) . . . .
C13 C14 C15 O2 179.38(15) . . . .
C13 C14 C15 C16 -0.8(3) . . . .
O2 C15 C16 C17 -179.18(17) . . . .
C14 C15 C16 C17 1.0(3) . . . .
C15 C16 C17 C12 -0.8(3) . . . .
C13 C12 C17 C16 0.3(3) . . . .
C11 C12 C17 C16 177.40(17) . . . .
C14 C13 C19 F4 -0.6(2) . . . .
C12 C13 C19 F4 177.26(15) . . . .
C14 C13 C19 F2 -120.79(18) . . . .
C12 C13 C19 F2 57.1(2) . . . .
C14 C13 C19 F3 119.89(17) . . . .
C12 C13 C19 F3 -62.2(2) . . . .
C16 C15 O2 C18 -2.8(3) . . . .
C14 C15 O2 C18 177.01(16) . . . .
