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#$Date: 2023-09-25 11:48:25 +0300 (Mon, 25 Sep 2023) $
#$Revision: 286504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107535.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_8107535
loop_
_publ_author_name
'Wei, Pan-Pan'
'Meng, Qing-Guo'
'Wang, Bao-Gang'
'Hou, Gui-Ge'
'Song, Ya-Bin'
_publ_section_title
;
 Crystal structure of
 (E)-7-fluoro-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one,
 C17H12F2O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              701
_journal_page_last               703
_journal_paper_doi               10.1515/ncrs-2023-0159
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C17 H12 F2 O'
_chemical_formula_sum            'C17 H12 F2 O'
_chemical_formula_weight         270.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                94.467(16)
_cell_angle_beta                 96.737(14)
_cell_angle_gamma                103.162(16)
_cell_formula_units_Z            2
_cell_length_a                   7.9570(14)
_cell_length_b                   8.9872(19)
_cell_length_c                   9.3974(16)
_cell_measurement_reflns_used    1305
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8960
_cell_measurement_theta_min      4.7790
_cell_volume                     646.0(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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'CCD plate'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4428
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.674
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²+0.0552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1652
_reflns_number_total             2400
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0159_suppl_001.cif
_cod_data_source_block           xf-1-15
_cod_database_code               8107535
_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   0.985
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_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_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 0.2897(2) 0.86379(17) 1.08772(17) 0.0506(4) Uani 1 1 d . . . . .
C2 C 0.2123(2) 0.74985(17) 0.95954(17) 0.0495(4) Uani 1 1 d . . . . .
C3 C 0.3155(2) 0.63419(18) 0.92180(19) 0.0572(4) Uani 1 1 d . . . . .
H3A H 0.271923 0.584786 0.824813 0.069 Uiso 1 1 calc R U . . .
H3B H 0.300575 0.555561 0.987450 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5082(2) 0.71159(19) 0.93126(18) 0.0578(4) Uani 1 1 d . . . . .
H4A H 0.572539 0.634308 0.912205 0.069 Uiso 1 1 calc R U . . .
H4B H 0.524186 0.782153 0.858237 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7488(2) 0.80928(19) 1.1405(2) 0.0606(5) Uani 1 1 d . . . . .
H5 H 0.821014 0.761959 1.091607 0.073 Uiso 1 1 calc R U . . .
C6 C 0.8127(2) 0.8891(2) 1.2743(2) 0.0641(5) Uani 1 1 d . . . . .
H6 H 0.926527 0.896022 1.315988 0.077 Uiso 1 1 calc R U . . .
C7 C 0.7039(2) 0.95811(19) 1.34421(19) 0.0605(5) Uani 1 1 d . . . . .
C8 C 0.5368(2) 0.95247(18) 1.28701(18) 0.0554(4) Uani 1 1 d . . . . .
H8 H 0.467020 1.001660 1.336998 0.066 Uiso 1 1 calc R U . . .
C9 C 0.47278(19) 0.87084(16) 1.15122(17) 0.0481(4) Uani 1 1 d . . . . .
C10 C 0.5789(2) 0.79775(17) 1.07690(17) 0.0510(4) Uani 1 1 d . . . . .
C11 C 0.0605(2) 0.75926(18) 0.88763(17) 0.0532(4) Uani 1 1 d . . . . .
H11 H 0.018322 0.843308 0.917254 0.064 Uiso 1 1 calc R U . . .
C12 C -0.0481(2) 0.65289(18) 0.76740(17) 0.0531(4) Uani 1 1 d . . . . .
C13 C -0.1454(2) 0.7082(2) 0.6616(2) 0.0706(5) Uani 1 1 d . . . . .
H13 H -0.142088 0.812596 0.667829 0.085 Uiso 1 1 calc R U . . .
C14 C -0.2477(3) 0.6113(3) 0.5467(2) 0.0832(6) Uani 1 1 d . . . . .
H14 H -0.310795 0.649882 0.474736 0.100 Uiso 1 1 calc R U . . .
C15 C -0.2541(3) 0.4580(2) 0.5411(2) 0.0737(6) Uani 1 1 d . . . . .
C16 C -0.1665(2) 0.3968(2) 0.6456(2) 0.0725(5) Uani 1 1 d . . . . .
H16 H -0.175645 0.291410 0.640775 0.087 Uiso 1 1 calc R U . . .
C17 C -0.0640(2) 0.49485(19) 0.7584(2) 0.0648(5) Uani 1 1 d . . . . .
H17 H -0.003718 0.454490 0.830773 0.078 Uiso 1 1 calc R U . . .
F1 F 0.76687(14) 1.03479(13) 1.47806(12) 0.0861(4) Uani 1 1 d . . . . .
F2 F -0.35490(17) 0.36137(16) 0.42858(13) 0.1097(5) Uani 1 1 d . . . . .
O1 O 0.20658(15) 0.94673(14) 1.14246(13) 0.0678(4) 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'
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'
H H 0.0000 0.0000 '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 C2 122.06(15) . .
O1 C1 C9 120.38(14) . .
C2 C1 C9 117.53(14) . .
C11 C2 C1 117.99(14) . .
C11 C2 C3 125.76(15) . .
C1 C2 C3 116.25(14) . .
C2 C3 C4 110.88(13) . .
C2 C3 H3A 109.5 . .
C4 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
C4 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C10 C4 C3 111.42(13) . .
C10 C4 H4A 109.3 . .
C3 C4 H4A 109.3 . .
C10 C4 H4B 109.3 . .
C3 C4 H4B 109.3 . .
H4A C4 H4B 108.0 . .
C6 C5 C10 121.55(16) . .
C6 C5 H5 119.2 . .
C10 C5 H5 119.2 . .
C7 C6 C5 118.17(17) . .
C7 C6 H6 120.9 . .
C5 C6 H6 120.9 . .
C8 C7 F1 118.92(16) . .
C8 C7 C6 123.10(17) . .
F1 C7 C6 117.97(16) . .
C7 C8 C9 118.35(16) . .
C7 C8 H8 120.8 . .
C9 C8 H8 120.8 . .
C10 C9 C8 120.34(15) . .
C10 C9 C1 120.91(14) . .
C8 C9 C1 118.75(14) . .
C5 C10 C9 118.48(15) . .
C5 C10 C4 122.01(15) . .
C9 C10 C4 119.50(15) . .
C2 C11 C12 127.91(15) . .
C2 C11 H11 116.0 . .
C12 C11 H11 116.0 . .
C13 C12 C17 117.55(16) . .
C13 C12 C11 119.91(16) . .
C17 C12 C11 122.47(16) . .
C12 C13 C14 121.31(18) . .
C12 C13 H13 119.3 . .
C14 C13 H13 119.3 . .
C15 C14 C13 118.5(2) . .
C15 C14 H14 120.7 . .
C13 C14 H14 120.7 . .
C16 C15 F2 118.40(19) . .
C16 C15 C14 122.52(18) . .
F2 C15 C14 119.1(2) . .
C15 C16 C17 118.20(18) . .
C15 C16 H16 120.9 . .
C17 C16 H16 120.9 . .
C16 C17 C12 121.81(18) . .
C16 C17 H17 119.1 . .
C12 C17 H17 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2256(17) .
C1 C2 1.492(2) .
C1 C9 1.493(2) .
C2 C11 1.337(2) .
C2 C3 1.510(2) .
C3 C4 1.521(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C10 1.498(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.377(2) .
C5 C10 1.390(2) .
C5 H5 0.9300 .
C6 C7 1.371(2) .
C6 H6 0.9300 .
C7 C8 1.363(2) .
C7 F1 1.3667(19) .
C8 C9 1.399(2) .
C8 H8 0.9300 .
C9 C10 1.397(2) .
C11 C12 1.471(2) .
C11 H11 0.9300 .
C12 C13 1.381(2) .
C12 C17 1.392(2) .
C13 C14 1.383(3) .
C13 H13 0.9300 .
C14 C15 1.364(3) .
C14 H14 0.9300 .
C15 C16 1.361(3) .
C15 F2 1.363(2) .
C16 C17 1.375(2) .
C16 H16 0.9300 .
C17 H17 0.9300 .
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
C16 H16 F1 0.93 2.58 3.400(2) 146.9 1_444 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 12.6(2) . . . .
C9 C1 C2 C11 -169.24(14) . . . .
O1 C1 C2 C3 -168.12(14) . . . .
C9 C1 C2 C3 10.1(2) . . . .
C11 C2 C3 C4 135.39(17) . . . .
C1 C2 C3 C4 -43.89(19) . . . .
C2 C3 C4 C10 55.66(18) . . . .
C10 C5 C6 C7 -0.1(3) . . . .
C5 C6 C7 C8 -0.6(3) . . . .
C5 C6 C7 F1 178.80(15) . . . .
F1 C7 C8 C9 -178.66(14) . . . .
C6 C7 C8 C9 0.8(3) . . . .
C7 C8 C9 C10 -0.2(2) . . . .
C7 C8 C9 C1 179.91(14) . . . .
O1 C1 C9 C10 -168.74(14) . . . .
C2 C1 C9 C10 13.0(2) . . . .
O1 C1 C9 C8 11.2(2) . . . .
C2 C1 C9 C8 -167.08(14) . . . .
C6 C5 C10 C9 0.6(2) . . . .
C6 C5 C10 C4 179.82(15) . . . .
C8 C9 C10 C5 -0.5(2) . . . .
C1 C9 C10 C5 179.41(14) . . . .
C8 C9 C10 C4 -179.69(14) . . . .
C1 C9 C10 C4 0.2(2) . . . .
C3 C4 C10 C5 145.94(16) . . . .
C3 C4 C10 C9 -34.9(2) . . . .
C1 C2 C11 C12 -174.00(14) . . . .
C3 C2 C11 C12 6.7(3) . . . .
C2 C11 C12 C13 -147.61(17) . . . .
C2 C11 C12 C17 35.5(3) . . . .
C17 C12 C13 C14 -3.5(3) . . . .
C11 C12 C13 C14 179.52(16) . . . .
C12 C13 C14 C15 1.5(3) . . . .
C13 C14 C15 C16 1.3(3) . . . .
C13 C14 C15 F2 179.79(17) . . . .
F2 C15 C16 C17 179.59(15) . . . .
C14 C15 C16 C17 -1.9(3) . . . .
C15 C16 C17 C12 -0.2(3) . . . .
C13 C12 C17 C16 2.8(3) . . . .
C11 C12 C17 C16 179.77(16) . . . .
