#------------------------------------------------------------------------------
#$Date: 2022-03-11 12:34:42 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273662 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104751.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_8104751
loop_
_publ_author_name
'Zhang, Xiao-Fan'
'Meng, Qing-Guo'
_publ_section_title
;
 Crystal structure of
 (E)-2-((2-methoxy-3-pyridyl)methylene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one,
 C17H14FNO2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              507
_journal_page_last               509
_journal_paper_doi               10.1515/ncrs-2020-0603
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 F N O2'
_chemical_formula_sum            'C17 H14 F N O2'
_chemical_formula_weight         283.29
_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                 113.165(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0279(13)
_cell_length_b                   7.0527(5)
_cell_length_c                   14.4150(16)
_cell_measurement_reflns_used    1983
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      28.6530
_cell_measurement_theta_min      3.0720
_cell_volume                     1311.2(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(3)
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4957
_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         25.500
_diffrn_reflns_theta_min         2.850
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62845
_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    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0524
_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)+(0.0621P)²+0.7092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1910
_reflns_number_total             2438
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0603_suppl.cif
_cod_data_source_block           XF-1-4_2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104751
_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   0.989
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 0.47372(16) 0.5363(3) 0.60726(15) 0.0216(5) Uani 1 1 d . . . . .
C2 C 0.52721(16) 0.7232(3) 0.64029(15) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.46085(16) 0.8992(3) 0.62279(16) 0.0229(5) Uani 1 1 d . . . . .
H3A H 0.447439 0.948526 0.555991 0.027 Uiso 1 1 calc R U . . .
H3B H 0.498772 0.995243 0.671525 0.027 Uiso 1 1 calc R U . . .
C4 C 0.35743(16) 0.8621(3) 0.63186(17) 0.0244(5) Uani 1 1 d . . . . .
H4A H 0.369926 0.842488 0.702299 0.029 Uiso 1 1 calc R U . . .
H4B H 0.313485 0.972875 0.608510 0.029 Uiso 1 1 calc R U . . .
C5 C 0.19429(16) 0.6850(3) 0.52630(16) 0.0252(5) Uani 1 1 d . . . . .
H5 H 0.155941 0.791073 0.528701 0.030 Uiso 1 1 calc R U . . .
C6 C 0.14291(17) 0.5233(3) 0.47724(17) 0.0277(5) Uani 1 1 d . . . . .
H6 H 0.070919 0.520037 0.446411 0.033 Uiso 1 1 calc R U . . .
C7 C 0.20129(17) 0.3674(3) 0.47532(16) 0.0250(5) Uani 1 1 d . . . . .
C8 C 0.30745(16) 0.3677(3) 0.51677(16) 0.0228(5) Uani 1 1 d . . . . .
H8 H 0.344735 0.260862 0.513213 0.027 Uiso 1 1 calc R U . . .
C9 C 0.35843(16) 0.5333(3) 0.56472(15) 0.0201(5) Uani 1 1 d . . . . .
C10 C 0.30175(16) 0.6922(3) 0.57194(15) 0.0213(5) Uani 1 1 d . . . . .
C11 C 0.63138(16) 0.7192(3) 0.68050(15) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.659874 0.598055 0.691636 0.026 Uiso 1 1 calc R U . . .
C12 C 0.70752(16) 0.8725(3) 0.70972(16) 0.0216(5) Uani 1 1 d . . . . .
C13 C 0.81155(16) 0.8328(3) 0.77370(16) 0.0225(5) Uani 1 1 d . . . . .
C14 C 0.86833(17) 1.1292(3) 0.75901(17) 0.0270(5) Uani 1 1 d . . . . .
H14 H 0.922433 1.215867 0.774860 0.032 Uiso 1 1 calc R U . . .
C15 C 0.77038(17) 1.1868(3) 0.69688(16) 0.0254(5) Uani 1 1 d . . . . .
H15 H 0.758412 1.310006 0.672016 0.031 Uiso 1 1 calc R U . . .
C16 C 0.69004(17) 1.0579(3) 0.67206(16) 0.0243(5) Uani 1 1 d . . . . .
H16 H 0.623403 1.094834 0.629762 0.029 Uiso 1 1 calc R U . . .
C17 C 0.93629(16) 0.6116(4) 0.87542(18) 0.0304(6) Uani 1 1 d . . . . .
H17A H 0.980048 0.637150 0.839771 0.046 Uiso 1 1 calc R U . . .
H17B H 0.942323 0.480371 0.894641 0.046 Uiso 1 1 calc R U . . .
H17C H 0.957201 0.689483 0.934725 0.046 Uiso 1 1 calc R U . . .
F1 F 0.15087(10) 0.2050(2) 0.42968(10) 0.0362(4) Uani 1 1 d . . . . .
N1 N 0.88976(14) 0.9528(3) 0.79815(13) 0.0254(5) Uani 1 1 d . . . . .
O1 O 0.52231(11) 0.3891(2) 0.61177(12) 0.0296(4) Uani 1 1 d . . . . .
O2 O 0.83063(11) 0.6529(2) 0.81134(11) 0.0279(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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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 120.00(19) . .
O1 C1 C2 121.87(19) . .
C9 C1 C2 118.09(18) . .
C11 C2 C1 116.24(19) . .
C11 C2 C3 125.6(2) . .
C1 C2 C3 118.08(18) . .
C2 C3 C4 112.78(18) . .
C2 C3 H3A 109.0 . .
C4 C3 H3A 109.0 . .
C2 C3 H3B 109.0 . .
C4 C3 H3B 109.0 . .
H3A C3 H3B 107.8 . .
C10 C4 C3 112.55(18) . .
C10 C4 H4A 109.1 . .
C3 C4 H4A 109.1 . .
C10 C4 H4B 109.1 . .
C3 C4 H4B 109.1 . .
H4A C4 H4B 107.8 . .
C6 C5 C10 121.5(2) . .
C6 C5 H5 119.3 . .
C10 C5 H5 119.3 . .
C7 C6 C5 118.3(2) . .
C7 C6 H6 120.9 . .
C5 C6 H6 120.9 . .
C8 C7 F1 118.6(2) . .
C8 C7 C6 122.9(2) . .
F1 C7 C6 118.56(19) . .
C7 C8 C9 118.2(2) . .
C7 C8 H8 120.9 . .
C9 C8 H8 120.9 . .
C10 C9 C8 120.57(19) . .
C10 C9 C1 120.98(19) . .
C8 C9 C1 118.44(19) . .
C5 C10 C9 118.5(2) . .
C5 C10 C4 121.56(19) . .
C9 C10 C4 119.87(18) . .
C2 C11 C12 131.0(2) . .
C2 C11 H11 114.5 . .
C12 C11 H11 114.5 . .
C16 C12 C13 114.6(2) . .
C16 C12 C11 125.66(19) . .
C13 C12 C11 119.4(2) . .
N1 C13 O2 118.55(19) . .
N1 C13 C12 125.7(2) . .
O2 C13 C12 115.73(19) . .
N1 C14 C15 123.1(2) . .
N1 C14 H14 118.5 . .
C15 C14 H14 118.5 . .
C14 C15 C16 118.7(2) . .
C14 C15 H15 120.7 . .
C16 C15 H15 120.7 . .
C15 C16 C12 120.9(2) . .
C15 C16 H16 119.5 . .
C12 C16 H16 119.5 . .
O2 C17 H17A 109.5 . .
O2 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
O2 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C13 N1 C14 117.04(19) . .
C13 O2 C17 115.89(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.230(3) .
C1 C9 1.487(3) .
C1 C2 1.499(3) .
C2 C11 1.344(3) .
C2 C3 1.512(3) .
C3 C4 1.530(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C10 1.503(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.385(3) .
C5 C10 1.388(3) .
C5 H5 0.9300 .
C6 C7 1.378(3) .
C6 H6 0.9300 .
C7 C8 1.369(3) .
C7 F1 1.371(2) .
C8 C9 1.402(3) .
C8 H8 0.9300 .
C9 C10 1.401(3) .
C11 C12 1.461(3) .
C11 H11 0.9300 .
C12 C16 1.400(3) .
C12 C13 1.414(3) .
C13 N1 1.319(3) .
C13 O2 1.364(3) .
C14 N1 1.350(3) .
C14 C15 1.373(3) .
C14 H14 0.9300 .
C15 C16 1.381(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 O2 1.435(2) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
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
C6 H6 N1 0.93 2.61 3.477(3) 156.3 4_475 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 -3.7(3) . . . .
C9 C1 C2 C11 178.47(18) . . . .
O1 C1 C2 C3 174.3(2) . . . .
C9 C1 C2 C3 -3.5(3) . . . .
C11 C2 C3 C4 -148.8(2) . . . .
C1 C2 C3 C4 33.4(3) . . . .
C2 C3 C4 C10 -48.9(2) . . . .
C10 C5 C6 C7 0.5(3) . . . .
C5 C6 C7 C8 -2.2(3) . . . .
C5 C6 C7 F1 177.98(19) . . . .
F1 C7 C8 C9 -179.01(18) . . . .
C6 C7 C8 C9 1.2(3) . . . .
C7 C8 C9 C10 1.6(3) . . . .
C7 C8 C9 C1 -178.26(19) . . . .
O1 C1 C9 C10 170.7(2) . . . .
C2 C1 C9 C10 -11.4(3) . . . .
O1 C1 C9 C8 -9.4(3) . . . .
C2 C1 C9 C8 168.41(18) . . . .
C6 C5 C10 C9 2.1(3) . . . .
C6 C5 C10 C4 -175.3(2) . . . .
C8 C9 C10 C5 -3.1(3) . . . .
C1 C9 C10 C5 176.67(19) . . . .
C8 C9 C10 C4 174.34(19) . . . .
C1 C9 C10 C4 -5.9(3) . . . .
C3 C4 C10 C5 -146.3(2) . . . .
C3 C4 C10 C9 36.3(3) . . . .
C1 C2 C11 C12 172.2(2) . . . .
C3 C2 C11 C12 -5.6(4) . . . .
C2 C11 C12 C16 -22.9(4) . . . .
C2 C11 C12 C13 163.8(2) . . . .
C16 C12 C13 N1 -0.8(3) . . . .
C11 C12 C13 N1 173.2(2) . . . .
C16 C12 C13 O2 -179.95(19) . . . .
C11 C12 C13 O2 -6.0(3) . . . .
N1 C14 C15 C16 -0.8(3) . . . .
C14 C15 C16 C12 0.4(3) . . . .
C13 C12 C16 C15 0.4(3) . . . .
C11 C12 C16 C15 -173.2(2) . . . .
O2 C13 N1 C14 179.51(19) . . . .
C12 C13 N1 C14 0.4(3) . . . .
C15 C14 N1 C13 0.5(3) . . . .
N1 C13 O2 C17 0.1(3) . . . .
C12 C13 O2 C17 179.36(19) . . . .
