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#$Date: 2022-03-07 12:25:21 +0200 (Mon, 07 Mar 2022) $
#$Revision: 273505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104677.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_8104677
loop_
_publ_author_name
'Su, Xiang-Yi'
'Zhang, Xiao-Fan'
'Meng, Qing-Guo'
'Li, Hong-Juan'
_publ_section_title
;
 Crystal structure of
 (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one,
 C17H14FNO2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1101
_journal_page_last               1103
_journal_paper_doi               10.1515/ncrs-2021-0236
_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                 101.032(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3840(6)
_cell_length_b                   10.9208(8)
_cell_length_c                   16.7006(15)
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.8920
_cell_measurement_theta_min      2.7990
_cell_volume                     1321.84(19)
_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_detector_area_resol_mean 5.2684
_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       'four-circle diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5104
_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         25.498
_diffrn_reflns_theta_min         2.241
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72520
_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    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0589
_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)+(0.0706P)²+0.0416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1867
_reflns_number_total             2453
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0236_suppl.cif
_cod_data_source_block           XF_1_3_2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104677
_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   0.986
_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 0.2117(3) 0.00748(19) 0.43809(14) 0.0275(5) Uani 1 1 d . . . . .
C2 C 0.2732(3) 0.05060(19) 0.52367(13) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.3043(3) 0.18629(19) 0.53626(14) 0.0292(5) Uani 1 1 d . . . . .
H3A H 0.426850 0.206829 0.527593 0.035 Uiso 1 1 calc R U . . .
H3B H 0.298193 0.206828 0.592197 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1625(3) 0.2624(2) 0.47879(14) 0.0325(6) Uani 1 1 d . . . . .
H4A H 0.042942 0.253385 0.494053 0.039 Uiso 1 1 calc R U . . .
H4B H 0.197013 0.348159 0.484535 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1106(3) 0.3090(2) 0.32763(14) 0.0302(6) Uani 1 1 d . . . . .
H5 H 0.098436 0.391404 0.339596 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0910(3) 0.2725(2) 0.24683(14) 0.0315(6) Uani 1 1 d . . . . .
H6 H 0.066815 0.329268 0.204651 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1083(3) 0.1498(2) 0.23084(14) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.1453(3) 0.0637(2) 0.29108(14) 0.0277(5) Uani 1 1 d . . . . .
H8 H 0.155816 -0.018492 0.278130 0.033 Uiso 1 1 calc R U . . .
C9 C 0.1672(3) 0.10092(19) 0.37264(14) 0.0259(5) Uani 1 1 d . . . . .
C10 C 0.1480(3) 0.2247(2) 0.39097(14) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.2970(3) -0.03436(19) 0.58291(14) 0.0270(5) Uani 1 1 d . . . . .
H11 H 0.266007 -0.113631 0.565020 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3636(3) -0.02293(19) 0.67091(13) 0.0259(5) Uani 1 1 d . . . . .
C13 C 0.4783(3) 0.0709(2) 0.70770(14) 0.0272(5) Uani 1 1 d . . . . .
H13 H 0.512809 0.130932 0.674096 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4925(3) -0.00514(19) 0.83521(14) 0.0264(5) Uani 1 1 d . . . . .
C15 C 0.3800(3) -0.10489(19) 0.80594(14) 0.0281(5) Uani 1 1 d . . . . .
H15 H 0.347781 -0.163197 0.841325 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3188(3) -0.11358(19) 0.72334(14) 0.0273(5) Uani 1 1 d . . . . .
H16 H 0.247123 -0.180150 0.701866 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6720(3) 0.1018(2) 0.94663(15) 0.0391(6) Uani 1 1 d . . . . .
H17A H 0.781281 0.097371 0.923508 0.059 Uiso 1 1 calc R U . . .
H17B H 0.705472 0.097424 1.005009 0.059 Uiso 1 1 calc R U . . .
H17C H 0.609516 0.177745 0.931174 0.059 Uiso 1 1 calc R U . . .
F1 F 0.08462(19) 0.11296(12) 0.15143(8) 0.0386(4) Uani 1 1 d . . . . .
N1 N 0.5424(2) 0.08038(16) 0.78830(12) 0.0282(5) Uani 1 1 d . . . . .
O1 O 0.2012(2) -0.10235(13) 0.42069(10) 0.0341(4) Uani 1 1 d . . . . .
O2 O 0.5520(2) 0.00144(14) 0.91702(9) 0.0336(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 120.0(2) . .
O1 C1 C2 121.8(2) . .
C9 C1 C2 118.19(18) . .
C11 C2 C1 117.4(2) . .
C11 C2 C3 125.5(2) . .
C1 C2 C3 117.03(18) . .
C2 C3 C4 112.37(18) . .
C2 C3 H3A 109.1 . .
C4 C3 H3A 109.1 . .
C2 C3 H3B 109.1 . .
C4 C3 H3B 109.1 . .
H3A C3 H3B 107.9 . .
C10 C4 C3 112.09(18) . .
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 121.2(2) . .
C6 C5 H5 119.4 . .
C10 C5 H5 119.4 . .
C7 C6 C5 118.2(2) . .
C7 C6 H6 120.9 . .
C5 C6 H6 120.9 . .
F1 C7 C8 118.9(2) . .
F1 C7 C6 118.4(2) . .
C8 C7 C6 122.7(2) . .
C7 C8 C9 119.1(2) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
C10 C9 C8 119.7(2) . .
C10 C9 C1 121.3(2) . .
C8 C9 C1 118.97(19) . .
C5 C10 C9 119.1(2) . .
C5 C10 C4 121.8(2) . .
C9 C10 C4 119.1(2) . .
C2 C11 C12 130.7(2) . .
C2 C11 H11 114.6 . .
C12 C11 H11 114.6 . .
C13 C12 C16 116.0(2) . .
C13 C12 C11 124.35(19) . .
C16 C12 C11 119.53(19) . .
N1 C13 C12 124.5(2) . .
N1 C13 H13 117.7 . .
C12 C13 H13 117.7 . .
N1 C14 O2 119.27(19) . .
N1 C14 C15 124.0(2) . .
O2 C14 C15 116.72(19) . .
C16 C15 C14 117.7(2) . .
C16 C15 H15 121.2 . .
C14 C15 H15 121.2 . .
C15 C16 C12 120.5(2) . .
C15 C16 H16 119.7 . .
C12 C16 H16 119.7 . .
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 . .
C14 N1 C13 117.16(19) . .
C14 O2 C17 116.57(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.233(2) .
C1 C9 1.485(3) .
C1 C2 1.491(3) .
C2 C11 1.343(3) .
C2 C3 1.508(3) .
C3 C4 1.524(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C10 1.507(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.388(3) .
C5 C10 1.390(3) .
C5 H5 0.9300 .
C6 C7 1.377(3) .
C6 H6 0.9300 .
C7 F1 1.365(3) .
C7 C8 1.366(3) .
C8 C9 1.401(3) .
C8 H8 0.9300 .
C9 C10 1.399(3) .
C11 C12 1.463(3) .
C11 H11 0.9300 .
C12 C13 1.395(3) .
C12 C16 1.402(3) .
C13 N1 1.343(3) .
C13 H13 0.9300 .
C14 N1 1.316(3) .
C14 O2 1.355(3) .
C14 C15 1.400(3) .
C15 C16 1.370(3) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 O2 1.437(3) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
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 -7.5(3) . . . .
C9 C1 C2 C11 174.22(19) . . . .
O1 C1 C2 C3 172.29(19) . . . .
C9 C1 C2 C3 -6.0(3) . . . .
C11 C2 C3 C4 -142.5(2) . . . .
C1 C2 C3 C4 37.8(3) . . . .
C2 C3 C4 C10 -51.9(2) . . . .
C10 C5 C6 C7 0.5(3) . . . .
C5 C6 C7 F1 178.38(17) . . . .
C5 C6 C7 C8 -0.6(3) . . . .
F1 C7 C8 C9 -179.13(17) . . . .
C6 C7 C8 C9 -0.2(3) . . . .
C7 C8 C9 C10 1.1(3) . . . .
C7 C8 C9 C1 -178.64(19) . . . .
O1 C1 C9 C10 169.30(19) . . . .
C2 C1 C9 C10 -12.3(3) . . . .
O1 C1 C9 C8 -11.0(3) . . . .
C2 C1 C9 C8 167.34(18) . . . .
C6 C5 C10 C9 0.4(3) . . . .
C6 C5 C10 C4 -177.68(18) . . . .
C8 C9 C10 C5 -1.2(3) . . . .
C1 C9 C10 C5 178.53(19) . . . .
C8 C9 C10 C4 176.97(19) . . . .
C1 C9 C10 C4 -3.3(3) . . . .
C3 C4 C10 C5 -146.3(2) . . . .
C3 C4 C10 C9 35.6(3) . . . .
C1 C2 C11 C12 176.72(19) . . . .
C3 C2 C11 C12 -3.0(4) . . . .
C2 C11 C12 C13 -24.8(3) . . . .
C2 C11 C12 C16 158.3(2) . . . .
C16 C12 C13 N1 -1.7(3) . . . .
C11 C12 C13 N1 -178.70(18) . . . .
N1 C14 C15 C16 0.2(3) . . . .
O2 C14 C15 C16 -179.75(18) . . . .
C14 C15 C16 C12 -2.1(3) . . . .
C13 C12 C16 C15 2.7(3) . . . .
C11 C12 C16 C15 179.88(18) . . . .
O2 C14 N1 C13 -179.20(17) . . . .
C15 C14 N1 C13 0.9(3) . . . .
C12 C13 N1 C14 -0.1(3) . . . .
N1 C14 O2 C17 -1.7(3) . . . .
C15 C14 O2 C17 178.17(19) . . . .
