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#$Date: 2023-03-10 10:59:20 +0200 (Fri, 10 Mar 2023) $
#$Revision: 281798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/69/8106906.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_8106906
loop_
_publ_author_name
'Meng, Xian-Fang'
'Liu, Li-Zeng'
'Bai, Zheng-Chen'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(4-fluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C16H13FN2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              455
_journal_page_last               456
_journal_paper_doi               10.1515/ncrs-2015-0134
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C16 H13 F N2 O2'
_chemical_formula_sum            'C16 H13 F N2 O2'
_chemical_formula_weight         284.28
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.803(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2587(16)
_cell_length_b                   10.8816(11)
_cell_length_c                   19.750(3)
_cell_measurement_reflns_used    1583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6310
_cell_measurement_theta_min      3.1440
_cell_volume                     2789.2(6)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5005
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0071(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0423
_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)+(0.0544P)²+0.5148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1804
_reflns_number_total             2452
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0134_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               8106906
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28732(13) 0.32845(15) 0.42696(8) 0.0414(4) Uani 1 1 d . . .
C2 C 0.26432(12) 0.44511(15) 0.44121(8) 0.0386(4) Uani 1 1 d . . .
C3 C 0.15685(12) 0.49852(14) 0.42145(9) 0.0388(4) Uani 1 1 d . . .
H3A H 0.1403 0.5365 0.4628 0.047 Uiso 1 1 calc R . .
C4 C 0.08181(12) 0.39582(15) 0.39957(9) 0.0403(4) Uani 1 1 d . . .
C5 C 0.11073(13) 0.28294(15) 0.38667(9) 0.0426(4) Uani 1 1 d . . .
C6 C 0.04077(15) 0.17878(17) 0.36172(11) 0.0581(5) Uani 1 1 d . . .
H6A H 0.0382 0.1236 0.3999 0.070 Uiso 1 1 calc R . .
H6B H 0.0672 0.1332 0.3269 0.070 Uiso 1 1 calc R . .
C7 C -0.06720(16) 0.2248(2) 0.33107(14) 0.0796(7) Uani 1 1 d . . .
H7A H -0.0679 0.2612 0.2862 0.096 Uiso 1 1 calc R . .
H7B H -0.1146 0.1559 0.3245 0.096 Uiso 1 1 calc R . .
C8 C -0.10259(16) 0.3180(2) 0.37690(14) 0.0787(7) Uani 1 1 d . . .
H8A H -0.1682 0.3515 0.3533 0.094 Uiso 1 1 calc R . .
H8B H -0.1135 0.2775 0.4186 0.094 Uiso 1 1 calc R . .
C9 C -0.02814(14) 0.42106(18) 0.39671(10) 0.0508(5) Uani 1 1 d . . .
C10 C 0.34453(14) 0.52205(16) 0.47472(9) 0.0468(5) Uani 1 1 d . . .
C11 C 0.14827(12) 0.59686(14) 0.36624(9) 0.0400(4) Uani 1 1 d . . .
C12 C 0.12684(14) 0.71646(15) 0.38059(11) 0.0522(5) Uani 1 1 d . . .
H12A H 0.1165 0.7365 0.4244 0.063 Uiso 1 1 calc R . .
C13 C 0.12040(15) 0.80717(18) 0.33129(14) 0.0675(6) Uani 1 1 d . . .
H13A H 0.1065 0.8881 0.3415 0.081 Uiso 1 1 calc R . .
C14 C 0.13472(16) 0.7760(2) 0.26785(13) 0.0706(7) Uani 1 1 d . . .
C15 C 0.15495(18) 0.6601(2) 0.25093(11) 0.0724(6) Uani 1 1 d . . .
H15A H 0.1639 0.6413 0.2066 0.087 Uiso 1 1 calc R . .
C16 C 0.16211(15) 0.56994(18) 0.30047(10) 0.0568(5) Uani 1 1 d . . .
H16A H 0.1765 0.4896 0.2895 0.068 Uiso 1 1 calc R . .
O1 O 0.21271(9) 0.24776(10) 0.39601(6) 0.0479(4) Uani 1 1 d . . .
O2 O -0.05629(10) 0.52143(13) 0.41282(8) 0.0666(4) Uani 1 1 d . . .
N1 N 0.37983(11) 0.27456(13) 0.44062(8) 0.0565(5) Uani 1 1 d . . .
H1A H 0.4331 0.3154 0.4608 0.068 Uiso 1 1 calc R . .
H1B H 0.3861 0.1991 0.4293 0.068 Uiso 1 1 calc R . .
N2 N 0.40913(13) 0.58567(15) 0.50216(9) 0.0682(5) Uani 1 1 d . . .
F1 F 0.12940(12) 0.86688(14) 0.21996(8) 0.1156(6) 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
N1 C1 C2 127.47(16) . .
N1 C1 O1 110.98(14) . .
C2 C1 O1 121.54(15) . .
C1 C2 C10 118.46(15) . .
C1 C2 C3 123.26(14) . .
C10 C2 C3 118.26(14) . .
C4 C3 C2 108.79(13) . .
C4 C3 C11 111.78(13) . .
C2 C3 C11 112.63(13) . .
C4 C3 H3A 107.8 . .
C2 C3 H3A 107.8 . .
C11 C3 H3A 107.8 . .
C5 C4 C9 119.19(16) . .
C5 C4 C3 122.98(15) . .
C9 C4 C3 117.71(15) . .
C4 C5 O1 122.98(15) . .
C4 C5 C6 125.84(16) . .
O1 C5 C6 111.17(15) . .
C5 C6 C7 110.76(16) . .
C5 C6 H6A 109.5 . .
C7 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C7 C6 H6B 109.5 . .
H6A C6 H6B 108.1 . .
C8 C7 C6 111.62(19) . .
C8 C7 H7A 109.3 . .
C6 C7 H7A 109.3 . .
C8 C7 H7B 109.3 . .
C6 C7 H7B 109.3 . .
H7A C7 H7B 108.0 . .
C9 C8 C7 113.29(18) . .
C9 C8 H8A 108.9 . .
C7 C8 H8A 108.9 . .
C9 C8 H8B 108.9 . .
C7 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
O2 C9 C4 120.74(17) . .
O2 C9 C8 121.40(18) . .
C4 C9 C8 117.79(17) . .
N2 C10 C2 179.3(2) . .
C12 C11 C16 117.91(17) . .
C12 C11 C3 120.58(16) . .
C16 C11 C3 121.50(15) . .
C11 C12 C13 121.3(2) . .
C11 C12 H12A 119.4 . .
C13 C12 H12A 119.4 . .
C14 C13 C12 118.5(2) . .
C14 C13 H13A 120.8 . .
C12 C13 H13A 120.8 . .
C15 C14 C13 122.6(2) . .
C15 C14 F1 119.6(3) . .
C13 C14 F1 117.8(2) . .
C14 C15 C16 118.7(2) . .
C14 C15 H15A 120.7 . .
C16 C15 H15A 120.7 . .
C15 C16 C11 121.03(19) . .
C15 C16 H16A 119.5 . .
C11 C16 H16A 119.5 . .
C1 O1 C5 118.69(13) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.336(2) .
C1 C2 1.349(2) .
C1 O1 1.3695(19) .
C2 C10 1.408(2) .
C2 C3 1.514(2) .
C3 C4 1.500(2) .
C3 C11 1.515(2) .
C3 H3A 0.9800 .
C4 C5 1.327(2) .
C4 C9 1.473(2) .
C5 O1 1.3809(19) .
C5 C6 1.483(2) .
C6 C7 1.521(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.498(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.492(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 O2 1.217(2) .
C10 N2 1.147(2) .
C11 C12 1.374(2) .
C11 C16 1.380(2) .
C12 C13 1.377(3) .
C12 H12A 0.9300 .
C13 C14 1.348(3) .
C13 H13A 0.9300 .
C14 C15 1.346(3) .
C14 F1 1.360(2) .
C15 C16 1.375(3) .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
