#------------------------------------------------------------------------------
#$Date: 2023-04-25 10:56:45 +0300 (Tue, 25 Apr 2023) $
#$Revision: 282819 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107110.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_8107110
loop_
_publ_author_name
'Lou, He'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C18H16F2N2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1091
_journal_page_last               1092
_journal_paper_doi               10.1515/ncrs-2016-0072
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C18 H16 F2 N2 O2'
_chemical_formula_sum            'C18 H16 F2 N2 O2'
_chemical_formula_weight         330.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.799(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.619(3)
_cell_length_b                   9.481(2)
_cell_length_c                   14.555(3)
_cell_measurement_reflns_used    3693
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4779
_cell_measurement_theta_min      2.5727
_cell_volume                     1584.5(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0107
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11299
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.6000
_exptl_crystal_size_mid          0.5000
_exptl_crystal_size_min          0.4000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.4902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2525
_reflns_number_total             2734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0072_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        1584.6(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8107110
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.07097(12) 0.26250(14) 0.89375(10) 0.0338(3) Uani 1 1 d . . .
C2 C 0.12584(12) 0.30672(14) 0.82477(10) 0.0326(3) Uani 1 1 d . . .
C3 C 0.25652(12) 0.29796(14) 0.83116(10) 0.0332(3) Uani 1 1 d . . .
H3A H 0.2743 0.2664 0.7708 0.040 Uiso 1 1 calc R . .
C4 C 0.29942(12) 0.18552(15) 0.90287(10) 0.0345(3) Uani 1 1 d . . .
C5 C 0.24004(12) 0.15389(15) 0.97376(11) 0.0350(3) Uani 1 1 d . . .
C6 C 0.40843(12) 0.12048(16) 0.90049(10) 0.0383(4) Uani 1 1 d . . .
C7 C 0.05618(13) 0.36614(16) 0.74153(11) 0.0380(3) Uani 1 1 d . . .
C8 C -0.07389(13) 0.3501(2) 0.73189(12) 0.0481(4) Uani 1 1 d . . .
H8A H -0.0952 0.2581 0.7056 0.058 Uiso 1 1 calc R . .
H8B H -0.1100 0.4205 0.6884 0.058 Uiso 1 1 calc R . .
C9 C -0.12304(12) 0.36518(17) 0.82315(11) 0.0403(4) Uani 1 1 d . . .
C10 C -0.05699(12) 0.26439(16) 0.89490(11) 0.0398(4) Uani 1 1 d . . .
H10A H -0.0711 0.2918 0.9564 0.048 Uiso 1 1 calc R . .
H10B H -0.0874 0.1698 0.8830 0.048 Uiso 1 1 calc R . .
C11 C -0.25227(14) 0.3250(2) 0.80660(15) 0.0600(5) Uani 1 1 d . . .
H11A H -0.2836 0.3344 0.8636 0.090 Uiso 1 1 calc R . .
H11B H -0.2605 0.2292 0.7853 0.090 Uiso 1 1 calc R . .
H11C H -0.2936 0.3864 0.7605 0.090 Uiso 1 1 calc R . .
C12 C -0.10949(16) 0.51693(19) 0.85768(14) 0.0552(5) Uani 1 1 d . . .
H12A H -0.1402 0.5255 0.9150 0.083 Uiso 1 1 calc R . .
H12B H -0.1513 0.5788 0.8121 0.083 Uiso 1 1 calc R . .
H12C H -0.0285 0.5420 0.8676 0.083 Uiso 1 1 calc R . .
C13 C 0.31868(12) 0.43831(15) 0.85461(10) 0.0346(3) Uani 1 1 d . . .
C14 C 0.42725(13) 0.46141(17) 0.82902(12) 0.0469(4) Uani 1 1 d . . .
H14A H 0.4613 0.3938 0.7954 0.056 Uiso 1 1 calc R . .
C15 C 0.48367(14) 0.58608(19) 0.85423(13) 0.0518(4) Uani 1 1 d . . .
C16 C 0.43780(15) 0.69134(18) 0.90220(13) 0.0511(4) Uani 1 1 d . . .
H16A H 0.4777 0.7749 0.9184 0.061 Uiso 1 1 calc R . .
C17 C 0.32970(15) 0.66567(18) 0.92461(12) 0.0477(4) Uani 1 1 d . . .
C18 C 0.26973(13) 0.54230(17) 0.90315(11) 0.0425(4) Uani 1 1 d . . .
H18A H 0.1970 0.5287 0.9210 0.051 Uiso 1 1 calc R . .
N1 N 0.27219(11) 0.07502(15) 1.04846(9) 0.0466(4) Uani 1 1 d . . .
H1A H 0.3396 0.0354 1.0569 0.056 Uiso 1 1 calc R . .
H1B H 0.2257 0.0634 1.0885 0.056 Uiso 1 1 calc R . .
N2 N 0.49584(12) 0.06725(17) 0.89667(11) 0.0553(4) Uani 1 1 d . . .
O1 O 0.12918(8) 0.20508(11) 0.97425(7) 0.0398(3) Uani 1 1 d . . .
O2 O 0.10285(10) 0.42306(14) 0.68146(8) 0.0528(3) Uani 1 1 d . . .
F1 F 0.59006(10) 0.60887(14) 0.82958(11) 0.0866(4) Uani 1 1 d . . .
F2 F 0.27743(11) 0.76884(12) 0.96812(10) 0.0779(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
C2 C1 O1 122.43(13) . .
C2 C1 C10 126.61(14) . .
O1 C1 C10 110.95(12) . .
C1 C2 C7 118.42(13) . .
C1 C2 C3 121.84(13) . .
C7 C2 C3 119.74(12) . .
C2 C3 C4 107.56(11) . .
C2 C3 C13 113.74(11) . .
C4 C3 C13 111.28(12) . .
C2 C3 H3A 108.0 . .
C4 C3 H3A 108.0 . .
C13 C3 H3A 108.0 . .
C5 C4 C6 118.87(13) . .
C5 C4 C3 121.61(12) . .
C6 C4 C3 119.30(12) . .
N1 C5 C4 129.42(13) . .
N1 C5 O1 109.94(12) . .
C4 C5 O1 120.64(13) . .
N2 C6 C4 178.58(17) . .
O2 C7 C2 120.83(14) . .
O2 C7 C8 121.81(14) . .
C2 C7 C8 117.33(13) . .
C7 C8 C9 114.37(13) . .
C7 C8 H8A 108.7 . .
C9 C8 H8A 108.7 . .
C7 C8 H8B 108.7 . .
C9 C8 H8B 108.7 . .
H8A C8 H8B 107.6 . .
C12 C9 C8 109.93(14) . .
C12 C9 C11 109.61(14) . .
C8 C9 C11 109.10(14) . .
C12 C9 C10 110.38(14) . .
C8 C9 C10 108.59(12) . .
C11 C9 C10 109.20(13) . .
C1 C10 C9 113.36(12) . .
C1 C10 H10A 108.9 . .
C9 C10 H10A 108.9 . .
C1 C10 H10B 108.9 . .
C9 C10 H10B 108.9 . .
H10A C10 H10B 107.7 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C18 C13 C14 119.09(14) . .
C18 C13 C3 121.14(13) . .
C14 C13 C3 119.75(13) . .
C15 C14 C13 118.73(15) . .
C15 C14 H14A 120.6 . .
C13 C14 H14A 120.6 . .
F1 C15 C16 117.37(15) . .
F1 C15 C14 118.90(16) . .
C16 C15 C14 123.72(15) . .
C17 C16 C15 115.77(15) . .
C17 C16 H16A 122.1 . .
C15 C16 H16A 122.1 . .
F2 C17 C16 118.41(15) . .
F2 C17 C18 118.18(15) . .
C16 C17 C18 123.38(15) . .
C17 C18 C13 119.28(14) . .
C17 C18 H18A 120.4 . .
C13 C18 H18A 120.4 . .
C5 N1 H1A 120.0 . .
C5 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C1 O1 C5 118.32(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.336(2) .
C1 O1 1.3726(18) .
C1 C10 1.4895(19) .
C2 C7 1.463(2) .
C2 C3 1.5092(18) .
C3 C4 1.522(2) .
C3 C13 1.5276(19) .
C3 H3A 0.9800 .
C4 C5 1.360(2) .
C4 C6 1.4140(19) .
C5 N1 1.325(2) .
C5 O1 1.3776(16) .
C6 N2 1.143(2) .
C7 O2 1.2226(19) .
C7 C8 1.504(2) .
C8 C9 1.531(2) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C12 1.524(2) .
C9 C11 1.532(2) .
C9 C10 1.532(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 C18 1.385(2) .
C13 C14 1.386(2) .
C14 C15 1.374(2) .
C14 H14A 0.9300 .
C15 F1 1.3562(19) .
C15 C16 1.372(3) .
C16 C17 1.367(2) .
C16 H16A 0.9300 .
C17 F2 1.3581(19) .
C17 C18 1.373(2) .
C18 H18A 0.9300 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
