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#$Date: 2023-04-25 11:01:57 +0300 (Tue, 25 Apr 2023) $
#$Revision: 282820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/71/8107111.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_8107111
loop_
_publ_author_name
'Zhang, Xi-Ping'
'Yu, Fei-Jiang'
'He, Xiang-Ming'
'Zou, De-Hong'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(3,4,5-trifluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C16H11F3N2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1093
_journal_page_last               1094
_journal_paper_doi               10.1515/ncrs-2016-0073
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C16 H11 F3 N2 O2'
_chemical_formula_weight         320.27
_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                111.488(7)
_cell_angle_beta                 94.705(6)
_cell_angle_gamma                99.107(6)
_cell_formula_units_Z            2
_cell_length_a                   8.3288(5)
_cell_length_b                   8.6385(8)
_cell_length_c                   11.6004(8)
_cell_measurement_temperature    293(2)
_cell_volume                     757.87(11)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4859
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         4.238
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0196(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.568
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.568
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0435
_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)+(0.0200P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1998
_reflns_number_total             2654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0073_suppl.cif
_cod_data_source_block           a
_cod_database_code               8107111
_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.
;
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
O1 O 0.48780(16) 0.40895(17) 0.31360(14) 0.0463(4) Uani 1 1 d . . . . .
O2 O 1.05477(18) 0.4175(2) 0.35629(16) 0.0587(4) Uani 1 1 d . . . . .
C3 C 0.8135(2) 0.6104(2) 0.35036(17) 0.0351(4) Uani 1 1 d . . . . .
H3A H 0.9062 0.6643 0.4190 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6647(2) 0.6809(2) 0.39365(17) 0.0366(4) Uani 1 1 d . . . . .
C4 C 0.7764(2) 0.4226(2) 0.32121(18) 0.0367(4) Uani 1 1 d . . . . .
C10 C 0.6822(2) 0.8582(3) 0.45636(19) 0.0426(5) Uani 1 1 d . . . . .
C5 C 0.6230(2) 0.3340(2) 0.29954(19) 0.0405(5) Uani 1 1 d . . . . .
C11 C 0.8612(2) 0.6444(2) 0.23621(18) 0.0365(4) Uani 1 1 d . . . . .
N1 N 0.3722(2) 0.6309(2) 0.39549(18) 0.0547(5) Uani 1 1 d . . . . .
H1A H 0.3707 0.7371 0.4315 0.066 Uiso 1 1 calc R U . . .
H1B H 0.2824 0.5562 0.3760 0.066 Uiso 1 1 calc R U . . .
C9 C 0.9140(3) 0.3369(3) 0.3229(2) 0.0454(5) Uani 1 1 d . . . . .
C1 C 0.5133(2) 0.5822(2) 0.37001(18) 0.0399(5) Uani 1 1 d . . . . .
N2 N 0.6974(2) 1.0025(2) 0.5071(2) 0.0621(6) Uani 1 1 d . . . . .
C6 C 0.5738(3) 0.1470(3) 0.2577(2) 0.0542(6) Uani 1 1 d . . . . .
H6A H 0.4765 0.1055 0.1944 0.065 Uiso 1 1 calc R U . . .
H6B H 0.5470 0.1181 0.3281 0.065 Uiso 1 1 calc R U . . .
C16 C 1.0141(3) 0.7360(3) 0.2405(2) 0.0506(6) Uani 1 1 d . . . . .
H16A H 1.0909 0.7771 0.3131 0.061 Uiso 1 1 calc R U . . .
F2 F 0.9825(3) 0.7442(3) -0.06930(17) 0.1153(7) Uani 1 1 d . . . . .
C12 C 0.7503(3) 0.5854(3) 0.1275(2) 0.0547(6) Uani 1 1 d . . . . .
H12A H 0.6462 0.5234 0.1229 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8746(3) 0.1492(3) 0.2888(3) 0.0673(7) Uani 1 1 d . . . . .
H8A H 0.8718 0.1273 0.3649 0.081 Uiso 1 1 calc R U . . .
H8B H 0.9618 0.1001 0.2477 0.081 Uiso 1 1 calc R U . . .
F1 F 0.6855(3) 0.5624(3) -0.08032(16) 0.1287(9) Uani 1 1 d . . . . .
C15 C 1.0526(3) 0.7662(3) 0.1370(3) 0.0670(7) Uani 1 1 d . . . . .
F3 F 1.2013(2) 0.8560(3) 0.1397(2) 0.1274(8) Uani 1 1 d . . . . .
C7 C 0.7129(3) 0.0627(3) 0.2038(3) 0.0697(8) Uani 1 1 d . . . . .
H7A H 0.6888 -0.0559 0.1927 0.084 Uiso 1 1 calc R U . . .
H7B H 0.7210 0.0676 0.1222 0.084 Uiso 1 1 calc R U . . .
C14 C 0.9440(4) 0.7100(3) 0.0303(3) 0.0664(7) Uani 1 1 d . . . . .
C13 C 0.7936(3) 0.6183(4) 0.0261(2) 0.0668(7) 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
C1 O1 C5 118.34(15) . .
C4 C3 C2 108.27(15) . .
C4 C3 C11 110.61(15) . .
C2 C3 C11 112.14(15) . .
C4 C3 H3A 108.6 . .
C2 C3 H3A 108.6 . .
C11 C3 H3A 108.6 . .
C1 C2 C10 118.30(18) . .
C1 C2 C3 122.77(17) . .
C10 C2 C3 118.86(16) . .
C5 C4 C9 119.19(18) . .
C5 C4 C3 122.20(18) . .
C9 C4 C3 118.55(17) . .
N2 C10 C2 179.6(2) . .
C4 C5 O1 122.86(18) . .
C4 C5 C6 125.99(19) . .
O1 C5 C6 111.14(17) . .
C12 C11 C16 118.85(19) . .
C12 C11 C3 120.22(17) . .
C16 C11 C3 120.92(18) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
O2 C9 C4 120.74(19) . .
O2 C9 C8 121.5(2) . .
C4 C9 C8 117.69(19) . .
N1 C1 C2 128.06(19) . .
N1 C1 O1 110.37(17) . .
C2 C1 O1 121.57(18) . .
C5 C6 C7 110.19(18) . .
C5 C6 H6A 109.6 . .
C7 C6 H6A 109.6 . .
C5 C6 H6B 109.6 . .
C7 C6 H6B 109.6 . .
H6A C6 H6B 108.1 . .
C15 C16 C11 119.6(2) . .
C15 C16 H16A 120.2 . .
C11 C16 H16A 120.2 . .
C13 C12 C11 119.8(2) . .
C13 C12 H12A 120.1 . .
C11 C12 H12A 120.1 . .
C9 C8 C7 113.4(2) . .
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 . .
F3 C15 C14 117.7(2) . .
F3 C15 C16 120.3(3) . .
C14 C15 C16 122.0(2) . .
C8 C7 C6 111.2(2) . .
C8 C7 H7A 109.4 . .
C6 C7 H7A 109.4 . .
C8 C7 H7B 109.4 . .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
F2 C14 C15 121.2(3) . .
F2 C14 C13 120.5(3) . .
C15 C14 C13 118.3(2) . .
F1 C13 C14 118.2(2) . .
F1 C13 C12 120.2(2) . .
C14 C13 C12 121.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.369(2) .
O1 C5 1.377(2) .
O2 C9 1.216(3) .
C3 C4 1.505(3) .
C3 C2 1.508(3) .
C3 C11 1.527(3) .
C3 H3A 0.9800 .
C2 C1 1.351(3) .
C2 C10 1.411(3) .
C4 C5 1.333(3) .
C4 C9 1.461(3) .
C10 N2 1.148(3) .
C5 C6 1.482(3) .
C11 C12 1.376(3) .
C11 C16 1.376(3) .
N1 C1 1.329(3) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
C9 C8 1.494(3) .
C6 C7 1.522(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C16 C15 1.370(3) .
C16 H16A 0.9300 .
F2 C14 1.344(3) .
C12 C13 1.370(3) .
C12 H12A 0.9300 .
C8 C7 1.506(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
F1 C13 1.346(3) .
C15 F3 1.345(3) .
C15 C14 1.350(4) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C14 C13 1.359(4) .
