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#$Date: 2023-04-07 10:21:57 +0300 (Fri, 07 Apr 2023) $
#$Revision: 282510 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107066.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_8107066
loop_
_publ_author_name
'Bu, Xian-Zhong'
'Shi, Juan-Juan'
'Gao, Ke'
'Long, Tao'
_publ_section_title
;
 Crystal structure of
 2-amino-4-(3-trifluoromethylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile,
 C17H13F3N2O2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              969
_journal_page_last               970
_journal_paper_doi               10.1515/ncrs-2016-0026
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 F3 N2 O2'
_chemical_formula_sum            'C17 H13 F3 N2 O2'
_chemical_formula_weight         334.29
_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                105.872(7)
_cell_angle_beta                 104.107(7)
_cell_angle_gamma                95.738(7)
_cell_formula_units_Z            2
_cell_length_a                   8.2615(7)
_cell_length_b                   8.7262(7)
_cell_length_c                   11.6521(9)
_cell_measurement_reflns_used    1479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8520
_cell_measurement_theta_min      2.5800
_cell_volume                     771.02(12)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0258
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_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       -13
_diffrn_reflns_number            4968
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    0.120
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.854
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.085
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1924
_reflns_number_total             2711
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0026_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        771.02(11)
_cod_database_code               8107066
_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
F1 F 1.1629(4) 0.9326(4) 0.5684(5) 0.1207(18) Uani 0.854(7) 1 d . . P A 1
F2 F 1.2744(4) 0.7974(7) 0.6759(4) 0.147(2) Uani 0.854(7) 1 d . . P A 1
F3 F 1.1687(5) 0.6941(5) 0.4826(4) 0.141(2) Uani 0.854(7) 1 d . . P A 1
F1A F 1.204(2) 0.929(2) 0.6674(17) 0.083(5) Uiso 0.146(7) 1 d . U P A 2
F2A F 1.114(2) 0.812(3) 0.4771(16) 0.083(5) Uiso 0.146(7) 1 d . U P A 2
F3A F 1.224(2) 0.682(2) 0.593(2) 0.083(5) Uiso 0.146(7) 1 d . U P A 2
C2 C 0.7636(3) 0.4481(3) 0.8211(2) 0.0358(6) Uani 1 1 d . . . . .
C4 C 0.7971(3) 0.6304(3) 0.8467(2) 0.0346(5) Uani 1 1 d . . . . .
H4A H 0.9060 0.6757 0.9106 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6585(3) 0.6986(3) 0.8969(2) 0.0367(6) Uani 1 1 d . . . . .
C6 C 0.8083(3) 0.6697(3) 0.7282(2) 0.0349(5) Uani 1 1 d . . . . .
C7 C 0.5058(3) 0.6073(3) 0.8762(2) 0.0376(6) Uani 1 1 d . . . . .
C8 C 0.6097(3) 0.3673(3) 0.8040(2) 0.0366(6) Uani 1 1 d . . . . .
C10 C 0.6854(3) 0.8659(3) 0.9605(3) 0.0444(6) Uani 1 1 d . . . . .
C11 C 0.6634(3) 0.6548(3) 0.6335(2) 0.0442(6) Uani 1 1 d . . . . .
H11A H 0.5576 0.6256 0.6437 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5587(3) 0.1880(3) 0.7670(3) 0.0473(7) Uani 1 1 d . . . . .
H13A H 0.4483 0.1547 0.7057 0.057 Uiso 1 1 calc R U . . .
H13B H 0.5496 0.1563 0.8390 0.057 Uiso 1 1 calc R U . . .
C14 C 0.9642(3) 0.7160(3) 0.7118(3) 0.0430(6) Uani 1 1 d . . . . .
H14A H 1.0630 0.7292 0.7751 0.052 Uiso 1 1 calc R U . . .
C15 C 0.9053(3) 0.3600(3) 0.8202(3) 0.0467(7) Uani 1 1 d . . . . .
C16 C 0.9741(4) 0.7426(3) 0.6018(3) 0.0491(7) Uani 1 1 d . . . . .
C17 C 0.6732(4) 0.6824(3) 0.5245(3) 0.0559(8) Uani 1 1 d . . . . .
H17A H 0.5742 0.6730 0.4623 0.067 Uiso 1 1 calc R U . . .
C18 C 0.8285(4) 0.7239(3) 0.5068(3) 0.0574(8) Uani 1 1 d . . . . .
H18A H 0.8354 0.7392 0.4320 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8656(4) 0.1786(3) 0.7929(4) 0.0662(9) Uani 1 1 d . . . . .
H19A H 0.9441 0.1292 0.7509 0.079 Uiso 1 1 calc R U . . .
H19B H 0.8830 0.1541 0.8709 0.079 Uiso 1 1 calc R U . . .
C20 C 0.6866(4) 0.1048(3) 0.7133(3) 0.0634(9) Uani 1 1 d . . . . .
H20A H 0.6741 0.1129 0.6303 0.076 Uiso 1 1 calc R U . . .
H20B H 0.6650 -0.0092 0.7065 0.076 Uiso 1 1 calc R U . . .
C24 C 1.1423(5) 0.7912(5) 0.5846(4) 0.0732(10) Uani 1 1 d . . . . .
O1 O 0.4745(2) 0.44312(19) 0.81856(16) 0.0432(5) Uani 1 1 d . . . . .
O2 O 1.0498(2) 0.4312(2) 0.8454(2) 0.0679(6) Uani 1 1 d . . . . .
N1 N 0.3685(3) 0.6539(3) 0.9055(2) 0.0505(6) Uani 1 1 d . . . . .
H1A H 0.3704 0.7541 0.9428 0.061 Uiso 1 1 calc R U . . .
H1B H 0.2779 0.5837 0.8873 0.061 Uiso 1 1 calc R U . . .
N2 N 0.7109(3) 1.0024(3) 1.0124(3) 0.0664(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
C8 C2 C15 119.2(2) . .
C8 C2 C4 121.6(2) . .
C15 C2 C4 119.1(2) . .
C5 C4 C2 108.05(18) . .
C5 C4 C6 113.0(2) . .
C2 C4 C6 109.95(19) . .
C5 C4 H4A 108.6 . .
C2 C4 H4A 108.6 . .
C6 C4 H4A 108.6 . .
C7 C5 C10 118.9(2) . .
C7 C5 C4 122.3(2) . .
C10 C5 C4 118.7(2) . .
C11 C6 C14 118.4(2) . .
C11 C6 C4 120.9(2) . .
C14 C6 C4 120.6(2) . .
N1 C7 C5 128.6(2) . .
N1 C7 O1 110.0(2) . .
C5 C7 O1 121.3(2) . .
C2 C8 O1 122.8(2) . .
C2 C8 C13 126.2(2) . .
O1 C8 C13 111.0(2) . .
N2 C10 C5 178.6(3) . .
C17 C11 C6 121.1(3) . .
C17 C11 H11A 119.5 . .
C6 C11 H11A 119.5 . .
C8 C13 C20 110.6(2) . .
C8 C13 H13A 109.5 . .
C20 C13 H13A 109.5 . .
C8 C13 H13B 109.5 . .
C20 C13 H13B 109.5 . .
H13A C13 H13B 108.1 . .
C16 C14 C6 120.4(3) . .
C16 C14 H14A 119.8 . .
C6 C14 H14A 119.8 . .
O2 C15 C2 121.1(2) . .
O2 C15 C19 121.6(3) . .
C2 C15 C19 117.3(2) . .
C18 C16 C14 120.6(3) . .
C18 C16 C24 119.4(3) . .
C14 C16 C24 120.1(3) . .
C11 C17 C18 120.4(3) . .
C11 C17 H17A 119.8 . .
C18 C17 H17A 119.8 . .
C17 C18 C16 119.0(3) . .
C17 C18 H18A 120.5 . .
C16 C18 H18A 120.5 . .
C20 C19 C15 113.2(3) . .
C20 C19 H19A 108.9 . .
C15 C19 H19A 108.9 . .
C20 C19 H19B 108.9 . .
C15 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C13 C20 C19 111.6(3) . .
C13 C20 H20A 109.3 . .
C19 C20 H20A 109.3 . .
C13 C20 H20B 109.3 . .
C19 C20 H20B 109.3 . .
H20A C20 H20B 108.0 . .
F3A C24 F1A 116.1(13) . .
F3A C24 F2A 112.7(12) . .
F1A C24 F2A 108.1(13) . .
F1 C24 F2 104.8(4) . .
F1 C24 F3 102.6(3) . .
F2 C24 F3 105.1(4) . .
F3A C24 C16 107.6(9) . .
F1A C24 C16 104.8(8) . .
F2A C24 C16 106.8(8) . .
F1 C24 C16 113.8(3) . .
F2 C24 C16 115.7(3) . .
F3 C24 C16 113.5(3) . .
C7 O1 C8 118.48(18) . .
C7 N1 H1A 120.0 . .
C7 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
F1 C24 1.300(4) .
F2 C24 1.311(5) .
F3 C24 1.338(5) .
F1A C24 1.283(17) .
F2A C24 1.284(16) .
F3A C24 1.230(18) .
C2 C8 1.332(3) .
C2 C15 1.464(4) .
C2 C4 1.519(3) .
C4 C5 1.510(3) .
C4 C6 1.532(3) .
C4 H4A 0.9800 .
C5 C7 1.353(3) .
C5 C10 1.411(3) .
C6 C11 1.384(3) .
C6 C14 1.385(3) .
C7 N1 1.332(3) .
C7 O1 1.373(3) .
C8 O1 1.375(3) .
C8 C13 1.490(3) .
C10 N2 1.150(3) .
C11 C17 1.375(4) .
C11 H11A 0.9300 .
C13 C20 1.505(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C16 1.383(4) .
C14 H14A 0.9300 .
C15 O2 1.216(3) .
C15 C19 1.512(4) .
C16 C18 1.382(4) .
C16 C24 1.488(4) .
C17 C18 1.378(4) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
C19 C20 1.509(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
