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#$Date: 2023-10-05 11:21:40 +0300 (Thu, 05 Oct 2023) $
#$Revision: 286673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107582.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_8107582
loop_
_publ_author_name
'Pu, Xuewei'
'Meng, Fanjie'
'Zhang, Shaoliang'
_publ_section_title
;
 The crystal structure of
 [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              857
_journal_page_last               859
_journal_paper_doi               10.1515/ncrs-2023-0240
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C16 H12 F3 N O'
_chemical_formula_sum            'C16 H12 F3 N O'
_chemical_formula_weight         291.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9928(6)
_cell_length_b                   8.9764(8)
_cell_length_c                   21.216(2)
_cell_measurement_reflns_used    5991
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.012
_cell_measurement_theta_min      2.408
_cell_volume                     1331.7(2)
_computing_cell_refinement       'SMART [1]'
_computing_data_collection       'SMART [1]'
_computing_data_reduction        'SMART [1]'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)[2]'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)[2]'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)[2]'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)[2]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5991
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.464
_diffrn_source                   'fine-focus sealed'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.310
_exptl_transmission_factor_max   0.963
_exptl_transmission_factor_min   0.954
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       0.061(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0818P)²+0.1094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                1800
_reflns_number_total             2329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0240_suppl_001.cif
_cod_data_source_block           g
_cod_database_code               8107582
_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   0.954
_shelx_estimated_absorpt_t_max   0.964
_shelxl_version_number           2014-3
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.5240(11) 0.4950(7) 0.2014(4) 0.100(2) Uani 0.611(5) 1 d . U P A 1
F2 F 0.4364(13) 0.5906(14) 0.2861(3) 0.120(3) Uani 0.611(5) 1 d . U P A 1
F3 F 0.6505(11) 0.6895(9) 0.2334(6) 0.117(3) Uani 0.611(5) 1 d . U P A 1
F1' F 0.4046(19) 0.5099(11) 0.2596(8) 0.100(2) Uani 0.389(5) 1 d . . P A 2
F2' F 0.625(2) 0.585(2) 0.2007(5) 0.120(3) Uani 0.389(5) 1 d . . P A 2
F3' F 0.5472(18) 0.6953(15) 0.2792(9) 0.117(3) Uani 0.389(5) 1 d . . P A 2
N1 N -0.0638(4) 0.9572(4) 0.09622(16) 0.0388(9) Uani 1 1 d . . . . .
O1 O -0.1864(4) 0.7488(4) 0.05416(18) 0.0568(9) Uani 1 1 d . . . . .
C1 C -0.1877(6) 0.8832(5) 0.0578(2) 0.0434(11) Uani 1 1 d . . . . .
C2 C -0.3150(7) 0.9794(6) 0.0192(2) 0.0570(13) Uani 1 1 d . . . . .
H2A H -0.4252 0.9220 0.0058 0.068 Uiso 1 1 calc R U . . .
H2B H -0.2468 1.0113 -0.0183 0.068 Uiso 1 1 calc R U . . .
C3 C -0.3814(6) 1.1136(6) 0.0548(3) 0.0596(14) Uani 1 1 d . . . . .
H3A H -0.4534 1.1781 0.0268 0.071 Uiso 1 1 calc R U . . .
H3B H -0.4655 1.0827 0.0887 0.071 Uiso 1 1 calc R U . . .
C4 C -0.2166(5) 1.1969(6) 0.0813(2) 0.0468(11) Uani 1 1 d . . . . .
C5 C -0.0591(5) 1.1130(5) 0.1010(2) 0.0374(10) Uani 1 1 d . . . . .
C6 C 0.0974(5) 1.1859(5) 0.1264(2) 0.0459(11) Uani 1 1 d . . . . .
H6 H 0.2034 1.1314 0.1394 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0973(7) 1.3366(6) 0.1326(2) 0.0570(13) Uani 1 1 d . . . . .
H7 H 0.2028 1.3843 0.1500 0.068 Uiso 1 1 calc R U . . .
C8 C -0.0563(8) 1.4181(6) 0.1134(3) 0.0605(14) Uani 1 1 d . . . . .
H8 H -0.0567 1.5211 0.1180 0.073 Uiso 1 1 calc R U . . .
C9 C -0.2088(7) 1.3475(6) 0.0874(2) 0.0576(14) Uani 1 1 d . . . . .
H9 H -0.3116 1.4042 0.0734 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0735(5) 0.8710(4) 0.1303(2) 0.0384(10) Uani 1 1 d . . . . .
C11 C 0.2299(5) 0.8155(6) 0.0997(2) 0.0456(11) Uani 1 1 d . . . . .
H11 H 0.2465 0.8334 0.0569 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3621(5) 0.7336(5) 0.1323(2) 0.0471(12) Uani 1 1 d . . . . .
H12 H 0.4674 0.6939 0.1114 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3396(5) 0.7101(4) 0.1952(2) 0.0410(10) Uani 1 1 d . . . . .
C14 C 0.1831(6) 0.7657(5) 0.2256(2) 0.0481(11) Uani 1 1 d . . . . .
H14 H 0.1670 0.7481 0.2685 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0498(6) 0.8470(5) 0.1934(2) 0.0459(11) Uani 1 1 d . . . . .
H15 H -0.0561 0.8857 0.2143 0.055 Uiso 1 1 calc R U . . .
C16 C 0.4824(7) 0.6224(6) 0.2297(3) 0.0571(13) Uani 1 1 d . U . . .
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 N1 C5 123.0(3) . .
C1 N1 C10 117.8(3) . .
C5 N1 C10 119.1(3) . .
O1 C1 N1 121.3(4) . .
O1 C1 C2 123.3(4) . .
N1 C1 C2 115.3(4) . .
C1 C2 C3 112.1(4) . .
C1 C2 H2A 109.2 . .
C3 C2 H2A 109.2 . .
C1 C2 H2B 109.2 . .
C3 C2 H2B 109.2 . .
H2A C2 H2B 107.9 . .
C4 C3 C2 110.8(4) . .
C4 C3 H3A 109.5 . .
C2 C3 H3A 109.5 . .
C4 C3 H3B 109.5 . .
C2 C3 H3B 109.5 . .
H3A C3 H3B 108.1 . .
C9 C4 C5 118.4(4) . .
C9 C4 C3 124.7(4) . .
C5 C4 C3 116.9(4) . .
C6 C5 C4 119.0(4) . .
C6 C5 N1 121.2(3) . .
C4 C5 N1 119.8(3) . .
C7 C6 C5 120.5(4) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C8 120.5(4) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C9 C8 C7 119.3(4) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C8 C9 C4 122.3(4) . .
C8 C9 H9 118.8 . .
C4 C9 H9 118.8 . .
C15 C10 C11 120.3(4) . .
C15 C10 N1 120.0(3) . .
C11 C10 N1 119.7(4) . .
C10 C11 C12 119.8(4) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C13 C12 C11 120.0(4) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C14 120.0(4) . .
C12 C13 C16 119.6(4) . .
C14 C13 C16 120.3(5) . .
C13 C14 C15 120.3(4) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C10 C15 C14 119.5(4) . .
C10 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
F2' C16 F1' 111.7(11) . .
F2 C16 F3 105.8(7) . .
F2 C16 F1 106.7(7) . .
F3 C16 F1 103.0(6) . .
F2' C16 F3' 105.1(10) . .
F1' C16 F3' 98.0(9) . .
F2' C16 C13 116.9(7) . .
F2 C16 C13 114.7(5) . .
F1' C16 C13 111.9(6) . .
F3 C16 C13 113.0(5) . .
F1 C16 C13 112.7(5) . .
F3' C16 C13 111.5(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C16 1.325(8) .
F2 C16 1.270(8) .
F3 C16 1.323(9) .
F1' C16 1.311(14) .
F2' C16 1.220(11) .
F3' C16 1.317(16) .
N1 C1 1.362(5) .
N1 C5 1.402(5) .
N1 C10 1.429(5) .
O1 C1 1.209(5) .
C1 C2 1.486(6) .
C2 C3 1.495(7) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.485(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C9 1.359(7) .
C4 C5 1.399(5) .
C5 C6 1.385(6) .
C6 C7 1.359(7) .
C6 H6 0.9300 .
C7 C8 1.362(7) .
C7 H7 0.9300 .
C8 C9 1.357(7) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C15 1.366(6) .
C10 C11 1.366(5) .
C11 C12 1.369(6) .
C11 H11 0.9300 .
C12 C13 1.361(6) .
C12 H12 0.9300 .
C13 C14 1.366(6) .
C13 C16 1.467(6) .
C14 C15 1.367(6) .
C14 H14 0.9300 .
C15 H15 0.9300 .
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
C5 N1 C1 O1 179.0(4) . . . .
C10 N1 C1 O1 2.5(6) . . . .
C5 N1 C1 C2 1.9(6) . . . .
C10 N1 C1 C2 -174.6(4) . . . .
O1 C1 C2 C3 144.7(5) . . . .
N1 C1 C2 C3 -38.3(6) . . . .
C1 C2 C3 C4 53.6(6) . . . .
C2 C3 C4 C9 145.7(5) . . . .
C2 C3 C4 C5 -34.2(6) . . . .
C9 C4 C5 C6 0.6(7) . . . .
C3 C4 C5 C6 -179.5(4) . . . .
C9 C4 C5 N1 179.0(4) . . . .
C3 C4 C5 N1 -1.1(7) . . . .
C1 N1 C5 C6 -162.5(4) . . . .
C10 N1 C5 C6 14.0(6) . . . .
C1 N1 C5 C4 19.2(6) . . . .
C10 N1 C5 C4 -164.4(4) . . . .
C4 C5 C6 C7 0.5(7) . . . .
N1 C5 C6 C7 -177.9(4) . . . .
C5 C6 C7 C8 -0.5(7) . . . .
C6 C7 C8 C9 -0.7(8) . . . .
C7 C8 C9 C4 1.8(8) . . . .
C5 C4 C9 C8 -1.7(7) . . . .
C3 C4 C9 C8 178.4(5) . . . .
C1 N1 C10 C15 -105.1(5) . . . .
C5 N1 C10 C15 78.3(5) . . . .
C1 N1 C10 C11 76.2(5) . . . .
C5 N1 C10 C11 -100.5(5) . . . .
C15 C10 C11 C12 1.0(7) . . . .
N1 C10 C11 C12 179.7(4) . . . .
C10 C11 C12 C13 -1.4(7) . . . .
C11 C12 C13 C14 1.4(7) . . . .
C11 C12 C13 C16 -179.8(4) . . . .
C12 C13 C14 C15 -1.0(6) . . . .
C16 C13 C14 C15 -179.8(4) . . . .
C11 C10 C15 C14 -0.6(6) . . . .
N1 C10 C15 C14 -179.4(4) . . . .
C13 C14 C15 C10 0.7(7) . . . .
C12 C13 C16 F2' 6.0(15) . . . .
C14 C13 C16 F2' -175.2(14) . . . .
C12 C13 C16 F2 -171.3(9) . . . .
C14 C13 C16 F2 7.5(10) . . . .
C12 C13 C16 F1' -124.6(9) . . . .
C14 C13 C16 F1' 54.2(9) . . . .
C12 C13 C16 F3 67.3(9) . . . .
C14 C13 C16 F3 -113.9(8) . . . .
C12 C13 C16 F1 -48.9(7) . . . .
C14 C13 C16 F1 129.9(6) . . . .
C12 C13 C16 F3' 126.8(10) . . . .
C14 C13 C16 F3' -54.4(10) . . . .
