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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554577.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_1554577
loop_
_publ_author_name
'Chen, Mu-Wang'
'Deng, Zhihong'
'Yang, Qin'
'Huang, Jian'
'Peng, Yiyuan'
_publ_section_title
;
 Enantioselective synthesis of trifluoromethylated dihydroquinoxalinones
 via palladium-catalyzed hydrogenation
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              746
_journal_paper_doi               10.1039/C8QO01361F
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C9 H9 F3 N2'
_chemical_formula_weight         202.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-11-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.17(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.799(3)
_cell_length_b                   7.486(4)
_cell_length_c                   10.479(6)
_cell_measurement_reflns_used    1544
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.293
_cell_measurement_theta_min      8.703
_cell_volume                     441.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.910
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.1383
_diffrn_reflns_Laue_measured_fraction_full 0.910
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3146
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.432
_diffrn_reflns_theta_min         4.351
_exptl_absorpt_coefficient_mu    1.204
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   -0.3(8)
_refine_ls_extinction_coef       0.4(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.398
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1387
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.397
_refine_ls_R_factor_all          0.2357
_refine_ls_R_factor_gt           0.0964
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2635
_refine_ls_wR_factor_ref         0.3757
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                807
_reflns_number_total             1387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01361f2.cif
_cod_data_source_block           d8v18757
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554577
_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. 
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.1008(14) 0.6951(10) 0.4666(13) 0.073(3) Uani 1 1 d . .
C2 C 0.0931(16) 0.6560(12) 0.5981(13) 0.072(3) Uani 1 1 d . .
H2 H -0.0407 0.6028 0.6157 0.086 Uiso 1 1 calc R U
C3 C 0.2865(17) 0.6978(13) 0.6994(15) 0.088(3) Uani 1 1 d . .
H3 H 0.2821 0.6732 0.7857 0.105 Uiso 1 1 calc R U
C4 C 0.4842(15) 0.7749(14) 0.6746(13) 0.082(3) Uani 1 1 d . .
H4 H 0.6128 0.8024 0.7442 0.098 Uiso 1 1 calc R U
C5 C 0.4955(14) 0.8129(12) 0.5467(12) 0.076(3) Uani 1 1 d . .
H5 H 0.6309 0.8655 0.5307 0.091 Uiso 1 1 calc R U
C6 C 0.3059(13) 0.7723(11) 0.4441(10) 0.066(3) Uani 1 1 d . .
C7 C -0.0385(15) 0.6331(14) 0.2345(14) 0.084(4) Uani 1 1 d . .
H7A H -0.1837 0.6246 0.1653 0.101 Uiso 1 1 calc R U
H7B H 0.0482 0.5218 0.2374 0.101 Uiso 1 1 calc R U
C8 C 0.1131(15) 0.7884(13) 0.2066(12) 0.081(3) Uani 1 1 d . .
H8 H 0.0212 0.8994 0.1996 0.097 Uiso 1 1 calc R U
C9 C 0.1867(19) 0.7572(15) 0.0797(14) 0.089(3) Uani 1 1 d . .
F1 F 0.3294(16) 0.8915(12) 0.0578(7) 0.118(3) Uani 1 1 d . .
F2 F 0.0033(16) 0.7558(13) -0.0221(9) 0.127(3) Uani 1 1 d . .
F3 F 0.3101(13) 0.6104(11) 0.0797(8) 0.114(3) Uani 1 1 d . .
N1 N -0.0952(13) 0.6645(10) 0.3604(10) 0.078(3) Uani 1 1 d . .
H1 H -0.2139 0.6235 0.3739 0.094 Uiso 1 1 d R U
N2 N 0.3235(13) 0.8033(13) 0.3145(10) 0.083(3) Uani 1 1 d . .
H2A H 0.3951 0.9027 0.3096 0.099 Uiso 1 1 d R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C6 C1 N1 119.6(11)
C6 C1 C2 118.7(9)
N1 C1 C2 121.6(9)
C3 C2 C1 119.2(9)
C3 C2 H2 120.4
C1 C2 H2 120.4
C4 C3 C2 120.9(14)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 120.8(10)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 119.6(8)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 120.9(10)
C5 C6 N2 119.2(8)
C1 C6 N2 119.9(8)
N1 C7 C8 108.6(9)
N1 C7 H7A 110.0
C8 C7 H7A 110.0
N1 C7 H7B 110.0
C8 C7 H7B 110.0
H7A C7 H7B 108.3
N2 C8 C9 109.4(8)
N2 C8 C7 108.8(8)
C9 C8 C7 110.5(9)
N2 C8 H8 109.3
C9 C8 H8 109.3
C7 C8 H8 109.3
F2 C9 F3 109.1(11)
F2 C9 F1 106.0(11)
F3 C9 F1 105.4(7)
F2 C9 C8 111.7(8)
F3 C9 C8 113.6(11)
F1 C9 C8 110.5(10)
C1 N1 C7 115.2(8)
C1 N1 H1 119.3
C7 N1 H1 119.7
C6 N2 C8 119.6(7)
C6 N2 H2A 110.5
C8 N2 H2A 110.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.393(13)
C1 N1 1.401(13)
C1 C2 1.421(17)
C2 C3 1.378(17)
C2 H2 0.9300
C3 C4 1.364(16)
C3 H3 0.9300
C4 C5 1.387(17)
C4 H4 0.9300
C5 C6 1.371(13)
C5 H5 0.9300
C6 N2 1.406(13)
C7 N1 1.454(17)
C7 C8 1.528(14)
C7 H7A 0.9700
C7 H7B 0.9700
C8 N2 1.450(13)
C8 C9 1.511(18)
C8 H8 0.9800
C9 F2 1.309(15)
C9 F3 1.312(14)
C9 F1 1.357(14)
N1 H1 0.7977
N2 H2A 0.8597
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
C6 C1 C2 C3 1.0(14)
N1 C1 C2 C3 -176.4(7)
C1 C2 C3 C4 -0.4(15)
C2 C3 C4 C5 -0.1(16)
C3 C4 C5 C6 -0.1(16)
C4 C5 C6 C1 0.7(15)
C4 C5 C6 N2 -177.0(8)
N1 C1 C6 C5 176.3(8)
C2 C1 C6 C5 -1.1(14)
N1 C1 C6 N2 -6.0(13)
C2 C1 C6 N2 176.5(8)
N1 C7 C8 N2 57.0(10)
N1 C7 C8 C9 177.2(8)
N2 C8 C9 F2 -175.4(8)
C7 C8 C9 F2 64.8(12)
N2 C8 C9 F3 60.6(12)
C7 C8 C9 F3 -59.2(11)
N2 C8 C9 F1 -57.6(11)
C7 C8 C9 F1 -177.5(8)
C6 C1 N1 C7 28.8(12)
C2 C1 N1 C7 -153.8(9)
C8 C7 N1 C1 -54.2(10)
C5 C6 N2 C8 -170.1(8)
C1 C6 N2 C8 12.2(13)
C9 C8 N2 C6 -158.6(9)
C7 C8 N2 C6 -37.7(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 154640225
