#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:32:10 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284936 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/24/7062473.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_7062473
loop_
_publ_author_name
'Zhao, Wei'
'Xuan, Liangming'
'Liu, Yang'
'Yin, Jiayi'
'Wang, Haifeng'
'Yan, Qiongjiao'
'Wang, Wei'
'Huang, Jin'
'Chen, Fener'
_publ_section_title
;
 Photoinduced tandem radical cyclization/heteroarylation of
 N-allylbromodifluoroacetamides with quinoxalin-2(1H)-ones or coumarins
 under metal- and photocatalyst-free conditions
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10744
_journal_page_last               10750
_journal_paper_doi               10.1039/D3NJ01329D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C17 H17 F2 N3 O2'
_chemical_formula_weight         333.33
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-11-12 deposited with the CCDC.	2023-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                108.912(7)
_cell_angle_beta                 101.164(6)
_cell_angle_gamma                96.073(6)
_cell_formula_units_Z            2
_cell_length_a                   7.850(2)
_cell_length_b                   10.152(3)
_cell_length_c                   10.835(3)
_cell_measurement_reflns_used    3820
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.28
_cell_measurement_theta_min      2.39
_cell_volume                     788.1(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20998
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.393
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       Block
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-Hexane/EtOAc'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0690
_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)+(0.1323P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.2173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1531
_reflns_number_total             2755
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj01329d2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7062473.cif.'
_cod_database_code               7062473
_shelx_shelxl_version_number     2014/7
_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   0.978
_shelx_estimated_absorpt_t_max   0.978
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
C1 C -0.2282(5) 0.3259(4) 0.2984(4) 0.0666(11) Uani 1 1 d . . . . .
H1A H -0.1245 0.3236 0.3625 0.080 Uiso 1 1 calc R U . . .
H1B H -0.3272 0.3523 0.3364 0.080 Uiso 1 1 calc R U . . .
C2 C -0.2674(5) 0.2211(4) 0.1607(4) 0.0661(11) Uani 1 1 d . . . . .
H2A H -0.3904 0.1834 0.1143 0.079 Uiso 1 1 calc R U . . .
H2B H -0.1877 0.1547 0.1404 0.079 Uiso 1 1 calc R U . . .
C3 C -0.2005(4) 0.3718(4) 0.1864(4) 0.0548(10) Uani 1 1 d . . . . .
H3 H -0.2870 0.4246 0.1562 0.066 Uiso 1 1 calc R U . . .
C4 C 0.0473(4) 0.3662(4) 0.0775(4) 0.0485(9) Uani 1 1 d . . . . .
C5 C 0.2396(4) 0.4331(4) 0.1220(3) 0.0465(9) Uani 1 1 d . . . . .
C6 C 0.2603(4) 0.5617(3) 0.2456(3) 0.0442(9) Uani 1 1 d . . . . .
H6 H 0.2448 0.6429 0.2172 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1005(4) 0.5259(4) 0.2987(3) 0.0512(9) Uani 1 1 d . . . . .
H7A H 0.1349 0.4915 0.3720 0.061 Uiso 1 1 calc R U . . .
H7B H 0.0467 0.6083 0.3302 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4385(4) 0.5971(3) 0.3448(3) 0.0480(9) Uani 1 1 d . . . . .
H8A H 0.4507 0.5203 0.3787 0.058 Uiso 1 1 calc R U . . .
H8B H 0.5303 0.6028 0.2974 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4672(4) 0.7319(3) 0.4612(3) 0.0428(8) Uani 1 1 d . . . . .
C10 C 0.6400(4) 0.7707(4) 0.5584(3) 0.0475(9) Uani 1 1 d . . . . .
C11 C 0.8373(5) 0.9372(4) 0.7639(4) 0.0778(13) Uani 1 1 d . . . . .
H11A H 0.9171 0.8770 0.7305 0.117 Uiso 1 1 calc R U . . .
H11B H 0.8225 0.9302 0.8476 0.117 Uiso 1 1 calc R U . . .
H11C H 0.8846 1.0335 0.7777 0.117 Uiso 1 1 calc R U . . .
C12 C 0.5326(2) 0.9721(2) 0.6838(2) 0.0434(9) Uani 1 1 d G . . . .
C13 C 0.3738(3) 0.92736(19) 0.58646(18) 0.0436(8) Uani 1 1 d G . . . .
C14 C 0.2372(2) 1.0031(2) 0.6024(2) 0.0607(10) Uani 1 1 d G . . . .
H14 H 0.1310 0.9732 0.5373 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2594(3) 1.1237(2) 0.7157(3) 0.0697(12) Uani 1 1 d G . . . .
H15 H 0.1680 1.1744 0.7263 0.084 Uiso 1 1 calc R U . . .
C16 C 0.4181(3) 1.1684(2) 0.8130(2) 0.0691(11) Uani 1 1 d G . . . .
H16 H 0.4329 1.2490 0.8887 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5548(3) 1.0926(2) 0.79703(19) 0.0573(10) Uani 1 1 d G . . . .
H17 H 0.6610 1.1225 0.8621 0.069 Uiso 1 1 calc R U . . .
F1 F 0.3351(2) 0.3348(2) 0.1469(2) 0.0629(7) Uani 1 1 d . . . . .
F2 F 0.2988(3) 0.4631(2) 0.0230(2) 0.0695(7) Uani 1 1 d . . . . .
N1 N -0.0211(3) 0.4151(3) 0.1828(3) 0.0456(7) Uani 1 1 d . . . . .
N2 N 0.3436(3) 0.8054(3) 0.4738(3) 0.0443(7) Uani 1 1 d . . . . .
N3 N 0.6649(3) 0.8926(3) 0.6655(3) 0.0475(8) Uani 1 1 d . . . . .
O1 O -0.0276(3) 0.2804(3) -0.0353(3) 0.0722(8) Uani 1 1 d . . . . .
O2 O 0.7531(3) 0.6965(3) 0.5417(3) 0.0685(8) 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
_geom_angle_publ_flag
C2 C1 C3 60.1(3) . . ?
C2 C1 H1A 117.8 . . ?
C3 C1 H1A 117.8 . . ?
C2 C1 H1B 117.8 . . ?
C3 C1 H1B 117.8 . . ?
H1A C1 H1B 114.9 . . ?
C1 C2 C3 60.0(2) . . ?
C1 C2 H2A 117.8 . . ?
C3 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
C3 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
N1 C3 C1 117.7(3) . . ?
N1 C3 C2 119.7(3) . . ?
C1 C3 C2 59.8(3) . . ?
N1 C3 H3 116.0 . . ?
C1 C3 H3 116.0 . . ?
C2 C3 H3 116.0 . . ?
O1 C4 N1 128.0(3) . . ?
O1 C4 C5 125.2(3) . . ?
N1 C4 C5 106.7(3) . . ?
F2 C5 F1 104.4(3) . . ?
F2 C5 C6 113.1(3) . . ?
F1 C5 C6 112.5(3) . . ?
F2 C5 C4 112.1(3) . . ?
F1 C5 C4 108.0(3) . . ?
C6 C5 C4 106.8(3) . . ?
C5 C6 C8 114.1(3) . . ?
C5 C6 C7 102.3(3) . . ?
C8 C6 C7 115.4(3) . . ?
C5 C6 H6 108.2 . . ?
C8 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
N1 C7 C6 104.4(2) . . ?
N1 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C6 114.6(3) . . ?
C9 C8 H8A 108.6 . . ?
C6 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C6 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 123.9(3) . . ?
N2 C9 C8 120.1(3) . . ?
C10 C9 C8 116.0(3) . . ?
O2 C10 N3 123.0(3) . . ?
O2 C10 C9 121.2(3) . . ?
N3 C10 C9 115.9(3) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 118.38(17) . . ?
N3 C12 C17 121.61(17) . . ?
C13 C12 C17 120.0 . . ?
N2 C13 C14 117.88(16) . . ?
N2 C13 C12 122.09(16) . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C4 N1 C3 125.2(3) . . ?
C4 N1 C7 114.1(3) . . ?
C3 N1 C7 120.7(3) . . ?
C9 N2 C13 118.1(2) . . ?
C10 N3 C12 121.6(2) . . ?
C10 N3 C11 117.8(3) . . ?
C12 N3 C11 120.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.476(5) . ?
C1 C3 1.478(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.480(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.442(4) . ?
C3 H3 0.9800 . ?
C4 O1 1.233(4) . ?
C4 N1 1.327(4) . ?
C4 C5 1.504(5) . ?
C5 F2 1.355(4) . ?
C5 F1 1.373(4) . ?
C5 C6 1.503(5) . ?
C6 C8 1.517(4) . ?
C6 C7 1.535(4) . ?
C6 H6 0.9800 . ?
C7 N1 1.465(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.490(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.286(4) . ?
C9 C10 1.473(4) . ?
C10 O2 1.226(4) . ?
C10 N3 1.359(4) . ?
C11 N3 1.474(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N3 1.386(3) . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 N2 1.388(3) . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 H17 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
_geom_torsion_publ_flag
C2 C1 C3 N1 -110.0(4) . . . . ?
C1 C2 C3 N1 106.7(4) . . . . ?
O1 C4 C5 F2 37.4(5) . . . . ?
N1 C4 C5 F2 -143.8(3) . . . . ?
O1 C4 C5 F1 -77.0(4) . . . . ?
N1 C4 C5 F1 101.7(3) . . . . ?
O1 C4 C5 C6 161.8(3) . . . . ?
N1 C4 C5 C6 -19.5(4) . . . . ?
F2 C5 C6 C8 -87.2(4) . . . . ?
F1 C5 C6 C8 30.7(4) . . . . ?
C4 C5 C6 C8 149.0(3) . . . . ?
F2 C5 C6 C7 147.4(3) . . . . ?
F1 C5 C6 C7 -94.6(3) . . . . ?
C4 C5 C6 C7 23.6(3) . . . . ?
C5 C6 C7 N1 -19.6(3) . . . . ?
C8 C6 C7 N1 -144.0(3) . . . . ?
C5 C6 C8 C9 174.4(3) . . . . ?
C7 C6 C8 C9 -67.5(4) . . . . ?
C6 C8 C9 N2 2.3(5) . . . . ?
C6 C8 C9 C10 -179.1(3) . . . . ?
N2 C9 C10 O2 179.8(3) . . . . ?
C8 C9 C10 O2 1.2(5) . . . . ?
N2 C9 C10 N3 -0.6(5) . . . . ?
C8 C9 C10 N3 -179.1(3) . . . . ?
N3 C12 C13 N2 1.0(3) . . . . ?
C17 C12 C13 N2 -178.0(2) . . . . ?
N3 C12 C13 C14 179.0(2) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
N2 C13 C14 C15 178.1(2) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
N3 C12 C17 C16 -179.0(2) . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
O1 C4 N1 C3 2.5(6) . . . . ?
C5 C4 N1 C3 -176.2(3) . . . . ?
O1 C4 N1 C7 -174.8(3) . . . . ?
C5 C4 N1 C7 6.4(4) . . . . ?
C1 C3 N1 C4 128.3(4) . . . . ?
C2 C3 N1 C4 59.0(5) . . . . ?
C1 C3 N1 C7 -54.6(4) . . . . ?
C2 C3 N1 C7 -123.8(4) . . . . ?
C6 C7 N1 C4 8.7(4) . . . . ?
C6 C7 N1 C3 -168.7(3) . . . . ?
C10 C9 N2 C13 -0.9(5) . . . . ?
C8 C9 N2 C13 177.6(3) . . . . ?
C14 C13 N2 C9 -177.4(2) . . . . ?
C12 C13 N2 C9 0.7(3) . . . . ?
O2 C10 N3 C12 -178.0(3) . . . . ?
C9 C10 N3 C12 2.3(5) . . . . ?
O2 C10 N3 C11 0.9(5) . . . . ?
C9 C10 N3 C11 -178.7(3) . . . . ?
C13 C12 N3 C10 -2.6(4) . . . . ?
C17 C12 N3 C10 176.4(2) . . . . ?
C13 C12 N3 C11 178.5(3) . . . . ?
C17 C12 N3 C11 -2.5(4) . . . . ?
