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#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/65/1516563.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_1516563
loop_
_publ_author_name
'Jin, Li-Mei'
'Lu, Hongjian'
'Cui, Yuan'
'Lizardi, Christopher L.'
'Arzua, Thiago N.'
'Wojtas, Lukasz'
'Cui, Xin'
'Zhang, X. Peter'
_publ_section_title
;
 Selective Radical Amination of Aldehydic C(sp(2))-H Bonds with Fluoroaryl
 Azides via Co(II)-Based Metalloradical Catalysis: Synthesis of
 N-Fluoroaryl Amides from Aldehydes under Neutral and Nonoxidative
 Conditions.
;
_journal_issue                   6
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              2422
_journal_page_last               2427
_journal_paper_doi               10.1039/C4SC00697F
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C14 H12 F N O2'
_chemical_formula_weight         245.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.520(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.7553(6)
_cell_length_b                   4.9562(2)
_cell_length_c                   13.1145(4)
_cell_measurement_temperature    100(2)
_cell_volume                     1148.71(7)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'APEX2 (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13588
_diffrn_reflns_theta_full        66.52
_diffrn_reflns_theta_max         66.52
_diffrn_reflns_theta_min         5.00
_diffrn_source                   'INCOATEC Imus micro-focus source'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.8860
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.5095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                1664
_reflns_number_total             2003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc00697f3.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1516563--1516564.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1516563
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.59192(5) 0.6389(2) 0.44330(7) 0.0288(3) Uani 1 1 d .
O1 O 0.94033(6) 0.9331(2) 0.09886(8) 0.0202(3) Uani 1 1 d .
O2 O 0.75618(6) 1.3920(2) 0.44886(8) 0.0205(3) Uani 1 1 d .
N1 N 0.71401(7) 0.9588(3) 0.45146(10) 0.0164(3) Uani 1 1 d .
C1 C 0.92045(10) 0.7281(3) 0.02432(12) 0.0217(4) Uani 1 1 d .
H1A H 0.9209 0.5517 0.0582 0.033 Uiso 1 1 calc R
H1B H 0.9571 0.7279 -0.0270 0.033 Uiso 1 1 calc R
H1C H 0.8697 0.7642 -0.0093 0.033 Uiso 1 1 calc R
C2 C 0.89300(8) 0.9692(3) 0.17419(11) 0.0163(3) Uani 1 1 d .
C3 C 0.82813(9) 0.8181(3) 0.18347(11) 0.0168(3) Uani 1 1 d .
H3 H 0.8140 0.6779 0.1360 0.020 Uiso 1 1 calc R
C4 C 0.78406(9) 0.8741(3) 0.26284(12) 0.0166(3) Uani 1 1 d .
H4 H 0.7401 0.7692 0.2700 0.020 Uiso 1 1 calc R
C5 C 0.80329(9) 1.0815(3) 0.33190(12) 0.0153(3) Uani 1 1 d .
C6 C 0.75618(8) 1.1601(3) 0.41542(11) 0.0151(3) Uani 1 1 d .
C7 C 0.66375(8) 0.9826(3) 0.52886(12) 0.0154(3) Uani 1 1 d .
C8 C 0.60222(9) 0.8105(3) 0.52425(12) 0.0191(4) Uani 1 1 d .
C9 C 0.55168(9) 0.8066(3) 0.59739(13) 0.0240(4) Uani 1 1 d .
H9 H 0.5102 0.6845 0.5921 0.029 Uiso 1 1 calc R
C10 C 0.56252(10) 0.9844(3) 0.67887(13) 0.0231(4) Uani 1 1 d .
H10 H 0.5284 0.9852 0.7304 0.028 Uiso 1 1 calc R
C11 C 0.86918(9) 1.2297(3) 0.32170(12) 0.0184(3) Uani 1 1 d .
H11 H 0.8832 1.3711 0.3686 0.022 Uiso 1 1 calc R
C12 C 0.91395(9) 1.1727(3) 0.24416(12) 0.0187(4) Uani 1 1 d .
H12 H 0.9591 1.2723 0.2386 0.022 Uiso 1 1 calc R
C13 C 0.67389(9) 1.1609(3) 0.61081(12) 0.0189(4) Uani 1 1 d .
H13 H 0.7154 1.2825 0.6161 0.023 Uiso 1 1 calc R
C14 C 0.62301(9) 1.1606(3) 0.68522(12) 0.0214(4) Uani 1 1 d .
H14 H 0.6300 1.2832 0.7410 0.026 Uiso 1 1 calc R
H1 H 0.7208(10) 0.793(4) 0.4284(14) 0.023(5) Uiso 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 0.0181 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'
O O 0.0492 0.0322 '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
C2 O1 C1 117.24(12)
C6 N1 C7 126.35(13)
C6 N1 H1 117.5(12)
C7 N1 H1 115.9(12)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C3 124.38(14)
O1 C2 C12 115.29(13)
C3 C2 C12 120.33(14)
C2 C3 C4 119.31(14)
C2 C3 H3 120.3
C4 C3 H3 120.3
C3 C4 C5 121.01(15)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C11 118.75(14)
C4 C5 C6 123.44(14)
C11 C5 C6 117.79(14)
O2 C6 N1 122.89(14)
O2 C6 C5 121.65(13)
N1 C6 C5 115.46(13)
C8 C7 C13 117.98(14)
C8 C7 N1 117.75(14)
C13 C7 N1 124.23(14)
F1 C8 C9 119.22(14)
F1 C8 C7 117.82(14)
C9 C8 C7 122.96(15)
C8 C9 C10 118.54(15)
C8 C9 H9 120.7
C10 C9 H9 120.7
C14 C10 C9 119.93(15)
C14 C10 H10 120.0
C9 C10 H10 120.0
C12 C11 C5 120.65(14)
C12 C11 H11 119.7
C5 C11 H11 119.7
C11 C12 C2 119.93(14)
C11 C12 H12 120.0
C2 C12 H12 120.0
C7 C13 C14 119.81(15)
C7 C13 H13 120.1
C14 C13 H13 120.1
C10 C14 C13 120.78(15)
C10 C14 H14 119.6
C13 C14 H14 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C8 1.3588(18)
O1 C2 1.3690(18)
O1 C1 1.4304(19)
O2 C6 1.2300(18)
N1 C6 1.359(2)
N1 C7 1.419(2)
N1 H1 0.89(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.389(2)
C2 C12 1.390(2)
C3 C4 1.389(2)
C3 H3 0.9500
C4 C5 1.391(2)
C4 H4 0.9500
C5 C11 1.399(2)
C5 C6 1.492(2)
C7 C8 1.383(2)
C7 C13 1.389(2)
C8 C9 1.375(2)
C9 C10 1.384(2)
C9 H9 0.9500
C10 C14 1.381(2)
C10 H10 0.9500
C11 C12 1.379(2)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.392(2)
C13 H13 0.9500
C14 H14 0.9500
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
C1 O1 C2 C3 1.0(2)
C1 O1 C2 C12 -179.21(13)
O1 C2 C3 C4 -179.59(13)
C12 C2 C3 C4 0.6(2)
C2 C3 C4 C5 1.0(2)
C3 C4 C5 C11 -1.6(2)
C3 C4 C5 C6 176.84(14)
C7 N1 C6 O2 1.4(2)
C7 N1 C6 C5 -178.74(13)
C4 C5 C6 O2 -151.66(15)
C11 C5 C6 O2 26.8(2)
C4 C5 C6 N1 28.5(2)
C11 C5 C6 N1 -153.07(14)
C6 N1 C7 C8 150.60(15)
C6 N1 C7 C13 -31.8(2)
C13 C7 C8 F1 179.15(14)
N1 C7 C8 F1 -3.1(2)
C13 C7 C8 C9 -0.8(2)
N1 C7 C8 C9 176.98(15)
F1 C8 C9 C10 -179.37(15)
C7 C8 C9 C10 0.5(3)
C8 C9 C10 C14 0.1(3)
C4 C5 C11 C12 0.5(2)
C6 C5 C11 C12 -178.01(14)
C5 C11 C12 C2 1.1(2)
O1 C2 C12 C11 178.51(14)
C3 C2 C12 C11 -1.6(2)
C8 C7 C13 C14 0.4(2)
N1 C7 C13 C14 -177.22(14)
C9 C10 C14 C13 -0.5(3)
C7 C13 C14 C10 0.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 796046
