#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/73/7157313.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_7157313
loop_
_publ_author_name
'Liao, Chunshu'
'Li, Jianrong'
'Chen, Xiaoqiong'
'Lu, Jingjun'
'Liu, Qiang'
'Chen, Lu'
'Huang, Yubing'
'Li, Yibiao'
_publ_section_title
;
 Selective synthesis of pyridyl pyridones and oxydipyridines by
 transition-metal-free hydroxylation and arylation of 2-fluoropyridine
 derivatives.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1185
_journal_page_last               1193
_journal_paper_doi               10.1039/c9ob02661d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C12 H4 F8 N2 O'
_chemical_formula_sum            'C12 H4 F8 N2 O'
_chemical_formula_weight         344.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-25 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.220(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.0204(10)
_cell_length_b                   7.9073(5)
_cell_length_c                   22.6326(16)
_cell_measurement_reflns_used    2181
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.3370
_cell_measurement_theta_min      2.9700
_cell_volume                     2442.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  65.00   1.00    4.50    --  -11.59  19.00-180.00  117
  2  ω    -81.00 -31.00   1.00    4.50    --  -11.59 -57.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0273951000
_diffrn_orient_matrix_UB_12      -0.0469103000
_diffrn_orient_matrix_UB_13      0.0171398000
_diffrn_orient_matrix_UB_21      0.0348456000
_diffrn_orient_matrix_UB_22      0.0204567000
_diffrn_orient_matrix_UB_23      0.0270649000
_diffrn_orient_matrix_UB_31      -0.0271200000
_diffrn_orient_matrix_UB_32      0.0735886000
_diffrn_orient_matrix_UB_33      0.0033920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4381
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.737
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0360
_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)+(0.0448P)²+0.8038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1791
_reflns_number_total             2121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob02661d2.cif
_cod_data_source_block           47p
_cod_depositor_comments
'Adding full bibliography for 7157313--7157314.cif.'
_cod_database_code               7157313
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C2(H2), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.621
_oxdiff_exptl_absorpt_empirical_full_min 0.521
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F4 F 0.56840(7) 0.36367(13) 0.83604(5) 0.0231(3) Uani 1 1 d .
F6 F 0.30177(8) 0.37205(15) 0.56536(5) 0.0316(3) Uani 1 1 d .
F5 F 0.70082(8) 0.63022(15) 0.67661(5) 0.0314(3) Uani 1 1 d .
F7 F 0.38500(8) 0.53025(15) 0.51820(5) 0.0312(3) Uani 1 1 d .
F3 F 0.26526(8) 0.74049(16) 0.92208(5) 0.0339(3) Uani 1 1 d .
F1 F 0.37861(8) 0.59456(17) 0.97953(5) 0.0364(3) Uani 1 1 d .
F8 F 0.42668(9) 0.27220(16) 0.53643(5) 0.0387(3) Uani 1 1 d .
F2 F 0.24787(9) 0.47354(17) 0.92912(6) 0.0419(4) Uani 1 1 d .
O1 O 0.62605(9) 0.63718(17) 0.77723(6) 0.0234(3) Uani 1 1 d .
N2 N 0.48319(10) 0.51472(19) 0.72456(6) 0.0162(3) Uani 1 1 d .
N1 N 0.35777(10) 0.6137(2) 0.76912(7) 0.0184(4) Uani 1 1 d .
C1 C 0.48728(12) 0.4575(2) 0.83184(8) 0.0172(4) Uani 1 1 d .
C9 C 0.45703(13) 0.4609(2) 0.61914(8) 0.0182(4) Uani 1 1 d .
C6 C 0.57862(13) 0.5784(2) 0.72965(8) 0.0181(4) Uani 1 1 d .
C10 C 0.42364(13) 0.4626(2) 0.67042(8) 0.0173(4) Uani 1 1 d .
H10 H 0.359807 0.428243 0.669292 0.021 Uiso 1 1 calc R
C3 C 0.36110(13) 0.5673(2) 0.87390(8) 0.0177(4) Uani 1 1 d .
C5 C 0.44158(12) 0.5290(2) 0.77664(8) 0.0166(4) Uani 1 1 d .
C4 C 0.31722(13) 0.6301(2) 0.81672(8) 0.0185(4) Uani 1 1 d .
H4 H 0.257370 0.685502 0.811468 0.022 Uiso 1 1 calc R
C2 C 0.44808(13) 0.4780(2) 0.88168(8) 0.0195(4) Uani 1 1 d .
H2 H 0.478776 0.433566 0.919272 0.023 Uiso 1 1 calc R
C8 C 0.55433(14) 0.5156(2) 0.62026(8) 0.0220(4) Uani 1 1 d .
H8 H 0.578502 0.513884 0.585271 0.026 Uiso 1 1 calc R
C7 C 0.61010(13) 0.5696(2) 0.67327(9) 0.0209(4) Uani 1 1 d .
C11 C 0.39227(14) 0.4088(3) 0.56037(8) 0.0230(5) Uani 1 1 d .
C12 C 0.31295(14) 0.5938(3) 0.92612(8) 0.0235(5) 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 N2 C5 117.50(14)
C10 N2 C6 123.37(15)
C10 N2 C5 118.46(14)
C5 N1 C4 118.22(15)
F4 C1 C5 119.88(16)
F4 C1 C2 119.92(15)
C2 C1 C5 120.17(17)
C10 C9 C8 120.08(16)
C10 C9 C11 120.80(17)
C8 C9 C11 119.07(16)
O1 C6 N2 121.56(17)
O1 C6 C7 125.66(17)
N2 C6 C7 112.75(15)
C9 C10 N2 120.64(16)
C4 C3 C12 119.93(16)
C2 C3 C4 119.29(17)
C2 C3 C12 120.76(16)
N1 C5 N2 116.63(15)
N1 C5 C1 122.24(17)
C1 C5 N2 121.14(16)
N1 C4 C3 122.48(17)
C1 C2 C3 117.52(16)
C7 C8 C9 118.13(17)
F5 C7 C6 114.16(16)
F5 C7 C8 120.89(17)
C8 C7 C6 124.85(17)
F6 C11 F7 107.32(15)
F6 C11 F8 107.17(16)
F6 C11 C9 112.54(15)
F7 C11 F8 105.30(15)
F7 C11 C9 111.69(16)
F8 C11 C9 112.37(15)
F3 C12 F1 106.74(16)
F3 C12 C3 112.08(16)
F1 C12 C3 111.72(15)
F2 C12 F3 106.65(16)
F2 C12 F1 107.14(16)
F2 C12 C3 112.15(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F4 C1 1.343(2)
F6 C11 1.331(2)
F5 C7 1.345(2)
F7 C11 1.341(2)
F3 C12 1.332(2)
F1 C12 1.342(2)
F8 C11 1.346(2)
F2 C12 1.330(2)
O1 C6 1.221(2)
N2 C6 1.410(2)
N2 C10 1.379(2)
N2 C5 1.434(2)
N1 C5 1.329(2)
N1 C4 1.334(2)
C1 C5 1.387(2)
C1 C2 1.373(3)
C9 C10 1.347(2)
C9 C8 1.426(3)
C9 C11 1.487(3)
C6 C7 1.444(3)
C3 C4 1.391(3)
C3 C2 1.385(3)
C3 C12 1.504(3)
C8 C7 1.343(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 154630726
