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#$Date: 2024-01-06 10:41:55 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/28/7062807.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_7062807
loop_
_publ_author_name
'Ramkumar, Nagarajan'
'Plantus, Ketrina'
'Ozola, Melita'
'Mishnev, Anatoly'
'Nikolajeva, Vizma'
'Senkovs, Maris'
'Ošeka, Maksim'
'Veliks, Janis'
_publ_section_title
;
 Photoredox-catalyzed direct C--H monofluoromethylation of heteroarenes
;
_journal_issue                   44
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20642
_journal_page_last               20652
_journal_paper_doi               10.1039/D3NJ04313D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C11 H8 F4 N2 O'
_chemical_formula_sum            'C11 H8 F4 N2 O'
_chemical_formula_weight         260.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4989(2)
_cell_length_b                   7.09040(10)
_cell_length_c                   20.0236(3)
_cell_measurement_reflns_used    6479
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      76.4180
_cell_measurement_theta_min      5.3570
_cell_volume                     2058.49(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.488
_diffrn_reflns_theta_min         4.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0354
_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)+(0.0564P)²+0.7159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1840
_reflns_number_total             2078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04313d2.cif
_cod_data_source_block           rkn_925
_cod_depositor_comments
'Adding full bibliography for 7062803--7062807.cif.'
_cod_database_code               7062807
_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.
;
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'
'-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
F12 F 0.10908(6) 0.54295(13) 0.76461(4) 0.0341(2) Uani 1 1 d . . . . .
F13 F 0.08832(7) 0.24603(14) 0.75734(5) 0.0419(3) Uani 1 1 d . . . . .
F16 F 0.21219(6) 0.11814(17) 0.38024(5) 0.0470(3) Uani 1 1 d . . . . .
F14 F 0.02409(6) 0.43109(19) 0.68656(5) 0.0492(3) Uani 1 1 d . . . . .
O17 O 0.47106(7) 0.1999(2) 0.45472(5) 0.0393(3) Uani 1 1 d . . . . .
N7 N 0.41686(7) 0.29198(17) 0.55689(6) 0.0229(3) Uani 1 1 d . . . . .
N4 N 0.23792(7) 0.23746(17) 0.50514(5) 0.0220(3) Uani 1 1 d . . . . .
C8 C 0.34068(8) 0.32450(18) 0.59755(6) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.18449(9) 0.38362(18) 0.67619(6) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.34982(9) 0.38219(19) 0.66417(7) 0.0223(3) Uani 1 1 d . . . . .
H9 H 0.409395 0.401813 0.682654 0.027 Uiso 1 1 calc R U . . .
C3 C 0.25174(9) 0.29733(19) 0.57069(6) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.17399(8) 0.32804(19) 0.61034(6) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.114033 0.310841 0.592199 0.024 Uiso 1 1 calc R U . . .
C10 C 0.27257(9) 0.41044(19) 0.70283(7) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.279209 0.448529 0.748063 0.027 Uiso 1 1 calc R U . . .
C5 C 0.31028(9) 0.2056(2) 0.46986(7) 0.0232(3) Uani 1 1 d . . . . .
C6 C 0.40649(9) 0.2310(2) 0.49252(7) 0.0256(3) Uani 1 1 d . . . . .
C11 C 0.10180(9) 0.4019(2) 0.72041(7) 0.0251(3) Uani 1 1 d . . . . .
C18 C 0.51083(9) 0.3224(3) 0.58247(8) 0.0321(4) Uani 1 1 d . . . . .
H18A H 0.555475 0.301228 0.546496 0.038 Uiso 1 1 calc R U . . .
H18B H 0.522988 0.234217 0.619099 0.038 Uiso 1 1 calc R U . . .
H18C H 0.516610 0.452157 0.598835 0.038 Uiso 1 1 calc R U . . .
C15 C 0.30339(10) 0.1370(3) 0.39892(7) 0.0315(3) Uani 1 1 d . . . . .
H15A H 0.334505 0.227737 0.368830 0.038 Uiso 1 1 calc R U . . .
H15B H 0.334989 0.013824 0.394712 0.038 Uiso 1 1 calc 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N7 C8 121.10(11) . . ?
C6 N7 C18 118.43(11) . . ?
C8 N7 C18 120.47(11) . . ?
C5 N4 C3 116.99(11) . . ?
N7 C8 C9 122.02(11) . . ?
N7 C8 C3 118.69(11) . . ?
C9 C8 C3 119.29(11) . . ?
C2 C1 C10 120.19(12) . . ?
C2 C1 C11 120.01(12) . . ?
C10 C1 C11 119.65(12) . . ?
C10 C9 C8 120.06(12) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N4 C3 C2 117.84(11) . . ?
N4 C3 C8 122.15(11) . . ?
C2 C3 C8 120.00(11) . . ?
C1 C2 C3 119.82(11) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C9 C10 C1 120.62(12) . . ?
C9 C10 H10 119.7 . . ?
C1 C10 H10 119.7 . . ?
N4 C5 C6 125.48(12) . . ?
N4 C5 C15 121.44(12) . . ?
C6 C5 C15 113.07(11) . . ?
O17 C6 N7 123.74(12) . . ?
O17 C6 C5 120.68(13) . . ?
N7 C6 C5 115.57(11) . . ?
F14 C11 F12 106.68(11) . . ?
F14 C11 F13 106.55(12) . . ?
F12 C11 F13 105.18(11) . . ?
F14 C11 C1 112.98(12) . . ?
F12 C11 C1 113.12(11) . . ?
F13 C11 C1 111.77(11) . . ?
N7 C18 H18A 109.5 . . ?
N7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F16 C15 C5 110.53(11) . . ?
F16 C15 H15A 109.5 . . ?
C5 C15 H15A 109.5 . . ?
F16 C15 H15B 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
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
F12 C11 1.3395(17) . ?
F13 C11 1.3442(17) . ?
F16 C15 1.3808(16) . ?
F14 C11 1.3311(16) . ?
O17 C6 1.2239(17) . ?
N7 C6 1.3679(18) . ?
N7 C8 1.3914(16) . ?
N7 C18 1.4714(16) . ?
N4 C5 1.2850(17) . ?
N4 C3 1.3939(16) . ?
C8 C9 1.4015(19) . ?
C8 C3 1.4105(17) . ?
C1 C2 1.3845(18) . ?
C1 C10 1.3970(18) . ?
C1 C11 1.4961(18) . ?
C9 C10 1.3761(19) . ?
C9 H9 0.9500 . ?
C3 C2 1.3959(17) . ?
C2 H2 0.9500 . ?
C10 H10 0.9500 . ?
C5 C6 1.4778(18) . ?
C5 C15 1.5046(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
