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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/7/06/28/7062804.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_7062804
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_sum            'C9 H7 F N2 O'
_chemical_formula_weight         178.17
_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-2018/3
_audit_update_record
;
2023-06-29 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                94.118(2)
_cell_angle_beta                 98.142(2)
_cell_angle_gamma                94.746(2)
_cell_formula_units_Z            2
_cell_length_a                   4.25810(10)
_cell_length_b                   8.4237(2)
_cell_length_c                   10.9697(3)
_cell_measurement_reflns_used    4337
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      75.9420
_cell_measurement_theta_min      4.0580
_cell_volume                     386.776(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.938
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7180
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.152
_diffrn_reflns_theta_min         4.086
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       needle
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0379
_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)+(0.0681P)²+0.0531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1366
_reflns_number_total             1532
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04313d2.cif
_cod_data_source_block           rkn_673
_cod_depositor_comments
'Adding full bibliography for 7062803--7062807.cif.'
_cod_database_code               7062804
_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, -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
F12 F 0.61360(19) 0.84862(9) 0.44088(7) 0.0452(3) Uani 1 1 d . . . . .
O13 O 0.04212(19) 0.66411(10) 0.11637(7) 0.0325(3) Uani 1 1 d . . . . .
N2 N 0.6423(2) 0.55285(11) 0.34658(9) 0.0255(3) Uani 1 1 d . . . . .
N9 N 0.3116(2) 0.44100(11) 0.11571(8) 0.0279(3) Uani 1 1 d . . . . .
H9 H 0.211071 0.406428 0.041688 0.033 Uiso 1 1 calc R U . . .
C1 C 0.4370(3) 0.63537(14) 0.28815(10) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.6899(3) 0.40456(13) 0.29184(10) 0.0253(3) Uani 1 1 d . . . . .
C10 C 0.2462(3) 0.58235(14) 0.16685(10) 0.0266(3) Uani 1 1 d . . . . .
C8 C 0.5297(3) 0.34744(14) 0.17411(11) 0.0263(3) Uani 1 1 d . . . . .
C4 C 0.9060(3) 0.31070(14) 0.35526(10) 0.0276(3) Uani 1 1 d . . . . .
H4 H 1.015096 0.348091 0.435060 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3799(3) 0.79734(14) 0.34181(11) 0.0305(3) Uani 1 1 d . . . . .
H11A H 0.381727 0.874350 0.277795 0.037 Uiso 1 1 calc R U . . .
H11B H 0.168162 0.792307 0.369471 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9592(3) 0.16484(15) 0.30173(11) 0.0317(3) Uani 1 1 d . . . . .
H5 H 1.102783 0.100638 0.345177 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5895(3) 0.20035(15) 0.11897(11) 0.0309(3) Uani 1 1 d . . . . .
H7 H 0.484931 0.163017 0.038473 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8020(3) 0.11027(15) 0.18291(12) 0.0324(3) Uani 1 1 d . . . . .
H6 H 0.842842 0.009909 0.146191 0.039 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
C1 N2 C3 118.17(10) . . ?
C10 N9 C8 123.10(10) . . ?
C10 N9 H9 118.4 . . ?
C8 N9 H9 118.4 . . ?
N2 C1 C10 124.36(11) . . ?
N2 C1 C11 120.47(10) . . ?
C10 C1 C11 115.17(10) . . ?
N2 C3 C8 121.46(11) . . ?
N2 C3 C4 119.17(10) . . ?
C8 C3 C4 119.36(11) . . ?
O13 C10 N9 123.22(10) . . ?
O13 C10 C1 121.82(11) . . ?
N9 C10 C1 114.95(10) . . ?
N9 C8 C7 121.66(10) . . ?
N9 C8 C3 117.83(11) . . ?
C7 C8 C3 120.50(11) . . ?
C5 C4 C3 119.92(11) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
F12 C11 C1 110.12(9) . . ?
F12 C11 H11A 109.6 . . ?
C1 C11 H11A 109.6 . . ?
F12 C11 H11B 109.6 . . ?
C1 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C4 C5 C6 120.20(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C6 C7 C8 119.11(11) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C6 C5 120.88(11) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
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 1.3830(14) . ?
O13 C10 1.2465(14) . ?
N2 C1 1.2897(15) . ?
N2 C3 1.3895(15) . ?
N9 C10 1.3465(15) . ?
N9 C8 1.3853(15) . ?
N9 H9 0.8800 . ?
C1 C10 1.4760(16) . ?
C1 C11 1.4991(16) . ?
C3 C8 1.4041(17) . ?
C3 C4 1.4048(16) . ?
C8 C7 1.3979(17) . ?
C4 C5 1.3734(17) . ?
C4 H4 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C5 C6 1.4050(17) . ?
C5 H5 0.9500 . ?
C7 C6 1.3773(17) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
