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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/7/06/28/7062805.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_7062805
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            'C17 H13 F2 N3 O2'
_chemical_formula_weight         329.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 102.227(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6303(5)
_cell_length_b                   4.6620(2)
_cell_length_c                   18.9217(6)
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      75.8780
_cell_measurement_theta_min      2.7160
_cell_volume                     1433.73(9)
_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 0.996
_diffrn_measured_fraction_theta_max 0.941
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13626
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.532
_diffrn_reflns_theta_min         2.719
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60810
_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    1.526
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0601
_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)+(0.0660P)²+1.2833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2260
_reflns_number_total             2827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj04313d2.cif
_cod_data_source_block           rkn_689
_cod_depositor_comments
'Adding full bibliography for 7062803--7062807.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062805
_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+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_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
F16 F 0.04834(9) 0.8768(4) 0.32519(8) 0.0610(5) Uani 1 1 d . . . . .
F24 F 0.72218(9) 0.3273(5) 0.73542(11) 0.0907(7) Uani 1 1 d . . . . .
O17 O 0.21888(11) 0.2286(4) 0.38102(13) 0.0676(6) Uani 1 1 d . . . . .
N14 N 0.41511(11) 0.0033(4) 0.58325(13) 0.0531(6) Uani 1 1 d . . . . .
H14 H 0.404072 -0.181270 0.579147 0.064 Uiso 1 1 calc R U . . .
N1 N 0.20862(12) 0.2525(4) 0.49947(14) 0.0547(6) Uani 1 1 d . . . . .
N2 N 0.09036(11) 0.6837(4) 0.45999(11) 0.0429(5) Uani 1 1 d . . . . .
O13 O 0.36293(12) 0.4461(4) 0.55438(19) 0.1028(11) Uani 1 1 d . . . . .
C3 C 0.12458(13) 0.5623(5) 0.41241(14) 0.0461(6) Uani 1 1 d . . . . .
C5 C 0.11206(13) 0.5893(5) 0.53090(14) 0.0450(6) Uani 1 1 d . . . . .
C6 C 0.07319(15) 0.7136(6) 0.58172(14) 0.0505(6) Uani 1 1 d . . . . .
H6 H 0.032943 0.858561 0.567152 0.061 Uiso 1 1 calc R U . . .
C2 C 0.18719(14) 0.3339(5) 0.42815(17) 0.0530(7) Uani 1 1 d . . . . .
C10 C 0.17188(14) 0.3744(5) 0.55222(16) 0.0526(7) Uani 1 1 d . . . . .
C18 C 0.49589(13) 0.0861(6) 0.62069(15) 0.0518(7) Uani 1 1 d . . . . .
C15 C 0.10378(15) 0.6514(6) 0.33560(15) 0.0536(6) Uani 1 1 d . . . . .
H15A H 0.154585 0.710290 0.320109 0.064 Uiso 1 1 calc R U . . .
H15B H 0.079776 0.486617 0.305351 0.064 Uiso 1 1 calc R U . . .
C7 C 0.09275(17) 0.6276(7) 0.65290(16) 0.0616(8) Uani 1 1 d . . . . .
H7 H 0.066019 0.711532 0.687497 0.074 Uiso 1 1 calc R U . . .
C9 C 0.19207(17) 0.2925(7) 0.62463(18) 0.0654(9) Uani 1 1 d . . . . .
H9 H 0.233300 0.151583 0.640061 0.079 Uiso 1 1 calc R U . . .
C21 C 0.64809(15) 0.2413(8) 0.69632(17) 0.0674(9) Uani 1 1 d . . . . .
C12 C 0.35556(15) 0.1851(5) 0.5542(2) 0.0648(9) Uani 1 1 d . . . . .
C11 C 0.27444(14) 0.0411(6) 0.5183(2) 0.0670(9) Uani 1 1 d . . . . .
H11A H 0.281550 -0.059964 0.473970 0.080 Uiso 1 1 calc R U . . .
H11B H 0.259247 -0.102741 0.551628 0.080 Uiso 1 1 calc R U . . .
C8 C 0.15247(19) 0.4153(7) 0.67363(18) 0.0709(9) Uani 1 1 d . . . . .
H8 H 0.165874 0.354792 0.722668 0.085 Uiso 1 1 calc R U . . .
C23 C 0.54127(18) 0.2822(10) 0.5929(2) 0.0839(11) Uani 1 1 d . . . . .
H23 H 0.520076 0.363351 0.546681 0.101 Uiso 1 1 calc R U . . .
C22 C 0.61830(18) 0.3650(10) 0.6316(2) 0.0916(12) Uani 1 1 d . . . . .
H22 H 0.649406 0.505925 0.612832 0.110 Uiso 1 1 calc R U . . .
C19 C 0.5277(2) -0.0349(10) 0.6865(2) 0.0974(13) Uani 1 1 d . . . . .
H19 H 0.496555 -0.172955 0.706171 0.117 Uiso 1 1 calc R U . . .
C20 C 0.6060(2) 0.0438(11) 0.7251(2) 0.1051(15) Uani 1 1 d . . . . .
H20 H 0.628817 -0.040825 0.770617 0.126 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
C12 N14 C18 124.8(2) . . ?
C12 N14 H14 117.6 . . ?
C18 N14 H14 117.6 . . ?
C2 N1 C10 121.8(2) . . ?
C2 N1 C11 116.8(3) . . ?
C10 N1 C11 121.3(3) . . ?
C3 N2 C5 118.2(2) . . ?
N2 C3 C2 124.8(2) . . ?
N2 C3 C15 121.0(2) . . ?
C2 C3 C15 114.1(2) . . ?
N2 C5 C6 118.2(2) . . ?
N2 C5 C10 121.8(2) . . ?
C6 C5 C10 120.0(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O17 C2 N1 122.7(2) . . ?
O17 C2 C3 122.3(3) . . ?
N1 C2 C3 115.0(2) . . ?
C9 C10 N1 122.7(3) . . ?
C9 C10 C5 119.0(3) . . ?
N1 C10 C5 118.3(2) . . ?
C23 C18 C19 119.3(3) . . ?
C23 C18 N14 121.9(3) . . ?
C19 C18 N14 118.7(3) . . ?
F16 C15 C3 111.3(2) . . ?
F16 C15 H15A 109.4 . . ?
C3 C15 H15A 109.4 . . ?
F16 C15 H15B 109.4 . . ?
C3 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C20 C21 C22 122.7(3) . . ?
C20 C21 F24 118.2(3) . . ?
C22 C21 F24 119.0(3) . . ?
O13 C12 N14 124.6(2) . . ?
O13 C12 C11 121.0(2) . . ?
N14 C12 C11 114.4(2) . . ?
N1 C11 C12 110.9(2) . . ?
N1 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C18 C23 C22 120.6(4) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C21 C22 C23 118.6(4) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 118.4(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
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
F16 C15 1.384(3) . ?
F24 C21 1.357(3) . ?
O17 C2 1.230(3) . ?
N14 C12 1.330(3) . ?
N14 C18 1.433(3) . ?
N14 H14 0.8800 . ?
N1 C2 1.374(4) . ?
N1 C10 1.397(4) . ?
N1 C11 1.460(3) . ?
N2 C3 1.293(3) . ?
N2 C5 1.385(3) . ?
O13 C12 1.223(3) . ?
C3 C2 1.475(3) . ?
C3 C15 1.480(4) . ?
C5 C6 1.393(4) . ?
C5 C10 1.409(3) . ?
C6 C7 1.376(4) . ?
C6 H6 0.9500 . ?
C10 C9 1.393(4) . ?
C18 C23 1.360(5) . ?
C18 C19 1.368(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C7 C8 1.398(5) . ?
C7 H7 0.9500 . ?
C9 C8 1.371(5) . ?
C9 H9 0.9500 . ?
C21 C20 1.340(6) . ?
C21 C22 1.350(5) . ?
C12 C11 1.531(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8 0.9500 . ?
C23 C22 1.388(4) . ?
C23 H23 0.9500 . ?
C22 H22 0.9500 . ?
C19 C20 1.401(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
