A radical approach towards polarity-reversed <i>para</i>-substitution of electron-deficient arenes.
Singh, Shashank; Kundu, Arindam; Empel, Claire; Koenigs, René Michael; Singh, Ravi P.; Chemical communications (Cambridge, England) 61 (2025) 3888–3891; doi:10.1039/d4cc04914d

data_7134207
_publ_section_title
;
 A radical approach towards polarity-reversed <i>para</i>-substitution of
 electron-deficient arenes.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3888
_journal_page_last               3891
_journal_paper_doi               10.1039/d4cc04914d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C19 H11 F3 N2'
_chemical_formula_sum            'C19 H11 F3 N2'
_chemical_formula_weight         324.30
_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_date             2023-12-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-12-29 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.895(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1854(9)
_cell_length_b                   8.7585(6)
_cell_length_c                   14.5343(11)
_cell_measurement_reflns_used    4943
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      20.54
_cell_measurement_theta_min      2.73
_cell_volume                     1642.4(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      303.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.731
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0742 after correction.
The Ratio of minimum to maximum transmission is 0.8601.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0826
_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/[\s^2^(Fo^2^)+(0.1322P)^2^+0.6936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2457
_refine_ls_wR_factor_ref         0.2981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2137
_reflns_number_total             4093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04914d2.cif
_cod_data_source_block           fdfgdh_0m_a
_cod_depositor_comments
'Adding full bibliography for 7134206--7134207.cif.'
_cod_database_code               7134207
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.999
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C18-F2 \\sim C18-F2A
 with sigma of 0.04
 C18-F3 \\sim C18-F3A
 with sigma of 0.02
 F2-F3 \\sim F2-F3A
 with sigma of 0.02
 C18-F1 \\sim C18-F1A
 with sigma of 0.02
 F1-F3 \\sim F1A-F3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2) = Uanis(F3A) = Uanis(F3) = Uanis(F1) = Uanis(F1A) = Uanis(F2A)
4. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F2A(0.5) F3A(0.5) F1A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              47513
_shelx_hkl_checksum              44730
_olex2_submission_special_instructions 'No special instructions were received'