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_7134206
_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         'C14 H11 F3 N2'
_chemical_formula_sum            'C14 H11 F3 N2'
_chemical_formula_weight         264.25
_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             2023-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-12-28 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.33(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.639(17)
_cell_length_b                   21.17(3)
_cell_length_c                   8.402(14)
_cell_measurement_reflns_used    1920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.64
_cell_volume                     1341(4)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_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  0.0517
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7313
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.252
_diffrn_reflns_theta_min         2.638
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1314 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.8688.
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    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0512P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1293
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04914d2.cif
_cod_data_source_block           pop_0m_c_a
_cod_depositor_comments
'Adding full bibliography for 7134206--7134207.cif.'
_cod_database_code               7134206
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1-C11 \\sim F1A-C11
 with sigma of 0.02
 F2-C11 \\sim F2A-C11
 with sigma of 0.02
 F3-C11 \\sim F3A-C11
 with sigma of 0.02
3. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F2A(0.5) F3A(0.5) F1A(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              33083
_shelx_hkl_checksum              32417
_olex2_submission_special_instructions 'No special instructions were received'