<i>Z</i>-selective radical difunctionalization of aromatic alkynes: synthesis of multi-substituted triarylethenes.
Wang, Xinxin; Wang, Jie; Ji, Meishan; Wu, Xinxin; Zhu, Chen; Chemical communications (Cambridge, England) 60 (2024) 4894–4897; doi:10.1039/d4cc01315h

data_7132943
_publ_section_title
;
 <i>Z</i>-selective radical difunctionalization of aromatic alkynes:
 synthesis of multi-substituted triarylethenes.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4894
_journal_page_last               4897
_journal_paper_doi               10.1039/d4cc01315h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C23 H16 F N O S'
_chemical_formula_sum            'C23 H16 F N O S'
_chemical_formula_weight         373.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-19 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0108(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5347(7)
_cell_length_b                   15.7748(8)
_cell_length_c                   19.3093(10)
_cell_measurement_reflns_used    9411
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.24
_cell_volume                     3780.8(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0475
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52411
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_min         2.237
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1289 before and 0.0598 after correction. The Ratio of minimum to maximum transmission is 0.9053. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.083
_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     245
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0674
_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/[\s^2^(Fo^2^)+(0.1226P)^2^+4.7031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3222
_reflns_number_total             4346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01315h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7132942--7132943.cif.'
_cod_database_code               7132943
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.927
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C1(H1), C15(H15), C4(H4), C13(H13), C19(H19), C22(H22),
 C12(H12), C2(H2), C3(H3), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              54682
_shelx_hkl_checksum              72505
_olex2_submission_special_instructions 'No special instructions were received'