<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_7132942
_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 H18 N2 O S'
_chemical_formula_sum            'C23 H18 N2 O S'
_chemical_formula_weight         370.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-19 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.548(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2520(7)
_cell_length_b                   14.7387(13)
_cell_length_c                   15.4992(13)
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.29
_cell_measurement_theta_min      2.65
_cell_volume                     1872.8(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1125
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.485
_diffrn_reflns_theta_min         2.646
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5561
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1643 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.7458.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0522P)^2^+0.0848P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2237
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01315h2.cif
_cod_data_source_block           b220725c_0m
_cod_depositor_comments
'Adding full bibliography for 7132942--7132943.cif.'
_cod_database_code               7132942
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.946
_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 Ternary CH refined with riding coordinates:
 C13(H13), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C8(H8), C10(H10), C12(H12), C3(H3), C15(H15), C2(H2),
 C17(H17), C9(H9), C21(H21), C11(H11)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              59759
_shelx_hkl_checksum              65936
_olex2_submission_special_instructions 'No special instructions were received'