Thioarylative Radical Cyclization of Yne-Dienone.
Mallick, Rajendra K.; Dutta, Shubham; Vanjari, Rajeshwer; Voituriez, Arnaud; Sahoo, Akhila K.; The Journal of organic chemistry 84 (2019) 10509–10517; doi:10.1021/acs.joc.9b01445

data_4034035
_publ_section_title
;
 Thioarylative Radical Cyclization of Yne-Dienone.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10509
_journal_page_last               10517
_journal_paper_doi               10.1021/acs.joc.9b01445
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H20 O2 S'
_chemical_formula_sum            'C22 H20 O2 S'
_chemical_formula_weight         348.44
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.479(9)
_cell_angle_beta                 87.969(10)
_cell_angle_gamma                77.882(9)
_cell_formula_units_Z            4
_cell_length_a                   11.189(3)
_cell_length_b                   11.474(2)
_cell_length_c                   14.860(3)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.30
_cell_volume                     1856.4(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.9884
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1711
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            80094
_diffrn_reflns_theta_full        27.7213
_diffrn_reflns_theta_max         27.72
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1759 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.8820.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             736.8152
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.5357
_refine_diff_density_min         -0.6301
_refine_diff_density_rms         0.1411
_refine_ls_d_res_high            0.7639
_refine_ls_d_res_low             9.3314
_refine_ls_goodness_of_fit_ref   1.0631
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0631
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.4162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                4762
_reflns_number_total             8632
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b01445_si_002.cif
_cod_data_source_block           aks109_0m_a
_cod_original_cell_volume        1856.3(7)
_cod_database_code               4034035
_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.a Ternary CH refined with riding coordinates:
 C37(H37), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30a,H30b), C7(H7a,H7b), C40(H40a,H40b), C6(H6a,H6b)
2.c Me refined with riding coordinates:
 C39(H39a,H39b,H39c), C18(H18a,H18b,H18c)
2.d Aromatic/amide H refined with riding coordinates:
 C43(H43), C42(H42), C19(H19), C20(H20), C36(H36), C27(H27), C11(H11),
 C23(H23), C25(H25), C26(H26), C15(H15), C24(H24), C32(H32), C35(H35), C12(H12),
  C5(H5), C34(H34), C14(H14), C13(H13), C33(H33), C4(H4), C3(H3), C2(H2),
 C1a(H1a)
;
_olex2_submission_special_instructions 'No special instructions were received'