Synthesis of β-hydroxysulfides via visible-light-driven and EDA complex-promoted hydroxysulfenylation of styrenes with heterocyclic thiols in EtOH under photocatalyst-free conditions
Chen, Ziren; Xue, Fei; Liu, Tianxiang; Wang, Bin; Zhang, Yonghong; Jin, Weiwei; Xia, Yu; Liu, Chenjiang; Green Chemistry 24 (2022) 3250–3256; doi:10.1039/D2GC00121G

data_7244626
_publ_section_title
;
 Synthesis of \b-hydroxysulfides via visible-light-driven and EDA
 complex-promoted hydroxysulfenylation of styrenes with heterocyclic
 thiols in EtOH under photocatalyst-free conditions
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              3250
_journal_page_last               3256
_journal_paper_doi               10.1039/D2GC00121G
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         '4(C21 H16 Cl2 N2 O S), 0.5(C6 H14)'
_chemical_formula_sum            'C87 H71 Cl8 N8 O4 S4'
_chemical_formula_weight         1704.35
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2021-04-26 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.148(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   24.764(5)
_cell_length_b                   12.538(3)
_cell_length_c                   13.430(3)
_cell_measurement_reflns_used    6694
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.38
_cell_volume                     4169.1(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25147
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.751
_diffrn_reflns_theta_min         2.312
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0296 after correction.
The Ratio of minimum to maximum transmission is 0.9056.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1762
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         9475
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0893P)^2^+0.2802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6404
_reflns_number_total             9475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00121g2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7244625--7244626.cif.'
_cod_original_cell_volume        4168.9(14)
_cod_database_code               7244626
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C43-C44
 1.5 with sigma of 0.02
 C46-C43
 1.5 with sigma of 0.02
 C46-C46_$1
 1.5 with sigma of 0.02
3. Others
 Fixed Sof: C43(0.5) H43A(0.5) H43B(0.5) C44(0.5) H44A(0.5) H44B(0.5)
 H44C(0.5) C46(0.5) H46A(0.5) H46B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B), C43(H43A,H43B), C46(H46A,H46B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C14(H14), C17(H17), C22(H22), C24(H24), C30(H30), C31(H31),
 C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), N3(H3), C19(H19), C20(H20),
 C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C34(H34), C40(H40),
  C41(H41), C42(H42)
4.c Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_shelx_res_checksum              90964
_olex2_submission_special_instructions 'No special instructions were received'