Polysulfide synthesis <i>via</i> visible-light-induced heteroarene-migratory dithiosulfonylation reaction.
Wang, Baoxu; Hu, Zijing; Huang, Lu; Ren, Xiaorui; Gao, Qianwen; Wang, Xi; Chemical communications (Cambridge, England) 59 (2023) 7247–7250; doi:10.1039/d3cc01994b

data_7131664
_publ_section_title
;
 Polysulfide synthesis <i>via</i> visible-light-induced
 heteroarene-migratory dithiosulfonylation reaction.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7247
_journal_page_last               7250
_journal_paper_doi               10.1039/d3cc01994b
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H27 F2 N O2 S4'
_chemical_formula_sum            'C23 H27 F2 N O2 S4'
_chemical_formula_weight         516.70
_chemical_melting_point          316
_chemical_name_systematic
2-(4-(tert-butyldisulfaneyl)-1-((3,5-difluorophenyl)sulfonyl)-4-methylpentan-2-yl)benzo[d]thiazole
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-05 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                99.5990(10)
_cell_angle_beta                 90.8580(10)
_cell_angle_gamma                94.4910(10)
_cell_formula_units_Z            2
_cell_length_a                   6.0073(2)
_cell_length_b                   11.3650(5)
_cell_length_c                   18.1482(7)
_cell_measurement_reflns_used    9666
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.389
_cell_measurement_theta_min      2.277
_cell_volume                     1217.44(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.15
_diffrn_detector                 CCD
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14324
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.307
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.0962
_exptl_absorpt_correction_T_min  0.0602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1746 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.6258.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.096
_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     294
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0919P)^2^+1.3767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3738
_reflns_number_total             4211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01994b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7131664--7131665.cif.'
_cod_database_code               7131664
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_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
2. Rigid bond restraints
 C16, C15, C14, C17
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C14 \\sim C17: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C17)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 N009(H009), C3(H3), C5(H5), C1(H1), C11(H11), C00Q(H00Q), C12(H12), C13(H13)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C16(H16A,H16B,
 H16C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              18291
_shelx_hkl_checksum              25494
_olex2_submission_special_instructions 'No special instructions were received'