Visible-light promoted dithioacetalization of aldehydes with thiols under aerobic and photocatalyst-free conditions
Xing, Zhimin; Yang, Mingyang; Sun, Haiyu; Wang, Zemin; Chen, Peng; Liu, Lin; Wang, Xiaolei; Xie, Xingang; She, Xuegong; Green Chemistry 20 (2018) 5117–; doi:10.1039/C8GC02237B

data_7231666
_publ_section_title
;
 Visible-light promoted dithioacetalization of aldehydes with thiols under
 aerobic and photocatalyst-free conditions
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              5117
_journal_paper_doi               10.1039/C8GC02237B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C12 H11 O2 S2'
_chemical_formula_sum            'C13.75 H12.5 N1.25 O1.25 S0.25'
_chemical_formula_weight         223.26
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-19 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.001(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6319(6)
_cell_length_b                   18.0068(13)
_cell_length_c                   7.8624(4)
_cell_measurement_reflns_used    1213
_cell_measurement_temperature    291.5(3)
_cell_measurement_theta_max      25.3070
_cell_measurement_theta_min      3.9680
_cell_volume                     1207.03(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      291.5(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -11.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000  -60.0000 32

  2 omega  -32.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000 -180.0000 78

  3 omega  -17.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000    0.0000 114
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0623828000
_diffrn_orient_matrix_UB_12      -0.0007698000
_diffrn_orient_matrix_UB_13      0.0704165000
_diffrn_orient_matrix_UB_21      0.0140625000
_diffrn_orient_matrix_UB_22      0.0382621000
_diffrn_orient_matrix_UB_23      -0.0123995000
_diffrn_orient_matrix_UB_31      -0.0532176000
_diffrn_orient_matrix_UB_32      0.0092596000
_diffrn_orient_matrix_UB_33      0.0569038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4468
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             471
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+1.0356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1639
_reflns_number_gt                1682
_reflns_number_total             2375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8gc02237b2.cif
_cod_data_source_block           xinzhj_0514
_cod_depositor_comments          'Adding full bibliography for 7231666.cif.'
_cod_original_cell_volume        1207.03(13)
_cod_original_formula_sum        'C13.75 H12.50 N1.25 O1.25 S0.25'
_cod_database_code               7231666
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_olex2_date_sample_data_collection 2018-05-16
_olex2_submission_special_instructions 'No special instructions were received'