Electrochemically-driven difunctionalization of the isocyanide and Mumm rearrangement cascade: expeditious synthesis of <i>N</i>-acyl-<i>N</i>-alkyl <i>S</i>-thiocarbamates.
Bhati, Kuldeep Singh; Sharma, Siddharth; Chemical communications (Cambridge, England) 60 (2024) 7355–7358; doi:10.1039/d4cc02287d

data_7133199
_publ_section_title
;
 Electrochemically-driven difunctionalization of the isocyanide and Mumm
 rearrangement cascade: expeditious synthesis of
 <i>N</i>-acyl-<i>N</i>-alkyl <i>S</i>-thiocarbamates.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7355
_journal_page_last               7358
_journal_paper_doi               10.1039/d4cc02287d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C23 H21 N O4 S, C23 H20 N O4 S'
_chemical_formula_sum            'C46 H41 N2 O8 S2'
_chemical_formula_weight         813.93
_chemical_name_systematic        sidharth
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2jqfl9
_audit_creation_date             2024-03-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-04-02 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                88.303(9)
_cell_angle_beta                 85.635(9)
_cell_angle_gamma                63.604(8)
_cell_formula_units_Z            2
_cell_length_a                   10.581(3)
_cell_length_b                   10.781(3)
_cell_length_c                   20.524(6)
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    197.00
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      1.99
_cell_volume                     2091.1(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      197.00
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  mo_siddharth_108502_0m_sx
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7113
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.990
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Rigaku
_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    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             854
_exptl_crystal_preparation       difussion
_exptl_crystal_recrystallization_method 'at RT'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         7113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0755
_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^)+(0.1260P)^2^+1.2816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2189
_refine_ls_wR_factor_ref         0.2217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6750
_reflns_number_total             7113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02287d2.cif
_cod_data_source_block           mo_siddharth_108502_0m_sx
_cod_depositor_comments          'Adding full bibliography for 7133199.cif.'
_cod_original_cell_volume        2090.9(10)
_cod_database_code               7133199
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.652(2)
 0.348(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All H(H,H) groups, All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C00D(H00E,H00F), C00H(H00A,H00B), C00U(H00C,H00D)
3.b Me refined with riding coordinates:
 C01D(H01D,H01E,H01F)
3.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C017(H017), C018(H018), C01A(H01H), C01B(H01J), C01E(H01K), C01F(H01L),
 C01G(H01G), C01H(H01M), C01I(H01I), C01J(H01N), C01K(H01O)
3.d Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C), C01L(H01P,H01Q,H01R), C01M(H01S,H01T,H01U)
;
_shelx_res_checksum              9650
_shelx_hkl_checksum              53330
_olex2_exptl_crystal_mounting_method nylon
_olex2_submission_special_instructions 'No special instructions were received'