A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds
Moghaddam, Firouz Matloubi; Goudarzi, Mehri; Chamani, Fatemeh; Dezag, Hamid Mohammadzadeh; New Journal of Chemistry 44 (2020) 9699–9702; doi:10.1039/D0NJ00691B

data_7059624
_publ_section_title
;
 A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based
 multicomponent reaction under ultrasound irradiation: synthesis of
 polysubstituted pyrrolidine compounds
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9699
_journal_page_last               9702
_journal_paper_doi               10.1039/D0NJ00691B
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C22 H28 N4 S2'
_chemical_formula_sum            'C22 H28 N4 S2'
_chemical_formula_weight         412.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-25
_audit_creation_method
;
(compiled 2018.05.29 svn.r3508 for, GUI svn.r5506)
;
_audit_update_record
;
2019-08-29 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.552(4)
_cell_length_b                   20.072(4)
_cell_length_c                   6.0258(12)
_cell_measurement_reflns_used    12960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.50
_cell_volume                     2243.9(8)
_computing_cell_refinement       'Automar software package (1.24-4, 2013)'
_computing_data_collection       'MAR345 dtb Program Manual(1.24-4, 2013)'
_computing_data_reduction        'Automar software package (1.24-4, 2013)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1595
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12362
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.495
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0776
_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^)+(0.1038P)^2^+1.2377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                3543
_reflns_number_total             3802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00691b2.cif
_cod_data_source_block           dd
_cod_depositor_comments
;Adding full bibliography for 7059624.cif.

 Adding full bibliography for 7059624.cif.
;
_cod_database_code               7059624
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.822
_refinement_description
;
1. Twinned data refinement
 Scales: 1.1(2)
 -0.1(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C9(H9), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C17(H17A,H17B), C21(H21A,H21B), C18(H18A,H18B),
 C20(H20A,H20B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C15(H15), C14(H14), C12(H12)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              97658
_submission_special_instructions 'No special instructions were received'