Highly Chemoselective Homologative Assembly of the α-Substituted Methylsulfinamide Motif from N-Sulfinylamines
Malik, Monika; Senatore, Raffaele; Castiglione, Davide; Roller, Alexander; Pace, Vittorio; Chemical Communications  (2023) –; doi:10.1039/D3CC03326K

data_7132033
_publ_section_title
;
 Highly Chemoselective Homologative Assembly of the \a-Substituted
 Methylsulfinamide Motif from N-Sulfinylamines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03326K
_journal_year                    2023
_chemical_formula_moiety         'C13 H12 Cl N3 O S'
_chemical_formula_sum            'C13 H12 Cl N3 O S'
_chemical_formula_weight         293.77
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-21 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                81.082(3)
_cell_angle_beta                 85.679(3)
_cell_angle_gamma                89.945(3)
_cell_formula_units_Z            4
_cell_length_a                   7.7841(8)
_cell_length_b                   10.3422(10)
_cell_length_c                   17.0738(17)
_cell_measurement_reflns_used    9408
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.110
_cell_measurement_theta_min      2.166
_cell_volume                     1354.0(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX 3'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28319
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         1.211
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_type              'Incoatec IuS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0997 before and 0.0582 after correction. 
The Ratio of minimum to maximum transmission is 0.9055. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0692P)^2^+2.5768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4261
_reflns_number_total             4975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03326k2.cif
_cod_data_source_block           vipars_453_p1
_cod_database_code               7132033
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.926
_shelx_res_checksum              83203
_shelx_hkl_checksum              68672