Scandium-catalyzed chemoselective carbene insertion into N-H over S-H: access to <i>o</i>-alkylamine-diaryl disulfides.
Sun, Haoyany; Pan, Junhong; Zhao, Wenying; Zhou, Tong; Song, Xizhong; Lin, Jun; Jin, Yi; Chemical communications (Cambridge, England) 60 (2024) 3798–3801; doi:10.1039/d4cc00557k

data_1571187
_publ_section_title
;
 Scandium-catalyzed chemoselective carbene insertion into N-H over S-H:
 access to <i>o</i>-alkylamine-diaryl disulfides.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3798
_journal_page_last               3801
_journal_paper_doi               10.1039/d4cc00557k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C30 H28 N2 O4 S2'
_chemical_formula_sum            'C30 H28 N2 O4 S2'
_chemical_formula_weight         544.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-29
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2024-02-01 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.702(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2168(12)
_cell_length_b                   12.1811(18)
_cell_length_c                   28.132(4)
_cell_measurement_reflns_used    3488
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.03
_cell_measurement_theta_min      2.54
_cell_volume                     2809.8(7)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      273.15
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1330
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28905
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.214
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1631 before and 0.0757 after correction.
The Ratio of minimum to maximum transmission is 0.8338.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1990
_refine_ls_R_factor_gt           0.1110
_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^)+(0.0145P)^2^+6.5060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2791
_reflns_number_total             4962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00557k2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1571187.cif.'
_cod_original_cell_volume        2809.9(7)
_cod_original_sg_symbol_H-M      'P  21/n'
_cod_database_code               1571187
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C18(H18), C19(H19), C20(H20), C21(H21), C2(H2A), C3(H3),
 C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C27(H27),
 C28(H28), C29(H29), C30(H30), C26(H26)
2.c Fitted hexagon refined as free rotating group:
 C17(C18,C19,C20,C21,C16), C1(C2,C3,C4,C5,C6), C11(C12,C13,C14,C15,C10),
 C27(C28,C29,C30,C25,C26)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.978
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              47316
_shelx_hkl_checksum              37060