BF3·OEt2 catalyzed S–H insertion reactions of α-diazo imidamides and enolizable thioamides under metal-free conditions
Mangali, Rofin; Muthusamy, Sengodagounder; New Journal of Chemistry 46 (2022) 23173–23178; doi:10.1039/D2NJ04964C

data_7062073
_publ_section_title
;
 BF3&#x00B7;OEt2 catalyzed S--H insertion reactions of \a-diazo imidamides
 and enolizable thioamides under metal-free conditions
;
_journal_issue                   48
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              23173
_journal_page_last               23178
_journal_paper_doi               10.1039/D2NJ04964C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C26 H27 N5 O2 S2, 3.5[H2O]'
_chemical_formula_sum            'C27 H35 N5 O7.5 S2'
_chemical_formula_weight         613.72
_chemical_name_systematic        'Substituted indole'
_chemical_properties_physical    Moisture-sensitive
_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
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-06-19 deposited with the CCDC.	2022-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                97.380(3)
_cell_angle_beta                 112.378(2)
_cell_angle_gamma                103.183(3)
_cell_formula_units_Z            2
_cell_length_a                   11.3439(9)
_cell_length_b                   11.8482(9)
_cell_length_c                   12.3204(9)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.7149
_cell_measurement_theta_min      2.2571
_cell_volume                     1447.6(2)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301.78
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            40102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.284
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0475P)^2^+0.4998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4019
_reflns_number_total             5111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04964c2.cif
_cod_data_source_block           smrm121_0m_a
_cod_depositor_comments          'Adding full bibliography for 7062073.cif.'
_cod_original_cell_volume        1447.62(19)
_cod_original_formula_sum        'C27 H35 N5 O7.50 S2'
_cod_database_code               7062073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.951
_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 Aromatic/amide H refined with riding coordinates:
 N5(H5), C2(H2A), C3(H3), C4(H4), C5(H5A), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              33868
_shelx_fab_checksum              76982
_olex2_submission_special_instructions 'No special instructions were received'