Light-induced intramolecular carbene C(sp<sup>3</sup>)-H insertion of <i>N</i>-tosylhydrazones; synthesis of functionalized coumarans and indolines.
Yamini, Pokhriyal; Duklan, Bhoomika; Nirmal, Mukesh; Yadagiri, Dongari; Chemical communications (Cambridge, England) 61 (2025) 17017–17020; doi:10.1039/d5cc04412j

data_7135021
_publ_section_title
;
 Light-induced intramolecular carbene C(sp<sup>3</sup>)-H insertion of
 <i>N</i>-tosylhydrazones; synthesis of functionalized coumarans and
 indolines.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17017
_journal_page_last               17020
_journal_paper_doi               10.1039/d5cc04412j
_journal_volume                  61
_journal_year                    2025
_chemical_compound_source        Methanol
_chemical_formula_moiety         '3(C26 H26 O4)'
_chemical_formula_sum            'C78 H78 O12'
_chemical_formula_weight         1207.40
_chemical_name_systematic        YD_YP_BIS_1631_YP
_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_creation_date             2025-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-05 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                107.5890(10)
_cell_angle_beta                 97.7310(10)
_cell_angle_gamma                95.8250(10)
_cell_formula_units_Z            1
_cell_length_a                   6.0018(2)
_cell_length_b                   16.2806(5)
_cell_length_c                   16.8345(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    103.00
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      2.49
_cell_volume                     1536.10(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      103.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0736
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            85285
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.727
_diffrn_reflns_theta_min         1.289
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1380 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The \l/2 correction factor is Not present.
;
_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    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             642
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.0891
_exptl_crystal_size_mid          0.0789
_exptl_crystal_size_min          0.0564
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         7915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0706
_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^)+(0.0833P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.1958
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5653
_reflns_number_total             7915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04412j2.cif
_cod_data_source_block           yd_yp_bis_1631_yp_0m_a
_cod_depositor_comments          'Adding full bibliography for 7135021.cif.'
_cod_database_code               7135021
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00V(H00V), C010(H010), C011(H011), C013(H013), C019(H019)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00H), C00D(H00I), C00F(H00F), C00G(H00G),
 C00J(H00J), C00M(H00M), C00P(H00P), C00R(H00R), C00S(H00S), C00U(H00U),
 C00Y(H00Y), C00Z(H00Z), C015(H015)
2.c Idealised Me refined as rotating group:
 C00W(H00A,H00C,H00D), C00X(H00K,H00L,H00N), C014(H01A,H01B,H01C), C016(H01D,
 H01E,H01F), C017(H01G,H01H,H01I), C018(H01J,H01K,H01L)
;
_shelx_res_checksum              10792
_shelx_hkl_checksum              30885
_olex2_submission_special_instructions 'No special instructions were received'