External photocatalyst-free photocycloaddition between triplet vinylnitrenes with 1,3-biradical character and activated olefins under 420 nm LEDs.
Malo, Sidhartha; Santra, Supriyo; Saha, Jayanta; Ghosh, Debashree; Das, Indrajit; Chemical communications (Cambridge, England) 60 (2024) 12545–12548; doi:10.1039/d4cc03484h

data_7133770
_publ_section_title
;
 External photocatalyst-free photocycloaddition between triplet
 vinylnitrenes with 1,3-biradical character and activated olefins under
 420 nm LEDs.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12545
_journal_page_last               12548
_journal_paper_doi               10.1039/d4cc03484h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H17 N O2 S'
_chemical_formula_sum            'C19 H17 N O2 S'
_chemical_formula_weight         323.39
_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
_audit_creation_date             2022-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-10 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                108.448(4)
_cell_angle_beta                 99.312(4)
_cell_angle_gamma                107.231(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7535(9)
_cell_length_b                   9.7512(10)
_cell_length_c                   11.0588(12)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      5.32
_cell_volume                     820.53(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      100.0
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21001
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.101
_diffrn_reflns_theta_min         5.323
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.821
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1503 before and 0.0852 after correction. The Ratio of minimum to maximum transmission is 0.7561. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       Block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0566P)^2^+0.5030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3036
_reflns_number_total             3125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03484h2.cif
_cod_data_source_block           sm_29cc_a
_cod_depositor_comments
'Adding full bibliography for 7133770--7133771.cif.'
_cod_database_code               7133770
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.735
_shelx_estimated_absorpt_t_min   0.712
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C12(H12), C13(H13), C16(H16), C2(H2), C14(H14), C1(H1),
 C15(H15), C6(H6)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              74497
_shelx_hkl_checksum              51376
_olex2_submission_special_instructions 'No special instructions were received'