Visible-light-induced generation of alkenyl radicals from alkenyl sulfonium salts: direct synthesis of 11-alkenyl-substituted dibenzodiazepines.
Wang, Jie; Xu, Xue-Cen; Gong, Yue; Meng, Yu-Xuan; Zhao, Yu-Long; Chemical communications (Cambridge, England) 62 (2026) 2330–2334; doi:10.1039/d5cc06510k

data_7135529
_publ_section_title
;
 Visible-light-induced generation of alkenyl radicals from alkenyl
 sulfonium salts: direct synthesis of 11-alkenyl-substituted
 dibenzodiazepines.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2330
_journal_page_last               2334
_journal_paper_doi               10.1039/d5cc06510k
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         '3(C28 H26 N2 O2 S2), C28 H27 N2 O2 S2'
_chemical_formula_sum            'C112 H105 N8 O8 S8'
_chemical_formula_weight         1947.51
_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             2025-10-17
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-11-03 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                89.436(2)
_cell_angle_beta                 73.799(2)
_cell_angle_gamma                87.024(2)
_cell_formula_units_Z            2
_cell_length_a                   14.0675(6)
_cell_length_b                   16.7852(7)
_cell_length_c                   21.3193(9)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      63.700
_cell_measurement_theta_min      3.276
_cell_volume                     4827.6(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0586
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35455
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        63.679
_diffrn_reflns_theta_max         63.679
_diffrn_reflns_theta_min         2.158
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.225
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5121
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1460 before and 0.0607 after correction.
The Ratio of minimum to maximum transmission is 0.6806.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             2050
_refine_diff_density_max         1.144
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1241
_refine_ls_number_reflns         15556
_refine_ls_number_restraints     2682
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+11.1123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11078
_reflns_number_total             15556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06510k2.cif
_cod_data_source_block           zhaoyl241025_1_0m
_cod_database_code               7135529
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C00U \\sim C00S \\sim C00P \\sim C00T \\sim C00X \\sim C00V \\sim C00W \\sim
C00Z \\sim C00R \\sim C00Y \\sim C00Q \\sim C00O \\sim C01D \\sim C01F \\sim
C01G \\sim C01E \\sim C01C \\sim C01B \\sim C01A \\sim C01N \\sim C01K \\sim
C01H \\sim C01U \\sim C01S \\sim C01T \\sim C01V \\sim C01X \\sim C01Y \\sim
C01Q \\sim C01W \\sim C01J \\sim C01P \\sim C01Z \\sim C01O \\sim C01R \\sim
C01L \\sim C01I \\sim C01M \\sim C02Z \\sim C02G \\sim C02H \\sim C02L \\sim
C02D \\sim C02K \\sim C02J \\sim C02I \\sim C02M \\sim C02Y \\sim C02A \\sim
C02Q \\sim C02B \\sim C02F \\sim C02C \\sim C02V \\sim C02O \\sim C02E \\sim
C02U \\sim C02S \\sim C02W \\sim C02N \\sim C02X \\sim C02R \\sim C02P \\sim
C03F \\sim C03G \\sim C03B \\sim C03I \\sim C03J \\sim C03A \\sim C03N \\sim
C03H \\sim C03Q \\sim C03R \\sim C03P \\sim C03M \\sim C03C \\sim C03O \\sim
C03E \\sim C03K \\sim C03L \\sim C03D \\sim C010 \\sim C011 \\sim C012 \\sim
C013 \\sim C014 \\sim C015 \\sim C016 \\sim C017 \\sim C018 \\sim C019 \\sim
C020 \\sim C021 \\sim C022 \\sim C023 \\sim C024 \\sim C025 \\sim C026 \\sim
C027 \\sim C028 \\sim C029 \\sim C030 \\sim C031 \\sim C032 \\sim C033 \\sim
C034 \\sim C035 \\sim C036 \\sim C037 \\sim C038 \\sim C039 \\sim C2: within
3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 3.8A
Uanis(C03N) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C02Z(H02E,H02G), C03A(H6,HD), C03P(H03D,H03E), C03M(H2,HK), C03C(H8,HL),
 C03O(H03F,H03G), C033(H03T,H03U), C039(H4,HS)
3.b Aromatic/amide H refined with riding coordinates:
 N00G(H00G), C00T(H00T), C01G(H01G), C01E(H01E), C01T(H01T), C01W(H01W),
 C01J(H01J), C01P(H01P), C01L(H01L), C01I(H01I), C02H(H02O), C02L(H02L),
 C02D(H02D), C02J(H02P), C02I(H02I), C02M(H02M), C02Y(H02Y), C02F(H02F),
 C02C(H02Q), C02V(H02V), C02E(H02H), C02U(H02U), C02S(H02S), C02W(H02W),
 C02N(H02R), C02P(H02T), C03F(H03O), C03L(H03S), C03D(H03K), C015(H015),
 C018(H018), C020(H020), C021(H021), C022(H022), C023(H023), C025(H025),
 C027(H027), C029(H029), C030(H030), C031(H031), C032(H032)
3.c Idealised Me refined as rotating group:
 C02G(H02J,H02K,H02N), C02X(H02A,H02B,H02C), C03G(H03Z,H,HA), C03B(H03P,H03Q,
 H03R), C03I(H5,HB,HC), C03J(H03A,H03B,H03C), C03H(H03,HE,HF), C03Q(H1,HG,HH),
 C03R(H7,HI,HJ), C03E(H9,HM,HN), C03K(H03H,H03I,H03J), C035(H03V,H03W,H03X),
 C036(H03Y,HO,HP), C037(H3,HQ,HR), C038(H03L,H03M,H03N), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              36831
_shelx_hkl_checksum              26002
_olex2_submission_special_instructions 'No special instructions were received'