Diastereoselective radical cascade cyclization to access indole-fused diazepine derivatives.
Wang, Yutong; Huang, Xiujuan; Chen, Jinglong; Xu, Jian; Song, Qiuling; Organic & biomolecular chemistry 23 (2025) 4349–4354; doi:10.1039/d5ob00219b

data_7160485
_publ_section_title
;
 Diastereoselective radical cascade cyclization to access indole-fused
 diazepine derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4349
_journal_page_last               4354
_journal_paper_doi               10.1039/d5ob00219b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C33 H29 N2 O4 P'
_chemical_formula_sum            'C33 H29 N2 O4 P'
_chemical_formula_weight         548.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-07 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.3930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7645(2)
_cell_length_b                   35.2767(6)
_cell_length_c                   8.46120(10)
_cell_measurement_reflns_used    9799
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.168
_cell_measurement_theta_min      3.759
_cell_volume                     2765.65(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32848
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         2.505
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0843 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8415.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00059(10)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0378P)^2^+1.9562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0947
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4836
_reflns_number_total             5033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00219b2.cif
_cod_data_source_block           hxj110202
_cod_depositor_comments
'Adding full bibliography for 7160484--7160485.cif.'
_cod_database_code               7160485
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.704
_shelx_estimated_absorpt_t_min   0.654
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              20874
_olex2_submission_special_instructions 'No special instructions were received'