A simple route to 2,3-benzodiazepines from substituted indenes.
Tarasova, Ekaterina S.; Shurupova, Olga V.; Rzhevskiy, Sergey A.; Minaeva, Lidiya I.; Topchiy, Maxim A.; Asachenko, Andrey F.; Organic & biomolecular chemistry 23 (2025) 4710–4717; doi:10.1039/d5ob00361j

data_7160497
_publ_section_title
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 A simple route to 2,3-benzodiazepines from substituted indenes.
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_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4710
_journal_page_last               4717
_journal_paper_doi               10.1039/d5ob00361j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C17 H17 N2 O, C2 H3 O2, C2 H4 O2'
_chemical_formula_sum            'C21 H24 N2 O5'
_chemical_formula_weight         384.42
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-25 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                78.875(5)
_cell_angle_beta                 83.922(4)
_cell_angle_gamma                70.003(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6144(9)
_cell_length_b                   9.7829(11)
_cell_length_c                   14.1330(15)
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.25
_cell_volume                     969.81(19)
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14029
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.247
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0769 before and 0.0365 after correction.
The Ratio of minimum to maximum transmission is 0.9425.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0673P)^2^+0.3245P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3065
_reflns_number_total             3792
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00361j2.cif
_cod_data_source_block           full
_cod_depositor_comments          'Adding full bibliography for 7160497.cif.'
_cod_database_code               7160497
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C28(H28A,H28B,
 H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_shelx_res_checksum              34261
_olex2_submission_special_instructions 'No special instructions were received'