Synthesis of indole-fused benzodiazepine derivatives by photocatalyzed cascade reaction.
Oishi, Tatsushi; Uchikura, Tatsuhiro; Akiyama, Takahiko; Chemical communications (Cambridge, England) 61 (2025) 2576–2579; doi:10.1039/d4cc05755d

data_7134167
_publ_section_title
;
 Synthesis of indole-fused benzodiazepine derivatives by photocatalyzed
 cascade reaction.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2576
_journal_page_last               2579
_journal_paper_doi               10.1039/d4cc05755d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H20 N2'
_chemical_formula_sum            'C23 H20 N2'
_chemical_formula_weight         324.41
_chemical_name_systematic        'reducted profuct'
_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     dual
_audit_creation_date             2024-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-09-13 deposited with the CCDC.	2025-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.011(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0423(8)
_cell_length_b                   15.3916(10)
_cell_length_c                   11.2723(8)
_cell_measurement_reflns_used    6424
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.6300
_cell_measurement_theta_min      2.1090
_cell_volume                     1706.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     44.00  69.50   0.50  220.00    --   20.00  54.00-180.00   51
  2  \w    -64.00 -38.50   0.50  220.00    --   20.00  54.00 -90.00   51
  3  \w     -8.00  17.50   0.50  220.00    --   20.00  54.00 -90.00   51
  4  \w    -74.00 106.50   0.50  220.00    --   20.00  54.00  30.00  361
  5  \w    -71.00 -43.50   0.50  220.00    --   20.00  54.00 120.00   55
  6  \w     -9.00  22.50   0.50  220.00    --   20.00  54.00 120.00   63
  7  \w    -65.00 -28.50   0.50  220.00    --   20.00  54.00   0.00   73
  8  \w     13.00  39.50   0.50  220.00    --   20.00  54.00   0.00   53
  9  \w     84.00 108.50   0.50  220.00    --   20.00  54.00   0.00   49
 10  \w    -67.00  35.50   0.50  220.00    --   20.00  54.00 -60.00  205
 11  \w    -69.00 -42.50   0.50  220.00    --   20.00  54.00  90.00   53
 12  \w    -71.00 -58.50   0.50  220.00    --   20.00  54.00-180.00   25
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0530110000
_diffrn_orient_matrix_UB_12      -0.0276342000
_diffrn_orient_matrix_UB_13      0.0435532000
_diffrn_orient_matrix_UB_21      0.0401302000
_diffrn_orient_matrix_UB_22      0.0368796000
_diffrn_orient_matrix_UB_23      0.0317606000
_diffrn_orient_matrix_UB_31      -0.0279277000
_diffrn_orient_matrix_UB_32      0.0006697000
_diffrn_orient_matrix_UB_33      0.0455818000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16263
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.721
_diffrn_reflns_theta_min         2.070
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.107a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method 'recrystallization from hexane/AcOEt'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0825P)^2^+0.3402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3645
_reflns_number_total             5054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05755d2.cif
_cod_data_source_block           to1024_2_auto
_cod_depositor_comments          'Adding full bibliography for 7134167.cif.'
_cod_database_code               7134167
_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.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C007(H007), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00P),
 C00O(H00Q), C00P(H00R)
2.d Idealised Me refined as rotating group:
 C00M(H00M,H00N,H00O)
;
_shelx_res_checksum              59154
_shelx_hkl_checksum              54624
_olex2_exptl_crystal_mounting_method 'sample loop'
_olex2_submission_original_sample_id TO1024
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.796