Synthesis of benzo[<i>b</i>][1,5]diazocin-6(5<i>H</i>)-one derivatives <i>via</i> the Cu-catalysed oxidative cyclization of 2-aryl-1<i>H</i>-indoles with 1,1-enediamines.
Chen, Yi-Hua; Yang, Jing; Lu, Zi-Han; Zhao, Ke-Hua; Xie, Qi-Ying; Yan, Sheng-Jiao; Chemical communications (Cambridge, England) 59 (2023) 1217–1220; doi:10.1039/d2cc06388c

data_7131153
_publ_section_title
;
 Synthesis of benzo[<i>b</i>][1,5]diazocin-6(5<i>H</i>)-one derivatives
 <i>via</i> the Cu-catalysed oxidative cyclization of
 2-aryl-1<i>H</i>-indoles with 1,1-enediamines.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1217
_journal_page_last               1220
_journal_paper_doi               10.1039/d2cc06388c
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C32 H28 N4 O5'
_chemical_formula_sum            'C32 H28 N4 O5'
_chemical_formula_weight         548.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-05-09
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8871(7)
_cell_length_b                   10.9414(9)
_cell_length_c                   30.867(3)
_cell_measurement_reflns_used    9736
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.64
_cell_volume                     2663.7(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0787
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            21745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         1.975
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1691 before and 0.1078 after correction.
The Ratio of minimum to maximum transmission is 0.8701.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       SLICE
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0501P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5083
_reflns_number_total             6628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06388c2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7131153.cif.'
_cod_database_code               7131153
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.978
_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 Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13), C19(H19), C20(H20), C22(H22), C23(H23), C27(H27), C28(H28),
 C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              90654
_shelx_hkl_checksum              45967
_olex2_submission_special_instructions 'No special instructions were received'