The new synthesis of pyrrole-fused dibenzo[<i>b</i>,<i>f</i>][1,4]oxazepine/thiazepines by the pseudo-Joullié-Ugi reaction <i>via</i> an unexpected route with high chemoselectivity.
Nazeri, Mohammad Taghi; Ahmadi, Masoomeh; Ghasemi, Maryam; Shaabani, Ahmad; Notash, Behrouz; Organic & biomolecular chemistry 21 (2023) 4095–4108; doi:10.1039/d3ob00250k

data_7159325
_publ_section_title
;
 The new synthesis of pyrrole-fused
 dibenzo[<i>b</i>,<i>f</i>][1,4]oxazepine/thiazepines by the
 pseudo-Joulli&#xe9;-Ugi reaction <i>via</i> an unexpected route with high
 chemoselectivity.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4095
_journal_page_last               4108
_journal_paper_doi               10.1039/d3ob00250k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C24 H24 N2 O5'
_chemical_formula_sum            'C24 H24 N2 O5'
_chemical_formula_weight         420.45
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-11-16 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                107.89(3)
_cell_angle_beta                 92.67(3)
_cell_angle_gamma                90.21(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1923(14)
_cell_length_b                   9.941(2)
_cell_length_c                   15.929(3)
_cell_measurement_reflns_used    3807
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.15
_cell_volume                     1082.5(4)
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8186
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0843P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                2479
_reflns_number_total             3807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ob00250k2.cif
_cod_data_source_block           khc1712h
_cod_depositor_comments          'Adding full bibliography for 7159325.cif.'
_cod_database_code               7159325