Ring expansion and fused cyclization catalysis to construct indoloquinazolinones with functionalization.
Baidya, Ramlal; Das, Prasenjit; Pratihar, Pintu; Maiti, Dilip K.; Chemical communications (Cambridge, England) 59 (2023) 7978–7981; doi:10.1039/d3cc01429k

data_7131638
_publ_section_title
;
 Ring expansion and fused cyclization catalysis to construct
 indoloquinazolinones with functionalization.
;
_journal_issue                   51
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7978
_journal_page_last               7981
_journal_paper_doi               10.1039/d3cc01429k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H15 Cl N2 O2, C2 H6 O S'
_chemical_formula_sum            'C25 H21 Cl N2 O3 S'
_chemical_formula_weight         464.95
_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
_audit_creation_date             2023-01-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-06 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                94.38(6)
_cell_angle_beta                 109.83(6)
_cell_angle_gamma                93.94(6)
_cell_formula_units_Z            2
_cell_length_a                   10.012(6)
_cell_length_b                   10.023(8)
_cell_length_c                   11.978(6)
_cell_measurement_reflns_used    745
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.76
_cell_measurement_theta_min      1.98
_cell_volume                     1121.7(13)
_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    'SHELX97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2528
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        16.644
_diffrn_reflns_theta_max         16.644
_diffrn_reflns_theta_min         1.818
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       cube
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         1182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0720
_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^)+(0.1531P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                760
_reflns_number_total             1182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01429k2.cif
_cod_data_source_block           rb316_0m
_cod_depositor_comments          'Adding full bibliography for 7131638.cif.'
_cod_original_cell_volume        1121.6(13)
_cod_database_code               7131638
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.930
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C25) = Uanis(C8)
Uanis(C22) = Uanis(C8) = Uanis(C13)
Uanis(C17) = Uanis(C8)
Uanis(C9) = Uanis(C8)
3.a Me refined with riding coordinates:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22)
;
_shelx_res_checksum              70164
_shelx_hkl_checksum              89504
_olex2_submission_special_instructions 'No special instructions were received'