Iodine-promoted amide formation via oxidative cleavage of indoles: novel quinazoline-4(3H)-one and tryptanthrin syntheses
Le, Phong Q.; Dinh, Van M.; Nguyen, Huong D. T.; Ha, Hiep Q.; Truong, Thanh V.; RSC Advances 14 (2024) 15597–15603; doi:10.1039/D4RA01807A

data_7248606
_publ_section_title
;
 Iodine-promoted amide formation via oxidative cleavage of indoles: novel
 quinazoline-4(3H)-one and tryptanthrin syntheses
;
_journal_issue                   22
_journal_name_full               'RSC Advances'
_journal_page_first              15597
_journal_page_last               15603
_journal_paper_doi               10.1039/D4RA01807A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C20 H13 Br N2 O'
_chemical_formula_sum            'C20 H13 Br N2 O'
_chemical_formula_weight         377.24
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2018-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-01-19 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.688(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0685(4)
_cell_length_b                   14.1345(4)
_cell_length_c                   18.6642(6)
_cell_measurement_reflns_used    9827
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.90
_cell_volume                     3168.10(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      0.0
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            96733
_diffrn_reflns_theta_full        28.3516
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.603
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.5817
_exptl_crystal_F_000             1518.3487
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.5308
_refine_diff_density_min         -0.6436
_refine_diff_density_rms         0.1155
_refine_ls_d_res_high            0.7483
_refine_ls_d_res_low             7.0672
_refine_ls_goodness_of_fit_ref   1.0404
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0404
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+2.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                6176
_reflns_number_total             7882
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ra01807a2.cif
_cod_data_source_block           L5_test_a
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H26 Br2 N4 O2'
_cod_original_formula_weight         754.48
_cod_original_formula_moiety         '2(C20 H13 Br N2 O)'
_cod_original_formula_units_Z            4
_cod_database_code               7248606
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: Br1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00U(H00U), C00O(H00O), C00N(H00N), C00H(H00H), C018(H018), C017(H017),
 C01B(H01B), C01A(H01A), C014(H014), C00Y(H00Y), C00T(H00T), C00Q(H00Q),
 C00S(H00S), C011(H011), C00W(H00W), C00D(H00D), C00A(H00A), C00Z(H00Z),
 C015(H015), C01C(H01C), C016(H016), C00K(H00K), C013(H013), C00X(H00X),
 C00V(H00V), C019(H019)
;
_olex2_submission_special_instructions 'No special instructions were received'