Efficient and metal-free synthesis of 2-aroyl 7-azaindoles <i>via</i> thermally induced denitrogenative intramolecular annulation of 1,2,3,4-tetrazolopyridines.
Chamakiya, Chirag A.; Chothani, Savankumar R.; Joshi, Rupal J.; Bhalodia, Jasmin; Ambasana, Mrunal A.; Bapodra, Atul H.; Kapuriya, Naval; Organic & biomolecular chemistry 22 (2024) 2192–2196; doi:10.1039/d4ob00078a

data_7159822
_publ_section_title
;
 Efficient and metal-free synthesis of 2-aroyl 7-azaindoles <i>via</i>
 thermally induced denitrogenative intramolecular annulation of
 1,2,3,4-tetrazolopyridines.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2192
_journal_page_last               2196
_journal_paper_doi               10.1039/d4ob00078a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H14 N2 O'
_chemical_formula_sum            'C20 H14 N2 O'
_chemical_formula_weight         298.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-09 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                80.01(2)
_cell_angle_beta                 88.13(2)
_cell_angle_gamma                87.10(2)
_cell_formula_units_Z            2
_cell_length_a                   4.045(3)
_cell_length_b                   12.408(11)
_cell_length_c                   15.626(14)
_cell_measurement_temperature    273(2)
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_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.990
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
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_diffrn_reflns_limit_h_min       -3
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_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_point_group_measured_fraction_full 0.990
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_exptl_absorpt_coefficient_mu    0.081
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_exptl_crystal_size_max          0.435
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_exptl_crystal_size_min          0.043
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_refine_diff_density_min         -0.185
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_refine_ls_extinction_coef       0.15(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.1148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                3231
_reflns_number_total             3901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00078a2.cif
_cod_data_source_block           cmp_2a_m_a
_cod_depositor_comments          'Adding full bibliography for 7159822.cif.'
_cod_original_cell_volume        771.2(12)
_cod_database_code               7159822
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N21(H21), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              24763
_olex2_submission_special_instructions 'No special instructions were received'