An amine template strategy to construct successive C-C bonds: synthesis of benzo[<i>h</i>]quinolines by a deaminative ring contraction cascade.
McFadden, Timothy Patrick; Nwachukwu, Chideraa Iheanyi; Roberts, Andrew George; Organic & biomolecular chemistry 20 (2022) 1379–1385; doi:10.1039/d1ob02245h

data_7158501
_publ_section_title
;
 An amine template strategy to construct successive C-C bonds: synthesis
 of benzo[<i>h</i>]quinolines by a deaminative ring contraction cascade.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1379
_journal_page_last               1385
_journal_paper_doi               10.1039/d1ob02245h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_common            deoxytoddaquinoline
_chemical_name_systematic
6-methyl-6,7-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]pyrido[2,3-e]azepine
_chemical_properties_physical    'Not sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
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_audit_update_record
;
2021-06-01 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
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_diffrn_ambient_temperature      100(2)
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_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0359
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_source                   'Fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.095
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       irregular
_exptl_crystal_F_000             268
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methylene chloride'
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         5526
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.0913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1244
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_reflns_number_gt                4242
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02245h2.cif
_cod_data_source_block           20210324AR_0m
_cod_depositor_comments
'Adding full bibliography for 7158501--7158502.cif.'
_cod_database_code               7158501
_shelx_shelxl_version_number     2017/1
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_shelx_res_checksum              56457