Tandem aza-Michael addition-vinylogous aldol condensation: synthesis of <i>N</i>-bridged pyridine fused quinolones.
Gummidi, Lalitha; Muddassar, Altaf; Sharma, Gangavaram V. M.; Murugesh, V.; Suresh, Surisetti; Organic & biomolecular chemistry 20 (2022) 773–777; doi:10.1039/d1ob02087k

data_7158475
_publ_section_title
;
 Tandem aza-Michael addition-vinylogous aldol condensation: synthesis of
 <i>N</i>-bridged pyridine fused quinolones.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              773
_journal_page_last               777
_journal_paper_doi               10.1039/d1ob02087k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C29 H23 N O3'
_chemical_formula_weight         433.48
_chemical_name_systematic
'Ethyl 6-oxo-1-phenyl-3-(p-tolyl)-6H-pyrido[1,2-a]quinoline-5-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.309
_cell_measurement_theta_min      2.319
_cell_volume                     2311.8(16)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22049
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.514
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile and Ethanol (1:1)'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5694
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0606P)^2^+0.5199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3145
_reflns_number_total             5694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02087k2.cif
_cod_data_source_block           KB272_0m
_cod_depositor_comments          'Adding full bibliography for 7158475.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158475
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              10713