Synthesis of Quinolines and Isoquinolines via Site-Selective, Domino Benzannulation of 2- and 3-Chloropyridyl Ynones with Nitromethane.
Beesu, Mallesh; Mehta, Goverdhan; The Journal of organic chemistry 84 (2019) 8731–8742; doi:10.1021/acs.joc.9b00950

data_4034147
_publ_section_title
;
 Synthesis of Quinolines and Isoquinolines via Site-Selective, Domino
 Benzannulation of 2- and 3-Chloropyridyl Ynones with Nitromethane.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8731
_journal_page_last               8742
_journal_paper_doi               10.1021/acs.joc.9b00950
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H12 N2 O4'
_chemical_formula_sum            'C16 H12 N2 O4'
_chemical_formula_weight         296.28
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_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 106.149(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4313(12)
_cell_length_b                   9.4929(10)
_cell_length_c                   14.4559(17)
_cell_measurement_reflns_used    9815
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.60
_cell_volume                     1375.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            91803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.299
_diffrn_reflns_theta_min         2.599
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            PALE-YELLOW
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             616
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0469P)^2^+0.6700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2351
_reflns_number_total             2770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00950_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034147
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              67876
_shelx_hkl_checksum              12254