Efficient synthesis of novel N-substituted 2-carboxy-4-quinolones via lithium bis(trimethylsilyl)amide (LiHMDS)-induced in situ cyclocondensation reaction
Hasan, Phool; Aneja, Babita; Masood, Mir M.; Ahmad, Md. Belal; Yadava, Umesh; Daniliuc, Constantin G.; Abid, Mohammad; RSC Adv. 7 (2017) 11367–; doi:10.1039/C6RA28631C

data_7227684
_publ_section_title
;
 Efficient synthesis of novel N-substituted 2-carboxy-4-quinolones via
 lithium bis(trimethylsilyl)amide (LiHMDS)-induced in situ
 cyclocondensation reaction
;
_journal_issue                   19
_journal_name_full               'RSC Adv.'
_journal_page_first              11367
_journal_paper_doi               10.1039/C6RA28631C
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C14 H13 Cl N2 O'
_chemical_formula_weight         260.71
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2017-01-31 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.257(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5288(10)
_cell_length_b                   5.2501(4)
_cell_length_c                   17.6225(12)
_cell_measurement_reflns_used    3649
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.9295
_cell_measurement_theta_min      5.0585
_cell_volume                     1234.98(16)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1326
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9359
_diffrn_reflns_theta_full        64.37
_diffrn_reflns_theta_max         64.37
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    2.642
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.545
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2017
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.327
_refine_ls_R_factor_all          0.2002
_refine_ls_R_factor_gt           0.1800
_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^)+(0.0001P)^2^+30.4509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3342
_refine_ls_wR_factor_ref         0.3428
_reflns_number_gt                1686
_reflns_number_total             2017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra28631c2.cif
_cod_data_source_block           dan8187
_cod_database_code               7227684
_shelx_res_checksum              19277