Reaction of isatins with 6-amino uracils and isoxazoles: isatin ring-opening vs. annulations and regioselective synthesis of isoxazole fused quinoline scaffolds in water
Poomathi, Nataraj; Mayakrishnan, Sivakalai; Muralidharan, Doraiswamy; Srinivasan, Rajagopal; Perumal, Paramasivan T.; Green Chem. 17 (2015) 3362–; doi:10.1039/C5GC00006H

data_7220062
_publ_section_title
;
 Reaction of isatins with 6-amino uracils and isoxazoles: isatin
 ring-opening vs. annulations and regioselective synthesis of isoxazole
 fused quinoline scaffolds in water
;
_journal_issue                   6
_journal_name_full               'Green Chem.'
_journal_page_first              3362
_journal_paper_doi               10.1039/C5GC00006H
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C22 H16 F N5 O3'
_chemical_formula_weight         417.40
_chemical_melting_point          340
_chemical_name_common            'quinoline fused isoxazole'
_chemical_name_systematic        quinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc13888x
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-08-24 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.8261(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3119(5)
_cell_length_b                   10.7033(4)
_cell_length_c                   13.8141(4)
_cell_measurement_reflns_used    5199
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.41
_cell_volume                     1967.25(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 1.000
_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  0.0214
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14836
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.408
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO-D6, DMF'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0496P)^2^+0.6326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2750
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5gc00006h2.cif
_cod_data_source_block           spiro
_cod_depositor_comments
'Adding full bibliography for 7220062--7220063.cif.'
_cod_database_code               7220062
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-4
_shelx_res_checksum              48429
_shelx_hkl_checksum              1866