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_7220063
_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            'C30 H22 N4 O4.5 S0.5'
_chemical_formula_weight         526.54
_chemical_melting_point          255.0(10)
_chemical_name_systematic        spiro
_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_creation_method           SHELXL-2012
_audit_update_record
;
2014-11-22 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.7230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.9048(6)
_cell_length_b                   9.4980(2)
_cell_length_c                   22.2694(6)
_cell_measurement_reflns_used    12338
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      1.75
_cell_volume                     4926.9(2)
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker smart apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_av_unetI/netI     0.1589
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46298
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_min         1.748
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.8451
_exptl_absorpt_correction_T_min  0.7418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO-D6'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     846
_refine_ls_number_reflns         12338
_refine_ls_number_restraints     284
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2374
_refine_ls_R_factor_gt           0.0662
_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^)+(0.0909P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.2177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4043
_reflns_number_total             12338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5gc00006h2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '254-256' was changed to '255.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 7220062--7220063.cif.
;
_cod_original_formula_sum        'C30 H22 N4 O4.50 S0.50'
_cod_database_code               7220063
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           2012-9
_shelx_res_checksum              26409
_shelx_hkl_checksum              41934