A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction.
Bakthadoss, Manickam; Vinayagam, Varathan; Organic & biomolecular chemistry 13 (2015) 10007–10014; doi:10.1039/c5ob01060h

data_7154739
_publ_section_title
;
 A novel protocol for the facile construction of tetrahydroquinoline fused
 tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide
 cycloaddition reaction.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10007
_journal_page_last               10014
_journal_paper_doi               10.1039/c5ob01060h
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        synthatic
_chemical_formula_moiety         'C24 H18 Cl N3 O3 S'
_chemical_formula_sum            'C24 H18 Cl N3 O3 S'
_chemical_formula_weight         463.92
_chemical_melting_point          435.15
_chemical_name_common
'3-(2-chlorophenyl)-5-tosyl-3,3a,4,5-tetrahydroisoxazolo [4,3-c] quinoline - 3a- carbonitrile'
_chemical_name_systematic
'3-(2-chlorophenyl)-5-tosyl-3,3a,4,5-tetrahydroisoxazolo [4,3-c] quinoline - 3a- carbonitrile'
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-19 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.398(2)
_cell_length_b                   9.776(2)
_cell_length_c                   24.059(6)
_cell_measurement_temperature    296(2)
_cell_volume                     2210.4(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.877
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10416
_diffrn_reflns_theta_full        66.66
_diffrn_reflns_theta_max         66.66
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    2.680
_exptl_crystal_colour            clourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strong
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethonal'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.41(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1427P)^2^+0.3352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1969
_reflns_number_gt                2703
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01060h2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7154739