Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction.
Bakthadoss, M.; Kannan, D.; Srinivasan, J.; Vinayagam, V.; Organic & biomolecular chemistry 13 (2015) 2870–2874; doi:10.1039/c4ob02203c

data_7154271
_publ_section_title
;
 Highly regio- and diastereo-selective synthesis of novel tri- and
 tetra-cyclic perhydroquinoline architectures via an intramolecular [3 +
 2] cycloaddition reaction.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2870
_journal_page_last               2874
_journal_paper_doi               10.1039/c4ob02203c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C32 H36 N2 O4 S'
_chemical_formula_weight         544.69
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-12-11 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                75.845(2)
_cell_angle_beta                 76.824(2)
_cell_angle_gamma                62.065(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3767(4)
_cell_length_b                   10.8064(4)
_cell_length_c                   15.0426(5)
_cell_measurement_reflns_used    7173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.44
_cell_measurement_theta_min      2.12
_cell_volume                     1432.29(9)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28853
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.9086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0661P)^2^+0.5189P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                5487
_reflns_number_total             6574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02203c2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7154269--7154271.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154271