Dual Behavior of Isatin-Based Cyclic Ketimines with Dicarbomethoxy Carbene: Expedient Synthesis of Highly Functionalized Spirooxindolyl Oxazolidines and Pyrrolines
Rajasekaran, T.; Karthik, G.; Sridhar, B.; Subba Reddy, B. V.; Organic Letters 15 (2013) 1512–; doi:10.1021/ol400287q

data_1511875
_publ_section_title
;
 Dual Behavior of Isatin-Based Cyclic Ketimines with Dicarbomethoxy
 Carbene: Expedient Synthesis of Highly Functionalized Spirooxindolyl
 Oxazolidines and Pyrrolines
;
_journal_issue                   7
_journal_name_full               'Organic Letters'
_journal_page_first              1512
_journal_paper_doi               10.1021/ol400287q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C32 H28 N2 O9'
_chemical_formula_sum            'C32 H28 N2 O9'
_chemical_formula_weight         584.56
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.901(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9805(11)
_cell_length_b                   19.764(3)
_cell_length_c                   17.862(3)
_cell_measurement_reflns_used    6946
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.31
_cell_volume                     2775.4(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w 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  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22205
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0423P)^2^+1.0981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                3520
_reflns_number_total             4878
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol400287q_si_002.cif
_cod_data_source_block           ao79
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1511875