Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes
Patra, Atanu; Bhunia, Anup; Yetra, Santhivardhana Reddy; Gonnade, Rajesh G.; Biju, Akkattu T.; Organic Chemistry Frontiers 2 (2015) 1584–; doi:10.1039/C5QO00242G

data_1553181
_publ_section_title
;
 Diastereoselective synthesis of cyclopentanone-fused spirooxindoles by
 N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1584
_journal_paper_doi               10.1039/C5QO00242G
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C29 H27 N O4'
_chemical_formula_sum            'C29 H27 N O4'
_chemical_formula_weight         453.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-20 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                88.719(3)
_cell_angle_beta                 87.476(3)
_cell_angle_gamma                80.292(3)
_cell_formula_units_Z            4
_cell_length_a                   10.7670(9)
_cell_length_b                   11.4830(9)
_cell_length_c                   19.2866(15)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.23
_cell_volume                     2347.8(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35150
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.799
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane-petroleum ether'
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         9223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0329P)^2^+1.1053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8423
_reflns_number_total             9223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00242g2.cif
_cod_data_source_block           shelx
_cod_database_code               1553181
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              92704
_shelx_hkl_checksum              21760