N-Heterocyclic carbene-catalyzed diastereoselective synthesis of beta-lactone-fused cyclopentanes using homoenolate annulation reaction
Subrata Mukherjee; Santigopal Mondal; Atanu Patra; Rajesh G. Gonnade; Akkattu T. Biju; Chem.Commun. 51 (2015) 9559–; doi:10.1039/C5cc02960K

data_7117228
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed diastereoselective synthesis of
 beta-lactone-fused cyclopentanes using homoenolate annulation reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              9559
_journal_paper_doi               10.1039/C5cc02960K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C23 H18 N2 O4'
_chemical_formula_sum            'C23 H18 N2 O4'
_chemical_formula_weight         386.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.356(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8247(5)
_cell_length_b                   12.1491(5)
_cell_length_c                   14.0090(6)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      35.53
_cell_measurement_theta_min      2.22
_cell_volume                     1831.00(14)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0102
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35378
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl Acetate-Petroleum Ether'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0336P)^2^+0.8563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                2962
_reflns_number_total             3226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02960k2.cif
_cod_data_source_block           sgm_se_67_0m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7117228