Enantioselective Synthesis of Functionalized β-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids.
Mondal, Santigopal; Mukherjee, Subrata; Das, Tamal Kanti; Gonnade, Rajesh G.; Biju, Akkattu T.; The Journal of organic chemistry 82 (2017) 9223–9228; doi:10.1021/acs.joc.7b01526

data_4032782
_publ_section_title
;
 Enantioselective Synthesis of Functionalized \b-Lactones by NHC-Catalyzed
 Aldol Lactonization of Ketoacids.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9223
_journal_page_last               9228
_journal_paper_doi               10.1021/acs.joc.7b01526
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H26 O6'
_chemical_formula_sum            'C17 H26 O6'
_chemical_formula_weight         326.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 118.017(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2074(17)
_cell_length_b                   11.5642(5)
_cell_length_c                   9.5785(18)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.48
_cell_measurement_theta_min      3.82
_cell_volume                     900.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_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      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21833
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.462
_diffrn_reflns_theta_min         10.934
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details
;
 Flack x determined using 1693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.070(16)
_refine_ls_extinction_coef       0.025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0226
_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^)+(0.0476P)^2^+0.0754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0653
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                3651
_reflns_number_total             3654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01526_si_002.cif
_cod_data_source_block           cu_SUM_SC_122_0m
_cod_database_code               4032782
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.790
_shelx_estimated_absorpt_t_max   0.871
_shelx_res_checksum              7303
_shelx_hkl_checksum              62130