Organocatalytic enantio- and diastereoselective synthesis of highly substituted ?-lactones via a Michael-cyclization cascade
Santosh Agrawal; Nagaraju Molleti; Vinod K. Singh; Chem.Commun. 51 (2015) 9793–; doi:10.1039/C5cc02776D

data_7117252
_publ_section_title
;
 Organocatalytic enantio- and diastereoselective synthesis of highly
 substituted ?-lactones via a Michael-cyclization cascade
;
_journal_name_full               Chem.Commun.
_journal_page_first              9793
_journal_paper_doi               10.1039/C5cc02776D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C21 H19 Cl N2 O3'
_chemical_formula_weight         382.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-01-22 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1999(5)
_cell_length_b                   13.2765(11)
_cell_length_c                   23.277(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1916.0(3)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11558
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         1.750
_exptl_absorpt_coefficient_mu    0.223
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             800.0
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0742P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1515
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2041
_reflns_number_total             3390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc02776d2.cif
_cod_data_source_block           4-Chloro
_cod_database_code               7117252
_shelxl_version_number           2014/6
_shelx_res_checksum              14488
_shelx_hkl_checksum              67540