Natural Product-Derived Chiral Pyrrolidine-2,5-diones, Their Molecular Structures and Conversion to Pharmacologically Important Skeletons.
Habel, Deenamma; Nair, Divya S.; Kallingathodi, Zabeera; Mohan, Chithra; Pillai, Sarath M.; Nair, Rani R.; Thomas, Grace; Haleema, Simimole; Gopinath, Chithra; Abdul, Rinshad V.; Fritz, Matthew; Puente, Andrew R.; Johnson, Jordan L.; Polavarapu, Prasad L.; Ibnusaud, Ibrahim; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.0c00211

data_1558431
_publ_section_title
;
 Natural Product-Derived Chiral Pyrrolidine-2,5-diones, Their Molecular
 Structures and Conversion to Pharmacologically Important Skeletons.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00211
_journal_year                    2020
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 101.050(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.693(5)
_cell_length_b                   5.0152(10)
_cell_length_c                   24.780(5)
_cell_measurement_reflns_used    2979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.95
_cell_measurement_theta_min      3.28
_cell_volume                     3011.9(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS Kappa Apex2 CMOS diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3499
_diffrn_reflns_av_unetI/netI     0.2481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         3.280
_diffrn_source                   'Sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruer, 1999)'
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.2375
_refine_ls_R_factor_gt           0.1008
_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^)+(0.0238P)^2^+13.5206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2467
_reflns_number_total             5247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00211_si_008.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3011.8(11)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1558431
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              13682
_shelx_hkl_checksum              58790