Enantioselective Hetero-Diels-Alder Reaction and the Synthesis of Spiropyrrolidone Derivatives.
Huang, Yekai; Li, Yanan; Sun, Jianan; Li, Jindong; Zha, Zhenggen; Wang, Zhiyong; The Journal of organic chemistry 83 (2018) 8464–8472; doi:10.1021/acs.joc.8b01057

data_4035613
_publ_section_title
;
 Enantioselective Hetero-Diels-Alder Reaction and the Synthesis of
 Spiropyrrolidone Derivatives.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8464
_journal_page_last               8472
_journal_paper_doi               10.1021/acs.joc.8b01057
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H21 N O4'
_chemical_formula_weight         375.41
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 94.850(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.56360(10)
_cell_length_b                   10.0307(3)
_cell_length_c                   17.1567(4)
_cell_measurement_reflns_used    12004
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.4270
_cell_measurement_theta_min      4.3130
_cell_volume                     954.03(4)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15426
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.662
_diffrn_reflns_theta_min         5.112
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.09(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0744P)^2^+0.0916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                3432
_reflns_number_total             3511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01057_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035613
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.856
_shelxl_version_number           2013-4
_shelx_res_checksum              65198
_shelx_hkl_checksum              26009