Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes.
Hu, Xinyue; Zhou, Yuhang; Lu, Yan; Zou, Sijia; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; The Journal of organic chemistry 83 (2018) 8679–8687; doi:10.1021/acs.joc.8b00839

data_4035587
_publ_section_title
;
 Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction
 of Dioxopyrrolidines with Hetero-Substituted Alkenes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8679
_journal_page_last               8687
_journal_paper_doi               10.1021/acs.joc.8b00839
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-13
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_a                   7.4368(2)
_cell_length_b                   13.4944(4)
_cell_length_c                   18.7500(6)
_cell_measurement_reflns_used    783
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.8500
_cell_measurement_theta_min      4.7130
_cell_volume                     1881.66(10)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
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_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000   26.5300
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000   60.0000 94

  2 omega   10.00  104.00   1.0000   26.5300
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -90.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0459984000
_diffrn_orient_matrix_UB_12      0.0935214000
_diffrn_orient_matrix_UB_13      0.0432737000
_diffrn_orient_matrix_UB_21      0.0021606000
_diffrn_orient_matrix_UB_22      -0.0614385000
_diffrn_orient_matrix_UB_23      0.0691291000
_diffrn_orient_matrix_UB_31      0.2017119000
_diffrn_orient_matrix_UB_32      0.0219841000
_diffrn_orient_matrix_UB_33      0.0091422000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0383
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_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5817
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.717
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
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_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0950P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1548
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_reflns_Friedel_fraction_full    0.847
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                2741
_reflns_number_total             3134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00839_si_002.cif
_cod_data_source_block           fxm-oet
_cod_database_code               4035587
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 29.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00F(H00E,H00F), C00H(H00H,H00I), C00I(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00G(H00G), C00J(H00L), C00K(H00M), C00L(H00N),
 C00M(H00O), C00N(H00P), C00P(H00T), C00Q(H00U)
2.d Idealised Me refined as rotating group:
 C00O(H00Q,H00R,H00S)
;
_olex2_date_sample_data_collection 2017-04-12
_olex2_submission_special_instructions 'No special instructions were received'