Organocatalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with N-itaconimides: facile access to optically active spiropyrroline succinimide derivatives
Zhao, Mei-Xin; Liu, Qiang; Yu, Kun-Ming; Zhao, Xiao-Li; Shi, Min; Organic Chemistry Frontiers 6 (2019) 3879–; doi:10.1039/C9QO00939F

data_1555125
_publ_section_title
;
 Organocatalyzed asymmetric formal [3 + 2] cycloaddition of
 isocyanoacetates with N-itaconimides: facile access to optically active
 spiropyrroline succinimide derivatives
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3879
_journal_paper_doi               10.1039/C9QO00939F
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 Br N2 O4, C H Cl3'
_chemical_formula_sum            'C22 H18 Br Cl3 N2 O4'
_chemical_formula_weight         560.64
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-11 deposited with the CCDC.	2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.145(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3229(3)
_cell_length_b                   6.20240(10)
_cell_length_c                   15.4655(4)
_cell_measurement_reflns_used    14508
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2650
_cell_measurement_theta_min      5.7210
_cell_volume                     1156.87(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -31.00  27.00   1.00    4.00    --    0.00  82.00-180.00   58
  2  \w    -19.00  28.00   1.00    4.00    --    0.00  38.00 -30.00   47
  3  \w    -49.00  19.00   1.00    4.00    --    0.00 -38.00-180.00   68
  4  \w    -15.00  11.00   1.00    4.00    --    0.00 -77.00-180.00   26
  5  \w    -14.00  31.00   1.00    4.00    --    0.00  38.00 -90.00   45
  6  \w     31.00  67.00   1.00    4.00    --    0.00  38.00 -30.00   36
  7  \w     46.00  89.00   1.00    4.00    --    0.00  38.00 -90.00   43
  8  \w     33.00  82.00   1.00    4.00    --    0.00  82.00-180.00   49
  9  \w    -85.00 -60.00   1.00    4.00    --    0.00 -77.00-180.00   25
 10  \w    -23.00  80.00   1.00    4.00    --    0.00  57.00  60.00  103
 11  \w    -86.00 -54.00   1.00    4.00    --    0.00 -38.00-180.00   32
 12  \w     47.00  86.00   1.00    4.00    --    0.00  38.00 120.00   39
 13  \w     64.00  89.00   1.00    4.00    --   95.80  82.00 -30.00   25
 14  \w    134.00 185.00   1.00    4.00    --   95.80  76.00 133.88   51
 15  \w    154.00 182.00   1.00    4.00    --   95.80  69.00-122.22   28
 16  \w     65.00  94.00   1.00    4.00    --   95.80  76.00 133.88   29
 17  \w    153.00 184.00   1.00    4.00    --   95.80  67.00 -35.23   31
 18  \w    104.00 130.00   1.00    4.00    --   95.80  69.00-122.22   26
 19  \w    122.00 183.00   1.00    4.00    --   95.80  58.00  17.89   61
 20  \w    160.00 185.00   1.00    4.00    --   95.80  82.00-150.00   25
 21  \w     65.00  91.00   1.00    4.00    --   95.80  77.00 120.00   26
 22  \w     70.00  95.00   1.00    4.00    --   95.80  67.00 -35.23   25
 23  \w     63.00  89.00   1.00    4.00    --   95.80  82.00  60.00   26
 24  \w     65.00  91.00   1.00    4.00    --   95.80  77.00-150.00   26
 25  \w      7.00  55.00   1.00    4.00    --   95.80 -82.00-120.00   48
 26  \w     58.00 118.00   1.00    4.00    --   95.80 -82.00-120.00   60
 27  \w    129.00 185.00   1.00    4.00    --   95.80  82.00  90.00   56
 28  \w     63.00  89.00   1.00    4.00    --   95.80  82.00  30.00   26
 29  \w    154.00 180.00   1.00    4.00    --   95.80  82.00  30.00   26
 30  \w     66.00  91.00   1.00    4.00    --   95.80  77.00-180.00   25
 31  \w     63.00  95.00   1.00    4.00    --   95.80  82.00  90.00   32
 32  \w     72.00 110.00   1.00    4.00    --   95.80  55.00 -31.18   38
 33  \w     68.00  95.00   1.00    4.00    --   95.80  69.00-122.22   27
 34  \w     95.00 126.00   1.00    4.00    --   95.80 -77.00  30.00   31
 35  \w     15.00 101.00   1.00    4.00    --   95.80 -82.00-180.00   86
 36  \w     13.00  80.00   1.00    4.00    --   95.80 -77.00  30.00   67
 37  \w     64.00  90.00   1.00    4.00    --   95.80  80.00   5.55   26
 38  \w     77.00 170.00   1.00    4.00    --   95.80  45.00  60.00   93
 39  \w     65.00  91.00   1.00    4.00    --   95.80  77.00 -90.00   26
 40  \w    134.00 183.00   1.00    4.00    --   95.80  77.00 -90.00   49
 41  \w     66.00 108.00   1.00    4.00    --   95.80  77.00 -30.00   42
 42  \w     65.00  91.00   1.00    4.00    --   95.80  77.00  90.00   26
 43  \w    141.00 166.00   1.00    4.00    --   95.80  77.00  90.00   25
 44  \w     63.00  89.00   1.00    4.00    --   95.80  82.00-150.00   26
 45  \w     76.00 139.00   1.00    4.00    --   95.80  45.00 120.00   63
 46  \w     88.00 127.00   1.00    4.00    --   95.80 -82.00  90.00   39
 47  \w     65.00  91.00   1.00    4.00    --   95.80  77.00 -60.00   26
 48  \w     65.00  91.00   1.00    4.00    --   95.80  77.00 150.00   26
 49  \w     76.00 117.00   1.00    4.00    --   95.80  30.00  60.00   41
 50  \w     79.00 131.00   1.00    4.00    --   95.80  45.00-180.00   52
 51  \w     75.00 183.00   1.00    4.00    --   95.80  45.00-150.00  108
 52  \w     76.00 150.00   1.00    4.00    --   95.80  45.00 -30.00   74
 53  \w     77.00 137.00   1.00    4.00    --   95.80  45.00 150.00   60
 54  \w     63.00  90.00   1.00    4.00    --   95.80  82.00 150.00   27
 55  \w      8.00 126.00   1.00    4.00    --   95.80 -82.00   0.00  118
 56  \w     64.00  89.00   1.00    4.00    --   95.80  79.00-109.85   25
 57  \w     84.00 125.00   1.00    4.00    --   95.80  30.00  30.00   41
 58  \w     76.00 165.00   1.00    4.00    --   95.80  45.00-120.00   89
 59  \w     72.00  97.00   1.00    4.00    --   95.80  61.00 -60.00   25
 60  \w     69.00 184.00   1.00    4.00    --   95.80  66.00  67.50  115
 61  \w     72.00  99.00   1.00    4.00    --   95.80  58.00  17.89   27
 62  \w     66.00  93.00   1.00    4.00    --   95.80  82.00-180.00   27
 63  \w     75.00 168.00   1.00    4.00    --   95.80  57.00 -96.89   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237878000
_diffrn_orient_matrix_UB_12      -0.0969476000
_diffrn_orient_matrix_UB_13      0.0985229000
_diffrn_orient_matrix_UB_21      0.1099946000
_diffrn_orient_matrix_UB_22      0.1259675000
_diffrn_orient_matrix_UB_23      0.0443841000
_diffrn_orient_matrix_UB_31      -0.0604892000
_diffrn_orient_matrix_UB_32      0.1908409000
_diffrn_orient_matrix_UB_33      0.0207054000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23138
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.806
_diffrn_reflns_theta_min         3.665
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.232
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+1.1260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4428
_reflns_number_total             4644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00939f2.cif
_cod_data_source_block           exp_745
_cod_database_code               1555125
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.799
_shelx_estimated_absorpt_t_min   0.226
_reflns_odcompleteness_completeness 99.91
_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:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;
_shelx_res_checksum              23451
_shelx_hkl_checksum              60540
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.648
_oxdiff_exptl_absorpt_empirical_full_min 0.384