Palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines: construction of sulfamate-fused pyrrolidines.
Sun, Honghao; Ding, Siyuan; Wang, Bo; Huang, Jiaxing; Guo, Hongchao; Organic & biomolecular chemistry 23 (2024) 90–93; doi:10.1039/d4ob01611d

data_7160206
_publ_section_title
;
 Palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones
 with sulfamate-derived cyclic imines: construction of sulfamate-fused
 pyrrolidines.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              90
_journal_page_last               93
_journal_paper_doi               10.1039/d4ob01611d
_journal_volume                  23
_journal_year                    2024
_chemical_formula_moiety         'C31 H26 O6'
_chemical_formula_sum            'C31 H26 O6'
_chemical_formula_weight         494.52
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2k1px7
_audit_creation_date             2024-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-11 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.201(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.62090(10)
_cell_length_b                   14.4274(2)
_cell_length_c                   20.7278(3)
_cell_measurement_reflns_used    14294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9590
_cell_measurement_theta_min      2.1750
_cell_volume                     2577.50(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.954
_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    -35.00  -9.00   0.50    0.50    --   42.30 -82.00   0.00   52
  2  \w    -41.00  13.00   0.50    0.50    --   42.30 -77.00  90.00  108
  3  \w     27.00  70.00   0.50    0.50    --   42.30 -82.00  90.00   86
  4  \w     25.00  70.00   0.50    0.50    --   42.30 -82.00   0.00   90
  5  \w     21.00  47.00   0.50    0.50    --   42.30 -65.00  30.00   52
  6  \w    -46.00  72.00   0.50    0.50    --   42.30 -54.00-180.00  236
  7  \w     41.00  66.00   0.50    0.50    --   42.30 -82.00-150.00   50
  8  \w     36.00  68.00   0.50    0.50    --   42.30 -82.00 150.00   64
  9  \w     33.00  59.00   0.50    0.50    --   42.30 -77.00  90.00   52
 10  \w    -46.00  23.00   0.50    0.50    --   42.30 -77.00 -90.00  138
 11  \w     21.00 132.00   0.50    0.50    --   42.30  82.00  90.00  222
 12  \w     28.00  53.00   0.50    0.50    --   42.30 -82.00  60.00   50
 13  \w    -26.00   0.00   0.50    0.50    --   42.30 -65.00  30.00   52
 14  \w    -37.00  16.00   0.50    0.50    --   42.30 -82.00  60.00  106
 15  \w     34.00  66.00   0.50    0.50    --   42.30 -77.00 -90.00   64
 16  \w     43.00  68.00   0.50    0.50    --   42.30 -82.00 -90.00   50
 17  \w     21.00  53.00   0.50    0.50    --   42.30  65.00  30.00   64
 18  \w    -44.00   7.00   0.50    0.50    --   42.30 -82.00-150.00  102
 19  \w    -47.00   8.00   0.50    0.50    --   42.30 -82.00 150.00  110
 20  \w     40.00  80.00   0.50    0.50    --   42.30  82.00 -30.00   80
 21  \w     59.00 113.00   0.50    0.50    --   93.40 -82.00  30.00  108
 22  \w      5.00 110.00   0.50    0.50    --   93.40 -59.00-180.00  210
 23  \w      4.00 182.00   0.50    0.50    --   93.40   0.00 -90.00  356
 24  \w     64.00  90.00   0.50    0.50    --   93.40 -82.00-120.00   52
 25  \w     40.00 128.00   0.50    0.50    --   93.40 -33.00   0.00  176
 26  \w     18.00 121.00   0.50    0.50    --   93.40 -82.00-180.00  206
 27  \w     16.00 127.00   0.50    0.50    --   93.40 -33.00-150.00  222
 28  \w     65.00  91.00   0.50    0.50    --   93.40 -82.00  90.00   52
 29  \w     88.00 113.00   0.50    0.50    --   93.40 -59.00   0.00   50
 30  \w     18.00  98.00   0.50    0.50    --   93.40 -82.00 150.00  160
 31  \w      5.00  56.00   0.50    0.50    --   93.40 -59.00   0.00  102
 32  \w      5.00  31.00   0.50    0.50    --   93.40 -33.00   0.00   52
 33  \w     28.00 121.00   0.50    0.50    --   93.40 -82.00 -30.00  186
 34  \w     67.00 106.00   0.50    0.50    --   93.40 -82.00-150.00   78
 35  \w     69.00  94.00   0.50    0.50    --   93.40 -82.00 -90.00   50
 36  \w     39.00  94.00   0.50    0.50    --   93.40 -82.00 -60.00  110
 37  \w     12.00  92.00   0.50    0.50    --   93.40 -82.00  60.00  160
 38  \w     84.00 125.00   0.50    0.50    --   93.40  59.00  60.00   82
 39  \w    133.00 158.00   0.50    0.50    --   93.40  59.00  60.00   50
 40  \w    143.00 168.00   0.50    0.50    --   93.40  50.00 -60.00   50
 41  \w    101.00 127.00   0.50    0.50    --   93.40  50.00 -60.00   52
 42  \w     11.00  90.00   0.50    0.50    --   93.40 -82.00 120.00  158
 43  \w      8.00  70.00   0.50    0.50    --   93.40 -33.00-180.00  124
 44  \w     86.00 112.00   0.50    0.50    --   93.40 -82.00   0.00   52
 45  \w     18.00  63.00   0.50    0.50    --   93.40 -82.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0664718000
_diffrn_orient_matrix_UB_12      -0.0824778000
_diffrn_orient_matrix_UB_13      0.0376841000
_diffrn_orient_matrix_UB_21      -0.0718237000
_diffrn_orient_matrix_UB_22      0.0676733000
_diffrn_orient_matrix_UB_23      0.0484652000
_diffrn_orient_matrix_UB_31      -0.1496503000
_diffrn_orient_matrix_UB_32      0.0041704000
_diffrn_orient_matrix_UB_33      -0.0418864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25388
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.146
_diffrn_reflns_theta_min         3.733
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0593P)^2^+0.3654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4058
_reflns_number_total             4596
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01611d2.cif
_cod_data_source_block           1_auto
_cod_depositor_comments          'Adding full bibliography for 7160206.cif.'
_cod_database_code               7160206
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.958
_diffrn_oxdiff_digest_frames
;
01fa35ad3f076ad3b14c7ef03003436d14000307995
;
_diffrn_oxdiff_digest_hkl
;
0161d1e73bc882892ed61843a24e4330ad03b0
;
_reflns_odcompleteness_completeness 97.53
_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:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.e Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              2799
_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 1.735
_oxdiff_exptl_absorpt_empirical_full_min 0.628