Palladium-catalyzed stereoselective (3 + 2) cycloaddition of vinylethylene carbonates with cyclic <i>N</i>-sulfonyl ketimines.
Gao, Xing; Zhu, Dongyu; Jiang, Feng; Liao, Jianning; Wang, Wei; Wu, Yongjun; Zheng, Lufei; Guo, Hongchao; Organic & biomolecular chemistry 19 (2021) 4877–4881; doi:10.1039/d1ob00614b

data_7158073
_publ_section_title
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 Palladium-catalyzed stereoselective (3 + 2) cycloaddition of
 vinylethylene carbonates with cyclic <i>N</i>-sulfonyl ketimines.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4877
_journal_page_last               4881
_journal_paper_doi               10.1039/d1ob00614b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C31 H25 N O4 S'
_chemical_formula_sum            'C31 H25 N O4 S'
_chemical_formula_weight         507.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-19 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                97.37(3)
_cell_angle_beta                 95.12(3)
_cell_angle_gamma                94.17(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6699(15)
_cell_length_b                   11.185(2)
_cell_length_c                   14.839(3)
_cell_measurement_reflns_used    3796
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.3907
_cell_volume                     1252.9(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11494
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         1.391
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5668
_refine_ls_number_restraints     310
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0291P)^2^+0.8649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5108
_reflns_number_total             5668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00614b2.cif
_cod_data_source_block           bww18543a
_cod_depositor_comments
'Adding full bibliography for 7158073--7158075.cif.'
_cod_database_code               7158073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C14A-C13A = C15A-C14A = C15A-C10A = C11A-C10A = C12A-C11A = C13A-C12A = C13-
 C12 = C14-C13 = C15-C14 = C15-C10 = C11-C10 = C12-C11
 1.39 with sigma of 0.02
 C9A-C10A = C9-C10
 1.51 with sigma of 0.02
 C8A-C7 = C8-C7
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C10A \\sim C15A
\\sim C14A \\sim C13A \\sim C12A \\sim C11A: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.01
C8 \\sim C9 \\sim C9A \\sim C8A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C9A)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C13A) \\sim Ueq,
Uanis(C12A) \\sim Ueq, Uanis(C11A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4. Others
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=
 Sof(H14A)=Sof(C13A)=Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=1-FVAR(1)
 Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=FVAR(1)
5.a Riding coordinates:
 C8A(H8A), C9A(H9A)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C15A(H15A), C14A(H14A), C13A(H13A),
 C12A(H12A), C11A(H11A)
5.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
;
_olex2_submission_special_instructions 'No special instructions were received'