Metal-Catalyzed (4 + 3) Cyclization of Vinyl Aziridines withpara-Quinone Methide Derivatives
Jiang, Fei; Yuan, Fu-Ru; Jin, Li-Wen; Mei, Guang-Jian; Shi, Feng; ACS Catalysis 8 (2018) 10234–; doi:10.1021/acscatal.8b03410

data_4515766
_publ_section_title
;
 Metal-Catalyzed (4 + 3) Cyclization of Vinyl Aziridines withpara-Quinone
 Methide Derivatives
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              10234
_journal_paper_doi               10.1021/acscatal.8b03410
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C32 H39 N O4 S'
_chemical_formula_sum            'C32 H39 N O4 S'
_chemical_formula_weight         533.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.254(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7118(6)
_cell_length_b                   39.9043(17)
_cell_length_c                   6.2660(3)
_cell_measurement_reflns_used    8808
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.33
_cell_volume                     2905.0(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      293.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            49266
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.328
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1574 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.7715. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5401
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+2.4520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.2012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3781
_reflns_number_total             5401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03410_si_002.cif
_cod_data_source_block           d8v17295
_cod_database_code               4515766
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.971
_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, All O(H) groups
2. Restrained distances
 C4-C3
 1.48 with sigma of 0.005
 H2-H25C
 2 with sigma of 0.02
 H2-H23A
 2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C17(H17), C27(H27),
 C28(H28), C30(H30), C31(H31)
3.d X=CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              63378
_shelx_hkl_checksum              45135
_olex2_submission_special_instructions 'No special instructions were received'