Gold/Lewis Acid Catalyzed Cycloisomerization/Diastereoselective [3 + 2] Cycloaddition Cascade: Synthesis of Diverse Nitrogen-Containing Spiro Heterocycles.
Wang, Bin; Liang, Man; Tang, Jian; Deng, Yuting; Zhao, Jinhong; Sun, Hao; Tung, Chen-Ho; Jia, Jiong; Xu, Zhenghu; Organic letters 18 (2016) 4614–4617; doi:10.1021/acs.orglett.6b02253

data_1555732
_publ_section_title
;
 Gold/Lewis Acid Catalyzed Cycloisomerization/Diastereoselective [3 + 2]
 Cycloaddition Cascade: Synthesis of Diverse Nitrogen-Containing Spiro
 Heterocycles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4614
_journal_page_last               4617
_journal_paper_doi               10.1021/acs.orglett.6b02253
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C33 H38 N2 O8 S2'
_chemical_formula_sum            'C33 H38 N2 O8 S2'
_chemical_formula_weight         654.77
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_cell_angle_alpha                91.087(2)
_cell_angle_beta                 95.709(2)
_cell_angle_gamma                107.236(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8389(2)
_cell_length_b                   10.1118(3)
_cell_length_c                   20.3650(6)
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.736
_cell_measurement_theta_min      2.728
_cell_volume                     1727.56(8)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15853
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9602
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.208
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0824
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1590P)^2^+1.1550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2329
_refine_ls_wR_factor_ref         0.2714
_reflns_number_gt                3711
_reflns_number_total             6039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02253_si_004.cif
_cod_data_source_block           p
_cod_database_code               1555732
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C19(H19A,H19B), C22(H22A,H22B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C28(H28), C29(H29), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'