TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclic <i>N</i>,<i>O</i>-acetals.
Feng, Yi-Man; Nie, Xiao-Di; Sun, Jian-Ting; Xu, Wen-Ke; Wei, Bang-Guo; Organic & biomolecular chemistry 19 (2021) 7883–7893; doi:10.1039/d1ob01370j

data_7158262
_publ_section_title
;
 TMSOTf-mediated synthesis of skipped dienes through the addition of
 olefins to imines and semicyclic <i>N</i>,<i>O</i>-acetals.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7883
_journal_page_last               7893
_journal_paper_doi               10.1039/d1ob01370j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C33 H32 O'
_chemical_formula_sum            'C33 H32 O'
_chemical_formula_weight         444.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-01-21
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.302(8)
_cell_length_b                   17.985(4)
_cell_length_c                   8.873(2)
_cell_measurement_reflns_used    4856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.098
_cell_measurement_theta_min      5.119
_cell_volume                     5793(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293.06
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1790
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            40663
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.028
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5131
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.019
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     104
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.0989
_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^)+(0.1620P)^2^+2.3925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2551
_refine_ls_wR_factor_ref         0.3205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2455
_reflns_number_total             5099
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01370j2.cif
_cod_data_source_block           mo_dd20131_0m
_cod_depositor_comments
'Adding full bibliography for 7158262--7158263.cif.'
_cod_database_code               7158262
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups 
 At 1.5 times of: 
  All O(H) groups 
2. Restrained distances 
 C10-C11 = C11-C12 = C12-C13 = C10-C11' = C11'-C12' = C12'-C13' 
 1.55 with sigma of 0.02 
 O1-C13 = O1'-C13' 
 1.38 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
C11 \\sim C12 \\sim C13 \\sim O1 \\sim C11' \\sim C12' \\sim C13' \\sim O1': 
within 2A with sigma of 0.004 and sigma for terminal atoms of 0.008 
4. Others 
 Fixed Sof: H10A(0.6) H10B(0.6) H10C(0.4) H10D(0.4) O1(0.4) H1A(0.4) C11(0.5) 
 H11A(0.5) H11B(0.5) C12(0.6) H12A(0.6) H12B(0.6) C13(0.5) H13A(0.5) H13B(0.5) 
 O1'(0.6) H1'(0.6) C11'(0.5) H11C(0.5) H11D(0.5) C12'(0.4) H12C(0.4) H12D(0.4) 
 C13'(0.5) H13C(0.5) H13D(0.5) 
5.a Riding coordinates: 
 C10(H10A,H10B,H10C,H10D) 
5.b Ternary CH refined with riding coordinates: 
 C9(H9) 
5.c Secondary CH2 refined with riding coordinates: 
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C11'(H11C,H11D), C12'(H12C, 
 H12D), C13'(H13C,H13D) 
5.d Aromatic/amide H refined with riding coordinates: 
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C15(H15), C16(H16), C17(H17), 
 C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), 
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33) 
5.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1A), O1'(H1') 
;
_shelx_res_checksum              48222
_shelx_hkl_checksum              13034
_shelx_fab_checksum              27271
_olex2_submission_special_instructions 'No special instructions were received'