One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties.
Li, Ji-Yao; Li, Zhi-Long; Zhao, Wei-Wei; Liu, Yan-Kai; Tong, Zhi-Ping; Tan, Rui; Organic & biomolecular chemistry 14 (2016) 2444–2453; doi:10.1039/c5ob02571k

data_7154925
_publ_section_title
;
 One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine
 derivatives bearing N,O- or N,N-acetal moieties.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2444
_journal_page_last               2453
_journal_paper_doi               10.1039/c5ob02571k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H31 N O5 S'
_chemical_formula_sum            'C28 H31 N O5 S'
_chemical_formula_weight         493.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-10-20 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0985(8)
_cell_length_b                   14.8716(11)
_cell_length_c                   17.4835(13)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.538
_cell_measurement_theta_min      2.329
_cell_volume                     2625.7(3)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0156
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20879
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.33
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0536P)^2^+0.4485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                4325
_reflns_number_total             4623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02571k2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7154924--7154925.cif.'
_cod_database_code               7154925
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C8A-C9 \\sim C9-C8B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8A) \\sim Ueq, Uanis(C8B) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.001
Uanis(C8A) = Uanis(C8B)
4. Others
 Sof(H9BC)=Sof(H9BD)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C20(H20), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C21(H21A,H21B), C22(H22A,H22B), C9(H9BC,H9BD), C9(H9AA,H9AB)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C24(H24), C17(H17), C19(H19), C27(H27), C6(H6), C26(H26), C16(H16),
 C5(H5), C4(H4), C25(H25), C18(H18), C3(H3A)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8B(H8BA,H8BB,H8BC), C8A(H8AA,H8AB,H8AC)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'