#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:39:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178436 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/57/4025779.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025779
loop_
_publ_author_name
'Manas K. Ghorai'
'Sandipan Halder'
'Raj Kumar Das'
_publ_section_title
;
 Domino Imino-Aldol-Aza-Michael Reaction: One-Pot Diastereo- and
 Enantioselective Synthesis of Piperidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7061
_journal_page_last               7072
_journal_paper_doi               10.1021/jo101680f
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C26 H31 N O5 S'
_chemical_formula_weight         469.58
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.443(5)
_cell_angle_beta                 98.737(4)
_cell_angle_gamma                94.167(6)
_cell_formula_units_Z            2
_cell_length_a                   8.179(5)
_cell_length_b                   9.871(4)
_cell_length_c                   15.334(6)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.11
_cell_volume                     1196.9(10)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 97'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0768
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6943
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0916P)²+0.9345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1966
_reflns_number_gt                3555
_reflns_number_total             4835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101680f_si_002_4.cif
_cod_data_source_block           Compound12a
_cod_database_code               4025779
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28151(9) 0.36355(8) 0.07882(5) 0.0213(2) Uani 1 1 d . . .
O1 O 0.2240(3) 0.4507(2) 0.01795(14) 0.0262(5) Uani 1 1 d . . .
O2 O 0.4155(3) 0.2825(2) 0.06231(14) 0.0258(5) Uani 1 1 d . . .
O3 O 0.2148(3) 0.4124(2) 0.42155(15) 0.0289(5) Uani 1 1 d . . .
O4 O 0.6717(3) 0.3168(3) 0.36253(15) 0.0352(6) Uani 1 1 d . . .
O5 O 0.5015(3) 0.3320(2) 0.46540(14) 0.0291(5) Uani 1 1 d . . .
N1 N 0.3400(3) 0.4635(3) 0.17777(16) 0.0204(5) Uani 1 1 d . . .
C1 C -0.3208(4) -0.0014(4) 0.1177(2) 0.0340(8) Uani 1 1 d . . .
H1A H -0.4197 0.0397 0.0988 0.051 Uiso 1 1 calc R . .
H1B H -0.3137 -0.0078 0.1799 0.051 Uiso 1 1 calc R . .
H1C H -0.3248 -0.0924 0.0818 0.051 Uiso 1 1 calc R . .
C2 C -0.1708(4) 0.0868(3) 0.1060(2) 0.0265(7) Uani 1 1 d . . .
C3 C -0.0104(4) 0.0495(3) 0.1284(2) 0.0290(7) Uani 1 1 d . . .
H3 H 0.0035 -0.0315 0.1504 0.035 Uiso 1 1 calc R . .
C4 C 0.1286(4) 0.1311(3) 0.1184(2) 0.0256(7) Uani 1 1 d . . .
H4 H 0.2347 0.1054 0.1338 0.031 Uiso 1 1 calc R . .
C5 C 0.1073(4) 0.2512(3) 0.08535(19) 0.0215(6) Uani 1 1 d . . .
C6 C -0.0508(4) 0.2903(3) 0.0617(2) 0.0240(7) Uani 1 1 d . . .
H6 H -0.0644 0.3709 0.0391 0.029 Uiso 1 1 calc R . .
C7 C -0.1877(4) 0.2077(3) 0.0722(2) 0.0264(7) Uani 1 1 d . . .
H7 H -0.2936 0.2335 0.0563 0.032 Uiso 1 1 calc R . .
C8 C 0.2174(4) 0.5527(3) 0.2138(2) 0.0204(6) Uani 1 1 d . . .
H8 H 0.1271 0.5522 0.1638 0.025 Uiso 1 1 calc R . .
C9 C 0.1422(4) 0.4866(3) 0.2836(2) 0.0241(7) Uani 1 1 d . . .
H9A H 0.0856 0.5547 0.3184 0.029 Uiso 1 1 calc R . .
H9B H 0.0601 0.4105 0.2526 0.029 Uiso 1 1 calc R . .
C10 C 0.2691(4) 0.4340(3) 0.3458(2) 0.0230(7) Uani 1 1 d . . .
C11 C 0.4206(4) 0.4069(3) 0.32771(19) 0.0214(6) Uani 1 1 d . . .
C12 C 0.4787(4) 0.4339(3) 0.24261(19) 0.0207(6) Uani 1 1 d . . .
H12 H 0.5197 0.3486 0.2145 0.025 Uiso 1 1 calc R . .
C13 C 0.5319(4) 0.3499(3) 0.3916(2) 0.0244(7) Uani 1 1 d . . .
C14 C 0.7956(6) 0.2664(5) 0.4238(3) 0.0535(12) Uani 1 1 d . . .
H14A H 0.8799 0.3414 0.4538 0.064 Uiso 1 1 calc R . .
H14B H 0.7436 0.2316 0.4693 0.064 Uiso 1 1 calc R . .
C15 C 0.8709(6) 0.1576(5) 0.3738(3) 0.0615(13) Uani 1 1 d . . .
H15A H 0.9531 0.1241 0.4139 0.092 Uiso 1 1 calc R . .
H15B H 0.9227 0.1928 0.3292 0.092 Uiso 1 1 calc R . .
H15C H 0.7871 0.0833 0.3448 0.092 Uiso 1 1 calc R . .
C16 C 0.6218(3) 0.5507(3) 0.25806(19) 0.0204(6) Uani 1 1 d . . .
C17 C 0.6748(4) 0.6371(3) 0.3410(2) 0.0254(7) Uani 1 1 d . . .
H17 H 0.6255 0.6235 0.3900 0.031 Uiso 1 1 calc R . .
C18 C 0.8011(4) 0.7442(3) 0.3518(2) 0.0275(7) Uani 1 1 d . . .
H18 H 0.8360 0.8015 0.4078 0.033 Uiso 1 1 calc R . .
C19 C 0.8750(4) 0.7656(3) 0.2792(2) 0.0263(7) Uani 1 1 d . . .
H19 H 0.9583 0.8378 0.2860 0.032 Uiso 1 1 calc R . .
C20 C 0.8233(4) 0.6777(3) 0.1961(2) 0.0256(7) Uani 1 1 d . . .
H20 H 0.8732 0.6908 0.1472 0.031 Uiso 1 1 calc R . .
C21 C 0.6978(4) 0.5707(3) 0.1857(2) 0.0220(6) Uani 1 1 d . . .
H21 H 0.6644 0.5121 0.1300 0.026 Uiso 1 1 calc R . .
C22 C 0.3427(4) 0.7668(3) 0.1693(2) 0.0303(7) Uani 1 1 d . . .
H22A H 0.3123 0.7018 0.1133 0.045 Uiso 1 1 calc R . .
H22B H 0.4604 0.7930 0.1801 0.045 Uiso 1 1 calc R . .
H22C H 0.2849 0.8475 0.1663 0.045 Uiso 1 1 calc R . .
C23 C 0.2962(4) 0.7008(3) 0.2448(2) 0.0227(6) Uani 1 1 d . . .
C24 C 0.3216(4) 0.7647(3) 0.3306(2) 0.0269(7) Uani 1 1 d . . .
H24 H 0.2861 0.7140 0.3710 0.032 Uiso 1 1 calc R . .
C25 C 0.4010(4) 0.9088(4) 0.3696(2) 0.0343(8) Uani 1 1 d . . .
H25A H 0.4624 0.9414 0.3267 0.041 Uiso 1 1 calc R . .
H25B H 0.4794 0.9077 0.4236 0.041 Uiso 1 1 calc R . .
C26 C 0.2731(5) 1.0082(4) 0.3925(3) 0.0388(9) Uani 1 1 d . . .
H26A H 0.3286 1.0992 0.4172 0.058 Uiso 1 1 calc R . .
H26B H 0.2135 0.9772 0.4358 0.058 Uiso 1 1 calc R . .
H26C H 0.1965 1.0109 0.3390 0.058 Uiso 1 1 calc R . .
H1O3 H 0.309(5) 0.378(4) 0.454(3) 0.051(12) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.95(13) . . ?
O2 S1 N1 106.62(13) . . ?
O1 S1 N1 106.96(13) . . ?
O2 S1 C5 108.53(14) . . ?
O1 S1 C5 106.63(14) . . ?
N1 S1 C5 107.62(13) . . ?
C13 O4 C14 117.4(3) . . ?
C12 N1 C8 117.6(2) . . ?
C12 N1 S1 121.6(2) . . ?
C8 N1 S1 117.42(19) . . ?
C7 C2 C3 118.1(3) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 121.0(3) . . ?
C4 C3 C2 121.2(3) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 S1 120.5(2) . . ?
C6 C5 S1 118.6(2) . . ?
C7 C6 C5 119.0(3) . . ?
C6 C7 C2 121.6(3) . . ?
N1 C8 C23 109.9(2) . . ?
N1 C8 C9 108.9(2) . . ?
C23 C8 C9 116.4(3) . . ?
C10 C9 C8 112.7(2) . . ?
C11 C10 O3 123.2(3) . . ?
C11 C10 C9 123.8(3) . . ?
O3 C10 C9 113.0(3) . . ?
C10 C11 C13 119.1(3) . . ?
C10 C11 C12 122.0(3) . . ?
C13 C11 C12 118.9(3) . . ?
N1 C12 C11 111.3(2) . . ?
N1 C12 C16 109.1(2) . . ?
C11 C12 C16 114.5(2) . . ?
O5 C13 O4 122.5(3) . . ?
O5 C13 C11 124.3(3) . . ?
O4 C13 C11 113.2(3) . . ?
C15 C14 O4 109.1(3) . . ?
C17 C16 C21 119.2(3) . . ?
C17 C16 C12 122.3(3) . . ?
C21 C16 C12 118.5(3) . . ?
C16 C17 C18 120.6(3) . . ?
C19 C18 C17 120.1(3) . . ?
C18 C19 C20 119.3(3) . . ?
C21 C20 C19 120.4(3) . . ?
C20 C21 C16 120.3(3) . . ?
C24 C23 C22 124.0(3) . . ?
C24 C23 C8 122.5(3) . . ?
C22 C23 C8 113.5(3) . . ?
C23 C24 C25 127.5(3) . . ?
C24 C25 C26 112.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.430(2) . ?
S1 O1 1.431(2) . ?
S1 N1 1.635(3) . ?
S1 C5 1.767(3) . ?
O3 C10 1.351(4) . ?
O4 C13 1.331(4) . ?
O4 C14 1.453(4) . ?
O5 C13 1.235(4) . ?
N1 C12 1.474(4) . ?
N1 C8 1.485(4) . ?
C1 C2 1.505(4) . ?
C2 C7 1.392(4) . ?
C2 C3 1.397(5) . ?
C3 C4 1.389(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.384(4) . ?
C8 C23 1.516(4) . ?
C8 C9 1.530(4) . ?
C9 C10 1.488(4) . ?
C10 C11 1.345(4) . ?
C11 C13 1.452(4) . ?
C11 C12 1.515(4) . ?
C12 C16 1.541(4) . ?
C14 C15 1.435(6) . ?
C16 C17 1.385(4) . ?
C16 C21 1.389(4) . ?
C17 C18 1.393(4) . ?
C18 C19 1.385(4) . ?
C19 C20 1.392(5) . ?
C20 C21 1.388(4) . ?
C22 C23 1.511(4) . ?
C23 C24 1.329(4) . ?
C24 C25 1.497(5) . ?
C25 C26 1.522(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C12 -17.7(3) . . . . ?
O1 S1 N1 C12 -147.2(2) . . . . ?
C5 S1 N1 C12 98.6(2) . . . . ?
O2 S1 N1 C8 -176.2(2) . . . . ?
O1 S1 N1 C8 54.4(2) . . . . ?
C5 S1 N1 C8 -59.9(2) . . . . ?
C7 C2 C3 C4 0.8(5) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C4 C5 S1 175.8(2) . . . . ?
O2 S1 C5 C4 31.7(3) . . . . ?
O1 S1 C5 C4 162.2(2) . . . . ?
N1 S1 C5 C4 -83.3(3) . . . . ?
O2 S1 C5 C6 -152.1(2) . . . . ?
O1 S1 C5 C6 -21.5(3) . . . . ?
N1 S1 C5 C6 92.9(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
S1 C5 C6 C7 -175.8(2) . . . . ?
C5 C6 C7 C2 0.1(5) . . . . ?
C3 C2 C7 C6 -0.7(5) . . . . ?
C1 C2 C7 C6 179.5(3) . . . . ?
C12 N1 C8 C23 71.1(3) . . . . ?
S1 N1 C8 C23 -129.6(2) . . . . ?
C12 N1 C8 C9 -57.5(3) . . . . ?
S1 N1 C8 C9 101.9(2) . . . . ?
N1 C8 C9 C10 43.7(3) . . . . ?
C23 C8 C9 C10 -81.1(3) . . . . ?
C8 C9 C10 C11 -19.6(4) . . . . ?
C8 C9 C10 O3 162.3(3) . . . . ?
O3 C10 C11 C13 0.8(5) . . . . ?
C9 C10 C11 C13 -177.2(3) . . . . ?
O3 C10 C11 C12 -179.3(3) . . . . ?
C9 C10 C11 C12 2.7(5) . . . . ?
C8 N1 C12 C11 40.7(3) . . . . ?
S1 N1 C12 C11 -117.8(2) . . . . ?
C8 N1 C12 C16 -86.6(3) . . . . ?
S1 N1 C12 C16 114.9(2) . . . . ?
C10 C11 C12 N1 -11.8(4) . . . . ?
C13 C11 C12 N1 168.2(3) . . . . ?
C10 C11 C12 C16 112.5(3) . . . . ?
C13 C11 C12 C16 -67.5(4) . . . . ?
C14 O4 C13 O5 -4.1(5) . . . . ?
C14 O4 C13 C11 176.5(3) . . . . ?
C10 C11 C13 O5 -4.8(5) . . . . ?
C12 C11 C13 O5 175.3(3) . . . . ?
C10 C11 C13 O4 174.6(3) . . . . ?
C12 C11 C13 O4 -5.4(4) . . . . ?
C13 O4 C14 C15 141.6(4) . . . . ?
N1 C12 C16 C17 116.1(3) . . . . ?
C11 C12 C16 C17 -9.4(4) . . . . ?
N1 C12 C16 C21 -62.8(3) . . . . ?
C11 C12 C16 C21 171.7(3) . . . . ?
C21 C16 C17 C18 0.9(4) . . . . ?
C12 C16 C17 C18 -178.1(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C18 C19 C20 C21 0.7(4) . . . . ?
C19 C20 C21 C16 0.4(4) . . . . ?
C17 C16 C21 C20 -1.2(4) . . . . ?
C12 C16 C21 C20 177.8(3) . . . . ?
N1 C8 C23 C24 -114.7(3) . . . . ?
C9 C8 C23 C24 9.6(4) . . . . ?
N1 C8 C23 C22 65.0(3) . . . . ?
C9 C8 C23 C22 -170.7(3) . . . . ?
C22 C23 C24 C25 -1.1(5) . . . . ?
C8 C23 C24 C25 178.6(3) . . . . ?
C23 C24 C25 C26 104.0(4) . . . . ?
