#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151150.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_7151150
loop_
_publ_author_name
'Walker, Stephen M.'
'Williams, Jodi T.'
'Russell, Alexander G.'
'Kariuki, Benson M.'
'Snaith, John S.'
_publ_section_title
;
 Stereoselective synthesis of 3,4-disubstituted and
 3,4,5-trisubstituted piperidines by Lewis acid-catalysed ene
 cyclisation of 4-aza-1,7-dienes.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2925
_journal_page_last               2931
_journal_paper_doi               10.1039/b708139a
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         'C16 H21 N O4 S'
_chemical_formula_sum            'C16 H21 N O4 S'
_chemical_formula_weight         323.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.330(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6072(3)
_cell_length_b                   12.0948(4)
_cell_length_c                   17.8368(6)
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      70.38
_cell_measurement_theta_min      4.43
_cell_volume                     1631.12(10)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10303
_diffrn_reflns_theta_full        70.38
_diffrn_reflns_theta_max         70.38
_diffrn_reflns_theta_min         4.43
_exptl_absorpt_coefficient_mu    1.916
_exptl_absorpt_correction_T_max  0.7006
_exptl_absorpt_correction_T_min  0.5537
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0396
_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/[σ²(Fo²)+(0.0617P)²+0.3571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2513
_reflns_number_total             3014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b708139a.txt
_cod_data_source_block           smw137
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1631.11(10)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7151150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.1515(2) 0.24524(14) 0.12282(10) 0.0369(4) Uani 1 1 d . . .
C2 C 0.0977(2) 0.27922(15) 0.04984(10) 0.0429(4) Uani 1 1 d . . .
H2 H 0.0255 0.2341 0.0174 0.051 Uiso 1 1 calc R . .
C3 C 0.1523(3) 0.38127(15) 0.02544(11) 0.0463(4) Uani 1 1 d . . .
H3 H 0.1170 0.4039 -0.0238 0.056 Uiso 1 1 calc R . .
C4 C 0.2591(2) 0.45029(15) 0.07339(12) 0.0455(4) Uani 1 1 d . . .
C5 C 0.3145(2) 0.41336(16) 0.14576(11) 0.0460(4) Uani 1 1 d . . .
H5 H 0.3879 0.4582 0.1780 0.055 Uiso 1 1 calc R . .
C6 C 0.2634(2) 0.31160(16) 0.17120(10) 0.0420(4) Uani 1 1 d . . .
H6 H 0.3028 0.2877 0.2197 0.050 Uiso 1 1 calc R . .
C7 C 0.3112(3) 0.56415(18) 0.04850(15) 0.0683(7) Uani 1 1 d . . .
H7A H 0.2562 0.5782 -0.0016 0.102 Uiso 1 1 calc R . .
H7B H 0.4374 0.5678 0.0490 0.102 Uiso 1 1 calc R . .
H7C H 0.2731 0.6186 0.0823 0.102 Uiso 1 1 calc R . .
C8 C 0.4042(2) 0.04451(16) 0.19417(10) 0.0424(4) Uani 1 1 d . . .
H8A H 0.3821 0.0642 0.2450 0.051 Uiso 1 1 calc R . .
H8B H 0.4672 0.1051 0.1736 0.051 Uiso 1 1 calc R . .
C9 C 0.5163(2) -0.06009(15) 0.19604(10) 0.0391(4) Uani 1 1 d . . .
H9 H 0.4546 -0.1190 0.2204 0.047 Uiso 1 1 calc R . .
C10 C 0.5423(3) -0.09693(16) 0.11625(11) 0.0438(4) Uani 1 1 d . . .
H10 H 0.6077 -0.0392 0.0925 0.053 Uiso 1 1 calc R . .
C11 C 0.3633(3) -0.11193(18) 0.07017(12) 0.0532(5) Uani 1 1 d . . .
H11A H 0.3806 -0.1325 0.0189 0.064 Uiso 1 1 calc R . .
H11B H 0.2993 -0.1713 0.0917 0.064 Uiso 1 1 calc R . .
C12 C 0.2552(3) -0.00679(18) 0.06897(11) 0.0516(5) Uani 1 1 d . . .
H12A H 0.3142 0.0516 0.0441 0.062 Uiso 1 1 calc R . .
H12B H 0.1399 -0.0189 0.0412 0.062 Uiso 1 1 calc R . .
C13 C 0.6941(2) -0.04002(17) 0.24189(11) 0.0447(4) Uani 1 1 d . . .
H13 H 0.7410 0.0301 0.2250 0.054 Uiso 1 1 calc R . .
C14 C 0.8215(3) -0.19287(18) 0.17272(12) 0.0553(5) Uani 1 1 d . . .
C15 C 0.6525(3) -0.20169(19) 0.12143(13) 0.0578(6) Uani 1 1 d . . .
H15A H 0.5823 -0.2613 0.1391 0.069 Uiso 1 1 calc R . .
H15B H 0.6802 -0.2211 0.0713 0.069 Uiso 1 1 calc R . .
C16 C 0.6847(3) -0.0316(2) 0.32564(12) 0.0651(6) Uani 1 1 d . . .
H16A H 0.6437 -0.1005 0.3440 0.098 Uiso 1 1 calc R . .
H16B H 0.6042 0.0263 0.3356 0.098 Uiso 1 1 calc R . .
H16C H 0.8000 -0.0153 0.3506 0.098 Uiso 1 1 calc R . .
N1 N 0.23445(19) 0.02615(12) 0.14719(8) 0.0402(4) Uani 1 1 d . . .
O1 O -0.07333(17) 0.08324(12) 0.10722(8) 0.0536(4) Uani 1 1 d . . .
O2 O 0.06593(18) 0.12995(12) 0.23537(8) 0.0515(4) Uani 1 1 d . . .
O3 O 0.8248(2) -0.12616(13) 0.23233(9) 0.0617(4) Uani 1 1 d . . .
O4 O 0.9509(2) -0.24756(17) 0.16513(11) 0.0846(6) Uani 1 1 d . . .
S1 S 0.07882(6) 0.11769(4) 0.15629(3) 0.04089(16) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C2 C1 C6 120.50(17) . . ?
C2 C1 S1 120.46(14) . . ?
C6 C1 S1 119.04(14) . . ?
C1 C2 C3 119.46(17) . . ?
C2 C3 C4 121.05(18) . . ?
C5 C4 C3 118.42(18) . . ?
C5 C4 C7 120.23(18) . . ?
C3 C4 C7 121.33(19) . . ?
C6 C5 C4 121.63(17) . . ?
C5 C6 C1 118.90(17) . . ?
N1 C8 C9 109.85(15) . . ?
C13 C9 C8 109.97(15) . . ?
C13 C9 C10 110.43(15) . . ?
C8 C9 C10 110.62(15) . . ?
C15 C10 C11 112.89(16) . . ?
C15 C10 C9 108.37(16) . . ?
C11 C10 C9 109.77(16) . . ?
C12 C11 C10 111.10(16) . . ?
N1 C12 C11 109.15(16) . . ?
O3 C13 C16 105.72(16) . . ?
O3 C13 C9 113.53(15) . . ?
C16 C13 C9 114.00(16) . . ?
O4 C14 O3 118.6(2) . . ?
O4 C14 C15 123.3(2) . . ?
O3 C14 C15 118.02(18) . . ?
C14 C15 C10 114.16(17) . . ?
C12 N1 C8 113.53(15) . . ?
C12 N1 S1 115.39(12) . . ?
C8 N1 S1 115.94(12) . . ?
C14 O3 C13 124.81(15) . . ?
O2 S1 O1 119.53(9) . . ?
O2 S1 N1 107.19(8) . . ?
O1 S1 N1 106.62(8) . . ?
O2 S1 C1 107.50(8) . . ?
O1 S1 C1 108.01(8) . . ?
N1 S1 C1 107.45(8) . . ?
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
C1 C2 1.383(3) . ?
C1 C6 1.397(2) . ?
C1 S1 1.7648(18) . ?
C2 C3 1.388(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.387(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.382(3) . ?
C8 N1 1.476(2) . ?
C8 C9 1.524(3) . ?
C9 C13 1.521(2) . ?
C9 C10 1.525(3) . ?
C10 C15 1.516(3) . ?
C10 C11 1.522(3) . ?
C11 C12 1.513(3) . ?
C12 N1 1.476(2) . ?
C13 O3 1.463(2) . ?
C13 C16 1.507(3) . ?
C14 O4 1.206(3) . ?
C14 O3 1.333(3) . ?
C14 C15 1.498(3) . ?
N1 S1 1.6420(15) . ?
O1 S1 1.4339(14) . ?
O2 S1 1.4323(14) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 23628408
