#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:09:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180290 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/04/7150407.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_7150407
loop_
_publ_author_name
'Cariou, Claire A. M.'
'Snaith, John S.'
_publ_section_title
;
 Stereoselective synthesis of 2,4,5-trisubstituted piperidines by
 carbonyl ene and Prins cyclisations.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              51
_journal_page_last               53
_journal_paper_doi               10.1039/b515547a
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C16 H23 N O3 S'
_chemical_formula_weight         309.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 112.1780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.4722(3)
_cell_length_b                   7.87270(10)
_cell_length_c                   19.9610(2)
_cell_measurement_temperature    296(2)
_cell_volume                     3270.17(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10104
_diffrn_reflns_theta_full        70.45
_diffrn_reflns_theta_max         70.45
_diffrn_reflns_theta_min         4.25
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  0.8978
_exptl_absorpt_correction_T_min  0.5270
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0392
_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)+(0.0599P)²+2.1762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                2689
_reflns_number_total             2943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b515547a.txt
_cod_data_source_block           clc76b
_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_sg_symbol_H-M      C2/c
_cod_database_code               7150407
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.12497(9) 0.3532(2) 0.50386(10) 0.0460(4) Uani 1 1 d . . .
H1 H 0.0815 0.3949 0.4764 0.055 Uiso 1 1 calc R . .
C2 C 0.13897(10) 0.3694(2) 0.58402(10) 0.0482(4) Uani 1 1 d . . .
H2A H 0.1353 0.4879 0.5954 0.058 Uiso 1 1 calc R . .
H2B H 0.1829 0.3339 0.6111 0.058 Uiso 1 1 calc R . .
C3 C 0.09390(9) 0.2641(2) 0.60814(10) 0.0430(4) Uani 1 1 d . . .
H3 H 0.1122 0.2606 0.6611 0.052 Uiso 1 1 calc R . .
C4 C 0.08128(9) 0.0647(2) 0.50558(9) 0.0437(4) Uani 1 1 d . . .
H4A H 0.0381 0.0999 0.4755 0.052 Uiso 1 1 calc R . .
H4B H 0.0855 -0.0547 0.4962 0.052 Uiso 1 1 calc R . .
C5 C 0.12959(8) 0.1673(2) 0.48479(9) 0.0410(4) Uani 1 1 d . . .
H5 H 0.1728 0.1269 0.5145 0.049 Uiso 1 1 calc R . .
C6 C 0.12039(9) 0.1446(3) 0.40611(10) 0.0505(5) Uani 1 1 d . . .
C7 C 0.17028(12) 0.1248(4) 0.38759(12) 0.0691(6) Uani 1 1 d . . .
H7A H 0.1643 0.1152 0.3390 0.083 Uiso 1 1 calc R . .
H7B H 0.2115 0.1204 0.4231 0.083 Uiso 1 1 calc R . .
C8 C 0.05361(12) 0.1521(4) 0.35008(12) 0.0807(8) Uani 1 1 d . . .
H8A H 0.0554 0.1577 0.3029 0.121 Uiso 1 1 calc R . .
H8B H 0.0322 0.2511 0.3579 0.121 Uiso 1 1 calc R . .
H8C H 0.0304 0.0522 0.3535 0.121 Uiso 1 1 calc R . .
C9 C 0.02663(11) 0.3379(3) 0.58542(14) 0.0632(6) Uani 1 1 d . . .
H9A H 0.0064 0.3373 0.5336 0.095 Uiso 1 1 calc R . .
H9B H 0.0292 0.4524 0.6028 0.095 Uiso 1 1 calc R . .
H9C H 0.0018 0.2705 0.6055 0.095 Uiso 1 1 calc R . .
C10 C 0.20343(9) -0.0809(2) 0.65721(10) 0.0433(4) Uani 1 1 d . . .
C11 C 0.24656(10) 0.0139(3) 0.71323(11) 0.0551(5) Uani 1 1 d . . .
H11 H 0.2320 0.0825 0.7418 0.066 Uiso 1 1 calc R . .
C12 C 0.31128(11) 0.0051(3) 0.72603(12) 0.0650(6) Uani 1 1 d . . .
H12 H 0.3401 0.0691 0.7634 0.078 Uiso 1 1 calc R . .
C13 C 0.33421(11) -0.0964(3) 0.68473(14) 0.0658(6) Uani 1 1 d . . .
C14 C 0.29043(12) -0.1895(3) 0.62910(14) 0.0660(6) Uani 1 1 d . . .
H14 H 0.3051 -0.2581 0.6007 0.079 Uiso 1 1 calc R . .
C15 C 0.22521(10) -0.1830(3) 0.61484(12) 0.0541(5) Uani 1 1 d . . .
H15 H 0.1964 -0.2464 0.5772 0.065 Uiso 1 1 calc R . .
C16 C 0.40558(13) -0.1104(5) 0.70066(19) 0.1015(11) Uani 1 1 d . . .
H16A H 0.4211 -0.2183 0.7227 0.152 Uiso 1 1 calc R . .
H16B H 0.4280 -0.0208 0.7330 0.152 Uiso 1 1 calc R . .
H16C H 0.4128 -0.1009 0.6564 0.152 Uiso 1 1 calc R . .
N1 N 0.09063(7) 0.08645(18) 0.58190(8) 0.0408(3) Uani 1 1 d . . .
O1 O 0.17029(9) 0.4582(2) 0.48898(9) 0.0680(4) Uani 1 1 d . . .
H1A H 0.1738 0.4261 0.4516 0.102 Uiso 1 1 calc R . .
O2 O 0.11313(7) -0.0197(2) 0.70447(7) 0.0591(4) Uani 1 1 d . . .
O3 O 0.09161(7) -0.22059(17) 0.60299(8) 0.0590(4) Uani 1 1 d . . .
S1 S 0.12025(2) -0.06673(5) 0.63883(2) 0.04278(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
O1 C1 C2 106.91(15) . . ?
O1 C1 C5 112.48(16) . . ?
C2 C1 C5 109.76(15) . . ?
C1 C2 C3 112.99(15) . . ?
N1 C3 C9 110.07(16) . . ?
N1 C3 C2 110.61(14) . . ?
C9 C3 C2 113.79(17) . . ?
N1 C4 C5 112.43(14) . . ?
C6 C5 C1 112.11(15) . . ?
C6 C5 C4 112.66(15) . . ?
C1 C5 C4 108.47(14) . . ?
C7 C6 C8 121.0(2) . . ?
C7 C6 C5 120.52(18) . . ?
C8 C6 C5 118.42(17) . . ?
C15 C10 C11 120.27(19) . . ?
C15 C10 S1 120.02(16) . . ?
C11 C10 S1 119.70(15) . . ?
C12 C11 C10 119.2(2) . . ?
C13 C12 C11 121.6(2) . . ?
C12 C13 C14 118.3(2) . . ?
C12 C13 C16 121.4(3) . . ?
C14 C13 C16 120.4(3) . . ?
C13 C14 C15 121.5(2) . . ?
C10 C15 C14 119.2(2) . . ?
C4 N1 C3 116.40(14) . . ?
C4 N1 S1 120.12(12) . . ?
C3 N1 S1 120.11(12) . . ?
O2 S1 O3 119.58(9) . . ?
O2 S1 N1 107.00(8) . . ?
O3 S1 N1 106.96(8) . . ?
O2 S1 C10 107.58(9) . . ?
O3 S1 C10 106.95(9) . . ?
N1 S1 C10 108.38(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 O1 1.427(2) . ?
C1 C2 1.515(3) . ?
C1 C5 1.525(3) . ?
C2 C3 1.521(3) . ?
C3 N1 1.486(2) . ?
C3 C9 1.520(3) . ?
C4 N1 1.467(2) . ?
C4 C5 1.531(2) . ?
C5 C6 1.515(2) . ?
C6 C7 1.316(3) . ?
C6 C8 1.496(3) . ?
C10 C15 1.383(3) . ?
C10 C11 1.389(3) . ?
C10 S1 1.7672(19) . ?
C11 C12 1.380(3) . ?
C12 C13 1.380(4) . ?
C13 C14 1.383(4) . ?
C13 C16 1.517(3) . ?
C14 C15 1.385(3) . ?
N1 S1 1.6179(15) . ?
O2 S1 1.4275(14) . ?
O3 S1 1.4302(15) . ?
