#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150986.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_7150986
loop_
_publ_author_name
'Cariou, Claire A. M.'
'Kariuki, Benson M.'
'Snaith, John S.'
_publ_section_title
;
 Stereoselective synthesis of 2,4,5-trisubstituted piperidines by
 carbonyl ene and Prins cyclisations
;
_journal_issue                   18
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3337
_journal_page_last               3348
_journal_paper_doi               10.1039/B808644c
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C21 H25 N O3 S'
_chemical_formula_sum            'C21 H25 N O3 S'
_chemical_formula_weight         371.48
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.075(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6771(12)
_cell_length_b                   8.3153(12)
_cell_length_c                   12.6634(17)
_cell_measurement_reflns_used    3237
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.16
_cell_volume                     992.6(2)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6142
_diffrn_reflns_theta_full        25.16
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0430
_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)+(0.0320P)²+0.2130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                3237
_reflns_number_total             3400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B808644c.txt
_cod_data_source_block           clc512g
_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      P21
_cod_database_code               7150986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.76759(7) 0.13508(8) 0.85658(5) 0.04856(17) Uani 1 1 d . . .
O1 O 0.6529(2) 0.7391(2) 1.04804(16) 0.0555(5) Uani 1 1 d . . .
H1A H 0.6705 0.8213 1.0178 0.083 Uiso 1 1 calc R . .
O2 O 0.90254(18) 0.1364(3) 0.82724(15) 0.0644(5) Uani 1 1 d . . .
O3 O 0.7410(3) 0.0063(2) 0.92553(17) 0.0682(7) Uani 1 1 d . . .
N1 N 0.7385(2) 0.3027(2) 0.91395(16) 0.0401(5) Uani 1 1 d . . .
C1 C 0.7487(2) 0.3016(3) 1.03279(18) 0.0388(5) Uani 1 1 d . . .
H1 H 0.6929 0.2102 1.0488 0.047 Uiso 1 1 calc R . .
C2 C 0.6782(3) 0.4546(3) 1.0614(2) 0.0422(6) Uani 1 1 d . . .
H2A H 0.5764 0.4452 1.0344 0.051 Uiso 1 1 calc R . .
H2B H 0.6966 0.4641 1.1397 0.051 Uiso 1 1 calc R . .
C3 C 0.7288(2) 0.6066(3) 1.01563(19) 0.0401(5) Uani 1 1 d . . .
H3 H 0.8302 0.6206 1.0477 0.048 Uiso 1 1 calc R . .
C4 C 0.7077(2) 0.5957(3) 0.8925(2) 0.0413(5) Uani 1 1 d . . .
H4 H 0.7512 0.6910 0.8680 0.050 Uiso 1 1 calc R . .
C5 C 0.7899(3) 0.4482(3) 0.8689(2) 0.0431(6) Uani 1 1 d . . .
H5A H 0.7780 0.4360 0.7912 0.052 Uiso 1 1 calc R . .
H5B H 0.8901 0.4626 0.9007 0.052 Uiso 1 1 calc R . .
C6 C 0.9027(2) 0.2788(3) 1.09902(19) 0.0461(6) Uani 1 1 d . . .
H6A H 0.9509 0.2012 1.0629 0.055 Uiso 1 1 calc R . .
H6B H 0.9532 0.3801 1.1026 0.055 Uiso 1 1 calc R . .
C7 C 0.9050(3) 0.2214(3) 1.2119(2) 0.0471(6) Uani 1 1 d . . .
C8 C 0.8849(3) 0.0604(4) 1.2306(3) 0.0641(8) Uani 1 1 d . . .
H8 H 0.8739 -0.0128 1.1737 0.077 Uiso 1 1 calc R . .
C9 C 0.8810(4) 0.0072(5) 1.3335(3) 0.0882(12) Uani 1 1 d . . .
H9 H 0.8682 -0.1015 1.3458 0.106 Uiso 1 1 calc R . .
C10 C 0.8959(4) 0.1146(8) 1.4168(3) 0.0990(15) Uani 1 1 d . . .
H10 H 0.8910 0.0790 1.4855 0.119 Uiso 1 1 calc R . .
C11 C 0.9179(4) 0.2744(7) 1.4002(3) 0.0941(13) Uani 1 1 d . . .
H11 H 0.9290 0.3469 1.4574 0.113 Uiso 1 1 calc R . .
C12 C 0.9235(3) 0.3268(5) 1.2981(2) 0.0699(9) Uani 1 1 d . . .
H12 H 0.9401 0.4350 1.2871 0.084 Uiso 1 1 calc R . .
C13 C 0.5543(3) 0.5912(3) 0.8333(2) 0.0472(6) Uani 1 1 d . . .
H13 H 0.5004 0.5034 0.8452 0.057 Uiso 1 1 calc R . .
C14 C 0.4916(3) 0.7022(4) 0.7661(2) 0.0635(8) Uani 1 1 d . . .
H14A H 0.5424 0.7917 0.7522 0.076 Uiso 1 1 calc R . .
H14B H 0.3962 0.6917 0.7322 0.076 Uiso 1 1 calc R . .
C15 C 0.6351(2) 0.1307(4) 0.73605(18) 0.0460(5) Uani 1 1 d . . .
C16 C 0.4949(3) 0.1562(3) 0.7376(2) 0.0531(7) Uani 1 1 d . . .
H16 H 0.4700 0.1853 0.8018 0.064 Uiso 1 1 calc R . .
C17 C 0.3917(3) 0.1383(5) 0.6435(2) 0.0621(7) Uani 1 1 d . . .
H17 H 0.2973 0.1566 0.6450 0.074 Uiso 1 1 calc R . .
C18 C 0.4248(3) 0.0942(4) 0.5475(2) 0.0724(10) Uani 1 1 d . . .
C19 C 0.5656(4) 0.0703(6) 0.5474(3) 0.0915(14) Uani 1 1 d . . .
H19 H 0.5902 0.0417 0.4831 0.110 Uiso 1 1 calc R . .
C20 C 0.6715(3) 0.0879(5) 0.6407(2) 0.0730(10) Uani 1 1 d . . .
H20 H 0.7660 0.0710 0.6391 0.088 Uiso 1 1 calc R . .
C21 C 0.3103(4) 0.0729(7) 0.4451(3) 0.1159(18) Uani 1 1 d . . .
H21A H 0.2230 0.0432 0.4638 0.174 Uiso 1 1 calc R . .
H21B H 0.3380 -0.0101 0.4013 0.174 Uiso 1 1 calc R . .
H21C H 0.2974 0.1720 0.4052 0.174 Uiso 1 1 calc R . .
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 O3 117.38(14) . . ?
O2 S1 N1 111.61(12) . . ?
O3 S1 N1 107.08(11) . . ?
O2 S1 C15 107.62(11) . . ?
O3 S1 C15 108.39(14) . . ?
N1 S1 C15 103.90(12) . . ?
C5 N1 C1 116.5(2) . . ?
C5 N1 S1 115.10(16) . . ?
C1 N1 S1 117.98(16) . . ?
N1 C1 C2 107.7(2) . . ?
N1 C1 C6 112.64(19) . . ?
C2 C1 C6 113.6(2) . . ?
C3 C2 C1 113.83(19) . . ?
O1 C3 C2 107.48(18) . . ?
O1 C3 C4 112.23(19) . . ?
C2 C3 C4 111.11(19) . . ?
C13 C4 C5 112.4(2) . . ?
C13 C4 C3 113.53(19) . . ?
C5 C4 C3 106.97(19) . . ?
N1 C5 C4 110.39(19) . . ?
C7 C6 C1 111.1(2) . . ?
C12 C7 C8 118.6(3) . . ?
C12 C7 C6 121.5(3) . . ?
C8 C7 C6 119.9(3) . . ?
C7 C8 C9 120.3(4) . . ?
C10 C9 C8 119.9(4) . . ?
C9 C10 C11 120.6(4) . . ?
C10 C11 C12 119.5(4) . . ?
C11 C12 C7 121.1(4) . . ?
C14 C13 C4 124.6(3) . . ?
C16 C15 C20 120.0(2) . . ?
C16 C15 S1 120.75(18) . . ?
C20 C15 S1 119.0(2) . . ?
C15 C16 C17 119.6(2) . . ?
C18 C17 C16 121.6(3) . . ?
C17 C18 C19 117.9(3) . . ?
C17 C18 C21 121.1(3) . . ?
C19 C18 C21 121.0(3) . . ?
C18 C19 C20 121.7(3) . . ?
C15 C20 C19 119.2(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 1.4364(18) . ?
S1 O3 1.441(2) . ?
S1 N1 1.625(2) . ?
S1 C15 1.758(2) . ?
O1 C3 1.435(3) . ?
N1 C5 1.471(3) . ?
N1 C1 1.486(3) . ?
C1 C2 1.525(3) . ?
C1 C6 1.547(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.528(3) . ?
C4 C13 1.505(3) . ?
C4 C5 1.528(3) . ?
C6 C7 1.503(3) . ?
C7 C12 1.379(4) . ?
C7 C8 1.381(4) . ?
C8 C9 1.385(5) . ?
C9 C10 1.365(6) . ?
C10 C11 1.369(7) . ?
C11 C12 1.377(5) . ?
C13 C14 1.308(4) . ?
C15 C16 1.378(3) . ?
C15 C20 1.378(3) . ?
C16 C17 1.379(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.377(4) . ?
C18 C21 1.513(5) . ?
C19 C20 1.386(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653435
