#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/71/2237149.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237149
loop_
_publ_author_name
'Pienaar, Daniel P.'
'Khorasani, Sanaz'
'de Koning, Charles B.'
'Michael, Joseph P.'
_publ_section_title
;
 (+-)-3-Benzyloxy-1-(4-methoxybenzyl)piperidine-2-thione
;
_journal_coeditor_code           GO2079
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o21
_journal_paper_doi               10.1107/S1600536812048854
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C20 H23 N O2 S'
_chemical_formula_moiety         'C20 H23 N O2 S'
_chemical_formula_sum            'C20 H23 N O2 S'
_chemical_formula_weight         341.45
_chemical_name_systematic
;
(+-)-3-Benzyloxy-1-(4-methoxybenzyl)piperidine-2-thione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.371(3)
_cell_length_b                   10.4844(15)
_cell_length_c                   18.467(3)
_cell_measurement_reflns_used    978
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      2.49
_cell_volume                     3556.9(10)
_computing_cell_refinement       'SAINT-NT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-NT (Bruker, 2005)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and SCHAKAL99
(Keller, 1999)
;
_computing_publication_material
;
WinGX  (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22717
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.5277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2949
_reflns_number_total             4286
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            go2079.cif
_cod_data_source_block           I
_cod_original_cell_volume        3556.9(9)
_cod_database_code               2237149
_cod_database_fobs_code          2237149
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C2 -0.00224(8) 0.06796(14) 0.61154(8) 0.0260(3) Uani d . 1 1
C C3 0.02325(8) 0.19576(13) 0.58013(8) 0.0278(3) Uani d . 1 1
H H3 0.0100 0.1991 0.5277 0.033 Uiso calc R 1 1
C C4 0.10388(8) 0.21947(16) 0.58763(9) 0.0339(4) Uani d . 1 1
H H4A 0.1153 0.3082 0.5733 0.041 Uiso calc R 1 1
H H4B 0.1311 0.1611 0.5553 0.041 Uiso calc R 1 1
C C5 0.12655(9) 0.19740(15) 0.66565(9) 0.0371(4) Uani d . 1 1
H H5A 0.1790 0.2166 0.6715 0.045 Uiso calc R 1 1
H H5B 0.0988 0.2548 0.6980 0.045 Uiso calc R 1 1
C C6 0.11198(8) 0.06000(15) 0.68586(9) 0.0339(4) Uani d . 1 1
H H6A 0.1511 0.0060 0.6654 0.041 Uiso calc R 1 1
H H6B 0.1140 0.0518 0.7392 0.041 Uiso calc R 1 1
C C7 0.02107(8) -0.11296(14) 0.69241(8) 0.0310(3) Uani d . 1 1
H H7A -0.0293 -0.1356 0.6782 0.037 Uiso calc R 1 1
H H7B 0.0225 -0.1057 0.7458 0.037 Uiso calc R 1 1
C C8 0.07247(8) -0.21843(14) 0.66849(8) 0.0265(3) Uani d . 1 1
C C9 0.09864(8) -0.22570(14) 0.59808(8) 0.0293(3) Uani d . 1 1
H H9 0.0846 -0.1624 0.5640 0.035 Uiso calc R 1 1
C C10 0.14501(8) -0.32359(14) 0.57614(8) 0.0295(3) Uani d . 1 1
H H10 0.1621 -0.3273 0.5276 0.035 Uiso calc R 1 1
C C11 0.16592(8) -0.41589(14) 0.62622(9) 0.0311(3) Uani d . 1 1
C C12 0.13904(9) -0.41094(14) 0.69669(9) 0.0353(4) Uani d . 1 1
H H12 0.1522 -0.4751 0.7306 0.042 Uiso calc R 1 1
C C13 0.09325(9) -0.31299(14) 0.71751(9) 0.0324(4) Uani d . 1 1
H H13 0.0757 -0.3100 0.7659 0.039 Uiso calc R 1 1
C C14 0.23736(9) -0.52714(17) 0.53823(10) 0.0434(4) Uani d . 1 1
H H14A 0.1953 -0.5379 0.5061 0.065 Uiso calc R 1 1
H H14B 0.2693 -0.6017 0.5342 0.065 Uiso calc R 1 1
H H14C 0.2643 -0.4503 0.5243 0.065 Uiso calc R 1 1
C C15 -0.02311(8) 0.40960(13) 0.58316(9) 0.0293(3) Uani d . 1 1
H H15A -0.0249 0.3973 0.5300 0.035 Uiso calc R 1 1
H H15B 0.0205 0.4611 0.5948 0.035 Uiso calc R 1 1
C C16 -0.09058(8) 0.47794(13) 0.60827(8) 0.0256(3) Uani d . 1 1
C C17 -0.15243(8) 0.41094(14) 0.62983(8) 0.0300(3) Uani d . 1 1
H H17 -0.1518 0.3203 0.6303 0.036 Uiso calc R 1 1
C C18 -0.21487(9) 0.47569(15) 0.65056(9) 0.0359(4) Uani d . 1 1
H H18 -0.2567 0.4292 0.6654 0.043 Uiso calc R 1 1
C C19 -0.21667(9) 0.60777(16) 0.64975(9) 0.0373(4) Uani d . 1 1
H H19 -0.2596 0.6518 0.6640 0.045 Uiso calc R 1 1
C C20 -0.15566(9) 0.67528(15) 0.62815(9) 0.0351(4) Uani d . 1 1
H H20 -0.1569 0.7658 0.6270 0.042 Uiso calc R 1 1
C C21 -0.09291(8) 0.61116(14) 0.60820(8) 0.0303(3) Uani d . 1 1
H H21 -0.0510 0.6582 0.5943 0.036 Uiso calc R 1 1
N N1 0.04038(6) 0.01121(11) 0.66005(6) 0.0267(3) Uani d . 1 1
S S1 -0.08302(2) 0.01240(4) 0.58307(2) 0.03658(12) Uani d . 1 1
O O1 0.21278(6) -0.51478(10) 0.61136(7) 0.0413(3) Uani d . 1 1
O O2 -0.01884(6) 0.28903(9) 0.61845(5) 0.0299(2) Uani d . 1 1
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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C2 C3 117.77(13)
N1 C2 S1 125.17(12)
C3 C2 S1 117.04(11)
O2 C3 C4 111.83(12)
O2 C3 C2 104.16(11)
C4 C3 C2 114.15(12)
O2 C3 H3 108.8
C4 C3 H3 108.8
C2 C3 H3 108.8
C3 C4 C5 109.36(13)
C3 C4 H4A 109.8
C5 C4 H4A 109.8
C3 C4 H4B 109.8
C5 C4 H4B 109.8
H4A C4 H4B 108.3
C6 C5 C4 109.33(13)
C6 C5 H5A 109.8
C4 C5 H5A 109.8
C6 C5 H5B 109.8
C4 C5 H5B 109.8
H5A C5 H5B 108.3
N1 C6 C5 113.86(13)
N1 C6 H6A 108.8
C5 C6 H6A 108.8
N1 C6 H6B 108.8
C5 C6 H6B 108.8
H6A C6 H6B 107.7
N1 C7 C8 112.02(12)
N1 C7 H7A 109.2
C8 C7 H7A 109.2
N1 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C9 C8 C13 118.27(14)
C9 C8 C7 121.82(13)
C13 C8 C7 119.89(13)
C8 C9 C10 121.62(14)
C8 C9 H9 119.2
C10 C9 H9 119.2
C11 C10 C9 119.16(14)
C11 C10 H10 120.4
C9 C10 H10 120.4
O1 C11 C12 115.88(14)
O1 C11 C10 124.33(15)
C12 C11 C10 119.78(14)
C13 C12 C11 120.22(14)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C8 120.93(15)
C12 C13 H13 119.5
C8 C13 H13 119.5
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O2 C15 C16 109.08(12)
O2 C15 H15A 109.9
C16 C15 H15A 109.9
O2 C15 H15B 109.9
C16 C15 H15B 109.9
H15A C15 H15B 108.3
C17 C16 C21 118.62(14)
C17 C16 C15 121.30(13)
C21 C16 C15 120.05(13)
C18 C17 C16 120.43(14)
C18 C17 H17 119.8
C16 C17 H17 119.8
C19 C18 C17 120.40(15)
C19 C18 H18 119.8
C17 C18 H18 119.8
C20 C19 C18 119.67(15)
C20 C19 H19 120.2
C18 C19 H19 120.2
C19 C20 C21 120.17(15)
C19 C20 H20 119.9
C21 C20 H20 119.9
C20 C21 C16 120.71(14)
C20 C21 H21 119.6
C16 C21 H21 119.6
C2 N1 C7 121.73(13)
C2 N1 C6 125.56(13)
C7 N1 C6 112.68(12)
C11 O1 C14 117.04(13)
C15 O2 C3 114.16(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N1 1.3302(19)
C2 C3 1.533(2)
C2 S1 1.6788(15)
C3 O2 1.4334(17)
C3 C4 1.509(2)
C3 H3 1.0000
C4 C5 1.518(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.512(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 N1 1.4897(19)
C6 H6A 0.9900
C6 H6B 0.9900
C7 N1 1.4756(18)
C7 C8 1.520(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.388(2)
C8 C13 1.396(2)
C9 C10 1.394(2)
C9 H9 0.9500
C10 C11 1.393(2)
C10 H10 0.9500
C11 O1 1.3752(19)
C11 C12 1.393(2)
C12 C13 1.382(2)
C12 H12 0.9500
C13 H13 0.9500
C14 O1 1.430(2)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 O2 1.4244(17)
C15 C16 1.505(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.394(2)
C16 C21 1.397(2)
C17 C18 1.387(2)
C17 H17 0.9500
C18 C19 1.385(2)
C18 H18 0.9500
C19 C20 1.384(2)
C19 H19 0.9500
C20 C21 1.384(2)
C20 H20 0.9500
C21 H21 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H7A S1 . 0.99 2.54 3.0760(16) 114 y
C13 H13 O2 4_546 0.95 2.59 3.4913(19) 158 y
C6 H6B Cg1 4_546 0.99 2.54 3.5066(19) 165 y
C14 H14A Cg1 5_556 0.98 2.61 3.455(2) 144 y
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
N1 C2 C3 O2 -101.85(14)
S1 C2 C3 O2 76.83(14)
N1 C2 C3 C4 20.40(19)
S1 C2 C3 C4 -160.92(11)
O2 C3 C4 C5 67.16(16)
C2 C3 C4 C5 -50.78(17)
C3 C4 C5 C6 62.00(17)
C4 C5 C6 N1 -43.34(18)
N1 C7 C8 C9 -39.1(2)
N1 C7 C8 C13 142.40(14)
C13 C8 C9 C10 -0.6(2)
C7 C8 C9 C10 -179.13(14)
C8 C9 C10 C11 -0.4(2)
C9 C10 C11 O1 -178.26(14)
C9 C10 C11 C12 1.5(2)
O1 C11 C12 C13 178.11(14)
C10 C11 C12 C13 -1.7(2)
C11 C12 C13 C8 0.7(2)
C9 C8 C13 C12 0.4(2)
C7 C8 C13 C12 179.00(14)
O2 C15 C16 C17 -29.49(19)
O2 C15 C16 C21 152.48(13)
C21 C16 C17 C18 0.2(2)
C15 C16 C17 C18 -177.91(15)
C16 C17 C18 C19 0.3(2)
C17 C18 C19 C20 -0.1(3)
C18 C19 C20 C21 -0.7(3)
C19 C20 C21 C16 1.2(2)
C17 C16 C21 C20 -0.9(2)
C15 C16 C21 C20 177.18(14)
C3 C2 N1 C7 -178.97(12)
S1 C2 N1 C7 2.5(2)
C3 C2 N1 C6 -1.2(2)
S1 C2 N1 C6 -179.75(12)
C8 C7 N1 C2 112.23(15)
C8 C7 N1 C6 -65.82(16)
C5 C6 N1 C2 13.5(2)
C5 C6 N1 C7 -168.55(13)
C12 C11 O1 C14 175.93(13)
C10 C11 O1 C14 -4.3(2)
C16 C15 O2 C3 155.93(12)
C4 C3 O2 C15 76.17(15)
C2 C3 O2 C15 -160.07(12)
