#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/36/2213647.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_2213647
loop_
_publ_author_name
'Li-You Zhou'
_publ_section_title
;
 4-Methyl-N-phenylpiperidine-1-thioamide
;
_journal_coeditor_code           AT2285
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2848
_journal_page_last               o2848
_journal_paper_doi               10.1107/S1600536807021691
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H18 N2 S'
_chemical_formula_moiety         'C13 H18 N2 S'
_chemical_formula_sum            'C13 H18 N2 S'
_chemical_formula_weight         234.35
_chemical_name_systematic
;
4-Methyl-N-phenylpiperidine-1-thioamide
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   11.654(6)
_cell_length_b                   11.335(6)
_cell_length_c                   9.711(5)
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.51
_cell_volume                     1282.8(12)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'φ and ω'
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6919
_diffrn_reflns_theta_full        26.31
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.197
_refine_ls_abs_structure_details 'Flack (1983), 1113 Freidel pairs'
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2500
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                1842
_reflns_number_total             2500
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2285.cif
_cod_data_source_block           I
_cod_original_cell_volume        1282.7(12)
_cod_database_code               2213647
_cod_database_fobs_code          2213647
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
S S1 0.15114(6) 0.85016(5) 0.69896(7) 0.0586(2) Uani d . 1
N N1 0.21408(18) 0.7337(2) 0.4733(2) 0.0561(6) Uani d D 1
H H1 0.230(3) 0.750(3) 0.393(3) 0.084 Uiso d D 1
N N2 0.06394(17) 0.86019(17) 0.4473(2) 0.0553(5) Uani d . 1
C C1 0.14138(18) 0.8122(2) 0.5322(2) 0.0449(5) Uani d . 1
C C2 -0.0131(3) 0.9545(2) 0.4919(3) 0.0666(8) Uani d . 1
H H2A -0.0173 1.0149 0.4213 0.080 Uiso calc R 1
H H2B 0.0163 0.9905 0.5754 0.080 Uiso calc R 1
C C3 -0.1314(2) 0.9046(3) 0.5182(3) 0.0714(8) Uani d . 1
H H3A -0.1823 0.9678 0.5465 0.086 Uiso calc R 1
H H3B -0.1272 0.8480 0.5930 0.086 Uiso calc R 1
C C4 -0.1804(2) 0.8449(2) 0.3921(3) 0.0625(7) Uani d . 1
H H4 -0.1920 0.9052 0.3211 0.075 Uiso calc R 1
C C5 -0.0940(2) 0.7553(3) 0.3370(3) 0.0618(7) Uani d . 1
H H5A -0.0902 0.6890 0.4000 0.074 Uiso calc R 1
H H5B -0.1210 0.7258 0.2489 0.074 Uiso calc R 1
C C6 0.0251(2) 0.8056(3) 0.3187(3) 0.0662(7) Uani d . 1
H H6A 0.0777 0.7432 0.2925 0.079 Uiso calc R 1
H H6B 0.0244 0.8641 0.2458 0.079 Uiso calc R 1
C C7 -0.2953(2) 0.7869(3) 0.4205(5) 0.1005(12) Uani d . 1
H H7A -0.2837 0.7163 0.4734 0.151 Uiso calc R 1
H H7B -0.3318 0.7672 0.3349 0.151 Uiso calc R 1
H H7C -0.3433 0.8403 0.4712 0.151 Uiso calc R 1
C C8 0.28608(18) 0.65270(19) 0.5418(2) 0.0442(6) Uani d . 1
C C9 0.24709(19) 0.58503(19) 0.6493(3) 0.0507(6) Uani d . 1
H H9 0.1727 0.5952 0.6820 0.061 Uiso calc R 1
C C10 0.3175(2) 0.5026(2) 0.7084(4) 0.0651(7) Uani d . 1
H H10 0.2910 0.4583 0.7826 0.078 Uiso calc R 1
C C11 0.4265(2) 0.4845(2) 0.6598(3) 0.0712(8) Uani d . 1
H H11 0.4733 0.4272 0.6992 0.085 Uiso calc R 1
C C12 0.4657(2) 0.5516(3) 0.5526(3) 0.0671(7) Uani d . 1
H H12 0.5397 0.5398 0.5194 0.081 Uiso calc R 1
C C13 0.3969(2) 0.6364(2) 0.4931(3) 0.0559(6) Uani d . 1
H H13 0.4246 0.6823 0.4210 0.067 Uiso calc R 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C8 126.9(2)
C1 N1 H1 113(2)
C8 N1 H1 118(2)
C1 N2 C2 122.0(2)
C1 N2 C6 124.2(2)
C2 N2 C6 111.8(2)
N2 C1 N1 115.4(2)
N2 C1 S1 122.40(18)
N1 C1 S1 122.20(18)
N2 C2 C3 109.7(2)
N2 C2 H2A 109.7
C3 C2 H2A 109.7
N2 C2 H2B 109.7
C3 C2 H2B 109.7
H2A C2 H2B 108.2
C2 C3 C4 112.0(2)
C2 C3 H3A 109.2
C4 C3 H3A 109.2
C2 C3 H3B 109.2
C4 C3 H3B 109.2
H3A C3 H3B 107.9
C3 C4 C7 112.3(3)
C3 C4 C5 109.4(2)
C7 C4 C5 110.9(2)
C3 C4 H4 108.0
C7 C4 H4 108.0
C5 C4 H4 108.0
C6 C5 C4 113.3(2)
C6 C5 H5A 108.9
C4 C5 H5A 108.9
C6 C5 H5B 108.9
C4 C5 H5B 108.9
H5A C5 H5B 107.7
N2 C6 C5 110.1(2)
N2 C6 H6A 109.6
C5 C6 H6A 109.6
N2 C6 H6B 109.6
C5 C6 H6B 109.6
H6A C6 H6B 108.2
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 119.5(2)
C9 C8 N1 121.7(2)
C13 C8 N1 118.7(2)
C10 C9 C8 120.1(2)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 120.8(3)
C9 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 119.2(3)
C12 C11 H11 120.4
C10 C11 H11 120.4
C11 C12 C13 120.8(2)
C11 C12 H12 119.6
C13 C12 H12 119.6
C12 C13 C8 119.5(3)
C12 C13 H13 120.3
C8 C13 H13 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.679(3)
N1 C1 1.355(3)
N1 C8 1.411(3)
N1 H1 0.83(2)
N2 C1 1.338(3)
N2 C2 1.462(3)
N2 C6 1.466(3)
C2 C3 1.511(4)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.512(4)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C7 1.518(4)
C4 C5 1.527(4)
C4 H4 0.9800
C5 C6 1.511(4)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.373(3)
C8 C13 1.388(3)
C9 C10 1.370(3)
C9 H9 0.9300
C10 C11 1.371(4)
C10 H10 0.9300
C11 C12 1.368(4)
C11 H11 0.9300
C12 C13 1.378(4)
C12 H12 0.9300
C13 H13 0.9300
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
N1 H1 S1 4_554 0.83(2) 2.60(2) 3.362(3) 155(3) yes
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
C2 N2 C1 N1 -174.0(2)
C6 N2 C1 N1 23.7(3)
C2 N2 C1 S1 3.8(3)
C6 N2 C1 S1 -158.5(2)
C8 N1 C1 N2 -165.4(2)
C8 N1 C1 S1 16.8(3)
C1 N2 C2 C3 -103.0(3)
C6 N2 C2 C3 61.3(3)
N2 C2 C3 C4 -58.1(3)
C2 C3 C4 C7 175.9(2)
C2 C3 C4 C5 52.2(3)
C3 C4 C5 C6 -50.4(3)
C7 C4 C5 C6 -174.9(3)
C1 N2 C6 C5 105.0(3)
C2 N2 C6 C5 -58.9(3)
C4 C5 C6 N2 53.6(3)
C1 N1 C8 C9 45.6(3)
C1 N1 C8 C13 -138.4(3)
C13 C8 C9 C10 0.4(4)
N1 C8 C9 C10 176.4(2)
C8 C9 C10 C11 -1.5(4)
C9 C10 C11 C12 1.4(5)
C10 C11 C12 C13 -0.2(4)
C11 C12 C13 C8 -0.8(4)
C9 C8 C13 C12 0.7(4)
N1 C8 C13 C12 -175.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 613376
