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In the title compound, C12H14ClNS, the piperidine ring adopts a chair conformation and the crystal structure is stabilized by C—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015978/hg2198sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015978/hg2198Isup2.hkl
Contains datablock I

CCDC reference: 651416

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.030
  • wR factor = 0.084
  • Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B .. CL .. 2.91 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.935 Tmax scaled 0.934 Tmin scaled 0.809 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _reflns_number_total 1316 Count of symmetry unique reflns 1270 Completeness (_total/calc) 103.62% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 46 Fraction of Friedel pairs measured 0.036 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL/PC.

Piperidin-4-chloro-phenyl-methanethione top
Crystal data top
C12H14ClNSF(000) = 504
Mr = 239.75Dx = 1.321 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.2251 (9) Åθ = 9.6–13.2°
b = 7.7283 (11) ŵ = 0.46 mm1
c = 25.061 (3) ÅT = 293 K
V = 1205.7 (3) Å3Needle, yellow
Z = 40.25 × 0.18 × 0.15 mm
Data collection top
MACH3-Nonius sealed tube
diffractometer
1046 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.004
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
ω–2θ scansh = 07
Absorption correction: ψ scan
[North et al., 1968]
k = 09
Tmin = 0.866, Tmax = 0.999l = 129
1333 measured reflections3 standard reflections every 60 min
1316 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0293P)2 + 0.5735P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1316 reflectionsΔρmax = 0.19 e Å3
136 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), 45 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.20 (15)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N0.6313 (5)0.6338 (4)0.39436 (12)0.0526 (8)
C20.8002 (6)0.6106 (6)0.43421 (15)0.0631 (11)
H2A0.87940.71780.43840.076*
H2B0.89970.52220.42230.076*
C30.7039 (7)0.5581 (6)0.48726 (15)0.0691 (12)
H3A0.61760.65250.50110.083*
H3B0.81850.53570.51260.083*
C40.5651 (7)0.3977 (6)0.48196 (16)0.0699 (12)
H4A0.65510.29850.47400.084*
H4B0.49200.37570.51550.084*
C50.4007 (6)0.4212 (6)0.43791 (16)0.0626 (11)
H5A0.32420.31330.43250.075*
H5B0.29710.50830.44860.075*
C60.5049 (6)0.4756 (5)0.38641 (14)0.0530 (9)
H6A0.59770.38360.37370.064*
H6B0.39520.49600.35970.064*
C70.5750 (6)0.7885 (5)0.37609 (13)0.0450 (9)
S0.6745 (2)0.97581 (13)0.39812 (4)0.0639 (3)
C80.4228 (6)0.7934 (5)0.33013 (13)0.0428 (8)
C90.2261 (6)0.8756 (5)0.33456 (15)0.0541 (10)
H90.18570.92410.36700.065*
C100.0904 (6)0.8865 (5)0.29169 (15)0.0561 (10)
H100.04240.94040.29510.067*
C110.1524 (6)0.8168 (5)0.24348 (14)0.0482 (9)
Cl0.01798 (18)0.83831 (15)0.18863 (4)0.0723 (3)
C120.3450 (6)0.7325 (4)0.23778 (13)0.0466 (9)
H120.38460.68480.20520.056*
C130.4787 (6)0.7202 (4)0.28152 (13)0.0467 (9)
H130.60870.66180.27840.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0502 (18)0.0525 (18)0.0550 (18)0.0052 (16)0.0174 (16)0.0003 (17)
C20.052 (2)0.072 (3)0.066 (3)0.002 (2)0.019 (2)0.002 (2)
C30.065 (3)0.087 (3)0.055 (3)0.015 (3)0.016 (2)0.011 (2)
C40.073 (3)0.084 (3)0.053 (2)0.004 (3)0.001 (2)0.014 (2)
C50.054 (2)0.059 (3)0.075 (3)0.003 (2)0.005 (2)0.007 (2)
C60.057 (2)0.0470 (19)0.055 (2)0.000 (2)0.017 (2)0.0007 (18)
C70.0445 (19)0.049 (2)0.0417 (18)0.0056 (18)0.0054 (16)0.0013 (17)
S0.0785 (7)0.0552 (6)0.0580 (6)0.0169 (6)0.0010 (6)0.0113 (5)
C80.0449 (19)0.0386 (18)0.0449 (18)0.0013 (16)0.0031 (16)0.0029 (16)
C90.053 (2)0.056 (2)0.053 (2)0.006 (2)0.0075 (18)0.0071 (19)
C100.047 (2)0.055 (2)0.066 (2)0.011 (2)0.001 (2)0.001 (2)
C110.049 (2)0.0418 (19)0.054 (2)0.000 (2)0.0076 (18)0.0114 (18)
Cl0.0670 (6)0.0822 (7)0.0678 (6)0.0088 (6)0.0204 (6)0.0155 (6)
C120.053 (2)0.045 (2)0.0418 (18)0.004 (2)0.0021 (18)0.0001 (16)
C130.0421 (19)0.046 (2)0.052 (2)0.0078 (19)0.0001 (17)0.0007 (17)
Geometric parameters (Å, º) top
N—C71.327 (4)C6—H6A0.9700
N—C21.461 (4)C6—H6B0.9700
N—C61.468 (4)C7—C81.492 (5)
C2—C31.514 (6)C7—S1.669 (4)
C2—H2A0.9700C8—C91.384 (5)
C2—H2B0.9700C8—C131.387 (4)
C3—C41.517 (6)C9—C101.369 (5)
C3—H3A0.9700C9—H90.9300
C3—H3B0.9700C10—C111.378 (5)
C4—C51.516 (5)C10—H100.9300
C4—H4A0.9700C11—C121.372 (5)
C4—H4B0.9700C11—Cl1.744 (3)
C5—C61.504 (5)C12—C131.379 (5)
C5—H5A0.9700C12—H120.9300
C5—H5B0.9700C13—H130.9300
C7—N—C2122.4 (3)N—C6—C5110.3 (3)
C7—N—C6124.2 (3)N—C6—H6A109.6
C2—N—C6112.1 (3)C5—C6—H6A109.6
N—C2—C3110.4 (3)N—C6—H6B109.6
N—C2—H2A109.6C5—C6—H6B109.6
C3—C2—H2A109.6H6A—C6—H6B108.1
N—C2—H2B109.6N—C7—C8117.2 (3)
C3—C2—H2B109.6N—C7—S124.7 (3)
H2A—C2—H2B108.1C8—C7—S118.0 (3)
C2—C3—C4111.6 (3)C9—C8—C13118.7 (3)
C2—C3—H3A109.3C9—C8—C7120.8 (3)
C4—C3—H3A109.3C13—C8—C7120.5 (3)
C2—C3—H3B109.3C10—C9—C8120.7 (3)
C4—C3—H3B109.3C10—C9—H9119.6
H3A—C3—H3B108.0C8—C9—H9119.6
C5—C4—C3110.5 (4)C9—C10—C11119.4 (4)
C5—C4—H4A109.6C9—C10—H10120.3
C3—C4—H4A109.6C11—C10—H10120.3
C5—C4—H4B109.6C12—C11—C10121.5 (3)
C3—C4—H4B109.6C12—C11—Cl119.6 (3)
H4A—C4—H4B108.1C10—C11—Cl118.9 (3)
C6—C5—C4111.6 (3)C11—C12—C13118.5 (3)
C6—C5—H5A109.3C11—C12—H12120.8
C4—C5—H5A109.3C13—C12—H12120.8
C6—C5—H5B109.3C12—C13—C8121.2 (3)
C4—C5—H5B109.3C12—C13—H13119.4
H5A—C5—H5B108.0C8—C13—H13119.4
C7—N—C2—C3108.7 (4)S—C7—C8—C963.7 (4)
C6—N—C2—C359.0 (5)N—C7—C8—C1361.7 (5)
N—C2—C3—C455.2 (5)S—C7—C8—C13114.3 (3)
C2—C3—C4—C552.3 (5)C13—C8—C9—C100.8 (6)
C3—C4—C5—C652.8 (5)C7—C8—C9—C10177.2 (4)
C7—N—C6—C5107.9 (4)C8—C9—C10—C111.0 (6)
C2—N—C6—C559.5 (4)C9—C10—C11—C121.8 (6)
C4—C5—C6—N56.0 (4)C9—C10—C11—Cl177.7 (3)
C2—N—C7—C8171.6 (3)C10—C11—C12—C130.8 (5)
C6—N—C7—C822.3 (5)Cl—C11—C12—C13178.8 (3)
C2—N—C7—S4.1 (5)C11—C12—C13—C81.0 (5)
C6—N—C7—S162.0 (3)C9—C8—C13—C121.8 (5)
N—C7—C8—C9120.3 (4)C7—C8—C13—C12176.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···Cli0.972.913.721 (4)142
Symmetry code: (i) x, y1/2, z+1/2.
 

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