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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2896.
Published online 2010 October 23. doi:  10.1107/S160053681004170X
PMCID: PMC3009313

N-[(Piperidin-1-yl)carbothioyl]benz­amide

Abstract

In the title compound, C13H16N2OS, the piperidine ring exhibit a classical chair conformation. In the crystal, the mol­ecules are linked by N—H(...)O hydrogen bonds, forming zigzag chains running parallel to the c axis.

Related literature

For complexes with the title compound as a ligand, see: Mohamadou et al. (1994 [triangle]); Salyn et al. (1977 [triangle]); Röbisch et al. (1982 [triangle]).

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Object name is e-66-o2896-scheme1.jpg

Experimental

Crystal data

  • C13H16N2OS
  • M r = 248.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2896-efi1.jpg
  • a = 10.913 (3) Å
  • b = 14.297 (4) Å
  • c = 8.323 (2) Å
  • β = 102.212 (6)°
  • V = 1269.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 K
  • 0.50 × 0.41 × 0.38 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.889, T max = 0.915
  • 7091 measured reflections
  • 2221 independent reflections
  • 1727 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.126
  • S = 1.08
  • 2221 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]), PARST (Nardelli, 1995 [triangle]) and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004170X/bt5376sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004170X/bt5376Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Universiti Kebangsaan Malaysia for providing facilities and a grant (UKM-GUP-BTT-07–30-190 and UKM-PTS-015–2010) and the Libyan Government for providing a scholarship for AA.

supplementary crystallographic information

Comment

N,N-dialkyl-N'-benzoyl thioureas are known to form stable complexes with lage number of transition metals. The title compound has been used extensivelly as ligand to form stable complexes with Cu, Ni, Co, Pt, Pd, Hg, Ru, Os, Rh and Ir (Mohamadou et al., 1994; Salyn et al., 1977; Röbisch et al., 1982). The six-membered piperidine ring has a classical chair conformation.

In the crystal, the molecules are linked by N—H···O hydrogen bonds forming zigzag chains running parallel to the crystallographic c-axis.

Experimental

A solution of benzoyl chloride (10 mmol) in acetone was added slowly to a equimolar solution of ammonium thiocyanate in acetone. The reaction mixture was stirred at room temperature before adding piperidine (10 mmol) slowly and left stirring at room temperature for 4 h. The mixture was poured on to a water-ice mixture and then filtered. The pure product was recrystallized to give colourless crystals (70% yield).

Refinement

H atom positions were calculated and they were refined using a riding model with Uiso=1.2Ueq(C,N) and with Caromatic-H = 0.93 Å or C-H = 0.97 Å, and N-H = 0.86 Å.

Figures

Fig. 1.
The molecular structure of N-(piperidine-1-carbamothioyl)benzamide, with displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing of the title compound viewed down the c-axis. Hydrogen bonds are drawn as dashed lines.

Crystal data

C13H16N2OSF(000) = 528
Mr = 248.34Dx = 1.300 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1679 reflections
a = 10.913 (3) Åθ = 1.9–25.0°
b = 14.297 (4) ŵ = 0.24 mm1
c = 8.323 (2) ÅT = 298 K
β = 102.212 (6)°Needle, colourless
V = 1269.2 (6) Å30.50 × 0.41 × 0.38 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer2221 independent reflections
Radiation source: fine-focus sealed tube1727 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scanθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −12→8
Tmin = 0.889, Tmax = 0.915k = −16→17
7091 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0702P)2 + 0.1087P] where P = (Fo2 + 2Fc2)/3
2221 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

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)

xyzUiso*/Ueq
S10.93006 (6)0.86988 (4)0.12334 (8)0.0562 (2)
O11.15395 (14)0.65828 (11)0.05387 (17)0.0500 (4)
N11.07366 (15)0.72851 (13)0.2538 (2)0.0419 (4)
H1A1.08640.74270.35640.050*
N20.88426 (17)0.68658 (13)0.0845 (2)0.0444 (5)
C11.2732 (2)0.63954 (15)0.4875 (3)0.0472 (6)
H1B1.19680.64240.52010.057*
C21.3821 (3)0.61791 (16)0.6010 (3)0.0546 (6)
H2A1.37900.60720.71020.066*
C31.4937 (2)0.61231 (16)0.5526 (3)0.0560 (7)
H3A1.56650.59810.62940.067*
C41.4996 (2)0.62748 (16)0.3912 (3)0.0526 (6)
H4A1.57600.62300.35900.063*
C51.3923 (2)0.64924 (15)0.2774 (3)0.0448 (5)
H5A1.39610.65890.16810.054*
C61.27884 (19)0.65682 (14)0.3256 (2)0.0385 (5)
C71.1646 (2)0.68059 (14)0.1983 (2)0.0393 (5)
C80.95923 (19)0.75579 (16)0.1496 (2)0.0404 (5)
C90.9072 (2)0.58599 (16)0.1188 (3)0.0521 (6)
H9A0.98040.57850.20710.062*
H9B0.92430.55540.02180.062*
C100.7954 (2)0.53997 (16)0.1670 (3)0.0502 (6)
H10A0.80990.47310.17820.060*
H10B0.78640.56400.27290.060*
C110.6756 (2)0.55748 (17)0.0417 (3)0.0576 (7)
H11A0.60510.53190.08130.069*
H11B0.67970.5264−0.06050.069*
C120.6569 (2)0.66148 (17)0.0119 (3)0.0511 (6)
H12A0.58260.6717−0.07360.061*
H12B0.64380.69140.11150.061*
C130.7685 (2)0.70500 (17)−0.0388 (3)0.0491 (6)
H13A0.77670.6796−0.14410.059*
H13B0.75590.7720−0.05140.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0585 (4)0.0490 (4)0.0571 (4)0.0034 (3)0.0029 (3)0.0042 (3)
O10.0432 (9)0.0702 (11)0.0352 (9)0.0035 (8)0.0048 (7)−0.0055 (7)
N10.0350 (10)0.0584 (11)0.0305 (9)0.0052 (9)0.0028 (7)−0.0008 (7)
N20.0314 (10)0.0495 (11)0.0489 (10)0.0030 (9)0.0009 (8)0.0062 (8)
C10.0428 (13)0.0551 (14)0.0431 (13)0.0013 (11)0.0078 (10)0.0043 (10)
C20.0624 (16)0.0561 (15)0.0399 (13)0.0032 (13)−0.0013 (11)0.0079 (10)
C30.0446 (14)0.0504 (14)0.0619 (16)0.0031 (11)−0.0136 (12)0.0039 (11)
C40.0352 (13)0.0545 (15)0.0653 (16)0.0000 (11)0.0044 (11)−0.0026 (11)
C50.0383 (12)0.0496 (13)0.0456 (12)−0.0010 (10)0.0065 (10)−0.0002 (10)
C60.0341 (12)0.0411 (11)0.0387 (11)−0.0015 (9)0.0042 (9)0.0004 (9)
C70.0342 (12)0.0475 (12)0.0359 (11)−0.0035 (10)0.0065 (9)0.0032 (9)
C80.0351 (11)0.0556 (13)0.0313 (10)0.0023 (10)0.0084 (9)0.0030 (9)
C90.0374 (13)0.0471 (13)0.0689 (16)0.0065 (11)0.0051 (11)0.0026 (11)
C100.0447 (14)0.0438 (12)0.0586 (13)−0.0018 (11)0.0033 (11)0.0000 (10)
C110.0454 (14)0.0603 (15)0.0625 (15)−0.0081 (12)0.0012 (12)−0.0025 (12)
C120.0338 (12)0.0640 (15)0.0505 (13)0.0001 (11)−0.0027 (10)−0.0025 (11)
C130.0396 (13)0.0599 (14)0.0420 (12)0.0039 (11)−0.0041 (10)0.0062 (10)

Geometric parameters (Å, °)

S1—C81.667 (2)C5—C61.385 (3)
O1—C71.225 (2)C5—H5A0.9300
N1—C71.364 (3)C6—C71.495 (3)
N1—C81.416 (3)C9—C101.514 (3)
N1—H1A0.8600C9—H9A0.9700
N2—C81.325 (3)C9—H9B0.9700
N2—C131.473 (3)C10—C111.511 (3)
N2—C91.477 (3)C10—H10A0.9700
C1—C61.385 (3)C10—H10B0.9700
C1—C21.388 (3)C11—C121.514 (3)
C1—H1B0.9300C11—H11A0.9700
C2—C31.364 (4)C11—H11B0.9700
C2—H2A0.9300C12—C131.506 (3)
C3—C41.376 (3)C12—H12A0.9700
C3—H3A0.9300C12—H12B0.9700
C4—C51.377 (3)C13—H13A0.9700
C4—H4A0.9300C13—H13B0.9700
C7—N1—C8122.74 (17)N2—C9—C10111.15 (18)
C7—N1—H1A118.6N2—C9—H9A109.4
C8—N1—H1A118.6C10—C9—H9A109.4
C8—N2—C13121.05 (18)N2—C9—H9B109.4
C8—N2—C9125.68 (18)C10—C9—H9B109.4
C13—N2—C9113.22 (18)H9A—C9—H9B108.0
C6—C1—C2119.6 (2)C11—C10—C9111.9 (2)
C6—C1—H1B120.2C11—C10—H10A109.2
C2—C1—H1B120.2C9—C10—H10A109.2
C3—C2—C1120.2 (2)C11—C10—H10B109.2
C3—C2—H2A119.9C9—C10—H10B109.2
C1—C2—H2A119.9H10A—C10—H10B107.9
C2—C3—C4120.5 (2)C10—C11—C12110.07 (19)
C2—C3—H3A119.7C10—C11—H11A109.6
C4—C3—H3A119.7C12—C11—H11A109.6
C3—C4—C5119.9 (2)C10—C11—H11B109.6
C3—C4—H4A120.0C12—C11—H11B109.6
C5—C4—H4A120.0H11A—C11—H11B108.2
C4—C5—C6120.1 (2)C13—C12—C11111.2 (2)
C4—C5—H5A120.0C13—C12—H12A109.4
C6—C5—H5A120.0C11—C12—H12A109.4
C1—C6—C5119.7 (2)C13—C12—H12B109.4
C1—C6—C7121.89 (19)C11—C12—H12B109.4
C5—C6—C7118.43 (18)H12A—C12—H12B108.0
O1—C7—N1122.59 (19)N2—C13—C12110.88 (18)
O1—C7—C6121.86 (19)N2—C13—H13A109.5
N1—C7—C6115.56 (17)C12—C13—H13A109.5
N2—C8—N1115.66 (19)N2—C13—H13B109.5
N2—C8—S1126.36 (16)C12—C13—H13B109.5
N1—C8—S1117.96 (16)H13A—C13—H13B108.1
C6—C1—C2—C3−1.0 (3)C13—N2—C8—N1−173.80 (17)
C1—C2—C3—C4−0.3 (4)C9—N2—C8—N13.5 (3)
C2—C3—C4—C50.5 (3)C13—N2—C8—S17.6 (3)
C3—C4—C5—C60.7 (3)C9—N2—C8—S1−175.12 (16)
C2—C1—C6—C52.2 (3)C7—N1—C8—N265.2 (3)
C2—C1—C6—C7−179.9 (2)C7—N1—C8—S1−116.00 (19)
C4—C5—C6—C1−2.0 (3)C8—N2—C9—C10128.2 (2)
C4—C5—C6—C7179.98 (19)C13—N2—C9—C10−54.3 (2)
C8—N1—C7—O10.5 (3)N2—C9—C10—C1153.4 (3)
C8—N1—C7—C6−179.52 (18)C9—C10—C11—C12−54.2 (3)
C1—C6—C7—O1−148.6 (2)C10—C11—C12—C1355.5 (3)
C5—C6—C7—O129.4 (3)C8—N2—C13—C12−126.5 (2)
C1—C6—C7—N131.4 (3)C9—N2—C13—C1255.8 (2)
C5—C6—C7—N1−150.61 (19)C11—C12—C13—N2−56.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.182.949 (2)149

Symmetry codes: (i) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5376).

References

  • Bruker (2000). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mohamadou, A., Dechamps-Olivier, I. & Barbier, J. (1994). Polyhedron, 13, 1363–1370.
  • Nardelli, M. (1995). J. Appl. Cryst.28, 659.
  • Röbisch, G., Ludwig, E., Bansse, W. R. & Szargan, R. (1982). Z. Anorg. Allg. Chem.493, 26–32.
  • Salyn, J. V., Zumadilov, E. K., Nefedov, V. I., Scheibe, R., Leonhardt, G., Beyer, L. & Hoyer, E. (1977). Z. Anorg. Allg. Chem.432, 275–279.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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