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

Al-abbasi, A.A.; Yarmo, M.A.; Kassim, M.B.

doi:10.1107/S160053681004170X

organic compounds

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Volume 66| Part 11| November 2010| Page o2896

https://doi.org/10.1107/S160053681004170X

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

Aisha A. Al-abbasi,^a Mohd Ambar Yarmo ^a and Mohammad B. Kassim ^a ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia
^*Correspondence e-mail: mbkassim@ukm.my

(Received 12 October 2010; accepted 15 October 2010; online 23 October 2010)

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 ); Salyn et al. (1977 ); Röbisch et al. (1982 ).

Experimental

Crystal data

C₁₃H₁₆N₂OS
M_r = 248.34
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.08
2221 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.18	2.949 (2)	149
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004170X/bt5376Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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).

Structure description top

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

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

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₃H₁₆N₂OS	F(000) = 528
M_r = 248.34	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1679 reflections
a = 10.913 (3) Å	θ = 1.9–25.0°
b = 14.297 (4) Å	µ = 0.24 mm⁻¹
c = 8.323 (2) Å	T = 298 K
β = 102.212 (6)°	Needle, colourless
V = 1269.2 (6) Å³	0.50 × 0.41 × 0.38 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2221 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scan	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→8
T_min = 0.889, T_max = 0.915	k = −16→17
7091 measured reflections	l = −9→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0702P)² + 0.1087P] where P = (F_o² + 2F_c²)/3
2221 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₃H₁₆N₂OS	V = 1269.2 (6) Å³
M_r = 248.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.913 (3) Å	µ = 0.24 mm⁻¹
b = 14.297 (4) Å	T = 298 K
c = 8.323 (2) Å	0.50 × 0.41 × 0.38 mm
β = 102.212 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2221 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1727 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.915	R_int = 0.031
7091 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.08	Δρ_max = 0.29 e Å⁻³
2221 reflections	Δρ_min = −0.27 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.93006 (6)	0.86988 (4)	0.12334 (8)	0.0562 (2)
O1	1.15395 (14)	0.65828 (11)	0.05387 (17)	0.0500 (4)
N1	1.07366 (15)	0.72851 (13)	0.2538 (2)	0.0419 (4)
H1A	1.0864	0.7427	0.3564	0.050*
N2	0.88426 (17)	0.68658 (13)	0.0845 (2)	0.0444 (5)
C1	1.2732 (2)	0.63954 (15)	0.4875 (3)	0.0472 (6)
H1B	1.1968	0.6424	0.5201	0.057*
C2	1.3821 (3)	0.61791 (16)	0.6010 (3)	0.0546 (6)
H2A	1.3790	0.6072	0.7102	0.066*
C3	1.4937 (2)	0.61231 (16)	0.5526 (3)	0.0560 (7)
H3A	1.5665	0.5981	0.6294	0.067*
C4	1.4996 (2)	0.62748 (16)	0.3912 (3)	0.0526 (6)
H4A	1.5760	0.6230	0.3590	0.063*
C5	1.3923 (2)	0.64924 (15)	0.2774 (3)	0.0448 (5)
H5A	1.3961	0.6589	0.1681	0.054*
C6	1.27884 (19)	0.65682 (14)	0.3256 (2)	0.0385 (5)
C7	1.1646 (2)	0.68059 (14)	0.1983 (2)	0.0393 (5)
C8	0.95923 (19)	0.75579 (16)	0.1496 (2)	0.0404 (5)
C9	0.9072 (2)	0.58599 (16)	0.1188 (3)	0.0521 (6)
H9A	0.9804	0.5785	0.2071	0.062*
H9B	0.9243	0.5554	0.0218	0.062*
C10	0.7954 (2)	0.53997 (16)	0.1670 (3)	0.0502 (6)
H10A	0.8099	0.4731	0.1782	0.060*
H10B	0.7864	0.5640	0.2729	0.060*
C11	0.6756 (2)	0.55748 (17)	0.0417 (3)	0.0576 (7)
H11A	0.6051	0.5319	0.0813	0.069*
H11B	0.6797	0.5264	−0.0605	0.069*
C12	0.6569 (2)	0.66148 (17)	0.0119 (3)	0.0511 (6)
H12A	0.5826	0.6717	−0.0736	0.061*
H12B	0.6438	0.6914	0.1115	0.061*
C13	0.7685 (2)	0.70500 (17)	−0.0388 (3)	0.0491 (6)
H13A	0.7767	0.6796	−0.1441	0.059*
H13B	0.7559	0.7720	−0.0514	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0585 (4)	0.0490 (4)	0.0571 (4)	0.0034 (3)	0.0029 (3)	0.0042 (3)
O1	0.0432 (9)	0.0702 (11)	0.0352 (9)	0.0035 (8)	0.0048 (7)	−0.0055 (7)
N1	0.0350 (10)	0.0584 (11)	0.0305 (9)	0.0052 (9)	0.0028 (7)	−0.0008 (7)
N2	0.0314 (10)	0.0495 (11)	0.0489 (10)	0.0030 (9)	0.0009 (8)	0.0062 (8)
C1	0.0428 (13)	0.0551 (14)	0.0431 (13)	0.0013 (11)	0.0078 (10)	0.0043 (10)
C2	0.0624 (16)	0.0561 (15)	0.0399 (13)	0.0032 (13)	−0.0013 (11)	0.0079 (10)
C3	0.0446 (14)	0.0504 (14)	0.0619 (16)	0.0031 (11)	−0.0136 (12)	0.0039 (11)
C4	0.0352 (13)	0.0545 (15)	0.0653 (16)	0.0000 (11)	0.0044 (11)	−0.0026 (11)
C5	0.0383 (12)	0.0496 (13)	0.0456 (12)	−0.0010 (10)	0.0065 (10)	−0.0002 (10)
C6	0.0341 (12)	0.0411 (11)	0.0387 (11)	−0.0015 (9)	0.0042 (9)	0.0004 (9)
C7	0.0342 (12)	0.0475 (12)	0.0359 (11)	−0.0035 (10)	0.0065 (9)	0.0032 (9)
C8	0.0351 (11)	0.0556 (13)	0.0313 (10)	0.0023 (10)	0.0084 (9)	0.0030 (9)
C9	0.0374 (13)	0.0471 (13)	0.0689 (16)	0.0065 (11)	0.0051 (11)	0.0026 (11)
C10	0.0447 (14)	0.0438 (12)	0.0586 (13)	−0.0018 (11)	0.0033 (11)	0.0000 (10)
C11	0.0454 (14)	0.0603 (15)	0.0625 (15)	−0.0081 (12)	0.0012 (12)	−0.0025 (12)
C12	0.0338 (12)	0.0640 (15)	0.0505 (13)	0.0001 (11)	−0.0027 (10)	−0.0025 (11)
C13	0.0396 (13)	0.0599 (14)	0.0420 (12)	0.0039 (11)	−0.0041 (10)	0.0062 (10)

Geometric parameters (Å, º) top

S1—C8	1.667 (2)	C5—C6	1.385 (3)
O1—C7	1.225 (2)	C5—H5A	0.9300
N1—C7	1.364 (3)	C6—C7	1.495 (3)
N1—C8	1.416 (3)	C9—C10	1.514 (3)
N1—H1A	0.8600	C9—H9A	0.9700
N2—C8	1.325 (3)	C9—H9B	0.9700
N2—C13	1.473 (3)	C10—C11	1.511 (3)
N2—C9	1.477 (3)	C10—H10A	0.9700
C1—C6	1.385 (3)	C10—H10B	0.9700
C1—C2	1.388 (3)	C11—C12	1.514 (3)
C1—H1B	0.9300	C11—H11A	0.9700
C2—C3	1.364 (4)	C11—H11B	0.9700
C2—H2A	0.9300	C12—C13	1.506 (3)
C3—C4	1.376 (3)	C12—H12A	0.9700
C3—H3A	0.9300	C12—H12B	0.9700
C4—C5	1.377 (3)	C13—H13A	0.9700
C4—H4A	0.9300	C13—H13B	0.9700

C7—N1—C8	122.74 (17)	N2—C9—C10	111.15 (18)
C7—N1—H1A	118.6	N2—C9—H9A	109.4
C8—N1—H1A	118.6	C10—C9—H9A	109.4
C8—N2—C13	121.05 (18)	N2—C9—H9B	109.4
C8—N2—C9	125.68 (18)	C10—C9—H9B	109.4
C13—N2—C9	113.22 (18)	H9A—C9—H9B	108.0
C6—C1—C2	119.6 (2)	C11—C10—C9	111.9 (2)
C6—C1—H1B	120.2	C11—C10—H10A	109.2
C2—C1—H1B	120.2	C9—C10—H10A	109.2
C3—C2—C1	120.2 (2)	C11—C10—H10B	109.2
C3—C2—H2A	119.9	C9—C10—H10B	109.2
C1—C2—H2A	119.9	H10A—C10—H10B	107.9
C2—C3—C4	120.5 (2)	C10—C11—C12	110.07 (19)
C2—C3—H3A	119.7	C10—C11—H11A	109.6
C4—C3—H3A	119.7	C12—C11—H11A	109.6
C3—C4—C5	119.9 (2)	C10—C11—H11B	109.6
C3—C4—H4A	120.0	C12—C11—H11B	109.6
C5—C4—H4A	120.0	H11A—C11—H11B	108.2
C4—C5—C6	120.1 (2)	C13—C12—C11	111.2 (2)
C4—C5—H5A	120.0	C13—C12—H12A	109.4
C6—C5—H5A	120.0	C11—C12—H12A	109.4
C1—C6—C5	119.7 (2)	C13—C12—H12B	109.4
C1—C6—C7	121.89 (19)	C11—C12—H12B	109.4
C5—C6—C7	118.43 (18)	H12A—C12—H12B	108.0
O1—C7—N1	122.59 (19)	N2—C13—C12	110.88 (18)
O1—C7—C6	121.86 (19)	N2—C13—H13A	109.5
N1—C7—C6	115.56 (17)	C12—C13—H13A	109.5
N2—C8—N1	115.66 (19)	N2—C13—H13B	109.5
N2—C8—S1	126.36 (16)	C12—C13—H13B	109.5
N1—C8—S1	117.96 (16)	H13A—C13—H13B	108.1

C6—C1—C2—C3	−1.0 (3)	C13—N2—C8—N1	−173.80 (17)
C1—C2—C3—C4	−0.3 (4)	C9—N2—C8—N1	3.5 (3)
C2—C3—C4—C5	0.5 (3)	C13—N2—C8—S1	7.6 (3)
C3—C4—C5—C6	0.7 (3)	C9—N2—C8—S1	−175.12 (16)
C2—C1—C6—C5	2.2 (3)	C7—N1—C8—N2	65.2 (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—C10	128.2 (2)
C4—C5—C6—C7	179.98 (19)	C13—N2—C9—C10	−54.3 (2)
C8—N1—C7—O1	0.5 (3)	N2—C9—C10—C11	53.4 (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—C13	55.5 (3)
C5—C6—C7—O1	29.4 (3)	C8—N2—C13—C12	−126.5 (2)
C1—C6—C7—N1	31.4 (3)	C9—N2—C13—C12	55.8 (2)
C5—C6—C7—N1	−150.61 (19)	C11—C12—C13—N2	−56.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.18	2.949 (2)	149

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂OS
M_r	248.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.913 (3), 14.297 (4), 8.323 (2)
β (°)	102.212 (6)
V (Å³)	1269.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.41 × 0.38

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.889, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	7091, 2221, 1727
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.08
No. of reflections	2221
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.18	2.949 (2)	149

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

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.

References

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