3-Amino-5-(piperidin-1-yl)thio-phene-2,4-dicarbonitrile.

In the title compound, C(11)H(12)N(4)S, the thio-phene ring is roughly planar, with a maximum deviation of 0.012 (1) Å for the S atom, and makes a dihedral angle of 7.89 (8)° with the mean plane of the piperidine ring, which is in a chair conformation. The crystal packing is stabilized by pairs of centrosymmetric inter-molecular N-H⋯N hydrogen bonds, which results in the formation of a step-wise chain parallel to [10[Formula: see text]].

Related literature

For the biological activity of amino­thio­phene derivatives, see: Abdel-Fattah et al. (2006 ▶). For related structures, see: El-Saghier (2002 ▶); Eller & Holzer (2006 ▶); Thomae et al. (2009 ▶); Al-Adiwish et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12N4S

M = 232.31

Monoclinic,

a = 14.1637 (3) Å

b = 11.2823 (3) Å

c = 14.4413 (3) Å

β = 98.131 (2)°

V = 2284.51 (9) Å3

Z = 8

Cu Kα radiation

μ = 2.33 mm−1

T = 423 K

0.18 × 0.14 × 0.11 mm

Data collection

Oxford Diffraction Gemini CCD area-detector’ diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.679, T max = 0.784

11636 measured reflections

2188 independent reflections

2026 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.05

2188 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052950/kp2376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052950/kp2376Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052950/kp2376Isup3.cml

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

C11H12N4S	F(000) = 976
Mr = 232.31	Dx = 1.351 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 1189 reflections
a = 14.1637 (3) Å	θ = 3–71°
b = 11.2823 (3) Å	µ = 2.33 mm−1
c = 14.4413 (3) Å	T = 423 K
β = 98.131 (2)°	Plate-like, brown
V = 2284.51 (9) Å3	0.18 × 0.14 × 0.11 mm
Z = 8

Oxford Diffraction Gemini CCD area-detector' diffractometer	2188 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω/2θ scans	θmax = 71.2°, θmin = 5.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −15→17
Tmin = 0.679, Tmax = 0.784	k = −12→13
11636 measured reflections	l = −17→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0635P)2 + 1.3435P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2188 reflections	Δρmax = 0.36 e Å−3
146 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00105 (16)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst.105 107.

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.

	x	y	z	Uiso*/Ueq
S1	0.05434 (2)	0.13968 (4)	0.64677 (2)	0.02482 (16)
N1	−0.09012 (9)	0.19216 (12)	0.39813 (8)	0.0267 (3)
H1A	−0.1472	0.2138	0.4039	0.032*
H1B	−0.0730	0.1865	0.3435	0.032*
N2	0.11711 (10)	0.11912 (13)	0.30576 (9)	0.0324 (3)
N3	−0.21230 (9)	0.19501 (13)	0.61321 (9)	0.0305 (3)
N4	0.21438 (8)	0.07773 (11)	0.58195 (8)	0.0227 (3)
C1	0.12328 (10)	0.11239 (13)	0.55838 (10)	0.0202 (3)
C2	0.06959 (10)	0.13264 (12)	0.47006 (10)	0.0193 (3)
C3	−0.02745 (10)	0.16710 (12)	0.47476 (10)	0.0201 (3)
C4	−0.04625 (10)	0.17282 (14)	0.56599 (10)	0.0225 (3)
C5	−0.13693 (10)	0.18534 (13)	0.59338 (9)	0.0229 (3)
C6	0.09988 (10)	0.12325 (13)	0.38096 (10)	0.0224 (3)
C7	0.25656 (11)	0.08466 (16)	0.68138 (10)	0.0294 (4)
H7A	0.2077	0.0677	0.7203	0.035*
H7B	0.2794	0.1646	0.6954	0.035*
C8	0.33845 (12)	−0.00184 (17)	0.70481 (11)	0.0363 (4)
H8A	0.3139	−0.0822	0.7006	0.044*
H8B	0.3685	0.0114	0.7686	0.044*
C9	0.41251 (11)	0.01221 (18)	0.63870 (12)	0.0394 (4)
H9A	0.4414	0.0902	0.6464	0.047*
H9B	0.4624	−0.0466	0.6531	0.047*
C10	0.36437 (11)	−0.00355 (16)	0.53838 (12)	0.0325 (4)
H10A	0.4110	0.0086	0.4961	0.039*
H10B	0.3407	−0.0841	0.5299	0.039*
C11	0.28218 (10)	0.08241 (15)	0.51370 (11)	0.0269 (3)
H11A	0.3071	0.1623	0.5116	0.032*
H11B	0.2490	0.0634	0.4520	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.0192 (2)	0.0380 (3)	0.0174 (2)	0.00484 (13)	0.00300 (14)	−0.00005 (13)
N1	0.0193 (6)	0.0404 (8)	0.0200 (6)	0.0078 (5)	0.0022 (5)	−0.0001 (5)
N2	0.0253 (7)	0.0511 (9)	0.0213 (7)	0.0034 (6)	0.0055 (5)	0.0012 (6)
N3	0.0237 (7)	0.0427 (8)	0.0257 (7)	0.0076 (6)	0.0057 (5)	0.0045 (6)
N4	0.0163 (6)	0.0318 (7)	0.0196 (6)	0.0015 (5)	0.0017 (5)	0.0014 (5)
C1	0.0192 (7)	0.0209 (7)	0.0211 (7)	−0.0018 (5)	0.0048 (5)	0.0001 (5)
C2	0.0181 (7)	0.0213 (7)	0.0188 (7)	−0.0003 (5)	0.0036 (5)	0.0001 (5)
C3	0.0192 (7)	0.0197 (7)	0.0214 (7)	−0.0006 (5)	0.0030 (5)	−0.0004 (5)
C4	0.0175 (7)	0.0283 (8)	0.0213 (7)	0.0031 (6)	0.0017 (5)	−0.0005 (6)
C5	0.0232 (8)	0.0263 (8)	0.0189 (7)	0.0041 (6)	0.0017 (6)	0.0010 (6)
C6	0.0171 (7)	0.0256 (8)	0.0240 (8)	0.0010 (5)	0.0011 (6)	0.0014 (6)
C7	0.0233 (7)	0.0427 (10)	0.0212 (7)	0.0020 (6)	−0.0002 (6)	−0.0022 (6)
C8	0.0271 (8)	0.0510 (11)	0.0277 (8)	0.0070 (7)	−0.0065 (7)	0.0017 (7)
C9	0.0192 (8)	0.0573 (12)	0.0395 (10)	0.0081 (7)	−0.0035 (7)	−0.0037 (8)
C10	0.0211 (7)	0.0432 (10)	0.0328 (9)	0.0077 (7)	0.0030 (6)	−0.0009 (7)
C11	0.0198 (7)	0.0339 (9)	0.0280 (8)	0.0019 (6)	0.0065 (6)	0.0038 (6)

S1—C1	1.7407 (14)	C7—C8	1.517 (2)
S1—C4	1.7493 (14)	C7—H7A	0.9700
N1—C3	1.3471 (19)	C7—H7B	0.9700
N1—H1A	0.8600	C8—C9	1.523 (2)
N1—H1B	0.8600	C8—H8A	0.9700
N2—C6	1.147 (2)	C8—H8B	0.9700
N3—C5	1.149 (2)	C9—C10	1.522 (2)
N4—C1	1.3452 (19)	C9—H9A	0.9700
N4—C11	1.4710 (18)	C9—H9B	0.9700
N4—C7	1.4773 (18)	C10—C11	1.518 (2)
C1—C2	1.408 (2)	C10—H10A	0.9700
C2—C6	1.417 (2)	C10—H10B	0.9700
C2—C3	1.439 (2)	C11—H11A	0.9700
C3—C4	1.382 (2)	C11—H11B	0.9700
C4—C5	1.403 (2)
C1—S1—C4	92.14 (7)	H7A—C7—H7B	107.9
C3—N1—H1A	120.0	C7—C8—C9	111.46 (14)
C3—N1—H1B	120.0	C7—C8—H8A	109.3
H1A—N1—H1B	120.0	C9—C8—H8A	109.3
C1—N4—C11	120.92 (12)	C7—C8—H8B	109.3
C1—N4—C7	118.17 (12)	C9—C8—H8B	109.3
C11—N4—C7	115.90 (12)	H8A—C8—H8B	108.0
N4—C1—C2	130.70 (13)	C10—C9—C8	109.21 (13)
N4—C1—S1	118.91 (10)	C10—C9—H9A	109.8
C2—C1—S1	110.39 (10)	C8—C9—H9A	109.8
C1—C2—C6	128.05 (13)	C10—C9—H9B	109.8
C1—C2—C3	113.45 (12)	C8—C9—H9B	109.8
C6—C2—C3	118.50 (13)	H9A—C9—H9B	108.3
N1—C3—C4	125.45 (13)	C11—C10—C9	111.98 (14)
N1—C3—C2	122.72 (13)	C11—C10—H10A	109.2
C4—C3—C2	111.82 (12)	C9—C10—H10A	109.2
C3—C4—C5	125.50 (13)	C11—C10—H10B	109.2
C3—C4—S1	112.16 (11)	C9—C10—H10B	109.2
C5—C4—S1	121.67 (11)	H10A—C10—H10B	107.9
N3—C5—C4	178.05 (15)	N4—C11—C10	111.79 (12)
N2—C6—C2	174.32 (16)	N4—C11—H11A	109.3
N4—C7—C8	111.97 (13)	C10—C11—H11A	109.3
N4—C7—H7A	109.2	N4—C11—H11B	109.3
C8—C7—H7A	109.2	C10—C11—H11B	109.3
N4—C7—H7B	109.2	H11A—C11—H11B	107.9
C8—C7—H7B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3i	0.86	2.22	3.0576 (19)	164
N1—H1B···N2ii	0.86	2.29	3.0293 (17)	145
C7—H7A···S1	0.97	2.42	2.9041 (16)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3i	0.86	2.22	3.0576 (19)	164
N1—H1B⋯N2ii	0.86	2.29	3.0293 (17)	145

Symmetry codes: (i) ; (ii) .