N-(1H-Indol-3-yl-methyl-idene)-4-methyl-piperazin-1-amine.

In the title compound, C14H18N4, the piperazine ring is in a slightly distorted chair conformation. The indole ring system is twisted from the piperazine ring, making a dihedral angle of 7.27 (11)°. In the crystal, N-H⋯N hydrogen bonds link mol-ecules into chains along [10-1].

Related literature

For a review of the current pharmacological and toxicological information for piperazine, see: Elliott (2011 ▶). For the biological activity of Schiff base ligands, see: Kharb et al. (2012 ▶); Savaliya et al. (2010 ▶); Xu et al. (2012 ▶). For related structures, see: Guo (2007 ▶); Ming-Lin et al. (2007 ▶); Xu et al. (2009 ▶); Zhou et al. (2011 ▶). For puckering parameters, see Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H18N4

M = 242.32

Monoclinic,

a = 7.5630 (5) Å

b = 6.5593 (4) Å

c = 13.2319 (9) Å

β = 100.072 (6)°

V = 646.29 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.48 × 0.33 × 0.18 mm

Data collection

Agilent Gemini Eos diffractometer

Absorption correction: multi-scan CrysAlis PRO and CrysAlis RED, Agilent (2012 ▶). T min = 0.868, T max = 1.000

7074 measured reflections

3857 independent reflections

3214 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.163

S = 1.06

3857 reflections

165 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028523/hg5354sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028523/hg5354Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028523/hg5354Isup3.cml

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

C14H18N4	F(000) = 260
Mr = 242.32	Dx = 1.245 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 7.5630 (5) Å	Cell parameters from 2079 reflections
b = 6.5593 (4) Å	θ = 3.4–33.0°
c = 13.2319 (9) Å	µ = 0.08 mm−1
β = 100.072 (6)°	T = 173 K
V = 646.29 (7) Å3	Irregular, yellow
Z = 2	0.48 × 0.33 × 0.18 mm

Agilent Gemini Eos diffractometer	3857 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3214 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.050
ω scans	θmax = 33.1°, θmin = 3.4°
Absorption correction: multi-scan CrysAlis PRO and CrysAlis RED, Agilent (2012).	h = −9→11
Tmin = 0.868, Tmax = 1.000	k = −6→9
7074 measured reflections	l = −19→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058	w = 1/[σ2(Fo2) + (0.0862P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.163	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.35 e Å−3
3857 reflections	Δρmin = −0.31 e Å−3
165 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.027 (9)
Primary atom site location: iterative

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

	x	y	z	Uiso*/Ueq
N1	0.5403 (3)	1.0302 (3)	0.32552 (17)	0.0256 (4)
N2	0.4353 (3)	0.8708 (3)	0.50758 (17)	0.0256 (5)
N3	0.4539 (3)	0.7746 (4)	0.60330 (19)	0.0283 (5)
N4	0.3483 (3)	0.2381 (3)	0.8128 (2)	0.0289 (5)
H4	0.3168	0.1197	0.8355	0.035*
C1	0.5358 (4)	1.1586 (4)	0.4158 (2)	0.0262 (5)
H1A	0.4167	1.2248	0.4097	0.031*
H1B	0.6279	1.2668	0.4196	0.031*
C2	0.5711 (3)	1.0305 (4)	0.5122 (2)	0.0252 (5)
H2A	0.6918	0.9678	0.5194	0.030*
H2B	0.5686	1.1181	0.5728	0.030*
C3	0.4253 (4)	0.7427 (4)	0.4164 (2)	0.0270 (5)
H3A	0.3232	0.6470	0.4125	0.032*
H3B	0.5369	0.6615	0.4214	0.032*
C4	0.4012 (3)	0.8721 (4)	0.3205 (2)	0.0287 (5)
H4A	0.4052	0.7834	0.2604	0.034*
H4B	0.2816	0.9379	0.3108	0.034*
C5	0.4143 (4)	0.5839 (4)	0.6077 (2)	0.0271 (5)
H5	0.3872	0.5075	0.5459	0.032*
C6	0.4101 (4)	0.4842 (4)	0.7047 (2)	0.0268 (5)
C7	0.3487 (4)	0.2858 (4)	0.7119 (2)	0.0276 (5)
H7	0.3125	0.1967	0.6555	0.033*
C8	0.4050 (3)	0.4047 (4)	0.8729 (2)	0.0256 (5)
C9	0.4229 (4)	0.4299 (5)	0.9786 (2)	0.0329 (6)
H9	0.3953	0.3224	1.0214	0.039*
C10	0.4827 (4)	0.6176 (5)	1.0192 (2)	0.0368 (6)
H10	0.4946	0.6398	1.0910	0.044*
C11	0.5260 (4)	0.7757 (5)	0.9559 (2)	0.0358 (7)
H11	0.5679	0.9023	0.9858	0.043*
C12	0.5083 (4)	0.7494 (4)	0.8510 (3)	0.0302 (6)
H12	0.5377	0.8569	0.8088	0.036*
C13	0.4467 (3)	0.5622 (4)	0.8078 (2)	0.0247 (5)
C14	0.5122 (4)	1.1517 (5)	0.2313 (2)	0.0363 (7)
H14A	0.3941	1.2173	0.2226	0.054*
H14B	0.5179	1.0628	0.1724	0.054*
H14C	0.6058	1.2563	0.2359	0.054*

	U11	U22	U33	U12	U13	U23
N1	0.0311 (10)	0.0236 (10)	0.0232 (10)	0.0024 (9)	0.0083 (8)	0.0033 (8)
N2	0.0341 (11)	0.0196 (9)	0.0250 (11)	−0.0007 (9)	0.0107 (8)	0.0011 (8)
N3	0.0346 (11)	0.0256 (11)	0.0272 (11)	0.0005 (9)	0.0121 (9)	0.0022 (9)
N4	0.0360 (12)	0.0201 (10)	0.0321 (12)	−0.0038 (9)	0.0098 (9)	0.0035 (9)
C1	0.0328 (12)	0.0182 (10)	0.0290 (13)	0.0009 (10)	0.0093 (10)	0.0015 (10)
C2	0.0313 (12)	0.0203 (11)	0.0256 (13)	−0.0021 (9)	0.0098 (9)	0.0002 (9)
C3	0.0328 (13)	0.0219 (11)	0.0269 (13)	−0.0018 (10)	0.0070 (10)	−0.0010 (10)
C4	0.0314 (12)	0.0290 (13)	0.0257 (13)	−0.0003 (10)	0.0052 (10)	−0.0005 (10)
C5	0.0332 (12)	0.0232 (12)	0.0271 (13)	−0.0017 (10)	0.0116 (10)	−0.0002 (10)
C6	0.0300 (12)	0.0224 (11)	0.0301 (13)	−0.0019 (9)	0.0112 (9)	0.0001 (10)
C7	0.0320 (12)	0.0223 (11)	0.0303 (14)	−0.0016 (10)	0.0101 (10)	0.0002 (10)
C8	0.0258 (11)	0.0207 (11)	0.0303 (13)	−0.0013 (10)	0.0048 (9)	0.0037 (10)
C9	0.0337 (13)	0.0340 (14)	0.0299 (14)	−0.0037 (12)	0.0026 (10)	0.0072 (12)
C10	0.0375 (15)	0.0410 (16)	0.0299 (15)	−0.0053 (13)	0.0002 (11)	0.0015 (12)
C11	0.0359 (15)	0.0325 (14)	0.0380 (17)	−0.0076 (12)	0.0040 (12)	−0.0043 (12)
C12	0.0268 (11)	0.0255 (12)	0.0388 (15)	−0.0048 (10)	0.0072 (10)	0.0011 (11)
C13	0.0217 (10)	0.0215 (11)	0.0318 (13)	0.0004 (9)	0.0073 (9)	0.0048 (10)
C14	0.0454 (16)	0.0343 (15)	0.0293 (14)	−0.0004 (13)	0.0069 (12)	0.0098 (12)

N1—C1	1.467 (3)	C4—H4B	0.9900
N1—C4	1.470 (3)	C5—H5	0.9500
N1—C14	1.463 (4)	C5—C6	1.446 (4)
N2—N3	1.400 (3)	C6—C7	1.390 (4)
N2—C2	1.461 (3)	C6—C13	1.438 (4)
N2—C3	1.462 (3)	C7—H7	0.9500
N3—C5	1.289 (4)	C8—C9	1.392 (4)
N4—H4	0.8800	C8—C13	1.416 (4)
N4—C7	1.371 (4)	C9—H9	0.9500
N4—C8	1.375 (4)	C9—C10	1.387 (4)
C1—H1A	0.9900	C10—H10	0.9500
C1—H1B	0.9900	C10—C11	1.407 (5)
C1—C2	1.511 (4)	C11—H11	0.9500
C2—H2A	0.9900	C11—C12	1.382 (4)
C2—H2B	0.9900	C12—H12	0.9500
C3—H3A	0.9900	C12—C13	1.399 (4)
C3—H3B	0.9900	C14—H14A	0.9800
C3—C4	1.510 (4)	C14—H14B	0.9800
C4—H4A	0.9900	C14—H14C	0.9800
C1—N1—C4	108.8 (2)	N3—C5—H5	119.3
C14—N1—C1	111.1 (2)	N3—C5—C6	121.3 (3)
C14—N1—C4	110.5 (2)	C6—C5—H5	119.3
N3—N2—C2	109.1 (2)	C7—C6—C5	122.9 (3)
N3—N2—C3	118.0 (2)	C7—C6—C13	106.2 (2)
C2—N2—C3	112.4 (2)	C13—C6—C5	130.6 (2)
C5—N3—N2	119.4 (2)	N4—C7—C6	109.8 (2)
C7—N4—H4	125.4	N4—C7—H7	125.1
C7—N4—C8	109.1 (2)	C6—C7—H7	125.1
C8—N4—H4	125.4	N4—C8—C9	129.9 (3)
N1—C1—H1A	109.7	N4—C8—C13	108.0 (2)
N1—C1—H1B	109.7	C9—C8—C13	122.1 (3)
N1—C1—C2	110.0 (2)	C8—C9—H9	121.2
H1A—C1—H1B	108.2	C10—C9—C8	117.6 (3)
C2—C1—H1A	109.7	C10—C9—H9	121.2
C2—C1—H1B	109.7	C9—C10—H10	119.4
N2—C2—C1	110.1 (2)	C9—C10—C11	121.2 (3)
N2—C2—H2A	109.6	C11—C10—H10	119.4
N2—C2—H2B	109.6	C10—C11—H11	119.5
C1—C2—H2A	109.6	C12—C11—C10	120.9 (3)
C1—C2—H2B	109.6	C12—C11—H11	119.5
H2A—C2—H2B	108.2	C11—C12—H12	120.4
N2—C3—H3A	109.5	C11—C12—C13	119.1 (3)
N2—C3—H3B	109.5	C13—C12—H12	120.4
N2—C3—C4	110.6 (2)	C8—C13—C6	106.9 (2)
H3A—C3—H3B	108.1	C12—C13—C6	134.0 (3)
C4—C3—H3A	109.5	C12—C13—C8	119.1 (3)
C4—C3—H3B	109.5	N1—C14—H14A	109.5
N1—C4—C3	112.2 (2)	N1—C14—H14B	109.5
N1—C4—H4A	109.2	N1—C14—H14C	109.5
N1—C4—H4B	109.2	H14A—C14—H14B	109.5
C3—C4—H4A	109.2	H14A—C14—H14C	109.5
C3—C4—H4B	109.2	H14B—C14—H14C	109.5
H4A—C4—H4B	107.9
N1—C1—C2—N2	−59.6 (3)	C5—C6—C13—C12	−5.0 (5)
N2—N3—C5—C6	−172.3 (2)	C7—N4—C8—C9	178.7 (3)
N2—C3—C4—N1	54.1 (3)	C7—N4—C8—C13	−1.3 (3)
N3—N2—C2—C1	−171.0 (2)	C7—C6—C13—C8	0.0 (3)
N3—N2—C3—C4	178.7 (2)	C7—C6—C13—C12	−179.1 (3)
N3—C5—C6—C7	172.6 (3)	C8—N4—C7—C6	1.4 (3)
N3—C5—C6—C13	−0.8 (4)	C8—C9—C10—C11	−0.9 (4)
N4—C8—C9—C10	−179.5 (3)	C9—C8—C13—C6	−179.2 (2)
N4—C8—C13—C6	0.8 (3)	C9—C8—C13—C12	0.1 (4)
N4—C8—C13—C12	−179.9 (2)	C9—C10—C11—C12	0.7 (5)
C1—N1—C4—C3	−57.8 (3)	C10—C11—C12—C13	−0.1 (4)
C2—N2—N3—C5	−148.2 (2)	C11—C12—C13—C6	178.8 (3)
C2—N2—C3—C4	−53.0 (3)	C11—C12—C13—C8	−0.3 (4)
C3—N2—N3—C5	−18.4 (3)	C13—C6—C7—N4	−0.9 (3)
C3—N2—C2—C1	56.1 (3)	C13—C8—C9—C10	0.5 (4)
C4—N1—C1—C2	60.0 (3)	C14—N1—C1—C2	−178.1 (2)
C5—C6—C7—N4	−175.6 (2)	C14—N1—C4—C3	179.9 (2)
C5—C6—C13—C8	174.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1i	0.88	2.29	2.947 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1i	0.88	2.29	2.947 (3)	131

Symmetry code: (i) .