4-(o-Tol-yl)piperazin-1-ium chloride.

In the title mol-ecular salt, C(11)H(17)N(2) (+)·Cl(-), the piperazin-1-ium ring adopts a chair conformation with the aromatic ring in a pseudo-equatorial orientation. The dihedral angle between the benzene ring and the mean plane of the piperazin-1-ium ring is 51.22 (6)°. In the crystal, N-H⋯Cl hydrogen bonds link the mol-ecules into chains propagating in [100]. Weak C-H⋯π inter-actions also ocur.

Related literature

For the medicinal applications of piperazine derivatives, see: Amir et al. (2004 ▶); Omar & AboulWafa (1986 ▶); El-Emam et al. (2004 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶). For a related structure, see: Ben Gharbia et al. (2008 ▶).

Experimental

Crystal data

C11H17N2 +·Cl−

M = 212.72

Orthorhombic,

a = 8.1572 (2) Å

b = 11.2821 (3) Å

c = 12.4256 (3) Å

V = 1143.53 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.54 × 0.33 × 0.23 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.854, T max = 0.936

8246 measured reflections

4871 independent reflections

4172 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 0.95

4871 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1943 Friedel pairs

Flack parameter: 0.02 (4)

Data collection: APEX2 (Bruker, 2009) ▶; cell refinement: SAINT (Bruker, 2009) ▶; data reduction: SAINT ▶; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044394/hb6474sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044394/hb6474Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044394/hb6474Isup3.cml

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

C11H17N2+·Cl−	F(000) = 456
Mr = 212.72	Dx = 1.236 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3871 reflections
a = 8.1572 (2) Å	θ = 2.4–35.1°
b = 11.2821 (3) Å	µ = 0.30 mm−1
c = 12.4256 (3) Å	T = 296 K
V = 1143.53 (5) Å3	Block, colourless
Z = 4	0.54 × 0.33 × 0.23 mm

Bruker APEX DUO CCD diffractometer	4871 independent reflections
Radiation source: fine-focus sealed tube	4172 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 35.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→13
Tmin = 0.854, Tmax = 0.936	k = −10→18
8246 measured reflections	l = −6→20

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.0493P] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
4871 reflections	Δρmax = 0.23 e Å−3
128 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1943 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (4)

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.

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 > 2sigma(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
Cl1	0.37470 (3)	0.15197 (3)	0.10255 (2)	0.04298 (7)
N1	1.02356 (12)	1.12619 (8)	1.00673 (8)	0.04027 (19)
H1N1	1.1142	1.1422	1.0407	0.048*
H2N1	0.9841	1.1900	0.9779	0.048*
N2	0.81569 (10)	0.94027 (7)	0.93398 (6)	0.03177 (15)
C1	0.93463 (14)	0.99338 (10)	0.86053 (8)	0.0381 (2)
H1A	0.8839	1.0581	0.8214	0.046*
H1B	0.9713	0.9347	0.8088	0.046*
C2	1.07872 (14)	1.03893 (12)	0.92397 (10)	0.0461 (2)
H2A	1.1337	0.9732	0.9590	0.055*
H2B	1.1563	1.0765	0.8757	0.055*
C3	0.89107 (15)	1.07704 (11)	1.07575 (8)	0.0427 (2)
H3A	0.8502	1.1384	1.1234	0.051*
H3B	0.9346	1.0134	1.1197	0.051*
C4	0.75240 (13)	1.03055 (10)	1.00711 (8)	0.0380 (2)
H4A	0.6679	0.9967	1.0526	0.046*
H4B	0.7042	1.0949	0.9662	0.046*
C5	0.69593 (12)	0.86761 (8)	0.88251 (6)	0.03052 (16)
C6	0.53332 (14)	0.90410 (10)	0.87004 (8)	0.0382 (2)
H6A	0.5015	0.9783	0.8951	0.046*
C7	0.41906 (15)	0.83147 (12)	0.82098 (9)	0.0468 (3)
H7A	0.3115	0.8571	0.8125	0.056*
C8	0.46538 (18)	0.72070 (12)	0.78461 (10)	0.0507 (3)
H8A	0.3895	0.6718	0.7507	0.061*
C9	0.62468 (18)	0.68295 (10)	0.79889 (9)	0.0451 (2)
H9A	0.6539	0.6076	0.7754	0.054*
C10	0.74324 (14)	0.75387 (9)	0.84727 (7)	0.03504 (18)
C11	0.91432 (17)	0.70764 (11)	0.86458 (11)	0.0482 (3)
H11A	0.9117	0.6227	0.8691	0.072*
H11B	0.9577	0.7396	0.9303	0.072*
H11C	0.9827	0.7312	0.8054	0.072*

	U11	U22	U33	U12	U13	U23
Cl1	0.03237 (11)	0.04279 (13)	0.05376 (13)	−0.00052 (10)	0.00001 (10)	0.00279 (11)
N1	0.0329 (4)	0.0355 (4)	0.0524 (5)	−0.0008 (3)	−0.0083 (3)	−0.0036 (3)
N2	0.0313 (4)	0.0318 (4)	0.0322 (3)	−0.0009 (3)	0.0029 (3)	−0.0031 (3)
C1	0.0336 (5)	0.0428 (5)	0.0377 (4)	−0.0050 (4)	0.0063 (4)	−0.0029 (4)
C2	0.0295 (4)	0.0507 (6)	0.0580 (6)	−0.0033 (4)	0.0039 (4)	−0.0098 (5)
C3	0.0469 (6)	0.0424 (5)	0.0388 (4)	−0.0020 (5)	−0.0015 (4)	−0.0088 (4)
C4	0.0343 (4)	0.0393 (5)	0.0404 (4)	−0.0028 (4)	0.0055 (4)	−0.0101 (4)
C5	0.0328 (4)	0.0306 (4)	0.0282 (3)	−0.0023 (3)	0.0012 (3)	0.0013 (3)
C6	0.0340 (4)	0.0396 (5)	0.0410 (4)	−0.0005 (4)	−0.0011 (4)	0.0005 (4)
C7	0.0363 (5)	0.0571 (7)	0.0470 (5)	−0.0074 (5)	−0.0054 (4)	0.0010 (5)
C8	0.0522 (7)	0.0509 (7)	0.0489 (5)	−0.0197 (6)	−0.0047 (5)	−0.0018 (5)
C9	0.0574 (7)	0.0347 (5)	0.0433 (5)	−0.0106 (5)	0.0040 (5)	−0.0040 (4)
C10	0.0425 (5)	0.0295 (4)	0.0331 (4)	−0.0009 (4)	0.0021 (3)	0.0016 (3)
C11	0.0518 (7)	0.0381 (5)	0.0548 (6)	0.0117 (5)	−0.0019 (5)	−0.0026 (5)

N1—C3	1.4869 (15)	C4—H4B	0.9700
N1—C2	1.4930 (15)	C5—C6	1.3974 (14)
N1—H1N1	0.8702	C5—C10	1.4098 (13)
N1—H2N1	0.8662	C6—C7	1.3827 (16)
N2—C5	1.4267 (12)	C6—H6A	0.9300
N2—C4	1.4593 (12)	C7—C8	1.382 (2)
N2—C1	1.4606 (13)	C7—H7A	0.9300
C1—C2	1.5056 (16)	C8—C9	1.379 (2)
C1—H1A	0.9700	C8—H8A	0.9300
C1—H1B	0.9700	C9—C10	1.3918 (16)
C2—H2A	0.9700	C9—H9A	0.9300
C2—H2B	0.9700	C10—C11	1.5053 (17)
C3—C4	1.5107 (15)	C11—H11A	0.9600
C3—H3A	0.9700	C11—H11B	0.9600
C3—H3B	0.9700	C11—H11C	0.9600
C4—H4A	0.9700
C3—N1—C2	111.74 (9)	C3—C4—H4A	109.8
C3—N1—H1N1	114.6	N2—C4—H4B	109.8
C2—N1—H1N1	102.4	C3—C4—H4B	109.8
C3—N1—H2N1	106.2	H4A—C4—H4B	108.3
C2—N1—H2N1	112.0	C6—C5—C10	119.57 (9)
H1N1—N1—H2N1	110.1	C6—C5—N2	122.03 (9)
C5—N2—C4	115.97 (8)	C10—C5—N2	118.35 (9)
C5—N2—C1	114.24 (7)	C7—C6—C5	120.94 (11)
C4—N2—C1	109.74 (8)	C7—C6—H6A	119.5
N2—C1—C2	109.36 (9)	C5—C6—H6A	119.5
N2—C1—H1A	109.8	C6—C7—C8	119.73 (12)
C2—C1—H1A	109.8	C6—C7—H7A	120.1
N2—C1—H1B	109.8	C8—C7—H7A	120.1
C2—C1—H1B	109.8	C9—C8—C7	119.67 (11)
H1A—C1—H1B	108.3	C9—C8—H8A	120.2
N1—C2—C1	110.51 (9)	C7—C8—H8A	120.2
N1—C2—H2A	109.5	C8—C9—C10	122.20 (11)
C1—C2—H2A	109.5	C8—C9—H9A	118.9
N1—C2—H2B	109.5	C10—C9—H9A	118.9
C1—C2—H2B	109.5	C9—C10—C5	117.86 (11)
H2A—C2—H2B	108.1	C9—C10—C11	120.45 (10)
N1—C3—C4	110.37 (8)	C5—C10—C11	121.65 (10)
N1—C3—H3A	109.6	C10—C11—H11A	109.5
C4—C3—H3A	109.6	C10—C11—H11B	109.5
N1—C3—H3B	109.6	H11A—C11—H11B	109.5
C4—C3—H3B	109.6	C10—C11—H11C	109.5
H3A—C3—H3B	108.1	H11A—C11—H11C	109.5
N2—C4—C3	109.21 (9)	H11B—C11—H11C	109.5
N2—C4—H4A	109.8
C5—N2—C1—C2	−164.57 (9)	C10—C5—C6—C7	−1.76 (15)
C4—N2—C1—C2	63.23 (11)	N2—C5—C6—C7	−179.23 (10)
C3—N1—C2—C1	53.08 (13)	C5—C6—C7—C8	0.65 (17)
N2—C1—C2—N1	−57.39 (13)	C6—C7—C8—C9	0.87 (18)
C2—N1—C3—C4	−53.24 (12)	C7—C8—C9—C10	−1.31 (18)
C5—N2—C4—C3	165.32 (8)	C8—C9—C10—C5	0.20 (16)
C1—N2—C4—C3	−63.38 (11)	C8—C9—C10—C11	177.96 (11)
N1—C3—C4—N2	57.89 (12)	C6—C5—C10—C9	1.32 (13)
C4—N2—C5—C6	22.41 (12)	N2—C5—C10—C9	178.88 (9)
C1—N2—C5—C6	−106.74 (10)	C6—C5—C10—C11	−176.42 (10)
C4—N2—C5—C10	−155.10 (9)	N2—C5—C10—C11	1.14 (13)
C1—N2—C5—C10	75.76 (11)

Cg2 is the centroid of C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···Cl1i	0.87	2.26	3.1155 (10)	167
N1—H2N1···Cl1ii	0.87	2.23	3.0956 (10)	177
C3—H3A···Cg2iii	0.97	2.79	3.5342 (11)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯Cl1i	0.87	2.26	3.1155 (10)	167
N1—H2N1⋯Cl1ii	0.87	2.23	3.0956 (10)	177
C3—H3A⋯Cg2iii	0.97	2.79	3.5342 (11)	134

Symmetry codes: (i) ; (ii) ; (iii) .