4-(Cyano-meth-yl)anilinium chloride.

The crystal structure of the title compound, C(8)H(9)N(2) (+)·Cl(-), is stabilized by N-H⋯Cl hydrogen bonds.

Related literature

For background to phase transition materials, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C8H9N2 +·Cl−

M = 168.62

Monoclinic,

a = 5.4348 (12) Å

b = 8.5630 (18) Å

c = 18.000 (4) Å

β = 93.734 (16)°

V = 835.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 293 K

0.45 × 0.28 × 0.25 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.5, T max = 0.5

8241 measured reflections

1890 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.139

S = 1.18

1890 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018076/jh2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018076/jh2157Isup2.hkl

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

C8H9N2+·Cl−	F(000) = 352
Mr = 168.62	Dx = 1.340 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2330 reflections
a = 5.4348 (12) Å	θ = 3.2–27.6°
b = 8.5630 (18) Å	µ = 0.39 mm−1
c = 18.000 (4) Å	T = 293 K
β = 93.734 (16)°	Prism, orange
V = 835.9 (3) Å3	0.45 × 0.28 × 0.25 mm
Z = 4

Rigaku SCXmini diffractometer	1890 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.3°
CCD_Profile_fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.5, Tmax = 0.5	l = −23→23
8241 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
1890 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

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 > 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
C1	0.4618 (3)	0.31846 (19)	0.11664 (9)	0.0300 (4)
C2	0.2846 (3)	0.3656 (2)	0.06362 (11)	0.0392 (4)
H2	0.1527	0.4266	0.0768	0.047*
C3	0.3045 (3)	0.3213 (2)	−0.00980 (11)	0.0399 (5)
H3	0.1846	0.3524	−0.0460	0.048*
C4	0.5017 (3)	0.2308 (2)	−0.02981 (9)	0.0318 (4)
C5	0.6768 (3)	0.1847 (2)	0.02470 (10)	0.0381 (4)
H5	0.8087	0.1233	0.0119	0.046*
C6	0.6587 (3)	0.2288 (2)	0.09839 (10)	0.0375 (4)
H6	0.7780	0.1981	0.1348	0.045*
C7	0.5134 (4)	0.1847 (3)	−0.11122 (11)	0.0424 (5)
H7A	0.3717	0.1201	−0.1257	0.051*
H7B	0.5031	0.2784	−0.1416	0.051*
C8	0.7369 (4)	0.1002 (2)	−0.12648 (10)	0.0380 (4)
N1	0.4471 (3)	0.36295 (19)	0.19498 (8)	0.0339 (4)
H1A	0.3056	0.4126	0.2005	0.051*
H1B	0.5727	0.4256	0.2087	0.051*
H1C	0.4541	0.2776	0.2233	0.051*
N2	0.9120 (4)	0.0349 (3)	−0.13867 (12)	0.0593 (6)
Cl1	0.94611 (8)	0.55382 (5)	0.21151 (3)	0.0395 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0310 (9)	0.0303 (8)	0.0290 (8)	−0.0016 (7)	0.0037 (7)	0.0014 (7)
C2	0.0324 (9)	0.0462 (11)	0.0391 (10)	0.0129 (8)	0.0023 (7)	−0.0008 (8)
C3	0.0344 (10)	0.0505 (11)	0.0339 (10)	0.0123 (8)	−0.0045 (7)	0.0023 (8)
C4	0.0309 (9)	0.0335 (9)	0.0310 (9)	0.0017 (7)	0.0011 (7)	0.0010 (7)
C5	0.0318 (9)	0.0460 (11)	0.0362 (10)	0.0116 (8)	0.0005 (7)	−0.0027 (8)
C6	0.0324 (9)	0.0471 (10)	0.0322 (9)	0.0095 (8)	−0.0030 (7)	0.0022 (8)
C7	0.0409 (11)	0.0528 (12)	0.0327 (10)	0.0119 (9)	−0.0024 (8)	−0.0024 (8)
C8	0.0395 (11)	0.0464 (10)	0.0279 (9)	0.0031 (9)	0.0011 (7)	0.0002 (8)
N1	0.0347 (8)	0.0367 (8)	0.0305 (8)	0.0031 (6)	0.0034 (6)	0.0007 (6)
N2	0.0484 (12)	0.0836 (15)	0.0463 (11)	0.0210 (10)	0.0059 (9)	−0.0014 (10)
Cl1	0.0360 (3)	0.0418 (3)	0.0404 (3)	0.00352 (17)	−0.0006 (2)	−0.00759 (18)

C1—C2	1.372 (3)	C5—H5	0.9300
C1—C6	1.374 (2)	C6—H6	0.9300
C1—N1	1.468 (2)	C7—C8	1.455 (3)
C2—C3	1.386 (3)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C4	1.389 (2)	C8—N2	1.137 (3)
C3—H3	0.9300	N1—H1A	0.8900
C4—C5	1.380 (3)	N1—H1B	0.8900
C4—C7	1.523 (3)	N1—H1C	0.8900
C5—C6	1.389 (3)
C2—C1—C6	121.37 (16)	C1—C6—H6	120.5
C2—C1—N1	120.80 (16)	C5—C6—H6	120.5
C6—C1—N1	117.82 (16)	C8—C7—C4	113.47 (16)
C1—C2—C3	119.20 (16)	C8—C7—H7A	108.9
C1—C2—H2	120.4	C4—C7—H7A	108.9
C3—C2—H2	120.4	C8—C7—H7B	108.9
C2—C3—C4	120.63 (17)	C4—C7—H7B	108.9
C2—C3—H3	119.7	H7A—C7—H7B	107.7
C4—C3—H3	119.7	N2—C8—C7	179.6 (3)
C5—C4—C3	118.92 (16)	C1—N1—H1A	109.5
C5—C4—C7	122.68 (16)	C1—N1—H1B	109.5
C3—C4—C7	118.39 (16)	H1A—N1—H1B	109.5
C4—C5—C6	120.85 (17)	C1—N1—H1C	109.5
C4—C5—H5	119.6	H1A—N1—H1C	109.5
C6—C5—H5	119.6	H1B—N1—H1C	109.5
C1—C6—C5	119.02 (17)
C6—C1—C2—C3	0.2 (3)	C2—C1—C6—C5	−0.3 (3)
N1—C1—C2—C3	−179.95 (17)	N1—C1—C6—C5	179.84 (17)
C1—C2—C3—C4	−0.3 (3)	C4—C5—C6—C1	0.5 (3)
C2—C3—C4—C5	0.5 (3)	C5—C4—C7—C8	−5.2 (3)
C2—C3—C4—C7	179.66 (19)	C3—C4—C7—C8	175.67 (19)
C3—C4—C5—C6	−0.6 (3)	C4—C7—C8—N2	−114 (37)
C7—C4—C5—C6	−179.74 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl1	0.89	2.31	3.1638 (17)	162
N1—H1A···Cl1i	0.89	2.32	3.2061 (16)	177
N1—H1C···Cl1ii	0.89	2.29	3.1700 (17)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl1	0.89	2.31	3.1638 (17)	162
N1—H1A⋯Cl1i	0.89	2.32	3.2061 (16)	177
N1—H1C⋯Cl1ii	0.89	2.29	3.1700 (17)	168

Symmetry codes: (i) ; (ii) .