3-Cyano-N-(2-hydroxy-benz-yl)anilinium chloride.

In the cation of the title compound, C(14)H(13)N(2)O(+)·Cl(-), the two benzene rings are roughly parallel and are twisted slightly from each other by a dihedral angle of only 2.87 (1)°. In the crystal, weak inter-molecular N-H⋯Cl and O-H⋯Cl hydrogen bonds link the cations and anions into chains extended along the b axis.

Related literature

For the crystal structures and properties of related compounds, see: Fu et al. (2007 ▶, 2008 ▶, 2009 ▶); Fu & Xiong (2008 ▶); Zhao et al. (2008 ▶); Loeb et al. (2005 ▶).

Experimental

Crystal data

C14H13N2O+·Cl−

M = 260.71

Monoclinic,

a = 13.071 (3) Å

b = 7.9437 (16) Å

c = 13.141 (3) Å

β = 90.18 (3)°

V = 1364.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 K

0.4 × 0.35 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.881, T max = 0.940

13632 measured reflections

3116 independent reflections

2264 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.127

S = 1.05

3116 reflections

163 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003521/dn2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003521/dn2531Isup2.hkl

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

C14H13N2O+·Cl−	F(000) = 544
Mr = 260.71	Dx = 1.269 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2264 reflections
a = 13.071 (3) Å	θ = 3.0–27.5°
b = 7.9437 (16) Å	µ = 0.27 mm−1
c = 13.141 (3) Å	T = 298 K
β = 90.18 (3)°	Block, colourless
V = 1364.4 (5) Å3	0.4 × 0.35 × 0.2 mm
Z = 4

Rigaku Mercury2 diffractometer	3116 independent reflections
Radiation source: fine-focus sealed tube	2264 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.881, Tmax = 0.940	l = −17→17
13632 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.2789P] where P = (Fo2 + 2Fc2)/3
3116 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.31 e Å−3
3 restraints	Δρmin = −0.26 e Å−3

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
N1	0.64724 (11)	0.46075 (18)	0.35772 (11)	0.0389 (4)
H1A	0.6623	0.5479	0.3166	0.058*
H1B	0.6961	0.3821	0.3496	0.058*
O1	0.70213 (12)	0.84372 (19)	0.41720 (13)	0.0677 (5)
H1	0.7241	0.9398	0.3990	0.102*
C12	0.42880 (16)	0.1649 (2)	0.33106 (15)	0.0474 (5)
C13	0.52443 (14)	0.2279 (2)	0.35670 (14)	0.0420 (4)
H13	0.5712	0.1625	0.3927	0.050*
C8	0.54865 (14)	0.3902 (2)	0.32752 (14)	0.0389 (4)
C11	0.35950 (16)	0.2619 (3)	0.27743 (17)	0.0559 (5)
H11	0.2953	0.2190	0.2610	0.067*
C9	0.48044 (15)	0.4880 (2)	0.27398 (17)	0.0499 (5)
H9	0.4978	0.5972	0.2552	0.060*
C6	0.74965 (16)	0.5918 (3)	0.49665 (15)	0.0487 (5)
C1	0.77360 (16)	0.7568 (3)	0.47075 (16)	0.0494 (5)
C7	0.64809 (17)	0.5202 (3)	0.46654 (16)	0.0552 (6)
H7A	0.5957	0.6054	0.4753	0.066*
H7B	0.6318	0.4265	0.5109	0.066*
C2	0.86690 (18)	0.8245 (3)	0.50023 (18)	0.0611 (6)
H2	0.8834	0.9346	0.4828	0.073*
C10	0.38606 (16)	0.4227 (3)	0.24836 (19)	0.0603 (6)
H10	0.3400	0.4877	0.2112	0.072*
C14	0.40186 (18)	−0.0046 (3)	0.36042 (19)	0.0601 (6)
C3	0.93473 (19)	0.7289 (4)	0.55504 (19)	0.0690 (7)
H3	0.9973	0.7747	0.5745	0.083*
C5	0.81903 (19)	0.4986 (3)	0.55185 (17)	0.0613 (6)
H5	0.8032	0.3882	0.5693	0.074*
C4	0.9113 (2)	0.5654 (4)	0.58170 (18)	0.0702 (7)
H4	0.9573	0.5013	0.6194	0.084*
N2	0.3796 (2)	−0.1368 (3)	0.3823 (2)	0.0900 (8)
Cl1	0.79799 (4)	0.17211 (7)	0.33575 (4)	0.05632 (19)

	U11	U22	U33	U12	U13	U23
N1	0.0389 (8)	0.0327 (8)	0.0452 (9)	−0.0017 (6)	0.0049 (6)	−0.0003 (7)
O1	0.0616 (10)	0.0608 (10)	0.0808 (12)	−0.0066 (8)	−0.0118 (8)	0.0039 (8)
C12	0.0514 (12)	0.0390 (10)	0.0519 (12)	−0.0115 (9)	0.0063 (9)	−0.0078 (9)
C13	0.0455 (11)	0.0337 (9)	0.0469 (11)	−0.0002 (8)	0.0006 (8)	0.0020 (8)
C8	0.0361 (10)	0.0360 (9)	0.0447 (10)	−0.0011 (8)	0.0059 (8)	−0.0030 (8)
C11	0.0419 (11)	0.0632 (14)	0.0625 (13)	−0.0077 (10)	−0.0020 (10)	−0.0044 (11)
C9	0.0440 (12)	0.0403 (11)	0.0654 (13)	0.0024 (9)	0.0048 (9)	0.0091 (9)
C6	0.0529 (12)	0.0520 (12)	0.0412 (10)	−0.0106 (10)	0.0068 (9)	−0.0092 (9)
C1	0.0490 (12)	0.0506 (12)	0.0487 (11)	−0.0075 (10)	−0.0008 (9)	−0.0096 (10)
C7	0.0590 (13)	0.0570 (13)	0.0497 (12)	−0.0183 (10)	0.0132 (10)	−0.0139 (10)
C2	0.0628 (15)	0.0572 (13)	0.0634 (14)	−0.0205 (11)	−0.0077 (11)	−0.0055 (11)
C10	0.0432 (12)	0.0614 (14)	0.0762 (16)	0.0049 (10)	−0.0043 (10)	0.0102 (12)
C14	0.0666 (15)	0.0466 (13)	0.0671 (14)	−0.0145 (11)	0.0020 (11)	−0.0045 (11)
C3	0.0585 (15)	0.0872 (18)	0.0613 (14)	−0.0176 (13)	−0.0128 (11)	−0.0104 (13)
C5	0.0781 (17)	0.0551 (13)	0.0507 (12)	−0.0046 (12)	0.0055 (11)	0.0002 (10)
C4	0.0719 (17)	0.0850 (18)	0.0537 (14)	0.0066 (14)	−0.0082 (12)	0.0000 (13)
N2	0.111 (2)	0.0551 (13)	0.1037 (19)	−0.0313 (13)	0.0078 (15)	0.0019 (12)
Cl1	0.0555 (3)	0.0508 (3)	0.0628 (3)	0.0132 (2)	0.0059 (2)	−0.0056 (2)

N1—C8	1.459 (2)	C6—C5	1.376 (3)
N1—C7	1.506 (3)	C6—C1	1.390 (3)
N1—H1A	0.9000	C6—C7	1.496 (3)
N1—H1B	0.9000	C1—C2	1.387 (3)
O1—C1	1.356 (3)	C7—H7A	0.9700
O1—H1	0.8500	C7—H7B	0.9700
C12—C11	1.381 (3)	C2—C3	1.370 (3)
C12—C13	1.387 (3)	C2—H2	0.9300
C12—C14	1.445 (3)	C10—H10	0.9300
C13—C8	1.382 (3)	C14—N2	1.127 (3)
C13—H13	0.9300	C3—C4	1.380 (4)
C8—C9	1.375 (3)	C3—H3	0.9300
C11—C10	1.378 (3)	C5—C4	1.373 (3)
C11—H11	0.9300	C5—H5	0.9300
C9—C10	1.379 (3)	C4—H4	0.9300
C9—H9	0.9300
C8—N1—C7	112.49 (14)	O1—C1—C2	123.5 (2)
C8—N1—H1A	109.1	O1—C1—C6	116.84 (18)
C7—N1—H1A	109.1	C2—C1—C6	119.7 (2)
C8—N1—H1B	109.1	C6—C7—N1	111.97 (16)
C7—N1—H1B	109.1	C6—C7—H7A	109.2
H1A—N1—H1B	107.8	N1—C7—H7A	109.2
C1—O1—H1	111.7	C6—C7—H7B	109.2
C11—C12—C13	120.78 (18)	N1—C7—H7B	109.2
C11—C12—C14	119.76 (19)	H7A—C7—H7B	107.9
C13—C12—C14	119.5 (2)	C3—C2—C1	119.9 (2)
C8—C13—C12	118.45 (18)	C3—C2—H2	120.0
C8—C13—H13	120.8	C1—C2—H2	120.0
C12—C13—H13	120.8	C11—C10—C9	120.5 (2)
C9—C8—C13	121.38 (18)	C11—C10—H10	119.8
C9—C8—N1	119.52 (16)	C9—C10—H10	119.8
C13—C8—N1	119.06 (17)	N2—C14—C12	178.9 (3)
C10—C11—C12	119.56 (19)	C2—C3—C4	120.7 (2)
C10—C11—H11	120.2	C2—C3—H3	119.6
C12—C11—H11	120.2	C4—C3—H3	119.6
C8—C9—C10	119.37 (19)	C4—C5—C6	121.3 (2)
C8—C9—H9	120.3	C4—C5—H5	119.4
C10—C9—H9	120.3	C6—C5—H5	119.4
C5—C6—C1	119.2 (2)	C5—C4—C3	119.1 (2)
C5—C6—C7	121.2 (2)	C5—C4—H4	120.4
C1—C6—C7	119.6 (2)	C3—C4—H4	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.90	2.29	3.1315 (17)	155
O1—H1···Cl1ii	0.85	2.24	3.0870 (18)	171
N1—H1B···Cl1	0.90	2.14	3.0376 (16)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.90	2.29	3.1315 (17)	155
O1—H1⋯Cl1ii	0.85	2.24	3.0870 (18)	171
N1—H1B⋯Cl1	0.90	2.14	3.0376 (16)	173

Symmetry codes: (i) ; (ii) .