3-Cyano-N-(2-hy-droxy-benz-yl)anilinium nitrate.

In the crystal structure of the title compound, C(14)H(13)N(2)O(+)·NO(3) (-), N-H⋯O and O-H⋯O hydrogen bonds link cations and anions into a two-dimensional network parallel to (100). The dihedral angle between the rings is 9.48 (2)°.

Related literature

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

Experimental

Crystal data

C14H13N2O+·n class="Chemical">NO3 −

M = 287.27

Monoclinic,

a = 12.060 (2) Å

b = 13.632 (3) Å

c = 8.8679 (18) Å

β = 93.71 (3)°

V = 1454.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

14660 measured reflections

2857 independent reflections

1931 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.187

S = 1.06

2857 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.17 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054231/dn2642sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054231/dn2642Isup2.hkl

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

C14H13N2O+·NO3−	F(000) = 600
Mr = 287.27	Dx = 1.312 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3326 reflections
a = 12.060 (2) Å	θ = 3.0–27.5°
b = 13.632 (3) Å	µ = 0.10 mm−1
c = 8.8679 (18) Å	T = 298 K
β = 93.71 (3)°	Block, colorless
V = 1454.9 (5) Å3	0.10 × 0.03 × 0.03 mm
Z = 4

Rigaku Mercury2 diffractometer	2857 independent reflections
Radiation source: fine-focus sealed tube	1931 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.0°
CCD profile fitting scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = 0→16
Tmin = 0.910, Tmax = 1.000	l = 0→10
14660 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0773P)2 + 0.7478P] where P = (Fo2 + 2Fc2)/3
2857 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.17 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 > 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
O1	0.01326 (17)	0.48563 (16)	0.7983 (2)	0.0641 (6)
H1	−0.0322	0.4598	0.8506	0.096*
N1	0.21801 (17)	0.60209 (15)	0.7364 (2)	0.0441 (5)
H1A	0.2317	0.6669	0.7312	0.053*
H1B	0.1804	0.5914	0.8192	0.053*
N2	0.4445 (3)	0.2610 (2)	1.0265 (5)	0.1039 (12)
C1	0.4388 (3)	0.3282 (3)	0.9493 (5)	0.0740 (10)
C2	0.4304 (2)	0.4142 (2)	0.8546 (3)	0.0561 (7)
C3	0.3305 (2)	0.46590 (19)	0.8403 (3)	0.0490 (7)
H3A	0.2691	0.4443	0.8893	0.059*
C4	0.3240 (2)	0.54951 (19)	0.7526 (3)	0.0433 (6)
C5	0.4133 (2)	0.5825 (2)	0.6785 (4)	0.0625 (8)
H5A	0.4077	0.6390	0.6197	0.075*
C6	0.5124 (3)	0.5300 (3)	0.6929 (4)	0.0796 (10)
H6A	0.5736	0.5520	0.6439	0.096*
C7	0.5207 (3)	0.4464 (3)	0.7782 (4)	0.0717 (9)
H7A	0.5868	0.4110	0.7850	0.086*
C8	0.1457 (2)	0.5717 (2)	0.5977 (3)	0.0502 (7)
H8A	0.1749	0.6002	0.5083	0.060*
H8B	0.1474	0.5009	0.5874	0.060*
C9	0.0277 (2)	0.6051 (2)	0.6099 (3)	0.0533 (7)
C10	−0.0376 (2)	0.5602 (2)	0.7136 (3)	0.0544 (7)
C11	−0.1472 (3)	0.5889 (2)	0.7271 (4)	0.0681 (9)
H11A	−0.1907	0.5586	0.7964	0.082*
C12	−0.1896 (3)	0.6633 (3)	0.6353 (5)	0.0850 (11)
H12A	−0.2629	0.6829	0.6435	0.102*
C13	−0.1275 (3)	0.7091 (3)	0.5326 (5)	0.0876 (12)
H13A	−0.1578	0.7598	0.4731	0.105*
C14	−0.0188 (3)	0.6792 (2)	0.5179 (4)	0.0724 (9)
H14A	0.0233	0.7088	0.4464	0.087*
O2	0.14630 (18)	0.90283 (15)	0.5332 (2)	0.0654 (6)
O3	0.2686 (2)	0.78798 (16)	0.5296 (3)	0.0731 (7)
O4	0.1883 (2)	0.81584 (17)	0.7324 (3)	0.0849 (8)
N3	0.20210 (19)	0.83479 (17)	0.5999 (3)	0.0507 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0621 (13)	0.0672 (13)	0.0624 (13)	−0.0158 (11)	−0.0006 (10)	0.0150 (10)
N1	0.0452 (12)	0.0400 (11)	0.0470 (12)	−0.0023 (9)	0.0019 (9)	0.0014 (9)
N2	0.103 (3)	0.068 (2)	0.137 (3)	0.0141 (18)	−0.023 (2)	0.021 (2)
C1	0.064 (2)	0.0563 (19)	0.099 (3)	0.0114 (16)	−0.0158 (18)	−0.0036 (19)
C2	0.0498 (16)	0.0494 (16)	0.0671 (19)	0.0044 (13)	−0.0115 (14)	−0.0084 (14)
C3	0.0471 (15)	0.0449 (15)	0.0549 (16)	−0.0032 (12)	0.0026 (12)	−0.0032 (12)
C4	0.0387 (14)	0.0440 (14)	0.0467 (14)	−0.0022 (11)	−0.0011 (11)	−0.0079 (11)
C5	0.0516 (17)	0.066 (2)	0.071 (2)	−0.0077 (15)	0.0078 (14)	0.0057 (15)
C6	0.0445 (18)	0.099 (3)	0.097 (3)	−0.0055 (18)	0.0136 (17)	−0.001 (2)
C7	0.0461 (18)	0.077 (2)	0.090 (2)	0.0110 (16)	−0.0057 (16)	−0.012 (2)
C8	0.0500 (16)	0.0561 (16)	0.0441 (15)	−0.0054 (13)	0.0000 (12)	−0.0036 (12)
C9	0.0527 (16)	0.0524 (16)	0.0541 (16)	−0.0072 (13)	−0.0036 (13)	−0.0028 (13)
C10	0.0521 (16)	0.0531 (16)	0.0571 (17)	−0.0073 (13)	−0.0033 (13)	−0.0035 (14)
C11	0.0539 (19)	0.068 (2)	0.083 (2)	−0.0026 (16)	0.0103 (16)	−0.0027 (17)
C12	0.062 (2)	0.075 (2)	0.118 (3)	0.0126 (19)	−0.002 (2)	0.006 (2)
C13	0.073 (2)	0.067 (2)	0.120 (3)	0.0169 (19)	−0.020 (2)	0.014 (2)
C14	0.071 (2)	0.067 (2)	0.078 (2)	−0.0063 (17)	−0.0055 (17)	0.0138 (17)
O2	0.0761 (14)	0.0616 (13)	0.0597 (12)	0.0242 (11)	0.0124 (10)	0.0147 (10)
O3	0.0754 (15)	0.0667 (14)	0.0767 (15)	0.0236 (12)	0.0015 (12)	−0.0026 (12)
O4	0.129 (2)	0.0768 (16)	0.0495 (13)	0.0135 (15)	0.0104 (13)	0.0155 (11)
N3	0.0569 (14)	0.0443 (13)	0.0501 (14)	−0.0026 (11)	−0.0032 (11)	0.0023 (11)

O1—C10	1.383 (3)	C7—H7A	0.9300
O1—H1	0.8200	C8—C9	1.504 (4)
N1—C4	1.465 (3)	C8—H8A	0.9700
N1—C8	1.518 (3)	C8—H8B	0.9700
N1—H1A	0.9000	C9—C10	1.391 (4)
N1—H1B	0.9000	C9—C14	1.393 (4)
N2—C1	1.143 (5)	C10—C11	1.391 (4)
C1—C2	1.442 (5)	C11—C12	1.378 (5)
C2—C7	1.390 (5)	C11—H11A	0.9300
C2—C3	1.395 (4)	C12—C13	1.368 (6)
C3—C4	1.379 (4)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.387 (5)
C4—C5	1.373 (4)	C13—H13A	0.9300
C5—C6	1.391 (5)	C14—H14A	0.9300
C5—H5A	0.9300	O2—N3	1.269 (3)
C6—C7	1.369 (5)	O3—N3	1.226 (3)
C6—H6A	0.9300	O4—N3	1.225 (3)
C10—O1—H1	109.5	C9—C8—H8A	109.5
C4—N1—C8	113.48 (19)	N1—C8—H8A	109.5
C4—N1—H1A	108.9	C9—C8—H8B	109.5
C8—N1—H1A	108.9	N1—C8—H8B	109.5
C4—N1—H1B	108.9	H8A—C8—H8B	108.1
C8—N1—H1B	108.9	C10—C9—C14	118.8 (3)
H1A—N1—H1B	107.7	C10—C9—C8	119.5 (3)
N2—C1—C2	178.7 (4)	C14—C9—C8	121.6 (3)
C7—C2—C3	119.7 (3)	O1—C10—C11	123.4 (3)
C7—C2—C1	120.9 (3)	O1—C10—C9	115.6 (3)
C3—C2—C1	119.4 (3)	C11—C10—C9	121.0 (3)
C4—C3—C2	119.1 (3)	C12—C11—C10	118.3 (3)
C4—C3—H3A	120.5	C12—C11—H11A	120.8
C2—C3—H3A	120.5	C10—C11—H11A	120.8
C5—C4—C3	121.5 (3)	C13—C12—C11	122.1 (3)
C5—C4—N1	120.0 (2)	C13—C12—H12A	119.0
C3—C4—N1	118.5 (2)	C11—C12—H12A	119.0
C4—C5—C6	118.9 (3)	C12—C13—C14	119.3 (3)
C4—C5—H5A	120.6	C12—C13—H13A	120.3
C6—C5—H5A	120.6	C14—C13—H13A	120.3
C7—C6—C5	120.7 (3)	C13—C14—C9	120.4 (3)
C7—C6—H6A	119.6	C13—C14—H14A	119.8
C5—C6—H6A	119.6	C9—C14—H14A	119.8
C6—C7—C2	120.1 (3)	O4—N3—O3	120.8 (2)
C6—C7—H7A	120.0	O4—N3—O2	120.0 (2)
C2—C7—H7A	120.0	O3—N3—O2	119.2 (2)
C9—C8—N1	110.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.93	2.753 (3)	177
N1—H1A···O4	0.90	2.10	2.936 (3)	155
N1—H1A···O3	0.90	2.49	3.209 (3)	137
N1—H1B···O2ii	0.90	1.97	2.824 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.93	2.753 (3)	177
N1—H1A⋯O4	0.90	2.10	2.936 (3)	155
N1—H1A⋯O3	0.90	2.49	3.209 (3)	137
N1—H1B⋯O2ii	0.90	1.97	2.824 (3)	158

Symmetry codes: (i) ; (ii) .