3-Cyano-anilinium iodide monohydrate.

In the crystal structure of the title compound, C(7)H(7)N(2) (+)·I(-)·H(2)O, [C(7)H(7)N(2) (+)](n) chains extending along the a-axis direction are linked via N-H⋯N hydrogen bonds. The cations are further connected to the anions by N-H⋯I, N-H⋯O and O-H⋯I hydrogen bonds, leading to the formation of a sheet parallel to the ac plane. π-π inter-actions [centroid-centroid distance = 3.8378 (7) Å] link the sheets into a three-dimensional network.

Related literature

For related structures, see: Oueslati et al. (2005 ▶); Messai et al. (2009 ▶). For applications of salts of amides as phase-transition dielectric materials, see: Fu et al. (2007 ▶, 2008 ▶, 2009 ▶); Fu & Xiong (2008 ▶).

Experimental

Crystal data

C7H7N2 +·I−·H2O

M = 264.06

Monoclinic,

a = 8.0436 (16) Å

b = 16.603 (3) Å

c = 7.6746 (15) Å

β = 115.39 (3)°

V = 925.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.41 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

9455 measured reflections

2117 independent reflections

1978 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.061

S = 1.21

2117 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.89 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/S1600536810048294/vm2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048294/vm2061Isup2.hkl

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

C7H7N2+·I−·H2O	F(000) = 504
Mr = 264.06	Dx = 1.894 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2117 reflections
a = 8.0436 (16) Å	θ = 3.1–27.5°
b = 16.603 (3) Å	µ = 3.41 mm−1
c = 7.6746 (15) Å	T = 298 K
β = 115.39 (3)°	Block, colorless
V = 925.9 (3) Å3	0.10 × 0.03 × 0.03 mm
Z = 4

Rigaku Mercury2 diffractometer	2117 independent reflections
Radiation source: fine-focus sealed tube	1978 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −21→21
Tmin = 0.910, Tmax = 1.000	l = −9→9
9455 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0103P)2 + 0.9565P] where P = (Fo2 + 2Fc2)/3
S = 1.21	(Δ/σ)max < 0.001
2117 reflections	Δρmax = 0.72 e Å−3
102 parameters	Δρmin = −0.89 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0824 (16)

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	1.0275 (3)	0.37559 (16)	0.8592 (4)	0.0332 (6)
H1A	0.9606	0.4146	0.8775	0.050*
H1B	1.0861	0.3949	0.7927	0.050*
H1C	1.1093	0.3575	0.9730	0.050*
N2	0.3209 (4)	0.3013 (2)	0.2122 (4)	0.0483 (8)
C1	0.4542 (4)	0.2842 (2)	0.3388 (4)	0.0350 (7)
C2	0.6270 (4)	0.26503 (19)	0.4998 (4)	0.0288 (6)
C3	0.6773 (4)	0.18539 (19)	0.5508 (5)	0.0343 (7)
H3	0.5995	0.1436	0.4829	0.041*
C4	0.8443 (4)	0.1692 (2)	0.7037 (5)	0.0365 (7)
H4	0.8788	0.1161	0.7394	0.044*
C5	0.9614 (4)	0.23118 (18)	0.8048 (4)	0.0306 (6)
H5	1.0747	0.2200	0.9065	0.037*
C6	0.9070 (4)	0.30971 (17)	0.7520 (4)	0.0257 (6)
C7	0.7422 (4)	0.32826 (19)	0.6002 (4)	0.0294 (6)
H7	0.7085	0.3815	0.5653	0.035*
O1W	0.2139 (3)	0.49557 (16)	0.1596 (4)	0.0488 (6)
H1WA	0.2348	0.4707	0.2806	0.073*
H1WB	0.3325	0.5071	0.1742	0.073*
I1	0.30166 (3)	0.451061 (14)	0.64728 (3)	0.04440 (13)

	U11	U22	U33	U12	U13	U23
N1	0.0275 (13)	0.0362 (14)	0.0302 (13)	−0.0081 (10)	0.0067 (10)	−0.0028 (11)
N2	0.0317 (15)	0.060 (2)	0.0379 (15)	0.0013 (13)	0.0001 (13)	−0.0064 (14)
C1	0.0271 (15)	0.0425 (18)	0.0300 (16)	−0.0034 (13)	0.0073 (13)	−0.0073 (13)
C2	0.0214 (13)	0.0374 (16)	0.0244 (14)	−0.0004 (12)	0.0068 (11)	−0.0034 (12)
C3	0.0298 (15)	0.0344 (16)	0.0380 (16)	−0.0077 (12)	0.0139 (13)	−0.0100 (13)
C4	0.0361 (16)	0.0293 (16)	0.0391 (17)	0.0031 (13)	0.0116 (14)	0.0000 (13)
C5	0.0244 (14)	0.0367 (16)	0.0277 (14)	0.0035 (12)	0.0083 (12)	0.0028 (12)
C6	0.0217 (13)	0.0311 (15)	0.0231 (13)	−0.0054 (11)	0.0086 (11)	−0.0033 (11)
C7	0.0258 (14)	0.0307 (15)	0.0278 (14)	0.0013 (11)	0.0079 (11)	0.0014 (11)
O1W	0.0377 (13)	0.0442 (14)	0.0516 (15)	−0.0006 (11)	0.0070 (11)	−0.0055 (11)
I1	0.03749 (16)	0.04184 (17)	0.05167 (18)	0.00206 (9)	0.01702 (12)	0.01218 (10)

N1—C6	1.459 (4)	C3—H3	0.9300
N1—H1A	0.8900	C4—C5	1.386 (4)
N1—H1B	0.8900	C4—H4	0.9300
N1—H1C	0.8900	C5—C6	1.380 (4)
N2—C1	1.132 (4)	C5—H5	0.9300
C1—C2	1.444 (4)	C6—C7	1.373 (4)
C2—C3	1.389 (4)	C7—H7	0.9300
C2—C7	1.394 (4)	O1W—H1WA	0.9626
C3—C4	1.380 (4)	O1W—H1WB	0.9316
C6—N1—H1A	109.5	C3—C4—C5	120.8 (3)
C6—N1—H1B	109.5	C3—C4—H4	119.6
H1A—N1—H1B	109.5	C5—C4—H4	119.6
C6—N1—H1C	109.5	C6—C5—C4	118.9 (3)
H1A—N1—H1C	109.5	C6—C5—H5	120.5
H1B—N1—H1C	109.5	C4—C5—H5	120.5
N2—C1—C2	178.0 (4)	C7—C6—C5	122.0 (3)
C3—C2—C7	121.1 (3)	C7—C6—N1	118.5 (3)
C3—C2—C1	120.5 (3)	C5—C6—N1	119.5 (3)
C7—C2—C1	118.3 (3)	C6—C7—C2	118.1 (3)
C4—C3—C2	119.0 (3)	C6—C7—H7	120.9
C4—C3—H3	120.5	C2—C7—H7	120.9
C2—C3—H3	120.5	H1WA—O1W—H1WB	103.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···N2i	0.89	2.11	2.991 (4)	169
N1—H1A···O1Wii	0.89	1.98	2.850 (4)	164
N1—H1B···I1iii	0.89	2.60	3.487 (3)	171
O1W—H1WB···I1ii	0.93	2.75	3.635 (3)	159
O1W—H1WA···I1	0.96	2.65	3.576 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯N2i	0.89	2.11	2.991 (4)	169
N1—H1A⋯O1Wii	0.89	1.98	2.850 (4)	164
N1—H1B⋯I1iii	0.89	2.60	3.487 (3)	171
O1W—H1WB⋯I1ii	0.93	2.75	3.635 (3)	159
O1W—H1WA⋯I1	0.96	2.65	3.576 (3)	162

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