4-Iodo-anilinium nitrate.

In the title compound, C(6)H(7)IN(+)·NO(3) (-), π-π stacking inter-actions [centroid-centroid distances = 4.014 (4) and 4.029 (4) Å] stabilize the crystal structure and strong N-H⋯O and N-H⋯N hydrogen bonds link the cations and anions into zigzag chains running parallel to the c axis. The asymmetric unit contains two unique cations and anions.

Related literature

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

Experimental

Crystal data

C6H7IN+·NO3 −

M = 282.04

Monoclinic,

a = 21.847 (4) Å

b = 5.6103 (11) Å

c = 15.928 (3) Å

β = 110.11 (3)°

V = 1833.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 3.47 mm−1

T = 298 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

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

17732 measured reflections

4196 independent reflections

3075 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.112

S = 1.13

4196 reflections

217 parameters

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −0.78 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/S1600536810016740/jh2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016740/jh2153Isup2.hkl

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

C6H7IN+·NO3−	F(000) = 1072
Mr = 282.04	Dx = 2.044 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7323 reflections
a = 21.847 (4) Å	θ = 3.2–27.6°
b = 5.6103 (11) Å	µ = 3.47 mm−1
c = 15.928 (3) Å	T = 298 K
β = 110.11 (3)°	Prism, colourless
V = 1833.2 (6) Å3	0.40 × 0.30 × 0.20 mm
Z = 8

Rigaku SCXmini diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	3075 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −28→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.5, Tmax = 0.5	l = −20→20
17732 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0174P)2 + 9.5262P] where P = (Fo2 + 2Fc2)/3
4196 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −0.78 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
I2	0.38469 (2)	0.37839 (12)	0.76874 (3)	0.0735 (2)
C10	0.5931 (3)	0.3846 (12)	0.9095 (4)	0.0471 (15)
H10A	0.6281	0.2874	0.9120	0.056*
N2	0.6682 (3)	0.6372 (10)	1.0215 (4)	0.0513 (14)
H2B	0.6678	0.7709	1.0513	0.062*
H2C	0.6947	0.6550	0.9901	0.062*
H2D	0.6823	0.5174	1.0599	0.062*
C11	0.5297 (3)	0.3288 (13)	0.8534 (4)	0.0507 (16)
H11A	0.5224	0.1926	0.8181	0.061*
C9	0.6020 (3)	0.5850 (11)	0.9604 (4)	0.0412 (14)
C8	0.5520 (3)	0.7336 (12)	0.9573 (4)	0.0503 (16)
H8A	0.5596	0.8706	0.9923	0.060*
C12	0.4790 (3)	0.4729 (12)	0.8504 (4)	0.0448 (15)
C7	0.4894 (3)	0.6768 (13)	0.9008 (5)	0.0514 (16)
H7A	0.4546	0.7769	0.8973	0.062*
I1	0.11990 (2)	0.89729 (11)	0.38039 (3)	0.06947 (19)
C3	−0.1001 (3)	1.0935 (11)	0.3605 (4)	0.0424 (14)
N1	−0.1670 (2)	1.1490 (10)	0.3549 (4)	0.0528 (14)
H1B	−0.1941	1.0391	0.3218	0.063*
H1C	−0.1783	1.2916	0.3299	0.063*
H1D	−0.1694	1.1499	0.4096	0.063*
C6	0.0249 (3)	0.9855 (12)	0.3725 (4)	0.0451 (15)
C2	−0.0884 (3)	0.8935 (12)	0.3196 (4)	0.0520 (16)
H2A	−0.1228	0.7944	0.2883	0.062*
C4	−0.0498 (3)	1.2412 (12)	0.4073 (4)	0.0497 (16)
H4A	−0.0581	1.3774	0.4349	0.060*
C5	0.0135 (3)	1.1858 (13)	0.4131 (5)	0.0543 (17)
H5A	0.0479	1.2850	0.4445	0.065*
C1	−0.0264 (3)	0.8386 (12)	0.3247 (4)	0.0511 (16)
H1A	−0.0185	0.7033	0.2962	0.061*
O6	0.3304 (2)	−0.1221 (9)	0.9162 (3)	0.0657 (14)
N4	0.2778 (3)	−0.1278 (12)	0.8524 (4)	0.0553 (15)
O5	0.2512 (3)	−0.3234 (10)	0.8268 (4)	0.0745 (16)
O4	0.2531 (3)	0.0559 (11)	0.8148 (4)	0.0826 (18)
N3	0.2248 (3)	0.3536 (11)	0.5730 (4)	0.0560 (15)
O3	0.2487 (3)	0.1485 (9)	0.5783 (4)	0.0686 (15)
O2	0.1727 (3)	0.3781 (10)	0.5883 (4)	0.0749 (16)
O1	0.2517 (3)	0.5249 (11)	0.5535 (5)	0.0885 (19)

	U11	U22	U33	U12	U13	U23
I2	0.0463 (3)	0.1119 (5)	0.0590 (3)	−0.0160 (3)	0.0141 (2)	−0.0082 (3)
C10	0.044 (3)	0.054 (4)	0.045 (3)	0.005 (3)	0.017 (3)	−0.002 (3)
N2	0.048 (3)	0.054 (4)	0.053 (3)	−0.010 (3)	0.019 (3)	−0.005 (3)
C11	0.059 (4)	0.054 (4)	0.040 (3)	−0.003 (3)	0.019 (3)	−0.009 (3)
C9	0.038 (3)	0.048 (4)	0.038 (3)	−0.005 (3)	0.013 (3)	0.002 (3)
C8	0.060 (4)	0.042 (4)	0.051 (4)	−0.005 (3)	0.021 (3)	−0.005 (3)
C12	0.043 (3)	0.059 (4)	0.035 (3)	−0.004 (3)	0.017 (3)	0.002 (3)
C7	0.045 (4)	0.053 (4)	0.059 (4)	0.007 (3)	0.021 (3)	0.002 (3)
I1	0.0449 (3)	0.0962 (4)	0.0641 (3)	0.0188 (3)	0.0146 (2)	−0.0032 (3)
C3	0.043 (3)	0.047 (4)	0.040 (3)	0.003 (3)	0.017 (3)	0.000 (3)
N1	0.043 (3)	0.060 (4)	0.055 (3)	0.006 (3)	0.016 (3)	−0.003 (3)
C6	0.044 (3)	0.056 (4)	0.036 (3)	0.014 (3)	0.013 (3)	0.005 (3)
C2	0.051 (4)	0.056 (4)	0.049 (4)	−0.007 (3)	0.017 (3)	−0.012 (3)
C4	0.055 (4)	0.040 (4)	0.052 (4)	0.004 (3)	0.016 (3)	−0.009 (3)
C5	0.047 (4)	0.056 (4)	0.054 (4)	0.000 (3)	0.009 (3)	−0.014 (3)
C1	0.059 (4)	0.052 (4)	0.045 (4)	−0.001 (3)	0.021 (3)	−0.014 (3)
O6	0.058 (3)	0.069 (4)	0.056 (3)	0.000 (3)	0.002 (2)	−0.001 (3)
N4	0.044 (3)	0.061 (4)	0.061 (4)	−0.004 (3)	0.017 (3)	−0.005 (3)
O5	0.063 (3)	0.063 (3)	0.099 (4)	−0.019 (3)	0.030 (3)	−0.016 (3)
O4	0.069 (4)	0.069 (4)	0.085 (4)	0.000 (3)	−0.006 (3)	0.009 (3)
N3	0.046 (3)	0.058 (4)	0.062 (4)	0.005 (3)	0.016 (3)	−0.007 (3)
O3	0.061 (3)	0.057 (3)	0.095 (4)	0.015 (3)	0.037 (3)	−0.001 (3)
O2	0.055 (3)	0.071 (4)	0.114 (5)	0.008 (3)	0.048 (3)	−0.007 (3)
O1	0.070 (4)	0.063 (4)	0.143 (6)	0.001 (3)	0.050 (4)	0.010 (4)

I2—C12	2.091 (6)	C3—N1	1.467 (7)
C10—C9	1.360 (9)	N1—H1B	0.8900
C10—C11	1.401 (9)	N1—H1C	0.8900
C10—H10A	0.9300	N1—H1D	0.8900
N2—C9	1.469 (7)	C6—C5	1.361 (9)
N2—H2B	0.8900	C6—C1	1.389 (9)
N2—H2C	0.8900	C2—C1	1.365 (9)
N2—H2D	0.8900	C2—H2A	0.9300
C11—C12	1.359 (9)	C4—C5	1.390 (9)
C11—H11A	0.9300	C4—H4A	0.9300
C9—C8	1.361 (9)	C5—H5A	0.9300
C8—C7	1.392 (9)	C1—H1A	0.9300
C8—H8A	0.9300	O6—N4	1.246 (7)
C12—C7	1.371 (9)	N4—O4	1.221 (8)
C7—H7A	0.9300	N4—O5	1.243 (7)
I1—C6	2.095 (6)	N3—O1	1.220 (8)
C3—C2	1.365 (9)	N3—O2	1.253 (7)
C3—C4	1.373 (9)	N3—O3	1.254 (7)
C9—C10—C11	118.2 (6)	C3—N1—H1B	109.5
C9—C10—H10A	120.9	C3—N1—H1C	109.5
C11—C10—H10A	120.9	H1B—N1—H1C	109.5
C9—N2—H2B	109.5	C3—N1—H1D	109.5
C9—N2—H2C	109.5	H1B—N1—H1D	109.5
H2B—N2—H2C	109.5	H1C—N1—H1D	109.5
C9—N2—H2D	109.5	C5—C6—C1	120.4 (6)
H2B—N2—H2D	109.5	C5—C6—I1	120.4 (5)
H2C—N2—H2D	109.5	C1—C6—I1	119.2 (5)
C12—C11—C10	120.3 (6)	C3—C2—C1	120.2 (6)
C12—C11—H11A	119.8	C3—C2—H2A	119.9
C10—C11—H11A	119.8	C1—C2—H2A	119.9
C10—C9—C8	122.4 (6)	C3—C4—C5	119.6 (6)
C10—C9—N2	117.7 (6)	C3—C4—H4A	120.2
C8—C9—N2	119.8 (6)	C5—C4—H4A	120.2
C9—C8—C7	118.8 (6)	C6—C5—C4	119.6 (6)
C9—C8—H8A	120.6	C6—C5—H5A	120.2
C7—C8—H8A	120.6	C4—C5—H5A	120.2
C11—C12—C7	120.5 (6)	C2—C1—C6	119.7 (6)
C11—C12—I2	119.2 (5)	C2—C1—H1A	120.1
C7—C12—I2	120.3 (5)	C6—C1—H1A	120.1
C12—C7—C8	119.8 (6)	O4—N4—O5	120.4 (6)
C12—C7—H7A	120.1	O4—N4—O6	120.4 (6)
C8—C7—H7A	120.1	O5—N4—O6	119.1 (7)
C2—C3—C4	120.6 (6)	O1—N3—O2	120.8 (6)
C2—C3—N1	119.4 (6)	O1—N3—O3	121.0 (6)
C4—C3—N1	120.0 (6)	O2—N3—O3	118.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O4i	0.89	2.18	2.945 (8)	144
N1—H1C···O2ii	0.89	2.24	2.819 (8)	122
N1—H1C···O5i	0.89	2.46	3.010 (8)	120
N1—H1D···O3i	0.89	2.46	2.898 (8)	111
N1—H1D···I1ii	0.89	3.15	3.990 (6)	157
N2—H2B···O6iii	0.89	2.03	2.892 (8)	162
N2—H2B···O4iii	0.89	2.44	3.104 (8)	132
N2—H2B···N4iii	0.89	2.55	3.372 (8)	153
N2—H2C···O3iv	0.89	1.91	2.795 (7)	173
N2—H2C···N3iv	0.89	2.56	3.407 (8)	159
N2—H2C···O1iv	0.89	2.59	3.264 (8)	133
N2—H2D···O5v	0.89	2.18	3.018 (8)	157
N2—H2D···O6v	0.89	2.28	3.053 (8)	145
N2—H2D···N4v	0.89	2.58	3.459 (9)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O4i	0.89	2.18	2.945 (8)	144
N1—H1C⋯O2ii	0.89	2.24	2.819 (8)	122
N1—H1C⋯O5i	0.89	2.46	3.010 (8)	120
N1—H1D⋯O3i	0.89	2.46	2.898 (8)	111
N1—H1D⋯I1ii	0.89	3.15	3.990 (6)	157
N2—H2B⋯O6iii	0.89	2.03	2.892 (8)	162
N2—H2B⋯O4iii	0.89	2.44	3.104 (8)	132
N2—H2B⋯N4iii	0.89	2.55	3.372 (8)	153
N2—H2C⋯O3iv	0.89	1.91	2.795 (7)	173
N2—H2C⋯N3iv	0.89	2.56	3.407 (8)	159
N2—H2C⋯O1iv	0.89	2.59	3.264 (8)	133
N2—H2D⋯O5v	0.89	2.18	3.018 (8)	157
N2—H2D⋯O6v	0.89	2.28	3.053 (8)	145
N2—H2D⋯N4v	0.89	2.58	3.459 (9)	170

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