4-Iodo­anilinium nitrate

Fu, X.

doi:10.1107/S1600536810016740

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1326

https://doi.org/10.1107/S1600536810016740

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4-Iodoanilinium nitrate

Xue-qun Fu ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fuxuequn222@163.com

(Received 4 May 2010; accepted 7 May 2010; online 12 May 2010)

In the title compound, C₆H₇IN⁺·NO₃⁻, π–π stacking interactions [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_r = 282.04
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.112
S = 1.13
4196 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 1.07 e Å⁻³
Δρ_min = −0.78 e Å⁻³

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⋯O3^iv	0.89	1.91	2.795 (7)	173
N2—H2C⋯N3^iv	0.89	2.56	3.407 (8)	159
N2—H2C⋯O1^iv	0.89	2.59	3.264 (8)	133
N2—H2D⋯O5^v	0.89	2.18	3.018 (8)	157
N2—H2D⋯O6^v	0.89	2.28	3.053 (8)	145
N2—H2D⋯N4^v	0.89	2.58	3.459 (9)	170
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+1, -z+2; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x+1, -y, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016740/jh2153sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016740/jh2153Isup2.hkl

checkCIF report

Comment top

As a continuation of our study of phase transition materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009 ), organic-inorganic hybrids, we studied the dielectric properties of the title compound, unfortunately, there was no distinct anomaly observed from 93 K to 380 K, (m.p. 408 K-410 K). In this article, the crystal structure of (I) has been presented.

The asymmetric unit of the title compound is built up from two 4-iodobenzenammnium cations wherein the dihedral angle between plans formed by non-hydrogen atoms is 15.3 (2)°,and two nitrate radical anions (Fig.1). The π-π packing interaction of adjacent benzene rings with Cg(1)—Cg(1), 4.029 (4)Å; Cg(2)—Cg(2), 4.014 (4)Å [Cg(1) and Cg(2) are the centroids of benzene rings, where Cg(1): C(1) to C(6); Cg(2): C(7) to C(12)], make great contribution to the stability of the crystal structure. The strong intermolecular N—H···O (N···O distances 2.795 (7)-3.264 (8)Å) and N—H···N (N···N distances 3.372 (8)-3.459 (9)Å) hydrogen bonding link cations and anions into zigzag chains along c axis.

Related literature top

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

Experimental top

Single crystals of 4-iodoanilinium nitrate were prepared by slow evaporation at room temperature of an ethanol solution of equal molar 4-iodobenzenamine and nitrate acid.

Structure description top

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

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and all H atoms have been omitted for clarity.
	Fig. 2. A view of the packing of the title compound, stacking along the c axis. Dashed lines indicate hydrogen bonds.

4-iodoanilinium nitrate top

Crystal data top

C₆H₇IN⁺·NO₃⁻	F(000) = 1072
M_r = 282.04	D_x = 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

Data collection top

Rigaku SCXmini diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	3075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −28→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
T_min = 0.5, T_max = 0.5	l = −20→20
17732 measured reflections

Refinement top

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(F_o²) + (0.0174P)² + 9.5262P] where P = (F_o² + 2F_c²)/3
4196 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 1.07 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

C₆H₇IN⁺·NO₃⁻	V = 1833.2 (6) Å³
M_r = 282.04	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.847 (4) Å	µ = 3.47 mm⁻¹
b = 5.6103 (11) Å	T = 298 K
c = 15.928 (3) Å	0.40 × 0.30 × 0.20 mm
β = 110.11 (3)°

Data collection top

Rigaku SCXmini diffractometer	4196 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3075 reflections with I > 2σ(I)
T_min = 0.5, T_max = 0.5	R_int = 0.041
17732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.13	Δρ_max = 1.07 e Å⁻³
4196 reflections	Δρ_min = −0.78 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.89	1.91	2.795 (7)	173
N2—H2C···N3^iv	0.89	2.56	3.407 (8)	159
N2—H2C···O1^iv	0.89	2.59	3.264 (8)	133
N2—H2D···O5^v	0.89	2.18	3.018 (8)	157
N2—H2D···O6^v	0.89	2.28	3.053 (8)	145
N2—H2D···N4^v	0.89	2.58	3.459 (9)	170

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₆H₇IN⁺·NO₃⁻
M_r	282.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	21.847 (4), 5.6103 (11), 15.928 (3)
β (°)	110.11 (3)
V (Å³)	1833.2 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.47
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.5, 0.5
No. of measured, independent and observed [I > 2σ(I)] reflections	17732, 4196, 3075
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.112, 1.13
No. of reflections	4196
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.07, −0.78

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O4ⁱ	0.89	2.18	2.945 (8)	143.5
N1—H1C···O2ⁱⁱ	0.89	2.24	2.819 (8)	122.1
N1—H1C···O5ⁱ	0.89	2.46	3.010 (8)	120.1
N1—H1D···O3ⁱ	0.89	2.46	2.898 (8)	110.6
N1—H1D···I1ⁱⁱ	0.89	3.15	3.990 (6)	157.4
N2—H2B···O6ⁱⁱⁱ	0.89	2.03	2.892 (8)	161.7
N2—H2B···O4ⁱⁱⁱ	0.89	2.44	3.104 (8)	132.0
N2—H2B···N4ⁱⁱⁱ	0.89	2.55	3.372 (8)	153.4
N2—H2C···O3^iv	0.89	1.91	2.795 (7)	172.5
N2—H2C···N3^iv	0.89	2.56	3.407 (8)	159.2
N2—H2C···O1^iv	0.89	2.59	3.264 (8)	132.9
N2—H2D···O5^v	0.89	2.18	3.018 (8)	157.1
N2—H2D···O6^v	0.89	2.28	3.053 (8)	144.6
N2—H2D···N4^v	0.89	2.58	3.459 (9)	170.2

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1, −y, −z+2.

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

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