m-Carboxy­phenyl­ammonium nitrate

The crystal structure of the title compound, C₇H₈NO₂⁺·NO₃^-, consists of anionic and cationic layers linked by a complex three-dimensional hydrogen-bond network. Each cationic layer contains organic groups (NH₃C₆H₄COOH)⁺, and each anionic layer contains inorganic (NO₃)^-. The structure is stabilized by two types of hydrogen-bonding interaction: anion-cation and cation-cation contacts.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.057
• Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1989); cell refinement: CAD-4 Operations Manual; data reduction: BEGIN_SDP (Frenz et al., 1985); program(s) used to solve structure: MULTAN (Main et al., 1980); program(s) used to refine structure: CAD-4 Operations Manual [Is this correct?]; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CIF VAX in MolEN (Fair, 1990).

m-carboxy phenyl ammonium nitrate

Crystal data

C7H8NO2^+·NO3^−	F(000) = 832
Mr = 200.15	Dx = 1.517 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 31.838 (2) Å	θ = 10–14°
b = 5.208 (1) Å	µ = 0.13 mm^−1
c = 11.117 (3) Å	T = 298 K
β = 108.06 (4)°	Prism, brown
V = 1752.4 (7) Å^3	0.60 × 0.40 × 0.30 mm
Z = 8

Data collection

MACH3 diffractometer	θmax = 30.0°
Radiation source: X-ray_tube	h = 0→44
θ/2θ scans	k = 0→7
2923 measured reflections	l = −15→14
2551 independent reflections	2 standard reflections every 60 reflections
1654 reflections with I > 3σ(I)	intensity decay: −4.2%
Rint = 0.018

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.057	All H-atom parameters refined
S = 1.13	w = 4Fo^2/[σ^2(Fo^2) + 0.0016Fo^4]
1654 reflections	(Δ/σ)max = 0.006
159 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.07 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.30481 (3)	−0.1207 (2)	0.0894 (1)	0.0461 (3)
O2	0.25276 (3)	−0.0041 (2)	−0.0883 (1)	0.0414 (3)
O3	0.45029 (4)	0.8578 (2)	0.1933 (1)	0.0479 (3)
O4	0.46750 (4)	0.6164 (2)	0.3578 (1)	0.0480 (3)
O5	0.45388 (6)	1.0155 (3)	0.3752 (1)	0.0814 (5)
N1	0.44230 (4)	0.3585 (3)	0.0853 (1)	0.0360 (3)
N2	0.45727 (4)	0.8322 (2)	0.3106 (1)	0.0381 (3)
C1	0.28983 (4)	0.0198 (3)	−0.0125 (1)	0.0317 (3)
C2	0.32174 (4)	0.2117 (3)	−0.0317 (1)	0.0296 (3)
C3	0.36613 (4)	0.2023 (3)	0.0409 (1)	0.0298 (3)
C4	0.39523 (4)	0.3744 (3)	0.0143 (1)	0.0299 (3)
C5	0.38102 (5)	0.5582 (3)	−0.0791 (1)	0.0378 (4)
C6	0.33674 (5)	0.5676 (3)	−0.1497 (1)	0.0408 (4)
C7	0.30705 (4)	0.3937 (3)	−0.1268 (1)	0.0357 (3)
H	0.2852 (6)	−0.244 (4)	0.091 (2)	0.053 (5)*
H1n	0.4564 (5)	0.347 (4)	0.027 (2)	0.047 (5)*
H2n	0.4483 (6)	0.217 (4)	0.137 (2)	0.053 (5)*
H3n	0.4502 (7)	0.498 (4)	0.137 (2)	0.074 (7)*
H3	0.3770 (5)	0.073 (3)	0.106 (2)	0.044 (5)*
H5	0.4014 (6)	0.677 (4)	−0.096 (2)	0.046 (5)*
H6	0.3260 (6)	0.701 (4)	−0.212 (2)	0.052 (5)*
H7	0.2761 (5)	0.392 (4)	−0.179 (2)	0.044 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (5)	0.0499 (6)	0.0455 (5)	−0.0145 (5)	0.0044 (4)	0.0171 (4)
O2	0.0292 (4)	0.0449 (6)	0.0444 (5)	−0.0033 (5)	0.0030 (4)	0.0120 (4)
O3	0.0444 (5)	0.0485 (6)	0.0463 (5)	−0.0085 (5)	0.0074 (4)	−0.0046 (5)
O4	0.0526 (5)	0.0356 (5)	0.0641 (6)	−0.0132 (5)	0.0303 (4)	−0.0094 (5)
O5	0.123 (1)	0.0476 (7)	0.0838 (8)	0.0141 (6)	0.0472 (6)	−0.0230 (7)
N1	0.0261 (4)	0.0385 (6)	0.0435 (5)	0.0055 (5)	0.0109 (4)	0.0097 (4)
N2	0.0334 (5)	0.0315 (6)	0.0523 (6)	−0.0003 (5)	0.0176 (4)	−0.0063 (5)
C1	0.0291 (5)	0.0331 (7)	0.0323 (5)	0.0006 (5)	0.0086 (4)	0.0061 (5)
C2	0.0274 (5)	0.0286 (6)	0.0329 (5)	0.0005 (5)	0.0097 (4)	0.0050 (5)
C3	0.0271 (5)	0.0279 (6)	0.0339 (6)	−0.0010 (5)	0.0085 (4)	0.0039 (5)
C4	0.0267 (5)	0.0288 (6)	0.0349 (6)	0.0038 (5)	0.0106 (4)	0.0047 (5)
C5	0.0385 (6)	0.0325 (7)	0.0459 (6)	−0.0032 (6)	0.0184 (5)	0.0074 (5)
C6	0.0446 (7)	0.0359 (7)	0.0421 (6)	−0.0109 (6)	0.0138 (5)	0.0002 (6)
C7	0.0328 (6)	0.0392 (7)	0.0334 (6)	−0.0035 (6)	0.0077 (5)	0.0009 (6)

Geometric parameters (Å, º)

O1—C1	1.308 (2)	C2—C3	1.394 (2)
O1—H	0.90 (2)	C2—C7	1.389 (2)
O2—C1	1.225 (1)	C3—C4	1.385 (2)
O3—N2	1.260 (2)	C3—H3	0.98 (2)
O4—N2	1.240 (2)	C4—C5	1.381 (2)
O5—N2	1.219 (2)	C5—C6	1.385 (2)
N1—C4	1.464 (2)	C5—H5	0.96 (2)
N1—H1n	0.90 (2)	C6—C7	1.388 (2)
N1—H2n	0.92 (2)	C6—H6	0.97 (2)
N1—H3n	0.91 (2)	C7—H7	0.98 (2)
C1—C2	1.487 (2)
C1—O1—H	110 (1)	C2—C3—C4	118.6 (1)
C4—N1—H1n	105.8 (9)	C2—C3—H3	121 (1)
C4—N1—H2n	111 (1)	C4—C3—H3	120 (1)
C4—N1—H3n	109 (1)	N1—C4—C3	119.3 (1)
H1n—N1—H2n	110 (2)	N1—C4—C5	119.1 (1)
H1n—N1—H3n	114 (2)	C3—C4—C5	121.6 (1)
H2n—N1—H3n	106 (2)	C4—C5—C6	119.3 (1)
O3—N2—O4	118.2 (1)	C4—C5—H5	120.8 (13)
O3—N2—O5	120.5 (1)	C6—C5—H5	119.9 (12)
O4—N2—O5	121.3 (1)	C5—C6—C7	120.3 (1)
O1—C1—O2	123.6 (1)	C5—C6—H6	120 (1)
O1—C1—C2	114.7 (1)	C7—C6—H6	119 (1)
O2—C1—C2	121.7 (1)	C2—C7—C6	119.8 (1)
C1—C2—C3	120.6 (1)	C2—C7—H7	119 (1)
C1—C2—C7	118.9 (1)	C6—C7—H7	121 (1)
C3—C2—C7	120.4 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H···O2^i	0.90 (2)	1.78 (2)	2.676 (1)	177 (2)
N1—H1n···O4^ii	0.90 (2)	2.03 (2)	2.883 (2)	159 (2)
N1—H3n···O3	0.91 (2)	1.98 (2)	2.842 (2)	158 (2)
N1—H2n···O3^iii	0.92 (2)	1.97 (2)	2.849 (2)	161 (2)

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