Guanidinium 3-nitro-benzoate.

The title compound, CH(6)N(3) (+)·C(7)H(4)NO(4) (-), an anhydrous guanidinium salt, shows a N-H⋯O hydrogen-bond network in which the guanidinium cation is involved in three cyclic R(2) (1)(6) hydrogen-bonding associations with separate carboxyl-ate O-atom acceptors. Further peripheral associations include a cyclic R(1) (2)(4) cation-anion inter-action, forming inter-linked undulating sheets in the three-dimensional structure.

Related literature

For the structures of other guanidinium benzoate salts, see: Kleb et al. (1998 ▶); Pereira Silva et al. (2007 ▶, 2010 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

CH6N3 +·C7H4NO4 −

M = 226.20

Orthorhombic,

a = 7.3978 (12) Å

b = 10.1302 (12) Å

c = 13.7118 (17) Å

V = 1027.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 297 K

0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.94, T max = 0.98

7455 measured reflections

1252 independent reflections

1092 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.03

1252 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002581X/bv2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002581X/bv2146Isup2.hkl

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

CH6N3+·C7H4NO4−	Dx = 1.462 Mg m−3
Mr = 226.20	Melting point: 514 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2964 reflections
a = 7.3978 (12) Å	θ = 3.0–28.9°
b = 10.1302 (12) Å	µ = 0.12 mm−1
c = 13.7118 (17) Å	T = 297 K
V = 1027.6 (2) Å3	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm
F(000) = 472

Oxford Diffraction Gemini-S CCD-detector diffractometer	1252 independent reflections
Radiation source: Enhance (Mo) X-ray source	1092 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.94, Tmax = 0.98	k = −12→11
7455 measured reflections	l = −17→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0716P)2] where P = (Fo2 + 2Fc2)/3
1252 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O11	0.8853 (3)	0.39642 (19)	−0.15616 (11)	0.0763 (7)
O12	0.8391 (3)	0.51830 (14)	−0.02410 (12)	0.0587 (5)
O31	0.9478 (4)	0.2929 (2)	0.29189 (13)	0.0891 (8)
O32	0.8919 (4)	0.0871 (2)	0.30563 (13)	0.0879 (8)
N31	0.9085 (3)	0.1871 (2)	0.25680 (14)	0.0582 (6)
C1	0.8552 (3)	0.28643 (18)	−0.00456 (13)	0.0395 (5)
C2	0.8834 (3)	0.29418 (19)	0.09621 (14)	0.0395 (5)
C3	0.8802 (3)	0.1785 (2)	0.15053 (15)	0.0438 (6)
C4	0.8496 (3)	0.0567 (2)	0.10846 (18)	0.0546 (7)
C5	0.8224 (3)	0.0507 (2)	0.00897 (18)	0.0579 (8)
C6	0.8262 (3)	0.1633 (2)	−0.04688 (16)	0.0487 (6)
C11	0.8592 (3)	0.4098 (2)	−0.06632 (14)	0.0472 (6)
N1G	0.5698 (4)	0.7518 (2)	0.02372 (14)	0.0596 (7)
N2G	0.5023 (3)	0.7924 (2)	0.18458 (16)	0.0624 (7)
N3G	0.6559 (3)	0.6050 (2)	0.14213 (17)	0.0599 (7)
C1G	0.5763 (3)	0.7166 (2)	0.11723 (14)	0.0468 (6)
H2	0.90390	0.37520	0.12620	0.0470*
H4	0.84730	−0.01950	0.14630	0.0660*
H5	0.80130	−0.03050	−0.02060	0.0690*
H6	0.80920	0.15720	−0.11390	0.0580*
H11G	0.617 (4)	0.701 (3)	−0.015 (2)	0.070 (9)*
H12G	0.514 (4)	0.821 (3)	0.012 (2)	0.072 (8)*
H21G	0.444 (4)	0.869 (3)	0.170 (2)	0.077 (9)*
H22G	0.506 (4)	0.767 (3)	0.244 (2)	0.065 (8)*
H31G	0.666 (4)	0.588 (3)	0.203 (2)	0.065 (8)*
H32G	0.715 (4)	0.563 (3)	0.093 (2)	0.073 (9)*

	U11	U22	U33	U12	U13	U23
O11	0.1174 (16)	0.0759 (12)	0.0357 (8)	0.0071 (13)	0.0050 (10)	0.0078 (8)
O12	0.0866 (12)	0.0375 (7)	0.0520 (8)	−0.0007 (8)	0.0034 (9)	0.0074 (6)
O31	0.148 (2)	0.0728 (12)	0.0464 (9)	−0.0228 (14)	−0.0197 (12)	0.0015 (9)
O32	0.1360 (19)	0.0687 (11)	0.0591 (11)	0.0044 (13)	0.0017 (12)	0.0305 (9)
N31	0.0728 (11)	0.0565 (11)	0.0452 (10)	0.0004 (11)	−0.0036 (9)	0.0113 (8)
C1	0.0411 (9)	0.0384 (10)	0.0390 (9)	−0.0016 (9)	0.0000 (9)	−0.0014 (8)
C2	0.0476 (10)	0.0313 (8)	0.0395 (9)	−0.0005 (9)	−0.0007 (8)	0.0007 (7)
C3	0.0486 (10)	0.0413 (10)	0.0415 (10)	0.0011 (9)	−0.0006 (9)	0.0044 (8)
C4	0.0643 (13)	0.0340 (10)	0.0656 (13)	−0.0007 (10)	0.0029 (12)	0.0083 (10)
C5	0.0679 (15)	0.0348 (10)	0.0710 (15)	−0.0073 (10)	0.0012 (13)	−0.0151 (10)
C6	0.0527 (11)	0.0490 (11)	0.0445 (10)	−0.0037 (10)	0.0000 (9)	−0.0100 (9)
C11	0.0597 (12)	0.0444 (10)	0.0375 (10)	0.0004 (10)	0.0016 (10)	0.0038 (9)
N1G	0.0873 (16)	0.0448 (10)	0.0467 (12)	0.0052 (11)	0.0022 (11)	0.0093 (9)
N2G	0.0885 (15)	0.0519 (11)	0.0469 (11)	0.0123 (12)	0.0033 (11)	−0.0015 (9)
N3G	0.0854 (14)	0.0511 (11)	0.0433 (10)	0.0130 (12)	0.0016 (11)	0.0069 (9)
C1G	0.0588 (12)	0.0398 (10)	0.0418 (11)	−0.0032 (10)	−0.0027 (9)	0.0025 (9)

O11—C11	1.254 (2)	N3G—H32G	0.91 (3)
O12—C11	1.251 (3)	C1—C6	1.392 (3)
O31—N31	1.210 (3)	C1—C11	1.510 (3)
O32—N31	1.221 (3)	C1—C2	1.400 (3)
N31—C3	1.475 (3)	C2—C3	1.389 (3)
N1G—C1G	1.332 (3)	C3—C4	1.381 (3)
N2G—C1G	1.320 (3)	C4—C5	1.380 (3)
N3G—C1G	1.320 (3)	C5—C6	1.374 (3)
N1G—H12G	0.83 (3)	C2—H2	0.9300
N1G—H11G	0.82 (3)	C4—H4	0.9300
N2G—H22G	0.86 (3)	C5—H5	0.9300
N2G—H21G	0.91 (3)	C6—H6	0.9300
N3G—H31G	0.86 (3)
O31—N31—O32	122.8 (2)	C2—C3—C4	122.2 (2)
O31—N31—C3	118.64 (19)	C3—C4—C5	118.4 (2)
O32—N31—C3	118.60 (19)	C4—C5—C6	120.8 (2)
C1G—N1G—H12G	115.5 (19)	C1—C6—C5	121.0 (2)
H11G—N1G—H12G	128 (3)	O11—C11—C1	117.67 (18)
C1G—N1G—H11G	116 (2)	O12—C11—C1	117.73 (17)
H21G—N2G—H22G	119 (3)	O11—C11—O12	124.6 (2)
C1G—N2G—H21G	122.6 (18)	C3—C2—H2	121.00
C1G—N2G—H22G	119 (2)	C1—C2—H2	121.00
H31G—N3G—H32G	126 (3)	C3—C4—H4	121.00
C1G—N3G—H32G	115.1 (19)	C5—C4—H4	121.00
C1G—N3G—H31G	118 (2)	C4—C5—H5	120.00
C6—C1—C11	120.72 (17)	C6—C5—H5	120.00
C2—C1—C11	120.29 (17)	C5—C6—H6	120.00
C2—C1—C6	118.99 (17)	C1—C6—H6	119.00
C1—C2—C3	118.66 (18)	N2G—C1G—N3G	120.2 (2)
N31—C3—C4	119.27 (19)	N1G—C1G—N2G	120.2 (2)
N31—C3—C2	118.53 (18)	N1G—C1G—N3G	119.6 (2)
O31—N31—C3—C2	−5.8 (3)	C2—C1—C11—O12	−18.9 (3)
O31—N31—C3—C4	174.9 (2)	C6—C1—C11—O11	−19.1 (3)
O32—N31—C3—C2	174.4 (2)	C6—C1—C11—O12	162.0 (2)
O32—N31—C3—C4	−4.9 (3)	C1—C2—C3—N31	−179.5 (2)
C6—C1—C2—C3	−0.4 (3)	C1—C2—C3—C4	−0.2 (3)
C11—C1—C2—C3	−179.5 (2)	N31—C3—C4—C5	179.6 (2)
C2—C1—C6—C5	1.0 (3)	C2—C3—C4—C5	0.4 (3)
C11—C1—C6—C5	−180.0 (2)	C3—C4—C5—C6	0.2 (3)
C2—C1—C11—O11	160.0 (2)	C4—C5—C6—C1	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1G—H11G···O12	0.82 (3)	2.48 (3)	3.161 (3)	142 (3)
N1G—H12G···O12i	0.83 (3)	2.09 (3)	2.887 (3)	162 (3)
N2G—H21G···O11i	0.91 (3)	2.42 (3)	3.292 (3)	160 (2)
N2G—H21G···O12i	0.91 (3)	2.43 (3)	3.159 (3)	137 (2)
N2G—H22G···O11ii	0.86 (3)	2.29 (3)	3.020 (3)	143 (3)
N3G—H31G···O11ii	0.86 (3)	1.97 (3)	2.783 (3)	157 (3)
N3G—H32G···O12	0.91 (3)	1.90 (3)	2.794 (3)	166 (3)
C4—H4···O31iii	0.93	2.57	3.355 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1G—H11G⋯O12	0.82 (3)	2.48 (3)	3.161 (3)	142 (3)
N1G—H12G⋯O12i	0.83 (3)	2.09 (3)	2.887 (3)	162 (3)
N2G—H21G⋯O11i	0.91 (3)	2.42 (3)	3.292 (3)	160 (2)
N2G—H21G⋯O12i	0.91 (3)	2.43 (3)	3.159 (3)	137 (2)
N2G—H22G⋯O11ii	0.86 (3)	2.29 (3)	3.020 (3)	143 (3)
N3G—H31G⋯O11ii	0.86 (3)	1.97 (3)	2.783 (3)	157 (3)
N3G—H32G⋯O12	0.91 (3)	1.90 (3)	2.794 (3)	166 (3)

Symmetry codes: (i) ; (ii) .