Guanidinium 2-phenyl-acetate.

In the structure of the title salt, CH(6)N(3) (+)·C(8)H(7)O(2) (-), the guanidinium cation gives three cyclic hydrogen-bonding inter-actions with O-atom acceptors of three independent phenyl-acetate anions, one R(2) (2)(8) and two R(2) (1)(6), giving one-dimensional columnar structures which extend down the 4(2) axis in the tetra-gonal cell. Within these structures, there are solvent-accessible voids of volume 86.5 Å(3).

Related literature

For the structures of simple monocyclic aromatic guanidinium carboxyl­ates, see: Pereira Silva et al. (2007 ▶, 2010 ▶); Kleb et al. (1998 ▶); Smith & Wermuth (2010 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

CH6N3 +·C8H7O2 −

M = 195.22

Tetragonal,

a = 16.8418 (10) Å

c = 7.8372 (6) Å

V = 2223.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

7477 measured reflections

2191 independent reflections

1430 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 0.93

2191 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025821/bv2147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025821/bv2147Isup2.hkl

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

CH6N3+·C8H7O2−	Dx = 1.167 Mg m−3
Mr = 195.22	Melting point: 443 K
Tetragonal, P42/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 4bc	Cell parameters from 2510 reflections
a = 16.8418 (10) Å	θ = 3.1–28.6°
c = 7.8372 (6) Å	µ = 0.09 mm−1
V = 2223.0 (3) Å3	T = 200 K
Z = 8	Block, colourless
F(000) = 832	0.30 × 0.25 × 0.20 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	1430 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray source	Rint = 0.027
graphite	θmax = 26.0°, θmin = 3.1°
ω scans	h = −20→18
7477 measured reflections	k = −10→20
2191 independent reflections	l = −9→8

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0592P)2] where P = (Fo2 + 2Fc2)/3
2191 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 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
O21	0.64098 (7)	0.43351 (6)	0.19316 (12)	0.0534 (4)
O22	0.62981 (7)	0.44279 (6)	−0.08684 (12)	0.0518 (4)
C1	0.61757 (8)	0.59370 (8)	0.25158 (18)	0.0364 (5)
C2	0.68820 (9)	0.61788 (9)	0.3219 (2)	0.0510 (6)
C3	0.69086 (15)	0.64720 (11)	0.4853 (3)	0.0775 (9)
C4	0.6222 (2)	0.65222 (12)	0.5811 (2)	0.0918 (11)
C5	0.55179 (15)	0.62730 (13)	0.5105 (3)	0.0817 (9)
C6	0.54971 (10)	0.59874 (10)	0.3487 (2)	0.0554 (6)
C11	0.61473 (11)	0.56093 (9)	0.07399 (18)	0.0550 (6)
C21	0.62985 (8)	0.47232 (9)	0.05979 (17)	0.0378 (5)
N1G	0.77589 (11)	0.40624 (9)	0.41545 (18)	0.0537 (5)
N2G	0.77186 (10)	0.40368 (9)	0.70667 (17)	0.0517 (5)
N3G	0.66128 (8)	0.43990 (8)	0.55565 (18)	0.0445 (5)
C1G	0.73652 (9)	0.41692 (8)	0.55946 (17)	0.0381 (5)
H2	0.73470	0.61440	0.25830	0.0610*
H3	0.73900	0.66370	0.53150	0.0930*
H4	0.62360	0.67210	0.69180	0.1100*
H5	0.50520	0.63000	0.57400	0.0980*
H6	0.50160	0.58230	0.30260	0.0670*
H11	0.65390	0.58860	0.00530	0.0660*
H12	0.56290	0.57230	0.02590	0.0660*
H11G	0.8248 (12)	0.3924 (10)	0.4193 (18)	0.054 (5)*
H12G	0.7504 (10)	0.4141 (10)	0.321 (2)	0.063 (5)*
H21G	0.7451 (10)	0.4104 (9)	0.795 (2)	0.049 (5)*
H22G	0.8201 (12)	0.3872 (10)	0.710 (2)	0.061 (6)*
H31G	0.6432 (9)	0.4549 (9)	0.453 (2)	0.049 (5)*
H32G	0.6410 (10)	0.4547 (10)	0.651 (2)	0.055 (5)*

	U11	U22	U33	U12	U13	U23
O21	0.0885 (9)	0.0400 (6)	0.0317 (6)	0.0054 (6)	−0.0136 (5)	−0.0003 (5)
O22	0.0728 (8)	0.0548 (7)	0.0279 (6)	−0.0017 (6)	0.0036 (5)	−0.0026 (5)
C1	0.0399 (8)	0.0297 (8)	0.0397 (8)	0.0033 (7)	−0.0008 (7)	0.0028 (6)
C2	0.0427 (9)	0.0458 (10)	0.0646 (11)	−0.0026 (8)	−0.0051 (8)	0.0073 (8)
C3	0.1009 (18)	0.0509 (12)	0.0807 (15)	−0.0161 (12)	−0.0466 (13)	0.0084 (11)
C4	0.185 (3)	0.0493 (12)	0.0411 (11)	0.0059 (15)	−0.0096 (14)	−0.0145 (9)
C5	0.1019 (18)	0.0733 (14)	0.0699 (14)	0.0135 (13)	0.0366 (13)	−0.0137 (12)
C6	0.0406 (10)	0.0558 (11)	0.0698 (12)	0.0006 (8)	0.0068 (8)	−0.0051 (9)
C11	0.0797 (13)	0.0446 (9)	0.0406 (9)	0.0064 (9)	−0.0023 (8)	0.0044 (7)
C21	0.0400 (8)	0.0445 (9)	0.0288 (8)	0.0002 (7)	0.0003 (6)	0.0004 (7)
N1G	0.0462 (9)	0.0832 (11)	0.0318 (8)	0.0094 (8)	0.0017 (7)	0.0011 (7)
N2G	0.0433 (9)	0.0805 (11)	0.0312 (8)	0.0052 (8)	−0.0022 (7)	−0.0033 (7)
N3G	0.0449 (8)	0.0599 (9)	0.0288 (8)	0.0051 (6)	0.0005 (6)	0.0030 (6)
C1G	0.0415 (9)	0.0413 (8)	0.0314 (8)	−0.0044 (7)	−0.0011 (7)	−0.0003 (6)

O21—C21	1.2470 (17)	C1—C2	1.373 (2)
O22—C21	1.2522 (17)	C2—C3	1.373 (3)
N1G—C1G	1.321 (2)	C3—C4	1.381 (4)
N2G—C1G	1.317 (2)	C4—C5	1.374 (4)
N3G—C1G	1.325 (2)	C5—C6	1.357 (3)
N1G—H11G	0.86 (2)	C11—C21	1.518 (2)
N1G—H12G	0.866 (16)	C2—H2	0.9300
N2G—H21G	0.834 (16)	C3—H3	0.9300
N2G—H22G	0.86 (2)	C4—H4	0.9300
N3G—H31G	0.897 (16)	C5—H5	0.9300
N3G—H32G	0.859 (16)	C6—H6	0.9300
C1—C6	1.376 (2)	C11—H12	0.9700
C1—C11	1.498 (2)	C11—H11	0.9700
C1G—N1G—H12G	117.4 (11)	O21—C21—O22	124.14 (14)
H11G—N1G—H12G	123.3 (15)	C1—C2—H2	120.00
C1G—N1G—H11G	119.3 (10)	C3—C2—H2	120.00
C1G—N2G—H22G	120.6 (11)	C2—C3—H3	120.00
H21G—N2G—H22G	122.0 (15)	C4—C3—H3	120.00
C1G—N2G—H21G	117.4 (11)	C5—C4—H4	120.00
C1G—N3G—H32G	116.5 (11)	C3—C4—H4	121.00
H31G—N3G—H32G	124.3 (15)	C4—C5—H5	120.00
C1G—N3G—H31G	115.3 (10)	C6—C5—H5	120.00
C2—C1—C6	118.65 (14)	C1—C6—H6	119.00
C2—C1—C11	120.66 (13)	C5—C6—H6	119.00
C6—C1—C11	120.68 (14)	C21—C11—H11	109.00
C1—C2—C3	120.62 (16)	C21—C11—H12	108.00
C2—C3—C4	120.1 (2)	H11—C11—H12	108.00
C3—C4—C5	119.00 (18)	C1—C11—H11	108.00
C4—C5—C6	120.5 (2)	C1—C11—H12	108.00
C1—C6—C5	121.17 (17)	N2G—C1G—N3G	120.08 (14)
C1—C11—C21	115.15 (12)	N1G—C1G—N2G	119.89 (15)
O21—C21—C11	118.63 (12)	N1G—C1G—N3G	120.02 (14)
O22—C21—C11	117.24 (12)
C6—C1—C2—C3	−0.6 (2)	C1—C2—C3—C4	0.4 (3)
C11—C1—C2—C3	−179.37 (15)	C2—C3—C4—C5	0.2 (3)
C2—C1—C6—C5	0.3 (2)	C3—C4—C5—C6	−0.5 (3)
C11—C1—C6—C5	179.08 (16)	C4—C5—C6—C1	0.2 (3)
C2—C1—C11—C21	86.98 (18)	C1—C11—C21—O21	2.0 (2)
C6—C1—C11—C21	−91.75 (18)	C1—C11—C21—O22	−178.42 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1G—H11G···O22i	0.86 (2)	2.02 (2)	2.876 (2)	173.9 (15)
N1G—H12G···O21	0.866 (16)	2.123 (17)	2.900 (2)	149.0 (15)
N2G—H21G···O22ii	0.834 (16)	2.219 (17)	2.9625 (19)	148.5 (15)
N2G—H22G···O21i	0.86 (2)	1.97 (2)	2.827 (2)	172.6 (15)
N3G—H31G···O21	0.897 (16)	2.068 (16)	2.8634 (17)	147.2 (13)
N3G—H32G···O22ii	0.859 (16)	2.073 (16)	2.8520 (17)	150.5 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1G—H11G⋯O22i	0.86 (2)	2.02 (2)	2.876 (2)	173.9 (15)
N1G—H12G⋯O21	0.866 (16)	2.123 (17)	2.900 (2)	149.0 (15)
N2G—H21G⋯O22ii	0.834 (16)	2.219 (17)	2.9625 (19)	148.5 (15)
N2G—H22G⋯O21i	0.86 (2)	1.97 (2)	2.827 (2)	172.6 (15)
N3G—H31G⋯O21	0.897 (16)	2.068 (16)	2.8634 (17)	147.2 (13)
N3G—H32G⋯O22ii	0.859 (16)	2.073 (16)	2.8520 (17)	150.5 (15)

Symmetry codes: (i) ; (ii) .