Guanidinium phenyl-arsonate-guanidine-water (1/1/2).

In the structure of the title compound, CH(6)N(3) (+)·C(6)H(6)AsO(3) (-)·CH(5)N(3)·2H(2)O, the phenyl-arsonate anion participates in two R(2) (2)(8) cyclic hydrogen-bonding inter-actions, one with a guanidinium cation, the other with a guanidine mol-ecule. The anions are also bridged by the water mol-ecules, one of which completes a cyclic R(5) (3)(9) hydrogen-bonding association with the guanidinum cation, conjoint with one of the three R(2) (2)(8) associations about that ion, as well as forming an R(2) (1)(6) cyclic association with the guanidine mol-ecule. The result is a three-dimensional framework structure.

Related literature

For chemical data on phenyl­arsonic acid, see: O’Neil (2001 ▶). For related guanidinium structures, see: Smith et al. (2001 ▶); Smith & Wermuth (2010 ▶); Sun et al. (2002 ▶); Swift & Ward (1998 ▶); Swift et al. (1998 ▶); Mak & Xue (2000 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

CH6N3 +·C6H6AsO3 −·CH5N3·2H2O

M = 356.23

Monoclinic,

a = 18.6545 (14) Å

b = 7.6394 (3) Å

c = 12.6319 (10) Å

β = 121.856 (10)°

V = 1529.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.25 mm−1

T = 200 K

0.27 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.935, T max = 0.985

4919 measured reflections

2095 independent reflections

1940 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.035

S = 0.96

2095 reflections

245 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 590 Friedel pairs

Flack parameter: 0.020 (7)

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 ▶) 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/S1600536810025043/tk2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025043/tk2684Isup2.hkl

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

CH6N3+·C6H6AsO3−·CH5N3·2H2O	F(000) = 736
Mr = 356.23	Dx = 1.548 Mg m−3
Monoclinic, Cc	Melting point: 505 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.6545 (14) Å	Cell parameters from 3772 reflections
b = 7.6394 (3) Å	θ = 3.1–28.7°
c = 12.6319 (10) Å	µ = 2.25 mm−1
β = 121.856 (10)°	T = 200 K
V = 1529.0 (2) Å3	Block, colourless
Z = 4	0.27 × 0.25 × 0.20 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	2095 independent reflections
Radiation source: Enhance (Mo) X-ray source	1940 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 16.08 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −22→21
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.935, Tmax = 0.985	l = −11→15
4919 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.035	w = 1/[σ2(Fo2) + (0.0159P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.002
2095 reflections	Δρmax = 0.17 e Å−3
245 parameters	Δρmin = −0.22 e Å−3
2 restraints	Absolute structure: Flack (1983), 590 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.020 (7)

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
As1	0.85472 (1)	0.69726 (3)	0.45636 (2)	0.0162 (1)
O1	0.85598 (11)	0.8928 (2)	0.39683 (17)	0.0220 (6)
O2	0.79876 (11)	0.5495 (2)	0.34181 (17)	0.0223 (6)
O3	0.81253 (10)	0.7081 (2)	0.54592 (15)	0.0209 (6)
C1	0.96902 (16)	0.6103 (3)	0.5496 (2)	0.0214 (8)
C2	1.00375 (19)	0.5330 (4)	0.6658 (3)	0.0312 (10)
C3	1.0834 (2)	0.4638 (5)	0.7248 (4)	0.0393 (12)
C4	1.1311 (2)	0.4729 (5)	0.6705 (3)	0.0388 (11)
C5	1.0978 (2)	0.5496 (5)	0.5556 (4)	0.0423 (16)
C6	1.0164 (2)	0.6166 (5)	0.4950 (3)	0.0326 (11)
N1A	0.81112 (15)	1.0554 (3)	0.6380 (3)	0.0214 (8)
N2A	0.79667 (18)	1.3549 (4)	0.6207 (3)	0.0253 (9)
N3A	0.80233 (15)	1.1956 (4)	0.4697 (2)	0.0259 (8)
C1A	0.80313 (16)	1.2018 (4)	0.5759 (2)	0.0185 (8)
N1B	0.50840 (19)	0.4864 (5)	0.2386 (4)	0.0452 (11)
N2B	0.6296 (2)	0.6056 (4)	0.4032 (3)	0.0391 (12)
N3B	0.6265 (2)	0.5171 (5)	0.2284 (4)	0.0391 (11)
C1B	0.5899 (2)	0.5383 (4)	0.2899 (4)	0.0301 (11)
O1W	0.88312 (19)	0.7021 (3)	0.7987 (2)	0.0416 (10)
O2W	0.99736 (15)	0.9183 (4)	0.9723 (2)	0.0421 (8)
H2	0.97270	0.52800	0.70410	0.0370*
H3	1.10560	0.41020	0.80200	0.0470*
H4	1.18560	0.42720	0.71170	0.0470*
H5	1.12960	0.55670	0.51860	0.0510*
H6	0.99350	0.66650	0.41640	0.0390*
H21	0.737 (3)	0.538 (7)	0.301 (4)	0.042 (11)*
H11A	0.8076 (16)	0.956 (4)	0.606 (3)	0.036 (8)*
H12A	0.823 (2)	1.061 (4)	0.717 (3)	0.043 (10)*
H21A	0.7921 (16)	1.368 (4)	0.680 (3)	0.038 (7)*
H22A	0.7998 (16)	1.461 (4)	0.585 (3)	0.045 (8)*
H31A	0.8017 (17)	1.287 (4)	0.436 (3)	0.035 (8)*
H32A	0.8159 (13)	1.093 (3)	0.441 (2)	0.037 (6)*
H11B	0.486 (2)	0.501 (5)	0.285 (3)	0.048 (11)*
H12B	0.480 (2)	0.444 (5)	0.166 (4)	0.052 (12)*
H21B	0.599 (2)	0.613 (5)	0.437 (4)	0.053 (12)*
H22B	0.683 (2)	0.653 (4)	0.436 (3)	0.055 (9)*
H31B	0.5958 (18)	0.495 (4)	0.156 (3)	0.050 (9)*
H11W	0.8672 (19)	0.702 (4)	0.714 (3)	0.052 (9)*
H12W	0.859 (2)	0.610 (4)	0.809 (3)	0.046 (10)*
H21W	0.960 (2)	0.982 (5)	0.954 (3)	0.046 (12)*
H22W	0.973 (2)	0.830 (5)	0.950 (4)	0.048 (12)*

	U11	U22	U33	U12	U13	U23
As1	0.0201 (1)	0.0152 (1)	0.0153 (1)	−0.0004 (2)	0.0107 (1)	−0.0003 (2)
O1	0.0286 (10)	0.0189 (10)	0.0231 (11)	−0.0003 (8)	0.0167 (9)	0.0020 (8)
O2	0.0206 (10)	0.0247 (10)	0.0215 (11)	−0.0028 (8)	0.0111 (8)	−0.0049 (8)
O3	0.0278 (10)	0.0226 (9)	0.0174 (10)	0.0002 (8)	0.0155 (8)	−0.0031 (8)
C1	0.0212 (14)	0.0191 (13)	0.0205 (15)	−0.0008 (11)	0.0087 (12)	−0.0026 (12)
C2	0.0302 (17)	0.0396 (18)	0.0248 (17)	0.0038 (14)	0.0153 (14)	0.0063 (14)
C3	0.034 (2)	0.051 (2)	0.027 (2)	0.0097 (18)	0.0121 (17)	0.0101 (18)
C4	0.0249 (19)	0.051 (2)	0.033 (2)	0.0132 (17)	0.0101 (15)	0.0051 (18)
C5	0.026 (2)	0.070 (3)	0.039 (3)	0.0116 (19)	0.0226 (19)	0.013 (2)
C6	0.0287 (19)	0.0407 (19)	0.0261 (18)	0.0037 (15)	0.0130 (14)	0.0105 (16)
N1A	0.0329 (14)	0.0147 (12)	0.0211 (14)	0.0015 (10)	0.0174 (12)	0.0009 (11)
N2A	0.0425 (18)	0.0191 (15)	0.0245 (16)	0.0001 (12)	0.0246 (14)	−0.0022 (12)
N3A	0.0440 (15)	0.0198 (12)	0.0223 (13)	0.0015 (12)	0.0233 (11)	0.0028 (12)
C1A	0.0165 (13)	0.0203 (14)	0.0167 (14)	−0.0022 (12)	0.0075 (11)	−0.0028 (13)
N1B	0.0262 (17)	0.061 (2)	0.046 (2)	−0.0091 (14)	0.0175 (16)	−0.0030 (17)
N2B	0.027 (2)	0.054 (2)	0.032 (2)	−0.0023 (15)	0.0127 (16)	0.0048 (15)
N3B	0.0340 (19)	0.049 (2)	0.031 (2)	−0.0045 (16)	0.0150 (17)	−0.0104 (17)
C1B	0.0252 (19)	0.027 (2)	0.034 (2)	−0.0006 (15)	0.0128 (19)	0.0063 (18)
O1W	0.068 (2)	0.0355 (17)	0.0222 (14)	−0.0275 (14)	0.0245 (14)	−0.0064 (13)
O2W	0.0281 (13)	0.0333 (14)	0.0532 (16)	0.0002 (12)	0.0134 (12)	−0.0182 (13)

As1—O1	1.6781 (17)	N2B—C1B	1.320 (5)
As1—O2	1.6921 (17)	N3B—C1B	1.287 (6)
As1—O3	1.687 (2)	N1B—H11B	0.89 (4)
As1—C1	1.930 (3)	N1B—H12B	0.85 (4)
O2—H21	0.99 (6)	N2B—H21B	0.88 (5)
O1W—H11W	0.95 (3)	N2B—H22B	0.93 (4)
O1W—H12W	0.88 (3)	N3B—H31B	0.80 (3)
O2W—H21W	0.78 (4)	C1—C2	1.385 (4)
O2W—H22W	0.78 (4)	C1—C6	1.379 (5)
N1A—C1A	1.329 (4)	C2—C3	1.369 (6)
N2A—C1A	1.332 (4)	C3—C4	1.383 (6)
N3A—C1A	1.335 (3)	C4—C5	1.373 (5)
N1A—H12A	0.90 (3)	C5—C6	1.388 (6)
N1A—H11A	0.85 (3)	C2—H2	0.9300
N2A—H21A	0.80 (3)	C3—H3	0.9300
N2A—H22A	0.94 (3)	C4—H4	0.9300
N3A—H31A	0.82 (3)	C5—H5	0.9300
N3A—H32A	0.95 (2)	C6—H6	0.9300
N1B—C1B	1.360 (6)
As1···H11A	3.16 (3)	As1···H32A	3.09 (2)
As1···H11W	3.14 (3)	As1···H12Wii	3.02 (3)
As1···H22Ai	2.95 (3)	As1···H21Aiii	3.08 (3)
As1···H22B	3.09 (4)	As1···H21Wiii	3.15 (4)
O1—As1—O2	111.03 (9)	As1—C1—C6	118.4 (2)
O1—As1—O3	112.25 (9)	C2—C1—C6	118.7 (3)
O1—As1—C1	107.92 (11)	As1—C1—C2	122.8 (3)
O2—As1—O3	108.09 (10)	C1—C2—C3	120.5 (4)
O2—As1—C1	106.05 (10)	C2—C3—C4	120.6 (4)
O3—As1—C1	111.34 (10)	C3—C4—C5	119.7 (4)
As1—O2—H21	122 (3)	C4—C5—C6	119.6 (4)
H11W—O1W—H12W	107 (3)	C1—C6—C5	121.0 (3)
H21W—O2W—H22W	100 (4)	C3—C2—H2	120.00
H11A—N1A—H12A	119 (3)	C1—C2—H2	120.00
C1A—N1A—H11A	121 (2)	C2—C3—H3	120.00
C1A—N1A—H12A	120 (2)	C4—C3—H3	120.00
H21A—N2A—H22A	114 (3)	C5—C4—H4	120.00
C1A—N2A—H21A	126 (2)	C3—C4—H4	120.00
C1A—N2A—H22A	121 (2)	C6—C5—H5	120.00
H31A—N3A—H32A	116 (3)	C4—C5—H5	120.00
C1A—N3A—H32A	123.2 (14)	C5—C6—H6	119.00
C1A—N3A—H31A	119 (2)	C1—C6—H6	120.00
C1B—N1B—H11B	117 (2)	N2A—C1A—N3A	120.2 (3)
H11B—N1B—H12B	121 (4)	N1A—C1A—N2A	119.7 (3)
C1B—N1B—H12B	122 (3)	N1A—C1A—N3A	120.1 (3)
C1B—N2B—H22B	120 (2)	N2B—C1B—N3B	122.1 (4)
C1B—N2B—H21B	115 (3)	N1B—C1B—N2B	118.5 (4)
H21B—N2B—H22B	125 (4)	N1B—C1B—N3B	119.5 (4)
C1B—N3B—H31B	115 (3)
O1—As1—C1—C2	136.3 (2)	C6—C1—C2—C3	−0.2 (5)
O1—As1—C1—C6	−47.5 (2)	As1—C1—C6—C5	−177.4 (3)
O2—As1—C1—C2	−104.7 (2)	C2—C1—C6—C5	−1.0 (5)
O2—As1—C1—C6	71.6 (2)	C1—C2—C3—C4	1.3 (5)
O3—As1—C1—C2	12.7 (2)	C2—C3—C4—C5	−1.0 (6)
O3—As1—C1—C6	−171.1 (2)	C3—C4—C5—C6	−0.3 (6)
As1—C1—C2—C3	176.0 (3)	C4—C5—C6—C1	1.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···N3B	0.99 (6)	1.77 (6)	2.753 (5)	180 (6)
N1A—H11A···O3	0.85 (3)	2.06 (3)	2.903 (3)	173 (3)
N1A—H12A···O1iv	0.90 (3)	2.05 (3)	2.943 (4)	172 (3)
N2A—H21A···O2iv	0.80 (3)	2.08 (3)	2.867 (4)	167 (3)
N2A—H22A···O3v	0.94 (3)	2.00 (3)	2.925 (4)	167 (3)
N3A—H31A···O2v	0.82 (3)	2.32 (3)	3.132 (3)	179 (5)
N3A—H32A···O1	0.95 (2)	1.91 (2)	2.859 (4)	174 (2)
N1B—H11B···O2Wvi	0.89 (4)	2.34 (3)	3.151 (5)	151 (3)
N2B—H21B···O2Wvi	0.88 (5)	2.18 (5)	3.026 (5)	163 (4)
N2B—H22B···O3	0.93 (4)	2.10 (4)	3.002 (4)	165 (3)
N3B—H31B···O2Wvii	0.80 (3)	2.15 (3)	2.935 (5)	169 (4)
O1W—H11W···O3	0.95 (3)	1.81 (3)	2.737 (3)	167 (4)
O1W—H12W···O2viii	0.88 (3)	1.85 (4)	2.715 (4)	168 (4)
O2W—H21W···O1iv	0.78 (4)	1.93 (4)	2.701 (4)	171 (4)
O2W—H22W···O1W	0.78 (4)	2.01 (4)	2.673 (4)	143 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H21⋯N3B	0.99 (6)	1.77 (6)	2.753 (5)	180 (6)
N1A—H11A⋯O3	0.85 (3)	2.06 (3)	2.903 (3)	173 (3)
N1A—H12A⋯O1i	0.90 (3)	2.05 (3)	2.943 (4)	172 (3)
N2A—H21A⋯O2i	0.80 (3)	2.08 (3)	2.867 (4)	167 (3)
N2A—H22A⋯O3ii	0.94 (3)	2.00 (3)	2.925 (4)	167 (3)
N3A—H31A⋯O2ii	0.82 (3)	2.32 (3)	3.132 (3)	179 (5)
N3A—H32A⋯O1	0.95 (2)	1.91 (2)	2.859 (4)	174 (2)
N1B—H11B⋯O2Wiii	0.89 (4)	2.34 (3)	3.151 (5)	151 (3)
N2B—H21B⋯O2Wiii	0.88 (5)	2.18 (5)	3.026 (5)	163 (4)
N2B—H22B⋯O3	0.93 (4)	2.10 (4)	3.002 (4)	165 (3)
N3B—H31B⋯O2Wiv	0.80 (3)	2.15 (3)	2.935 (5)	169 (4)
O1W—H11W⋯O3	0.95 (3)	1.81 (3)	2.737 (3)	167 (4)
O1W—H12W⋯O2v	0.88 (3)	1.85 (4)	2.715 (4)	168 (4)
O2W—H21W⋯O1i	0.78 (4)	1.93 (4)	2.701 (4)	171 (4)
O2W—H22W⋯O1W	0.78 (4)	2.01 (4)	2.673 (4)	143 (4)

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