Bis(guanidinium) chloranilate.

The asymmetric unit of the title co-crystal, 2CH(6)N(3) (+)·C(6)Cl(2)O(4) (2-), contains one half of a chloranilate anion and one guanidinium cation, which are connected by strong N-H⋯O hydrogen bonds into a two-dimensional network.

Related literature

For organic co-crystals containing 2,5-dihy­droxy-3,6-dichloro-1,4-benzoquinone (chloranilic acid), see: Andersen & Andersen (1975 ▶); Horiuchi et al. (2005 ▶, 2007 ▶); Zaman et al. (1999a ▶,b ▶, 2010 ▶). For inorganic co-ordination polymers containing chloranilic acid, see: Kitagawa et al. (2002 ▶). For guanidine and guanidinium structures, see: Abrahams et al. (2004 ▶, 2005 ▶); Best et al. (2003 ▶); Said et al. (2006 ▶); Smith & Wermuth (2010 ▶, 2011 ▶).

Experimental

Crystal data

2CH6N3 +·C6Cl2O4 2−

M = 327.14

Monoclinic,

a = 19.5224 (14) Å

b = 3.7316 (3) Å

c = 18.4103 (14) Å

β = 116.087 (1)°

V = 1204.56 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.57 mm−1

T = 173 K

0.45 × 0.40 × 0.30 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS, Sheldrick, 1996 ▶) T min = 0.785, T max = 0.849

6965 measured reflections

1674 independent reflections

1525 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.078

S = 1.08

1674 reflections

116 parameters

All H-atom parameters refined

Δρmax = 0.47 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036373/vm2118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036373/vm2118Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036373/vm2118Isup3.cml

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

2CH6N3+·C6Cl2O42−	F(000) = 672
Mr = 327.14	Dx = 1.804 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 220 reflections
a = 19.5224 (14) Å	θ = 4.0–29.0°
b = 3.7316 (3) Å	µ = 0.57 mm−1
c = 18.4103 (14) Å	T = 173 K
β = 116.087 (1)°	Block, yellow
V = 1204.56 (16) Å3	0.45 × 0.40 × 0.30 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	1674 independent reflections
Radiation source: fine-focus sealed tube	1525 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 29.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS, Sheldrick, 1996)	h = −27→27
Tmin = 0.785, Tmax = 0.849	k = −5→5
6965 measured reflections	l = −25→25

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.7637P] where P = (Fo2 + 2Fc2)/3
1674 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

	x	y	z	Uiso*/Ueq
Cl1	0.036370 (14)	0.71393 (8)	0.174949 (15)	0.01677 (10)
O2	0.14122 (4)	1.0852 (3)	0.12281 (5)	0.01823 (18)
O3	0.11119 (5)	1.3347 (3)	−0.02492 (5)	0.01949 (19)
N1	0.23429 (6)	1.5093 (3)	−0.07912 (6)	0.0213 (2)
H2	0.2183 (11)	1.461 (6)	−0.0438 (12)	0.037 (5)*
H1	0.2810 (10)	1.436 (5)	−0.0711 (10)	0.028 (4)*
N2	0.11581 (6)	1.7324 (3)	−0.16016 (7)	0.0201 (2)
H4	0.0871 (10)	1.852 (5)	−0.1996 (11)	0.024 (4)*
H3	0.1026 (10)	1.648 (5)	−0.1273 (11)	0.030 (5)*
N3	0.21154 (6)	1.7664 (3)	−0.20145 (7)	0.0211 (2)
H6	0.2549 (12)	1.736 (5)	−0.1912 (12)	0.034 (5)*
H5	0.1782 (11)	1.824 (6)	−0.2505 (13)	0.039 (5)*
C1	0.01581 (6)	0.8726 (3)	0.07862 (6)	0.0143 (2)
C2	0.07504 (6)	1.0395 (3)	0.06811 (6)	0.0140 (2)
C3	0.05815 (6)	1.1811 (3)	−0.01681 (6)	0.0139 (2)
C4	0.18720 (6)	1.6695 (3)	−0.14746 (7)	0.0154 (2)

	U11	U22	U33	U12	U13	U23
Cl1	0.01745 (15)	0.02061 (16)	0.01101 (15)	−0.00081 (9)	0.00514 (11)	0.00188 (9)
O2	0.0120 (3)	0.0267 (4)	0.0132 (4)	−0.0009 (3)	0.0030 (3)	0.0000 (3)
O3	0.0147 (4)	0.0274 (5)	0.0165 (4)	−0.0040 (3)	0.0069 (3)	0.0016 (3)
N1	0.0181 (5)	0.0293 (5)	0.0165 (5)	0.0044 (4)	0.0077 (4)	0.0056 (4)
N2	0.0150 (4)	0.0270 (5)	0.0191 (5)	0.0023 (4)	0.0082 (4)	0.0045 (4)
N3	0.0154 (5)	0.0326 (6)	0.0154 (5)	0.0012 (4)	0.0069 (4)	0.0049 (4)
C1	0.0139 (4)	0.0182 (5)	0.0099 (4)	−0.0003 (4)	0.0043 (4)	0.0014 (4)
C2	0.0133 (4)	0.0161 (5)	0.0119 (4)	0.0007 (4)	0.0051 (4)	−0.0008 (4)
C3	0.0129 (5)	0.0166 (5)	0.0120 (5)	0.0004 (4)	0.0053 (4)	0.0000 (4)
C4	0.0142 (5)	0.0168 (5)	0.0142 (5)	−0.0013 (4)	0.0052 (4)	−0.0015 (4)

Cl1—C1	1.7409 (11)	N2—H3	0.818 (19)
O2—C2	1.2522 (13)	N3—C4	1.3267 (15)
O3—C3	1.2487 (13)	N3—H6	0.79 (2)
N1—C4	1.3297 (15)	N3—H5	0.88 (2)
N1—H2	0.85 (2)	C1—C2	1.3997 (14)
N1—H1	0.901 (17)	C1—C3i	1.4051 (14)
N2—C4	1.3287 (14)	C2—C3	1.5423 (15)
N2—H4	0.827 (18)	C3—C1i	1.4052 (14)
C4—N1—H2	118.9 (13)	C3i—C1—Cl1	118.10 (8)
C4—N1—H1	121.3 (11)	O2—C2—C1	124.91 (10)
H2—N1—H1	119.6 (17)	O2—C2—C3	116.98 (9)
C4—N2—H4	120.2 (12)	C1—C2—C3	118.10 (9)
C4—N2—H3	116.7 (13)	O3—C3—C1i	125.41 (10)
H4—N2—H3	123.1 (17)	O3—C3—C2	117.36 (9)
C4—N3—H6	118.7 (14)	C1i—C3—C2	117.23 (9)
C4—N3—H5	119.3 (13)	N3—C4—N2	120.90 (11)
H6—N3—H5	121.0 (18)	N3—C4—N1	120.33 (11)
C2—C1—C3i	124.66 (10)	N2—C4—N1	118.76 (11)
C2—C1—Cl1	117.24 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O3	0.85 (2)	2.32 (2)	3.0504 (13)	144.4 (16)
N1—H1···O2ii	0.901 (17)	2.117 (17)	2.8978 (13)	144.4 (15)
N1—H1···O3ii	0.901 (17)	2.303 (18)	3.0555 (13)	140.9 (15)
N2—H3···O3	0.818 (19)	2.161 (19)	2.9337 (14)	157.7 (17)
N3—H6···O2ii	0.79 (2)	2.21 (2)	2.9016 (14)	146.3 (18)
N3—H5···O2iii	0.88 (2)	2.14 (2)	2.9586 (13)	154.4 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O3	0.85 (2)	2.32 (2)	3.0504 (13)	144.4 (16)
N1—H1⋯O2i	0.901 (17)	2.117 (17)	2.8978 (13)	144.4 (15)
N1—H1⋯O3i	0.901 (17)	2.303 (18)	3.0555 (13)	140.9 (15)
N2—H3⋯O3	0.818 (19)	2.161 (19)	2.9337 (14)	157.7 (17)
N3—H6⋯O2i	0.79 (2)	2.21 (2)	2.9016 (14)	146.3 (18)
N3—H5⋯O2ii	0.88 (2)	2.14 (2)	2.9586 (13)	154.4 (17)

Symmetry codes: (i) ; (ii) .