Bis(tri-ethyl-ammonium) chloranilate.

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: bis-(tri-ethyl-ammonium) 2,5-di-chloro-3,6-dioxo-cyclo-hexa-1,4-diene-1,4-diolate], 2C6H16N(+)·C6Cl2O4 (2-), the chloranilate anion lies on an inversion center. The tri-ethyl-ammonium cations are linked on both sides of the anion via bifurcated N-H⋯(O,O) and weak C-H⋯O hydrogen bonds to give a centrosymmetric 2:1 aggregate. The 2:1 aggregates are further linked by C-H⋯O hydrogen bonds into a zigzag chain running along [01-1].

Related literature

For related structures, see: Dayananda et al. (2012 ▶); Gotoh et al. (2009 ▶, 2010 ▶); Yang (2007 ▶).

Experimental

Crystal data

2C6H16N+·C6Cl2O4 2−

M = 411.37

Triclinic,

a = 7.7347 (5) Å

b = 8.5151 (8) Å

c = 9.3913 (7) Å

α = 64.388 (4)°

β = 68.435 (3)°

γ = 79.060 (5)°

V = 518.36 (7) Å3

Z = 1

Mo Kα radiation

μ = 0.34 mm−1

T = 180 K

0.65 × 0.31 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.858, T max = 0.932

10264 measured reflections

3012 independent reflections

2561 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.121

S = 1.06

3012 reflections

125 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.26 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536813021405/lh5635sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021405/lh5635Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021405/lh5635Isup3.cml

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

2C6H16N+·C6Cl2O42−	Z = 1
Mr = 411.37	F(000) = 220.00
Triclinic, P1	Dx = 1.318 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.7347 (5) Å	Cell parameters from 8559 reflections
b = 8.5151 (8) Å	θ = 3.1–30.1°
c = 9.3913 (7) Å	µ = 0.34 mm−1
α = 64.388 (4)°	T = 180 K
β = 68.435 (3)°	Block, brown
γ = 79.060 (5)°	0.65 × 0.31 × 0.21 mm
V = 518.36 (7) Å3

Rigaku R-AXIS RAPID II diffractometer	2561 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.078
ω scans	θmax = 30.0°, θmin = 3.1°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −10→10
Tmin = 0.858, Tmax = 0.932	k = −11→11
10264 measured reflections	l = −13→13
3012 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0654P)2] where P = (Fo2 + 2Fc2)/3
3012 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.26 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	0.14870 (4)	0.93266 (4)	0.32667 (3)	0.03021 (13)
O1	0.44257 (12)	0.67475 (10)	0.24001 (11)	0.0322 (2)
O2	0.26077 (12)	1.26690 (10)	0.03171 (10)	0.0326 (2)
N1	0.67048 (13)	0.38363 (13)	0.23709 (12)	0.0242 (2)
C1	0.46352 (15)	0.82853 (14)	0.13459 (13)	0.0237 (2)
C2	0.34397 (15)	0.96966 (14)	0.14976 (13)	0.0235 (2)
C3	0.36699 (15)	1.13964 (14)	0.02453 (14)	0.0235 (2)
C4	0.54491 (18)	0.26759 (16)	0.40054 (15)	0.0313 (3)
H4A	0.5321	0.3103	0.4868	0.038*
H4B	0.6024	0.1485	0.4333	0.038*
C5	0.35317 (19)	0.25958 (19)	0.39536 (18)	0.0396 (3)
H5A	0.2712	0.1966	0.5086	0.059*
H5B	0.3625	0.1988	0.3247	0.059*
H5C	0.3018	0.3782	0.3494	0.059*
C6	0.69491 (17)	0.33514 (16)	0.09491 (15)	0.0297 (3)
H6A	0.7649	0.4268	−0.0105	0.036*
H6B	0.5708	0.3319	0.0884	0.036*
C7	0.7960 (2)	0.1614 (2)	0.1098 (2)	0.0435 (4)
H7A	0.8200	0.1442	0.0075	0.065*
H7B	0.7191	0.0679	0.2051	0.065*
H7C	0.9143	0.1595	0.1265	0.065*
C8	0.85542 (16)	0.39642 (17)	0.24970 (15)	0.0295 (3)
H8A	0.9018	0.2780	0.3091	0.035*
H8B	0.9459	0.4451	0.1360	0.035*
C9	0.84408 (19)	0.50912 (17)	0.34006 (17)	0.0342 (3)
H9A	0.9693	0.5226	0.3355	0.051*
H9B	0.7662	0.4542	0.4567	0.051*
H9C	0.7894	0.6239	0.2868	0.051*
H1	0.618 (2)	0.487 (2)	0.209 (2)	0.034 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02658 (19)	0.03015 (19)	0.02264 (18)	0.00392 (12)	−0.00412 (13)	−0.00561 (13)
O1	0.0340 (5)	0.0216 (4)	0.0265 (4)	0.0031 (3)	−0.0046 (4)	−0.0025 (3)
O2	0.0326 (5)	0.0247 (4)	0.0290 (5)	0.0080 (3)	−0.0055 (4)	−0.0078 (4)
N1	0.0252 (5)	0.0216 (5)	0.0220 (4)	0.0037 (3)	−0.0086 (4)	−0.0062 (4)
C1	0.0254 (5)	0.0227 (5)	0.0216 (5)	0.0019 (4)	−0.0092 (4)	−0.0072 (4)
C2	0.0235 (5)	0.0233 (5)	0.0196 (5)	0.0023 (4)	−0.0067 (4)	−0.0063 (4)
C3	0.0246 (5)	0.0219 (5)	0.0230 (5)	0.0030 (4)	−0.0094 (4)	−0.0082 (4)
C4	0.0327 (6)	0.0267 (6)	0.0254 (6)	0.0000 (4)	−0.0062 (5)	−0.0054 (5)
C5	0.0352 (7)	0.0392 (7)	0.0414 (7)	−0.0081 (5)	−0.0058 (6)	−0.0159 (6)
C6	0.0326 (6)	0.0317 (6)	0.0267 (6)	0.0028 (5)	−0.0139 (5)	−0.0114 (5)
C7	0.0479 (8)	0.0454 (8)	0.0561 (9)	0.0166 (6)	−0.0296 (7)	−0.0339 (7)
C8	0.0262 (6)	0.0355 (6)	0.0272 (6)	0.0026 (4)	−0.0106 (5)	−0.0128 (5)
C9	0.0355 (7)	0.0370 (7)	0.0330 (6)	−0.0009 (5)	−0.0120 (5)	−0.0159 (6)

Cl1—C2	1.7390 (11)	C5—H5B	0.9800
O1—C1	1.2502 (13)	C5—H5C	0.9800
O2—C3	1.2403 (13)	C6—C7	1.5103 (18)
N1—C4	1.4943 (15)	C6—H6A	0.9900
N1—C6	1.5002 (15)	C6—H6B	0.9900
N1—C8	1.5056 (15)	C7—H7A	0.9800
N1—H1	0.867 (18)	C7—H7B	0.9800
C1—C2	1.3960 (15)	C7—H7C	0.9800
C1—C3i	1.5394 (16)	C8—C9	1.5054 (17)
C2—C3	1.4079 (15)	C8—H8A	0.9900
C3—C1i	1.5394 (16)	C8—H8B	0.9900
C4—C5	1.517 (2)	C9—H9A	0.9800
C4—H4A	0.9900	C9—H9B	0.9800
C4—H4B	0.9900	C9—H9C	0.9800
C5—H5A	0.9800
C4—N1—C6	113.81 (10)	H5B—C5—H5C	109.5
C4—N1—C8	111.29 (9)	N1—C6—C7	113.74 (10)
C6—N1—C8	111.25 (9)	N1—C6—H6A	108.8
C4—N1—H1	108.1 (10)	C7—C6—H6A	108.8
C6—N1—H1	103.7 (10)	N1—C6—H6B	108.8
C8—N1—H1	108.2 (10)	C7—C6—H6B	108.8
O1—C1—C2	125.01 (10)	H6A—C6—H6B	107.7
O1—C1—C3i	116.31 (9)	C6—C7—H7A	109.5
C2—C1—C3i	118.67 (9)	C6—C7—H7B	109.5
C1—C2—C3	123.37 (10)	H7A—C7—H7B	109.5
C1—C2—Cl1	118.69 (8)	C6—C7—H7C	109.5
C3—C2—Cl1	117.83 (8)	H7A—C7—H7C	109.5
O2—C3—C2	125.12 (10)	H7B—C7—H7C	109.5
O2—C3—C1i	116.95 (9)	C9—C8—N1	112.57 (10)
C2—C3—C1i	117.93 (9)	C9—C8—H8A	109.1
N1—C4—C5	112.84 (11)	N1—C8—H8A	109.1
N1—C4—H4A	109.0	C9—C8—H8B	109.1
C5—C4—H4A	109.0	N1—C8—H8B	109.1
N1—C4—H4B	109.0	H8A—C8—H8B	107.8
C5—C4—H4B	109.0	C8—C9—H9A	109.5
H4A—C4—H4B	107.8	C8—C9—H9B	109.5
C4—C5—H5A	109.5	H9A—C9—H9B	109.5
C4—C5—H5B	109.5	C8—C9—H9C	109.5
H5A—C5—H5B	109.5	H9A—C9—H9C	109.5
C4—C5—H5C	109.5	H9B—C9—H9C	109.5
H5A—C5—H5C	109.5
O1—C1—C2—C3	−176.68 (11)	Cl1—C2—C3—C1i	−178.12 (8)
C3i—C1—C2—C3	1.97 (19)	C6—N1—C4—C5	−56.62 (13)
O1—C1—C2—Cl1	−0.54 (17)	C8—N1—C4—C5	176.71 (10)
C3i—C1—C2—Cl1	178.11 (8)	C4—N1—C6—C7	−66.29 (14)
C1—C2—C3—O2	177.84 (11)	C8—N1—C6—C7	60.39 (14)
Cl1—C2—C3—O2	1.67 (17)	C4—N1—C8—C9	−74.58 (13)
C1—C2—C3—C1i	−1.95 (18)	C6—N1—C8—C9	157.36 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.867 (18)	1.942 (18)	2.7601 (15)	156.9 (15)
N1—H1···O2i	0.867 (18)	2.339 (17)	2.9377 (14)	126.4 (14)
C5—H5C···O1	0.98	2.57	3.2911 (19)	131
C9—H9B···O1ii	0.98	2.55	3.5315 (17)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.867 (18)	1.942 (18)	2.7601 (15)	156.9 (15)
N1—H1⋯O2i	0.867 (18)	2.339 (17)	2.9377 (14)	126.4 (14)
C5—H5C⋯O1	0.98	2.57	3.2911 (19)	131
C9—H9B⋯O1ii	0.98	2.55	3.5315 (17)	177

Symmetry codes: (i) ; (ii) .