Ethane-1,2-diaminium 4,5-dichloro-phthalate.

In the structure of the title compound, C(2)H(10)N(2) (2+)·C(8)H(2)Cl(2)O(4) (2-), the dications and dianions form hydrogen-bonded ribbon substructures which enclose conjoint cyclic R(2) (1)(7), R(1) (2)(7) and R(4) (2)(8) associations and extend down the c-axis direction. These ribbons inter-associate down b, giving a two-dimensional sheet structure. In the dianions, one of the carboxyl-ate groups is essentially coplanar with the benzene ring, while the other is normal to it [C-C-C-O torsion angles = 177.67 (12) and 81.94 (17)°, respectively].

Related literature

For structures of 4,5-dichloro­phthalates, see: Mattes & Dorau (1986 ▶); Bozkurt et al. (2006 ▶); Smith & Wermuth (2010a ▶,b ▶); Smith et al. (2009 ▶). For the structure of a dianionic 4,5-dichloro­phthalate, see: Büyükgüngör & Odabaşoğlu (2007 ▶). For ring associations, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C2H10N2 2+·C8H2Cl2O4 2−

M = 295.12

Monoclinic,

a = 12.892 (1) Å

b = 8.3881 (5) Å

c = 11.8873 (8) Å

β = 104.761 (7)°

V = 1243.06 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.53 mm−1

T = 200 K

0.35 × 0.30 × 0.28 mm

Data collection

Oxford Diffraction Gemini-S CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.980

15108 measured reflections

2442 independent reflections

2174 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.071

S = 1.09

2442 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.24 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/S1600536809054427/pv2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054427/pv2246Isup2.hkl

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

C2H10N22+·C8H2Cl2O42−	F(000) = 608
Mr = 295.12	Dx = 1.577 Mg m−3
Monoclinic, P21/c	Melting point: 529 K
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.892 (1) Å	Cell parameters from 7149 reflections
b = 8.3881 (5) Å	θ = 3.2–28.8°
c = 11.8873 (8) Å	µ = 0.53 mm−1
β = 104.761 (7)°	T = 200 K
V = 1243.06 (15) Å3	Block, colourless
Z = 4	0.35 × 0.30 × 0.28 mm

Oxford Diffraction Gemini-S CCD detector diffractometer	2442 independent reflections
Radiation source: Enhance (Mo) X-ray source	2174 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.955, Tmax = 0.980	k = −10→10
15108 measured reflections	l = −14→14

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) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.2917P] where P = (Fo2 + 2Fc2)/3
2442 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.24 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
Cl4	1.04287 (3)	0.27191 (5)	0.51216 (3)	0.0296 (1)
Cl5	1.08544 (3)	0.02709 (6)	0.72577 (4)	0.0387 (2)
O11	0.70606 (8)	−0.03906 (13)	0.79920 (9)	0.0278 (3)
O12	0.59071 (7)	0.12464 (13)	0.68133 (9)	0.0241 (3)
O21	0.58818 (8)	0.28845 (12)	0.44570 (8)	0.0219 (3)
O22	0.63839 (8)	0.45072 (12)	0.59914 (8)	0.0212 (3)
C1	0.77314 (10)	0.12670 (16)	0.67229 (11)	0.0161 (4)
C2	0.75625 (11)	0.24125 (16)	0.58269 (11)	0.0157 (3)
C3	0.83974 (11)	0.28193 (16)	0.53312 (12)	0.0179 (4)
C4	0.94056 (11)	0.21453 (17)	0.57457 (12)	0.0199 (4)
C5	0.95892 (11)	0.10573 (18)	0.66647 (13)	0.0218 (4)
C6	0.87486 (11)	0.06009 (17)	0.71298 (12)	0.0209 (4)
C11	0.68289 (10)	0.06677 (16)	0.72250 (11)	0.0164 (4)
C21	0.65154 (11)	0.33073 (16)	0.53918 (11)	0.0160 (4)
N1A	0.60404 (10)	1.02002 (15)	0.31902 (11)	0.0207 (4)
N2A	0.58594 (10)	0.68181 (14)	0.42855 (11)	0.0180 (3)
C1A	0.69095 (11)	0.91156 (17)	0.38430 (13)	0.0209 (4)
C2A	0.65833 (11)	0.81624 (17)	0.47846 (12)	0.0212 (4)
H3	0.82780	0.35450	0.47200	0.0220*
H6	0.88660	−0.01580	0.77190	0.0250*
H11A	0.6007 (14)	1.117 (2)	0.3654 (15)	0.034 (5)*
H12A	0.6168 (15)	1.044 (2)	0.2495 (18)	0.040 (5)*
H13A	0.5379 (16)	0.975 (2)	0.3039 (16)	0.033 (5)*
H14A	0.75380	0.97470	0.41970	0.0250*
H15A	0.71040	0.83840	0.32990	0.0250*
H21A	0.5195 (15)	0.718 (2)	0.3925 (15)	0.029 (5)*
H22A	0.6153 (15)	0.623 (2)	0.3789 (16)	0.036 (5)*
H23A	0.5786 (15)	0.610 (2)	0.4847 (17)	0.038 (5)*
H24A	0.72210	0.77460	0.53250	0.0250*
H25A	0.62220	0.88600	0.52140	0.0250*

	U11	U22	U33	U12	U13	U23
Cl4	0.0202 (2)	0.0375 (2)	0.0362 (2)	−0.0003 (2)	0.0163 (2)	0.0087 (2)
Cl5	0.0177 (2)	0.0531 (3)	0.0476 (3)	0.0126 (2)	0.0126 (2)	0.0243 (2)
O11	0.0252 (5)	0.0276 (6)	0.0354 (6)	0.0057 (4)	0.0163 (5)	0.0159 (5)
O12	0.0151 (5)	0.0308 (6)	0.0275 (5)	0.0017 (4)	0.0073 (4)	0.0096 (4)
O21	0.0203 (5)	0.0256 (6)	0.0190 (5)	0.0050 (4)	0.0038 (4)	−0.0004 (4)
O22	0.0263 (5)	0.0179 (5)	0.0222 (5)	0.0040 (4)	0.0113 (4)	0.0004 (4)
C1	0.0164 (6)	0.0151 (6)	0.0183 (7)	−0.0008 (5)	0.0070 (5)	−0.0009 (5)
C2	0.0169 (6)	0.0146 (6)	0.0162 (6)	−0.0008 (5)	0.0054 (5)	−0.0021 (5)
C3	0.0199 (7)	0.0177 (7)	0.0173 (7)	−0.0013 (5)	0.0067 (5)	0.0017 (5)
C4	0.0178 (7)	0.0212 (7)	0.0235 (7)	−0.0028 (5)	0.0106 (6)	−0.0009 (6)
C5	0.0151 (7)	0.0243 (8)	0.0267 (7)	0.0040 (6)	0.0067 (6)	0.0035 (6)
C6	0.0202 (7)	0.0211 (7)	0.0220 (7)	0.0021 (6)	0.0067 (6)	0.0066 (6)
C11	0.0178 (7)	0.0149 (6)	0.0180 (7)	−0.0013 (5)	0.0073 (5)	−0.0012 (5)
C21	0.0180 (7)	0.0156 (7)	0.0172 (7)	0.0008 (5)	0.0098 (5)	0.0040 (5)
N1A	0.0227 (7)	0.0195 (6)	0.0224 (6)	−0.0010 (5)	0.0105 (5)	0.0022 (5)
N2A	0.0183 (6)	0.0159 (6)	0.0220 (6)	0.0010 (5)	0.0092 (5)	0.0003 (5)
C1A	0.0181 (7)	0.0183 (7)	0.0283 (7)	−0.0013 (5)	0.0095 (6)	−0.0008 (6)
C2A	0.0220 (7)	0.0207 (7)	0.0202 (7)	−0.0012 (6)	0.0041 (6)	−0.0020 (6)

Cl4—C4	1.7379 (15)	C1—C11	1.5220 (19)
Cl5—C5	1.7340 (15)	C1—C6	1.394 (2)
O11—C11	1.2529 (17)	C2—C21	1.516 (2)
O12—C11	1.2614 (16)	C2—C3	1.395 (2)
O21—C21	1.2511 (16)	C3—C4	1.388 (2)
O22—C21	1.2694 (17)	C4—C5	1.397 (2)
N1A—C1A	1.497 (2)	C5—C6	1.390 (2)
N2A—C2A	1.4874 (19)	C3—H3	0.9300
N1A—H13A	0.91 (2)	C6—H6	0.9300
N1A—H12A	0.91 (2)	C1A—C2A	1.520 (2)
N1A—H11A	0.990 (17)	C1A—H14A	0.9700
N2A—H22A	0.921 (18)	C1A—H15A	0.9700
N2A—H21A	0.907 (19)	C2A—H24A	0.9700
N2A—H23A	0.922 (18)	C2A—H25A	0.9700
C1—C2	1.4096 (18)
H12A—N1A—H13A	107.0 (17)	C4—C5—C6	119.81 (13)
H11A—N1A—H13A	106.3 (16)	C1—C6—C5	120.77 (13)
C1A—N1A—H12A	108.8 (12)	O11—C11—C1	117.07 (12)
C1A—N1A—H13A	113.0 (11)	O12—C11—C1	117.36 (11)
C1A—N1A—H11A	110.1 (10)	O11—C11—O12	125.55 (13)
H11A—N1A—H12A	111.7 (15)	O21—C21—O22	124.97 (13)
C2A—N2A—H22A	110.1 (12)	O21—C21—C2	119.07 (12)
C2A—N2A—H23A	112.1 (12)	O22—C21—C2	115.84 (11)
C2A—N2A—H21A	110.8 (11)	C2—C3—H3	120.00
H21A—N2A—H23A	107.6 (17)	C4—C3—H3	120.00
H22A—N2A—H23A	104.4 (16)	C1—C6—H6	120.00
H21A—N2A—H22A	111.7 (16)	C5—C6—H6	120.00
C2—C1—C6	119.08 (13)	N1A—C1A—C2A	112.98 (12)
C2—C1—C11	122.35 (12)	N2A—C2A—C1A	111.62 (11)
C6—C1—C11	118.50 (12)	N1A—C1A—H14A	109.00
C3—C2—C12	116.79 (12)	N1A—C1A—H15A	109.00
C1—C2—C3	119.92 (13)	C2A—C1A—H14A	109.00
C1—C2—C12	123.24 (12)	C2A—C1A—H15A	109.00
C2—C3—C4	120.28 (13)	H14A—C1A—H15A	108.00
C3—C4—C5	120.05 (13)	N2A—C2A—H24A	109.00
Cl4—C4—C5	121.27 (11)	N2A—C2A—H25A	109.00
Cl4—C4—C3	118.67 (11)	C1A—C2A—H24A	109.00
Cl5—C5—C4	121.40 (11)	C1A—C2A—H25A	109.00
Cl5—C5—C6	118.78 (11)	H24A—C2A—H25A	108.00
C6—C1—C2—C3	2.4 (2)	C1—C2—C21—O22	81.94 (17)
C6—C1—C2—C12	−174.79 (12)	C3—C2—C21—O21	80.75 (17)
C11—C1—C2—C3	−174.55 (12)	C3—C2—C21—O22	−95.33 (15)
C11—C1—C2—C12	8.3 (2)	C2—C3—C4—Cl4	−178.67 (11)
C2—C1—C6—C5	0.2 (2)	C2—C3—C4—C5	−0.2 (2)
C11—C1—C6—C5	177.24 (13)	Cl4—C4—C5—Cl5	1.97 (18)
C2—C1—C11—O11	177.67 (12)	Cl4—C4—C5—C6	−178.80 (11)
C2—C1—C11—O12	−0.51 (19)	C3—C4—C5—Cl5	−176.52 (11)
C6—C1—C11—O11	0.70 (18)	C3—C4—C5—C6	2.7 (2)
C6—C1—C11—O12	−177.48 (12)	Cl5—C5—C6—C1	176.53 (11)
C1—C2—C3—C4	−2.4 (2)	C4—C5—C6—C1	−2.7 (2)
C12—C2—C3—C4	174.95 (12)	N1A—C1A—C2A—N2A	76.45 (15)
C1—C2—C21—O21	−101.99 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O21i	0.990 (17)	1.756 (17)	2.7452 (16)	177.3 (18)
N1A—H12A···O22ii	0.91 (2)	1.88 (2)	2.7709 (16)	168.3 (16)
N1A—H13A···O12iii	0.91 (2)	1.90 (2)	2.7876 (17)	163.8 (17)
N2A—H21A···O12iii	0.907 (19)	1.974 (18)	2.8306 (16)	157.0 (16)
N2A—H21A···O22iii	0.907 (19)	2.502 (19)	3.0370 (17)	118.2 (13)
N2A—H22A···O11iv	0.921 (18)	1.824 (19)	2.7221 (17)	164.2 (17)
N2A—H23A···O22	0.922 (18)	1.922 (18)	2.7619 (16)	150.5 (18)
C6—H6···O11	0.93	2.44	2.7594 (18)	100
C1A—H15A···O11iv	0.97	2.54	3.3052 (18)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O21i	0.990 (17)	1.756 (17)	2.7452 (16)	177.3 (18)
N1A—H12A⋯O22ii	0.91 (2)	1.88 (2)	2.7709 (16)	168.3 (16)
N1A—H13A⋯O12iii	0.91 (2)	1.90 (2)	2.7876 (17)	163.8 (17)
N2A—H21A⋯O12iii	0.907 (19)	1.974 (18)	2.8306 (16)	157.0 (16)
N2A—H21A⋯O22iii	0.907 (19)	2.502 (19)	3.0370 (17)	118.2 (13)
N2A—H22A⋯O11iv	0.921 (18)	1.824 (19)	2.7221 (17)	164.2 (17)
N2A—H23A⋯O22	0.922 (18)	1.922 (18)	2.7619 (16)	150.5 (18)

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