Isopropyl-aminium 2-carb-oxy-4,5-di-chloro-benzoate.

In the structure of the 1:1 proton-transfer compound of isopropyl-amine with 4,5-dichloro-phthalic acid, C(3)H(10)N(+)·C(8)H(3)Cl(2)O(4) (-), the three cation H-atom donors associate with three separate carboxyl O-atom anion acceptors, giving conjoint cyclic R(4) (4)(12), R(4) (4)(16) hydrogen-bonding cation-anion inter-actions in a one-dimensional ribbon structure. In the anions, the carboxyl groups lie slightly out of the plane of the benzene ring [maximum deviations = 0.439 (1) for a carboxylic acid O atom and 0.433 (1) Å for a carboxyl-ate O atom]. However, the syn-related proton of the carboxylic acid group forms the common short intra-molecular O-H⋯O(carbox-yl) hydrogen bond.

Related literature

For the structures of other hydrogen 4,5-dichloro­phthalate salts, see: Mattes & Dorau (1986 ▶); Mallinson et al. (2003 ▶); Bozkurt et al. (2006 ▶); Odabaşoğlu & Büyükgüngör (2007 ▶); Smith et al. (2007 ▶, 2008a ▶,b ▶, 2009a ▶,b ▶,c ▶); Smith & Wermuth (2010 ▶). For graph-set analysis see: Etter et al. (1990 ▶).

Experimental

Crystal data

C3H10N+·C8H3Cl2O4 −

M = 294.12

Monoclinic,

a = 5.8362 (7) Å

b = 21.040 (2) Å

c = 10.3641 (13) Å

β = 95.064 (12)°

V = 1267.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 200 K

0.40 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.982

8508 measured reflections

2484 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.11

2484 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 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/S1600536809052672/sj2696sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052672/sj2696Isup2.hkl

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

C3H10N+·C8H3Cl2O4−	F(000) = 608
Mr = 294.12	Dx = 1.541 Mg m−3
Monoclinic, P21/n	Melting point: 533 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.8362 (7) Å	Cell parameters from 3787 reflections
b = 21.040 (2) Å	θ = 3.5–28.9°
c = 10.3641 (13) Å	µ = 0.52 mm−1
β = 95.064 (12)°	T = 200 K
V = 1267.7 (3) Å3	Prism, colourless
Z = 4	0.40 × 0.20 × 0.18 mm

Oxford Diffraction Gemini-S CCD detector diffractometer	2484 independent reflections
Radiation source: Enhance (Mo) X-ray source	2103 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 26.0°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.942, Tmax = 0.982	k = −25→25
8508 measured reflections	l = −11→12

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0418P)2] where P = (Fo2 + 2Fc2)/3
2484 reflections	(Δ/σ)max = 0.001
179 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 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	−0.02700 (6)	0.21328 (2)	0.79371 (4)	0.0321 (1)
Cl5	−0.07644 (7)	0.22223 (2)	0.48482 (4)	0.0381 (1)
O11	0.51763 (18)	0.06697 (6)	0.34762 (10)	0.0380 (4)
O12	0.79781 (18)	0.04757 (5)	0.49757 (11)	0.0363 (4)
O21	0.85388 (16)	0.04986 (5)	0.73467 (10)	0.0284 (3)
O22	0.61961 (18)	0.05281 (5)	0.89173 (10)	0.0319 (3)
C1	0.4642 (2)	0.10656 (6)	0.55707 (13)	0.0208 (4)
C2	0.4887 (2)	0.10301 (6)	0.69407 (13)	0.0197 (4)
C3	0.3362 (2)	0.13730 (6)	0.76294 (14)	0.0214 (4)
C4	0.1622 (2)	0.17415 (6)	0.70180 (14)	0.0230 (4)
C5	0.1406 (2)	0.17807 (6)	0.56719 (14)	0.0247 (4)
C6	0.2902 (2)	0.14478 (6)	0.49726 (14)	0.0241 (4)
C11	0.5991 (2)	0.07119 (6)	0.46084 (14)	0.0250 (4)
C21	0.6660 (2)	0.06527 (6)	0.78049 (14)	0.0225 (4)
N1A	0.8171 (2)	0.04013 (6)	0.15582 (13)	0.0231 (4)
C1A	0.9564 (2)	0.10018 (7)	0.17227 (15)	0.0271 (4)
C2A	0.7999 (3)	0.15688 (8)	0.14539 (19)	0.0420 (6)
C3A	1.1460 (3)	0.09810 (8)	0.08332 (17)	0.0350 (5)
H3	0.35150	0.13540	0.85290	0.0260*
H6	0.27510	0.14780	0.40740	0.0290*
H12	0.821 (4)	0.0490 (11)	0.594 (3)	0.087 (8)*
H1A	1.02480	0.10260	0.26190	0.0330*
H11A	0.694 (3)	0.0418 (8)	0.2138 (18)	0.040 (5)*
H12A	0.907 (3)	0.0072 (9)	0.1720 (17)	0.036 (5)*
H13A	0.751 (3)	0.0384 (8)	0.072 (2)	0.037 (5)*
H21A	0.68170	0.15660	0.20420	0.0500*
H22A	0.73080	0.15470	0.05790	0.0500*
H23A	0.88790	0.19530	0.15700	0.0500*
H31A	1.24140	0.06160	0.10360	0.0420*
H32A	1.23720	0.13600	0.09430	0.0420*
H33A	1.08070	0.09530	−0.00480	0.0420*

	U11	U22	U33	U12	U13	U23
Cl4	0.0289 (2)	0.0304 (2)	0.0377 (2)	0.0045 (1)	0.0069 (2)	−0.0040 (2)
Cl5	0.0363 (2)	0.0352 (2)	0.0399 (3)	0.0086 (2)	−0.0133 (2)	0.0045 (2)
O11	0.0356 (6)	0.0582 (7)	0.0205 (6)	−0.0017 (5)	0.0050 (5)	−0.0080 (5)
O12	0.0341 (6)	0.0470 (6)	0.0286 (7)	0.0119 (5)	0.0069 (5)	0.0007 (5)
O21	0.0221 (5)	0.0317 (6)	0.0309 (6)	0.0035 (4)	−0.0002 (4)	0.0045 (4)
O22	0.0368 (6)	0.0395 (6)	0.0187 (6)	0.0064 (4)	−0.0014 (4)	0.0048 (4)
C1	0.0216 (7)	0.0217 (7)	0.0189 (7)	−0.0057 (5)	0.0008 (5)	0.0006 (5)
C2	0.0196 (6)	0.0194 (6)	0.0196 (7)	−0.0048 (5)	−0.0010 (5)	0.0012 (5)
C3	0.0248 (7)	0.0226 (7)	0.0168 (7)	−0.0038 (5)	0.0011 (5)	0.0007 (5)
C4	0.0223 (7)	0.0200 (7)	0.0268 (8)	−0.0029 (5)	0.0024 (6)	−0.0014 (5)
C5	0.0249 (7)	0.0208 (7)	0.0268 (8)	−0.0018 (5)	−0.0069 (6)	0.0028 (5)
C6	0.0275 (7)	0.0265 (7)	0.0174 (8)	−0.0055 (5)	−0.0033 (6)	0.0021 (5)
C11	0.0273 (7)	0.0268 (7)	0.0214 (8)	−0.0060 (6)	0.0052 (6)	0.0006 (6)
C21	0.0246 (7)	0.0208 (7)	0.0212 (8)	−0.0029 (5)	−0.0030 (6)	−0.0004 (5)
N1A	0.0237 (6)	0.0269 (6)	0.0183 (7)	0.0018 (5)	−0.0003 (5)	0.0007 (5)
C1A	0.0315 (8)	0.0281 (7)	0.0208 (8)	−0.0026 (6)	−0.0031 (6)	−0.0018 (6)
C2A	0.0512 (10)	0.0287 (8)	0.0474 (11)	0.0071 (7)	0.0111 (8)	−0.0027 (7)
C3A	0.0291 (8)	0.0354 (8)	0.0408 (10)	−0.0019 (6)	0.0041 (7)	0.0071 (7)

Cl4—C4	1.7292 (14)	C2—C3	1.3908 (18)
Cl5—C5	1.7337 (14)	C3—C4	1.3858 (18)
O11—C11	1.2298 (18)	C4—C5	1.392 (2)
O12—C11	1.2880 (16)	C5—C6	1.3747 (18)
O21—C21	1.2747 (16)	C3—H3	0.9300
O22—C21	1.2354 (18)	C6—H6	0.9300
O12—H12	1.00 (3)	C1A—C2A	1.513 (2)
N1A—C1A	1.5039 (19)	C1A—C3A	1.502 (2)
N1A—H11A	0.977 (18)	C1A—H1A	0.9800
N1A—H13A	0.92 (2)	C2A—H21A	0.9600
N1A—H12A	0.876 (19)	C2A—H22A	0.9600
C1—C6	1.3968 (18)	C2A—H23A	0.9600
C1—C11	1.5189 (18)	C3A—H31A	0.9600
C1—C2	1.4164 (19)	C3A—H32A	0.9600
C2—C21	1.5297 (18)	C3A—H33A	0.9600
C11—O12—H12	108.9 (14)	O21—C21—C2	118.27 (12)
H11A—N1A—H12A	111.8 (15)	O22—C21—C2	117.64 (11)
C1A—N1A—H13A	108.5 (11)	C2—C3—H3	119.00
C1A—N1A—H11A	108.6 (10)	C4—C3—H3	119.00
H11A—N1A—H13A	108.2 (16)	C1—C6—H6	119.00
H12A—N1A—H13A	110.1 (16)	C5—C6—H6	119.00
C1A—N1A—H12A	109.5 (12)	C2A—C1A—C3A	112.05 (14)
C6—C1—C11	112.92 (12)	N1A—C1A—C2A	109.27 (11)
C2—C1—C6	118.71 (12)	N1A—C1A—C3A	109.03 (12)
C2—C1—C11	128.32 (11)	N1A—C1A—H1A	109.00
C1—C2—C21	128.14 (11)	C2A—C1A—H1A	109.00
C1—C2—C3	118.33 (12)	C3A—C1A—H1A	109.00
C3—C2—C21	113.53 (12)	C1A—C2A—H21A	110.00
C2—C3—C4	122.13 (13)	C1A—C2A—H22A	109.00
Cl4—C4—C5	121.21 (10)	C1A—C2A—H23A	109.00
C3—C4—C5	119.29 (12)	H21A—C2A—H22A	109.00
Cl4—C4—C3	119.49 (11)	H21A—C2A—H23A	109.00
Cl5—C5—C4	121.52 (10)	H22A—C2A—H23A	110.00
C4—C5—C6	119.51 (12)	C1A—C3A—H31A	109.00
Cl5—C5—C6	118.94 (11)	C1A—C3A—H32A	110.00
C1—C6—C5	122.01 (13)	C1A—C3A—H33A	109.00
O11—C11—O12	121.09 (13)	H31A—C3A—H32A	109.00
O11—C11—C1	118.87 (11)	H31A—C3A—H33A	109.00
O12—C11—C1	120.03 (12)	H32A—C3A—H33A	109.00
O21—C21—O22	124.07 (12)
C6—C1—C2—C3	0.72 (18)	C1—C2—C21—O21	22.83 (19)
C6—C1—C2—C21	−179.34 (12)	C1—C2—C21—O22	−158.69 (13)
C11—C1—C2—C3	−176.37 (12)	C3—C2—C21—O21	−157.23 (12)
C11—C1—C2—C21	3.6 (2)	C3—C2—C21—O22	21.26 (17)
C2—C1—C6—C5	−1.04 (19)	C2—C3—C4—Cl4	177.78 (10)
C11—C1—C6—C5	176.47 (11)	C2—C3—C4—C5	−1.10 (19)
C2—C1—C11—O11	161.01 (13)	Cl4—C4—C5—Cl5	−0.02 (16)
C2—C1—C11—O12	−20.7 (2)	Cl4—C4—C5—C6	−178.09 (10)
C6—C1—C11—O11	−16.22 (17)	C3—C4—C5—Cl5	178.86 (10)
C6—C1—C11—O12	162.10 (12)	C3—C4—C5—C6	0.78 (18)
C1—C2—C3—C4	0.34 (19)	Cl5—C5—C6—C1	−177.84 (10)
C21—C2—C3—C4	−179.61 (11)	C4—C5—C6—C1	0.29 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O21	1.00 (3)	1.45 (3)	2.4507 (16)	179 (3)
N1A—H11A···O11	0.977 (18)	1.875 (18)	2.8175 (17)	161.2 (15)
N1A—H12A···O21i	0.876 (19)	2.021 (18)	2.8593 (16)	159.6 (16)
N1A—H13A···O22ii	0.92 (2)	1.98 (2)	2.8869 (17)	168.8 (15)
C3—H3···O22	0.93	2.35	2.6996 (17)	102
C6—H6···O11	0.93	2.33	2.6853 (18)	102
C3A—H31A···O22i	0.96	2.54	3.458 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯O21	1.00 (3)	1.45 (3)	2.4507 (16)	179 (3)
N1A—H11A⋯O11	0.977 (18)	1.875 (18)	2.8175 (17)	161.2 (15)
N1A—H12A⋯O21i	0.876 (19)	2.021 (18)	2.8593 (16)	159.6 (16)
N1A—H13A⋯O22ii	0.92 (2)	1.98 (2)	2.8869 (17)	168.8 (15)

Symmetry codes: (i) ; (ii) .