tert-Butyl-aminium 2-carb-oxy-4,5-dichloro-benzoate.

In the structure of the title anhydrous salt, C(4)H(12)N(+)·C(8)H(3)Cl(2)O(4) (-), the 4,5-dichloro-phthalate monoanions have the common 'planar' conformation with the carboxyl groups close to coplanar with the benzene ring and with a short intra-molecular carb-oxy-lic acid O-H⋯O hydrogen bond. In the crystal, a two-dimensional sheet structure is formed through aminium N-H⋯O(carbox-yl) hydrogen-bonding associations.

Related literature

For structures of 1:1 salts of 4,5-dichloro­phthalic acid with acyclic aliphatic amines, see: Mattes & Dorau (1986 ▶); Bozkurt et al. (2006 ▶); Smith & Wermuth (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C4H12N+·C8H3Cl2O4 −

M = 308.15

Monoclinic,

a = 6.1778 (2) Å

b = 12.7158 (4) Å

c = 17.7125 (7) Å

β = 96.784 (4)°

V = 1381.68 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 200 K

0.45 × 0.26 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.977, T max = 0.990

8677 measured reflections

2719 independent reflections

2307 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 0.90

2719 reflections

188 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811034131/bt5620sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034131/bt5620Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034131/bt5620Isup3.cml

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

C4H12N+·C8H3Cl2O4−	F(000) = 640
Mr = 308.15	Dx = 1.481 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4272 reflections
a = 6.1778 (2) Å	θ = 3.3–28.8°
b = 12.7158 (4) Å	µ = 0.48 mm−1
c = 17.7125 (7) Å	T = 200 K
β = 96.784 (4)°	Plate, colourless
V = 1381.68 (8) Å3	0.45 × 0.26 × 0.18 mm
Z = 4

Oxford Diffraction Gemini-S CCD-detector diffractometer	2719 independent reflections
Radiation source: Enhance (Mo) X-ray source	2307 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −15→15
Tmin = 0.977, Tmax = 0.990	l = −21→21
8677 measured 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.4558P] where P = (Fo2 + 2Fc2)/3
2719 reflections	(Δ/σ)max = 0.001
188 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 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
Cl1	0.77566 (7)	−0.08494 (3)	0.92701 (3)	0.0313 (1)
Cl2	0.29591 (7)	−0.09103 (3)	0.84148 (3)	0.0370 (2)
O11	0.8896 (2)	0.29012 (10)	1.01297 (8)	0.0394 (4)
O12	0.6289 (2)	0.40012 (9)	0.97033 (8)	0.0353 (4)
O21	0.2615 (2)	0.39679 (10)	0.90835 (10)	0.0452 (5)
O22	0.0363 (2)	0.28642 (11)	0.84456 (9)	0.0475 (5)
C1	0.5836 (3)	0.21454 (12)	0.93969 (9)	0.0218 (5)
C2	0.3705 (3)	0.21275 (13)	0.90024 (9)	0.0230 (5)
C3	0.2876 (3)	0.11656 (13)	0.87218 (10)	0.0239 (5)
C4	0.4066 (3)	0.02459 (12)	0.87963 (9)	0.0233 (5)
C5	0.6169 (3)	0.02693 (12)	0.91703 (9)	0.0221 (5)
C6	0.7012 (3)	0.12081 (13)	0.94635 (9)	0.0236 (5)
C11	0.7102 (3)	0.30722 (13)	0.97701 (9)	0.0268 (5)
C21	0.2089 (3)	0.30285 (14)	0.88234 (11)	0.0311 (6)
N1A	−0.0938 (3)	0.54459 (13)	0.90362 (9)	0.0257 (5)
C1A	−0.2152 (3)	0.58740 (13)	0.83097 (10)	0.0255 (5)
C2A	−0.0614 (3)	0.66054 (18)	0.79557 (12)	0.0450 (7)
C3A	−0.2819 (3)	0.49408 (16)	0.77986 (11)	0.0380 (6)
C4A	−0.4120 (3)	0.64663 (15)	0.85216 (12)	0.0373 (6)
H3	0.14630	0.11430	0.84740	0.0290*
H6	0.84200	0.12160	0.97160	0.0280*
H21	0.400 (6)	0.399 (3)	0.936 (2)	0.109 (12)*
H11A	0.016 (3)	0.5023 (18)	0.8953 (12)	0.039 (6)*
H12A	−0.036 (4)	0.5995 (18)	0.9325 (13)	0.044 (6)*
H13A	−0.185 (4)	0.5080 (18)	0.9289 (13)	0.042 (6)*
H21A	0.06120	0.62120	0.78220	0.0670*
H22A	−0.01140	0.71450	0.83140	0.0670*
H23A	−0.13660	0.69220	0.75070	0.0670*
H31A	−0.37940	0.44980	0.80390	0.0570*
H32A	−0.15460	0.45460	0.77120	0.0570*
H33A	−0.35380	0.51880	0.73220	0.0570*
H41A	−0.50720	0.59880	0.87410	0.0560*
H42A	−0.48830	0.67810	0.80740	0.0560*
H43A	−0.36510	0.70060	0.88840	0.0560*

	U11	U22	U33	U12	U13	U23
Cl1	0.0293 (2)	0.0232 (2)	0.0394 (3)	0.0066 (2)	−0.0041 (2)	−0.0007 (2)
Cl2	0.0298 (3)	0.0252 (2)	0.0534 (3)	−0.0039 (2)	−0.0061 (2)	−0.0113 (2)
O11	0.0394 (8)	0.0314 (7)	0.0433 (8)	−0.0070 (6)	−0.0116 (6)	−0.0082 (6)
O12	0.0367 (7)	0.0208 (6)	0.0486 (8)	−0.0044 (5)	0.0059 (6)	−0.0061 (5)
O21	0.0321 (8)	0.0228 (7)	0.0798 (11)	0.0057 (6)	0.0025 (8)	−0.0041 (7)
O22	0.0377 (8)	0.0409 (8)	0.0591 (10)	0.0146 (6)	−0.0148 (7)	−0.0028 (7)
C1	0.0250 (8)	0.0205 (8)	0.0198 (8)	−0.0024 (6)	0.0028 (7)	−0.0010 (6)
C2	0.0228 (8)	0.0233 (8)	0.0231 (8)	0.0017 (6)	0.0031 (7)	0.0010 (6)
C3	0.0180 (8)	0.0274 (8)	0.0257 (8)	−0.0004 (7)	0.0004 (7)	−0.0007 (7)
C4	0.0231 (8)	0.0216 (8)	0.0249 (8)	−0.0033 (6)	0.0012 (7)	−0.0026 (7)
C5	0.0223 (8)	0.0213 (8)	0.0225 (8)	0.0018 (6)	0.0018 (6)	0.0016 (6)
C6	0.0204 (8)	0.0265 (8)	0.0228 (8)	−0.0016 (6)	−0.0020 (7)	−0.0007 (7)
C11	0.0311 (9)	0.0247 (9)	0.0251 (9)	−0.0068 (7)	0.0049 (8)	−0.0032 (7)
C21	0.0316 (10)	0.0258 (9)	0.0361 (10)	0.0067 (7)	0.0053 (8)	0.0027 (8)
N1A	0.0236 (8)	0.0251 (8)	0.0268 (8)	0.0001 (7)	−0.0037 (7)	−0.0033 (6)
C1A	0.0245 (9)	0.0262 (9)	0.0246 (9)	0.0016 (7)	−0.0021 (7)	−0.0001 (7)
C2A	0.0437 (12)	0.0542 (13)	0.0374 (11)	−0.0117 (10)	0.0066 (9)	0.0081 (10)
C3A	0.0385 (11)	0.0404 (11)	0.0315 (10)	0.0050 (9)	−0.0108 (8)	−0.0097 (8)
C4A	0.0328 (10)	0.0329 (10)	0.0451 (11)	0.0079 (8)	0.0004 (9)	0.0001 (9)

Cl1—C5	1.7251 (17)	C4—C5	1.387 (3)
Cl2—C4	1.7253 (16)	C5—C6	1.379 (2)
O11—C11	1.231 (2)	C3—H3	0.9300
O12—C11	1.284 (2)	C6—H6	0.9300
O21—C21	1.307 (2)	C1A—C2A	1.517 (3)
O22—C21	1.208 (2)	C1A—C3A	1.520 (3)
O21—H21	0.94 (4)	C1A—C4A	1.515 (3)
N1A—C1A	1.512 (2)	C2A—H21A	0.9600
N1A—H11A	0.89 (2)	C2A—H22A	0.9600
N1A—H13A	0.89 (2)	C2A—H23A	0.9600
N1A—H12A	0.91 (2)	C3A—H31A	0.9600
C1—C11	1.522 (2)	C3A—H32A	0.9600
C1—C6	1.394 (2)	C3A—H33A	0.9600
C1—C2	1.416 (3)	C4A—H41A	0.9600
C2—C3	1.395 (2)	C4A—H42A	0.9600
C2—C21	1.528 (3)	C4A—H43A	0.9600
C3—C4	1.379 (2)
Cl1···Cl2	3.1661 (7)	O11···C21v	3.217 (2)
Cl1···O11i	3.4197 (14)	O11···Cl1i	3.4197 (14)
Cl1···C3ii	3.6461 (18)	O11···N1Avi	2.784 (2)
Cl2···Cl1	3.1661 (7)	O12···C21	3.120 (2)
Cl1···H43Aiii	2.9200	O12···O12vi	3.2387 (17)
Cl1···H6i	2.8300	O12···O21	2.4021 (19)
Cl2···H22Aiv	3.1100	O12···N1Av	2.861 (2)
O11···O22v	3.219 (2)	O21···C11	3.109 (2)
C21—O21—H21	113 (2)	C4—C3—H3	119.00
C1A—N1A—H11A	112.8 (14)	C1—C6—H6	119.00
C1A—N1A—H12A	108.9 (14)	C5—C6—H6	119.00
H11A—N1A—H12A	107 (2)	C3A—C1A—C4A	111.52 (15)
H11A—N1A—H13A	108 (2)	N1A—C1A—C2A	107.49 (15)
C1A—N1A—H13A	109.6 (15)	N1A—C1A—C3A	107.35 (14)
H12A—N1A—H13A	110 (2)	N1A—C1A—C4A	107.46 (15)
C2—C1—C11	128.84 (15)	C2A—C1A—C3A	111.81 (16)
C6—C1—C11	112.93 (15)	C2A—C1A—C4A	110.97 (15)
C2—C1—C6	118.24 (15)	C1A—C2A—H21A	109.00
C1—C2—C21	129.57 (15)	C1A—C2A—H22A	109.00
C1—C2—C3	118.09 (15)	C1A—C2A—H23A	109.00
C3—C2—C21	112.35 (16)	H21A—C2A—H22A	109.00
C2—C3—C4	122.71 (17)	H21A—C2A—H23A	109.00
Cl2—C4—C5	120.72 (12)	H22A—C2A—H23A	109.00
Cl2—C4—C3	120.19 (14)	C1A—C3A—H31A	110.00
C3—C4—C5	119.08 (15)	C1A—C3A—H32A	109.00
Cl1—C5—C4	121.35 (12)	C1A—C3A—H33A	109.00
Cl1—C5—C6	119.36 (14)	H31A—C3A—H32A	109.00
C4—C5—C6	119.28 (15)	H31A—C3A—H33A	109.00
C1—C6—C5	122.58 (17)	H32A—C3A—H33A	109.00
O11—C11—C1	118.25 (15)	C1A—C4A—H41A	109.00
O11—C11—O12	121.94 (16)	C1A—C4A—H42A	109.00
O12—C11—C1	119.82 (15)	C1A—C4A—H43A	109.00
O21—C21—C2	118.87 (16)	H41A—C4A—H42A	110.00
O21—C21—O22	121.30 (17)	H41A—C4A—H43A	109.00
O22—C21—C2	119.83 (16)	H42A—C4A—H43A	109.00
C2—C3—H3	119.00
C6—C1—C2—C3	1.9 (2)	C1—C2—C21—O21	−3.2 (3)
C6—C1—C2—C21	−177.99 (17)	C1—C2—C21—O22	176.59 (18)
C11—C1—C2—C3	−178.68 (16)	C3—C2—C21—O21	176.90 (17)
C11—C1—C2—C21	1.4 (3)	C3—C2—C21—O22	−3.3 (2)
C2—C1—C6—C5	−0.9 (2)	C2—C3—C4—Cl2	−178.43 (14)
C11—C1—C6—C5	179.57 (15)	C2—C3—C4—C5	0.5 (3)
C2—C1—C11—O11	175.26 (17)	Cl2—C4—C5—Cl1	−0.1 (2)
C2—C1—C11—O12	−4.8 (3)	Cl2—C4—C5—C6	179.48 (13)
C6—C1—C11—O11	−5.3 (2)	C3—C4—C5—Cl1	−179.02 (13)
C6—C1—C11—O12	174.65 (15)	C3—C4—C5—C6	0.5 (2)
C1—C2—C3—C4	−1.8 (3)	Cl1—C5—C6—C1	179.23 (13)
C21—C2—C3—C4	178.14 (16)	C4—C5—C6—C1	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O21	0.89 (2)	2.02 (2)	2.883 (2)	164 (2)
N1A—H12A···O11vi	0.91 (2)	1.88 (2)	2.784 (2)	174 (2)
N1A—H13A···O12vii	0.89 (2)	1.99 (2)	2.861 (2)	167 (2)
O21—H21···O12	0.94 (4)	1.47 (4)	2.4021 (19)	173 (4)
C3—H3···O22	0.93	2.29	2.671 (2)	104
C6—H6···O11	0.93	2.27	2.657 (2)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O21	0.89 (2)	2.02 (2)	2.883 (2)	164 (2)
N1A—H12A⋯O11i	0.91 (2)	1.88 (2)	2.784 (2)	174 (2)
N1A—H13A⋯O12ii	0.89 (2)	1.99 (2)	2.861 (2)	167 (2)
O21—H21⋯O12	0.94 (4)	1.47 (4)	2.4021 (19)	173 (4)

Symmetry codes: (i) ; (ii) .