rac-cis-Cyclo-hexane-1,2-dicarb-oxy-lic acid-isoquinoline (1/1).

In the crystal structure of the title mol-ecular adduct, C(9)H(7)N·C(8)H(12)O(4), the two species are -linked through a carb-oxy-lic acid-isoquinoline O-H⋯N hydrogen bond. These mol-ecular pairs then inter-associate through the second acid group of the cis-cyclo-hexane-1,2-dicarb-oxy-lic acid molecules, forming a classic centrosymmetric cyclic head-to-head carb-oxy-lic acid-carboxyl O-H⋯O hydrogen-bonding association [graph-set R(2) (2)(8)], giving a zero-dimensional (cluster) structure, consisting of two of each species.

Related literature

For the structure of racemic cis-cyclo­hexane-1,2-dicarb­oxy­lic acid, see: Benedetti et al. (1970 ▶). For the structures of the racemic 1:1 ammonium and 2-amino­pyridinium salts of this acid, see: Smith & Wermuth (2011a ▶,b ▶). For the structure of the 1:1 adduct with 4,4′-bipyridine, see: Bhogala et al. (2005 ▶). For hydrogen bonding in carb­oxy­lic acids and graph-set analysis, see: Leiserowitz (1976 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C9H7N·C8H12O4

M = 301.33

Triclinic,

a = 6.2459 (3) Å

b = 11.4238 (6) Å

c = 11.9970 (6) Å

α = 64.082 (5)°

β = 77.793 (4)°

γ = 82.756 (4)°

V = 751.95 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.40 × 0.28 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.974, T max = 0.990

9094 measured reflections

2952 independent reflections

2463 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 1.02

2952 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 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 (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030613/nk2108sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030613/nk2108Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030613/nk2108Isup3.cml

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

C9H7N·C8H12O4	Z = 2
Mr = 301.33	F(000) = 320
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Melting point = 439–441 K
a = 6.2459 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4238 (6) Å	Cell parameters from 4474 reflections
c = 11.9970 (6) Å	θ = 3.3–28.7°
α = 64.082 (5)°	µ = 0.10 mm−1
β = 77.793 (4)°	T = 200 K
γ = 82.756 (4)°	Block, colourless
V = 751.95 (7) Å3	0.40 × 0.28 × 0.20 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	2952 independent reflections
Radiation source: Enhance (Mo) X-ray source	2463 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
Tmin = 0.974, Tmax = 0.990	l = −14→14
9094 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0354P)2 + 0.20P] where P = (Fo2 + 2Fc2)/3
2952 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 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
O11	0.70832 (16)	1.07685 (11)	0.86864 (10)	0.0405 (4)
O12	0.37261 (16)	1.01881 (10)	0.88359 (9)	0.0371 (3)
O21	0.49576 (18)	0.88369 (10)	0.70388 (12)	0.0476 (4)
O22	0.17799 (18)	0.95466 (11)	0.63667 (11)	0.0468 (4)
C1	0.5909 (2)	1.13098 (13)	0.67706 (12)	0.0272 (4)
C2	0.4067 (2)	1.11424 (13)	0.61893 (12)	0.0272 (4)
C3	0.1978 (2)	1.19528 (13)	0.63551 (13)	0.0298 (4)
C4	0.2466 (2)	1.33837 (14)	0.58905 (14)	0.0338 (4)
C5	0.4233 (2)	1.35310 (13)	0.65186 (13)	0.0314 (4)
C6	0.6329 (2)	1.27692 (13)	0.62795 (13)	0.0309 (4)
C11	0.5440 (2)	1.06979 (12)	0.81900 (13)	0.0271 (4)
C21	0.3661 (2)	0.97179 (14)	0.65964 (13)	0.0308 (4)
N2A	0.1006 (2)	0.70353 (12)	0.71708 (12)	0.0366 (4)
C1A	0.2157 (2)	0.61693 (14)	0.79877 (14)	0.0343 (5)
C3A	−0.0816 (3)	0.66352 (15)	0.69941 (14)	0.0375 (5)
C4A	−0.1451 (2)	0.53805 (15)	0.76063 (14)	0.0357 (5)
C5A	−0.0839 (3)	0.31194 (15)	0.92123 (15)	0.0390 (5)
C6A	0.0362 (3)	0.22778 (16)	1.00839 (16)	0.0434 (5)
C7A	0.2218 (3)	0.26877 (16)	1.02899 (15)	0.0421 (5)
C8A	0.2845 (2)	0.39437 (15)	0.96060 (14)	0.0365 (5)
C9A	0.1621 (2)	0.48468 (14)	0.87014 (13)	0.0304 (4)
C10A	−0.0255 (2)	0.44335 (14)	0.84987 (13)	0.0303 (4)
H1	0.72500	1.08880	0.64990	0.0410*
H2	0.46140	1.14950	0.52810	0.0410*
H11	0.669 (3)	1.037 (2)	0.959 (2)	0.080 (7)*
H22	0.158 (3)	0.862 (2)	0.663 (2)	0.078 (6)*
H31	0.09420	1.18840	0.58900	0.0450*
H32	0.13100	1.16090	0.72380	0.0450*
H41	0.29490	1.37600	0.49850	0.0510*
H42	0.11370	1.38550	0.60730	0.0510*
H51	0.37080	1.32150	0.74180	0.0470*
H52	0.45410	1.44450	0.61900	0.0470*
H61	0.74230	1.28670	0.66960	0.0460*
H62	0.68990	1.31220	0.53830	0.0460*
H1A	0.34010	0.64420	0.81040	0.0410*
H3A	−0.16580	0.72460	0.64320	0.0450*
H4A	−0.26770	0.51450	0.74370	0.0430*
H5A	−0.20530	0.28290	0.90850	0.0470*
H6A	−0.00490	0.14190	1.05510	0.0520*
H7A	0.30170	0.21020	1.08930	0.0510*
H8A	0.40850	0.42070	0.97350	0.0440*

	U11	U22	U33	U12	U13	U23
O11	0.0362 (6)	0.0521 (7)	0.0326 (6)	−0.0141 (5)	−0.0111 (5)	−0.0120 (5)
O12	0.0331 (6)	0.0448 (6)	0.0305 (5)	−0.0113 (5)	−0.0061 (4)	−0.0105 (5)
O21	0.0450 (6)	0.0329 (6)	0.0715 (8)	0.0055 (5)	−0.0211 (6)	−0.0251 (6)
O22	0.0487 (7)	0.0313 (6)	0.0680 (8)	−0.0050 (5)	−0.0269 (6)	−0.0197 (6)
C1	0.0240 (7)	0.0283 (7)	0.0305 (7)	−0.0012 (5)	−0.0032 (5)	−0.0141 (6)
C2	0.0303 (7)	0.0285 (7)	0.0247 (7)	−0.0036 (6)	−0.0036 (5)	−0.0128 (6)
C3	0.0272 (7)	0.0299 (7)	0.0326 (7)	−0.0030 (6)	−0.0061 (6)	−0.0126 (6)
C4	0.0332 (7)	0.0284 (7)	0.0380 (8)	−0.0008 (6)	−0.0084 (6)	−0.0116 (6)
C5	0.0372 (8)	0.0241 (7)	0.0319 (7)	−0.0056 (6)	−0.0045 (6)	−0.0106 (6)
C6	0.0300 (7)	0.0322 (8)	0.0298 (7)	−0.0085 (6)	−0.0029 (6)	−0.0116 (6)
C11	0.0275 (7)	0.0228 (7)	0.0334 (7)	0.0003 (5)	−0.0081 (6)	−0.0131 (6)
C21	0.0345 (7)	0.0326 (8)	0.0300 (7)	−0.0022 (6)	−0.0053 (6)	−0.0174 (6)
N2A	0.0422 (7)	0.0331 (7)	0.0390 (7)	−0.0029 (5)	−0.0073 (6)	−0.0189 (6)
C1A	0.0326 (8)	0.0379 (8)	0.0420 (8)	−0.0036 (6)	−0.0051 (6)	−0.0256 (7)
C3A	0.0438 (9)	0.0391 (8)	0.0354 (8)	0.0015 (7)	−0.0132 (7)	−0.0190 (7)
C4A	0.0350 (8)	0.0431 (9)	0.0393 (8)	−0.0030 (6)	−0.0101 (6)	−0.0249 (7)
C5A	0.0368 (8)	0.0376 (8)	0.0493 (9)	−0.0062 (6)	−0.0046 (7)	−0.0247 (8)
C6A	0.0498 (10)	0.0316 (8)	0.0468 (9)	−0.0026 (7)	−0.0025 (8)	−0.0172 (7)
C7A	0.0483 (9)	0.0386 (9)	0.0417 (9)	0.0091 (7)	−0.0118 (7)	−0.0201 (7)
C8A	0.0347 (8)	0.0414 (9)	0.0429 (9)	0.0045 (6)	−0.0108 (7)	−0.0262 (7)
C9A	0.0308 (7)	0.0347 (8)	0.0333 (7)	0.0003 (6)	−0.0037 (6)	−0.0225 (6)
C10A	0.0312 (7)	0.0345 (8)	0.0330 (7)	−0.0015 (6)	−0.0025 (6)	−0.0226 (6)

O11—C11	1.3175 (17)	C4—H41	0.9700
O12—C11	1.2237 (17)	C5—H51	0.9700
O21—C21	1.2082 (19)	C5—H52	0.9700
O22—C21	1.3178 (18)	C6—H62	0.9700
O11—H11	0.96 (2)	C6—H61	0.9700
O22—H22	0.98 (2)	C1A—C9A	1.415 (2)
N2A—C3A	1.366 (2)	C3A—C4A	1.361 (2)
N2A—C1A	1.314 (2)	C4A—C10A	1.413 (2)
C1—C2	1.5356 (19)	C5A—C6A	1.361 (3)
C1—C11	1.5081 (19)	C5A—C10A	1.415 (2)
C1—C6	1.543 (2)	C6A—C7A	1.408 (3)
C2—C21	1.519 (2)	C7A—C8A	1.365 (3)
C2—C3	1.532 (2)	C8A—C9A	1.414 (2)
C3—C4	1.527 (2)	C9A—C10A	1.420 (2)
C4—C5	1.5243 (19)	C1A—H1A	0.9300
C5—C6	1.525 (2)	C3A—H3A	0.9300
C1—H1	0.9800	C4A—H4A	0.9300
C2—H2	0.9800	C5A—H5A	0.9300
C3—H31	0.9700	C6A—H6A	0.9300
C3—H32	0.9700	C7A—H7A	0.9300
C4—H42	0.9700	C8A—H8A	0.9300
C11—O11—H11	109.3 (12)	C6—C5—H51	110.00
C21—O22—H22	110.7 (12)	C4—C5—H51	109.00
C1A—N2A—C3A	118.09 (14)	H51—C5—H52	108.00
C2—C1—C6	110.04 (11)	C6—C5—H52	110.00
C6—C1—C11	109.54 (12)	C1—C6—H61	109.00
C2—C1—C11	113.10 (11)	C1—C6—H62	109.00
C1—C2—C21	112.12 (11)	C5—C6—H62	109.00
C3—C2—C21	113.55 (11)	H61—C6—H62	108.00
C1—C2—C3	113.23 (12)	C5—C6—H61	109.00
C2—C3—C4	111.43 (11)	N2A—C1A—C9A	124.04 (13)
C3—C4—C5	111.18 (12)	N2A—C3A—C4A	122.78 (15)
C4—C5—C6	110.73 (13)	C3A—C4A—C10A	120.23 (14)
C1—C6—C5	111.33 (11)	C6A—C5A—C10A	120.47 (17)
O11—C11—C1	112.94 (11)	C5A—C6A—C7A	121.01 (17)
O12—C11—C1	124.77 (12)	C6A—C7A—C8A	120.05 (16)
O11—C11—O12	122.29 (13)	C7A—C8A—C9A	120.39 (14)
O22—C21—C2	112.83 (13)	C1A—C9A—C8A	122.95 (13)
O21—C21—C2	123.78 (13)	C1A—C9A—C10A	117.55 (13)
O21—C21—O22	123.33 (16)	C8A—C9A—C10A	119.49 (14)
C2—C1—H1	108.00	C4A—C10A—C5A	124.13 (14)
C11—C1—H1	108.00	C4A—C10A—C9A	117.27 (14)
C6—C1—H1	108.00	C5A—C10A—C9A	118.58 (14)
C1—C2—H2	106.00	N2A—C1A—H1A	118.00
C21—C2—H2	106.00	C9A—C1A—H1A	118.00
C3—C2—H2	106.00	N2A—C3A—H3A	119.00
C2—C3—H31	109.00	C4A—C3A—H3A	119.00
C2—C3—H32	109.00	C3A—C4A—H4A	120.00
C4—C3—H32	109.00	C10A—C4A—H4A	120.00
H31—C3—H32	108.00	C6A—C5A—H5A	120.00
C4—C3—H31	109.00	C10A—C5A—H5A	120.00
C3—C4—H42	109.00	C5A—C6A—H6A	120.00
C5—C4—H41	109.00	C7A—C6A—H6A	119.00
C5—C4—H42	109.00	C6A—C7A—H7A	120.00
H41—C4—H42	108.00	C8A—C7A—H7A	120.00
C3—C4—H41	109.00	C7A—C8A—H8A	120.00
C4—C5—H52	110.00	C9A—C8A—H8A	120.00
C3A—N2A—C1A—C9A	−0.3 (2)	C3—C4—C5—C6	57.52 (15)
C1A—N2A—C3A—C4A	−1.4 (2)	C4—C5—C6—C1	−58.31 (15)
C6—C1—C2—C3	−52.58 (14)	N2A—C1A—C9A—C8A	−177.79 (15)
C11—C1—C2—C21	−59.79 (16)	N2A—C1A—C9A—C10A	1.2 (2)
C6—C1—C2—C21	177.35 (11)	N2A—C3A—C4A—C10A	2.1 (3)
C11—C1—C2—C3	70.29 (16)	C3A—C4A—C10A—C5A	177.60 (16)
C2—C1—C11—O11	175.82 (13)	C3A—C4A—C10A—C9A	−1.0 (2)
C2—C1—C11—O12	−4.5 (2)	C10A—C5A—C6A—C7A	−0.5 (3)
C6—C1—C11—O11	−61.03 (16)	C6A—C5A—C10A—C4A	−177.82 (16)
C6—C1—C11—O12	118.67 (16)	C6A—C5A—C10A—C9A	0.8 (2)
C11—C1—C6—C5	−69.79 (14)	C5A—C6A—C7A—C8A	−0.4 (3)
C2—C1—C6—C5	55.15 (14)	C6A—C7A—C8A—C9A	1.0 (3)
C21—C2—C3—C4	−178.03 (11)	C7A—C8A—C9A—C1A	178.30 (16)
C1—C2—C3—C4	52.62 (15)	C7A—C8A—C9A—C10A	−0.7 (2)
C3—C2—C21—O21	−148.08 (14)	C1A—C9A—C10A—C4A	−0.5 (2)
C3—C2—C21—O22	34.64 (16)	C1A—C9A—C10A—C5A	−179.24 (14)
C1—C2—C21—O21	−18.2 (2)	C8A—C9A—C10A—C4A	178.53 (14)
C1—C2—C21—O22	164.55 (12)	C8A—C9A—C10A—C5A	−0.2 (2)
C2—C3—C4—C5	−54.27 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O12i	0.96 (2)	1.68 (2)	2.6362 (14)	171.7 (18)
O22—H22···N2A	0.98 (2)	1.69 (2)	2.670 (2)	174.5 (19)
C3—H32···O12	0.97	2.54	3.1126 (17)	117
C6—H61···O11	0.97	2.53	2.8841 (18)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O12i	0.96 (2)	1.68 (2)	2.6362 (14)	171.7 (18)
O22—H22⋯N2A	0.98 (2)	1.69 (2)	2.670 (2)	174.5 (19)

Symmetry code: (i) .