rac-Ammonium cis-2-carb-oxy-cyclo-hexane-1-carboxyl-ate.

In the structure of the title compound, NH(4) (+)·C(8)H(11)O(4) (-), the carboxyl and carboxyl-ate groups of the cation adopt C-C-C-O torsion angles of 174.9 (2) and -145.4 (2)°, respectively, with the alicyclic ring. The ammonium H atoms of the cations give a total of five hydrogen-bonding associations with carboxyl-ate O-atom acceptors of the anion which, together with a carboxyl O-H⋯O(carboxyl-ate) inter-action give sheet structures which lie in the (101) planes.

Related literature

For the structure of the isomeric racemic ammonium salt of trans-cyclo­hexane-1,2-dicarb­oxy­lic acid (TCDA), see: Stibrany et al. (2004 ▶). For the structures of rac-cis-CDA, rac-trans-CDA and (+)-trans-CDA, see: Benedetti et al. (1970 ▶); Benedetti, Corradini, Pedone & Post (1969 ▶); Benedetti, Corradini & Pedone (1969 ▶); Rizal & Ng (2008 ▶). The cis,trans-isomer exists as an essentially unresolvable racemate, see: Eliel (1962 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

NH4 +·C8H11O4 −

M = 189.21

Monoclinic,

a = 15.4908 (13) Å

b = 5.3475 (3) Å

c = 12.1716 (9) Å

β = 109.795 (9)°

V = 948.68 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.30 × 0.22 × 0.10 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.86, T max = 0.98

5997 measured reflections

1862 independent reflections

1313 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.141

S = 0.99

1862 reflections

138 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051883/ng5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051883/ng5083Isup2.hkl

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

NH4+·C8H11O4−	F(000) = 408
Mr = 189.21	Dx = 1.325 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2294 reflections
a = 15.4908 (13) Å	θ = 3.4–28.6°
b = 5.3475 (3) Å	µ = 0.11 mm−1
c = 12.1716 (9) Å	T = 200 K
β = 109.795 (9)°	Plate, colourless
V = 948.68 (13) Å3	0.30 × 0.22 × 0.10 mm
Z = 4

Oxford Diffraction Gemini-S CCD-detector diffractometer	1862 independent reflections
Radiation source: Enhance (Mo) X-ray source	1313 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −19→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.86, Tmax = 0.98	l = −15→15
5997 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0838P)2] where P = (Fo2 + 2Fc2)/3
1862 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.44 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
O11	0.13732 (12)	0.9964 (3)	0.33214 (13)	0.0306 (5)
O12	0.08448 (12)	1.2330 (3)	0.44276 (14)	0.0329 (6)
O21	0.16061 (13)	0.7624 (3)	0.59854 (14)	0.0368 (6)
O22	0.20622 (15)	0.9149 (4)	0.77916 (15)	0.0450 (7)
C1	0.24584 (16)	1.1450 (4)	0.51309 (18)	0.0243 (7)
C2	0.24599 (17)	1.1538 (4)	0.63967 (18)	0.0242 (7)
C3	0.34336 (18)	1.1894 (4)	0.7268 (2)	0.0323 (8)
C4	0.40930 (18)	0.9929 (5)	0.7113 (2)	0.0345 (8)
C5	0.41077 (18)	0.9927 (5)	0.5871 (2)	0.0383 (9)
C6	0.31483 (17)	0.9528 (5)	0.4989 (2)	0.0302 (8)
C11	0.14981 (17)	1.1222 (4)	0.42428 (19)	0.0253 (7)
C21	0.20048 (16)	0.9222 (4)	0.66831 (19)	0.0245 (7)
N1	−0.01140 (18)	0.6903 (5)	0.3749 (2)	0.0320 (8)
H1	0.26870	1.30850	0.49890	0.0290*
H2	0.20960	1.29920	0.64640	0.0290*
H22	0.192 (3)	0.764 (8)	0.796 (3)	0.088 (13)*
H31	0.36540	1.35430	0.71610	0.0390*
H32	0.34180	1.18000	0.80560	0.0390*
H41	0.47050	1.02650	0.76520	0.0410*
H42	0.39080	0.82920	0.72960	0.0410*
H51	0.45100	0.86070	0.57860	0.0460*
H52	0.43490	1.15090	0.57130	0.0460*
H61	0.29390	0.78600	0.50860	0.0360*
H62	0.31740	0.96480	0.42050	0.0360*
H1A	0.016 (2)	0.832 (6)	0.363 (3)	0.057 (10)*
H1B	0.031 (3)	0.566 (7)	0.402 (3)	0.071 (11)*
H1C	−0.057 (2)	0.647 (5)	0.300 (2)	0.044 (8)*
H1D	−0.038 (2)	0.728 (6)	0.436 (3)	0.072 (11)*

	U11	U22	U33	U12	U13	U23
O11	0.0415 (11)	0.0289 (9)	0.0191 (8)	0.0057 (8)	0.0071 (7)	−0.0059 (7)
O12	0.0338 (11)	0.0378 (10)	0.0264 (9)	0.0104 (8)	0.0093 (7)	−0.0021 (7)
O21	0.0556 (13)	0.0292 (9)	0.0254 (9)	−0.0167 (9)	0.0134 (8)	−0.0038 (7)
O22	0.0814 (16)	0.0360 (11)	0.0207 (9)	−0.0190 (11)	0.0215 (9)	−0.0004 (8)
C1	0.0336 (14)	0.0186 (11)	0.0232 (12)	−0.0030 (10)	0.0130 (10)	0.0004 (9)
C2	0.0328 (14)	0.0171 (11)	0.0227 (11)	0.0002 (10)	0.0094 (10)	−0.0009 (9)
C3	0.0398 (16)	0.0259 (13)	0.0288 (13)	−0.0043 (11)	0.0086 (11)	−0.0033 (10)
C4	0.0258 (14)	0.0362 (14)	0.0349 (14)	0.0010 (12)	0.0017 (11)	−0.0002 (11)
C5	0.0302 (15)	0.0431 (16)	0.0434 (16)	0.0057 (13)	0.0148 (12)	0.0011 (12)
C6	0.0367 (15)	0.0315 (14)	0.0260 (13)	0.0026 (11)	0.0153 (11)	0.0003 (10)
C11	0.0386 (15)	0.0173 (11)	0.0225 (12)	0.0017 (11)	0.0137 (10)	0.0037 (9)
C21	0.0301 (13)	0.0216 (11)	0.0212 (12)	0.0020 (10)	0.0081 (10)	0.0016 (9)
N1	0.0373 (14)	0.0327 (13)	0.0244 (12)	−0.0003 (11)	0.0085 (10)	0.0038 (10)

O11—C11	1.265 (3)	C3—C4	1.521 (4)
O12—C11	1.257 (3)	C4—C5	1.520 (3)
O21—C21	1.216 (3)	C5—C6	1.525 (4)
O22—C21	1.322 (3)	C1—H1	0.9800
O22—H22	0.88 (4)	C2—H2	0.9800
N1—H1D	0.99 (3)	C3—H31	0.9700
N1—H1B	0.91 (4)	C3—H32	0.9700
N1—H1C	0.97 (2)	C4—H41	0.9700
N1—H1A	0.90 (3)	C4—H42	0.9700
C1—C11	1.519 (3)	C5—H52	0.9700
C1—C2	1.541 (3)	C5—H51	0.9700
C1—C6	1.534 (4)	C6—H61	0.9700
C2—C3	1.534 (4)	C6—H62	0.9700
C2—C21	1.523 (3)
C21—O22—H22	109 (2)	C6—C1—H1	106.00
H1B—N1—H1C	112 (3)	C1—C2—H2	108.00
H1C—N1—H1D	114 (3)	C3—C2—H2	108.00
H1B—N1—H1D	108 (3)	C21—C2—H2	108.00
H1A—N1—H1D	107 (3)	H31—C3—H32	108.00
H1A—N1—H1B	110 (3)	C2—C3—H31	109.00
H1A—N1—H1C	106 (3)	C2—C3—H32	109.00
C6—C1—C11	114.70 (18)	C4—C3—H31	109.00
C2—C1—C6	111.59 (18)	C4—C3—H32	109.00
C2—C1—C11	112.6 (2)	C3—C4—H42	109.00
C1—C2—C3	111.3 (2)	C5—C4—H41	109.00
C1—C2—C21	111.10 (18)	C3—C4—H41	109.00
C3—C2—C21	111.46 (18)	H41—C4—H42	108.00
C2—C3—C4	111.90 (19)	C5—C4—H42	109.00
C3—C4—C5	111.2 (2)	C6—C5—H51	109.00
C4—C5—C6	111.2 (2)	C4—C5—H52	109.00
C1—C6—C5	112.2 (2)	C4—C5—H51	109.00
O11—C11—O12	121.2 (2)	C6—C5—H52	109.00
O11—C11—C1	119.5 (2)	H51—C5—H52	108.00
O12—C11—C1	119.25 (19)	H61—C6—H62	108.00
O21—C21—O22	122.3 (2)	C1—C6—H61	109.00
O21—C21—C2	125.2 (2)	C1—C6—H62	109.00
O22—C21—C2	112.41 (19)	C5—C6—H61	109.00
C11—C1—H1	106.00	C5—C6—H62	109.00
C2—C1—H1	106.00
C6—C1—C2—C3	52.1 (2)	C1—C2—C3—C4	−54.1 (2)
C6—C1—C2—C21	−72.7 (3)	C21—C2—C3—C4	70.6 (3)
C11—C1—C2—C3	−177.29 (17)	C1—C2—C21—O21	−7.1 (4)
C11—C1—C2—C21	57.9 (2)	C1—C2—C21—O22	174.9 (2)
C2—C1—C6—C5	−53.0 (3)	C3—C2—C21—O21	−131.9 (3)
C11—C1—C6—C5	177.5 (2)	C3—C2—C21—O22	50.1 (3)
C2—C1—C11—O11	−145.4 (2)	C2—C3—C4—C5	56.3 (3)
C2—C1—C11—O12	36.0 (3)	C3—C4—C5—C6	−56.4 (3)
C6—C1—C11—O11	−16.4 (3)	C4—C5—C6—C1	55.1 (3)
C6—C1—C11—O12	165.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O11	0.90 (3)	2.22 (3)	3.012 (3)	146 (3)
N1—H1A···O12	0.90 (3)	2.44 (3)	3.237 (3)	147 (3)
N1—H1B···O12i	0.91 (4)	1.96 (4)	2.835 (3)	161 (4)
N1—H1C···O11ii	0.97 (2)	1.85 (3)	2.811 (3)	168 (2)
N1—H1D···O12iii	0.99 (3)	1.86 (3)	2.842 (3)	174 (3)
O22—H22···O11iv	0.88 (4)	1.76 (4)	2.619 (3)	165 (5)
C2—H2···O21v	0.98	2.60	3.485 (3)	150
C3—H32···O22	0.97	2.46	2.827 (4)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O11	0.90 (3)	2.22 (3)	3.012 (3)	146 (3)
N1—H1A⋯O12	0.90 (3)	2.44 (3)	3.237 (3)	147 (3)
N1—H1B⋯O12i	0.91 (4)	1.96 (4)	2.835 (3)	161 (4)
N1—H1C⋯O11ii	0.97 (2)	1.85 (3)	2.811 (3)	168 (2)
N1—H1D⋯O12iii	0.99 (3)	1.86 (3)	2.842 (3)	174 (3)
O22—H22⋯O11iv	0.88 (4)	1.76 (4)	2.619 (3)	165 (5)

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