rac-4-Carbamoylpiperidinium cis-2-car-boxy-cyclo-hexane-1-carboxyl-ate.

In the title racemic salt, C(6)H(13)N(2)O(+)·C(8)H(11)O(4) (-), formed from the reaction of cis-cyclo-hexane-1,2-dicarb-oxy-lic anhydride with isonipecotamide, the cations are linked into duplex chain substructures through both centrosymmetric cyclic head-to-head 'amide motif' hydrogen-bonding associations [graph set R(2) (2)(8)] and 'side-by-side' R(2) (2)(14) associations. The anions are incorporated into the chains through cyclic R(4) (3)(10) inter-actions involving amide and piperidinium N-H⋯O(carbox-yl) hydrogen bonds which, together with inter-anion carb-oxy-lic acid O-H⋯O(carbox-yl) hydrogen bonds, give a two-dimensional layered structure extending along (011).

Related literature

For examples of structures of 1:1 Lewis base salts of cis-cyclo­hexane-1,2-dicarb­oxy­lic acid, see: Smith & Wermuth (2011a ▶,b ▶). For examples of isonipecotamide proton-transfer salts, see: Smith & Wermuth (2010 ▶). For graph-set analysis, see: Etter et al. (1990 ▶). For hydrogen-bonding motifs, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C6H13N2O+·C8H11O4 −

M = 300.35

Monoclinic,

a = 19.0097 (14) Å

b = 9.0667 (7) Å

c = 9.1999 (8) Å

β = 92.022 (7)°

V = 1584.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.40 × 0.35 × 0.10 mm

Data collection

Oxford Gemini-S CCD area-detector diffractometer

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

10518 measured reflections

3100 independent reflections

2146 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.182

S = 1.06

3100 reflections

210 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.20 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/S1600536812004710/nk2139sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004710/nk2139Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004710/nk2139Isup3.cml

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

C6H13N2O+·C8H11O4−	F(000) = 644
Mr = 300.35	Dx = 1.255 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3793 reflections
a = 19.0097 (14) Å	θ = 3.2–28.9°
b = 9.0667 (7) Å	µ = 0.10 mm−1
c = 9.1999 (8) Å	T = 200 K
β = 92.022 (7)°	Plate, colourless
V = 1584.7 (2) Å3	0.40 × 0.35 × 0.10 mm
Z = 4

Oxford Gemini-S CCD area-detector diffractometer	3100 independent reflections
Radiation source: Enhance (Mo) X-ray source	2146 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −23→22
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.86, Tmax = 0.98	l = −11→11
10518 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0845P)2 + 0.9949P] where P = (Fo2 + 2Fc2)/3
3100 reflections	(Δ/σ)max = 0.002
210 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.20 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	0.21833 (13)	0.8455 (3)	0.0243 (3)	0.0522 (9)
O12	0.23582 (11)	1.0432 (3)	−0.1098 (2)	0.0415 (8)
O21	0.25201 (12)	1.1290 (3)	0.2369 (3)	0.0487 (9)
O22	0.31747 (13)	1.3299 (3)	0.2117 (3)	0.0485 (9)
C1	0.33119 (16)	0.9592 (3)	0.0442 (4)	0.0362 (10)
C2	0.35236 (15)	1.1183 (4)	0.0836 (4)	0.0337 (10)
C3	0.42799 (19)	1.1251 (5)	0.1462 (5)	0.0634 (16)
C4	0.4392 (2)	1.0232 (6)	0.2741 (6)	0.086 (2)
C5	0.4211 (2)	0.8668 (6)	0.2325 (6)	0.085 (2)
C6	0.3456 (2)	0.8519 (4)	0.1711 (5)	0.0586 (14)
C11	0.25621 (15)	0.9481 (3)	−0.0177 (3)	0.0306 (9)
C21	0.30223 (16)	1.1903 (4)	0.1864 (3)	0.0337 (10)
O41A	−0.00706 (10)	0.2052 (2)	−0.0339 (2)	0.0298 (7)
N1A	0.13089 (14)	0.6330 (3)	−0.0339 (3)	0.0293 (8)
N41A	0.08655 (16)	0.0589 (3)	−0.0669 (3)	0.0286 (8)
C2A	0.11125 (16)	0.5811 (3)	−0.1821 (3)	0.0290 (9)
C3A	0.06735 (15)	0.4418 (3)	−0.1727 (3)	0.0257 (9)
C4A	0.10386 (14)	0.3218 (3)	−0.0845 (3)	0.0251 (8)
C5A	0.12773 (16)	0.3800 (3)	0.0645 (3)	0.0292 (9)
C6A	0.17115 (17)	0.5201 (3)	0.0524 (3)	0.0325 (10)
C41A	0.05649 (14)	0.1901 (3)	−0.0612 (3)	0.0236 (8)
H1	0.36180	0.92850	−0.03370	0.0430*
H2	0.35070	1.17570	−0.00670	0.0400*
H22	0.288 (3)	1.369 (5)	0.281 (5)	0.082 (15)*
H31	0.46020	1.09850	0.07100	0.0760*
H32	0.43860	1.22540	0.17640	0.0760*
H41	0.41000	1.05460	0.35270	0.1030*
H42	0.48800	1.02810	0.30850	0.1030*
H51	0.42710	0.80410	0.31750	0.1020*
H52	0.45340	0.83290	0.16040	0.1020*
H61	0.31300	0.87170	0.24740	0.0700*
H62	0.33780	0.75160	0.13760	0.0700*
H4A	0.14530	0.28900	−0.13600	0.0300*
H11A	0.0869 (17)	0.663 (3)	0.007 (3)	0.027 (8)*
H12A	0.161 (2)	0.722 (4)	−0.035 (4)	0.061 (11)*
H21A	0.15340	0.56100	−0.23520	0.0350*
H22A	0.08450	0.65690	−0.23390	0.0350*
H31A	0.02300	0.46550	−0.12910	0.0310*
H32A	0.05690	0.40530	−0.27020	0.0310*
H41A	0.0623 (18)	−0.017 (4)	−0.045 (3)	0.037 (10)*
H42A	0.1263 (17)	0.054 (3)	−0.082 (3)	0.017 (8)*
H51A	0.08680	0.40010	0.12130	0.0350*
H52A	0.15560	0.30510	0.11510	0.0350*
H61A	0.18260	0.55830	0.14880	0.0390*
H62A	0.21480	0.49810	0.00550	0.0390*

	U11	U22	U33	U12	U13	U23
O11	0.0398 (14)	0.0352 (14)	0.0811 (19)	−0.0182 (11)	−0.0039 (13)	0.0027 (13)
O12	0.0305 (12)	0.0545 (16)	0.0393 (13)	−0.0007 (11)	−0.0015 (10)	0.0068 (11)
O21	0.0385 (14)	0.0496 (15)	0.0590 (16)	−0.0112 (11)	0.0170 (12)	−0.0067 (12)
O22	0.0473 (15)	0.0479 (16)	0.0512 (15)	−0.0127 (12)	0.0156 (12)	−0.0159 (12)
C1	0.0240 (16)	0.0363 (19)	0.0483 (19)	0.0031 (14)	0.0016 (14)	−0.0011 (15)
C2	0.0211 (15)	0.0402 (19)	0.0398 (18)	−0.0042 (13)	0.0006 (13)	−0.0027 (14)
C3	0.028 (2)	0.074 (3)	0.088 (3)	−0.0069 (19)	−0.001 (2)	−0.025 (2)
C4	0.043 (3)	0.111 (5)	0.102 (4)	0.009 (3)	−0.035 (3)	−0.007 (3)
C5	0.053 (3)	0.097 (4)	0.103 (4)	0.028 (3)	−0.022 (3)	0.026 (3)
C6	0.046 (2)	0.047 (2)	0.082 (3)	0.0090 (18)	−0.008 (2)	0.020 (2)
C11	0.0273 (16)	0.0242 (16)	0.0403 (17)	−0.0002 (13)	−0.0005 (13)	−0.0073 (14)
C21	0.0277 (17)	0.0436 (19)	0.0294 (16)	−0.0014 (15)	−0.0036 (13)	−0.0003 (14)
O41A	0.0228 (11)	0.0265 (11)	0.0401 (12)	−0.0011 (9)	0.0010 (9)	0.0013 (9)
N1A	0.0274 (15)	0.0253 (14)	0.0351 (14)	0.0002 (12)	−0.0004 (11)	−0.0009 (11)
N41A	0.0188 (14)	0.0291 (15)	0.0381 (15)	−0.0049 (12)	0.0026 (11)	0.0020 (11)
C2A	0.0288 (16)	0.0317 (16)	0.0264 (15)	0.0014 (13)	−0.0010 (12)	0.0075 (13)
C3A	0.0257 (15)	0.0310 (16)	0.0200 (14)	−0.0011 (13)	−0.0046 (11)	0.0013 (12)
C4A	0.0217 (14)	0.0258 (15)	0.0278 (15)	0.0000 (12)	−0.0006 (12)	0.0001 (12)
C5A	0.0326 (17)	0.0284 (16)	0.0259 (15)	0.0002 (13)	−0.0092 (12)	0.0037 (12)
C6A	0.0378 (18)	0.0270 (16)	0.0318 (16)	−0.0027 (14)	−0.0123 (13)	0.0051 (13)
C41A	0.0240 (15)	0.0253 (15)	0.0211 (14)	−0.0014 (12)	−0.0063 (11)	0.0014 (12)

O11—C11	1.246 (4)	C3—H31	0.9700
O12—C11	1.260 (4)	C3—H32	0.9700
O21—C21	1.211 (4)	C4—H42	0.9700
O22—C21	1.317 (4)	C4—H41	0.9700
O22—H22	0.93 (5)	C5—H52	0.9700
O41A—C41A	1.250 (3)	C5—H51	0.9700
N1A—C6A	1.490 (4)	C6—H62	0.9700
N1A—C2A	1.478 (4)	C6—H61	0.9700
N41A—C41A	1.322 (4)	C2A—C3A	1.518 (4)
N1A—H12A	0.99 (4)	C3A—C4A	1.511 (4)
N1A—H11A	0.97 (3)	C4A—C41A	1.515 (4)
N41A—H41A	0.86 (3)	C4A—C5A	1.523 (4)
N41A—H42A	0.77 (3)	C5A—C6A	1.521 (4)
C1—C2	1.538 (5)	C2A—H21A	0.9700
C1—C6	1.537 (5)	C2A—H22A	0.9700
C1—C11	1.520 (4)	C3A—H31A	0.9700
C2—C3	1.531 (5)	C3A—H32A	0.9700
C2—C21	1.514 (5)	C4A—H4A	0.9800
C3—C4	1.505 (7)	C5A—H51A	0.9700
C4—C5	1.506 (8)	C5A—H52A	0.9700
C5—C6	1.530 (6)	C6A—H61A	0.9700
C1—H1	0.9800	C6A—H62A	0.9700
C2—H2	0.9800
C21—O22—H22	111 (3)	C4—C5—H51	109.00
C2A—N1A—C6A	112.4 (2)	C4—C5—H52	109.00
C6A—N1A—H11A	114.9 (16)	H51—C5—H52	108.00
H11A—N1A—H12A	106 (3)	C6—C5—H52	109.00
C6A—N1A—H12A	106 (2)	C1—C6—H62	109.00
C2A—N1A—H12A	112 (2)	C1—C6—H61	109.00
C2A—N1A—H11A	104.7 (17)	C5—C6—H62	109.00
H41A—N41A—H42A	122 (3)	H61—C6—H62	108.00
C41A—N41A—H42A	119 (2)	C5—C6—H61	109.00
C41A—N41A—H41A	119 (2)	N1A—C2A—C3A	109.5 (2)
C6—C1—C11	112.5 (3)	C2A—C3A—C4A	112.7 (2)
C2—C1—C6	112.1 (3)	C3A—C4A—C41A	112.3 (2)
C2—C1—C11	112.6 (2)	C5A—C4A—C41A	107.8 (2)
C1—C2—C21	112.7 (3)	C3A—C4A—C5A	110.5 (2)
C3—C2—C21	110.6 (3)	C4A—C5A—C6A	111.6 (2)
C1—C2—C3	111.2 (3)	N1A—C6A—C5A	110.1 (2)
C2—C3—C4	112.0 (3)	O41A—C41A—C4A	121.7 (2)
C3—C4—C5	110.8 (4)	N41A—C41A—C4A	116.3 (2)
C4—C5—C6	112.3 (4)	O41A—C41A—N41A	121.9 (3)
C1—C6—C5	111.4 (3)	N1A—C2A—H21A	110.00
O11—C11—O12	123.5 (3)	N1A—C2A—H22A	110.00
O11—C11—C1	118.6 (3)	C3A—C2A—H21A	110.00
O12—C11—C1	118.0 (3)	C3A—C2A—H22A	110.00
O21—C21—C2	124.3 (3)	H21A—C2A—H22A	108.00
O22—C21—C2	112.7 (3)	C2A—C3A—H31A	109.00
O21—C21—O22	123.0 (3)	C2A—C3A—H32A	109.00
C6—C1—H1	106.00	C4A—C3A—H31A	109.00
C2—C1—H1	106.00	C4A—C3A—H32A	109.00
C11—C1—H1	106.00	H31A—C3A—H32A	108.00
C3—C2—H2	107.00	C3A—C4A—H4A	109.00
C1—C2—H2	107.00	C5A—C4A—H4A	109.00
C21—C2—H2	107.00	C41A—C4A—H4A	109.00
C4—C3—H31	109.00	C4A—C5A—H51A	109.00
C2—C3—H31	109.00	C4A—C5A—H52A	109.00
H31—C3—H32	108.00	C6A—C5A—H51A	109.00
C4—C3—H32	109.00	C6A—C5A—H52A	109.00
C2—C3—H32	109.00	H51A—C5A—H52A	108.00
C5—C4—H42	109.00	N1A—C6A—H61A	110.00
C3—C4—H42	110.00	N1A—C6A—H62A	110.00
H41—C4—H42	108.00	C5A—C6A—H61A	110.00
C5—C4—H41	110.00	C5A—C6A—H62A	110.00
C3—C4—H41	109.00	H61A—C6A—H62A	108.00
C6—C5—H51	109.00
C2A—N1A—C6A—C5A	−58.9 (3)	C3—C2—C21—O22	59.5 (4)
C6A—N1A—C2A—C3A	58.5 (3)	C1—C2—C21—O21	2.3 (5)
C11—C1—C2—C3	179.7 (3)	C2—C3—C4—C5	57.2 (5)
C11—C1—C2—C21	55.0 (4)	C3—C4—C5—C6	−56.7 (5)
C6—C1—C2—C21	−73.1 (3)	C4—C5—C6—C1	53.8 (5)
C11—C1—C6—C5	−179.3 (3)	N1A—C2A—C3A—C4A	−55.6 (3)
C2—C1—C11—O11	−137.0 (3)	C2A—C3A—C4A—C5A	53.0 (3)
C2—C1—C11—O12	43.4 (4)	C2A—C3A—C4A—C41A	173.4 (2)
C6—C1—C11—O11	−9.1 (4)	C41A—C4A—C5A—C6A	−175.6 (2)
C6—C1—C11—O12	171.3 (3)	C3A—C4A—C41A—O41A	−40.5 (4)
C2—C1—C6—C5	−51.1 (4)	C3A—C4A—C41A—N41A	141.6 (3)
C6—C1—C2—C3	51.7 (4)	C5A—C4A—C41A—O41A	81.5 (3)
C1—C2—C3—C4	−54.8 (5)	C5A—C4A—C41A—N41A	−96.5 (3)
C21—C2—C3—C4	71.2 (4)	C3A—C4A—C5A—C6A	−52.5 (3)
C1—C2—C21—O22	−175.4 (3)	C4A—C5A—C6A—N1A	55.2 (3)
C3—C2—C21—O21	−122.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O41Ai	0.97 (3)	1.95 (3)	2.861 (3)	155 (2)
N1A—H12A···O11	0.99 (4)	1.64 (4)	2.588 (4)	158 (3)
N41A—H41A···O41Aii	0.86 (3)	2.14 (4)	2.996 (3)	174 (2)
N41A—H42A···O12iii	0.77 (3)	2.11 (3)	2.882 (4)	177 (3)
O22—H22···O12iv	0.93 (5)	1.64 (5)	2.571 (3)	173 (4)
C4A—H4A···O21v	0.98	2.49	3.340 (4)	145
C2A—H21A···O21v	0.97	2.57	3.389 (4)	143
C2A—H22A···O41Avi	0.97	2.59	3.413 (3)	143
C3—H32···O22	0.97	2.52	2.884 (5)	102
C6A—H61A···O12vii	0.97	2.58	3.351 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O41Ai	0.97 (3)	1.95 (3)	2.861 (3)	155 (2)
N1A—H12A⋯O11	0.99 (4)	1.64 (4)	2.588 (4)	158 (3)
N41A—H41A⋯O41Aii	0.86 (3)	2.14 (4)	2.996 (3)	174 (2)
N41A—H42A⋯O12iii	0.77 (3)	2.11 (3)	2.882 (4)	177 (3)
O22—H22⋯O12iv	0.93 (5)	1.64 (5)	2.571 (3)	173 (4)

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