4-Carbamoylpiperidinium 5-nitro-salicylate.

In the crystal structure of the title compound, C(6)H(13)N(2)O(+)·C(7)H(4)NO(5) (-), the isonipecotamide cations and the 5-nitro-salicylate anions form hydrogen-bonded chain substructures through head-to-tail piperidinium-carboxyl-ate N-H⋯O hydrogen bonds and through centrosymmetric cyclic head-to-head amide-amide hydrogen-bonding associations [graph set R(2) (2)(8)]. These chains are cross-linked by amide-carboxyl-ate N-H⋯O and piperidinium-nitro N-H⋯O associations, giving a sheet structure.

Related literature

For structural data on isonipecotamide salts, see: Smith et al. (2010 ▶); Smith & Wermuth (2010a ▶,b ▶,c ▶,d ▶). For structures of 5-nitro­salicylates, see: Smith et al. (2005 ▶). For hydrogen-bonding graph-set and motif classification, see: Etter et al. (1990 ▶); Allen et al. (1998 ▶).

Experimental

Crystal data

C6H13N2O+·C7H4NO5 −

M = 311.30

Monoclinic,

a = 15.0442 (10) Å

b = 5.5851 (3) Å

c = 17.1939 (10) Å

β = 91.466 (6)°

V = 1444.22 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 200 K

0.40 × 0.25 × 0.16 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.912, T max = 0.980

9191 measured reflections

2833 independent reflections

1850 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.092

S = 0.95

2833 reflections

219 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.17 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 datablocks global, I. DOI: 10.1107/S1600536810050129/bt5426sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050129/bt5426Isup2.hkl

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

C6H13N2O+·C7H4NO5−	F(000) = 656
Mr = 311.30	Dx = 1.432 Mg m−3
Monoclinic, P21/n	Melting point: 463 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.0442 (10) Å	Cell parameters from 3270 reflections
b = 5.5851 (3) Å	θ = 3.6–28.7°
c = 17.1939 (10) Å	µ = 0.12 mm−1
β = 91.466 (6)°	T = 200 K
V = 1444.22 (15) Å3	Prism, pale yellow
Z = 4	0.40 × 0.25 × 0.16 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	2833 independent reflections
Radiation source: Enhance (Mo)X-ray source	1850 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.077 pixels mm-1	θmax = 26.0°, θmin = 3.6°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.912, Tmax = 0.980	l = −12→21
9191 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
2833 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.17 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
O41A	0.44900 (9)	0.0250 (2)	0.90133 (7)	0.0575 (5)
N1A	0.39663 (10)	0.5656 (3)	0.69549 (9)	0.0452 (6)
N41A	0.54984 (11)	0.2658 (4)	0.96084 (10)	0.0480 (6)
C2A	0.49383 (12)	0.5253 (3)	0.70538 (12)	0.0545 (7)
C3A	0.51390 (12)	0.3391 (3)	0.76686 (10)	0.0516 (7)
C4A	0.47324 (11)	0.4101 (3)	0.84420 (9)	0.0423 (6)
C5A	0.37359 (11)	0.4529 (3)	0.83207 (10)	0.0451 (6)
C6A	0.35478 (11)	0.6369 (3)	0.76956 (10)	0.0463 (6)
C41A	0.48930 (12)	0.2177 (3)	0.90488 (10)	0.0435 (6)
O2	0.40541 (10)	−0.1530 (2)	0.42604 (8)	0.0605 (5)
O11	0.32739 (8)	0.1529 (2)	0.63160 (7)	0.0507 (4)
O12	0.39253 (9)	−0.1469 (3)	0.57010 (7)	0.0600 (5)
O51	0.16400 (10)	0.7176 (3)	0.34253 (8)	0.0729 (6)
O52	0.17024 (9)	0.7584 (2)	0.46713 (8)	0.0562 (5)
N5	0.19077 (10)	0.6528 (3)	0.40756 (9)	0.0510 (6)
C1	0.32654 (11)	0.1565 (3)	0.49283 (9)	0.0388 (6)
C2	0.35489 (12)	0.0445 (3)	0.42422 (10)	0.0460 (6)
C3	0.32936 (13)	0.1368 (4)	0.35198 (10)	0.0550 (7)
C4	0.27649 (13)	0.3354 (4)	0.34625 (10)	0.0529 (7)
C5	0.24816 (11)	0.4452 (3)	0.41392 (9)	0.0423 (6)
C6	0.27300 (11)	0.3580 (3)	0.48665 (9)	0.0396 (6)
C11	0.35061 (12)	0.0510 (3)	0.57113 (10)	0.0443 (6)
H4A	0.50110	0.55900	0.86250	0.0510*
H11A	0.3874 (12)	0.689 (4)	0.6540 (12)	0.065 (6)*
H12A	0.3699 (12)	0.422 (4)	0.6763 (11)	0.063 (6)*
H21A	0.52260	0.67460	0.72000	0.0650*
H22A	0.51770	0.47330	0.65630	0.0650*
H31A	0.57780	0.32230	0.77390	0.0620*
H32A	0.49000	0.18580	0.75010	0.0620*
H41A	0.5753 (13)	0.398 (4)	0.9620 (11)	0.054 (7)*
H42A	0.5568 (13)	0.147 (4)	1.0029 (12)	0.075 (7)*
H51A	0.34480	0.30340	0.81770	0.0540*
H52A	0.34870	0.50710	0.88050	0.0540*
H61A	0.29100	0.65250	0.76110	0.0560*
H62A	0.37790	0.79110	0.78630	0.0560*
H2	0.4119 (15)	−0.184 (4)	0.4809 (14)	0.109 (9)*
H3	0.34850	0.06260	0.30700	0.0660*
H4	0.25970	0.39640	0.29770	0.0630*
H6	0.25380	0.43450	0.53130	0.0470*

	U11	U22	U33	U12	U13	U23
O41A	0.0736 (9)	0.0473 (8)	0.0500 (8)	0.0056 (7)	−0.0280 (7)	−0.0127 (6)
N1A	0.0518 (10)	0.0467 (10)	0.0368 (9)	−0.0015 (8)	−0.0070 (7)	−0.0078 (8)
N41A	0.0472 (10)	0.0463 (10)	0.0495 (10)	0.0124 (9)	−0.0208 (8)	−0.0123 (9)
C2A	0.0482 (12)	0.0624 (13)	0.0531 (12)	0.0009 (10)	0.0056 (9)	−0.0120 (10)
C3A	0.0439 (11)	0.0576 (12)	0.0530 (12)	0.0122 (9)	−0.0014 (9)	−0.0134 (10)
C4A	0.0421 (10)	0.0420 (10)	0.0420 (10)	0.0090 (8)	−0.0125 (8)	−0.0149 (8)
C5A	0.0422 (10)	0.0580 (11)	0.0348 (10)	0.0155 (9)	−0.0066 (8)	−0.0066 (9)
C6A	0.0429 (10)	0.0561 (11)	0.0396 (10)	0.0127 (9)	−0.0066 (8)	−0.0080 (9)
C41A	0.0418 (10)	0.0454 (11)	0.0426 (10)	0.0189 (9)	−0.0139 (8)	−0.0195 (9)
O2	0.0834 (10)	0.0489 (8)	0.0501 (8)	−0.0077 (8)	0.0216 (8)	−0.0104 (7)
O11	0.0597 (8)	0.0621 (8)	0.0303 (7)	−0.0163 (7)	−0.0002 (6)	−0.0097 (6)
O12	0.0762 (10)	0.0563 (8)	0.0474 (8)	0.0017 (8)	0.0024 (7)	−0.0007 (7)
O51	0.0929 (11)	0.0800 (11)	0.0455 (8)	−0.0009 (8)	−0.0025 (8)	0.0174 (7)
O52	0.0630 (9)	0.0544 (8)	0.0516 (9)	−0.0081 (7)	0.0075 (7)	−0.0025 (7)
N5	0.0580 (10)	0.0546 (10)	0.0406 (10)	−0.0209 (9)	0.0067 (8)	0.0033 (8)
C1	0.0423 (10)	0.0414 (10)	0.0331 (10)	−0.0211 (9)	0.0064 (7)	−0.0067 (8)
C2	0.0590 (12)	0.0407 (10)	0.0390 (11)	−0.0221 (9)	0.0148 (9)	−0.0066 (9)
C3	0.0810 (15)	0.0528 (12)	0.0322 (11)	−0.0223 (11)	0.0224 (10)	−0.0069 (9)
C4	0.0715 (14)	0.0585 (12)	0.0291 (10)	−0.0264 (11)	0.0099 (9)	0.0020 (9)
C5	0.0483 (11)	0.0438 (11)	0.0352 (10)	−0.0184 (9)	0.0073 (8)	0.0017 (8)
C6	0.0430 (10)	0.0457 (10)	0.0302 (9)	−0.0230 (9)	0.0056 (7)	−0.0079 (8)
C11	0.0453 (11)	0.0505 (11)	0.0369 (11)	−0.0208 (9)	0.0001 (8)	−0.0070 (9)

O41A—C41A	1.236 (2)	C2A—H22A	0.9700
O2—C2	1.340 (2)	C2A—H21A	0.9700
O11—C11	1.243 (2)	C3A—H31A	0.9700
O12—C11	1.273 (2)	C3A—H32A	0.9700
O51—N5	1.233 (2)	C4A—H4A	0.9800
O52—N5	1.228 (2)	C5A—H51A	0.9700
O2—H2	0.96 (2)	C5A—H52A	0.9700
N1A—C6A	1.489 (2)	C6A—H62A	0.9700
N1A—C2A	1.485 (2)	C6A—H61A	0.9700
N41A—C41A	1.335 (2)	C1—C6	1.386 (2)
N1A—H12A	0.95 (2)	C1—C11	1.505 (2)
N1A—H11A	1.00 (2)	C1—C2	1.411 (2)
N41A—H41A	0.83 (2)	C2—C3	1.390 (3)
N41A—H42A	0.99 (2)	C3—C4	1.367 (3)
N5—C5	1.448 (2)	C4—C5	1.392 (2)
C2A—C3A	1.508 (3)	C5—C6	1.385 (2)
C3A—C4A	1.530 (2)	C3—H3	0.9300
C4A—C5A	1.527 (2)	C4—H4	0.9300
C4A—C41A	1.513 (2)	C6—H6	0.9300
C5A—C6A	1.509 (2)
C2—O2—H2	102.4 (13)	C5A—C4A—H4A	109.00
C2A—N1A—C6A	112.29 (14)	C3A—C4A—H4A	109.00
C2A—N1A—H12A	108.5 (12)	C4A—C5A—H52A	109.00
C6A—N1A—H11A	111.8 (12)	C6A—C5A—H51A	109.00
H11A—N1A—H12A	106.5 (17)	C4A—C5A—H51A	109.00
C6A—N1A—H12A	109.7 (11)	C6A—C5A—H52A	109.00
C2A—N1A—H11A	107.8 (11)	H51A—C5A—H52A	108.00
H41A—N41A—H42A	122.7 (18)	H61A—C6A—H62A	108.00
C41A—N41A—H42A	116.8 (12)	C5A—C6A—H61A	110.00
C41A—N41A—H41A	120.1 (13)	C5A—C6A—H62A	110.00
O51—N5—O52	122.14 (16)	N1A—C6A—H61A	109.00
O51—N5—C5	118.93 (15)	N1A—C6A—H62A	110.00
O52—N5—C5	118.93 (14)	C2—C1—C11	120.22 (15)
N1A—C2A—C3A	111.33 (15)	C6—C1—C11	120.82 (14)
C2A—C3A—C4A	110.68 (14)	C2—C1—C6	118.90 (15)
C3A—C4A—C41A	110.79 (14)	O2—C2—C1	121.94 (15)
C5A—C4A—C41A	110.14 (14)	O2—C2—C3	118.03 (16)
C3A—C4A—C5A	109.56 (13)	C1—C2—C3	120.02 (16)
C4A—C5A—C6A	111.69 (14)	C2—C3—C4	120.82 (17)
N1A—C6A—C5A	110.57 (14)	C3—C4—C5	119.17 (16)
O41A—C41A—N41A	122.38 (17)	N5—C5—C6	119.77 (14)
N41A—C41A—C4A	116.62 (16)	C4—C5—C6	121.25 (16)
O41A—C41A—C4A	120.99 (15)	N5—C5—C4	118.98 (15)
N1A—C2A—H21A	109.00	C1—C6—C5	119.84 (15)
N1A—C2A—H22A	109.00	O11—C11—C1	120.16 (15)
C3A—C2A—H21A	109.00	O12—C11—C1	115.81 (15)
C3A—C2A—H22A	109.00	O11—C11—O12	123.99 (16)
H21A—C2A—H22A	108.00	C2—C3—H3	120.00
C2A—C3A—H32A	110.00	C4—C3—H3	120.00
C4A—C3A—H31A	109.00	C3—C4—H4	120.00
C2A—C3A—H31A	110.00	C5—C4—H4	120.00
C4A—C3A—H32A	109.00	C1—C6—H6	120.00
H31A—C3A—H32A	108.00	C5—C6—H6	120.00
C41A—C4A—H4A	109.00
C6A—N1A—C2A—C3A	56.83 (19)	C6—C1—C2—C3	0.2 (3)
C2A—N1A—C6A—C5A	−56.01 (18)	C11—C1—C2—O2	−1.8 (3)
O51—N5—C5—C4	4.5 (2)	C11—C1—C2—C3	177.28 (17)
O51—N5—C5—C6	−174.74 (16)	C2—C1—C6—C5	0.2 (2)
O52—N5—C5—C4	−175.57 (16)	C11—C1—C6—C5	−176.88 (16)
O52—N5—C5—C6	5.2 (2)	C2—C1—C11—O11	178.30 (16)
N1A—C2A—C3A—C4A	−56.37 (19)	C2—C1—C11—O12	−3.8 (2)
C2A—C3A—C4A—C5A	55.43 (18)	C6—C1—C11—O11	−4.7 (3)
C2A—C3A—C4A—C41A	177.15 (14)	C6—C1—C11—O12	173.26 (16)
C5A—C4A—C41A—O41A	49.2 (2)	O2—C2—C3—C4	178.81 (18)
C5A—C4A—C41A—N41A	−132.02 (17)	C1—C2—C3—C4	−0.3 (3)
C3A—C4A—C41A—O41A	−72.2 (2)	C2—C3—C4—C5	0.0 (3)
C3A—C4A—C5A—C6A	−55.62 (18)	C3—C4—C5—N5	−178.83 (17)
C41A—C4A—C5A—C6A	−177.72 (14)	C3—C4—C5—C6	0.4 (3)
C3A—C4A—C41A—N41A	106.61 (18)	N5—C5—C6—C1	178.76 (15)
C4A—C5A—C6A—N1A	55.72 (18)	C4—C5—C6—C1	−0.5 (3)
C6—C1—C2—O2	−178.84 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O12i	1.00 (2)	1.71 (2)	2.688 (2)	164.2 (18)
N1A—H12A···O11	0.95 (2)	1.80 (2)	2.747 (2)	173.9 (17)
N41A—H41A···O52ii	0.83 (2)	2.39 (2)	3.216 (2)	170.8 (19)
N41A—H42A···O41Aiii	0.99 (2)	1.91 (2)	2.873 (2)	164.8 (18)
O2—H2···O12	0.96 (2)	1.58 (2)	2.4897 (18)	156 (2)
C2A—H22A···O2iv	0.97	2.57	3.450 (2)	150
C6A—H61A···O11v	0.97	2.60	3.263 (2)	126
C6A—H62A···O41Ai	0.97	2.58	3.417 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O12i	1.00 (2)	1.71 (2)	2.688 (2)	164.2 (18)
N1A—H12A⋯O11	0.95 (2)	1.80 (2)	2.747 (2)	173.9 (17)
N41A—H41A⋯O52ii	0.83 (2)	2.39 (2)	3.216 (2)	170.8 (19)
N41A—H42A⋯O41Aiii	0.99 (2)	1.91 (2)	2.873 (2)	164.8 (18)
O2—H2⋯O12	0.96 (2)	1.58 (2)	2.4897 (18)	156 (2)

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