2,2,6,6-Tetra­methyl-4-oxopiperi­din­ium nitrate

In the title compound, C₉H₁₈NO⁺·NO₃^-, the piperidinium ring adopts a slightly deformed chair conformation and the nitrate anion is disordered. The ions are arranged in hydrogen-bonded chains parallel to [001], in which the cations alternate with the anions. The intra­chain hydrogen bonds are bifurcated and link the O atoms of the anions to the N atoms of the cations.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PLATON (Spek, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2,2,6,6-Tetramethyl-4-oxopiperidinium nitrate

Crystal data

C9H18NO^+·NO3^−	F(000) = 472
Mr = 218.25	Dx = 1.251 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.7170 (4) Å	θ = 7.3–27.8°
b = 19.7883 (8) Å	µ = 0.82 mm^−1
c = 9.6468 (8) Å	T = 290 K
β = 128.155 (5)°	Plate, red
V = 1158.38 (15) Å^3	0.3 × 0.2 × 0.05 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1474 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 72.5°, θmin = 4.5°
profile data from ω–2θ scans	h = −9→5
Absorption correction: ψ scan (North et al., 1968)	k = −24→22
Tmin = 0.854, Tmax = 0.959	l = −9→11
3417 measured reflections	3 standard reflections every 180 min
2301 independent reflections	intensity decay: 5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.191	w = 1/[σ^2(Fo^2) + (0.0858P)^2 + 0.4726P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2301 reflections	Δρmax = 0.29 e Å^−3
167 parameters	Δρmin = −0.27 e Å^−3
29 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (14)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.9456 (3)	0.15056 (10)	0.1572 (3)	0.0456 (5)
H1A	0.9808	0.1474	0.0842	0.055*
H1B	0.9782	0.1930	0.2001	0.055*
C2	1.0986 (4)	0.10338 (13)	0.3113 (3)	0.0479 (6)
C2A	1.3267 (5)	0.13565 (19)	0.4162 (4)	0.0718 (9)
H2A1	1.3715	0.1390	0.3432	0.108*
H2A2	1.4303	0.1083	0.5174	0.108*
H2A3	1.3216	0.1800	0.4540	0.108*
C2B	1.1062 (6)	0.03357 (15)	0.2487 (4)	0.0742 (10)
H2B1	0.9701	0.0104	0.1991	0.111*
H2B2	1.2262	0.0082	0.3468	0.111*
H2B3	1.1271	0.0381	0.1609	0.111*
C3	1.0190 (5)	0.09970 (14)	0.4229 (3)	0.0550 (7)
H3A	1.0930	0.0624	0.5053	0.066*
H3B	1.0612	0.1410	0.4910	0.066*
C4	0.7743 (5)	0.09031 (14)	0.3158 (4)	0.0567 (7)
O4	0.6911 (4)	0.04634 (12)	0.3446 (3)	0.0830 (8)
C5	0.6398 (5)	0.14080 (16)	0.1716 (4)	0.0627 (8)
H5A	0.6641	0.1853	0.2230	0.075*
H5B	0.4849	0.1299	0.1058	0.075*
C6	0.6966 (4)	0.14245 (14)	0.0453 (3)	0.0520 (6)
C6A	0.5985 (6)	0.20456 (18)	−0.0740 (5)	0.0789 (10)
H6A1	0.6532	0.2447	−0.0029	0.118*
H6A2	0.4408	0.2032	−0.1444	0.118*
H6A3	0.6399	0.2048	−0.1496	0.118*
C6B	0.6171 (6)	0.07914 (18)	−0.0666 (4)	0.0753 (9)
H6B1	0.6814	0.0767	−0.1256	0.113*
H6B2	0.4594	0.0804	−0.1525	0.113*
H6B3	0.6599	0.0402	0.0073	0.113*
N2	1.0332 (4)	0.31899 (13)	0.3471 (3)	0.0632 (7)
O1A	1.0031 (12)	0.3734 (3)	0.3927 (10)	0.0538 (17)*	0.394 (4)
O2A	1.0105 (15)	0.2979 (5)	0.2168 (10)	0.069 (2)*	0.394 (4)
O3A	1.0950 (14)	0.2720 (4)	0.4723 (11)	0.087 (2)*	0.394 (4)
O1B	1.053 (2)	0.3803 (6)	0.363 (2)	0.079 (5)*	0.198 (10)
O2B	1.084 (2)	0.2953 (8)	0.2544 (16)	0.053 (4)*	0.198 (10)
O3B	0.983 (3)	0.2741 (6)	0.408 (2)	0.060 (4)*	0.198 (10)
O1C	1.0849 (17)	0.3723 (4)	0.4386 (16)	0.029 (3)*	0.233 (13)
O2C	0.985 (3)	0.3342 (8)	0.1918 (18)	0.089 (5)*	0.233 (13)
O3C	1.026 (2)	0.2645 (4)	0.3915 (17)	0.051 (3)*	0.233 (13)
O1D	1.097 (3)	0.3630 (11)	0.470 (3)	0.104 (11)*	0.175 (13)
O2D	1.086 (3)	0.3288 (8)	0.2473 (18)	0.049 (5)*	0.175 (13)
O3D	0.925 (4)	0.2705 (7)	0.334 (3)	0.086 (6)*	0.175 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0561 (12)	0.0392 (10)	0.0488 (11)	0.0011 (9)	0.0360 (10)	0.0041 (8)
C2	0.0583 (15)	0.0422 (12)	0.0462 (12)	0.0064 (11)	0.0336 (12)	0.0040 (10)
C2A	0.0595 (18)	0.082 (2)	0.0676 (18)	0.0023 (16)	0.0360 (16)	0.0048 (17)
C2B	0.101 (2)	0.0509 (16)	0.074 (2)	0.0250 (16)	0.0558 (19)	0.0068 (14)
C3	0.0691 (17)	0.0534 (15)	0.0460 (13)	−0.0011 (13)	0.0372 (13)	0.0018 (12)
C4	0.0771 (19)	0.0528 (15)	0.0593 (15)	−0.0024 (13)	0.0517 (15)	0.0000 (12)
O4	0.0961 (18)	0.0798 (16)	0.0949 (17)	−0.0093 (13)	0.0700 (15)	0.0152 (13)
C5	0.0623 (17)	0.0622 (17)	0.0743 (18)	0.0064 (14)	0.0476 (16)	0.0066 (14)
C6	0.0521 (15)	0.0491 (14)	0.0523 (14)	−0.0005 (11)	0.0310 (12)	0.0063 (11)
C6A	0.066 (2)	0.074 (2)	0.080 (2)	0.0133 (16)	0.0373 (18)	0.0303 (18)
C6B	0.076 (2)	0.073 (2)	0.0591 (17)	−0.0171 (16)	0.0325 (16)	−0.0127 (15)
N2	0.0829 (17)	0.0608 (16)	0.0715 (15)	−0.0122 (13)	0.0605 (15)	−0.0192 (12)

Geometric parameters (Å, º)

N1—C2	1.519 (3)	C6—C6B	1.514 (4)
N1—C6	1.523 (3)	C6—C6A	1.527 (4)
N1—H1A	0.9000	C6A—H6A1	0.9600
N1—H1B	0.9000	C6A—H6A2	0.9600
C2—C2B	1.523 (4)	C6A—H6A3	0.9600
C2—C2A	1.526 (4)	C6B—H6B1	0.9600
C2—C3	1.535 (3)	C6B—H6B2	0.9600
C2A—H2A1	0.9600	C6B—H6B3	0.9600
C2A—H2A2	0.9600	N2—O1A	1.239 (5)
C2A—H2A3	0.9600	N2—O2A	1.230 (6)
C2B—H2B1	0.9600	N2—O3A	1.357 (7)
C2B—H2B2	0.9600	N2—O1B	1.220 (11)
C2B—H2B3	0.9600	N2—O2B	1.267 (9)
C3—C4	1.502 (4)	N2—O3B	1.256 (10)
C3—H3A	0.9700	N2—O1C	1.272 (7)
C3—H3B	0.9700	N2—O2C	1.335 (11)
C4—O4	1.211 (3)	N2—O3C	1.176 (8)
C4—C5	1.492 (4)	N2—O1D	1.295 (13)
C5—C6	1.530 (4)	N2—O2D	1.270 (9)
C5—H5A	0.9700	N2—O3D	1.224 (12)
C5—H5B	0.9700
C2—N1—C6	120.44 (19)	C6—C5—H5A	109.1
C2—N1—H1A	107.2	C4—C5—H5B	109.1
C6—N1—H1A	107.2	C6—C5—H5B	109.1
C2—N1—H1B	107.2	H5A—C5—H5B	107.9
C6—N1—H1B	107.2	C6B—C6—N1	111.8 (2)
H1A—N1—H1B	106.8	C6B—C6—C6A	109.6 (3)
N1—C2—C2B	111.5 (2)	N1—C6—C6A	105.7 (2)
N1—C2—C2A	105.8 (2)	C6B—C6—C5	111.1 (3)
C2B—C2—C2A	109.4 (3)	N1—C6—C5	107.1 (2)
N1—C2—C3	108.0 (2)	C6A—C6—C5	111.4 (3)
C2B—C2—C3	111.4 (2)	C6—C6A—H6A1	109.5
C2A—C2—C3	110.6 (2)	C6—C6A—H6A2	109.5
C2—C2A—H2A1	109.5	H6A1—C6A—H6A2	109.5
C2—C2A—H2A2	109.5	C6—C6A—H6A3	109.5
H2A1—C2A—H2A2	109.5	H6A1—C6A—H6A3	109.5
C2—C2A—H2A3	109.5	H6A2—C6A—H6A3	109.5
H2A1—C2A—H2A3	109.5	C6—C6B—H6B1	109.5
H2A2—C2A—H2A3	109.5	C6—C6B—H6B2	109.5
C2—C2B—H2B1	109.5	H6B1—C6B—H6B2	109.5
C2—C2B—H2B2	109.5	C6—C6B—H6B3	109.5
H2B1—C2B—H2B2	109.5	H6B1—C6B—H6B3	109.5
C2—C2B—H2B3	109.5	H6B2—C6B—H6B3	109.5
H2B1—C2B—H2B3	109.5	O1A—N2—O2A	135.9 (6)
H2B2—C2B—H2B3	109.5	O2A—N2—O3A	115.3 (6)
C4—C3—C2	113.6 (2)	O3A—N2—O1A	108.6 (5)
C4—C3—H3A	108.8	O1B—N2—O2B	112.9 (10)
C2—C3—H3A	108.8	O2B—N2—O3B	113.1 (9)
C4—C3—H3B	108.8	O3B—N2—O1B	133.9 (10)
C2—C3—H3B	108.8	O1C—N2—O2C	110.0 (9)
H3A—C3—H3B	107.7	O2C—N2—O3C	125.0 (8)
O4—C4—C5	122.2 (3)	O3C—N2—O1C	125.0 (9)
O4—C4—C3	123.4 (3)	O1D—N2—O2D	117.9 (11)
C5—C4—C3	114.4 (2)	O2D—N2—O3D	123.7 (10)
C4—C5—C6	112.3 (2)	O3D—N2—O1D	118.4 (12)
C4—C5—H5A	109.1
C6—N1—C2—C2B	73.9 (3)	O4—C4—C5—C6	−125.0 (3)
C6—N1—C2—C2A	−167.3 (2)	C3—C4—C5—C6	56.1 (3)
C6—N1—C2—C3	−48.8 (3)	C2—N1—C6—C6B	−70.2 (3)
N1—C2—C3—C4	45.8 (3)	C2—N1—C6—C6A	170.6 (2)
C2B—C2—C3—C4	−77.0 (3)	C2—N1—C6—C5	51.8 (3)
C2A—C2—C3—C4	161.1 (2)	C4—C5—C6—C6B	70.8 (3)
C2—C3—C4—O4	128.1 (3)	C4—C5—C6—N1	−51.6 (3)
C2—C3—C4—C5	−53.0 (3)	C4—C5—C6—C6A	−166.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1A^i	0.90	2.00	2.886 (7)	167
N1—H1A···O3A^i	0.90	2.38	3.066 (9)	133
N1—H1B···O2A	0.90	2.09	2.955 (9)	162

Symmetry code: (i) x, −y+1/2, z−1/2.