Adamantane-1-ammonium acetate.

In the title compound, C(10)H(18)N(+)·C(2)H(3)O(2) (-), the ammonium H atoms of the cation are linked to three acetate anions via N-H⋯O hydrogen bonds, forming a chain structure extending along the b axis.

Related literature

For related structures, see: Mullica et al. (1999 ▶); He & Wen (2006 ▶). For their applications in virology, see: Hoffmann (1973) ▶; Dolin et al. (1982 ▶); Bright et al. (2005 ▶); Betakova (2007 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶). For Csp 3—O bond lengths, see: Orpen et al. (1989 ▶).

Experimental

Crystal data

C10H18N+·C2H3O2 −

M = 211.30

Monoclinic,

a = 25.7625 (12) Å

b = 6.4852 (3) Å

c = 17.3970 (9) Å

β = 127.377 (2)°

V = 2309.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

15067 measured reflections

2261 independent reflections

1471 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.134

S = 1.01

2261 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: X-SEED.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012670/zs2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012670/zs2106Isup2.hkl

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

C10H18N+·C2H3O2−	F(000) = 928
Mr = 211.30	Dx = 1.215 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1706 reflections
a = 25.7625 (12) Å	θ = 3.0–25.1°
b = 6.4852 (3) Å	µ = 0.08 mm−1
c = 17.3970 (9) Å	T = 296 K
β = 127.377 (2)°	Needle, colourless
V = 2309.8 (2) Å3	0.40 × 0.07 × 0.05 mm
Z = 8

Bruker APEXII CCD diffractometer	1471 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.077
graphite	θmax = 26.0°, θmin = 2.0°
φ and ω scans	h = −31→31
15067 measured reflections	k = −8→8
2261 independent reflections	l = −21→20

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0546P)2 + 1.9569P] where P = (Fo2 + 2Fc2)/3
2261 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.32323 (7)	0.4743 (2)	0.78287 (11)	0.0299 (4)
N1	0.19171 (10)	0.5670 (3)	0.68283 (14)	0.0240 (5)
C1	0.16138 (10)	0.5443 (3)	0.57747 (15)	0.0218 (5)
O2	0.36698 (8)	0.7678 (2)	0.78092 (12)	0.0347 (4)
C2	0.17908 (11)	0.3319 (3)	0.56130 (15)	0.0252 (5)
H2B	0.2271	0.3184	0.6007	0.030*
H2A	0.1628	0.2229	0.5815	0.030*
C3	0.14826 (10)	0.3069 (3)	0.45404 (15)	0.0264 (5)
H3A	0.1595	0.1679	0.4430	0.032*
C4	0.07403 (11)	0.3266 (4)	0.39419 (17)	0.0327 (6)
H4A	0.0570	0.2184	0.4137	0.039*
H4B	0.0537	0.3075	0.3248	0.039*
C5	0.05648 (11)	0.5400 (4)	0.41012 (17)	0.0299 (6)
H5A	0.0079	0.5534	0.3705	0.036*
C6	0.08313 (11)	0.7061 (4)	0.38012 (17)	0.0315 (6)
H6A	0.0715	0.8443	0.3896	0.038*
H6B	0.0633	0.6903	0.3107	0.038*
C7	0.15743 (11)	0.6867 (3)	0.44084 (16)	0.0270 (5)
H7A	0.1746	0.7962	0.4213	0.032*
C8	0.18804 (10)	0.7119 (3)	0.54849 (15)	0.0243 (5)
H8A	0.2362	0.7003	0.5881	0.029*
H8B	0.1773	0.8496	0.5598	0.029*
C9	0.08731 (10)	0.5654 (4)	0.51785 (16)	0.0267 (5)
H9A	0.0761	0.7024	0.5291	0.032*
H9B	0.0701	0.4585	0.5376	0.032*
C10	0.17474 (11)	0.4742 (3)	0.42404 (17)	0.0287 (6)
H10A	0.2227	0.4608	0.4626	0.034*
H10B	0.1554	0.4578	0.3549	0.034*
C11	0.36787 (11)	0.5780 (3)	0.79083 (16)	0.0251 (5)
C12	0.42684 (13)	0.4608 (4)	0.8153 (2)	0.0465 (7)
H12A	0.4638	0.4855	0.8832	0.070*
H12B	0.4381	0.5079	0.7736	0.070*
H12C	0.4169	0.3130	0.8052	0.070*
H1A	0.2392 (15)	0.544 (4)	0.723 (2)	0.055 (8)*
H1B	0.1765 (12)	0.461 (4)	0.7010 (17)	0.037 (7)*
H1C	0.1835 (11)	0.704 (3)	0.6961 (17)	0.043 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0225 (9)	0.0286 (9)	0.0383 (10)	0.0000 (7)	0.0183 (8)	0.0033 (7)
N1	0.0244 (11)	0.0242 (11)	0.0265 (10)	0.0001 (9)	0.0170 (10)	0.0004 (9)
C1	0.0183 (11)	0.0227 (11)	0.0218 (11)	−0.0014 (9)	0.0109 (10)	0.0002 (9)
O2	0.0440 (11)	0.0258 (9)	0.0491 (11)	0.0017 (8)	0.0360 (9)	0.0018 (8)
C2	0.0240 (12)	0.0228 (11)	0.0282 (12)	0.0003 (10)	0.0155 (11)	0.0017 (10)
C3	0.0261 (13)	0.0210 (12)	0.0313 (13)	0.0004 (10)	0.0170 (11)	−0.0029 (10)
C4	0.0267 (13)	0.0352 (13)	0.0307 (13)	−0.0096 (11)	0.0145 (11)	−0.0073 (11)
C5	0.0171 (12)	0.0380 (14)	0.0286 (12)	−0.0004 (10)	0.0108 (10)	0.0007 (11)
C6	0.0287 (14)	0.0342 (14)	0.0277 (12)	0.0070 (11)	0.0151 (11)	0.0067 (11)
C7	0.0289 (13)	0.0265 (12)	0.0307 (13)	−0.0009 (10)	0.0208 (11)	0.0036 (10)
C8	0.0228 (12)	0.0206 (11)	0.0312 (12)	−0.0017 (9)	0.0173 (11)	−0.0015 (9)
C9	0.0218 (12)	0.0295 (13)	0.0326 (13)	0.0001 (10)	0.0185 (11)	0.0009 (10)
C10	0.0260 (13)	0.0354 (14)	0.0269 (12)	−0.0003 (10)	0.0171 (11)	−0.0038 (10)
C11	0.0258 (13)	0.0276 (12)	0.0255 (12)	0.0022 (10)	0.0174 (11)	0.0001 (10)
C12	0.0401 (16)	0.0417 (16)	0.072 (2)	0.0117 (13)	0.0416 (16)	0.0143 (14)

O1—C11	1.265 (3)	C5—C9	1.537 (3)
N1—C1	1.501 (3)	C5—H5A	1.0000
N1—H1A	0.98 (3)	C6—C7	1.530 (3)
N1—H1B	0.94 (3)	C6—H6A	0.9900
N1—H1C	0.976 (17)	C6—H6B	0.9900
C1—C8	1.526 (3)	C7—C10	1.530 (3)
C1—C9	1.527 (3)	C7—C8	1.537 (3)
C1—C2	1.530 (3)	C7—H7A	1.0000
O2—C11	1.241 (3)	C8—H8A	0.9900
C2—C3	1.530 (3)	C8—H8B	0.9900
C2—H2B	0.9900	C9—H9A	0.9900
C2—H2A	0.9900	C9—H9B	0.9900
C3—C4	1.530 (3)	C10—H10A	0.9900
C3—C10	1.532 (3)	C10—H10B	0.9900
C3—H3A	1.0000	C11—C12	1.510 (3)
C4—C5	1.533 (3)	C12—H12A	0.9800
C4—H4A	0.9900	C12—H12B	0.9800
C4—H4B	0.9900	C12—H12C	0.9800
C5—C6	1.529 (3)
C1—N1—H1A	110.6 (16)	C7—C6—H6A	109.7
C1—N1—H1B	109.1 (15)	C5—C6—H6B	109.7
H1A—N1—H1B	104 (2)	C7—C6—H6B	109.7
C1—N1—H1C	110.6 (14)	H6A—C6—H6B	108.2
H1A—N1—H1C	109 (2)	C6—C7—C10	109.25 (18)
H1B—N1—H1C	113 (2)	C6—C7—C8	109.50 (18)
N1—C1—C8	109.19 (17)	C10—C7—C8	109.58 (18)
N1—C1—C9	109.28 (17)	C6—C7—H7A	109.5
C8—C1—C9	109.84 (17)	C10—C7—H7A	109.5
N1—C1—C2	108.69 (17)	C8—C7—H7A	109.5
C8—C1—C2	109.66 (17)	C1—C8—C7	109.02 (17)
C9—C1—C2	110.15 (17)	C1—C8—H8A	109.9
C3—C2—C1	109.15 (17)	C7—C8—H8A	109.9
C3—C2—H2B	109.9	C1—C8—H8B	109.9
C1—C2—H2B	109.9	C7—C8—H8B	109.9
C3—C2—H2A	109.9	H8A—C8—H8B	108.3
C1—C2—H2A	109.9	C1—C9—C5	109.05 (18)
H2B—C2—H2A	108.3	C1—C9—H9A	109.9
C2—C3—C4	109.27 (19)	C5—C9—H9A	109.9
C2—C3—C10	109.36 (18)	C1—C9—H9B	109.9
C4—C3—C10	109.87 (19)	C5—C9—H9B	109.9
C2—C3—H3A	109.4	H9A—C9—H9B	108.3
C4—C3—H3A	109.4	C7—C10—C3	109.35 (18)
C10—C3—H3A	109.4	C7—C10—H10A	109.8
C3—C4—C5	109.68 (18)	C3—C10—H10A	109.8
C3—C4—H4A	109.7	C7—C10—H10B	109.8
C5—C4—H4A	109.7	C3—C10—H10B	109.8
C3—C4—H4B	109.7	H10A—C10—H10B	108.3
C5—C4—H4B	109.7	O2—C11—O1	125.0 (2)
H4A—C4—H4B	108.2	O2—C11—C12	118.0 (2)
C6—C5—C4	109.34 (19)	O1—C11—C12	117.1 (2)
C6—C5—C9	109.52 (18)	C11—C12—H12A	109.5
C4—C5—C9	109.03 (18)	C11—C12—H12B	109.5
C6—C5—H5A	109.6	H12A—C12—H12B	109.5
C4—C5—H5A	109.6	C11—C12—H12C	109.5
C9—C5—H5A	109.6	H12A—C12—H12C	109.5
C5—C6—C7	109.83 (18)	H12B—C12—H12C	109.5
C5—C6—H6A	109.7
N1—C1—C2—C3	179.86 (18)	C9—C1—C8—C7	−60.8 (2)
C8—C1—C2—C3	−60.8 (2)	C2—C1—C8—C7	60.4 (2)
C9—C1—C2—C3	60.2 (2)	C6—C7—C8—C1	59.8 (2)
C1—C2—C3—C4	−59.9 (2)	C10—C7—C8—C1	−60.0 (2)
C1—C2—C3—C10	60.4 (2)	N1—C1—C9—C5	−179.49 (17)
C2—C3—C4—C5	60.6 (2)	C8—C1—C9—C5	60.7 (2)
C10—C3—C4—C5	−59.4 (2)	C2—C1—C9—C5	−60.1 (2)
C3—C4—C5—C6	59.2 (2)	C6—C5—C9—C1	−59.7 (2)
C3—C4—C5—C9	−60.5 (2)	C4—C5—C9—C1	59.9 (2)
C4—C5—C6—C7	−59.9 (2)	C6—C7—C10—C3	−60.0 (2)
C9—C5—C6—C7	59.5 (2)	C8—C7—C10—C3	59.9 (2)
C5—C6—C7—C10	60.5 (2)	C2—C3—C10—C7	−60.2 (2)
C5—C6—C7—C8	−59.5 (2)	C4—C3—C10—C7	59.8 (2)
N1—C1—C8—C7	179.39 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.99 (4)	1.80 (4)	2.777 (3)	171 (3)
N1—H1B···O2i	0.94 (3)	1.83 (3)	2.758 (3)	170 (3)
N1—H1C···O1ii	0.97 (2)	1.82 (2)	2.786 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.99 (4)	1.80 (4)	2.777 (3)	171 (3)
N1—H1B⋯O2i	0.94 (3)	1.83 (3)	2.758 (3)	170 (3)
N1—H1C⋯O1ii	0.97 (2)	1.82 (2)	2.786 (2)	171 (3)

Symmetry codes: (i) ; (ii) .