[1-(1-Adamantylamino)ethyl-idene]oxonium methane-sulfonate.

In the title salt, C(12)H(20)NO(+)·CH(3)SO(3) (-), the [1-(1-adamantyl-amino)ethyl-idene]oxonium cations and methane-sulfonate anions are linked into chains along the a axis via O-H⋯O and N-H⋯O hydrogen bonds. All non-H atoms of the acetamido group are essentially planar, with a maximum deviation of 0.0085 (12) Å. In comparison with related structures, the carbonyl C=O bond is slightly elongated [1.249 (2) Å], whereas the amide C-N bond is shortened [1.292 (2) Å].

Related literature

For previously published structures of N-(1-adamant­yl)­acetamide, see: Pröhl et al. (1997 ▶); Kashino et al. (1998 ▶); Mizoguchi et al. (1997 ▶). For the preparation of N-(1-adaman­t­yl)­acetamide, see: Bach et al. (1979 ▶, 1980 ▶); Gerzon et al. (1963 ▶); Stetter et al. (1959 ▶, 1960 ▶). For the biological activity of related adamantane derivatives, see: Davies et al. (1964 ▶); Aldrich et al. (1971 ▶).

Experimental

Crystal data

C12H20NO+·CH3SO3 −

M = 289.38

Orthorhombic,

a = 12.9848 (7) Å

b = 11.2625 (6) Å

c = 19.0037 (10) Å

V = 2779.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 120 K

0.40 × 0.40 × 0.35 mm

Data collection

Kuma KM-4 CCD diffractometer

Absorption correction: multi-scan (Xcalibur; Oxford Diffraction, 2006 ▶) T min = 0.824, T max = 0.914

19453 measured reflections

2454 independent reflections

2000 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.102

S = 1.09

2454 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.47 e Å−3

Data collection: Xcalibur (Oxford Diffraction, 2006 ▶); cell refinement: Xcalibur (Oxford Diffraction, 2006 ▶); data reduction: Xcalibur (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017632/pk2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017632/pk2161Isup2.hkl

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

C12H20NO+·CH3SO3−	Dx = 1.383 Mg m−3
Mr = 289.38	Melting point: 445 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2454 reflections
a = 12.9848 (7) Å	θ = 3.1–25.0°
b = 11.2625 (6) Å	µ = 0.24 mm−1
c = 19.0037 (10) Å	T = 120 K
V = 2779.1 (3) Å3	Block, colourless
Z = 8	0.40 × 0.40 × 0.35 mm
F(000) = 1248

Kuma KM-4 CCD diffractometer	2454 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 0.06 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −15→14
Absorption correction: multi-scan (Xcalibur; Oxford Diffraction, 2006)	k = −13→13
Tmin = 0.824, Tmax = 0.914	l = −21→22
19453 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.054P)2 + 1.529P] where P = (Fo2 + 2Fc2)/3
2454 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.47 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 > 2σ(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
C1	−0.09044 (13)	0.28700 (14)	0.34406 (9)	0.0181 (4)
C2	−0.00380 (13)	0.22857 (15)	0.30176 (9)	0.0195 (4)
H2A	0.0621	0.2698	0.3111	0.023*
H2B	0.0038	0.1445	0.3162	0.023*
C3	−0.10319 (14)	0.41701 (15)	0.32215 (9)	0.0201 (4)
H3A	−0.1594	0.4541	0.3496	0.024*
H3B	−0.0388	0.4613	0.3317	0.024*
C4	−0.19133 (14)	0.22087 (16)	0.33012 (9)	0.0229 (4)
H4A	−0.1846	0.1370	0.3451	0.027*
H4B	−0.2477	0.2576	0.3576	0.027*
C5	−0.21663 (15)	0.22635 (17)	0.25177 (10)	0.0251 (4)
H5	−0.2824	0.1828	0.2427	0.030*
C6	−0.13002 (15)	0.16913 (16)	0.20928 (10)	0.0262 (4)
H6A	−0.1467	0.1724	0.1585	0.031*
H6B	−0.1225	0.0847	0.2230	0.031*
C7	−0.02922 (14)	0.23530 (16)	0.22322 (10)	0.0225 (4)
H7	0.0276	0.1979	0.1954	0.027*
C8	−0.04113 (14)	0.36523 (15)	0.20149 (9)	0.0224 (4)
H8A	−0.0567	0.3702	0.1506	0.027*
H8B	0.0240	0.4084	0.2103	0.027*
C9	−0.12838 (13)	0.42199 (15)	0.24371 (9)	0.0213 (4)
H9	−0.1362	0.5068	0.2291	0.026*
C10	−0.22900 (14)	0.35595 (17)	0.22953 (10)	0.0256 (4)
H10A	−0.2461	0.3603	0.1788	0.031*
H10B	−0.2858	0.3932	0.2564	0.031*
C11	0.00322 (13)	0.32640 (15)	0.45588 (9)	0.0211 (4)
C12	0.01287 (15)	0.30548 (18)	0.53284 (10)	0.0271 (4)
H12A	0.0762	0.2609	0.5424	0.041*
H12B	−0.0467	0.2599	0.5495	0.041*
H12C	0.0155	0.3819	0.5575	0.041*
N1	−0.06903 (11)	0.27539 (13)	0.42026 (8)	0.0195 (3)
H1	−0.1102 (15)	0.2308 (18)	0.4446 (11)	0.023*
O1	0.06855 (10)	0.39456 (12)	0.42407 (6)	0.0268 (3)
H2	0.1158 (17)	0.436 (2)	0.4560 (12)	0.040*
S1	0.29158 (4)	0.49446 (4)	0.50332 (2)	0.02087 (16)
O2	0.17962 (12)	0.51334 (12)	0.50208 (7)	0.0302 (3)
O3	0.31512 (12)	0.37147 (12)	0.48779 (7)	0.0342 (4)
O4	0.33796 (11)	0.54034 (13)	0.56618 (7)	0.0357 (4)
C13	0.33885 (17)	0.57840 (19)	0.43323 (10)	0.0356 (5)
H13A	0.3191	0.6617	0.4396	0.053*
H13B	0.3099	0.5485	0.3890	0.053*
H13C	0.4141	0.5721	0.4318	0.053*

	U11	U22	U33	U12	U13	U23
C1	0.0179 (9)	0.0183 (8)	0.0179 (9)	0.0002 (7)	0.0006 (7)	0.0014 (7)
C2	0.0182 (9)	0.0204 (9)	0.0201 (9)	0.0034 (7)	−0.0005 (7)	−0.0017 (7)
C3	0.0235 (9)	0.0163 (8)	0.0206 (9)	0.0009 (7)	0.0028 (7)	−0.0011 (7)
C4	0.0213 (9)	0.0212 (9)	0.0261 (10)	−0.0034 (7)	−0.0001 (7)	0.0048 (7)
C5	0.0213 (9)	0.0250 (10)	0.0289 (10)	−0.0074 (8)	−0.0056 (7)	0.0029 (8)
C6	0.0341 (11)	0.0185 (9)	0.0259 (10)	−0.0019 (8)	−0.0061 (8)	−0.0019 (7)
C7	0.0250 (9)	0.0230 (9)	0.0195 (9)	0.0043 (8)	−0.0002 (7)	−0.0037 (7)
C8	0.0238 (9)	0.0260 (9)	0.0176 (9)	−0.0027 (8)	−0.0004 (7)	0.0002 (7)
C9	0.0254 (9)	0.0150 (8)	0.0236 (9)	0.0005 (7)	−0.0008 (7)	0.0027 (7)
C10	0.0209 (9)	0.0281 (10)	0.0277 (10)	0.0022 (8)	−0.0044 (8)	0.0042 (8)
C11	0.0207 (9)	0.0209 (9)	0.0216 (9)	0.0041 (7)	0.0029 (7)	−0.0015 (7)
C12	0.0311 (11)	0.0299 (10)	0.0202 (10)	0.0010 (8)	−0.0021 (8)	0.0001 (8)
N1	0.0214 (8)	0.0187 (7)	0.0183 (8)	−0.0001 (6)	0.0022 (6)	0.0015 (6)
O1	0.0257 (7)	0.0330 (7)	0.0216 (7)	−0.0080 (6)	−0.0009 (5)	−0.0008 (6)
S1	0.0221 (3)	0.0229 (3)	0.0175 (3)	−0.00163 (17)	−0.00125 (16)	0.00108 (17)
O2	0.0240 (7)	0.0328 (8)	0.0337 (8)	−0.0003 (6)	0.0006 (5)	−0.0114 (6)
O3	0.0433 (9)	0.0270 (8)	0.0323 (8)	0.0092 (6)	−0.0058 (6)	0.0028 (6)
O4	0.0406 (8)	0.0440 (8)	0.0226 (7)	−0.0109 (7)	−0.0093 (6)	0.0014 (6)
C13	0.0489 (13)	0.0353 (11)	0.0227 (10)	−0.0117 (10)	0.0030 (9)	0.0021 (8)

C1—N1	1.480 (2)	C8—H8A	0.9900
C1—C4	1.530 (2)	C8—H8B	0.9900
C1—C3	1.531 (2)	C9—C10	1.527 (2)
C1—C2	1.531 (2)	C9—H9	1.0000
C2—C7	1.530 (3)	C10—H10A	0.9900
C2—H2A	0.9900	C10—H10B	0.9900
C2—H2B	0.9900	C11—N1	1.292 (2)
C3—C9	1.527 (2)	C11—O1	1.294 (2)
C3—H3A	0.9900	C11—C12	1.487 (3)
C3—H3B	0.9900	C12—H12A	0.9800
C4—C5	1.526 (3)	C12—H12B	0.9800
C4—H4A	0.9900	C12—H12C	0.9800
C4—H4B	0.9900	N1—H1	0.87 (2)
C5—C6	1.527 (3)	O1—H2	0.98 (2)
C5—C10	1.528 (2)	S1—O4	1.4343 (14)
C5—H5	1.0000	S1—O3	1.4489 (14)
C6—C7	1.529 (3)	S1—O2	1.4695 (15)
C6—H6A	0.9900	S1—C13	1.7448 (19)
C6—H6B	0.9900	C13—H13A	0.9800
C7—C8	1.528 (2)	C13—H13B	0.9800
C7—H7	1.0000	C13—H13C	0.9800
C8—C9	1.528 (2)
N1—C1—C4	106.69 (13)	C7—C8—H8A	109.8
N1—C1—C3	111.76 (14)	C9—C8—H8A	109.8
C4—C1—C3	109.01 (14)	C7—C8—H8B	109.8
N1—C1—C2	109.73 (14)	C9—C8—H8B	109.8
C4—C1—C2	109.20 (14)	H8A—C8—H8B	108.2
C3—C1—C2	110.34 (14)	C3—C9—C10	109.73 (14)
C7—C2—C1	109.40 (14)	C3—C9—C8	109.77 (14)
C7—C2—H2A	109.8	C10—C9—C8	109.74 (14)
C1—C2—H2A	109.8	C3—C9—H9	109.2
C7—C2—H2B	109.8	C10—C9—H9	109.2
C1—C2—H2B	109.8	C8—C9—H9	109.2
H2A—C2—H2B	108.2	C9—C10—C5	109.05 (14)
C9—C3—C1	108.89 (14)	C9—C10—H10A	109.9
C9—C3—H3A	109.9	C5—C10—H10A	109.9
C1—C3—H3A	109.9	C9—C10—H10B	109.9
C9—C3—H3B	109.9	C5—C10—H10B	109.9
C1—C3—H3B	109.9	H10A—C10—H10B	108.3
H3A—C3—H3B	108.3	N1—C11—O1	119.67 (16)
C5—C4—C1	109.48 (14)	N1—C11—C12	120.42 (16)
C5—C4—H4A	109.8	O1—C11—C12	119.90 (16)
C1—C4—H4A	109.8	C11—C12—H12A	109.5
C5—C4—H4B	109.8	C11—C12—H12B	109.5
C1—C4—H4B	109.8	H12A—C12—H12B	109.5
H4A—C4—H4B	108.2	C11—C12—H12C	109.5
C4—C5—C6	109.89 (15)	H12A—C12—H12C	109.5
C4—C5—C10	109.34 (15)	H12B—C12—H12C	109.5
C6—C5—C10	109.53 (15)	C11—N1—C1	127.58 (15)
C4—C5—H5	109.4	C11—N1—H1	115.2 (14)
C6—C5—H5	109.4	C1—N1—H1	117.2 (14)
C10—C5—H5	109.4	C11—O1—H2	113.8 (13)
C5—C6—C7	109.45 (14)	O4—S1—O3	115.18 (9)
C5—C6—H6A	109.8	O4—S1—O2	112.12 (8)
C7—C6—H6A	109.8	O3—S1—O2	110.11 (8)
C5—C6—H6B	109.8	O4—S1—C13	107.03 (9)
C7—C6—H6B	109.8	O3—S1—C13	106.76 (9)
H6A—C6—H6B	108.2	O2—S1—C13	104.92 (10)
C8—C7—C6	109.47 (15)	S1—C13—H13A	109.5
C8—C7—C2	109.44 (14)	S1—C13—H13B	109.5
C6—C7—C2	109.23 (15)	H13A—C13—H13B	109.5
C8—C7—H7	109.6	S1—C13—H13C	109.5
C6—C7—H7	109.6	H13A—C13—H13C	109.5
C2—C7—H7	109.6	H13B—C13—H13C	109.5
C7—C8—C9	109.49 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.87 (2)	1.98 (2)	2.838 (2)	170.1 (19)
O1—H2···O2	0.98 (2)	1.49 (2)	2.4632 (18)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.87 (2)	1.98 (2)	2.838 (2)	170.1 (19)
O1—H2⋯O2	0.98 (2)	1.49 (2)	2.4632 (18)	173 (2)

Symmetry code: (i) .