2-(Tricyclo[3.3.1.1]dec-2-ylamino)ethanol hemihydrate.

The title adamantane derivative, C(12)H(21)NO·0.5H(2)O, was synthesized as part of an investigation into the biological activities of cage amino-alcohol compounds as potential anti-tuberculosis agents. The structure displays inter-molecular O-H⋯N, N-H⋯O, O-H⋯O hydrogen bonding and a layered packing structure with distinct hydro-philic and hydro-phobic regions. The water molecule lies on a twofold rotation axis.

Related literature

For related literature, see: Bogatcheva et al. (2006 ▶); du Pont de Nemours and Co. (1969 ▶); Lee et al. (2003 ▶); Tripathi et al. (2006 ▶).

Experimental

Crystal data

C12H21NO·0.5H2O

M = 204.31

Monoclinic,

a = 11.6739 (3) Å

b = 6.5043 (2) Å

c = 28.6241 (7) Å

β = 99.8620 (10)°

V = 2141.33 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 173 (2) K

0.56 × 0.43 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

13147 measured reflections

2584 independent reflections

2352 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.07

2584 reflections

141 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016851/hg2403sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016851/hg2403Isup2.hkl

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

C12H21NO·0.5H2O	F(000) = 904
Mr = 204.31	Dx = 1.267 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7587 reflections
a = 11.6739 (3) Å	θ = 2.9–28.3°
b = 6.5043 (2) Å	µ = 0.08 mm−1
c = 28.6241 (7) Å	T = 173 K
β = 99.862 (1)°	Plate, colourless
V = 2141.33 (10) Å3	0.56 × 0.43 × 0.18 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2352 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
graphite	θmax = 28.0°, θmin = 1.4°
phi and ω scans	h = −15→15
13147 measured reflections	k = −8→8
2584 independent reflections	l = −37→37

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0507P)2 + 1.5961P] where P = (Fo2 + 2Fc2)/3
2584 reflections	(Δ/σ)max = 0.001
141 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.19 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
C1	0.76341 (9)	−0.06132 (17)	0.61221 (4)	0.0189 (2)
H1	0.6899	−0.0946	0.6241	0.023*
C2	0.81420 (9)	0.13986 (16)	0.63482 (3)	0.0156 (2)
H2	0.7582	0.2520	0.6229	0.019*
C3	0.92859 (10)	0.18681 (17)	0.61700 (4)	0.0181 (2)
H3	0.9635	0.3162	0.6321	0.022*
C4	1.01487 (10)	0.00885 (18)	0.62888 (4)	0.0205 (2)
H4A	1.0880	0.0411	0.6173	0.025*
H4B	1.0334	−0.0096	0.6637	0.025*
C5	0.96251 (10)	−0.18982 (17)	0.60569 (4)	0.0208 (2)
H5	1.0189	−0.3054	0.6137	0.025*
C6	0.93562 (11)	−0.16124 (19)	0.55178 (4)	0.0243 (3)
H6A	1.0082	−0.1301	0.5396	0.029*
H6B	0.9023	−0.2896	0.5366	0.029*
C7	0.84905 (11)	0.01531 (19)	0.53962 (4)	0.0240 (3)
H7	0.8313	0.0338	0.5044	0.029*
C8	0.73704 (10)	−0.0346 (2)	0.55821 (4)	0.0250 (3)
H8A	0.7025	−0.1627	0.5433	0.030*
H8B	0.6802	0.0781	0.5499	0.030*
C9	0.85024 (10)	−0.23740 (17)	0.62443 (4)	0.0208 (2)
H9A	0.8159	−0.3668	0.6101	0.025*
H9B	0.8677	−0.2561	0.6593	0.025*
C10	0.90159 (11)	0.21388 (18)	0.56282 (4)	0.0241 (3)
H10A	0.8462	0.3288	0.5546	0.029*
H10B	0.9739	0.2475	0.5507	0.029*
C11	0.83975 (9)	0.33596 (16)	0.70953 (4)	0.0170 (2)
H11A	0.7728	0.4258	0.6973	0.020*
H11B	0.9109	0.4007	0.7018	0.020*
C12	0.85067 (10)	0.31373 (16)	0.76292 (4)	0.0186 (2)
H12A	0.7770	0.2587	0.7706	0.022*
H12B	0.9132	0.2141	0.7745	0.022*
N1	0.82297 (8)	0.13298 (14)	0.68680 (3)	0.0156 (2)
O1	0.87618 (7)	0.50454 (12)	0.78653 (3)	0.01947 (19)
H1C	0.8167	0.5477	0.7963	0.029*
O1W	1.0000	0.82045 (19)	0.7500	0.0240 (3)
H1B	0.8774 (13)	0.053 (2)	0.6990 (5)	0.024 (4)*
H1W	1.0445 (14)	0.737 (3)	0.7380 (6)	0.037 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0192 (5)	0.0197 (5)	0.0178 (5)	−0.0041 (4)	0.0030 (4)	−0.0029 (4)
C2	0.0175 (5)	0.0146 (5)	0.0146 (5)	0.0007 (4)	0.0027 (4)	0.0003 (4)
C3	0.0224 (5)	0.0155 (5)	0.0172 (5)	−0.0032 (4)	0.0059 (4)	−0.0004 (4)
C4	0.0178 (5)	0.0236 (6)	0.0200 (5)	0.0000 (4)	0.0033 (4)	−0.0024 (4)
C5	0.0247 (6)	0.0180 (5)	0.0198 (5)	0.0045 (4)	0.0038 (4)	−0.0010 (4)
C6	0.0310 (6)	0.0236 (6)	0.0193 (5)	0.0008 (5)	0.0072 (4)	−0.0046 (4)
C7	0.0313 (6)	0.0265 (6)	0.0138 (5)	0.0015 (5)	0.0030 (4)	0.0010 (4)
C8	0.0245 (6)	0.0296 (6)	0.0188 (5)	−0.0003 (5)	−0.0023 (4)	−0.0036 (4)
C9	0.0300 (6)	0.0137 (5)	0.0189 (5)	−0.0029 (4)	0.0048 (4)	−0.0006 (4)
C10	0.0339 (6)	0.0206 (6)	0.0195 (5)	0.0004 (5)	0.0092 (4)	0.0040 (4)
C11	0.0207 (5)	0.0133 (5)	0.0170 (5)	0.0003 (4)	0.0033 (4)	−0.0009 (4)
C12	0.0239 (5)	0.0151 (5)	0.0172 (5)	−0.0006 (4)	0.0049 (4)	−0.0010 (4)
N1	0.0189 (4)	0.0131 (4)	0.0149 (4)	0.0008 (3)	0.0033 (3)	−0.0003 (3)
O1	0.0195 (4)	0.0188 (4)	0.0208 (4)	−0.0012 (3)	0.0054 (3)	−0.0058 (3)
O1W	0.0293 (6)	0.0175 (6)	0.0259 (6)	0.000	0.0064 (5)	0.000

C1—C9	1.5297 (16)	C7—C8	1.5287 (17)
C1—C8	1.5334 (15)	C7—C10	1.5316 (17)
C1—C2	1.5334 (14)	C7—H7	1.0000
C1—H1	1.0000	C8—H8A	0.9900
C2—N1	1.4745 (12)	C8—H8B	0.9900
C2—C3	1.5395 (15)	C9—H9A	0.9900
C2—H2	1.0000	C9—H9B	0.9900
C3—C4	1.5339 (15)	C10—H10A	0.9900
C3—C10	1.5388 (15)	C10—H10B	0.9900
C3—H3	1.0000	C11—N1	1.4700 (13)
C4—C5	1.5314 (16)	C11—C12	1.5187 (14)
C4—H4A	0.9900	C11—H11A	0.9900
C4—H4B	0.9900	C11—H11B	0.9900
C5—C9	1.5305 (16)	C12—O1	1.4200 (13)
C5—C6	1.5324 (15)	C12—H12A	0.9900
C5—H5	1.0000	C12—H12B	0.9900
C6—C7	1.5299 (17)	N1—H1B	0.849 (16)
C6—H6A	0.9900	O1—H1C	0.8400
C6—H6B	0.9900	O1W—H1W	0.863 (16)
C9—C1—C8	109.03 (9)	C6—C7—C10	109.54 (10)
C9—C1—C2	110.44 (9)	C8—C7—H7	109.5
C8—C1—C2	108.97 (9)	C6—C7—H7	109.5
C9—C1—H1	109.5	C10—C7—H7	109.5
C8—C1—H1	109.5	C7—C8—C1	109.82 (9)
C2—C1—H1	109.5	C7—C8—H8A	109.7
N1—C2—C1	110.79 (8)	C1—C8—H8A	109.7
N1—C2—C3	115.22 (8)	C7—C8—H8B	109.7
C1—C2—C3	108.91 (8)	C1—C8—H8B	109.7
N1—C2—H2	107.2	H8A—C8—H8B	108.2
C1—C2—H2	107.2	C1—C9—C5	110.01 (9)
C3—C2—H2	107.2	C1—C9—H9A	109.7
C4—C3—C10	108.86 (9)	C5—C9—H9A	109.7
C4—C3—C2	110.53 (9)	C1—C9—H9B	109.7
C10—C3—C2	108.48 (9)	C5—C9—H9B	109.7
C4—C3—H3	109.6	H9A—C9—H9B	108.2
C10—C3—H3	109.6	C7—C10—C3	109.77 (9)
C2—C3—H3	109.6	C7—C10—H10A	109.7
C5—C4—C3	110.03 (9)	C3—C10—H10A	109.7
C5—C4—H4A	109.7	C7—C10—H10B	109.7
C3—C4—H4A	109.7	C3—C10—H10B	109.7
C5—C4—H4B	109.7	H10A—C10—H10B	108.2
C3—C4—H4B	109.7	N1—C11—C12	109.98 (8)
H4A—C4—H4B	108.2	N1—C11—H11A	109.7
C9—C5—C4	108.72 (9)	C12—C11—H11A	109.7
C9—C5—C6	109.72 (9)	N1—C11—H11B	109.7
C4—C5—C6	109.38 (9)	C12—C11—H11B	109.7
C9—C5—H5	109.7	H11A—C11—H11B	108.2
C4—C5—H5	109.7	O1—C12—C11	111.73 (8)
C6—C5—H5	109.7	O1—C12—H12A	109.3
C7—C6—C5	109.49 (9)	C11—C12—H12A	109.3
C7—C6—H6A	109.8	O1—C12—H12B	109.3
C5—C6—H6A	109.8	C11—C12—H12B	109.3
C7—C6—H6B	109.8	H12A—C12—H12B	107.9
C5—C6—H6B	109.8	C11—N1—C2	113.60 (8)
H6A—C6—H6B	108.2	C11—N1—H1B	109.6 (10)
C8—C7—C6	109.42 (10)	C2—N1—H1B	110.6 (10)
C8—C7—C10	109.34 (10)	C12—O1—H1C	109.5
C9—C1—C2—N1	−69.54 (11)	C6—C7—C8—C1	60.43 (12)
C8—C1—C2—N1	170.72 (9)	C10—C7—C8—C1	−59.53 (12)
C9—C1—C2—C3	58.18 (11)	C9—C1—C8—C7	−60.00 (12)
C8—C1—C2—C3	−61.56 (11)	C2—C1—C8—C7	60.61 (12)
N1—C2—C3—C4	67.40 (11)	C8—C1—C9—C5	59.43 (11)
C1—C2—C3—C4	−57.78 (11)	C2—C1—C9—C5	−60.27 (11)
N1—C2—C3—C10	−173.32 (9)	C4—C5—C9—C1	60.16 (11)
C1—C2—C3—C10	61.50 (11)	C6—C5—C9—C1	−59.42 (11)
C10—C3—C4—C5	−59.70 (12)	C8—C7—C10—C3	59.75 (12)
C2—C3—C4—C5	59.36 (11)	C6—C7—C10—C3	−60.14 (12)
C3—C4—C5—C9	−59.71 (11)	C4—C3—C10—C7	59.61 (12)
C3—C4—C5—C6	60.09 (12)	C2—C3—C10—C7	−60.72 (12)
C9—C5—C6—C7	59.30 (12)	N1—C11—C12—O1	175.36 (9)
C4—C5—C6—C7	−59.87 (12)	C12—C11—N1—C2	−178.67 (8)
C5—C6—C7—C8	−59.80 (12)	C1—C2—N1—C11	−164.04 (9)
C5—C6—C7—C10	60.05 (12)	C3—C2—N1—C11	71.76 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N1i	0.84	1.86	2.7007 (12)	175
N1—H1B···O1Wii	0.849 (16)	2.398 (16)	3.2241 (12)	164.6 (14)
O1W—H1W···O1iii	0.863 (16)	1.963 (17)	2.8147 (12)	168.7 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯N1i	0.84	1.86	2.7007 (12)	175
N1—H1B⋯O1Wii	0.849 (16)	2.398 (16)	3.2241 (12)	164.6 (14)
O1W—H1W⋯O1iii	0.863 (16)	1.963 (17)	2.8147 (12)	168.7 (16)

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