organic compounds
2-[(Adamantan-1-yl)aminomethyl]-4-chlorophenol hemihydrate
aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
*Correspondence e-mail: jinxudong@yahoo.com
In the title compound, C17H22ClNO·0.5H2O, the water molecule O atom resides on a twofold rotation axis. In the organic molecule, the phenol group forms an intramolecular O—H⋯N hydrogen bond. In the crystal, pairs of organic molecules are hydrogen bonded through bridging solvent water molecules, forming chains along the b-axis direction.
Related literature
For the synthesis and ). For the synthesis and applications of amantadine derivatives, see: Camps et al. (2008).
of 2-[(adamantan-1-ylamino)methyl]phenol, see: Wang & Tao (2012Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812045175/ld2073sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812045175/ld2073Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812045175/ld2073Isup3.cml
Amantadine hydrochloride (0.376 g, 2.0 mmol) and KOH (0.112 g, 2.0 mmol) were stirred in 10 ml of anhydrous alcohol for 2 h. The produced white precipitate was filtered out and the transparent filtrate was added dropwise to 5-chloro-2-hydroxybenzaldehyde (0.312 g, 2.0 mmol) in 10 ml of anhydrous alcohol under constant stirring. The resulting solution was refluxed for ca. 3 h, concentrated to about 5 ml through reduced pressure distillation and then left at room temperature. A yellow Schiff base precipitate was obtained after one week under slow solvent evaporation.
NaBH4 (0.303 g, 8 mmol) was added into solution of the Schiff base (0.580 g, 2 mmol) in anhydrous methanol (10 ml). After 1 h stirring, a light-yellow solid, 4-chloro-2-((adamantan-1-ylamino)methyl)phenol was filtered and dried. A crystal of the title compound suitable for X-ray analysis has developed from a solution in H2O/EtOH mixture (1:2 v/v) after 5 days of slow solvent evaporation.
The C-bound H atoms were positioned geometrically with C—H = 0.93–0.98 Å, and treated as riding with Uiso(H) = 1.2 Ueq(C). H atoms bonded to N and O atoms were located in difference Fourier series and refined isotropically.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C17H22ClNO·0.5H2O | F(000) = 1288 |
Mr = 300.82 | Dx = 1.347 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 941 reflections |
a = 25.469 (16) Å | θ = 3.3–22.6° |
b = 6.365 (4) Å | µ = 0.26 mm−1 |
c = 18.306 (11) Å | T = 296 K |
β = 91.815 (12)° | Block, yellow |
V = 2966 (3) Å3 | 0.35 × 0.30 × 0.16 mm |
Z = 8 |
Bruker APEXII CCD area-detector diffractometer | 2606 independent reflections |
Radiation source: fine-focus sealed tube | 1798 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −30→28 |
Tmin = 0.915, Tmax = 0.960 | k = −7→7 |
6372 measured reflections | l = −13→21 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0716P)2 + 4.2412P] where P = (Fo2 + 2Fc2)/3 |
2606 reflections | (Δ/σ)max = 0.001 |
198 parameters | Δρmax = 0.39 e Å−3 |
3 restraints | Δρmin = −0.40 e Å−3 |
C17H22ClNO·0.5H2O | V = 2966 (3) Å3 |
Mr = 300.82 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.469 (16) Å | µ = 0.26 mm−1 |
b = 6.365 (4) Å | T = 296 K |
c = 18.306 (11) Å | 0.35 × 0.30 × 0.16 mm |
β = 91.815 (12)° |
Bruker APEXII CCD area-detector diffractometer | 2606 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1798 reflections with I > 2σ(I) |
Tmin = 0.915, Tmax = 0.960 | Rint = 0.098 |
6372 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 3 restraints |
wR(F2) = 0.216 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.39 e Å−3 |
2606 reflections | Δρmin = −0.40 e Å−3 |
198 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.68802 (17) | 0.9819 (7) | 0.1855 (2) | 0.0245 (10) | |
H1C | 0.6718 | 1.0857 | 0.2164 | 0.029* | |
H1D | 0.7254 | 1.0115 | 0.1847 | 0.029* | |
C2 | 0.67926 (18) | 0.7615 (7) | 0.2166 (2) | 0.0276 (11) | |
H2 | 0.6948 | 0.7526 | 0.2662 | 0.033* | |
C3 | 0.61919 (16) | 0.7207 (7) | 0.2187 (2) | 0.0225 (10) | |
H3A | 0.6128 | 0.5828 | 0.2392 | 0.027* | |
H3B | 0.6030 | 0.8246 | 0.2495 | 0.027* | |
C4 | 0.59505 (16) | 0.7331 (6) | 0.1410 (2) | 0.0181 (9) | |
C5 | 0.60470 (15) | 0.9535 (6) | 0.1103 (2) | 0.0194 (9) | |
H5A | 0.5884 | 1.0577 | 0.1410 | 0.023* | |
H5B | 0.5890 | 0.9646 | 0.0615 | 0.023* | |
C6 | 0.66397 (17) | 0.9950 (7) | 0.1079 (2) | 0.0222 (10) | |
H6 | 0.6700 | 1.1354 | 0.0879 | 0.027* | |
C7 | 0.68971 (16) | 0.8294 (6) | 0.0594 (2) | 0.0194 (9) | |
H7A | 0.6748 | 0.8377 | 0.0101 | 0.023* | |
H7B | 0.7271 | 0.8560 | 0.0575 | 0.023* | |
C8 | 0.70416 (16) | 0.5981 (7) | 0.1683 (3) | 0.0256 (10) | |
H8A | 0.6985 | 0.4590 | 0.1882 | 0.031* | |
H8B | 0.7417 | 0.6221 | 0.1671 | 0.031* | |
C9 | 0.68029 (16) | 0.6101 (6) | 0.0909 (2) | 0.0217 (10) | |
H9 | 0.6967 | 0.5042 | 0.0601 | 0.026* | |
C10 | 0.62049 (16) | 0.5697 (7) | 0.0927 (2) | 0.0215 (10) | |
H10A | 0.6052 | 0.5776 | 0.0435 | 0.026* | |
H10B | 0.6140 | 0.4301 | 0.1117 | 0.026* | |
C11 | 0.50199 (15) | 0.7241 (6) | 0.0828 (2) | 0.0195 (9) | |
H11A | 0.4970 | 0.8739 | 0.0758 | 0.023* | |
H11B | 0.5173 | 0.6669 | 0.0393 | 0.023* | |
C12 | 0.45058 (16) | 0.6210 (6) | 0.0955 (2) | 0.0182 (9) | |
C13 | 0.44999 (15) | 0.4119 (6) | 0.1226 (2) | 0.0190 (9) | |
C14 | 0.40219 (17) | 0.3142 (7) | 0.1333 (2) | 0.0225 (10) | |
H14 | 0.4017 | 0.1768 | 0.1506 | 0.027* | |
C15 | 0.35494 (16) | 0.4183 (7) | 0.1187 (2) | 0.0220 (9) | |
H15 | 0.3230 | 0.3522 | 0.1263 | 0.026* | |
C16 | 0.35647 (16) | 0.6241 (7) | 0.0923 (2) | 0.0196 (9) | |
C17 | 0.40353 (16) | 0.7250 (6) | 0.0811 (2) | 0.0184 (9) | |
H17 | 0.4037 | 0.8626 | 0.0640 | 0.022* | |
Cl1 | 0.29758 (4) | 0.75941 (17) | 0.07489 (6) | 0.0262 (4) | |
H1 | 0.5251 (19) | 0.367 (15) | 0.133 (6) | 0.16 (5)* | |
H1A | 0.5178 (18) | 0.748 (7) | 0.181 (2) | 0.045 (16)* | |
N1 | 0.53801 (14) | 0.6858 (6) | 0.14802 (19) | 0.0207 (8) | |
O1 | 0.49570 (13) | 0.3128 (5) | 0.13804 (18) | 0.0272 (8) | |
O1W | 0.5000 | 1.0204 (8) | 0.2500 | 0.0532 (17) | |
H1W | 0.491 (2) | 1.097 (7) | 0.286 (2) | 0.040 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.025 (2) | 0.030 (2) | 0.019 (2) | −0.0099 (19) | 0.0030 (17) | −0.0067 (19) |
C2 | 0.027 (2) | 0.038 (3) | 0.017 (2) | −0.005 (2) | −0.0043 (18) | 0.005 (2) |
C3 | 0.021 (2) | 0.028 (2) | 0.019 (2) | −0.0037 (18) | 0.0025 (17) | 0.0021 (18) |
C4 | 0.017 (2) | 0.015 (2) | 0.022 (2) | −0.0023 (16) | 0.0028 (16) | 0.0003 (17) |
C5 | 0.019 (2) | 0.020 (2) | 0.020 (2) | 0.0036 (17) | 0.0064 (16) | −0.0012 (17) |
C6 | 0.029 (2) | 0.016 (2) | 0.022 (2) | −0.0015 (18) | 0.0032 (18) | −0.0026 (18) |
C7 | 0.019 (2) | 0.020 (2) | 0.020 (2) | −0.0029 (17) | 0.0056 (16) | −0.0023 (17) |
C8 | 0.015 (2) | 0.025 (2) | 0.036 (3) | −0.0031 (18) | 0.0000 (18) | 0.006 (2) |
C9 | 0.020 (2) | 0.018 (2) | 0.028 (3) | 0.0019 (17) | 0.0057 (17) | −0.0041 (18) |
C10 | 0.025 (2) | 0.018 (2) | 0.021 (2) | −0.0047 (18) | 0.0019 (17) | −0.0019 (17) |
C11 | 0.018 (2) | 0.022 (2) | 0.019 (2) | 0.0006 (17) | −0.0007 (16) | 0.0023 (17) |
C12 | 0.024 (2) | 0.018 (2) | 0.013 (2) | 0.0003 (17) | −0.0001 (16) | −0.0017 (16) |
C13 | 0.021 (2) | 0.021 (2) | 0.016 (2) | 0.0025 (17) | 0.0014 (16) | −0.0028 (17) |
C14 | 0.030 (2) | 0.015 (2) | 0.022 (2) | −0.0027 (18) | −0.0010 (18) | 0.0008 (18) |
C15 | 0.021 (2) | 0.029 (2) | 0.016 (2) | −0.0024 (18) | −0.0002 (16) | −0.0037 (18) |
C16 | 0.022 (2) | 0.026 (2) | 0.011 (2) | 0.0057 (18) | −0.0022 (16) | −0.0013 (17) |
C17 | 0.024 (2) | 0.018 (2) | 0.013 (2) | 0.0010 (17) | 0.0009 (16) | 0.0015 (16) |
Cl1 | 0.0204 (6) | 0.0357 (7) | 0.0225 (6) | 0.0044 (5) | 0.0000 (4) | 0.0045 (5) |
N1 | 0.0196 (18) | 0.029 (2) | 0.0139 (19) | 0.0023 (16) | −0.0018 (14) | −0.0034 (15) |
O1 | 0.0271 (18) | 0.0216 (16) | 0.0326 (19) | 0.0043 (14) | −0.0043 (14) | 0.0000 (14) |
O1W | 0.037 (3) | 0.017 (3) | 0.106 (6) | 0.000 | 0.012 (3) | 0.000 |
C1—C6 | 1.531 (6) | C8—H8B | 0.9700 |
C1—C2 | 1.533 (6) | C9—C10 | 1.546 (6) |
C1—H1C | 0.9700 | C9—H9 | 0.9800 |
C1—H1D | 0.9700 | C10—H10A | 0.9700 |
C2—C8 | 1.517 (6) | C10—H10B | 0.9700 |
C2—C3 | 1.553 (6) | C11—C12 | 1.489 (6) |
C2—H2 | 0.9800 | C11—N1 | 1.502 (5) |
C3—C4 | 1.534 (6) | C11—H11A | 0.9700 |
C3—H3A | 0.9700 | C11—H11B | 0.9700 |
C3—H3B | 0.9700 | C12—C17 | 1.387 (6) |
C4—N1 | 1.493 (5) | C12—C13 | 1.421 (6) |
C4—C10 | 1.523 (6) | C13—O1 | 1.346 (5) |
C4—C5 | 1.534 (5) | C13—C14 | 1.387 (6) |
C5—C6 | 1.534 (6) | C14—C15 | 1.392 (6) |
C5—H5A | 0.9700 | C14—H14 | 0.9300 |
C5—H5B | 0.9700 | C15—C16 | 1.397 (6) |
C6—C7 | 1.539 (6) | C15—H15 | 0.9300 |
C6—H6 | 0.9800 | C16—C17 | 1.381 (6) |
C7—C9 | 1.532 (6) | C16—Cl1 | 1.750 (4) |
C7—H7A | 0.9700 | C17—H17 | 0.9300 |
C7—H7B | 0.9700 | N1—H1A | 0.90 (2) |
C8—C9 | 1.524 (6) | O1—H1 | 0.83 (2) |
C8—H8A | 0.9700 | O1W—H1W | 0.847 (19) |
C6—C1—C2 | 109.6 (3) | C9—C8—H8A | 109.6 |
C6—C1—H1C | 109.8 | C2—C8—H8B | 109.6 |
C2—C1—H1C | 109.8 | C9—C8—H8B | 109.6 |
C6—C1—H1D | 109.8 | H8A—C8—H8B | 108.1 |
C2—C1—H1D | 109.8 | C8—C9—C7 | 109.4 (3) |
H1C—C1—H1D | 108.2 | C8—C9—C10 | 109.7 (3) |
C8—C2—C1 | 110.0 (4) | C7—C9—C10 | 109.0 (3) |
C8—C2—C3 | 109.3 (4) | C8—C9—H9 | 109.6 |
C1—C2—C3 | 108.5 (4) | C7—C9—H9 | 109.6 |
C8—C2—H2 | 109.7 | C10—C9—H9 | 109.6 |
C1—C2—H2 | 109.7 | C4—C10—C9 | 109.6 (3) |
C3—C2—H2 | 109.7 | C4—C10—H10A | 109.7 |
C4—C3—C2 | 109.5 (3) | C9—C10—H10A | 109.7 |
C4—C3—H3A | 109.8 | C4—C10—H10B | 109.7 |
C2—C3—H3A | 109.8 | C9—C10—H10B | 109.7 |
C4—C3—H3B | 109.8 | H10A—C10—H10B | 108.2 |
C2—C3—H3B | 109.8 | C12—C11—N1 | 108.9 (3) |
H3A—C3—H3B | 108.2 | C12—C11—H11A | 109.9 |
N1—C4—C10 | 110.2 (3) | N1—C11—H11A | 109.9 |
N1—C4—C5 | 112.6 (3) | C12—C11—H11B | 109.9 |
C10—C4—C5 | 109.7 (3) | N1—C11—H11B | 109.9 |
N1—C4—C3 | 105.8 (3) | H11A—C11—H11B | 108.3 |
C10—C4—C3 | 109.7 (3) | C17—C12—C13 | 119.7 (4) |
C5—C4—C3 | 108.8 (3) | C17—C12—C11 | 121.3 (4) |
C4—C5—C6 | 109.7 (3) | C13—C12—C11 | 119.1 (3) |
C4—C5—H5A | 109.7 | O1—C13—C14 | 121.2 (4) |
C6—C5—H5A | 109.7 | O1—C13—C12 | 119.6 (4) |
C4—C5—H5B | 109.7 | C14—C13—C12 | 119.3 (4) |
C6—C5—H5B | 109.7 | C13—C14—C15 | 121.1 (4) |
H5A—C5—H5B | 108.2 | C13—C14—H14 | 119.4 |
C1—C6—C5 | 109.2 (3) | C15—C14—H14 | 119.4 |
C1—C6—C7 | 109.5 (3) | C14—C15—C16 | 118.6 (4) |
C5—C6—C7 | 109.7 (3) | C14—C15—H15 | 120.7 |
C1—C6—H6 | 109.5 | C16—C15—H15 | 120.7 |
C5—C6—H6 | 109.5 | C17—C16—C15 | 121.4 (4) |
C7—C6—H6 | 109.5 | C17—C16—Cl1 | 119.2 (3) |
C9—C7—C6 | 109.4 (3) | C15—C16—Cl1 | 119.4 (3) |
C9—C7—H7A | 109.8 | C16—C17—C12 | 119.9 (4) |
C6—C7—H7A | 109.8 | C16—C17—H17 | 120.0 |
C9—C7—H7B | 109.8 | C12—C17—H17 | 120.0 |
C6—C7—H7B | 109.8 | C4—N1—C11 | 118.0 (3) |
H7A—C7—H7B | 108.2 | C4—N1—H1A | 123 (4) |
C2—C8—C9 | 110.2 (3) | C11—N1—H1A | 96 (4) |
C2—C8—H8A | 109.6 | C13—O1—H1 | 124 (7) |
C6—C1—C2—C8 | 59.0 (5) | C5—C4—C10—C9 | 60.1 (4) |
C6—C1—C2—C3 | −60.5 (4) | C3—C4—C10—C9 | −59.4 (4) |
C8—C2—C3—C4 | −59.4 (4) | C8—C9—C10—C4 | 59.3 (4) |
C1—C2—C3—C4 | 60.6 (4) | C7—C9—C10—C4 | −60.5 (4) |
C2—C3—C4—N1 | 178.3 (3) | N1—C11—C12—C17 | 134.1 (4) |
C2—C3—C4—C10 | 59.5 (4) | N1—C11—C12—C13 | −46.0 (5) |
C2—C3—C4—C5 | −60.5 (4) | C17—C12—C13—O1 | −178.6 (4) |
N1—C4—C5—C6 | 177.4 (3) | C11—C12—C13—O1 | 1.5 (6) |
C10—C4—C5—C6 | −59.5 (4) | C17—C12—C13—C14 | 0.9 (6) |
C3—C4—C5—C6 | 60.5 (4) | C11—C12—C13—C14 | −179.0 (4) |
C2—C1—C6—C5 | 60.9 (4) | O1—C13—C14—C15 | 178.8 (4) |
C2—C1—C6—C7 | −59.2 (4) | C12—C13—C14—C15 | −0.7 (6) |
C4—C5—C6—C1 | −60.7 (4) | C13—C14—C15—C16 | 0.4 (6) |
C4—C5—C6—C7 | 59.3 (4) | C14—C15—C16—C17 | −0.4 (6) |
C1—C6—C7—C9 | 59.9 (4) | C14—C15—C16—Cl1 | −178.9 (3) |
C5—C6—C7—C9 | −59.9 (4) | C15—C16—C17—C12 | 0.7 (6) |
C1—C2—C8—C9 | −59.3 (4) | Cl1—C16—C17—C12 | 179.2 (3) |
C3—C2—C8—C9 | 59.7 (4) | C13—C12—C17—C16 | −0.9 (6) |
C2—C8—C9—C7 | 59.7 (4) | C11—C12—C17—C16 | 179.0 (4) |
C2—C8—C9—C10 | −59.8 (4) | C10—C4—N1—C11 | −72.3 (4) |
C6—C7—C9—C8 | −59.8 (4) | C5—C4—N1—C11 | 50.5 (5) |
C6—C7—C9—C10 | 60.1 (4) | C3—C4—N1—C11 | 169.2 (3) |
N1—C4—C10—C9 | −175.5 (3) | C12—C11—N1—C4 | 166.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.83 (6) | 2.07 (9) | 2.611 (5) | 122 (7) |
O1W—H1W···O1i | 0.84 (4) | 1.99 (4) | 2.768 (5) | 153 (5) |
N1—H1A···O1W | 0.90 (4) | 2.20 (4) | 3.012 (5) | 150 (4) |
Symmetry code: (i) −x+1, y+1, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H22ClNO·0.5H2O |
Mr | 300.82 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 25.469 (16), 6.365 (4), 18.306 (11) |
β (°) | 91.815 (12) |
V (Å3) | 2966 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.35 × 0.30 × 0.16 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.915, 0.960 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6372, 2606, 1798 |
Rint | 0.098 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.216, 1.08 |
No. of reflections | 2606 |
No. of parameters | 198 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.40 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.83 (6) | 2.07 (9) | 2.611 (5) | 122 (7) |
O1W—H1W···O1i | 0.84 (4) | 1.99 (4) | 2.768 (5) | 153 (5) |
N1—H1A···O1W | 0.90 (4) | 2.20 (4) | 3.012 (5) | 150 (4) |
Symmetry code: (i) −x+1, y+1, −z+1/2. |
Acknowledgements
This work was supported financially by the Foundation of Liaoning Educational Department (No. 2008T073<2012001), the Science and Technology Foundation of Liaoning Province (No. 20071027), the Liaoning University Foundation of 211 Project for Innovative Talents Training and the Technology Major Projects Research Foundation (No. 2011ZX09102–007–02), China.
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Amantadine and its derivatives attract interest because of their biological activity and many potential applications (Camps et al., 2008). As an extension of our previous work on the compounds containing an adamantane group, we synthesized the title compound by reduction of the corresponding Schiff base. It crystallizes with solvent water. Asymmetric unit contains one molecule of the title compound and one half of solvent water (Fig. 1). In the organic molecule, all bond lengths and angles are normal and comparable with another reported compound, N-(2-Hydroxybenzyl)adamantan-1-amine (Wang et al., 2012). The hydroxyl O atom is involved in hydrogen bond (Table 1) with amino N atom with the OH···N distance of 2.611 (5) Å. This intra-molecular hydrogen bond formally results in a chiral center at the nitrogen atom, but the centrosymmetric crystal represents a racemate. The intramolecular hydrogen bond forms a R21(6) ring which stabilizes the molecular conformation (Table 1). In the crystal, the couples of organic molecules are alternated with crystallization water molecules along b axis forming intermolecular O(W)—H···O and N—H···O(W) hydrogen bonds (Fig. 2).