2-[(Adamantan-1-yl)amino-meth-yl]-4-chloro-phenol hemihydrate.

In the title compound, C17H22ClNO·0.5H2O, the water mol-ecule O atom resides on a twofold rotation axis. In the organic mol-ecule, the phenol group forms an intra-molecular O-H⋯N hydrogen bond. In the crystal, pairs of organic mol-ecules are hydrogen bonded through bridging solvent water mol-ecules, forming chains along the b-axis direction.

Related literature

For the synthesis and crystal structure of 2-[(adamantan-1-yl­amino)­meth­yl]phenol, see: Wang & Tao (2012 ▶). For the synthesis and applications of n class="Chemical">amantadine derivatives, see: Camps et al. (2008 ▶).

Experimental

Crystal data

C17H22ClNO·0.5n class="Chemical">H2O

M = 300.82

Monoclinic,

a = 25.469 (16) Å

b = 6.365 (4) Å

c = 18.306 (11) Å

β = 91.815 (12)°

V = 2966 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.35 × 0.30 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.915, T max = 0.960

6372 measured reflections

2606 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.216

S = 1.08

2606 reflections

198 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045175/ld2073sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045175/ld2073Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045175/ld2073Isup3.cml

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

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

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) .