Memanti-nium chloride 0.1-hydrate.

The crystal structure of the title compound, C(12)H(22)N(+)·Cl(-)·0.1H(2)O, consists of (3,5-dimethyl-1-adamantyl)ammonium chloride (memanti-nium chloride) and uncoordinated water mol-ecules. The four six-membered rings of the memanti-nium cation assume typical chair conformations. The Cl(-) counter-anion links with the memanti-nium cation via N-H⋯Cl hydrogen bonding, forming channels where the disordered crystal water molecules are located. The O atom of the water mol-ecule is located on a threefold rotation axis, its two H atoms symmetrically distributed over six sites; the water mol-ecule links with the Cl(-) anions via O-H⋯Cl hydrogen bonding.

Related literature

For applications of memantine in medicine, see: Parsons et al. (1999 ▶); Tariot et al. (2004 ▶). For a related structure, see: Zahid et al. (2009 ▶). The H atoms of the ncoordinated water mol­ecule were placed at calculated positions, see: Nardelli (1999 ▶).

Experimental

Crystal data

C12H22N+·Cl−·0.1H2O

M = 217.56

Trigonal,

a = 28.3787 (11) Å

c = 8.5236 (4) Å

V = 5944.8 (4) Å3

Z = 18

Mo Kα radiation

μ = 0.26 mm−1

T = 294 K

0.41 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.888, T max = 0.959

18491 measured reflections

2845 independent reflections

1671 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.104

S = 1.09

2845 reflections

132 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 1329 Friedel pairs

Flack parameter: 0.06 (9)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031791/xu2585sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031791/xu2585Isup2.hkl

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

C12H22N·Cl·0.1(H2O)	Dx = 1.094 Mg m−3
Mr = 217.56	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3c	Cell parameters from 10816 reflections
Hall symbol: R 3 -2"c	θ = 3.2–27.4°
a = 28.3787 (11) Å	µ = 0.26 mm−1
c = 8.5236 (4) Å	T = 294 K
V = 5944.8 (4) Å3	Block, colorless
Z = 18	0.41 × 0.18 × 0.16 mm
F(000) = 2142

Rigaku R-AXIS RAPID diffractometer	2845 independent reflections
Radiation source: rolling anode	1671 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −36→36
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −36→36
Tmin = 0.888, Tmax = 0.959	l = −11→9
18491 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0331P)2 + 3.5112P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.28 e Å−3
2845 reflections	Δρmin = −0.31 e Å−3
132 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.00185 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1329 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.06 (9)

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 > 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	Occ. (<1)
N1	0.33309 (10)	0.56273 (9)	0.6470 (3)	0.0597 (6)
H1A	0.3632	0.5911	0.6098	0.090*
H1B	0.3320	0.5656	0.7508	0.090*
H1C	0.3041	0.5620	0.6046	0.090*
C1	0.33298 (13)	0.51132 (11)	0.6066 (3)	0.0552 (7)
C7	0.28247 (16)	0.41097 (14)	0.6378 (5)	0.0840 (10)
H7	0.2498	0.3798	0.6813	0.101*
C5	0.38468 (14)	0.46190 (13)	0.6423 (4)	0.0727 (9)
C4	0.38361 (11)	0.51418 (10)	0.6791 (3)	0.0621 (7)
H4A	0.3833	0.5187	0.7918	0.074*
H4B	0.4160	0.5453	0.6370	0.074*
C12	0.43554 (15)	0.46469 (17)	0.7130 (5)	0.1084 (13)
H12A	0.4674	0.4950	0.6689	0.130*
H12B	0.4357	0.4317	0.6898	0.130*
H12C	0.4355	0.4691	0.8246	0.130*
C2	0.28213 (12)	0.46352 (12)	0.6771 (4)	0.0720 (8)
H2A	0.2498	0.4621	0.6339	0.086*
H2B	0.2819	0.4678	0.7899	0.086*
C10	0.38348 (15)	0.45520 (14)	0.4635 (4)	0.0764 (9)
H10A	0.4159	0.4856	0.4190	0.092*
H10B	0.3841	0.4222	0.4388	0.092*
C3	0.33333 (14)	0.50494 (13)	0.4295 (3)	0.0647 (9)
H3A	0.3653	0.5360	0.3853	0.078*
H3B	0.3014	0.5037	0.3844	0.078*
C6	0.33304 (14)	0.41367 (13)	0.7103 (5)	0.0874 (10)
H6A	0.3331	0.3801	0.6888	0.105*
H6B	0.3324	0.4177	0.8232	0.105*
C9	0.33374 (13)	0.45250 (12)	0.3886 (4)	0.0732 (8)
C11	0.33487 (18)	0.44638 (16)	0.2099 (4)	0.1064 (14)
H11A	0.3670	0.4769	0.1678	0.128*
H11B	0.3032	0.4450	0.1644	0.128*
H11C	0.3351	0.4134	0.1858	0.128*
C8	0.28330 (16)	0.40466 (14)	0.4610 (5)	0.0876 (11)
H8A	0.2509	0.4025	0.4157	0.105*
H8B	0.2829	0.3711	0.4369	0.105*
Cl1	0.22918 (3)	0.56280 (3)	0.51793 (11)	0.0756 (2)
O1	0.3333	0.6667	0.800 (4)	0.181 (9)	0.30
H1E	0.3330	0.6410	0.8557	0.272*	0.10
H1F	0.3070	0.6480	0.7275	0.272*	0.10

	U11	U22	U33	U12	U13	U23
N1	0.0637 (13)	0.0571 (13)	0.0653 (14)	0.0355 (12)	−0.0009 (11)	0.0000 (11)
C1	0.0562 (17)	0.0471 (16)	0.065 (2)	0.0274 (14)	0.0031 (14)	0.0011 (13)
C7	0.077 (2)	0.0513 (19)	0.112 (3)	0.0234 (17)	0.011 (2)	0.0112 (17)
C5	0.074 (2)	0.0604 (19)	0.094 (3)	0.0408 (18)	−0.0034 (17)	0.0013 (17)
C4	0.0613 (16)	0.0568 (16)	0.0704 (18)	0.0312 (13)	−0.0010 (14)	0.0009 (14)
C12	0.110 (3)	0.110 (3)	0.137 (4)	0.079 (3)	−0.029 (3)	−0.011 (2)
C2	0.0639 (18)	0.0590 (17)	0.088 (2)	0.0269 (15)	0.0116 (15)	0.0076 (15)
C10	0.083 (2)	0.066 (2)	0.091 (2)	0.0453 (18)	0.0076 (18)	−0.0068 (18)
C3	0.074 (2)	0.0591 (18)	0.066 (2)	0.0364 (17)	−0.0033 (17)	−0.0064 (14)
C6	0.102 (3)	0.064 (2)	0.101 (3)	0.0448 (19)	0.009 (2)	0.0171 (18)
C9	0.088 (2)	0.0599 (17)	0.077 (2)	0.0406 (17)	−0.0032 (17)	−0.0150 (15)
C11	0.150 (4)	0.094 (3)	0.085 (3)	0.069 (3)	−0.009 (2)	−0.028 (2)
C8	0.086 (3)	0.0538 (19)	0.115 (3)	0.0293 (19)	−0.011 (2)	−0.016 (2)
Cl1	0.0867 (6)	0.0914 (6)	0.0679 (4)	0.0589 (4)	−0.0076 (5)	−0.0064 (5)
O1	0.145 (9)	0.145 (9)	0.25 (3)	0.073 (4)	0.000	0.000

N1—C1	1.497 (3)	C2—H2A	0.9700
N1—H1A	0.8900	C2—H2B	0.9700
N1—H1B	0.8900	C10—C9	1.516 (5)
N1—H1C	0.8900	C10—H10A	0.9700
C1—C3	1.521 (3)	C10—H10B	0.9700
C1—C2	1.525 (4)	C3—C9	1.534 (4)
C1—C4	1.529 (4)	C3—H3A	0.9700
C7—C8	1.519 (5)	C3—H3B	0.9700
C7—C6	1.529 (5)	C6—H6A	0.9700
C7—C2	1.533 (5)	C6—H6B	0.9700
C7—H7	0.9800	C9—C8	1.526 (5)
C5—C12	1.529 (4)	C9—C11	1.535 (5)
C5—C4	1.532 (4)	C11—H11A	0.9600
C5—C10	1.534 (4)	C11—H11B	0.9600
C5—C6	1.533 (5)	C11—H11C	0.9600
C4—H4A	0.9700	C8—H8A	0.9700
C4—H4B	0.9700	C8—H8B	0.9700
C12—H12A	0.9600	O1—H1E	0.8634
C12—H12B	0.9600	O1—H1F	0.9108
C12—H12C	0.9600
C1—N1—H1A	109.5	C7—C2—H2B	110.0
C1—N1—H1B	109.5	H2A—C2—H2B	108.4
H1A—N1—H1B	109.5	C9—C10—C5	112.8 (3)
C1—N1—H1C	109.5	C9—C10—H10A	109.0
H1A—N1—H1C	109.5	C5—C10—H10A	109.0
H1B—N1—H1C	109.5	C9—C10—H10B	109.0
N1—C1—C3	110.3 (3)	C5—C10—H10B	109.0
N1—C1—C2	108.4 (2)	H10A—C10—H10B	107.8
C3—C1—C2	110.2 (2)	C1—C3—C9	110.2 (3)
N1—C1—C4	108.1 (2)	C1—C3—H3A	109.6
C3—C1—C4	110.2 (2)	C9—C3—H3A	109.6
C2—C1—C4	109.5 (2)	C1—C3—H3B	109.6
C8—C7—C6	109.7 (3)	C9—C3—H3B	109.6
C8—C7—C2	109.8 (3)	H3A—C3—H3B	108.1
C6—C7—C2	109.0 (3)	C7—C6—C5	110.2 (3)
C8—C7—H7	109.4	C7—C6—H6A	109.6
C6—C7—H7	109.4	C5—C6—H6A	109.6
C2—C7—H7	109.4	C7—C6—H6B	109.6
C12—C5—C4	110.2 (3)	C5—C6—H6B	109.6
C12—C5—C10	111.1 (3)	H6A—C6—H6B	108.1
C4—C5—C10	108.2 (2)	C10—C9—C8	108.1 (3)
C12—C5—C6	110.7 (3)	C10—C9—C3	108.3 (3)
C4—C5—C6	108.3 (3)	C8—C9—C3	108.2 (3)
C10—C5—C6	108.2 (3)	C10—C9—C11	110.6 (3)
C1—C4—C5	109.8 (2)	C8—C9—C11	111.3 (3)
C1—C4—H4A	109.7	C3—C9—C11	110.2 (3)
C5—C4—H4A	109.7	C9—C11—H11A	109.5
C1—C4—H4B	109.7	C9—C11—H11B	109.5
C5—C4—H4B	109.7	H11A—C11—H11B	109.5
H4A—C4—H4B	108.2	C9—C11—H11C	109.5
C5—C12—H12A	109.5	H11A—C11—H11C	109.5
C5—C12—H12B	109.5	H11B—C11—H11C	109.5
H12A—C12—H12B	109.5	C7—C8—C9	111.0 (3)
C5—C12—H12C	109.5	C7—C8—H8A	109.4
H12A—C12—H12C	109.5	C9—C8—H8A	109.4
H12B—C12—H12C	109.5	C7—C8—H8B	109.4
C1—C2—C7	108.4 (3)	C9—C8—H8B	109.4
C1—C2—H2A	110.0	H8A—C8—H8B	108.0
C7—C2—H2A	110.0	H1E—O1—H1F	102.8
C1—C2—H2B	110.0
N1—C1—C4—C5	179.2 (2)	C8—C7—C6—C5	59.3 (4)
C3—C1—C4—C5	−60.1 (3)	C2—C7—C6—C5	−61.0 (4)
C2—C1—C4—C5	61.2 (3)	C12—C5—C6—C7	−179.5 (3)
C12—C5—C4—C1	179.4 (3)	C4—C5—C6—C7	59.6 (4)
C10—C5—C4—C1	57.8 (3)	C10—C5—C6—C7	−57.5 (4)
C6—C5—C4—C1	−59.4 (3)	C5—C10—C9—C8	−58.5 (3)
N1—C1—C2—C7	−179.1 (3)	C5—C10—C9—C3	58.5 (3)
C3—C1—C2—C7	60.0 (3)	C5—C10—C9—C11	179.4 (3)
C4—C1—C2—C7	−61.4 (3)	C1—C3—C9—C10	−58.1 (3)
C8—C7—C2—C1	−59.2 (4)	C1—C3—C9—C8	58.8 (3)
C6—C7—C2—C1	61.0 (4)	C1—C3—C9—C11	−179.2 (3)
C12—C5—C10—C9	−179.7 (3)	C6—C7—C8—C9	−59.8 (4)
C4—C5—C10—C9	−58.7 (3)	C2—C7—C8—C9	60.0 (4)
C6—C5—C10—C9	58.5 (3)	C10—C9—C8—C7	58.3 (4)
N1—C1—C3—C9	179.5 (3)	C3—C9—C8—C7	−58.8 (4)
C2—C1—C3—C9	−60.8 (3)	C11—C9—C8—C7	180.0 (3)
C4—C1—C3—C9	60.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.89	2.26	3.147 (3)	176
N1—H1B···Cl1ii	0.89	2.28	3.161 (2)	171
N1—H1C···Cl1	0.89	2.26	3.148 (3)	175
O1—H1E···Cl1ii	0.86	2.62	3.486 (17)	179
O1—H1F···Cl1	0.91	2.93	3.81 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.89	2.26	3.147 (3)	176
N1—H1B⋯Cl1ii	0.89	2.28	3.161 (2)	171
N1—H1C⋯Cl1	0.89	2.26	3.148 (3)	175
O1—H1E⋯Cl1ii	0.86	2.62	3.486 (17)	179
O1—H1F⋯Cl1	0.91	2.93	3.81 (2)	163

Symmetry codes: (i) ; (ii) .