Bis(adamantan-1-aminium) carbonate.

In the title compound, 2C(10)H(18)N(+)·CO(3) (2-), the adamantan-1-aminium cation forms three N-H⋯O hydrogen bonds to three carbonate ions, resulting in a layer parallel to (001) with the adamantane groups located on its surface so that adjacent layers form only C-H⋯H-C contacts. The carbonate anions occupy special positions of 32 symmetry, whereas the adamantan-1-aminium cations occupy special positions of 3 symmetry.

Related literature

For related structures, see: de Vries et al. (2011 ▶); Mullica et al. (1999 ▶); He & Wen (2006 ▶); Liu et al. (2009 ▶); Zhao et al. (2003 ▶). For applications of adamantane–ammonium salts in virology, see: Hoffmann (1973 ▶); Dolin et al. (1982 ▶); Bright et al. (2005 ▶); Betakova (2007 ▶). For applications of amines for the capture of CO2 from the atmosphere, see: Yang et al. (2008 ▶).

Experimental

Crystal data

2C10H18N+·CO3 2−

M = 364.52

Trigonal,

a = 6.4340 (6) Å

c = 25.474 (2) Å

V = 913.25 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.30 × 0.22 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

3187 measured reflections

629 independent reflections

493 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.08

629 reflections

45 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus and XPREP (Bruker 2005 ▶); 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 ▶), Mercury (Macrae et al., 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011828/gk2467sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011828/gk2467Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011828/gk2467Isup3.cml

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

2C10H18N+·CO32−	Dx = 1.326 Mg m−3
Mr = 364.52	Mo Kα radiation, λ = 0.71069 Å
Trigonal, P3c1	Cell parameters from 819 reflections
Hall symbol: -P 3 2"c	θ = 3.2–25.8°
a = 6.4340 (6) Å	µ = 0.09 mm−1
c = 25.474 (2) Å	T = 173 K
V = 913.25 (14) Å3	Prism, colourless
Z = 2	0.30 × 0.22 × 0.08 mm
F(000) = 400

Bruker APEXII CCD diffractometer	Rint = 0.062
Graphite monochromator	θmax = 26.4°, θmin = 1.6°
φ and ω scans	h = −8→5
3187 measured reflections	k = −2→8
629 independent reflections	l = −31→31
493 reflections with I > 2σ(I)

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) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.010P] where P = (Fo2 + 2Fc2)/3
629 reflections	(Δ/σ)max < 0.001
45 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 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	0.6667	0.3333	0.16486 (9)	0.0236 (6)
C2	0.9213 (2)	0.5034 (2)	0.14518 (6)	0.0278 (4)
H2A	1.032	0.4505	0.1584	0.033*
H2B	0.977	0.6678	0.1583	0.033*
C3	0.9215 (2)	0.5033 (3)	0.08498 (6)	0.0309 (4)
H3	1.0877	0.614	0.0719	0.037*
C4	0.8365 (3)	0.2482 (3)	0.06502 (6)	0.0346 (4)
H4A	0.838	0.2474	0.0262	0.042*
H4B	0.9464	0.1932	0.0777	0.042*
C5	0	0	0.25	0.0219 (7)
N1	0.6667	0.3333	0.22372 (8)	0.0278 (5)
O1	0	0.1993 (2)	0.25	0.0343 (4)
H1	0.732 (4)	0.502 (3)	0.2358 (7)	0.060 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0198 (8)	0.0198 (8)	0.0312 (12)	0.0099 (4)	0	0
C2	0.0195 (8)	0.0205 (7)	0.0415 (9)	0.0087 (6)	−0.0018 (6)	−0.0014 (6)
C3	0.0217 (8)	0.0262 (8)	0.0404 (9)	0.0085 (6)	0.0061 (6)	0.0039 (6)
C4	0.0317 (9)	0.0350 (9)	0.0397 (8)	0.0185 (8)	0.0055 (6)	−0.0016 (7)
C5	0.0214 (10)	0.0214 (10)	0.0228 (15)	0.0107 (5)	0	0
N1	0.0253 (7)	0.0253 (7)	0.0328 (11)	0.0127 (3)	0	0
O1	0.0299 (8)	0.0221 (6)	0.0536 (10)	0.0149 (4)	−0.0091 (7)	−0.0045 (3)

C1—N1	1.500 (3)	C3—C4	1.534 (2)
C1—C2	1.5295 (14)	C3—H3	1
C2—C3	1.5335 (19)	C4—H4A	0.99
C2—H2A	0.99	C4—H4B	0.99
C2—H2B	0.99	C5—O1	1.2820 (13)
C3—C4i	1.532 (2)	N1—H1	0.999 (16)
N1—C1—C2	109.13 (9)	C2—C3—C4	109.40 (12)
C2ii—C1—C2	109.81 (9)	C2—C3—H3	109.5
C1—C2—C3	109.18 (12)	C4—C3—H3	109.5
C1—C2—H2A	109.8	C3ii—C4—C3	109.57 (13)
C3—C2—H2A	109.8	C3—C4—H4A	109.8
C1—C2—H2B	109.8	C3—C4—H4B	109.8
C3—C2—H2B	109.8	H4A—C4—H4B	108.2
H2A—C2—H2B	108.3	O1iii—C5—O1	120
C4i—C3—C2	109.29 (11)	C1—N1—H1	107.9 (11)
C4i—C3—C4	109.58 (14)
N1—C1—C2—C3	179.92 (8)	C1—C2—C3—C4	−59.84 (12)
C2ii—C1—C2—C3	60.34 (13)	C4i—C3—C4—C3ii	−59.76 (18)
C2i—C1—C2—C3	−60.50 (13)	C2—C3—C4—C3ii	60.04 (15)
C1—C2—C3—C4i	60.13 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1iv	0.999 (16)	1.778 (15)	2.7644 (11)	168.7 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.999 (16)	1.778 (15)	2.764 (1)	168.7 (18)

Symmetry code: (i) .