Adeninium perchlorate.

IN THE TITLE SALT (SYSTEMATIC NAME: 6-amino-9H-purin-1-ium perchlorate), C(5)H(6)N(5) (+)·ClO(4) (-), the adeninium cation is essentially planar, with a maximum deviation of 0.038 (1) Å. The whole of the perchlorate anion is disordered over two sets of sites with an occupancy ratio of 0.589 (13):0.411 (13). In the crystal, the adeninium cations are linked by pairs of N-H⋯N hydrogen bond into inversion dimers. The dimers and the anions are further inter-connected into a three-dimensional supra-molecular structure via inter-molecular N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For general background to and applications of the title adeninium salt, see: Biradha et al. (2010 ▶); Goswami et al. (2007 ▶). For a closely related adeninium structure, see: Zeleňák et al. (2004 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H6N5 +·ClO4 −

M = 235.60

Monoclinic,

a = 8.7614 (2) Å

b = 4.8234 (1) Å

c = 21.0758 (4) Å

β = 112.070 (1)°

V = 825.39 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 105 K

0.29 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.878, T max = 0.911

13078 measured reflections

3149 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.04

3149 reflections

200 parameters

10 restraints

All H-atom parameters refined

Δρmax = 0.45 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001528/is2652sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001528/is2652Isup2.hkl

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

C5H6N5+·ClO4−	F(000) = 480
Mr = 235.60	Dx = 1.896 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4267 reflections
a = 8.7614 (2) Å	θ = 3.8–33.0°
b = 4.8234 (1) Å	µ = 0.47 mm−1
c = 21.0758 (4) Å	T = 105 K
β = 112.070 (1)°	Block, colourless
V = 825.39 (3) Å3	0.29 × 0.28 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	2538 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 33.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.878, Tmax = 0.911	k = −7→7
13078 measured reflections	l = −30→32

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.043P)2 + 0.4566P] where P = (Fo2 + 2Fc2)/3
3149 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.45 e Å−3
10 restraints	Δρmin = −0.42 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 105.0 (1)K.

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	Occ. (<1)
N1	0.14134 (14)	0.5810 (3)	0.41768 (6)	0.0152 (2)
N2	0.14035 (14)	0.7456 (3)	0.52342 (6)	0.0169 (2)
N3	0.33327 (15)	0.4802 (3)	0.61809 (6)	0.0177 (2)
N4	0.43640 (13)	0.1928 (3)	0.56071 (6)	0.0153 (2)
N5	0.30483 (15)	0.2191 (3)	0.40417 (6)	0.0162 (2)
C1	0.32179 (15)	0.3695 (3)	0.51586 (7)	0.0137 (2)
C2	0.25906 (15)	0.3820 (3)	0.44387 (7)	0.0134 (2)
C3	0.08746 (17)	0.7514 (3)	0.45686 (7)	0.0167 (3)
C4	0.25733 (16)	0.5486 (3)	0.55077 (7)	0.0148 (2)
C5	0.43785 (16)	0.2674 (3)	0.62123 (7)	0.0174 (3)
Cl1	0.7997 (9)	0.4578 (14)	0.7670 (3)	0.0170 (6)	0.589 (13)
O1	0.9452 (8)	0.4076 (15)	0.8255 (3)	0.0317 (11)	0.589 (13)
O2	0.7796 (6)	0.7499 (5)	0.7523 (3)	0.0294 (9)	0.589 (13)
O3	0.8120 (11)	0.3197 (11)	0.7080 (3)	0.0183 (8)	0.589 (13)
O4	0.6558 (10)	0.359 (2)	0.7785 (5)	0.020 (2)	0.589 (13)
Cl1X	0.8150 (12)	0.4603 (19)	0.7747 (5)	0.0155 (7)	0.411 (13)
O1X	0.9454 (11)	0.3192 (15)	0.8286 (5)	0.0216 (11)	0.411 (13)
O2X	0.8317 (7)	0.7552 (7)	0.7882 (5)	0.0285 (16)	0.411 (13)
O3X	0.8155 (16)	0.398 (2)	0.7091 (5)	0.0242 (16)	0.411 (13)
O4X	0.6614 (13)	0.362 (3)	0.7772 (7)	0.020 (3)	0.411 (13)
H1N1	0.098 (2)	0.598 (4)	0.3760 (10)	0.024*
H1N3	0.322 (2)	0.554 (4)	0.6494 (11)	0.024*
H1N5	0.382 (3)	0.103 (4)	0.4224 (10)	0.024*
H2N5	0.259 (2)	0.223 (4)	0.3606 (10)	0.024*
H3	0.005 (2)	0.880 (4)	0.4324 (10)	0.024*
H5	0.501 (2)	0.182 (4)	0.6632 (10)	0.024*

	U11	U22	U33	U12	U13	U23
N1	0.0165 (5)	0.0140 (6)	0.0156 (5)	0.0027 (4)	0.0068 (4)	0.0033 (4)
N2	0.0161 (5)	0.0142 (6)	0.0212 (5)	0.0006 (5)	0.0079 (4)	−0.0016 (5)
N3	0.0183 (5)	0.0202 (6)	0.0150 (5)	0.0007 (5)	0.0068 (4)	−0.0037 (5)
N4	0.0143 (5)	0.0144 (5)	0.0158 (5)	0.0004 (4)	0.0042 (4)	0.0003 (4)
N5	0.0183 (5)	0.0157 (6)	0.0143 (5)	0.0049 (5)	0.0058 (4)	0.0006 (4)
C1	0.0140 (5)	0.0118 (6)	0.0151 (5)	−0.0008 (5)	0.0053 (4)	−0.0007 (5)
C2	0.0140 (5)	0.0108 (6)	0.0160 (5)	−0.0001 (5)	0.0065 (4)	0.0012 (5)
C3	0.0168 (5)	0.0121 (6)	0.0227 (6)	0.0013 (5)	0.0091 (5)	0.0017 (5)
C4	0.0149 (5)	0.0122 (6)	0.0176 (6)	−0.0020 (5)	0.0067 (4)	−0.0022 (5)
C5	0.0159 (5)	0.0190 (7)	0.0161 (6)	−0.0006 (5)	0.0047 (4)	−0.0008 (5)
Cl1	0.0164 (11)	0.0164 (7)	0.0169 (10)	−0.0001 (6)	0.0049 (8)	0.0010 (5)
O1	0.0236 (13)	0.050 (3)	0.0164 (13)	0.002 (2)	0.0015 (9)	0.003 (2)
O2	0.0461 (18)	0.0134 (10)	0.035 (2)	−0.0033 (10)	0.0222 (18)	−0.0004 (10)
O3	0.0203 (13)	0.020 (2)	0.0154 (11)	−0.0009 (18)	0.0073 (9)	0.0004 (14)
O4	0.016 (3)	0.026 (4)	0.024 (4)	−0.007 (2)	0.015 (3)	−0.001 (3)
Cl1X	0.0133 (13)	0.0132 (9)	0.021 (2)	−0.0005 (8)	0.0080 (15)	0.0022 (11)
O1X	0.0182 (16)	0.026 (3)	0.0145 (16)	0.007 (2)	−0.0008 (12)	0.005 (2)
O2X	0.033 (2)	0.0076 (12)	0.050 (4)	−0.0005 (13)	0.022 (2)	−0.0003 (16)
O3X	0.0252 (19)	0.037 (4)	0.0128 (17)	−0.007 (4)	0.0098 (13)	0.003 (3)
O4X	0.024 (5)	0.022 (6)	0.013 (4)	0.005 (4)	0.006 (3)	0.007 (4)

N1—C2	1.3646 (18)	C1—C4	1.3855 (19)
N1—C3	1.3686 (18)	C1—C2	1.4075 (18)
N1—H1N1	0.82 (2)	C3—H3	0.95 (2)
N2—C3	1.3018 (18)	C5—H5	0.942 (19)
N2—C4	1.3571 (18)	Cl1—O1	1.423 (7)
N3—C5	1.361 (2)	Cl1—O2	1.439 (7)
N3—C4	1.3620 (18)	Cl1—O3	1.449 (7)
N3—H1N3	0.79 (2)	Cl1—O4	1.450 (7)
N4—C5	1.3208 (18)	Cl1X—O3X	1.417 (10)
N4—C1	1.3837 (17)	Cl1X—O1X	1.443 (9)
N5—C2	1.3153 (18)	Cl1X—O4X	1.446 (10)
N5—H1N5	0.85 (2)	Cl1X—O2X	1.447 (9)
N5—H2N5	0.85 (2)
C2—N1—C3	123.92 (12)	N1—C3—H3	115.6 (12)
C2—N1—H1N1	118.7 (14)	N2—C4—N3	127.42 (13)
C3—N1—H1N1	117.4 (14)	N2—C4—C1	127.20 (12)
C3—N2—C4	112.27 (12)	N3—C4—C1	105.37 (12)
C5—N3—C4	106.86 (12)	N4—C5—N3	113.36 (12)
C5—N3—H1N3	126.2 (15)	N4—C5—H5	125.2 (12)
C4—N3—H1N3	126.9 (15)	N3—C5—H5	121.4 (12)
C5—N4—C1	103.49 (12)	O1—Cl1—O2	110.5 (5)
C2—N5—H1N5	119.2 (13)	O1—Cl1—O3	109.5 (6)
C2—N5—H2N5	122.7 (13)	O2—Cl1—O3	108.0 (5)
H1N5—N5—H2N5	118.0 (18)	O1—Cl1—O4	110.6 (6)
N4—C1—C4	110.93 (12)	O2—Cl1—O4	108.2 (6)
N4—C1—C2	130.69 (12)	O3—Cl1—O4	110.0 (7)
C4—C1—C2	118.28 (12)	O3X—Cl1X—O1X	112.0 (8)
N5—C2—N1	121.84 (12)	O3X—Cl1X—O4X	108.0 (10)
N5—C2—C1	124.83 (12)	O1X—Cl1X—O4X	106.8 (8)
N1—C2—C1	113.32 (12)	O3X—Cl1X—O2X	111.3 (7)
N2—C3—N1	125.00 (13)	O1X—Cl1X—O2X	108.5 (6)
N2—C3—H3	119.4 (12)	O4X—Cl1X—O2X	110.0 (9)
C5—N4—C1—C4	0.39 (15)	C3—N2—C4—N3	−177.16 (14)
C5—N4—C1—C2	−175.98 (14)	C3—N2—C4—C1	1.0 (2)
C3—N1—C2—N5	178.65 (13)	C5—N3—C4—N2	178.41 (14)
C3—N1—C2—C1	−0.51 (19)	C5—N3—C4—C1	−0.11 (15)
N4—C1—C2—N5	−1.6 (2)	N4—C1—C4—N2	−178.70 (13)
C4—C1—C2—N5	−177.75 (13)	C2—C1—C4—N2	−1.8 (2)
N4—C1—C2—N1	177.53 (13)	N4—C1—C4—N3	−0.17 (16)
C4—C1—C2—N1	1.38 (18)	C2—C1—C4—N3	176.70 (12)
C4—N2—C3—N1	0.0 (2)	C1—N4—C5—N3	−0.47 (16)
C2—N1—C3—N2	−0.2 (2)	C4—N3—C5—N4	0.38 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.82 (2)	2.23 (2)	2.868 (7)	135.2 (17)
N3—H1N3···O4ii	0.79 (2)	2.07 (2)	2.818 (10)	158.2 (19)
N5—H1N5···N4iii	0.85 (2)	2.07 (2)	2.8938 (19)	164.3 (19)
N5—H2N5···O2i	0.85 (2)	2.28 (2)	3.100 (6)	162.0 (18)
C3—H3···N2iv	0.945 (19)	2.577 (19)	3.266 (2)	130.0 (15)
C3—H3···O1v	0.945 (19)	2.35 (2)	3.055 (6)	131.2 (16)
C5—H5···O4	0.94 (2)	2.45 (2)	3.174 (10)	133.6 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.82 (2)	2.23 (2)	2.868 (7)	135.2 (17)
N3—H1N3⋯O4ii	0.79 (2)	2.07 (2)	2.818 (10)	158.2 (19)
N5—H1N5⋯N4iii	0.85 (2)	2.07 (2)	2.8938 (19)	164.3 (19)
N5—H2N5⋯O2i	0.85 (2)	2.28 (2)	3.100 (6)	162.0 (18)
C3—H3⋯N2iv	0.945 (19)	2.577 (19)	3.266 (2)	130.0 (15)
C3—H3⋯O1v	0.945 (19)	2.35 (2)	3.055 (6)	131.2 (16)
C5—H5⋯O4	0.94 (2)	2.45 (2)	3.174 (10)	133.6 (15)

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