Adeninium perchlorate adenine dihydrate

The structure of the title compound, C₅H₆N₅⁺·ClO₄^-·C₅H₅N₅·2H₂O, contains both an adeninium cation (AdeH⁺) and an adenine mol­ecule (Ade). As a result of the protonation, the C-N-C angle at the protonated N atom is larger by 4° than the corresponding angle in the neutral adenine mol­ecule. The crystal packing is governed by classical hydrogen bonds, connecting the Ade and AdeH⁺ moieties in the crystallographic [101] direction. In addition, AdeH⁺ and Ade form hydrogen bonds with the water mol­ecules. These hydrogen bonds increase the dimensionality of the system to three-dimensional space. The water mol­ecules are connected to each other by hydrogen bonds in the [001] direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.138
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving .   ?

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT128_ALERT_4_C Non-standard setting of Space group P21/m   ....    P21/c
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        Cl1

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999).

Adeninium perchlorate adenine dihydrate

Crystal data

C5H6N5^+·ClO4^−·C5H5N5·2H2O	F(000) = 840
Mr = 406.77	Dx = 1.680 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 27858 reflections
a = 7.7750 (2) Å	θ = 1–27.5°
b = 20.1180 (5) Å	µ = 0.30 mm^−1
c = 10.5900 (3) Å	T = 150 K
β = 103.8880 (15)°	Needle, colourless
V = 1608.04 (7) Å^3	0.35 × 0.3 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	2341 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
Detector resolution: 9.091 pixels mm^-1	h = −10→10
φ and ω scans to fill the Ewald sphere	k = −26→26
28827 measured reflections	l = −13→13
3656 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: difference Fourier map
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.3603P] where P = (Fo^2 + 2Fc^2)/3
3656 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.28 e Å^−3
4 restraints	Δρmin = −0.52 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.35916 (19)	0.36311 (7)	0.45548 (14)	0.0260 (3)
H1A	0.4142	0.3257	0.4659	0.031*
C2A	0.2359 (2)	0.37342 (9)	0.34262 (17)	0.0284 (4)
H2A	0.2158	0.3390	0.2822	0.034*
N3A	0.14305 (19)	0.42773 (8)	0.31194 (14)	0.0284 (4)
C4A	0.1844 (2)	0.47472 (9)	0.40740 (17)	0.0254 (4)
C5A	0.3064 (2)	0.46880 (9)	0.52606 (17)	0.0251 (4)
C6A	0.4007 (2)	0.40867 (9)	0.55324 (16)	0.0254 (4)
N7A	0.3118 (2)	0.52665 (7)	0.59758 (14)	0.0278 (4)
C8A	0.1938 (2)	0.56477 (9)	0.52124 (17)	0.0284 (4)
H8A	0.1678	0.6076	0.5441	0.034*
N9A	0.1131 (2)	0.53603 (7)	0.40572 (14)	0.0274 (4)
H9A	0.0330	0.5534	0.3442	0.033*
N10A	0.5204 (2)	0.39478 (9)	0.66077 (15)	0.0293 (4)
H10A	0.573 (3)	0.3552 (11)	0.6702 (19)	0.034 (6)*
H10B	0.541 (3)	0.4259 (12)	0.721 (2)	0.045 (7)*
N1B	0.36710 (19)	0.36247 (7)	0.96288 (14)	0.0260 (4)
C2B	0.2430 (2)	0.37627 (9)	0.85329 (18)	0.0293 (4)
H2B	0.2195	0.3427	0.7911	0.035*
N3B	0.15013 (19)	0.43191 (8)	0.82334 (14)	0.0290 (4)
C4B	0.1934 (2)	0.47738 (9)	0.92023 (17)	0.0254 (4)
C5B	0.3154 (2)	0.46920 (8)	1.03849 (17)	0.0249 (4)
C6B	0.4060 (2)	0.40806 (9)	1.05971 (17)	0.0257 (4)
N7B	0.32336 (19)	0.52611 (7)	1.11364 (14)	0.0274 (4)
C8B	0.2075 (2)	0.56619 (9)	1.04005 (17)	0.0281 (4)
H8B	0.1837	0.6088	1.0656	0.034*
N9B	0.1259 (2)	0.53939 (7)	0.92320 (14)	0.0282 (4)
H9B	0.0469	0.5581	0.8628	0.034*
N10B	0.5264 (2)	0.39323 (9)	1.16862 (16)	0.0311 (4)
H10C	0.578 (3)	0.3547 (11)	1.1747 (19)	0.034 (6)*
H10D	0.551 (3)	0.4226 (12)	1.228 (2)	0.042 (6)*
Cl1	0.05683 (6)	0.249214 (19)	1.05999 (4)	0.02610 (17)
O1	0.23872 (19)	0.24654 (6)	1.13033 (14)	0.0332 (4)
O2	−0.0377 (2)	0.19529 (8)	1.10012 (16)	0.0537 (5)
O3	0.0439 (2)	0.24459 (7)	0.92269 (15)	0.0502 (5)
O4	−0.0203 (2)	0.31023 (8)	1.08812 (15)	0.0541 (5)
O5	0.5541 (2)	0.24940 (6)	0.96252 (15)	0.0314 (3)
H1W	0.623 (3)	0.2487 (8)	1.0404 (18)	0.038*
H2W	0.488 (2)	0.2865 (8)	0.9636 (19)	0.038*
O6	0.6842 (2)	0.25904 (8)	0.74230 (16)	0.0503 (5)
H3W	0.794 (2)	0.2568 (10)	0.773 (3)	0.060*
H4W	0.640 (4)	0.2533 (10)	0.811 (2)	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0300 (8)	0.0221 (8)	0.0250 (8)	−0.0010 (6)	0.0046 (6)	−0.0014 (6)
C2A	0.0320 (10)	0.0281 (10)	0.0241 (9)	−0.0044 (8)	0.0047 (8)	−0.0018 (8)
N3A	0.0303 (9)	0.0305 (9)	0.0229 (8)	−0.0034 (7)	0.0035 (6)	0.0004 (7)
C4A	0.0257 (10)	0.0266 (10)	0.0239 (9)	−0.0035 (7)	0.0062 (7)	0.0019 (7)
C5A	0.0240 (9)	0.0264 (9)	0.0249 (9)	−0.0049 (7)	0.0057 (7)	−0.0016 (7)
C6A	0.0252 (9)	0.0287 (10)	0.0223 (9)	−0.0056 (8)	0.0055 (7)	−0.0008 (7)
N7A	0.0280 (9)	0.0280 (8)	0.0271 (8)	−0.0033 (6)	0.0057 (7)	−0.0020 (6)
C8A	0.0294 (10)	0.0263 (10)	0.0293 (10)	−0.0024 (8)	0.0066 (8)	−0.0007 (8)
N9A	0.0272 (8)	0.0285 (8)	0.0252 (8)	−0.0002 (6)	0.0034 (6)	0.0019 (6)
N10A	0.0301 (9)	0.0311 (9)	0.0240 (9)	0.0014 (7)	0.0009 (7)	−0.0010 (7)
N1B	0.0289 (8)	0.0261 (8)	0.0226 (8)	−0.0052 (6)	0.0052 (6)	−0.0022 (6)
C2B	0.0315 (10)	0.0296 (10)	0.0269 (10)	−0.0049 (8)	0.0073 (8)	−0.0008 (8)
N3B	0.0317 (9)	0.0301 (9)	0.0242 (8)	−0.0028 (7)	0.0049 (7)	0.0003 (7)
C4B	0.0254 (10)	0.0261 (10)	0.0249 (9)	−0.0045 (7)	0.0067 (7)	0.0013 (7)
C5B	0.0259 (10)	0.0250 (9)	0.0243 (9)	−0.0040 (7)	0.0067 (7)	−0.0011 (7)
C6B	0.0249 (9)	0.0302 (10)	0.0226 (9)	−0.0046 (8)	0.0066 (7)	0.0006 (8)
N7B	0.0290 (9)	0.0263 (8)	0.0260 (8)	−0.0027 (6)	0.0051 (6)	−0.0030 (6)
C8B	0.0304 (10)	0.0255 (9)	0.0286 (10)	−0.0037 (8)	0.0073 (8)	−0.0012 (8)
N9B	0.0287 (8)	0.0287 (8)	0.0253 (8)	−0.0007 (7)	0.0030 (7)	0.0036 (7)
N10B	0.0318 (9)	0.0313 (10)	0.0266 (9)	0.0020 (8)	0.0003 (7)	−0.0026 (8)
Cl1	0.0261 (3)	0.0276 (3)	0.0229 (3)	0.00119 (17)	0.00239 (18)	−0.00148 (16)
O1	0.0265 (7)	0.0423 (8)	0.0268 (8)	0.0015 (5)	−0.0013 (6)	0.0021 (5)
O2	0.0493 (9)	0.0480 (10)	0.0571 (10)	−0.0221 (7)	−0.0006 (8)	0.0080 (8)
O3	0.0398 (9)	0.0861 (14)	0.0213 (8)	0.0093 (7)	0.0009 (7)	−0.0048 (7)
O4	0.0546 (10)	0.0417 (9)	0.0546 (10)	0.0210 (7)	−0.0092 (8)	−0.0128 (7)
O5	0.0327 (8)	0.0305 (8)	0.0282 (8)	0.0032 (5)	0.0019 (6)	−0.0001 (6)
O6	0.0284 (8)	0.0887 (13)	0.0321 (9)	0.0047 (8)	0.0037 (7)	0.0008 (8)

Geometric parameters (Å, º)

N1A—C2A	1.357 (2)	N3B—C4B	1.355 (2)
N1A—C6A	1.362 (2)	C4B—N9B	1.356 (2)
N1A—H1A	0.8600	C4B—C5B	1.387 (2)
C2A—N3A	1.307 (2)	C5B—N7B	1.387 (2)
C2A—H2A	0.9300	C5B—C6B	1.409 (3)
N3A—C4A	1.365 (2)	C6B—N10B	1.333 (2)
C4A—N9A	1.351 (2)	N7B—C8B	1.316 (2)
C4A—C5A	1.386 (2)	C8B—N9B	1.359 (2)
C5A—N7A	1.384 (2)	C8B—H8B	0.9300
C5A—C6A	1.408 (3)	N9B—H9B	0.8600
C6A—N10A	1.316 (2)	N10B—H10C	0.87 (2)
N7A—C8A	1.314 (2)	N10B—H10D	0.85 (2)
C8A—N9A	1.362 (2)	Cl1—O4	1.4287 (15)
C8A—H8A	0.9300	Cl1—O2	1.4311 (15)
N9A—H9A	0.8600	Cl1—O1	1.4325 (15)
N10A—H10A	0.89 (2)	Cl1—O3	1.4362 (16)
N10A—H10B	0.88 (2)	O5—H1W	0.868 (17)
N1B—C2B	1.348 (2)	O5—H2W	0.907 (15)
N1B—C6B	1.355 (2)	O6—H3W	0.841 (18)
C2B—N3B	1.328 (2)	O6—H4W	0.881 (18)
C2B—H2B	0.9300
C2A—N1A—C6A	123.71 (16)	N1B—C2B—H2B	116.0
C2A—N1A—H1A	118.1	C2B—N3B—C4B	111.48 (16)
C6A—N1A—H1A	118.1	N3B—C4B—N9B	127.67 (17)
N3A—C2A—N1A	125.33 (17)	N3B—C4B—C5B	126.51 (17)
N3A—C2A—H2A	117.3	N9B—C4B—C5B	105.82 (15)
N1A—C2A—H2A	117.3	N7B—C5B—C4B	110.29 (15)
C2A—N3A—C4A	112.16 (15)	N7B—C5B—C6B	132.64 (17)
N9A—C4A—N3A	126.87 (16)	C4B—C5B—C6B	117.07 (16)
N9A—C4A—C5A	106.24 (15)	N10B—C6B—N1B	119.08 (17)
N3A—C4A—C5A	126.89 (17)	N10B—C6B—C5B	123.65 (17)
N7A—C5A—C4A	110.39 (16)	N1B—C6B—C5B	117.27 (16)
N7A—C5A—C6A	131.66 (16)	C8B—N7B—C5B	103.65 (15)
C4A—C5A—C6A	117.95 (16)	N7B—C8B—N9B	113.54 (16)
N10A—C6A—N1A	120.27 (17)	N7B—C8B—H8B	123.2
N10A—C6A—C5A	125.78 (17)	N9B—C8B—H8B	123.2
N1A—C6A—C5A	113.95 (15)	C4B—N9B—C8B	106.71 (15)
C8A—N7A—C5A	103.24 (14)	C4B—N9B—H9B	126.6
N7A—C8A—N9A	114.06 (16)	C8B—N9B—H9B	126.6
N7A—C8A—H8A	123.0	C6B—N10B—H10C	118.7 (14)
N9A—C8A—H8A	123.0	C6B—N10B—H10D	118.2 (15)
C4A—N9A—C8A	106.07 (15)	H10C—N10B—H10D	123 (2)
C4A—N9A—H9A	127.0	O4—Cl1—O2	108.54 (12)
C8A—N9A—H9A	127.0	O4—Cl1—O1	109.60 (8)
C6A—N10A—H10A	119.9 (13)	O2—Cl1—O1	109.30 (8)
C6A—N10A—H10B	116.2 (15)	O4—Cl1—O3	109.63 (9)
H10A—N10A—H10B	124 (2)	O2—Cl1—O3	109.61 (9)
C2B—N1B—C6B	119.72 (16)	O1—Cl1—O3	110.15 (10)
N3B—C2B—N1B	127.93 (17)	H1W—O5—H2W	102.7 (17)
N3B—C2B—H2B	116.0	H3W—O6—H4W	104 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O5^i	0.86	1.87	2.715 (2)	169
N9A—H9A···N3B^ii	0.86	2.01	2.847 (2)	163
N10A—H10A···O6	0.89 (2)	2.18 (2)	3.049 (2)	165 (2)
N10A—H10B···N7B^iii	0.88 (2)	2.06 (2)	2.885 (2)	156 (2)
N9B—H9B···N3A^ii	0.86	2.09	2.918 (2)	161
N10B—H10C···O6^iv	0.87 (2)	2.48 (2)	3.322 (2)	164 (2)
N10B—H10D···N7A^iii	0.85 (2)	2.15 (2)	2.969 (2)	160 (2)
O5—H1W···O6^iv	0.88 (2)	2.08 (2)	2.897 (2)	156 (2)
O5—H2W···N1B	0.91 (2)	1.79 (2)	2.700 (2)	177 (2)
O6—H3W···O3^v	0.84 (2)	2.21 (2)	2.999 (2)	157 (3)
O6—H4W···O5	0.88 (2)	1.88 (2)	2.763 (3)	174 (2)
C2A—H2A···O1^vi	0.93	2.49	3.405 (2)	167
C2A—H2A···O4^vi	0.93	2.47	3.205 (2)	136
C2B—H2B···O1^i	0.93	2.50	3.412 (2)	166
C2B—H2B···O2^i	0.93	2.59	3.349 (2)	139
C8A—H8A···O2^vii	0.93	2.39	3.045 (2)	127
C8B—H8B···O4^viii	0.93	2.43	3.032 (2)	122

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x, −y+1/2, z+1/2; (v) x+1, y, z; (vi) x, y, z−1; (vii) −x, y+1/2, −z+3/2; (viii) −x, −y+1, −z+2.