7-(1,3-Dioxolan-2-ylmeth­yl)-1,3-di­methyl­purine-2,6(1H,3H)-dione trichloro­acetic acid solvate

Wu, X.-X.; Shu, Z.; Ma, L.L.; Ding, Z.W.; Jin, Z.-M.

doi:10.1107/S1600536807067025

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o347

https://doi.org/10.1107/S1600536807067025

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7-(1,3-Dioxolan-2-ylmethyl)-1,3-dimethylpurine-2,6(1H,3H)-dione trichloroacetic acid solvate

Xiang-Xiang Wu,^a Zhan Shu,^b Lin-Lin Ma,^b Zhe-Wu Ding ^b and Zhi-Min Jin ^b ^*

^aCollege of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: apharm@sina.com

(Received 23 October 2007; accepted 14 December 2007; online 21 December 2007)

In the title compound, C₁₁H₁₄N₄O₄·C₂HCl₃O₂, the dioxolane ring adopts an envelope conformation. Doxophylline [7-(1,3-dioxolan-2-yl-methyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione] and trichloroacetic acid molecules are linked by O—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Chen et al. (2006 , 2007 ); Feng et al. (2007 ); Franzone et al. (1981 ); Li et al. (1995 ); Villani et al. (1997 ).

Experimental

Crystal data

C₁₁H₁₄N₄O₄·C₂HCl₃O₂
M_r = 429.64
Triclinic, $[P \overline 1]$
a = 5.656 (3) Å
b = 10.825 (5) Å
c = 14.962 (7) Å
α = 93.217 (9)°
β = 91.090 (8)°
γ = 101.725 (9)°
V = 895.1 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 293 (2) K
0.38 × 0.28 × 0.17 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.818, T_max = 0.912
4717 measured reflections
3124 independent reflections
2915 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.167
S = 1.15
3124 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N4	0.82	1.82	2.635 (4)	176
C5—H5⋯O5	0.93	2.48	3.079 (5)	123
C7—H7⋯O1ⁱ	0.98	2.44	3.410 (5)	171
C10—H10B⋯O2ⁱⁱ	0.96	2.51	3.351 (3)	147
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x, -y, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807067025/cs2059sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807067025/cs2059Isup2.hkl

checkCIF report

Comment top

Doxophylline, 2-(7'-theophyllinemethyl)1,3-dioxolane, is a theophylline derivative which shows interesting bronchodilating activity (Franzone et al., 1981; Villani et al., 1997). Previously, we have reported some compounds containing doxophylline (Chen et al., 2006; Chen et al., 2007; Feng et al., 2007).

Association of one doxophylline and one trichloroacetic acid molecule leads to the title compound (Fig. 1). The geometric features of the purine ring system are similar to those in doxophylline (Chen et al., 2006;Chen et al., 2007; Feng et al., 2007).

As shown in Fig. 2, the O6—H6···N4 hydrogen bond between trichloroacetic acid and doxophylline molecule is one of the essential forces in crystal formation. In addtion the weak hydrogen bonds of C7—H7···O1ⁱ, C10—H10B···O2ⁱⁱ and C5—H5···O5 help to increase the stability of the crystal (Table 2 & Fig. 2).

Related literature top

For related literature, see: Chen et al. (2006, 2007); Feng et al. (2007); Franzone et al. (1981); Li et al. (1995); Villani et al. (1997).

Experimental top

Doxophylline was synthesized according with a published procedure (Li et al., 1995), from theophylline by subsitution, oxidation and condensation. Trichloroacetic acid (10 mmol) was added to a solution of doxophylline (10 mm l) in ethanol (20 ml). The mixture was heated to boiling and a clear solution was obtained. Crystals of the title compound were formed by gradual evaporation of ethanol over a period of one week at 293 K.

Structure description top

For related literature, see: Chen et al. (2006, 2007); Feng et al. (2007); Franzone et al. (1981); Li et al. (1995); Villani et al. (1997).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL(Bruker, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. A view of the asymmetric unit with atomic labelling, showing 30% probability displacement ellipsoids. Hydrogen bonds are illustrated in broken lines.
	Fig. 2. A view of a portion of the crystal packing. Hydrogen bonds are illustrated in broken lines.

7-(1,3-Dioxolan-2-ylmethyl)-1,3-dimethylpurine-2,6(1H,3H)-dione trichloroacetic acid solvate top

Crystal data top

C₁₁H₁₄N₄O₄·C₂HCl₃O₂	Z = 2
M_r = 429.64	F(000) = 440
Triclinic, P1	D_x = 1.594 Mg m⁻³
a = 5.656 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.825 (5) Å	Cell parameters from 1931 reflections
c = 14.962 (7) Å	θ = 2.4–24.7°
α = 93.217 (9)°	µ = 0.55 mm⁻¹
β = 91.090 (8)°	T = 293 K
γ = 101.725 (9)°	Block, colorless
V = 895.1 (8) Å³	0.38 × 0.28 × 0.17 mm

Data collection top

Bruker APEX area-detector diffractometer	3124 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→6
T_min = 0.818, T_max = 0.912	k = −12→10
4717 measured reflections	l = −16→17

Refinement top

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0594P)² + 1.1669P] where P = (F_o² + 2F_c²)/3
3124 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₁H₁₄N₄O₄·C₂HCl₃O₂	γ = 101.725 (9)°
M_r = 429.64	V = 895.1 (8) Å³
Triclinic, P1	Z = 2
a = 5.656 (3) Å	Mo Kα radiation
b = 10.825 (5) Å	µ = 0.55 mm⁻¹
c = 14.962 (7) Å	T = 293 K
α = 93.217 (9)°	0.38 × 0.28 × 0.17 mm
β = 91.090 (8)°

Data collection top

Bruker APEX area-detector diffractometer	3124 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2915 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.912	R_int = 0.015
4717 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.15	Δρ_max = 0.32 e Å⁻³
3124 reflections	Δρ_min = −0.41 e Å⁻³
238 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	1.5096 (2)	0.72892 (10)	0.71995 (10)	0.0764 (4)
Cl2	1.8985 (2)	0.61490 (16)	0.77278 (12)	0.1021 (6)
Cl3	1.7335 (3)	0.59298 (13)	0.58909 (10)	0.0997 (6)
O1	0.3256 (5)	−0.0373 (3)	0.80906 (17)	0.0546 (7)
O2	0.3073 (6)	0.0976 (3)	0.5250 (2)	0.0733 (9)
O3	0.4973 (4)	0.1851 (3)	0.96858 (18)	0.0602 (8)
O4	0.8810 (5)	0.2918 (3)	0.99418 (19)	0.0623 (8)
O5	1.4500 (7)	0.4439 (4)	0.7965 (2)	0.1070 (15)
O6	1.3136 (5)	0.4325 (3)	0.65695 (18)	0.0636 (8)
H6	1.2045	0.3777	0.6741	0.095*
N1	0.3188 (5)	0.0331 (3)	0.66788 (19)	0.0419 (7)
N2	0.6381 (6)	0.1835 (3)	0.61213 (18)	0.0449 (7)
N3	0.8290 (5)	0.1395 (3)	0.83050 (18)	0.0405 (7)
N4	0.9777 (5)	0.2545 (3)	0.71822 (18)	0.0430 (7)
C1	0.4252 (6)	0.0310 (3)	0.7528 (2)	0.0393 (8)
C2	0.4147 (7)	0.1040 (4)	0.5965 (2)	0.0478 (9)
C3	0.7539 (6)	0.1868 (3)	0.6938 (2)	0.0366 (7)
C4	0.6551 (6)	0.1155 (3)	0.7615 (2)	0.0359 (7)
C5	1.0141 (6)	0.2218 (3)	0.8011 (2)	0.0453 (9)
C6	0.8182 (7)	0.0864 (4)	0.9184 (2)	0.0503 (9)
C7	0.7322 (7)	0.1697 (4)	0.9889 (2)	0.0556 (10)
C8	0.4837 (8)	0.3052 (6)	1.0101 (4)	0.0819 (16)
C9	0.7308 (9)	0.3811 (5)	1.0075 (4)	0.0873 (16)
C10	0.0798 (7)	−0.0510 (4)	0.6519 (3)	0.0571 (10)
C11	0.7596 (9)	0.2537 (4)	0.5391 (3)	0.0668 (12)
C12	1.4565 (7)	0.4789 (4)	0.7231 (3)	0.0495 (9)
C13	1.6453 (7)	0.5977 (4)	0.7006 (3)	0.0510 (9)
H5	1.1551	0.2535	0.8350	0.054*
H6A	0.9776	0.0744	0.9360	0.060*
H6B	0.7100	0.0042	0.9144	0.060*
H7	0.7354	0.1325	1.0470	0.067*
H8A	0.4326	0.2969	1.0714	0.098*
H8B	0.3708	0.3438	0.9774	0.098*
H9A	0.7445	0.4373	0.9588	0.105*
H9B	0.7747	0.4312	1.0634	0.105*
H10A	0.0989	−0.1371	0.6447	0.086*
H10B	0.0050	−0.0289	0.5986	0.086*
H10C	−0.0200	−0.0418	0.7020	0.086*
H11A	0.8042	0.3418	0.5577	0.100*
H11B	0.6521	0.2428	0.4875	0.100*
H11C	0.9019	0.2223	0.5242	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0576 (7)	0.0484 (6)	0.1235 (11)	0.0101 (5)	0.0154 (6)	0.0069 (6)
Cl2	0.0387 (6)	0.1176 (12)	0.1433 (14)	−0.0071 (7)	−0.0153 (7)	0.0424 (10)
Cl3	0.1202 (12)	0.0764 (9)	0.0881 (9)	−0.0186 (8)	0.0608 (9)	0.0041 (7)
O1	0.0479 (15)	0.0548 (16)	0.0536 (16)	−0.0104 (12)	0.0042 (12)	0.0136 (13)
O2	0.072 (2)	0.090 (2)	0.0536 (17)	0.0053 (17)	−0.0215 (15)	0.0125 (16)
O3	0.0333 (14)	0.082 (2)	0.0569 (16)	−0.0045 (13)	0.0028 (12)	−0.0057 (15)
O4	0.0353 (14)	0.079 (2)	0.0644 (18)	−0.0036 (14)	−0.0027 (12)	−0.0114 (15)
O5	0.104 (3)	0.112 (3)	0.075 (2)	−0.056 (2)	−0.026 (2)	0.045 (2)
O6	0.0586 (18)	0.069 (2)	0.0498 (16)	−0.0202 (14)	0.0089 (13)	0.0087 (14)
N1	0.0351 (15)	0.0415 (16)	0.0468 (17)	0.0035 (12)	−0.0024 (12)	0.0012 (13)
N2	0.0542 (18)	0.0444 (17)	0.0354 (15)	0.0063 (14)	0.0030 (13)	0.0088 (13)
N3	0.0389 (16)	0.0432 (16)	0.0365 (15)	0.0000 (13)	0.0013 (12)	0.0077 (12)
N4	0.0443 (17)	0.0416 (16)	0.0383 (16)	−0.0031 (13)	0.0063 (12)	0.0038 (12)
C1	0.0368 (18)	0.0346 (17)	0.0459 (19)	0.0054 (14)	0.0054 (15)	0.0030 (15)
C2	0.047 (2)	0.050 (2)	0.045 (2)	0.0095 (17)	−0.0058 (16)	0.0038 (16)
C3	0.0375 (18)	0.0328 (17)	0.0380 (17)	0.0035 (14)	0.0047 (14)	0.0021 (13)
C4	0.0342 (17)	0.0352 (17)	0.0378 (17)	0.0054 (13)	0.0032 (13)	0.0033 (14)
C5	0.0369 (19)	0.050 (2)	0.044 (2)	−0.0031 (16)	0.0009 (15)	0.0002 (16)
C6	0.047 (2)	0.056 (2)	0.047 (2)	0.0045 (17)	−0.0028 (16)	0.0192 (17)
C7	0.045 (2)	0.081 (3)	0.038 (2)	0.000 (2)	−0.0019 (16)	0.0173 (19)
C8	0.048 (3)	0.111 (4)	0.079 (3)	0.006 (3)	−0.002 (2)	−0.024 (3)
C9	0.056 (3)	0.091 (4)	0.107 (4)	0.005 (3)	−0.005 (3)	−0.022 (3)
C10	0.042 (2)	0.056 (2)	0.068 (3)	0.0014 (18)	−0.0051 (18)	−0.005 (2)
C11	0.082 (3)	0.073 (3)	0.041 (2)	0.002 (2)	0.007 (2)	0.019 (2)
C12	0.043 (2)	0.048 (2)	0.054 (2)	−0.0007 (17)	0.0092 (17)	0.0112 (18)
C13	0.038 (2)	0.050 (2)	0.063 (2)	0.0029 (17)	0.0123 (17)	0.0080 (18)

Geometric parameters (Å, º) top

Cl1—C13	1.760 (4)	N4—C5	1.331 (5)
Cl2—C13	1.750 (4)	N4—C3	1.359 (4)
Cl3—C13	1.752 (4)	C1—C4	1.429 (5)
O1—C1	1.222 (4)	C4—C3	1.366 (5)
O2—C2	1.212 (4)	C5—H5	0.9300
O3—C7	1.402 (5)	C6—C7	1.501 (6)
O3—C8	1.426 (6)	C6—H6A	0.9700
O4—C7	1.413 (5)	C6—H6B	0.9700
O4—C9	1.419 (6)	C7—H7	0.9800
O5—C12	1.181 (5)	C8—C9	1.472 (7)
O6—C12	1.278 (5)	C8—H8A	0.9700
O6—H6	0.8200	C8—H8B	0.9700
N1—C1	1.398 (4)	C9—H9A	0.9700
N1—C2	1.403 (5)	C9—H9B	0.9700
N1—C10	1.475 (5)	C10—H10A	0.9600
N2—C3	1.371 (4)	C10—H10B	0.9600
N2—C2	1.384 (5)	C10—H10C	0.9600
N2—C11	1.468 (5)	C11—H11A	0.9600
N3—C5	1.330 (4)	C11—H11B	0.9600
N3—C4	1.388 (4)	C11—H11C	0.9600
N3—C6	1.462 (4)	C12—C13	1.553 (5)

C1—N1—C2	127.5 (3)	O3—C8—H8A	110.8
C1—N1—C10	115.6 (3)	O3—C8—H8B	110.8
C2—N1—C10	116.9 (3)	O4—C7—C6	110.6 (3)
C2—N2—C11	120.1 (3)	O4—C7—H7	109.5
C3—N2—C2	119.3 (3)	O4—C9—C8	105.2 (4)
C3—N2—C11	120.4 (3)	O4—C9—H9A	110.7
C3—C4—N3	105.3 (3)	O4—C9—H9B	110.7
C3—C4—C1	123.0 (3)	O5—C12—O6	126.9 (4)
C4—N3—C6	128.3 (3)	O5—C12—C13	119.8 (4)
C4—C3—N2	122.3 (3)	O6—C12—C13	113.1 (3)
C5—N3—C4	106.2 (3)	N1—C1—C4	111.3 (3)
C5—N3—C6	125.5 (3)	N1—C10—H10A	109.5
C5—N4—C3	104.1 (3)	N1—C10—H10B	109.5
C6—C7—H7	109.5	N1—C10—H10C	109.5
C7—O3—C8	104.9 (3)	N2—C2—N1	116.6 (3)
C7—O4—C9	108.0 (3)	N2—C11—H11A	109.5
C7—C6—H6A	109.1	N2—C11—H11B	109.5
C7—C6—H6B	109.1	N2—C11—H11C	109.5
C8—C9—H9A	110.7	N3—C4—C1	131.6 (3)
C8—C9—H9B	110.7	N3—C5—N4	113.3 (3)
C9—C8—H8A	110.8	N3—C5—H5	123.3
C9—C8—H8B	110.8	N3—C6—C7	112.3 (3)
C12—O6—H6	109.5	N3—C6—H6A	109.1
C12—C13—Cl2	109.4 (3)	N3—C6—H6B	109.1
C12—C13—Cl3	113.0 (3)	N4—C3—C4	111.1 (3)
Cl2—C13—Cl3	109.9 (2)	N4—C3—N2	126.6 (3)
C12—C13—Cl1	107.0 (3)	N4—C5—H5	123.3
Cl2—C13—Cl1	108.7 (2)	H6A—C6—H6B	107.9
Cl3—C13—Cl1	108.6 (2)	H8A—C8—H8B	108.9
O1—C1—N1	121.5 (3)	H9A—C9—H9B	108.8
O1—C1—C4	127.2 (3)	H10A—C10—H10B	109.5
O2—C2—N2	121.3 (4)	H10A—C10—H10C	109.5
O2—C2—N1	122.1 (4)	H10B—C10—H10C	109.5
O3—C7—O4	106.5 (3)	H11A—C11—H11B	109.5
O3—C7—C6	111.3 (3)	H11A—C11—H11C	109.5
O3—C7—H7	109.5	H11B—C11—H11C	109.5
O3—C8—C9	104.8 (4)

C1—C4—C3—N4	−177.2 (3)	C9—O4—C7—O3	19.5 (4)
C1—C4—C3—N2	0.6 (5)	C9—O4—C7—C6	140.7 (4)
C1—N1—C2—O2	179.3 (4)	C10—N1—C1—O1	0.6 (5)
C1—N1—C2—N2	−1.6 (5)	C10—N1—C1—C4	−179.9 (3)
C2—N1—C1—O1	−178.2 (3)	C10—N1—C2—O2	0.4 (6)
C2—N1—C1—C4	1.2 (5)	C10—N1—C2—N2	179.5 (3)
C2—N2—C3—N4	176.5 (3)	C11—N2—C3—N4	2.5 (5)
C2—N2—C3—C4	−1.0 (5)	C11—N2—C3—C4	−175.0 (4)
C3—N2—C2—O2	−179.5 (4)	C11—N2—C2—O2	−5.5 (6)
C3—N2—C2—N1	1.4 (5)	C11—N2—C2—N1	175.4 (3)
C3—N4—C5—N3	−0.4 (4)	N1—C1—C4—C3	−0.7 (5)
C4—N3—C5—N4	−0.1 (4)	N1—C1—C4—N3	−176.0 (3)
C4—N3—C6—C7	−94.6 (4)	N3—C4—C3—N4	−0.9 (4)
C5—N3—C6—C7	85.8 (4)	N3—C4—C3—N2	177.0 (3)
C5—N3—C4—C3	0.6 (4)	N3—C6—C7—O3	61.6 (4)
C5—N3—C4—C1	176.4 (4)	N3—C6—C7—O4	−56.6 (4)
C5—N4—C3—C4	0.8 (4)	O1—C1—C4—C3	178.8 (3)
C5—N4—C3—N2	−176.9 (3)	O1—C1—C4—N3	3.5 (6)
C6—N3—C5—N4	179.6 (3)	O3—C8—C9—O4	−19.2 (6)
C6—N3—C4—C3	−179.2 (3)	O5—C12—C13—Cl2	27.5 (5)
C6—N3—C4—C1	−3.3 (6)	O5—C12—C13—Cl3	150.4 (4)
C7—O3—C8—C9	31.3 (5)	O5—C12—C13—Cl1	−90.1 (5)
C7—O4—C9—C8	0.1 (5)	O6—C12—C13—Cl2	−155.6 (3)
C8—O3—C7—O4	−31.7 (4)	O6—C12—C13—Cl3	−32.7 (4)
C8—O3—C7—C6	−152.3 (4)	O6—C12—C13—Cl1	86.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N4	0.82	1.82	2.635 (4)	176
C5—H5···O5	0.93	2.48	3.079 (5)	123
C7—H7···O1ⁱ	0.98	2.44	3.410 (5)	171
C10—H10B···O2ⁱⁱ	0.96	2.51	3.351 (3)	147

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₄O₄·C₂HCl₃O₂
M_r	429.64
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.656 (3), 10.825 (5), 14.962 (7)
α, β, γ (°)	93.217 (9), 91.090 (8), 101.725 (9)
V (Å³)	895.1 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.38 × 0.28 × 0.17

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.818, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	4717, 3124, 2915
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.167, 1.15
No. of reflections	3124
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.41

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL(Bruker, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N4	0.82	1.82	2.635 (4)	175.9
C5—H5···O5	0.93	2.48	3.079 (5)	122.6
C7—H7···O1ⁱ	0.98	2.44	3.410 (5)	171.0
C10—H10B···O2ⁱⁱ	0.96	2.51	3.351 (3)	146.9

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1.

References

Bruker (2000). SMART (Version 5.618), SADABS (Version 2.05), SAINT (Version 6.02a) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-H., Tu, B. & Jin, Z.-M. (2007). Acta Cryst. E63, o2676–o2677. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, H. X., Tu, B., Shu, Z., Ma, X. J. & Jin, Z. M. (2007). Acta Cryst. E63, o726–o727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Feng, W.-J., Ma, X.-J., Shu, Z. & Jin, Z.-M. (2007). Acta Cryst. E63, o3609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Franzone, J. S., Reboani, C. & Fonzo, D. (1981). Farmacol. Sci. 36, 201–219. CAS Google Scholar
Li, C. H., Luo, Z. & Li, Z. H. (1995). Chin. J. Pharm. 26, 385–386. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Villani, F., De Maria, P., Ronchi, E. & Galimberti, M. (1997). Int. J. Clin. Pharmacol. Ther. 35, 107–111. CAS PubMed Web of Science Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

7-(1,3-Dioxolan-2-ylmeth­yl)-1,3-di­methyl­purine-2,6(1H,3H)-dione tri­chloro­acetic acid solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

7-(1,3-Dioxolan-2-ylmethyl)-1,3-dimethylpurine-2,6(1H,3H)-dione trichloroacetic acid solvate