7-(1,3-Dioxolan-2-ylmeth-yl)-1,3-di-methyl-purine-2,6(1H,3H)-dione trichloro-acetic acid solvate.

In the title compound, C(11)H(14)N(4)O(4)·C(2)HCl(3)O(2), the dioxolane ring adopts an envelope conformation. Doxophylline [7-(1,3-dioxolan-2-yl-meth-yl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione] and trichloro-acetic acid mol-ecules 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 = 429.64

Triclinic,

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[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.167

S = 1.15

3124 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.41 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067025/cs2059Isup2.hkl

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

C11H14N4O4·C2HCl3O2	Z = 2
Mr = 429.64	F000 = 440
Triclinic, P1	Dx = 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 = 2.4–24.7º
α = 93.217 (9)º	µ = 0.55 mm−1
β = 91.090 (8)º	T = 293 (2) K
γ = 101.725 (9)º	Block, colorless
V = 895.1 (8) Å3	0.38 × 0.28 × 0.17 mm

Bruker APEX area-detector diffractometer	3124 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.015
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −6→6
Tmin = 0.818, Tmax = 0.912	k = −12→10
4717 measured reflections	l = −16→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073	H-atom parameters constrained
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0594P)2 + 1.1669P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
3124 reflections	Δρmax = 0.32 e Å−3
238 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .