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In the title compound, C11H14N4O4·C2H4O2, the doxofylline and acetic acid mol­ecules are linked by O—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014341/sa2043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014341/sa2043Isup2.hkl
Contains datablock I

CCDC reference: 647317

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.067
  • wR factor = 0.169
  • Data-to-parameter ratio = 6.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.32 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H9A .. H10B .. 2.12 Ang. PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.03
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 1340 Count of symmetry unique reflns 1345 Completeness (_total/calc) 99.63% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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.

7-(1,3-Dioxolan-2-ylmethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione acetic acid solvate top
Crystal data top
C11H14N4O4·C2H4O2F(000) = 344
Mr = 326.31Dx = 1.468 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 843 reflections
a = 5.3724 (11) Åθ = 2.7–25.0°
b = 18.223 (4) ŵ = 0.12 mm1
c = 7.6663 (16) ÅT = 298 K
β = 100.474 (4)°Block, colorless
V = 738.0 (3) Å30.33 × 0.21 × 0.17 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
1340 independent reflections
Radiation source: fine-focus sealed tube1321 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 66
Tmin = 0.962, Tmax = 0.976k = 021
6377 measured reflectionsl = 09
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0816P)2 + 0.4926P]
where P = (Fo2 + 2Fc2)/3
S = 1.29(Δ/σ)max = 0.005
1340 reflectionsΔρmax = 0.32 e Å3
212 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (3)
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.3733 (10)0.2747 (2)0.2065 (6)0.0481 (11)
O20.3000 (9)0.5237 (3)0.1522 (7)0.0525 (13)
O30.5612 (8)0.2287 (2)0.6509 (6)0.0443 (11)
O40.9673 (7)0.2076 (2)0.7760 (6)0.0455 (11)
N10.3421 (9)0.3994 (3)0.1765 (7)0.0373 (12)
N20.6496 (9)0.4803 (3)0.3286 (7)0.0367 (12)
N30.8815 (9)0.3057 (3)0.4575 (7)0.0354 (11)
N41.0097 (10)0.4199 (3)0.5094 (7)0.0415 (12)
C10.4629 (11)0.3345 (3)0.2486 (7)0.0333 (13)
C40.6931 (11)0.3504 (3)0.3671 (7)0.0322 (12)
C30.7857 (10)0.4195 (3)0.4031 (8)0.0326 (12)
C20.4218 (12)0.4716 (3)0.2178 (8)0.0385 (14)
C51.0615 (11)0.3487 (4)0.5395 (8)0.0407 (15)
H51.20890.33150.61070.049*
C100.1116 (13)0.3907 (4)0.0440 (10)0.0515 (17)
H10A0.02810.41260.08690.077*
H10B0.07850.33940.02230.077*
H10C0.13290.41420.06430.077*
C110.7578 (14)0.5539 (3)0.3646 (9)0.0477 (16)
H11A0.62550.58980.34040.072*
H11B0.88020.56270.29000.072*
H11C0.83860.55710.48670.072*
C60.8760 (14)0.2239 (3)0.4623 (9)0.0474 (16)
H6A1.04460.20520.46060.057*
H6B0.76450.20600.35710.057*
C70.7873 (10)0.1954 (3)0.6230 (8)0.0394 (14)
H70.75890.14240.60900.047*
C80.5891 (13)0.2458 (4)0.8337 (9)0.0468 (16)
H8A0.44640.22780.88260.056*
H8B0.60430.29830.85300.056*
C90.8286 (13)0.2071 (3)0.9148 (9)0.0439 (15)
H9A0.91720.23331.01770.053*
H9B0.79470.15730.94900.053*
O50.4369 (11)0.0531 (3)0.1979 (9)0.0754 (18)
O60.6795 (10)0.0333 (3)0.3375 (7)0.0640 (15)
H60.77290.00160.36950.096*
C120.4820 (13)0.0108 (4)0.2284 (9)0.0483 (16)
C130.3080 (15)0.0708 (5)0.1447 (10)0.061 (2)
H13A0.20030.05220.04030.092*
H13B0.40660.11090.11280.092*
H13C0.20610.08750.22740.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.057 (3)0.025 (2)0.057 (3)0.007 (2)0.003 (2)0.0045 (19)
O20.045 (3)0.031 (2)0.076 (3)0.005 (2)0.005 (2)0.005 (2)
O30.033 (2)0.043 (3)0.056 (3)0.0040 (18)0.0037 (19)0.007 (2)
O40.034 (2)0.041 (3)0.060 (3)0.0042 (19)0.0037 (18)0.011 (2)
N10.035 (3)0.029 (3)0.045 (3)0.005 (2)0.001 (2)0.002 (2)
N20.039 (3)0.020 (2)0.049 (3)0.001 (2)0.003 (2)0.002 (2)
N30.040 (3)0.026 (2)0.042 (3)0.001 (2)0.012 (2)0.0086 (19)
N40.040 (3)0.030 (3)0.053 (3)0.005 (2)0.003 (2)0.004 (2)
C10.042 (3)0.026 (3)0.036 (3)0.003 (3)0.017 (2)0.000 (2)
C40.038 (3)0.022 (3)0.038 (3)0.001 (2)0.012 (2)0.000 (2)
C30.033 (3)0.026 (3)0.038 (3)0.003 (2)0.006 (2)0.000 (2)
C20.045 (3)0.028 (3)0.043 (3)0.005 (3)0.010 (3)0.009 (2)
C50.027 (3)0.050 (4)0.042 (3)0.006 (3)0.001 (2)0.012 (3)
C100.051 (4)0.041 (4)0.059 (4)0.003 (3)0.002 (3)0.002 (3)
C110.058 (4)0.023 (3)0.058 (4)0.006 (3)0.001 (3)0.004 (3)
C60.056 (4)0.024 (3)0.062 (4)0.011 (3)0.012 (3)0.002 (3)
C70.033 (3)0.023 (3)0.058 (4)0.008 (2)0.002 (3)0.007 (2)
C80.045 (4)0.040 (4)0.054 (4)0.004 (3)0.006 (3)0.004 (3)
C90.053 (3)0.024 (3)0.051 (3)0.006 (3)0.001 (3)0.003 (3)
O50.062 (4)0.048 (4)0.109 (5)0.003 (3)0.004 (3)0.004 (3)
O60.061 (3)0.043 (3)0.077 (4)0.010 (2)0.017 (3)0.007 (3)
C120.049 (4)0.049 (4)0.048 (4)0.002 (3)0.011 (3)0.002 (3)
C130.059 (5)0.061 (5)0.060 (4)0.018 (4)0.002 (4)0.000 (4)
Geometric parameters (Å, º) top
O1—C11.212 (7)C10—H10B0.9600
O2—C21.210 (8)C10—H10C0.9600
O3—C71.409 (7)C11—H11A0.9600
O3—C81.417 (8)C11—H11B0.9600
O4—C71.396 (7)C11—H11C0.9600
O4—C91.405 (8)C6—C71.492 (9)
N1—C21.402 (8)C6—H6A0.9700
N1—C11.412 (8)C6—H6B0.9700
N1—C101.460 (8)C7—H70.9800
N2—C21.367 (8)C8—C91.500 (10)
N2—C31.392 (8)C8—H8A0.9700
N2—C111.467 (8)C8—H8B0.9700
N3—C51.312 (8)C9—H9A0.9700
N3—C41.384 (8)C9—H9B0.9700
N3—C61.492 (8)O5—C121.204 (9)
N4—C31.325 (8)O6—C121.293 (9)
N4—C51.338 (9)O6—H60.8200
C1—C41.425 (8)C12—C131.504 (11)
C4—C31.363 (8)C13—H13A0.9600
C5—H50.9300C13—H13B0.9600
C10—H10A0.9600C13—H13C0.9600
C7—O3—C8107.8 (5)H11A—C11—H11C109.5
C7—O4—C9104.7 (5)H11B—C11—H11C109.5
C2—N1—C1126.7 (5)N3—C6—C7112.3 (5)
C2—N1—C10116.4 (5)N3—C6—H6A109.1
C1—N1—C10116.9 (5)C7—C6—H6A109.1
C2—N2—C3120.4 (5)N3—C6—H6B109.1
C2—N2—C11120.2 (5)C7—C6—H6B109.1
C3—N2—C11119.3 (5)H6A—C6—H6B107.9
C5—N3—C4107.3 (5)O4—C7—O3106.7 (5)
C5—N3—C6126.9 (6)O4—C7—C6111.2 (5)
C4—N3—C6125.8 (6)O3—C7—C6112.8 (5)
C3—N4—C5103.8 (5)O4—C7—H7108.7
O1—C1—N1121.1 (5)O3—C7—H7108.7
O1—C1—C4127.6 (6)C6—C7—H7108.7
N1—C1—C4111.3 (5)O3—C8—C9103.6 (5)
C3—C4—N3103.6 (5)O3—C8—H8A111.0
C3—C4—C1124.0 (5)C9—C8—H8A111.0
N3—C4—C1132.1 (5)O3—C8—H8B111.0
N4—C3—C4112.7 (5)C9—C8—H8B111.0
N4—C3—N2126.8 (5)H8A—C8—H8B109.0
C4—C3—N2120.5 (5)O4—C9—C8102.4 (5)
O2—C2—N2121.5 (6)O4—C9—H9A111.3
O2—C2—N1121.6 (6)C8—C9—H9A111.3
N2—C2—N1116.9 (5)O4—C9—H9B111.3
N3—C5—N4112.5 (5)C8—C9—H9B111.3
N3—C5—H5123.7H9A—C9—H9B109.2
N4—C5—H5123.7C12—O6—H6109.5
N1—C10—H10A109.5O5—C12—O6123.0 (7)
N1—C10—H10B109.5O5—C12—C13122.2 (7)
H10A—C10—H10B109.5O6—C12—C13114.8 (7)
N1—C10—H10C109.5C12—C13—H13A109.5
H10A—C10—H10C109.5C12—C13—H13B109.5
H10B—C10—H10C109.5H13A—C13—H13B109.5
N2—C11—H11A109.5C12—C13—H13C109.5
N2—C11—H11B109.5H13A—C13—H13C109.5
H11A—C11—H11B109.5H13B—C13—H13C109.5
N2—C11—H11C109.5
C2—N1—C1—O1178.0 (6)C3—N2—C2—O2179.7 (6)
C10—N1—C1—O12.5 (8)C11—N2—C2—O22.8 (9)
C2—N1—C1—C43.2 (8)C3—N2—C2—N13.5 (8)
C10—N1—C1—C4176.2 (5)C11—N2—C2—N1174.1 (6)
C5—N3—C4—C31.1 (6)C1—N1—C2—O2177.7 (6)
C6—N3—C4—C3179.9 (5)C10—N1—C2—O22.9 (9)
C5—N3—C4—C1175.7 (6)C1—N1—C2—N25.5 (9)
C6—N3—C4—C15.3 (10)C10—N1—C2—N2173.9 (6)
O1—C1—C4—C3177.6 (6)C4—N3—C5—N40.7 (7)
N1—C1—C4—C31.0 (7)C6—N3—C5—N4179.7 (6)
O1—C1—C4—N34.0 (10)C3—N4—C5—N30.1 (7)
N1—C1—C4—N3174.7 (6)C5—N3—C6—C782.4 (8)
C5—N4—C3—C40.8 (7)C4—N3—C6—C796.3 (7)
C5—N4—C3—N2178.2 (6)C9—O4—C7—O333.2 (6)
N3—C4—C3—N41.2 (6)C9—O4—C7—C6156.7 (5)
C1—C4—C3—N4176.4 (5)C8—O3—C7—O413.3 (6)
N3—C4—C3—N2177.9 (5)C8—O3—C7—C6135.8 (6)
C1—C4—C3—N22.7 (8)N3—C6—C7—O470.3 (7)
C2—N2—C3—N4178.6 (6)N3—C6—C7—O349.6 (8)
C11—N2—C3—N41.1 (9)C7—O3—C8—C910.3 (6)
C2—N2—C3—C40.3 (8)C7—O4—C9—C838.6 (6)
C11—N2—C3—C4177.8 (6)O3—C8—C9—O429.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···N4i0.821.972.779 (7)170
C8—H8A···O4ii0.972.583.362 (6)138
C9—H9B···O2iii0.972.583.432 (7)147
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x1, y, z; (iii) x+1, y1/2, z+1.
 

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