In the title compound, C
11H
14N
4O
4·C
2H
4O
2, the doxofylline and acetic acid molecules are linked by O—H
N hydrogen bonds.
Supporting information
CCDC reference: 647317
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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-1
H-purine-2,6-dione
acetic acid solvate
top
Crystal data top
C11H14N4O4·C2H4O2 | F(000) = 344 |
Mr = 326.31 | Dx = 1.468 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 843 reflections |
a = 5.3724 (11) Å | θ = 2.7–25.0° |
b = 18.223 (4) Å | µ = 0.12 mm−1 |
c = 7.6663 (16) Å | T = 298 K |
β = 100.474 (4)° | Block, colorless |
V = 738.0 (3) Å3 | 0.33 × 0.21 × 0.17 mm |
Z = 2 | |
Data collection top
Bruker APEX area-detector diffractometer | 1340 independent reflections |
Radiation source: fine-focus sealed tube | 1321 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −6→6 |
Tmin = 0.962, Tmax = 0.976 | k = 0→21 |
6377 measured reflections | l = 0→9 |
Refinement top
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)] = 0.067 | H-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 reflections | Δρmax = 0.32 e Å−3 |
212 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.3733 (10) | 0.2747 (2) | 0.2065 (6) | 0.0481 (11) | |
O2 | 0.3000 (9) | 0.5237 (3) | 0.1522 (7) | 0.0525 (13) | |
O3 | 0.5612 (8) | 0.2287 (2) | 0.6509 (6) | 0.0443 (11) | |
O4 | 0.9673 (7) | 0.2076 (2) | 0.7760 (6) | 0.0455 (11) | |
N1 | 0.3421 (9) | 0.3994 (3) | 0.1765 (7) | 0.0373 (12) | |
N2 | 0.6496 (9) | 0.4803 (3) | 0.3286 (7) | 0.0367 (12) | |
N3 | 0.8815 (9) | 0.3057 (3) | 0.4575 (7) | 0.0354 (11) | |
N4 | 1.0097 (10) | 0.4199 (3) | 0.5094 (7) | 0.0415 (12) | |
C1 | 0.4629 (11) | 0.3345 (3) | 0.2486 (7) | 0.0333 (13) | |
C4 | 0.6931 (11) | 0.3504 (3) | 0.3671 (7) | 0.0322 (12) | |
C3 | 0.7857 (10) | 0.4195 (3) | 0.4031 (8) | 0.0326 (12) | |
C2 | 0.4218 (12) | 0.4716 (3) | 0.2178 (8) | 0.0385 (14) | |
C5 | 1.0615 (11) | 0.3487 (4) | 0.5395 (8) | 0.0407 (15) | |
H5 | 1.2089 | 0.3315 | 0.6107 | 0.049* | |
C10 | 0.1116 (13) | 0.3907 (4) | 0.0440 (10) | 0.0515 (17) | |
H10A | −0.0281 | 0.4126 | 0.0869 | 0.077* | |
H10B | 0.0785 | 0.3394 | 0.0223 | 0.077* | |
H10C | 0.1329 | 0.4142 | −0.0643 | 0.077* | |
C11 | 0.7578 (14) | 0.5539 (3) | 0.3646 (9) | 0.0477 (16) | |
H11A | 0.6255 | 0.5898 | 0.3404 | 0.072* | |
H11B | 0.8802 | 0.5627 | 0.2900 | 0.072* | |
H11C | 0.8386 | 0.5571 | 0.4867 | 0.072* | |
C6 | 0.8760 (14) | 0.2239 (3) | 0.4623 (9) | 0.0474 (16) | |
H6A | 1.0446 | 0.2052 | 0.4606 | 0.057* | |
H6B | 0.7645 | 0.2060 | 0.3571 | 0.057* | |
C7 | 0.7873 (10) | 0.1954 (3) | 0.6230 (8) | 0.0394 (14) | |
H7 | 0.7589 | 0.1424 | 0.6090 | 0.047* | |
C8 | 0.5891 (13) | 0.2458 (4) | 0.8337 (9) | 0.0468 (16) | |
H8A | 0.4464 | 0.2278 | 0.8826 | 0.056* | |
H8B | 0.6043 | 0.2983 | 0.8530 | 0.056* | |
C9 | 0.8286 (13) | 0.2071 (3) | 0.9148 (9) | 0.0439 (15) | |
H9A | 0.9172 | 0.2333 | 1.0177 | 0.053* | |
H9B | 0.7947 | 0.1573 | 0.9490 | 0.053* | |
O5 | 0.4369 (11) | −0.0531 (3) | 0.1979 (9) | 0.0754 (18) | |
O6 | 0.6795 (10) | 0.0333 (3) | 0.3375 (7) | 0.0640 (15) | |
H6 | 0.7729 | −0.0016 | 0.3695 | 0.096* | |
C12 | 0.4820 (13) | 0.0108 (4) | 0.2284 (9) | 0.0483 (16) | |
C13 | 0.3080 (15) | 0.0708 (5) | 0.1447 (10) | 0.061 (2) | |
H13A | 0.2003 | 0.0522 | 0.0403 | 0.092* | |
H13B | 0.4066 | 0.1109 | 0.1128 | 0.092* | |
H13C | 0.2061 | 0.0875 | 0.2274 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.057 (3) | 0.025 (2) | 0.057 (3) | −0.007 (2) | −0.003 (2) | −0.0045 (19) |
O2 | 0.045 (3) | 0.031 (2) | 0.076 (3) | 0.005 (2) | −0.005 (2) | 0.005 (2) |
O3 | 0.033 (2) | 0.043 (3) | 0.056 (3) | 0.0040 (18) | 0.0037 (19) | 0.007 (2) |
O4 | 0.034 (2) | 0.041 (3) | 0.060 (3) | 0.0042 (19) | 0.0037 (18) | 0.011 (2) |
N1 | 0.035 (3) | 0.029 (3) | 0.045 (3) | −0.005 (2) | −0.001 (2) | 0.002 (2) |
N2 | 0.039 (3) | 0.020 (2) | 0.049 (3) | −0.001 (2) | 0.003 (2) | 0.002 (2) |
N3 | 0.040 (3) | 0.026 (2) | 0.042 (3) | 0.001 (2) | 0.012 (2) | 0.0086 (19) |
N4 | 0.040 (3) | 0.030 (3) | 0.053 (3) | −0.005 (2) | 0.003 (2) | 0.004 (2) |
C1 | 0.042 (3) | 0.026 (3) | 0.036 (3) | −0.003 (3) | 0.017 (2) | 0.000 (2) |
C4 | 0.038 (3) | 0.022 (3) | 0.038 (3) | −0.001 (2) | 0.012 (2) | 0.000 (2) |
C3 | 0.033 (3) | 0.026 (3) | 0.038 (3) | −0.003 (2) | 0.006 (2) | 0.000 (2) |
C2 | 0.045 (3) | 0.028 (3) | 0.043 (3) | 0.005 (3) | 0.010 (3) | 0.009 (2) |
C5 | 0.027 (3) | 0.050 (4) | 0.042 (3) | 0.006 (3) | −0.001 (2) | 0.012 (3) |
C10 | 0.051 (4) | 0.041 (4) | 0.059 (4) | −0.003 (3) | −0.002 (3) | 0.002 (3) |
C11 | 0.058 (4) | 0.023 (3) | 0.058 (4) | −0.006 (3) | −0.001 (3) | 0.004 (3) |
C6 | 0.056 (4) | 0.024 (3) | 0.062 (4) | 0.011 (3) | 0.012 (3) | 0.002 (3) |
C7 | 0.033 (3) | 0.023 (3) | 0.058 (4) | 0.008 (2) | −0.002 (3) | 0.007 (2) |
C8 | 0.045 (4) | 0.040 (4) | 0.054 (4) | 0.004 (3) | 0.006 (3) | −0.004 (3) |
C9 | 0.053 (3) | 0.024 (3) | 0.051 (3) | −0.006 (3) | 0.001 (3) | 0.003 (3) |
O5 | 0.062 (4) | 0.048 (4) | 0.109 (5) | −0.003 (3) | −0.004 (3) | −0.004 (3) |
O6 | 0.061 (3) | 0.043 (3) | 0.077 (4) | 0.010 (2) | −0.017 (3) | −0.007 (3) |
C12 | 0.049 (4) | 0.049 (4) | 0.048 (4) | −0.002 (3) | 0.011 (3) | −0.002 (3) |
C13 | 0.059 (5) | 0.061 (5) | 0.060 (4) | 0.018 (4) | 0.002 (4) | 0.000 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.212 (7) | C10—H10B | 0.9600 |
O2—C2 | 1.210 (8) | C10—H10C | 0.9600 |
O3—C7 | 1.409 (7) | C11—H11A | 0.9600 |
O3—C8 | 1.417 (8) | C11—H11B | 0.9600 |
O4—C7 | 1.396 (7) | C11—H11C | 0.9600 |
O4—C9 | 1.405 (8) | C6—C7 | 1.492 (9) |
N1—C2 | 1.402 (8) | C6—H6A | 0.9700 |
N1—C1 | 1.412 (8) | C6—H6B | 0.9700 |
N1—C10 | 1.460 (8) | C7—H7 | 0.9800 |
N2—C2 | 1.367 (8) | C8—C9 | 1.500 (10) |
N2—C3 | 1.392 (8) | C8—H8A | 0.9700 |
N2—C11 | 1.467 (8) | C8—H8B | 0.9700 |
N3—C5 | 1.312 (8) | C9—H9A | 0.9700 |
N3—C4 | 1.384 (8) | C9—H9B | 0.9700 |
N3—C6 | 1.492 (8) | O5—C12 | 1.204 (9) |
N4—C3 | 1.325 (8) | O6—C12 | 1.293 (9) |
N4—C5 | 1.338 (9) | O6—H6 | 0.8200 |
C1—C4 | 1.425 (8) | C12—C13 | 1.504 (11) |
C4—C3 | 1.363 (8) | C13—H13A | 0.9600 |
C5—H5 | 0.9300 | C13—H13B | 0.9600 |
C10—H10A | 0.9600 | C13—H13C | 0.9600 |
| | | |
C7—O3—C8 | 107.8 (5) | H11A—C11—H11C | 109.5 |
C7—O4—C9 | 104.7 (5) | H11B—C11—H11C | 109.5 |
C2—N1—C1 | 126.7 (5) | N3—C6—C7 | 112.3 (5) |
C2—N1—C10 | 116.4 (5) | N3—C6—H6A | 109.1 |
C1—N1—C10 | 116.9 (5) | C7—C6—H6A | 109.1 |
C2—N2—C3 | 120.4 (5) | N3—C6—H6B | 109.1 |
C2—N2—C11 | 120.2 (5) | C7—C6—H6B | 109.1 |
C3—N2—C11 | 119.3 (5) | H6A—C6—H6B | 107.9 |
C5—N3—C4 | 107.3 (5) | O4—C7—O3 | 106.7 (5) |
C5—N3—C6 | 126.9 (6) | O4—C7—C6 | 111.2 (5) |
C4—N3—C6 | 125.8 (6) | O3—C7—C6 | 112.8 (5) |
C3—N4—C5 | 103.8 (5) | O4—C7—H7 | 108.7 |
O1—C1—N1 | 121.1 (5) | O3—C7—H7 | 108.7 |
O1—C1—C4 | 127.6 (6) | C6—C7—H7 | 108.7 |
N1—C1—C4 | 111.3 (5) | O3—C8—C9 | 103.6 (5) |
C3—C4—N3 | 103.6 (5) | O3—C8—H8A | 111.0 |
C3—C4—C1 | 124.0 (5) | C9—C8—H8A | 111.0 |
N3—C4—C1 | 132.1 (5) | O3—C8—H8B | 111.0 |
N4—C3—C4 | 112.7 (5) | C9—C8—H8B | 111.0 |
N4—C3—N2 | 126.8 (5) | H8A—C8—H8B | 109.0 |
C4—C3—N2 | 120.5 (5) | O4—C9—C8 | 102.4 (5) |
O2—C2—N2 | 121.5 (6) | O4—C9—H9A | 111.3 |
O2—C2—N1 | 121.6 (6) | C8—C9—H9A | 111.3 |
N2—C2—N1 | 116.9 (5) | O4—C9—H9B | 111.3 |
N3—C5—N4 | 112.5 (5) | C8—C9—H9B | 111.3 |
N3—C5—H5 | 123.7 | H9A—C9—H9B | 109.2 |
N4—C5—H5 | 123.7 | C12—O6—H6 | 109.5 |
N1—C10—H10A | 109.5 | O5—C12—O6 | 123.0 (7) |
N1—C10—H10B | 109.5 | O5—C12—C13 | 122.2 (7) |
H10A—C10—H10B | 109.5 | O6—C12—C13 | 114.8 (7) |
N1—C10—H10C | 109.5 | C12—C13—H13A | 109.5 |
H10A—C10—H10C | 109.5 | C12—C13—H13B | 109.5 |
H10B—C10—H10C | 109.5 | H13A—C13—H13B | 109.5 |
N2—C11—H11A | 109.5 | C12—C13—H13C | 109.5 |
N2—C11—H11B | 109.5 | H13A—C13—H13C | 109.5 |
H11A—C11—H11B | 109.5 | H13B—C13—H13C | 109.5 |
N2—C11—H11C | 109.5 | | |
| | | |
C2—N1—C1—O1 | 178.0 (6) | C3—N2—C2—O2 | 179.7 (6) |
C10—N1—C1—O1 | −2.5 (8) | C11—N2—C2—O2 | −2.8 (9) |
C2—N1—C1—C4 | −3.2 (8) | C3—N2—C2—N1 | −3.5 (8) |
C10—N1—C1—C4 | 176.2 (5) | C11—N2—C2—N1 | 174.1 (6) |
C5—N3—C4—C3 | 1.1 (6) | C1—N1—C2—O2 | −177.7 (6) |
C6—N3—C4—C3 | −179.9 (5) | C10—N1—C2—O2 | 2.9 (9) |
C5—N3—C4—C1 | 175.7 (6) | C1—N1—C2—N2 | 5.5 (9) |
C6—N3—C4—C1 | −5.3 (10) | C10—N1—C2—N2 | −173.9 (6) |
O1—C1—C4—C3 | 177.6 (6) | C4—N3—C5—N4 | −0.7 (7) |
N1—C1—C4—C3 | −1.0 (7) | C6—N3—C5—N4 | −179.7 (6) |
O1—C1—C4—N3 | 4.0 (10) | C3—N4—C5—N3 | −0.1 (7) |
N1—C1—C4—N3 | −174.7 (6) | C5—N3—C6—C7 | 82.4 (8) |
C5—N4—C3—C4 | 0.8 (7) | C4—N3—C6—C7 | −96.3 (7) |
C5—N4—C3—N2 | −178.2 (6) | C9—O4—C7—O3 | 33.2 (6) |
N3—C4—C3—N4 | −1.2 (6) | C9—O4—C7—C6 | 156.7 (5) |
C1—C4—C3—N4 | −176.4 (5) | C8—O3—C7—O4 | −13.3 (6) |
N3—C4—C3—N2 | 177.9 (5) | C8—O3—C7—C6 | −135.8 (6) |
C1—C4—C3—N2 | 2.7 (8) | N3—C6—C7—O4 | −70.3 (7) |
C2—N2—C3—N4 | 178.6 (6) | N3—C6—C7—O3 | 49.6 (8) |
C11—N2—C3—N4 | 1.1 (9) | C7—O3—C8—C9 | −10.3 (6) |
C2—N2—C3—C4 | −0.3 (8) | C7—O4—C9—C8 | −38.6 (6) |
C11—N2—C3—C4 | −177.8 (6) | O3—C8—C9—O4 | 29.9 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···N4i | 0.82 | 1.97 | 2.779 (7) | 170 |
C8—H8A···O4ii | 0.97 | 2.58 | 3.362 (6) | 138 |
C9—H9B···O2iii | 0.97 | 2.58 | 3.432 (7) | 147 |
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1. |