In the title molecule, C
11H
14N
4O
4, all bond lengths and angles are normal. The crystal packing is stabilized by weak intermolecular C—H
O hydrogen bonds and π–π stacking interactions.
Supporting information
CCDC reference: 654886
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.088
- wR factor = 0.188
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.07 Ratio
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.93 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C8 - C9 ... 1.37 Ang.
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
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.
Ethyl (1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetate
top
Crystal data top
C11H14N4O4 | F(000) = 560 |
Mr = 266.26 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1254 reflections |
a = 8.502 (5) Å | θ = 2.5–24.1° |
b = 20.702 (12) Å | µ = 0.11 mm−1 |
c = 7.399 (4) Å | T = 298 K |
β = 107.492 (12)° | Block, colourless |
V = 1242.0 (12) Å3 | 0.15 × 0.14 × 0.13 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 2188 independent reflections |
Radiation source: fine-focus sealed tube | 1715 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.984, Tmax = 0.991 | k = −22→24 |
6459 measured reflections | l = −7→8 |
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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0527P)2 + 1.4768P] where P = (Fo2 + 2Fc2)/3 |
2188 reflections | (Δ/σ)max < 0.001 |
175 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−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 | 0.6561 (4) | 0.42446 (13) | 0.0833 (4) | 0.0650 (9) | |
O2 | 0.2499 (3) | 0.29210 (15) | −0.2752 (4) | 0.0642 (9) | |
O3 | 1.1062 (4) | 0.43953 (15) | 0.3271 (4) | 0.0730 (10) | |
O4 | 1.0342 (4) | 0.37959 (15) | 0.0653 (4) | 0.0661 (9) | |
N1 | 0.4544 (4) | 0.35752 (15) | −0.0998 (4) | 0.0446 (8) | |
N2 | 0.4821 (4) | 0.24456 (15) | −0.0911 (4) | 0.0435 (8) | |
N3 | 0.8481 (3) | 0.29969 (15) | 0.2261 (4) | 0.0417 (8) | |
N4 | 0.7383 (4) | 0.20414 (15) | 0.1230 (5) | 0.0476 (8) | |
C1 | 0.6097 (5) | 0.37010 (18) | 0.0332 (5) | 0.0432 (9) | |
C2 | 0.3874 (5) | 0.2973 (2) | −0.1615 (5) | 0.0449 (10) | |
C3 | 0.6349 (4) | 0.25227 (18) | 0.0387 (5) | 0.0382 (9) | |
C4 | 0.6960 (4) | 0.31178 (17) | 0.0960 (5) | 0.0374 (9) | |
C5 | 0.8650 (5) | 0.23573 (19) | 0.2349 (6) | 0.0486 (10) | |
H5 | 0.9580 | 0.2152 | 0.3130 | 0.058* | |
C6 | 0.9595 (5) | 0.3477 (2) | 0.3397 (6) | 0.0511 (11) | |
H6A | 1.0471 | 0.3259 | 0.4352 | 0.061* | |
H6B | 0.8996 | 0.3743 | 0.4045 | 0.061* | |
C7 | 1.0342 (5) | 0.3902 (2) | 0.2229 (6) | 0.0493 (10) | |
C8 | 1.1918 (9) | 0.4854 (3) | 0.2416 (9) | 0.108 (2) | |
H8A | 1.2806 | 0.4637 | 0.2089 | 0.129* | |
H8B | 1.1159 | 0.5024 | 0.1258 | 0.129* | |
C9 | 1.2548 (12) | 0.5351 (3) | 0.3629 (10) | 0.152 (4) | |
H9A | 1.1665 | 0.5578 | 0.3911 | 0.228* | |
H9B | 1.3132 | 0.5642 | 0.3050 | 0.228* | |
H9C | 1.3290 | 0.5183 | 0.4780 | 0.228* | |
C10 | 0.3485 (6) | 0.4137 (2) | −0.1735 (7) | 0.0662 (13) | |
H10A | 0.3303 | 0.4172 | −0.3076 | 0.099* | |
H10B | 0.4013 | 0.4522 | −0.1121 | 0.099* | |
H10C | 0.2446 | 0.4083 | −0.1490 | 0.099* | |
C11 | 0.4140 (5) | 0.1801 (2) | −0.1439 (6) | 0.0591 (12) | |
H11A | 0.3549 | 0.1666 | −0.0584 | 0.089* | |
H11B | 0.5020 | 0.1503 | −0.1372 | 0.089* | |
H11C | 0.3402 | 0.1810 | −0.2709 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0668 (19) | 0.0378 (17) | 0.077 (2) | −0.0005 (14) | 0.0017 (16) | 0.0002 (15) |
O2 | 0.0416 (17) | 0.091 (2) | 0.0507 (18) | −0.0067 (15) | −0.0010 (14) | −0.0006 (16) |
O3 | 0.091 (2) | 0.063 (2) | 0.0550 (19) | −0.0302 (18) | 0.0077 (17) | −0.0030 (16) |
O4 | 0.077 (2) | 0.075 (2) | 0.0465 (19) | −0.0188 (17) | 0.0181 (16) | 0.0029 (16) |
N1 | 0.0393 (18) | 0.049 (2) | 0.0432 (19) | 0.0091 (15) | 0.0089 (15) | 0.0062 (15) |
N2 | 0.0416 (18) | 0.0447 (19) | 0.0449 (19) | −0.0096 (15) | 0.0141 (16) | −0.0044 (15) |
N3 | 0.0346 (17) | 0.0464 (19) | 0.0413 (18) | 0.0014 (14) | 0.0074 (14) | 0.0076 (15) |
N4 | 0.049 (2) | 0.0402 (18) | 0.056 (2) | 0.0068 (16) | 0.0194 (17) | 0.0056 (16) |
C1 | 0.046 (2) | 0.040 (2) | 0.043 (2) | 0.0011 (18) | 0.0134 (19) | 0.0039 (18) |
C2 | 0.040 (2) | 0.060 (3) | 0.038 (2) | −0.003 (2) | 0.0160 (19) | −0.0016 (19) |
C3 | 0.039 (2) | 0.042 (2) | 0.038 (2) | 0.0013 (17) | 0.0176 (18) | 0.0008 (16) |
C4 | 0.0347 (19) | 0.038 (2) | 0.038 (2) | 0.0000 (16) | 0.0092 (17) | 0.0022 (16) |
C5 | 0.040 (2) | 0.054 (3) | 0.051 (2) | 0.013 (2) | 0.013 (2) | 0.014 (2) |
C6 | 0.038 (2) | 0.066 (3) | 0.041 (2) | −0.0078 (19) | 0.0007 (18) | 0.004 (2) |
C7 | 0.038 (2) | 0.053 (3) | 0.048 (3) | −0.0042 (19) | 0.0000 (19) | 0.006 (2) |
C8 | 0.149 (6) | 0.077 (4) | 0.085 (4) | −0.059 (4) | 0.017 (4) | 0.008 (3) |
C9 | 0.263 (10) | 0.096 (5) | 0.113 (5) | −0.092 (6) | 0.080 (6) | −0.029 (4) |
C10 | 0.061 (3) | 0.066 (3) | 0.065 (3) | 0.023 (2) | 0.009 (2) | 0.008 (2) |
C11 | 0.062 (3) | 0.061 (3) | 0.062 (3) | −0.020 (2) | 0.029 (2) | −0.016 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.213 (4) | C3—C4 | 1.355 (5) |
O2—C2 | 1.222 (4) | C5—H5 | 0.9300 |
O3—C7 | 1.315 (5) | C6—C7 | 1.501 (6) |
O3—C8 | 1.453 (6) | C6—H6A | 0.9700 |
O4—C7 | 1.187 (5) | C6—H6B | 0.9700 |
N1—C2 | 1.390 (5) | C8—C9 | 1.364 (7) |
N1—C1 | 1.413 (5) | C8—H8A | 0.9700 |
N1—C10 | 1.471 (5) | C8—H8B | 0.9700 |
N2—C2 | 1.364 (5) | C9—H9A | 0.9600 |
N2—C3 | 1.373 (4) | C9—H9B | 0.9600 |
N2—C11 | 1.461 (5) | C9—H9C | 0.9600 |
N3—C5 | 1.331 (5) | C10—H10A | 0.9600 |
N3—C4 | 1.383 (4) | C10—H10B | 0.9600 |
N3—C6 | 1.453 (5) | C10—H10C | 0.9600 |
N4—C5 | 1.318 (5) | C11—H11A | 0.9600 |
N4—C3 | 1.351 (5) | C11—H11B | 0.9600 |
C1—C4 | 1.417 (5) | C11—H11C | 0.9600 |
| | | |
C7—O3—C8 | 117.3 (4) | C7—C6—H6B | 109.1 |
C2—N1—C1 | 126.8 (3) | H6A—C6—H6B | 107.8 |
C2—N1—C10 | 116.2 (3) | O4—C7—O3 | 125.6 (4) |
C1—N1—C10 | 116.9 (3) | O4—C7—C6 | 125.6 (4) |
C2—N2—C3 | 120.0 (3) | O3—C7—C6 | 108.7 (4) |
C2—N2—C11 | 119.2 (3) | C9—C8—O3 | 110.8 (5) |
C3—N2—C11 | 120.6 (3) | C9—C8—H8A | 109.5 |
C5—N3—C4 | 106.2 (3) | O3—C8—H8A | 109.5 |
C5—N3—C6 | 127.6 (3) | C9—C8—H8B | 109.5 |
C4—N3—C6 | 126.1 (3) | O3—C8—H8B | 109.5 |
C5—N4—C3 | 102.7 (3) | H8A—C8—H8B | 108.1 |
O1—C1—N1 | 122.3 (3) | C8—C9—H9A | 109.5 |
O1—C1—C4 | 127.0 (4) | C8—C9—H9B | 109.5 |
N1—C1—C4 | 110.8 (3) | H9A—C9—H9B | 109.5 |
O2—C2—N2 | 121.7 (4) | C8—C9—H9C | 109.5 |
O2—C2—N1 | 121.2 (4) | H9A—C9—H9C | 109.5 |
N2—C2—N1 | 117.1 (3) | H9B—C9—H9C | 109.5 |
N4—C3—C4 | 113.0 (3) | N1—C10—H10A | 109.5 |
N4—C3—N2 | 125.8 (3) | N1—C10—H10B | 109.5 |
C4—C3—N2 | 121.2 (3) | H10A—C10—H10B | 109.5 |
C3—C4—N3 | 104.1 (3) | N1—C10—H10C | 109.5 |
C3—C4—C1 | 124.1 (3) | H10A—C10—H10C | 109.5 |
N3—C4—C1 | 131.8 (3) | H10B—C10—H10C | 109.5 |
N4—C5—N3 | 114.0 (3) | N2—C11—H11A | 109.5 |
N4—C5—H5 | 123.0 | N2—C11—H11B | 109.5 |
N3—C5—H5 | 123.0 | H11A—C11—H11B | 109.5 |
N3—C6—C7 | 112.5 (3) | N2—C11—H11C | 109.5 |
N3—C6—H6A | 109.1 | H11A—C11—H11C | 109.5 |
C7—C6—H6A | 109.1 | H11B—C11—H11C | 109.5 |
N3—C6—H6B | 109.1 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···O2i | 0.97 | 2.42 | 3.363 (5) | 166 |
Symmetry code: (i) x+1, y, z+1. |