A low-temperature [163 (2) K] redetermination of the crystal structure of the title compound, C13H14N2O3 [originally determined by Bideau, Marly & Housty (1969). C. R. Acad. Sci. Ser. C, 269, 549-551], has been performed. Although no gross strucural differences have been observed, H atoms have been located and the extended structure examined.
Supporting information
CCDC reference: 270521
Key indicators
- Single-crystal X-ray study
- T = 163 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.127
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(±)-5-Ethyl-1-methyl-5-phenylpyrimidine-2,4,6-trione
top
Crystal data top
C13H14N2O3 | F(000) = 520 |
Mr = 246.26 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/c | Melting point: 452 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.636 (6) Å | Cell parameters from 3964 reflections |
b = 7.218 (3) Å | θ = 6.2–54.5° |
c = 12.467 (6) Å | µ = 0.10 mm−1 |
β = 105.398 (6)° | T = 163 K |
V = 1183.1 (9) Å3 | Plate, colourless |
Z = 4 | 0.80 × 0.50 × 0.10 mm |
Data collection top
Bruker SMART CCD diffractometer | 2670 independent reflections |
Radiation source: fine-focus sealed tube | 1969 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 8.192 pixels mm-1 | θmax = 27.9°, θmin = 3.1° |
φ and ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | k = −9→5 |
Tmin = 0.884, Tmax = 1.000 | l = −16→16 |
15219 measured reflections | |
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)] = 0.042 | Only H-atom coordinates refined |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + 0.1704P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2670 reflections | Δρmax = 0.32 e Å−3 |
216 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.028 (4) |
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 | Occ. (<1) |
N1 | 0.65348 (10) | 0.07027 (18) | 0.33475 (10) | 0.0254 (3) | |
C1 | 0.65070 (18) | 0.1255 (3) | 0.44783 (16) | 0.0385 (5) | |
H1A | 0.602 (4) | 0.220 (8) | 0.440 (4) | 0.058* | 0.55 (4) |
H1B | 0.727 (4) | 0.157 (7) | 0.490 (4) | 0.058* | 0.55 (4) |
H1C | 0.629 (4) | 0.010 (7) | 0.489 (4) | 0.058* | 0.55 (4) |
H1D | 0.714 (5) | 0.086 (9) | 0.502 (5) | 0.058* | 0.45 (4) |
H1E | 0.586 (5) | 0.092 (10) | 0.456 (5) | 0.058* | 0.45 (4) |
H1F | 0.653 (5) | 0.268 (9) | 0.445 (4) | 0.058* | 0.45 (4) |
C2 | 0.57740 (11) | 0.1397 (2) | 0.24633 (13) | 0.0237 (4) | |
O2 | 0.51654 (8) | 0.25406 (16) | 0.2588 (1) | 0.0329 (3) | |
N3 | 0.57365 (10) | 0.06980 (18) | 0.14236 (11) | 0.0228 (3) | |
H3A | 0.5184 (14) | 0.097 (2) | 0.0901 (15) | 0.027* | |
C4 | 0.63173 (11) | −0.0714 (2) | 0.11971 (12) | 0.0220 (3) | |
O4 | 0.60741 (8) | −0.15259 (16) | 0.03090 (9) | 0.0305 (3) | |
C5 | 0.73205 (11) | −0.1082 (2) | 0.20687 (12) | 0.0224 (3) | |
C6 | 0.72608 (12) | −0.0576 (2) | 0.32398 (13) | 0.0250 (4) | |
O6 | 0.78634 (9) | −0.12010 (17) | 0.40561 (9) | 0.0353 (3) | |
C7 | 0.81121 (11) | 0.0195 (2) | 0.17474 (13) | 0.0230 (4) | |
C8 | 0.86655 (12) | 0.1522 (2) | 0.24645 (15) | 0.0292 (4) | |
H8A | 0.8597 (14) | 0.168 (3) | 0.3228 (16) | 0.035* | |
C9 | 0.93700 (13) | 0.2632 (3) | 0.21351 (17) | 0.0377 (5) | |
H9A | 0.9758 (16) | 0.353 (3) | 0.2670 (17) | 0.045* | |
C10 | 0.95306 (13) | 0.2430 (3) | 0.10971 (17) | 0.0384 (5) | |
H10A | 1.0011 (16) | 0.323 (3) | 0.0815 (17) | 0.046* | |
C11 | 0.89899 (13) | 0.1096 (3) | 0.03816 (16) | 0.0345 (4) | |
H11A | 0.9099 (14) | 0.088 (3) | −0.0339 (16) | 0.041* | |
C12 | 0.82846 (12) | −0.0014 (2) | 0.06987 (14) | 0.0291 (4) | |
H12A | 0.7939 (14) | −0.096 (3) | 0.0196 (15) | 0.035* | |
C13 | 0.76509 (12) | −0.3121 (2) | 0.20458 (15) | 0.0267 (4) | |
H13A | 0.7730 (13) | −0.332 (2) | 0.1261 (16) | 0.032* | |
H13B | 0.8342 (15) | −0.326 (2) | 0.2599 (15) | 0.032* | |
C14 | 0.69212 (14) | −0.4507 (2) | 0.23351 (17) | 0.0333 (4) | |
H14A | 0.7204 (16) | −0.568 (3) | 0.2292 (16) | 0.050* | |
H14B | 0.6232 (18) | −0.441 (3) | 0.1783 (18) | 0.050* | |
H14C | 0.6850 (16) | −0.428 (3) | 0.3103 (19) | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0289 (7) | 0.0251 (7) | 0.0227 (7) | −0.0013 (5) | 0.0076 (6) | −0.0019 (5) |
C1 | 0.0446 (12) | 0.0456 (13) | 0.0271 (10) | 0.0027 (10) | 0.0128 (9) | −0.0052 (8) |
C2 | 0.0232 (8) | 0.0188 (8) | 0.0294 (8) | −0.0035 (6) | 0.0076 (6) | −0.0006 (6) |
O2 | 0.0298 (6) | 0.0280 (7) | 0.0428 (7) | 0.0047 (5) | 0.0125 (5) | −0.0037 (5) |
N3 | 0.0201 (6) | 0.0225 (7) | 0.0239 (7) | 0.0031 (5) | 0.0024 (5) | 0.0024 (5) |
C4 | 0.0215 (7) | 0.0211 (8) | 0.0226 (8) | −0.0006 (5) | 0.0043 (6) | 0.0022 (6) |
O4 | 0.0257 (6) | 0.0327 (7) | 0.0288 (6) | 0.0037 (5) | −0.0002 (5) | −0.0057 (5) |
C5 | 0.0213 (8) | 0.0216 (8) | 0.0227 (8) | 0.0019 (6) | 0.0028 (6) | 0.0002 (6) |
C6 | 0.0260 (8) | 0.0225 (8) | 0.0258 (8) | −0.0028 (6) | 0.0055 (7) | 0.0028 (6) |
O6 | 0.0377 (7) | 0.0390 (7) | 0.0253 (6) | 0.0062 (5) | 0.0018 (5) | 0.0055 (5) |
C7 | 0.0184 (7) | 0.0208 (8) | 0.0280 (8) | 0.0033 (6) | 0.0031 (6) | 0.0026 (6) |
C8 | 0.0250 (8) | 0.0275 (9) | 0.0338 (9) | −0.0005 (6) | 0.0056 (7) | −0.0045 (7) |
C9 | 0.0275 (9) | 0.0318 (10) | 0.0523 (12) | −0.0063 (7) | 0.0081 (8) | −0.0054 (8) |
C10 | 0.0274 (9) | 0.0364 (10) | 0.0525 (12) | −0.0012 (7) | 0.0128 (8) | 0.0108 (9) |
C11 | 0.0302 (9) | 0.0402 (10) | 0.0348 (10) | 0.0062 (7) | 0.0113 (8) | 0.0104 (8) |
C12 | 0.0292 (9) | 0.0291 (9) | 0.0273 (8) | 0.0030 (7) | 0.0046 (7) | 0.0023 (7) |
C13 | 0.0219 (8) | 0.0224 (8) | 0.0340 (9) | 0.0031 (6) | 0.0043 (7) | 0.0003 (7) |
C14 | 0.0312 (9) | 0.0216 (9) | 0.0462 (11) | 0.0019 (7) | 0.0090 (8) | 0.0039 (8) |
Geometric parameters (Å, º) top
N1—C6 | 1.386 (2) | C6—O6 | 1.2126 (19) |
N1—C2 | 1.391 (2) | C7—C8 | 1.389 (2) |
N1—C1 | 1.475 (2) | C7—C12 | 1.397 (2) |
C1—H1A | 0.94 (5) | C8—C9 | 1.394 (2) |
C1—H1B | 1.06 (5) | C8—H8A | 0.988 (19) |
C1—H1C | 1.06 (5) | C9—C10 | 1.376 (3) |
C1—H1D | 0.99 (7) | C9—H9A | 0.98 (2) |
C1—H1E | 0.95 (6) | C10—C11 | 1.385 (3) |
C1—H1F | 1.03 (6) | C10—H10A | 1.00 (2) |
C2—O2 | 1.2095 (19) | C11—C12 | 1.387 (2) |
C2—N3 | 1.379 (2) | C11—H11A | 0.962 (19) |
N3—C4 | 1.365 (2) | C12—H12A | 0.963 (19) |
N3—H3A | 0.876 (18) | C13—C14 | 1.520 (2) |
C4—O4 | 1.2184 (19) | C13—H13A | 1.023 (18) |
C4—C5 | 1.528 (2) | C13—H13B | 1.014 (19) |
C5—C6 | 1.528 (2) | C14—H14A | 0.94 (2) |
C5—C13 | 1.541 (2) | C14—H14B | 1.01 (2) |
C5—C7 | 1.551 (2) | C14—H14C | 1.00 (2) |
| | | |
C6—N1—C2 | 124.39 (13) | N1—C6—C5 | 118.20 (13) |
C6—N1—C1 | 118.22 (14) | C8—C7—C12 | 118.64 (15) |
C2—N1—C1 | 117.19 (15) | C8—C7—C5 | 122.71 (14) |
N1—C1—H1A | 107 (3) | C12—C7—C5 | 118.65 (14) |
N1—C1—H1B | 105 (3) | C7—C8—C9 | 120.40 (16) |
H1A—C1—H1B | 118 (4) | C7—C8—H8A | 121.8 (11) |
N1—C1—H1C | 109 (2) | C9—C8—H8A | 117.7 (11) |
H1A—C1—H1C | 110 (4) | C10—C9—C8 | 120.68 (17) |
H1B—C1—H1C | 107 (3) | C10—C9—H9A | 121.2 (12) |
N1—C1—H1D | 110 (3) | C8—C9—H9A | 118.1 (12) |
N1—C1—H1E | 107 (3) | C9—C10—C11 | 119.27 (17) |
H1D—C1—H1E | 121 (5) | C9—C10—H10A | 123.4 (12) |
N1—C1—H1F | 103 (3) | C11—C10—H10A | 117.3 (12) |
H1D—C1—H1F | 107 (5) | C10—C11—C12 | 120.59 (17) |
H1E—C1—H1F | 107 (5) | C10—C11—H11A | 121.9 (12) |
O2—C2—N3 | 121.00 (14) | C12—C11—H11A | 117.5 (12) |
O2—C2—N1 | 122.47 (15) | C11—C12—C7 | 120.41 (17) |
N3—C2—N1 | 116.52 (13) | C11—C12—H12A | 118.8 (11) |
C4—N3—C2 | 126.06 (13) | C7—C12—H12A | 120.7 (11) |
C4—N3—H3A | 116.2 (12) | C14—C13—C5 | 114.26 (14) |
C2—N3—H3A | 115.3 (11) | C14—C13—H13A | 112 (1) |
O4—C4—N3 | 120.94 (14) | C5—C13—H13A | 105 (1) |
O4—C4—C5 | 122.61 (14) | C14—C13—H13B | 108.8 (10) |
N3—C4—C5 | 116.23 (13) | C5—C13—H13B | 107.7 (10) |
C4—C5—C6 | 111.91 (13) | H13A—C13—H13B | 108.8 (14) |
C4—C5—C13 | 111.34 (12) | C13—C14—H14A | 105.9 (13) |
C6—C5—C13 | 109.63 (13) | C13—C14—H14B | 110.1 (12) |
C4—C5—C7 | 105.43 (12) | H14A—C14—H14B | 110.2 (17) |
C6—C5—C7 | 108.79 (12) | C13—C14—H14C | 110.8 (13) |
C13—C5—C7 | 109.62 (12) | H14A—C14—H14C | 110.3 (17) |
O6—C6—N1 | 120.59 (14) | H14B—C14—H14C | 109.4 (17) |
O6—C6—C5 | 121.11 (14) | | |
| | | |
C6—N1—C2—O2 | −178.51 (14) | C4—C5—C6—N1 | −23.27 (19) |
C1—N1—C2—O2 | 6.8 (2) | C13—C5—C6—N1 | −147.32 (14) |
C6—N1—C2—N3 | 2.2 (2) | C7—C5—C6—N1 | 92.82 (16) |
C1—N1—C2—N3 | −172.47 (15) | C4—C5—C7—C8 | 121.60 (15) |
O2—C2—N3—C4 | −173.37 (14) | C6—C5—C7—C8 | 1.41 (19) |
N1—C2—N3—C4 | 5.9 (2) | C13—C5—C7—C8 | −118.46 (16) |
C2—N3—C4—O4 | 162.33 (15) | C4—C5—C7—C12 | −59.21 (17) |
C2—N3—C4—C5 | −23.0 (2) | C6—C5—C7—C12 | −179.40 (13) |
O4—C4—C5—C6 | −155.56 (14) | C13—C5—C7—C12 | 60.73 (18) |
N3—C4—C5—C6 | 29.84 (18) | C12—C7—C8—C9 | 0.7 (2) |
O4—C4—C5—C13 | −32.5 (2) | C5—C7—C8—C9 | 179.84 (14) |
N3—C4—C5—C13 | 152.93 (14) | C7—C8—C9—C10 | −0.1 (3) |
O4—C4—C5—C7 | 86.33 (17) | C8—C9—C10—C11 | −0.6 (3) |
N3—C4—C5—C7 | −88.27 (15) | C9—C10—C11—C12 | 0.7 (3) |
C2—N1—C6—O6 | −175.56 (14) | C10—C11—C12—C7 | −0.2 (3) |
C1—N1—C6—O6 | −0.9 (2) | C8—C7—C12—C11 | −0.5 (2) |
C2—N1—C6—C5 | 8.1 (2) | C5—C7—C12—C11 | −179.71 (14) |
C1—N1—C6—C5 | −177.30 (15) | C4—C5—C13—C14 | −63.03 (19) |
C4—C5—C6—O6 | 160.39 (14) | C6—C5—C13—C14 | 61.36 (18) |
C13—C5—C6—O6 | 36.3 (2) | C7—C5—C13—C14 | −179.29 (14) |
C7—C5—C6—O6 | −83.52 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O4i | 0.876 (18) | 2.003 (19) | 2.8787 (19) | 178.8 (17) |
C12—H12A···O6ii | 0.963 (19) | 2.48 (2) | 3.371 (2) | 154.1 (15) |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y−1/2, z−1/2. |