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The title compound, C
8H
12N
2O
2, belongs to the class of 5-substituted 1,2,3,4-tetrahydropyrimidin-2-ones, which exhibit a wide spectrum of biological activities. The conformation of the tetrahydropyrimidine ring is that of a distorted boat. In the crystal structure, N—H
O hydrogen bonds form molecular dimers and also link these dimers into chains along the
c axis of the unit cell.
Supporting information
CCDC reference: 263709
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.095
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT391_ALERT_3_C Deviating Methyl C6' H-C-H Bond Angle ...... 100.80 Deg.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: CAD-4-PC Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 and CIFTAB (Sheldrick, 1997).
5-acetyl-4,6-dimethyl-1,2,3,4-tetrahydropyrimidin-2-one
top
Crystal data top
C8H12N2O2 | F(000) = 720 |
Mr = 168.20 | Dx = 1.319 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 24 reflections |
a = 14.473 (3) Å | θ = 11.7–12.4° |
b = 6.994 (1) Å | µ = 0.10 mm−1 |
c = 17.200 (3) Å | T = 293 K |
β = 103.37 (3)° | Prism, colourless |
V = 1693.9 (6) Å3 | 0.46 × 0.42 × 0.12 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.4° |
Beta-filter monochromator | h = −17→15 |
θ–2θ scans | k = 0→8 |
1712 measured reflections | l = −21→15 |
1660 independent reflections | 3 standard reflections every 60 min |
1187 reflections with I > 2σ(I) | intensity decay: 0.5% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | All H-atom parameters refined |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.1584P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1660 reflections | Δρmax = 0.19 e Å−3 |
158 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (12) |
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 | 0.31811 (7) | 0.72513 (15) | 0.42729 (5) | 0.0529 (3) | |
O2 | 0.11886 (8) | −0.00279 (14) | 0.27906 (6) | 0.0581 (3) | |
N1 | 0.19369 (8) | 0.53897 (15) | 0.44034 (6) | 0.0407 (3) | |
N3 | 0.27067 (7) | 0.48107 (15) | 0.34084 (6) | 0.0387 (3) | |
C2 | 0.26391 (9) | 0.59101 (17) | 0.40215 (7) | 0.0375 (3) | |
C4 | 0.19446 (8) | 0.35429 (17) | 0.30044 (7) | 0.0376 (3) | |
C5 | 0.14675 (8) | 0.26497 (17) | 0.36127 (7) | 0.0356 (3) | |
C5' | 0.10586 (9) | 0.07488 (18) | 0.33966 (7) | 0.0396 (3) | |
C5'' | 0.04751 (11) | −0.0303 (2) | 0.38736 (9) | 0.0506 (4) | |
C6 | 0.14486 (8) | 0.36756 (17) | 0.42763 (7) | 0.0358 (3) | |
C4' | 0.12405 (11) | 0.4592 (2) | 0.23516 (8) | 0.0519 (4) | |
C6' | 0.09575 (11) | 0.3223 (2) | 0.49339 (8) | 0.0473 (3) | |
H1 | 0.1901 (11) | 0.607 (2) | 0.4810 (9) | 0.049 (4)* | |
H3 | 0.3106 (11) | 0.510 (2) | 0.3153 (9) | 0.042 (4)* | |
H4 | 0.2235 (9) | 0.255 (2) | 0.2758 (8) | 0.039 (3)* | |
H41' | 0.1562 (13) | 0.509 (2) | 0.1965 (11) | 0.069 (5)* | |
H42' | 0.0723 (13) | 0.378 (3) | 0.2094 (10) | 0.067 (5)* | |
H43' | 0.0966 (12) | 0.569 (2) | 0.2588 (10) | 0.057 (4)* | |
H51'' | 0.0255 (13) | −0.147 (3) | 0.3555 (11) | 0.075 (5)* | |
H52'' | 0.0840 (14) | −0.061 (3) | 0.4421 (12) | 0.080 (6)* | |
H53'' | −0.0068 (13) | 0.047 (3) | 0.3957 (10) | 0.071 (5)* | |
H61' | 0.1204 (16) | 0.213 (3) | 0.5214 (13) | 0.095 (7)* | |
H62' | 0.0987 (13) | 0.435 (3) | 0.5288 (11) | 0.076 (5)* | |
H63' | 0.0284 (16) | 0.309 (3) | 0.4739 (12) | 0.089 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0623 (6) | 0.0563 (6) | 0.0438 (5) | −0.0194 (5) | 0.0197 (4) | −0.0117 (4) |
O2 | 0.0692 (7) | 0.0551 (6) | 0.0602 (7) | −0.0178 (5) | 0.0360 (5) | −0.0197 (5) |
N1 | 0.0500 (6) | 0.0413 (5) | 0.0353 (5) | −0.0029 (5) | 0.0189 (4) | −0.0063 (4) |
N3 | 0.0398 (5) | 0.0449 (6) | 0.0351 (5) | −0.0054 (4) | 0.0164 (4) | −0.0017 (4) |
C2 | 0.0418 (6) | 0.0402 (6) | 0.0307 (5) | −0.0008 (5) | 0.0088 (5) | 0.0007 (5) |
C4 | 0.0432 (6) | 0.0392 (6) | 0.0343 (6) | −0.0034 (5) | 0.0171 (5) | −0.0060 (5) |
C5 | 0.0364 (6) | 0.0392 (6) | 0.0339 (6) | 0.0022 (5) | 0.0140 (4) | 0.0015 (5) |
C5' | 0.0383 (6) | 0.0425 (6) | 0.0404 (6) | 0.0006 (5) | 0.0144 (5) | −0.0017 (5) |
C5'' | 0.0597 (9) | 0.0486 (8) | 0.0472 (8) | −0.0113 (7) | 0.0198 (7) | 0.0013 (6) |
C6 | 0.0366 (6) | 0.0383 (6) | 0.0346 (6) | 0.0047 (5) | 0.0124 (4) | 0.0027 (5) |
C4' | 0.0551 (8) | 0.0644 (9) | 0.0351 (6) | −0.0096 (7) | 0.0081 (6) | 0.0031 (6) |
C6' | 0.0558 (8) | 0.0506 (8) | 0.0429 (7) | 0.0000 (7) | 0.0265 (6) | −0.0004 (6) |
Geometric parameters (Å, º) top
O1—C2 | 1.2350 (15) | C5—C5' | 1.4677 (17) |
O2—C5' | 1.2279 (15) | C5'—C5'' | 1.4993 (18) |
N1—C2 | 1.3803 (16) | C5''—H51'' | 0.991 (19) |
N1—C6 | 1.3831 (16) | C5''—H52'' | 0.99 (2) |
N1—H1 | 0.858 (16) | C5''—H53'' | 0.991 (19) |
N3—C2 | 1.3270 (15) | C6—C6' | 1.5021 (16) |
N3—C4 | 1.4598 (16) | C4'—H41' | 0.960 (19) |
N3—H3 | 0.828 (17) | C4'—H42' | 0.963 (19) |
C4—C5 | 1.5152 (15) | C4'—H43' | 0.997 (18) |
C4—C4' | 1.5192 (19) | C6'—H61' | 0.93 (2) |
C4—H4 | 0.959 (14) | C6'—H62' | 0.99 (2) |
C5—C6 | 1.3538 (16) | C6'—H63' | 0.96 (2) |
| | | |
C2—N1—C6 | 123.98 (10) | C5'—C5''—H51'' | 104.5 (11) |
C2—N1—H1 | 115.5 (10) | C5'—C5''—H52'' | 112.4 (11) |
C6—N1—H1 | 119.1 (10) | H51''—C5''—H52'' | 112.5 (15) |
C2—N3—C4 | 122.94 (10) | C5'—C5''—H53'' | 112.2 (11) |
C2—N3—H3 | 117.9 (10) | H51''—C5''—H53'' | 111.3 (15) |
C4—N3—H3 | 116.1 (10) | H52''—C5''—H53'' | 104.2 (15) |
O1—C2—N3 | 124.11 (11) | C5—C6—N1 | 118.90 (10) |
O1—C2—N1 | 120.77 (11) | C5—C6—C6' | 128.93 (12) |
N3—C2—N1 | 115.03 (11) | N1—C6—C6' | 112.16 (10) |
N3—C4—C5 | 109.67 (9) | C4—C4'—H41' | 109.6 (10) |
N3—C4—C4' | 111.24 (11) | C4—C4'—H42' | 111.8 (10) |
C5—C4—C4' | 111.99 (11) | H41'—C4'—H42' | 110.2 (14) |
N3—C4—H4 | 106.8 (8) | C4—C4'—H43' | 109.5 (9) |
C5—C4—H4 | 108.9 (8) | H41'—C4'—H43' | 107.9 (14) |
C4'—C4—H4 | 108.0 (8) | H42'—C4'—H43' | 107.7 (15) |
C6—C5—C5' | 127.45 (10) | C6—C6'—H61' | 111.8 (15) |
C6—C5—C4 | 117.71 (10) | C6—C6'—H62' | 109.5 (11) |
C5'—C5—C4 | 114.83 (10) | H61'—C6'—H62' | 112.3 (16) |
O2—C5'—C5 | 118.93 (11) | C6—C6'—H63' | 112.1 (13) |
O2—C5'—C5'' | 117.63 (12) | H61'—C6'—H63' | 109.8 (18) |
C5—C5'—C5'' | 123.43 (11) | H62'—C6'—H63' | 100.8 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.858 (16) | 1.991 (17) | 2.8487 (15) | 177.7 (14) |
N3—H3···O2ii | 0.828 (17) | 2.110 (17) | 2.8891 (16) | 156.8 (13) |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y+1/2, −z+1/2. |
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