In the molecular structure of the title compound, C
8H
7N
5O
3S, the thiazole ring is oriented with respect to the barbituric acid ring at a dihedral angle of 5.14 (9)°. In the crystal structure, intermolecular N—H
N and N—H
O hydrogen bonds link the molecules, forming a layer parallel to the
ac plane.
Supporting information
CCDC reference: 640395
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.106
- wR factor = 0.341
- Data-to-parameter ratio = 20.2
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.106
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.341
PLAT082_ALERT_2_C High R1 Value .................................. 0.11
PLAT084_ALERT_2_C High R2 Value .................................. 0.34
PLAT320_ALERT_2_C Check Hybridisation of C4 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C7 .. 2.93 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C8 H7 N5 O3 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 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
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
5-[(5-Methylthiazol-2-yl)diazenyl]pyrimidine-2,4,6(1
H,3H,5
H)-trione
top
Crystal data top
C8H7N5O3S | F(000) = 520 |
Mr = 253.24 | Dx = 1.564 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4440 reflections |
a = 13.092 (2) Å | θ = 3.0–30.5° |
b = 7.0989 (9) Å | µ = 0.31 mm−1 |
c = 12.913 (2) Å | T = 294 K |
β = 116.321 (7)° | Block, orange |
V = 1075.7 (3) Å3 | 0.35 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID-S diffractometer | 2154 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
Graphite monochromator | θmax = 30.7°, θmin = 3.2° |
ω scans | h = −18→18 |
28688 measured reflections | k = −9→10 |
3294 independent reflections | l = −18→18 |
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)] = 0.106 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.341 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.1678P)2 + 0.1113P] where P = (Fo2 + 2Fc2)/3 |
3294 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.66 e Å−3 |
2 restraints | Δρmin = −0.54 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 | |
S1 | 0.37726 (9) | 0.23263 (15) | 0.03524 (8) | 0.0671 (4) | |
O1 | 0.2817 (3) | −0.3123 (5) | −0.2114 (3) | 0.0797 (9) | |
O2 | 0.0564 (3) | −0.7936 (4) | −0.2091 (3) | 0.0770 (9) | |
O3 | 0.0793 (3) | −0.2922 (4) | 0.0151 (3) | 0.0725 (8) | |
N1 | 0.2537 (3) | 0.2369 (4) | 0.1443 (3) | 0.0625 (8) | |
N2 | 0.2224 (3) | −0.0299 (5) | 0.0301 (3) | 0.0616 (8) | |
N3 | 0.2420 (3) | −0.1211 (4) | −0.0487 (3) | 0.0583 (7) | |
N4 | 0.1665 (3) | −0.5484 (5) | −0.2112 (3) | 0.0612 (8) | |
H41 | 0.192 (4) | −0.609 (6) | −0.253 (3) | 0.079 (13)* | |
N5 | 0.0725 (3) | −0.5440 (4) | −0.0942 (3) | 0.0586 (8) | |
H51 | 0.025 (3) | −0.602 (5) | −0.075 (4) | 0.085 (15)* | |
C1 | 0.2765 (3) | 0.1377 (6) | 0.0721 (3) | 0.0588 (9) | |
C2 | 0.3170 (3) | 0.4032 (5) | 0.1712 (3) | 0.0649 (9) | |
H2 | 0.3107 | 0.4934 | 0.2204 | 0.078* | |
C3 | 0.3879 (3) | 0.4254 (5) | 0.1217 (3) | 0.0653 (10) | |
C4 | 0.1908 (3) | −0.2806 (5) | −0.0883 (3) | 0.0552 (8) | |
H4 | 0.1278 | −0.2138 | −0.1503 | 0.066* | |
C5 | 0.2180 (3) | −0.3760 (5) | −0.1750 (3) | 0.0583 (9) | |
C6 | 0.0960 (3) | −0.6400 (6) | −0.1750 (3) | 0.0600 (9) | |
C7 | 0.1099 (3) | −0.3692 (6) | −0.0524 (3) | 0.0598 (9) | |
C8 | 0.4671 (4) | 0.5860 (6) | 0.1347 (4) | 0.0826 (13) | |
H8A | 0.4532 | 0.6865 | 0.1765 | 0.124* | |
H8B | 0.4543 | 0.6303 | 0.0596 | 0.124* | |
H8C | 0.5445 | 0.5440 | 0.1762 | 0.124* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0795 (8) | 0.0753 (8) | 0.0595 (6) | −0.0113 (5) | 0.0426 (5) | −0.0054 (4) |
O1 | 0.105 (2) | 0.0856 (19) | 0.0773 (19) | −0.0128 (17) | 0.0665 (17) | −0.0054 (16) |
O2 | 0.097 (2) | 0.0778 (19) | 0.0672 (18) | −0.0196 (16) | 0.0458 (16) | −0.0164 (14) |
O3 | 0.090 (2) | 0.0817 (18) | 0.0692 (17) | −0.0189 (15) | 0.0569 (16) | −0.0152 (14) |
N1 | 0.076 (2) | 0.0658 (19) | 0.0560 (17) | −0.0021 (15) | 0.0388 (16) | 0.0005 (13) |
N2 | 0.078 (2) | 0.0658 (18) | 0.0515 (16) | −0.0104 (15) | 0.0384 (15) | −0.0053 (13) |
N3 | 0.0721 (18) | 0.0641 (18) | 0.0492 (15) | −0.0005 (15) | 0.0366 (14) | 0.0004 (13) |
N4 | 0.079 (2) | 0.0673 (19) | 0.0495 (15) | −0.0011 (15) | 0.0395 (15) | −0.0046 (13) |
N5 | 0.0686 (18) | 0.0688 (19) | 0.0472 (15) | −0.0078 (15) | 0.0338 (14) | −0.0030 (13) |
C1 | 0.067 (2) | 0.070 (2) | 0.0473 (18) | −0.0034 (17) | 0.0321 (16) | 0.0015 (15) |
C2 | 0.084 (3) | 0.058 (2) | 0.056 (2) | 0.0001 (18) | 0.0339 (18) | −0.0011 (16) |
C3 | 0.072 (2) | 0.069 (2) | 0.059 (2) | −0.0020 (18) | 0.0322 (18) | 0.0006 (17) |
C4 | 0.063 (2) | 0.062 (2) | 0.0462 (17) | −0.0016 (15) | 0.0292 (15) | 0.0019 (13) |
C5 | 0.073 (2) | 0.063 (2) | 0.0488 (18) | −0.0039 (17) | 0.0366 (17) | −0.0011 (14) |
C6 | 0.067 (2) | 0.069 (2) | 0.0483 (18) | 0.0001 (17) | 0.0295 (16) | −0.0003 (15) |
C7 | 0.074 (2) | 0.070 (2) | 0.0437 (17) | −0.0056 (17) | 0.0332 (16) | −0.0005 (14) |
C8 | 0.086 (3) | 0.075 (3) | 0.085 (3) | −0.019 (2) | 0.037 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
S1—C1 | 1.726 (4) | C2—H2 | 0.9300 |
S1—C3 | 1.732 (4) | C3—C2 | 1.350 (5) |
O3—C7 | 1.237 (4) | C3—C8 | 1.500 (6) |
N1—C1 | 1.304 (5) | C4—N3 | 1.299 (5) |
N1—C2 | 1.395 (5) | C4—C7 | 1.473 (5) |
N2—N3 | 1.324 (4) | C4—C5 | 1.481 (5) |
N2—C1 | 1.368 (5) | C4—H4 | 0.9800 |
N4—C6 | 1.369 (5) | C5—O1 | 1.211 (4) |
N4—C5 | 1.376 (5) | C6—O2 | 1.204 (5) |
N4—H41 | 0.87 (5) | C8—H8A | 0.9600 |
N5—C7 | 1.355 (5) | C8—H8B | 0.9600 |
N5—C6 | 1.390 (5) | C8—H8C | 0.9600 |
N5—H51 | 0.87 (4) | | |
| | | |
C1—S1—C3 | 89.03 (18) | N3—C4—C5 | 116.2 (3) |
C1—N1—C2 | 109.6 (3) | C7—C4—C5 | 119.4 (3) |
N3—N2—C1 | 119.2 (3) | N3—C4—H4 | 90.0 |
C4—N3—N2 | 119.1 (3) | C7—C4—H4 | 90.0 |
C6—N4—C5 | 127.6 (3) | C5—C4—H4 | 90.0 |
C6—N4—H41 | 119 (3) | O1—C5—N4 | 121.3 (3) |
C5—N4—H41 | 113 (3) | O1—C5—C4 | 124.1 (4) |
C7—N5—C6 | 125.9 (3) | N4—C5—C4 | 114.7 (3) |
C7—N5—H51 | 120 (3) | O2—C6—N4 | 123.5 (3) |
C6—N5—H51 | 114 (3) | O2—C6—N5 | 121.0 (3) |
N1—C1—N2 | 120.7 (3) | N4—C6—N5 | 115.5 (3) |
N1—C1—S1 | 115.6 (3) | O3—C7—N5 | 120.8 (3) |
N2—C1—S1 | 123.7 (3) | O3—C7—C4 | 122.4 (4) |
C3—C2—N1 | 116.0 (3) | N5—C7—C4 | 116.7 (3) |
C3—C2—H2 | 122.0 | C3—C8—H8A | 109.5 |
N1—C2—H2 | 122.0 | C3—C8—H8B | 109.5 |
C2—C3—C8 | 128.5 (4) | H8A—C8—H8B | 109.5 |
C2—C3—S1 | 109.8 (3) | C3—C8—H8C | 109.5 |
C8—C3—S1 | 121.8 (3) | H8A—C8—H8C | 109.5 |
N3—C4—C7 | 124.5 (3) | H8B—C8—H8C | 109.5 |
| | | |
C3—S1—C1—N1 | −1.3 (3) | C7—N5—C6—N4 | 2.2 (6) |
C3—S1—C1—N2 | 178.6 (3) | C6—N5—C7—O3 | 176.4 (4) |
C1—S1—C3—C2 | 0.5 (3) | C6—N5—C7—C4 | −5.8 (6) |
C1—S1—C3—C8 | −179.9 (4) | C8—C3—C2—N1 | −179.2 (4) |
C2—N1—C1—N2 | −178.2 (3) | S1—C3—C2—N1 | 0.4 (5) |
C2—N1—C1—S1 | 1.8 (4) | C7—C4—N3—N2 | 0.6 (6) |
C1—N1—C2—C3 | −1.4 (5) | C5—C4—N3—N2 | −179.2 (3) |
N3—N2—C1—N1 | 175.6 (3) | N3—C4—C5—O1 | −1.7 (6) |
N3—N2—C1—S1 | −4.3 (5) | C7—C4—C5—O1 | 178.5 (4) |
C1—N2—N3—C4 | 179.8 (3) | N3—C4—C5—N4 | 177.1 (3) |
C6—N4—C5—O1 | 177.7 (4) | C7—C4—C5—N4 | −2.7 (5) |
C6—N4—C5—C4 | −1.1 (6) | N3—C4—C7—O3 | 3.9 (6) |
C5—N4—C6—O2 | −178.1 (4) | C5—C4—C7—O3 | −176.3 (4) |
C5—N4—C6—N5 | 1.6 (6) | N3—C4—C7—N5 | −174.0 (3) |
C7—N5—C6—O2 | −178.1 (4) | C5—C4—C7—N5 | 5.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H41···N1i | 0.87 (5) | 2.05 (5) | 2.910 (5) | 177 (4) |
N5—H51···O3ii | 0.87 (4) | 1.99 (4) | 2.853 (6) | 172 (3) |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x, −y−1, −z. |