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organic compounds
G. S. Nichol and W. Clegg
The title compound, C12H18N2O3, also known as quinal barbitone, crystallizes from aqueous solution in an anhydrous form, with one molecule in the asymmetric unit. Intermolecular N—HO hydrogen bonding forms a one-dimensional tape structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009610/lh2321sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009610/lh2321Isup2.hkl |
CCDC reference: 643052
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.045
- wR factor = 0.118
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 1 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.01 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
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 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
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXTL and local programs.
5-(1-Methylbutyl)-5-propenylbarbituric acid (quinal barbitone) top
Crystal data top
C12H18N2O3 | F(000) = 512 |
Mr = 238.28 | Dx = 1.230 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6170 reflections |
a = 11.4382 (8) Å | θ = 2.3–25.0° |
b = 6.7983 (5) Å | µ = 0.09 mm−1 |
c = 16.7218 (12) Å | T = 150 K |
β = 98.163 (2)° | Plate, colourless |
V = 1287.12 (16) Å3 | 0.57 × 0.23 × 0.05 mm |
Z = 4 |
Data collection top
Bruker SMART 1K CCD diffractometer | 2255 independent reflections |
Radiation source: sealed tube | 1842 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.192 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
thin–slice ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −8→8 |
Tmin = 0.857, Tmax = 0.995 | l = −19→19 |
8938 measured reflections |
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0437P)2 + 1.1535P] where P = (Fo2 + 2Fc2)/3 |
2255 reflections | (Δ/σ)max < 0.001 |
166 parameters | Δρmax = 0.57 e Å−3 |
9 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.15309 (13) | 0.5681 (2) | 0.51193 (9) | 0.0388 (4) | |
O2 | 0.46742 (12) | 0.5693 (2) | 0.70762 (8) | 0.0287 (3) | |
O3 | 0.32374 (13) | −0.0221 (2) | 0.62399 (9) | 0.0351 (4) | |
N1 | 0.31041 (14) | 0.5646 (2) | 0.60884 (10) | 0.0243 (4) | |
H1N | 0.309 (2) | 0.692 (4) | 0.6096 (14) | 0.040 (7)* | |
N2 | 0.39387 (14) | 0.2740 (2) | 0.66360 (10) | 0.0227 (4) | |
H2N | 0.441 (2) | 0.220 (4) | 0.6993 (14) | 0.035 (6)* | |
C1 | 0.23294 (16) | 0.2488 (3) | 0.54786 (11) | 0.0231 (4) | |
C2 | 0.22687 (16) | 0.4726 (3) | 0.55418 (11) | 0.0244 (4) | |
C3 | 0.39548 (15) | 0.4761 (3) | 0.66285 (10) | 0.0198 (4) | |
C4 | 0.31875 (16) | 0.1542 (3) | 0.61452 (11) | 0.0226 (4) | |
C5 | 0.10799 (17) | 0.1668 (3) | 0.55394 (12) | 0.0289 (5) | |
H5A | 0.0521 | 0.2155 | 0.5075 | 0.035* | |
H5B | 0.1099 | 0.0214 | 0.5506 | 0.035* | |
C6 | 0.06454 (19) | 0.2254 (4) | 0.63060 (14) | 0.0393 (6) | |
H6 | 0.0379 | 0.3568 | 0.6348 | 0.047* | |
C7 | 0.0605 (2) | 0.1097 (5) | 0.69195 (17) | 0.0596 (8) | |
H7A | 0.0864 | −0.0228 | 0.6899 | 0.072* | |
H7B | 0.0317 | 0.1575 | 0.7388 | 0.072* | |
C8 | 0.3964 (2) | 0.2893 (4) | 0.45927 (14) | 0.0449 (6) | |
H8A | 0.4548 | 0.2179 | 0.4970 | 0.067* | |
H8B | 0.3978 | 0.4289 | 0.4739 | 0.067* | |
H8C | 0.4155 | 0.2749 | 0.4043 | 0.067* | |
C9 | 0.27320 (18) | 0.2050 (3) | 0.46332 (12) | 0.0339 (5) | |
H9 | 0.2177 | 0.2787 | 0.4224 | 0.041* | 0.869 (6) |
H9X | 0.3036 | 0.0707 | 0.4794 | 0.041* | 0.131 (6) |
C10 | 0.2659 (2) | −0.0059 (3) | 0.43782 (14) | 0.0293 (7) | 0.869 (6) |
H10A | 0.1897 | −0.0606 | 0.4490 | 0.035* | 0.869 (6) |
H10B | 0.3298 | −0.0800 | 0.4710 | 0.035* | 0.869 (6) |
C11 | 0.27619 (17) | −0.0382 (3) | 0.34805 (11) | 0.0556 (7) | |
H11A | 0.2109 | 0.0313 | 0.3143 | 0.067* | 0.869 (6) |
H11B | 0.3516 | 0.0179 | 0.3360 | 0.067* | 0.869 (6) |
H11X | 0.2804 | 0.0220 | 0.2946 | 0.067* | 0.131 (6) |
H11Y | 0.3572 | −0.0256 | 0.3775 | 0.067* | 0.131 (6) |
C12 | 0.27144 (17) | −0.2508 (3) | 0.32762 (11) | 0.0546 (7) | |
H12A | 0.3370 | −0.3191 | 0.3602 | 0.082* | |
H12B | 0.2778 | −0.2675 | 0.2702 | 0.082* | |
H12C | 0.1964 | −0.3060 | 0.3389 | 0.082* | |
C10X | 0.2036 (12) | 0.139 (2) | 0.3934 (8) | 0.033 (5)* | 0.131 (6) |
H10C | 0.1844 | 0.2502 | 0.3557 | 0.039* | 0.131 (6) |
H10D | 0.1285 | 0.0848 | 0.4071 | 0.039* | 0.131 (6) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0328 (8) | 0.0306 (8) | 0.0478 (9) | 0.0002 (7) | −0.0124 (7) | 0.0128 (7) |
O2 | 0.0312 (8) | 0.0253 (7) | 0.0272 (7) | −0.0068 (6) | −0.0042 (6) | −0.0052 (6) |
O3 | 0.0465 (9) | 0.0126 (7) | 0.0435 (9) | −0.0006 (6) | −0.0025 (7) | 0.0012 (6) |
N1 | 0.0269 (9) | 0.0122 (8) | 0.0317 (9) | −0.0014 (6) | −0.0028 (7) | 0.0009 (7) |
N2 | 0.0234 (8) | 0.0164 (8) | 0.0255 (9) | 0.0017 (6) | −0.0059 (7) | 0.0027 (6) |
C1 | 0.0232 (10) | 0.0204 (10) | 0.0242 (10) | −0.0062 (7) | −0.0019 (8) | −0.0011 (7) |
C2 | 0.0227 (9) | 0.0213 (10) | 0.0279 (10) | −0.0020 (8) | −0.0010 (8) | 0.0060 (8) |
C3 | 0.0217 (9) | 0.0169 (9) | 0.0205 (9) | −0.0013 (7) | 0.0025 (7) | −0.0013 (7) |
C4 | 0.0248 (10) | 0.0153 (10) | 0.0273 (10) | −0.0026 (7) | 0.0026 (8) | −0.0013 (7) |
C5 | 0.0235 (10) | 0.0274 (11) | 0.0348 (11) | −0.0081 (8) | 0.0009 (8) | −0.0013 (9) |
C6 | 0.0298 (11) | 0.0406 (13) | 0.0497 (14) | −0.0070 (10) | 0.0126 (10) | −0.0024 (11) |
C7 | 0.0530 (16) | 0.076 (2) | 0.0539 (16) | 0.0054 (15) | 0.0226 (13) | 0.0110 (15) |
C8 | 0.0420 (13) | 0.0566 (16) | 0.0388 (13) | −0.0202 (12) | 0.0150 (10) | −0.0108 (11) |
C9 | 0.0319 (11) | 0.0421 (13) | 0.0276 (11) | −0.0104 (10) | 0.0037 (9) | −0.0059 (9) |
C10 | 0.0330 (13) | 0.0276 (13) | 0.0278 (13) | −0.0028 (10) | 0.0058 (10) | −0.0003 (10) |
C11 | 0.0648 (17) | 0.0676 (19) | 0.0377 (13) | −0.0191 (15) | 0.0185 (12) | −0.0166 (13) |
C12 | 0.0552 (16) | 0.0640 (19) | 0.0471 (15) | −0.0050 (13) | 0.0161 (12) | −0.0005 (13) |
Geometric parameters (Å, º) top
O1—C2 | 1.210 (2) | C8—H8B | 0.980 |
O2—C3 | 1.210 (2) | C8—H8C | 0.980 |
O3—C4 | 1.209 (2) | C8—C9 | 1.532 (3) |
N1—H1N | 0.86 (3) | C9—H9 | 1.000 |
N1—C2 | 1.376 (2) | C9—H9X | 1.000 |
N1—C3 | 1.369 (2) | C9—C10 | 1.495 (3) |
N2—H2N | 0.83 (2) | C9—C10X | 1.393 (13) |
N2—C3 | 1.374 (2) | C10—H10A | 0.990 |
N2—C4 | 1.369 (2) | C10—H10B | 0.990 |
C1—C2 | 1.527 (3) | C10—C11 | 1.538 (3) |
C1—C4 | 1.519 (3) | C11—H11A | 0.990 |
C1—C5 | 1.551 (3) | C11—H11B | 0.990 |
C1—C9 | 1.576 (3) | C11—H11X | 0.990 |
C5—H5A | 0.990 | C11—H11Y | 0.990 |
C5—H5B | 0.990 | C11—C12 | 1.4844 |
C5—C6 | 1.493 (3) | C11—C10X | 1.700 (13) |
C6—H6 | 0.950 | C12—H12A | 0.980 |
C6—C7 | 1.299 (4) | C12—H12B | 0.980 |
C7—H7A | 0.950 | C12—H12C | 0.980 |
C7—H7B | 0.950 | C10X—H10C | 0.990 |
C8—H8A | 0.980 | C10X—H10D | 0.990 |
H1N—N1—C2 | 116.9 (15) | C1—C9—H9X | 93.8 |
H1N—N1—C3 | 116.2 (15) | C1—C9—C10 | 115.18 (18) |
C2—N1—C3 | 126.87 (16) | C1—C9—C10X | 127.5 (6) |
H2N—N2—C3 | 116.0 (17) | C8—C9—H9 | 106.3 |
H2N—N2—C4 | 117.2 (17) | C8—C9—H9X | 93.8 |
C3—N2—C4 | 126.66 (16) | C8—C9—C10 | 111.1 (2) |
C2—C1—C4 | 113.67 (15) | C8—C9—C10X | 120.2 (7) |
C2—C1—C5 | 107.58 (16) | H9—C9—C10 | 106.3 |
C2—C1—C9 | 105.79 (16) | H9X—C9—C10X | 93.8 |
C4—C1—C5 | 107.78 (15) | C9—C10—H10A | 108.8 |
C4—C1—C9 | 109.73 (16) | C9—C10—H10B | 108.8 |
C5—C1—C9 | 112.35 (15) | C9—C10—C11 | 113.98 (19) |
O1—C2—N1 | 120.33 (18) | H10A—C10—H10B | 107.7 |
O1—C2—C1 | 121.95 (17) | H10A—C10—C11 | 108.8 |
N1—C2—C1 | 117.71 (16) | H10B—C10—C11 | 108.8 |
O2—C3—N1 | 122.36 (17) | C10—C11—H11A | 109.4 |
O2—C3—N2 | 121.78 (17) | C10—C11—H11B | 109.4 |
N1—C3—N2 | 115.85 (16) | C10—C11—C12 | 110.99 (12) |
O3—C4—N2 | 119.80 (17) | H11A—C11—H11B | 108.0 |
O3—C4—C1 | 121.93 (17) | H11A—C11—C12 | 109.4 |
N2—C4—C1 | 118.26 (16) | H11B—C11—C12 | 109.4 |
C1—C5—H5A | 109.1 | H11B—C11—C10X | 108.3 |
C1—C5—H5B | 109.1 | H11X—C11—H11Y | 104.6 |
C1—C5—C6 | 112.49 (16) | H11X—C11—C12 | 101.5 |
H5A—C5—H5B | 107.8 | H11X—C11—C10X | 101.5 |
H5A—C5—C6 | 109.1 | H11Y—C11—C12 | 101.5 |
H5B—C5—C6 | 109.1 | H11Y—C11—C10X | 101.5 |
C5—C6—H6 | 117.6 | C12—C11—C10X | 141.9 (6) |
C5—C6—C7 | 124.7 (2) | C11—C12—H12A | 109.5 |
H6—C6—C7 | 117.6 | C11—C12—H12B | 109.5 |
C6—C7—H7A | 120.0 | C11—C12—H12C | 109.5 |
C6—C7—H7B | 120.0 | H12A—C12—H12B | 109.5 |
H7A—C7—H7B | 120.0 | H12A—C12—H12C | 109.5 |
H8A—C8—H8B | 109.5 | H12B—C12—H12C | 109.5 |
H8A—C8—H8C | 109.5 | C9—C10X—C11 | 110.2 (8) |
H8A—C8—C9 | 109.5 | C9—C10X—H10C | 109.6 |
H8B—C8—H8C | 109.5 | C9—C10X—H10D | 109.6 |
H8B—C8—C9 | 109.5 | C11—C10X—H10C | 109.6 |
H8C—C8—C9 | 109.5 | C11—C10X—H10D | 109.6 |
C1—C9—C8 | 110.91 (16) | H10C—C10X—H10D | 108.1 |
C1—C9—H9 | 106.3 | ||
C3—N1—C2—O1 | 176.84 (19) | C2—C1—C5—C6 | −58.2 (2) |
C3—N1—C2—C1 | −4.5 (3) | C4—C1—C5—C6 | 64.8 (2) |
C4—C1—C2—O1 | −170.93 (18) | C9—C1—C5—C6 | −174.20 (18) |
C4—C1—C2—N1 | 10.5 (3) | C1—C5—C6—C7 | −104.3 (3) |
C5—C1—C2—O1 | −51.7 (2) | C2—C1—C9—C8 | 62.5 (2) |
C5—C1—C2—N1 | 129.71 (18) | C2—C1—C9—C10 | −170.23 (18) |
C9—C1—C2—O1 | 68.6 (2) | C2—C1—C9—C10X | −104.3 (8) |
C9—C1—C2—N1 | −110.01 (18) | C4—C1—C9—C8 | −60.5 (2) |
C2—N1—C3—O2 | 178.24 (18) | C4—C1—C9—C10 | 66.8 (2) |
C2—N1—C3—N2 | −2.2 (3) | C4—C1—C9—C10X | 132.7 (8) |
C4—N2—C3—O2 | −178.27 (17) | C5—C1—C9—C8 | 179.58 (19) |
C4—N2—C3—N1 | 2.1 (3) | C5—C1—C9—C10 | −53.1 (2) |
C3—N2—C4—O3 | −176.83 (19) | C5—C1—C9—C10X | 12.8 (9) |
C3—N2—C4—C1 | 4.7 (3) | C1—C9—C10—C11 | 165.91 (17) |
C2—C1—C4—O3 | 170.97 (18) | C8—C9—C10—C11 | −66.9 (2) |
C2—C1—C4—N2 | −10.5 (2) | C9—C10—C11—C12 | 178.50 (14) |
C5—C1—C4—O3 | 51.8 (2) | C1—C9—C10X—C11 | −137.2 (6) |
C5—C1—C4—N2 | −129.69 (18) | C8—C9—C10X—C11 | 57.1 (11) |
C9—C1—C4—O3 | −70.8 (2) | C12—C11—C10X—C9 | 113.8 (8) |
C9—C1—C4—N2 | 107.67 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3i | 0.86 (3) | 1.97 (3) | 2.824 (2) | 172 (2) |
N2—H2N···O2ii | 0.83 (2) | 2.03 (3) | 2.850 (2) | 171 (2) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+3/2. |
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