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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—H...O hydrogen bonding forms a one-dimensional tape structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009610/lh2321sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009610/lh2321Isup2.hkl
Contains datablock I

CCDC reference: 643052

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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
C12H18N2O3F(000) = 512
Mr = 238.28Dx = 1.230 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6170 reflections
a = 11.4382 (8) Åθ = 2.3–25.0°
b = 6.7983 (5) ŵ = 0.09 mm1
c = 16.7218 (12) ÅT = 150 K
β = 98.163 (2)°Plate, colourless
V = 1287.12 (16) Å30.57 × 0.23 × 0.05 mm
Z = 4
Data collection top
Bruker SMART 1K CCD
diffractometer
2255 independent reflections
Radiation source: sealed tube1842 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.192 pixels mm-1θmax = 25.0°, θmin = 1.8°
thin–slice ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 88
Tmin = 0.857, Tmax = 0.995l = 1919
8938 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: difference Fourier map
wR(F2) = 0.118H 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 parametersΔρmax = 0.57 e Å3
9 restraintsΔρmin = 0.33 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.15309 (13)0.5681 (2)0.51193 (9)0.0388 (4)
O20.46742 (12)0.5693 (2)0.70762 (8)0.0287 (3)
O30.32374 (13)0.0221 (2)0.62399 (9)0.0351 (4)
N10.31041 (14)0.5646 (2)0.60884 (10)0.0243 (4)
H1N0.309 (2)0.692 (4)0.6096 (14)0.040 (7)*
N20.39387 (14)0.2740 (2)0.66360 (10)0.0227 (4)
H2N0.441 (2)0.220 (4)0.6993 (14)0.035 (6)*
C10.23294 (16)0.2488 (3)0.54786 (11)0.0231 (4)
C20.22687 (16)0.4726 (3)0.55418 (11)0.0244 (4)
C30.39548 (15)0.4761 (3)0.66285 (10)0.0198 (4)
C40.31875 (16)0.1542 (3)0.61452 (11)0.0226 (4)
C50.10799 (17)0.1668 (3)0.55394 (12)0.0289 (5)
H5A0.05210.21550.50750.035*
H5B0.10990.02140.55060.035*
C60.06454 (19)0.2254 (4)0.63060 (14)0.0393 (6)
H60.03790.35680.63480.047*
C70.0605 (2)0.1097 (5)0.69195 (17)0.0596 (8)
H7A0.08640.02280.68990.072*
H7B0.03170.15750.73880.072*
C80.3964 (2)0.2893 (4)0.45927 (14)0.0449 (6)
H8A0.45480.21790.49700.067*
H8B0.39780.42890.47390.067*
H8C0.41550.27490.40430.067*
C90.27320 (18)0.2050 (3)0.46332 (12)0.0339 (5)
H90.21770.27870.42240.041*0.869 (6)
H9X0.30360.07070.47940.041*0.131 (6)
C100.2659 (2)0.0059 (3)0.43782 (14)0.0293 (7)0.869 (6)
H10A0.18970.06060.44900.035*0.869 (6)
H10B0.32980.08000.47100.035*0.869 (6)
C110.27619 (17)0.0382 (3)0.34805 (11)0.0556 (7)
H11A0.21090.03130.31430.067*0.869 (6)
H11B0.35160.01790.33600.067*0.869 (6)
H11X0.28040.02200.29460.067*0.131 (6)
H11Y0.35720.02560.37750.067*0.131 (6)
C120.27144 (17)0.2508 (3)0.32762 (11)0.0546 (7)
H12A0.33700.31910.36020.082*
H12B0.27780.26750.27020.082*
H12C0.19640.30600.33890.082*
C10X0.2036 (12)0.139 (2)0.3934 (8)0.033 (5)*0.131 (6)
H10C0.18440.25020.35570.039*0.131 (6)
H10D0.12850.08480.40710.039*0.131 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0328 (8)0.0306 (8)0.0478 (9)0.0002 (7)0.0124 (7)0.0128 (7)
O20.0312 (8)0.0253 (7)0.0272 (7)0.0068 (6)0.0042 (6)0.0052 (6)
O30.0465 (9)0.0126 (7)0.0435 (9)0.0006 (6)0.0025 (7)0.0012 (6)
N10.0269 (9)0.0122 (8)0.0317 (9)0.0014 (6)0.0028 (7)0.0009 (7)
N20.0234 (8)0.0164 (8)0.0255 (9)0.0017 (6)0.0059 (7)0.0027 (6)
C10.0232 (10)0.0204 (10)0.0242 (10)0.0062 (7)0.0019 (8)0.0011 (7)
C20.0227 (9)0.0213 (10)0.0279 (10)0.0020 (8)0.0010 (8)0.0060 (8)
C30.0217 (9)0.0169 (9)0.0205 (9)0.0013 (7)0.0025 (7)0.0013 (7)
C40.0248 (10)0.0153 (10)0.0273 (10)0.0026 (7)0.0026 (8)0.0013 (7)
C50.0235 (10)0.0274 (11)0.0348 (11)0.0081 (8)0.0009 (8)0.0013 (9)
C60.0298 (11)0.0406 (13)0.0497 (14)0.0070 (10)0.0126 (10)0.0024 (11)
C70.0530 (16)0.076 (2)0.0539 (16)0.0054 (15)0.0226 (13)0.0110 (15)
C80.0420 (13)0.0566 (16)0.0388 (13)0.0202 (12)0.0150 (10)0.0108 (11)
C90.0319 (11)0.0421 (13)0.0276 (11)0.0104 (10)0.0037 (9)0.0059 (9)
C100.0330 (13)0.0276 (13)0.0278 (13)0.0028 (10)0.0058 (10)0.0003 (10)
C110.0648 (17)0.0676 (19)0.0377 (13)0.0191 (15)0.0185 (12)0.0166 (13)
C120.0552 (16)0.0640 (19)0.0471 (15)0.0050 (13)0.0161 (12)0.0005 (13)
Geometric parameters (Å, º) top
O1—C21.210 (2)C8—H8B0.980
O2—C31.210 (2)C8—H8C0.980
O3—C41.209 (2)C8—C91.532 (3)
N1—H1N0.86 (3)C9—H91.000
N1—C21.376 (2)C9—H9X1.000
N1—C31.369 (2)C9—C101.495 (3)
N2—H2N0.83 (2)C9—C10X1.393 (13)
N2—C31.374 (2)C10—H10A0.990
N2—C41.369 (2)C10—H10B0.990
C1—C21.527 (3)C10—C111.538 (3)
C1—C41.519 (3)C11—H11A0.990
C1—C51.551 (3)C11—H11B0.990
C1—C91.576 (3)C11—H11X0.990
C5—H5A0.990C11—H11Y0.990
C5—H5B0.990C11—C121.4844
C5—C61.493 (3)C11—C10X1.700 (13)
C6—H60.950C12—H12A0.980
C6—C71.299 (4)C12—H12B0.980
C7—H7A0.950C12—H12C0.980
C7—H7B0.950C10X—H10C0.990
C8—H8A0.980C10X—H10D0.990
H1N—N1—C2116.9 (15)C1—C9—H9X93.8
H1N—N1—C3116.2 (15)C1—C9—C10115.18 (18)
C2—N1—C3126.87 (16)C1—C9—C10X127.5 (6)
H2N—N2—C3116.0 (17)C8—C9—H9106.3
H2N—N2—C4117.2 (17)C8—C9—H9X93.8
C3—N2—C4126.66 (16)C8—C9—C10111.1 (2)
C2—C1—C4113.67 (15)C8—C9—C10X120.2 (7)
C2—C1—C5107.58 (16)H9—C9—C10106.3
C2—C1—C9105.79 (16)H9X—C9—C10X93.8
C4—C1—C5107.78 (15)C9—C10—H10A108.8
C4—C1—C9109.73 (16)C9—C10—H10B108.8
C5—C1—C9112.35 (15)C9—C10—C11113.98 (19)
O1—C2—N1120.33 (18)H10A—C10—H10B107.7
O1—C2—C1121.95 (17)H10A—C10—C11108.8
N1—C2—C1117.71 (16)H10B—C10—C11108.8
O2—C3—N1122.36 (17)C10—C11—H11A109.4
O2—C3—N2121.78 (17)C10—C11—H11B109.4
N1—C3—N2115.85 (16)C10—C11—C12110.99 (12)
O3—C4—N2119.80 (17)H11A—C11—H11B108.0
O3—C4—C1121.93 (17)H11A—C11—C12109.4
N2—C4—C1118.26 (16)H11B—C11—C12109.4
C1—C5—H5A109.1H11B—C11—C10X108.3
C1—C5—H5B109.1H11X—C11—H11Y104.6
C1—C5—C6112.49 (16)H11X—C11—C12101.5
H5A—C5—H5B107.8H11X—C11—C10X101.5
H5A—C5—C6109.1H11Y—C11—C12101.5
H5B—C5—C6109.1H11Y—C11—C10X101.5
C5—C6—H6117.6C12—C11—C10X141.9 (6)
C5—C6—C7124.7 (2)C11—C12—H12A109.5
H6—C6—C7117.6C11—C12—H12B109.5
C6—C7—H7A120.0C11—C12—H12C109.5
C6—C7—H7B120.0H12A—C12—H12B109.5
H7A—C7—H7B120.0H12A—C12—H12C109.5
H8A—C8—H8B109.5H12B—C12—H12C109.5
H8A—C8—H8C109.5C9—C10X—C11110.2 (8)
H8A—C8—C9109.5C9—C10X—H10C109.6
H8B—C8—H8C109.5C9—C10X—H10D109.6
H8B—C8—C9109.5C11—C10X—H10C109.6
H8C—C8—C9109.5C11—C10X—H10D109.6
C1—C9—C8110.91 (16)H10C—C10X—H10D108.1
C1—C9—H9106.3
C3—N1—C2—O1176.84 (19)C2—C1—C5—C658.2 (2)
C3—N1—C2—C14.5 (3)C4—C1—C5—C664.8 (2)
C4—C1—C2—O1170.93 (18)C9—C1—C5—C6174.20 (18)
C4—C1—C2—N110.5 (3)C1—C5—C6—C7104.3 (3)
C5—C1—C2—O151.7 (2)C2—C1—C9—C862.5 (2)
C5—C1—C2—N1129.71 (18)C2—C1—C9—C10170.23 (18)
C9—C1—C2—O168.6 (2)C2—C1—C9—C10X104.3 (8)
C9—C1—C2—N1110.01 (18)C4—C1—C9—C860.5 (2)
C2—N1—C3—O2178.24 (18)C4—C1—C9—C1066.8 (2)
C2—N1—C3—N22.2 (3)C4—C1—C9—C10X132.7 (8)
C4—N2—C3—O2178.27 (17)C5—C1—C9—C8179.58 (19)
C4—N2—C3—N12.1 (3)C5—C1—C9—C1053.1 (2)
C3—N2—C4—O3176.83 (19)C5—C1—C9—C10X12.8 (9)
C3—N2—C4—C14.7 (3)C1—C9—C10—C11165.91 (17)
C2—C1—C4—O3170.97 (18)C8—C9—C10—C1166.9 (2)
C2—C1—C4—N210.5 (2)C9—C10—C11—C12178.50 (14)
C5—C1—C4—O351.8 (2)C1—C9—C10X—C11137.2 (6)
C5—C1—C4—N2129.69 (18)C8—C9—C10X—C1157.1 (11)
C9—C1—C4—O370.8 (2)C12—C11—C10X—C9113.8 (8)
C9—C1—C4—N2107.67 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.86 (3)1.97 (3)2.824 (2)172 (2)
N2—H2N···O2ii0.83 (2)2.03 (3)2.850 (2)171 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1/2, z+3/2.
 

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