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The title compound, C11H16N2O3, crystallizes in the triclinic space group P\overline 1. The mol­ecules form dimers in the solid state, through hydrogen bonding involving the β-hydroxy ketone functionality.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022894/cv6160sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022894/cv6160Isup2.hkl
Contains datablock I

CCDC reference: 203004

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.113
  • Data-to-parameter ratio = 18.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-Ethyl-3-hydroxy-1-morpholinepyridin-4(1H)-one top
Crystal data top
C11H16N2O3Z = 2
Mr = 224.26F(000) = 240
Triclinic, P1Dx = 1.368 Mg m3
Hall symbol: -P 1Melting point: 258-260°C K
a = 8.4379 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9209 (9) ÅCell parameters from 3224 reflections
c = 9.3312 (12) Åθ = 2.6–33.1°
α = 64.020 (3)°µ = 0.10 mm1
β = 63.198 (2)°T = 173 K
γ = 66.178 (2)°Irregular, colourless
V = 544.62 (10) Å30.35 × 0.20 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 32.5°, θmin = 2.6°
φ and ω scansh = 1212
6121 measured reflectionsk = 1312
3838 independent reflectionsl = 1414
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)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.113All H-atom parameters refined
S = 0.90 w = 1/[σ2(Fo2) + (0.0687P)2]
where P = (Fo2 + 2Fc2)/3
3838 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.13 e Å3
Special details top

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

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
xyzUiso*/Ueq
N10.20667 (11)0.75423 (10)0.38575 (9)0.02456 (17)
C20.05575 (12)0.69746 (12)0.50905 (11)0.02295 (18)
C30.05143 (12)0.62696 (12)0.67385 (11)0.02453 (19)
C40.20088 (13)0.60724 (12)0.72222 (12)0.0262 (2)
C50.35109 (13)0.66842 (13)0.58608 (12)0.0272 (2)
C60.35094 (13)0.73972 (13)0.42439 (12)0.0276 (2)
C70.10135 (13)0.71681 (13)0.46174 (12)0.0266 (2)
C80.24269 (15)0.88937 (15)0.46478 (15)0.0345 (2)
O10.09949 (10)0.57419 (11)0.79449 (9)0.03401 (19)
O20.19415 (10)0.54078 (11)0.87449 (9)0.0374 (2)
N20.20694 (11)0.83302 (10)0.21517 (10)0.02551 (17)
C90.36042 (15)0.73425 (15)0.10604 (13)0.0321 (2)
C100.35731 (17)0.82376 (17)0.07319 (14)0.0380 (3)
O30.36454 (11)0.99896 (11)0.13165 (9)0.0382 (2)
C110.21048 (15)1.09190 (15)0.02686 (14)0.0354 (2)
C120.21099 (14)1.01480 (13)0.15310 (13)0.0290 (2)
H10.096 (2)0.5318 (19)0.898 (2)0.059 (4)*
H50.4586 (15)0.6568 (14)0.6107 (14)0.027 (3)*
H60.4478 (16)0.7853 (15)0.3297 (15)0.029 (3)*
H7A0.0533 (15)0.7008 (15)0.3487 (16)0.031 (3)*
H7B0.1627 (15)0.6227 (15)0.5475 (15)0.027 (3)*
H8A0.1890 (17)0.9816 (17)0.3825 (17)0.037 (3)*
H8B0.3479 (19)0.8966 (17)0.4371 (18)0.050 (4)*
H8C0.2947 (19)0.9030 (17)0.5801 (19)0.050 (4)*
H9A0.4777 (18)0.7212 (16)0.1083 (17)0.040 (3)*
H9B0.3477 (18)0.6195 (17)0.1442 (16)0.042 (3)*
H10A0.4639 (18)0.7629 (16)0.1456 (17)0.040 (3)*
H10B0.2463 (17)0.8197 (16)0.0789 (16)0.039 (3)*
H11A0.2199 (17)1.2111 (17)0.0713 (17)0.037 (3)*
H11B0.0959 (17)1.0912 (16)0.0285 (16)0.036 (3)*
H12A0.3203 (16)1.0256 (15)0.1548 (15)0.029 (3)*
H12B0.1027 (16)1.0754 (15)0.2255 (15)0.029 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0261 (4)0.0266 (4)0.0180 (4)0.0104 (3)0.0052 (3)0.0034 (3)
C20.0242 (4)0.0214 (4)0.0213 (4)0.0084 (3)0.0051 (3)0.0053 (3)
C30.0251 (4)0.0243 (5)0.0210 (4)0.0101 (3)0.0044 (3)0.0044 (4)
C40.0282 (5)0.0249 (5)0.0225 (4)0.0089 (4)0.0078 (4)0.0037 (4)
C50.0256 (4)0.0303 (5)0.0246 (5)0.0102 (4)0.0079 (4)0.0055 (4)
C60.0251 (4)0.0303 (5)0.0234 (4)0.0117 (4)0.0050 (4)0.0043 (4)
C70.0280 (5)0.0292 (5)0.0230 (4)0.0121 (4)0.0072 (4)0.0055 (4)
C80.0314 (5)0.0361 (6)0.0341 (6)0.0057 (4)0.0137 (5)0.0092 (5)
O10.0327 (4)0.0479 (5)0.0191 (3)0.0225 (3)0.0056 (3)0.0006 (3)
O20.0366 (4)0.0508 (5)0.0218 (4)0.0203 (4)0.0106 (3)0.0004 (3)
N20.0293 (4)0.0271 (4)0.0167 (3)0.0117 (3)0.0055 (3)0.0022 (3)
C90.0343 (5)0.0343 (6)0.0250 (5)0.0109 (4)0.0054 (4)0.0096 (4)
C100.0416 (6)0.0509 (7)0.0244 (5)0.0215 (5)0.0052 (4)0.0114 (5)
O30.0409 (4)0.0512 (5)0.0222 (4)0.0267 (4)0.0070 (3)0.0015 (3)
C110.0358 (5)0.0378 (6)0.0294 (5)0.0186 (5)0.0138 (4)0.0034 (4)
C120.0310 (5)0.0268 (5)0.0260 (5)0.0114 (4)0.0085 (4)0.0032 (4)
Geometric parameters (Å, º) top
N1—C61.3624 (12)C8—H8C1.005 (15)
N1—C21.3752 (11)O1—H10.879 (16)
N1—N21.4302 (10)N2—C91.4716 (13)
C2—C31.3719 (12)N2—C121.4732 (13)
C2—C71.5027 (12)C9—C101.5126 (15)
C3—O11.3556 (11)C9—H9A0.958 (13)
C3—C41.4455 (12)C9—H9B0.960 (13)
C4—O21.2609 (11)C10—O31.4297 (15)
C4—C51.4204 (13)C10—H10A0.969 (13)
C5—C61.3569 (13)C10—H10B0.978 (13)
C5—H50.989 (10)O3—C111.4236 (14)
C6—H60.957 (12)C11—C121.5117 (14)
C7—C81.5224 (15)C11—H11A0.980 (13)
C7—H7A0.999 (12)C11—H11B0.977 (12)
C7—H7B1.001 (12)C12—H12A0.973 (11)
C8—H8A0.951 (13)C12—H12B0.973 (12)
C8—H8B1.002 (14)
C6—N1—C2121.29 (8)C3—O1—H1114.2 (9)
C6—N1—N2120.49 (7)N1—N2—C9110.63 (7)
C2—N1—N2118.21 (7)N1—N2—C12110.53 (7)
C3—C2—N1118.67 (8)C9—N2—C12112.01 (8)
C3—C2—C7121.55 (8)N2—C9—C10108.80 (9)
N1—C2—C7119.76 (8)N2—C9—H9A113.0 (8)
O1—C3—C2118.08 (8)C10—C9—H9A109.7 (8)
O1—C3—C4119.44 (8)N2—C9—H9B109.8 (8)
C2—C3—C4122.48 (8)C10—C9—H9B109.4 (8)
O2—C4—C5124.03 (8)H9A—C9—H9B106.0 (10)
O2—C4—C3121.26 (9)O3—C10—C9111.33 (9)
C5—C4—C3114.71 (8)O3—C10—H10A108.7 (8)
C6—C5—C4121.65 (8)C9—C10—H10A108.3 (8)
C6—C5—H5119.7 (7)O3—C10—H10B109.9 (7)
C4—C5—H5118.6 (7)C9—C10—H10B109.7 (8)
C5—C6—N1121.19 (9)H10A—C10—H10B108.9 (10)
C5—C6—H6124.2 (7)C11—O3—C10110.14 (8)
N1—C6—H6114.6 (7)O3—C11—C12110.73 (9)
C2—C7—C8111.86 (8)O3—C11—H11A107.7 (7)
C2—C7—H7A109.7 (6)C12—C11—H11A109.0 (7)
C8—C7—H7A111.3 (7)O3—C11—H11B110.6 (7)
C2—C7—H7B107.4 (6)C12—C11—H11B109.4 (7)
C8—C7—H7B108.3 (6)H11A—C11—H11B109.4 (10)
H7A—C7—H7B108.1 (9)N2—C12—C11108.38 (8)
C7—C8—H8A110.2 (7)N2—C12—H12A111.7 (7)
C7—C8—H8B110.0 (8)C11—C12—H12A108.8 (7)
H8A—C8—H8B107.9 (11)N2—C12—H12B108.5 (7)
C7—C8—H8C111.2 (8)C11—C12—H12B110.6 (7)
H8A—C8—H8C110.2 (11)H12A—C12—H12B108.9 (9)
H8B—C8—H8C107.2 (11)
 

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