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Analysis of C12H11NO3 revealed a coplanar N-substituted phenyl group on a pyrrolidine ring with two keto moieties and a hydroxy­ethyl­idene functionality. The hydroxy group forms part of a hydrogen-bonding network characterized by a short intramolecular H...O distance of 1.81 (3) Å, and a longer intermolecular interaction with an H...O distance of 2.38 (3) Å. Both keto groups form additional intra- and intermolecular C—H...O contacts with H...O distances ranging from 2.26 to 2.41 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020758/na1499sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020758/na1499Isup2.hkl
Contains datablock I

CCDC reference: 163915

Computing details top

Data collection: Locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: PLATON.

(I) top
Crystal data top
C12H11NO3Z = 2
Mr = 217.22F(000) = 228
Triclinic, P1Dx = 1.449 Mg m3
a = 6.5984 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.1839 (4) ÅCell parameters from 25 reflections
c = 11.2817 (6) Åθ = 8.7–15.4°
α = 103.084 (4)°µ = 0.11 mm1
β = 98.380 (5)°T = 150 K
γ = 102.485 (5)°Plate, colorless
V = 497.81 (5) Å30.5 × 0.5 × 0.08 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.068
Radiation source: rotating anodeθmax = 27.5°, θmin = 1.9°
Graphite monochromatorh = 88
ω scansk = 99
4924 measured reflectionsl = 1414
2279 independent reflections3 standard reflections every 60 min
1652 reflections with I > 2σ(I) intensity decay: <1%
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0494P)2 + 0.0415P]
where P = (Fo2 + 2Fc2)/3
2279 reflections(Δ/σ)max = 0.001
150 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N10.47500 (18)0.2735 (2)0.03260 (12)0.0184 (3)
O10.64505 (18)0.0406 (2)0.30332 (12)0.0297 (3)
H10.740 (4)0.123 (5)0.225 (3)0.087 (10)*
O20.76248 (17)0.25770 (19)0.06444 (12)0.0273 (3)
O30.02648 (17)0.02524 (19)0.19521 (12)0.0286 (3)
C10.2841 (3)0.1079 (3)0.39485 (17)0.0255 (4)
H1A0.32380.07450.46940.038*
H1B0.14760.07960.38570.038*
H1C0.27220.24870.40280.038*
C20.4485 (2)0.0119 (2)0.28416 (16)0.0194 (3)
C30.4062 (2)0.0885 (2)0.17068 (16)0.0186 (3)
C40.2024 (2)0.0700 (2)0.13554 (16)0.0206 (4)
C50.2429 (2)0.1946 (3)0.00265 (15)0.0207 (4)
H5A0.17160.30330.00270.025*
H5B0.19100.11300.05200.025*
C60.5700 (2)0.2136 (2)0.06489 (16)0.0187 (3)
C70.5727 (2)0.3948 (2)0.15333 (15)0.0192 (3)
C80.4440 (3)0.4370 (3)0.23868 (16)0.0226 (4)
H80.29470.38360.21480.027*
C90.5332 (3)0.5563 (3)0.35773 (16)0.0268 (4)
H90.44400.58470.41460.032*
C100.7509 (3)0.6351 (3)0.39540 (17)0.0280 (4)
H100.81120.71700.47720.034*
C110.8785 (3)0.5917 (3)0.31090 (18)0.0284 (4)
H111.02780.64420.33580.034*
C120.7925 (2)0.4731 (3)0.19057 (16)0.0237 (4)
H120.88240.44540.13400.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0135 (6)0.0221 (7)0.0179 (7)0.0033 (5)0.0032 (5)0.0029 (6)
O10.0202 (6)0.0461 (8)0.0228 (7)0.0106 (6)0.0068 (5)0.0056 (6)
O20.0152 (5)0.0386 (7)0.0246 (7)0.0057 (5)0.0049 (5)0.0020 (6)
O30.0174 (6)0.0360 (7)0.0248 (7)0.0004 (5)0.0023 (5)0.0016 (6)
C10.0255 (8)0.0258 (9)0.0218 (9)0.0058 (7)0.0028 (7)0.0017 (7)
C20.0185 (7)0.0207 (8)0.0208 (8)0.0079 (6)0.0044 (6)0.0063 (7)
C30.0165 (7)0.0192 (8)0.0192 (8)0.0045 (6)0.0028 (6)0.0042 (7)
C40.0189 (7)0.0213 (8)0.0220 (9)0.0048 (6)0.0041 (6)0.0068 (7)
C50.0151 (7)0.0249 (9)0.0208 (8)0.0031 (6)0.0055 (6)0.0044 (7)
C60.0182 (7)0.0205 (8)0.0176 (8)0.0054 (6)0.0038 (6)0.0054 (7)
C70.0218 (8)0.0178 (8)0.0172 (8)0.0050 (6)0.0022 (6)0.0046 (7)
C80.0213 (8)0.0254 (9)0.0214 (9)0.0073 (7)0.0045 (6)0.0058 (7)
C90.0361 (10)0.0270 (9)0.0195 (9)0.0121 (8)0.0085 (7)0.0048 (8)
C100.0369 (10)0.0240 (9)0.0180 (9)0.0060 (8)0.0018 (7)0.0018 (7)
C110.0250 (8)0.0259 (9)0.0281 (10)0.0012 (7)0.0013 (7)0.0042 (8)
C120.0210 (8)0.0249 (9)0.0231 (9)0.0046 (7)0.0032 (6)0.0046 (7)
Geometric parameters (Å, º) top
N1—C51.4732 (18)C4—C51.514 (2)
N1—C61.375 (2)C5—H5A0.9900
N1—C71.412 (2)C5—H5B0.9900
O1—C21.3258 (19)C7—C81.399 (2)
O1—H10.99 (3)C7—C121.400 (2)
O2—C61.2398 (18)C8—C91.384 (2)
O3—C41.2205 (19)C8—H80.9500
C1—C21.480 (2)C9—C101.387 (2)
C1—H1A0.9800C9—H90.9500
C1—H1B0.9800C10—C111.388 (3)
C1—H1C0.9800C10—H100.9500
C2—C31.368 (2)C11—C121.390 (2)
C3—C41.444 (2)C11—H110.9500
C3—C61.456 (2)C12—H120.9500
C6—N1—C7128.11 (13)C4—C5—H5B110.8
C6—N1—C5111.22 (13)H5A—C5—H5B108.9
C7—N1—C5120.66 (12)O2—C6—N1126.41 (15)
C2—O1—H1107.4 (17)O2—C6—C3124.97 (15)
C2—C1—H1A109.5N1—C6—C3108.62 (13)
C2—C1—H1B109.5C8—C7—C12119.06 (16)
H1A—C1—H1B109.5C8—C7—N1118.43 (14)
C2—C1—H1C109.5C12—C7—N1122.51 (14)
H1A—C1—H1C109.5C9—C8—C7120.28 (15)
H1B—C1—H1C109.5C9—C8—H8119.9
O1—C2—C3121.62 (14)C7—C8—H8119.9
O1—C2—C1114.26 (15)C8—C9—C10121.08 (16)
C3—C2—C1124.13 (14)C8—C9—H9119.5
C2—C3—C4128.07 (15)C10—C9—H9119.5
C2—C3—C6123.00 (14)C9—C10—C11118.55 (17)
C4—C3—C6108.89 (15)C9—C10—H10120.7
O3—C4—C3129.85 (16)C11—C10—H10120.7
O3—C4—C5123.46 (14)C10—C11—C12121.46 (16)
C3—C4—C5106.69 (13)C10—C11—H11119.3
N1—C5—C4104.54 (12)C12—C11—H11119.3
N1—C5—H5A110.8C11—C12—C7119.57 (15)
C4—C5—H5A110.8C11—C12—H12120.2
N1—C5—H5B110.8C7—C12—H12120.2
O1—C2—C3—C4179.90 (16)C2—C3—C6—O22.8 (3)
C1—C2—C3—C40.2 (3)C4—C3—C6—O2179.58 (16)
O1—C2—C3—C62.9 (3)C2—C3—C6—N1177.11 (15)
C1—C2—C3—C6176.99 (16)C4—C3—C6—N10.54 (18)
C2—C3—C4—O34.7 (3)C6—N1—C7—C8179.93 (16)
C6—C3—C4—O3177.83 (17)C5—N1—C7—C80.4 (2)
C2—C3—C4—C5175.89 (16)C6—N1—C7—C120.2 (3)
C6—C3—C4—C51.60 (18)C5—N1—C7—C12179.86 (16)
C6—N1—C5—C41.74 (18)C12—C7—C8—C90.7 (3)
C7—N1—C5—C4178.52 (14)N1—C7—C8—C9179.58 (15)
O3—C4—C5—N1177.48 (15)C7—C8—C9—C100.5 (3)
C3—C4—C5—N11.99 (17)C8—C9—C10—C110.1 (3)
C7—N1—C6—O20.6 (3)C9—C10—C11—C120.4 (3)
C5—N1—C6—O2179.08 (16)C10—C11—C12—C70.2 (3)
C7—N1—C6—C3179.49 (14)C8—C7—C12—C110.3 (3)
C5—N1—C6—C30.81 (18)N1—C7—C12—C11179.93 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.99 (3)1.81 (3)2.6948 (18)147 (2)
O1—H1···O3i0.99 (3)2.38 (3)2.8155 (18)106 (2)
C5—H5B···O3ii0.992.413.328 (2)154
C1—H1B···O30.982.383.043 (2)124
C12—H12···O20.952.262.898 (2)124
Symmetry codes: (i) x+1, y, z; (ii) x, y, z.
 

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