Analysis of C
12H
11NO
3 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
CCDC reference: 163915
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.
Crystal data top
C12H11NO3 | Z = 2 |
Mr = 217.22 | F(000) = 228 |
Triclinic, P1 | Dx = 1.449 Mg m−3 |
a = 6.5984 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.1839 (4) Å | Cell parameters from 25 reflections |
c = 11.2817 (6) Å | θ = 8.7–15.4° |
α = 103.084 (4)° | µ = 0.11 mm−1 |
β = 98.380 (5)° | T = 150 K |
γ = 102.485 (5)° | Plate, colorless |
V = 497.81 (5) Å3 | 0.5 × 0.5 × 0.08 mm |
Data collection top
Nonius CAD4 diffractometer | Rint = 0.068 |
Radiation source: rotating anode | θmax = 27.5°, θmin = 1.9° |
Graphite monochromator | h = −8→8 |
ω scans | k = −9→9 |
4924 measured reflections | l = −14→14 |
2279 independent reflections | 3 standard reflections every 60 min |
1652 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H 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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.22 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 | |
N1 | 0.47500 (18) | 0.2735 (2) | 0.03260 (12) | 0.0184 (3) | |
O1 | 0.64505 (18) | 0.0406 (2) | −0.30332 (12) | 0.0297 (3) | |
H1 | 0.740 (4) | 0.123 (5) | −0.225 (3) | 0.087 (10)* | |
O2 | 0.76248 (17) | 0.25770 (19) | −0.06444 (12) | 0.0273 (3) | |
O3 | 0.02648 (17) | −0.02524 (19) | −0.19521 (12) | 0.0286 (3) | |
C1 | 0.2841 (3) | −0.1079 (3) | −0.39485 (17) | 0.0255 (4) | |
H1A | 0.3238 | −0.0745 | −0.4694 | 0.038* | |
H1B | 0.1476 | −0.0796 | −0.3857 | 0.038* | |
H1C | 0.2722 | −0.2487 | −0.4028 | 0.038* | |
C2 | 0.4485 (2) | 0.0119 (2) | −0.28416 (16) | 0.0194 (3) | |
C3 | 0.4062 (2) | 0.0885 (2) | −0.17068 (16) | 0.0186 (3) | |
C4 | 0.2024 (2) | 0.0700 (2) | −0.13554 (16) | 0.0206 (4) | |
C5 | 0.2429 (2) | 0.1946 (3) | −0.00265 (15) | 0.0207 (4) | |
H5A | 0.1716 | 0.3033 | 0.0027 | 0.025* | |
H5B | 0.1910 | 0.1130 | 0.0520 | 0.025* | |
C6 | 0.5700 (2) | 0.2136 (2) | −0.06489 (16) | 0.0187 (3) | |
C7 | 0.5727 (2) | 0.3948 (2) | 0.15333 (15) | 0.0192 (3) | |
C8 | 0.4440 (3) | 0.4370 (3) | 0.23868 (16) | 0.0226 (4) | |
H8 | 0.2947 | 0.3836 | 0.2148 | 0.027* | |
C9 | 0.5332 (3) | 0.5563 (3) | 0.35773 (16) | 0.0268 (4) | |
H9 | 0.4440 | 0.5847 | 0.4146 | 0.032* | |
C10 | 0.7509 (3) | 0.6351 (3) | 0.39540 (17) | 0.0280 (4) | |
H10 | 0.8112 | 0.7170 | 0.4772 | 0.034* | |
C11 | 0.8785 (3) | 0.5917 (3) | 0.31090 (18) | 0.0284 (4) | |
H11 | 1.0278 | 0.6442 | 0.3358 | 0.034* | |
C12 | 0.7925 (2) | 0.4731 (3) | 0.19057 (16) | 0.0237 (4) | |
H12 | 0.8824 | 0.4454 | 0.1340 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0135 (6) | 0.0221 (7) | 0.0179 (7) | 0.0033 (5) | 0.0032 (5) | 0.0029 (6) |
O1 | 0.0202 (6) | 0.0461 (8) | 0.0228 (7) | 0.0106 (6) | 0.0068 (5) | 0.0056 (6) |
O2 | 0.0152 (5) | 0.0386 (7) | 0.0246 (7) | 0.0057 (5) | 0.0049 (5) | 0.0020 (6) |
O3 | 0.0174 (6) | 0.0360 (7) | 0.0248 (7) | −0.0004 (5) | 0.0023 (5) | 0.0016 (6) |
C1 | 0.0255 (8) | 0.0258 (9) | 0.0218 (9) | 0.0058 (7) | 0.0028 (7) | 0.0017 (7) |
C2 | 0.0185 (7) | 0.0207 (8) | 0.0208 (8) | 0.0079 (6) | 0.0044 (6) | 0.0063 (7) |
C3 | 0.0165 (7) | 0.0192 (8) | 0.0192 (8) | 0.0045 (6) | 0.0028 (6) | 0.0042 (7) |
C4 | 0.0189 (7) | 0.0213 (8) | 0.0220 (9) | 0.0048 (6) | 0.0041 (6) | 0.0068 (7) |
C5 | 0.0151 (7) | 0.0249 (9) | 0.0208 (8) | 0.0031 (6) | 0.0055 (6) | 0.0044 (7) |
C6 | 0.0182 (7) | 0.0205 (8) | 0.0176 (8) | 0.0054 (6) | 0.0038 (6) | 0.0054 (7) |
C7 | 0.0218 (8) | 0.0178 (8) | 0.0172 (8) | 0.0050 (6) | 0.0022 (6) | 0.0046 (7) |
C8 | 0.0213 (8) | 0.0254 (9) | 0.0214 (9) | 0.0073 (7) | 0.0045 (6) | 0.0058 (7) |
C9 | 0.0361 (10) | 0.0270 (9) | 0.0195 (9) | 0.0121 (8) | 0.0085 (7) | 0.0048 (8) |
C10 | 0.0369 (10) | 0.0240 (9) | 0.0180 (9) | 0.0060 (8) | −0.0018 (7) | 0.0018 (7) |
C11 | 0.0250 (8) | 0.0259 (9) | 0.0281 (10) | 0.0012 (7) | −0.0013 (7) | 0.0042 (8) |
C12 | 0.0210 (8) | 0.0249 (9) | 0.0231 (9) | 0.0046 (7) | 0.0032 (6) | 0.0046 (7) |
Geometric parameters (Å, º) top
N1—C5 | 1.4732 (18) | C4—C5 | 1.514 (2) |
N1—C6 | 1.375 (2) | C5—H5A | 0.9900 |
N1—C7 | 1.412 (2) | C5—H5B | 0.9900 |
O1—C2 | 1.3258 (19) | C7—C8 | 1.399 (2) |
O1—H1 | 0.99 (3) | C7—C12 | 1.400 (2) |
O2—C6 | 1.2398 (18) | C8—C9 | 1.384 (2) |
O3—C4 | 1.2205 (19) | C8—H8 | 0.9500 |
C1—C2 | 1.480 (2) | C9—C10 | 1.387 (2) |
C1—H1A | 0.9800 | C9—H9 | 0.9500 |
C1—H1B | 0.9800 | C10—C11 | 1.388 (3) |
C1—H1C | 0.9800 | C10—H10 | 0.9500 |
C2—C3 | 1.368 (2) | C11—C12 | 1.390 (2) |
C3—C4 | 1.444 (2) | C11—H11 | 0.9500 |
C3—C6 | 1.456 (2) | C12—H12 | 0.9500 |
| | | |
C6—N1—C7 | 128.11 (13) | C4—C5—H5B | 110.8 |
C6—N1—C5 | 111.22 (13) | H5A—C5—H5B | 108.9 |
C7—N1—C5 | 120.66 (12) | O2—C6—N1 | 126.41 (15) |
C2—O1—H1 | 107.4 (17) | O2—C6—C3 | 124.97 (15) |
C2—C1—H1A | 109.5 | N1—C6—C3 | 108.62 (13) |
C2—C1—H1B | 109.5 | C8—C7—C12 | 119.06 (16) |
H1A—C1—H1B | 109.5 | C8—C7—N1 | 118.43 (14) |
C2—C1—H1C | 109.5 | C12—C7—N1 | 122.51 (14) |
H1A—C1—H1C | 109.5 | C9—C8—C7 | 120.28 (15) |
H1B—C1—H1C | 109.5 | C9—C8—H8 | 119.9 |
O1—C2—C3 | 121.62 (14) | C7—C8—H8 | 119.9 |
O1—C2—C1 | 114.26 (15) | C8—C9—C10 | 121.08 (16) |
C3—C2—C1 | 124.13 (14) | C8—C9—H9 | 119.5 |
C2—C3—C4 | 128.07 (15) | C10—C9—H9 | 119.5 |
C2—C3—C6 | 123.00 (14) | C9—C10—C11 | 118.55 (17) |
C4—C3—C6 | 108.89 (15) | C9—C10—H10 | 120.7 |
O3—C4—C3 | 129.85 (16) | C11—C10—H10 | 120.7 |
O3—C4—C5 | 123.46 (14) | C10—C11—C12 | 121.46 (16) |
C3—C4—C5 | 106.69 (13) | C10—C11—H11 | 119.3 |
N1—C5—C4 | 104.54 (12) | C12—C11—H11 | 119.3 |
N1—C5—H5A | 110.8 | C11—C12—C7 | 119.57 (15) |
C4—C5—H5A | 110.8 | C11—C12—H12 | 120.2 |
N1—C5—H5B | 110.8 | C7—C12—H12 | 120.2 |
| | | |
O1—C2—C3—C4 | −179.90 (16) | C2—C3—C6—O2 | −2.8 (3) |
C1—C2—C3—C4 | 0.2 (3) | C4—C3—C6—O2 | 179.58 (16) |
O1—C2—C3—C6 | 2.9 (3) | C2—C3—C6—N1 | 177.11 (15) |
C1—C2—C3—C6 | −176.99 (16) | C4—C3—C6—N1 | −0.54 (18) |
C2—C3—C4—O3 | 4.7 (3) | C6—N1—C7—C8 | −179.93 (16) |
C6—C3—C4—O3 | −177.83 (17) | C5—N1—C7—C8 | 0.4 (2) |
C2—C3—C4—C5 | −175.89 (16) | C6—N1—C7—C12 | −0.2 (3) |
C6—C3—C4—C5 | 1.60 (18) | C5—N1—C7—C12 | −179.86 (16) |
C6—N1—C5—C4 | 1.74 (18) | C12—C7—C8—C9 | 0.7 (3) |
C7—N1—C5—C4 | −178.52 (14) | N1—C7—C8—C9 | −179.58 (15) |
O3—C4—C5—N1 | 177.48 (15) | C7—C8—C9—C10 | −0.5 (3) |
C3—C4—C5—N1 | −1.99 (17) | C8—C9—C10—C11 | −0.1 (3) |
C7—N1—C6—O2 | −0.6 (3) | C9—C10—C11—C12 | 0.4 (3) |
C5—N1—C6—O2 | 179.08 (16) | C10—C11—C12—C7 | −0.2 (3) |
C7—N1—C6—C3 | 179.49 (14) | C8—C7—C12—C11 | −0.3 (3) |
C5—N1—C6—C3 | −0.81 (18) | N1—C7—C12—C11 | 179.93 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.99 (3) | 1.81 (3) | 2.6948 (18) | 147 (2) |
O1—H1···O3i | 0.99 (3) | 2.38 (3) | 2.8155 (18) | 106 (2) |
C5—H5B···O3ii | 0.99 | 2.41 | 3.328 (2) | 154 |
C1—H1B···O3 | 0.98 | 2.38 | 3.043 (2) | 124 |
C12—H12···O2 | 0.95 | 2.26 | 2.898 (2) | 124 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z. |