Acta Cryst. (2011). E67, o365 [ doi:10.1107/S1600536811000717 ]
The C=C double-bond in the title compound, C13H13ClO3, has a Z configuration. The aliphatic substituents at one end of the double bond, i.e. the CH3CO- and C2H5O2C- groups, are aligned at 82.1 (3)° with respect to each other.
Trizma (0.01 mol), p-chlorobenzaldehyde (0.01 mol) and ethyl acetoacetate (0.02 mol) were heated in ethanol (50 ml) for 3 h. The reaction was monitored with TLC. The solid that separated was collected and recrystallized from ethanol to give a colorless crystals, m.p. 373 K (60% yield).
Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.97 Å; U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
![[Figure 1]](./hg2789fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C13H13ClO3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
| C13H13ClO3 | F(000) = 528 |
| Mr = 252.68 | Dx = 1.351 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3560 reflections |
| a = 9.9956 (6) Å | θ = 2.2–27.8° |
| b = 7.7487 (5) Å | µ = 0.30 mm−1 |
| c = 16.2709 (10) Å | T = 295 K |
| β = 99.624 (1)° | Prism, colorless |
| V = 1242.49 (13) Å3 | 0.20 × 0.20 × 0.20 mm |
| Z = 4 |
| Bruker APEXII diffractometer | 2790 independent reflections |
| Radiation source: fine-focus sealed tube | 1968 reflections with I > 2σ(I) |
| graphite | Rint = 0.069 |
| φ and ω scans | θmax = 27.5°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
| Tmin = 0.942, Tmax = 0.942 | k = −10→9 |
| 11255 measured reflections | l = −21→21 |
| 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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.201 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.1314P)2] where P = (Fo2 + 2Fc2)/3 |
| 2790 reflections | (Δ/σ)max = 0.001 |
| 156 parameters | Δρmax = 0.40 e Å−3 |
| 0 restraints | Δρmin = −0.52 e Å−3 |
| C13H13ClO3 | V = 1242.49 (13) Å3 |
| Mr = 252.68 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 9.9956 (6) Å | µ = 0.30 mm−1 |
| b = 7.7487 (5) Å | T = 295 K |
| c = 16.2709 (10) Å | 0.20 × 0.20 × 0.20 mm |
| β = 99.624 (1)° |
| Bruker APEXII diffractometer | 1968 reflections with I > 2σ(I) |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | Rint = 0.069 |
| Tmin = 0.942, Tmax = 0.942 | θmax = 27.5° |
| 11255 measured reflections | Standard reflections: 0 |
| 2790 independent reflections |
| R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
| wR(F2) = 0.201 | Δρmax = 0.40 e Å−3 |
| S = 1.01 | Δρmin = −0.52 e Å−3 |
| 2790 reflections | Absolute structure: ? |
| 156 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.17886 (7) | 0.43778 (11) | 0.15024 (4) | 0.0663 (3) | |
| O1 | 0.2270 (2) | 0.3753 (3) | 0.72305 (11) | 0.0703 (6) | |
| O2 | 0.42363 (15) | 0.4336 (2) | 0.59728 (11) | 0.0555 (5) | |
| O3 | 0.27248 (13) | 0.6486 (2) | 0.56982 (10) | 0.0452 (4) | |
| C1 | 0.13562 (19) | 0.3488 (3) | 0.41918 (13) | 0.0399 (5) | |
| C2 | 0.2540 (2) | 0.4199 (3) | 0.39776 (14) | 0.0453 (6) | |
| H2A | 0.3252 | 0.4497 | 0.4397 | 0.054* | |
| C3 | 0.2669 (2) | 0.4463 (3) | 0.31626 (14) | 0.0467 (6) | |
| H3 | 0.3460 | 0.4940 | 0.3031 | 0.056* | |
| C4 | 0.1611 (2) | 0.4015 (3) | 0.25368 (14) | 0.0437 (5) | |
| C5 | 0.0440 (2) | 0.3274 (3) | 0.27150 (14) | 0.0490 (6) | |
| H5 | −0.0258 | 0.2957 | 0.2290 | 0.059* | |
| C6 | 0.03270 (19) | 0.3015 (3) | 0.35374 (14) | 0.0453 (5) | |
| H6 | −0.0458 | 0.2509 | 0.3662 | 0.054* | |
| C7 | 0.11396 (19) | 0.3175 (3) | 0.50496 (14) | 0.0418 (5) | |
| H7 | 0.0387 | 0.2501 | 0.5098 | 0.050* | |
| C8 | 0.18613 (19) | 0.3714 (3) | 0.57758 (13) | 0.0405 (5) | |
| C9 | 0.1549 (2) | 0.3219 (3) | 0.66085 (15) | 0.0501 (6) | |
| C10 | 0.0339 (3) | 0.2111 (4) | 0.66738 (18) | 0.0693 (8) | |
| H10A | 0.0333 | 0.1832 | 0.7248 | 0.104* | |
| H10B | 0.0385 | 0.1068 | 0.6362 | 0.104* | |
| H10C | −0.0476 | 0.2727 | 0.6453 | 0.104* | |
| C11 | 0.3088 (2) | 0.4853 (3) | 0.58325 (13) | 0.0395 (5) | |
| C12 | 0.3811 (2) | 0.7742 (3) | 0.57098 (17) | 0.0535 (6) | |
| H12A | 0.4275 | 0.7563 | 0.5239 | 0.064* | |
| H12B | 0.4466 | 0.7634 | 0.6219 | 0.064* | |
| C13 | 0.3162 (3) | 0.9486 (3) | 0.56615 (18) | 0.0592 (7) | |
| H13A | 0.3836 | 1.0353 | 0.5626 | 0.089* | |
| H13B | 0.2764 | 0.9679 | 0.6151 | 0.089* | |
| H13C | 0.2470 | 0.9546 | 0.5176 | 0.089* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0540 (4) | 0.0967 (7) | 0.0483 (4) | 0.0031 (3) | 0.0085 (3) | 0.0024 (3) |
| O1 | 0.0600 (11) | 0.0996 (17) | 0.0513 (11) | −0.0032 (11) | 0.0095 (9) | 0.0006 (10) |
| O2 | 0.0281 (8) | 0.0621 (12) | 0.0735 (12) | 0.0041 (7) | −0.0001 (7) | 0.0076 (8) |
| O3 | 0.0282 (7) | 0.0479 (10) | 0.0601 (9) | −0.0011 (6) | 0.0091 (6) | −0.0004 (7) |
| C1 | 0.0237 (8) | 0.0445 (12) | 0.0514 (12) | −0.0006 (8) | 0.0061 (8) | −0.0051 (9) |
| C2 | 0.0235 (9) | 0.0614 (15) | 0.0504 (12) | −0.0061 (9) | 0.0049 (8) | −0.0091 (10) |
| C3 | 0.0280 (10) | 0.0594 (15) | 0.0533 (13) | −0.0052 (9) | 0.0086 (9) | −0.0040 (10) |
| C4 | 0.0335 (10) | 0.0524 (13) | 0.0446 (11) | 0.0046 (9) | 0.0050 (8) | −0.0025 (10) |
| C5 | 0.0295 (10) | 0.0605 (14) | 0.0540 (13) | −0.0031 (10) | −0.0013 (9) | −0.0107 (11) |
| C6 | 0.0237 (9) | 0.0528 (13) | 0.0590 (13) | −0.0075 (9) | 0.0060 (8) | −0.0092 (10) |
| C7 | 0.0246 (9) | 0.0464 (12) | 0.0555 (12) | −0.0016 (8) | 0.0099 (8) | −0.0030 (10) |
| C8 | 0.0280 (9) | 0.0422 (12) | 0.0522 (12) | 0.0038 (9) | 0.0092 (8) | 0.0033 (9) |
| C9 | 0.0405 (11) | 0.0575 (15) | 0.0545 (13) | 0.0068 (10) | 0.0147 (10) | 0.0040 (11) |
| C10 | 0.0592 (16) | 0.080 (2) | 0.0759 (18) | −0.0097 (14) | 0.0314 (14) | 0.0065 (15) |
| C11 | 0.0284 (9) | 0.0499 (13) | 0.0400 (10) | 0.0034 (9) | 0.0046 (8) | 0.0021 (9) |
| C12 | 0.0379 (11) | 0.0576 (16) | 0.0653 (14) | −0.0090 (10) | 0.0092 (10) | 0.0009 (12) |
| C13 | 0.0581 (16) | 0.0522 (15) | 0.0686 (17) | −0.0050 (12) | 0.0140 (13) | −0.0020 (12) |
| Cl1—C4 | 1.745 (2) | C6—H6 | 0.9300 |
| O1—C9 | 1.213 (3) | C7—C8 | 1.344 (3) |
| O2—C11 | 1.201 (2) | C7—H7 | 0.9300 |
| O3—C11 | 1.325 (3) | C8—C9 | 1.491 (3) |
| O3—C12 | 1.456 (3) | C8—C11 | 1.501 (3) |
| C1—C6 | 1.400 (3) | C9—C10 | 1.502 (4) |
| C1—C2 | 1.401 (3) | C10—H10A | 0.9600 |
| C1—C7 | 1.468 (3) | C10—H10B | 0.9600 |
| C2—C3 | 1.369 (3) | C10—H10C | 0.9600 |
| C2—H2A | 0.9300 | C12—C13 | 1.495 (4) |
| C3—C4 | 1.384 (3) | C12—H12A | 0.9700 |
| C3—H3 | 0.9300 | C12—H12B | 0.9700 |
| C4—C5 | 1.377 (3) | C13—H13A | 0.9600 |
| C5—C6 | 1.376 (3) | C13—H13B | 0.9600 |
| C5—H5 | 0.9300 | C13—H13C | 0.9600 |
| C11—O3—C12 | 116.98 (16) | O1—C9—C8 | 119.1 (2) |
| C6—C1—C2 | 117.2 (2) | O1—C9—C10 | 120.6 (2) |
| C6—C1—C7 | 118.26 (18) | C8—C9—C10 | 120.3 (2) |
| C2—C1—C7 | 124.50 (19) | C9—C10—H10A | 109.5 |
| C3—C2—C1 | 121.34 (19) | C9—C10—H10B | 109.5 |
| C3—C2—H2A | 119.3 | H10A—C10—H10B | 109.5 |
| C1—C2—H2A | 119.3 | C9—C10—H10C | 109.5 |
| C2—C3—C4 | 119.4 (2) | H10A—C10—H10C | 109.5 |
| C2—C3—H3 | 120.3 | H10B—C10—H10C | 109.5 |
| C4—C3—H3 | 120.3 | O2—C11—O3 | 125.2 (2) |
| C5—C4—C3 | 121.4 (2) | O2—C11—C8 | 124.1 (2) |
| C5—C4—Cl1 | 119.85 (17) | O3—C11—C8 | 110.72 (16) |
| C3—C4—Cl1 | 118.72 (18) | O3—C12—C13 | 106.71 (18) |
| C6—C5—C4 | 118.5 (2) | O3—C12—H12A | 110.4 |
| C6—C5—H5 | 120.8 | C13—C12—H12A | 110.4 |
| C4—C5—H5 | 120.8 | O3—C12—H12B | 110.4 |
| C5—C6—C1 | 122.12 (19) | C13—C12—H12B | 110.4 |
| C5—C6—H6 | 118.9 | H12A—C12—H12B | 108.6 |
| C1—C6—H6 | 118.9 | C12—C13—H13A | 109.5 |
| C8—C7—C1 | 130.0 (2) | C12—C13—H13B | 109.5 |
| C8—C7—H7 | 115.0 | H13A—C13—H13B | 109.5 |
| C1—C7—H7 | 115.0 | C12—C13—H13C | 109.5 |
| C7—C8—C9 | 123.8 (2) | H13A—C13—H13C | 109.5 |
| C7—C8—C11 | 123.3 (2) | H13B—C13—H13C | 109.5 |
| C9—C8—C11 | 112.85 (19) | ||
| C6—C1—C2—C3 | 1.7 (3) | C1—C7—C8—C11 | 1.8 (4) |
| C7—C1—C2—C3 | −179.6 (2) | C7—C8—C9—O1 | 179.1 (2) |
| C1—C2—C3—C4 | −0.2 (4) | C11—C8—C9—O1 | 0.2 (3) |
| C2—C3—C4—C5 | −1.3 (4) | C7—C8—C9—C10 | −2.4 (4) |
| C2—C3—C4—Cl1 | 179.48 (18) | C11—C8—C9—C10 | 178.7 (2) |
| C3—C4—C5—C6 | 1.2 (4) | C12—O3—C11—O2 | 1.0 (3) |
| Cl1—C4—C5—C6 | −179.59 (18) | C12—O3—C11—C8 | −178.29 (18) |
| C4—C5—C6—C1 | 0.4 (4) | C7—C8—C11—O2 | −99.3 (3) |
| C2—C1—C6—C5 | −1.8 (3) | C9—C8—C11—O2 | 79.6 (3) |
| C7—C1—C6—C5 | 179.4 (2) | C7—C8—C11—O3 | 80.1 (3) |
| C6—C1—C7—C8 | −169.6 (2) | C9—C8—C11—O3 | −101.1 (2) |
| C2—C1—C7—C8 | 11.7 (4) | C11—O3—C12—C13 | −172.43 (19) |
| C1—C7—C8—C9 | −177.0 (2) |
We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, P.-F., Chen, G.-B., Feng, Y.-Q. & Song, J. (2007). Acta Cryst. E63, o3532.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Shi, X. (2008). Acta Cryst. E64, o2462.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Trizma is a mildly-basic primary aminoalcohol that catalyzes Knoevenagel condensation reactions. The yield can be high under microwave irradiation; the title compound has been synthesized albeit by a conventional route. The carbon-carbon double-bond in C13H13ClO3 has a Z-configuration. The aliphatic substituents at one end of the double-bond, i.e., the CH3CO– and planar C2H5O2C– groups, are aligned at 82.1 (3) ° with respect to each other. Bond dimensions in the molecule compare favorably with those found in similar molecules (Deng et al., 2007; Shi, 2008).