Acta Cryst. (2009). E65, o2976 [ doi:10.1107/S1600536809045553 ]
There are two independent molecules in the asymmetric unit of the title compound, C15H12ClN2O2. In each molecule, the two benzene rings adopt a cis configuration with respect to the epoxy ring. The dihedral angles between the epoxy ring and chlorophenyl rings are essentially identical in the two molecules [62.50 (9) and 62.67 (9)°]. Intermolecualar N-H
O and C-HO hydrogen bonding is present in the crystal structure.
2-Chloro-N-phenylacetamide (0.17 g, 1.0 mmol) and potassium hydroxide (0.112 g, 2.0 mmol) were dissolved in acetonitrile (2 ml). To the solution was added 3-chlorophenylaldehyde (0.15 g, 1.0 mmol) at 298 K, the solution was stirred for 60 min and removal of solvent under reduced pressure, the residue was purified through column chromatography. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature for 2 d.
H atoms on N atoms were located in a difference Fourier map and refined isotropically, with restrains of N—H = 0.89±0.01 Å. Other H atoms were positioned geometrically with C—H = 0.93 and 0.98 Å, for aromatic and methine H atoms, respectively, and refined using a riding model, with Uiso(H) =1.2Ueq(C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./xu2659fig1thm.gif)
| Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). |
| C15H12ClNO2 | F(000) = 568 |
| Mr = 273.71 | Dx = 1.409 Mg m−3 |
| Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
| Hall symbol: P 2yb | Cell parameters from 12871 reflections |
| a = 5.4480 (1) Å | θ = 2.1–69.4° |
| b = 11.1481 (2) Å | µ = 2.60 mm−1 |
| c = 21.3152 (4) Å | T = 295 K |
| β = 94.472 (2)° | Block, colorless |
| V = 1290.63 (4) Å3 | 0.40 × 0.30 × 0.30 mm |
| Z = 4 |
| Oxford Diffraction Gemini S Ultra diffractometer | 4775 independent reflections |
| Radiation source: Enhance Ultra (Cu) X-ray Source | 4453 reflections with I > 2σ(I) |
| mirror | Rint = 0.030 |
| Detector resolution: 15.9149 pixels mm-1 | θmax = 69.7°, θmin = 2.1° |
| ω scans | h = −6→5 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −13→13 |
| Tmin = 0.423, Tmax = 0.510 | l = −25→25 |
| 19148 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.044P)2 + 0.0893P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.001 |
| 4775 reflections | Δρmax = 0.16 e Å−3 |
| 351 parameters | Δρmin = −0.32 e Å−3 |
| 3 restraints | Absolute structure: Flack (1983), 2223 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.000 (9) |
| C15H12ClNO2 | V = 1290.63 (4) Å3 |
| Mr = 273.71 | Z = 4 |
| Monoclinic, P21 | Cu Kα radiation |
| a = 5.4480 (1) Å | µ = 2.60 mm−1 |
| b = 11.1481 (2) Å | T = 295 K |
| c = 21.3152 (4) Å | 0.40 × 0.30 × 0.30 mm |
| β = 94.472 (2)° |
| Oxford Diffraction Gemini S Ultra diffractometer | 4775 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 4453 reflections with I > 2σ(I) |
| Tmin = 0.423, Tmax = 0.510 | Rint = 0.030 |
| 19148 measured reflections | θmax = 69.7° |
| R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.072 | Δρmax = 0.16 e Å−3 |
| S = 1.00 | Δρmin = −0.32 e Å−3 |
| 4775 reflections | Absolute structure: Flack (1983), 2223 Friedel pairs |
| 351 parameters | Flack parameter: 0.000 (9) |
| 3 restraints |
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. |
| x | y | z | Uiso*/Ueq | ||
| Cl2 | 0.94031 (10) | 0.56442 (6) | 0.21597 (3) | 0.07852 (18) | |
| Cl1 | 0.50893 (11) | 0.28922 (5) | 0.71602 (3) | 0.07628 (16) | |
| N2 | 1.1469 (2) | 0.78718 (12) | −0.07435 (6) | 0.0417 (3) | |
| O4 | 0.7412 (2) | 0.80333 (12) | −0.05625 (5) | 0.0544 (3) | |
| O3 | 1.2753 (2) | 0.95679 (10) | 0.01702 (6) | 0.0532 (3) | |
| O2 | 0.7705 (2) | 0.71550 (11) | 0.52655 (6) | 0.0574 (3) | |
| O1 | 0.2463 (2) | 0.56111 (12) | 0.44875 (5) | 0.0550 (3) | |
| N1 | 0.6527 (2) | 0.55043 (12) | 0.43108 (6) | 0.0451 (3) | |
| C6 | 0.5906 (3) | 0.47577 (15) | 0.63907 (7) | 0.0465 (4) | |
| H6 | 0.4543 | 0.5115 | 0.6550 | 0.056* | |
| C20 | 1.1985 (3) | 0.78579 (15) | 0.08902 (7) | 0.0403 (3) | |
| C22 | 1.1318 (3) | 0.90707 (14) | 0.06459 (7) | 0.0445 (3) | |
| H22 | 1.0876 | 0.9645 | 0.0967 | 0.053* | |
| C21 | 1.0566 (3) | 0.73574 (15) | 0.13417 (7) | 0.0462 (4) | |
| H21 | 0.9217 | 0.7772 | 0.1474 | 0.055* | |
| C25 | 1.1310 (3) | 0.69572 (13) | −0.12107 (6) | 0.0364 (3) | |
| C13 | 0.6367 (3) | 0.29390 (16) | 0.28639 (7) | 0.0467 (3) | |
| H13 | 0.6364 | 0.2383 | 0.2539 | 0.056* | |
| C10 | 0.6416 (3) | 0.46247 (13) | 0.38252 (7) | 0.0384 (3) | |
| C24 | 0.9560 (3) | 0.83310 (14) | −0.04600 (7) | 0.0423 (3) | |
| C26 | 0.9306 (3) | 0.68800 (14) | −0.16549 (6) | 0.0406 (3) | |
| H26 | 0.8009 | 0.7420 | −0.1645 | 0.049* | |
| C2 | 0.8708 (3) | 0.30841 (17) | 0.63764 (9) | 0.0579 (4) | |
| H2 | 0.9211 | 0.2329 | 0.6521 | 0.069* | |
| C29 | 1.3159 (3) | 0.52760 (15) | −0.16920 (8) | 0.0473 (4) | |
| H29 | 1.4457 | 0.4737 | −0.1706 | 0.057* | |
| C5 | 0.7174 (3) | 0.53523 (15) | 0.59396 (7) | 0.0439 (3) | |
| C30 | 1.3245 (3) | 0.61452 (14) | −0.12309 (7) | 0.0430 (3) | |
| H30 | 1.4589 | 0.6189 | −0.0935 | 0.052* | |
| C16 | 1.1176 (3) | 0.62478 (16) | 0.15900 (8) | 0.0501 (4) | |
| C9 | 0.4602 (3) | 0.59164 (14) | 0.46030 (7) | 0.0433 (3) | |
| C7 | 0.6352 (3) | 0.65669 (15) | 0.57293 (7) | 0.0477 (4) | |
| H7 | 0.5868 | 0.7092 | 0.6067 | 0.057* | |
| C8 | 0.5170 (3) | 0.68526 (15) | 0.51004 (8) | 0.0484 (4) | |
| H8 | 0.4025 | 0.7532 | 0.5088 | 0.058* | |
| C1 | 0.6677 (3) | 0.36400 (16) | 0.65992 (8) | 0.0509 (4) | |
| C17 | 1.3165 (3) | 0.56100 (17) | 0.14013 (8) | 0.0560 (4) | |
| H17 | 1.3554 | 0.4859 | 0.1571 | 0.067* | |
| C14 | 0.8318 (3) | 0.29880 (17) | 0.33223 (8) | 0.0546 (4) | |
| H14 | 0.9620 | 0.2452 | 0.3306 | 0.066* | |
| C11 | 0.4450 (3) | 0.45718 (14) | 0.33707 (7) | 0.0446 (4) | |
| H11 | 0.3143 | 0.5105 | 0.3385 | 0.053* | |
| C4 | 0.9242 (3) | 0.48034 (18) | 0.57174 (8) | 0.0555 (4) | |
| H4 | 1.0134 | 0.5193 | 0.5423 | 0.067* | |
| C27 | 0.9252 (3) | 0.59935 (16) | −0.21130 (7) | 0.0461 (4) | |
| H27 | 0.7906 | 0.5940 | −0.2408 | 0.055* | |
| C23 | 1.0199 (3) | 0.93147 (14) | 0.00091 (8) | 0.0463 (4) | |
| H23 | 0.9122 | 1.0019 | −0.0028 | 0.056* | |
| C19 | 1.3997 (3) | 0.72225 (16) | 0.07008 (7) | 0.0485 (4) | |
| H19 | 1.4960 | 0.7548 | 0.0402 | 0.058* | |
| C3 | 0.9960 (4) | 0.36815 (19) | 0.59349 (9) | 0.0620 (5) | |
| H3 | 1.1325 | 0.3319 | 0.5779 | 0.074* | |
| C18 | 1.4563 (3) | 0.61121 (17) | 0.09554 (8) | 0.0569 (4) | |
| H18 | 1.5909 | 0.5693 | 0.0825 | 0.068* | |
| C28 | 1.1165 (3) | 0.51936 (15) | −0.21357 (7) | 0.0465 (4) | |
| H28 | 1.1122 | 0.4604 | −0.2445 | 0.056* | |
| C15 | 0.8354 (3) | 0.38212 (16) | 0.38009 (8) | 0.0484 (4) | |
| H15 | 0.9669 | 0.3845 | 0.4106 | 0.058* | |
| C12 | 0.4439 (3) | 0.37255 (15) | 0.28980 (7) | 0.0465 (4) | |
| H12 | 0.3107 | 0.3687 | 0.2598 | 0.056* | |
| H1 | 0.804 (2) | 0.578 (2) | 0.4432 (9) | 0.068 (6)* | |
| H16 | 1.299 (2) | 0.8100 (17) | −0.0620 (8) | 0.057 (5)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl2 | 0.0624 (3) | 0.0986 (4) | 0.0746 (3) | −0.0042 (3) | 0.0055 (2) | 0.0396 (3) |
| Cl1 | 0.0844 (4) | 0.0729 (3) | 0.0736 (3) | 0.0089 (3) | 0.0196 (3) | 0.0186 (3) |
| N2 | 0.0410 (7) | 0.0456 (6) | 0.0381 (6) | −0.0039 (6) | 0.0015 (5) | −0.0040 (5) |
| O4 | 0.0458 (7) | 0.0632 (8) | 0.0550 (7) | −0.0043 (6) | 0.0089 (5) | −0.0090 (6) |
| O3 | 0.0640 (8) | 0.0475 (6) | 0.0487 (6) | −0.0142 (5) | 0.0080 (5) | −0.0033 (5) |
| O2 | 0.0684 (8) | 0.0541 (7) | 0.0502 (6) | −0.0205 (6) | 0.0078 (6) | −0.0091 (5) |
| O1 | 0.0466 (6) | 0.0663 (8) | 0.0527 (6) | −0.0062 (6) | 0.0083 (5) | −0.0134 (6) |
| N1 | 0.0435 (7) | 0.0504 (8) | 0.0411 (6) | −0.0064 (6) | 0.0025 (5) | −0.0109 (6) |
| C6 | 0.0432 (8) | 0.0540 (9) | 0.0422 (8) | 0.0039 (7) | 0.0029 (6) | −0.0088 (7) |
| C20 | 0.0404 (8) | 0.0451 (7) | 0.0347 (7) | −0.0003 (7) | −0.0013 (5) | −0.0062 (6) |
| C22 | 0.0544 (9) | 0.0407 (8) | 0.0387 (8) | −0.0025 (7) | 0.0059 (7) | −0.0073 (6) |
| C21 | 0.0426 (9) | 0.0527 (9) | 0.0433 (8) | 0.0036 (7) | 0.0033 (6) | 0.0012 (7) |
| C25 | 0.0375 (7) | 0.0392 (7) | 0.0327 (6) | −0.0048 (6) | 0.0043 (5) | 0.0008 (6) |
| C13 | 0.0534 (9) | 0.0470 (8) | 0.0408 (8) | −0.0052 (8) | 0.0096 (6) | −0.0101 (7) |
| C10 | 0.0401 (8) | 0.0411 (7) | 0.0343 (7) | −0.0047 (6) | 0.0047 (6) | −0.0038 (6) |
| C24 | 0.0503 (9) | 0.0402 (7) | 0.0365 (7) | −0.0025 (7) | 0.0041 (6) | 0.0023 (6) |
| C26 | 0.0413 (8) | 0.0456 (8) | 0.0347 (7) | 0.0025 (6) | 0.0010 (6) | 0.0027 (6) |
| C2 | 0.0575 (10) | 0.0558 (11) | 0.0589 (10) | 0.0108 (9) | −0.0044 (8) | −0.0112 (8) |
| C29 | 0.0414 (8) | 0.0453 (8) | 0.0560 (9) | 0.0021 (7) | 0.0097 (7) | −0.0029 (7) |
| C5 | 0.0422 (8) | 0.0523 (9) | 0.0367 (7) | −0.0031 (7) | −0.0004 (6) | −0.0134 (6) |
| C30 | 0.0356 (8) | 0.0489 (8) | 0.0443 (8) | −0.0037 (6) | 0.0013 (6) | 0.0005 (7) |
| C16 | 0.0461 (9) | 0.0588 (10) | 0.0441 (8) | −0.0067 (7) | −0.0045 (7) | 0.0052 (7) |
| C9 | 0.0509 (9) | 0.0428 (8) | 0.0362 (7) | −0.0029 (7) | 0.0031 (6) | −0.0031 (6) |
| C7 | 0.0532 (9) | 0.0488 (8) | 0.0415 (8) | −0.0052 (7) | 0.0065 (7) | −0.0130 (7) |
| C8 | 0.0595 (10) | 0.0426 (8) | 0.0437 (8) | −0.0021 (7) | 0.0071 (7) | −0.0070 (7) |
| C1 | 0.0498 (9) | 0.0571 (10) | 0.0452 (8) | −0.0007 (7) | 0.0001 (7) | −0.0057 (7) |
| C17 | 0.0622 (10) | 0.0495 (9) | 0.0540 (9) | 0.0070 (8) | −0.0099 (8) | 0.0016 (8) |
| C14 | 0.0404 (8) | 0.0599 (10) | 0.0640 (10) | 0.0072 (8) | 0.0066 (7) | −0.0137 (9) |
| C11 | 0.0481 (9) | 0.0469 (8) | 0.0376 (8) | 0.0080 (7) | −0.0030 (6) | −0.0010 (6) |
| C4 | 0.0454 (9) | 0.0731 (11) | 0.0487 (9) | −0.0022 (8) | 0.0086 (7) | −0.0116 (8) |
| C27 | 0.0444 (9) | 0.0590 (10) | 0.0343 (7) | −0.0092 (7) | −0.0006 (6) | 0.0003 (7) |
| C23 | 0.0557 (9) | 0.0383 (7) | 0.0451 (8) | 0.0016 (7) | 0.0057 (7) | −0.0007 (6) |
| C19 | 0.0438 (9) | 0.0607 (10) | 0.0413 (8) | 0.0030 (7) | 0.0042 (6) | −0.0066 (7) |
| C3 | 0.0488 (10) | 0.0725 (12) | 0.0648 (11) | 0.0149 (9) | 0.0050 (8) | −0.0172 (10) |
| C18 | 0.0538 (10) | 0.0642 (11) | 0.0520 (9) | 0.0178 (8) | −0.0001 (8) | −0.0079 (8) |
| C28 | 0.0553 (10) | 0.0442 (8) | 0.0414 (8) | −0.0111 (7) | 0.0119 (7) | −0.0069 (6) |
| C15 | 0.0358 (8) | 0.0588 (10) | 0.0500 (9) | −0.0003 (7) | −0.0013 (6) | −0.0076 (7) |
| C12 | 0.0525 (10) | 0.0515 (9) | 0.0344 (7) | 0.0001 (7) | −0.0043 (6) | −0.0018 (6) |
| Cl2—C16 | 1.7446 (18) | C26—H26 | 0.9300 |
| Cl1—C1 | 1.7419 (19) | C2—C3 | 1.376 (3) |
| N2—C24 | 1.344 (2) | C2—C1 | 1.384 (2) |
| N2—C25 | 1.4231 (19) | C2—H2 | 0.9300 |
| N2—H16 | 0.886 (9) | C29—C30 | 1.379 (2) |
| O4—C24 | 1.2198 (19) | C29—C28 | 1.387 (2) |
| O3—C23 | 1.435 (2) | C29—H29 | 0.9300 |
| O3—C22 | 1.4388 (19) | C5—C4 | 1.397 (2) |
| O2—C7 | 1.437 (2) | C5—C7 | 1.484 (2) |
| O2—C8 | 1.439 (2) | C30—H30 | 0.9300 |
| O1—C9 | 1.220 (2) | C16—C17 | 1.382 (3) |
| N1—C9 | 1.342 (2) | C9—C8 | 1.503 (2) |
| N1—C10 | 1.4237 (19) | C7—C8 | 1.476 (2) |
| N1—H1 | 0.898 (9) | C7—H7 | 0.9800 |
| C6—C1 | 1.378 (2) | C8—H8 | 0.9800 |
| C6—C5 | 1.394 (2) | C17—C18 | 1.382 (3) |
| C6—H6 | 0.9300 | C17—H17 | 0.9300 |
| C20—C19 | 1.391 (2) | C14—C15 | 1.379 (2) |
| C20—C21 | 1.397 (2) | C14—H14 | 0.9300 |
| C20—C22 | 1.484 (2) | C11—C12 | 1.380 (2) |
| C22—C23 | 1.469 (2) | C11—H11 | 0.9300 |
| C22—H22 | 0.9800 | C4—C3 | 1.380 (3) |
| C21—C16 | 1.376 (2) | C4—H4 | 0.9300 |
| C21—H21 | 0.9300 | C27—C28 | 1.376 (3) |
| C25—C26 | 1.391 (2) | C27—H27 | 0.9300 |
| C25—C30 | 1.393 (2) | C23—H23 | 0.9800 |
| C13—C12 | 1.374 (2) | C19—C18 | 1.377 (3) |
| C13—C14 | 1.388 (2) | C19—H19 | 0.9300 |
| C13—H13 | 0.9300 | C3—H3 | 0.9300 |
| C10—C11 | 1.388 (2) | C18—H18 | 0.9300 |
| C10—C15 | 1.388 (2) | C28—H28 | 0.9300 |
| C24—C23 | 1.506 (2) | C15—H15 | 0.9300 |
| C26—C27 | 1.388 (2) | C12—H12 | 0.9300 |
| C24—N2—C25 | 125.48 (13) | N1—C9—C8 | 116.11 (14) |
| C24—N2—H16 | 119.6 (12) | O2—C7—C8 | 59.18 (11) |
| C25—N2—H16 | 114.7 (12) | O2—C7—C5 | 117.74 (14) |
| C23—O3—C22 | 61.51 (10) | C8—C7—C5 | 124.83 (13) |
| C7—O2—C8 | 61.78 (11) | O2—C7—H7 | 114.5 |
| C9—N1—C10 | 125.66 (13) | C8—C7—H7 | 114.5 |
| C9—N1—H1 | 119.0 (14) | C5—C7—H7 | 114.5 |
| C10—N1—H1 | 115.4 (14) | O2—C8—C7 | 59.04 (11) |
| C1—C6—C5 | 119.83 (15) | O2—C8—C9 | 118.44 (14) |
| C1—C6—H6 | 120.1 | C7—C8—C9 | 122.83 (14) |
| C5—C6—H6 | 120.1 | O2—C8—H8 | 115.0 |
| C19—C20—C21 | 119.18 (15) | C7—C8—H8 | 115.0 |
| C19—C20—C22 | 122.63 (14) | C9—C8—H8 | 115.0 |
| C21—C20—C22 | 118.17 (14) | C6—C1—C2 | 121.74 (17) |
| O3—C22—C23 | 59.11 (10) | C6—C1—Cl1 | 119.94 (14) |
| O3—C22—C20 | 117.82 (13) | C2—C1—Cl1 | 118.31 (14) |
| C23—C22—C20 | 124.43 (13) | C16—C17—C18 | 118.58 (17) |
| O3—C22—H22 | 114.6 | C16—C17—H17 | 120.7 |
| C23—C22—H22 | 114.6 | C18—C17—H17 | 120.7 |
| C20—C22—H22 | 114.6 | C15—C14—C13 | 120.88 (16) |
| C16—C21—C20 | 119.60 (16) | C15—C14—H14 | 119.6 |
| C16—C21—H21 | 120.2 | C13—C14—H14 | 119.6 |
| C20—C21—H21 | 120.2 | C12—C11—C10 | 119.85 (15) |
| C26—C25—C30 | 119.64 (13) | C12—C11—H11 | 120.1 |
| C26—C25—N2 | 121.50 (13) | C10—C11—H11 | 120.1 |
| C30—C25—N2 | 118.84 (13) | C3—C4—C5 | 119.86 (18) |
| C12—C13—C14 | 118.97 (15) | C3—C4—H4 | 120.1 |
| C12—C13—H13 | 120.5 | C5—C4—H4 | 120.1 |
| C14—C13—H13 | 120.5 | C28—C27—C26 | 120.77 (14) |
| C11—C10—C15 | 119.60 (14) | C28—C27—H27 | 119.6 |
| C11—C10—N1 | 121.55 (14) | C26—C27—H27 | 119.6 |
| C15—C10—N1 | 118.84 (13) | O3—C23—C22 | 59.38 (10) |
| O4—C24—N2 | 125.52 (14) | O3—C23—C24 | 118.15 (14) |
| O4—C24—C23 | 119.07 (15) | C22—C23—C24 | 122.42 (13) |
| N2—C24—C23 | 115.39 (14) | O3—C23—H23 | 115.1 |
| C27—C26—C25 | 119.72 (14) | C22—C23—H23 | 115.1 |
| C27—C26—H26 | 120.1 | C24—C23—H23 | 115.1 |
| C25—C26—H26 | 120.1 | C18—C19—C20 | 120.05 (16) |
| C3—C2—C1 | 118.03 (17) | C18—C19—H19 | 120.0 |
| C3—C2—H2 | 121.0 | C20—C19—H19 | 120.0 |
| C1—C2—H2 | 121.0 | C2—C3—C4 | 121.72 (17) |
| C30—C29—C28 | 120.94 (15) | C2—C3—H3 | 119.1 |
| C30—C29—H29 | 119.5 | C4—C3—H3 | 119.1 |
| C28—C29—H29 | 119.5 | C19—C18—C17 | 121.11 (17) |
| C6—C5—C4 | 118.79 (16) | C19—C18—H18 | 119.4 |
| C6—C5—C7 | 119.21 (14) | C17—C18—H18 | 119.4 |
| C4—C5—C7 | 121.95 (16) | C27—C28—C29 | 119.25 (15) |
| C29—C30—C25 | 119.69 (14) | C27—C28—H28 | 120.4 |
| C29—C30—H30 | 120.2 | C29—C28—H28 | 120.4 |
| C25—C30—H30 | 120.2 | C14—C15—C10 | 119.71 (14) |
| C21—C16—C17 | 121.48 (17) | C14—C15—H15 | 120.1 |
| C21—C16—Cl2 | 118.95 (14) | C10—C15—H15 | 120.1 |
| C17—C16—Cl2 | 119.56 (13) | C13—C12—C11 | 120.99 (15) |
| O1—C9—N1 | 125.40 (14) | C13—C12—H12 | 119.5 |
| O1—C9—C8 | 118.47 (14) | C11—C12—H12 | 119.5 |
| C23—O3—C22—C20 | 115.43 (15) | O1—C9—C8—C7 | 106.3 (2) |
| C19—C20—C22—O3 | 3.3 (2) | N1—C9—C8—C7 | −75.2 (2) |
| C21—C20—C22—O3 | −178.56 (13) | C5—C6—C1—C2 | 0.5 (2) |
| C19—C20—C22—C23 | 73.3 (2) | C5—C6—C1—Cl1 | −179.73 (12) |
| C21—C20—C22—C23 | −108.56 (18) | C3—C2—C1—C6 | 0.0 (3) |
| C19—C20—C21—C16 | −0.1 (2) | C3—C2—C1—Cl1 | −179.76 (14) |
| C22—C20—C21—C16 | −178.28 (14) | C21—C16—C17—C18 | 0.4 (2) |
| C24—N2—C25—C26 | 35.2 (2) | Cl2—C16—C17—C18 | −179.17 (13) |
| C24—N2—C25—C30 | −146.60 (14) | C12—C13—C14—C15 | −0.9 (3) |
| C9—N1—C10—C11 | 36.7 (2) | C15—C10—C11—C12 | −0.2 (2) |
| C9—N1—C10—C15 | −144.72 (16) | N1—C10—C11—C12 | 178.34 (15) |
| C25—N2—C24—O4 | −0.2 (2) | C6—C5—C4—C3 | 1.4 (2) |
| C25—N2—C24—C23 | −178.62 (13) | C7—C5—C4—C3 | 178.88 (15) |
| C30—C25—C26—C27 | 0.1 (2) | C25—C26—C27—C28 | −0.4 (2) |
| N2—C25—C26—C27 | 178.31 (14) | C22—O3—C23—C24 | −112.95 (15) |
| C1—C6—C5—C4 | −1.2 (2) | C20—C22—C23—O3 | −104.43 (17) |
| C1—C6—C5—C7 | −178.74 (14) | O3—C22—C23—C24 | 105.87 (17) |
| C28—C29—C30—C25 | −0.3 (2) | C20—C22—C23—C24 | 1.4 (3) |
| C26—C25—C30—C29 | 0.2 (2) | O4—C24—C23—O3 | 173.79 (14) |
| N2—C25—C30—C29 | −178.00 (14) | N2—C24—C23—O3 | −7.7 (2) |
| C20—C21—C16—C17 | −0.2 (2) | O4—C24—C23—C22 | 103.94 (19) |
| C20—C21—C16—Cl2 | 179.30 (12) | N2—C24—C23—C22 | −77.5 (2) |
| C10—N1—C9—O1 | −1.3 (3) | C21—C20—C19—C18 | 0.3 (2) |
| C10—N1—C9—C8 | −179.71 (14) | C22—C20—C19—C18 | 178.39 (14) |
| C8—O2—C7—C5 | 115.96 (15) | C1—C2—C3—C4 | 0.2 (3) |
| C6—C5—C7—O2 | 179.81 (14) | C5—C4—C3—C2 | −0.9 (3) |
| C4—C5—C7—O2 | 2.4 (2) | C20—C19—C18—C17 | −0.2 (3) |
| C6—C5—C7—C8 | −110.02 (19) | C16—C17—C18—C19 | −0.2 (3) |
| C4—C5—C7—C8 | 72.5 (2) | C26—C27—C28—C29 | 0.4 (2) |
| C7—O2—C8—C9 | −113.21 (16) | C30—C29—C28—C27 | 0.0 (2) |
| C5—C7—C8—O2 | −104.19 (18) | C13—C14—C15—C10 | −0.1 (3) |
| O2—C7—C8—C9 | 105.89 (18) | C11—C10—C15—C14 | 0.7 (2) |
| C5—C7—C8—C9 | 1.7 (3) | N1—C10—C15—C14 | −177.90 (16) |
| O1—C9—C8—O2 | 175.98 (14) | C14—C13—C12—C11 | 1.4 (3) |
| N1—C9—C8—O2 | −5.5 (2) | C10—C11—C12—C13 | −0.9 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1i | 0.90 (1) | 2.41 (1) | 3.2287 (15) | 152 |
| N2—H16···O4i | 0.89 (1) | 2.40 (1) | 3.2357 (16) | 156 |
| C4—H4···O1i | 0.93 | 2.49 | 3.388 (2) | 162 |
| C15—H15···O1i | 0.93 | 2.58 | 3.259 (2) | 130 |
| C19—H19···O4i | 0.93 | 2.59 | 3.5087 (19) | 168 |
| Symmetry codes: (i) x+1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O1i | 0.90 (1) | 2.41 (1) | 3.2287 (15) | 152 |
| N2—H16···O4i | 0.89 (1) | 2.40 (1) | 3.2357 (16) | 156 |
| C4—H4···O1i | 0.93 | 2.49 | 3.388 (2) | 162 |
| C15—H15···O1i | 0.93 | 2.58 | 3.259 (2) | 130 |
| C19—H19···O4i | 0.93 | 2.59 | 3.5087 (19) | 168 |
| Symmetry codes: (i) x+1, y, z. |
The diffraction measurements were made at the Centre for Testing and Analysis, Sichuan university. We acknowledge financial support from China West Normal University.
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Epoxides are particularly versatile synthetic intermediates which can readily be converted into a wide range of polyfunctional compounds (Imashiro et al. 2004; Porter et al. 2000; Shing et al. 2006). A useful method for the synthesis of α, β-epoxy carbonyl compounds and related compounds is the Darzens condensation between a carbonyl compound and α-halo-carbonyl compound (Zhu et al. 1995). We report herein the crystal structure of the title compound.
The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The asymmetric unit of the title compound consists of two crystallographically independent molecules (Fig. 1) each of which adopts a cis configuration about the epoxides ring. The dihedral angle between the C1—C6 and C10—C15 ring is 82.14 (5)° and that between C16–21 and C25–30 phenyl ring is 84.15 (4)°. The dihedral angles between the epoxy ring and chlorophenyl rings are essentially identical for the two independent molecules [62.50 (9)° and 62.67 (9)°]. The crystal packing is stabilized by N—H···0 and C—H···0 hydrogen bonding (Table 1).