Acta Cryst. (2008). E64, o2103 [ doi:10.1107/S1600536808031930 ]
There are two independent molecules of the title compound, C15H8Cl3NO, in the asymmetric unit. Both form inversion dimers via pairs of hydrazide-carbonyl N-H
O hydrogen bonds.
The title compound was synthesized by the condensation of 2,6-dichlorobenzaldehyde (1 mmol) with 5-chloro-oxindole (1 mmol) in ethanol (10 ml) in the presence of catalytic amount of piperidine (0.1 mmol). After refluxing for 3 hrs, the reaction mixture was left to stand overnight. The resulting crude solid was filtered, washed with cold ethanol (10 ml) and dried. Orange colored single crystals of the compound suitable for X-ray structure determination were recrystallized from ethanol.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008).
![[Figure 1]](./jh2068fig1thm.gif)
| Fig. 1. A view of one of the independent molecules with displacement ellipsoids drawn at the 40% probability level. H atoms are presented as open circles with arbitrary radii. Atoms of another independent molecule were labeled as N21 C22 O22 C23 through C35 C36 Cl36. |
![[Figure 2]](./jh2068fig2thm.gif)
| Fig. 2. A unit cell packing view of the title compound. Dash lines indicate hydrogen bonds. For clarity, H atoms not involved in H-bonding were omitted. |
| C15H8Cl3NO | Z = 4 |
| Mr = 324.57 | F(000) = 656 |
| Triclinic, P1 | Dx = 1.568 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.0809 (6) Å | Cell parameters from 9259 reflections |
| b = 13.4944 (11) Å | θ = 2.6–28.2° |
| c = 14.3698 (16) Å | µ = 0.66 mm−1 |
| α = 63.116 (1)° | T = 296 K |
| β = 82.973 (2)° | Rod, orange |
| γ = 80.162 (1)° | 0.39 × 0.28 × 0.21 mm |
| V = 1375.3 (2) Å3 |
| Bruker APEX CCD area-detector diffractometer | 6438 independent reflections |
| Radiation source: fine-focus sealed tube | 5292 reflections with I > 2σ(I) |
| graphite | Rint = 0.028 |
| Detector resolution: 83.33 pixels mm-1 | θmax = 28.2°, θmin = 1.6° |
| φ and ω scans | h = −10→10 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −17→17 |
| Tmin = 0.785, Tmax = 0.874 | l = −18→18 |
| 16659 measured reflections |
| 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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.158 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0786P)2 + 0.7214P] where P = (Fo2 + 2Fc2)/3 |
| 6438 reflections | (Δ/σ)max < 0.001 |
| 361 parameters | Δρmax = 0.53 e Å−3 |
| 0 restraints | Δρmin = −0.39 e Å−3 |
| C15H8Cl3NO | γ = 80.162 (1)° |
| Mr = 324.57 | V = 1375.3 (2) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 8.0809 (6) Å | Mo Kα radiation |
| b = 13.4944 (11) Å | µ = 0.66 mm−1 |
| c = 14.3698 (16) Å | T = 296 K |
| α = 63.116 (1)° | 0.39 × 0.28 × 0.21 mm |
| β = 82.973 (2)° |
| Bruker APEX CCD area-detector diffractometer | 6438 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5292 reflections with I > 2σ(I) |
| Tmin = 0.785, Tmax = 0.874 | Rint = 0.028 |
| 16659 measured reflections | θmax = 28.2° |
| R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
| wR(F2) = 0.158 | Δρmax = 0.53 e Å−3 |
| S = 1.08 | Δρmin = −0.39 e Å−3 |
| 6438 reflections | Absolute structure: ? |
| 361 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. 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. |
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 | ||
| N1 | 0.8654 (3) | 0.07885 (18) | 0.38440 (16) | 0.0441 (5) | |
| H1 | 0.8834 | 0.0942 | 0.4340 | 0.053* | |
| C2 | 0.9186 (3) | −0.0212 (2) | 0.38197 (19) | 0.0419 (5) | |
| O2 | 1.0019 (3) | −0.10122 (17) | 0.44698 (16) | 0.0564 (5) | |
| C3 | 0.8546 (3) | −0.0123 (2) | 0.28386 (18) | 0.0366 (5) | |
| C4 | 0.6911 (3) | 0.1609 (2) | 0.13832 (19) | 0.0407 (5) | |
| H4 | 0.6838 | 0.1275 | 0.0950 | 0.049* | |
| C5 | 0.6255 (4) | 0.2711 (2) | 0.1105 (2) | 0.0465 (6) | |
| Cl5 | 0.53114 (14) | 0.34756 (7) | −0.00817 (7) | 0.0780 (3) | |
| C6 | 0.6336 (4) | 0.3220 (2) | 0.1745 (2) | 0.0532 (7) | |
| H6 | 0.5871 | 0.3964 | 0.1540 | 0.064* | |
| C7 | 0.7100 (4) | 0.2633 (2) | 0.2680 (2) | 0.0497 (6) | |
| H7 | 0.7157 | 0.2968 | 0.3114 | 0.060* | |
| C8 | 0.7778 (3) | 0.1536 (2) | 0.29584 (19) | 0.0399 (5) | |
| C9 | 0.7679 (3) | 0.10133 (19) | 0.23239 (18) | 0.0355 (5) | |
| C10 | 0.8876 (3) | −0.0984 (2) | 0.26019 (19) | 0.0396 (5) | |
| H10 | 0.9537 | −0.1608 | 0.3067 | 0.047* | |
| C11 | 0.8348 (3) | −0.10953 (18) | 0.17102 (18) | 0.0358 (5) | |
| C12 | 0.6685 (3) | −0.1043 (2) | 0.15124 (19) | 0.0405 (5) | |
| Cl12 | 0.50744 (9) | −0.07520 (7) | 0.23006 (6) | 0.0552 (2) | |
| C13 | 0.6254 (4) | −0.1275 (3) | 0.0740 (2) | 0.0534 (7) | |
| H13 | 0.5128 | −0.1237 | 0.0632 | 0.064* | |
| C14 | 0.7491 (4) | −0.1563 (3) | 0.0131 (2) | 0.0614 (8) | |
| H14 | 0.7202 | −0.1718 | −0.0393 | 0.074* | |
| C15 | 0.9149 (4) | −0.1623 (3) | 0.0288 (2) | 0.0559 (7) | |
| H15 | 0.9991 | −0.1817 | −0.0124 | 0.067* | |
| C16 | 0.9551 (3) | −0.1393 (2) | 0.1065 (2) | 0.0426 (5) | |
| Cl16 | 1.16558 (10) | −0.14706 (9) | 0.12559 (7) | 0.0693 (3) | |
| N21 | 0.3669 (3) | 0.12638 (17) | 0.40122 (17) | 0.0442 (5) | |
| H21 | 0.3913 | 0.0600 | 0.4054 | 0.053* | |
| C22 | 0.4168 (4) | 0.1590 (2) | 0.4684 (2) | 0.0441 (6) | |
| O22 | 0.5053 (3) | 0.10166 (16) | 0.54222 (16) | 0.0602 (6) | |
| C23 | 0.3436 (3) | 0.28014 (19) | 0.43404 (19) | 0.0411 (5) | |
| C24 | 0.1590 (4) | 0.4078 (2) | 0.2758 (2) | 0.0457 (6) | |
| H24 | 0.1457 | 0.4719 | 0.2863 | 0.055* | |
| C25 | 0.0844 (4) | 0.4072 (2) | 0.1947 (2) | 0.0522 (7) | |
| Cl25 | −0.04299 (14) | 0.52723 (8) | 0.11626 (7) | 0.0819 (3) | |
| C26 | 0.1041 (4) | 0.3135 (3) | 0.1766 (2) | 0.0560 (7) | |
| H26 | 0.0546 | 0.3164 | 0.1201 | 0.067* | |
| C27 | 0.1976 (4) | 0.2155 (2) | 0.2423 (2) | 0.0517 (7) | |
| H27 | 0.2107 | 0.1517 | 0.2313 | 0.062* | |
| C28 | 0.2706 (3) | 0.2145 (2) | 0.32410 (19) | 0.0412 (5) | |
| C29 | 0.2540 (3) | 0.3105 (2) | 0.34098 (19) | 0.0399 (5) | |
| C30 | 0.3666 (3) | 0.3334 (2) | 0.48909 (19) | 0.0433 (6) | |
| H30 | 0.4207 | 0.2894 | 0.5511 | 0.052* | |
| C31 | 0.3183 (3) | 0.4519 (2) | 0.46532 (19) | 0.0414 (6) | |
| C32 | 0.3765 (4) | 0.5398 (2) | 0.3753 (2) | 0.0451 (6) | |
| Cl32 | 0.50911 (12) | 0.51303 (6) | 0.28279 (6) | 0.0612 (2) | |
| C33 | 0.3398 (4) | 0.6498 (2) | 0.3583 (2) | 0.0524 (7) | |
| H33 | 0.3818 | 0.7061 | 0.2979 | 0.063* | |
| C34 | 0.2410 (4) | 0.6762 (2) | 0.4306 (3) | 0.0569 (8) | |
| H34 | 0.2143 | 0.7507 | 0.4185 | 0.068* | |
| C35 | 0.1809 (4) | 0.5927 (2) | 0.5213 (3) | 0.0562 (7) | |
| H35 | 0.1142 | 0.6102 | 0.5707 | 0.067* | |
| C36 | 0.2217 (4) | 0.4827 (2) | 0.5371 (2) | 0.0459 (6) | |
| Cl36 | 0.14997 (12) | 0.37906 (7) | 0.65309 (6) | 0.0650 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0581 (13) | 0.0448 (12) | 0.0374 (11) | 0.0013 (10) | −0.0110 (9) | −0.0257 (9) |
| C2 | 0.0491 (14) | 0.0430 (13) | 0.0377 (12) | 0.0000 (11) | −0.0068 (10) | −0.0222 (11) |
| O2 | 0.0766 (14) | 0.0497 (11) | 0.0483 (11) | 0.0148 (10) | −0.0283 (10) | −0.0281 (9) |
| C3 | 0.0419 (12) | 0.0388 (12) | 0.0302 (11) | −0.0033 (10) | −0.0057 (9) | −0.0157 (10) |
| C4 | 0.0504 (14) | 0.0393 (13) | 0.0345 (12) | −0.0049 (10) | −0.0047 (10) | −0.0177 (10) |
| C5 | 0.0551 (15) | 0.0406 (13) | 0.0372 (13) | −0.0008 (11) | −0.0103 (11) | −0.0113 (11) |
| Cl5 | 0.1182 (8) | 0.0484 (4) | 0.0584 (5) | 0.0115 (4) | −0.0432 (5) | −0.0139 (4) |
| C6 | 0.0665 (18) | 0.0371 (13) | 0.0557 (16) | 0.0052 (12) | −0.0096 (14) | −0.0228 (12) |
| C7 | 0.0644 (17) | 0.0419 (14) | 0.0500 (15) | 0.0009 (12) | −0.0068 (13) | −0.0284 (12) |
| C8 | 0.0436 (13) | 0.0435 (13) | 0.0361 (12) | −0.0038 (10) | −0.0026 (10) | −0.0212 (11) |
| C9 | 0.0399 (12) | 0.0341 (11) | 0.0340 (11) | −0.0038 (9) | −0.0019 (9) | −0.0166 (9) |
| C10 | 0.0469 (13) | 0.0360 (12) | 0.0351 (12) | 0.0021 (10) | −0.0104 (10) | −0.0156 (10) |
| C11 | 0.0456 (13) | 0.0287 (11) | 0.0329 (11) | −0.0020 (9) | −0.0061 (9) | −0.0133 (9) |
| C12 | 0.0447 (13) | 0.0397 (12) | 0.0381 (12) | −0.0058 (10) | −0.0012 (10) | −0.0182 (10) |
| Cl12 | 0.0485 (4) | 0.0678 (5) | 0.0578 (4) | −0.0124 (3) | 0.0077 (3) | −0.0361 (4) |
| C13 | 0.0503 (15) | 0.0683 (19) | 0.0521 (16) | −0.0161 (14) | −0.0043 (13) | −0.0325 (15) |
| C14 | 0.071 (2) | 0.082 (2) | 0.0520 (17) | −0.0184 (17) | −0.0036 (14) | −0.0451 (17) |
| C15 | 0.0613 (18) | 0.0677 (19) | 0.0483 (15) | −0.0050 (14) | 0.0028 (13) | −0.0364 (15) |
| C16 | 0.0408 (13) | 0.0451 (14) | 0.0415 (13) | −0.0020 (10) | −0.0053 (10) | −0.0193 (11) |
| Cl16 | 0.0433 (4) | 0.1032 (7) | 0.0631 (5) | 0.0028 (4) | −0.0077 (3) | −0.0411 (5) |
| N21 | 0.0630 (14) | 0.0297 (10) | 0.0405 (11) | −0.0003 (9) | −0.0007 (10) | −0.0185 (9) |
| C22 | 0.0616 (16) | 0.0313 (12) | 0.0376 (13) | −0.0003 (11) | 0.0006 (11) | −0.0164 (10) |
| O22 | 0.0968 (16) | 0.0346 (9) | 0.0476 (11) | 0.0152 (10) | −0.0217 (11) | −0.0203 (9) |
| C23 | 0.0538 (14) | 0.0291 (11) | 0.0378 (12) | 0.0022 (10) | −0.0015 (11) | −0.0153 (10) |
| C24 | 0.0586 (16) | 0.0361 (13) | 0.0421 (13) | 0.0010 (11) | −0.0035 (12) | −0.0192 (11) |
| C25 | 0.0617 (17) | 0.0485 (15) | 0.0395 (14) | 0.0050 (13) | −0.0093 (12) | −0.0160 (12) |
| Cl25 | 0.1096 (8) | 0.0673 (5) | 0.0607 (5) | 0.0255 (5) | −0.0378 (5) | −0.0257 (4) |
| C26 | 0.0694 (19) | 0.0619 (18) | 0.0438 (15) | −0.0053 (15) | −0.0094 (13) | −0.0290 (14) |
| C27 | 0.0702 (19) | 0.0472 (15) | 0.0478 (15) | −0.0081 (13) | −0.0006 (13) | −0.0303 (13) |
| C28 | 0.0498 (14) | 0.0355 (12) | 0.0387 (12) | −0.0042 (10) | 0.0040 (10) | −0.0185 (10) |
| C29 | 0.0515 (14) | 0.0366 (12) | 0.0337 (12) | −0.0051 (10) | −0.0003 (10) | −0.0178 (10) |
| C30 | 0.0601 (16) | 0.0306 (12) | 0.0365 (12) | 0.0034 (10) | −0.0111 (11) | −0.0137 (10) |
| C31 | 0.0559 (15) | 0.0325 (12) | 0.0390 (12) | 0.0039 (10) | −0.0152 (11) | −0.0187 (10) |
| C32 | 0.0595 (16) | 0.0380 (13) | 0.0397 (13) | 0.0004 (11) | −0.0133 (11) | −0.0184 (11) |
| Cl32 | 0.0888 (6) | 0.0524 (4) | 0.0433 (4) | −0.0095 (4) | 0.0018 (3) | −0.0231 (3) |
| C33 | 0.0693 (18) | 0.0329 (13) | 0.0535 (16) | −0.0012 (12) | −0.0223 (14) | −0.0148 (12) |
| C34 | 0.0660 (19) | 0.0317 (13) | 0.077 (2) | 0.0092 (12) | −0.0240 (16) | −0.0275 (14) |
| C35 | 0.0593 (17) | 0.0475 (15) | 0.071 (2) | 0.0038 (13) | −0.0068 (15) | −0.0374 (15) |
| C36 | 0.0572 (16) | 0.0380 (13) | 0.0453 (14) | −0.0020 (11) | −0.0082 (12) | −0.0210 (11) |
| Cl36 | 0.0868 (6) | 0.0549 (4) | 0.0561 (4) | −0.0154 (4) | 0.0106 (4) | −0.0283 (4) |
| N1—C2 | 1.360 (3) | N21—C22 | 1.352 (3) |
| N1—C8 | 1.398 (3) | N21—C28 | 1.397 (3) |
| N1—H1 | 0.8600 | N21—H21 | 0.8600 |
| C2—O2 | 1.219 (3) | C22—O22 | 1.220 (3) |
| C2—C3 | 1.508 (3) | C22—C23 | 1.509 (3) |
| C3—C10 | 1.329 (3) | C23—C30 | 1.331 (3) |
| C3—C9 | 1.457 (3) | C23—C29 | 1.456 (4) |
| C4—C5 | 1.378 (4) | C24—C25 | 1.378 (4) |
| C4—C9 | 1.383 (3) | C24—C29 | 1.382 (4) |
| C4—H4 | 0.9300 | C24—H24 | 0.9300 |
| C5—C6 | 1.387 (4) | C25—C26 | 1.383 (4) |
| C5—Cl5 | 1.736 (3) | C25—Cl25 | 1.737 (3) |
| C6—C7 | 1.373 (4) | C26—C27 | 1.385 (4) |
| C6—H6 | 0.9300 | C26—H26 | 0.9300 |
| C7—C8 | 1.375 (4) | C27—C28 | 1.372 (4) |
| C7—H7 | 0.9300 | C27—H27 | 0.9300 |
| C8—C9 | 1.397 (3) | C28—C29 | 1.404 (3) |
| C10—C11 | 1.475 (3) | C30—C31 | 1.467 (3) |
| C10—H10 | 0.9300 | C30—H30 | 0.9300 |
| C11—C12 | 1.391 (4) | C31—C36 | 1.388 (4) |
| C11—C16 | 1.395 (3) | C31—C32 | 1.398 (4) |
| C12—C13 | 1.378 (4) | C32—C33 | 1.374 (4) |
| C12—Cl12 | 1.732 (3) | C32—Cl32 | 1.733 (3) |
| C13—C14 | 1.370 (4) | C33—C34 | 1.370 (4) |
| C13—H13 | 0.9300 | C33—H33 | 0.9300 |
| C14—C15 | 1.369 (5) | C34—C35 | 1.381 (5) |
| C14—H14 | 0.9300 | C34—H34 | 0.9300 |
| C15—C16 | 1.373 (4) | C35—C36 | 1.382 (4) |
| C15—H15 | 0.9300 | C35—H35 | 0.9300 |
| C16—Cl16 | 1.734 (3) | C36—Cl36 | 1.733 (3) |
| C2—N1—C8 | 111.2 (2) | C22—N21—C28 | 111.3 (2) |
| C2—N1—H1 | 124.4 | C22—N21—H21 | 124.4 |
| C8—N1—H1 | 124.4 | C28—N21—H21 | 124.4 |
| O2—C2—N1 | 125.9 (2) | O22—C22—N21 | 126.6 (2) |
| O2—C2—C3 | 127.6 (2) | O22—C22—C23 | 126.5 (2) |
| N1—C2—C3 | 106.4 (2) | N21—C22—C23 | 106.9 (2) |
| C10—C3—C9 | 134.2 (2) | C30—C23—C29 | 134.6 (2) |
| C10—C3—C2 | 120.2 (2) | C30—C23—C22 | 120.1 (2) |
| C9—C3—C2 | 105.53 (19) | C29—C23—C22 | 105.2 (2) |
| C5—C4—C9 | 118.1 (2) | C25—C24—C29 | 118.2 (2) |
| C5—C4—H4 | 120.9 | C25—C24—H24 | 120.9 |
| C9—C4—H4 | 120.9 | C29—C24—H24 | 120.9 |
| C4—C5—C6 | 121.8 (2) | C24—C25—C26 | 122.0 (3) |
| C4—C5—Cl5 | 118.7 (2) | C24—C25—Cl25 | 118.4 (2) |
| C6—C5—Cl5 | 119.6 (2) | C26—C25—Cl25 | 119.6 (2) |
| C7—C6—C5 | 120.3 (2) | C25—C26—C27 | 120.0 (3) |
| C7—C6—H6 | 119.8 | C25—C26—H26 | 120.0 |
| C5—C6—H6 | 119.8 | C27—C26—H26 | 120.0 |
| C6—C7—C8 | 118.4 (2) | C28—C27—C26 | 118.5 (2) |
| C6—C7—H7 | 120.8 | C28—C27—H27 | 120.8 |
| C8—C7—H7 | 120.8 | C26—C27—H27 | 120.8 |
| C7—C8—C9 | 121.6 (2) | C27—C28—N21 | 129.1 (2) |
| C7—C8—N1 | 128.7 (2) | C27—C28—C29 | 121.5 (2) |
| C9—C8—N1 | 109.7 (2) | N21—C28—C29 | 109.5 (2) |
| C4—C9—C8 | 119.8 (2) | C24—C29—C28 | 119.8 (2) |
| C4—C9—C3 | 133.0 (2) | C24—C29—C23 | 133.0 (2) |
| C8—C9—C3 | 107.1 (2) | C28—C29—C23 | 107.2 (2) |
| C3—C10—C11 | 129.5 (2) | C23—C30—C31 | 128.8 (2) |
| C3—C10—H10 | 115.3 | C23—C30—H30 | 115.6 |
| C11—C10—H10 | 115.3 | C31—C30—H30 | 115.6 |
| C12—C11—C16 | 115.2 (2) | C36—C31—C32 | 115.6 (2) |
| C12—C11—C10 | 124.4 (2) | C36—C31—C30 | 120.8 (2) |
| C16—C11—C10 | 120.0 (2) | C32—C31—C30 | 123.4 (2) |
| C13—C12—C11 | 122.5 (2) | C33—C32—C31 | 122.4 (3) |
| C13—C12—Cl12 | 117.7 (2) | C33—C32—Cl32 | 116.8 (2) |
| C11—C12—Cl12 | 119.70 (19) | C31—C32—Cl32 | 120.63 (19) |
| C14—C13—C12 | 119.7 (3) | C34—C33—C32 | 119.7 (3) |
| C14—C13—H13 | 120.1 | C34—C33—H33 | 120.1 |
| C12—C13—H13 | 120.1 | C32—C33—H33 | 120.1 |
| C15—C14—C13 | 120.3 (3) | C33—C34—C35 | 120.4 (2) |
| C15—C14—H14 | 119.9 | C33—C34—H34 | 119.8 |
| C13—C14—H14 | 119.9 | C35—C34—H34 | 119.8 |
| C14—C15—C16 | 119.0 (3) | C34—C35—C36 | 118.7 (3) |
| C14—C15—H15 | 120.5 | C34—C35—H35 | 120.7 |
| C16—C15—H15 | 120.5 | C36—C35—H35 | 120.7 |
| C15—C16—C11 | 123.3 (2) | C35—C36—C31 | 123.2 (3) |
| C15—C16—Cl16 | 118.6 (2) | C35—C36—Cl36 | 117.9 (2) |
| C11—C16—Cl16 | 118.14 (19) | C31—C36—Cl36 | 118.92 (19) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O2i | 0.86 | 2.09 | 2.919 (3) | 162 |
| N21—H21···O22ii | 0.86 | 2.02 | 2.838 (3) | 159 |
| Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O2i | 0.86 | 2.09 | 2.919 (3) | 162 |
| N21—H21···O22ii | 0.86 | 2.02 | 2.838 (3) | 159 |
| Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1. |
The authors are grateful for grants from the Welch Foundation (grant No. N-118) and DARPA (grant No. HR0011-06-1-0032).
Ali, H. M., Laila, M., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, o921.
Andreani, A., Burnelli, S., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Varoli, L. & Kunkel, M. W. (2006). J. Med. Chem. 49, 6922–6924.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
De, A. (2008). Acta Cryst. E64, o562.
D'Mello et al. (2005). [Please provide full details for missing reference]
Gayathri, D., Velmurugan, D., Shanthi, G., Perumal, P. T. & Ravikumar, K. (2008). Acta Cryst. E64, o501–o502.
Johnson, K., Liu, L., Majdzadeh, N., Chavez, C., Chin, P. C., Morrison, B., Wang, L., Park, J., Chugh, P., Chen, H. & D'Mello, S. R. (2005). J. Neurochem. 93, 538–548. [Reference not cited - may it be removed?]
Li, S., Tran, N., Tang, F., App, H., Hirth, P., McMahon, G. & Tang, C. (1998). J. Med. Chem. 41, 2588–2603. [Reference not cited - may it be removed?]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Sun et al. (1998). [Please provide full details for missing reference]
Westrip, S. P. (2008). publCIF. In preparation.
3-Substituted indoline-2-ones have well recognized pharmacological activities, including antitumor properties (Andreani et al., 2006), receptor tyrosine kinase (RTK) inhibitors (Sun et al., 1998) and neuroprotective agents (D'Mello et al., 2005). To study their neuroprotective activity, a series of 3- and 3,5-substituted indoline-2-one derivatives have been synthesized and crystallized in our laboratory. As part of our studies on structure–activity relationships of 3-substituted indoline-2-ones and the importance of substituent at the 5-postion, the title compound was synthesized and its crystal structure was carried out. The study found the title compound adopted an E conformation in the structure (Fig. 1) and that converted into a mixture of E and Z isomers in DMSO-d6 solution. As expected, the substituent, O2, Cl5, and C10, lie essentially in the plane of the indole ring. The indolyl plane with that of phenyl are twisted, with the dihedral angles between the rings are 62.16 (10), 63.06 (6)°, respectively, for each independent molecule. It's similar to other indolin-2-one compounds (Gayathri et al., 2008; Ali et al., 2008; De, 2008) containing intermolecular hydrazide–carbonyl N—H···O hydrogen bonds. The H-bonds link two inverted molecules and a dimer is formed (Table 1).