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organic compounds
The title compound, C16H9Cl2NO3, contains two planar ring systems and, in the crystal structure, there are intermolecular π–π stacking interactions between neighboring benzene rings of the phthalimide groups.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001412/wn6209sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001412/wn6209Isup2.hkl |
CCDC reference: 234918
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.002 Å - R factor = 0.037
- wR factor = 0.111
- Data-to-parameter ratio = 13.0
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.002 ÅcheckCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1-(2,4-Dichlorophenyl)-2-phthalimidoethanone top
Crystal data top
| C16H9Cl2NO3 | F(000) = 680 |
| Mr = 334.14 | Dx = 1.541 Mg m−3 |
| Monoclinic, P21/c | Melting point: 363 K |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 12.9211 (5) Å | Cell parameters from 684 reflections |
| b = 14.0305 (5) Å | θ = 2.4–21.4° |
| c = 8.0488 (3) Å | µ = 0.46 mm−1 |
| β = 99.341 (2)° | T = 273 K |
| V = 1439.81 (9) Å3 | Block, colorless |
| Z = 4 | 0.39 × 0.34 × 0.22 mm |
Data collection top
| Bruker SMART APEX CCD area-detector diffractometer | 2592 independent reflections |
| Radiation source: fine-focus sealed tube | 2226 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.018 |
| φ and ω scans | θmax = 25.2°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −15→15 |
| Tmin = 0.840, Tmax = 0.905 | k = −16→16 |
| 7571 measured reflections | l = −8→9 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.111 | H-atom parameters constrained |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0658P)2 + 0.1986P] where P = (Fo2 + 2Fc2)/3 |
| 2592 reflections | (Δ/σ)max < 0.001 |
| 199 parameters | Δρmax = 0.31 e Å−3 |
| 0 restraints | Δρmin = −0.28 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 | ||
| Cl1 | 0.34280 (4) | 0.62955 (4) | 0.70746 (7) | 0.0711 (2) | |
| Cl2 | 0.47616 (4) | 0.60202 (5) | 0.12180 (6) | 0.0684 (2) | |
| O1 | 0.69916 (11) | 0.63367 (12) | 0.17402 (19) | 0.0708 (4) | |
| O2 | 0.92807 (11) | 0.44565 (9) | 0.34617 (19) | 0.0612 (4) | |
| O3 | 0.90678 (11) | 0.76832 (9) | 0.2890 (2) | 0.0635 (4) | |
| N1 | 0.89656 (11) | 0.60740 (10) | 0.3349 (2) | 0.0481 (4) | |
| C1 | 0.44821 (15) | 0.63029 (13) | 0.5982 (2) | 0.0498 (4) | |
| C2 | 0.42751 (14) | 0.61993 (12) | 0.4261 (2) | 0.0505 (5) | |
| H2 | 0.3588 | 0.6138 | 0.3709 | 0.061* | |
| C3 | 0.51012 (14) | 0.61875 (12) | 0.3360 (2) | 0.0452 (4) | |
| C4 | 0.61423 (13) | 0.62786 (11) | 0.4166 (2) | 0.0425 (4) | |
| C5 | 0.62980 (15) | 0.63873 (13) | 0.5910 (2) | 0.0506 (4) | |
| H5 | 0.6981 | 0.6456 | 0.6475 | 0.061* | |
| C6 | 0.54909 (16) | 0.63989 (13) | 0.6840 (3) | 0.0540 (5) | |
| H6 | 0.5622 | 0.6469 | 0.8004 | 0.065* | |
| C7 | 0.70605 (14) | 0.62497 (12) | 0.3249 (2) | 0.0452 (4) | |
| C8 | 0.81284 (14) | 0.60999 (14) | 0.4327 (3) | 0.0513 (5) | |
| H8A | 0.8259 | 0.6611 | 0.5145 | 0.062* | |
| H8B | 0.8121 | 0.5505 | 0.4940 | 0.062* | |
| C9 | 0.94004 (14) | 0.68880 (12) | 0.2766 (2) | 0.0476 (4) | |
| C10 | 0.95016 (13) | 0.52474 (12) | 0.3039 (2) | 0.0459 (4) | |
| C11 | 1.03633 (13) | 0.55634 (12) | 0.2152 (2) | 0.0439 (4) | |
| C12 | 1.11199 (14) | 0.50478 (13) | 0.1527 (2) | 0.0512 (4) | |
| H12 | 1.1147 | 0.4387 | 0.1614 | 0.061* | |
| C13 | 1.18374 (15) | 0.55455 (15) | 0.0767 (3) | 0.0577 (5) | |
| H13 | 1.2358 | 0.5214 | 0.0336 | 0.069* | |
| C14 | 1.17964 (15) | 0.65298 (15) | 0.0634 (3) | 0.0605 (5) | |
| H14 | 1.2294 | 0.6847 | 0.0124 | 0.073* | |
| C15 | 1.10278 (14) | 0.70509 (14) | 0.1247 (3) | 0.0553 (5) | |
| H15 | 1.0998 | 0.7711 | 0.1152 | 0.066* | |
| C16 | 1.03106 (13) | 0.65534 (12) | 0.2002 (2) | 0.0447 (4) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0604 (3) | 0.0939 (4) | 0.0652 (4) | 0.0076 (3) | 0.0286 (3) | 0.0004 (3) |
| Cl2 | 0.0532 (3) | 0.1094 (5) | 0.0411 (3) | −0.0062 (3) | 0.0034 (2) | −0.0079 (3) |
| O1 | 0.0519 (8) | 0.1144 (12) | 0.0474 (9) | 0.0077 (8) | 0.0118 (6) | 0.0079 (8) |
| O2 | 0.0648 (9) | 0.0453 (7) | 0.0741 (10) | −0.0072 (6) | 0.0126 (7) | 0.0057 (6) |
| O3 | 0.0638 (9) | 0.0462 (7) | 0.0830 (10) | 0.0087 (6) | 0.0194 (7) | 0.0026 (7) |
| N1 | 0.0395 (8) | 0.0491 (8) | 0.0557 (9) | 0.0007 (6) | 0.0078 (7) | 0.0078 (7) |
| C1 | 0.0523 (10) | 0.0495 (10) | 0.0503 (11) | 0.0049 (8) | 0.0166 (9) | −0.0005 (8) |
| C2 | 0.0423 (9) | 0.0569 (11) | 0.0520 (11) | 0.0022 (8) | 0.0071 (8) | −0.0013 (8) |
| C3 | 0.0472 (10) | 0.0472 (9) | 0.0409 (9) | 0.0029 (7) | 0.0059 (8) | −0.0005 (7) |
| C4 | 0.0441 (9) | 0.0411 (8) | 0.0422 (10) | 0.0023 (7) | 0.0065 (7) | −0.0010 (7) |
| C5 | 0.0479 (10) | 0.0579 (10) | 0.0455 (10) | 0.0030 (8) | 0.0056 (8) | −0.0030 (8) |
| C6 | 0.0593 (11) | 0.0604 (11) | 0.0435 (10) | 0.0021 (9) | 0.0120 (9) | −0.0064 (8) |
| C7 | 0.0446 (9) | 0.0465 (9) | 0.0445 (10) | 0.0024 (7) | 0.0072 (8) | −0.0001 (7) |
| C8 | 0.0439 (10) | 0.0595 (11) | 0.0505 (11) | −0.0010 (8) | 0.0073 (8) | 0.0060 (8) |
| C9 | 0.0433 (9) | 0.0459 (9) | 0.0513 (10) | 0.0003 (8) | 0.0011 (8) | 0.0033 (8) |
| C10 | 0.0430 (9) | 0.0456 (9) | 0.0458 (10) | −0.0012 (7) | −0.0026 (7) | 0.0023 (8) |
| C11 | 0.0400 (9) | 0.0462 (9) | 0.0424 (9) | −0.0016 (7) | −0.0029 (7) | −0.0004 (7) |
| C12 | 0.0478 (10) | 0.0498 (10) | 0.0525 (11) | 0.0045 (8) | −0.0020 (8) | −0.0046 (8) |
| C13 | 0.0472 (10) | 0.0733 (13) | 0.0524 (11) | 0.0062 (9) | 0.0075 (9) | −0.0100 (10) |
| C14 | 0.0510 (11) | 0.0718 (13) | 0.0612 (12) | −0.0080 (10) | 0.0165 (9) | 0.0034 (10) |
| C15 | 0.0540 (11) | 0.0507 (10) | 0.0611 (12) | −0.0049 (8) | 0.0094 (9) | 0.0049 (9) |
| C16 | 0.0404 (9) | 0.0471 (9) | 0.0447 (10) | 0.0000 (7) | 0.0011 (7) | 0.0029 (8) |
Geometric parameters (Å, º) top
| Cl1—C1 | 1.7371 (18) | C6—H6 | 0.9300 |
| Cl2—C3 | 1.7243 (19) | C7—C8 | 1.521 (3) |
| O1—C7 | 1.209 (2) | C8—H8A | 0.9700 |
| O2—C10 | 1.208 (2) | C8—H8B | 0.9700 |
| O3—C9 | 1.205 (2) | C9—C16 | 1.489 (2) |
| N1—C9 | 1.388 (2) | C10—C11 | 1.485 (2) |
| N1—C10 | 1.394 (2) | C11—C12 | 1.375 (2) |
| N1—C8 | 1.438 (2) | C11—C16 | 1.395 (2) |
| C1—C2 | 1.375 (3) | C12—C13 | 1.381 (3) |
| C1—C6 | 1.379 (3) | C12—H12 | 0.9300 |
| C2—C3 | 1.385 (3) | C13—C14 | 1.386 (3) |
| C2—H2 | 0.9300 | C13—H13 | 0.9300 |
| C3—C4 | 1.401 (2) | C14—C15 | 1.387 (3) |
| C4—C5 | 1.394 (3) | C14—H14 | 0.9300 |
| C4—C7 | 1.496 (2) | C15—C16 | 1.378 (2) |
| C5—C6 | 1.379 (3) | C15—H15 | 0.9300 |
| C5—H5 | 0.9300 | ||
| C9—N1—C10 | 112.58 (15) | N1—C8—H8B | 109.1 |
| C9—N1—C8 | 123.10 (15) | C7—C8—H8B | 109.1 |
| C10—N1—C8 | 123.98 (15) | H8A—C8—H8B | 107.8 |
| C2—C1—C6 | 121.89 (17) | O3—C9—N1 | 124.37 (17) |
| C2—C1—Cl1 | 117.97 (15) | O3—C9—C16 | 129.93 (16) |
| C6—C1—Cl1 | 120.13 (15) | N1—C9—C16 | 105.70 (14) |
| C1—C2—C3 | 119.25 (18) | O2—C10—N1 | 124.53 (17) |
| C1—C2—H2 | 120.4 | O2—C10—C11 | 129.75 (16) |
| C3—C2—H2 | 120.4 | N1—C10—C11 | 105.71 (14) |
| C2—C3—C4 | 121.32 (17) | C12—C11—C16 | 121.32 (16) |
| C2—C3—Cl2 | 115.65 (14) | C12—C11—C10 | 130.68 (16) |
| C4—C3—Cl2 | 123.01 (14) | C16—C11—C10 | 108.00 (14) |
| C5—C4—C3 | 116.56 (16) | C11—C12—C13 | 117.67 (17) |
| C5—C4—C7 | 120.23 (16) | C11—C12—H12 | 121.2 |
| C3—C4—C7 | 123.20 (16) | C13—C12—H12 | 121.2 |
| C6—C5—C4 | 123.35 (18) | C12—C13—C14 | 121.22 (17) |
| C6—C5—H5 | 118.3 | C12—C13—H13 | 119.4 |
| C4—C5—H5 | 118.3 | C14—C13—H13 | 119.4 |
| C5—C6—C1 | 117.62 (18) | C13—C14—C15 | 121.24 (17) |
| C5—C6—H6 | 121.2 | C13—C14—H14 | 119.4 |
| C1—C6—H6 | 121.2 | C15—C14—H14 | 119.4 |
| O1—C7—C4 | 123.89 (17) | C16—C15—C14 | 117.50 (17) |
| O1—C7—C8 | 119.93 (17) | C16—C15—H15 | 121.3 |
| C4—C7—C8 | 116.18 (16) | C14—C15—H15 | 121.3 |
| N1—C8—C7 | 112.64 (16) | C15—C16—C11 | 121.04 (16) |
| N1—C8—H8A | 109.1 | C15—C16—C9 | 130.96 (16) |
| C7—C8—H8A | 109.1 | C11—C16—C9 | 108.00 (14) |
