Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015665/ci6063sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015665/ci6063Isup2.hkl |
CCDC reference: 175379
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.132
- Data-to-parameter ratio = 18.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(B) H4A \P(B) PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(B) H8A \P(B) PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(A) H14A \P(A) PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(B) C4 \P(B) PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(B) C8 \P(B) PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(A) C14 \P(A) PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(B) C4 H4A \P(B) PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(B) C8 H8A \P(B) PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(A) C14 H14A \P(A)
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
9 Alert Level C = Please check
The title compound, (I), was prepared by a photoinduced [2 + 2] cycloaddition reaction. A solution of 1-phenyl-2,3-dichloromaleimide (0.05 M) and phenylethylene (0.2 M) in benzene (40 ml) was photolysed by irradiation of light using a medium-pressure mercury lamp through a Pyrex filter and under constant nitrogen purging. Single crystals suitable for X-ray diffraction were obtained from slow evaporation of petroleum ether–ethyl acetate solution.
After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on the parent C atoms and refined isotropically.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C18H11Cl2NO2 | Dx = 1.438 Mg m−3 |
Mr = 344.18 | Melting point: 425K K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1468 (2) Å | Cell parameters from 7131 reflections |
b = 14.8464 (5) Å | θ = 2.7–28.3° |
c = 15.1091 (5) Å | µ = 0.42 mm−1 |
β = 97.410 (1)° | T = 293 K |
V = 1589.75 (9) Å3 | Slab, colorless |
Z = 4 | 0.44 × 0.34 × 0.24 mm |
F(000) = 704 |
Siemens SMART CCD area-detector diffractometer | 3864 independent reflections |
Radiation source: fine-focus sealed tube | 2514 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.7° |
ω scans | h = −9→8 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −19→19 |
Tmin = 0.838, Tmax = 0.907 | l = −20→12 |
10982 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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
3864 reflections | Δρmax = 0.38 e Å−3 |
209 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (2) |
C18H11Cl2NO2 | V = 1589.75 (9) Å3 |
Mr = 344.18 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.1468 (2) Å | µ = 0.42 mm−1 |
b = 14.8464 (5) Å | T = 293 K |
c = 15.1091 (5) Å | 0.44 × 0.34 × 0.24 mm |
β = 97.410 (1)° |
Siemens SMART CCD area-detector diffractometer | 3864 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2514 reflections with I > 2σ(I) |
Tmin = 0.838, Tmax = 0.907 | Rint = 0.084 |
10982 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.38 e Å−3 |
3864 reflections | Δρmin = −0.43 e Å−3 |
209 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0,88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | ||
Cl1 | 0.30319 (8) | 0.57153 (4) | 0.15060 (4) | 0.0508 (2) | |
Cl2 | 0.05751 (8) | 0.51319 (5) | 0.30901 (4) | 0.0594 (2) | |
O1 | 0.6777 (2) | 0.64442 (10) | 0.26076 (10) | 0.0464 (4) | |
O2 | 0.3266 (2) | 0.56671 (10) | 0.48054 (10) | 0.0486 (4) | |
N1 | 0.5330 (2) | 0.61295 (11) | 0.38447 (11) | 0.0328 (4) | |
C1 | 0.6444 (3) | 0.39557 (14) | 0.21529 (13) | 0.0347 (5) | |
C2 | 0.7193 (3) | 0.43853 (15) | 0.14621 (15) | 0.0459 (6) | |
H2A | 0.6700 | 0.4935 | 0.1248 | 0.055* | |
C3 | 0.8669 (4) | 0.3997 (2) | 0.10929 (18) | 0.0600 (7) | |
H3A | 0.9158 | 0.4284 | 0.0626 | 0.072* | |
C4 | 0.9420 (4) | 0.3192 (2) | 0.14115 (19) | 0.0664 (8) | |
H4A | 1.0437 | 0.2942 | 0.1172 | 0.080* | |
C5 | 0.8667 (4) | 0.27549 (19) | 0.20838 (19) | 0.0623 (7) | |
H5A | 0.9164 | 0.2204 | 0.2290 | 0.075* | |
C6 | 0.7183 (3) | 0.31244 (15) | 0.24559 (15) | 0.0470 (6) | |
H6A | 0.6674 | 0.2821 | 0.2908 | 0.056* | |
C7 | 0.4951 (3) | 0.43752 (12) | 0.25893 (13) | 0.0333 (4) | |
C8 | 0.3941 (3) | 0.41459 (14) | 0.32373 (15) | 0.0405 (5) | |
H8A | 0.3830 | 0.3611 | 0.3547 | 0.049* | |
C9 | 0.3044 (3) | 0.50597 (14) | 0.32907 (14) | 0.0362 (5) | |
C10 | 0.3805 (3) | 0.56330 (13) | 0.40906 (14) | 0.0345 (5) | |
C11 | 0.5609 (3) | 0.60431 (13) | 0.29577 (13) | 0.0327 (4) | |
C12 | 0.4226 (3) | 0.53394 (13) | 0.25349 (13) | 0.0325 (4) | |
C13 | 0.6479 (3) | 0.66940 (13) | 0.44723 (12) | 0.0333 (4) | |
C14 | 0.5749 (4) | 0.74981 (15) | 0.47258 (17) | 0.0513 (6) | |
H14A | 0.4548 | 0.7683 | 0.4485 | 0.062* | |
C15 | 0.6841 (5) | 0.80231 (18) | 0.53459 (19) | 0.0650 (8) | |
H15A | 0.6361 | 0.8564 | 0.5531 | 0.078* | |
C16 | 0.8616 (4) | 0.7760 (2) | 0.56919 (17) | 0.0636 (8) | |
H16A | 0.9338 | 0.8121 | 0.6107 | 0.076* | |
C17 | 0.9337 (4) | 0.69586 (19) | 0.54259 (16) | 0.0557 (7) | |
H17A | 1.0548 | 0.6780 | 0.5659 | 0.067* | |
C18 | 0.8260 (3) | 0.64218 (15) | 0.48137 (14) | 0.0413 (5) | |
H18A | 0.8737 | 0.5879 | 0.4633 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0509 (4) | 0.0541 (4) | 0.0439 (3) | 0.0078 (3) | −0.0069 (2) | 0.0023 (3) |
Cl2 | 0.0280 (3) | 0.0772 (5) | 0.0731 (5) | −0.0066 (3) | 0.0064 (3) | −0.0184 (3) |
O1 | 0.0522 (10) | 0.0444 (9) | 0.0452 (9) | −0.0121 (8) | 0.0154 (7) | −0.0001 (7) |
O2 | 0.0508 (10) | 0.0531 (10) | 0.0452 (9) | −0.0093 (8) | 0.0195 (7) | −0.0088 (7) |
N1 | 0.0346 (9) | 0.0293 (9) | 0.0350 (9) | −0.0044 (7) | 0.0070 (7) | −0.0036 (7) |
C1 | 0.0368 (11) | 0.0275 (10) | 0.0395 (11) | −0.0006 (8) | 0.0038 (8) | −0.0092 (8) |
C2 | 0.0531 (15) | 0.0357 (12) | 0.0508 (14) | 0.0008 (10) | 0.0146 (11) | −0.0039 (10) |
C3 | 0.0591 (17) | 0.0685 (18) | 0.0568 (16) | −0.0032 (14) | 0.0241 (12) | −0.0161 (14) |
C4 | 0.0579 (18) | 0.078 (2) | 0.0649 (18) | 0.0177 (15) | 0.0121 (13) | −0.0283 (16) |
C5 | 0.0688 (19) | 0.0518 (15) | 0.0636 (17) | 0.0269 (14) | −0.0013 (13) | −0.0164 (13) |
C6 | 0.0580 (15) | 0.0370 (12) | 0.0453 (13) | 0.0055 (11) | 0.0035 (10) | −0.0033 (10) |
C7 | 0.0372 (11) | 0.0256 (10) | 0.0372 (11) | −0.0012 (8) | 0.0054 (8) | −0.0037 (8) |
C8 | 0.0459 (13) | 0.0293 (11) | 0.0480 (13) | −0.0047 (9) | 0.0121 (10) | −0.0008 (9) |
C9 | 0.0282 (10) | 0.0374 (11) | 0.0440 (12) | −0.0034 (9) | 0.0086 (8) | −0.0066 (9) |
C10 | 0.0318 (11) | 0.0317 (11) | 0.0408 (12) | 0.0010 (8) | 0.0078 (8) | −0.0016 (9) |
C11 | 0.0359 (11) | 0.0258 (10) | 0.0368 (11) | 0.0044 (8) | 0.0066 (8) | 0.0028 (8) |
C12 | 0.0323 (11) | 0.0303 (10) | 0.0346 (10) | 0.0023 (8) | 0.0030 (8) | 0.0010 (8) |
C13 | 0.0394 (12) | 0.0304 (10) | 0.0309 (10) | −0.0060 (9) | 0.0073 (8) | −0.0020 (8) |
C14 | 0.0559 (16) | 0.0394 (13) | 0.0571 (15) | 0.0040 (11) | 0.0021 (11) | −0.0094 (11) |
C15 | 0.087 (2) | 0.0429 (15) | 0.0659 (17) | −0.0083 (14) | 0.0124 (15) | −0.0236 (13) |
C16 | 0.079 (2) | 0.0665 (19) | 0.0457 (15) | −0.0360 (16) | 0.0079 (13) | −0.0167 (13) |
C17 | 0.0433 (14) | 0.0727 (19) | 0.0495 (14) | −0.0180 (13) | 0.0001 (10) | 0.0032 (13) |
C18 | 0.0393 (12) | 0.0427 (13) | 0.0429 (12) | −0.0044 (10) | 0.0092 (9) | 0.0012 (10) |
Cl1—C12 | 1.765 (2) | C7—C8 | 1.333 (3) |
Cl2—C9 | 1.755 (2) | C7—C12 | 1.521 (3) |
O1—C11 | 1.202 (2) | C8—C9 | 1.507 (3) |
O2—C10 | 1.194 (2) | C8—H8A | 0.93 |
N1—C11 | 1.386 (2) | C9—C10 | 1.520 (3) |
N1—C10 | 1.404 (2) | C9—C12 | 1.562 (3) |
N1—C13 | 1.441 (3) | C11—C12 | 1.521 (3) |
C1—C2 | 1.388 (3) | C13—C18 | 1.371 (3) |
C1—C6 | 1.396 (3) | C13—C14 | 1.377 (3) |
C1—C7 | 1.464 (3) | C14—C15 | 1.381 (4) |
C2—C3 | 1.382 (3) | C14—H14A | 0.93 |
C2—H2A | 0.93 | C15—C16 | 1.366 (4) |
C3—C4 | 1.372 (4) | C15—H15A | 0.93 |
C3—H3A | 0.93 | C16—C17 | 1.376 (4) |
C4—C5 | 1.372 (4) | C16—H16A | 0.93 |
C4—H4A | 0.93 | C17—C18 | 1.378 (3) |
C5—C6 | 1.377 (3) | C17—H17A | 0.93 |
C5—H5A | 0.93 | C18—H18A | 0.93 |
C6—H6A | 0.93 | ||
C11—N1—C10 | 114.88 (17) | C12—C9—Cl2 | 118.95 (15) |
C11—N1—C13 | 123.30 (16) | O2—C10—N1 | 124.69 (19) |
C10—N1—C13 | 121.82 (16) | O2—C10—C9 | 128.22 (19) |
C2—C1—C6 | 119.13 (19) | N1—C10—C9 | 107.09 (16) |
C2—C1—C7 | 121.15 (19) | O1—C11—N1 | 125.1 (2) |
C6—C1—C7 | 119.68 (19) | O1—C11—C12 | 127.31 (19) |
C3—C2—C1 | 120.0 (2) | N1—C11—C12 | 107.61 (16) |
C3—C2—H2A | 120.0 | C7—C12—C11 | 115.17 (17) |
C1—C2—H2A | 120.0 | C7—C12—C9 | 85.58 (14) |
C4—C3—C2 | 120.4 (2) | C11—C12—C9 | 105.01 (16) |
C4—C3—H3A | 119.8 | C7—C12—Cl1 | 117.90 (15) |
C2—C3—H3A | 119.8 | C11—C12—Cl1 | 111.52 (14) |
C3—C4—C5 | 119.9 (2) | C9—C12—Cl1 | 118.86 (14) |
C3—C4—H4A | 120.0 | C18—C13—C14 | 121.2 (2) |
C5—C4—H4A | 120.0 | C18—C13—N1 | 119.94 (18) |
C4—C5—C6 | 120.7 (2) | C14—C13—N1 | 118.9 (2) |
C4—C5—H5A | 119.7 | C13—C14—C15 | 118.5 (3) |
C6—C5—H5A | 119.7 | C13—C14—H14A | 120.8 |
C5—C6—C1 | 119.8 (2) | C15—C14—H14A | 120.8 |
C5—C6—H6A | 120.1 | C16—C15—C14 | 120.9 (2) |
C1—C6—H6A | 120.1 | C16—C15—H15A | 119.5 |
C8—C7—C1 | 135.83 (19) | C14—C15—H15A | 119.5 |
C8—C7—C12 | 93.84 (16) | C15—C16—C17 | 120.0 (2) |
C1—C7—C12 | 129.73 (17) | C15—C16—H16A | 120.0 |
C7—C8—C9 | 94.81 (17) | C17—C16—H16A | 120.0 |
C7—C8—H8A | 132.6 | C16—C17—C18 | 119.9 (3) |
C9—C8—H8A | 132.6 | C16—C17—H17A | 120.1 |
C8—C9—C10 | 115.81 (18) | C18—C17—H17A | 120.1 |
C8—C9—C12 | 85.76 (15) | C13—C18—C17 | 119.5 (2) |
C10—C9—C12 | 105.10 (16) | C13—C18—H18A | 120.2 |
C8—C9—Cl2 | 118.11 (15) | C17—C18—H18A | 120.2 |
C10—C9—Cl2 | 110.61 (13) | ||
C6—C1—C2—C3 | −1.0 (4) | C1—C7—C12—C11 | −67.8 (3) |
C7—C1—C2—C3 | 176.6 (2) | C8—C7—C12—C9 | −0.26 (17) |
C1—C2—C3—C4 | −0.7 (4) | C1—C7—C12—C9 | −172.4 (2) |
C2—C3—C4—C5 | 1.8 (4) | C8—C7—C12—Cl1 | −120.72 (17) |
C3—C4—C5—C6 | −1.2 (4) | C1—C7—C12—Cl1 | 67.2 (3) |
C4—C5—C6—C1 | −0.6 (4) | O1—C11—C12—C7 | 88.5 (3) |
C2—C1—C6—C5 | 1.7 (3) | N1—C11—C12—C7 | −89.78 (19) |
C7—C1—C6—C5 | −176.0 (2) | O1—C11—C12—C9 | −179.3 (2) |
C2—C1—C7—C8 | 178.6 (3) | N1—C11—C12—C9 | 2.4 (2) |
C6—C1—C7—C8 | −3.8 (4) | O1—C11—C12—Cl1 | −49.3 (3) |
C2—C1—C7—C12 | −12.7 (3) | N1—C11—C12—Cl1 | 132.40 (14) |
C6—C1—C7—C12 | 164.9 (2) | C8—C9—C12—C7 | 0.23 (15) |
C1—C7—C8—C9 | 171.5 (2) | C10—C9—C12—C7 | 115.84 (17) |
C12—C7—C8—C9 | 0.27 (18) | Cl2—C9—C12—C7 | −119.69 (16) |
C7—C8—C9—C10 | −105.0 (2) | C8—C9—C12—C11 | −114.66 (17) |
C7—C8—C9—C12 | −0.27 (17) | C10—C9—C12—C11 | 0.9 (2) |
C7—C8—C9—Cl2 | 120.45 (17) | Cl2—C9—C12—C11 | 125.42 (15) |
C11—N1—C10—O2 | −174.8 (2) | C8—C9—C12—Cl1 | 119.79 (16) |
C13—N1—C10—O2 | 4.2 (3) | C10—C9—C12—Cl1 | −124.61 (16) |
C11—N1—C10—C9 | 6.0 (2) | Cl2—C9—C12—Cl1 | −0.1 (2) |
C13—N1—C10—C9 | −175.04 (17) | C11—N1—C13—C18 | −75.6 (3) |
C8—C9—C10—O2 | −90.5 (3) | C10—N1—C13—C18 | 105.5 (2) |
C12—C9—C10—O2 | 176.9 (2) | C11—N1—C13—C14 | 105.1 (2) |
Cl2—C9—C10—O2 | 47.3 (3) | C10—N1—C13—C14 | −73.8 (3) |
C8—C9—C10—N1 | 88.7 (2) | C18—C13—C14—C15 | −1.0 (3) |
C12—C9—C10—N1 | −3.9 (2) | N1—C13—C14—C15 | 178.2 (2) |
Cl2—C9—C10—N1 | −133.50 (15) | C13—C14—C15—C16 | 0.9 (4) |
C10—N1—C11—O1 | 176.3 (2) | C14—C15—C16—C17 | −0.3 (4) |
C13—N1—C11—O1 | −2.7 (3) | C15—C16—C17—C18 | −0.3 (4) |
C10—N1—C11—C12 | −5.4 (2) | C14—C13—C18—C17 | 0.4 (3) |
C13—N1—C11—C12 | 175.68 (17) | N1—C13—C18—C17 | −178.83 (18) |
C8—C7—C12—C11 | 104.3 (2) | C16—C17—C18—C13 | 0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···π(B)i | 0.93 | 2.74 | 3.618 (3) | 159 |
C8—H8A···π(B)ii | 0.93 | 2.71 | 3.528 (2) | 147 |
C14—H14A···π(A)iii | 0.93 | 2.76 | 3.612 (3) | 153 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H11Cl2NO2 |
Mr | 344.18 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.1468 (2), 14.8464 (5), 15.1091 (5) |
β (°) | 97.410 (1) |
V (Å3) | 1589.75 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.42 |
Crystal size (mm) | 0.44 × 0.34 × 0.24 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.838, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10982, 3864, 2514 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.132, 0.89 |
No. of reflections | 3864 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.43 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Cl1—C12 | 1.765 (2) | C1—C7 | 1.464 (3) |
Cl2—C9 | 1.755 (2) | C7—C8 | 1.333 (3) |
O1—C11 | 1.202 (2) | C7—C12 | 1.521 (3) |
O2—C10 | 1.194 (2) | C8—C9 | 1.507 (3) |
N1—C11 | 1.386 (2) | C9—C10 | 1.520 (3) |
N1—C13 | 1.441 (3) | C9—C12 | 1.562 (3) |
C12—C9—Cl2 | 118.95 (15) | C9—C12—Cl1 | 118.86 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···π(B)i | 0.93 | 2.74 | 3.618 (3) | 158.7 |
C8—H8A···π(B)ii | 0.93 | 2.71 | 3.528 (2) | 147.1 |
C14—H14A···π(A)iii | 0.93 | 2.76 | 3.612 (3) | 152.7 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2. |
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The photo-induced reactions of 1-phenyl-3,4-dichloromaleimide with diphenylethylene to give 3-azabicyclo[3.2.0]petanedione derivatives have been intensively investigated. Recently, we have reported the structure of one such derivative, 1,5-dichloro-3,6,6-triphenyl-3-azabicyclo[3.2.0]hepta-2,4-dione, (II) (Usman et al., 2001). In a continuation of this study, we have undertaken the X-ray structure analysis of the title compound, (I), a product obtained by the photoreaction of 1-phenyl-3,4-dichloromaleimide with phenylethylene.
In the succinimide–cyclobutene ring system of (I) (Fig. 1), the five-membered ring is planar compared to a half-chair conformation adopted in the succinimide–cyclobutane ring system of (II) (Usman et al., 2001). The mean plane through the five-membered ring, with N1 deviating by a maximum of -0.032 (2) Å, form a dihedral angle of 66.02 (14)° with the planar cyclobutene ring. The O1 and O2 atoms deviate from the plane of the attached ring by 0.047 (1) and 0.086 (1) Å, respectively. The phenyl ring substituent at C7 is almost coplanar with the cyclobutene [dihedral angle 12.86 (14)°], whereas that at N1 forms a dihedral of 74.83 (12)° with the five-membered ring.
The bond lengths and angles in (I) show normal values (Allen et al., 1987), and agree with those of (II) (Usman et al., 2001), except for the geometry of the cyclobutene ring (Table 1). The C7—C12 bond length of 1.521 (3) Å is slightly longer than that of the typical Csp3—Csp2 bond distance and is considered to be the steric effect of the bulky substituent attached at C7. In the title molecule, C9 and C12 are the chiral center atoms.
In the crystal, the molecular packing is stabilized by C—H···π interactions (Table 2) involving the phenyl rings. In Table 2, π(A) and π(B) denote the centre of gravity of the pheny rings C1–C6 and C13–C18, respectively.