Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802014769/cv6137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802014769/cv6137Isup2.hkl |
CCDC reference: 197483
The title compound was prepared by thermolysis of 1,5-dichloro-3,6,6-triphenyl-3-azabicyclo[3.2.0]hepta-2,4-dione in N,N-dimethylacetamide (Zhao & Xu, 2002). Single crystals suitable for X-ray diffraction were obtained from slow evaporation of a petroleum ether–acetone solution.
The H atoms were fixed geometrically and treated as riding atoms on the parent C atoms, with C—H distances in the range 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C). Due to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS; 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).
C26H20F2N2O2 | Dx = 1.325 Mg m−3 |
Mr = 430.44 | Melting point: 430(1)K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.4125 (7) Å | Cell parameters from 2961 reflections |
b = 7.4776 (4) Å | θ = 2.9–28.3° |
c = 20.3189 (7) Å | µ = 0.10 mm−1 |
β = 99.787 (2)° | T = 213 K |
V = 2157.9 (2) Å3 | Needle, yellow |
Z = 4 | 0.34 × 0.20 × 0.14 mm |
F(000) = 896 |
Siemens SMART CCD area-detector diffractometer | 3743 independent reflections |
Radiation source: fine-focus sealed tube | 1914 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.107 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.9° |
ω scans | h = −16→17 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.968, Tmax = 0.987 | l = −24→17 |
9770 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)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.0818P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
3743 reflections | Δρmax = 0.37 e Å−3 |
292 parameters | Δρmin = −0.41 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: 0.042 (3) |
C26H20F2N2O2 | V = 2157.9 (2) Å3 |
Mr = 430.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.4125 (7) Å | µ = 0.10 mm−1 |
b = 7.4776 (4) Å | T = 213 K |
c = 20.3189 (7) Å | 0.34 × 0.20 × 0.14 mm |
β = 99.787 (2)° |
Siemens SMART CCD area-detector diffractometer | 3743 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 1914 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.987 | Rint = 0.107 |
9770 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.37 e Å−3 |
3743 reflections | Δρmin = −0.41 e Å−3 |
292 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 | ||
O1 | 0.44129 (17) | 0.8544 (3) | 0.57000 (12) | 0.0282 (7) | |
O2 | 0.72378 (17) | 0.5711 (3) | 0.58317 (12) | 0.0309 (7) | |
F1 | 0.98744 (17) | 1.0583 (4) | 0.59089 (13) | 0.0716 (9) | |
F2 | 0.89085 (19) | 0.1524 (4) | 0.24394 (13) | 0.0680 (9) | |
N1 | 0.58615 (19) | 0.7150 (4) | 0.59470 (13) | 0.0240 (8) | |
C1 | 0.6913 (3) | 0.8310 (5) | 0.6927 (2) | 0.0345 (10) | |
H1A | 0.7354 | 0.8598 | 0.6658 | 0.041* | |
C2 | 0.7087 (3) | 0.8688 (5) | 0.7604 (2) | 0.0442 (12) | |
H2A | 0.7645 | 0.9251 | 0.7790 | 0.053* | |
C3 | 0.6449 (3) | 0.8245 (6) | 0.7999 (2) | 0.0476 (13) | |
H3B | 0.6569 | 0.8524 | 0.8452 | 0.057* | |
C4 | 0.5631 (3) | 0.7389 (6) | 0.7732 (2) | 0.0451 (12) | |
H4B | 0.5210 | 0.7050 | 0.8009 | 0.054* | |
C5 | 0.5422 (3) | 0.7022 (5) | 0.70527 (18) | 0.0311 (10) | |
H5A | 0.4859 | 0.6470 | 0.6870 | 0.037* | |
C6 | 0.6068 (2) | 0.7494 (5) | 0.66545 (17) | 0.0257 (9) | |
C7 | 0.6505 (3) | 0.6384 (5) | 0.55653 (18) | 0.0219 (8) | |
C8 | 0.5068 (2) | 0.7751 (5) | 0.55264 (17) | 0.0230 (9) | |
C9 | 0.5211 (2) | 0.7270 (5) | 0.48267 (17) | 0.0207 (8) | |
C10 | 0.6087 (2) | 0.6532 (4) | 0.48595 (17) | 0.0195 (8) | |
C11 | 0.6550 (2) | 0.5737 (5) | 0.43462 (17) | 0.0221 (9) | |
H11A | 0.6168 | 0.5087 | 0.4015 | 0.027* | |
C12 | 0.7471 (2) | 0.5837 (5) | 0.42970 (17) | 0.0224 (9) | |
C13 | 0.8121 (2) | 0.7095 (5) | 0.47195 (18) | 0.0243 (9) | |
C14 | 0.7890 (3) | 0.8895 (5) | 0.4752 (2) | 0.0319 (10) | |
H14A | 0.7333 | 0.9317 | 0.4501 | 0.038* | |
C15 | 0.8478 (3) | 1.0069 (6) | 0.5154 (2) | 0.0434 (12) | |
H15A | 0.8325 | 1.1274 | 0.5173 | 0.052* | |
C16 | 0.9282 (3) | 0.9411 (7) | 0.5518 (2) | 0.0422 (12) | |
C17 | 0.9555 (3) | 0.7669 (7) | 0.5496 (2) | 0.0462 (12) | |
H17A | 1.0121 | 0.7280 | 0.5744 | 0.055* | |
C18 | 0.8965 (3) | 0.6492 (6) | 0.50932 (19) | 0.0326 (10) | |
H18A | 0.9134 | 0.5296 | 0.5073 | 0.039* | |
C19 | 0.7862 (2) | 0.4691 (5) | 0.38081 (17) | 0.0243 (9) | |
C20 | 0.7526 (3) | 0.2990 (6) | 0.36610 (19) | 0.0351 (11) | |
H20A | 0.7050 | 0.2558 | 0.3875 | 0.042* | |
C21 | 0.7871 (3) | 0.1887 (6) | 0.3204 (2) | 0.0421 (12) | |
H21A | 0.7651 | 0.0727 | 0.3119 | 0.051* | |
C22 | 0.8549 (3) | 0.2599 (7) | 0.2889 (2) | 0.0432 (12) | |
C23 | 0.8914 (3) | 0.4257 (6) | 0.3010 (2) | 0.0421 (11) | |
H23A | 0.9385 | 0.4675 | 0.2788 | 0.050* | |
C24 | 0.8567 (3) | 0.5321 (6) | 0.34767 (19) | 0.0346 (10) | |
H24A | 0.8809 | 0.6464 | 0.3568 | 0.042* | |
N2 | 0.45456 (18) | 0.7695 (4) | 0.43011 (14) | 0.0235 (7) | |
C26 | 0.4758 (3) | 0.7706 (5) | 0.36173 (18) | 0.0345 (10) | |
H26A | 0.4420 | 0.8662 | 0.3368 | 0.052* | |
H26B | 0.4572 | 0.6586 | 0.3404 | 0.052* | |
H26C | 0.5422 | 0.7877 | 0.3634 | 0.052* | |
C25 | 0.3584 (2) | 0.8236 (5) | 0.43560 (19) | 0.0298 (10) | |
H25A | 0.3174 | 0.8006 | 0.3941 | 0.045* | |
H25B | 0.3575 | 0.9489 | 0.4457 | 0.045* | |
H25C | 0.3375 | 0.7566 | 0.4706 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0272 (14) | 0.0314 (16) | 0.0273 (15) | 0.0047 (12) | 0.0084 (12) | −0.0030 (12) |
O2 | 0.0258 (14) | 0.0382 (17) | 0.0282 (15) | 0.0066 (13) | 0.0027 (12) | 0.0065 (13) |
F1 | 0.0546 (16) | 0.097 (2) | 0.0643 (19) | −0.0334 (17) | 0.0144 (15) | −0.0476 (17) |
F2 | 0.080 (2) | 0.077 (2) | 0.0574 (18) | 0.0012 (16) | 0.0414 (16) | −0.0298 (15) |
N1 | 0.0207 (16) | 0.034 (2) | 0.0155 (16) | 0.0017 (15) | −0.0015 (13) | −0.0002 (14) |
C1 | 0.037 (2) | 0.026 (2) | 0.037 (3) | −0.002 (2) | −0.002 (2) | 0.0030 (19) |
C2 | 0.048 (3) | 0.035 (3) | 0.041 (3) | −0.001 (2) | −0.018 (2) | −0.009 (2) |
C3 | 0.056 (3) | 0.057 (3) | 0.026 (2) | 0.015 (3) | −0.005 (2) | −0.009 (2) |
C4 | 0.050 (3) | 0.059 (3) | 0.026 (2) | 0.009 (3) | 0.008 (2) | −0.006 (2) |
C5 | 0.034 (2) | 0.035 (3) | 0.024 (2) | −0.0034 (19) | 0.0039 (19) | −0.0026 (18) |
C6 | 0.029 (2) | 0.029 (2) | 0.018 (2) | −0.0004 (18) | 0.0016 (17) | −0.0004 (17) |
C7 | 0.021 (2) | 0.018 (2) | 0.027 (2) | −0.0017 (17) | 0.0044 (17) | 0.0035 (17) |
C8 | 0.023 (2) | 0.025 (2) | 0.023 (2) | −0.0087 (18) | 0.0085 (17) | −0.0006 (17) |
C9 | 0.0197 (18) | 0.022 (2) | 0.020 (2) | −0.0078 (17) | 0.0031 (16) | −0.0012 (16) |
C10 | 0.0186 (19) | 0.0162 (19) | 0.024 (2) | −0.0003 (16) | 0.0053 (16) | 0.0014 (16) |
C11 | 0.0217 (19) | 0.024 (2) | 0.020 (2) | 0.0000 (17) | 0.0009 (16) | −0.0018 (17) |
C12 | 0.024 (2) | 0.021 (2) | 0.024 (2) | 0.0015 (17) | 0.0060 (17) | 0.0045 (16) |
C13 | 0.0185 (19) | 0.035 (2) | 0.022 (2) | −0.0017 (18) | 0.0107 (16) | 0.0002 (17) |
C14 | 0.026 (2) | 0.030 (3) | 0.041 (3) | 0.0022 (19) | 0.0109 (19) | −0.0017 (19) |
C15 | 0.036 (2) | 0.041 (3) | 0.059 (3) | −0.007 (2) | 0.026 (2) | −0.019 (2) |
C16 | 0.032 (2) | 0.059 (3) | 0.039 (3) | −0.019 (2) | 0.015 (2) | −0.024 (2) |
C17 | 0.031 (2) | 0.074 (4) | 0.032 (3) | −0.006 (3) | 0.001 (2) | −0.008 (2) |
C18 | 0.027 (2) | 0.035 (2) | 0.036 (2) | −0.002 (2) | 0.0075 (19) | −0.003 (2) |
C19 | 0.0191 (19) | 0.033 (2) | 0.021 (2) | 0.0010 (18) | 0.0033 (16) | 0.0021 (17) |
C20 | 0.031 (2) | 0.040 (3) | 0.036 (2) | −0.003 (2) | 0.013 (2) | −0.002 (2) |
C21 | 0.044 (3) | 0.042 (3) | 0.044 (3) | −0.003 (2) | 0.017 (2) | −0.016 (2) |
C22 | 0.045 (3) | 0.060 (3) | 0.027 (2) | 0.005 (3) | 0.013 (2) | −0.017 (2) |
C23 | 0.040 (2) | 0.052 (3) | 0.039 (3) | −0.005 (2) | 0.022 (2) | −0.005 (2) |
C24 | 0.029 (2) | 0.040 (3) | 0.038 (3) | −0.004 (2) | 0.012 (2) | −0.004 (2) |
N2 | 0.0170 (15) | 0.0327 (19) | 0.0213 (17) | 0.0019 (14) | 0.0048 (14) | 0.0028 (14) |
C26 | 0.035 (2) | 0.044 (3) | 0.023 (2) | 0.011 (2) | 0.0034 (18) | 0.0035 (19) |
C25 | 0.021 (2) | 0.031 (2) | 0.035 (2) | −0.0006 (18) | −0.0011 (18) | 0.0019 (18) |
O1—C8 | 1.217 (4) | C13—C18 | 1.395 (5) |
O2—C7 | 1.211 (4) | C14—C15 | 1.385 (5) |
F1—C16 | 1.377 (4) | C14—H14A | 0.9300 |
F2—C22 | 1.382 (4) | C15—C16 | 1.357 (6) |
N1—C8 | 1.381 (4) | C15—H15A | 0.9300 |
N1—C7 | 1.427 (4) | C16—C17 | 1.364 (6) |
N1—C6 | 1.441 (4) | C17—C18 | 1.389 (5) |
C1—C2 | 1.385 (6) | C17—H17A | 0.9300 |
C1—C6 | 1.390 (5) | C18—H18A | 0.9300 |
C1—H1A | 0.9300 | C19—C20 | 1.375 (5) |
C2—C3 | 1.361 (6) | C19—C24 | 1.393 (5) |
C2—H2A | 0.9300 | C20—C21 | 1.396 (5) |
C3—C4 | 1.370 (6) | C20—H20A | 0.9300 |
C3—H3B | 0.9300 | C21—C22 | 1.363 (6) |
C4—C5 | 1.389 (5) | C21—H21A | 0.9300 |
C4—H4B | 0.9300 | C22—C23 | 1.353 (6) |
C5—C6 | 1.379 (5) | C23—C24 | 1.394 (5) |
C5—H5A | 0.9300 | C23—H23A | 0.9300 |
C7—C10 | 1.462 (5) | C24—H24A | 0.9300 |
C8—C9 | 1.514 (5) | N2—C25 | 1.465 (4) |
C9—N2 | 1.346 (4) | N2—C26 | 1.473 (4) |
C9—C10 | 1.370 (5) | C26—H26A | 0.9600 |
C10—C11 | 1.457 (5) | C26—H26B | 0.9600 |
C11—C12 | 1.351 (4) | C26—H26C | 0.9600 |
C11—H11A | 0.9300 | C25—H25A | 0.9600 |
C12—C13 | 1.492 (5) | C25—H25B | 0.9600 |
C12—C19 | 1.493 (5) | C25—H25C | 0.9600 |
C13—C14 | 1.391 (5) | ||
C8—N1—C7 | 109.9 (3) | C16—C15—C14 | 118.2 (4) |
C8—N1—C6 | 124.6 (3) | C16—C15—H15A | 120.9 |
C7—N1—C6 | 124.8 (3) | C14—C15—H15A | 120.9 |
C2—C1—C6 | 118.9 (4) | C15—C16—C17 | 123.5 (4) |
C2—C1—H1A | 120.6 | C15—C16—F1 | 118.2 (4) |
C6—C1—H1A | 120.6 | C17—C16—F1 | 118.2 (4) |
C3—C2—C1 | 120.7 (4) | C16—C17—C18 | 118.3 (4) |
C3—C2—H2A | 119.6 | C16—C17—H17A | 120.9 |
C1—C2—H2A | 119.6 | C18—C17—H17A | 120.9 |
C2—C3—C4 | 120.1 (4) | C17—C18—C13 | 120.4 (4) |
C2—C3—H3B | 120.0 | C17—C18—H18A | 119.8 |
C4—C3—H3B | 120.0 | C13—C18—H18A | 119.8 |
C3—C4—C5 | 120.8 (4) | C20—C19—C24 | 117.8 (4) |
C3—C4—H4B | 119.6 | C20—C19—C12 | 121.1 (3) |
C5—C4—H4B | 119.6 | C24—C19—C12 | 121.1 (3) |
C6—C5—C4 | 118.6 (4) | C19—C20—C21 | 122.6 (4) |
C6—C5—H5A | 120.7 | C19—C20—H20A | 118.7 |
C4—C5—H5A | 120.7 | C21—C20—H20A | 118.7 |
C5—C6—C1 | 120.8 (3) | C22—C21—C20 | 116.5 (4) |
C5—C6—N1 | 119.6 (3) | C22—C21—H21A | 121.7 |
C1—C6—N1 | 119.6 (3) | C20—C21—H21A | 121.7 |
O2—C7—N1 | 121.5 (3) | C23—C22—C21 | 124.0 (4) |
O2—C7—C10 | 130.7 (3) | C23—C22—F2 | 118.4 (4) |
N1—C7—C10 | 107.8 (3) | C21—C22—F2 | 117.5 (4) |
O1—C8—N1 | 125.5 (3) | C22—C23—C24 | 118.3 (4) |
O1—C8—C9 | 128.6 (3) | C22—C23—H23A | 120.9 |
N1—C8—C9 | 105.9 (3) | C24—C23—H23A | 120.9 |
N2—C9—C10 | 131.3 (3) | C19—C24—C23 | 120.8 (4) |
N2—C9—C8 | 119.8 (3) | C19—C24—H24A | 119.6 |
C10—C9—C8 | 108.8 (3) | C23—C24—H24A | 119.6 |
C9—C10—C11 | 131.3 (3) | C9—N2—C25 | 124.0 (3) |
C9—C10—C7 | 107.5 (3) | C9—N2—C26 | 121.0 (3) |
C11—C10—C7 | 120.6 (3) | C25—N2—C26 | 114.9 (3) |
C12—C11—C10 | 127.3 (3) | N2—C26—H26A | 109.5 |
C12—C11—H11A | 116.4 | N2—C26—H26B | 109.5 |
C10—C11—H11A | 116.4 | H26A—C26—H26B | 109.5 |
C11—C12—C13 | 121.4 (3) | N2—C26—H26C | 109.5 |
C11—C12—C19 | 120.3 (3) | H26A—C26—H26C | 109.5 |
C13—C12—C19 | 118.3 (3) | H26B—C26—H26C | 109.5 |
C14—C13—C18 | 118.7 (4) | N2—C25—H25A | 109.5 |
C14—C13—C12 | 120.4 (3) | N2—C25—H25B | 109.5 |
C18—C13—C12 | 120.9 (3) | H25A—C25—H25B | 109.5 |
C15—C14—C13 | 120.9 (4) | N2—C25—H25C | 109.5 |
C15—C14—H14A | 119.5 | H25A—C25—H25C | 109.5 |
C13—C14—H14A | 119.5 | H25B—C25—H25C | 109.5 |
C6—C1—C2—C3 | 1.0 (6) | C10—C11—C12—C13 | −11.1 (6) |
C1—C2—C3—C4 | 1.1 (7) | C10—C11—C12—C19 | 169.5 (3) |
C2—C3—C4—C5 | −2.5 (7) | C11—C12—C13—C14 | −51.4 (5) |
C3—C4—C5—C6 | 1.7 (6) | C19—C12—C13—C14 | 128.0 (4) |
C4—C5—C6—C1 | 0.4 (6) | C11—C12—C13—C18 | 128.1 (4) |
C4—C5—C6—N1 | −179.1 (3) | C19—C12—C13—C18 | −52.5 (5) |
C2—C1—C6—C5 | −1.7 (6) | C18—C13—C14—C15 | −0.9 (5) |
C2—C1—C6—N1 | 177.8 (4) | C12—C13—C14—C15 | 178.6 (3) |
C8—N1—C6—C5 | 55.5 (5) | C13—C14—C15—C16 | −0.5 (6) |
C7—N1—C6—C5 | −134.5 (4) | C14—C15—C16—C17 | 1.9 (6) |
C8—N1—C6—C1 | −124.0 (4) | C14—C15—C16—F1 | 178.9 (3) |
C7—N1—C6—C1 | 46.0 (5) | C15—C16—C17—C18 | −1.9 (6) |
C8—N1—C7—O2 | −177.3 (3) | F1—C16—C17—C18 | −178.9 (3) |
C6—N1—C7—O2 | 11.4 (5) | C16—C17—C18—C13 | 0.5 (6) |
C8—N1—C7—C10 | 0.5 (4) | C14—C13—C18—C17 | 0.8 (5) |
C6—N1—C7—C10 | −170.7 (3) | C12—C13—C18—C17 | −178.6 (3) |
C7—N1—C8—O1 | −176.3 (3) | C11—C12—C19—C20 | −34.4 (5) |
C6—N1—C8—O1 | −5.0 (6) | C13—C12—C19—C20 | 146.2 (3) |
C7—N1—C8—C9 | 1.9 (4) | C11—C12—C19—C24 | 144.4 (4) |
C6—N1—C8—C9 | 173.2 (3) | C13—C12—C19—C24 | −35.0 (5) |
O1—C8—C9—N2 | −1.7 (5) | C24—C19—C20—C21 | 0.7 (6) |
N1—C8—C9—N2 | −179.9 (3) | C12—C19—C20—C21 | 179.6 (4) |
O1—C8—C9—C10 | 174.3 (4) | C19—C20—C21—C22 | −1.9 (6) |
N1—C8—C9—C10 | −3.9 (4) | C20—C21—C22—C23 | 2.2 (7) |
N2—C9—C10—C11 | −9.5 (7) | C20—C21—C22—F2 | 179.3 (4) |
C8—C9—C10—C11 | 175.2 (3) | C21—C22—C23—C24 | −1.3 (7) |
N2—C9—C10—C7 | 179.5 (3) | F2—C22—C23—C24 | −178.3 (4) |
C8—C9—C10—C7 | 4.2 (4) | C20—C19—C24—C23 | 0.3 (5) |
O2—C7—C10—C9 | 174.6 (4) | C12—C19—C24—C23 | −178.6 (4) |
N1—C7—C10—C9 | −3.0 (4) | C22—C23—C24—C19 | −0.1 (6) |
O2—C7—C10—C11 | 2.4 (6) | C10—C9—N2—C25 | 170.5 (4) |
N1—C7—C10—C11 | −175.2 (3) | C8—C9—N2—C25 | −14.6 (5) |
C9—C10—C11—C12 | 144.1 (4) | C10—C9—N2—C26 | −11.8 (6) |
C7—C10—C11—C12 | −45.8 (5) | C8—C9—N2—C26 | 163.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···F1i | 0.93 | 2.48 | 3.266 (5) | 142 |
C20—H20A···O1ii | 0.93 | 2.55 | 3.470 (5) | 172 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H20F2N2O2 |
Mr | 430.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 213 |
a, b, c (Å) | 14.4125 (7), 7.4776 (4), 20.3189 (7) |
β (°) | 99.787 (2) |
V (Å3) | 2157.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.34 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.968, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9770, 3743, 1914 |
Rint | 0.107 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.181, 0.89 |
No. of reflections | 3743 |
No. of parameters | 292 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.41 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···F1i | 0.93 | 2.48 | 3.266 (5) | 142 |
C20—H20A···O1ii | 0.93 | 2.55 | 3.470 (5) | 172 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1. |
The photoinduced reactions of 1-phenyl-3,4-dichloromaleimide with diphenylethylene give the cyclobutane product, namely 1,5-dichloro-3,6,6-triphenyl-3-azabicyclo[3.2.0]hepta-2,4-dione, (II), whose crystal structure has been reported previously (Usman et al., 2001). This compound undergoes thermal cyclobutane ring opening reaction in N,N-dimethylacetamide to give the title compound, (I) (Zhao & Xu, 2002). In order to establish the conformation of (I), we have undertaken X-ray crystal structure analysis and the results are presented here.
The bond lengths and angles in (I) listed in Table 1 are within normal ranges (Allen et al., 1987), except for the values within the maleimide moiety (N1/C7—C10). The C8—C9 bond length lengthens, whereas the N1—C8 bond length shortens, compared with typical Csp2—Csp2 and Csp2—Nsp2 distances, respectively, due to interactions between the bulky substituents attached at the maleimide moiety. This also affects the N2—C9—C10 bond angle, which is about 11.5° larger than N2—C9—C8. The dimethylamino group (N2/C15/C26) attached at C9 is nearly coplanar with the maleimide. This substituent is twisted out about the N2—C9 bond by 13.7 (2)° with respect to the maleimide. Atoms O1 and O2 are displaced on opposite sides of the maleimide plane, by 0.090 (2) and 0.075 (2) Å, respectively.
The C1—C6 phenyl ring attached at atom N1 forms a dihedral angle of 51.0 (2)° with the maleimide, which is much smaller compared with that in (II) [74.8 (1)°; Usman et al., 2001].
The C11/C12/C13/C19 plane containing the ethylene double bond is planar and makes dihedral angles of 50.1 (2), 52.3 (2) and 35.0 (2)° with the maleimide and C13—C18 and C19—C24 phenyl rings, respectively (Fig. 1). The dihedral angle between the two phenyl rings is 74.5 (2)°, which is comparable with that of the 2,2-diphenylethenyl moiety in another structure [75.5 (1)°; Usman et al., 2002]. Atoms F1 and F2 also lie in the planes of their attached phenyl rings, with deviations of 0.015 (3) and 0.023 (3) Å, respectively.
In the packing, two adjacent molecules form dimers (Fig. 2) through C—H···O intermolecular contacts (Table 1). The molecular dimers are further interconnected by C—H···F interactions (Table 1) to form a three-dimensional network (Fig. 3).