Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199014596/ja1009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270199014596/ja1009Isup2.hkl |
CCDC reference: 142769
The title compound was prepared by condensing p-methoxybenzenealdehyde with freshly prepared p-cyanophenylhydroxylamine in absolute ethanol? at room temperature for 48 h. Evaporation of the solvent yielded a red oil, which was twice crystallized from ethanol. A yellow single-crystal of (I) was coated with lacquer prior to mounting on the diffractometer, because of its instability in air.
All non-H atoms were refined anisotropically. The positions of the H atoms were refined, but their isotropic U values were constrained.
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998).
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms are shown as spheres of arbitrary radii. |
C15H12N2O2 | Z = 4 |
Mr = 252.27 | F(000) = 528 |
Triclinic, P1 | Dx = 1.339 Mg m−3 |
a = 7.5821 (16) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 7.613 (2) Å | Cell parameters from 25 reflections |
c = 22.270 (3) Å | θ = 11.3–14.2° |
α = 99.469 (16)° | µ = 0.09 mm−1 |
β = 96.999 (12)° | T = 293 K |
γ = 94.79 (2)° | Plate, yellow |
V = 1251.5 (5) Å3 | 0.50 × 0.30 × 0.13 mm |
Enraf Nonius CAD-4 diffractometer | Rint = 0.054 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.7° |
Graphite monochromator | h = −9→8 |
non–profiled ω/2θ scans | k = −9→8 |
4490 measured reflections | l = 0→26 |
4370 independent reflections | 3 standard reflections every 300 min |
2688 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | Only H-atom coordinates refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.0037P] where P = (Fo2 + 2Fc2)/3 |
4370 reflections | (Δ/σ)max < 0.001 |
415 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C15H12N2O2 | γ = 94.79 (2)° |
Mr = 252.27 | V = 1251.5 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.5821 (16) Å | Mo Kα radiation |
b = 7.613 (2) Å | µ = 0.09 mm−1 |
c = 22.270 (3) Å | T = 293 K |
α = 99.469 (16)° | 0.50 × 0.30 × 0.13 mm |
β = 96.999 (12)° |
Enraf Nonius CAD-4 diffractometer | Rint = 0.054 |
4490 measured reflections | 3 standard reflections every 300 min |
4370 independent reflections | intensity decay: 1% |
2688 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.177 | Only H-atom coordinates refined |
S = 1.01 | Δρmax = 0.24 e Å−3 |
4370 reflections | Δρmin = −0.22 e Å−3 |
415 parameters |
Refinement. Refinement was based on F2, using 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 | 0.7959 (3) | 0.9605 (3) | 0.27680 (10) | 0.0433 (5) | |
N2 | 0.1462 (4) | 0.7417 (5) | 0.44413 (15) | 0.0917 (10) | |
N1' | 0.7037 (3) | 0.4843 (3) | 0.21981 (10) | 0.0434 (5) | |
N2' | 1.3438 (4) | 0.7014 (4) | 0.04902 (15) | 0.0909 (10) | |
O1 | 1.1627 (2) | 1.1878 (3) | 0.04454 (8) | 0.0566 (5) | |
O2 | 0.9563 (2) | 0.9373 (3) | 0.29949 (9) | 0.0661 (6) | |
O1' | 0.3274 (3) | 0.2712 (3) | 0.45091 (9) | 0.0643 (6) | |
O2' | 0.5471 (2) | 0.4284 (3) | 0.18879 (9) | 0.0654 (6) | |
C1 | 1.3531 (4) | 1.1915 (5) | 0.04987 (15) | 0.0617 (8) | |
H1A | 1.384 (4) | 1.240 (4) | 0.0143 (17) | 0.092* | |
H1B | 1.395 (4) | 1.065 (5) | 0.0522 (15) | 0.092* | |
H1C | 1.414 (4) | 1.282 (4) | 0.0882 (16) | 0.092* | |
C2 | 1.0789 (3) | 1.1401 (3) | 0.09096 (11) | 0.0421 (6) | |
C3 | 1.1630 (4) | 1.0999 (4) | 0.14506 (12) | 0.0444 (6) | |
H3 | 1.290 (4) | 1.105 (3) | 0.1518 (12) | 0.053* | |
C4 | 1.0646 (3) | 1.0580 (4) | 0.19024 (12) | 0.0436 (6) | |
H4 | 1.121 (3) | 1.018 (3) | 0.2271 (13) | 0.052* | |
C5 | 0.8786 (3) | 1.0564 (3) | 0.18225 (11) | 0.0406 (6) | |
C6 | 0.7974 (4) | 1.0983 (4) | 0.12670 (13) | 0.0485 (7) | |
H6 | 0.670 (4) | 1.097 (3) | 0.1205 (12) | 0.058* | |
C7 | 0.8937 (4) | 1.1374 (4) | 0.08193 (13) | 0.0485 (7) | |
H7 | 0.830 (3) | 1.175 (3) | 0.0442 (13) | 0.058* | |
C8 | 0.7604 (4) | 1.0176 (4) | 0.22476 (13) | 0.0451 (7) | |
H8 | 0.643 (4) | 1.037 (3) | 0.2172 (12) | 0.054* | |
C9 | 0.6541 (3) | 0.9175 (3) | 0.31210 (11) | 0.0404 (6) | |
C10 | 0.4801 (3) | 0.8680 (4) | 0.28446 (13) | 0.0486 (7) | |
H10 | 0.449 (3) | 0.865 (3) | 0.2395 (13) | 0.058* | |
C11 | 0.3493 (4) | 0.8268 (4) | 0.31945 (13) | 0.0519 (7) | |
H11 | 0.227 (4) | 0.788 (4) | 0.3017 (13) | 0.062* | |
C12 | 0.3947 (3) | 0.8296 (3) | 0.38184 (13) | 0.0468 (7) | |
C13 | 0.5692 (4) | 0.8775 (4) | 0.40908 (14) | 0.0574 (8) | |
H13 | 0.597 (4) | 0.867 (4) | 0.4524 (14) | 0.069* | |
C14 | 0.6993 (4) | 0.9201 (4) | 0.37420 (13) | 0.0534 (7) | |
H14 | 0.820 (4) | 0.948 (4) | 0.3916 (13) | 0.064* | |
C15 | 0.2571 (4) | 0.7820 (4) | 0.41726 (14) | 0.0620 (8) | |
C1' | 0.1378 (5) | 0.2319 (6) | 0.43870 (19) | 0.0759 (10) | |
H1'A | 0.098 (5) | 0.205 (5) | 0.4759 (19) | 0.114* | |
H1'B | 0.100 (5) | 0.129 (5) | 0.4023 (19) | 0.114* | |
H1'C | 0.088 (5) | 0.336 (5) | 0.4291 (19) | 0.114* | |
C2' | 0.4158 (4) | 0.3222 (4) | 0.40574 (12) | 0.0482 (7) | |
C3' | 0.3397 (4) | 0.3088 (4) | 0.34534 (13) | 0.0499 (7) | |
H3' | 0.227 (4) | 0.258 (4) | 0.3331 (13) | 0.060* | |
C4' | 0.4415 (3) | 0.3612 (4) | 0.30258 (13) | 0.0476 (7) | |
H4' | 0.386 (4) | 0.361 (3) | 0.2604 (13) | 0.057* | |
C5' | 0.6195 (3) | 0.4309 (3) | 0.31936 (11) | 0.0398 (6) | |
C6' | 0.6921 (4) | 0.4450 (4) | 0.38139 (13) | 0.0508 (7) | |
H6' | 0.820 (4) | 0.493 (4) | 0.3937 (13) | 0.061* | |
C7' | 0.5928 (4) | 0.3908 (4) | 0.42374 (13) | 0.0547 (8) | |
H7' | 0.644 (4) | 0.396 (4) | 0.4641 (14) | 0.066* | |
C8' | 0.7382 (3) | 0.4901 (4) | 0.27943 (12) | 0.0437 (6) | |
H8' | 0.856 (3) | 0.550 (3) | 0.2976 (12) | 0.052* | |
C9' | 0.8423 (3) | 0.5360 (3) | 0.18473 (11) | 0.0402 (6) | |
C10' | 1.0201 (3) | 0.5209 (3) | 0.20360 (12) | 0.0430 (6) | |
H10' | 1.050 (3) | 0.467 (3) | 0.2398 (12) | 0.052* | |
C11' | 1.1471 (4) | 0.5627 (4) | 0.16765 (12) | 0.0467 (7) | |
H11' | 1.266 (4) | 0.549 (4) | 0.1781 (13) | 0.056* | |
C12' | 1.0962 (3) | 0.6208 (3) | 0.11273 (12) | 0.0461 (7) | |
C13' | 0.9180 (4) | 0.6361 (4) | 0.09377 (13) | 0.0512 (7) | |
H13' | 0.889 (4) | 0.682 (3) | 0.0543 (13) | 0.061* | |
C14' | 0.7899 (4) | 0.5930 (4) | 0.12963 (12) | 0.0466 (7) | |
H14' | 0.665 (4) | 0.592 (3) | 0.1169 (12) | 0.056* | |
C15' | 1.2334 (4) | 0.6654 (4) | 0.07651 (14) | 0.0594 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0340 (12) | 0.0558 (14) | 0.0421 (12) | 0.0057 (9) | 0.0077 (10) | 0.0124 (10) |
N2 | 0.0696 (19) | 0.128 (3) | 0.096 (2) | 0.0106 (17) | 0.0412 (18) | 0.052 (2) |
N1' | 0.0332 (12) | 0.0552 (14) | 0.0418 (13) | 0.0043 (9) | 0.0058 (10) | 0.0083 (10) |
N2' | 0.074 (2) | 0.123 (3) | 0.097 (2) | 0.0177 (17) | 0.0457 (19) | 0.054 (2) |
O1 | 0.0475 (12) | 0.0852 (14) | 0.0403 (11) | 0.0015 (10) | 0.0128 (9) | 0.0182 (10) |
O2 | 0.0322 (10) | 0.1174 (18) | 0.0549 (12) | 0.0120 (10) | 0.0048 (9) | 0.0324 (12) |
O1' | 0.0608 (13) | 0.0868 (15) | 0.0474 (12) | −0.0075 (11) | 0.0176 (10) | 0.0185 (10) |
O2' | 0.0313 (10) | 0.1156 (18) | 0.0479 (12) | −0.0013 (10) | 0.0024 (9) | 0.0169 (11) |
C1 | 0.0450 (18) | 0.092 (3) | 0.0511 (18) | 0.0016 (16) | 0.0138 (14) | 0.0194 (18) |
C2 | 0.0458 (15) | 0.0444 (15) | 0.0362 (14) | 0.0025 (11) | 0.0099 (12) | 0.0055 (11) |
C3 | 0.0360 (14) | 0.0544 (17) | 0.0436 (15) | 0.0042 (12) | 0.0057 (12) | 0.0106 (12) |
C4 | 0.0414 (15) | 0.0525 (16) | 0.0393 (15) | 0.0055 (12) | 0.0075 (12) | 0.0132 (12) |
C5 | 0.0383 (14) | 0.0421 (15) | 0.0422 (15) | 0.0029 (11) | 0.0070 (12) | 0.0092 (11) |
C6 | 0.0384 (15) | 0.0596 (18) | 0.0493 (16) | 0.0042 (13) | 0.0038 (13) | 0.0171 (13) |
C7 | 0.0457 (16) | 0.0597 (18) | 0.0415 (15) | 0.0053 (13) | 0.0042 (13) | 0.0148 (13) |
C8 | 0.0352 (14) | 0.0553 (17) | 0.0487 (16) | 0.0082 (12) | 0.0079 (12) | 0.0173 (13) |
C9 | 0.0378 (14) | 0.0431 (15) | 0.0424 (15) | 0.0052 (11) | 0.0106 (12) | 0.0092 (11) |
C10 | 0.0413 (15) | 0.0619 (18) | 0.0444 (16) | 0.0029 (12) | 0.0050 (13) | 0.0160 (14) |
C11 | 0.0343 (15) | 0.067 (2) | 0.0563 (18) | 0.0029 (13) | 0.0081 (13) | 0.0177 (14) |
C12 | 0.0428 (15) | 0.0513 (17) | 0.0518 (17) | 0.0070 (12) | 0.0170 (13) | 0.0158 (13) |
C13 | 0.0526 (18) | 0.079 (2) | 0.0433 (17) | 0.0016 (15) | 0.0105 (14) | 0.0178 (15) |
C14 | 0.0405 (16) | 0.074 (2) | 0.0449 (17) | −0.0036 (14) | 0.0043 (13) | 0.0152 (14) |
C15 | 0.0537 (19) | 0.074 (2) | 0.067 (2) | 0.0091 (15) | 0.0228 (16) | 0.0270 (17) |
C1' | 0.061 (2) | 0.099 (3) | 0.075 (2) | −0.0007 (19) | 0.0321 (19) | 0.024 (2) |
C2' | 0.0536 (17) | 0.0506 (17) | 0.0435 (16) | 0.0030 (13) | 0.0154 (13) | 0.0126 (12) |
C3' | 0.0370 (15) | 0.0622 (19) | 0.0493 (17) | −0.0038 (13) | 0.0088 (13) | 0.0091 (14) |
C4' | 0.0412 (15) | 0.0586 (18) | 0.0424 (15) | 0.0002 (12) | 0.0045 (13) | 0.0110 (13) |
C5' | 0.0396 (14) | 0.0407 (14) | 0.0390 (14) | 0.0050 (11) | 0.0058 (11) | 0.0064 (11) |
C6' | 0.0411 (15) | 0.0652 (19) | 0.0458 (16) | −0.0010 (13) | 0.0042 (13) | 0.0134 (14) |
C7' | 0.0571 (19) | 0.066 (2) | 0.0399 (16) | −0.0028 (14) | 0.0033 (14) | 0.0132 (14) |
C8' | 0.0368 (14) | 0.0545 (17) | 0.0386 (15) | −0.0002 (12) | 0.0048 (12) | 0.0073 (12) |
C9' | 0.0397 (14) | 0.0424 (15) | 0.0379 (14) | 0.0034 (11) | 0.0072 (11) | 0.0047 (11) |
C10' | 0.0400 (15) | 0.0512 (17) | 0.0389 (15) | 0.0047 (12) | 0.0058 (12) | 0.0103 (12) |
C11' | 0.0359 (15) | 0.0552 (17) | 0.0502 (16) | 0.0052 (12) | 0.0086 (13) | 0.0107 (13) |
C12' | 0.0458 (16) | 0.0480 (16) | 0.0468 (16) | 0.0038 (12) | 0.0141 (13) | 0.0102 (12) |
C13' | 0.0540 (18) | 0.0588 (18) | 0.0463 (16) | 0.0099 (13) | 0.0132 (14) | 0.0190 (14) |
C14' | 0.0405 (15) | 0.0565 (17) | 0.0452 (16) | 0.0094 (12) | 0.0049 (13) | 0.0148 (13) |
C15' | 0.0553 (19) | 0.069 (2) | 0.0615 (19) | 0.0087 (15) | 0.0192 (16) | 0.0241 (15) |
N1—O2 | 1.297 (3) | C11—H11 | 0.96 (3) |
N1—C8 | 1.309 (3) | C12—C13 | 1.379 (4) |
N1—C9 | 1.454 (3) | C12—C15 | 1.440 (4) |
N2—C15 | 1.139 (3) | C13—C14 | 1.377 (4) |
O1—C2 | 1.360 (3) | C13—H13 | 0.98 (3) |
O1—C1 | 1.432 (3) | C14—H14 | 0.94 (3) |
N1'—O2' | 1.299 (3) | C1'—H1'A | 0.96 (4) |
N1'—C8' | 1.314 (3) | C1'—H1'B | 1.03 (4) |
N1'—C9' | 1.450 (3) | C1'—H1'C | 0.95 (4) |
N2'—C15' | 1.137 (4) | C2'—C3' | 1.382 (4) |
O1'—C2' | 1.364 (3) | C2'—C7' | 1.385 (4) |
O1'—C1' | 1.427 (4) | C3'—C4' | 1.384 (4) |
C1—H1A | 0.97 (4) | C3'—H3' | 0.90 (3) |
C1—H1B | 1.05 (3) | C4'—C5' | 1.391 (4) |
C1—H1C | 1.04 (3) | C4'—H4' | 0.98 (3) |
C2—C3 | 1.385 (4) | C5'—C6' | 1.407 (4) |
C2—C7 | 1.392 (4) | C5'—C8' | 1.436 (3) |
C3—C4 | 1.386 (4) | C6'—C7' | 1.370 (4) |
C3—H3 | 0.96 (3) | C6'—H6' | 0.99 (3) |
C4—C5 | 1.398 (3) | C7'—H7' | 0.93 (3) |
C4—H4 | 0.98 (3) | C8'—H8' | 0.98 (3) |
C5—C6 | 1.410 (4) | C9'—C10' | 1.383 (3) |
C5—C8 | 1.429 (3) | C9'—C14' | 1.392 (4) |
C6—C7 | 1.362 (4) | C10'—C11' | 1.375 (3) |
C6—H6 | 0.95 (3) | C10'—H10' | 0.97 (3) |
C7—H7 | 1.01 (3) | C11'—C12' | 1.390 (4) |
C8—H8 | 0.91 (3) | C11'—H11' | 0.92 (3) |
C9—C10 | 1.380 (4) | C12'—C13' | 1.386 (4) |
C9—C14 | 1.380 (4) | C12'—C15' | 1.443 (4) |
C10—C11 | 1.380 (4) | C13'—C14' | 1.383 (4) |
C10—H10 | 1.00 (3) | C13'—H13' | 1.01 (3) |
C11—C12 | 1.386 (4) | C14'—H14' | 0.96 (3) |
O2—N1—C8 | 122.8 (2) | C14—C13—H13 | 122.2 (17) |
O2—N1—C9 | 116.3 (2) | C9—C14—C13 | 119.8 (3) |
C8—N1—C9 | 120.9 (2) | C9—C14—H14 | 118.7 (18) |
C8'—N1'—C9' | 121.1 (2) | C13—C14—H14 | 121.4 (18) |
C2—O1—C1 | 118.5 (2) | O1'—C1'—H1'A | 107 (2) |
N1—C8—C5 | 129.0 (2) | O1'—C1'—H1'B | 112 (2) |
N2—C15—C12 | 178.4 (4) | H1'A—C1'—H1'B | 112 (3) |
O2'—N1'—C8' | 122.6 (2) | O1'—C1'—H1'C | 108 (2) |
O2'—N1'—C9' | 116.3 (2) | H1'A—C1'—H1'C | 109 (3) |
C2'—O1'—C1' | 118.5 (2) | H1'B—C1'—H1'C | 109 (3) |
O1—C1—H1A | 104 (2) | O1'—C2'—C3' | 124.2 (2) |
O1—C1—H1B | 111.7 (18) | O1'—C2'—C7' | 115.7 (2) |
H1A—C1—H1B | 114 (3) | C3'—C2'—C7' | 120.1 (2) |
O1—C1—H1C | 110.9 (19) | C2'—C3'—C4' | 119.9 (2) |
H1A—C1—H1C | 106 (3) | C2'—C3'—H3' | 120.1 (18) |
H1B—C1—H1C | 109 (3) | C4'—C3'—H3' | 119.9 (18) |
O1—C2—C3 | 125.4 (2) | C3'—C4'—C5' | 121.3 (3) |
O1—C2—C7 | 115.0 (2) | C3'—C4'—H4' | 120.3 (16) |
C3—C2—C7 | 119.5 (2) | C5'—C4'—H4' | 118.2 (16) |
C2—C3—C4 | 120.6 (2) | C4'—C5'—C6' | 117.4 (2) |
C2—C3—H3 | 119.6 (16) | C4'—C5'—C8' | 126.4 (2) |
C4—C3—H3 | 119.7 (16) | C6'—C5'—C8' | 116.2 (2) |
C3—C4—C5 | 120.7 (2) | C7'—C6'—C5' | 121.6 (3) |
C3—C4—H4 | 121.6 (15) | C7'—C6'—H6' | 120.3 (16) |
C5—C4—H4 | 117.5 (15) | C5'—C6'—H6' | 118.0 (16) |
C4—C5—C6 | 117.2 (2) | C6'—C7'—C2' | 119.7 (3) |
C4—C5—C8 | 126.9 (2) | C6'—C7'—H7' | 120.6 (18) |
C6—C5—C8 | 115.9 (2) | C2'—C7'—H7' | 119.7 (18) |
C7—C6—C5 | 122.2 (3) | N1'—C8'—C5' | 127.5 (2) |
C7—C6—H6 | 119.7 (17) | N1'—C8'—H8' | 113.8 (15) |
C5—C6—H6 | 118.1 (17) | C5'—C8'—H8' | 118.6 (15) |
C6—C7—C2 | 119.8 (3) | C10'—C9'—C14' | 120.8 (2) |
C6—C7—H7 | 119.0 (15) | C10'—C9'—N1' | 121.3 (2) |
C2—C7—H7 | 121.0 (15) | C14'—C9'—N1' | 117.8 (2) |
N1—C8—H8 | 111.7 (17) | C11'—C10'—C9' | 119.8 (2) |
C5—C8—H8 | 119.2 (17) | C11'—C10'—H10' | 121.6 (15) |
C10—C9—C14 | 120.3 (2) | C9'—C10'—H10' | 118.2 (15) |
C10—C9—N1 | 121.6 (2) | C10'—C11'—C12' | 119.8 (2) |
C14—C9—N1 | 118.1 (2) | C10'—C11'—H11' | 121.6 (17) |
C9—C10—C11 | 119.9 (3) | C12'—C11'—H11' | 118.5 (17) |
C9—C10—H10 | 119.6 (15) | C13'—C12'—C11' | 120.5 (2) |
C11—C10—H10 | 120.5 (15) | C13'—C12'—C15' | 121.2 (2) |
C10—C11—C12 | 119.8 (3) | C11'—C12'—C15' | 118.3 (2) |
C10—C11—H11 | 122.3 (17) | C14'—C13'—C12' | 119.8 (3) |
C12—C11—H11 | 117.8 (17) | C14'—C13'—H13' | 123.0 (16) |
C13—C12—C11 | 120.1 (2) | C12'—C13'—H13' | 117.2 (16) |
C13—C12—C15 | 121.0 (3) | C13'—C14'—C9' | 119.3 (3) |
C11—C12—C15 | 118.9 (3) | C13'—C14'—H14' | 122.8 (16) |
C12—C13—C14 | 120.1 (3) | C9'—C14'—H14' | 117.7 (16) |
C12—C13—H13 | 117.3 (17) | N2'—C15'—C12' | 178.6 (4) |
C1—O1—C2—C3 | 2.4 (4) | C1'—O1'—C2'—C3' | −11.9 (4) |
C1—O1—C2—C7 | −179.1 (3) | C1'—O1'—C2'—C7' | 168.2 (3) |
O1—C2—C3—C4 | 178.0 (2) | O1'—C2'—C3'—C4' | −178.8 (3) |
C7—C2—C3—C4 | −0.3 (4) | C7'—C2'—C3'—C4' | 1.1 (4) |
C2—C3—C4—C5 | −0.3 (4) | C2'—C3'—C4'—C5' | −1.2 (4) |
C3—C4—C5—C6 | 0.2 (4) | C3'—C4'—C5'—C6' | 0.3 (4) |
C3—C4—C5—C8 | −179.4 (3) | C3'—C4'—C5'—C8' | −179.9 (3) |
C4—C5—C6—C7 | 0.6 (4) | C4'—C5'—C6'—C7' | 0.7 (4) |
C8—C5—C6—C7 | −179.8 (3) | C8'—C5'—C6'—C7' | −179.1 (3) |
C5—C6—C7—C2 | −1.2 (4) | C5'—C6'—C7'—C2' | −0.8 (5) |
O1—C2—C7—C6 | −177.4 (2) | O1'—C2'—C7'—C6' | 179.8 (3) |
C3—C2—C7—C6 | 1.1 (4) | C3'—C2'—C7'—C6' | −0.1 (4) |
O2—N1—C8—C5 | 3.3 (4) | O2'—N1'—C8'—C5' | 3.3 (4) |
C9—N1—C8—C5 | −176.0 (2) | C9'—N1'—C8'—C5' | −175.0 (2) |
C4—C5—C8—N1 | −6.8 (5) | C4'—C5'—C8'—N1' | −2.4 (4) |
C6—C5—C8—N1 | 173.6 (3) | C6'—C5'—C8'—N1' | 177.3 (3) |
O2—N1—C9—C10 | −154.1 (2) | O2'—N1'—C9'—C10' | −150.9 (2) |
C8—N1—C9—C10 | 25.3 (4) | C8'—N1'—C9'—C10' | 27.4 (4) |
O2—N1—C9—C14 | 23.3 (3) | O2'—N1'—C9'—C14' | 25.9 (3) |
C8—N1—C9—C14 | −157.4 (3) | C8'—N1'—C9'—C14' | −155.8 (2) |
C14—C9—C10—C11 | 2.2 (4) | C14'—C9'—C10'—C11' | 0.1 (4) |
N1—C9—C10—C11 | 179.5 (2) | N1'—C9'—C10'—C11' | 176.8 (2) |
C9—C10—C11—C12 | −2.2 (4) | C9'—C10'—C11'—C12' | 0.3 (4) |
C10—C11—C12—C13 | 1.6 (4) | C10'—C11'—C12'—C13' | −0.3 (4) |
C10—C11—C12—C15 | −178.5 (3) | C10'—C11'—C12'—C15' | 179.3 (3) |
C11—C12—C13—C14 | −1.0 (5) | C11'—C12'—C13'—C14' | −0.2 (4) |
C15—C12—C13—C14 | 179.1 (3) | C15'—C12'—C13'—C14' | −179.8 (3) |
C10—C9—C14—C13 | −1.7 (4) | C12'—C13'—C14'—C9' | 0.5 (4) |
N1—C9—C14—C13 | −179.0 (3) | C10'—C9'—C14'—C13' | −0.5 (4) |
C12—C13—C14—C9 | 1.0 (5) | N1'—C9'—C14'—C13' | −177.3 (2) |
C13—C12—C15—N2 | −148 (12) | C13'—C12'—C15'—N2' | 152 (14) |
C11—C12—C15—N2 | 32 (12) | C11'—C12'—C15'—N2' | −28 (14) |
Experimental details
Crystal data | |
Chemical formula | C15H12N2O2 |
Mr | 252.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5821 (16), 7.613 (2), 22.270 (3) |
α, β, γ (°) | 99.469 (16), 96.999 (12), 94.79 (2) |
V (Å3) | 1251.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.30 × 0.13 |
Data collection | |
Diffractometer | Enraf Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4490, 4370, 2688 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.177, 1.01 |
No. of reflections | 4370 |
No. of parameters | 415 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.22 |
Computer programs: CAD-4 EXPRESS (Enraf Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1998).
N1—O2 | 1.297 (3) | N1'—O2' | 1.299 (3) |
N1—C8 | 1.309 (3) | N1'—C8' | 1.314 (3) |
N1—C9 | 1.454 (3) | N1'—C9' | 1.450 (3) |
N2—C15 | 1.139 (3) | N2'—C15' | 1.137 (4) |
O1—C2 | 1.360 (3) | O1'—C2' | 1.364 (3) |
O1—C1 | 1.432 (3) | O1'—C1' | 1.427 (4) |
O2—N1—C8 | 122.8 (2) | O2'—N1'—C8' | 122.6 (2) |
O2—N1—C9 | 116.3 (2) | O2'—N1'—C9' | 116.3 (2) |
C2—O1—C1 | 118.5 (2) | C2'—O1'—C1' | 118.5 (2) |
N1—C8—C5 | 129.0 (2) | N1'—C8'—C5' | 127.5 (2) |
N2—C15—C12 | 178.4 (4) | N2'—C15'—C12' | 178.6 (4) |
O2—N1—C8—C5 | 3.3 (4) | O2'—N1'—C8'—C5' | 3.3 (4) |
C9—N1—C8—C5 | −176.0 (2) | C9'—N1'—C8'—C5' | −175.0 (2) |
C4—C5—C8—N1 | −6.8 (5) | C4'—C5'—C8'—N1' | −2.4 (4) |
C6—C5—C8—N1 | 173.6 (3) | C6'—C5'—C8'—N1' | 177.3 (3) |
O2—N1—C9—C10 | −154.1 (2) | O2'—N1'—C9'—C10' | −150.9 (2) |
C8—N1—C9—C10 | 25.3 (4) | C8'—N1'—C9'—C10' | 27.4 (4) |
O2—N1—C9—C14 | 23.3 (3) | O2'—N1'—C9'—C14' | 25.9 (3) |
C8—N1—C9—C14 | −157.4 (3) | C8'—N1'—C9'—C14' | −155.8 (2) |
N1—C9—C14—C13 | −179.0 (3) | N1'—C9'—C14'—C13' | −177.3 (2) |
The title compound, (I), was synthesized for use as a photobleachable material. The crystal structure of (I) confirms that it exists as a nitrone. \scheme
The asymmetric unit of (I) consists of two crystallographically independent molecules, A (unprimed labels) and B (primed labels), as shown in Fig. 1. The nitrone units in each molecule are closely planar, with displacements of −0.016 (2) [−0.022 (2)], 0.0329 (2) [0.039 (2)], 0.012 (2) [0.019 (2)], 0.000 (2) [0.000 (2)] and −0.015 (2) [−0.021 (2)]Å, respectively, for atoms C5, C8, N1, O2 and C9 (values for molecule B, here and elsewhere, are given in square brackets). The nitrone unit is closely coplanar with the 4-methoxyphenyl group: the dihedral angle is 5.2 (1)° [3.0 (1)°]. The 4-cyanophenyl unit is substantially twisted with respect to the nitrone unit and the 4-methoxyphenyl group, with dihedral angles of 24.2 (1) [27.1 (1)] and 19.4 (1)° [26.5 (1)°], respectively. Similar planarity of the nitrone moiety is found in N-methyl benzaldehyde nitrone (Bedford et al., 1991) and N-(p-hydroxybenzylidene)phenylamine N-oxide (Vijayalakshmi et al., 1997).
Both molecule A and molecule B adopt the more commonly observed Z isomer. The torsion angle about the C=N bond, O2—N1—C8—C5, is 3.3 (4)° [3.3 (4)°]. The N1—O2 bond lengths are nearly equal to the value of 1.293 (3) Å reported by Bedford et al. (1991). The phenyl bond lengths and angles are in agreement with the expected values reported by Allen et al. (1987).
As apparent from Fig. 1, the two molecules are related to each other by a pseudo inversion centre. Deviations are manifest in different intramolecular dihedral angles between the 4-cyanophenyl and 4-methoxymethyl groups and in intermolecular dihedral angles of 6.4 (1)° and 4.4 (1)° between pseudo-symmetrically related 4-cyanomethyl and 4-methoxyphenyl groups. Please check all s.u.s added above and correct as necessary.