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In the crystal structure of the title compound, 4-cyano-N-(4-methoxy­benzyl­idene)­phenyl­amine N-oxide, C15H12N2O2, the 4-methoxy­phenyl is approximately coplanar with the nitrone moiety but significantly rotated with respect to the 4-cyano­phenyl moiety. The extent of this rotation is significantly different for the two crystallographically independent mol­ecules of the asymmetric unit [dihedral angles of 19.4 (1) and 26.5 (1)°]. The geometry about the C=N bond is Z. The two mol­ecules are related to one another by a pseudo inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199014596/ja1009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199014596/ja1009Isup2.hkl
Contains datablock I

CCDC reference: 142769

Comment top

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.

Experimental top

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.

Refinement top

All non-H atoms were refined anisotropically. The positions of the H atoms were refined, but their isotropic U values were constrained.

Computing details top

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).

Figures top
[Figure 1] 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.
4-cyano-N-(4-methoxybenzylidene)phenylamine N-oxide top
Crystal data top
C15H12N2O2Z = 4
Mr = 252.27F(000) = 528
Triclinic, P1Dx = 1.339 Mg m3
a = 7.5821 (16) ÅMo Kα radiation, λ = 0.71069 Å
b = 7.613 (2) ÅCell parameters from 25 reflections
c = 22.270 (3) Åθ = 11.3–14.2°
α = 99.469 (16)°µ = 0.09 mm1
β = 96.999 (12)°T = 293 K
γ = 94.79 (2)°Plate, yellow
V = 1251.5 (5) Å30.50 × 0.30 × 0.13 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.054
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.7°
Graphite monochromatorh = 98
non–profiled ω/2θ scansk = 98
4490 measured reflectionsl = 026
4370 independent reflections3 standard reflections every 300 min
2688 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177Only 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 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C15H12N2O2γ = 94.79 (2)°
Mr = 252.27V = 1251.5 (5) Å3
Triclinic, P1Z = 4
a = 7.5821 (16) ÅMo Kα radiation
b = 7.613 (2) ŵ = 0.09 mm1
c = 22.270 (3) ÅT = 293 K
α = 99.469 (16)°0.50 × 0.30 × 0.13 mm
β = 96.999 (12)°
Data collection top
Enraf Nonius CAD-4
diffractometer
Rint = 0.054
4490 measured reflections3 standard reflections every 300 min
4370 independent reflections intensity decay: 1%
2688 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.177Only H-atom coordinates refined
S = 1.01Δρmax = 0.24 e Å3
4370 reflectionsΔρmin = 0.22 e Å3
415 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7959 (3)0.9605 (3)0.27680 (10)0.0433 (5)
N20.1462 (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)
O11.1627 (2)1.1878 (3)0.04454 (8)0.0566 (5)
O20.9563 (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)
C11.3531 (4)1.1915 (5)0.04987 (15)0.0617 (8)
H1A1.384 (4)1.240 (4)0.0143 (17)0.092*
H1B1.395 (4)1.065 (5)0.0522 (15)0.092*
H1C1.414 (4)1.282 (4)0.0882 (16)0.092*
C21.0789 (3)1.1401 (3)0.09096 (11)0.0421 (6)
C31.1630 (4)1.0999 (4)0.14506 (12)0.0444 (6)
H31.290 (4)1.105 (3)0.1518 (12)0.053*
C41.0646 (3)1.0580 (4)0.19024 (12)0.0436 (6)
H41.121 (3)1.018 (3)0.2271 (13)0.052*
C50.8786 (3)1.0564 (3)0.18225 (11)0.0406 (6)
C60.7974 (4)1.0983 (4)0.12670 (13)0.0485 (7)
H60.670 (4)1.097 (3)0.1205 (12)0.058*
C70.8937 (4)1.1374 (4)0.08193 (13)0.0485 (7)
H70.830 (3)1.175 (3)0.0442 (13)0.058*
C80.7604 (4)1.0176 (4)0.22476 (13)0.0451 (7)
H80.643 (4)1.037 (3)0.2172 (12)0.054*
C90.6541 (3)0.9175 (3)0.31210 (11)0.0404 (6)
C100.4801 (3)0.8680 (4)0.28446 (13)0.0486 (7)
H100.449 (3)0.865 (3)0.2395 (13)0.058*
C110.3493 (4)0.8268 (4)0.31945 (13)0.0519 (7)
H110.227 (4)0.788 (4)0.3017 (13)0.062*
C120.3947 (3)0.8296 (3)0.38184 (13)0.0468 (7)
C130.5692 (4)0.8775 (4)0.40908 (14)0.0574 (8)
H130.597 (4)0.867 (4)0.4524 (14)0.069*
C140.6993 (4)0.9201 (4)0.37420 (13)0.0534 (7)
H140.820 (4)0.948 (4)0.3916 (13)0.064*
C150.2571 (4)0.7820 (4)0.41726 (14)0.0620 (8)
C1'0.1378 (5)0.2319 (6)0.43870 (19)0.0759 (10)
H1'A0.098 (5)0.205 (5)0.4759 (19)0.114*
H1'B0.100 (5)0.129 (5)0.4023 (19)0.114*
H1'C0.088 (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)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0340 (12)0.0558 (14)0.0421 (12)0.0057 (9)0.0077 (10)0.0124 (10)
N20.0696 (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)
O10.0475 (12)0.0852 (14)0.0403 (11)0.0015 (10)0.0128 (9)0.0182 (10)
O20.0322 (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)
C10.0450 (18)0.092 (3)0.0511 (18)0.0016 (16)0.0138 (14)0.0194 (18)
C20.0458 (15)0.0444 (15)0.0362 (14)0.0025 (11)0.0099 (12)0.0055 (11)
C30.0360 (14)0.0544 (17)0.0436 (15)0.0042 (12)0.0057 (12)0.0106 (12)
C40.0414 (15)0.0525 (16)0.0393 (15)0.0055 (12)0.0075 (12)0.0132 (12)
C50.0383 (14)0.0421 (15)0.0422 (15)0.0029 (11)0.0070 (12)0.0092 (11)
C60.0384 (15)0.0596 (18)0.0493 (16)0.0042 (13)0.0038 (13)0.0171 (13)
C70.0457 (16)0.0597 (18)0.0415 (15)0.0053 (13)0.0042 (13)0.0148 (13)
C80.0352 (14)0.0553 (17)0.0487 (16)0.0082 (12)0.0079 (12)0.0173 (13)
C90.0378 (14)0.0431 (15)0.0424 (15)0.0052 (11)0.0106 (12)0.0092 (11)
C100.0413 (15)0.0619 (18)0.0444 (16)0.0029 (12)0.0050 (13)0.0160 (14)
C110.0343 (15)0.067 (2)0.0563 (18)0.0029 (13)0.0081 (13)0.0177 (14)
C120.0428 (15)0.0513 (17)0.0518 (17)0.0070 (12)0.0170 (13)0.0158 (13)
C130.0526 (18)0.079 (2)0.0433 (17)0.0016 (15)0.0105 (14)0.0178 (15)
C140.0405 (16)0.074 (2)0.0449 (17)0.0036 (14)0.0043 (13)0.0152 (14)
C150.0537 (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)
Geometric parameters (Å, º) top
N1—O21.297 (3)C11—H110.96 (3)
N1—C81.309 (3)C12—C131.379 (4)
N1—C91.454 (3)C12—C151.440 (4)
N2—C151.139 (3)C13—C141.377 (4)
O1—C21.360 (3)C13—H130.98 (3)
O1—C11.432 (3)C14—H140.94 (3)
N1'—O2'1.299 (3)C1'—H1'A0.96 (4)
N1'—C8'1.314 (3)C1'—H1'B1.03 (4)
N1'—C9'1.450 (3)C1'—H1'C0.95 (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—H1A0.97 (4)C3'—H3'0.90 (3)
C1—H1B1.05 (3)C4'—C5'1.391 (4)
C1—H1C1.04 (3)C4'—H4'0.98 (3)
C2—C31.385 (4)C5'—C6'1.407 (4)
C2—C71.392 (4)C5'—C8'1.436 (3)
C3—C41.386 (4)C6'—C7'1.370 (4)
C3—H30.96 (3)C6'—H6'0.99 (3)
C4—C51.398 (3)C7'—H7'0.93 (3)
C4—H40.98 (3)C8'—H8'0.98 (3)
C5—C61.410 (4)C9'—C10'1.383 (3)
C5—C81.429 (3)C9'—C14'1.392 (4)
C6—C71.362 (4)C10'—C11'1.375 (3)
C6—H60.95 (3)C10'—H10'0.97 (3)
C7—H71.01 (3)C11'—C12'1.390 (4)
C8—H80.91 (3)C11'—H11'0.92 (3)
C9—C101.380 (4)C12'—C13'1.386 (4)
C9—C141.380 (4)C12'—C15'1.443 (4)
C10—C111.380 (4)C13'—C14'1.383 (4)
C10—H101.00 (3)C13'—H13'1.01 (3)
C11—C121.386 (4)C14'—H14'0.96 (3)
O2—N1—C8122.8 (2)C14—C13—H13122.2 (17)
O2—N1—C9116.3 (2)C9—C14—C13119.8 (3)
C8—N1—C9120.9 (2)C9—C14—H14118.7 (18)
C8'—N1'—C9'121.1 (2)C13—C14—H14121.4 (18)
C2—O1—C1118.5 (2)O1'—C1'—H1'A107 (2)
N1—C8—C5129.0 (2)O1'—C1'—H1'B112 (2)
N2—C15—C12178.4 (4)H1'A—C1'—H1'B112 (3)
O2'—N1'—C8'122.6 (2)O1'—C1'—H1'C108 (2)
O2'—N1'—C9'116.3 (2)H1'A—C1'—H1'C109 (3)
C2'—O1'—C1'118.5 (2)H1'B—C1'—H1'C109 (3)
O1—C1—H1A104 (2)O1'—C2'—C3'124.2 (2)
O1—C1—H1B111.7 (18)O1'—C2'—C7'115.7 (2)
H1A—C1—H1B114 (3)C3'—C2'—C7'120.1 (2)
O1—C1—H1C110.9 (19)C2'—C3'—C4'119.9 (2)
H1A—C1—H1C106 (3)C2'—C3'—H3'120.1 (18)
H1B—C1—H1C109 (3)C4'—C3'—H3'119.9 (18)
O1—C2—C3125.4 (2)C3'—C4'—C5'121.3 (3)
O1—C2—C7115.0 (2)C3'—C4'—H4'120.3 (16)
C3—C2—C7119.5 (2)C5'—C4'—H4'118.2 (16)
C2—C3—C4120.6 (2)C4'—C5'—C6'117.4 (2)
C2—C3—H3119.6 (16)C4'—C5'—C8'126.4 (2)
C4—C3—H3119.7 (16)C6'—C5'—C8'116.2 (2)
C3—C4—C5120.7 (2)C7'—C6'—C5'121.6 (3)
C3—C4—H4121.6 (15)C7'—C6'—H6'120.3 (16)
C5—C4—H4117.5 (15)C5'—C6'—H6'118.0 (16)
C4—C5—C6117.2 (2)C6'—C7'—C2'119.7 (3)
C4—C5—C8126.9 (2)C6'—C7'—H7'120.6 (18)
C6—C5—C8115.9 (2)C2'—C7'—H7'119.7 (18)
C7—C6—C5122.2 (3)N1'—C8'—C5'127.5 (2)
C7—C6—H6119.7 (17)N1'—C8'—H8'113.8 (15)
C5—C6—H6118.1 (17)C5'—C8'—H8'118.6 (15)
C6—C7—C2119.8 (3)C10'—C9'—C14'120.8 (2)
C6—C7—H7119.0 (15)C10'—C9'—N1'121.3 (2)
C2—C7—H7121.0 (15)C14'—C9'—N1'117.8 (2)
N1—C8—H8111.7 (17)C11'—C10'—C9'119.8 (2)
C5—C8—H8119.2 (17)C11'—C10'—H10'121.6 (15)
C10—C9—C14120.3 (2)C9'—C10'—H10'118.2 (15)
C10—C9—N1121.6 (2)C10'—C11'—C12'119.8 (2)
C14—C9—N1118.1 (2)C10'—C11'—H11'121.6 (17)
C9—C10—C11119.9 (3)C12'—C11'—H11'118.5 (17)
C9—C10—H10119.6 (15)C13'—C12'—C11'120.5 (2)
C11—C10—H10120.5 (15)C13'—C12'—C15'121.2 (2)
C10—C11—C12119.8 (3)C11'—C12'—C15'118.3 (2)
C10—C11—H11122.3 (17)C14'—C13'—C12'119.8 (3)
C12—C11—H11117.8 (17)C14'—C13'—H13'123.0 (16)
C13—C12—C11120.1 (2)C12'—C13'—H13'117.2 (16)
C13—C12—C15121.0 (3)C13'—C14'—C9'119.3 (3)
C11—C12—C15118.9 (3)C13'—C14'—H14'122.8 (16)
C12—C13—C14120.1 (3)C9'—C14'—H14'117.7 (16)
C12—C13—H13117.3 (17)N2'—C15'—C12'178.6 (4)
C1—O1—C2—C32.4 (4)C1'—O1'—C2'—C3'11.9 (4)
C1—O1—C2—C7179.1 (3)C1'—O1'—C2'—C7'168.2 (3)
O1—C2—C3—C4178.0 (2)O1'—C2'—C3'—C4'178.8 (3)
C7—C2—C3—C40.3 (4)C7'—C2'—C3'—C4'1.1 (4)
C2—C3—C4—C50.3 (4)C2'—C3'—C4'—C5'1.2 (4)
C3—C4—C5—C60.2 (4)C3'—C4'—C5'—C6'0.3 (4)
C3—C4—C5—C8179.4 (3)C3'—C4'—C5'—C8'179.9 (3)
C4—C5—C6—C70.6 (4)C4'—C5'—C6'—C7'0.7 (4)
C8—C5—C6—C7179.8 (3)C8'—C5'—C6'—C7'179.1 (3)
C5—C6—C7—C21.2 (4)C5'—C6'—C7'—C2'0.8 (5)
O1—C2—C7—C6177.4 (2)O1'—C2'—C7'—C6'179.8 (3)
C3—C2—C7—C61.1 (4)C3'—C2'—C7'—C6'0.1 (4)
O2—N1—C8—C53.3 (4)O2'—N1'—C8'—C5'3.3 (4)
C9—N1—C8—C5176.0 (2)C9'—N1'—C8'—C5'175.0 (2)
C4—C5—C8—N16.8 (5)C4'—C5'—C8'—N1'2.4 (4)
C6—C5—C8—N1173.6 (3)C6'—C5'—C8'—N1'177.3 (3)
O2—N1—C9—C10154.1 (2)O2'—N1'—C9'—C10'150.9 (2)
C8—N1—C9—C1025.3 (4)C8'—N1'—C9'—C10'27.4 (4)
O2—N1—C9—C1423.3 (3)O2'—N1'—C9'—C14'25.9 (3)
C8—N1—C9—C14157.4 (3)C8'—N1'—C9'—C14'155.8 (2)
C14—C9—C10—C112.2 (4)C14'—C9'—C10'—C11'0.1 (4)
N1—C9—C10—C11179.5 (2)N1'—C9'—C10'—C11'176.8 (2)
C9—C10—C11—C122.2 (4)C9'—C10'—C11'—C12'0.3 (4)
C10—C11—C12—C131.6 (4)C10'—C11'—C12'—C13'0.3 (4)
C10—C11—C12—C15178.5 (3)C10'—C11'—C12'—C15'179.3 (3)
C11—C12—C13—C141.0 (5)C11'—C12'—C13'—C14'0.2 (4)
C15—C12—C13—C14179.1 (3)C15'—C12'—C13'—C14'179.8 (3)
C10—C9—C14—C131.7 (4)C12'—C13'—C14'—C9'0.5 (4)
N1—C9—C14—C13179.0 (3)C10'—C9'—C14'—C13'0.5 (4)
C12—C13—C14—C91.0 (5)N1'—C9'—C14'—C13'177.3 (2)
C13—C12—C15—N2148 (12)C13'—C12'—C15'—N2'152 (14)
C11—C12—C15—N232 (12)C11'—C12'—C15'—N2'28 (14)

Experimental details

Crystal data
Chemical formulaC15H12N2O2
Mr252.27
Crystal system, space groupTriclinic, 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)
V3)1251.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.30 × 0.13
Data collection
DiffractometerEnraf Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4490, 4370, 2688
Rint0.054
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.177, 1.01
No. of reflections4370
No. of parameters415
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)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).

Selected geometric parameters (Å, º) top
N1—O21.297 (3)N1'—O2'1.299 (3)
N1—C81.309 (3)N1'—C8'1.314 (3)
N1—C91.454 (3)N1'—C9'1.450 (3)
N2—C151.139 (3)N2'—C15'1.137 (4)
O1—C21.360 (3)O1'—C2'1.364 (3)
O1—C11.432 (3)O1'—C1'1.427 (4)
O2—N1—C8122.8 (2)O2'—N1'—C8'122.6 (2)
O2—N1—C9116.3 (2)O2'—N1'—C9'116.3 (2)
C2—O1—C1118.5 (2)C2'—O1'—C1'118.5 (2)
N1—C8—C5129.0 (2)N1'—C8'—C5'127.5 (2)
N2—C15—C12178.4 (4)N2'—C15'—C12'178.6 (4)
O2—N1—C8—C53.3 (4)O2'—N1'—C8'—C5'3.3 (4)
C9—N1—C8—C5176.0 (2)C9'—N1'—C8'—C5'175.0 (2)
C4—C5—C8—N16.8 (5)C4'—C5'—C8'—N1'2.4 (4)
C6—C5—C8—N1173.6 (3)C6'—C5'—C8'—N1'177.3 (3)
O2—N1—C9—C10154.1 (2)O2'—N1'—C9'—C10'150.9 (2)
C8—N1—C9—C1025.3 (4)C8'—N1'—C9'—C10'27.4 (4)
O2—N1—C9—C1423.3 (3)O2'—N1'—C9'—C14'25.9 (3)
C8—N1—C9—C14157.4 (3)C8'—N1'—C9'—C14'155.8 (2)
N1—C9—C14—C13179.0 (3)N1'—C9'—C14'—C13'177.3 (2)
 

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