The title compound, C
24H
18N
4O, is a bis-bidentate Schiff base ligand exhibiting pseudo-
C2 symmetry. The molecule is twisted about the central ether linkage and exhibits an imine
E configuration. In the crystal, the molecules are linked by weak intermolecular C—H
N hydrogen bonds.
Supporting information
CCDC reference: 163946
Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97).
Crystal data top
C24H18N4O | F(000) = 792 |
Mr = 378.42 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3403 (8) Å | Cell parameters from 5000 reflections |
b = 18.3849 (17) Å | θ = 2.0–25.9° |
c = 8.5868 (6) Å | µ = 0.08 mm−1 |
β = 91.958 (8)° | T = 153 K |
V = 1947.0 (3) Å3 | Block, yellow |
Z = 4 | 0.55 × 0.50 × 0.35 mm |
Data collection top
STOE IPDS diffractometer | 2904 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.9°, θmin = 2.0° |
Detector resolution: 0.81Å pixels mm-1 | h = −14→15 |
φ oscillation scans | k = −22→22 |
14238 measured reflections | l = −10→10 |
3716 independent reflections | |
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)] = 0.035 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.094 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1419P] where P = (Fo2 + 2Fc2)/3 |
3716 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.13 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 | |
N1 | 0.19492 (9) | 0.18318 (8) | −0.25245 (15) | 0.0586 (3) | |
N2 | 0.42393 (7) | 0.11855 (5) | −0.03145 (11) | 0.0353 (2) | |
N3 | 0.89625 (8) | −0.04533 (6) | 0.85138 (13) | 0.0444 (3) | |
N4 | 1.15560 (9) | −0.12726 (7) | 0.83900 (13) | 0.0531 (3) | |
O1 | 0.62405 (7) | 0.15817 (4) | 0.55555 (10) | 0.0415 (2) | |
C1 | 0.15263 (14) | 0.18432 (10) | −0.3984 (2) | 0.0676 (5) | |
H1 | 0.0842 (16) | 0.2090 (11) | −0.410 (2) | 0.094 (6)* | |
C2 | 0.20045 (13) | 0.15302 (9) | −0.52382 (18) | 0.0585 (4) | |
H2 | 0.1649 (13) | 0.1581 (9) | −0.625 (2) | 0.070 (5)* | |
C3 | 0.29796 (12) | 0.11791 (8) | −0.49962 (17) | 0.0509 (3) | |
H3 | 0.3340 (14) | 0.0957 (9) | −0.590 (2) | 0.072 (5)* | |
C4 | 0.34383 (10) | 0.11572 (7) | −0.35085 (15) | 0.0416 (3) | |
H4 | 0.4160 (13) | 0.0922 (8) | −0.3283 (18) | 0.060 (4)* | |
C5 | 0.28982 (9) | 0.14844 (6) | −0.23027 (14) | 0.0383 (3) | |
C6 | 0.33588 (10) | 0.15064 (7) | −0.06976 (15) | 0.0388 (3) | |
H6 | 0.2944 (11) | 0.1796 (8) | 0.0061 (18) | 0.052 (4)* | |
C7 | 0.47095 (8) | 0.12860 (6) | 0.11985 (13) | 0.0326 (2) | |
C8 | 0.47424 (9) | 0.19635 (6) | 0.19436 (14) | 0.0347 (3) | |
H8 | 0.4408 (10) | 0.2389 (8) | 0.1432 (16) | 0.047 (4)* | |
C9 | 0.52812 (9) | 0.20472 (6) | 0.33687 (14) | 0.0348 (3) | |
H9 | 0.5329 (10) | 0.2512 (7) | 0.3860 (15) | 0.040 (3)* | |
C10 | 0.57698 (9) | 0.14531 (6) | 0.40985 (13) | 0.0334 (3) | |
C11 | 0.57441 (10) | 0.07771 (6) | 0.33773 (15) | 0.0385 (3) | |
H11 | 0.6093 (10) | 0.0376 (7) | 0.3857 (16) | 0.042 (3)* | |
C12 | 0.52391 (9) | 0.07033 (6) | 0.19232 (15) | 0.0370 (3) | |
H12 | 0.5232 (10) | 0.0246 (8) | 0.1399 (16) | 0.045 (4)* | |
C13 | 0.69384 (9) | 0.10627 (6) | 0.62260 (14) | 0.0360 (3) | |
C14 | 0.66890 (10) | 0.07921 (7) | 0.76643 (15) | 0.0387 (3) | |
H14 | 0.6027 (12) | 0.0929 (7) | 0.8145 (17) | 0.048 (4)* | |
C15 | 0.73845 (9) | 0.02957 (7) | 0.83957 (15) | 0.0387 (3) | |
H15 | 0.7213 (10) | 0.0097 (7) | 0.9386 (17) | 0.045 (4)* | |
C16 | 0.83293 (9) | 0.00778 (7) | 0.77040 (14) | 0.0389 (3) | |
C17 | 0.85625 (11) | 0.03622 (8) | 0.62480 (16) | 0.0476 (3) | |
H17 | 0.9225 (12) | 0.0224 (8) | 0.5713 (19) | 0.060 (4)* | |
C18 | 0.78724 (11) | 0.08536 (8) | 0.55046 (16) | 0.0456 (3) | |
H18 | 0.8029 (12) | 0.1044 (8) | 0.449 (2) | 0.061 (4)* | |
C19 | 0.99335 (11) | −0.05683 (8) | 0.81938 (16) | 0.0475 (3) | |
H19 | 1.0315 (14) | −0.0257 (10) | 0.740 (2) | 0.081 (5)* | |
C20 | 1.05838 (9) | −0.11380 (7) | 0.89892 (15) | 0.0414 (3) | |
C21 | 1.02147 (11) | −0.15013 (8) | 1.02727 (18) | 0.0514 (3) | |
H21 | 0.9473 (13) | −0.1382 (9) | 1.0666 (19) | 0.067 (5)* | |
C22 | 1.08610 (12) | −0.20248 (8) | 1.0971 (2) | 0.0576 (4) | |
H22 | 1.0636 (14) | −0.2306 (10) | 1.180 (2) | 0.076 (5)* | |
C23 | 1.18595 (11) | −0.21664 (8) | 1.03724 (18) | 0.0515 (3) | |
H23 | 1.2346 (12) | −0.2519 (9) | 1.0876 (19) | 0.061 (4)* | |
C24 | 1.21686 (11) | −0.17804 (8) | 0.90864 (17) | 0.0519 (4) | |
H24 | 1.2860 (13) | −0.1873 (8) | 0.8612 (18) | 0.062 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0478 (6) | 0.0782 (9) | 0.0491 (8) | 0.0168 (6) | −0.0072 (5) | −0.0018 (6) |
N2 | 0.0390 (5) | 0.0333 (5) | 0.0335 (6) | −0.0007 (4) | −0.0015 (4) | 0.0010 (4) |
N3 | 0.0428 (6) | 0.0512 (6) | 0.0390 (6) | 0.0065 (5) | −0.0031 (4) | 0.0056 (5) |
N4 | 0.0460 (6) | 0.0752 (8) | 0.0381 (7) | 0.0124 (6) | 0.0015 (5) | 0.0025 (6) |
O1 | 0.0518 (5) | 0.0380 (4) | 0.0339 (5) | 0.0091 (4) | −0.0092 (4) | −0.0047 (3) |
C1 | 0.0585 (9) | 0.0865 (12) | 0.0565 (11) | 0.0204 (8) | −0.0176 (8) | 0.0026 (8) |
C2 | 0.0673 (9) | 0.0655 (9) | 0.0414 (9) | −0.0043 (7) | −0.0161 (7) | 0.0052 (7) |
C3 | 0.0579 (8) | 0.0541 (8) | 0.0403 (8) | −0.0079 (6) | −0.0028 (6) | −0.0046 (6) |
C4 | 0.0437 (7) | 0.0401 (6) | 0.0406 (8) | −0.0033 (5) | −0.0029 (5) | −0.0025 (5) |
C5 | 0.0376 (6) | 0.0380 (6) | 0.0391 (7) | −0.0020 (5) | −0.0022 (5) | 0.0041 (5) |
C6 | 0.0387 (6) | 0.0423 (6) | 0.0355 (7) | 0.0015 (5) | 0.0024 (5) | 0.0006 (5) |
C7 | 0.0332 (5) | 0.0347 (6) | 0.0300 (6) | −0.0003 (4) | 0.0019 (4) | 0.0008 (5) |
C8 | 0.0389 (6) | 0.0328 (6) | 0.0326 (7) | 0.0055 (5) | 0.0029 (5) | 0.0027 (5) |
C9 | 0.0421 (6) | 0.0295 (6) | 0.0330 (7) | 0.0035 (4) | 0.0033 (5) | −0.0033 (5) |
C10 | 0.0350 (6) | 0.0358 (6) | 0.0293 (6) | 0.0011 (4) | −0.0005 (4) | −0.0008 (4) |
C11 | 0.0451 (6) | 0.0293 (6) | 0.0405 (7) | 0.0045 (5) | −0.0071 (5) | 0.0017 (5) |
C12 | 0.0438 (6) | 0.0291 (6) | 0.0379 (7) | 0.0018 (5) | −0.0033 (5) | −0.0037 (5) |
C13 | 0.0403 (6) | 0.0347 (6) | 0.0325 (7) | 0.0009 (5) | −0.0072 (5) | −0.0027 (5) |
C14 | 0.0366 (6) | 0.0422 (6) | 0.0371 (7) | −0.0004 (5) | 0.0003 (5) | −0.0021 (5) |
C15 | 0.0405 (6) | 0.0435 (6) | 0.0319 (7) | −0.0029 (5) | −0.0006 (5) | 0.0033 (5) |
C16 | 0.0396 (6) | 0.0422 (6) | 0.0345 (7) | 0.0011 (5) | −0.0056 (5) | 0.0012 (5) |
C17 | 0.0436 (7) | 0.0613 (8) | 0.0382 (8) | 0.0110 (6) | 0.0046 (5) | 0.0051 (6) |
C18 | 0.0501 (7) | 0.0542 (8) | 0.0325 (7) | 0.0072 (6) | 0.0028 (5) | 0.0065 (6) |
C19 | 0.0449 (7) | 0.0593 (8) | 0.0381 (8) | 0.0040 (6) | −0.0030 (5) | 0.0064 (6) |
C20 | 0.0390 (6) | 0.0496 (7) | 0.0350 (7) | 0.0025 (5) | −0.0057 (5) | −0.0018 (5) |
C21 | 0.0406 (7) | 0.0599 (8) | 0.0537 (9) | 0.0028 (6) | 0.0018 (6) | 0.0090 (7) |
C22 | 0.0547 (8) | 0.0578 (9) | 0.0602 (10) | 0.0007 (7) | 0.0004 (7) | 0.0192 (7) |
C23 | 0.0512 (8) | 0.0462 (7) | 0.0562 (9) | 0.0082 (6) | −0.0107 (6) | −0.0022 (6) |
C24 | 0.0446 (7) | 0.0685 (9) | 0.0422 (8) | 0.0148 (6) | −0.0033 (6) | −0.0093 (7) |
Geometric parameters (Å, º) top
N1—C1 | 1.341 (2) | C9—H9 | 0.954 (13) |
N1—C5 | 1.3418 (16) | C10—C11 | 1.3885 (16) |
N2—C6 | 1.2698 (15) | C11—C12 | 1.3830 (17) |
N2—C7 | 1.4167 (15) | C11—H11 | 0.941 (14) |
N3—C19 | 1.2564 (17) | C12—H12 | 0.953 (14) |
N3—C16 | 1.4179 (15) | C13—C14 | 1.3760 (18) |
N4—C24 | 1.3302 (18) | C13—C18 | 1.3816 (18) |
N4—C20 | 1.3445 (16) | C14—C15 | 1.3882 (17) |
O1—C10 | 1.3817 (14) | C14—H14 | 0.961 (15) |
O1—C13 | 1.3963 (13) | C15—C16 | 1.3857 (17) |
C1—C2 | 1.372 (2) | C15—H15 | 0.955 (15) |
C1—H1 | 0.96 (2) | C16—C17 | 1.3943 (19) |
C2—C3 | 1.375 (2) | C17—C18 | 1.3827 (18) |
C2—H2 | 0.965 (17) | C17—H17 | 0.984 (16) |
C3—C4 | 1.3800 (19) | C18—H18 | 0.966 (17) |
C3—H3 | 0.995 (18) | C19—C20 | 1.4731 (18) |
C4—C5 | 1.3874 (18) | C19—H19 | 1.02 (2) |
C4—H4 | 1.003 (16) | C20—C21 | 1.3793 (19) |
C5—C6 | 1.4734 (17) | C21—C22 | 1.375 (2) |
C6—H6 | 0.996 (15) | C21—H21 | 1.010 (16) |
C7—C12 | 1.3908 (16) | C22—C23 | 1.376 (2) |
C7—C8 | 1.4002 (16) | C22—H22 | 0.932 (19) |
C8—C9 | 1.3811 (17) | C23—C24 | 1.377 (2) |
C8—H8 | 0.981 (14) | C23—H23 | 0.974 (16) |
C9—C10 | 1.3869 (16) | C24—H24 | 0.973 (16) |
| | | |
C1—N1—C5 | 116.74 (13) | C11—C12—H12 | 120.7 (8) |
C6—N2—C7 | 119.80 (10) | C7—C12—H12 | 118.1 (8) |
C19—N3—C16 | 121.48 (12) | C14—C13—C18 | 121.16 (11) |
C24—N4—C20 | 117.26 (12) | C14—C13—O1 | 117.61 (11) |
C10—O1—C13 | 119.39 (9) | C18—C13—O1 | 121.17 (11) |
N1—C1—C2 | 124.25 (15) | C13—C14—C15 | 119.34 (12) |
N1—C1—H1 | 114.6 (12) | C13—C14—H14 | 120.7 (9) |
C2—C1—H1 | 121.2 (12) | C15—C14—H14 | 120.0 (9) |
C1—C2—C3 | 118.42 (14) | C16—C15—C14 | 120.82 (12) |
C1—C2—H2 | 118.2 (10) | C16—C15—H15 | 119.1 (8) |
C3—C2—H2 | 123.4 (10) | C14—C15—H15 | 120.1 (8) |
C2—C3—C4 | 118.86 (14) | C15—C16—C17 | 118.58 (11) |
C2—C3—H3 | 119.1 (10) | C15—C16—N3 | 116.52 (11) |
C4—C3—H3 | 122.1 (10) | C17—C16—N3 | 124.81 (11) |
C3—C4—C5 | 119.07 (12) | C18—C17—C16 | 121.09 (12) |
C3—C4—H4 | 121.6 (9) | C18—C17—H17 | 117.5 (9) |
C5—C4—H4 | 119.3 (9) | C16—C17—H17 | 121.4 (9) |
N1—C5—C4 | 122.66 (12) | C13—C18—C17 | 119.01 (12) |
N1—C5—C6 | 115.25 (11) | C13—C18—H18 | 120.0 (9) |
C4—C5—C6 | 122.02 (11) | C17—C18—H18 | 121.0 (9) |
N2—C6—C5 | 121.93 (11) | N3—C19—C20 | 121.79 (13) |
N2—C6—H6 | 122.2 (8) | N3—C19—H19 | 121.2 (10) |
C5—C6—H6 | 115.9 (8) | C20—C19—H19 | 117.0 (10) |
C12—C7—C8 | 118.35 (10) | N4—C20—C21 | 122.68 (12) |
C12—C7—N2 | 118.77 (10) | N4—C20—C19 | 115.63 (12) |
C8—C7—N2 | 122.66 (10) | C21—C20—C19 | 121.68 (12) |
C9—C8—C7 | 120.63 (10) | C22—C21—C20 | 119.03 (13) |
C9—C8—H8 | 119.3 (8) | C22—C21—H21 | 121.6 (9) |
C7—C8—H8 | 120.0 (8) | C20—C21—H21 | 119.3 (9) |
C8—C9—C10 | 120.09 (10) | C21—C22—C23 | 118.87 (15) |
C8—C9—H9 | 120.8 (8) | C21—C22—H22 | 122.6 (11) |
C10—C9—H9 | 119.1 (8) | C23—C22—H22 | 118.4 (11) |
O1—C10—C9 | 115.93 (10) | C22—C23—C24 | 118.56 (13) |
O1—C10—C11 | 124.02 (10) | C22—C23—H23 | 120.4 (9) |
C9—C10—C11 | 120.03 (11) | C24—C23—H23 | 121.0 (9) |
C12—C11—C10 | 119.55 (11) | N4—C24—C23 | 123.59 (13) |
C12—C11—H11 | 120.2 (8) | N4—C24—H24 | 115.3 (9) |
C10—C11—H11 | 120.2 (8) | C23—C24—H24 | 121.1 (9) |
C11—C12—C7 | 121.25 (11) | | |
| | | |
C5—N1—C1—C2 | −0.5 (3) | C10—O1—C13—C14 | −123.27 (12) |
N1—C1—C2—C3 | 0.2 (3) | C10—O1—C13—C18 | 59.70 (15) |
C1—C2—C3—C4 | −0.2 (2) | C18—C13—C14—C15 | −0.55 (18) |
C2—C3—C4—C5 | 0.5 (2) | O1—C13—C14—C15 | −177.59 (10) |
C1—N1—C5—C4 | 0.8 (2) | C13—C14—C15—C16 | 0.80 (18) |
C1—N1—C5—C6 | 177.80 (14) | C14—C15—C16—C17 | −0.64 (19) |
C3—C4—C5—N1 | −0.88 (19) | C14—C15—C16—N3 | −177.49 (11) |
C3—C4—C5—C6 | −177.64 (12) | C19—N3—C16—C15 | −163.59 (13) |
C7—N2—C6—C5 | 173.27 (10) | C19—N3—C16—C17 | 19.8 (2) |
N1—C5—C6—N2 | 178.26 (12) | C15—C16—C17—C18 | 0.2 (2) |
C4—C5—C6—N2 | −4.75 (18) | N3—C16—C17—C18 | 176.82 (12) |
C6—N2—C7—C12 | 144.52 (11) | C14—C13—C18—C17 | 0.17 (19) |
C6—N2—C7—C8 | −40.95 (16) | O1—C13—C18—C17 | 177.09 (11) |
C12—C7—C8—C9 | −0.50 (17) | C16—C17—C18—C13 | 0.0 (2) |
N2—C7—C8—C9 | −175.05 (10) | C16—N3—C19—C20 | −177.65 (12) |
C7—C8—C9—C10 | −1.88 (17) | C24—N4—C20—C21 | 0.1 (2) |
C13—O1—C10—C9 | −166.65 (10) | C24—N4—C20—C19 | 179.52 (12) |
C13—O1—C10—C11 | 14.86 (17) | N3—C19—C20—N4 | 171.04 (13) |
C8—C9—C10—O1 | −176.76 (10) | N3—C19—C20—C21 | −9.5 (2) |
C8—C9—C10—C11 | 1.79 (17) | N4—C20—C21—C22 | −0.2 (2) |
O1—C10—C11—C12 | 179.13 (11) | C19—C20—C21—C22 | −179.61 (14) |
C9—C10—C11—C12 | 0.70 (18) | C20—C21—C22—C23 | 0.4 (2) |
C10—C11—C12—C7 | −3.15 (19) | C21—C22—C23—C24 | −0.5 (2) |
C8—C7—C12—C11 | 3.04 (17) | C20—N4—C24—C23 | −0.2 (2) |
N2—C7—C12—C11 | 177.80 (11) | C22—C23—C24—N4 | 0.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···N4i | 0.966 (17) | 2.575 (17) | 3.5265 (18) | 168.1 (13) |
C21—H21···N1ii | 1.010 (16) | 2.550 (17) | 3.4046 (19) | 142.2 (12) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z+1. |