In the structure of the title compound, C
22H
24N
2O
3, short intermolecular C—H
O contacts influence the crystal packing and molecular ladders are formed. Intramolecular N—H
O hydrogen bonds make the
Z configuration stable by formation of six-membered rings.
Supporting information
CCDC reference: 189663
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.106
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
PLAT_724 Alert A Contact Calc 24.26760, Rep 2.54000, Dev. 21.73 Ang.
H8C -O2 1.555 4.565
PLAT_724 Alert A Contact Calc 21.90940, Rep 2.60000, Dev. 19.31 Ang.
H16 -O2 1.555 4.465
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
The title compound was prepared by the condensation in ethanol of 4,4'-diamino-diphenyl ether (0.5 mol) with 2,4-dipentone (1.0 mol). The solution was stirred for 2 h at 433 K. Crystals suitable for diffraction study were obtained after one month (m.p. 428 K). Spectroscopic analysis, 1H NMR (CDCl3, δ, p.p.m.): 1.97 (s, 6H), 2.10 (s, 6H), 5.19 (s, 1H), 7.04 (m, 8H), 12.39 (s, 1H).
All H atoms were generated geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H atoms and 0.96 Å for methyl H atoms, N—H = 0.86 Å, and Uiso(H) = 1.2Ueq of the parent atoms.
Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
(
Z)-4-(4-{4-[(
Z)-1-Methyl-3-oxobut-1-enylamino]phenoxy}phenylamino)pent-3-en- 2-one
top
Crystal data top
C22H24N2O3 | F(000) = 776 |
Mr = 364.43 | Dx = 1.209 Mg m−3 |
Monoclinic, P21/c | Melting point: 160 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.769 (1) Å | Cell parameters from 26 reflections |
b = 20.073 (4) Å | θ = 3.2–15.2° |
c = 11.928 (2) Å | µ = 0.08 mm−1 |
β = 107.53 (1)° | T = 296 K |
V = 2002.1 (6) Å3 | Monoclinic, yellow |
Z = 4 | 0.54 × 0.52 × 0.44 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.010 |
Radiation source: normal-focus sealed tube | θmax = 25.0°, θmin = 2.0° |
Graphite monochromator | h = 0→10 |
ω scans | k = 0→23 |
3762 measured reflections | l = −14→13 |
3520 independent reflections | 3 standard reflections every 97 reflections |
2338 reflections with I > 2σ(I) | intensity decay: 4.4% |
Refinement top
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
3520 reflections | Δρmax = 0.16 e Å−3 |
249 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0223 (19) |
Crystal data top
C22H24N2O3 | V = 2002.1 (6) Å3 |
Mr = 364.43 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.769 (1) Å | µ = 0.08 mm−1 |
b = 20.073 (4) Å | T = 296 K |
c = 11.928 (2) Å | 0.54 × 0.52 × 0.44 mm |
β = 107.53 (1)° | |
Data collection top
Siemens P4 diffractometer | Rint = 0.010 |
3762 measured reflections | 3 standard reflections every 97 reflections |
3520 independent reflections | intensity decay: 4.4% |
2338 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.16 e Å−3 |
3520 reflections | Δρmin = −0.15 e Å−3 |
249 parameters | |
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 | |
O1 | 0.92145 (14) | 0.62846 (6) | 0.35108 (10) | 0.0635 (4) | |
O2 | 1.69208 (15) | 0.81683 (6) | 0.35141 (11) | 0.0683 (4) | |
O3 | 0.35937 (14) | 0.60130 (6) | 0.73952 (10) | 0.0636 (4) | |
N1 | 1.47304 (16) | 0.78311 (7) | 0.45227 (12) | 0.0559 (4) | |
H1N | 1.5035 | 0.7881 | 0.3907 | 0.067* | |
N2 | 0.60387 (17) | 0.55880 (7) | 0.67380 (12) | 0.0546 (4) | |
H2N | 0.5336 | 0.5885 | 0.6751 | 0.066* | |
C1 | 1.05639 (19) | 0.66896 (8) | 0.38356 (14) | 0.0487 (4) | |
C2 | 1.0751 (2) | 0.71426 (9) | 0.30265 (15) | 0.0583 (5) | |
H2 | 0.9956 | 0.7192 | 0.2311 | 0.070* | |
C3 | 1.2122 (2) | 0.75256 (9) | 0.32761 (14) | 0.0563 (5) | |
H3 | 1.2247 | 0.7833 | 0.2727 | 0.068* | |
C4 | 1.33097 (19) | 0.74546 (8) | 0.43388 (14) | 0.0482 (4) | |
C5 | 1.3103 (2) | 0.69937 (8) | 0.51422 (14) | 0.0512 (4) | |
H5 | 1.3899 | 0.6938 | 0.5855 | 0.061* | |
C6 | 1.1729 (2) | 0.66161 (8) | 0.48979 (15) | 0.0519 (4) | |
H6 | 1.1591 | 0.6313 | 0.5449 | 0.062* | |
C7 | 1.5679 (2) | 0.81219 (8) | 0.54934 (14) | 0.0492 (4) | |
C8 | 1.5212 (2) | 0.81218 (9) | 0.66039 (15) | 0.0659 (5) | |
H8A | 1.4071 | 0.8158 | 0.6413 | 0.079* | |
H8B | 1.5707 | 0.8493 | 0.7085 | 0.079* | |
H8C | 1.5560 | 0.7714 | 0.7024 | 0.079* | |
C9 | 1.7058 (2) | 0.84277 (9) | 0.54584 (15) | 0.0562 (5) | |
H9 | 1.7661 | 0.8647 | 0.6133 | 0.067* | |
C10 | 1.7636 (2) | 0.84345 (9) | 0.44711 (18) | 0.0596 (5) | |
C11 | 1.9204 (3) | 0.87707 (13) | 0.4580 (2) | 0.0959 (8) | |
H11A | 2.0058 | 0.8455 | 0.4850 | 0.115* | |
H11B | 1.9357 | 0.9131 | 0.5132 | 0.115* | |
H11C | 1.9199 | 0.8941 | 0.3827 | 0.115* | |
C12 | 0.85222 (19) | 0.61089 (9) | 0.43774 (14) | 0.0506 (4) | |
C13 | 0.8098 (2) | 0.54588 (9) | 0.44410 (15) | 0.0593 (5) | |
H13 | 0.8358 | 0.5141 | 0.3960 | 0.071* | |
C14 | 0.7283 (2) | 0.52713 (9) | 0.52186 (16) | 0.0589 (5) | |
H14 | 0.6963 | 0.4831 | 0.5240 | 0.071* | |
C15 | 0.69427 (19) | 0.57348 (8) | 0.59622 (14) | 0.0484 (4) | |
C16 | 0.7400 (2) | 0.63882 (8) | 0.59033 (17) | 0.0598 (5) | |
H16 | 0.7189 | 0.6703 | 0.6409 | 0.072* | |
C17 | 0.8168 (2) | 0.65795 (9) | 0.50999 (17) | 0.0630 (5) | |
H17 | 0.8444 | 0.7023 | 0.5048 | 0.076* | |
C18 | 0.6086 (2) | 0.50707 (8) | 0.74516 (15) | 0.0523 (4) | |
C19 | 0.7301 (3) | 0.45345 (10) | 0.7543 (2) | 0.0850 (7) | |
H19A | 0.6895 | 0.4215 | 0.6926 | 0.102* | |
H19B | 0.7519 | 0.4317 | 0.8292 | 0.102* | |
H19C | 0.8269 | 0.4727 | 0.7470 | 0.102* | |
C20 | 0.5030 (2) | 0.50409 (9) | 0.80976 (15) | 0.0558 (5) | |
H20 | 0.5128 | 0.4687 | 0.8617 | 0.067* | |
C21 | 0.3804 (2) | 0.55107 (9) | 0.80295 (14) | 0.0526 (4) | |
C22 | 0.2654 (3) | 0.53914 (11) | 0.87256 (19) | 0.0815 (6) | |
H22A | 0.2664 | 0.5768 | 0.9224 | 0.098* | |
H22B | 0.2970 | 0.5000 | 0.9200 | 0.098* | |
H22C | 0.1596 | 0.5330 | 0.8197 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0600 (8) | 0.0837 (9) | 0.0490 (7) | −0.0247 (7) | 0.0197 (6) | −0.0044 (6) |
O2 | 0.0692 (8) | 0.0803 (9) | 0.0606 (8) | −0.0169 (7) | 0.0274 (7) | −0.0014 (7) |
O3 | 0.0677 (8) | 0.0636 (8) | 0.0643 (8) | 0.0171 (7) | 0.0273 (7) | 0.0143 (7) |
N1 | 0.0555 (9) | 0.0692 (10) | 0.0445 (8) | −0.0133 (7) | 0.0174 (7) | 0.0023 (7) |
N2 | 0.0556 (9) | 0.0495 (8) | 0.0658 (9) | 0.0063 (7) | 0.0289 (8) | 0.0091 (7) |
C1 | 0.0471 (10) | 0.0572 (10) | 0.0445 (9) | −0.0062 (8) | 0.0180 (8) | −0.0025 (8) |
C2 | 0.0558 (11) | 0.0734 (12) | 0.0436 (9) | −0.0089 (9) | 0.0117 (8) | 0.0063 (9) |
C3 | 0.0628 (11) | 0.0629 (11) | 0.0432 (9) | −0.0090 (9) | 0.0158 (9) | 0.0103 (8) |
C4 | 0.0474 (9) | 0.0533 (10) | 0.0473 (9) | −0.0041 (8) | 0.0193 (8) | 0.0019 (8) |
C5 | 0.0467 (10) | 0.0579 (10) | 0.0474 (9) | 0.0015 (8) | 0.0115 (8) | 0.0091 (8) |
C6 | 0.0534 (10) | 0.0552 (10) | 0.0505 (10) | −0.0023 (9) | 0.0208 (8) | 0.0097 (8) |
C7 | 0.0535 (10) | 0.0446 (9) | 0.0470 (9) | 0.0045 (8) | 0.0114 (8) | 0.0044 (8) |
C8 | 0.0803 (14) | 0.0636 (12) | 0.0566 (11) | −0.0011 (10) | 0.0249 (10) | −0.0035 (9) |
C9 | 0.0552 (10) | 0.0549 (10) | 0.0535 (10) | −0.0048 (9) | 0.0085 (9) | −0.0021 (8) |
C10 | 0.0516 (11) | 0.0558 (11) | 0.0690 (12) | −0.0033 (9) | 0.0147 (10) | 0.0052 (9) |
C11 | 0.0664 (14) | 0.117 (2) | 0.1059 (18) | −0.0299 (13) | 0.0282 (13) | −0.0030 (15) |
C12 | 0.0429 (9) | 0.0645 (12) | 0.0446 (9) | −0.0096 (8) | 0.0136 (8) | 0.0008 (8) |
C13 | 0.0638 (12) | 0.0634 (12) | 0.0545 (10) | −0.0129 (9) | 0.0235 (9) | −0.0136 (9) |
C14 | 0.0670 (12) | 0.0500 (10) | 0.0638 (11) | −0.0144 (9) | 0.0257 (10) | −0.0062 (9) |
C15 | 0.0438 (9) | 0.0493 (10) | 0.0540 (10) | 0.0007 (8) | 0.0174 (8) | 0.0036 (8) |
C16 | 0.0683 (12) | 0.0471 (10) | 0.0751 (12) | 0.0030 (9) | 0.0384 (10) | −0.0005 (9) |
C17 | 0.0712 (12) | 0.0464 (10) | 0.0819 (13) | −0.0042 (9) | 0.0387 (11) | 0.0048 (10) |
C18 | 0.0511 (10) | 0.0492 (10) | 0.0556 (10) | 0.0034 (8) | 0.0149 (9) | 0.0062 (8) |
C19 | 0.0886 (16) | 0.0806 (15) | 0.0990 (16) | 0.0319 (12) | 0.0481 (14) | 0.0344 (13) |
C20 | 0.0611 (11) | 0.0551 (11) | 0.0535 (10) | 0.0037 (9) | 0.0207 (9) | 0.0130 (8) |
C21 | 0.0526 (10) | 0.0615 (11) | 0.0445 (9) | −0.0005 (9) | 0.0158 (8) | 0.0007 (9) |
C22 | 0.0814 (14) | 0.0997 (17) | 0.0770 (13) | 0.0151 (13) | 0.0443 (12) | 0.0142 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.3911 (19) | C9—H9 | 0.930 |
O1—C12 | 1.3926 (19) | C10—C11 | 1.502 (3) |
O2—C10 | 1.245 (2) | C11—H11A | 0.960 |
O3—C21 | 1.2406 (19) | C11—H11B | 0.960 |
N1—C7 | 1.339 (2) | C11—H11C | 0.960 |
N1—C4 | 1.417 (2) | C12—C13 | 1.365 (2) |
N1—H1N | 0.860 | C12—C17 | 1.376 (2) |
N2—C18 | 1.335 (2) | C13—C14 | 1.383 (2) |
N2—C15 | 1.419 (2) | C13—H13 | 0.930 |
N2—H2N | 0.860 | C14—C15 | 1.379 (2) |
C1—C2 | 1.371 (2) | C14—H14 | 0.930 |
C1—C6 | 1.375 (2) | C15—C16 | 1.380 (2) |
C2—C3 | 1.382 (2) | C16—C17 | 1.381 (2) |
C2—H2 | 0.930 | C16—H16 | 0.930 |
C3—C4 | 1.385 (2) | C17—H17 | 0.930 |
C3—H3 | 0.930 | C18—C20 | 1.373 (2) |
C4—C5 | 1.383 (2) | C18—C19 | 1.495 (2) |
C5—C6 | 1.378 (2) | C19—H19A | 0.960 |
C5—H5 | 0.930 | C19—H19B | 0.960 |
C6—H6 | 0.930 | C19—H19C | 0.960 |
C7—C9 | 1.368 (2) | C20—C21 | 1.414 (2) |
C7—C8 | 1.500 (2) | C20—H20 | 0.930 |
C8—H8A | 0.960 | C21—C22 | 1.505 (2) |
C8—H8B | 0.960 | C22—H22A | 0.960 |
C8—H8C | 0.960 | C22—H22B | 0.960 |
C9—C10 | 1.415 (2) | C22—H22C | 0.960 |
| | | |
H8C···O2i | 2.54 | H16···O2ii | 2.60 |
| | | |
C1—O1—C12 | 117.75 (12) | C10—C11—H11C | 109.5 |
C7—N1—C4 | 130.90 (14) | H11A—C11—H11C | 109.5 |
C7—N1—H1N | 114.5 | H11B—C11—H11C | 109.5 |
C4—N1—H1N | 114.5 | C13—C12—C17 | 120.31 (15) |
C18—N2—C15 | 131.37 (14) | C13—C12—O1 | 118.05 (15) |
C18—N2—H2N | 114.3 | C17—C12—O1 | 121.48 (15) |
C15—N2—H2N | 114.3 | C12—C13—C14 | 120.13 (17) |
C2—C1—C6 | 120.43 (15) | C12—C13—H13 | 119.9 |
C2—C1—O1 | 117.61 (15) | C14—C13—H13 | 119.9 |
C6—C1—O1 | 121.84 (14) | C15—C14—C13 | 120.24 (16) |
C1—C2—C3 | 119.86 (16) | C15—C14—H14 | 119.9 |
C1—C2—H2 | 120.1 | C13—C14—H14 | 119.9 |
C3—C2—H2 | 120.1 | C14—C15—C16 | 119.09 (16) |
C2—C3—C4 | 120.40 (15) | C14—C15—N2 | 123.45 (15) |
C2—C3—H3 | 119.8 | C16—C15—N2 | 117.30 (15) |
C4—C3—H3 | 119.8 | C15—C16—C17 | 120.64 (16) |
C5—C4—C3 | 118.94 (15) | C15—C16—H16 | 119.7 |
C5—C4—N1 | 122.85 (15) | C17—C16—H16 | 119.7 |
C3—C4—N1 | 118.10 (14) | C12—C17—C16 | 119.53 (16) |
C6—C5—C4 | 120.67 (16) | C12—C17—H17 | 120.2 |
C6—C5—H5 | 119.7 | C16—C17—H17 | 120.2 |
C4—C5—H5 | 119.7 | N2—C18—C20 | 119.66 (15) |
C1—C6—C5 | 119.70 (15) | N2—C18—C19 | 119.41 (16) |
C1—C6—H6 | 120.2 | C20—C18—C19 | 120.92 (16) |
C5—C6—H6 | 120.2 | C18—C19—H19A | 109.5 |
N1—C7—C9 | 119.59 (15) | C18—C19—H19B | 109.5 |
N1—C7—C8 | 119.99 (15) | H19A—C19—H19B | 109.5 |
C9—C7—C8 | 120.41 (16) | C18—C19—H19C | 109.5 |
C7—C8—H8A | 109.5 | H19A—C19—H19C | 109.5 |
C7—C8—H8B | 109.5 | H19B—C19—H19C | 109.5 |
H8A—C8—H8B | 109.5 | C18—C20—C21 | 124.65 (16) |
C7—C8—H8C | 109.5 | C18—C20—H20 | 117.7 |
H8A—C8—H8C | 109.5 | C21—C20—H20 | 117.7 |
H8B—C8—H8C | 109.5 | O3—C21—C20 | 123.20 (16) |
C7—C9—C10 | 124.82 (17) | O3—C21—C22 | 117.68 (16) |
C7—C9—H9 | 117.6 | C20—C21—C22 | 119.09 (16) |
C10—C9—H9 | 117.6 | C21—C22—H22A | 109.5 |
O2—C10—C9 | 123.44 (16) | C21—C22—H22B | 109.5 |
O2—C10—C11 | 117.84 (18) | H22A—C22—H22B | 109.5 |
C9—C10—C11 | 118.71 (19) | C21—C22—H22C | 109.5 |
C10—C11—H11A | 109.5 | H22A—C22—H22C | 109.5 |
C10—C11—H11B | 109.5 | H22B—C22—H22C | 109.5 |
H11A—C11—H11B | 109.5 | | |
| | | |
C12—O1—C1—C2 | −145.43 (16) | C1—O1—C12—C13 | −134.49 (16) |
C12—O1—C1—C6 | 38.6 (2) | C1—O1—C12—C17 | 50.0 (2) |
C6—C1—C2—C3 | 0.3 (3) | C17—C12—C13—C14 | 1.2 (3) |
O1—C1—C2—C3 | −175.70 (15) | O1—C12—C13—C14 | −174.42 (15) |
C1—C2—C3—C4 | 0.0 (3) | C12—C13—C14—C15 | −2.2 (3) |
C2—C3—C4—C5 | 0.2 (3) | C13—C14—C15—C16 | 1.2 (3) |
C2—C3—C4—N1 | 176.38 (16) | C13—C14—C15—N2 | 176.52 (16) |
C7—N1—C4—C5 | −40.1 (3) | C18—N2—C15—C14 | 44.0 (3) |
C7—N1—C4—C3 | 143.88 (18) | C18—N2—C15—C16 | −140.55 (19) |
C3—C4—C5—C6 | −0.8 (2) | C14—C15—C16—C17 | 0.9 (3) |
N1—C4—C5—C6 | −176.80 (15) | N2—C15—C16—C17 | −174.69 (16) |
C2—C1—C6—C5 | −1.0 (3) | C13—C12—C17—C16 | 0.9 (3) |
O1—C1—C6—C5 | 174.93 (15) | O1—C12—C17—C16 | 176.37 (16) |
C4—C5—C6—C1 | 1.2 (3) | C15—C16—C17—C12 | −2.0 (3) |
C4—N1—C7—C9 | 175.96 (17) | C15—N2—C18—C20 | −178.18 (16) |
C4—N1—C7—C8 | −5.1 (3) | C15—N2—C18—C19 | 2.4 (3) |
N1—C7—C9—C10 | −3.6 (3) | N2—C18—C20—C21 | 3.3 (3) |
C8—C7—C9—C10 | 177.49 (17) | C19—C18—C20—C21 | −177.29 (18) |
C7—C9—C10—O2 | 1.3 (3) | C18—C20—C21—O3 | −2.3 (3) |
C7—C9—C10—C11 | −177.81 (19) | C18—C20—C21—C22 | 175.70 (18) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.86 | 1.94 | 2.643 (2) | 139 |
N2—H2N···O3 | 0.86 | 1.92 | 2.637 (2) | 139 |
C6—H6···O3iii | 0.93 | 2.53 | 3.175 (2) | 127 |
Symmetry code: (iii) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | C22H24N2O3 |
Mr | 364.43 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 8.769 (1), 20.073 (4), 11.928 (2) |
β (°) | 107.53 (1) |
V (Å3) | 2002.1 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.54 × 0.52 × 0.44 |
|
Data collection |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3762, 3520, 2338 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.106, 0.98 |
No. of reflections | 3520 |
No. of parameters | 249 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 |
Selected geometric parameters (Å, º) topO1—C1 | 1.3911 (19) | N1—C4 | 1.417 (2) |
O1—C12 | 1.3926 (19) | N2—C18 | 1.335 (2) |
O2—C10 | 1.245 (2) | N2—C15 | 1.419 (2) |
O3—C21 | 1.2406 (19) | C7—C9 | 1.368 (2) |
N1—C7 | 1.339 (2) | C18—C20 | 1.373 (2) |
| | | |
H8C···O2i | 2.54 | H16···O2ii | 2.60 |
| | | |
C1—O1—C12 | 117.75 (12) | N1—C7—C8 | 119.99 (15) |
C7—N1—C4 | 130.90 (14) | C14—C15—N2 | 123.45 (15) |
C18—N2—C15 | 131.37 (14) | C16—C15—N2 | 117.30 (15) |
C5—C4—N1 | 122.85 (15) | N2—C18—C20 | 119.66 (15) |
C3—C4—N1 | 118.10 (14) | N2—C18—C19 | 119.41 (16) |
N1—C7—C9 | 119.59 (15) | | |
| | | |
C4—N1—C7—C9 | 175.96 (17) | C15—N2—C18—C20 | −178.18 (16) |
N1—C7—C9—C10 | −3.6 (3) | N2—C18—C20—C21 | 3.3 (3) |
C7—C9—C10—O2 | 1.3 (3) | C18—C20—C21—O3 | −2.3 (3) |
C7—C9—C10—C11 | −177.81 (19) | C18—C20—C21—C22 | 175.70 (18) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.86 | 1.94 | 2.643 (2) | 138.5 |
N2—H2N···O3 | 0.86 | 1.92 | 2.637 (2) | 139.4 |
C6—H6···O3iii | 0.93 | 2.53 | 3.175 (2) | 127.1 |
Symmetry code: (iii) x+1, y, z. |
Schiff bases are becoming increasingly important as biological, analytical, pharmacological and antimicrobial reagents in coordination chemistry. There are many reports of Schiff bases obtained by condensation between the NH2 group of an amine and the carbonyl group of aldehydes/ketones (Ismail, 2000; Raman et al., 2001; Daniel Thangadurai & Natarajan, 2000). A literature survey revealed fewer results involving isomers of Schiff bases. We obtained the title compound, (I), by the usual type of condensation; however, the expected C—C═N group is, in fact, C═C—N.
A view of the molecule of (I) is shown in Fig. 1. The dihedral angle between the two planes defined by O1 and each of the two phenyl rings is 73.39 (7)%. The N1—H1N···O2 and N2—H2N···O3 hydrogen bond stablize the Z configuration of the C═C bonds by forming six-membered rings (Table 2). The torsion angles C7—C9—C10—O2 [1.3 (3)%] and C7—C9—C10—C11 [−177.81 (19)%] indicate that the group N1/C7/C8/C9/C10/C11/O2 is nearly planar; the group N2/C18/C19/C20/C21/C22/O3 is not slightly more non-planar, as is evident from the torsion angles C18—C20—C21—O3 [−2.3 (3)%] and C18—C20—C21—C22 [175.70 (18)%]. The dihedral angle between these two groups is 88.21 (6)%. The two halves of the molecule resemble each other in geometry (Table 1).
The short intermolecular C—H···O contacts (Table 2) involving both ketone functions are respectively 0.19, 0.18 and 0.12 Å shorter than the sum of van der Waals radii (Bondi, 1964). They may be classified as weak to very weak hydrogen bonds (Desiraju & Steiner, 1999), and the second is near-linear (Jeffrey et al., 1985). Examination of the structure with PLATON (Spek, 2002) shows that there are no solvent-accessible voids.
The intermolecular C—H···O contacts link molecules into dimers, dimers face-to-face to form four-molecule aggregates, and aggregates into ladders, to give a two-demensional network (Fig. 2).