organic compounds
2-((E)-{4-[Bis(4-ethoxyphenyl)amino]phenyl}iminomethyl)phenol
aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, bKey Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China, and cDepartment of Chemistry, Bengbu Medical College, Bengbu 233030, People's Republic of China
*Correspondence e-mail: yptian@ahu.edu.cn
In the title Schiff base molecule, C29H28N2O3, the three terminal benzene rings are twisted by 73.84 (15), 81.25 (16) and 12.1 (2)° with respect to the central benzene ring. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal, molecules are linked via weak C—H⋯π interactions into a three-dimensional supramolecular architecture.
CCDC reference: 986499
Related literature
For background and the synthesis of the title compound, see: Dharmaraj et al. (2001); Feng (2014). For a related structure, see: Tanak et al. (2013).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 986499
10.1107/S1600536814003201/xu5765sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003201/xu5765Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003201/xu5765Isup3.cml
A hot solution of N1,N1 -bis (4-ethoxyphenyl) benzene -1,4 - diamine (3.48 g, 10 mmol) in ethanol 50 mL was mixed with a salicylaldehyde (1.83 g, 15 mmol) in ethanol 5 mL, a yellow solid was appeared immediately, then the reaction mixture was reflux for 2 h. Under cooling the room temperature, the light yellow crystals were separated by filtration and recrystallized from ethanol. Yield: 96%. 1H NMR (400 MHz, DMSO-d6) 1.34 (t, 6H), 4.03 (m, 4H), 6.82 (d, 2H), 6.97 (m, 6H), 7.04 (d, 4H), 7.31 (d, 2H), 7.38 (t, 1H), 7.59 (d, 1H), 8.90 (s, 1H), 13.37 (s, 1H).
All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). As no significant
Friedel pairs were merged.Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. : The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. : The H-bond diagram of the title molecule(I). |
C29H28N2O3 | Dx = 1.211 Mg m−3 |
Mr = 452.53 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2336 reflections |
a = 9.765 (3) Å | θ = 2.3–20.7° |
b = 13.113 (4) Å | µ = 0.08 mm−1 |
c = 19.378 (6) Å | T = 296 K |
V = 2481.2 (14) Å3 | Block, yellow |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
F(000) = 960 |
Bruker SMART CCD area-detector diffractometer | 2486 independent reflections |
Radiation source: fine-focus sealed tube | 1747 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
phi and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→11 |
Tmin = 0.969, Tmax = 0.984 | k = −15→15 |
17684 measured reflections | l = −22→22 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0561P)2] where P = (Fo2 + 2Fc2)/3 |
2486 reflections | (Δ/σ)max < 0.001 |
310 parameters | Δρmax = 0.12 e Å−3 |
6 restraints | Δρmin = −0.18 e Å−3 |
C29H28N2O3 | V = 2481.2 (14) Å3 |
Mr = 452.53 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.765 (3) Å | µ = 0.08 mm−1 |
b = 13.113 (4) Å | T = 296 K |
c = 19.378 (6) Å | 0.40 × 0.30 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 2486 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1747 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.984 | Rint = 0.051 |
17684 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 6 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.12 e Å−3 |
2486 reflections | Δρmin = −0.18 e Å−3 |
310 parameters |
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 | ||
C1 | 0.1807 (5) | 0.6157 (3) | 1.2427 (2) | 0.0891 (13) | |
H1A | 0.1266 | 0.6695 | 1.2231 | 0.134* | |
H1B | 0.2698 | 0.6414 | 1.2543 | 0.134* | |
H1C | 0.1367 | 0.5904 | 1.2835 | 0.134* | |
C2 | 0.1945 (4) | 0.5321 (3) | 1.1919 (2) | 0.0741 (11) | |
H2A | 0.2332 | 0.5582 | 1.1493 | 0.089* | |
H2B | 0.2555 | 0.4800 | 1.2098 | 0.089* | |
C3 | 0.0558 (3) | 0.4027 (2) | 1.13890 (15) | 0.0476 (8) | |
C4 | 0.1641 (3) | 0.3628 (2) | 1.10191 (16) | 0.0554 (9) | |
H4 | 0.2488 | 0.3953 | 1.1023 | 0.066* | |
C5 | 0.1461 (3) | 0.2750 (3) | 1.06451 (17) | 0.0569 (9) | |
H5 | 0.2196 | 0.2478 | 1.0402 | 0.068* | |
C6 | 0.0203 (3) | 0.2259 (2) | 1.06227 (15) | 0.0484 (8) | |
C7 | −0.0875 (3) | 0.2676 (3) | 1.09885 (16) | 0.0560 (9) | |
H7 | −0.1727 | 0.2361 | 1.0976 | 0.067* | |
C8 | −0.0708 (4) | 0.3548 (2) | 1.13691 (16) | 0.0551 (9) | |
H8 | −0.1442 | 0.3819 | 1.1614 | 0.066* | |
C9 | −0.2070 (4) | −0.3382 (3) | 1.25128 (19) | 0.0800 (12) | |
H9A | −0.1536 | −0.3916 | 1.2306 | 0.120* | |
H9B | −0.2961 | −0.3639 | 1.2629 | 0.120* | |
H9C | −0.1621 | −0.3145 | 1.2923 | 0.120* | |
C10 | −0.2213 (4) | −0.2511 (3) | 1.2010 (2) | 0.0757 (11) | |
H10A | −0.2586 | −0.2754 | 1.1576 | 0.091* | |
H10B | −0.2823 | −0.1995 | 1.2195 | 0.091* | |
C11 | −0.0768 (4) | −0.1254 (2) | 1.14919 (16) | 0.0546 (8) | |
C12 | 0.0506 (4) | −0.0825 (3) | 1.14815 (18) | 0.0648 (10) | |
H12 | 0.1200 | −0.1098 | 1.1753 | 0.078* | |
C13 | 0.0772 (4) | 0.0010 (3) | 1.10721 (17) | 0.0584 (9) | |
H13 | 0.1647 | 0.0290 | 1.1063 | 0.070* | |
C14 | −0.0254 (4) | 0.0431 (2) | 1.06752 (16) | 0.0513 (8) | |
C15 | −0.1533 (4) | 0.0009 (3) | 1.06924 (18) | 0.0613 (9) | |
H15 | −0.2233 | 0.0293 | 1.0430 | 0.074* | |
C16 | −0.1797 (3) | −0.0843 (3) | 1.11010 (18) | 0.0631 (10) | |
H16 | −0.2667 | −0.1132 | 1.1108 | 0.076* | |
C17 | 0.0234 (3) | 0.1219 (2) | 0.95562 (15) | 0.0486 (8) | |
C18 | 0.0227 (3) | 0.2085 (2) | 0.91266 (15) | 0.0494 (8) | |
H18 | 0.0144 | 0.2732 | 0.9318 | 0.059* | |
C19 | 0.0345 (3) | 0.1973 (2) | 0.84202 (16) | 0.0524 (8) | |
H19 | 0.0340 | 0.2552 | 0.8142 | 0.063* | |
C20 | 0.0470 (3) | 0.1022 (2) | 0.81143 (15) | 0.0483 (8) | |
C21 | 0.0489 (4) | 0.0180 (2) | 0.85418 (17) | 0.0556 (9) | |
H21 | 0.0576 | −0.0465 | 0.8348 | 0.067* | |
C22 | 0.0384 (4) | 0.0268 (2) | 0.92461 (16) | 0.0562 (9) | |
H22 | 0.0413 | −0.0314 | 0.9519 | 0.067* | |
N2 | 0.0527 (3) | 0.0833 (2) | 0.73886 (13) | 0.0539 (7) | |
C24 | 0.0683 (4) | 0.1357 (3) | 0.62156 (17) | 0.0636 (9) | |
C25 | 0.0822 (7) | 0.2158 (4) | 0.5769 (2) | 0.129 (2) | |
H25 | 0.0939 | 0.2812 | 0.5944 | 0.154* | |
C26 | 0.0793 (8) | 0.2014 (4) | 0.5064 (2) | 0.146 (2) | |
H26 | 0.0878 | 0.2568 | 0.4767 | 0.175* | |
C27 | 0.0637 (7) | 0.1046 (4) | 0.4803 (2) | 0.125 (2) | |
H27 | 0.0633 | 0.0945 | 0.4328 | 0.150* | |
C28 | 0.0490 (5) | 0.0243 (3) | 0.52299 (19) | 0.0818 (12) | |
H28 | 0.0381 | −0.0409 | 0.5050 | 0.098* | |
C29 | 0.0503 (4) | 0.0392 (3) | 0.59391 (17) | 0.0615 (9) | |
N1 | 0.0028 (3) | 0.13169 (19) | 1.02609 (13) | 0.0572 (8) | |
C23 | 0.0688 (4) | 0.1534 (3) | 0.69541 (17) | 0.0633 (9) | |
H23 | 0.0816 | 0.2197 | 0.7113 | 0.076* | |
O1 | −0.0896 (3) | −0.21002 (19) | 1.19072 (13) | 0.0745 (7) | |
O2 | 0.0625 (2) | 0.48898 (16) | 1.17876 (11) | 0.0613 (6) | |
O3 | 0.0333 (4) | −0.04181 (18) | 0.63487 (13) | 0.0933 (10) | |
H3 | 0.0383 | −0.0239 | 0.6753 | 0.140* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.095 (3) | 0.078 (3) | 0.093 (3) | −0.022 (2) | 0.003 (3) | −0.023 (3) |
C2 | 0.069 (3) | 0.069 (2) | 0.085 (3) | −0.015 (2) | 0.005 (2) | −0.012 (2) |
C3 | 0.053 (2) | 0.0494 (19) | 0.0401 (17) | 0.0010 (16) | 0.0005 (15) | −0.0007 (15) |
C4 | 0.0502 (18) | 0.062 (2) | 0.054 (2) | −0.0089 (17) | 0.0027 (17) | −0.0064 (19) |
C5 | 0.053 (2) | 0.065 (2) | 0.0527 (19) | −0.0001 (18) | 0.0150 (17) | −0.0058 (18) |
C6 | 0.058 (2) | 0.0510 (19) | 0.0365 (16) | −0.0029 (17) | 0.0009 (15) | 0.0031 (15) |
C7 | 0.0462 (19) | 0.067 (2) | 0.0550 (19) | −0.0081 (17) | 0.0033 (16) | 0.0012 (19) |
C8 | 0.049 (2) | 0.064 (2) | 0.052 (2) | 0.0052 (17) | 0.0050 (16) | −0.0077 (18) |
C9 | 0.097 (3) | 0.072 (3) | 0.071 (2) | −0.023 (2) | 0.002 (2) | 0.014 (2) |
C10 | 0.073 (3) | 0.072 (2) | 0.082 (3) | −0.010 (2) | 0.002 (2) | 0.008 (2) |
C11 | 0.068 (2) | 0.0469 (19) | 0.0492 (18) | 0.0013 (18) | 0.0059 (18) | 0.0055 (17) |
C12 | 0.061 (2) | 0.067 (2) | 0.067 (2) | 0.002 (2) | −0.0060 (19) | 0.012 (2) |
C13 | 0.054 (2) | 0.061 (2) | 0.060 (2) | −0.0035 (17) | 0.0025 (18) | 0.0040 (19) |
C14 | 0.060 (2) | 0.0538 (19) | 0.0398 (17) | −0.0022 (17) | 0.0059 (16) | −0.0005 (16) |
C15 | 0.063 (2) | 0.059 (2) | 0.062 (2) | −0.0035 (19) | −0.0084 (18) | 0.0085 (19) |
C16 | 0.053 (2) | 0.063 (2) | 0.073 (2) | −0.0079 (18) | 0.000 (2) | 0.007 (2) |
C17 | 0.0502 (19) | 0.056 (2) | 0.0397 (17) | −0.0035 (17) | 0.0018 (14) | −0.0008 (16) |
C18 | 0.054 (2) | 0.0496 (18) | 0.0443 (18) | −0.0055 (16) | −0.0008 (15) | −0.0019 (15) |
C19 | 0.055 (2) | 0.0566 (19) | 0.0460 (18) | −0.0032 (17) | 0.0010 (17) | 0.0040 (16) |
C20 | 0.0463 (19) | 0.059 (2) | 0.0395 (16) | 0.0027 (17) | −0.0015 (15) | −0.0018 (16) |
C21 | 0.070 (2) | 0.0464 (18) | 0.0508 (19) | 0.0026 (18) | 0.0012 (18) | −0.0051 (16) |
C22 | 0.072 (2) | 0.0481 (19) | 0.0479 (19) | 0.0053 (18) | 0.0019 (18) | 0.0021 (16) |
N2 | 0.0578 (17) | 0.0597 (17) | 0.0440 (15) | 0.0038 (14) | 0.0024 (14) | 0.0000 (15) |
C24 | 0.081 (2) | 0.065 (2) | 0.0452 (19) | −0.015 (2) | 0.0012 (19) | 0.0000 (19) |
C25 | 0.233 (7) | 0.091 (3) | 0.061 (3) | −0.055 (4) | 0.010 (4) | 0.006 (3) |
C26 | 0.259 (7) | 0.115 (4) | 0.063 (3) | −0.054 (4) | 0.009 (4) | 0.019 (3) |
C27 | 0.208 (6) | 0.123 (4) | 0.044 (2) | −0.050 (4) | 0.001 (3) | −0.006 (3) |
C28 | 0.112 (3) | 0.083 (3) | 0.051 (2) | −0.011 (3) | −0.009 (2) | −0.007 (2) |
C29 | 0.067 (2) | 0.067 (2) | 0.051 (2) | 0.001 (2) | −0.0048 (19) | 0.002 (2) |
N1 | 0.085 (2) | 0.0491 (16) | 0.0381 (14) | −0.0123 (15) | 0.0043 (14) | −0.0009 (13) |
C23 | 0.076 (2) | 0.060 (2) | 0.053 (2) | −0.014 (2) | 0.005 (2) | −0.0069 (19) |
O1 | 0.0706 (17) | 0.0684 (15) | 0.0846 (17) | −0.0048 (14) | 0.0022 (14) | 0.0202 (14) |
O2 | 0.0602 (15) | 0.0605 (14) | 0.0630 (15) | −0.0050 (12) | 0.0041 (12) | −0.0160 (12) |
O3 | 0.159 (3) | 0.0601 (16) | 0.0610 (16) | 0.0017 (19) | −0.008 (2) | −0.0043 (14) |
C1—C2 | 1.479 (5) | C14—C15 | 1.367 (5) |
C1—H1A | 0.9600 | C14—N1 | 1.439 (4) |
C1—H1B | 0.9600 | C15—C16 | 1.394 (4) |
C1—H1C | 0.9600 | C15—H15 | 0.9300 |
C2—O2 | 1.431 (4) | C16—H16 | 0.9300 |
C2—H2A | 0.9700 | C17—N1 | 1.386 (4) |
C2—H2B | 0.9700 | C17—C22 | 1.392 (4) |
C3—O2 | 1.371 (3) | C17—C18 | 1.407 (4) |
C3—C4 | 1.380 (4) | C18—C19 | 1.381 (4) |
C3—C8 | 1.387 (5) | C18—H18 | 0.9300 |
C4—C5 | 1.372 (4) | C19—C20 | 1.387 (4) |
C4—H4 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.388 (4) | C20—C21 | 1.380 (4) |
C5—H5 | 0.9300 | C20—N2 | 1.429 (4) |
C6—C7 | 1.382 (4) | C21—C22 | 1.373 (4) |
C6—N1 | 1.431 (4) | C21—H21 | 0.9300 |
C7—C8 | 1.370 (4) | C22—H22 | 0.9300 |
C7—H7 | 0.9300 | N2—C23 | 1.257 (4) |
C8—H8 | 0.9300 | C24—C25 | 1.368 (5) |
C9—C10 | 1.508 (5) | C24—C29 | 1.385 (5) |
C9—H9A | 0.9600 | C24—C23 | 1.450 (5) |
C9—H9B | 0.9600 | C25—C26 | 1.379 (6) |
C9—H9C | 0.9600 | C25—H25 | 0.9300 |
C10—O1 | 1.408 (4) | C26—C27 | 1.375 (6) |
C10—H10A | 0.9700 | C26—H26 | 0.9300 |
C10—H10B | 0.9700 | C27—C28 | 1.347 (6) |
C11—C12 | 1.366 (5) | C27—H27 | 0.9300 |
C11—C16 | 1.369 (5) | C28—C29 | 1.388 (5) |
C11—O1 | 1.376 (4) | C28—H28 | 0.9300 |
C12—C13 | 1.376 (5) | C29—O3 | 1.337 (4) |
C12—H12 | 0.9300 | C23—H23 | 0.9300 |
C13—C14 | 1.379 (4) | O3—H3 | 0.8200 |
C13—H13 | 0.9300 | ||
C2—C1—H1A | 109.5 | C13—C14—N1 | 119.8 (3) |
C2—C1—H1B | 109.5 | C14—C15—C16 | 120.5 (3) |
H1A—C1—H1B | 109.5 | C14—C15—H15 | 119.7 |
C2—C1—H1C | 109.5 | C16—C15—H15 | 119.7 |
H1A—C1—H1C | 109.5 | C11—C16—C15 | 119.6 (3) |
H1B—C1—H1C | 109.5 | C11—C16—H16 | 120.2 |
O2—C2—C1 | 109.2 (3) | C15—C16—H16 | 120.2 |
O2—C2—H2A | 109.8 | N1—C17—C22 | 121.5 (3) |
C1—C2—H2A | 109.8 | N1—C17—C18 | 120.5 (3) |
O2—C2—H2B | 109.8 | C22—C17—C18 | 117.9 (3) |
C1—C2—H2B | 109.8 | C19—C18—C17 | 120.0 (3) |
H2A—C2—H2B | 108.3 | C19—C18—H18 | 120.0 |
O2—C3—C4 | 124.7 (3) | C17—C18—H18 | 120.0 |
O2—C3—C8 | 115.6 (3) | C18—C19—C20 | 121.7 (3) |
C4—C3—C8 | 119.8 (3) | C18—C19—H19 | 119.1 |
C5—C4—C3 | 119.6 (3) | C20—C19—H19 | 119.1 |
C5—C4—H4 | 120.2 | C21—C20—C19 | 117.6 (3) |
C3—C4—H4 | 120.2 | C21—C20—N2 | 116.8 (3) |
C4—C5—C6 | 121.3 (3) | C19—C20—N2 | 125.5 (3) |
C4—C5—H5 | 119.4 | C22—C21—C20 | 121.9 (3) |
C6—C5—H5 | 119.4 | C22—C21—H21 | 119.1 |
C7—C6—C5 | 118.3 (3) | C20—C21—H21 | 119.1 |
C7—C6—N1 | 120.1 (3) | C21—C22—C17 | 120.8 (3) |
C5—C6—N1 | 121.5 (3) | C21—C22—H22 | 119.6 |
C8—C7—C6 | 121.0 (3) | C17—C22—H22 | 119.6 |
C8—C7—H7 | 119.5 | C23—N2—C20 | 122.5 (3) |
C6—C7—H7 | 119.5 | C25—C24—C29 | 117.9 (3) |
C7—C8—C3 | 119.9 (3) | C25—C24—C23 | 120.1 (3) |
C7—C8—H8 | 120.0 | C29—C24—C23 | 121.9 (3) |
C3—C8—H8 | 120.0 | C24—C25—C26 | 121.4 (4) |
C10—C9—H9A | 109.5 | C24—C25—H25 | 119.3 |
C10—C9—H9B | 109.5 | C26—C25—H25 | 119.3 |
H9A—C9—H9B | 109.5 | C27—C26—C25 | 119.5 (4) |
C10—C9—H9C | 109.5 | C27—C26—H26 | 120.3 |
H9A—C9—H9C | 109.5 | C25—C26—H26 | 120.3 |
H9B—C9—H9C | 109.5 | C28—C27—C26 | 120.5 (4) |
O1—C10—C9 | 107.3 (3) | C28—C27—H27 | 119.7 |
O1—C10—H10A | 110.3 | C26—C27—H27 | 119.7 |
C9—C10—H10A | 110.3 | C27—C28—C29 | 119.8 (4) |
O1—C10—H10B | 110.3 | C27—C28—H28 | 120.1 |
C9—C10—H10B | 110.3 | C29—C28—H28 | 120.1 |
H10A—C10—H10B | 108.5 | O3—C29—C24 | 120.8 (3) |
C12—C11—C16 | 119.9 (3) | O3—C29—C28 | 118.3 (3) |
C12—C11—O1 | 115.1 (3) | C24—C29—C28 | 120.9 (4) |
C16—C11—O1 | 125.0 (3) | C17—N1—C6 | 123.0 (3) |
C11—C12—C13 | 120.5 (3) | C17—N1—C14 | 120.2 (3) |
C11—C12—H12 | 119.7 | C6—N1—C14 | 116.5 (2) |
C13—C12—H12 | 119.7 | N2—C23—C24 | 122.9 (3) |
C12—C13—C14 | 120.2 (3) | N2—C23—H23 | 118.5 |
C12—C13—H13 | 119.9 | C24—C23—H23 | 118.5 |
C14—C13—H13 | 119.9 | C11—O1—C10 | 118.3 (3) |
C15—C14—C13 | 119.2 (3) | C3—O2—C2 | 118.0 (3) |
C15—C14—N1 | 121.0 (3) | C29—O3—H3 | 109.5 |
O2—C3—C4—C5 | 179.0 (3) | C29—C24—C25—C26 | −0.3 (8) |
C8—C3—C4—C5 | −1.2 (5) | C23—C24—C25—C26 | −178.7 (5) |
C3—C4—C5—C6 | 0.9 (5) | C24—C25—C26—C27 | −0.8 (11) |
C4—C5—C6—C7 | 0.0 (5) | C25—C26—C27—C28 | 1.1 (11) |
C4—C5—C6—N1 | −176.9 (3) | C26—C27—C28—C29 | −0.3 (9) |
C5—C6—C7—C8 | −0.5 (5) | C25—C24—C29—O3 | −178.7 (4) |
N1—C6—C7—C8 | 176.4 (3) | C23—C24—C29—O3 | −0.3 (6) |
C6—C7—C8—C3 | 0.2 (5) | C25—C24—C29—C28 | 1.1 (7) |
O2—C3—C8—C7 | −179.6 (3) | C23—C24—C29—C28 | 179.5 (4) |
C4—C3—C8—C7 | 0.7 (5) | C27—C28—C29—O3 | 178.9 (5) |
C16—C11—C12—C13 | −1.1 (5) | C27—C28—C29—C24 | −0.8 (7) |
O1—C11—C12—C13 | 178.3 (3) | C22—C17—N1—C6 | 164.1 (3) |
C11—C12—C13—C14 | 1.0 (5) | C18—C17—N1—C6 | −19.1 (5) |
C12—C13—C14—C15 | −0.2 (5) | C22—C17—N1—C14 | −9.9 (5) |
C12—C13—C14—N1 | 178.6 (3) | C18—C17—N1—C14 | 166.8 (3) |
C13—C14—C15—C16 | −0.6 (5) | C7—C6—N1—C17 | 121.5 (3) |
N1—C14—C15—C16 | −179.4 (3) | C5—C6—N1—C17 | −61.7 (4) |
C12—C11—C16—C15 | 0.3 (5) | C7—C6—N1—C14 | −64.3 (4) |
O1—C11—C16—C15 | −179.1 (3) | C5—C6—N1—C14 | 112.6 (4) |
C14—C15—C16—C11 | 0.6 (5) | C15—C14—N1—C17 | −79.1 (4) |
N1—C17—C18—C19 | −175.8 (3) | C13—C14—N1—C17 | 102.1 (4) |
C22—C17—C18—C19 | 1.1 (5) | C15—C14—N1—C6 | 106.4 (4) |
C17—C18—C19—C20 | 0.0 (5) | C13—C14—N1—C6 | −72.3 (4) |
C18—C19—C20—C21 | −0.7 (5) | C20—N2—C23—C24 | −177.0 (3) |
C18—C19—C20—N2 | 176.7 (3) | C25—C24—C23—N2 | 178.0 (4) |
C19—C20—C21—C22 | 0.2 (5) | C29—C24—C23—N2 | −0.3 (6) |
N2—C20—C21—C22 | −177.3 (3) | C12—C11—O1—C10 | 172.5 (3) |
C20—C21—C22—C17 | 0.9 (6) | C16—C11—O1—C10 | −8.2 (5) |
N1—C17—C22—C21 | 175.3 (3) | C9—C10—O1—C11 | −176.7 (3) |
C18—C17—C22—C21 | −1.5 (5) | C4—C3—O2—C2 | −10.3 (4) |
C21—C20—N2—C23 | −170.9 (3) | C8—C3—O2—C2 | 170.0 (3) |
C19—C20—N2—C23 | 11.7 (5) | C1—C2—O2—C3 | −172.8 (3) |
Cg1 Cg2 and Cg3 are the centroids of the C3–C8, C11–C16 and C17–C22 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N2 | 0.82 | 1.87 | 2.605 (4) | 148 |
C1—H1C···Cg2i | 0.96 | 2.84 | 3.760 (4) | 162 |
C4—H4···Cg3ii | 0.93 | 2.82 | 3.655 (3) | 150 |
C9—H9C···Cg1iii | 0.96 | 2.94 | 3.872 (4) | 164 |
C28—H28···Cg1iv | 0.93 | 2.88 | 3.742 (4) | 154 |
Symmetry codes: (i) −x, y+1/2, −z+5/2; (ii) x+1/2, −y+1/2, −z+2; (iii) −x, y−1/2, −z+5/2; (iv) −x, y−1/2, −z+3/2. |
Cg1 Cg2 and Cg3 are the centroids of the C3–C8, C11–C16 and C17–C22 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N2 | 0.82 | 1.87 | 2.605 (4) | 148 |
C1—H1C···Cg2i | 0.96 | 2.8370 | 3.760 (4) | 162 |
C4—H4···Cg3ii | 0.93 | 2.8182 | 3.655 (3) | 150 |
C9—H9C···Cg1iii | 0.96 | 2.9417 | 3.872 (4) | 164 |
C28—H28···Cg1iv | 0.93 | 2.8839 | 3.742 (4) | 154 |
Symmetry codes: (i) −x, y+1/2, −z+5/2; (ii) x+1/2, −y+1/2, −z+2; (iii) −x, y−1/2, −z+5/2; (iv) −x, y−1/2, −z+3/2. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (51372003, 21271004).
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In the past few decades, the researchers have witnessed a great deal of interest in the chemistry of transition metal Schiff base chelates bacause of their importance as catalysts in reactions such as carbonylation, hydroformylation, reduction, oxidation, epoxidation and hydrolysis (Dharmaraj et al., 2001). Schiff bases derived from salicyladehyde and fluoroaniline, specifically, have been considered as potential pharmaceutically interesting compounds as several of the members of this family of molecules have shown antimicrobial, antitumor or antiviral activities (Feng et al., 2014). As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound (I) is reported.
In (I) (Fig.1), the molecular structure of title compound shows an E configuration, with a C(20)—N(2)=C(23)—C(24) torsion angle of -176.9 (3)°. The bond distance of N(2)=C(23) at 1.258 (3) Å is a typical double bond. The dihedral angles between the salicyladehyde moiety and the aniline ring is 12.1 (2)°, indicating they are nearly coplanar. Intramolecular O—H···N hydrogen bond exists, similar to that found in a related structure (Tanak et al. 2013). In the crystal, the molecules are linked via weak C—H···π interaction into the three dimensional supramolecular architecture.