organic compounds
2-{(E)-[4-(Diphenylamino)phenyl]iminomethyl}phenol
aDepartment of Chemistry, Bengbu Medical College, Bengbu 233030, People's Republic of China, bDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and cKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
*Correspondence e-mail: jywu1957@163.com
The 25H20N2O, contains two independent molecules. In each molecule, the C=N bond is in an E conformation. The most significant difference between the two molecules is seen for the dihedral angles between the methoxy-substituted benzene ring and the two phenyl rings, which are 85.5 (1) and 82.3 (1)° in the first molecule, and 49.0 (1) and 40.4 (1)° in the second. This conformational difference is reflected in the central C=N—C C torsion angle, which is 28.7 (2)° in the first molecule and −29.8 (3)° in the other. In each molecule, there is an intramolecular O—H⋯N hydrogen bond.
of the title Schiff base molecule, CCCDC reference: 908853
Experimental
Crystal data
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); 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: 908853
10.1107/S1600536814003195/lh5685sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003195/lh5685Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003195/lh5685Isup3.cml
A solution of N1,N1-diphenylbenzene-1,4-diamine (13.00 g, 50 ammol) in 30 ml of ethanol was mixed with 2-hydroxybenzaldehyde (9.15 g, 75 mmol) in ethanol 5 ml. The mixture was refluxed for 4h under cooling to room temperature, the soild was filtrated and recrystallized from ethnol to give X-ray quality crystals. Yield: 85%. 1H NMR (400 MHz, d6-(CD3)2CO) 6.99 (t, 2H), 7.12 (m, 8H), 7.36 (t, 4H), 7.41 (d, 3H), 7.59 (d, 1H), 8.93(d, 1H), 13.28 (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, O—H = 0.82Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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). Displacement ellipsoids are drawn at the 30% probability level. |
C25H20N2O | F(000) = 1536 |
Mr = 364.43 | Dx = 1.230 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9854 reflections |
a = 18.4128 (4) Å | θ = 2.2–24.7° |
b = 21.2523 (4) Å | µ = 0.08 mm−1 |
c = 10.2080 (2) Å | T = 298 K |
β = 99.834 (1)° | Block, yellow |
V = 3935.84 (14) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 8961 independent reflections |
Radiation source: fine-focus sealed tube | 6499 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→18 |
Tmin = 0.978, Tmax = 0.985 | k = −27→23 |
65034 measured reflections | l = −13→13 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.5243P] where P = (Fo2 + 2Fc2)/3 |
8961 reflections | (Δ/σ)max = 0.001 |
507 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C25H20N2O | V = 3935.84 (14) Å3 |
Mr = 364.43 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.4128 (4) Å | µ = 0.08 mm−1 |
b = 21.2523 (4) Å | T = 298 K |
c = 10.2080 (2) Å | 0.30 × 0.20 × 0.20 mm |
β = 99.834 (1)° |
Bruker SMART CCD diffractometer | 8961 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6499 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.985 | Rint = 0.029 |
65034 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.13 e Å−3 |
8961 reflections | Δρmin = −0.18 e Å−3 |
507 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 | ||
N2 | 0.65015 (7) | 0.18511 (7) | 0.70724 (14) | 0.0475 (3) | |
O1 | 0.52431 (8) | 0.12577 (8) | 0.67606 (13) | 0.0767 (4) | |
H1 | 0.5657 | 0.1359 | 0.7130 | 0.115* | |
C35 | 0.71752 (14) | 0.54098 (15) | 1.1730 (2) | 0.0880 (8) | |
H35 | 0.7229 | 0.5554 | 1.2602 | 0.106* | |
N4 | 0.41701 (8) | 0.39242 (7) | 0.52112 (15) | 0.0553 (4) | |
N1 | 0.91196 (7) | 0.25341 (7) | 1.04786 (15) | 0.0546 (4) | |
O2 | 0.28230 (8) | 0.36766 (9) | 0.54581 (15) | 0.0775 (4) | |
H2 | 0.3237 | 0.3829 | 0.5651 | 0.116* | |
N3 | 0.69482 (8) | 0.47621 (8) | 0.77970 (15) | 0.0589 (4) | |
C16 | 0.71657 (8) | 0.20425 (7) | 0.78898 (16) | 0.0440 (3) | |
C13 | 0.84654 (8) | 0.23704 (7) | 0.96105 (16) | 0.0455 (4) | |
C20 | 0.56131 (8) | 0.19141 (8) | 0.50738 (16) | 0.0462 (4) | |
C7 | 0.96755 (8) | 0.20695 (8) | 1.08522 (17) | 0.0463 (4) | |
C19 | 0.63139 (9) | 0.20661 (8) | 0.58888 (17) | 0.0483 (4) | |
H19 | 0.6639 | 0.2328 | 0.5543 | 0.058* | |
C1 | 0.92484 (9) | 0.31669 (7) | 1.09053 (16) | 0.0467 (4) | |
C32 | 0.70191 (10) | 0.49776 (9) | 0.91339 (18) | 0.0550 (4) | |
C45 | 0.33276 (10) | 0.34029 (8) | 0.35242 (19) | 0.0557 (4) | |
C15 | 0.74933 (9) | 0.26249 (8) | 0.77910 (17) | 0.0518 (4) | |
H15 | 0.7277 | 0.2911 | 0.7152 | 0.062* | |
C39 | 0.62060 (9) | 0.40697 (8) | 0.61860 (18) | 0.0537 (4) | |
H39 | 0.6634 | 0.3878 | 0.6016 | 0.064* | |
C26 | 0.75879 (9) | 0.47338 (8) | 0.71989 (17) | 0.0489 (4) | |
C8 | 1.00166 (10) | 0.20185 (9) | 1.21639 (18) | 0.0573 (4) | |
H8 | 0.9875 | 0.2279 | 1.2807 | 0.069* | |
C25 | 0.50993 (9) | 0.15246 (9) | 0.55383 (17) | 0.0545 (4) | |
C21 | 0.54279 (10) | 0.21685 (9) | 0.38024 (18) | 0.0581 (4) | |
H21 | 0.5768 | 0.2422 | 0.3475 | 0.070* | |
C17 | 0.74919 (9) | 0.16321 (8) | 0.88735 (16) | 0.0470 (4) | |
H17 | 0.7276 | 0.1242 | 0.8961 | 0.056* | |
C40 | 0.55297 (10) | 0.38645 (9) | 0.55257 (18) | 0.0549 (4) | |
H40 | 0.5507 | 0.3540 | 0.4909 | 0.066* | |
C38 | 0.62562 (9) | 0.45600 (8) | 0.71015 (17) | 0.0512 (4) | |
C18 | 0.81303 (9) | 0.17920 (8) | 0.97237 (17) | 0.0482 (4) | |
H18 | 0.8338 | 0.1510 | 1.0378 | 0.058* | |
C12 | 0.98805 (9) | 0.16712 (8) | 0.99112 (18) | 0.0528 (4) | |
H12 | 0.9648 | 0.1699 | 0.9030 | 0.063* | |
C2 | 0.86863 (10) | 0.35225 (8) | 1.12765 (18) | 0.0535 (4) | |
H2A | 0.8223 | 0.3345 | 1.1259 | 0.064* | |
C11 | 1.04306 (10) | 0.12317 (9) | 1.0277 (2) | 0.0616 (5) | |
H11 | 1.0566 | 0.0963 | 0.9640 | 0.074* | |
C14 | 0.81354 (9) | 0.27842 (8) | 0.86274 (18) | 0.0533 (4) | |
H14 | 0.8352 | 0.3173 | 0.8535 | 0.064* | |
C6 | 0.99364 (10) | 0.34357 (9) | 1.0969 (2) | 0.0612 (5) | |
H6 | 1.0320 | 0.3203 | 1.0727 | 0.073* | |
C44 | 0.40457 (10) | 0.36586 (9) | 0.40703 (19) | 0.0580 (4) | |
H44 | 0.4425 | 0.3629 | 0.3579 | 0.070* | |
C41 | 0.48819 (9) | 0.41398 (9) | 0.57765 (17) | 0.0524 (4) | |
C50 | 0.27411 (10) | 0.34239 (9) | 0.4237 (2) | 0.0612 (5) | |
C9 | 1.05702 (11) | 0.15786 (11) | 1.2517 (2) | 0.0680 (5) | |
H9 | 1.0802 | 0.1548 | 1.3398 | 0.082* | |
C27 | 0.75680 (10) | 0.49235 (9) | 0.58993 (19) | 0.0574 (4) | |
H27 | 0.7128 | 0.5063 | 0.5397 | 0.069* | |
C43 | 0.56070 (10) | 0.48410 (10) | 0.73322 (19) | 0.0606 (5) | |
H43 | 0.5628 | 0.5177 | 0.7922 | 0.073* | |
C31 | 0.82527 (10) | 0.45261 (9) | 0.7935 (2) | 0.0595 (5) | |
H31 | 0.8274 | 0.4396 | 0.8811 | 0.071* | |
C30 | 0.88793 (11) | 0.45130 (9) | 0.7362 (3) | 0.0705 (6) | |
H30 | 0.9322 | 0.4375 | 0.7856 | 0.085* | |
C28 | 0.82003 (12) | 0.49053 (10) | 0.5349 (2) | 0.0696 (5) | |
H28 | 0.8183 | 0.5033 | 0.4473 | 0.083* | |
C46 | 0.32167 (12) | 0.31212 (11) | 0.2265 (2) | 0.0757 (6) | |
H46 | 0.3602 | 0.3108 | 0.1784 | 0.091* | |
C29 | 0.88547 (12) | 0.47023 (10) | 0.6072 (3) | 0.0732 (6) | |
H29 | 0.9278 | 0.4693 | 0.5690 | 0.088* | |
C3 | 0.88131 (12) | 0.41414 (10) | 1.1674 (2) | 0.0673 (5) | |
H3 | 0.8430 | 0.4380 | 1.1902 | 0.081* | |
C22 | 0.47585 (12) | 0.20549 (11) | 0.3023 (2) | 0.0676 (5) | |
H22 | 0.4645 | 0.2230 | 0.2178 | 0.081* | |
C42 | 0.49353 (10) | 0.46248 (10) | 0.6692 (2) | 0.0605 (5) | |
H42 | 0.4506 | 0.4809 | 0.6879 | 0.073* | |
C24 | 0.44245 (10) | 0.14073 (12) | 0.4740 (2) | 0.0704 (6) | |
H24 | 0.4085 | 0.1144 | 0.5042 | 0.084* | |
C10 | 1.07792 (10) | 0.11884 (10) | 1.1578 (2) | 0.0666 (5) | |
H10 | 1.1154 | 0.0896 | 1.1819 | 0.080* | |
C23 | 0.42569 (11) | 0.16797 (12) | 0.3502 (2) | 0.0726 (6) | |
H23 | 0.3798 | 0.1608 | 0.2983 | 0.087* | |
C37 | 0.74217 (11) | 0.55151 (10) | 0.9510 (2) | 0.0651 (5) | |
H37 | 0.7642 | 0.5734 | 0.8893 | 0.078* | |
C33 | 0.66962 (13) | 0.46571 (11) | 1.0058 (2) | 0.0724 (6) | |
H33 | 0.6427 | 0.4293 | 0.9814 | 0.087* | |
C4 | 0.94920 (14) | 0.44041 (10) | 1.1734 (3) | 0.0803 (6) | |
H4 | 0.9574 | 0.4820 | 1.2004 | 0.096* | |
C36 | 0.74966 (13) | 0.57282 (12) | 1.0814 (2) | 0.0815 (7) | |
H36 | 0.7768 | 0.6091 | 1.1066 | 0.098* | |
C5 | 1.00554 (13) | 0.40513 (11) | 1.1393 (3) | 0.0801 (7) | |
H5 | 1.0522 | 0.4228 | 1.1447 | 0.096* | |
C49 | 0.20642 (12) | 0.31691 (12) | 0.3675 (3) | 0.0850 (7) | |
H49 | 0.1671 | 0.3186 | 0.4137 | 0.102* | |
C47 | 0.25461 (16) | 0.28644 (12) | 0.1733 (3) | 0.0941 (8) | |
H47 | 0.2478 | 0.2673 | 0.0902 | 0.113* | |
C34 | 0.67742 (15) | 0.48791 (15) | 1.1355 (2) | 0.0883 (8) | |
H34 | 0.6551 | 0.4664 | 1.1974 | 0.106* | |
C48 | 0.19746 (14) | 0.28941 (13) | 0.2448 (3) | 0.0976 (9) | |
H48 | 0.1519 | 0.2724 | 0.2086 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0392 (7) | 0.0522 (8) | 0.0498 (8) | −0.0011 (6) | 0.0035 (6) | −0.0029 (6) |
O1 | 0.0643 (8) | 0.1061 (12) | 0.0574 (8) | −0.0312 (8) | 0.0041 (6) | 0.0169 (8) |
C35 | 0.0838 (16) | 0.117 (2) | 0.0560 (12) | 0.0424 (15) | −0.0093 (11) | −0.0196 (14) |
N4 | 0.0454 (7) | 0.0602 (9) | 0.0582 (9) | −0.0063 (6) | 0.0029 (6) | −0.0003 (7) |
N1 | 0.0470 (7) | 0.0417 (7) | 0.0671 (9) | 0.0048 (6) | −0.0129 (6) | −0.0055 (7) |
O2 | 0.0627 (8) | 0.0956 (12) | 0.0762 (10) | 0.0009 (8) | 0.0177 (7) | 0.0033 (8) |
N3 | 0.0485 (8) | 0.0746 (10) | 0.0523 (8) | −0.0128 (7) | 0.0052 (6) | −0.0119 (7) |
C16 | 0.0364 (7) | 0.0464 (8) | 0.0484 (8) | 0.0006 (6) | 0.0043 (6) | −0.0021 (7) |
C13 | 0.0415 (8) | 0.0411 (8) | 0.0505 (9) | 0.0025 (6) | −0.0017 (6) | −0.0028 (7) |
C20 | 0.0411 (8) | 0.0505 (9) | 0.0462 (8) | −0.0019 (6) | 0.0054 (6) | −0.0053 (7) |
C7 | 0.0381 (7) | 0.0426 (8) | 0.0556 (9) | 0.0010 (6) | 0.0006 (6) | 0.0021 (7) |
C19 | 0.0412 (8) | 0.0530 (9) | 0.0507 (9) | −0.0044 (7) | 0.0079 (7) | −0.0017 (7) |
C1 | 0.0483 (8) | 0.0418 (8) | 0.0469 (8) | −0.0017 (6) | −0.0012 (7) | −0.0014 (7) |
C32 | 0.0509 (9) | 0.0603 (10) | 0.0511 (9) | 0.0002 (8) | 0.0010 (7) | −0.0055 (8) |
C45 | 0.0487 (9) | 0.0498 (10) | 0.0647 (11) | −0.0001 (7) | −0.0010 (8) | −0.0008 (8) |
C15 | 0.0522 (9) | 0.0434 (9) | 0.0548 (10) | 0.0044 (7) | −0.0051 (7) | 0.0049 (7) |
C39 | 0.0464 (9) | 0.0543 (10) | 0.0596 (10) | 0.0001 (7) | 0.0067 (7) | −0.0062 (8) |
C26 | 0.0464 (8) | 0.0418 (8) | 0.0571 (10) | −0.0062 (7) | 0.0046 (7) | −0.0027 (7) |
C8 | 0.0530 (9) | 0.0629 (11) | 0.0530 (10) | 0.0075 (8) | 0.0001 (8) | −0.0029 (8) |
C25 | 0.0464 (9) | 0.0667 (11) | 0.0500 (9) | −0.0082 (8) | 0.0074 (7) | −0.0037 (8) |
C21 | 0.0576 (10) | 0.0627 (11) | 0.0527 (10) | −0.0075 (8) | 0.0055 (8) | 0.0019 (8) |
C17 | 0.0459 (8) | 0.0429 (8) | 0.0511 (9) | −0.0043 (7) | 0.0052 (7) | 0.0030 (7) |
C40 | 0.0517 (9) | 0.0536 (10) | 0.0576 (10) | −0.0033 (7) | 0.0046 (8) | −0.0090 (8) |
C38 | 0.0467 (9) | 0.0546 (10) | 0.0509 (9) | −0.0070 (7) | 0.0045 (7) | −0.0031 (7) |
C18 | 0.0498 (9) | 0.0407 (8) | 0.0507 (9) | 0.0024 (7) | −0.0009 (7) | 0.0056 (7) |
C12 | 0.0527 (9) | 0.0535 (10) | 0.0501 (9) | 0.0021 (7) | 0.0032 (7) | 0.0005 (8) |
C2 | 0.0507 (9) | 0.0490 (9) | 0.0596 (10) | 0.0017 (7) | 0.0057 (7) | −0.0010 (8) |
C11 | 0.0525 (10) | 0.0597 (11) | 0.0734 (12) | 0.0094 (8) | 0.0130 (9) | −0.0049 (9) |
C14 | 0.0529 (9) | 0.0380 (8) | 0.0637 (10) | −0.0046 (7) | −0.0048 (8) | 0.0051 (7) |
C6 | 0.0512 (10) | 0.0577 (11) | 0.0738 (12) | −0.0053 (8) | 0.0085 (9) | −0.0066 (9) |
C44 | 0.0460 (9) | 0.0674 (12) | 0.0600 (11) | −0.0042 (8) | 0.0076 (8) | −0.0023 (9) |
C41 | 0.0450 (8) | 0.0571 (10) | 0.0537 (9) | −0.0073 (7) | 0.0047 (7) | −0.0001 (8) |
C50 | 0.0475 (9) | 0.0579 (11) | 0.0757 (13) | −0.0002 (8) | 0.0039 (8) | 0.0104 (10) |
C9 | 0.0566 (10) | 0.0810 (14) | 0.0599 (11) | 0.0139 (10) | −0.0090 (9) | 0.0049 (10) |
C27 | 0.0554 (10) | 0.0523 (10) | 0.0636 (11) | −0.0042 (8) | 0.0074 (8) | 0.0057 (8) |
C43 | 0.0554 (10) | 0.0631 (11) | 0.0630 (11) | −0.0019 (8) | 0.0092 (8) | −0.0172 (9) |
C31 | 0.0565 (10) | 0.0492 (10) | 0.0684 (11) | −0.0023 (8) | −0.0019 (9) | 0.0008 (8) |
C30 | 0.0488 (10) | 0.0493 (10) | 0.1082 (18) | 0.0018 (8) | −0.0011 (10) | −0.0123 (11) |
C28 | 0.0740 (13) | 0.0618 (12) | 0.0772 (13) | −0.0143 (10) | 0.0252 (11) | 0.0013 (10) |
C46 | 0.0661 (12) | 0.0793 (14) | 0.0757 (14) | 0.0055 (10) | −0.0050 (10) | −0.0161 (12) |
C29 | 0.0601 (12) | 0.0543 (11) | 0.1110 (19) | −0.0119 (9) | 0.0310 (12) | −0.0178 (12) |
C3 | 0.0758 (13) | 0.0549 (11) | 0.0682 (12) | 0.0126 (9) | 0.0038 (10) | −0.0106 (9) |
C22 | 0.0696 (12) | 0.0754 (13) | 0.0517 (10) | −0.0030 (10) | −0.0071 (9) | 0.0001 (9) |
C42 | 0.0463 (9) | 0.0679 (12) | 0.0672 (11) | 0.0000 (8) | 0.0097 (8) | −0.0129 (9) |
C24 | 0.0500 (10) | 0.0926 (16) | 0.0674 (13) | −0.0241 (10) | 0.0064 (9) | −0.0085 (11) |
C10 | 0.0463 (9) | 0.0671 (12) | 0.0825 (14) | 0.0162 (8) | 0.0002 (9) | 0.0043 (11) |
C23 | 0.0538 (10) | 0.0930 (16) | 0.0644 (12) | −0.0107 (10) | −0.0088 (9) | −0.0120 (11) |
C37 | 0.0570 (10) | 0.0642 (12) | 0.0691 (12) | −0.0007 (9) | −0.0039 (9) | −0.0094 (10) |
C33 | 0.0802 (14) | 0.0755 (14) | 0.0623 (12) | −0.0020 (11) | 0.0149 (10) | 0.0035 (10) |
C4 | 0.0904 (16) | 0.0478 (11) | 0.0958 (17) | −0.0088 (11) | −0.0037 (13) | −0.0152 (11) |
C36 | 0.0690 (13) | 0.0803 (15) | 0.0833 (16) | 0.0147 (11) | −0.0211 (12) | −0.0294 (13) |
C5 | 0.0685 (13) | 0.0657 (13) | 0.1025 (17) | −0.0241 (11) | 0.0046 (12) | −0.0100 (12) |
C49 | 0.0499 (11) | 0.0879 (17) | 0.113 (2) | −0.0064 (11) | 0.0006 (12) | 0.0179 (15) |
C47 | 0.0868 (17) | 0.0775 (16) | 0.1023 (19) | 0.0035 (13) | −0.0287 (15) | −0.0260 (14) |
C34 | 0.0930 (17) | 0.114 (2) | 0.0592 (13) | 0.0266 (16) | 0.0154 (12) | 0.0115 (14) |
C48 | 0.0638 (14) | 0.0815 (16) | 0.132 (2) | −0.0167 (12) | −0.0281 (15) | 0.0068 (16) |
N2—C19 | 1.283 (2) | C18—H18 | 0.9300 |
N2—C16 | 1.4173 (19) | C12—C11 | 1.382 (2) |
O1—C25 | 1.355 (2) | C12—H12 | 0.9300 |
O1—H1 | 0.8200 | C2—C3 | 1.385 (3) |
C35—C34 | 1.366 (4) | C2—H2A | 0.9300 |
C35—C36 | 1.368 (4) | C11—C10 | 1.376 (3) |
C35—H35 | 0.9300 | C11—H11 | 0.9300 |
N4—C44 | 1.279 (2) | C14—H14 | 0.9300 |
N4—C41 | 1.415 (2) | C6—C5 | 1.384 (3) |
N1—C13 | 1.4115 (19) | C6—H6 | 0.9300 |
N1—C1 | 1.421 (2) | C44—H44 | 0.9300 |
N1—C7 | 1.427 (2) | C41—C42 | 1.384 (3) |
O2—C50 | 1.342 (2) | C50—C49 | 1.390 (3) |
O2—H2 | 0.8200 | C9—C10 | 1.371 (3) |
N3—C38 | 1.415 (2) | C9—H9 | 0.9300 |
N3—C26 | 1.418 (2) | C27—C28 | 1.377 (3) |
N3—C32 | 1.424 (2) | C27—H27 | 0.9300 |
C16—C17 | 1.387 (2) | C43—C42 | 1.376 (3) |
C16—C15 | 1.388 (2) | C43—H43 | 0.9300 |
C13—C18 | 1.389 (2) | C31—C30 | 1.380 (3) |
C13—C14 | 1.393 (2) | C31—H31 | 0.9300 |
C20—C21 | 1.393 (2) | C30—C29 | 1.371 (3) |
C20—C25 | 1.399 (2) | C30—H30 | 0.9300 |
C20—C19 | 1.447 (2) | C28—C29 | 1.371 (3) |
C7—C12 | 1.380 (2) | C28—H28 | 0.9300 |
C7—C8 | 1.383 (2) | C46—C47 | 1.374 (3) |
C19—H19 | 0.9300 | C46—H46 | 0.9300 |
C1—C6 | 1.381 (2) | C29—H29 | 0.9300 |
C1—C2 | 1.385 (2) | C3—C4 | 1.361 (3) |
C32—C33 | 1.378 (3) | C3—H3 | 0.9300 |
C32—C37 | 1.380 (3) | C22—C23 | 1.372 (3) |
C45—C46 | 1.400 (3) | C22—H22 | 0.9300 |
C45—C50 | 1.402 (3) | C42—H42 | 0.9300 |
C45—C44 | 1.450 (2) | C24—C23 | 1.377 (3) |
C15—C14 | 1.377 (2) | C24—H24 | 0.9300 |
C15—H15 | 0.9300 | C10—H10 | 0.9300 |
C39—C40 | 1.381 (2) | C23—H23 | 0.9300 |
C39—C38 | 1.392 (2) | C37—C36 | 1.391 (3) |
C39—H39 | 0.9300 | C37—H37 | 0.9300 |
C26—C27 | 1.381 (2) | C33—C34 | 1.390 (3) |
C26—C31 | 1.394 (2) | C33—H33 | 0.9300 |
C8—C9 | 1.385 (3) | C4—C5 | 1.372 (3) |
C8—H8 | 0.9300 | C4—H4 | 0.9300 |
C25—C24 | 1.387 (2) | C36—H36 | 0.9300 |
C21—C22 | 1.369 (3) | C5—H5 | 0.9300 |
C21—H21 | 0.9300 | C49—C48 | 1.367 (4) |
C17—C18 | 1.379 (2) | C49—H49 | 0.9300 |
C17—H17 | 0.9300 | C47—C48 | 1.380 (4) |
C40—C41 | 1.391 (3) | C47—H47 | 0.9300 |
C40—H40 | 0.9300 | C34—H34 | 0.9300 |
C38—C43 | 1.392 (3) | C48—H48 | 0.9300 |
C19—N2—C16 | 121.25 (14) | C1—C6—H6 | 120.0 |
C25—O1—H1 | 109.5 | C5—C6—H6 | 120.0 |
C34—C35—C36 | 119.5 (2) | N4—C44—C45 | 121.68 (17) |
C34—C35—H35 | 120.2 | N4—C44—H44 | 119.2 |
C36—C35—H35 | 120.2 | C45—C44—H44 | 119.2 |
C44—N4—C41 | 121.57 (16) | C42—C41—C40 | 118.26 (15) |
C13—N1—C1 | 120.37 (13) | C42—C41—N4 | 118.07 (16) |
C13—N1—C7 | 119.58 (13) | C40—C41—N4 | 123.53 (16) |
C1—N1—C7 | 119.90 (13) | O2—C50—C49 | 119.3 (2) |
C50—O2—H2 | 109.5 | O2—C50—C45 | 121.35 (16) |
C38—N3—C26 | 120.95 (14) | C49—C50—C45 | 119.3 (2) |
C38—N3—C32 | 120.38 (14) | C10—C9—C8 | 120.57 (18) |
C26—N3—C32 | 118.64 (13) | C10—C9—H9 | 119.7 |
C17—C16—C15 | 118.26 (14) | C8—C9—H9 | 119.7 |
C17—C16—N2 | 117.98 (14) | C28—C27—C26 | 119.87 (18) |
C15—C16—N2 | 123.72 (14) | C28—C27—H27 | 120.1 |
C18—C13—C14 | 118.24 (14) | C26—C27—H27 | 120.1 |
C18—C13—N1 | 120.63 (14) | C42—C43—C38 | 120.32 (17) |
C14—C13—N1 | 121.13 (15) | C42—C43—H43 | 119.8 |
C21—C20—C25 | 118.23 (15) | C38—C43—H43 | 119.8 |
C21—C20—C19 | 120.08 (15) | C30—C31—C26 | 119.92 (19) |
C25—C20—C19 | 121.68 (15) | C30—C31—H31 | 120.0 |
C12—C7—C8 | 119.53 (15) | C26—C31—H31 | 120.0 |
C12—C7—N1 | 120.49 (15) | C29—C30—C31 | 120.57 (19) |
C8—C7—N1 | 119.98 (16) | C29—C30—H30 | 119.7 |
N2—C19—C20 | 122.16 (15) | C31—C30—H30 | 119.7 |
N2—C19—H19 | 118.9 | C29—C28—C27 | 121.1 (2) |
C20—C19—H19 | 118.9 | C29—C28—H28 | 119.5 |
C6—C1—C2 | 118.92 (16) | C27—C28—H28 | 119.5 |
C6—C1—N1 | 120.64 (16) | C47—C46—C45 | 120.9 (2) |
C2—C1—N1 | 120.44 (15) | C47—C46—H46 | 119.6 |
C33—C32—C37 | 119.53 (19) | C45—C46—H46 | 119.6 |
C33—C32—N3 | 121.15 (18) | C30—C29—C28 | 119.42 (19) |
C37—C32—N3 | 119.32 (18) | C30—C29—H29 | 120.3 |
C46—C45—C50 | 119.02 (18) | C28—C29—H29 | 120.3 |
C46—C45—C44 | 119.56 (18) | C4—C3—C2 | 120.7 (2) |
C50—C45—C44 | 121.42 (17) | C4—C3—H3 | 119.6 |
C14—C15—C16 | 120.79 (15) | C2—C3—H3 | 119.6 |
C14—C15—H15 | 119.6 | C21—C22—C23 | 119.31 (19) |
C16—C15—H15 | 119.6 | C21—C22—H22 | 120.3 |
C40—C39—C38 | 120.99 (16) | C23—C22—H22 | 120.3 |
C40—C39—H39 | 119.5 | C43—C42—C41 | 121.61 (17) |
C38—C39—H39 | 119.5 | C43—C42—H42 | 119.2 |
C27—C26—C31 | 119.14 (17) | C41—C42—H42 | 119.2 |
C27—C26—N3 | 120.91 (15) | C23—C24—C25 | 120.10 (18) |
C31—C26—N3 | 119.94 (16) | C23—C24—H24 | 119.9 |
C7—C8—C9 | 119.82 (18) | C25—C24—H24 | 119.9 |
C7—C8—H8 | 120.1 | C9—C10—C11 | 119.59 (17) |
C9—C8—H8 | 120.1 | C9—C10—H10 | 120.2 |
O1—C25—C24 | 118.70 (17) | C11—C10—H10 | 120.2 |
O1—C25—C20 | 121.50 (15) | C22—C23—C24 | 120.84 (18) |
C24—C25—C20 | 119.80 (17) | C22—C23—H23 | 119.6 |
C22—C21—C20 | 121.70 (18) | C24—C23—H23 | 119.6 |
C22—C21—H21 | 119.2 | C32—C37—C36 | 119.8 (2) |
C20—C21—H21 | 119.2 | C32—C37—H37 | 120.1 |
C18—C17—C16 | 121.19 (15) | C36—C37—H37 | 120.1 |
C18—C17—H17 | 119.4 | C32—C33—C34 | 119.9 (2) |
C16—C17—H17 | 119.4 | C32—C33—H33 | 120.1 |
C39—C40—C41 | 120.48 (17) | C34—C33—H33 | 120.1 |
C39—C40—H40 | 119.8 | C3—C4—C5 | 119.5 (2) |
C41—C40—H40 | 119.8 | C3—C4—H4 | 120.2 |
C43—C38—C39 | 118.32 (15) | C5—C4—H4 | 120.2 |
C43—C38—N3 | 120.70 (16) | C35—C36—C37 | 120.6 (2) |
C39—C38—N3 | 120.98 (16) | C35—C36—H36 | 119.7 |
C17—C18—C13 | 120.57 (15) | C37—C36—H36 | 119.7 |
C17—C18—H18 | 119.7 | C4—C5—C6 | 120.6 (2) |
C13—C18—H18 | 119.7 | C4—C5—H5 | 119.7 |
C7—C12—C11 | 120.09 (17) | C6—C5—H5 | 119.7 |
C7—C12—H12 | 120.0 | C48—C49—C50 | 120.3 (2) |
C11—C12—H12 | 120.0 | C48—C49—H49 | 119.9 |
C3—C2—C1 | 120.12 (17) | C50—C49—H49 | 119.9 |
C3—C2—H2A | 119.9 | C46—C47—C48 | 119.2 (2) |
C1—C2—H2A | 119.9 | C46—C47—H47 | 120.4 |
C10—C11—C12 | 120.39 (18) | C48—C47—H47 | 120.4 |
C10—C11—H11 | 119.8 | C35—C34—C33 | 120.7 (3) |
C12—C11—H11 | 119.8 | C35—C34—H34 | 119.7 |
C15—C14—C13 | 120.93 (15) | C33—C34—H34 | 119.7 |
C15—C14—H14 | 119.5 | C49—C48—C47 | 121.4 (2) |
C13—C14—H14 | 119.5 | C49—C48—H48 | 119.3 |
C1—C6—C5 | 120.06 (19) | C47—C48—H48 | 119.3 |
C19—N2—C16—C17 | −153.60 (16) | N1—C13—C14—C15 | −179.37 (16) |
C19—N2—C16—C15 | 28.7 (2) | C2—C1—C6—C5 | −0.3 (3) |
C1—N1—C13—C18 | −144.94 (17) | N1—C1—C6—C5 | −179.68 (19) |
C7—N1—C13—C18 | 39.5 (2) | C41—N4—C44—C45 | 176.17 (17) |
C1—N1—C13—C14 | 34.5 (3) | C46—C45—C44—N4 | 179.45 (19) |
C7—N1—C13—C14 | −141.05 (17) | C50—C45—C44—N4 | −1.4 (3) |
C13—N1—C7—C12 | 44.6 (2) | C39—C40—C41—C42 | 0.5 (3) |
C1—N1—C7—C12 | −130.95 (18) | C39—C40—C41—N4 | −175.25 (17) |
C13—N1—C7—C8 | −135.76 (18) | C44—N4—C41—C42 | 154.47 (19) |
C1—N1—C7—C8 | 48.6 (2) | C44—N4—C41—C40 | −29.8 (3) |
C16—N2—C19—C20 | −175.25 (15) | C46—C45—C50—O2 | 178.58 (19) |
C21—C20—C19—N2 | 178.81 (17) | C44—C45—C50—O2 | −0.6 (3) |
C25—C20—C19—N2 | 0.3 (3) | C46—C45—C50—C49 | −0.4 (3) |
C13—N1—C1—C6 | −137.97 (18) | C44—C45—C50—C49 | −179.59 (19) |
C7—N1—C1—C6 | 37.6 (2) | C7—C8—C9—C10 | −0.6 (3) |
C13—N1—C1—C2 | 42.6 (2) | C31—C26—C27—C28 | 0.0 (3) |
C7—N1—C1—C2 | −141.80 (17) | N3—C26—C27—C28 | 178.53 (17) |
C38—N3—C32—C33 | 44.7 (3) | C39—C38—C43—C42 | 1.7 (3) |
C26—N3—C32—C33 | −133.12 (19) | N3—C38—C43—C42 | −177.35 (18) |
C38—N3—C32—C37 | −135.65 (19) | C27—C26—C31—C30 | 0.1 (3) |
C26—N3—C32—C37 | 46.5 (2) | N3—C26—C31—C30 | −178.45 (16) |
C17—C16—C15—C14 | 1.6 (3) | C26—C31—C30—C29 | −0.1 (3) |
N2—C16—C15—C14 | 179.25 (16) | C26—C27—C28—C29 | −0.1 (3) |
C38—N3—C26—C27 | 43.8 (2) | C50—C45—C46—C47 | −0.4 (3) |
C32—N3—C26—C27 | −138.44 (18) | C44—C45—C46—C47 | 178.8 (2) |
C38—N3—C26—C31 | −137.73 (18) | C31—C30—C29—C28 | 0.0 (3) |
C32—N3—C26—C31 | 40.1 (2) | C27—C28—C29—C30 | 0.1 (3) |
C12—C7—C8—C9 | 1.4 (3) | C1—C2—C3—C4 | −1.4 (3) |
N1—C7—C8—C9 | −178.22 (18) | C20—C21—C22—C23 | −0.2 (3) |
C21—C20—C25—O1 | 179.59 (18) | C38—C43—C42—C41 | −2.1 (3) |
C19—C20—C25—O1 | −1.8 (3) | C40—C41—C42—C43 | 0.9 (3) |
C21—C20—C25—C24 | −0.6 (3) | N4—C41—C42—C43 | 176.91 (18) |
C19—C20—C25—C24 | 177.94 (18) | O1—C25—C24—C23 | 178.9 (2) |
C25—C20—C21—C22 | 1.2 (3) | C20—C25—C24—C23 | −0.8 (3) |
C19—C20—C21—C22 | −177.42 (18) | C8—C9—C10—C11 | −0.6 (3) |
C15—C16—C17—C18 | −0.8 (2) | C12—C11—C10—C9 | 0.9 (3) |
N2—C16—C17—C18 | −178.64 (15) | C21—C22—C23—C24 | −1.3 (3) |
C38—C39—C40—C41 | −0.8 (3) | C25—C24—C23—C22 | 1.8 (4) |
C40—C39—C38—C43 | −0.3 (3) | C33—C32—C37—C36 | −0.1 (3) |
C40—C39—C38—N3 | 178.76 (17) | N3—C32—C37—C36 | −179.76 (18) |
C26—N3—C38—C43 | −148.57 (18) | C37—C32—C33—C34 | 0.4 (3) |
C32—N3—C38—C43 | 33.7 (3) | N3—C32—C33—C34 | −179.92 (19) |
C26—N3—C38—C39 | 32.4 (3) | C2—C3—C4—C5 | 0.2 (4) |
C32—N3—C38—C39 | −145.35 (18) | C34—C35—C36—C37 | −0.3 (3) |
C16—C17—C18—C13 | −0.3 (3) | C32—C37—C36—C35 | 0.0 (3) |
C14—C13—C18—C17 | 0.6 (3) | C3—C4—C5—C6 | 1.1 (4) |
N1—C13—C18—C17 | −179.89 (16) | C1—C6—C5—C4 | −1.0 (4) |
C8—C7—C12—C11 | −1.0 (3) | O2—C50—C49—C48 | −178.2 (2) |
N1—C7—C12—C11 | 178.60 (16) | C45—C50—C49—C48 | 0.8 (3) |
C6—C1—C2—C3 | 1.5 (3) | C45—C46—C47—C48 | 0.9 (4) |
N1—C1—C2—C3 | −179.12 (17) | C36—C35—C34—C33 | 0.6 (4) |
C7—C12—C11—C10 | −0.2 (3) | C32—C33—C34—C35 | −0.7 (4) |
C16—C15—C14—C13 | −1.2 (3) | C50—C49—C48—C47 | −0.3 (4) |
C18—C13—C14—C15 | 0.1 (3) | C46—C47—C48—C49 | −0.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.82 | 1.88 | 2.609 (2) | 147 |
O2—H2···N4 | 0.82 | 1.86 | 2.590 (2) | 148 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.82 | 1.88 | 2.609 (2) | 147 |
O2—H2···N4 | 0.82 | 1.86 | 2.590 (2) | 148 |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (grant Nos. 51372003 and 21271004).
References
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Schiff bases are considered important compounds because of their wide range of biological activities, and also because of their use as ligands in conjunction with transition metals (Damous et al., 2013). Schiff bases derived from salicyladehyde and methylaniline with various substituents have exhibited potential application in pharmaceutical fields for their antitumor, antimicrobial and antiviral activities (Zheng et al., 2013). Herein, with we report the crystal structure of the title compound (I).
In (I) (Fig.1), the Schiff base moiety shows an E configuration about the C16═N2 and C19═C20 bonds. The most significant difference between the two molecules are the dihedral angles between the methoxy-substituted benzene ring and the two phenyl rings, which are 85.5 (1)° [C20-C25/C1-C6] and 82.3 (1)° [C20-C25/C7-C12] in one molecule and 49.0 (1)° [C40-C50C26-C31] and 40.4 (1)° [C45-C50/C32-C37] in the other. This conformational difference is reflected in the central C═N—C≐C torsion angle which is 28.7 (2)° in one molecule [C19-N2-C16-C15] and -29.8 (3)° [C44-N4-C41-C40] in the other. The bond distances of the two independent molecules are the same within experimental error.