organic compounds
of 5-diethylamino-2-({[4-(diethylamino)phenyl]imino}methyl)phenol
aPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, India, bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and cPG & Research Department of Chemistry, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, jothivenkateswaran@yahoo.co.in
In the title compound, C21H29N3O, the dihedral angle between the planes of the aromatic rings is 8.1 (2)°. The ethyl groups at one terminal site of the compound are disordered over two sets of sites with occupancies of 0.775 (9) and 0.225 (9). The molecule has an E conformation about the N=C bond. The molecular structure features an intramolecular O—H⋯N hydrogen bond, which closes an S(6) loop. In the crystal, weak C—H⋯π interactions leads to the formation of a three-dimensional network.
Keywords: crystal structure; phenol; Schiff base; intramolecular hydrogen bond; C—H⋯π interactions; biological activity; pharmacological activity.
CCDC reference: 1422036
1. Related literature
For biological and pharmacological activities of Schiff base compounds and their derivatives, see: Khandar et al. (2005); Chen et al. (2006); Kidwai et al. (2000). For similar structures, see: Manvizhi et al. (2011); Thirugnanasundar et al. (2011); Rani et al. (2015).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 1422036
10.1107/S205698901501645X/rk2432sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S205698901501645X/rk2432Isup2.hkl
Supporting information file. DOI: 10.1107/S205698901501645X/rk2432Isup3.cml
For the preparation of Schiff base, an ethanolic solution (10 ml) of 5–(diethylamino)–2–hydroxybenzaldehyde (0.5 mol) and the same volume of ethanolic solution of N,N–diethylbenzene–1,4–diamine (0.5 mol) are mixed. The solution is mixed on magnetic stirrer with addition of 2 to 3 drops of glacial acetic acid. The reaction mixture is refluxed for 2 hrs and allowed to cool down to room temperature, crystalline solid precipitate from the mixture is separated out. Crystalline products are washed with ice cold ethanol and dried in vacuo over anhydrous CaCl2. Single crystals suitable for the X-ray diffraction are obtained by slow evaporation of a solution of the title compound in DMF at room temperature.
The H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3. H atom for O atom is found from Fourier map and refined freely with Uiso(H) = 1.5Ueq(O) and distance restraint 0.82 Å. The components of the anisotropic displacement parameters in the direction of the bond between C9 and O1 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command. The N1—C2, N1—C3, N1—C2A, N1—C3A distances were restraint to 1.46 (1) Å and C1—C2, C1A—C2A, C3—C4 and C3A—C4A distances were restraint to 1.53 (1) Å
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of title compaund, with the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. The intramolecular hydrogen bond is depicted by a dashed line. Only the major occupancy component of the disordered diethylamino–group [—N1(C2H5)2] is shown. |
C21H29N3O | F(000) = 736 |
Mr = 339.47 | Dx = 1.160 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7089 reflections |
a = 8.1986 (4) Å | θ = 2.5–25.3° |
b = 9.7128 (4) Å | µ = 0.07 mm−1 |
c = 24.4172 (12) Å | T = 295 K |
V = 1944.38 (16) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.26 × 0.24 mm |
Bruker Kappa APEX II CCD diffractometer | 3556 independent reflections |
Radiation source: fine–focus sealed tube | 2130 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω and φ scans | θmax = 25.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.980, Tmax = 0.983 | k = −11→11 |
29557 measured reflections | l = −29→29 |
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)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.205 | w = 1/[σ2(Fo2) + (0.0727P)2 + 1.5032P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3556 reflections | Δρmax = 0.44 e Å−3 |
272 parameters | Δρmin = −0.20 e Å−3 |
10 restraints | Absolute structure: Flack (1983), 1466 Friedel pairs |
Primary atom site location: structure-invariant direct methods |
C21H29N3O | V = 1944.38 (16) Å3 |
Mr = 339.47 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.1986 (4) Å | µ = 0.07 mm−1 |
b = 9.7128 (4) Å | T = 295 K |
c = 24.4172 (12) Å | 0.28 × 0.26 × 0.24 mm |
Bruker Kappa APEX II CCD diffractometer | 3556 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2130 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.983 | Rint = 0.046 |
29557 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 10 restraints |
wR(F2) = 0.205 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.44 e Å−3 |
3556 reflections | Δρmin = −0.20 e Å−3 |
272 parameters | Absolute structure: Flack (1983), 1466 Friedel pairs |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 | Occ. (<1) | |
C1 | 0.7266 (10) | 0.9101 (7) | −0.0244 (3) | 0.084 (2) | 0.775 (9) |
H1A | 0.7411 | 0.8690 | 0.0111 | 0.125* | 0.775 (9) |
H1B | 0.6538 | 0.9871 | −0.0214 | 0.125* | 0.775 (9) |
H1C | 0.8302 | 0.9409 | −0.0380 | 0.125* | 0.775 (9) |
C2 | 0.6555 (11) | 0.8049 (8) | −0.0633 (4) | 0.067 (3) | 0.775 (9) |
H2A | 0.5577 | 0.7651 | −0.0475 | 0.080* | 0.775 (9) |
H2B | 0.6260 | 0.8492 | −0.0975 | 0.080* | 0.775 (9) |
C3 | 0.9082 (10) | 0.7205 (8) | −0.1156 (3) | 0.073 (2) | 0.775 (9) |
H3A | 0.9375 | 0.8172 | −0.1161 | 0.088* | 0.775 (9) |
H3B | 1.0047 | 0.6674 | −0.1065 | 0.088* | 0.775 (9) |
C4 | 0.8438 (10) | 0.6778 (8) | −0.1703 (3) | 0.093 (3) | 0.775 (9) |
H4A | 0.8211 | 0.5809 | −0.1699 | 0.140* | 0.775 (9) |
H4B | 0.9237 | 0.6975 | −0.1979 | 0.140* | 0.775 (9) |
H4C | 0.7454 | 0.7277 | −0.1780 | 0.140* | 0.775 (9) |
C1A | 0.586 (4) | 0.847 (5) | −0.0615 (19) | 0.122 (16) | 0.225 (9) |
H1A1 | 0.5521 | 0.9397 | −0.0545 | 0.183* | 0.225 (9) |
H1A2 | 0.5193 | 0.7847 | −0.0405 | 0.183* | 0.225 (9) |
H1A3 | 0.5730 | 0.8267 | −0.0998 | 0.183* | 0.225 (9) |
C2A | 0.764 (4) | 0.8291 (15) | −0.0453 (9) | 0.085 (9) | 0.225 (9) |
H2A1 | 0.8345 | 0.8993 | −0.0607 | 0.102* | 0.225 (9) |
H2A2 | 0.7798 | 0.8221 | −0.0061 | 0.102* | 0.225 (9) |
C3A | 0.787 (3) | 0.6858 (16) | −0.1341 (4) | 0.061 (7) | 0.225 (9) |
H3A1 | 0.7019 | 0.7390 | −0.1519 | 0.073* | 0.225 (9) |
H3A2 | 0.7824 | 0.5911 | −0.1467 | 0.073* | 0.225 (9) |
C4A | 0.955 (3) | 0.749 (3) | −0.1425 (13) | 0.080 (9) | 0.225 (9) |
H4A1 | 0.9478 | 0.8474 | −0.1389 | 0.120* | 0.225 (9) |
H4A2 | 0.9944 | 0.7263 | −0.1783 | 0.120* | 0.225 (9) |
H4A3 | 1.0288 | 0.7136 | −0.1154 | 0.120* | 0.225 (9) |
C5 | 0.7811 (6) | 0.5793 (4) | −0.04177 (17) | 0.0666 (12) | |
C6 | 0.8764 (6) | 0.4644 (5) | −0.05697 (19) | 0.0725 (13) | |
H6 | 0.9326 | 0.4651 | −0.0901 | 0.087* | |
C7 | 0.8865 (6) | 0.3522 (5) | −0.02341 (19) | 0.0680 (12) | |
H7 | 0.9509 | 0.2782 | −0.0342 | 0.082* | |
C8 | 0.8054 (5) | 0.3444 (4) | 0.02559 (16) | 0.0541 (10) | |
C9 | 0.7068 (6) | 0.4550 (5) | 0.03971 (16) | 0.0613 (11) | |
C10 | 0.6941 (6) | 0.5712 (4) | 0.00699 (17) | 0.0662 (12) | |
H10 | 0.6274 | 0.6438 | 0.0177 | 0.079* | |
C11 | 0.8246 (6) | 0.2245 (5) | 0.06113 (19) | 0.0643 (12) | |
H11 | 0.8909 | 0.1522 | 0.0499 | 0.077* | |
C12 | 0.7727 (5) | 0.1017 (4) | 0.14256 (17) | 0.0574 (11) | |
C13 | 0.8522 (6) | −0.0207 (5) | 0.12960 (18) | 0.0706 (13) | |
H13 | 0.9012 | −0.0306 | 0.0955 | 0.085* | |
C14 | 0.8591 (6) | −0.1287 (5) | 0.16721 (18) | 0.0679 (12) | |
H14 | 0.9130 | −0.2094 | 0.1577 | 0.082* | |
C15 | 0.7872 (5) | −0.1183 (4) | 0.21878 (16) | 0.0515 (10) | |
C16 | 0.7109 (5) | 0.0078 (4) | 0.23007 (17) | 0.0616 (11) | |
H16 | 0.6638 | 0.0210 | 0.2643 | 0.074* | |
C17 | 0.7033 (5) | 0.1122 (5) | 0.19253 (18) | 0.0622 (11) | |
H17 | 0.6487 | 0.1929 | 0.2017 | 0.075* | |
C18 | 0.8789 (6) | −0.3514 (5) | 0.2453 (2) | 0.0726 (13) | |
H18A | 0.9128 | −0.3912 | 0.2799 | 0.087* | |
H18B | 0.9765 | −0.3306 | 0.2244 | 0.087* | |
C19 | 0.7787 (9) | −0.4567 (6) | 0.2141 (2) | 0.109 (2) | |
H19A | 0.6855 | −0.4825 | 0.2356 | 0.164* | |
H19B | 0.8443 | −0.5366 | 0.2070 | 0.164* | |
H19C | 0.7429 | −0.4176 | 0.1801 | 0.164* | |
C20 | 0.7125 (6) | −0.2143 (5) | 0.3091 (2) | 0.0764 (14) | |
H20A | 0.6822 | −0.3058 | 0.3213 | 0.092* | |
H20B | 0.6132 | −0.1607 | 0.3054 | 0.092* | |
C21 | 0.8191 (9) | −0.1487 (7) | 0.3515 (2) | 0.113 (2) | |
H21A | 0.9208 | −0.1975 | 0.3535 | 0.170* | |
H21B | 0.7657 | −0.1521 | 0.3864 | 0.170* | |
H21C | 0.8393 | −0.0546 | 0.3417 | 0.170* | |
N1 | 0.7767 (7) | 0.6954 (4) | −0.07378 (16) | 0.1047 (19) | |
N2 | 0.7542 (4) | 0.2174 (4) | 0.10594 (14) | 0.0626 (10) | |
N3 | 0.7918 (5) | −0.2243 (4) | 0.25593 (14) | 0.0654 (10) | |
O1 | 0.6208 (5) | 0.4508 (4) | 0.08624 (14) | 0.0858 (11) | |
H1 | 0.643 (8) | 0.379 (4) | 0.105 (2) | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.091 (5) | 0.071 (5) | 0.089 (5) | 0.010 (4) | 0.006 (4) | −0.013 (4) |
C2 | 0.084 (8) | 0.057 (5) | 0.059 (4) | 0.014 (5) | −0.005 (5) | 0.004 (3) |
C3 | 0.081 (6) | 0.061 (4) | 0.078 (6) | −0.007 (4) | 0.005 (4) | 0.004 (4) |
C4 | 0.099 (6) | 0.105 (6) | 0.075 (5) | 0.017 (5) | 0.000 (4) | −0.008 (4) |
C1A | 0.11 (3) | 0.11 (3) | 0.15 (3) | −0.01 (2) | 0.04 (3) | 0.01 (3) |
C2A | 0.12 (3) | 0.08 (2) | 0.058 (16) | −0.004 (18) | −0.006 (17) | 0.015 (14) |
C3A | 0.13 (2) | 0.021 (8) | 0.036 (11) | 0.008 (11) | 0.021 (12) | 0.000 (7) |
C4A | 0.076 (17) | 0.080 (19) | 0.09 (2) | −0.020 (14) | 0.023 (15) | −0.010 (16) |
C5 | 0.091 (3) | 0.054 (3) | 0.055 (2) | 0.012 (3) | 0.019 (3) | 0.003 (2) |
C6 | 0.090 (4) | 0.061 (3) | 0.067 (3) | 0.008 (3) | 0.018 (3) | −0.006 (2) |
C7 | 0.075 (3) | 0.054 (3) | 0.075 (3) | 0.010 (2) | 0.004 (3) | −0.005 (2) |
C8 | 0.050 (2) | 0.048 (2) | 0.064 (3) | 0.000 (2) | −0.010 (2) | 0.0036 (19) |
C9 | 0.059 (2) | 0.071 (3) | 0.054 (2) | −0.004 (2) | 0.0005 (17) | 0.001 (2) |
C10 | 0.081 (3) | 0.059 (3) | 0.059 (2) | 0.017 (3) | 0.015 (2) | 0.005 (2) |
C11 | 0.056 (3) | 0.071 (3) | 0.065 (3) | −0.002 (2) | −0.012 (2) | −0.003 (2) |
C12 | 0.052 (2) | 0.049 (2) | 0.071 (3) | 0.000 (2) | −0.017 (2) | 0.010 (2) |
C13 | 0.081 (3) | 0.080 (3) | 0.050 (2) | −0.005 (3) | −0.002 (2) | 0.002 (2) |
C14 | 0.078 (3) | 0.061 (3) | 0.065 (3) | 0.013 (2) | −0.007 (2) | 0.006 (2) |
C15 | 0.051 (2) | 0.046 (2) | 0.058 (2) | −0.002 (2) | −0.011 (2) | 0.0053 (19) |
C16 | 0.056 (2) | 0.062 (3) | 0.067 (3) | 0.001 (2) | −0.003 (2) | 0.004 (2) |
C17 | 0.056 (3) | 0.064 (3) | 0.067 (3) | 0.001 (2) | −0.006 (2) | 0.002 (2) |
C18 | 0.077 (3) | 0.063 (3) | 0.077 (3) | 0.015 (3) | −0.004 (3) | 0.014 (3) |
C19 | 0.144 (6) | 0.066 (3) | 0.116 (4) | 0.001 (4) | −0.014 (5) | −0.014 (3) |
C20 | 0.073 (3) | 0.063 (3) | 0.093 (3) | −0.001 (3) | 0.001 (3) | 0.018 (3) |
C21 | 0.145 (6) | 0.123 (5) | 0.072 (3) | −0.005 (5) | −0.001 (4) | −0.008 (3) |
N1 | 0.176 (5) | 0.065 (3) | 0.072 (3) | 0.038 (3) | 0.061 (3) | 0.020 (2) |
N2 | 0.061 (2) | 0.065 (2) | 0.061 (2) | 0.0032 (19) | −0.0139 (19) | −0.0030 (18) |
N3 | 0.081 (2) | 0.054 (2) | 0.062 (2) | 0.011 (2) | 0.000 (2) | 0.0053 (17) |
O1 | 0.105 (3) | 0.084 (2) | 0.068 (2) | 0.028 (2) | 0.0249 (18) | 0.0131 (18) |
C1—C2 | 1.513 (8) | C8—C9 | 1.388 (6) |
C1—H1A | 0.9600 | C8—C11 | 1.461 (6) |
C1—H1B | 0.9600 | C9—O1 | 1.338 (5) |
C1—H1C | 0.9600 | C9—C10 | 1.387 (6) |
C2—N1 | 1.478 (7) | C10—H10 | 0.9300 |
C2—H2A | 0.9700 | C11—N2 | 1.239 (5) |
C2—H2B | 0.9700 | C11—H11 | 0.9300 |
C3—C4 | 1.495 (7) | C12—C17 | 1.350 (6) |
C3—N1 | 1.504 (7) | C12—C13 | 1.392 (6) |
C3—H3A | 0.9700 | C12—N2 | 1.444 (5) |
C3—H3B | 0.9700 | C13—C14 | 1.395 (6) |
C4—H4A | 0.9600 | C13—H13 | 0.9300 |
C4—H4B | 0.9600 | C14—C15 | 1.394 (6) |
C4—H4C | 0.9600 | C14—H14 | 0.9300 |
C1A—C2A | 1.523 (10) | C15—N3 | 1.373 (5) |
C1A—H1A1 | 0.9600 | C15—C16 | 1.403 (6) |
C1A—H1A2 | 0.9600 | C16—C17 | 1.368 (6) |
C1A—H1A3 | 0.9600 | C16—H16 | 0.9300 |
C2A—N1 | 1.477 (10) | C17—H17 | 0.9300 |
C2A—H2A1 | 0.9700 | C18—N3 | 1.450 (5) |
C2A—H2A2 | 0.9700 | C18—C19 | 1.516 (7) |
C3A—N1 | 1.478 (9) | C18—H18A | 0.9700 |
C3A—C4A | 1.524 (10) | C18—H18B | 0.9700 |
C3A—H3A1 | 0.9700 | C19—H19A | 0.9600 |
C3A—H3A2 | 0.9700 | C19—H19B | 0.9600 |
C4A—H4A1 | 0.9600 | C19—H19C | 0.9600 |
C4A—H4A2 | 0.9600 | C20—N3 | 1.455 (6) |
C4A—H4A3 | 0.9600 | C20—C21 | 1.497 (7) |
C5—N1 | 1.372 (5) | C20—H20A | 0.9700 |
C5—C10 | 1.390 (6) | C20—H20B | 0.9700 |
C5—C6 | 1.412 (6) | C21—H21A | 0.9600 |
C6—C7 | 1.366 (6) | C21—H21B | 0.9600 |
C6—H6 | 0.9300 | C21—H21C | 0.9600 |
C7—C8 | 1.371 (6) | O1—H1 | 0.86 (2) |
C7—H7 | 0.9300 | ||
N1—C2—C1 | 109.6 (7) | C17—C12—C13 | 117.8 (4) |
N1—C2—H2A | 109.8 | C17—C12—N2 | 117.2 (4) |
C1—C2—H2A | 109.8 | C13—C12—N2 | 125.0 (4) |
N1—C2—H2B | 109.8 | C12—C13—C14 | 120.8 (4) |
C1—C2—H2B | 109.8 | C12—C13—H13 | 119.6 |
H2A—C2—H2B | 108.2 | C14—C13—H13 | 119.6 |
C4—C3—N1 | 107.9 (7) | C15—C14—C13 | 121.5 (4) |
C4—C3—H3A | 110.1 | C15—C14—H14 | 119.2 |
N1—C3—H3A | 110.1 | C13—C14—H14 | 119.2 |
C4—C3—H3B | 110.1 | N3—C15—C14 | 122.1 (4) |
N1—C3—H3B | 110.1 | N3—C15—C16 | 122.5 (4) |
H3A—C3—H3B | 108.4 | C14—C15—C16 | 115.4 (4) |
C2A—C1A—H1A1 | 109.5 | C17—C16—C15 | 122.4 (4) |
C2A—C1A—H1A2 | 109.5 | C17—C16—H16 | 118.8 |
H1A1—C1A—H1A2 | 109.5 | C15—C16—H16 | 118.8 |
C2A—C1A—H1A3 | 109.5 | C12—C17—C16 | 122.0 (4) |
H1A1—C1A—H1A3 | 109.5 | C12—C17—H17 | 119.0 |
H1A2—C1A—H1A3 | 109.5 | C16—C17—H17 | 119.0 |
N1—C2A—C1A | 93 (2) | N3—C18—C19 | 113.4 (4) |
N1—C2A—H2A1 | 113.2 | N3—C18—H18A | 108.9 |
C1A—C2A—H2A1 | 113.2 | C19—C18—H18A | 108.9 |
N1—C2A—H2A2 | 113.2 | N3—C18—H18B | 108.9 |
C1A—C2A—H2A2 | 113.2 | C19—C18—H18B | 108.9 |
H2A1—C2A—H2A2 | 110.5 | H18A—C18—H18B | 107.7 |
N1—C3A—C4A | 99.1 (15) | C18—C19—H19A | 109.5 |
N1—C3A—H3A1 | 111.9 | C18—C19—H19B | 109.5 |
C4A—C3A—H3A1 | 111.9 | H19A—C19—H19B | 109.5 |
N1—C3A—H3A2 | 111.9 | C18—C19—H19C | 109.5 |
C4A—C3A—H3A2 | 111.9 | H19A—C19—H19C | 109.5 |
H3A1—C3A—H3A2 | 109.6 | H19B—C19—H19C | 109.5 |
C3A—C4A—H4A1 | 109.5 | N3—C20—C21 | 112.6 (4) |
C3A—C4A—H4A2 | 109.5 | N3—C20—H20A | 109.1 |
H4A1—C4A—H4A2 | 109.5 | C21—C20—H20A | 109.1 |
C3A—C4A—H4A3 | 109.5 | N3—C20—H20B | 109.1 |
H4A1—C4A—H4A3 | 109.5 | C21—C20—H20B | 109.1 |
H4A2—C4A—H4A3 | 109.5 | H20A—C20—H20B | 107.8 |
N1—C5—C10 | 121.4 (4) | C20—C21—H21A | 109.5 |
N1—C5—C6 | 120.9 (4) | C20—C21—H21B | 109.5 |
C10—C5—C6 | 117.7 (4) | H21A—C21—H21B | 109.5 |
C7—C6—C5 | 120.4 (4) | C20—C21—H21C | 109.5 |
C7—C6—H6 | 119.8 | H21A—C21—H21C | 109.5 |
C5—C6—H6 | 119.8 | H21B—C21—H21C | 109.5 |
C6—C7—C8 | 122.6 (4) | C5—N1—C2A | 117.2 (10) |
C6—C7—H7 | 118.7 | C5—N1—C3A | 120.9 (7) |
C8—C7—H7 | 118.7 | C2A—N1—C3A | 121.9 (12) |
C7—C8—C9 | 117.2 (4) | C5—N1—C2 | 120.7 (5) |
C7—C8—C11 | 120.7 (4) | C2A—N1—C2 | 40.3 (12) |
C9—C8—C11 | 122.1 (4) | C3A—N1—C2 | 104.8 (9) |
O1—C9—C10 | 118.3 (4) | C5—N1—C3 | 120.0 (5) |
O1—C9—C8 | 119.7 (4) | C2A—N1—C3 | 103.2 (12) |
C10—C9—C8 | 122.0 (4) | C3A—N1—C3 | 45.1 (8) |
C9—C10—C5 | 120.1 (4) | C2—N1—C3 | 118.8 (6) |
C9—C10—H10 | 120.0 | C11—N2—C12 | 122.8 (4) |
C5—C10—H10 | 120.0 | C15—N3—C18 | 122.3 (4) |
N2—C11—C8 | 121.3 (4) | C15—N3—C20 | 121.8 (4) |
N2—C11—H11 | 119.4 | C18—N3—C20 | 115.9 (4) |
C8—C11—H11 | 119.4 | C9—O1—H1 | 112 (4) |
N1—C5—C6—C7 | 176.6 (5) | C6—C5—N1—C2 | 169.0 (6) |
C10—C5—C6—C7 | −2.5 (8) | C10—C5—N1—C3 | 160.6 (5) |
C5—C6—C7—C8 | 0.6 (8) | C6—C5—N1—C3 | −18.5 (8) |
C6—C7—C8—C9 | 1.8 (7) | C1A—C2A—N1—C5 | −106 (2) |
C6—C7—C8—C11 | −177.7 (4) | C1A—C2A—N1—C3A | 75 (3) |
C7—C8—C9—O1 | 177.9 (4) | C1A—C2A—N1—C2 | 0 (2) |
C11—C8—C9—O1 | −2.7 (6) | C1A—C2A—N1—C3 | 120 (2) |
C7—C8—C9—C10 | −2.2 (6) | C4A—C3A—N1—C5 | −110.9 (14) |
C11—C8—C9—C10 | 177.2 (4) | C4A—C3A—N1—C2A | 68 (2) |
O1—C9—C10—C5 | −179.8 (4) | C4A—C3A—N1—C2 | 108.3 (15) |
C8—C9—C10—C5 | 0.3 (7) | C4A—C3A—N1—C3 | −7.8 (14) |
N1—C5—C10—C9 | −177.1 (5) | C1—C2—N1—C5 | 91.1 (9) |
C6—C5—C10—C9 | 2.1 (7) | C1—C2—N1—C2A | −5.8 (16) |
C7—C8—C11—N2 | 178.7 (4) | C1—C2—N1—C3A | −128.1 (9) |
C9—C8—C11—N2 | −0.8 (6) | C1—C2—N1—C3 | −81.6 (8) |
C17—C12—C13—C14 | 0.2 (6) | C4—C3—N1—C5 | 99.5 (7) |
N2—C12—C13—C14 | −177.9 (4) | C4—C3—N1—C2A | −127.9 (12) |
C12—C13—C14—C15 | 0.0 (7) | C4—C3—N1—C3A | −5.7 (10) |
C13—C14—C15—N3 | 179.3 (4) | C4—C3—N1—C2 | −87.8 (7) |
C13—C14—C15—C16 | −1.0 (6) | C8—C11—N2—C12 | −178.8 (4) |
N3—C15—C16—C17 | −178.5 (4) | C17—C12—N2—C11 | 173.3 (4) |
C14—C15—C16—C17 | 1.8 (6) | C13—C12—N2—C11 | −8.6 (6) |
C13—C12—C17—C16 | 0.7 (6) | C14—C15—N3—C18 | 3.3 (7) |
N2—C12—C17—C16 | 178.9 (4) | C16—C15—N3—C18 | −176.3 (4) |
C15—C16—C17—C12 | −1.7 (7) | C14—C15—N3—C20 | −178.2 (4) |
C10—C5—N1—C2A | 34.3 (15) | C16—C15—N3—C20 | 2.1 (6) |
C6—C5—N1—C2A | −144.8 (15) | C19—C18—N3—C15 | −86.1 (5) |
C10—C5—N1—C3A | −146.5 (10) | C19—C18—N3—C20 | 95.3 (5) |
C6—C5—N1—C3A | 34.4 (12) | C21—C20—N3—C15 | −86.4 (6) |
C10—C5—N1—C2 | −11.9 (9) | C21—C20—N3—C18 | 92.1 (5) |
Cg1 and Cg2 are the centroids of the C5–C10 and C12–C17 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.86 (2) | 1.81 (4) | 2.563 (5) | 144 (6) |
C18—H18A···Cg2i | 0.97 | 2.92 | 3.660 (5) | 134 |
C1A—H1A1···Cg1ii | 0.96 | 2.80 | 3.49 (4) | 130 |
Symmetry codes: (i) −x+5/2, −y−1, z+1/2; (ii) −x−1, y+3/2, −z+1/2. |
Cg1 and Cg2 are the centroids of the C5–C10 and C12–C17 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.86 (2) | 1.81 (4) | 2.563 (5) | 144 (6) |
C18—H18A···Cg2i | 0.97 | 2.92 | 3.660 (5) | 134 |
C1A—H1A1···Cg1ii | 0.96 | 2.80 | 3.49 (4) | 130 |
Symmetry codes: (i) −x+5/2, −y−1, z+1/2; (ii) −x−1, y+3/2, −z+1/2. |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Schiff base derivatives serve as intermediates in certain enzymatic reactions and are also found in proteins that form the connective tissue (Khandar et al., 2005; Chen et al., 2006) and in the pharmaceutical field (Kidwai et al., 2000). We herein report the crystal structure of the title compound (Fig.1). The geometric parameters of the title compound are comparable to the reported structures (Manvizhi et al., 2011; Thirugnanasundar et al., 2011; Rani et al., 2015). The dihedral angle between the rings (C5–C10) and (C12–C17) is 8.1 (2)°. The ethyl groups at one terminal site (N1) of the compound are disordered over two positions, with the site occupancies of 0.775 (9) and 0.225 (9). The molecular structure is stabilized by weak intramolecular O—H···N hydrogen bond (Table 1). The crystal structure is influenced by weak C—H···π (Table 1) interactions to form a three dimensional network.