organic compounds
(±)-trans-6,6′-Diethoxy-2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol monohydrate
aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com
In the title hydrate, C24H30N2O4·H2O, the organic molecule adopts an E conformation with respect to the azomethine double bonds. The cyclohexane ring is in a chair conformation. The dihedral angle between benzene rings is 79.6 (2)°. Two intramolecular O—H⋯N hydrogen bonds are present. In the crystal, the components are linked by O–H⋯O hydrogen bonds and weak C—H⋯π interactions, generating a three-dimensional supramolecular architecture.
CCDC reference: 981065
Related literature
For applications of et al. (1999); Hwang et al. (1998); Popović et al. (2002); Jones et al. (1979). For a related structure, see: Ambili et al. (2012). For the synthesis of see: Tümer (2000). For ring puckering analysis, see: Cremer & Pople (1975).
see: FranceschiExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 981065
10.1107/S1600536814000713/fj2654sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000713/fj2654Isup2.hkl
The title compound was prepared by following the reported procedure (Tümer, 2000). 3-Ethoxy-2-hydroxybenzaldehyde (0.166 g,1 mmol) was dissolved in ethanol and an ethanolic solution of 1, 2-diaminocyclohexane (0.044 g, 0.5 mmol) was added to it. The mixture was refluxed for 5 h. Slow evaporation of the solution yielded 0.183 g (95%) yellow block type crystals of (±)-trans-6,6'-Diethoxy-2,2'-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol monohydrate. The compound melts at 115 °C.
IR (KBr, \v in cm-1): 1626, 3530, 2930, 1468, 1249 1H NMR (400 MHz, CDCl3, δ in p.p.m.): 13.871 (s, 2H), 8.231 (s, 2H), 4.093–4.041 (q, 4H), 1.442–1.477 (t, 6H), 6.679–6.686 (m, 6H), 1.589–1.953 (m, 10H)
All H atoms on C were placed in calculated positions, guided by difference maps, with C—H bond distances 0.93–0.97 Å. H atoms were assigned as Uiso=1.2Ueq (1.5 for Me). The O bound H atoms were located in a difference Fourier map and their Uiso values tied to 1.5 times of O5 atom. The O–H distances of water molecule are restrained by DFIX and DANG instructions. The phenolic O–H distances, O2–H2' and O3–H3' were restrained to 0.084±0.001 Å. Omitting owing to bad disagreement were the reflections (0 0 2), (1 1 0) and (1 1 1).
Schiff bases are an important class of ligands in
devoted to energy storage such as molecular batteries (Franceschi, et al. 1999) and also in transition metal catalysis (Hwang, et al. 1998). Schiff base having intramolecular hydrogen bonding shows photophysical properties such as thermochromism and (Popović, et al. 2002). also have an ability to reversibly bind oxygen (Jones, et al.1979).The title compound crystallizes in the monoclinic, P21/c
The bond lengths and the bond angles agree with the related structure (Ambili, et al., 2012). The torsional angle, 177.9 (3)° of the azomethine linkage, C9—N2—C14—C15 reveals that the title compound adopts E conformation (Fig. 1). The mean plane deviation calculations show that the molecule as a whole is non-planar. Ring puckering analysis (Cremer & Pople, 1975) and least square plane calculations show that the cyclohexyl ring adopts a chair conformation (QT = 0.565 (4) Å) with the equatorial substitution at C9 for N2 and axial substitution at C8 for N1.Crystal system consists of intramolecular hydrogen bonds of lengths 1.79 (3) Å and 1.85 (3) Å which exists between the azomethine N atom and the neighbouring phenolic O atom leading to the formation of two six membered rings comprising of atoms C14—C15—C20—O3—H3'···N2 and C7—C6—C5—O2—H2'···N1 (Fig. 2). A C—H···π interaction between one of the hydrogen attached at C21 and the aromatic ring (C15—C20) with H···Cg distance of 2.92 Å (Fig. 3) dominates the packing of molecules in the lattice. Fig. 4 shows the packing diagram of the title compound along a axis.
For applications of
see: Franceschi et al. (1999); Hwang et al. (1998); Popović et al. (2002); Jones et al. (1979). For a related structure, see: Ambili et al. (2012). For the synthesis of see: Tümer (2000). For ring puckering analysis, see: Cremer & Pople (1975).Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).C24H30N2O4·H2O | F(000) = 920 |
Mr = 428.52 | Dx = 1.214 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3026 reflections |
a = 9.8241 (18) Å | θ = 2.8–23.5° |
b = 11.6975 (19) Å | µ = 0.09 mm−1 |
c = 21.881 (4) Å | T = 293 K |
β = 111.144 (8)° | Block, yellow |
V = 2345.2 (7) Å3 | 0.40 × 0.20 × 0.20 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 5586 independent reflections |
Radiation source: fine-focus sealed tube | 2701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.0°, θmin = 2.4° |
ω and φ scan | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −15→15 |
Tmin = 0.977, Tmax = 0.980 | l = −28→28 |
16141 measured reflections |
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)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.0561P)2 + 1.8063P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5586 reflections | Δρmax = 0.24 e Å−3 |
299 parameters | Δρmin = −0.21 e Å−3 |
5 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0022 (8) |
C24H30N2O4·H2O | V = 2345.2 (7) Å3 |
Mr = 428.52 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.8241 (18) Å | µ = 0.09 mm−1 |
b = 11.6975 (19) Å | T = 293 K |
c = 21.881 (4) Å | 0.40 × 0.20 × 0.20 mm |
β = 111.144 (8)° |
Bruker APEXII CCD diffractometer | 5586 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2701 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.980 | Rint = 0.048 |
16141 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 5 restraints |
wR(F2) = 0.190 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.24 e Å−3 |
5586 reflections | Δρmin = −0.21 e Å−3 |
299 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 | ||
O1 | 0.7073 (2) | 0.08906 (17) | 0.34718 (12) | 0.0591 (6) | |
O2 | 0.8516 (2) | 0.28131 (19) | 0.35839 (14) | 0.0629 (7) | |
O3 | 0.7204 (3) | 0.4164 (2) | 0.18225 (11) | 0.0538 (6) | |
O4 | 0.5589 (2) | 0.32967 (18) | 0.06864 (10) | 0.0547 (6) | |
N1 | 0.8533 (3) | 0.5022 (2) | 0.35838 (12) | 0.0449 (6) | |
N2 | 0.9286 (3) | 0.5466 (2) | 0.24970 (12) | 0.0466 (6) | |
C1 | 0.4960 (3) | 0.3961 (3) | 0.34503 (16) | 0.0508 (8) | |
H1 | 0.4499 | 0.4658 | 0.3442 | 0.061* | |
C2 | 0.4199 (4) | 0.2961 (3) | 0.34086 (17) | 0.0574 (9) | |
H2 | 0.3232 | 0.2984 | 0.3380 | 0.069* | |
C3 | 0.4869 (3) | 0.1916 (3) | 0.34092 (15) | 0.0496 (8) | |
H3 | 0.4339 | 0.1243 | 0.3369 | 0.060* | |
C4 | 0.6311 (3) | 0.1869 (2) | 0.34687 (14) | 0.0420 (7) | |
C5 | 0.7104 (3) | 0.2888 (2) | 0.35266 (14) | 0.0400 (7) | |
C6 | 0.6415 (3) | 0.3937 (2) | 0.35044 (13) | 0.0382 (7) | |
C7 | 0.7186 (3) | 0.5000 (2) | 0.35060 (14) | 0.0424 (7) | |
H7A | 0.6677 | 0.5686 | 0.3448 | 0.051* | |
C8 | 0.9215 (3) | 0.6119 (2) | 0.35447 (16) | 0.0471 (8) | |
H8 | 0.8450 | 0.6678 | 0.3328 | 0.056* | |
C9 | 1.0171 (3) | 0.5952 (3) | 0.31316 (15) | 0.0462 (8) | |
H9 | 1.0533 | 0.6701 | 0.3058 | 0.055* | |
C10 | 1.1468 (3) | 0.5191 (3) | 0.34789 (16) | 0.0539 (8) | |
H10A | 1.2077 | 0.5135 | 0.3217 | 0.065* | |
H10B | 1.1125 | 0.4430 | 0.3524 | 0.065* | |
C11 | 1.2369 (4) | 0.5653 (3) | 0.41526 (18) | 0.0676 (10) | |
H11A | 1.2790 | 0.6384 | 0.4106 | 0.081* | |
H11B | 1.3162 | 0.5129 | 0.4369 | 0.081* | |
C12 | 1.1432 (4) | 0.5804 (3) | 0.45706 (18) | 0.0711 (11) | |
H12A | 1.1098 | 0.5063 | 0.4657 | 0.085* | |
H12B | 1.2013 | 0.6145 | 0.4987 | 0.085* | |
C13 | 1.0126 (4) | 0.6560 (3) | 0.42242 (18) | 0.0642 (10) | |
H13A | 1.0466 | 0.7326 | 0.4185 | 0.077* | |
H13B | 0.9517 | 0.6606 | 0.4487 | 0.077* | |
C14 | 0.9536 (3) | 0.5704 (3) | 0.19771 (16) | 0.0497 (8) | |
H14 | 1.0277 | 0.6217 | 0.2002 | 0.060* | |
C15 | 0.8699 (3) | 0.5199 (3) | 0.13530 (14) | 0.0426 (7) | |
C16 | 0.9044 (4) | 0.5437 (3) | 0.07977 (17) | 0.0597 (9) | |
H16 | 0.9810 | 0.5929 | 0.0830 | 0.072* | |
C17 | 0.8259 (4) | 0.4948 (3) | 0.02104 (17) | 0.0640 (10) | |
H17 | 0.8501 | 0.5100 | −0.0155 | 0.077* | |
C18 | 0.7098 (4) | 0.4224 (3) | 0.01536 (15) | 0.0535 (8) | |
H18 | 0.6567 | 0.3899 | −0.0250 | 0.064* | |
C19 | 0.6726 (3) | 0.3985 (2) | 0.06895 (15) | 0.0419 (7) | |
C20 | 0.7557 (3) | 0.4444 (2) | 0.13042 (14) | 0.0403 (7) | |
C21 | 0.4662 (4) | 0.2842 (3) | 0.00700 (16) | 0.0575 (9) | |
H21A | 0.5221 | 0.2365 | −0.0117 | 0.069* | |
H21B | 0.4222 | 0.3458 | −0.0235 | 0.069* | |
C22 | 0.3504 (4) | 0.2149 (3) | 0.0195 (2) | 0.0823 (12) | |
H22A | 0.2975 | 0.2627 | 0.0389 | 0.124* | |
H22B | 0.3951 | 0.1532 | 0.0487 | 0.124* | |
H22C | 0.2844 | 0.1846 | −0.0212 | 0.124* | |
C23 | 0.7313 (5) | −0.1081 (3) | 0.3322 (2) | 0.0803 (12) | |
H23A | 0.8103 | −0.1114 | 0.3737 | 0.120* | |
H23B | 0.7691 | −0.0918 | 0.2983 | 0.120* | |
H23C | 0.6814 | −0.1803 | 0.3234 | 0.120* | |
C24 | 0.6272 (4) | −0.0162 (3) | 0.33377 (19) | 0.0616 (9) | |
H24A | 0.5469 | −0.0118 | 0.2920 | 0.074* | |
H24B | 0.5878 | −0.0319 | 0.3677 | 0.074* | |
O1W | 0.5867 (5) | 0.1883 (3) | 0.1898 (2) | 0.1125 (13) | |
H3' | 0.786 (3) | 0.447 (3) | 0.2150 (13) | 0.108 (17)* | |
H2' | 0.890 (4) | 0.3467 (17) | 0.362 (2) | 0.091 (14)* | |
H1A | 0.635 (10) | 0.203 (8) | 0.2306 (13) | 0.32 (6)* | |
H1B | 0.573 (11) | 0.255 (3) | 0.172 (4) | 0.31 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0575 (15) | 0.0360 (12) | 0.0902 (17) | 0.0028 (11) | 0.0343 (13) | −0.0022 (11) |
O2 | 0.0410 (13) | 0.0402 (14) | 0.118 (2) | 0.0047 (11) | 0.0407 (14) | −0.0023 (14) |
O3 | 0.0549 (14) | 0.0642 (15) | 0.0469 (13) | −0.0202 (12) | 0.0240 (12) | −0.0055 (12) |
O4 | 0.0559 (14) | 0.0564 (14) | 0.0502 (13) | −0.0196 (11) | 0.0172 (11) | −0.0078 (11) |
N1 | 0.0388 (15) | 0.0399 (14) | 0.0600 (16) | 0.0007 (12) | 0.0225 (13) | −0.0034 (12) |
N2 | 0.0411 (15) | 0.0477 (15) | 0.0517 (16) | −0.0072 (12) | 0.0175 (13) | −0.0053 (12) |
C1 | 0.0396 (18) | 0.0480 (18) | 0.071 (2) | 0.0099 (15) | 0.0274 (17) | 0.0086 (16) |
C2 | 0.0392 (18) | 0.062 (2) | 0.078 (2) | 0.0021 (17) | 0.0295 (17) | 0.0112 (18) |
C3 | 0.0453 (19) | 0.0455 (18) | 0.062 (2) | −0.0063 (15) | 0.0246 (16) | 0.0087 (15) |
C4 | 0.0448 (18) | 0.0382 (16) | 0.0466 (17) | 0.0036 (14) | 0.0207 (14) | 0.0044 (13) |
C5 | 0.0339 (16) | 0.0414 (16) | 0.0485 (17) | 0.0059 (13) | 0.0193 (14) | 0.0030 (14) |
C6 | 0.0351 (16) | 0.0401 (16) | 0.0422 (16) | 0.0070 (13) | 0.0173 (13) | 0.0034 (13) |
C7 | 0.0432 (18) | 0.0379 (16) | 0.0493 (18) | 0.0074 (14) | 0.0204 (15) | −0.0012 (14) |
C8 | 0.0428 (18) | 0.0366 (16) | 0.063 (2) | −0.0031 (14) | 0.0207 (16) | −0.0086 (15) |
C9 | 0.0417 (18) | 0.0417 (17) | 0.0575 (19) | −0.0112 (14) | 0.0206 (15) | −0.0078 (15) |
C10 | 0.0363 (18) | 0.060 (2) | 0.068 (2) | −0.0026 (16) | 0.0219 (16) | −0.0094 (17) |
C11 | 0.045 (2) | 0.079 (3) | 0.071 (2) | −0.0057 (19) | 0.0107 (18) | 0.000 (2) |
C12 | 0.069 (3) | 0.080 (3) | 0.060 (2) | −0.015 (2) | 0.017 (2) | −0.009 (2) |
C13 | 0.071 (2) | 0.056 (2) | 0.074 (2) | −0.0132 (19) | 0.036 (2) | −0.0205 (19) |
C14 | 0.0391 (18) | 0.0450 (18) | 0.068 (2) | −0.0075 (14) | 0.0234 (16) | 0.0032 (16) |
C15 | 0.0343 (16) | 0.0479 (17) | 0.0481 (18) | −0.0030 (14) | 0.0178 (14) | −0.0008 (14) |
C16 | 0.051 (2) | 0.073 (2) | 0.062 (2) | −0.0134 (18) | 0.0286 (18) | 0.0062 (18) |
C17 | 0.061 (2) | 0.086 (3) | 0.054 (2) | −0.009 (2) | 0.0308 (19) | 0.005 (2) |
C18 | 0.053 (2) | 0.064 (2) | 0.0451 (18) | 0.0004 (17) | 0.0188 (16) | −0.0038 (16) |
C19 | 0.0383 (17) | 0.0400 (16) | 0.0498 (18) | 0.0002 (14) | 0.0187 (14) | −0.0014 (14) |
C20 | 0.0406 (17) | 0.0381 (16) | 0.0467 (17) | 0.0015 (13) | 0.0209 (14) | 0.0029 (13) |
C21 | 0.059 (2) | 0.053 (2) | 0.056 (2) | −0.0073 (17) | 0.0149 (17) | −0.0087 (17) |
C22 | 0.080 (3) | 0.074 (3) | 0.086 (3) | −0.036 (2) | 0.020 (2) | −0.016 (2) |
C23 | 0.098 (3) | 0.047 (2) | 0.101 (3) | 0.008 (2) | 0.042 (3) | −0.010 (2) |
C24 | 0.068 (2) | 0.0397 (18) | 0.078 (2) | −0.0062 (17) | 0.028 (2) | −0.0051 (17) |
O1W | 0.177 (4) | 0.085 (2) | 0.090 (2) | −0.048 (2) | 0.066 (3) | −0.0119 (18) |
O1—C4 | 1.366 (3) | C11—H11A | 0.9700 |
O1—C24 | 1.433 (4) | C11—H11B | 0.9700 |
O2—C5 | 1.350 (3) | C12—C13 | 1.517 (5) |
O2—H2' | 0.846 (10) | C12—H12A | 0.9700 |
O3—C20 | 1.341 (3) | C12—H12B | 0.9700 |
O3—H3' | 0.850 (10) | C13—H13A | 0.9700 |
O4—C19 | 1.375 (3) | C13—H13B | 0.9700 |
O4—C21 | 1.430 (4) | C14—C15 | 1.442 (4) |
N1—C7 | 1.272 (3) | C14—H14 | 0.9300 |
N1—C8 | 1.465 (4) | C15—C20 | 1.401 (4) |
N2—C14 | 1.278 (4) | C15—C16 | 1.402 (4) |
N2—C9 | 1.461 (4) | C16—C17 | 1.363 (5) |
C1—C2 | 1.373 (4) | C16—H16 | 0.9300 |
C1—C6 | 1.392 (4) | C17—C18 | 1.389 (5) |
C1—H1 | 0.9300 | C17—H17 | 0.9300 |
C2—C3 | 1.388 (4) | C18—C19 | 1.377 (4) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.377 (4) | C19—C20 | 1.404 (4) |
C3—H3 | 0.9300 | C21—C22 | 1.501 (5) |
C4—C5 | 1.405 (4) | C21—H21A | 0.9700 |
C5—C6 | 1.394 (4) | C21—H21B | 0.9700 |
C6—C7 | 1.455 (4) | C22—H22A | 0.9600 |
C7—H7A | 0.9300 | C22—H22B | 0.9600 |
C8—C13 | 1.522 (5) | C22—H22C | 0.9600 |
C8—C9 | 1.533 (4) | C23—C24 | 1.493 (5) |
C8—H8 | 0.9800 | C23—H23A | 0.9600 |
C9—C10 | 1.514 (4) | C23—H23B | 0.9600 |
C9—H9 | 0.9800 | C23—H23C | 0.9600 |
C10—C11 | 1.519 (4) | C24—H24A | 0.9700 |
C10—H10A | 0.9700 | C24—H24B | 0.9700 |
C10—H10B | 0.9700 | O1W—H1A | 0.864 (10) |
C11—C12 | 1.524 (5) | O1W—H1B | 0.866 (10) |
C4—O1—C24 | 117.3 (2) | C11—C12—H12B | 109.5 |
C5—O2—H2' | 111 (3) | H12A—C12—H12B | 108.1 |
C20—O3—H3' | 105 (3) | C12—C13—C8 | 112.6 (3) |
C19—O4—C21 | 117.5 (2) | C12—C13—H13A | 109.1 |
C7—N1—C8 | 119.0 (2) | C8—C13—H13A | 109.1 |
C14—N2—C9 | 121.5 (3) | C12—C13—H13B | 109.1 |
C2—C1—C6 | 120.5 (3) | C8—C13—H13B | 109.1 |
C2—C1—H1 | 119.8 | H13A—C13—H13B | 107.8 |
C6—C1—H1 | 119.8 | N2—C14—C15 | 121.8 (3) |
C1—C2—C3 | 120.2 (3) | N2—C14—H14 | 119.1 |
C1—C2—H2 | 119.9 | C15—C14—H14 | 119.1 |
C3—C2—H2 | 119.9 | C20—C15—C16 | 119.7 (3) |
C4—C3—C2 | 120.4 (3) | C20—C15—C14 | 119.8 (3) |
C4—C3—H3 | 119.8 | C16—C15—C14 | 120.4 (3) |
C2—C3—H3 | 119.8 | C17—C16—C15 | 120.2 (3) |
O1—C4—C3 | 125.2 (3) | C17—C16—H16 | 119.9 |
O1—C4—C5 | 115.2 (2) | C15—C16—H16 | 119.9 |
C3—C4—C5 | 119.6 (3) | C16—C17—C18 | 120.5 (3) |
O2—C5—C6 | 122.0 (3) | C16—C17—H17 | 119.8 |
O2—C5—C4 | 118.1 (2) | C18—C17—H17 | 119.8 |
C6—C5—C4 | 119.8 (2) | C19—C18—C17 | 120.6 (3) |
C1—C6—C5 | 119.4 (3) | C19—C18—H18 | 119.7 |
C1—C6—C7 | 120.1 (3) | C17—C18—H18 | 119.7 |
C5—C6—C7 | 120.4 (2) | O4—C19—C18 | 125.4 (3) |
N1—C7—C6 | 122.2 (3) | O4—C19—C20 | 114.8 (2) |
N1—C7—H7A | 118.9 | C18—C19—C20 | 119.8 (3) |
C6—C7—H7A | 118.9 | O3—C20—C15 | 122.3 (3) |
N1—C8—C13 | 111.1 (3) | O3—C20—C19 | 118.6 (3) |
N1—C8—C9 | 108.2 (2) | C15—C20—C19 | 119.1 (3) |
C13—C8—C9 | 110.5 (3) | O4—C21—C22 | 107.2 (3) |
N1—C8—H8 | 109.0 | O4—C21—H21A | 110.3 |
C13—C8—H8 | 109.0 | C22—C21—H21A | 110.3 |
C9—C8—H8 | 109.0 | O4—C21—H21B | 110.3 |
N2—C9—C10 | 110.7 (2) | C22—C21—H21B | 110.3 |
N2—C9—C8 | 109.2 (2) | H21A—C21—H21B | 108.5 |
C10—C9—C8 | 111.3 (3) | C21—C22—H22A | 109.5 |
N2—C9—H9 | 108.6 | C21—C22—H22B | 109.5 |
C10—C9—H9 | 108.6 | H22A—C22—H22B | 109.5 |
C8—C9—H9 | 108.6 | C21—C22—H22C | 109.5 |
C9—C10—C11 | 111.6 (3) | H22A—C22—H22C | 109.5 |
C9—C10—H10A | 109.3 | H22B—C22—H22C | 109.5 |
C11—C10—H10A | 109.3 | C24—C23—H23A | 109.5 |
C9—C10—H10B | 109.3 | C24—C23—H23B | 109.5 |
C11—C10—H10B | 109.3 | H23A—C23—H23B | 109.5 |
H10A—C10—H10B | 108.0 | C24—C23—H23C | 109.5 |
C10—C11—C12 | 110.9 (3) | H23A—C23—H23C | 109.5 |
C10—C11—H11A | 109.5 | H23B—C23—H23C | 109.5 |
C12—C11—H11A | 109.5 | O1—C24—C23 | 107.1 (3) |
C10—C11—H11B | 109.5 | O1—C24—H24A | 110.3 |
C12—C11—H11B | 109.5 | C23—C24—H24A | 110.3 |
H11A—C11—H11B | 108.0 | O1—C24—H24B | 110.3 |
C13—C12—C11 | 110.6 (3) | C23—C24—H24B | 110.3 |
C13—C12—H12A | 109.5 | H24A—C24—H24B | 108.6 |
C11—C12—H12A | 109.5 | H1A—O1W—H1B | 103 (2) |
C13—C12—H12B | 109.5 | ||
C6—C1—C2—C3 | −1.1 (5) | C8—C9—C10—C11 | −56.0 (3) |
C1—C2—C3—C4 | 1.7 (5) | C9—C10—C11—C12 | 56.5 (4) |
C24—O1—C4—C3 | 6.5 (4) | C10—C11—C12—C13 | −55.5 (4) |
C24—O1—C4—C5 | −172.9 (3) | C11—C12—C13—C8 | 55.4 (4) |
C2—C3—C4—O1 | −179.7 (3) | N1—C8—C13—C12 | 65.6 (3) |
C2—C3—C4—C5 | −0.2 (5) | C9—C8—C13—C12 | −54.6 (4) |
O1—C4—C5—O2 | −0.5 (4) | C9—N2—C14—C15 | 177.9 (3) |
C3—C4—C5—O2 | −180.0 (3) | N2—C14—C15—C20 | 1.4 (5) |
O1—C4—C5—C6 | 177.6 (3) | N2—C14—C15—C16 | −177.0 (3) |
C3—C4—C5—C6 | −1.9 (4) | C20—C15—C16—C17 | 0.9 (5) |
C2—C1—C6—C5 | −1.0 (5) | C14—C15—C16—C17 | 179.3 (3) |
C2—C1—C6—C7 | 176.1 (3) | C15—C16—C17—C18 | 0.9 (6) |
O2—C5—C6—C1 | −179.5 (3) | C16—C17—C18—C19 | −0.3 (5) |
C4—C5—C6—C1 | 2.5 (4) | C21—O4—C19—C18 | −3.8 (4) |
O2—C5—C6—C7 | 3.5 (4) | C21—O4—C19—C20 | 177.3 (3) |
C4—C5—C6—C7 | −174.6 (3) | C17—C18—C19—O4 | 179.0 (3) |
C8—N1—C7—C6 | 176.8 (3) | C17—C18—C19—C20 | −2.2 (5) |
C1—C6—C7—N1 | 176.8 (3) | C16—C15—C20—O3 | 178.3 (3) |
C5—C6—C7—N1 | −6.2 (4) | C14—C15—C20—O3 | −0.1 (4) |
C7—N1—C8—C13 | 102.7 (3) | C16—C15—C20—C19 | −3.3 (4) |
C7—N1—C8—C9 | −135.8 (3) | C14—C15—C20—C19 | 178.2 (3) |
C14—N2—C9—C10 | −89.5 (3) | O4—C19—C20—O3 | 1.4 (4) |
C14—N2—C9—C8 | 147.7 (3) | C18—C19—C20—O3 | −177.6 (3) |
N1—C8—C9—N2 | 54.9 (3) | O4—C19—C20—C15 | −177.1 (2) |
C13—C8—C9—N2 | 176.7 (3) | C18—C19—C20—C15 | 4.0 (4) |
N1—C8—C9—C10 | −67.5 (3) | C19—O4—C21—C22 | −178.9 (3) |
C13—C8—C9—C10 | 54.3 (3) | C4—O1—C24—C23 | 176.0 (3) |
N2—C9—C10—C11 | −177.6 (3) |
Cg is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3′···N2 | 0.85 (1) | 1.77 (3) | 2.550 (4) | 152 (3) |
O2—H2′···N1 | 0.84 (1) | 1.85 (2) | 2.584 (3) | 144 (4) |
O1W—H1B···O3 | 0.86 (5) | 2.34 (7) | 3.005 (5) | 134 (8) |
O1W—H1B···O4 | 0.86 (5) | 2.38 (8) | 3.052 (5) | 135 (6) |
C21—H21B···Cg | 0.97 | 2.92 | 3.810 (4) | 153 |
Cg is the centroid of the C15–C20 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3'···N2 | 0.850 (3) | 1.77 (3) | 2.550 (4) | 152 (3) |
O2—H2'···N1 | 0.840 (3) | 1.85 (2) | 2.584 (3) | 144 (4) |
O1W—H1B···O3 | 0.86 (5) | 2.34 (7) | 3.005 (5) | 134 (8) |
O1W—H1B···O4 | 0.86 (5) | 2.38 (8) | 3.052 (5) | 135 (6) |
C21—H21B···Cg | 0.9700 | 2.92 | 3.810 (4) | 153 |
Acknowledgements
We thank the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, for the diffraction measurements. MRPK, NM and SSS thank the Defence Research Development Organization, New Delhi, India, for financial support.
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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 bases are an important class of ligands in molecular design devoted to energy storage such as molecular batteries (Franceschi, et al. 1999) and also in transition metal catalysis (Hwang, et al. 1998). Schiff base having intramolecular hydrogen bonding shows photophysical properties such as thermochromism and photochromism (Popović, et al. 2002). Schiff bases also have an ability to reversibly bind oxygen (Jones, et al.1979).
The title compound crystallizes in the monoclinic, P21/c space group. The bond lengths and the bond angles agree with the related structure (Ambili, et al., 2012). The torsional angle, 177.9 (3)° of the azomethine linkage, C9—N2—C14—C15 reveals that the title compound adopts E conformation (Fig. 1). The mean plane deviation calculations show that the molecule as a whole is non-planar. Ring puckering analysis (Cremer & Pople, 1975) and least square plane calculations show that the cyclohexyl ring adopts a chair conformation (QT = 0.565 (4) Å) with the equatorial substitution at C9 for N2 and axial substitution at C8 for N1.
Crystal system consists of intramolecular hydrogen bonds of lengths 1.79 (3) Å and 1.85 (3) Å which exists between the azomethine N atom and the neighbouring phenolic O atom leading to the formation of two six membered rings comprising of atoms C14—C15—C20—O3—H3'···N2 and C7—C6—C5—O2—H2'···N1 (Fig. 2). A C—H···π interaction between one of the hydrogen attached at C21 and the aromatic ring (C15—C20) with H···Cg distance of 2.92 Å (Fig. 3) dominates the packing of molecules in the lattice. Fig. 4 shows the packing diagram of the title compound along a axis.