In the crystal, the molecule of the title compound has crystallographically imposed twofold rotation symmetry. The crystal packing consists of layers parallel to the ab plane formed by O—H⋯N and C—H⋯O hydrogen bonds.
Keywords: crystal structure, hydrogen bond, phenol, aromatic ether, phenoxy, azomethines, Hirshfeld surface analysis
Abstract
In the crystal, the molecule of the title compound, C26H20N2O3, has crystallographically imposed twofold rotation symmetry. The crystal packing consists of layers parallel to the ab plane formed by O—H⋯N and C—H⋯O hydrogen bonds. Between the layers, C—H⋯π interactions are observed.
Chemical context
Several Schiff bases have been reported for their significant biological activities such as antitumor (Mansouri et al., 2013 ▸), anti-inflammatory (Shukla & Mishra, 2019 ▸), antibacterial (Van Zee & Coates, 2015 ▸) or antimicrobial (Pagadala et al., 2015 ▸). Schiff bases are also used as versatile components in nucleophilic addition with organometallic reagents and in cycloaddition reactions (Mohan et al., 2012 ▸). These findings prompted us to investigate the crystal structure of the title compound.
Structural commentary
The molecule of the title compound has crystallographically imposed twofold rotation symmetry (Fig. 1 ▸). The dihedral angle between the two unique benzene rings is 40.68 (6)° while the dihedral angle between the two central benzene rings is 77.71 (6)°. Bond lengths are typical for this kind of compounds.
Figure 1.
The title molecule with labeling scheme and 50% probability ellipsoids [symmetry code: (i) −x + 1, y, −z + 
].
Supramolecular features
In the crystal, O2—H2A⋯N1 and C5—H5⋯O2 hydrogen bonds link the molecules into layers parallel to the ab plane (Table 1 ▸, Fig. 2 ▸). The layers are hold together by C—H⋯π contacts (Table 1 ▸, Fig. 3 ▸) and by other van der Waals interactions (Table 2 ▸).
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 is the centroid of the C1–C6 benzene ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O2—H2A⋯N1i | 0.972 (19) | 1.828 (19) | 2.7615 (12) | 160.1 (16) |
| C5—H5⋯O2ii | 0.973 (13) | 2.431 (14) | 3.1121 (14) | 126.7 (10) |
| C12—H11⋯Cg1ii | 1.004 (14) | 2.986 (15) | 3.9882 (12) | 178.7 (19) |
Symmetry codes: (i) -x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}; (ii) -x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}.
Figure 2.
The layer structure viewed along the c-axis direction. The intermolecular O—H⋯N and C—H⋯O hydrogen bonds are shown as red and black dashed lines, respectively.
Figure 3.
Side view of two layers seen along the b-axis direction. Hydrogen bonds and C—H⋯π interactions are depicted by dashed lines.
Table 2. Short intermolecular contacts (Å) in the title structure.
| Contact | Distance | Symmetry operation |
|---|---|---|
| H12⋯O1 | 2.763 (14) | 1 − x, 2 − y, 1 − z |
| H6⋯H11 | 2.53 (2) | x, 2 − y, −{1\over 2} + z |
| C3⋯C6 | 3.5155 (15) | x, −1 + y, z |
| C6⋯H11 | 2.892 (15) | x, 1 − y, −{1\over 2} + z |
| C11⋯C11 | 3.319 (2) | {1\over 2} − x, {1\over 2} − y, 1 − z |
| H11⋯H2 | 2.40 (3) | 1 − x, 1 − y, 1 − z |
Hirshfeld surface analysis
Hirshfeld surface analysis, together with two-dimensional fingerprint plots, is an important tool for visualizing and analyzing intermolecular contacts in molecular crystals. The corresponding surfaces and fingerprint plots were prepared by CrystalExplorer (Turner et al., 2017 ▸). Fig. 4 ▸ shows the d norm map for the title molecule, with red spots indicating the positions of H⋯N contacts arising from the O—H⋯N hydrogen bonds.
Figure 4.
A view of the three-dimensional Hirshfeld surface for the title compound, plotted over d norm in the range −1.1242 to 1.4437 a.u.
Fig. 5 ▸ shows the two-dimensional fingerprint plots, which give the contributions of intermolecular contacts to the Hirshfeld surface. The most important contribution to the Hirshfeld surface (41.6%) is from H⋯H contacts. C⋯H/H⋯C and O⋯H/H⋯O interactions follow with 28.1% and 13.8% contributions, respectively. Other minor contributors are C⋯C (5.3%), N⋯H/H⋯N (4.8%), O⋯C/C⋯O (3.8%) and N⋯C/C⋯N (2.6%) contacts.
Figure 5.
A view of the two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O interactions. The d i and d e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.
Database survey
Five related compounds with a 4-[(E)-benzylideneamino]phenol skeleton are: (E)-2-{[(2-aminophenyl)imino]methyl}-5-(benzyloxy)phenol (NIBRIC; Ghichi et al., 2018 ▸), (Z)-3-(benzyloxy)-6-{[(5-chloro-2-hydroxyphenyl)amino]methylidene}cyclohexa-2,4-dien-1-one (NIBROI; Ghichi et al., 2018 ▸), 2-{(E)-[(2-methyl-3-nitrophenyl)imino]methyl}-4-nitrophenol (AFOPUI; Tanak et al., 2013 ▸), 2-[(E)-(2-chlorophenyl)iminomethyl]-6-methylphenol (SABKOX; Zhu et al., 2010 ▸) and 2-{[(2,4-dimethylphenyl)imino]methyl}-6-methylphenol (MUCDIY; Tanak et al., 2009 ▸).
In the crystal of NIBRIC, strong N—H⋯O hydrogen bonds form zigzag chains of molecules along the b-axis direction. Weaker C—H⋯π and offset π–π stacking interactions also contribute to the packing. For NIBROI, pairs of strong O—H⋯O hydrogen bonds form centrosymmetric dimers that enclose 
(18) rings. These combine with weaker C—H⋯Cl hydrogen bonds, which also generate centrosymmetric dimers, but with (14) motifs. Inversion-related C—H⋯π contacts lead to the formation of sheets of molecules parallel to (120), which are stacked approximately along the b-axis direction. In the crystal of AFOPUI, molecules are linked by C—H⋯O interactions, forming two-dimensional sheets parallel to the bc plane. In the structure of SABKOX, the hydroxy H atom is involved in a strong intramolecular O—H⋯N hydrogen bond, generating a S(6) ring. The molecular structure of MUCDIY is stabilized by an intramolecular O—H⋯N hydrogen bond, which generates a six membered ring.
Synthesis and crystallization
Condensation of 1 mmol of 4,4′-oxydibenzaldehyde (226 mg) with 2 mmol of 3-aminophenol (218 mg) in ethanol under reflux for 4 h afforded the crude product of the title compound. The product was crystallized from ethanol by slow evaporation to obtain good quality crystals for X-ray diffraction. Yield 82%.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. All H atoms were located in a difference-Fourier map and refined freely.
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C26H20N2O3 |
| M r | 408.44 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 150 |
| a, b, c (Å) | 26.8396 (6), 5.1174 (1), 17.2574 (4) |
| β (°) | 121.764 (1) |
| V (Å3) | 2015.27 (8) |
| Z | 4 |
| Radiation type | Cu Kα |
| μ (mm−1) | 0.72 |
| Crystal size (mm) | 0.25 × 0.06 × 0.06 |
| Data collection | |
| Diffractometer | Bruker D8 VENTURE PHOTON 100 CMOS |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.90, 0.96 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 15449, 1880, 1767 |
| R int | 0.031 |
| (sin θ/λ)max (Å−1) | 0.609 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.033, 0.086, 1.05 |
| No. of reflections | 1880 |
| No. of parameters | 182 |
| H-atom treatment | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.19, −0.16 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698902100181X/yk2146sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S205698902100181X/yk2146Isup2.hkl
Supporting information file. DOI: 10.1107/S205698902100181X/yk2146Isup3.cml
CCDC reference: 2062957
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| C26H20N2O3 | F(000) = 856 |
| Mr = 408.44 | Dx = 1.346 Mg m−3 |
| Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 26.8396 (6) Å | Cell parameters from 9934 reflections |
| b = 5.1174 (1) Å | θ = 3.9–69.8° |
| c = 17.2574 (4) Å | µ = 0.72 mm−1 |
| β = 121.764 (1)° | T = 150 K |
| V = 2015.27 (8) Å3 | Column, colourless |
| Z = 4 | 0.25 × 0.06 × 0.06 mm |
Data collection
| Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 1880 independent reflections |
| Radiation source: INCOATEC IµS micro–focus source | 1767 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.031 |
| Detector resolution: 10.4167 pixels mm-1 | θmax = 69.8°, θmin = 3.9° |
| ω scans | h = −32→32 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −6→6 |
| Tmin = 0.90, Tmax = 0.96 | l = −20→20 |
| 15449 measured reflections |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.033 | All H-atom parameters refined |
| wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.043P)2 + 1.3008P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 1880 reflections | Δρmax = 0.19 e Å−3 |
| 182 parameters | Δρmin = −0.16 e Å−3 |
| 0 restraints | Extinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0031 (2) |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.500000 | 1.3874 (2) | 0.250000 | 0.0267 (3) | |
| O2 | 0.21618 (3) | 0.09976 (18) | 0.33558 (6) | 0.0336 (2) | |
| H2A | 0.1966 (8) | 0.182 (4) | 0.2759 (13) | 0.066 (5)* | |
| N1 | 0.36195 (4) | 0.78690 (18) | 0.33726 (6) | 0.0233 (2) | |
| C1 | 0.46708 (5) | 1.2402 (2) | 0.27573 (7) | 0.0228 (3) | |
| C2 | 0.49250 (5) | 1.0380 (2) | 0.33777 (8) | 0.0288 (3) | |
| H2 | 0.5331 (6) | 0.994 (3) | 0.3625 (9) | 0.035 (3)* | |
| C3 | 0.45903 (5) | 0.8917 (2) | 0.36148 (8) | 0.0276 (3) | |
| H3 | 0.4769 (6) | 0.743 (3) | 0.4038 (9) | 0.033 (3)* | |
| C4 | 0.39966 (4) | 0.9482 (2) | 0.32294 (7) | 0.0220 (3) | |
| C5 | 0.37512 (5) | 1.1545 (2) | 0.26182 (7) | 0.0244 (3) | |
| H5 | 0.3337 (6) | 1.192 (3) | 0.2353 (9) | 0.031 (3)* | |
| C6 | 0.40866 (5) | 1.3034 (2) | 0.23883 (7) | 0.0242 (3) | |
| H6 | 0.3914 (5) | 1.445 (3) | 0.1965 (9) | 0.030 (3)* | |
| C7 | 0.38127 (5) | 0.6916 (2) | 0.41641 (7) | 0.0254 (3) | |
| H7 | 0.4211 (6) | 0.744 (3) | 0.4696 (10) | 0.035 (4)* | |
| C8 | 0.35036 (5) | 0.4960 (2) | 0.43754 (7) | 0.0238 (3) | |
| C9 | 0.29481 (5) | 0.4001 (2) | 0.37197 (7) | 0.0242 (3) | |
| H9 | 0.2735 (5) | 0.460 (3) | 0.3094 (9) | 0.026 (3)* | |
| C10 | 0.26950 (5) | 0.2038 (2) | 0.39519 (7) | 0.0242 (3) | |
| H10 | 0.2803 (6) | −0.038 (3) | 0.4990 (9) | 0.030 (3)* | |
| C11 | 0.29889 (5) | 0.1028 (2) | 0.48379 (8) | 0.0262 (3) | |
| H11 | 0.3729 (6) | 0.127 (3) | 0.6118 (10) | 0.034 (3)* | |
| C12 | 0.35320 (5) | 0.2004 (2) | 0.54851 (8) | 0.0278 (3) | |
| H12 | 0.4190 (6) | 0.465 (3) | 0.5730 (9) | 0.030 (3)* | |
| C13 | 0.37916 (5) | 0.3963 (2) | 0.52590 (8) | 0.0268 (3) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0298 (6) | 0.0206 (5) | 0.0400 (6) | 0.000 | 0.0254 (5) | 0.000 |
| O2 | 0.0266 (4) | 0.0395 (5) | 0.0285 (5) | −0.0111 (4) | 0.0103 (4) | −0.0010 (4) |
| N1 | 0.0218 (5) | 0.0235 (5) | 0.0265 (5) | 0.0009 (4) | 0.0141 (4) | 0.0018 (4) |
| C1 | 0.0256 (5) | 0.0208 (5) | 0.0278 (6) | −0.0023 (4) | 0.0181 (5) | −0.0032 (4) |
| C2 | 0.0204 (5) | 0.0313 (6) | 0.0344 (6) | 0.0025 (5) | 0.0142 (5) | 0.0046 (5) |
| C3 | 0.0240 (6) | 0.0273 (6) | 0.0304 (6) | 0.0030 (5) | 0.0136 (5) | 0.0066 (5) |
| C4 | 0.0224 (5) | 0.0226 (5) | 0.0235 (5) | −0.0011 (4) | 0.0138 (4) | −0.0019 (4) |
| C5 | 0.0221 (5) | 0.0262 (6) | 0.0275 (6) | 0.0037 (4) | 0.0148 (5) | 0.0013 (4) |
| C6 | 0.0276 (6) | 0.0215 (5) | 0.0277 (6) | 0.0042 (4) | 0.0175 (5) | 0.0020 (4) |
| C7 | 0.0237 (5) | 0.0276 (6) | 0.0247 (6) | −0.0018 (4) | 0.0125 (5) | −0.0010 (4) |
| C8 | 0.0235 (5) | 0.0251 (6) | 0.0249 (6) | −0.0002 (4) | 0.0142 (5) | −0.0010 (4) |
| C9 | 0.0238 (5) | 0.0275 (6) | 0.0219 (6) | 0.0008 (4) | 0.0124 (5) | 0.0012 (4) |
| C10 | 0.0209 (5) | 0.0267 (6) | 0.0257 (6) | −0.0014 (4) | 0.0128 (5) | −0.0035 (4) |
| C11 | 0.0274 (6) | 0.0254 (6) | 0.0299 (6) | −0.0001 (4) | 0.0179 (5) | 0.0021 (4) |
| C12 | 0.0271 (6) | 0.0317 (6) | 0.0249 (6) | 0.0033 (5) | 0.0140 (5) | 0.0046 (5) |
| C13 | 0.0224 (5) | 0.0325 (6) | 0.0237 (6) | −0.0011 (5) | 0.0109 (5) | −0.0003 (5) |
Geometric parameters (Å, º)
| O1—C1i | 1.3992 (12) | C5—H5 | 0.973 (13) |
| O1—C1 | 1.3993 (12) | C6—H6 | 0.959 (14) |
| O2—C10 | 1.3563 (13) | C7—C8 | 1.4634 (15) |
| O2—H2A | 0.972 (19) | C7—H7 | 1.012 (14) |
| N1—C7 | 1.2755 (14) | C8—C13 | 1.3935 (15) |
| N1—C4 | 1.4250 (13) | C8—C9 | 1.4028 (15) |
| C1—C2 | 1.3831 (16) | C9—C10 | 1.3848 (16) |
| C1—C6 | 1.3849 (15) | C9—H9 | 0.967 (13) |
| C2—C3 | 1.3865 (16) | C10—C11 | 1.3991 (16) |
| C2—H2 | 0.965 (14) | C11—C12 | 1.3812 (16) |
| C3—C4 | 1.3961 (15) | C11—H10 | 0.988 (14) |
| C3—H3 | 0.988 (15) | C12—C13 | 1.3888 (16) |
| C4—C5 | 1.3891 (16) | C12—H11 | 1.004 (14) |
| C5—C6 | 1.3871 (15) | C13—H12 | 1.007 (13) |
| C1i—O1—C1 | 114.87 (11) | N1—C7—C8 | 124.35 (10) |
| C10—O2—H2A | 113.5 (11) | N1—C7—H7 | 120.7 (8) |
| C7—N1—C4 | 118.81 (9) | C8—C7—H7 | 114.9 (8) |
| C2—C1—C6 | 120.56 (10) | C13—C8—C9 | 119.77 (10) |
| C2—C1—O1 | 120.77 (9) | C13—C8—C7 | 117.53 (10) |
| C6—C1—O1 | 118.66 (9) | C9—C8—C7 | 122.65 (10) |
| C1—C2—C3 | 120.01 (10) | C10—C9—C8 | 119.69 (10) |
| C1—C2—H2 | 119.8 (9) | C10—C9—H9 | 117.3 (8) |
| C3—C2—H2 | 120.1 (9) | C8—C9—H9 | 122.9 (8) |
| C2—C3—C4 | 120.12 (10) | O2—C10—C9 | 123.21 (10) |
| C2—C3—H3 | 119.8 (8) | O2—C10—C11 | 116.53 (10) |
| C4—C3—H3 | 120.0 (8) | C9—C10—C11 | 120.26 (10) |
| C5—C4—C3 | 119.03 (10) | C12—C11—C10 | 119.88 (10) |
| C5—C4—N1 | 118.41 (9) | C12—C11—H10 | 121.0 (8) |
| C3—C4—N1 | 122.28 (10) | C10—C11—H10 | 119.1 (8) |
| C6—C5—C4 | 120.99 (10) | C11—C12—C13 | 120.38 (10) |
| C6—C5—H5 | 120.6 (8) | C11—C12—H11 | 118.1 (8) |
| C4—C5—H5 | 118.4 (8) | C13—C12—H11 | 121.5 (8) |
| C1—C6—C5 | 119.23 (10) | C12—C13—C8 | 120.02 (10) |
| C1—C6—H6 | 120.2 (8) | C12—C13—H12 | 120.2 (8) |
| C5—C6—H6 | 120.5 (8) | C8—C13—H12 | 119.8 (8) |
| C1i—O1—C1—C2 | 49.26 (9) | C4—N1—C7—C8 | −171.34 (10) |
| C1i—O1—C1—C6 | −131.68 (11) | N1—C7—C8—C13 | 175.25 (11) |
| C6—C1—C2—C3 | 1.91 (17) | N1—C7—C8—C9 | −2.15 (18) |
| O1—C1—C2—C3 | −179.04 (10) | C13—C8—C9—C10 | −1.16 (16) |
| C1—C2—C3—C4 | −0.10 (18) | C7—C8—C9—C10 | 176.18 (10) |
| C2—C3—C4—C5 | −0.88 (17) | C8—C9—C10—O2 | −179.55 (10) |
| C2—C3—C4—N1 | 173.02 (10) | C8—C9—C10—C11 | 0.54 (16) |
| C7—N1—C4—C5 | −145.80 (11) | O2—C10—C11—C12 | −179.50 (10) |
| C7—N1—C4—C3 | 40.26 (15) | C9—C10—C11—C12 | 0.42 (17) |
| C3—C4—C5—C6 | 0.06 (16) | C10—C11—C12—C13 | −0.76 (17) |
| N1—C4—C5—C6 | −174.08 (10) | C11—C12—C13—C8 | 0.15 (17) |
| C2—C1—C6—C5 | −2.71 (16) | C9—C8—C13—C12 | 0.82 (17) |
| O1—C1—C6—C5 | 178.23 (9) | C7—C8—C13—C12 | −176.66 (10) |
| C4—C5—C6—C1 | 1.72 (16) |
Symmetry code: (i) −x+1, y, −z+1/2.
Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C1–C6 benzene ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N1ii | 0.972 (19) | 1.828 (19) | 2.7615 (12) | 160.1 (16) |
| C5—H5···O2iii | 0.973 (13) | 2.431 (14) | 3.1121 (14) | 126.7 (10) |
| C12—H11···Cg1iii | 1.004 (14) | 2.986 (15) | 3.9882 (12) | 178.7 (19) |
Symmetry codes: (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+3/2, −z+1/2.
Funding Statement
This work was funded by National Science Foundation grant 1228232. Tulane University grant .
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698902100181X/yk2146sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S205698902100181X/yk2146Isup2.hkl
Supporting information file. DOI: 10.1107/S205698902100181X/yk2146Isup3.cml
CCDC reference: 2062957
Additional supporting information: crystallographic information; 3D view; checkCIF report