The title Schiff base compound was synthesized via the condensation reaction of 1,2-diaminebenzene with 4-benzyloxy-2-hydroxybenzaldehyde. The molecule is V-shaped and possesses mirror symmetry; the mirror bisects the central benzene ring. There are two intramolecular O—H⋯N hydrogen bonds present forming S(6) ring motifs.
Keywords: crystal structure, Schiff base, antioxidant capacity, CUPRAC, hydrogen bonding, C—H⋯π interactions, Hirshfeld surface analysis
Abstract
The whole molecule of the title Schiff base compound, C34H28N2O4, is generated by mirror symmetry, with the mirror bisecting the central benzene ring. It was synthesized via the condensation reaction of 1,2-diaminebenzene with 4-benzyloxy-2-hydroxybenzaldehyde. The molecule is V-shaped and there are two intramolecular O—H⋯N hydrogen bonds present forming S(6) ring motifs. The configuration about the C=N imine bonds is E. The central benzene ring makes dihedral angles of 41.9 (2) and 43.6 (2)° with the phenol ring and the outer benzyloxy ring, respectively. The latter two rings are inclined to each other by 84.4 (2)°. In the crystal, molecules are linked by C—H⋯π interactions, forming layers lying parallel to the ab plane. The Hirshfeld surface analysis and the two-dimensional fingerprint plots confirm the predominance of these interactions in the crystal structure. The antioxidant capacity of the compound was determined by the cupric reducing antioxidant capacity (CUPRAC) process.
Chemical context
Schiff base derivatives are a biologically versatile class of compounds possessing diverse activities, such as anti-oxidant (Haribabu et al., 2015 ▸, 2016 ▸), anti-inflammatory (Alam et al., 2012 ▸), antianxiety, antidepressant (Jubie et al., 2011 ▸), anti-tumour, antibacterial, and fungicidal properties (Refat et al., 2008 ▸; Kannan & Ramesh, 2006 ▸). Bis-bidentate Schiff base ligands have been studied extensively and used as building blocks in metallo-supramolecular chemistry (Birkedal & Pattison, 2006 ▸; Shahverdizadeh & Tiekink, 2011 ▸; Chu & Huang, 2007 ▸; Yoshida & Ichikawa, 1997 ▸; Kruger et al., 2001 ▸). The common structural feature of these compounds is the presence of an azomethine group, linked by a η methylene bridge, which can act as a hydrogen-bond acceptor. In view of this interest we have synthesized the title compound, (I), and report herein on its crystal structure. The 1H NMR NMR spectrum reveals the presence of an imino group (N=CH) in the range δ = 8.5–8.7 p.p.m. The antioxidant capacity of the compound was determined by the cupric reducing antioxidant capacity (CUPRAC) process.
Structural commentary
The molecular structure of compound (I) is illustrated in Fig. 1 ▸. The asymmetric unit consists of half a molecule, with the whole molecule being generated by mirror symmetry. The mirror bisects the central benzene ring, viz. bonds C1—C1i and C3—C3i [symmetry code: (i) −x, y, z]. In the molecule there are two intramolecular O—H⋯N hydrogen bonds present (Table 1 ▸), which form S(6) ring motifs as shown in Fig. 1 ▸. The configuration of the C4=N1 imine bonds is E and the C4=N1 bond length is 1.278 (6) Å. The C3—N1=C4 bond angles are less than 120° [118.9 (4)°], and the imine group has a C3—N1—C4—C5 torsion angle of −176.8 (4)°. The molecule is V-shaped and the two arms are non-planar; the central benzene ring forms dihedral angles of 41.9 (2) and 43.6 (2)° with the phenol ring (C5-C10) and the outer benzyloxy ring (C12–C17), respectively. The latter two rings are almost normal to each other, with a dihedral angle of 84.4 (2)°.
Figure 1.
View of the molecular structure of compound (I), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Unlabelled atoms are related to labelled atoms by the mirror symmetry code: (i) −x, y, z. The intramolecular O—H⋯N hydrogen bonds (see Table 1 ▸) are shown as dashed lines.
Table 1. Hydrogen-bond geometry (Å, °).
Cg2 is the centroid of the C5–C10 phenol ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1O⋯N1 | 0.82 | 1.90 | 2.622 (5) | 147 |
| C2—H2⋯Cg2i | 0.93 | 2.88 | 3.499 (5) | 125 |
| C13—H13⋯Cg2ii | 0.93 | 2.60 | 3.493 (5) | 161 |
Symmetry codes: (i) 
; (ii) 
.
Supramolecular features and Hirshfeld surface analysis
In the crystal of (I), molecules are linked by C—H⋯π interactions (Table 1 ▸), forming layers parallel to the (001) plane, as illustrated in Fig. 2 ▸.
Figure 2.
Crystal packing of compound (I) viewed along the c axis, with the O—H⋯N intramolecular hydrogen bonds and the C—H⋯π interactions (see Table 1 ▸) illustrated as dashed lines.
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) were performed with CrystalExplorer17 (Turner et al., 2017 ▸). The Hirshfeld surface of compound (I) mapped over d norm is given in Fig. 3 ▸, and the fingerprint plots are given in Fig. 4 ▸. They reveal that the principal intermolecular interactions are H⋯H at 45.7% (Fig. 4 ▸ b) and H⋯C/C⋯H at 34.6% (Fig. 4 ▸ c), followed by the H⋯O/O⋯H interactions at 13.6% (Fig. 4 ▸ d).
Figure 3.
View of the Hirshfeld surface of (I) mapped over d norm.
Figure 4.
The two-dimensional fingerprint plots of (I): (a) all interactions; (b) H⋯H; (c) H⋯C/C⋯H; (d) H⋯O/O⋯H.
Database survey
A search of the Cambridge Structural Database (CSD, Version 5.39, last update February 2018; Groom et al., 2016 ▸) for similar compounds yielded four hits. These compounds (see Fig. 5 ▸) include 5,5′-dihydroxy-2,2′-[o-phenylenebis(nitrilomethylene)]diphenol ethanol solvate (II) (CSD refcode HUVXUT; Soroceanu et al., 2013 ▸), 5,5′-dimethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenol (III) (KUSJIS; Kargar et al., 2010 ▸), 1,2-bis{[(2-hydroxy-4-methoxyphenyl)(phenyl)methylene]amino}benzene (IV) (SOXCIS; Lippe et al., 2009 ▸) and 5,5′-dimethoxy-2,2′-1,2-phenylenebis(nitrilomethylidyne)]diphenol (V) (XIFREK; Eltayeb et al., 2007 ▸). In all four compounds there are two intramolecular O—H⋯N hydrogen bonds present forming S(6) ring motifs.
Figure 5.
Similar compounds to that of the title compound, (I), in the CSD; see Section 4, Database survey.
In (II) the phenol rings are inclined to the central benzene ring by 53.9 (3) and 4.0 (2)° and to each other by 49.9 (2)°. In (III) the corresponding dihedral angles are 48.12 (8), 21.44 (8) and 47.70 (8)°, while in (V) the corresponding dihedral angles are 58.29 (12), 2.20 (12) and 57.60 (12)°. In compound (IV), that possesses twofold rotational symmetry with the twofold axis bisecting the central benzene ring, the phenol rings are inclined to the central benzene ring by 82.30 (5)° and to each other by 63.76 (5)°. In the title compound, which possesses mirror symmetry, the corresponding dihedral angles are 41.9 (2) and 68.9 (2)°.
A search of the CSD for metal complexes of compounds similar to compound (I) gave over 30 hits. The ligands always coordinate in a tetradentate manner. For example, there were 13 hits for transition metal complexes of compound (II). The majority involve square-planar coordinated metal atoms, such as in complexes (5,5′-dihydroxy-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato)nickel(II) dihydrate (POFFOG; Fun et al., 2008 ▸) and (4,4′-{1,2-phenylenebis[(nitrilo-κN)methylylidene]}dibenzene-1,3-diolato-κO 3)copper(II) methanol solvate (DUQBEX; Niu et al., 2010 ▸). For compound (V), five hits were found; they include three sixfold-coordinated tin complexes (DOSCOF, DOSDAS, DOSFOI; Muñoz-Flores et al., 2014 ▸) and two square-pyramidal manganese complexes (ODESEY, Ghaemi et al., 2016 ▸; XIYQOM, Eltayeb et al., 2008 ▸).
Antioxidant activity
The antioxidant activity profile of the synthesized compound (I) was determined by utilizing the copper(II)–neocuprine [CuII-Nc] (CUPRAC) method (Apak et al., 2004 ▸). The CUPRAC method (Fig. 6 ▸) (cupric ion reducing antioxidant capacity) is based on the follow-up of the decrease in the increased absorbance of the neocuproene (Nc), copper (Cu+2)Nc2–Cu+2 complex. Indeed, in the presence of an antioxidant agent, the copper–neocuproene complex is reduced and this reaction is quantified spectrophotometrically at a wavelength of 450 nm.
Figure 6.
Reduction of the chromogenic complex of Cu+2–Nc
According to the cupric ion reducing antioxidant capacity assay, the title compound displayed activity with variable potency in all tested concentrations, because the percentage (%) inhibition in the CUPRAC assay is good [A0.50 = 15.03 ± 1.50 for a 4 mg dosage, compared to the results for buthylated toluene (BHT) [A0.50 = 8.97 ± 3.94], used as a positive control (see Table 2 ▸). Note: In CUPRAC antioxidant activity, the values expressed are the mean ± s.u.s of three parallel measurements (p < 0.05).
Table 2. Cupric ion reducing antioxidant capacity of compound (I).
| Percentage (%) Inhibition | ||||||||
|---|---|---|---|---|---|---|---|---|
| 12.5 µg | 25 µg | 50 µg | 100 µg | 200 µg | 400 µg | 800 µg | A0.50 (μg ml−1) | |
| Compound (I) | 0.39±0.01 | 0.59±0.01 | 0.91±0.03 | 1.42±0.02 | 1.84±0.36 | 3.12±0.25 | 4.29±0.11 | 15.03±1.50 |
| BHT | 1.41±0.03 | 2.22±0.05 | 2.42±0.02 | 2.50±0.01 | 2.56±0.05 | 2.86±0.07 | 3.38±0.13 | 8.97±3.94 |
Synthesis and crystallization
1,2-Diaminebenzene (0.027 g) and 4-benzyloxy-2-hydroxybenzaldehyde (0.1141 g) in ethanol (15 ml) were refluxed for 1 h, then the solvent was evaporated in vacuo. The residue was recrystallized from ethanol, yielding yellow block-like crystals of the title compound on slow evaporation of the solvent. The purity of the compound was characterized by its NMR spectrum (250 MHz, CDCl3). The azomethine proton appears in the 8.5–8.7 p.p.m. range, while the imine bond is characterized in the 13C RMN spectrum with the imine C and OH signals in the range 162.23–163.34 p.p.m. 1H NMR: δ = 6.5–7.6 (m, 12H; H-ar), δ = 13.7 (s, 1H; OH), δ = 5.1 (s, 1H; CH2–O). 13C NMR: 70.15, 120.33, 127.30, 127.64, 128.26, 128.75, 142.32, 162.23, 163.33, 163.34.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The hydroxyl H atom was located in a difference-Fourier map and initially freely refined. In the final cycles of refinements it was positioned geometrically (O—H = 0.82 Å) and refined as riding with U iso(H) = 1.5U eq(O). The C-bound H atoms were positioned geometrically (C–H = 0.93–0.97 Å) and refined as riding with U iso(H) = 1.2U eq(C).
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C34H28N2O4 |
| M r | 528.58 |
| Crystal system, space group | Orthorhombic, C m c21 |
| Temperature (K) | 293 |
| a, b, c (Å) | 35.297 (3), 9.3902 (6), 8.3603 (5) |
| V (Å3) | 2771.0 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.08 |
| Crystal size (mm) | 0.03 × 0.02 × 0.01 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 4493, 2516, 1691 |
| R int | 0.042 |
| (sin θ/λ)max (Å−1) | 0.651 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.053, 0.158, 1.02 |
| No. of reflections | 2516 |
| No. of parameters | 185 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.29, −0.24 |
Supplementary Material
Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S2056989018005832/su5438sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018005832/su5438Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989018005832/su5438Isup3.cml
CCDC reference: 1837095
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| C34H28N2O4 | F(000) = 1112 |
| Mr = 528.58 | Dx = 1.267 Mg m−3 |
| Orthorhombic, Cmc21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: C 2c -2 | Cell parameters from 1621 reflections |
| a = 35.297 (3) Å | θ = 2.2–21.3° |
| b = 9.3902 (6) Å | µ = 0.08 mm−1 |
| c = 8.3603 (5) Å | T = 293 K |
| V = 2771.0 (3) Å3 | Block, yellow |
| Z = 4 | 0.03 × 0.02 × 0.01 mm |
Data collection
| Bruker APEXII CCD diffractometer | Rint = 0.042 |
| Detector resolution: 18.4 pixels mm-1 | θmax = 27.5°, θmin = 3.7° |
| φ and ω scans | h = −45→40 |
| 4493 measured reflections | k = −12→5 |
| 2516 independent reflections | l = −10→6 |
| 1691 reflections with I > 2σ(I) |
Refinement
| 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)] = 0.053 | Hydrogen site location: mixed |
| wR(F2) = 0.158 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0817P)2] where P = (Fo2 + 2Fc2)/3 |
| 2516 reflections | (Δ/σ)max < 0.001 |
| 185 parameters | Δρmax = 0.29 e Å−3 |
| 1 restraint | Δρmin = −0.24 e Å−3 |
Special details
| Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.05052 (9) | 0.2350 (3) | 0.3234 (5) | 0.0693 (13) | |
| O2 | 0.15676 (8) | 0.0288 (3) | 0.5919 (4) | 0.0546 (9) | |
| N1 | 0.03881 (9) | 0.5084 (4) | 0.3640 (5) | 0.0487 (10) | |
| C1 | 0.01955 (13) | 0.8879 (4) | 0.2654 (7) | 0.0639 (15) | |
| C2 | 0.03890 (12) | 0.7645 (4) | 0.2985 (6) | 0.0567 (14) | |
| C3 | 0.01982 (11) | 0.6379 (4) | 0.3322 (5) | 0.0481 (11) | |
| C4 | 0.06841 (12) | 0.5103 (4) | 0.4519 (6) | 0.0495 (14) | |
| C5 | 0.09057 (11) | 0.3828 (4) | 0.4833 (5) | 0.0454 (11) | |
| C6 | 0.08042 (11) | 0.2506 (4) | 0.4207 (5) | 0.0475 (11) | |
| C7 | 0.10168 (11) | 0.1285 (4) | 0.4566 (5) | 0.0488 (11) | |
| C8 | 0.13349 (11) | 0.1401 (4) | 0.5523 (5) | 0.0463 (12) | |
| C9 | 0.14420 (12) | 0.2710 (4) | 0.6146 (6) | 0.0560 (16) | |
| C10 | 0.12269 (12) | 0.3889 (4) | 0.5813 (5) | 0.0560 (16) | |
| C11 | 0.14781 (12) | −0.1086 (4) | 0.5260 (6) | 0.0547 (16) | |
| C12 | 0.17886 (11) | −0.2104 (4) | 0.5695 (5) | 0.0449 (11) | |
| C13 | 0.17544 (12) | −0.2993 (4) | 0.6998 (6) | 0.0543 (16) | |
| C14 | 0.20330 (16) | −0.3988 (4) | 0.7345 (6) | 0.0677 (17) | |
| C15 | 0.23502 (14) | −0.4070 (5) | 0.6404 (7) | 0.0700 (19) | |
| C16 | 0.23920 (14) | −0.3165 (6) | 0.5124 (7) | 0.0697 (17) | |
| C17 | 0.21118 (13) | −0.2190 (5) | 0.4765 (6) | 0.0617 (17) | |
| H1 | 0.03276 | 0.97121 | 0.24301 | 0.0770* | |
| H1O | 0.04038 | 0.31254 | 0.30933 | 0.1040* | |
| H2 | 0.06524 | 0.76529 | 0.29851 | 0.0680* | |
| H4 | 0.0777 (10) | 0.604 (4) | 0.509 (5) | 0.041 (9)* | |
| H7 | 0.09442 | 0.04030 | 0.41635 | 0.0580* | |
| H9 | 0.16571 | 0.27872 | 0.67824 | 0.0670* | |
| H10 | 0.12968 | 0.47594 | 0.62529 | 0.0670* | |
| H11A | 0.12385 | −0.14214 | 0.56862 | 0.0660* | |
| H11B | 0.14557 | −0.10203 | 0.41061 | 0.0660* | |
| H13 | 0.15420 | −0.29259 | 0.76516 | 0.0650* | |
| H14 | 0.20047 | −0.45974 | 0.82141 | 0.0810* | |
| H15 | 0.25371 | −0.47378 | 0.66311 | 0.0840* | |
| H16 | 0.26095 | −0.32099 | 0.44979 | 0.0840* | |
| H17 | 0.21407 | −0.15860 | 0.38915 | 0.0740* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0640 (19) | 0.0400 (16) | 0.104 (3) | 0.0056 (14) | −0.0359 (19) | −0.0063 (17) |
| O2 | 0.0595 (17) | 0.0386 (14) | 0.0658 (17) | 0.0080 (12) | −0.0166 (15) | −0.0028 (14) |
| N1 | 0.0416 (17) | 0.0335 (16) | 0.071 (2) | 0.0021 (14) | 0.0019 (18) | 0.0024 (15) |
| C1 | 0.063 (3) | 0.0317 (19) | 0.097 (3) | −0.0042 (16) | −0.001 (3) | 0.003 (2) |
| C2 | 0.047 (2) | 0.041 (2) | 0.082 (3) | −0.0048 (17) | −0.002 (2) | 0.000 (2) |
| C3 | 0.049 (2) | 0.0322 (18) | 0.063 (2) | 0.0022 (16) | 0.002 (2) | −0.0028 (17) |
| C4 | 0.049 (2) | 0.0345 (19) | 0.065 (3) | 0.0002 (17) | 0.003 (2) | −0.0024 (18) |
| C5 | 0.042 (2) | 0.0373 (19) | 0.057 (2) | −0.0015 (16) | 0.002 (2) | −0.0033 (18) |
| C6 | 0.042 (2) | 0.0364 (19) | 0.064 (2) | −0.0017 (16) | −0.008 (2) | −0.0015 (17) |
| C7 | 0.051 (2) | 0.0365 (18) | 0.059 (2) | −0.0007 (16) | −0.010 (2) | −0.0041 (19) |
| C8 | 0.047 (2) | 0.039 (2) | 0.053 (2) | 0.0063 (16) | −0.0047 (19) | 0.0005 (17) |
| C9 | 0.058 (3) | 0.045 (2) | 0.065 (3) | −0.0010 (18) | −0.017 (2) | −0.003 (2) |
| C10 | 0.060 (3) | 0.039 (2) | 0.069 (3) | −0.0035 (18) | −0.011 (2) | −0.006 (2) |
| C11 | 0.059 (3) | 0.041 (2) | 0.064 (3) | 0.0043 (19) | −0.013 (2) | −0.0047 (19) |
| C12 | 0.043 (2) | 0.0378 (19) | 0.054 (2) | 0.0001 (16) | −0.0069 (18) | −0.0056 (18) |
| C13 | 0.054 (3) | 0.049 (2) | 0.060 (3) | 0.0042 (18) | −0.004 (2) | −0.001 (2) |
| C14 | 0.082 (3) | 0.051 (3) | 0.070 (3) | 0.013 (2) | −0.021 (3) | 0.005 (2) |
| C15 | 0.060 (3) | 0.055 (3) | 0.095 (4) | 0.020 (2) | −0.023 (3) | −0.028 (3) |
| C16 | 0.053 (3) | 0.075 (3) | 0.081 (3) | 0.006 (2) | 0.001 (3) | −0.021 (3) |
| C17 | 0.062 (3) | 0.057 (3) | 0.066 (3) | −0.005 (2) | −0.002 (2) | −0.001 (2) |
Geometric parameters (Å, º)
| O1—C6 | 1.341 (5) | C12—C13 | 1.378 (6) |
| O2—C8 | 1.370 (5) | C13—C14 | 1.387 (6) |
| O2—C11 | 1.438 (5) | C14—C15 | 1.371 (8) |
| N1—C3 | 1.414 (5) | C15—C16 | 1.374 (8) |
| N1—C4 | 1.278 (6) | C16—C17 | 1.381 (7) |
| O1—H1O | 0.8200 | C1—H1 | 0.9300 |
| C1—C1i | 1.380 (6) | C2—H2 | 0.9300 |
| C1—C2 | 1.373 (6) | C4—H4 | 1.05 (4) |
| C2—C3 | 1.395 (5) | C7—H7 | 0.9300 |
| C3—C3i | 1.399 (5) | C9—H9 | 0.9300 |
| C4—C5 | 1.454 (5) | C10—H10 | 0.9300 |
| C5—C10 | 1.400 (6) | C11—H11A | 0.9700 |
| C5—C6 | 1.394 (5) | C11—H11B | 0.9700 |
| C6—C7 | 1.403 (5) | C13—H13 | 0.9300 |
| C7—C8 | 1.383 (6) | C14—H14 | 0.9300 |
| C8—C9 | 1.388 (6) | C15—H15 | 0.9300 |
| C9—C10 | 1.371 (6) | C16—H16 | 0.9300 |
| C11—C12 | 1.499 (6) | C17—H17 | 0.9300 |
| C12—C17 | 1.383 (6) | ||
| C8—O2—C11 | 117.4 (3) | C12—C17—C16 | 120.5 (5) |
| C3—N1—C4 | 118.9 (4) | C2—C1—H1 | 120.00 |
| C6—O1—H1O | 109.00 | C1i—C1—H1 | 120.00 |
| C1i—C1—C2 | 119.8 (4) | C1—C2—H2 | 119.00 |
| C1—C2—C3 | 121.3 (4) | C3—C2—H2 | 119.00 |
| N1—C3—C3i | 118.3 (3) | N1—C4—H4 | 122 (2) |
| C2—C3—C3i | 118.9 (4) | C5—C4—H4 | 116 (2) |
| N1—C3—C2 | 122.8 (4) | C6—C7—H7 | 120.00 |
| N1—C4—C5 | 122.2 (4) | C8—C7—H7 | 120.00 |
| C4—C5—C10 | 120.5 (4) | C8—C9—H9 | 120.00 |
| C6—C5—C10 | 117.7 (3) | C10—C9—H9 | 120.00 |
| C4—C5—C6 | 121.8 (4) | C5—C10—H10 | 119.00 |
| O1—C6—C7 | 117.5 (3) | C9—C10—H10 | 119.00 |
| C5—C6—C7 | 120.7 (4) | O2—C11—H11A | 110.00 |
| O1—C6—C5 | 121.8 (3) | O2—C11—H11B | 110.00 |
| C6—C7—C8 | 119.6 (4) | C12—C11—H11A | 110.00 |
| O2—C8—C9 | 115.0 (4) | C12—C11—H11B | 110.00 |
| C7—C8—C9 | 120.5 (4) | H11A—C11—H11B | 108.00 |
| O2—C8—C7 | 124.5 (3) | C12—C13—H13 | 120.00 |
| C8—C9—C10 | 119.2 (4) | C14—C13—H13 | 120.00 |
| C5—C10—C9 | 122.3 (4) | C13—C14—H14 | 120.00 |
| O2—C11—C12 | 108.6 (3) | C15—C14—H14 | 120.00 |
| C11—C12—C13 | 120.9 (4) | C14—C15—H15 | 120.00 |
| C13—C12—C17 | 118.8 (4) | C16—C15—H15 | 120.00 |
| C11—C12—C17 | 120.3 (4) | C15—C16—H16 | 120.00 |
| C12—C13—C14 | 120.8 (4) | C17—C16—H16 | 120.00 |
| C13—C14—C15 | 119.8 (4) | C12—C17—H17 | 120.00 |
| C14—C15—C16 | 120.0 (5) | C16—C17—H17 | 120.00 |
| C15—C16—C17 | 120.2 (5) | ||
| C11—O2—C8—C7 | 1.5 (6) | C4—C5—C10—C9 | 179.6 (4) |
| C11—O2—C8—C9 | −177.8 (4) | C6—C5—C10—C9 | 0.9 (6) |
| C8—O2—C11—C12 | 174.0 (3) | O1—C6—C7—C8 | 177.9 (4) |
| C4—N1—C3—C2 | 41.3 (6) | C5—C6—C7—C8 | −1.4 (6) |
| C4—N1—C3—C3i | −139.8 (4) | C6—C7—C8—O2 | −178.4 (4) |
| C3—N1—C4—C5 | −176.8 (4) | C6—C7—C8—C9 | 0.9 (6) |
| C1i—C1—C2—C3 | 0.1 (8) | O2—C8—C9—C10 | 179.9 (4) |
| C2—C1—C1i—C2i | 0.0 (9) | C7—C8—C9—C10 | 0.5 (7) |
| C1—C2—C3—N1 | 178.9 (5) | C8—C9—C10—C5 | −1.4 (7) |
| C1—C2—C3—C3i | −0.1 (7) | O2—C11—C12—C13 | 96.8 (4) |
| N1—C3—C3i—N1i | 0.0 (6) | O2—C11—C12—C17 | −84.8 (5) |
| N1—C3—C3i—C2i | −179.0 (4) | C11—C12—C13—C14 | 176.4 (4) |
| C2—C3—C3i—N1i | 179.0 (4) | C17—C12—C13—C14 | −2.0 (6) |
| C2—C3—C3i—C2i | 0.0 (6) | C11—C12—C17—C16 | −177.4 (4) |
| N1—C4—C5—C6 | −0.9 (7) | C13—C12—C17—C16 | 1.0 (7) |
| N1—C4—C5—C10 | −179.5 (4) | C12—C13—C14—C15 | 1.4 (7) |
| C4—C5—C6—O1 | 2.6 (6) | C13—C14—C15—C16 | 0.2 (7) |
| C4—C5—C6—C7 | −178.2 (4) | C14—C15—C16—C17 | −1.2 (8) |
| C10—C5—C6—O1 | −178.8 (4) | C15—C16—C17—C12 | 0.6 (8) |
| C10—C5—C6—C7 | 0.5 (6) |
Symmetry code: (i) −x, y, z.
Hydrogen-bond geometry (Å, º)
Cg2 is the centroid of the C5–C10 phenol ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1O···N1 | 0.82 | 1.90 | 2.622 (5) | 147 |
| C2—H2···Cg2ii | 0.93 | 2.88 | 3.499 (5) | 125 |
| C13—H13···Cg2iii | 0.93 | 2.60 | 3.493 (5) | 161 |
Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x, −y, z+1/2.
Funding Statement
This work was funded by Ministère de l’Enseignement Supérieur et de la Recherche Scientifique grant . University of Constantine1, Algeria grant .
References
- Alam, M. S., Choi, J.-H. & Lee, D.-U. (2012). Bioorg. Med. Chem. 20, 4103–4108. [DOI] [PubMed]
- Apak, R., Güçlü, K., Özyürek, M. & Karademir, S. E. (2004). J. Agric. Food Chem. 52, 7970–7981. [DOI] [PubMed]
- Birkedal, H. & Pattison, P. (2006). Acta Cryst. C62, o139–o141. [DOI] [PubMed]
- Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsion, USA.
- Chu, Z. & Huang, W. (2007). J. Mol. Struct. 837, 15–22.
- Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, m670–m671. [DOI] [PMC free article] [PubMed]
- Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, o3094–o3095.
- Fun, H.-K., Kia, R., Mirkhani, V. & Zargoshi, H. (2008). Acta Cryst. E64, m1181–m1182. [DOI] [PMC free article] [PubMed]
- Ghaemi, A., Keyvani, B., Rayati, S., Zarei, S. & Notash, B. (2016). Zh. Strukt. Khim. (Russ. J. Struct. Chem.), 57, 1027–1030.
- Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
- Haribabu, J., Subhashree, G. R., Saranya, S., Gomathi, K., Karvembu, R. & Gayathri, D. (2015). J. Mol. Struct. 1094, 281–291.
- Haribabu, J., Subhashree, G. R., Saranya, S., Gomathi, K., Karvembu, R. & Gayathri, D. (2016). J. Mol. Struct. 1110, 185–195.
- Jubie, S., Sikdar, P., Antony, S., Kalirajan, R., Gowramma, B., Gomathy, S. & Elango, K. (2011). Pak. J. Pharm. Sci. 24, 109–112. [PubMed]
- Kannan, M. & Ramesh, R. (2006). Polyhedron, 25, 3095–3103.
- Kargar, H., Kia, R., Khan, I. U., Sahraei, A. & Aberoomand Azar, P. (2010). Acta Cryst. E66, o728. [DOI] [PMC free article] [PubMed]
- Kruger, P. E., Martin, N. & Nieuwenhuyzen, M. (2001). J. Chem. Soc. Dalton Trans. pp. 1966–1970.
- Lippe, K., Gerlach, D., Kroke, E. & Wagler, J. (2009). Organometallics, 28, 621–629.
- Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.
- McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]
- Muñoz-Flores, B. M., Santillán, R., Farfán, N., Álvarez-Venicio, V., Jiménez-Pérez, V. M., Rodríguez, M., Morales-Saavedra, O. G., Lacroix, P. G., Lepetit, C. & Nakatani, K. (2014). J. Organomet. Chem. 769, 64–71.
- Niu, M., Fan, S., Liu, K., Cao, Z. & Wang, D. (2010). Acta Cryst. E66, m77. [DOI] [PMC free article] [PubMed]
- Refat, M. S., El-Korashy, S. A., Kumar, D. N. & Ahmed, A. S. (2008). Spectrochim. Acta Part A, 70, 898–906. [DOI] [PubMed]
- Shahverdizadeh, G. H. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o798. [DOI] [PMC free article] [PubMed]
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
- Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
- Soroceanu, A., Shova, S., Cazacu, M., Balan, I., Gorinchoy, N. & Turta, C. (2013). J. Chem. Crystallogr. 43, 310–318.
- Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. http://hirshfeldsurface.net
- Yoshida, N. & Ichikawa, K. (1997). Chem. Commun. pp. 1091–1092.
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/S2056989018005832/su5438sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018005832/su5438Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989018005832/su5438Isup3.cml
CCDC reference: 1837095
Additional supporting information: crystallographic information; 3D view; checkCIF report