research communications
Zwitterionic 1-{(1E)-[(4-hydroxyphenyl)iminio]methyl}naphthalen-2-olate: and Hirshfeld surface analysis
aResearch & Development Centre, Bharathiar University, Coimbatore 641 046, India, bGovt. Science College, Nrupathunga Road, Bangalore 560 001, India, cSSMRV College, Jayanagar 4th T block, Bangalore 560 041, India, dDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380 001, India, and eResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my
The title zwitterion, C17H13NO2 (systematic name: 1-{(1E)-[(4-hydroxyphenyl)iminiumyl]methyl}naphthalen-2-olate), features an intramolecular charge-assisted N+—H⋯O− hydrogen bond. A twist in the molecule is evident around the N—C(hydroxybenzene) bond [C—N—C—C torsion angle = 39.42 (8)°] and is reflected in the dihedral angle of 39.42 (8)° formed between the aromatic regions of the molecule. In the crystal, zigzag supramolecular chains along the a axis are formed by charge-assisted hydroxy-O—H⋯O(phenoxide) hydrogen bonding. These are connected into a layer in the ab plane by charge-assisted hydroxybenzene-C—H⋯O(phenoxide) interactions and π–π contacts [inter-centroid distance between naphthyl-C6 rings = 3.4905 (12) Å]. Layers stack along the c axis with no specific interactions between them. The Hirshfeld surface analysis points to the significance C⋯H contacts between layers.
CCDC reference: 1429885
1. Chemical context
o-hydroxynaphthalehyde have attracted significant attention owing to their biological properties, such as anti-tumour activity (Richardson & Bernhardt, 1999; Gou et al., 2015), and their photophysical properties, such as thermo- and (Matijević-Sosa et al., 2006). Furthermore, the physical properties of these molecules led to their application in various areas of materials science, such as in the control and measurement of radiation intensity, display systems and optical memory devices (Dürr, 1989; Hadjoudis & Mavridis, 2004). These have also been used as tools for assessing the nature of hydrogen bonding (Richardson & Bernhardt, 1999), as well as keto–amine and phenol–imine (Ünver et al., 2000) in related molecules. In view of these various applications, our recent investigations have focused on the of of this type, e.g. of (E)-N-[(2-methoxynaphthalen-1-yl)methylidene]-3-nitroaniline (Bhai et al., 2015). As a continuation of these studies, the crystal and molecular structures of the title compound, (I), are described herein along with an analysis of the Hirshfeld surface, performed in order to gain more information on the nature of the molecular packing.
derived from2. Structural commentary
The molecular structure of (I) is shown in Fig. 1. Crystallography established the molecule to exist in a zwitterionic form with the putative H atom of the naphthyl-hydroxy group being located on the imine-N atom. This assignment is supported by the short C9—O2 bond length of 1.283 (2) Å. The molecule features two planar regions connected by an imine (iminiumyl) bridge; the configuration about the imine bond [C1=N = 1.308 (2) Å] is E. The twist in the molecule occurs around the N1—C2 bond, is seen in the value of the C1—N1—C2—C7 torsion angle of 31.1 (3)°. The dihedral angle between the two aromatic regions is 39.42 (8)°. The coplanar relationship between the imine and naphthyl residues is stabilized by an intramolecular charge-assisted N+—H⋯O− hydrogen bond, Table 1.
3. Supramolecular features
The most prominent feature of the molecular packing is the formation of a zigzag (glide symmetry) supramolecular chain along the a axis mediated by hydroxy-O—H⋯O(phenoxide) charge-assisted hydrogen bonding, Fig. 2a and Table 1. Chains are connected into a supramolecular layer in the ab plane by charge-assisted hydroxybenzene-C—H⋯O(phenoxide) interactions, Table 1, as well as π–π contacts between the two rings of the naphthyl residue; the inter-centroid separation for (C8–C12,C17)⋯(C12–C17)i = 3.4905 (12) Å and angle of inclination = 2.68 (8)° [symmetry code (i) − x, + y, z], Fig. 2b. Layers stack along the c axis with no directional interactions between them, Fig. 2c.
4. Analysis of the Hirshfeld surface
The Hirshfeld surface was calculated for (I) according to earlier work on organic molecules (Tan et al., 2017) and provides more detailed information on the intermolecular interactions influential in the crystal. In addition to the bright-red spots near those atoms participating in charge-assisted O1—H1O⋯O2 and C7—H7⋯O1 interactions on the Hirshfeld surface mapped over dnorm, Fig. 3, the bright-red spots appearing near the benzene-C4, -C5 and -H7, and naphthyl-H13 atoms are indicative of short interatomic C⋯H/H⋯C contacts significant in the crystal, Table 2. The C4⋯H13 contact occurs in the inter-layer region. Further, the short interatomic C⋯C contacts between the naphthyl-C9 and -C17 atoms, Table 2, assigned to π–π stacking interactions, appear as faint-red spots in Fig. 3. The donors and acceptors of the aforementioned interactions appear as blue and red regions, respectively, around the atoms on the Hirshfeld surface mapped over electrostatic potential in the views shown in Fig. 4. The short interatomic contacts together with the charge-assisted O—H⋯O and C—H⋯O interactions formed with the atoms of a reference molecule within shape-index mapped Hirshfeld surface are highlighted in the views of Fig. 5.
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The overall two-dimensional fingerprint plot, Fig. 6a, and those delineated into H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and C⋯C contacts (McKinnon et al., 2007) are illustrated in Figs. 6b–e, respectively; the relative contributions from different interatomic contacts to the Hirshfeld surfaces are summarized in Table 3. The presence of a small peak in the centre at de + di ∼ 2.3 Å in the fingerprint plot delineated into H⋯H contacts, Fig. 6b, results from the short interatomic H⋯H contact between symmetry related naphthyl-H15 and -H16 atoms, Table 2. In the fingerprint plot delineated into C⋯H/H⋯C contacts, Fig. 6c, the short interatomic contacts summarized in Table 2 appear as the points distributed as the pair of thick spikes with tips at de + di ∼ 2.6 Å. The presence of charge-assisted O—H⋯O hydrogen bonds in the structure are characterized by the distinctive spikes with tips at de + di ∼ 1.7 Å, Fig. 6d, whereas the points belong to intermolecular C—H⋯O hydrogen bond are merged within the plot. The fingerprint plot delineated into C⋯C contacts, Fig. 6e, indicate the presence of the π–π stacking interactions between symmetry related naphthyl-(C8–C12/C17) and -(C12–C17) rings through the arrow-shaped distribution with the green points spread about de = di = 1.8 Å. The small contributions from other interatomic contacts summarized in Table 3 have negligible effect on the molecular packing.
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5. Database survey
The most closely related structure to (I) in the crystallographic literature (Groom et al., 2016) is that of the ethanol hemisolvate of (I), i.e. (I)·0.5EtOH (Safia et al., 2015). Here, there are two molecules in the and each exists in the zwitterionic form with C—O− = 1.288 (4) and 1.2943 (19) Å. By contrast to (I), the in (I)·0.5EtOH are more planar than in (I), with the dihedral angles between the aromatic residues being 7.59 (4)° in one of the independent and 8.01 (4)° in the other. The other structure deserving of comment is that of 2-{[(4-hydroxyphenyl)imino]methyl}phenol, where the 2-oxidonaphthyl group of (I) has been replaced by a 2-oxidobenzene residue. This has been crystallized in two forms, viz. a P21/c form with Z′ = 2 (Ersanlı et al., 2004) and a C2/c form with Z′ = 1 (Wang et al., 2011). The common feature of the three molecules is the formation of hydroxyl/imine tautomer, as opposed to zwitterionic (I) and (I)·0.5EtOH (Safia et al., 2015). The three molecules have smaller deviations from planarity than (I), as seen in the dihedral angles between the aromatic rings of 10.43 (6) and 15.70 (6)° for the P21/c form, and 14.91 (9)° for the C2/c form. Finally, a deprotonated form of (I), with the 4-hydroxy group intact, forms a six-membered {Pd—O—C C—C=N} chelate ring in its bis-complex with palladium(II) (Tardiff et al., 2007).
6. Synthesis and crystallization
4-Hydroxyaniline (0.00916 mol, 1.00 g) was added to a solution of 2-hydroxy-1-napthaldehyde (0.00916 mol, 1.58 g) in ethanol (25 ml). The resulting mixture was refluxed at 333 K and stirred for 2.5 h. The reaction mixture was cooled to room temperature and the resulting orange precipitate was filtered off and washed with cold ethanol to obtain the pure product in 65% yield. Crystals of (I) were grown from a mixture of chloroform and methanol (1:1 v/v) by slow evaporation.
7. Refinement
Crystal data, data collection and structure . The carbon-bound H atoms were placed in calculated positions (C—H = 0.95 Å) and were included in the in the riding-model approximation, with Uiso(H) values set at 1.2Ueq(C). The O- and N-bound H atoms were located in a difference Fourier map, but were refined with distance restraints of O—H = 0.82±0.01 Å and N—H = 0.86±0.01 Å, and with Uiso(H) values set at 1.5Ueq(O) and 1.2Ueq(N), respectively. To confirm the positions of the acidic-H atoms, a separate was conducted whereby no distance restraints were applied resulting in O—H and N—H bond lengths of 0.93 (2) and 1.00 (3) Å, respectively.
details are summarized in Table 4Supporting information
CCDC reference: 1429885
https://doi.org/10.1107/S205698901701458X/ex2001sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901701458X/ex2001Isup2.hkl
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C17H13NO2 | Dx = 1.338 Mg m−3 |
Mr = 263.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 3652 reflections |
a = 15.7473 (14) Å | θ = 2.5–22.5° |
b = 7.3042 (5) Å | µ = 0.09 mm−1 |
c = 22.7257 (19) Å | T = 293 K |
V = 2613.9 (4) Å3 | Block, colourless |
Z = 8 | 0.35 × 0.25 × 0.10 mm |
F(000) = 1104 |
Bruker AXS Kappa APEXII CCD diffractometer | 1518 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.043 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 24.8°, θmin = 2.2° |
Tmin = 0.941, Tmax = 0.982 | h = −17→18 |
17744 measured reflections | k = −8→5 |
2253 independent reflections | l = −26→26 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3444P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.115 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.15 e Å−3 |
2253 reflections | Δρmin = −0.16 e Å−3 |
189 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0094 (11) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.50441 (9) | 0.2166 (2) | 0.36926 (6) | 0.0610 (4) | |
O2 | 0.85495 (9) | 0.0585 (2) | 0.13238 (6) | 0.0619 (4) | |
N1 | 0.70553 (11) | 0.0841 (2) | 0.17521 (7) | 0.0508 (4) | |
C1 | 0.68015 (13) | 0.0167 (2) | 0.12484 (8) | 0.0478 (5) | |
H1 | 0.6223 | −0.0034 | 0.1199 | 0.057* | |
C2 | 0.65339 (12) | 0.1142 (3) | 0.22458 (8) | 0.0466 (5) | |
C3 | 0.67240 (12) | 0.2537 (3) | 0.26274 (8) | 0.0510 (5) | |
H3 | 0.7199 | 0.3265 | 0.2562 | 0.061* | |
C4 | 0.62150 (13) | 0.2861 (3) | 0.31052 (8) | 0.0522 (5) | |
H4 | 0.6342 | 0.3821 | 0.3359 | 0.063* | |
C5 | 0.55214 (12) | 0.1784 (3) | 0.32124 (7) | 0.0471 (5) | |
C6 | 0.53407 (13) | 0.0373 (3) | 0.28381 (8) | 0.0606 (6) | |
H62 | 0.4873 | −0.0373 | 0.2908 | 0.073* | |
C7 | 0.58493 (14) | 0.0058 (3) | 0.23593 (9) | 0.0617 (6) | |
H7 | 0.5725 | −0.0910 | 0.2108 | 0.074* | |
C8 | 0.73349 (12) | −0.0267 (2) | 0.07838 (7) | 0.0436 (5) | |
C9 | 0.82215 (13) | −0.0075 (2) | 0.08526 (9) | 0.0492 (5) | |
C10 | 0.87583 (14) | −0.0632 (3) | 0.03806 (10) | 0.0588 (6) | |
H10 | 0.9345 | −0.0557 | 0.0423 | 0.071* | |
C11 | 0.84314 (15) | −0.1261 (3) | −0.01218 (10) | 0.0643 (6) | |
H11 | 0.8801 | −0.1621 | −0.0419 | 0.077* | |
C12 | 0.75490 (14) | −0.1402 (3) | −0.02208 (8) | 0.0533 (5) | |
C13 | 0.72247 (18) | −0.1984 (3) | −0.07628 (10) | 0.0704 (7) | |
H13 | 0.7599 | −0.2305 | −0.1062 | 0.084* | |
C14 | 0.63811 (19) | −0.2091 (3) | −0.08611 (10) | 0.0742 (7) | |
H14 | 0.6176 | −0.2476 | −0.1224 | 0.089* | |
C15 | 0.58281 (16) | −0.1625 (3) | −0.04171 (10) | 0.0679 (6) | |
H15 | 0.5246 | −0.1697 | −0.0482 | 0.082* | |
C16 | 0.61235 (14) | −0.1058 (3) | 0.01170 (9) | 0.0571 (5) | |
H16 | 0.5737 | −0.0761 | 0.0411 | 0.069* | |
C17 | 0.69907 (13) | −0.0913 (2) | 0.02326 (8) | 0.0460 (5) | |
H1O | 0.4563 (9) | 0.154 (2) | 0.3685 (9) | 0.069* | |
H1N | 0.7609 (7) | 0.095 (3) | 0.1766 (9) | 0.082 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0498 (9) | 0.0847 (11) | 0.0486 (8) | −0.0037 (7) | 0.0043 (7) | −0.0102 (7) |
O2 | 0.0443 (9) | 0.0836 (10) | 0.0577 (9) | 0.0018 (7) | 0.0002 (7) | 0.0086 (7) |
N1 | 0.0434 (11) | 0.0608 (11) | 0.0482 (10) | −0.0001 (8) | 0.0060 (8) | 0.0034 (7) |
C1 | 0.0427 (12) | 0.0513 (11) | 0.0493 (12) | 0.0016 (9) | 0.0034 (9) | 0.0052 (9) |
C2 | 0.0397 (11) | 0.0558 (11) | 0.0444 (11) | −0.0003 (9) | 0.0040 (9) | 0.0028 (9) |
C3 | 0.0431 (12) | 0.0576 (12) | 0.0524 (12) | −0.0095 (9) | −0.0018 (9) | 0.0015 (9) |
C4 | 0.0519 (13) | 0.0567 (12) | 0.0480 (11) | −0.0030 (10) | −0.0056 (9) | −0.0067 (9) |
C5 | 0.0394 (12) | 0.0626 (12) | 0.0392 (10) | 0.0029 (9) | −0.0030 (9) | −0.0021 (8) |
C6 | 0.0510 (13) | 0.0763 (14) | 0.0546 (12) | −0.0212 (11) | 0.0115 (10) | −0.0124 (11) |
C7 | 0.0611 (15) | 0.0691 (14) | 0.0550 (13) | −0.0174 (11) | 0.0104 (10) | −0.0177 (10) |
C8 | 0.0409 (12) | 0.0443 (10) | 0.0455 (10) | 0.0046 (8) | 0.0055 (9) | 0.0082 (8) |
C9 | 0.0467 (12) | 0.0484 (11) | 0.0527 (12) | 0.0055 (9) | 0.0060 (10) | 0.0132 (9) |
C10 | 0.0441 (13) | 0.0581 (13) | 0.0743 (15) | 0.0068 (10) | 0.0167 (11) | 0.0091 (11) |
C11 | 0.0722 (17) | 0.0536 (13) | 0.0671 (15) | 0.0053 (11) | 0.0281 (13) | 0.0009 (11) |
C12 | 0.0642 (15) | 0.0428 (11) | 0.0530 (12) | 0.0023 (10) | 0.0136 (11) | 0.0065 (9) |
C13 | 0.098 (2) | 0.0580 (13) | 0.0553 (14) | 0.0023 (12) | 0.0181 (13) | −0.0011 (10) |
C14 | 0.104 (2) | 0.0611 (14) | 0.0575 (14) | −0.0012 (13) | −0.0080 (15) | −0.0014 (11) |
C15 | 0.0748 (17) | 0.0584 (14) | 0.0706 (15) | 0.0020 (11) | −0.0147 (13) | 0.0028 (11) |
C16 | 0.0608 (15) | 0.0538 (12) | 0.0568 (13) | 0.0057 (10) | −0.0004 (11) | 0.0038 (10) |
C17 | 0.0520 (13) | 0.0366 (10) | 0.0495 (11) | 0.0049 (8) | 0.0053 (9) | 0.0085 (8) |
O1—C5 | 1.354 (2) | C8—C9 | 1.412 (3) |
O1—H1O | 0.886 (10) | C8—C17 | 1.444 (3) |
O2—C9 | 1.283 (2) | C9—C10 | 1.425 (3) |
N1—C1 | 1.308 (2) | C10—C11 | 1.334 (3) |
N1—C2 | 1.408 (2) | C10—H10 | 0.9300 |
N1—H1N | 0.877 (10) | C11—C12 | 1.411 (3) |
C1—C8 | 1.386 (2) | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | C12—C13 | 1.400 (3) |
C2—C7 | 1.362 (3) | C12—C17 | 1.401 (3) |
C2—C3 | 1.371 (2) | C13—C14 | 1.349 (3) |
C3—C4 | 1.370 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.376 (3) |
C4—C5 | 1.368 (3) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.364 (3) |
C5—C6 | 1.366 (2) | C15—H15 | 0.9300 |
C6—C7 | 1.371 (3) | C16—C17 | 1.395 (3) |
C6—H62 | 0.9300 | C16—H16 | 0.9300 |
C7—H7 | 0.9300 | ||
C5—O1—H1O | 110.6 (13) | O2—C9—C8 | 121.87 (17) |
C1—N1—C2 | 125.31 (18) | O2—C9—C10 | 119.78 (19) |
C1—N1—H1N | 111.7 (15) | C8—C9—C10 | 118.35 (19) |
C2—N1—H1N | 122.5 (15) | C11—C10—C9 | 120.9 (2) |
N1—C1—C8 | 124.56 (19) | C11—C10—H10 | 119.5 |
N1—C1—H1 | 117.7 | C9—C10—H10 | 119.5 |
C8—C1—H1 | 117.7 | C10—C11—C12 | 122.8 (2) |
C7—C2—C3 | 119.01 (17) | C10—C11—H11 | 118.6 |
C7—C2—N1 | 121.44 (17) | C12—C11—H11 | 118.6 |
C3—C2—N1 | 119.55 (17) | C13—C12—C17 | 119.7 (2) |
C4—C3—C2 | 120.11 (18) | C13—C12—C11 | 121.5 (2) |
C4—C3—H3 | 119.9 | C17—C12—C11 | 118.81 (19) |
C2—C3—H3 | 119.9 | C14—C13—C12 | 121.5 (2) |
C5—C4—C3 | 120.62 (18) | C14—C13—H13 | 119.3 |
C5—C4—H4 | 119.7 | C12—C13—H13 | 119.3 |
C3—C4—H4 | 119.7 | C13—C14—C15 | 119.2 (2) |
O1—C5—C6 | 122.77 (18) | C13—C14—H14 | 120.4 |
O1—C5—C4 | 117.95 (17) | C15—C14—H14 | 120.4 |
C6—C5—C4 | 119.28 (17) | C16—C15—C14 | 120.8 (2) |
C5—C6—C7 | 119.95 (19) | C16—C15—H15 | 119.6 |
C5—C6—H62 | 120.0 | C14—C15—H15 | 119.6 |
C7—C6—H62 | 120.0 | C15—C16—C17 | 121.6 (2) |
C2—C7—C6 | 121.01 (18) | C15—C16—H16 | 119.2 |
C2—C7—H7 | 119.5 | C17—C16—H16 | 119.2 |
C6—C7—H7 | 119.5 | C16—C17—C12 | 117.17 (19) |
C1—C8—C9 | 119.49 (18) | C16—C17—C8 | 123.76 (17) |
C1—C8—C17 | 120.53 (18) | C12—C17—C8 | 119.06 (19) |
C9—C8—C17 | 119.98 (17) | ||
C2—N1—C1—C8 | −174.22 (17) | C8—C9—C10—C11 | 2.3 (3) |
C1—N1—C2—C7 | 31.1 (3) | C9—C10—C11—C12 | 0.5 (3) |
C1—N1—C2—C3 | −149.93 (18) | C10—C11—C12—C13 | 176.90 (19) |
C7—C2—C3—C4 | −1.9 (3) | C10—C11—C12—C17 | −1.9 (3) |
N1—C2—C3—C4 | 179.13 (17) | C17—C12—C13—C14 | −0.1 (3) |
C2—C3—C4—C5 | 1.0 (3) | C11—C12—C13—C14 | −178.9 (2) |
C3—C4—C5—O1 | 179.76 (17) | C12—C13—C14—C15 | −0.3 (3) |
C3—C4—C5—C6 | 0.2 (3) | C13—C14—C15—C16 | 0.1 (3) |
O1—C5—C6—C7 | −179.99 (19) | C14—C15—C16—C17 | 0.6 (3) |
C4—C5—C6—C7 | −0.5 (3) | C15—C16—C17—C12 | −0.9 (3) |
C3—C2—C7—C6 | 1.7 (3) | C15—C16—C17—C8 | 178.00 (18) |
N1—C2—C7—C6 | −179.39 (19) | C13—C12—C17—C16 | 0.7 (3) |
C5—C6—C7—C2 | −0.5 (3) | C11—C12—C17—C16 | 179.54 (17) |
N1—C1—C8—C9 | 3.4 (3) | C13—C12—C17—C8 | −178.30 (16) |
N1—C1—C8—C17 | −176.69 (16) | C11—C12—C17—C8 | 0.6 (3) |
C1—C8—C9—O2 | −3.8 (3) | C1—C8—C17—C16 | 3.3 (3) |
C17—C8—C9—O2 | 176.27 (16) | C9—C8—C17—C16 | −176.73 (17) |
C1—C8—C9—C10 | 176.36 (16) | C1—C8—C17—C12 | −177.76 (16) |
C17—C8—C9—C10 | −3.6 (2) | C9—C8—C17—C12 | 2.2 (2) |
O2—C9—C10—C11 | −177.56 (18) |
Hydrogen-bond geometry (Å, °) for (I). |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.88 (1) | 1.81 (2) | 2.553 (2) | 141 (2) |
O1—H1O···O2i | 0.89 (1) | 1.74 (1) | 2.622 (2) | 173 (1) |
C7—H7···O1ii | 0.93 | 2.60 | 3.487 (3) | 160 |
Symmetry codes: (i) −x−3/2, y−1/2, z; (ii) −x+3/2, −y−1, z+1/2. |
Contact | Distance | Symmetry operation |
C4···H13 | 2.69 | 1 1/2 - x, - y, 1/2 + z |
C5···H7 | 2.69 | 1 - x, 1/2 + y, 1/2 - z |
C9···H1O | 2.638 (16) | 1/2 + x, y, 1/2 - z |
C9···C17 | 3.367 (2) | 1 1/2 - x, - 1/2 + y, z |
H15···H16 | 2.38 | 1 - x, - y, - z |
Contact | Percentage contribution |
H···H | 46.5 |
C···H/H···C | 24.9 |
O···H/H···O | 14.9 |
C···C | 10.5 |
C···O/O···C | 1.0 |
N···H/H···N | 1.0 |
N···O /O···N | 0.6 |
C···N/N···C | 0.6 |
Footnotes
‡Additional correspondence author: girija.shivakumar@rediffmail.com.
Acknowledgements
CRG is thankful to the Government Science College, Bangalore, and SSMRV Degree College, Bangalore, for providing necessary facilities to carry out the present work. The authors also acknowledge SAIF, IIT, Chennai, for providing the
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