Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one

Kansiz, S.; Aydin, A.S.; Dege, N.; Agar, E.; Fritsky, I.O.

doi:10.1107/S2056989019006583

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ISSN: 2056-9890

Volume 75| Part 6| June 2019| Pages 785-788

https://doi.org/10.1107/S2056989019006583

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Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one

Sevgi Kansiz,^a ^* Alev Sema Aydin,^b Necmi Dege,^b Erbil Agar ^c and Igor O. Fritsky ^d ^*

^aOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey, ^bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, ^cOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, and ^dTaras Shevchenko National University of Kyiv, Department of Chemistry, 64, Vladimirska Str., Kiev 01601, Ukraine
^*Correspondence e-mail: sevgi.kansiz85@gmail.com, ifritsky@univ.kiev.ua

Edited by M. Weil, Vienna University of Technology, Austria (Received 22 April 2019; accepted 8 May 2019; online 14 May 2019)

The title compound, C₁₅H₁₅NO₂, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intramolecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds link adjacent molecules into inversion dimers with an R²₂(18) ring motif. The dimers are linked by very weak π–π interactions, forming layers parallel to ( $[\overline{2}]$ 01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions, indicating that the most important contributions for the crystal packing are from H⋯H (55.2%), C⋯H/H⋯C (22.3%) and O⋯H/H⋯O (13.6%) interactions.

Keywords: crystal structure; Schiff base; hydrogen bonding; Hirshfeld surface analysis.

CCDC reference: 1902148

1. Chemical context

Schiff bases contain the azomethine moiety (–RCH=N–R′) and are prepared by condensation reactions between amines and active carbonyl compounds (Schiff, 1864 ). In the majority of cases, the synthesis involves an aromatic amine and an aldehyde (Schiff et al., 1881 ). Schiff bases are very important for production of chemical specialties such as pharmaceuticals including antibiotics, and of antiallergic, antitumor, antifungal, antibacterial, antimalarial or antiviral drugs. Schiff bases are also employed as catalyst carriers (Grigoras et al., 2001 ), thermo-stable materials (Vančo et al., 2004 ), metal–cation complexing agents or in biological systems (Taggi et al., 2002 ). Schiff bases containing phenol indicate two possible tautomeric forms, viz. phenol–imine and keto–enamine.

In the current study, a new Schiff base, (Z)-6-{[(2-hydroxy-4-methylphenyl)amino]methylidene}-4-methylcyclohexa-2,4-dien-1-one, was obtained in crystalline form from the reaction of 2-amino-5-methylphenol with 2-hydroxy-5-methylbenzaldehyde. We report here its synthesis conditions and the molecular and crystal structures, supplemented by Hirshfeld surface analysis.

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The asymmetric unit comprises one molecule that adopts the keto–enamine tautomeric form, i.e. the H atom is located at the amine functionality (N1). The molecule is almost planar, with an r.m.s. deviation of 0.1061 Å for the complete molecule except the H atoms [largest deviation 0.176 (3) Å for C8]. The two phenyl rings (C1–C6 and C9–C14) are inclined by 9.60 (18)°. The C1—O1 bond length [1.356 (3) Å] to the hydroxy group is in the normal range, while the C14=O2 bond length is comparatively elongated [1.302 (4) Å] due to the involvement of the carbonyl O atom in an intramolecular N—H⋯O hydrogen bond, forming an S(6) ring motif. The C6—N1 and C8=N1 bond lengths are 1.404 (4) and 1.310 (4) Å, respectively. Overall, the bond lengths in the title structure compare well with those of other keto–enamine tautomers known from the literature (see: Database Survey).

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level. Dashed lines denote the intramolecular N—H⋯O hydrogen bond (Table 1

) forming an S(6) ring motif.

3. Supramolecular features

The molecules are linked by mutual O—H⋯O hydrogen bonds forming pairs of inversion dimers with an $[R_{2}^{2}]$ (18) ring motif (Table 1, Figs. 2 and 3). The dimers are linked by very weak π-stacking interactions [Cg1⋯Cg2 = 4.721 (2) Å; Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively], forming layers parallel to ( $[\overline{2}]$ 01).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.82	2.627 (3)	168
N1—H1A⋯O2	0.87 (4)	1.83 (4)	2.585 (4)	144 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 2
A view of the crystal packing of the title compound. Dashed lines denote the intermolecular O—H⋯O hydrogen bonds (Table 1

) forming an inversion dimer with an $[R_{2}^{2}]$ (18) ring motif.

Figure 3
The crystal packing of the title compound.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, update November 2018; Groom et al., 2016 ) for the (E)-2-[(2-hydroxyphenyliminio)methyl]phenolate fragment revealed 25 hits where this fragment adopts the keto–enamine tautomeric form. Nearly all bond lengths in the title structure are the same within standard uncertainties as the corresponding bond lengths in the structures of 2,4-dichloro-6-{[(2-methoxyphenyl)iminio]methyl}phenolate hydrate (VUYFEC; Tsuchimoto et al., 2016 ), 2-{(E)-[(2-hydroxyphenyl)iminio]methyl}-4-methylphenolate (XULSOO; Shalini et al., 2015 ), (E)-4-hydroxy-2-[(2-hydroxyphenyl)iminiomethyl]phenolate (QUYGOH; Eltayeb et al., 2010 ) or 2-{(E)-[(2-hydroxy-5-methylphenyl)iminio]methyl}-4-(trifluoromethoxy)phenolate (QAJYUX; Karadağ et al., 2011 ). For example, in the structures of these typical keto–enamine tautomers, the corresponding C14=O2 and C8—C9 bond lengths are in the ranges 1.279–1.316 Å and 1.410–1.427 Å, respectively. It is likely that the intermolecular O—H⋯O hydrogen bond, where the keto O atom acts as an hydrogen-bond acceptor, is an important prerequisite for the tautomeric shift toward the keto–enamine form. In fact, in all 25 structures of the keto–enamine tautomers, hydrogen bonds of this type are observed.

5. Hirshfeld surface analysis

A 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 ) for specifying the intermolecular interactions in the title compound. Fig. 4a illustrates the Hirshfeld surface mapped over d_norm. The red spots highlight the interatomic contacts included in O—H⋯O hydrogen bonding. The three-dimensional d_norm surfaces were plotted with a colour scale of −0.7370 to 1.3366 Å with a standard (high) surface resolution. Fig. 4b shows the molecular electrostatic potential plotted over the three-dimensional Hirshfeld surface using the STO-3G basis set in the range −0.0975 to 0.2197 a.u. within the Hartree–Fock level of theory. The O—H⋯O hydrogen-bond donors and acceptors are shown as blue and red areas around the atoms related with positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials, respectively.

Figure 4
(a) The Hirshfeld surface mapped over d_norm, and (b) the molecular electrostatic potential surface showing the O—H⋯O interactions.

Fig. 5a shows the two-dimensional fingerprint of the sum of all contacts contributing to the Hirshfeld surface indicated in normal mode. Fig. 5b illustrates the two-dimensional fingerprint of (d_i, d_e) points related to H⋯H contacts that represent a 55.2% contribution in the title structure. In Fig. 5c, two symmetrical wings on the left and right sides indicate C⋯H/H⋯C interactions with a contribution of 22.3%. Furthermore, there are O⋯H/H⋯O (13.6%; Fig. 5d), C⋯C (4.9%) and C⋯N/N⋯C (2.6%) contacts.

Figure 5
Two-dimensional fingerprint plots for the title compound giving the relative contribution of atom pairs to the Hirshfeld surface.

Fig. 6 shows the molecular electrostatic potential surface generated using the STO-3G basis set in the range −0.050 to 0.050 a.u. within the Hartree–Fock level of theory. The blue and red regions are associated with positive and negative molecular electrostatic potentials and represent the donor and acceptor groups, respectively, in hydrogen bonding.

Figure 6
A view of the molecular electrostatic potential, in the range −0.0500 to 0.0500 a.u. calculated using the STO-3 G basis set in the range −0.050 to 0.050 a.u. within the Hartree–Fock level of theory.

6. Synthesis and crystallization

The title compound was prepared by refluxing a mixture of 2-hydroxy-5-methylbenzaldehyde (34.0 mg, 0.25 mmol) in ethanol (15 ml) and 2-amino-5-methylphenol (30.8 mg, 0.25 mmol) in ethanol (15 ml) for 5 h. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 65%, m.p. 446–448 K).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The O- and N-bound H atoms were located in a difference-Fourier map and refined with O—H = 0.82 Å and N—H = 0.85 Å, and with U_iso(H) = 1.5U_eq(N,O). The C-bound H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 and U_iso(H) = 1.2U_eq(C) for aromatic H atoms, and with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₂
M_r	241.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.3954 (19), 11.746 (2), 10.3067 (17)
β (°)	115.940 (12)
V (Å³)	1240.6 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.57 × 0.50 × 0.44

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.962, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	6997, 2417, 1261
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.156, 0.99
No. of reflections	2417
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14
Computer programs: X-AREA and X-RED (Stoe & Cie, 2002), SHELXT2017 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), WinGX (Farrugia, 2012 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1902148

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019006583/wm5504sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019006583/wm5504Isup2.hkl

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(Z)-6-[(2-Hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one top

Crystal data top

C₁₅H₁₅NO₂	F(000) = 512
M_r = 241.28	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3954 (19) Å	Cell parameters from 15101 reflections
b = 11.746 (2) Å	θ = 2.8–30.9°
c = 10.3067 (17) Å	µ = 0.09 mm⁻¹
β = 115.940 (12)°	T = 296 K
V = 1240.6 (4) Å³	Prism, red
Z = 4	0.57 × 0.50 × 0.44 mm

Data collection top

Stoe IPDS 2 diffractometer	2417 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1261 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.061
rotation method scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −14→13
T_min = 0.962, T_max = 0.975	k = −14→11
6997 measured reflections	l = −12→12

Refinement top

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)] = 0.064	w = 1/[σ²(F_o²) + (0.0717P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.156	(Δ/σ)_max < 0.001
S = 0.99	Δρ_max = 0.16 e Å⁻³
2417 reflections	Δρ_min = −0.14 e Å⁻³
171 parameters	Extinction correction: SHELXL2017 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.007 (2)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3892 (2)	0.58075 (18)	0.4721 (3)	0.0775 (7)
H1	0.379271	0.539357	0.530605	0.116*
O2	0.6238 (2)	0.57505 (18)	0.3518 (2)	0.0735 (7)
N1	0.4922 (3)	0.7437 (3)	0.3822 (3)	0.0581 (7)
C9	0.6549 (3)	0.7665 (2)	0.2975 (3)	0.0544 (7)
C1	0.3454 (3)	0.6868 (3)	0.4791 (3)	0.0563 (7)
C8	0.5565 (3)	0.8082 (3)	0.3317 (3)	0.0599 (8)
H8	0.536018	0.885293	0.317983	0.072*
C6	0.3978 (3)	0.7746 (2)	0.4288 (3)	0.0546 (7)
C2	0.2544 (3)	0.7113 (3)	0.5301 (3)	0.0613 (8)
H2A	0.219587	0.652120	0.562261	0.074*
C3	0.2140 (3)	0.8211 (3)	0.5343 (3)	0.0592 (8)
C11	0.8287 (3)	0.8104 (3)	0.2270 (3)	0.0603 (8)
C14	0.6898 (3)	0.6484 (3)	0.3155 (3)	0.0599 (8)
C10	0.7254 (3)	0.8436 (3)	0.2515 (3)	0.0628 (8)
H10	0.700067	0.919577	0.237683	0.075*
C5	0.3571 (3)	0.8851 (3)	0.4324 (3)	0.0642 (8)
H5	0.390952	0.944514	0.399559	0.077*
C4	0.2668 (3)	0.9080 (3)	0.4843 (3)	0.0670 (8)
H4	0.240644	0.982737	0.485967	0.080*
C12	0.8638 (3)	0.6949 (3)	0.2488 (3)	0.0681 (9)
H12	0.934719	0.670249	0.234291	0.082*
C13	0.7972 (3)	0.6170 (3)	0.2906 (3)	0.0688 (9)
H13	0.823971	0.541368	0.302935	0.083*
C7	0.1151 (3)	0.8461 (3)	0.5909 (3)	0.0762 (10)
H7A	0.031563	0.816866	0.524800	0.114*
H7B	0.109049	0.926922	0.600598	0.114*
H7C	0.141812	0.810509	0.683322	0.114*
C15	0.9064 (3)	0.8936 (3)	0.1829 (4)	0.0769 (10)
H15A	0.861304	0.965184	0.157474	0.115*
H15B	0.916047	0.863810	0.101333	0.115*
H15C	0.990962	0.904493	0.261813	0.115*
H1A	0.516 (4)	0.673 (4)	0.387 (4)	0.088 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1026 (18)	0.0475 (13)	0.1056 (17)	0.0073 (13)	0.0671 (15)	0.0093 (11)
O2	0.0894 (16)	0.0526 (13)	0.0949 (14)	−0.0002 (12)	0.0555 (13)	0.0079 (11)
N1	0.0611 (17)	0.0488 (17)	0.0674 (15)	0.0035 (14)	0.0308 (13)	0.0064 (12)
C9	0.0583 (18)	0.0501 (18)	0.0558 (16)	0.0016 (15)	0.0259 (15)	0.0034 (13)
C1	0.0612 (19)	0.0484 (18)	0.0586 (16)	0.0013 (16)	0.0254 (15)	0.0019 (13)
C8	0.0620 (19)	0.0505 (18)	0.0669 (17)	−0.0019 (16)	0.0281 (15)	0.0050 (14)
C6	0.0550 (18)	0.0498 (18)	0.0602 (16)	0.0033 (15)	0.0262 (14)	0.0031 (13)
C2	0.068 (2)	0.056 (2)	0.0655 (17)	−0.0049 (16)	0.0342 (16)	0.0039 (14)
C3	0.0591 (19)	0.063 (2)	0.0557 (16)	0.0044 (17)	0.0251 (14)	0.0027 (14)
C11	0.063 (2)	0.063 (2)	0.0601 (16)	−0.0045 (17)	0.0318 (15)	−0.0012 (14)
C14	0.065 (2)	0.0535 (19)	0.0620 (16)	−0.0024 (16)	0.0288 (15)	−0.0002 (14)
C10	0.067 (2)	0.0563 (19)	0.0648 (17)	−0.0033 (17)	0.0283 (16)	0.0005 (14)
C5	0.0658 (19)	0.0512 (19)	0.0800 (19)	−0.0004 (17)	0.0359 (17)	0.0060 (15)
C4	0.072 (2)	0.0526 (19)	0.084 (2)	0.0078 (17)	0.0406 (18)	0.0011 (16)
C12	0.071 (2)	0.069 (2)	0.0735 (19)	0.0016 (18)	0.0400 (17)	−0.0055 (16)
C13	0.082 (2)	0.0532 (19)	0.081 (2)	0.0030 (18)	0.0450 (19)	−0.0030 (16)
C7	0.073 (2)	0.085 (3)	0.078 (2)	0.0082 (19)	0.0403 (18)	0.0022 (17)
C15	0.078 (2)	0.081 (3)	0.084 (2)	−0.011 (2)	0.0477 (19)	−0.0013 (18)

Geometric parameters (Å, º) top

O1—C1	1.356 (3)	C11—C10	1.365 (4)
O1—H1	0.8200	C11—C12	1.405 (4)
O2—C14	1.302 (4)	C11—C15	1.516 (4)
N1—C8	1.310 (4)	C14—C13	1.404 (4)
N1—C6	1.404 (4)	C10—H10	0.9300
N1—H1A	0.87 (4)	C5—C4	1.377 (4)
C9—C8	1.403 (4)	C5—H5	0.9300
C9—C10	1.422 (4)	C4—H4	0.9300
C9—C14	1.433 (4)	C12—C13	1.373 (4)
C1—C2	1.383 (4)	C12—H12	0.9300
C1—C6	1.400 (4)	C13—H13	0.9300
C8—H8	0.9300	C7—H7A	0.9600
C6—C5	1.385 (4)	C7—H7B	0.9600
C2—C3	1.377 (4)	C7—H7C	0.9600
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.393 (4)	C15—H15B	0.9600
C3—C7	1.506 (4)	C15—H15C	0.9600

C1—O1—H1	109.5	C11—C10—C9	122.6 (3)
C8—N1—C6	129.1 (3)	C11—C10—H10	118.7
C8—N1—H1A	111 (2)	C9—C10—H10	118.7
C6—N1—H1A	120 (2)	C4—C5—C6	120.6 (3)
C8—C9—C10	119.4 (3)	C4—C5—H5	119.7
C8—C9—C14	120.9 (2)	C6—C5—H5	119.7
C10—C9—C14	119.6 (3)	C5—C4—C3	121.2 (3)
O1—C1—C2	124.5 (3)	C5—C4—H4	119.4
O1—C1—C6	115.5 (2)	C3—C4—H4	119.4
C2—C1—C6	120.0 (3)	C13—C12—C11	122.4 (3)
N1—C8—C9	123.0 (3)	C13—C12—H12	118.8
N1—C8—H8	118.5	C11—C12—H12	118.8
C9—C8—H8	118.5	C12—C13—C14	121.9 (3)
C5—C6—C1	118.5 (3)	C12—C13—H13	119.1
C5—C6—N1	124.6 (3)	C14—C13—H13	119.1
C1—C6—N1	116.8 (3)	C3—C7—H7A	109.5
C3—C2—C1	121.6 (3)	C3—C7—H7B	109.5
C3—C2—H2A	119.2	H7A—C7—H7B	109.5
C1—C2—H2A	119.2	C3—C7—H7C	109.5
C2—C3—C4	118.0 (3)	H7A—C7—H7C	109.5
C2—C3—C7	120.8 (3)	H7B—C7—H7C	109.5
C4—C3—C7	121.2 (3)	C11—C15—H15A	109.5
C10—C11—C12	117.0 (3)	C11—C15—H15B	109.5
C10—C11—C15	122.4 (3)	H15A—C15—H15B	109.5
C12—C11—C15	120.5 (3)	C11—C15—H15C	109.5
O2—C14—C13	122.6 (3)	H15A—C15—H15C	109.5
O2—C14—C9	121.0 (3)	H15B—C15—H15C	109.5
C13—C14—C9	116.4 (3)

C6—N1—C8—C9	175.8 (3)	C10—C9—C14—C13	2.3 (4)
C10—C9—C8—N1	−176.2 (3)	C12—C11—C10—C9	0.1 (4)
C14—C9—C8—N1	0.5 (4)	C15—C11—C10—C9	−177.9 (3)
O1—C1—C6—C5	179.8 (3)	C8—C9—C10—C11	174.9 (3)
C2—C1—C6—C5	0.4 (4)	C14—C9—C10—C11	−1.8 (4)
O1—C1—C6—N1	−2.2 (4)	C1—C6—C5—C4	−0.1 (4)
C2—C1—C6—N1	178.4 (3)	N1—C6—C5—C4	−177.9 (3)
C8—N1—C6—C5	−1.7 (5)	C6—C5—C4—C3	0.0 (5)
C8—N1—C6—C1	−179.5 (3)	C2—C3—C4—C5	−0.2 (4)
O1—C1—C2—C3	180.0 (3)	C7—C3—C4—C5	−179.9 (3)
C6—C1—C2—C3	−0.7 (4)	C10—C11—C12—C13	1.0 (5)
C1—C2—C3—C4	0.6 (4)	C15—C11—C12—C13	179.1 (3)
C1—C2—C3—C7	−179.7 (3)	C11—C12—C13—C14	−0.5 (5)
C8—C9—C14—O2	6.1 (4)	O2—C14—C13—C12	178.3 (3)
C10—C9—C14—O2	−177.2 (3)	C9—C14—C13—C12	−1.2 (4)
C8—C9—C14—C13	−174.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.82	2.627 (3)	168
N1—H1A···O2	0.87 (4)	1.83 (4)	2.585 (4)	144 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Funding information

This study was supported by Ondokuz Mayıs University under Project No. PYO·FEN.1906.19.001.

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