Structural study and Hirshfeld surface analysis of (Z)-4-(2-meth­oxy­benzyl­idene)-3-phenyl­isoxazol-5(4H)-one

Benouatas, A.; Laroum, R.; Hamdouni, N.; Zemamouche, W.; Debache, A.; Boudjada, A.

doi:10.1107/S2056989021004308

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 77| Part 5| May 2021| Pages 564-568

https://doi.org/10.1107/S2056989021004308

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Structural study and Hirshfeld surface analysis of (Z)-4-(2-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one

Assia Benouatas,^a Rima Laroum,^b Noudjoud Hamdouni,^a ^* Wissame Zemamouche,^a Abdelmadjid Debache ^b and Ali Boudjada ^a

^aLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, Algeria, and ^bLaboratoire de Synthèse de Molécules, d'Intérêts Biologiques, Département de Chimie, Université Mentouri-Constantine, 25000 Constantine, Algeria
^*Correspondence e-mail: n_hamdouni@yahoo.fr

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 10 March 2021; accepted 21 April 2021; online 27 April 2021)

The title compound, C₁₇H₁₃NO₃, adopts a Z configuration about the C=C bond. The isoxazole and methoxybenzylidene rings are almost coplanar with a dihedral angle of 9.63 (7)° between them. In contrast, the phenyl substituent is twisted significantly out of the plane of the oxazole ring, with the two rings inclined to each other by 46.22 (4)°. The crystal structure features C—H⋯O, C—H⋯N and C—H⋯π hydrogen bonds and π–π contacts. An analysis of the Hirshfeld surfaces points to the importance of H⋯H, H⋯C/C⋯H and H⋯O/O⋯H contacts. The included surface areas of the title compound were compared to those of the isomeric structure (Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one [Zhang et al. (2015 ). CrystEngComm, 17, 7316–7322].

Keywords: crystal structure; methoxybenzylidene; isoxazole; hydrogen bonding; π–π stacking; Hirshfeld surface analysis.

CCDC reference: 2079211

1. Chemical context

Isoxazolones are known to be inhibitors of the factorization of tumor necrosis alpha (TNF-α) (Laughlin et al., 2005 ), antimicrobial agents (Mazimba et al., 2014 ), as drugs for the treatment of cerebrovascular disorders and as muscle relaxants. In agriculture, they are used as herbicides (Guo, et al., 2020 ) and fungicides (Miyake et al., 2012 ). They undergo various chemical transformations (Batra et al., 1994 ) and are excellent intermediates in the synthesis of various heterocycles, including pyridopyrimidines (Tu et al., 2006 ), quinolines (Abbiati et al., 2003 ) and polycycles (Badrey & Gomha, 2014 ). Because of their importance, these compounds have been studied extensively and several procedures for their synthesis are described using a three-component polycondensation between an aromatic aldehyde, ethyl acetoacetate and hydroxylamine hydrochloride under different conditions (Liu et al., 2011 ; Fozooni et al., 2013 ).

We report here on the use of K₂CO₃ as very inexpensive, highly available and safe catalyst in an organic medium for isoxazolone formation and we describe the synthesis, molecular and crystal structures, and Hirshfeld surface analysis of the title isoxazole derivative, 1 (Fig. 1).

Figure 1
The molecular structure of the title compound, with atom labelling and displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is shown as a black dashed line.

2. Structural commentary

The asymmetric unit contains one molecule and the molecule adopts a Z configuration about the C8=C10 bond. The entire (Z)-4-(2-methoxybenzylideneisoxazolone) segment of the molecule is almost planar with an r.m.s. deviation from the mean plane through all 15 non-hydrogen atoms of the fragment of only 0.0927 Å. This conformation is supported by the formation of an intramolecular C12—H12⋯O1 hydrogen bond (Table 1), which links the isoxazole ring and the benzene ring of the 2-methoxybenzylidene substituent. These two rings are inclined to one another at an angle of 9.63 (7)°. The (C1–C6) phenyl substituent is twisted out of this plane, the phenyl and isoxazole rings being inclined to one another by 46.22 (4)°. Bond lengths and angles agree well with those found in the isomeric derivative 2 (Zhang et al., 2015) and also with the values observed for the related compound (4Z)-4-benzylidene-2-phenyl-1,3-oxazol5(4H)-one (Asiri et al., 2012 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.53	3.463 (2)	176
C5—H5⋯O2ⁱⁱ	0.93	2.81	3.728 (2)	169
C10—H10⋯O3	0.93	2.26	2.7009 (18)	108
C12—H12⋯O2	0.93	2.15	2.998 (2)	151
C14—H14⋯N1ⁱⁱⁱ	0.93	2.58	3.396 (2)	147
C17—H17A⋯O3^iv	0.96	2.78	3.615 (2)	147
C17—H17C⋯Cg^iv	0.96	2.82	3.606 (2)	139
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) ; (iii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[-x+1, y, -z+{\script{3\over 2}}]$ .

3. Supramolecular features

In the crystal, molecules stack along the b-axis direction (Fig. 2). Molecules are connected by C4—H4⋯O1ⁱ and C14—H14⋯N1ⁱⁱⁱ hydrogen bonds, leading to the formation of sheets in the ac plane, Fig. 3. C—H⋯π contacts between the methoxymethyl group and the C1–C6 phenyl ring form double chains of molecules along the a-axis direction, supported by the above-mentioned C14—H14⋯N1ⁱⁱⁱ hydrogen bonds, Fig. 4. Intermolecular H⋯O short contacts are also present [C17—H17A⋯O3^iv = 2.78 Å and C5—H5⋯O2ⁱⁱ = 2.81 Å]. Two π–π contacts [3.7049 (9) and 3.9200 (9) Å] are found between the centroids of the isoxazolone ring and the methoxy-substituted benzene ring, which stack adjacent molecules in an obverse fashion along b.

Figure 2
Sheets of molecules of 1 in the ac plane.

Figure 3
Double rows of molecules of 1 along the a-axis direction. Cg2 is the centroid of the C1–C6 phenyl ring, shown here as an orange sphere, with the C—H⋯π contacts drawn as orange dashed lines.

Figure 4
π–π contacts for 1 stacking molecules along the b-axis direction. Cg1 and Cg3 are the centroids of the N1/O2/C7–C9 isoxazole and the C11–C16 benzene rings, respectively. The two discrete π–π contacts Cg1⋯Cg3 = 3.7049 (9) and 3.9200 (9) Å are shown as green and blue dashed lines, respectively.

4. Analysis of the Hirshfeld surfaces

Further details of the intermolecular interactions in 1 were obtained using Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) with Hirshfeld surfaces and two-dimensional fingerprint plots (McKinnon et al., 2007 ) generated using CrystalExplorer (Turner et al. 2017 ). Fig. 5 shows the Hirshfeld surfaces for opposite faces of the asymmetric unit of molecule 1. The bright red circles correspond to C—H⋯N and C—H⋯O hydrogen bonds while a weaker C—H⋯π contact appears as a faint red circle. Fingerprint plots for 1 are shown in Fig. 6. As the CIF file for the isomeric molecule, 2, was available from the CCD, it was of interest to compare and contrast contributions to the included surface areas from the two isomers as shown in Table 2. As expected, H⋯H contacts are the most prolific in both cases. Other contributions were generally very similar, the sole exception being that the C⋯O/O⋯C contacts made up almost twice the surface area for 2 as for 1. The change from the 2- to the 4-position in 2 may allow the methoxy substituent in 2 to contribute more substantially to the surface of the molecule.

Table 2
Short contacts and contributions (%) to the Hirshfeld surface for 1 and 2

Contact	1	2
H⋯H	40.8	40.5
H⋯C/C⋯H	19.4	18.1
H⋯O/O⋯H	19.7	19.6
H⋯N/N⋯H	6.4	5.3
C⋯C	7.9	6.5
C⋯O/O⋯C	3.6	6.9
C⋯N/N⋯C	1.8	2.9
O⋯O	0.6	0.1
N⋯N	0.1

Figure 5
Hirshfeld surfaces for opposite faces of the molecule of 1, mapped over d_norm in the range −0.1701 to 1.4088 a.u.

Figure 6
(a) The two-dimensional fingerprint plot for all interactions, together with those (b)–(h) delineated into individual contact types with included surface areas for the major individual contacts. Minor contacts contributing less than 1% to the total surface area are not shown here but, for completeness, are included in Table 2

5. Database survey

A search of the Cambridge Structural Database (CSD, V3.59, last update February 2019; Groom et al., 2016 ) for (Z)-4-benzylidene-3-phenylsoxazol-5(4H)-one yielded seventeen hits. Importantly, one of these, i.e. (Z)-4-(4-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one (SULZAC; Zhang et al., 2015) is an isomer (2) of the title compound with the methoxy substituent in the 4-position of the benzene ring. Another paper (Jiang et al., 2013 ) included the closely related compound (Z)-4-(4-[dimethylamino)benzylidene]-3-phenylisoxazol-5(4H)-one (IDIBEE) together with two other related compounds, IDIBII and IDIBOO, that exhibit large second harmonic generation effects. The search also revealed four other structures in which the configuration about the C=C bond is Z, namely 4-(2-hydroxybenzylidene)-3-methylisoxazol-5(4H)-one (AJESAK; Cheng et al., 2009 ), (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one (YAXMUH; Asiri et al., 2012), (Z)-4-benzylidene-3-methylisoxazol-5(4H)-one [MBYIOZ (Meunier-Piret et al., 1972 ) and MBYIOZ01 (Chandra et al., 2012 )] and a recent addition, (Z)-4-(4-hydroxybenzylidene)-3-methylisoxazol-5(4H)-one (Zemamouche et al., 2018 ).

6. Synthesis and crystallization

2-Methoxybenzaldehyde (1 mmol), hydroxyamine hydrochloride (1 mmol), ethyl benzoylacetate (1 mmol) and K₂CO₃ (5 mol%) were mixed in a 25 ml flask equipped with a magnetic stirrer. The mixture was refluxed in 5 ml of water for 2.5 h (the reaction was monitored by TLC). On completion of the reaction, the mixture was gradually poured into ice-cold water. Stirring was maintained for a few minutes and the resulting solid was filtered and purified by crystallization from ethanol.

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C-methyl).

Table 3
Experimental details

Crystal data
Chemical formula	C₁₇H₁₃NO₃
M_r	279.28
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	20.3883 (6), 7.5925 (2), 17.9858 (5)
β (°)	95.791 (1)
V (Å³)	2769.96 (13)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.23 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.98, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	35544, 2495, 1548
R_int	0.12
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.101, 1.00
No. of reflections	2495
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2009), SIR92 (Altomare et al., 1994 ), SHELXL2018/3 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2020 ) and WinGX publication routines (Farrugia, 2012).

Supporting information

CCDC reference: 2079211

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989021004308/ex2043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021004308/ex2043Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021004308/ex2043Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: APEX2 (Bruker, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

(Z)-4-(2-Methoxybenzylidene)-3-phenylisoxazol-5(4H)-one top

Crystal data top

C₁₇H₁₃NO₃	F(000) = 1168
M_r = 279.28	D_x = 1.339 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.3883 (6) Å	Cell parameters from 1218 reflections
b = 7.5925 (2) Å	θ = 2.3–33.4°
c = 17.9858 (5) Å	µ = 0.09 mm⁻¹
β = 95.791 (1)°	T = 293 K
V = 2769.96 (13) Å³	Needle, white
Z = 8	0.32 × 0.23 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	1548 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θ_max = 25.3°, θ_min = 2.3°
T_min = 0.98, T_max = 0.99	h = −24→24
35544 measured reflections	k = −9→9
2495 independent reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0548P)²] where P = (F_o² + 2F_c²)/3
2495 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.09 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

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	0.63879 (5)	0.40128 (15)	0.44786 (5)	0.0604 (3)
O2	0.53785 (6)	0.34750 (15)	0.39356 (6)	0.0641 (4)
O3	0.44474 (6)	0.07225 (16)	0.65984 (6)	0.0672 (4)
N1	0.67268 (6)	0.40557 (18)	0.52191 (7)	0.0559 (4)
C11	0.45217 (7)	0.17739 (18)	0.53778 (8)	0.0423 (4)
C10	0.51760 (7)	0.23684 (17)	0.56343 (8)	0.0409 (4)
H10	0.528401	0.219863	0.614403	0.049*
C6	0.65205 (7)	0.35594 (18)	0.64799 (8)	0.0419 (4)
C5	0.61267 (8)	0.43223 (19)	0.69787 (8)	0.0499 (4)
H5	0.571966	0.479668	0.680373	0.060*
C8	0.56690 (7)	0.31231 (18)	0.52928 (7)	0.0376 (4)
C7	0.63081 (7)	0.35667 (18)	0.56711 (8)	0.0400 (4)
C12	0.42284 (8)	0.1993 (2)	0.46438 (9)	0.0566 (5)
H12	0.446785	0.253003	0.429297	0.068*
C1	0.71264 (8)	0.2846 (2)	0.67501 (9)	0.0518 (4)
H1	0.739346	0.232764	0.642170	0.062*
C16	0.41449 (8)	0.0947 (2)	0.58918 (9)	0.0511 (4)
C3	0.69408 (9)	0.3668 (2)	0.79957 (9)	0.0633 (5)
H3	0.708286	0.370488	0.850331	0.076*
C9	0.57442 (8)	0.3509 (2)	0.45076 (8)	0.0474 (4)
C2	0.73315 (9)	0.2905 (2)	0.75030 (10)	0.0632 (5)
H2	0.773723	0.242656	0.768033	0.076*
C4	0.63365 (9)	0.4380 (2)	0.77336 (9)	0.0593 (5)
H4	0.607189	0.489740	0.806480	0.071*
C15	0.35023 (8)	0.0404 (2)	0.56730 (11)	0.0633 (5)
H15	0.325381	−0.013537	0.601461	0.076*
C14	0.32368 (9)	0.0672 (2)	0.49456 (12)	0.0717 (6)
H14	0.280483	0.032695	0.480253	0.086*
C13	0.35978 (9)	0.1436 (2)	0.44307 (11)	0.0710 (6)
H13	0.341624	0.157705	0.393888	0.085*
C17	0.41045 (9)	−0.0215 (3)	0.71332 (9)	0.0764 (6)
H17A	0.437527	−0.026963	0.760129	0.115*
H17B	0.370029	0.038399	0.720143	0.115*
H17C	0.400829	−0.138807	0.695475	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0531 (8)	0.0810 (9)	0.0494 (6)	−0.0098 (6)	0.0165 (5)	0.0092 (5)
O2	0.0606 (8)	0.0864 (9)	0.0452 (6)	−0.0005 (6)	0.0045 (5)	0.0073 (5)
O3	0.0630 (8)	0.0842 (9)	0.0568 (7)	−0.0219 (6)	0.0176 (6)	0.0039 (6)
N1	0.0455 (9)	0.0667 (9)	0.0564 (8)	−0.0096 (7)	0.0101 (7)	0.0045 (7)
C11	0.0345 (9)	0.0357 (8)	0.0577 (9)	−0.0008 (7)	0.0086 (7)	−0.0027 (7)
C10	0.0416 (9)	0.0378 (9)	0.0437 (7)	0.0012 (7)	0.0055 (7)	−0.0010 (6)
C6	0.0362 (9)	0.0402 (9)	0.0494 (8)	−0.0053 (7)	0.0054 (7)	−0.0032 (7)
C5	0.0447 (10)	0.0503 (10)	0.0545 (9)	−0.0012 (8)	0.0036 (8)	−0.0042 (7)
C8	0.0354 (9)	0.0362 (8)	0.0421 (7)	−0.0012 (7)	0.0083 (6)	0.0011 (6)
C7	0.0353 (9)	0.0371 (9)	0.0490 (8)	−0.0024 (7)	0.0103 (7)	0.0008 (6)
C12	0.0477 (11)	0.0553 (11)	0.0653 (10)	−0.0036 (8)	−0.0009 (8)	0.0075 (8)
C1	0.0401 (10)	0.0558 (10)	0.0593 (9)	−0.0014 (8)	0.0042 (8)	−0.0076 (8)
C16	0.0454 (11)	0.0462 (10)	0.0639 (10)	−0.0059 (8)	0.0161 (8)	−0.0066 (8)
C3	0.0719 (14)	0.0657 (12)	0.0499 (9)	−0.0098 (10)	−0.0056 (9)	−0.0071 (8)
C9	0.0471 (11)	0.0485 (10)	0.0478 (8)	−0.0001 (8)	0.0109 (8)	0.0042 (7)
C2	0.0525 (11)	0.0653 (12)	0.0680 (11)	−0.0018 (9)	−0.0123 (10)	−0.0009 (9)
C4	0.0619 (13)	0.0622 (12)	0.0547 (9)	−0.0024 (9)	0.0112 (9)	−0.0136 (8)
C15	0.0442 (12)	0.0619 (12)	0.0865 (13)	−0.0126 (9)	0.0204 (9)	−0.0081 (10)
C14	0.0387 (11)	0.0725 (13)	0.1023 (15)	−0.0101 (9)	−0.0008 (11)	−0.0090 (11)
C13	0.0491 (12)	0.0754 (14)	0.0847 (13)	−0.0095 (10)	−0.0118 (10)	0.0106 (10)
C17	0.0838 (14)	0.0802 (14)	0.0719 (11)	−0.0161 (11)	0.0400 (10)	0.0042 (10)

Geometric parameters (Å, º) top

O1—C9	1.3729 (18)	C12—C13	1.371 (2)
O1—N1	1.4376 (15)	C12—H12	0.9300
O2—C9	1.2085 (17)	C1—C2	1.377 (2)
O3—C16	1.3663 (18)	C1—H1	0.9300
O3—C17	1.4341 (18)	C16—C15	1.392 (2)
N1—C7	1.2914 (18)	C3—C2	1.378 (2)
C11—C12	1.403 (2)	C3—C4	1.384 (2)
C11—C16	1.408 (2)	C3—H3	0.9300
C11—C10	1.4394 (19)	C2—H2	0.9300
C10—C8	1.3566 (19)	C4—H4	0.9300
C10—H10	0.9300	C15—C14	1.379 (2)
C6—C5	1.389 (2)	C15—H15	0.9300
C6—C1	1.391 (2)	C14—C13	1.369 (2)
C6—C7	1.4754 (19)	C14—H14	0.9300
C5—C4	1.3824 (19)	C13—H13	0.9300
C5—H5	0.9300	C17—H17A	0.9600
C8—C7	1.4475 (19)	C17—H17B	0.9600
C8—C9	1.4654 (18)	C17—H17C	0.9600

C9—O1—N1	110.05 (10)	C15—C16—C11	120.45 (16)
C16—O3—C17	118.75 (13)	C2—C3—C4	119.86 (15)
C7—N1—O1	106.87 (12)	C2—C3—H3	120.1
C12—C11—C16	117.50 (15)	C4—C3—H3	120.1
C12—C11—C10	123.89 (14)	O2—C9—O1	118.92 (13)
C16—C11—C10	118.61 (14)	O2—C9—C8	134.47 (15)
C8—C10—C11	133.82 (13)	O1—C9—C8	106.61 (12)
C8—C10—H10	113.1	C1—C2—C3	120.56 (16)
C11—C10—H10	113.1	C1—C2—H2	119.7
C5—C6—C1	119.18 (14)	C3—C2—H2	119.7
C5—C6—C7	120.26 (14)	C5—C4—C3	119.91 (16)
C1—C6—C7	120.52 (14)	C5—C4—H4	120.0
C4—C5—C6	120.39 (15)	C3—C4—H4	120.0
C4—C5—H5	119.8	C14—C15—C16	119.51 (17)
C6—C5—H5	119.8	C14—C15—H15	120.2
C10—C8—C7	123.95 (12)	C16—C15—H15	120.2
C10—C8—C9	132.47 (13)	C13—C14—C15	121.19 (17)
C7—C8—C9	103.27 (12)	C13—C14—H14	119.4
N1—C7—C8	113.07 (13)	C15—C14—H14	119.4
N1—C7—C6	118.35 (13)	C14—C13—C12	119.65 (17)
C8—C7—C6	128.56 (13)	C14—C13—H13	120.2
C13—C12—C11	121.68 (17)	C12—C13—H13	120.2
C13—C12—H12	119.2	O3—C17—H17A	109.5
C11—C12—H12	119.2	O3—C17—H17B	109.5
C2—C1—C6	120.10 (16)	H17A—C17—H17B	109.5
C2—C1—H1	119.9	O3—C17—H17C	109.5
C6—C1—H1	119.9	H17A—C17—H17C	109.5
O3—C16—C15	123.35 (16)	H17B—C17—H17C	109.5
O3—C16—C11	116.20 (14)

C9—O1—N1—C7	1.14 (16)	C17—O3—C16—C15	4.0 (2)
C12—C11—C10—C8	−4.4 (3)	C17—O3—C16—C11	−175.92 (14)
C16—C11—C10—C8	176.65 (15)	C12—C11—C16—O3	178.84 (14)
C1—C6—C5—C4	0.4 (2)	C10—C11—C16—O3	−2.2 (2)
C7—C6—C5—C4	−177.39 (13)	C12—C11—C16—C15	−1.1 (2)
C11—C10—C8—C7	−177.90 (14)	C10—C11—C16—C15	177.91 (14)
C11—C10—C8—C9	−5.5 (3)	N1—O1—C9—O2	176.89 (13)
O1—N1—C7—C8	1.18 (17)	N1—O1—C9—C8	−2.88 (15)
O1—N1—C7—C6	−177.58 (11)	C10—C8—C9—O2	10.1 (3)
C10—C8—C7—N1	171.42 (14)	C7—C8—C9—O2	−176.37 (17)
C9—C8—C7—N1	−2.85 (17)	C10—C8—C9—O1	−170.22 (15)
C10—C8—C7—C6	−10.0 (2)	C7—C8—C9—O1	3.35 (15)
C9—C8—C7—C6	175.75 (14)	C6—C1—C2—C3	0.0 (2)
C5—C6—C7—N1	132.05 (16)	C4—C3—C2—C1	0.1 (2)
C1—C6—C7—N1	−45.7 (2)	C6—C5—C4—C3	−0.3 (2)
C5—C6—C7—C8	−46.5 (2)	C2—C3—C4—C5	0.1 (2)
C1—C6—C7—C8	135.77 (16)	O3—C16—C15—C14	−179.53 (15)
C16—C11—C12—C13	0.3 (2)	C11—C16—C15—C14	0.4 (2)
C10—C11—C12—C13	−178.59 (15)	C16—C15—C14—C13	1.1 (3)
C5—C6—C1—C2	−0.2 (2)	C15—C14—C13—C12	−1.9 (3)
C7—C6—C1—C2	177.52 (14)	C11—C12—C13—C14	1.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.53	3.463 (2)	176
C5—H5···O2ⁱⁱ	0.93	2.81	3.728 (2)	169
C10—H10···O3	0.93	2.26	2.7009 (18)	108
C12—H12···O2	0.93	2.15	2.998 (2)	151
C14—H14···N1ⁱⁱⁱ	0.93	2.58	3.396 (2)	147
C17—H17A···O3^iv	0.96	2.78	3.615 (2)	147
C17—H17C···Cg^iv	0.96	2.82	3.606 (2)	139

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, y−1/2, z; (iv) −x+1, y, −z+3/2.

Short contacts and contributions (%) to the Hirshfeld surface for 1 and 2 top

Contact	1	2
H···H	40.8	40.5
H···C/C···H	19.4	18.1
H···O/O···H	19.7	19.6
H···N/N···H	6.4	5.3
C···C	7.9	6.5
C···O/O···C	3.6	6.9
C···N/N···C	1.8	2.9
O···O	0.6	0.1
N···N	0.1

Acknowledgements

The authors gratefully acknowledge Université Ferhat Abbas Setif 1 for assistance with the data collection.

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