Crystal structure and Hirshfeld surface analysis of (E)-6-(4-hy­droxy-3-meth­oxy­styr­yl)-4,5-di­hydro­pyridazin-3(2H)-one

Daoui, S.; Baydere, C.; El Kalai, F.; Saddik, R.; Dege, N.; Karrouchi, K.; Benchat, N.

doi:10.1107/S2056989019014130

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 75| Part 11| November 2019| Pages 1734-1737

https://doi.org/10.1107/S2056989019014130

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Crystal structure and Hirshfeld surface analysis of (E)-6-(4-hydroxy-3-methoxystyryl)-4,5-dihydropyridazin-3(2H)-one

Said Daoui,^a ^* Cemile Baydere,^b Fouad El Kalai,^a Rafik Saddik,^c Necmi Dege,^b Khalid Karrouchi ^d and Noureddine Benchat ^a

^aLaboratory of Applied Chemistry and Environment (LCAE), Faculty of Sciences, Mohamed I University, 60000 Oujda, Morocco, ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, ^cLaboratory for Organic Synthesis, Extraction and Valorization, Faculty of Sciences, Ain Chok, University Hassan II, Casablanca, Rabat, Morocco, and ^dLaboratory of Plant Chemistry, Organic and Bioorganic Synthesis, URAC23, Faculty of Science, BP 1014, GEOPAC Research Center, Mohammed V University, Rabat, Morocco
^*Correspondence e-mail: saiddaoui26@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 2 September 2019; accepted 16 October 2019; online 31 October 2019)

In the title compound, C₁₃H₁₄N₂O₃, the dihydropyridazine ring (r.m.s. deviation = 0.166 Å) has a screw-boat conformation. The dihedral angle between its mean plane and the benzene ring is 0.77 (12)°. In the crystal, intermolecular O—H⋯O hydrogen bonds generate C(5) chains and N—H⋯O hydrogen bonds produce R₂²(8) motifs. These types of interactions lead to the formation of layers parallel to (12 $[\overline{1}]$ ). The three-dimensional network is achieved by C—H⋯O interactions, including R₂⁴(8) motifs. Intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are by H⋯H (43.3%), H⋯C/C⋯H (19.3%), H⋯O/H⋯O (22.6%), C⋯N/N⋯C (3.0%) and H⋯N/N⋯H (5.8%) contacts. C—H⋯π interactions and aromatic π–π stacking interactions are not observed.

Keywords: crystal structure; hydrogen bonding; Hirshfeld surface analysis; pyridazine.

CCDC references: 1959568; 1959568

1. Chemical context

For decades the chemistry of pyridazinones has been an interesting field. This nitrogen heterocycle became a scaffold of choice for the development of potential drug candidates (Akhtar et al., 2016 ; Dubey & Bhosle, 2015 ) because pyridazinone and its substituted derivatives are important pharmacophores possessing many different biological applications (Asif, 2014 ). Such compounds are used as anti-HIV (Livermore et al., 1993 ), antimicrobial (Sönmez et al., 2006 ), anticonvulsant (Partap et al., 2018 ), antihypertensive (Siddiqui et al., 2011 ), antidepressant (Boukharsa et al., 2016 ), analgesic (Gökçe et al., 2009 ), anti-inflammatory (Barberot et al., 2018 ), antihistaminic (Tao et al. 2012 ), cardiotonic (Wang et al., 2008 ) and herbicidal agents (Asif, 2013 ) or as glucan synthase inhibitors (Zhou et al., 2011 ).

In continuation of our studies related to molecular structures and Hirshfeld surface analysis of new heterocyclic derivatives (Daoui et al., 2019a ,b ; El Kalai et al., 2019 ; Karrouchi et al., 2015 ), we report herein on the synthesis, molecular and crystal structures of (E)-6-(4-hydroxy-3-methoxystyryl)-4,5-dihydropyridazin-3(2H)-one, as well as an analysis of the Hirshfeld surfaces.

2. Structural commentary

In the title molecule (Fig. 1), the configuration relative to the double bond at C5 and C6 is E. The dihydropyridazine ring has a screw-boat conformation, with an r.m.s. deviation of 0.166 Å for the ring atoms, with the maximum deviation from the ring being 0.178 (3) Å for the C3 atom; the C2 atom lies −0.177 (3) Å out of the plane in the opposite direction relative to the C3 atom. The dihedral angle between the dihydropyridazine ring mean plane and the benzene ring (C7–C12) is 0.77 (12)°, indicating an almost planar conformation of the molecule favouring delocalization over the C4—C5=C6—C7 bridge.

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, molecules are stacked in rows parallel to [100]. Notably, no significant C—H⋯π or π–π interactions are observed. O2—H2⋯O1ⁱ hydrogen bonds between the phenolic OH group and the carbonyl O atom of a neighbouring molecule generate C(5) chains extending parallel to [101]. Likewise, N1—H1⋯O1ⁱⁱ hydrogen bonds between the N—H function of the dihydropyridazine ring and the carbonyl O atom generate centrosymmetric dimers with an R₂²(8) motif. The two types of hydrogen bonding result in the formation of layers parallel to (12 $[\overline{1}]$ ). A three-dimensional supramolecular network is eventually formed through intermolecular C13—H13A⋯O2ⁱⁱⁱ and C13—H13C⋯O2^iv hydrogen bonds with R₂⁴(8) motifs (Fig. 2 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.86	2.671 (2)	168
N1—H1⋯O1ⁱⁱ	0.86	2.02	2.875 (3)	170
C13—H13A⋯O2ⁱⁱⁱ	0.96	2.51	3.465 (3)	172
C13—H13C⋯O2^iv	0.96	2.57	3.489 (4)	159
Symmetry codes: (i) x-1, y, z-1; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z; (iv) x+1, y, z.

Figure 2
The crystal packing of the title compound, with N—H⋯O, O—H⋯O and C—H⋯O interactions shown as blue, green and black dashed lines, respectively.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, update November 2018; Groom et al., 2016 ) revealed two structures containing a similar pyridazinone moiety as in the title structure but with different substituents, viz. 6-phenyl-4,5-dihydropyridazin-3(2H)-one (CSD refcode TADQUL; Abourichaa et al., 2003 ) and (R)-(−)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one (ADIGOK; Zhang et al., 2006 ). In the structure of TADQUL, the dihydropyridazine ring adopts a half-chair conformation, with atoms C1, N2, N3 and C4 in a common plane, with C5 0.222 (2) Å and C6 0.262 (2) Å on opposite sides of this plane. The plane is almost coplanar with the 4-aminophenyl ring, the dihedral angle between the two planes being 1.73 (9) Å. In the crystal, hydrogen-bonded centrosymmetric dimers are observed. The O1=C1 bond length is 1.2316 (14) Å. The N3—C4, N2—N3 and N2—C1 bond lengths are 1.3464 (15), 1.3877 (14) and 1.2830 (15) Å, respectively. In the structure of ADIGOK, the asymmetric unit consists of two molecules of the same enantiomer, and the crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds.

5. Hirshfeld surface analysis

Hirshfeld surface analysis was used to quantify the intermolecular interactions of the title compound, using CrystalExplorer17.5 (Turner et al., 2017 ). The Hirshfeld surface analysis was planned using a standard (high) surface resolution with the three-dimensional d_norm surfaces plotted over a fixed colour scale of −0.7021 (red) to 2.2382 a.u. (blue). The surfaces mapped over relevant intermolecular contacts are illustrated in Fig. 3. The Hirshfeld surface representations with the function d_norm plotted onto the surface are shown for the H⋯H, H⋯C/C⋯H, H⋯O/O⋯H, C⋯N/N⋯C and H⋯N/N⋯H interactions in Figs. 4(a)–(e), respectively. The overall two-dimensional fingerprint plot and those delineated into H⋯H, H⋯C/C⋯H, H⋯O/O⋯H, C⋯N/N⋯C and H⋯N/N⋯H contacts are illustrated in Figs. 5(a)–(f), respectively. The largest interaction is that of H⋯H, contributing 43.3% to the overall crystal packing. H⋯C/C⋯H contacts add a 19.3% contribution to the Hirshfeld surface, with the tips at d_e + d_i ∼ 2.72 Å. H⋯O/O⋯H contacts make a 22.6% contribution to the Hirshfeld surface and are represented by a pair of sharp spikes in the region d_e + d_i ∼ 2.70 Å in the fingerprint plot. H⋯O/O⋯H interactions arise from intermolecular O—H⋯O hydrogen bonding and C—H⋯O contacts. The contributions of the other contacts to the Hirshfeld surface are negligible, i.e. C⋯N/N⋯C of 3.0% and H⋯N/N⋯H of 5.8%.

Figure 3
(a) d_norm mapped on the Hirshfeld surface for visualizing the intermolecular interactions, (b) d_e mapped on the surface, (c) shape-index map of the title compound and (d) curvedness map of the title compound using a range from −4 to 4 Å.

Figure 4
The Hirshfeld surface representations with the function d_norm plotted onto the surface for (a) H⋯H, (b) H⋯C/ C⋯H, (c) H⋯O/O⋯H, (d) C⋯N/N⋯C and (e) H⋯N/N⋯H interactions.

Figure 5
The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯C/ C⋯H, (d) H⋯O/O⋯H, (e) C⋯N/N⋯C and (f) H⋯N/N⋯H interactions.

6. Synthesis and crystallization

To a solution of 6-(4-hydroxy-3-methoxyphenyl)-4-oxohex-5-enoic acid (0.25 g, 1 mmol) in 20 ml of ethanol, an equimolar amount of hydrazine hydrate was added. The mixture was maintained under reflux until thin-layer chromatography (TLC) indicated the end of the reaction. After cooling, the precipitate which formed was filtered off, washed with ethanol and recrystallized from ethanol. Slow evaporation at room temperature led to the formation of single crystals of the title compound.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms on C atoms were placed in idealized positions and refined as riding, with C—H = 0.93–0.97 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) otherwise. The NH and OH hydrogens were located in a difference Fourier map and were constrained with N—H = 0.86 Å and U_iso(H) = 1.2U_eq(N), and O—H = 0.86 Å and U_iso(H) = 1.5U_eq(O), using a riding model.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂O₃
M_r	246.26
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	6.0828 (9), 9.4246 (13), 11.1724 (16)
α, β, γ (°)	75.838 (11), 83.099 (12), 84.059 (11)
V (Å³)	614.70 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.72 × 0.39 × 0.16

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.944, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6563, 2426, 1506
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.147, 1.00
No. of reflections	2426
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXT2017 (Sheldrick, 2015a ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ), WinGX (Farrugia, 2012 ), SHELXL2018 (Sheldrick, 2015b ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1959568; 1959568

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989019014130/wm5521sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019014130/wm5521Isup3.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: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-6-(4-Hydroxy-3-methoxystyryl)-4,5-dihydropyridazin-3(2H)-\ one top

Crystal data top

C₁₃H₁₄N₂O₃	Z = 2
M_r = 246.26	F(000) = 260
Triclinic, P1	D_x = 1.330 Mg m⁻³
a = 6.0828 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4246 (13) Å	Cell parameters from 13077 reflections
c = 11.1724 (16) Å	θ = 2.2–30.7°
α = 75.838 (11)°	µ = 0.10 mm⁻¹
β = 83.099 (12)°	T = 293 K
γ = 84.059 (11)°	Prism, yellow
V = 614.70 (16) Å³	0.72 × 0.39 × 0.16 mm

Data collection top

Stoe IPDS 2 diffractometer	1506 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.054
rotation method scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −7→7
T_min = 0.944, T_max = 0.989	k = −11→11
6563 measured reflections	l = −13→13
2426 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0747P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2426 reflections	Δρ_max = 0.17 e Å⁻³
165 parameters	Δρ_min = −0.17 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	0.7518 (3)	0.88682 (19)	0.99156 (15)	0.0601 (5)
O3	0.4960 (3)	0.58008 (19)	0.11563 (16)	0.0614 (5)
O2	0.1290 (3)	0.7317 (2)	0.05778 (16)	0.0636 (5)
H2	0.016474	0.786724	0.044599	0.095*
N1	0.4947 (3)	0.9323 (2)	0.85757 (17)	0.0525 (5)
H1	0.429651	0.995567	0.896673	0.063*
N2	0.3918 (3)	0.9139 (2)	0.75870 (17)	0.0519 (5)
C9	0.3982 (4)	0.6576 (2)	0.1986 (2)	0.0497 (6)
C5	0.3927 (4)	0.8291 (3)	0.5807 (2)	0.0506 (6)
H5	0.252921	0.878478	0.572201	0.061*
C1	0.6829 (4)	0.8631 (3)	0.8987 (2)	0.0492 (6)
C4	0.5043 (4)	0.8412 (2)	0.6851 (2)	0.0472 (6)
C8	0.4803 (4)	0.6645 (3)	0.3066 (2)	0.0521 (6)
H8	0.616062	0.614251	0.326018	0.062*
C11	0.0780 (4)	0.8118 (3)	0.2494 (2)	0.0538 (6)
H11	−0.059111	0.860442	0.230853	0.065*
C7	0.3664 (4)	0.7445 (2)	0.3875 (2)	0.0496 (6)
C10	0.1954 (4)	0.7364 (2)	0.1681 (2)	0.0487 (6)
C6	0.4707 (4)	0.7544 (3)	0.4962 (2)	0.0549 (6)
H6	0.607897	0.702171	0.507391	0.066*
C12	0.1607 (4)	0.8164 (3)	0.3580 (2)	0.0552 (6)
H12	0.078822	0.867751	0.411814	0.066*
C13	0.7007 (4)	0.4965 (3)	0.1419 (3)	0.0614 (7)
H13A	0.745228	0.441469	0.079994	0.092*
H13B	0.682204	0.430200	0.222071	0.092*
H13C	0.812721	0.561367	0.141331	0.092*
C2	0.7972 (5)	0.7565 (3)	0.8299 (3)	0.0694 (8)
H2A	0.761992	0.658432	0.875007	0.083*
H2B	0.956271	0.761159	0.827335	0.083*
C3	0.7375 (4)	0.7807 (3)	0.7002 (2)	0.0673 (8)
H3A	0.836608	0.847839	0.645178	0.081*
H3B	0.760060	0.688125	0.675416	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0632 (11)	0.0804 (12)	0.0479 (10)	0.0136 (8)	−0.0292 (8)	−0.0331 (8)
O3	0.0642 (11)	0.0739 (11)	0.0579 (10)	0.0218 (8)	−0.0273 (9)	−0.0392 (9)
O2	0.0633 (12)	0.0859 (13)	0.0537 (10)	0.0146 (9)	−0.0326 (9)	−0.0349 (9)
N1	0.0536 (12)	0.0686 (13)	0.0448 (11)	0.0094 (9)	−0.0204 (9)	−0.0299 (10)
N2	0.0510 (12)	0.0670 (13)	0.0450 (11)	0.0068 (9)	−0.0213 (9)	−0.0237 (10)
C9	0.0569 (14)	0.0515 (13)	0.0479 (13)	0.0029 (11)	−0.0190 (11)	−0.0217 (11)
C5	0.0550 (14)	0.0602 (14)	0.0422 (12)	0.0029 (11)	−0.0196 (11)	−0.0185 (11)
C1	0.0539 (14)	0.0552 (14)	0.0427 (12)	0.0056 (11)	−0.0182 (11)	−0.0172 (11)
C4	0.0524 (14)	0.0522 (13)	0.0416 (12)	0.0007 (10)	−0.0152 (11)	−0.0168 (10)
C8	0.0533 (14)	0.0584 (14)	0.0511 (14)	0.0074 (11)	−0.0248 (12)	−0.0207 (11)
C11	0.0495 (13)	0.0675 (15)	0.0506 (14)	0.0090 (11)	−0.0211 (11)	−0.0237 (12)
C7	0.0579 (14)	0.0565 (14)	0.0412 (12)	0.0011 (11)	−0.0181 (11)	−0.0204 (11)
C10	0.0540 (14)	0.0560 (14)	0.0432 (13)	−0.0004 (11)	−0.0192 (11)	−0.0202 (11)
C6	0.0601 (15)	0.0640 (15)	0.0467 (13)	0.0033 (12)	−0.0229 (12)	−0.0197 (12)
C12	0.0558 (15)	0.0681 (15)	0.0490 (14)	0.0056 (12)	−0.0149 (12)	−0.0274 (12)
C13	0.0656 (16)	0.0634 (15)	0.0600 (16)	0.0144 (12)	−0.0203 (13)	−0.0248 (13)
C2	0.0734 (18)	0.0867 (19)	0.0599 (16)	0.0316 (14)	−0.0365 (14)	−0.0406 (14)
C3	0.0576 (16)	0.098 (2)	0.0593 (16)	0.0136 (14)	−0.0231 (13)	−0.0423 (15)

Geometric parameters (Å, º) top

O1—C1	1.241 (3)	C8—H8	0.9300
O3—C9	1.362 (3)	C11—C10	1.377 (3)
O3—C13	1.424 (3)	C11—C12	1.379 (3)
O2—C10	1.355 (2)	C11—H11	0.9300
O2—H2	0.8200	C7—C12	1.396 (3)
N1—C1	1.331 (3)	C7—C6	1.462 (3)
N1—N2	1.387 (2)	C6—H6	0.9300
N1—H1	0.8600	C12—H12	0.9300
N2—C4	1.288 (3)	C13—H13A	0.9600
C9—C8	1.378 (3)	C13—H13B	0.9600
C9—C10	1.406 (3)	C13—H13C	0.9600
C5—C6	1.327 (3)	C2—C3	1.493 (3)
C5—C4	1.451 (3)	C2—H2A	0.9700
C5—H5	0.9300	C2—H2B	0.9700
C1—C2	1.480 (3)	C3—H3A	0.9700
C4—C3	1.486 (3)	C3—H3B	0.9700
C8—C7	1.394 (3)

C9—O3—C13	117.98 (17)	O2—C10—C11	124.3 (2)
C10—O2—H2	109.5	O2—C10—C9	116.1 (2)
C1—N1—N2	127.3 (2)	C11—C10—C9	119.54 (19)
C1—N1—H1	116.4	C5—C6—C7	127.7 (2)
N2—N1—H1	116.4	C5—C6—H6	116.1
C4—N2—N1	117.42 (18)	C7—C6—H6	116.1
O3—C9—C8	126.0 (2)	C11—C12—C7	120.5 (2)
O3—C9—C10	115.23 (18)	C11—C12—H12	119.8
C8—C9—C10	118.8 (2)	C7—C12—H12	119.8
C6—C5—C4	126.4 (2)	O3—C13—H13A	109.5
C6—C5—H5	116.8	O3—C13—H13B	109.5
C4—C5—H5	116.8	H13A—C13—H13B	109.5
O1—C1—N1	120.4 (2)	O3—C13—H13C	109.5
O1—C1—C2	123.3 (2)	H13A—C13—H13C	109.5
N1—C1—C2	116.36 (19)	H13B—C13—H13C	109.5
N2—C4—C5	115.5 (2)	C1—C2—C3	114.4 (2)
N2—C4—C3	122.97 (19)	C1—C2—H2A	108.7
C5—C4—C3	121.5 (2)	C3—C2—H2A	108.7
C9—C8—C7	122.0 (2)	C1—C2—H2B	108.7
C9—C8—H8	119.0	C3—C2—H2B	108.7
C7—C8—H8	119.0	H2A—C2—H2B	107.6
C10—C11—C12	121.0 (2)	C4—C3—C2	113.3 (2)
C10—C11—H11	119.5	C4—C3—H3A	108.9
C12—C11—H11	119.5	C2—C3—H3A	108.9
C8—C7—C12	118.02 (19)	C4—C3—H3B	108.9
C8—C7—C6	118.9 (2)	C2—C3—H3B	108.9
C12—C7—C6	123.1 (2)	H3A—C3—H3B	107.7

C1—N1—N2—C4	−12.5 (4)	O3—C9—C10—O2	−3.3 (3)
C13—O3—C9—C8	0.8 (3)	C8—C9—C10—O2	176.6 (2)
C13—O3—C9—C10	−179.3 (2)	O3—C9—C10—C11	176.6 (2)
N2—N1—C1—O1	−177.3 (2)	C8—C9—C10—C11	−3.5 (4)
N2—N1—C1—C2	1.2 (4)	C4—C5—C6—C7	−177.5 (2)
N1—N2—C4—C5	−177.97 (19)	C8—C7—C6—C5	177.4 (3)
N1—N2—C4—C3	−1.5 (3)	C12—C7—C6—C5	0.0 (4)
C6—C5—C4—N2	−176.7 (3)	C10—C11—C12—C7	0.2 (4)
C6—C5—C4—C3	6.8 (4)	C8—C7—C12—C11	−2.2 (4)
O3—C9—C8—C7	−178.7 (2)	C6—C7—C12—C11	175.2 (2)
C10—C9—C8—C7	1.4 (4)	O1—C1—C2—C3	−159.6 (3)
C9—C8—C7—C12	1.4 (4)	N1—C1—C2—C3	21.9 (4)
C9—C8—C7—C6	−176.1 (2)	N2—C4—C3—C2	23.8 (4)
C12—C11—C10—O2	−177.4 (2)	C5—C4—C3—C2	−160.0 (2)
C12—C11—C10—C9	2.7 (4)	C1—C2—C3—C4	−32.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.86	2.671 (2)	168
N1—H1···O1ⁱⁱ	0.86	2.02	2.875 (3)	170
C13—H13A···O2ⁱⁱⁱ	0.96	2.51	3.465 (3)	172
C13—H13C···O2^iv	0.96	2.57	3.489 (4)	159

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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