Crystal structure of 4-(4-chloro­phen­yl)-6-(morpholin-4-yl)pyridazin-3(2H)-one

Aydın, A.; Akkurt, M.; Şüküroğlu, M.; Büyükgüngör, O.

doi:10.1107/S2056989015012980

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ISSN: 2056-9890

Volume 71| Part 8| August 2015| Pages 944-946

https://doi.org/10.1107/S2056989015012980

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Crystal structure of 4-(4-chlorophenyl)-6-(morpholin-4-yl)pyridazin-3(2H)-one

Abdullah Aydın,^a ^* Mehmet Akkurt,^b Murat Şüküroğlu ^c and Orhan Büyükgüngör ^d

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: aaydin@kastamonu.edu.tr

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 30 June 2015; accepted 6 July 2015; online 17 July 2015)

In the title compound, C₁₄H₁₄ClN₃O₂, the morpholine ring adopts a chair conformation, with the exocyclic N—C bond in an equatorial orientation. The 1,6-dihydropyridazine ring is essentially planar, with a maximum deviation of 0.014 (1) Å, and forms a dihedral angle of 40.16 (7)° with the plane of the benzene ring. In the crystal, pairs of centrosymmetrically related molecules are linked into dimers via N—H⋯O hydrogen bonds, forming R₂²(8) ring motifs. The dimers are connected via C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three-dimensional network. Aromatic π–π stacking interactions [centroid–centroid distance = 3.6665 (9) Å] are also observed. Semi-empirical molecular orbital calculations were carried out using the AM1 method. The calculated dihedral angles between the pyridizine and benzene rings and between the pyridizine and morpholine (all atoms) rings are 34.49 and 76.96°, respectively·The corresponding values obtained from the X-ray structure determination are 40.16 (7) and 12.97 (9)°, respectively. The morpholine ring of the title compound in the calculated gas-phase seems to have a quite different orientation compared to that indicated by the X-ray structure determination.

Keywords: crystal structure; pyridazinone derivative; hydrogen bonding; π–π stacking interactions.

CCDC reference: 1410873

1. Chemical context

The title compound was first synthesized by Şüküroğlu et al. (2006 ). The pharmacological properties of the compound have been investigated and it was found it possesses an analgesic effect close to that of aspirin. In recent years, the 3(2H)-pyridazinone system has aroused a great deal of attention due to its structural relationship to pyrazolone derivatives such as aminopyrine and dipyrone in view of the ring enlargement of pyrazolone to pyridazinone. These drugs possess analgesic and anti-inflammatory activities although they have limitations for their clinical use due to serious side effects such as blood dyscrasias (Şüküroğlu et al., 2006; Brogden, 1986 ).

2. Structural commentary

In the title compound (Fig. 1) the morpholine ring (N3/O2/C11–C14) adopts a chair conformation, with the puckering parameters Q_T = 0.551 (2) Å, θ = 174.33 (19) and φ = 175 (2)°. The 1,6-dihydropyridazine ring (N1/N2/C7–C10) is essentially planar, with a maximum deviation of 0.014 (1) Å for atom N1 and forms a dihedral angle of 40.16 (7)° with the C1–C6 benzene ring. The dihedral angle between the morpholine ring (all atoms) and the pyridizine ring is 12.97 (9)°. The bond lengths and angles are in the normal range. The Cl1—C4, N1—N2 and O1—C12 bond lengths [1.7379 (17), 1.3620 (16), and 1.417 (3) Å, respectively] are consistent with those reported previously [1.753 (5), 1.275 (7) and 1.432 (7) Å in molecule A; Aydin et al., 2015 ]. In addition, the C8—O1 bond length of 1.2500 (16) Å compares well with the value of 1.2343 (17) Å reported by Aydın et al. (2011 ).

Figure 1
View of the title molecule with displacement ellipsoids for non-H atoms drawn at the 30% probability level.

3. Supramolecular features

In the crystal, N—H⋯O hydrogen bonds (Table 1, Fig. 2) form dimers between centrosymmetric pairs of molecules with $[R_{2}^{2}]$ (8) ring motifs. The dimers are connected by C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three-dimensional network (Table 1, Fig. 3). In addition, π–π stacking interactions [Cg2⋯Cg3ⁱ = 3.6665 (9) Å; Cg2 and Cg3 are the centroids of the 1,6-dihydropyridazine ring (N1/N2/C7–C10) and the benzene ring (C1–C6); symmetry code: (i) 1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z)] contribute to the cohesion of the structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.92	2.7705 (15)	170
C5—H5⋯O2ⁱⁱ	0.93	2.56	3.4737 (19)	166
C10—H10⋯O1ⁱⁱⁱ	0.93	2.43	3.1614 (17)	136
C12—H12B⋯Cl1^iv	0.97	2.79	3.754 (2)	173
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
View of a dimer, with $[R_{2}^{2}]$ (8) ring motif, formed by N—H⋯O hydrogen bonds (dashed lines) between two centrosymmetrically related molecules.

Figure 3
Crystal packing and hydrogen bonding (dashed lines) in the title compound, viewed down the b axis. H atoms not involved in hydrogen bonding have been omitted.

4. Semi-empirical molecular orbital calculations

Semi-empirical molecular orbital calculations of the title compound were carried out using the AM1 method (Dewar et al., 1985 ) with WinMopac7.2 software (Shchepin & Litvinov, 1998 ). A spatial view of the single molecule of the title compound calculated in the gas phase is shown in Fig. 4. The calculated dihedral angles between the pyridizine and benzene rings and between the pyridizine and morpholine (all atoms) ring sare 34.49 and 76.96°, respectively. The corresponding values obtained from the X-ray structure determination are 40.16 (7) and 12.97 (9)°, respectively. The morpholine ring of the title compound in the calculated gas phase seems to have a quite different orientation compared to that indicated by the X-ray structure determination. The calculated dipole moment is 2.13 Debye. The HOMO and LUMO energy levels are −9.05 and −1.01 eV, respectively.

Figure 4
Spatial view of the title compound calculated using the AM1 method.

5. Synthesis and crystallization

4-(4-Chlorophenyl)-6-(morpholin-4-yl)pyridazin-3(2H)-one was prepared by a reported literature protocol (Şüküroğlu et al., 2006). A solution of 3-chloro-4-phenyl-6-(morpholin-4-yl)-pyridazine (0.06 mol) and potassium acetate (0.08 mol) in 100 ml of acetic acid was refluxed for 10 h. The reaction mixture was then cooled and poured into ice–water. The precipitate was filtered off, washed with water and recrystallized from ethanol, giving yellow prismatic crystals. Yield 96%, m. p. 558 K. ¹H NMR (CDCl₃) δ 9.92 (s, 1H, NH), 7.76 (m, 2H, phenyl-H3, H5), 7.44 (m, 2H, phenyl-H2, H6), 7.23 (s, 1H, pyridazinone-H5), 3.85 (t, 4H, morpholine-H2, H6), 3.29 (t, 4H, morpholine-H3, H5) p.p.m. IR v_max cm⁻¹ (KBr): 3124, 3053, 2960, 2861, 1656. Analysis C, H, N (C₁₄H₁₄ClN₃O₂)

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically and refined using a riding model with N—H = 0.86 Å, C—H = 0.93–0.97 Å, and with U_iso(H) = 1.2U_eq(C, N).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClN₃O₂
M_r	291.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.0977 (9), 7.4932 (4), 14.1123 (9)
β (°)	90.149 (5)
V (Å³)	1385.03 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.28
Crystal size (mm)	0.80 × 0.38 × 0.08

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.880, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	8760, 2868, 2267
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.04
No. of reflections	2868
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.23
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1410873

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015012980/rz5163sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012980/rz5163Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012980/rz5163Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-(4-Chlorophenyl)-6-(morpholin-4-yl)pyridazin-3(2H)-one top

Crystal data top

C₁₄H₁₄ClN₃O₂	F(000) = 608
M_r = 291.73	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11553 reflections
a = 13.0977 (9) Å	θ = 1.6–28.0°
b = 7.4932 (4) Å	µ = 0.28 mm⁻¹
c = 14.1123 (9) Å	T = 296 K
β = 90.149 (5)°	Prism, yellow
V = 1385.03 (15) Å³	0.80 × 0.38 × 0.08 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	2868 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2267 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.028
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.6°
ω scans	h = −16→16
Absorption correction: integration (XRED-32; Stoe & Cie, 2002)	k = −9→9
T_min = 0.880, T_max = 0.978	l = −17→17
8760 measured reflections

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0578P)² + 0.1445P] where P = (F_o² + 2F_c²)/3
2868 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Cl1	0.16215 (4)	0.21784 (11)	0.00258 (4)	0.0999 (2)
O1	0.42246 (7)	0.04185 (14)	0.40107 (6)	0.0472 (3)
O2	0.99398 (9)	0.3320 (2)	0.22281 (11)	0.0764 (5)
N1	0.58954 (8)	0.10751 (17)	0.41972 (8)	0.0454 (4)
N2	0.68499 (9)	0.16004 (17)	0.39371 (8)	0.0465 (4)
N3	0.78867 (9)	0.28188 (18)	0.27895 (9)	0.0499 (4)
C1	0.42580 (10)	0.17384 (18)	0.20628 (9)	0.0394 (4)
C2	0.43734 (11)	0.1304 (2)	0.11136 (10)	0.0500 (5)
C3	0.35657 (13)	0.1423 (2)	0.04893 (11)	0.0585 (5)
C4	0.26364 (12)	0.1993 (2)	0.08154 (11)	0.0563 (5)
C5	0.24891 (11)	0.2423 (2)	0.17507 (12)	0.0534 (5)
C6	0.33006 (10)	0.2283 (2)	0.23759 (10)	0.0455 (4)
C7	0.51501 (10)	0.16802 (18)	0.27082 (9)	0.0382 (4)
C8	0.50364 (10)	0.10152 (19)	0.36713 (9)	0.0393 (4)
C9	0.69357 (10)	0.21801 (19)	0.30668 (10)	0.0423 (4)
C10	0.60866 (10)	0.22402 (19)	0.24347 (10)	0.0427 (4)
C11	0.87216 (12)	0.2561 (3)	0.34556 (13)	0.0625 (6)
C12	0.96240 (13)	0.3681 (3)	0.31683 (15)	0.0724 (7)
C13	0.91285 (13)	0.3718 (4)	0.16077 (15)	0.0835 (8)
C14	0.81944 (13)	0.2585 (3)	0.18073 (14)	0.0745 (7)
H1	0.58330	0.07350	0.47760	0.0550*
H2	0.50070	0.09260	0.08950	0.0600*
H3	0.36500	0.11210	−0.01450	0.0700*
H5	0.18530	0.28040	0.19610	0.0640*
H6	0.32050	0.25550	0.30120	0.0550*
H10	0.61770	0.26720	0.18230	0.0510*
H11A	0.89160	0.13120	0.34680	0.0750*
H11B	0.85030	0.28970	0.40870	0.0750*
H12A	0.94450	0.49330	0.32220	0.0870*
H12B	1.01870	0.34500	0.35990	0.0870*
H13A	0.93470	0.35190	0.09600	0.1000*
H13B	0.89500	0.49690	0.16710	0.1000*
H14A	0.76410	0.29350	0.13890	0.0890*
H14B	0.83490	0.13390	0.16890	0.0890*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0672 (3)	0.1570 (6)	0.0753 (3)	−0.0021 (3)	−0.0358 (2)	0.0166 (3)
O1	0.0438 (5)	0.0619 (6)	0.0358 (5)	−0.0068 (5)	0.0003 (4)	0.0016 (4)
O2	0.0386 (5)	0.0910 (10)	0.0996 (10)	0.0011 (6)	0.0060 (6)	0.0097 (8)
N1	0.0441 (6)	0.0552 (7)	0.0370 (6)	−0.0050 (5)	−0.0037 (4)	0.0043 (5)
N2	0.0401 (6)	0.0511 (7)	0.0482 (6)	−0.0027 (5)	−0.0062 (5)	0.0051 (5)
N3	0.0353 (6)	0.0576 (8)	0.0569 (7)	−0.0008 (5)	−0.0028 (5)	0.0103 (6)
C1	0.0399 (7)	0.0394 (7)	0.0390 (6)	−0.0022 (5)	−0.0027 (5)	0.0050 (5)
C2	0.0474 (8)	0.0604 (9)	0.0422 (7)	0.0042 (7)	0.0001 (6)	0.0033 (6)
C3	0.0631 (9)	0.0735 (11)	0.0389 (7)	−0.0033 (8)	−0.0075 (6)	0.0036 (7)
C4	0.0480 (8)	0.0671 (11)	0.0537 (8)	−0.0070 (7)	−0.0159 (6)	0.0131 (7)
C5	0.0378 (7)	0.0626 (10)	0.0598 (9)	0.0002 (6)	−0.0038 (6)	0.0085 (7)
C6	0.0405 (7)	0.0524 (8)	0.0437 (7)	−0.0010 (6)	−0.0017 (5)	0.0017 (6)
C7	0.0389 (6)	0.0372 (7)	0.0386 (7)	0.0030 (5)	−0.0018 (5)	0.0009 (5)
C8	0.0411 (6)	0.0404 (7)	0.0365 (6)	−0.0006 (5)	−0.0019 (5)	−0.0023 (5)
C9	0.0371 (6)	0.0403 (7)	0.0496 (7)	0.0024 (5)	−0.0029 (5)	0.0037 (6)
C10	0.0399 (7)	0.0441 (8)	0.0440 (7)	0.0039 (6)	−0.0010 (5)	0.0079 (6)
C11	0.0414 (8)	0.0720 (11)	0.0740 (11)	−0.0014 (7)	−0.0124 (7)	0.0149 (9)
C12	0.0418 (8)	0.0806 (13)	0.0947 (14)	−0.0067 (8)	−0.0117 (8)	0.0124 (11)
C13	0.0474 (9)	0.1222 (19)	0.0809 (13)	−0.0066 (10)	0.0089 (8)	0.0210 (13)
C14	0.0456 (9)	0.1111 (16)	0.0669 (11)	−0.0097 (9)	0.0074 (8)	0.0022 (11)

Geometric parameters (Å, º) top

Cl1—C4	1.7379 (17)	C7—C8	1.4556 (18)
O1—C8	1.2500 (16)	C7—C10	1.3535 (19)
O2—C12	1.417 (3)	C9—C10	1.4246 (19)
O2—C13	1.407 (2)	C11—C12	1.506 (3)
N1—N2	1.3620 (16)	C13—C14	1.516 (3)
N1—C8	1.3470 (17)	C2—H2	0.9300
N2—C9	1.3079 (18)	C3—H3	0.9300
N3—C9	1.3915 (18)	C5—H5	0.9300
N3—C11	1.453 (2)	C6—H6	0.9300
N3—C14	1.455 (2)	C10—H10	0.9300
N1—H1	0.8600	C11—H11A	0.9700
C1—C2	1.3872 (19)	C11—H11B	0.9700
C1—C6	1.3918 (19)	C12—H12A	0.9700
C1—C7	1.4803 (18)	C12—H12B	0.9700
C2—C3	1.378 (2)	C13—H13A	0.9700
C3—C4	1.371 (2)	C13—H13B	0.9700
C4—C5	1.373 (2)	C14—H14A	0.9700
C5—C6	1.384 (2)	C14—H14B	0.9700

C12—O2—C13	108.69 (14)	N3—C14—C13	109.58 (16)
N2—N1—C8	128.84 (11)	C1—C2—H2	119.00
N1—N2—C9	115.48 (11)	C3—C2—H2	119.00
C9—N3—C11	116.43 (13)	C2—C3—H3	120.00
C9—N3—C14	118.48 (13)	C4—C3—H3	120.00
C11—N3—C14	112.98 (13)	C4—C5—H5	120.00
C8—N1—H1	116.00	C6—C5—H5	120.00
N2—N1—H1	116.00	C1—C6—H6	120.00
C2—C1—C7	119.96 (12)	C5—C6—H6	120.00
C2—C1—C6	118.42 (12)	C7—C10—H10	119.00
C6—C1—C7	121.58 (12)	C9—C10—H10	119.00
C1—C2—C3	121.12 (14)	N3—C11—H11A	110.00
C2—C3—C4	119.11 (14)	N3—C11—H11B	110.00
Cl1—C4—C3	119.21 (12)	C12—C11—H11A	110.00
Cl1—C4—C5	119.25 (12)	C12—C11—H11B	110.00
C3—C4—C5	121.54 (15)	H11A—C11—H11B	108.00
C4—C5—C6	119.06 (14)	O2—C12—H12A	109.00
C1—C6—C5	120.73 (13)	O2—C12—H12B	109.00
C8—C7—C10	117.86 (12)	C11—C12—H12A	109.00
C1—C7—C10	122.00 (12)	C11—C12—H12B	109.00
C1—C7—C8	120.14 (11)	H12A—C12—H12B	108.00
O1—C8—N1	120.72 (12)	O2—C13—H13A	109.00
O1—C8—C7	124.71 (12)	O2—C13—H13B	109.00
N1—C8—C7	114.57 (12)	C14—C13—H13A	109.00
N2—C9—N3	117.23 (12)	C14—C13—H13B	109.00
N3—C9—C10	120.73 (13)	H13A—C13—H13B	108.00
N2—C9—C10	121.98 (12)	N3—C14—H14A	110.00
C7—C10—C9	121.21 (13)	N3—C14—H14B	110.00
N3—C11—C12	109.97 (16)	C13—C14—H14A	110.00
O2—C12—C11	112.14 (16)	C13—C14—H14B	110.00
O2—C13—C14	111.97 (19)	H14A—C14—H14B	108.00

C13—O2—C12—C11	60.9 (2)	C7—C1—C6—C5	176.41 (13)
C12—O2—C13—C14	−61.1 (2)	C2—C1—C7—C10	39.3 (2)
C8—N1—N2—C9	2.5 (2)	C6—C1—C7—C10	−138.37 (15)
N2—N1—C8—C7	−2.9 (2)	C1—C2—C3—C4	0.5 (2)
N2—N1—C8—O1	176.78 (13)	C2—C3—C4—Cl1	178.98 (12)
N1—N2—C9—C10	−0.5 (2)	C2—C3—C4—C5	−0.9 (2)
N1—N2—C9—N3	176.65 (12)	C3—C4—C5—C6	0.3 (2)
C11—N3—C9—C10	−175.00 (15)	Cl1—C4—C5—C6	−179.64 (12)
C14—N3—C11—C12	51.2 (2)	C4—C5—C6—C1	0.9 (2)
C9—N3—C11—C12	−166.70 (15)	C1—C7—C8—O1	2.1 (2)
C11—N3—C9—N2	7.8 (2)	C10—C7—C8—O1	−178.24 (14)
C14—N3—C9—N2	147.76 (15)	C10—C7—C8—N1	1.46 (19)
C11—N3—C14—C13	−51.3 (2)	C8—C7—C10—C9	0.1 (2)
C14—N3—C9—C10	−35.0 (2)	C1—C7—C10—C9	179.78 (13)
C9—N3—C14—C13	167.46 (16)	C1—C7—C8—N1	−178.23 (12)
C2—C1—C7—C8	−141.00 (14)	N3—C9—C10—C7	−177.67 (13)
C7—C1—C2—C3	−177.11 (13)	N2—C9—C10—C7	−0.6 (2)
C6—C1—C2—C3	0.7 (2)	N3—C11—C12—O2	−55.9 (2)
C6—C1—C7—C8	41.30 (19)	O2—C13—C14—N3	56.5 (2)
C2—C1—C6—C5	−1.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.92	2.7705 (15)	170
C5—H5···O2ⁱⁱ	0.93	2.56	3.4737 (19)	166
C6—H6···O1	0.93	2.51	2.9538 (17)	109
C10—H10···O1ⁱⁱⁱ	0.93	2.43	3.1614 (17)	136
C12—H12B···Cl1^iv	0.97	2.79	3.754 (2)	173

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

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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