(E)-1-[2-(3,4-Di­methyl­phen­yl)diazen-2-ium-1-yl]naphthalen-2-olate

Chetioui, S.; Boutebdja, M.; Boudraa, M.; Touzani, R.; Merazig, H.

doi:10.1107/S2414314617002590

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170259

https://doi.org/10.1107/S2414314617002590

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(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

Souheyla Chetioui,^a ^* Mehdi Boutebdja,^a Mhamed Boudraa,^a Rachid Touzani ^b,^c and Hocine Merazig ^a

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria, ^bLaboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, and ^cFaculté Pluridisciplinaire Nador BP 300, Selouane, 62702, Nador, Morocco
^*Correspondence e-mail: souheilachetioui@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 February 2017; accepted 14 February 2017; online 17 February 2017)

The title zwitterion, C₁₈H₁₆N₂O, features an intramolecular N—H⋯O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°. In the crystal, aromatic π–π stacking occurs [shortest centroid–centroid distance = 3.574 (3) Å] and C—H⋯O interactions are also observed.

Keywords: crystal structure; zwitterion; azo dyes; hydrogen bonding; π–π stacking.

CCDC reference: 1532675

Structure description

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Navarro & Sanz (1999 ); Tao et al. (1999 ).

The title azo dye adopts the zwitterionic form in the crystal (Fig. 1), with proton transfer from the phenol group to the azo group, which allows for the formation of an intramolecular N—H⋯O hydrogen bond (Table 1). The dimethyl benzene ring is disordered by ∼180° rotation about the N2—C11 bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.82	2.5347 (15)	140
C12A—H12A⋯O1ⁱ	0.93	2.54	3.325 (2)	143
Symmetry code: (i) -x+1, -y+1, -z.

Figure 1
The molecular structure of the title compound, with 50% probability displacement ellipsoids.

In the crystal, molecules are linked by aromatic π–π stacking between the benzene rings and the naphthalene ring systems of adjacent molecules, the centroid–centroid distances of 3.574 (3) and 3.5754 (12) Å, respectively, between the C5–C10 and C11B–C16B(x, y − 1, z) rings and between the C5–C10 and C11A–C16A(x, y − 1, z) rings. C—H—O hydrogen bonds are also observed, forming chains running parallel to the a-axis direction (Table 1, Fig. 2).

Figure 2
The crystal packing of the title compound, viewed along the b-axis direction.

Synthesis and crystallization

The title compound was synthesized according to a literature method (Wang et al., 2003 ), viz. the diazotization of 3,4-dimethylaniline followed by a coupling reaction with 2-naphthol. Red prisms were obtained by slow evaporation of an acetone solution at room temperature (yield 88%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O
M_r	276.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.6326 (5), 6.1866 (2), 20.1712 (8)
β (°)	98.023 (2)
V (Å³)	1437.44 (10)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.15 × 0.08 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	13963, 3654, 2479
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.04
No. of reflections	3654
No. of parameters	254
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2006 ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1532675

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617002590/hb4118sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002590/hb4118Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002590/hb4118Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate top

Crystal data top

C₁₈H₁₆N₂O	F(000) = 584
M_r = 276.33	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3155 reflections
a = 11.6326 (5) Å	θ = 2.5–28.1°
b = 6.1866 (2) Å	µ = 0.08 mm⁻¹
c = 20.1712 (8) Å	T = 173 K
β = 98.023 (2)°	Prism, red
V = 1437.44 (10) Å³	0.15 × 0.08 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2479 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 28.5°, θ_min = 2.9°
φ and ω scans	h = −15→15
13963 measured reflections	k = −8→8
3654 independent reflections	l = −27→27

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0491P)² + 0.2765P] where P = (F_o² + 2F_c²)/3
3654 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.25 e Å⁻³
7 restraints	Δρ_min = −0.23 e Å⁻³
0 constraints

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 esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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	Occ. (<1)
O1	0.53655 (9)	0.28137 (15)	0.04401 (5)	0.0423 (3)
N1	0.71280 (9)	0.43066 (15)	0.14740 (5)	0.0306 (3)
N2	0.69480 (9)	0.54119 (16)	0.09243 (6)	0.0330 (3)
C1	0.75035 (12)	0.2025 (2)	0.26821 (7)	0.0410 (5)
C2	0.77274 (15)	0.0808 (3)	0.32550 (8)	0.0542 (6)
C3	0.71594 (15)	−0.1166 (3)	0.33086 (8)	0.0572 (6)
C4	0.63748 (13)	−0.1890 (2)	0.27889 (8)	0.0450 (5)
C5	0.61249 (11)	−0.0680 (2)	0.21974 (7)	0.0331 (4)
C6	0.53071 (11)	−0.1422 (2)	0.16480 (7)	0.0353 (4)
C7	0.50626 (11)	−0.0288 (2)	0.10759 (7)	0.0347 (4)
C8	0.56216 (11)	0.17470 (19)	0.09888 (6)	0.0306 (4)
C9	0.64717 (10)	0.25164 (18)	0.15195 (6)	0.0271 (3)
C10	0.67092 (10)	0.13066 (19)	0.21396 (6)	0.0300 (4)
C11A	0.75837 (19)	0.7234 (4)	0.08101 (11)	0.0240 (6)	0.750
C12A	0.73667 (19)	0.8278 (4)	0.01928 (10)	0.0317 (6)	0.750
C13A	0.7995 (2)	1.0103 (3)	0.00825 (12)	0.0358 (6)	0.750
C14A	0.8830 (2)	1.0934 (3)	0.05681 (16)	0.0308 (7)	0.750
C15A	0.9037 (2)	0.9908 (4)	0.11911 (16)	0.0308 (7)	0.750
C16A	0.8410 (3)	0.8045 (6)	0.13063 (13)	0.0296 (8)	0.750
C17A	0.94946 (19)	1.2939 (3)	0.04259 (12)	0.0460 (7)	0.750
C18A	0.98974 (19)	1.0814 (3)	0.17419 (11)	0.0488 (7)	0.750
C17B	0.9986 (5)	1.2864 (9)	0.0922 (4)	0.0434 (19)	0.250
C11B	0.7842 (8)	0.7320 (16)	0.1026 (4)	0.0278 (12)	0.250
C12B	0.8620 (9)	0.7828 (16)	0.1558 (4)	0.029 (2)	0.250
C13B	0.9316 (6)	0.9638 (11)	0.1505 (4)	0.0309 (19)	0.250
C14B	0.9186 (6)	1.0878 (11)	0.0925 (4)	0.0277 (19)	0.250
C15B	0.8400 (7)	1.0352 (11)	0.0381 (4)	0.0278 (12)	0.250
C16B	0.7699 (5)	0.8488 (11)	0.0447 (3)	0.0278 (12)	0.250
C18B	0.8259 (5)	1.1641 (8)	−0.0252 (3)	0.0397 (17)	0.250
H1	0.78830	0.33380	0.26540	0.0490*
H16A	0.85510	0.73500	0.17190	0.0360*	0.750
H17A	0.94450	1.39880	0.07720	0.0690*	0.750
H17B	0.91670	1.35310	0.00010	0.0690*	0.750
H17C	1.02930	1.25720	0.04140	0.0690*	0.750
H18A	0.96720	1.22560	0.18440	0.0730*	0.750
H18B	1.06530	1.08450	0.16020	0.0730*	0.750
H18C	0.99190	0.99230	0.21330	0.0730*	0.750
H2	0.64080	0.49950	0.06150	0.0400*
H2A	0.82600	0.12990	0.36100	0.0650*
H3	0.73160	−0.19840	0.36980	0.0690*
H4	0.60010	−0.32030	0.28270	0.0540*
H6	0.49320	−0.27330	0.16880	0.0420*
H7	0.45240	−0.08290	0.07320	0.0420*
H12A	0.68040	0.77500	−0.01410	0.0380*	0.750
H13A	0.78520	1.07920	−0.03310	0.0430*	0.750
H12B	0.86920	0.70040	0.19470	0.0340*	0.250
H13B	0.98730	1.00200	0.18630	0.0370*	0.250
H16B	0.71430	0.80710	0.00940	0.0330*	0.250
H17D	0.95230	1.41420	0.08330	0.0650*	0.250
H17E	1.04770	1.26890	0.05800	0.0650*	0.250
H17F	1.04580	1.29960	0.13500	0.0650*	0.250
H18D	0.79660	1.30500	−0.01680	0.0600*	0.250
H18E	0.77250	1.09190	−0.05850	0.0600*	0.250
H18F	0.89980	1.17800	−0.04090	0.0600*	0.250

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0527 (6)	0.0378 (5)	0.0358 (5)	−0.0014 (5)	0.0037 (4)	0.0018 (4)
N1	0.0310 (6)	0.0229 (5)	0.0405 (6)	0.0030 (4)	0.0137 (5)	0.0008 (4)
N2	0.0350 (6)	0.0236 (5)	0.0429 (6)	0.0000 (4)	0.0146 (5)	0.0035 (5)
C1	0.0379 (8)	0.0428 (8)	0.0426 (8)	−0.0006 (6)	0.0067 (6)	0.0035 (6)
C2	0.0505 (10)	0.0671 (11)	0.0436 (9)	0.0047 (8)	0.0014 (7)	0.0092 (8)
C3	0.0562 (10)	0.0673 (11)	0.0509 (9)	0.0157 (9)	0.0169 (8)	0.0304 (8)
C4	0.0427 (8)	0.0402 (8)	0.0569 (9)	0.0067 (7)	0.0239 (7)	0.0183 (7)
C5	0.0315 (7)	0.0277 (6)	0.0442 (7)	0.0046 (5)	0.0197 (6)	0.0058 (6)
C6	0.0343 (7)	0.0210 (6)	0.0554 (9)	−0.0021 (5)	0.0233 (6)	−0.0022 (6)
C7	0.0338 (7)	0.0283 (6)	0.0438 (7)	−0.0032 (5)	0.0121 (6)	−0.0086 (6)
C8	0.0338 (7)	0.0256 (6)	0.0347 (7)	0.0023 (5)	0.0132 (5)	−0.0022 (5)
C9	0.0282 (6)	0.0207 (6)	0.0346 (6)	0.0012 (5)	0.0124 (5)	−0.0003 (5)
C10	0.0287 (6)	0.0268 (6)	0.0368 (7)	0.0044 (5)	0.0132 (5)	0.0029 (5)
C11A	0.0219 (11)	0.0186 (8)	0.0329 (13)	0.0009 (8)	0.0090 (8)	0.0007 (10)
C12A	0.0317 (11)	0.0314 (9)	0.0328 (11)	0.0002 (8)	0.0078 (8)	0.0052 (9)
C13A	0.0395 (12)	0.0331 (10)	0.0369 (11)	0.0019 (9)	0.0127 (9)	0.0109 (9)
C14A	0.0312 (13)	0.0248 (11)	0.0390 (14)	0.0043 (9)	0.0146 (10)	0.0043 (11)
C15A	0.0263 (12)	0.0271 (12)	0.0398 (14)	0.0049 (9)	0.0070 (11)	−0.0004 (12)
C16A	0.0292 (16)	0.0276 (11)	0.0326 (15)	0.0044 (10)	0.0065 (13)	0.0048 (13)
C17A	0.0479 (12)	0.0290 (9)	0.0653 (14)	−0.0034 (9)	0.0227 (11)	0.0082 (10)
C18A	0.0447 (12)	0.0417 (11)	0.0579 (13)	−0.0088 (10)	−0.0004 (10)	0.0026 (10)
C17B	0.038 (3)	0.026 (3)	0.067 (4)	−0.010 (2)	0.010 (3)	0.001 (3)
C11B	0.024 (2)	0.030 (2)	0.028 (2)	0.0008 (17)	−0.0014 (16)	−0.0009 (19)
C12B	0.023 (4)	0.023 (3)	0.039 (5)	−0.004 (3)	0.001 (4)	0.000 (4)
C13B	0.018 (3)	0.034 (3)	0.039 (4)	−0.002 (3)	−0.002 (3)	−0.005 (3)
C14B	0.032 (3)	0.022 (3)	0.032 (4)	0.002 (2)	0.015 (3)	0.011 (3)
C15B	0.024 (2)	0.030 (2)	0.028 (2)	0.0008 (17)	−0.0014 (16)	−0.0009 (19)
C16B	0.024 (2)	0.030 (2)	0.028 (2)	0.0008 (17)	−0.0014 (16)	−0.0009 (19)
C18B	0.045 (3)	0.027 (3)	0.052 (3)	−0.001 (2)	0.024 (3)	0.014 (2)

Geometric parameters (Å, º) top

O1—C8	1.2873 (15)	C15A—C18A	1.497 (4)
N1—N2	1.2946 (15)	C15A—C16A	1.401 (4)
N1—C9	1.3555 (15)	C15B—C16B	1.429 (10)
N2—C11A	1.385 (3)	C15B—C18B	1.495 (10)
N2—C11B	1.568 (10)	C1—H1	0.9300
N2—H2	0.8600	C2—H2A	0.9300
C1—C2	1.373 (2)	C3—H3	0.9300
C1—C10	1.4023 (18)	C4—H4	0.9300
C2—C3	1.400 (3)	C6—H6	0.9300
C3—C4	1.366 (2)	C7—H7	0.9300
C4—C5	1.404 (2)	C12A—H12A	0.9300
C5—C10	1.4171 (17)	C12B—H12B	0.9300
C5—C6	1.4316 (19)	C13A—H13A	0.9300
C6—C7	1.3465 (19)	C13B—H13B	0.9300
C7—C8	1.4390 (17)	C16A—H16A	0.9300
C8—C9	1.4335 (17)	C16B—H16B	0.9300
C9—C10	1.4507 (17)	C17A—H17C	0.9600
C11A—C12A	1.394 (3)	C17A—H17A	0.9600
C11A—C16A	1.382 (4)	C17A—H17B	0.9600
C11B—C16B	1.364 (11)	C17B—H17E	0.9600
C11B—C12B	1.341 (12)	C17B—H17F	0.9600
C12A—C13A	1.380 (3)	C17B—H17D	0.9600
C12B—C13B	1.395 (12)	C18A—H18C	0.9600
C13A—C14A	1.379 (4)	C18A—H18A	0.9600
C13B—C14B	1.390 (11)	C18A—H18B	0.9600
C14A—C17A	1.510 (3)	C18B—H18D	0.9600
C14A—C15A	1.398 (4)	C18B—H18E	0.9600
C14B—C17B	1.542 (9)	C18B—H18F	0.9600
C14B—C15B	1.366 (11)

N2—N1—C9	117.66 (10)	C2—C1—H1	120.00
N1—N2—C11A	123.10 (13)	C10—C1—H1	120.00
N1—N2—C11B	105.1 (3)	C1—C2—H2A	120.00
C11B—N2—H2	136.00	C3—C2—H2A	120.00
N1—N2—H2	118.00	C2—C3—H3	120.00
C11A—N2—H2	118.00	C4—C3—H3	120.00
C2—C1—C10	120.65 (13)	C3—C4—H4	120.00
C1—C2—C3	120.47 (15)	C5—C4—H4	119.00
C2—C3—C4	119.93 (15)	C5—C6—H6	119.00
C3—C4—C5	120.95 (13)	C7—C6—H6	119.00
C6—C5—C10	119.27 (12)	C6—C7—H7	119.00
C4—C5—C6	121.55 (12)	C8—C7—H7	120.00
C4—C5—C10	119.18 (12)	C11A—C12A—H12A	120.00
C5—C6—C7	122.30 (12)	C13A—C12A—H12A	120.00
C6—C7—C8	121.03 (12)	C11B—C12B—H12B	121.00
O1—C8—C7	119.95 (11)	C13B—C12B—H12B	121.00
O1—C8—C9	121.64 (11)	C12A—C13A—H13A	119.00
C7—C8—C9	118.41 (11)	C14A—C13A—H13A	119.00
N1—C9—C10	116.02 (10)	C14B—C13B—H13B	120.00
C8—C9—C10	120.07 (10)	C12B—C13B—H13B	120.00
N1—C9—C8	123.86 (11)	C15A—C16A—H16A	120.00
C1—C10—C9	122.33 (11)	C11A—C16A—H16A	120.00
C1—C10—C5	118.82 (11)	C11B—C16B—H16B	120.00
C5—C10—C9	118.85 (11)	C15B—C16B—H16B	120.00
N2—C11A—C12A	119.43 (19)	H17A—C17A—H17B	110.00
N2—C11A—C16A	120.6 (2)	H17A—C17A—H17C	110.00
C12A—C11A—C16A	120.0 (2)	C14A—C17A—H17A	109.00
N2—C11B—C12B	130.0 (8)	C14A—C17A—H17B	109.00
C12B—C11B—C16B	123.3 (9)	C14A—C17A—H17C	109.00
N2—C11B—C16B	106.7 (6)	H17B—C17A—H17C	109.00
C11A—C12A—C13A	119.3 (2)	C14B—C17B—H17D	110.00
C11B—C12B—C13B	117.5 (8)	H17D—C17B—H17E	109.00
C12A—C13A—C14A	121.8 (2)	H17D—C17B—H17F	110.00
C12B—C13B—C14B	120.8 (7)	H17E—C17B—H17F	109.00
C13A—C14A—C15A	119.0 (2)	C14B—C17B—H17E	109.00
C15A—C14A—C17A	121.0 (2)	C14B—C17B—H17F	110.00
C13A—C14A—C17A	120.0 (2)	H18B—C18A—H18C	109.00
C13B—C14B—C17B	116.6 (7)	H18A—C18A—H18B	109.00
C13B—C14B—C15B	121.8 (7)	H18A—C18A—H18C	110.00
C15B—C14B—C17B	121.6 (7)	C15A—C18A—H18A	109.00
C14A—C15A—C16A	119.6 (2)	C15A—C18A—H18B	110.00
C14A—C15A—C18A	120.7 (2)	C15A—C18A—H18C	109.00
C16A—C15A—C18A	119.7 (3)	C15B—C18B—H18D	109.00
C14B—C15B—C16B	116.4 (7)	C15B—C18B—H18E	109.00
C14B—C15B—C18B	122.7 (6)	C15B—C18B—H18F	109.00
C16B—C15B—C18B	120.9 (6)	H18D—C18B—H18E	110.00
C11A—C16A—C15A	120.3 (3)	H18D—C18B—H18F	109.00
C11B—C16B—C15B	120.3 (7)	H18E—C18B—H18F	109.00

C9—N1—N2—C11A	−178.13 (15)	O1—C8—C9—N1	−4.99 (19)
N2—N1—C9—C8	2.05 (17)	O1—C8—C9—C10	177.92 (11)
N2—N1—C9—C10	179.25 (10)	C7—C8—C9—N1	174.01 (11)
N1—N2—C11A—C12A	177.29 (17)	C7—C8—C9—C10	−3.08 (17)
N1—N2—C11A—C16A	−4.1 (3)	N1—C9—C10—C1	4.86 (17)
C10—C1—C2—C3	−0.4 (2)	N1—C9—C10—C5	−174.62 (11)
C2—C1—C10—C5	1.2 (2)	C8—C9—C10—C1	−177.83 (12)
C2—C1—C10—C9	−178.34 (13)	C8—C9—C10—C5	2.69 (17)
C1—C2—C3—C4	−0.1 (3)	N2—C11A—C12A—C13A	179.48 (19)
C2—C3—C4—C5	−0.1 (2)	C16A—C11A—C12A—C13A	0.8 (4)
C3—C4—C5—C6	179.81 (14)	N2—C11A—C16A—C15A	−179.0 (2)
C3—C4—C5—C10	0.8 (2)	C12A—C11A—C16A—C15A	−0.4 (4)
C4—C5—C6—C7	−179.60 (13)	C11A—C12A—C13A—C14A	−0.4 (3)
C10—C5—C6—C7	−0.6 (2)	C12A—C13A—C14A—C15A	−0.6 (3)
C4—C5—C10—C1	−1.30 (19)	C12A—C13A—C14A—C17A	−179.8 (2)
C4—C5—C10—C9	178.20 (12)	C13A—C14A—C15A—C16A	1.1 (4)
C6—C5—C10—C1	179.63 (12)	C13A—C14A—C15A—C18A	−177.2 (2)
C6—C5—C10—C9	−0.87 (18)	C17A—C14A—C15A—C16A	−179.7 (2)
C5—C6—C7—C8	0.1 (2)	C17A—C14A—C15A—C18A	2.0 (3)
C6—C7—C8—O1	−179.29 (12)	C14A—C15A—C16A—C11A	−0.6 (4)
C6—C7—C8—C9	1.69 (19)	C18A—C15A—C16A—C11A	177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.82	2.5347 (15)	140
C12A—H12A···O1ⁱ	0.93	2.54	3.325 (2)	143

Symmetry code: (i) −x+1, −y+1, −z.

Funding information

Funding for this research was provided by: Ministère de l'Enseignement Supérieur et de la Recherche ScientifiqueDirection Générale de la Recherche Scientifique et du Développement TechnologiqueUniversity of Constantine

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