1-(Cyclo­hex-1-en-1-yl)-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)meth­yl]-1H-benzimidazol-2(3H)-one

Adardour, M.; Loughzail, M.; Dahaoui, S.; Baouid, A.; Berraho, M.

doi:10.1107/S2414314617009075

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170907

https://doi.org/10.1107/S2414314617009075

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1-(Cyclohex-1-en-1-yl)-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzimidazol-2(3H)-one

Mohamed Adardour,^a Mohamed Loughzail,^a ^* Slimane Dahaoui,^b Abdesselam Baouid ^a and Moha Berraho ^c

^aLaboratoire de Chimie Moléculaire, Département de Chimie, Faculté des Sciences Semlalia, BP 2390, Université Cadi Ayyad, 40001 Marrakech, Morocco, ^bCristallographie, Résonance Magnétique et Modélisation (CRM2), Université Henri Poincaré, Nancy 1, Faculté des Sciences, BP 70239, 54506 Vandoeuvre lès Nancy Cedex, France, and ^cLaboratoire de Chimie des Substances Naturelles, Unité Associé au CNRST (URAC16), Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, Université Cadi Ayyad, 40000 Marrakech, Morocco
^*Correspondence e-mail: loughzail@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 13 June 2017; accepted 17 June 2017; online 23 June 2017)

In the title compound, C₂₂H₂₁N₅O, the triazole ring is inclined at 16.88 (12)° to its phenyl substituent and is almost normal to the benzimidazole ring system, making a dihedral angle of 88.40 (8)°. The cyclohexenyl ring adopts a half-chair conformation and its mean plane is inclined to the benzimidazole ring system by 78.75 (12)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure; benzimidazolone; benzyl azide; triazole; hydrogen bonding.

CCDC reference: 1556697

Structure description

Heterocyclic triazole derivatives are important components of materials with both agrochemical (Bowyer & Denning, 2014 ) and medicinal (Kumar et al., 2013 ) applications. 1,2,3-Triazoles display a wide range of interesting biological activities, and are used as anti-inflammatory (De Simone et al., 2011 ), anti-allergic (Buckle et al., 1986 ) and anti-HIV agents (Giffin et al., 2008 ; Whiting et al., 2006 ). They are also effective in the inhibition of histidine biosynthesis (Ventura et al., 1997 ). The most widely used method for the synthesis of 1,2,3-triazoles is the Huisgen (1963 ) 1,3-dipolar cycloaddition of alkynes with organic azides. The condensation reaction of 1-cyclohexenyl-3-prop-2-ynyl-1,3-dihydro-benzoimidazol-2-one with azidobenzene in the presence of copper iodide (CuI) under reflux in acetonitrile for one hour gives a single regioisomer of the title compound in good yield.

The molecular structure of the title compound is illustrated in Fig. 1. The triazole ring (N3/N4/N5/C10/C9) is almost normal to the plane of the benzimidazole ring system, making a dihedral angle of 88.36 (8)°. The cyclohexenyl ring (C17/C18–C22), displays a half chair conformation, as indicated by the total puckering amplitude Q_T = 0.494 (3) Å and the spherical polar angle θ₂ = 52.3 (3)° with φ₂ = 144.4 (4)°. This ring makes a dihedral angle of 78.75 (12)° with the benzimidazole ring system.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, pairs of C16—H16⋯N4 and C10—H10⋯O1 hydrogen bonds (Table 1) each form inversion dimers, enclosing R₂²(10) and R₂²(14) rings, respectively. These combine with an additional C4—H4⋯O2 hydrogen bond to link the molecules into a three-dimensional network, as shown in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.93	2.53	3.303 (2)	141
C16—H16⋯N4ⁱⁱ	0.93	2.62	3.413 (3)	144
C10—H10⋯O1ⁱⁱⁱ	0.93	2.26	3.174 (2)	167
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+2; (iii) -x+1, -y, -z+1.

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

Synthesis and crystallization

To a solution of 1-cyclohexenyl-3-prop-2-ynyl-1,3-dihydro-benzoimidazol-2-one (3.96 mmole) dissolved in acetonitrile was added azidobenzene (4.69 mmol), in the presence of CuI. The mixture was refluxed for 1 h; the reaction was monitored by thin layer chromatography. The mixture was filtered and the solvent removed under vacuum. The solid was purified by column chromatography on silica gel using hexane/ethyl acetate as eluent. The solid product was recrystallized from ethanol solution.

¹H NMR (300 MHz, CDCl₃), δ (p.p.m.): 1.78, 1.90, 2.33, 2.43 (4 m, 8H, CH₂–cyclohexenyl), 5.31 (s, 2H, N—CH2), 5.98 (m, 1H, C=CH; H–cyclohexenyl), 7.06–7,74 (m, 9H, H—Ar), 8.09 (s, 1H, H-triazolic). ¹³C NMR (75 MHz, CDCl₃), δ (p.p.m.): 21.66, 22.60, 24.73, 26.85 (4 C, CH₂–cyclohexenyl), 36.35 (N—CH₂), 127.36 (CH=C, C–cyclohexenyl), 121.21 (N—CH=C, C-triazolic), 108.68, 120.56, 121.58, 128.89, 129.74 (C, CH=C, C—Ar), 121.67, 129.53, 132.21, 136.92, 144.00 (6C, =C–), 152,92 (1C, C=O).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₁N₅O
M_r	371.43
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	8.5878 (8), 9.0603 (8), 12.8566 (12)
α, β, γ (°)	85.076 (7), 82.558 (7), 70.917 (8)
V (Å³)	936.40 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.20 × 0.15

Data collection
Diffractometer	Bruker X8 APEX Diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.811, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	5162, 3592, 2866
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.143, 1.03
No. of reflections	3592
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1556697

Crystal structure: contains datablocks I, block. DOI: https://doi.org/10.1107/S2414314617009075/sj4122sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617009075/sj4122Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617009075/sj4122Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

1-(Cyclohex-1-en-1-yl)-3-[(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzimidazol-2(3H)-one top

Crystal data top

C₂₂H₂₁N₅O	Z = 2
M_r = 371.43	F(000) = 392
Triclinic, P1	D_x = 1.317 Mg m⁻³
a = 8.5878 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0603 (8) Å	Cell parameters from 3592 reflections
c = 12.8566 (12) Å	θ = 3.1–26.4°
α = 85.076 (7)°	µ = 0.09 mm⁻¹
β = 82.558 (7)°	T = 293 K
γ = 70.917 (8)°	Block, colourless
V = 936.40 (16) Å³	0.48 × 0.20 × 0.15 mm

Data collection top

Bruker X8 APEX Diffractometer	2866 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.029
φ and ω scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→8
T_min = 0.811, T_max = 1.0	k = −11→11
5162 measured reflections	l = −10→16
3592 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.143	w = 1/[σ²(F_o²) + (0.0628P)² + 0.6025P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3592 reflections	Δρ_max = 0.67 e Å⁻³
253 parameters	Δρ_min = −0.30 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.

Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (methylene), 0.98 Å (methyl), 1.0Å (methine) with U_iso(H) = 1.2U_eq(CH and CH₂). The coordinates of H atoms attached to N atoms were freely refined with U_iso(H) = 1.2U_eq(N) and the H attached to hydroxyl O atoms were fixed geometrically and treated as riding with O—H = 0.84Å and U_iso(H) = 1.5U_eq(O).

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

	x	y	z	U_iso*/U_eq
C12	0.3923 (3)	−0.3191 (2)	0.80138 (16)	0.0229 (5)
H12	0.4612	−0.2984	0.7440	0.028*
C16	0.1680 (3)	−0.2279 (3)	0.93894 (17)	0.0280 (5)
H16	0.0878	−0.1458	0.9733	0.034*
C21	0.3016 (3)	0.1477 (3)	0.10909 (17)	0.0319 (5)
H21A	0.3956	0.1775	0.0756	0.038*
H21B	0.2138	0.1851	0.0635	0.038*
C18	0.2255 (3)	−0.0204 (2)	0.30745 (17)	0.0315 (5)
H18A	0.1314	−0.0343	0.3528	0.038*
H18B	0.3255	−0.0812	0.3385	0.038*
C19	0.2295 (3)	−0.0802 (3)	0.19899 (19)	0.0332 (5)
H19A	0.2611	−0.1934	0.2033	0.040*
H19B	0.1199	−0.0393	0.1754	0.040*
C14	0.3050 (3)	−0.5029 (3)	0.92148 (19)	0.0363 (6)
H14	0.3161	−0.6057	0.9442	0.044*
C15	0.1856 (3)	−0.3810 (3)	0.97239 (19)	0.0361 (6)
H15	0.1166	−0.4022	1.0295	0.043*
C20	0.3520 (3)	−0.0292 (3)	0.12117 (18)	0.0321 (5)
H20A	0.3574	−0.0717	0.0536	0.039*
H20B	0.4613	−0.0699	0.1451	0.039*
C13	0.4079 (3)	−0.4719 (3)	0.83683 (19)	0.0324 (5)
H13	0.4887	−0.5542	0.8031	0.039*
C22	0.2430 (3)	0.2252 (3)	0.21187 (17)	0.0300 (5)
H22	0.2268	0.3316	0.2137	0.036*
O1	0.43046 (16)	0.19506 (16)	0.44443 (11)	0.0200 (3)
N1	0.1877 (2)	0.29311 (18)	0.55563 (12)	0.0159 (3)
N2	0.1672 (2)	0.22461 (19)	0.39825 (13)	0.0170 (4)
N5	0.2507 (2)	−0.03975 (19)	0.81699 (12)	0.0168 (4)
N4	0.1623 (2)	0.0792 (2)	0.87935 (13)	0.0226 (4)
C1	0.0200 (2)	0.3188 (2)	0.54935 (15)	0.0163 (4)
C2	−0.1186 (2)	0.3784 (2)	0.61908 (16)	0.0191 (4)
H2	−0.1105	0.4075	0.6853	0.023*
C6	0.0074 (2)	0.2742 (2)	0.45008 (15)	0.0165 (4)
N3	0.1596 (2)	0.2099 (2)	0.82603 (13)	0.0231 (4)
C10	0.3051 (2)	0.0162 (2)	0.72346 (15)	0.0179 (4)
H10	0.3686	−0.0407	0.6671	0.021*
C7	0.2799 (2)	0.2326 (2)	0.46372 (15)	0.0164 (4)
C8	0.2612 (2)	0.3012 (2)	0.64997 (15)	0.0180 (4)
H8A	0.2064	0.4025	0.6797	0.022*
H8B	0.3774	0.2906	0.6317	0.022*
C11	0.2720 (2)	−0.1982 (2)	0.85310 (15)	0.0190 (4)
C9	0.2458 (2)	0.1753 (2)	0.73019 (15)	0.0163 (4)
C5	−0.1435 (3)	0.2862 (2)	0.41806 (16)	0.0207 (4)
H5	−0.1512	0.2551	0.3524	0.025*
C17	0.2133 (2)	0.1475 (2)	0.30030 (15)	0.0169 (4)
C3	−0.2715 (2)	0.3932 (2)	0.58592 (17)	0.0224 (4)
H3	−0.3676	0.4351	0.6306	0.027*
C4	−0.2841 (3)	0.3470 (2)	0.48808 (17)	0.0225 (5)
H4	−0.3879	0.3567	0.4690	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C12	0.0240 (11)	0.0246 (11)	0.0192 (10)	−0.0076 (9)	−0.0007 (8)	0.0013 (8)
C16	0.0344 (13)	0.0270 (11)	0.0227 (11)	−0.0129 (10)	0.0054 (9)	−0.0021 (9)
C21	0.0428 (14)	0.0381 (13)	0.0183 (11)	−0.0185 (11)	−0.0018 (10)	−0.0001 (9)
C18	0.0492 (15)	0.0207 (11)	0.0211 (11)	−0.0067 (10)	−0.0038 (10)	0.0003 (9)
C19	0.0457 (15)	0.0244 (11)	0.0303 (13)	−0.0120 (10)	−0.0033 (11)	−0.0033 (9)
C14	0.0582 (17)	0.0238 (12)	0.0281 (12)	−0.0177 (11)	0.0003 (11)	0.0037 (9)
C15	0.0497 (16)	0.0322 (13)	0.0276 (12)	−0.0204 (12)	0.0085 (11)	0.0020 (10)
C20	0.0310 (12)	0.0407 (14)	0.0251 (12)	−0.0096 (11)	−0.0021 (9)	−0.0127 (10)
C13	0.0435 (14)	0.0206 (11)	0.0286 (12)	−0.0060 (10)	0.0007 (10)	−0.0018 (9)
C22	0.0463 (14)	0.0250 (11)	0.0227 (11)	−0.0168 (10)	−0.0048 (10)	0.0002 (9)
O1	0.0151 (7)	0.0224 (7)	0.0216 (7)	−0.0051 (6)	0.0006 (5)	−0.0039 (6)
N1	0.0161 (8)	0.0175 (8)	0.0148 (8)	−0.0058 (6)	−0.0022 (6)	−0.0011 (6)
N2	0.0167 (8)	0.0190 (8)	0.0159 (8)	−0.0059 (7)	−0.0015 (6)	−0.0031 (6)
N5	0.0183 (8)	0.0190 (8)	0.0135 (8)	−0.0065 (7)	−0.0017 (6)	−0.0011 (6)
N4	0.0283 (10)	0.0211 (9)	0.0167 (9)	−0.0065 (7)	0.0022 (7)	−0.0033 (7)
C1	0.0181 (10)	0.0128 (9)	0.0181 (10)	−0.0059 (7)	−0.0021 (7)	0.0026 (7)
C2	0.0217 (10)	0.0166 (10)	0.0176 (10)	−0.0057 (8)	0.0002 (8)	0.0016 (8)
C6	0.0175 (10)	0.0141 (9)	0.0181 (10)	−0.0060 (8)	−0.0007 (7)	0.0012 (7)
N3	0.0284 (10)	0.0205 (9)	0.0184 (9)	−0.0057 (7)	−0.0001 (7)	−0.0018 (7)
C10	0.0193 (10)	0.0223 (10)	0.0123 (9)	−0.0075 (8)	0.0001 (7)	−0.0019 (7)
C7	0.0189 (10)	0.0139 (9)	0.0157 (9)	−0.0048 (8)	−0.0011 (7)	0.0000 (7)
C8	0.0214 (10)	0.0187 (10)	0.0157 (10)	−0.0078 (8)	−0.0041 (8)	−0.0014 (7)
C11	0.0230 (10)	0.0198 (10)	0.0166 (10)	−0.0093 (8)	−0.0062 (8)	0.0015 (8)
C9	0.0159 (9)	0.0203 (10)	0.0139 (9)	−0.0067 (8)	−0.0033 (7)	−0.0015 (7)
C5	0.0236 (11)	0.0179 (10)	0.0226 (10)	−0.0080 (8)	−0.0076 (8)	0.0009 (8)
C17	0.0161 (9)	0.0179 (10)	0.0167 (9)	−0.0050 (8)	−0.0016 (7)	−0.0028 (7)
C3	0.0174 (10)	0.0199 (10)	0.0265 (11)	−0.0042 (8)	0.0025 (8)	0.0025 (8)
C4	0.0168 (10)	0.0207 (10)	0.0300 (11)	−0.0067 (8)	−0.0040 (8)	0.0051 (8)

Geometric parameters (Å, º) top

C12—C11	1.384 (3)	N1—C7	1.382 (2)
C12—C13	1.388 (3)	N1—C1	1.394 (2)
C12—H12	0.9300	N1—C8	1.455 (2)
C16—C15	1.382 (3)	N2—C7	1.385 (2)
C16—C11	1.392 (3)	N2—C6	1.393 (2)
C16—H16	0.9300	N2—C17	1.439 (2)
C21—C22	1.500 (3)	N5—C10	1.351 (2)
C21—C20	1.517 (3)	N5—N4	1.355 (2)
C21—H21A	0.9700	N5—C11	1.431 (2)
C21—H21B	0.9700	N4—N3	1.312 (2)
C18—C17	1.486 (3)	C1—C2	1.378 (3)
C18—C19	1.531 (3)	C1—C6	1.399 (3)
C18—H18A	0.9700	C2—C3	1.394 (3)
C18—H18B	0.9700	C2—H2	0.9300
C19—C20	1.512 (3)	C6—C5	1.378 (3)
C19—H19A	0.9700	N3—C9	1.358 (3)
C19—H19B	0.9700	C10—C9	1.370 (3)
C14—C13	1.380 (3)	C10—H10	0.9300
C14—C15	1.381 (4)	C8—C9	1.498 (3)
C14—H14	0.9300	C8—H8A	0.9700
C15—H15	0.9300	C8—H8B	0.9700
C20—H20A	0.9700	C5—C4	1.393 (3)
C20—H20B	0.9700	C5—H5	0.9300
C13—H13	0.9300	C3—C4	1.387 (3)
C22—C17	1.326 (3)	C3—H3	0.9300
C22—H22	0.9300	C4—H4	0.9300
O1—C7	1.222 (2)

C11—C12—C13	118.7 (2)	C7—N2—C17	123.90 (16)
C11—C12—H12	120.7	C6—N2—C17	125.19 (16)
C13—C12—H12	120.7	C10—N5—N4	110.57 (16)
C15—C16—C11	119.1 (2)	C10—N5—C11	129.19 (17)
C15—C16—H16	120.5	N4—N5—C11	120.23 (16)
C11—C16—H16	120.5	N3—N4—N5	107.21 (16)
C22—C21—C20	112.85 (19)	C2—C1—N1	131.87 (18)
C22—C21—H21A	109.0	C2—C1—C6	121.32 (18)
C20—C21—H21A	109.0	N1—C1—C6	106.80 (17)
C22—C21—H21B	109.0	C1—C2—C3	117.01 (18)
C20—C21—H21B	109.0	C1—C2—H2	121.5
H21A—C21—H21B	107.8	C3—C2—H2	121.5
C17—C18—C19	111.21 (18)	C5—C6—N2	131.24 (18)
C17—C18—H18A	109.4	C5—C6—C1	121.64 (19)
C19—C18—H18A	109.4	N2—C6—C1	107.10 (16)
C17—C18—H18B	109.4	N4—N3—C9	108.87 (16)
C19—C18—H18B	109.4	N5—C10—C9	104.52 (17)
H18A—C18—H18B	108.0	N5—C10—H10	127.7
C20—C19—C18	110.10 (19)	C9—C10—H10	127.7
C20—C19—H19A	109.6	O1—C7—N1	126.60 (18)
C18—C19—H19A	109.6	O1—C7—N2	127.29 (18)
C20—C19—H19B	109.6	N1—C7—N2	106.11 (16)
C18—C19—H19B	109.6	N1—C8—C9	111.45 (15)
H19A—C19—H19B	108.2	N1—C8—H8A	109.3
C13—C14—C15	119.9 (2)	C9—C8—H8A	109.3
C13—C14—H14	120.0	N1—C8—H8B	109.3
C15—C14—H14	120.0	C9—C8—H8B	109.3
C14—C15—C16	120.4 (2)	H8A—C8—H8B	108.0
C14—C15—H15	119.8	C12—C11—C16	121.16 (19)
C16—C15—H15	119.8	C12—C11—N5	119.89 (18)
C19—C20—C21	110.9 (2)	C16—C11—N5	118.93 (19)
C19—C20—H20A	109.5	N3—C9—C10	108.83 (17)
C21—C20—H20A	109.5	N3—C9—C8	121.42 (17)
C19—C20—H20B	109.5	C10—C9—C8	129.73 (18)
C21—C20—H20B	109.5	C6—C5—C4	117.29 (19)
H20A—C20—H20B	108.0	C6—C5—H5	121.4
C14—C13—C12	120.8 (2)	C4—C5—H5	121.4
C14—C13—H13	119.6	C22—C17—N2	120.40 (18)
C12—C13—H13	119.6	C22—C17—C18	124.28 (19)
C17—C22—C21	122.4 (2)	N2—C17—C18	115.31 (17)
C17—C22—H22	118.8	C4—C3—C2	121.76 (19)
C21—C22—H22	118.8	C4—C3—H3	119.1
C7—N1—C1	110.11 (15)	C2—C3—H3	119.1
C7—N1—C8	123.32 (16)	C3—C4—C5	120.95 (19)
C1—N1—C8	125.74 (16)	C3—C4—H4	119.5
C7—N2—C6	109.84 (16)	C5—C4—H4	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.93	2.53	3.303 (2)	141
C16—H16···N4ⁱⁱ	0.93	2.62	3.413 (3)	144
C10—H10···O1ⁱⁱⁱ	0.93	2.26	3.174 (2)	167

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

Acknowledgements

The authors thank the Laboratoire de Cristallographie, Résonance Magnétique et Modélization (CRM2), Université Henri Poincaré, Nancy 1, Faculté des Sciences, BP 70239, 54506 Vandoeuvre lès Nancy CEDEX, France, for the data collection.

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