4-[(1H-Imidazol-1-yl)meth­yl]-1-(4-nitro­benz­yl)-1H-1,2,3-triazole

Sahbi, A.; Mague, J.T.; Ben-Tama, A.; El Hadrami, E.M.; Gaamoussi, I.; Ouzidan, Y.

doi:10.1107/S2414314617005156

organic compounds

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ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170515

https://doi.org/10.1107/S2414314617005156

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4-[(1H-Imidazol-1-yl)methyl]-1-(4-nitrobenzyl)-1H-1,2,3-triazole

Azzeddine Sahbi,^a ^* Joel T. Mague,^b Abdeslem Ben-Tama,^a El Mestafa El Hadrami,^a Issam Gaamoussi ^a and Younes Ouzidan ^a

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: azzeddinesahbi1982@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 26 March 2017; accepted 3 April 2017; online 7 April 2017)

The title molecule, C₁₃H₁₂N₆O₂, adopts a slightly twisted zigzag conformation in the crystal, with the dihedral angles between the central triazole ring and the 4-nitrophenyl and imidazole rings being 79.81 (11) and 81.21 (13)°, respectively. The packing features weak C—H⋯O and C—H⋯N hydrogen bonds, as well as unusual N=O⋯π stacking interactions.

Keywords: crystal structure; triazole; imidazole; hydrogen bond.

CCDC reference: 1541939

Structure description

Triazoles and their derivatives are of great importance in medicinal chemistry and can be used for the synthesis of numerous heterocyclic compounds with different biological activities, including antimicrobial (Sheremet et al. 2004 ), cytotoxic (Sanghvi et al., 1990 ) and antibacterial activities (Sebbar et al., 2016 ). They have also been reported to be inhibitors of glycogen synthase kinase-3 (Olesen et al., 2003 ) and agonists of muscarine receptors (Moltzen et al., 1994 ). Herein we report the synthesis of 4-[(1H-imidazol-1-yl)methyl]-1-(4-nitrobenzyl)-1H-1,2,3-triazole by the 1,3-dipolar cycloaddition reaction of 1-(azidomethyl)-4-nitrobenzene with 1-(prop-2-yn-1-yl)-1H-imidazole.

The title molecule adopts a slightly twisted, zigzag conformation (Fig. 1) with the dihedral angles between the mean plane of the N2–N4/C8/C9 ring and those of the C1–C6 and N5/N6/C11–C13 rings being, 79.81 (11) and 81.21 (13)°, respectively. The crystal packing features weak C—H⋯O and C—H⋯N hydrogen bonds (Table 1, Figs. 2 and 3). In addition, unusual Cg1⋯Cg2^v contacts, where Cg1 is the centroid of the C1–C6 ring and Cg2^v is the mid-point of the N1=O2 bond [Cg1⋯Cg2 = 2.540 Å; symmetry code: (v) x, y, z − 1] link molecules into chains along the c-axis direction (Fig. 4). An N—O⋯π interaction is also observed: O2⋯Cg1 = 3.626 (2) Å, N1⋯Cg1 = 3.5578 (19) Å and N1—O2⋯Cg1 = 77.05 (12)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.98 (2)	2.55 (2)	3.189 (2)	123.0 (18)
C7—H7B⋯N6ⁱⁱ	0.95 (3)	2.60 (3)	3.478 (3)	154 (2)
C11—H11⋯O2ⁱⁱⁱ	0.98 (3)	2.66 (3)	3.535 (3)	149 (2)
C6—H6⋯N3^iv	1.00 (2)	2.54 (3)	3.299 (3)	133 (2)
Symmetry codes: (i) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+1]$ ; (iv) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The title molecule with labeling scheme and 50% probability ellipsoids.

Figure 2
Details of the intermolecular C—H⋯O and C—H⋯N hydrogen bonds shown, respectively, as purple and black dashed lines. For symmetry codes see Table 1

Figure 3
Overall packing viewed along the c-axis direction with hydrogen bonds depicted as in Fig. 2

Figure 4
Details of the N=O⋯π(ring) interactions (dashed lines).

Synthesis and crystallization

In a vial fitted with a screw cap, 1-(azidomethyl)-4-nitrobenzene (100 mg, 0.56 mmol) and 1-(prop-2-yn-1-yl)-1H-imidazole (62.5 mg, 0.58 mmol) were added to a mixture of copper(II) sulfate pentahydrate (7 mg, 0.028 mmol), sodium ascorbate (16.6 mg, 0.083 mmol), and β-cyclodextrin (15.9 mg, 0.014 mmol) dissolved in H₂O (1 ml) at room temperature. The reaction mixture was stirred for 15 min at room temperature. The resulting mixture was poured into CH₂Cl₂ (3 ml) and H₂O (3 ml) and the organic layer was separated. The aqueous layer was extracted with CH₂Cl₂ (3 ml) three times. The product was obtained as colorless crystals in 94% yield.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₆O₂
M_r	284.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	150
a, b, c (Å)	20.3330 (4), 14.2764 (3), 4.5089 (1)
V (Å³)	1308.85 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.86
Crystal size (mm)	0.12 × 0.06 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.88, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	10013, 2611, 2410
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 1.05
No. of reflections	2611
No. of parameters	239
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12
Absolute structure	Flack x determined using 956 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.10 (15)
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1541939

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617005156/sj4100sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005156/sj4100Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005156/sj4100Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617005156/sj4100Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-[(1H-Imidazol-1-yl)methyl]-1-(4-nitrobenzyl)-1H-1,2,3-triazole top

Crystal data top

C₁₃H₁₂N₆O₂	D_x = 1.443 Mg m⁻³
M_r = 284.29	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna2₁	Cell parameters from 8050 reflections
a = 20.3330 (4) Å	θ = 3.8–74.4°
b = 14.2764 (3) Å	µ = 0.86 mm⁻¹
c = 4.5089 (1) Å	T = 150 K
V = 1308.85 (5) Å³	Column, colourless
Z = 4	0.12 × 0.06 × 0.04 mm
F(000) = 592

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2611 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2410 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.5°, θ_min = 3.8°
ω scans	h = −25→23
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −17→17
T_min = 0.88, T_max = 0.96	l = −5→5
10013 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0321P)² + 0.151P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.070	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.12 e Å⁻³
2611 reflections	Δρ_min = −0.12 e Å⁻³
239 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0044 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 956 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.10 (15)

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. 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
O1	0.40535 (8)	0.03081 (10)	0.1143 (4)	0.0449 (4)
O2	0.34070 (8)	0.14915 (12)	0.0656 (6)	0.0567 (5)
N1	0.38941 (8)	0.11157 (12)	0.1721 (4)	0.0344 (4)
N2	0.59199 (8)	0.39660 (11)	0.7619 (4)	0.0284 (3)
N3	0.57204 (8)	0.48647 (12)	0.7668 (5)	0.0339 (4)
N4	0.61097 (8)	0.53343 (11)	0.5897 (4)	0.0335 (4)
N5	0.75335 (8)	0.57154 (12)	0.4154 (4)	0.0327 (4)
N6	0.80031 (10)	0.70206 (14)	0.5784 (6)	0.0528 (5)
H6	0.4522 (12)	0.3802 (17)	0.622 (7)	0.049 (7)*
C1	0.51128 (9)	0.26847 (13)	0.7407 (4)	0.0286 (4)
C2	0.52185 (10)	0.17309 (14)	0.7039 (5)	0.0320 (4)
H2	0.5594 (12)	0.1453 (17)	0.805 (6)	0.038 (6)*
C3	0.48152 (10)	0.12100 (14)	0.5201 (5)	0.0316 (4)
H3	0.4875 (12)	0.0537 (16)	0.492 (6)	0.039 (6)*
C4	0.43084 (9)	0.16574 (13)	0.3753 (4)	0.0285 (4)
C5	0.41831 (10)	0.26072 (13)	0.4096 (5)	0.0311 (4)
H5	0.3822 (13)	0.2882 (17)	0.298 (6)	0.043 (7)*
C6	0.45909 (9)	0.31160 (13)	0.5940 (5)	0.0319 (4)
C7	0.55609 (11)	0.32640 (15)	0.9344 (5)	0.0336 (4)
H7B	0.5873 (12)	0.2880 (16)	1.032 (7)	0.043 (7)*
H7A	0.5293 (12)	0.3618 (17)	1.084 (7)	0.044 (6)*
C8	0.64394 (9)	0.38588 (13)	0.5772 (5)	0.0317 (4)
H8	0.6659 (13)	0.3258 (19)	0.555 (8)	0.054 (7)*
C9	0.65557 (9)	0.47370 (14)	0.4683 (4)	0.0298 (4)
C10	0.70753 (10)	0.50886 (16)	0.2624 (5)	0.0370 (5)
H10A	0.7336 (12)	0.4564 (18)	0.173 (6)	0.048 (7)*
H10B	0.6876 (13)	0.5447 (17)	0.095 (8)	0.052 (7)*
C11	0.80043 (10)	0.54527 (16)	0.6156 (5)	0.0371 (5)
H11	0.8066 (13)	0.4795 (18)	0.667 (6)	0.052 (8)*
C12	0.82835 (11)	0.62560 (17)	0.7119 (6)	0.0436 (5)
H12	0.8633 (14)	0.6326 (19)	0.854 (8)	0.061 (9)*
C13	0.75485 (11)	0.66629 (16)	0.4020 (6)	0.0443 (5)
H13	0.7231 (14)	0.7000 (18)	0.274 (8)	0.059 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0482 (9)	0.0308 (8)	0.0556 (10)	0.0012 (6)	−0.0044 (8)	−0.0094 (7)
O2	0.0456 (9)	0.0427 (9)	0.0819 (14)	0.0054 (7)	−0.0269 (10)	−0.0052 (10)
N1	0.0338 (8)	0.0297 (9)	0.0396 (11)	−0.0019 (7)	−0.0001 (7)	−0.0005 (7)
N2	0.0324 (8)	0.0256 (8)	0.0271 (8)	−0.0006 (6)	−0.0003 (7)	−0.0004 (7)
N3	0.0363 (8)	0.0265 (8)	0.0388 (9)	0.0011 (7)	0.0046 (8)	−0.0026 (8)
N4	0.0355 (8)	0.0289 (8)	0.0361 (9)	0.0012 (7)	0.0019 (8)	0.0007 (8)
N5	0.0309 (8)	0.0378 (9)	0.0294 (8)	−0.0041 (7)	0.0007 (7)	0.0024 (8)
N6	0.0511 (11)	0.0437 (11)	0.0638 (14)	−0.0126 (9)	−0.0085 (11)	0.0014 (11)
C1	0.0319 (9)	0.0278 (9)	0.0260 (9)	−0.0025 (7)	0.0047 (8)	0.0026 (8)
C2	0.0334 (9)	0.0296 (10)	0.0329 (11)	0.0033 (8)	0.0005 (8)	0.0038 (8)
C3	0.0343 (10)	0.0246 (10)	0.0360 (11)	0.0031 (8)	0.0019 (8)	0.0010 (8)
C4	0.0279 (9)	0.0265 (9)	0.0309 (10)	−0.0028 (7)	0.0031 (7)	−0.0001 (8)
C5	0.0310 (9)	0.0277 (10)	0.0345 (10)	0.0049 (8)	0.0007 (9)	0.0015 (9)
C6	0.0356 (9)	0.0242 (9)	0.0359 (10)	0.0022 (8)	0.0018 (9)	0.0009 (8)
C7	0.0418 (11)	0.0319 (10)	0.0270 (10)	−0.0053 (9)	−0.0004 (9)	0.0031 (9)
C8	0.0331 (9)	0.0294 (10)	0.0326 (10)	0.0032 (8)	0.0003 (9)	−0.0041 (9)
C9	0.0325 (9)	0.0307 (10)	0.0262 (10)	−0.0017 (8)	−0.0023 (8)	−0.0035 (8)
C10	0.0376 (11)	0.0449 (12)	0.0284 (10)	−0.0076 (10)	0.0004 (9)	−0.0014 (10)
C11	0.0331 (10)	0.0447 (12)	0.0333 (11)	0.0009 (9)	0.0011 (9)	0.0048 (10)
C12	0.0343 (10)	0.0543 (14)	0.0422 (13)	−0.0087 (10)	−0.0033 (10)	0.0033 (11)
C13	0.0421 (12)	0.0383 (12)	0.0526 (14)	−0.0043 (10)	−0.0047 (11)	0.0062 (12)

Geometric parameters (Å, º) top

O1—N1	1.226 (2)	C3—C4	1.377 (3)
O2—N1	1.225 (2)	C3—H3	0.98 (2)
N1—C4	1.465 (3)	C4—C5	1.388 (3)
N2—N3	1.346 (2)	C5—C6	1.381 (3)
N2—C8	1.354 (3)	C5—H5	0.97 (3)
N2—C7	1.464 (3)	C6—H6	1.00 (2)
N3—N4	1.309 (3)	C7—H7B	0.95 (3)
N4—C9	1.360 (3)	C7—H7A	1.00 (3)
N5—C13	1.354 (3)	C8—C9	1.367 (3)
N5—C11	1.368 (3)	C8—H8	0.97 (3)
N5—C10	1.465 (3)	C9—C10	1.493 (3)
N6—C13	1.322 (3)	C10—H10A	1.00 (3)
N6—C12	1.371 (3)	C10—H10B	1.00 (3)
C1—C2	1.389 (3)	C11—C12	1.351 (3)
C1—C6	1.394 (3)	C11—H11	0.98 (3)
C1—C7	1.509 (3)	C12—H12	0.96 (3)
C2—C3	1.383 (3)	C13—H13	0.99 (3)
C2—H2	0.97 (2)

O2—N1—O1	122.87 (19)	C1—C6—H6	118.7 (16)
O2—N1—C4	118.62 (17)	N2—C7—C1	111.65 (17)
O1—N1—C4	118.51 (16)	N2—C7—H7B	108.0 (15)
N3—N2—C8	110.68 (16)	C1—C7—H7B	110.9 (15)
N3—N2—C7	119.58 (17)	N2—C7—H7A	106.5 (14)
C8—N2—C7	129.69 (17)	C1—C7—H7A	109.7 (14)
N4—N3—N2	107.21 (16)	H7B—C7—H7A	110 (2)
N3—N4—C9	109.13 (16)	N2—C8—C9	104.62 (17)
C13—N5—C11	106.72 (19)	N2—C8—H8	121.6 (18)
C13—N5—C10	127.11 (19)	C9—C8—H8	133.7 (18)
C11—N5—C10	126.05 (19)	N4—C9—C8	108.36 (17)
C13—N6—C12	104.3 (2)	N4—C9—C10	120.75 (18)
C2—C1—C6	119.61 (19)	C8—C9—C10	130.85 (19)
C2—C1—C7	120.89 (18)	N5—C10—C9	111.25 (18)
C6—C1—C7	119.49 (18)	N5—C10—H10A	108.0 (15)
C3—C2—C1	120.49 (19)	C9—C10—H10A	111.9 (15)
C3—C2—H2	121.8 (14)	N5—C10—H10B	107.5 (15)
C1—C2—H2	117.7 (14)	C9—C10—H10B	110.8 (16)
C4—C3—C2	118.59 (18)	H10A—C10—H10B	107 (2)
C4—C3—H3	119.2 (14)	C12—C11—N5	105.9 (2)
C2—C3—H3	122.2 (14)	C12—C11—H11	133.4 (16)
C3—C4—C5	122.51 (19)	N5—C11—H11	120.7 (16)
C3—C4—N1	118.82 (17)	C11—C12—N6	111.1 (2)
C5—C4—N1	118.66 (18)	C11—C12—H12	127.8 (17)
C6—C5—C4	118.09 (19)	N6—C12—H12	121.1 (17)
C6—C5—H5	123.6 (15)	N6—C13—N5	112.0 (2)
C4—C5—H5	118.3 (15)	N6—C13—H13	128.2 (16)
C5—C6—C1	120.70 (18)	N5—C13—H13	119.8 (16)
C5—C6—H6	120.6 (16)

C8—N2—N3—N4	−0.6 (2)	C2—C1—C7—N2	115.3 (2)
C7—N2—N3—N4	−178.28 (17)	C6—C1—C7—N2	−63.8 (2)
N2—N3—N4—C9	0.6 (2)	N3—N2—C8—C9	0.3 (2)
C6—C1—C2—C3	0.8 (3)	C7—N2—C8—C9	177.69 (19)
C7—C1—C2—C3	−178.38 (18)	N3—N4—C9—C8	−0.5 (2)
C1—C2—C3—C4	0.0 (3)	N3—N4—C9—C10	−178.35 (19)
C2—C3—C4—C5	−0.8 (3)	N2—C8—C9—N4	0.1 (2)
C2—C3—C4—N1	177.84 (17)	N2—C8—C9—C10	177.7 (2)
O2—N1—C4—C3	173.1 (2)	C13—N5—C10—C9	−102.5 (3)
O1—N1—C4—C3	−7.5 (3)	C11—N5—C10—C9	73.0 (3)
O2—N1—C4—C5	−8.2 (3)	N4—C9—C10—N5	65.4 (2)
O1—N1—C4—C5	171.22 (19)	C8—C9—C10—N5	−112.0 (2)
C3—C4—C5—C6	0.8 (3)	C13—N5—C11—C12	−0.4 (2)
N1—C4—C5—C6	−177.84 (19)	C10—N5—C11—C12	−176.6 (2)
C4—C5—C6—C1	0.0 (3)	N5—C11—C12—N6	0.0 (3)
C2—C1—C6—C5	−0.8 (3)	C13—N6—C12—C11	0.4 (3)
C7—C1—C6—C5	178.39 (19)	C12—N6—C13—N5	−0.6 (3)
N3—N2—C7—C1	102.0 (2)	C11—N5—C13—N6	0.7 (3)
C8—N2—C7—C1	−75.2 (3)	C10—N5—C13—N6	176.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.98 (2)	2.55 (2)	3.189 (2)	123.0 (18)
C7—H7B···N6ⁱⁱ	0.95 (3)	2.60 (3)	3.478 (3)	154 (2)
C11—H11···O2ⁱⁱⁱ	0.98 (3)	2.66 (3)	3.535 (3)	149 (2)
C6—H6···N3^iv	1.00 (2)	2.54 (3)	3.299 (3)	133 (2)

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

Acknowledgements

The support of NSF-MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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