2-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth­oxy]-1-naphthaldehyde

Vishnupriya, R.; Venkateshan, M.; Suresh, J.; Jaabil, G.; Ponnuswamy, A.; Lakshman, P.L.N.

doi:10.1107/S2414314619015256

organic compounds

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ISSN: 2414-3146

Volume 4| Part 11| November 2019| x191525

https://doi.org/10.1107/S2414314619015256

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2-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-1-naphthaldehyde

R. Vishnupriya,^a M. Venkateshan,^a J. Suresh,^a G. Jaabil,^b A. Ponnuswamy ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food, Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 October 2019; accepted 12 November 2019; online 19 November 2019)

In the title compound, C₂₁H₁₇N₃O₂, the triazole ring system is inclined at dihedral angles of 4.14 (18) and 69.24 (11)° with the naphthalene ring system and phenyl ring, respectively. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into double columns propagating along the b-axis direction.

Keywords: crystal structure; triazole; hydrogen bonding.

CCDC references: 1965225; 1965225

Structure description

Aldehyde derivatives are starting materials for obtaining Schiff bases and oxime-type ligands and their transition-metal complexes (Vigato & Tamburini, 2004 ). Heterocycles containing a 1,2,3-triazole ring have been utilized in cancer cell treatment (Yadav et al., 2017 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound (Fig. 1).

Figure 1
The molecular structure of the compound, showing 30% probability displacement ellipsoids.

The 1,2,3-triazole ring (C13/C14/N1–N3) is almost planar with an r.m.s. deviation of 0.0006 Å. The triazole ring subtends dihedral angles of 4.14 (18) and 69.24 (11)° with the naphthalene ring system (C1–C10) and the phenyl ring (C15–C21), respectively. The aldehyde and methoxy groups are slightly twisted away from the naphthalene ring system [C8—C7—C11—O2 = 2.7 (5)° and C12—O1—C6—C5 = −2.2 (4)°]. Atom C13 shows a distorted sp² hybridization state with bond angles of 108.5 (3) (N3—C13—C14), 131.4 (2) (C12—C13—C14) and 120.0 (3)° (N3—C13—C12), which are similar to the equivalent bond angles reported for other triazole derivatives (Zhao et al., 2010 ; Gao et al., 2011 ).

In the crystal (Fig. 2), atom O2 is a double acceptor of hydrogen bonds (Table 1) from C14—H14 and C21—H21, which generates [010] double columns.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O2ⁱ	0.93	2.53	3.462 (5)	175
C14—H14⋯O2ⁱ	0.93	2.62	3.497 (4)	157
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A partial view of the crystal packing of the title compound, illustrating the formation of [010] chains linked by C—H⋯O hydrogen bonds (dashed lines).

Synthesis and crystallization

A mixture of o-propargyloxynaphthaldehyde, (1.0 mmol), benzyl azide (1.0 mmol) and CuI (0.01 mmol) in water (5 ml) was refluxed for 30 minutes. After the completion of the reaction (monitored by TLC), the mixture was poured onto excess of crushed ice. Then, the reaction mixture was washed with a saturated solution of NH₄Cl and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using petroleum ether:ethyl acetate (90:10) as eluents to afford the title compound in 85% yield; m.p. 165°C. Colourless blocks were recrystallized from ethanol solution after one week at room temperature.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₃O₂
M_r	343.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.013 (3), 5.4123 (11), 22.901 (5)
β (°)	93.157 (5)
V (Å³)	1734.3 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.967, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	15604, 3076, 1363
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.199, 0.87
No. of reflections	3076
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS2013 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), SHELXL2014 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC references: 1965225; 1965225

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314619015256/hb4324sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619015256/hb4324Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619015256/hb4324Isup3.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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

2-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]-1-naphthaldehyde top

Crystal data top

C₂₁H₁₇N₃O₂	F(000) = 720
M_r = 343.38	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.013 (3) Å	Cell parameters from 3076 reflections
b = 5.4123 (11) Å	θ = 2.9–25.1°
c = 22.901 (5) Å	µ = 0.09 mm⁻¹
β = 93.157 (5)°	T = 296 K
V = 1734.3 (6) Å³	Block, colourless
Z = 4	0.20 × 0.15 × 0.15 mm

Data collection top

Bruker Kappa APEXII diffractometer	3076 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Detector resolution: 0 pixels mm^-1	R_int = 0.063
ω and φ scans	θ_max = 25.1°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.967, T_max = 0.974	k = −6→6
15604 measured reflections	l = −27→27

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.1156P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.199	(Δ/σ)_max < 0.001
S = 0.87	Δρ_max = 0.14 e Å⁻³
3076 reflections	Δρ_min = −0.13 e Å⁻³
236 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.005 (2)

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. H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å and N—H = 0.86 Å. The constrain U_iso(H) = 1.2U_eq(C) was applied.

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

	x	y	z	U_iso*/U_eq
O1	0.63383 (15)	0.3041 (4)	0.10577 (8)	0.0701 (7)
N1	0.4963 (2)	−0.2659 (5)	0.18506 (12)	0.0755 (8)
O2	0.82063 (19)	0.6602 (5)	0.20521 (10)	0.1081 (9)
N3	0.4565 (2)	−0.1807 (6)	0.09637 (12)	0.0799 (9)
C6	0.6788 (2)	0.4857 (6)	0.07659 (12)	0.0576 (8)
C7	0.7493 (2)	0.6202 (6)	0.10804 (12)	0.0582 (8)
C13	0.5244 (2)	−0.0183 (6)	0.11562 (13)	0.0590 (8)
N2	0.4390 (2)	−0.3342 (5)	0.13932 (15)	0.0886 (9)
C8	0.7996 (2)	0.8086 (6)	0.07856 (13)	0.0620 (9)
C12	0.5595 (2)	0.1707 (6)	0.07551 (13)	0.0646 (9)
H12A	0.5834	0.0924	0.0411	0.077*
H12B	0.5080	0.2817	0.0631	0.077*
C3	0.7745 (2)	0.8597 (6)	0.01888 (13)	0.0633 (9)
C14	0.5501 (2)	−0.0716 (6)	0.17178 (13)	0.0670 (9)
H14	0.5953	0.0092	0.1961	0.080*
C4	0.7012 (2)	0.7178 (6)	−0.00971 (14)	0.0713 (10)
H4	0.6840	0.7515	−0.0487	0.086*
C5	0.6555 (2)	0.5365 (6)	0.01725 (13)	0.0673 (9)
H5	0.6086	0.4446	−0.0032	0.081*
C16	0.4240 (3)	−0.2729 (7)	0.28069 (14)	0.0746 (10)
C11	0.7662 (2)	0.5597 (7)	0.16993 (14)	0.0792 (10)
H11	0.7309	0.4286	0.1838	0.095*
C21	0.4500 (3)	−0.0592 (7)	0.30988 (16)	0.0855 (11)
H21	0.5098	0.0091	0.3045	0.103*
C2	0.8223 (3)	1.0431 (7)	−0.01081 (16)	0.0858 (11)
H2	0.8048	1.0744	−0.0499	0.103*
C9	0.8753 (3)	0.9526 (7)	0.10500 (16)	0.0849 (11)
H9	0.8943	0.9267	0.1441	0.102*
C20	0.3902 (4)	0.0555 (8)	0.34662 (17)	0.0959 (12)
H20	0.4098	0.1994	0.3659	0.115*
C1	0.8937 (3)	1.1764 (7)	0.0161 (2)	0.1008 (13)
H1	0.9246	1.2994	−0.0041	0.121*
C17	0.3341 (4)	−0.3686 (8)	0.29026 (17)	0.0987 (13)
H17	0.3139	−0.5131	0.2714	0.118*
C15	0.4910 (3)	−0.3965 (7)	0.24094 (15)	0.0984 (13)
H15A	0.5543	−0.4039	0.2603	0.118*
H15B	0.4696	−0.5647	0.2335	0.118*
C18	0.2738 (3)	−0.2500 (10)	0.3279 (2)	0.1062 (14)
H18	0.2140	−0.3153	0.3344	0.127*
C19	0.3036 (4)	−0.0381 (10)	0.35497 (18)	0.1032 (13)
H19	0.2633	0.0429	0.3796	0.124*
C10	0.9201 (3)	1.1267 (8)	0.0741 (2)	0.1047 (13)
H10	0.9701	1.2156	0.0924	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0646 (15)	0.0955 (15)	0.0485 (12)	−0.0082 (12)	−0.0110 (11)	0.0004 (11)
N1	0.094 (2)	0.075 (2)	0.0581 (18)	0.0211 (17)	0.0069 (17)	0.0016 (16)
O2	0.101 (2)	0.158 (2)	0.0619 (15)	−0.0213 (18)	−0.0268 (15)	−0.0169 (15)
N3	0.081 (2)	0.094 (2)	0.0638 (18)	−0.0140 (18)	−0.0010 (16)	−0.0077 (17)
C6	0.051 (2)	0.075 (2)	0.0471 (17)	0.0086 (17)	0.0010 (15)	−0.0053 (16)
C7	0.0511 (19)	0.074 (2)	0.0482 (17)	0.0112 (17)	−0.0057 (15)	−0.0151 (16)
C13	0.060 (2)	0.070 (2)	0.0463 (18)	0.0099 (18)	0.0025 (16)	−0.0082 (16)
N2	0.100 (3)	0.092 (2)	0.074 (2)	−0.0071 (18)	0.0064 (19)	−0.0061 (18)
C8	0.057 (2)	0.070 (2)	0.059 (2)	0.0109 (18)	−0.0025 (17)	−0.0159 (17)
C12	0.060 (2)	0.083 (2)	0.0495 (18)	0.0016 (18)	−0.0069 (16)	−0.0110 (17)
C3	0.058 (2)	0.071 (2)	0.061 (2)	0.0074 (17)	0.0051 (17)	−0.0032 (17)
C14	0.071 (2)	0.073 (2)	0.057 (2)	0.0108 (19)	−0.0024 (17)	−0.0062 (17)
C4	0.069 (2)	0.095 (2)	0.0494 (19)	0.005 (2)	−0.0019 (18)	0.0007 (18)
C5	0.062 (2)	0.091 (2)	0.0479 (18)	−0.0009 (19)	−0.0100 (16)	−0.0042 (17)
C16	0.105 (3)	0.063 (2)	0.056 (2)	0.013 (2)	0.006 (2)	0.0117 (18)
C11	0.071 (2)	0.109 (3)	0.056 (2)	0.000 (2)	−0.0137 (18)	−0.008 (2)
C21	0.099 (3)	0.083 (3)	0.077 (2)	0.012 (2)	0.018 (2)	0.011 (2)
C2	0.092 (3)	0.089 (2)	0.077 (2)	−0.006 (2)	0.005 (2)	−0.002 (2)
C9	0.082 (3)	0.099 (3)	0.072 (2)	−0.006 (2)	−0.006 (2)	−0.019 (2)
C20	0.116 (4)	0.088 (3)	0.084 (3)	0.012 (3)	0.013 (3)	0.003 (2)
C1	0.102 (3)	0.094 (3)	0.106 (3)	−0.017 (3)	0.009 (3)	−0.004 (3)
C17	0.137 (4)	0.092 (3)	0.065 (3)	−0.014 (3)	−0.006 (3)	0.011 (2)
C15	0.139 (4)	0.085 (2)	0.073 (2)	0.035 (2)	0.012 (2)	0.016 (2)
C18	0.100 (3)	0.143 (4)	0.077 (3)	−0.010 (3)	0.016 (3)	0.019 (3)
C19	0.115 (4)	0.117 (4)	0.079 (3)	0.020 (3)	0.015 (3)	0.006 (3)
C10	0.099 (3)	0.108 (3)	0.106 (4)	−0.034 (3)	−0.004 (3)	−0.018 (3)

Geometric parameters (Å, º) top

O1—C6	1.362 (3)	C5—H5	0.9300
O1—C12	1.416 (3)	C16—C21	1.375 (5)
N1—N2	1.337 (4)	C16—C17	1.391 (5)
N1—C14	1.338 (4)	C16—C15	1.501 (5)
N1—C15	1.467 (4)	C11—H11	0.9300
O2—C11	1.210 (3)	C21—C20	1.369 (5)
N3—N2	1.321 (4)	C21—H21	0.9300
N3—C13	1.352 (4)	C2—C1	1.354 (5)
C6—C7	1.395 (4)	C2—H2	0.9300
C6—C5	1.407 (4)	C9—C10	1.353 (5)
C7—C8	1.430 (4)	C9—H9	0.9300
C7—C11	1.461 (4)	C20—C19	1.338 (5)
C13—C14	1.347 (4)	C20—H20	0.9300
C13—C12	1.477 (4)	C1—C10	1.386 (5)
C8—C3	1.420 (4)	C1—H1	0.9300
C8—C9	1.425 (4)	C17—C18	1.396 (6)
C12—H12A	0.9700	C17—H17	0.9300
C12—H12B	0.9700	C15—H15A	0.9700
C3—C2	1.395 (4)	C15—H15B	0.9700
C3—C4	1.415 (4)	C18—C19	1.358 (5)
C14—H14	0.9300	C18—H18	0.9300
C4—C5	1.341 (4)	C19—H19	0.9300
C4—H4	0.9300	C10—H10	0.9300

C6—O1—C12	118.4 (2)	C17—C16—C15	122.1 (4)
N2—N1—C14	111.1 (3)	O2—C11—C7	127.6 (3)
N2—N1—C15	119.5 (3)	O2—C11—H11	116.2
C14—N1—C15	129.3 (3)	C7—C11—H11	116.2
N2—N3—C13	108.8 (3)	C20—C21—C16	121.7 (4)
O1—C6—C7	117.2 (3)	C20—C21—H21	119.2
O1—C6—C5	121.7 (3)	C16—C21—H21	119.2
C7—C6—C5	121.1 (3)	C1—C2—C3	121.4 (4)
C6—C7—C8	118.8 (3)	C1—C2—H2	119.3
C6—C7—C11	117.1 (3)	C3—C2—H2	119.3
C8—C7—C11	124.1 (3)	C10—C9—C8	121.0 (3)
C14—C13—N3	108.5 (3)	C10—C9—H9	119.5
C14—C13—C12	131.4 (3)	C8—C9—H9	119.5
N3—C13—C12	120.0 (3)	C19—C20—C21	120.5 (4)
N3—N2—N1	106.3 (3)	C19—C20—H20	119.8
C3—C8—C9	116.2 (3)	C21—C20—H20	119.8
C3—C8—C7	119.4 (3)	C2—C1—C10	118.9 (4)
C9—C8—C7	124.4 (3)	C2—C1—H1	120.5
O1—C12—C13	108.0 (2)	C10—C1—H1	120.5
O1—C12—H12A	110.1	C16—C17—C18	120.7 (4)
C13—C12—H12A	110.1	C16—C17—H17	119.7
O1—C12—H12B	110.1	C18—C17—H17	119.7
C13—C12—H12B	110.1	N1—C15—C16	112.2 (3)
H12A—C12—H12B	108.4	N1—C15—H15A	109.2
C2—C3—C4	121.1 (3)	C16—C15—H15A	109.2
C2—C3—C8	120.5 (3)	N1—C15—H15B	109.2
C4—C3—C8	118.3 (3)	C16—C15—H15B	109.2
N1—C14—C13	105.2 (3)	H15A—C15—H15B	107.9
N1—C14—H14	127.4	C19—C18—C17	119.3 (4)
C13—C14—H14	127.4	C19—C18—H18	120.3
C5—C4—C3	122.5 (3)	C17—C18—H18	120.3
C5—C4—H4	118.8	C20—C19—C18	120.8 (5)
C3—C4—H4	118.8	C20—C19—H19	119.6
C4—C5—C6	119.8 (3)	C18—C19—H19	119.6
C4—C5—H5	120.1	C9—C10—C1	122.0 (4)
C6—C5—H5	120.1	C9—C10—H10	119.0
C21—C16—C17	117.1 (4)	C1—C10—H10	119.0
C21—C16—C15	120.8 (4)

C12—O1—C6—C7	177.7 (2)	C2—C3—C4—C5	178.4 (3)
C12—O1—C6—C5	−2.2 (4)	C8—C3—C4—C5	−0.6 (5)
O1—C6—C7—C8	178.6 (2)	C3—C4—C5—C6	1.4 (5)
C5—C6—C7—C8	−1.4 (4)	O1—C6—C5—C4	179.6 (3)
O1—C6—C7—C11	−2.0 (4)	C7—C6—C5—C4	−0.3 (4)
C5—C6—C7—C11	177.9 (3)	C6—C7—C11—O2	−176.7 (3)
N2—N3—C13—C14	0.1 (4)	C8—C7—C11—O2	2.7 (5)
N2—N3—C13—C12	178.3 (3)	C17—C16—C21—C20	−0.2 (5)
C13—N3—N2—N1	0.0 (4)	C15—C16—C21—C20	−179.6 (3)
C14—N1—N2—N3	−0.1 (4)	C4—C3—C2—C1	−178.8 (3)
C15—N1—N2—N3	177.6 (3)	C8—C3—C2—C1	0.2 (5)
C6—C7—C8—C3	2.1 (4)	C3—C8—C9—C10	−0.3 (5)
C11—C7—C8—C3	−177.2 (3)	C7—C8—C9—C10	179.5 (3)
C6—C7—C8—C9	−177.6 (3)	C16—C21—C20—C19	−0.3 (6)
C11—C7—C8—C9	3.1 (5)	C3—C2—C1—C10	0.7 (6)
C6—O1—C12—C13	178.4 (2)	C21—C16—C17—C18	0.1 (5)
C14—C13—C12—O1	1.3 (4)	C15—C16—C17—C18	179.5 (3)
N3—C13—C12—O1	−176.4 (3)	N2—N1—C15—C16	−93.1 (4)
C9—C8—C3—C2	−0.4 (4)	C14—N1—C15—C16	84.2 (4)
C7—C8—C3—C2	179.8 (3)	C21—C16—C15—N1	−75.5 (4)
C9—C8—C3—C4	178.6 (3)	C17—C16—C15—N1	105.3 (4)
C7—C8—C3—C4	−1.1 (4)	C16—C17—C18—C19	0.5 (6)
N2—N1—C14—C13	0.2 (3)	C21—C20—C19—C18	0.9 (6)
C15—N1—C14—C13	−177.3 (3)	C17—C18—C19—C20	−1.0 (6)
N3—C13—C14—N1	−0.2 (3)	C8—C9—C10—C1	1.2 (6)
C12—C13—C14—N1	−178.1 (3)	C2—C1—C10—C9	−1.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O2ⁱ	0.93	2.53	3.462 (5)	175
C14—H14···O2ⁱ	0.93	2.62	3.497 (4)	157

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

JS and RV thank the management of The Madura College for their support.

Funding information

JS thanks the UGC for funds under project No. F MRP-7018/16(SERO/UGC).

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