2-(4-Phenyl-1H-1,2,3-triazol-1-yl)-N-(p-tol­yl)acetamide

Chu, Q.-Z.; Qi, B.-P.; Zhang, X.-R.

doi:10.1107/S1600536808023209

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1612

doi:10.1107/S1600536808023209

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2-(4-Phenyl-1H-1,2,3-triazol-1-yl)-N-(p-tolyl)acetamide

Qing-Zhu Chu,^a Bao-Ping Qi ^a and Xiao-Ru Zhang ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 266042 Qingdao, Shandong, People's Republic of China
^*Correspondence e-mail: qustchemistry@126.com

(Received 14 July 2008; accepted 23 July 2008; online 31 July 2008)

In the title molecule, C₁₇H₁₆N₄O, the triazole ring makes dihedral angles of 29.00 (1) and 77.74 (1)°, respectively, with the phenyl and benzene rings. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains extending along the c axis.

Related literature

For related literature, see: Kolb et al. (2001 ); Kolb & Sharpless (2003 ); Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₆N₄O
M_r = 292.34
Monoclinic, P 2₁ /c
a = 5.5923 (7) Å
b = 30.438 (4) Å
c = 9.6112 (10) Å
β = 115.595 (6)°
V = 1475.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.39 × 0.26 × 0.04 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.997
8229 measured reflections
2896 independent reflections
1970 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.136
S = 1.00
2896 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1ⁱ	0.86	2.09	2.878 (3)	152
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023209/cv2432sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023209/cv2432Isup2.hkl

checkCIF report

Comment top

The Huisgen 1,3-dipolar cycloaddition of alkynes with azides via Cu(I) catalysis is the most well known example of click chemistry (Kolb & Sharpless, 2003; Kolb et al., 2001), which leads to the synthesis of 1,4-disubstituted 1,2,3-triazoles. In this study, a new 1,2,3-triazole derivative was prepared by such "click" reaction and its structure was characterized by X-ray crystallographic analysis.

In the title compound, (I), all bond lengths and angles are within normal ranges (Allen et al., 1987). The N1–N3/C7/C8 triazole ring makes dihedral angles of 29.00 (1) and 77.74 (1)° with C1–C6 and C11–C16 rings, respectively, and the dihedral angle between the latter two aromatic rings is 88.00 (1)°.

In the crystal, intermolecular N—H···O hydrogen bond (Table 1) link the molecules into chains extended along c axis.

Related literature top

For related literature, see: Kolb et al. (2001); Kolb & Sharpless (2003); Allen et al. (1987).

Experimental top

To a solution of 4-methylaniline (2.61 g, 24.36 mmol), triethylamine (3.05 ml, 21.92 mmol) in dry CH₂Cl₂ (90 ml), chloroacetyl chloride (1.74 ml, 21.92 mmol) in dry CH₂Cl₂ (10 ml) was added dropwisely at 273 K under an inert atmosphere. The mixture was stirred at r.t. for 5 h, followed by dilution with CH₂Cl₂ (50 ml). Then washed by water for three times and the organic phase was dried over anhydrous sodium sulfate. After removal of the solvents in vacuo, 2-chloro-N-(4-methylphenyl)acetamide (3.82 g, 94.76%) was obtaind. To a solution of 2-chloro-N-(4-methylxyphenyl)acetamide (1.72 g, 9.37 mmol) in 50 ml DMF/H₂O (1:1, v/v), NaN₃ (0.79 g, 12.15 mmol), phenylacetylene (3.08 ml, 28.08 mmol), CuSO₄.5H₂O (0.24 g, 0.94 mmol), L-Ascorbic acid sodium salt (0.37 g, 1.87 mmol) were added successively. The mixture was stirred at 333 K for 36 h. Then NH₃.H₂O (25 ml) was added, and the solvent was extracted with ethyl acetate, washed with water for three times. The organic phase was dried over anhydrous Na₂SO₄. After evaporation, the resulting solid was recrystallized from ethyl acetate, yielding the title compound (I) (2.13 g, 77.9%). Colourless single crystals suitable for X-ray crystallographic analysis were grown by slow evaporation of ethyl acetate.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the a axis. Dashed lines denote N—H···O hydrogen bonds.

2-(4-Phenyl-1H-1,2,3-triazol-1-yl)-N-(p-tolyl)acetamide top

Crystal data top

C₁₇H₁₆N₄O	F(000) = 616
M_r = 292.34	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.5923 (7) Å	Cell parameters from 1236 reflections
b = 30.438 (4) Å	θ = 2.4–21.9°
c = 9.6112 (10) Å	µ = 0.09 mm⁻¹
β = 115.595 (6)°	T = 293 K
V = 1475.5 (3) Å³	Plate, colourless
Z = 4	0.39 × 0.26 × 0.04 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2896 independent reflections
Radiation source: fine-focus sealed tube	1970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.1°, θ_min = 2.4°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −37→33
T_min = 0.967, T_max = 0.997	l = −9→11
8229 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0529P)² + 0.5144P] where P = (F_o² + 2F_c²)/3
2896 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₆N₄O	V = 1475.5 (3) Å³
M_r = 292.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.5923 (7) Å	µ = 0.09 mm⁻¹
b = 30.438 (4) Å	T = 293 K
c = 9.6112 (10) Å	0.39 × 0.26 × 0.04 mm
β = 115.595 (6)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2896 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1970 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.997	R_int = 0.039
8229 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
2896 reflections	Δρ_min = −0.17 e Å⁻³
199 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N4	0.5557 (4)	0.72043 (6)	0.6455 (2)	0.0390 (5)
H4A	0.6141	0.7249	0.7431	0.047*
N3	0.9051 (4)	0.81474 (6)	0.5865 (2)	0.0386 (5)
O1	0.5915 (4)	0.74454 (5)	0.43200 (19)	0.0558 (5)
C7	0.9236 (4)	0.87351 (7)	0.4663 (3)	0.0372 (5)
N1	1.1547 (4)	0.85049 (7)	0.5105 (2)	0.0481 (5)
N2	1.1417 (4)	0.81467 (7)	0.5828 (2)	0.0495 (6)
C11	0.3715 (4)	0.68575 (7)	0.5825 (2)	0.0348 (5)
C8	0.7636 (5)	0.85028 (7)	0.5150 (3)	0.0385 (6)
H8A	0.5935	0.8576	0.5014	0.046*
C16	0.3509 (5)	0.66145 (7)	0.4563 (3)	0.0383 (6)
H16A	0.4596	0.6679	0.4081	0.046*
C12	0.2094 (5)	0.67507 (8)	0.6535 (3)	0.0412 (6)
H12A	0.2224	0.6909	0.7393	0.049*
C10	0.6489 (5)	0.74713 (7)	0.5694 (3)	0.0373 (6)
C15	0.1688 (5)	0.62767 (7)	0.4016 (3)	0.0422 (6)
H15A	0.1568	0.6117	0.3164	0.051*
C6	0.8802 (5)	0.91601 (8)	0.3866 (3)	0.0409 (6)
C14	0.0036 (5)	0.61689 (8)	0.4702 (3)	0.0445 (6)
C13	0.0295 (5)	0.64126 (8)	0.5975 (3)	0.0465 (6)
H13A	−0.0775	0.6346	0.6465	0.056*
C9	0.8423 (5)	0.78126 (8)	0.6729 (3)	0.0474 (6)
H9A	0.7666	0.7952	0.7355	0.057*
H9B	1.0047	0.7667	0.7420	0.057*
C5	0.6276 (5)	0.92969 (9)	0.2884 (3)	0.0533 (7)
H5A	0.4834	0.9117	0.2715	0.064*
C1	1.0916 (6)	0.94323 (9)	0.4090 (3)	0.0557 (7)
H1B	1.2632	0.9345	0.4743	0.067*
C4	0.5868 (6)	0.96997 (10)	0.2147 (4)	0.0668 (8)
H4B	0.4158	0.9788	0.1487	0.080*
C3	0.7971 (7)	0.99692 (10)	0.2385 (4)	0.0690 (9)
H3A	0.7693	1.0241	0.1900	0.083*
C2	1.0483 (7)	0.98348 (9)	0.3341 (4)	0.0694 (9)
H2B	1.1918	1.0015	0.3492	0.083*
C17	−0.1951 (6)	0.58006 (9)	0.4079 (4)	0.0701 (9)
H17A	−0.1834	0.5672	0.3198	0.105*
H17B	−0.3706	0.5914	0.3780	0.105*
H17C	−0.1578	0.5581	0.4862	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0487 (12)	0.0423 (11)	0.0276 (10)	−0.0047 (9)	0.0180 (9)	−0.0002 (9)
N3	0.0409 (12)	0.0390 (11)	0.0379 (11)	−0.0043 (9)	0.0190 (9)	0.0001 (9)
O1	0.0874 (14)	0.0507 (11)	0.0314 (10)	−0.0180 (10)	0.0277 (10)	−0.0014 (8)
C7	0.0375 (13)	0.0394 (13)	0.0394 (13)	−0.0022 (10)	0.0210 (11)	−0.0007 (10)
N1	0.0435 (13)	0.0523 (13)	0.0560 (14)	0.0042 (10)	0.0285 (11)	0.0084 (11)
N2	0.0462 (13)	0.0533 (13)	0.0556 (14)	0.0078 (10)	0.0283 (11)	0.0093 (11)
C11	0.0370 (13)	0.0343 (12)	0.0314 (12)	0.0033 (10)	0.0131 (10)	0.0036 (10)
C8	0.0334 (13)	0.0410 (13)	0.0440 (14)	−0.0011 (11)	0.0194 (11)	−0.0024 (11)
C16	0.0424 (14)	0.0383 (13)	0.0363 (13)	0.0012 (11)	0.0191 (11)	0.0034 (10)
C12	0.0489 (15)	0.0392 (13)	0.0403 (14)	0.0035 (11)	0.0238 (12)	0.0031 (11)
C10	0.0469 (14)	0.0344 (13)	0.0319 (13)	0.0023 (10)	0.0184 (11)	0.0016 (10)
C15	0.0456 (15)	0.0372 (13)	0.0407 (14)	0.0042 (11)	0.0157 (12)	−0.0029 (11)
C6	0.0460 (14)	0.0402 (13)	0.0451 (14)	−0.0018 (11)	0.0279 (12)	−0.0018 (11)
C14	0.0394 (14)	0.0376 (13)	0.0536 (16)	0.0006 (11)	0.0175 (12)	0.0011 (12)
C13	0.0439 (15)	0.0489 (15)	0.0532 (16)	0.0009 (12)	0.0270 (13)	0.0072 (13)
C9	0.0616 (17)	0.0450 (15)	0.0367 (14)	−0.0083 (12)	0.0221 (13)	0.0006 (12)
C5	0.0494 (16)	0.0478 (16)	0.0624 (18)	0.0007 (12)	0.0239 (14)	0.0063 (13)
C1	0.0520 (17)	0.0538 (17)	0.0674 (19)	−0.0052 (13)	0.0315 (15)	0.0039 (14)
C4	0.069 (2)	0.0564 (18)	0.073 (2)	0.0146 (16)	0.0296 (18)	0.0155 (16)
C3	0.096 (3)	0.0428 (16)	0.085 (2)	0.0112 (17)	0.056 (2)	0.0156 (16)
C2	0.078 (2)	0.0487 (17)	0.097 (2)	−0.0096 (16)	0.052 (2)	0.0070 (17)
C17	0.065 (2)	0.0576 (18)	0.095 (2)	−0.0155 (15)	0.0414 (19)	−0.0156 (17)

Geometric parameters (Å, º) top

N4—C10	1.341 (3)	C15—H15A	0.9300
N4—C11	1.415 (3)	C6—C5	1.381 (3)
N4—H4A	0.8600	C6—C1	1.382 (3)
N3—N2	1.339 (3)	C14—C13	1.384 (3)
N3—C8	1.341 (3)	C14—C17	1.508 (3)
N3—C9	1.450 (3)	C13—H13A	0.9300
O1—C10	1.219 (3)	C9—H9A	0.9700
C7—N1	1.367 (3)	C9—H9B	0.9700
C7—C8	1.372 (3)	C5—C4	1.385 (4)
C7—C6	1.469 (3)	C5—H5A	0.9300
N1—N2	1.312 (3)	C1—C2	1.388 (4)
C11—C16	1.383 (3)	C1—H1B	0.9300
C11—C12	1.388 (3)	C4—C3	1.370 (4)
C8—H8A	0.9300	C4—H4B	0.9300
C16—C15	1.381 (3)	C3—C2	1.368 (4)
C16—H16A	0.9300	C3—H3A	0.9300
C12—C13	1.376 (3)	C2—H2B	0.9300
C12—H12A	0.9300	C17—H17A	0.9600
C10—C9	1.520 (3)	C17—H17B	0.9600
C15—C14	1.386 (3)	C17—H17C	0.9600

C10—N4—C11	126.96 (19)	C13—C14—C17	121.8 (2)
C10—N4—H4A	116.5	C15—C14—C17	121.0 (2)
C11—N4—H4A	116.5	C12—C13—C14	121.8 (2)
N2—N3—C8	111.02 (18)	C12—C13—H13A	119.1
N2—N3—C9	120.0 (2)	C14—C13—H13A	119.1
C8—N3—C9	128.7 (2)	N3—C9—C10	112.66 (19)
N1—C7—C8	107.4 (2)	N3—C9—H9A	109.1
N1—C7—C6	122.3 (2)	C10—C9—H9A	109.1
C8—C7—C6	130.3 (2)	N3—C9—H9B	109.1
N2—N1—C7	109.24 (18)	C10—C9—H9B	109.1
N1—N2—N3	107.11 (19)	H9A—C9—H9B	107.8
C16—C11—C12	118.8 (2)	C6—C5—C4	120.7 (3)
C16—C11—N4	123.0 (2)	C6—C5—H5A	119.7
C12—C11—N4	118.3 (2)	C4—C5—H5A	119.7
N3—C8—C7	105.3 (2)	C6—C1—C2	120.2 (3)
N3—C8—H8A	127.4	C6—C1—H1B	119.9
C7—C8—H8A	127.4	C2—C1—H1B	119.9
C15—C16—C11	120.0 (2)	C3—C4—C5	120.3 (3)
C15—C16—H16A	120.0	C3—C4—H4B	119.8
C11—C16—H16A	120.0	C5—C4—H4B	119.8
C13—C12—C11	120.3 (2)	C2—C3—C4	119.5 (3)
C13—C12—H12A	119.8	C2—C3—H3A	120.3
C11—C12—H12A	119.8	C4—C3—H3A	120.3
O1—C10—N4	124.7 (2)	C3—C2—C1	120.7 (3)
O1—C10—C9	122.2 (2)	C3—C2—H2B	119.6
N4—C10—C9	113.05 (19)	C1—C2—H2B	119.6
C16—C15—C14	121.9 (2)	C14—C17—H17A	109.5
C16—C15—H15A	119.0	C14—C17—H17B	109.5
C14—C15—H15A	119.0	H17A—C17—H17B	109.5
C5—C6—C1	118.6 (2)	C14—C17—H17C	109.5
C5—C6—C7	120.8 (2)	H17A—C17—H17C	109.5
C1—C6—C7	120.6 (2)	H17B—C17—H17C	109.5
C13—C14—C15	117.2 (2)

C8—C7—N1—N2	0.1 (3)	N1—C7—C6—C1	−27.7 (3)
C6—C7—N1—N2	178.1 (2)	C8—C7—C6—C1	149.7 (3)
C7—N1—N2—N3	−0.5 (3)	C16—C15—C14—C13	−0.5 (4)
C8—N3—N2—N1	0.7 (3)	C16—C15—C14—C17	179.6 (2)
C9—N3—N2—N1	−173.9 (2)	C11—C12—C13—C14	0.0 (4)
C10—N4—C11—C16	30.6 (3)	C15—C14—C13—C12	0.6 (4)
C10—N4—C11—C12	−151.1 (2)	C17—C14—C13—C12	−179.5 (2)
N2—N3—C8—C7	−0.7 (3)	N2—N3—C9—C10	−106.1 (2)
C9—N3—C8—C7	173.4 (2)	C8—N3—C9—C10	80.4 (3)
N1—C7—C8—N3	0.3 (3)	O1—C10—C9—N3	11.7 (3)
C6—C7—C8—N3	−177.4 (2)	N4—C10—C9—N3	−169.56 (19)
C12—C11—C16—C15	0.9 (3)	C1—C6—C5—C4	−0.5 (4)
N4—C11—C16—C15	179.2 (2)	C7—C6—C5—C4	179.3 (2)
C16—C11—C12—C13	−0.8 (3)	C5—C6—C1—C2	0.3 (4)
N4—C11—C12—C13	−179.2 (2)	C7—C6—C1—C2	−179.5 (2)
C11—N4—C10—O1	−1.9 (4)	C6—C5—C4—C3	−0.1 (4)
C11—N4—C10—C9	179.3 (2)	C5—C4—C3—C2	0.9 (5)
C11—C16—C15—C14	−0.2 (4)	C4—C3—C2—C1	−1.0 (5)
N1—C7—C6—C5	152.5 (2)	C6—C1—C2—C3	0.5 (4)
C8—C7—C6—C5	−30.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.86	2.09	2.878 (3)	152

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₄O
M_r	292.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.5923 (7), 30.438 (4), 9.6112 (10)
β (°)	115.595 (6)
V (Å³)	1475.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.26 × 0.04

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	8229, 2896, 1970
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.136, 1.01
No. of reflections	2896
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.17

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ⁱ	0.86	2.092	2.878 (3)	151.61

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant No. Y2006B07).

References

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