Crystal structure of 1-meth­oxy-5-methyl-N-phenyl-1,2,3-triazole-4-carboxamide

Khazhieva, I.S.; Glukhareva, T.V.; Slepukhin, P.A.; Morzherin, Y.Y.

doi:10.1107/S2056989015017776

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Page o798

doi:10.1107/S2056989015017776

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Crystal structure of 1-methoxy-5-methyl-N-phenyl-1,2,3-triazole-4-carboxamide

Inna S. Khazhieva,^a ^* Tatiana V. Glukhareva,^a Pavel A. Slepukhin ^b and Yury Yu. Morzherin ^a

^aUral Federal University, Mira 19 Ekaterinburg 620002, Russian Federation, and ^bI. Postovsky Institute of Organic Synthesis, Kovalevskoy 22 Ekaterinburg 620090, Russian Federation
^*Correspondence e-mail: i.s.khazhieva@urfu.ru

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 September 2015; accepted 22 September 2015; online 26 September 2015)

The title compound, C₁₁H₁₂N₄O₂,was prepared via the transformation of sodium 4-acetyl-1-phenyl-1H-[1.2.3]triazolate under the action of methoxyamine hydrochloride. The dihedral angle between the triazole and phenyl rings is 25.12 (16)° and the C atom of the methoxy group deviates from the triazole plane by 0.894 (4)Å. The conformation of the CONHR-group is consolodated by an intramolecular N—H⋯N hydrogen bond to an N-atom of the triazole ring, which closes an S(5) ring. In the crystal, weak N—H⋯N hydrogen bonds link the molecules into C(6) [010] chains.

Keywords: crystal structure; 1,2,3-triazole; rearrangements; hydrogen bonding.

CCDC reference: 1426448

1. Related literature

For biological activities of 1.2.3-triazoles, see: Sathish Kumar & Kavitha (2013 ); Khazhieva et al. (2015a ). For the synthesis, see: Khazhieva et al. (2015b ).

2. Experimental

2.1. Crystal data

C₁₁H₁₂N₄O₂
M_r = 232.25
Monoclinic, P 2₁ /c
a = 11.4637 (8) Å
b = 6.4345 (13) Å
c = 15.822 (3) Å
β = 100.367 (12)°
V = 1148.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.21 × 0.16 × 0.09 mm

2.2. Data collection

Agilent Xcalibur S CCD diffractometer
7259 measured reflections
2302 independent reflections
1077 reflections with I > 2σ(I)
R_int = 0.040

2.3. Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.147
S = 1.00
2302 reflections
160 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2	0.86 (2)	2.33 (3)	2.780 (4)	113 (2)
N1—H1⋯N3ⁱ	0.86 (2)	2.41 (2)	3.184 (3)	150 (2)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2006 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: publCIF (Westrip, 2010 ); software used to prepare material for publication: publCIF (Westrip, 2010).

Supporting information

CCDC reference: 1426448

Crystal structure: contains datablocks I, exp_221. DOI: 10.1107/S2056989015017776/hb7511sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015017776/hb7511Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015017776/hb7511Isup3.cml

checkCIF report

Synthesis and crystallization top

The titled compound was prepared as previously reported (Khazhieva et al., 2015b). Crystals were obtained by slow evaporation of a solution in ethanol.

Related literature top

For biological activities of 1.2.3-triazoles, see: Sathish Kumar & Kavitha (2013); Khazhieva et al. (2015a). For the synthesis, see: Khazhieva et al. (2015b).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2006); cell refinement: CrysAlis PRO (Agilent, 2006); data reduction: CrysAlis PRO (Agilent, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: publCIF (Westrip, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids for non-H atoms.

1-Methoxy-5-methyl-N-phenyl-1,2,3-triazole-4-carboxamide top

Crystal data top

C₁₁H₁₂N₄O₂	D_x = 1.344 Mg m⁻³
M_r = 232.25	Melting point: 310 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.4637 (8) Å	Cell parameters from 1077 reflections
b = 6.4345 (13) Å	θ = 2.9–26.4°
c = 15.822 (3) Å	µ = 0.10 mm⁻¹
β = 100.367 (12)°	T = 295 K
V = 1148.0 (3) Å³	Prism, colorless
Z = 4	0.21 × 0.16 × 0.09 mm
F(000) = 488

Data collection top

Agilent Xcalibur S CCD diffractometer	1077 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −7→14
7259 measured reflections	k = −5→8
2302 independent reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0682P)²] where P = (F_o² + 2F_c²)/3
2302 reflections	(Δ/σ)_max < 0.001
160 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₁H₁₂N₄O₂	V = 1148.0 (3) Å³
M_r = 232.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4637 (8) Å	µ = 0.10 mm⁻¹
b = 6.4345 (13) Å	T = 295 K
c = 15.822 (3) Å	0.21 × 0.16 × 0.09 mm
β = 100.367 (12)°

Data collection top

Agilent Xcalibur S CCD diffractometer	1077 reflections with I > 2σ(I)
7259 measured reflections	R_int = 0.040
2302 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.43 e Å⁻³
2302 reflections	Δρ_min = −0.22 e Å⁻³
160 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
O1	0.61315 (16)	0.0563 (3)	0.15704 (14)	0.0777 (7)
C8	0.7887 (2)	0.1712 (4)	0.24262 (18)	0.0475 (7)
C6	0.7399 (2)	−0.2566 (4)	0.08075 (18)	0.0496 (7)
C7	0.7204 (2)	0.0365 (4)	0.17728 (19)	0.0533 (7)
N2	0.90562 (18)	0.1400 (4)	0.27423 (17)	0.0605 (7)
N4	0.8463 (2)	0.3915 (4)	0.33811 (19)	0.0708 (8)
C9	0.7489 (2)	0.3375 (4)	0.28291 (19)	0.0553 (8)
N1	0.7844 (2)	−0.1083 (4)	0.14353 (16)	0.0530 (6)
N3	0.9416 (2)	0.2771 (4)	0.3343 (2)	0.0759 (8)
O2	0.8515 (2)	0.5302 (4)	0.40535 (18)	0.0956 (8)
C1	0.7975 (2)	−0.4450 (5)	0.0824 (2)	0.0589 (8)
H1A	0.8634	−0.4721	0.1246	0.071*
C5	0.6434 (3)	−0.2172 (5)	0.0169 (2)	0.0641 (8)
H5A	0.6049	−0.0896	0.0148	0.077*
C3	0.6605 (3)	−0.5520 (6)	−0.0411 (2)	0.0809 (10)
H3A	0.6331	−0.6524	−0.0821	0.097*
C2	0.7571 (3)	−0.5924 (5)	0.0214 (2)	0.0739 (9)
H2A	0.7955	−0.7200	0.0225	0.089*
C4	0.6048 (3)	−0.3651 (6)	−0.0430 (2)	0.0769 (10)
H4A	0.5395	−0.3381	−0.0857	0.092*
C11	0.9070 (4)	0.7045 (6)	0.3901 (3)	0.137 (2)
H11A	0.8970	0.8073	0.4321	0.205*
H11B	0.8741	0.7551	0.3337	0.205*
H11C	0.9900	0.6765	0.3933	0.205*
C10	0.6343 (3)	0.4512 (5)	0.2740 (2)	0.0818 (10)
H10A	0.6298	0.5214	0.3268	0.123*
H10B	0.5699	0.3543	0.2609	0.123*
H10C	0.6292	0.5511	0.2284	0.123*
H1	0.858 (2)	−0.109 (4)	0.1666 (17)	0.048 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0365 (12)	0.1021 (17)	0.0930 (17)	0.0057 (10)	0.0076 (11)	−0.0186 (13)
C8	0.0393 (15)	0.0458 (16)	0.0589 (18)	0.0007 (12)	0.0134 (13)	0.0056 (14)
C6	0.0414 (15)	0.0538 (18)	0.0549 (19)	−0.0035 (14)	0.0117 (14)	0.0045 (16)
C7	0.0418 (16)	0.0582 (18)	0.062 (2)	−0.0016 (14)	0.0146 (15)	0.0066 (16)
N2	0.0444 (14)	0.0516 (15)	0.0836 (19)	−0.0032 (11)	0.0062 (13)	−0.0019 (14)
N4	0.0607 (17)	0.0658 (17)	0.089 (2)	−0.0011 (13)	0.0206 (15)	−0.0268 (16)
C9	0.0400 (16)	0.065 (2)	0.0624 (19)	−0.0028 (14)	0.0117 (15)	−0.0013 (16)
N1	0.0354 (13)	0.0558 (15)	0.0661 (17)	0.0045 (11)	0.0041 (12)	−0.0011 (13)
N3	0.0465 (15)	0.0710 (17)	0.107 (2)	0.0004 (13)	0.0059 (14)	−0.0188 (17)
O2	0.0967 (18)	0.0961 (18)	0.102 (2)	−0.0125 (14)	0.0395 (15)	−0.0152 (16)
C1	0.0573 (17)	0.0563 (19)	0.064 (2)	0.0021 (15)	0.0140 (15)	0.0062 (17)
C5	0.0512 (18)	0.073 (2)	0.067 (2)	0.0069 (15)	0.0089 (16)	0.0035 (19)
C3	0.077 (2)	0.093 (3)	0.075 (3)	−0.018 (2)	0.018 (2)	−0.024 (2)
C2	0.081 (2)	0.061 (2)	0.085 (3)	−0.0020 (18)	0.030 (2)	−0.004 (2)
C4	0.061 (2)	0.098 (3)	0.070 (2)	−0.005 (2)	0.0055 (17)	−0.010 (2)
C11	0.171 (4)	0.055 (2)	0.221 (5)	−0.019 (2)	0.133 (4)	−0.005 (3)
C10	0.0566 (19)	0.098 (2)	0.092 (3)	0.0195 (17)	0.0172 (17)	−0.016 (2)

Geometric parameters (Å, º) top

O1—C7	1.220 (3)	C1—C2	1.372 (4)
C8—N2	1.359 (3)	C1—H1A	0.9300
C8—C9	1.365 (3)	C5—C4	1.359 (4)
C8—C7	1.463 (4)	C5—H5A	0.9300
C6—C1	1.379 (4)	C3—C4	1.360 (5)
C6—C5	1.381 (4)	C3—C2	1.370 (5)
C6—N1	1.405 (3)	C3—H3A	0.9300
C7—N1	1.354 (3)	C2—H2A	0.9300
N2—N3	1.308 (3)	C4—H4A	0.9300
N4—N3	1.327 (3)	C11—H11A	0.9600
N4—C9	1.334 (3)	C11—H11B	0.9600
N4—O2	1.382 (3)	C11—H11C	0.9600
C9—C10	1.488 (4)	C10—H10A	0.9600
N1—H1	0.85 (3)	C10—H10B	0.9600
O2—C11	1.333 (4)	C10—H10C	0.9600

N2—C8—C9	109.5 (2)	C4—C5—C6	120.0 (3)
N2—C8—C7	122.6 (2)	C4—C5—H5A	120.0
C9—C8—C7	127.8 (2)	C6—C5—H5A	120.0
C1—C6—C5	119.6 (3)	C4—C3—C2	120.0 (3)
C1—C6—N1	118.1 (3)	C4—C3—H3A	120.0
C5—C6—N1	122.3 (3)	C2—C3—H3A	120.0
O1—C7—N1	124.1 (3)	C3—C2—C1	120.2 (3)
O1—C7—C8	120.6 (2)	C3—C2—H2A	119.9
N1—C7—C8	115.3 (2)	C1—C2—H2A	119.9
N3—N2—C8	109.2 (2)	C5—C4—C3	120.7 (3)
N3—N4—C9	115.2 (2)	C5—C4—H4A	119.6
N3—N4—O2	118.1 (3)	C3—C4—H4A	119.6
C9—N4—O2	125.9 (2)	O2—C11—H11A	109.5
N4—C9—C8	101.5 (2)	O2—C11—H11B	109.5
N4—C9—C10	123.7 (3)	H11A—C11—H11B	109.5
C8—C9—C10	134.8 (3)	O2—C11—H11C	109.5
C7—N1—C6	126.3 (3)	H11A—C11—H11C	109.5
C7—N1—H1	113.4 (17)	H11B—C11—H11C	109.5
C6—N1—H1	120.2 (17)	C9—C10—H10A	109.5
N2—N3—N4	104.6 (2)	C9—C10—H10B	109.5
C11—O2—N4	111.1 (3)	H10A—C10—H10B	109.5
C2—C1—C6	119.6 (3)	C9—C10—H10C	109.5
C2—C1—H1A	120.2	H10A—C10—H10C	109.5
C6—C1—H1A	120.2	H10B—C10—H10C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2	0.86 (2)	2.33 (3)	2.780 (4)	113 (2)
N1—H1···N3ⁱ	0.86 (2)	2.41 (2)	3.184 (3)	150 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2	0.86 (2)	2.33 (3)	2.780 (4)	113 (2)
N1—H1···N3ⁱ	0.86 (2)	2.41 (2)	3.184 (3)	150 (2)

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

Acknowledgements

We thank the Russian Foundation for Basic Research (grant 13–03-00137), State task Ministry of Education and Science of the Russian Federation No. 4.560.2014-K and the Project Enhance Competitiveness of the Ural Federal University (Project 5–100-2020)

References

Agilent (2006). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England. Google Scholar
Khazhieva, I. S., Glukhareva, T. V., El'tsov, O. S., Morzherin, Yu. Yu., Minin, A. A., Pozdina, V. A. & Ulitko, M. V. (2015b). Khim. Farm. Zh. 49, 12–15. Google Scholar
Khazhieva, I. S., Glukhareva, T. V. & Morzherin, Yu. Yu. (2015a). Chim. Tech. Acta, 2, 52–58. CrossRef Google Scholar
Sathish Kumar, S. & Kavitha, H. P. (2013). Mini-Rev. Org. Chem. 10, 40–65. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar