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

Abstract

The title compound, C ₁₁H₁₂N₄O₂,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.

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 ▸).

Experimental  

Crystal data  

• C₁₁H₁₂N₄O₂

• M _r = 232.25

• Monoclinic,

• a = 11.4637 (8) Å

• b = 6.4345 (13) Å

• c = 15.822 (3) Å

• β = 100.367 (12)°

• V = 1148.0 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 295 K

• 0.21 × 0.16 × 0.09 mm

Data collection  

• Agilent Xcalibur S CCD diffractometer

• 7259 measured reflections

• 2302 independent reflections

• 1077 reflections with I > 2σ(I)

• R _int = 0.040

Refinement  

• R[F ² > 2σ(F ²)] = 0.055

• wR(F ²) = 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

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 ▸).

Supplementary Material

CCDC reference: 1426448

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1N2	0.86(2)	2.33(3)	2.780(4)	113(2)
N1H1N3i	0.86(2)	2.41(2)	3.184(3)	150(2)

Symmetry code: (i) .

supplementary crystallographic information

S1. Synthesis and crystallization

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

Figures

Fig. 1.

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

Crystal data

C11H12N4O2	Dx = 1.344 Mg m−3
Mr = 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

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

Refinement

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(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3
2302 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.