Ethyl 5-methyl-1-(4-nitro-phen-yl)-1H-1,2,3-triazole-4-carboxyl-ate.

In the title compound, C(12)H(12)N(4)O(4), the 1,2,3-triazole ring and the nitro group form dihedral angles of 37.93 (5) and 8.97 (12)°, respectively, with the phenyl ring. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds into layers lying parallel to (100). The crystal structure is further consolidated by π-π [centroid-centroid distance = 3.6059 (6) Å] inter-actions.

Related literature

For general background to and the biological activity of 1,2,3-triazole derivatives, see: Sherement et al. (2004 ▶); Danoun et al. (1998 ▶); Manfredini et al. (2000 ▶); Biagi et al. (2004 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Fun, Quah, Chandrakantha et al. (2011 ▶); Fun, Quah, Nithinchandra et al. (2011 ▶).

Experimental

Crystal data

C12H12N4O4

M = 276.26

Monoclinic,

a = 13.5309 (3) Å

b = 7.3014 (2) Å

c = 12.6058 (3) Å

β = 99.574 (1)°

V = 1228.04 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.50 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.944, T max = 0.982

16800 measured reflections

4469 independent reflections

3699 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.03

4469 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033940/hb6375sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033940/hb6375Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033940/hb6375Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H12N4O4	F(000) = 576
Mr = 276.26	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8459 reflections
a = 13.5309 (3) Å	θ = 3.1–32.6°
b = 7.3014 (2) Å	µ = 0.12 mm−1
c = 12.6058 (3) Å	T = 100 K
β = 99.574 (1)°	Plate, colourless
V = 1228.04 (5) Å3	0.50 × 0.16 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4469 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 32.6°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→18
Tmin = 0.944, Tmax = 0.982	k = −11→8
16800 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.3698P] where P = (Fo2 + 2Fc2)/3
4469 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.17538 (5)	0.16665 (10)	−0.05384 (5)	0.01804 (15)
O2	0.81492 (6)	0.19872 (12)	0.56912 (6)	0.02603 (18)
O3	0.88912 (6)	0.04601 (13)	0.45702 (7)	0.02874 (19)
O4	0.14766 (5)	0.02184 (11)	0.09686 (6)	0.02182 (16)
N1	0.45814 (6)	0.12739 (11)	0.18124 (6)	0.01308 (15)
N2	0.46803 (6)	0.17529 (12)	0.07841 (6)	0.01609 (16)
N3	0.37872 (6)	0.17308 (12)	0.02083 (6)	0.01568 (16)
N4	0.81564 (6)	0.12105 (13)	0.48264 (7)	0.01954 (17)
C1	0.63468 (7)	0.05446 (13)	0.22772 (7)	0.01570 (17)
H1A	0.6336	0.0113	0.1564	0.019*
C2	0.72344 (7)	0.05470 (13)	0.30098 (7)	0.01654 (17)
H2A	0.7841	0.0126	0.2807	0.020*
C3	0.72162 (7)	0.11789 (13)	0.40463 (7)	0.01516 (17)
C4	0.63467 (7)	0.17883 (13)	0.43757 (7)	0.01519 (17)
H4A	0.6358	0.2197	0.5093	0.018*
C5	0.54574 (7)	0.17947 (13)	0.36424 (7)	0.01414 (16)
H5A	0.4852	0.2209	0.3850	0.017*
C6	0.54695 (6)	0.11829 (13)	0.25977 (7)	0.01296 (16)
C7	0.36061 (6)	0.09299 (12)	0.18864 (7)	0.01266 (16)
C8	0.31097 (7)	0.12254 (13)	0.08482 (7)	0.01365 (16)
C9	0.20306 (7)	0.09756 (13)	0.04465 (7)	0.01549 (17)
C10	0.32346 (7)	0.03491 (14)	0.28808 (7)	0.01660 (18)
H10A	0.3749	−0.0389	0.3327	0.025*
H10B	0.2624	−0.0381	0.2686	0.025*
H10C	0.3087	0.1434	0.3284	0.025*
C11	0.06813 (7)	0.14784 (16)	−0.09678 (8)	0.0212 (2)
H11A	0.0276	0.1941	−0.0440	0.025*
H11B	0.0510	0.0175	−0.1116	0.025*
C12	0.04675 (8)	0.25753 (17)	−0.19890 (8)	0.0252 (2)
H12A	−0.0243	0.2459	−0.2301	0.038*
H12B	0.0879	0.2116	−0.2502	0.038*
H12C	0.0627	0.3866	−0.1830	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0132 (3)	0.0239 (4)	0.0165 (3)	−0.0003 (3)	0.0008 (2)	0.0035 (3)
O2	0.0228 (4)	0.0363 (5)	0.0175 (3)	−0.0044 (3)	−0.0011 (3)	0.0009 (3)
O3	0.0157 (3)	0.0370 (5)	0.0330 (4)	0.0053 (3)	0.0024 (3)	0.0051 (4)
O4	0.0167 (3)	0.0304 (4)	0.0189 (3)	−0.0049 (3)	0.0043 (2)	0.0031 (3)
N1	0.0132 (3)	0.0159 (4)	0.0106 (3)	−0.0003 (3)	0.0035 (2)	0.0001 (3)
N2	0.0153 (3)	0.0219 (4)	0.0116 (3)	−0.0003 (3)	0.0039 (3)	0.0019 (3)
N3	0.0146 (3)	0.0198 (4)	0.0130 (3)	−0.0003 (3)	0.0036 (3)	0.0011 (3)
N4	0.0155 (4)	0.0227 (4)	0.0197 (4)	−0.0016 (3)	0.0009 (3)	0.0060 (3)
C1	0.0166 (4)	0.0165 (4)	0.0150 (4)	0.0002 (3)	0.0056 (3)	−0.0009 (3)
C2	0.0143 (4)	0.0169 (4)	0.0194 (4)	0.0013 (3)	0.0057 (3)	0.0007 (3)
C3	0.0136 (4)	0.0156 (4)	0.0159 (4)	−0.0009 (3)	0.0013 (3)	0.0030 (3)
C4	0.0159 (4)	0.0164 (4)	0.0133 (3)	−0.0003 (3)	0.0027 (3)	0.0012 (3)
C5	0.0141 (4)	0.0158 (4)	0.0130 (3)	0.0006 (3)	0.0037 (3)	0.0001 (3)
C6	0.0130 (4)	0.0132 (4)	0.0128 (3)	−0.0004 (3)	0.0028 (3)	0.0008 (3)
C7	0.0136 (4)	0.0121 (4)	0.0129 (3)	−0.0009 (3)	0.0041 (3)	−0.0005 (3)
C8	0.0141 (4)	0.0152 (4)	0.0124 (3)	−0.0004 (3)	0.0042 (3)	−0.0003 (3)
C9	0.0149 (4)	0.0175 (4)	0.0142 (4)	0.0006 (3)	0.0027 (3)	−0.0014 (3)
C10	0.0176 (4)	0.0198 (4)	0.0134 (4)	−0.0026 (3)	0.0057 (3)	0.0010 (3)
C11	0.0130 (4)	0.0282 (5)	0.0213 (4)	−0.0002 (4)	−0.0007 (3)	0.0024 (4)
C12	0.0207 (5)	0.0312 (6)	0.0220 (4)	0.0025 (4)	−0.0015 (4)	0.0047 (4)

O1—C9	1.3348 (11)	C4—C5	1.3901 (12)
O1—C11	1.4685 (11)	C4—H4A	0.9500
O2—N4	1.2303 (12)	C5—C6	1.3933 (12)
O3—N4	1.2246 (12)	C5—H5A	0.9500
O4—C9	1.2103 (12)	C7—C8	1.3849 (12)
N1—C7	1.3616 (11)	C7—C10	1.4878 (12)
N1—N2	1.3705 (10)	C8—C9	1.4751 (13)
N1—C6	1.4258 (11)	C10—H10A	0.9800
N2—N3	1.3022 (11)	C10—H10B	0.9800
N3—C8	1.3686 (11)	C10—H10C	0.9800
N4—C3	1.4730 (12)	C11—C12	1.5029 (14)
C1—C2	1.3879 (13)	C11—H11A	0.9900
C1—C6	1.3962 (13)	C11—H11B	0.9900
C1—H1A	0.9500	C12—H12A	0.9800
C2—C3	1.3897 (13)	C12—H12B	0.9800
C2—H2A	0.9500	C12—H12C	0.9800
C3—C4	1.3846 (13)
C9—O1—C11	114.50 (8)	N1—C7—C8	103.28 (7)
C7—N1—N2	111.11 (7)	N1—C7—C10	125.27 (8)
C7—N1—C6	131.17 (7)	C8—C7—C10	131.44 (8)
N2—N1—C6	117.71 (7)	N3—C8—C7	109.38 (8)
N3—N2—N1	107.24 (7)	N3—C8—C9	123.56 (8)
N2—N3—C8	108.98 (7)	C7—C8—C9	127.01 (8)
O3—N4—O2	124.49 (9)	O4—C9—O1	125.10 (9)
O3—N4—C3	117.77 (9)	O4—C9—C8	122.48 (8)
O2—N4—C3	117.74 (8)	O1—C9—C8	112.41 (8)
C2—C1—C6	119.36 (8)	C7—C10—H10A	109.5
C2—C1—H1A	120.3	C7—C10—H10B	109.5
C6—C1—H1A	120.3	H10A—C10—H10B	109.5
C1—C2—C3	118.52 (8)	C7—C10—H10C	109.5
C1—C2—H2A	120.7	H10A—C10—H10C	109.5
C3—C2—H2A	120.7	H10B—C10—H10C	109.5
C4—C3—C2	122.51 (8)	O1—C11—C12	107.67 (8)
C4—C3—N4	118.52 (8)	O1—C11—H11A	110.2
C2—C3—N4	118.97 (8)	C12—C11—H11A	110.2
C3—C4—C5	119.11 (8)	O1—C11—H11B	110.2
C3—C4—H4A	120.4	C12—C11—H11B	110.2
C5—C4—H4A	120.4	H11A—C11—H11B	108.5
C4—C5—C6	118.85 (8)	C11—C12—H12A	109.5
C4—C5—H5A	120.6	C11—C12—H12B	109.5
C6—C5—H5A	120.6	H12A—C12—H12B	109.5
C5—C6—C1	121.66 (8)	C11—C12—H12C	109.5
C5—C6—N1	120.02 (8)	H12A—C12—H12C	109.5
C1—C6—N1	118.27 (8)	H12B—C12—H12C	109.5
C7—N1—N2—N3	0.42 (10)	C7—N1—C6—C1	142.62 (10)
C6—N1—N2—N3	179.36 (8)	N2—N1—C6—C1	−36.07 (12)
N1—N2—N3—C8	−0.58 (10)	N2—N1—C7—C8	−0.07 (10)
C6—C1—C2—C3	0.41 (14)	C6—N1—C7—C8	−178.83 (9)
C1—C2—C3—C4	0.58 (14)	N2—N1—C7—C10	179.02 (9)
C1—C2—C3—N4	−179.20 (8)	C6—N1—C7—C10	0.27 (15)
O3—N4—C3—C4	171.06 (9)	N2—N3—C8—C7	0.56 (11)
O2—N4—C3—C4	−8.86 (13)	N2—N3—C8—C9	−177.07 (9)
O3—N4—C3—C2	−9.16 (13)	N1—C7—C8—N3	−0.28 (10)
O2—N4—C3—C2	170.93 (9)	C10—C7—C8—N3	−179.30 (9)
C2—C3—C4—C5	−0.85 (14)	N1—C7—C8—C9	177.24 (9)
N4—C3—C4—C5	178.93 (8)	C10—C7—C8—C9	−1.78 (17)
C3—C4—C5—C6	0.12 (14)	C11—O1—C9—O4	1.16 (14)
C4—C5—C6—C1	0.87 (14)	C11—O1—C9—C8	−179.05 (8)
C4—C5—C6—N1	−176.36 (8)	N3—C8—C9—O4	166.28 (9)
C2—C1—C6—C5	−1.14 (14)	C7—C8—C9—O4	−10.92 (16)
C2—C1—C6—N1	176.14 (8)	N3—C8—C9—O1	−13.51 (13)
C7—N1—C6—C5	−40.05 (14)	C7—C8—C9—O1	169.29 (9)
N2—N1—C6—C5	141.26 (9)	C9—O1—C11—C12	171.11 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N3i	0.95	2.59	3.5243 (12)	168
C5—H5A···N2ii	0.95	2.60	3.2347 (12)	125
C5—H5A···N3ii	0.95	2.54	3.4127 (12)	154
C10—H10B···O4	0.98	2.48	3.0936 (12)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N3i	0.95	2.59	3.5243 (12)	168
C5—H5A⋯N2ii	0.95	2.60	3.2347 (12)	125
C5—H5A⋯N3ii	0.95	2.54	3.4127 (12)	154
C10—H10B⋯O4	0.98	2.48	3.0936 (12)	120

Symmetry codes: (i) ; (ii) .