5-Methyl-1-(3-nitro-benz-yl)-1H-1,2,3-triazole-4-carboxylic acid monohydrate.

The title compound, C(11)H(10)N(4)O(4)·H(2)O, was synthesized from 1-azido-methyl-3-nitro-benzene and ethyl acetyl-acetate. Single-crystal X-ray analysis reveals that the dihedral angle between the triazole and benzene ring planes is 84.80 (2)°. The packing of the mol-ecules is stabilized by strong O-H⋯O hydrogen bonds involving the solvent water mol-ecules as donors and acceptors. The resulting layers are arranged into a three-dimensional framework via weak C-H⋯O inter-actions.

Related literature

For the synthesis of the title compound, see: El Khadem et al. (1968 ▶). For related literature about biological activity of triazole-based compounds, see: Olesen et al. (2003 ▶); Tian et al. (2005 ▶).

Experimental

Crystal data

C11H10N4O4·H2O

M = 280.25

Triclinic,

a = 7.1649 (14) Å

b = 8.2064 (16) Å

c = 11.281 (2) Å

α = 84.88 (3)°

β = 77.70 (2)°

γ = 89.38 (3)°

V = 645.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293.1 K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.965, T max = 0.977

6749 measured reflections

2959 independent reflections

1824 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.181

S = 1.02

2959 reflections

186 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030584/bh2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030584/bh2192Isup2.hkl

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

C11H10N4O4·H2O	Z = 2
Mr = 280.25	F(000) = 292
Triclinic, P1	Dx = 1.442 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1649 (14) Å	Cell parameters from 5670 reflections
b = 8.2064 (16) Å	θ = 3.1–27.5°
c = 11.281 (2) Å	µ = 0.12 mm−1
α = 84.88 (3)°	T = 293 K
β = 77.70 (2)°	Prism, colourless
γ = 89.38 (3)°	0.20 × 0.18 × 0.15 mm
V = 645.5 (2) Å3

Rigaku SCXmini diffractometer	2959 independent reflections
Radiation source: fine-focus sealed tube	1824 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.965, Tmax = 0.977	l = −14→14
6749 measured reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0847P)2 + 0.0594P] where P = (Fo2 + 2Fc2)/3
2959 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.21 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.7354 (3)	−0.2576 (3)	0.1023 (2)	0.0489 (6)
C2	0.8477 (3)	−0.1276 (3)	0.13603 (19)	0.0445 (5)
C3	0.7947 (3)	0.0281 (3)	0.16613 (19)	0.0453 (5)
C4	0.6141 (4)	0.1200 (3)	0.1754 (3)	0.0662 (7)
H4A	0.5476	0.1149	0.2591	0.099*
H4B	0.5357	0.0725	0.1281	0.099*
H4C	0.6419	0.2321	0.1451	0.099*
C5	0.9906 (4)	0.2546 (3)	0.2222 (2)	0.0552 (6)
H5A	0.9527	0.3352	0.1637	0.066*
H5B	1.1266	0.2683	0.2166	0.066*
C6	0.8858 (3)	0.2880 (3)	0.3486 (2)	0.0481 (6)
C7	0.8471 (3)	0.4501 (3)	0.3709 (2)	0.0490 (6)
H7	0.8787	0.5334	0.3083	0.059*
C8	0.7616 (3)	0.4858 (3)	0.4866 (2)	0.0525 (6)
C9	0.7117 (4)	0.3678 (4)	0.5813 (2)	0.0673 (7)
H9	0.6549	0.3952	0.6589	0.081*
C10	0.7481 (5)	0.2061 (4)	0.5582 (2)	0.0755 (8)
H10	0.7139	0.1233	0.6209	0.091*
C11	0.8352 (4)	0.1670 (3)	0.4426 (2)	0.0634 (7)
H11	0.8597	0.0582	0.4282	0.076*
N1	1.0337 (3)	−0.1508 (2)	0.14233 (18)	0.0543 (5)
N2	1.0999 (3)	−0.0190 (2)	0.17513 (19)	0.0584 (6)
N3	0.9557 (3)	0.0908 (2)	0.18882 (17)	0.0487 (5)
N4	0.7247 (3)	0.6596 (3)	0.5081 (3)	0.0710 (7)
O1	0.8110 (3)	−0.3876 (2)	0.07308 (19)	0.0758 (6)
O2	0.5593 (3)	−0.2220 (3)	0.1079 (2)	0.0867 (7)
H2	0.506 (8)	−0.295 (6)	0.091 (5)	0.18 (2)*
O3	0.7575 (4)	0.7611 (3)	0.4204 (3)	0.1067 (9)
O4	0.6635 (3)	0.6915 (3)	0.6118 (2)	0.1040 (8)
O1W	0.2862 (2)	0.5822 (2)	0.09151 (18)	0.0707 (6)
H1A	0.2667	0.5412	0.0287	0.106*
H1B	0.1813	0.6510	0.1111	0.106*

	U11	U22	U33	U12	U13	U23
C1	0.0516 (14)	0.0470 (13)	0.0509 (14)	−0.0009 (11)	−0.0142 (10)	−0.0120 (10)
C2	0.0458 (13)	0.0474 (12)	0.0410 (12)	0.0008 (10)	−0.0070 (9)	−0.0130 (9)
C3	0.0468 (13)	0.0465 (12)	0.0426 (12)	−0.0009 (10)	−0.0066 (9)	−0.0113 (9)
C4	0.0578 (16)	0.0592 (16)	0.085 (2)	0.0136 (13)	−0.0185 (13)	−0.0156 (14)
C5	0.0648 (16)	0.0449 (13)	0.0547 (14)	−0.0102 (11)	−0.0053 (11)	−0.0150 (11)
C6	0.0523 (14)	0.0444 (13)	0.0492 (13)	−0.0073 (10)	−0.0112 (10)	−0.0122 (10)
C7	0.0528 (14)	0.0455 (13)	0.0500 (13)	−0.0056 (11)	−0.0120 (10)	−0.0087 (10)
C8	0.0467 (13)	0.0567 (14)	0.0573 (15)	−0.0022 (11)	−0.0113 (11)	−0.0218 (12)
C9	0.0653 (17)	0.086 (2)	0.0511 (15)	−0.0053 (15)	−0.0088 (12)	−0.0182 (14)
C10	0.093 (2)	0.077 (2)	0.0520 (17)	−0.0084 (17)	−0.0088 (14)	0.0071 (14)
C11	0.0809 (19)	0.0481 (14)	0.0610 (17)	−0.0022 (13)	−0.0148 (13)	−0.0049 (12)
N1	0.0478 (12)	0.0561 (12)	0.0629 (13)	0.0029 (9)	−0.0125 (9)	−0.0257 (10)
N2	0.0509 (12)	0.0593 (13)	0.0689 (14)	0.0023 (10)	−0.0136 (10)	−0.0255 (11)
N3	0.0495 (11)	0.0448 (11)	0.0521 (11)	−0.0024 (9)	−0.0068 (8)	−0.0163 (9)
N4	0.0608 (14)	0.0758 (17)	0.0824 (18)	0.0047 (12)	−0.0141 (12)	−0.0429 (15)
O1	0.0991 (15)	0.0526 (11)	0.0874 (14)	0.0051 (10)	−0.0357 (11)	−0.0311 (10)
O2	0.0653 (14)	0.0731 (14)	0.132 (2)	−0.0111 (11)	−0.0395 (13)	−0.0188 (13)
O3	0.144 (2)	0.0529 (13)	0.115 (2)	−0.0030 (14)	−0.0029 (17)	−0.0215 (13)
O4	0.1111 (19)	0.1131 (19)	0.0943 (17)	0.0254 (15)	−0.0156 (14)	−0.0625 (15)
O1W	0.0632 (12)	0.0561 (11)	0.0935 (14)	−0.0015 (9)	−0.0099 (10)	−0.0259 (10)

C1—O1	1.230 (3)	C7—C8	1.374 (3)
C1—O2	1.282 (3)	C7—H7	0.9300
C1—C2	1.467 (3)	C8—C9	1.366 (4)
C2—N1	1.360 (3)	C8—N4	1.479 (3)
C2—C3	1.380 (3)	C9—C10	1.386 (4)
C3—N3	1.350 (3)	C9—H9	0.9300
C3—C4	1.479 (3)	C10—C11	1.385 (4)
C4—H4A	0.9600	C10—H10	0.9300
C4—H4B	0.9600	C11—H11	0.9300
C4—H4C	0.9600	N1—N2	1.300 (3)
C5—N3	1.466 (3)	N2—N3	1.356 (3)
C5—C6	1.510 (3)	N4—O4	1.210 (3)
C5—H5A	0.9700	N4—O3	1.219 (3)
C5—H5B	0.9700	O2—H2	0.77 (5)
C6—C11	1.377 (3)	O1W—H1B	0.9349
C6—C7	1.391 (3)	O1W—H1A	0.8483
O1—C1—O2	125.6 (2)	C8—C7—H7	120.4
O1—C1—C2	120.3 (2)	C6—C7—H7	120.4
O2—C1—C2	114.1 (2)	C9—C8—C7	122.6 (2)
N1—C2—C3	109.06 (19)	C9—C8—N4	119.4 (2)
N1—C2—C1	121.1 (2)	C7—C8—N4	118.0 (2)
C3—C2—C1	129.8 (2)	C8—C9—C10	118.1 (2)
N3—C3—C2	103.26 (19)	C8—C9—H9	121.0
N3—C3—C4	123.4 (2)	C10—C9—H9	121.0
C2—C3—C4	133.4 (2)	C11—C10—C9	120.4 (2)
C3—C4—H4A	109.5	C11—C10—H10	119.8
C3—C4—H4B	109.5	C9—C10—H10	119.8
H4A—C4—H4B	109.5	C6—C11—C10	120.6 (2)
C3—C4—H4C	109.5	C6—C11—H11	119.7
H4A—C4—H4C	109.5	C10—C11—H11	119.7
H4B—C4—H4C	109.5	N2—N1—C2	109.17 (19)
N3—C5—C6	114.05 (19)	N1—N2—N3	106.90 (18)
N3—C5—H5A	108.7	C3—N3—N2	111.60 (18)
C6—C5—H5A	108.7	C3—N3—C5	129.1 (2)
N3—C5—H5B	108.7	N2—N3—C5	119.26 (18)
C6—C5—H5B	108.7	O4—N4—O3	124.3 (3)
H5A—C5—H5B	107.6	O4—N4—C8	117.7 (3)
C11—C6—C7	119.2 (2)	O3—N4—C8	118.0 (2)
C11—C6—C5	123.2 (2)	C1—O2—H2	110 (4)
C7—C6—C5	117.5 (2)	H1B—O1W—H1A	102.8
C8—C7—C6	119.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O4i	0.96	2.52	3.267 (3)	135
O1W—H1A···O1ii	0.85	1.94	2.755 (3)	161
O1W—H1B···N1iii	0.93	1.95	2.846 (3)	160
C11—H11···O3iv	0.93	2.57	3.423 (4)	153
O2—H2···O1Wiv	0.77 (5)	1.88 (5)	2.592 (3)	153 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O4i	0.96	2.52	3.267 (3)	135
O1W—H1A⋯O1ii	0.85	1.94	2.755 (3)	161
O1W—H1B⋯N1iii	0.93	1.95	2.846 (3)	160
C11—H11⋯O3iv	0.93	2.57	3.423 (4)	153
O2—H2⋯O1Wiv	0.77 (5)	1.88 (5)	2.592 (3)	153 (6)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .