3-(2-Ethoxy­phen­yl)-5-methyl­sulfanyl-4H-1,2,4-triazol-4-amine monohydrate

In the title compound, C₁₁H₁₄N₄OS·H₂O, the dihedral angle between the ethoxy­benzene group and the triazole ring is 48.20 (8)°. Inter­molecular N—H...O and O—H...N hydrogen bonds involving the water mol­ecules form a chain along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.044
• wR factor = 0.114
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

3-(2-Ethoxyphenyl)-5-methylsulfanyl-4H-1,2,4-triazol-4-amine monohydrate

Crystal data

C11H14N4OS·H2O	Z = 2
Mr = 268.34	F(000) = 284
Triclinic, P1	Dx = 1.319 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5828 (13) Å	Cell parameters from 1447 reflections
b = 8.9824 (15) Å	θ = 2.5–25.0°
c = 11.5308 (19) Å	µ = 0.24 mm^−1
α = 109.542 (3)°	T = 298 K
β = 98.836 (3)°	Block, colourless
γ = 107.754 (3)°	0.29 × 0.17 × 0.15 mm
V = 675.7 (2) Å^3

Data collection

Bruker APEX area-detector diffractometer	2350 independent reflections
Radiation source: fine-focus sealed tube	2036 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→5
Tmin = 0.934, Tmax = 0.960	k = −10→10
3570 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0558P)^2 + 0.2204P] where P = (Fo^2 + 2Fc^2)/3
2350 reflections	(Δ/σ)max = 0.001
179 parameters	Δρmax = 0.21 e Å^−3
5 restraints	Δρmin = −0.27 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
S1	0.51827 (8)	0.78535 (7)	0.92583 (6)	0.0519 (2)
O1	0.2879 (2)	0.22987 (17)	0.50608 (13)	0.0450 (4)
O2	0.9684 (3)	0.2667 (3)	0.86389 (16)	0.0681 (5)
N1	0.6639 (2)	0.3926 (2)	0.83462 (16)	0.0437 (4)
N2	0.7055 (2)	0.5641 (2)	0.90802 (16)	0.0451 (4)
N3	0.4096 (2)	0.4481 (2)	0.78349 (15)	0.0377 (4)
N4	0.2235 (3)	0.4397 (3)	0.7338 (2)	0.0507 (5)
C1	0.3890 (3)	0.1456 (3)	0.66862 (19)	0.0379 (5)
C2	0.2934 (3)	0.0994 (2)	0.54047 (18)	0.0373 (4)
C3	0.2167 (3)	−0.0707 (3)	0.4548 (2)	0.0436 (5)
H3	0.1534	−0.1014	0.3695	0.052*
C4	0.2344 (3)	−0.1940 (3)	0.4960 (2)	0.0492 (5)
H4	0.1829	−0.3079	0.4380	0.059*
C5	0.3272 (3)	−0.1513 (3)	0.6218 (2)	0.0512 (6)
H5	0.3373	−0.2357	0.6490	0.061*
C6	0.4049 (3)	0.0177 (3)	0.7069 (2)	0.0449 (5)
H6	0.4692	0.0470	0.7916	0.054*
C7	0.4867 (3)	0.3254 (3)	0.76118 (18)	0.0372 (4)
C8	0.5516 (3)	0.5933 (3)	0.87391 (18)	0.0384 (5)
C9	0.7634 (4)	0.9284 (3)	1.0083 (3)	0.0719 (8)
H9A	0.8102	0.9036	1.0791	0.108*
H9B	0.7705	1.0441	1.0399	0.108*
H9C	0.8413	0.9144	0.9503	0.108*
C10	0.1908 (4)	0.1875 (3)	0.3751 (2)	0.0494 (6)
H10A	0.0579	0.1094	0.3519	0.059*
H10B	0.2550	0.1336	0.3175	0.059*
C11	0.1985 (4)	0.3522 (3)	0.3665 (3)	0.0679 (7)
H11A	0.1379	0.4058	0.4258	0.102*
H11B	0.1317	0.3293	0.2808	0.102*
H11C	0.3307	0.4270	0.3872	0.102*
H2A	0.880 (3)	0.306 (4)	0.862 (3)	0.081*
H2B	1.048 (3)	0.319 (3)	0.9388 (19)	0.081*
H4A	0.194 (3)	0.385 (3)	0.6518 (16)	0.057 (7)*
H4B	0.153 (3)	0.390 (3)	0.774 (2)	0.064 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0499 (4)	0.0439 (3)	0.0520 (4)	0.0204 (3)	0.0055 (3)	0.0094 (3)
O1	0.0564 (9)	0.0381 (8)	0.0350 (7)	0.0166 (7)	0.0026 (6)	0.0141 (6)
O2	0.0591 (11)	0.0787 (13)	0.0470 (10)	0.0382 (10)	−0.0073 (8)	0.0019 (9)
N1	0.0399 (10)	0.0431 (10)	0.0403 (9)	0.0173 (8)	−0.0006 (8)	0.0117 (8)
N2	0.0401 (10)	0.0437 (10)	0.0388 (9)	0.0142 (8)	−0.0016 (8)	0.0092 (8)
N3	0.0307 (8)	0.0398 (9)	0.0337 (9)	0.0116 (7)	0.0009 (7)	0.0098 (7)
N4	0.0376 (10)	0.0560 (12)	0.0470 (12)	0.0211 (9)	0.0002 (9)	0.0096 (10)
C1	0.0337 (10)	0.0409 (11)	0.0359 (10)	0.0138 (8)	0.0067 (8)	0.0135 (9)
C2	0.0351 (10)	0.0383 (11)	0.0371 (11)	0.0136 (8)	0.0068 (8)	0.0154 (9)
C3	0.0433 (12)	0.0386 (11)	0.0395 (11)	0.0142 (9)	0.0030 (9)	0.0101 (9)
C4	0.0500 (13)	0.0352 (11)	0.0536 (13)	0.0157 (10)	0.0071 (10)	0.0115 (10)
C5	0.0555 (14)	0.0446 (13)	0.0600 (14)	0.0244 (10)	0.0118 (11)	0.0262 (11)
C6	0.0455 (12)	0.0505 (13)	0.0411 (11)	0.0206 (10)	0.0077 (9)	0.0215 (10)
C7	0.0371 (11)	0.0404 (11)	0.0329 (10)	0.0155 (8)	0.0054 (8)	0.0148 (9)
C8	0.0364 (11)	0.0400 (11)	0.0329 (10)	0.0122 (8)	0.0056 (8)	0.0120 (9)
C9	0.0539 (16)	0.0455 (14)	0.088 (2)	0.0100 (11)	0.0113 (14)	0.0060 (13)
C10	0.0593 (14)	0.0532 (13)	0.0366 (11)	0.0243 (11)	0.0059 (10)	0.0203 (10)
C11	0.089 (2)	0.0668 (17)	0.0584 (15)	0.0315 (15)	0.0161 (14)	0.0381 (14)

Geometric parameters (Å, º)

S1—C8	1.738 (2)	C2—C3	1.385 (3)
S1—C9	1.787 (3)	C3—C4	1.377 (3)
O1—C2	1.367 (2)	C3—H3	0.93
O1—C10	1.439 (2)	C4—C5	1.377 (3)
O2—H2A	0.846 (16)	C4—H4	0.93
O2—H2B	0.852 (16)	C5—C6	1.377 (3)
N1—C7	1.304 (3)	C5—H5	0.93
N1—N2	1.393 (2)	C6—H6	0.93
N2—C8	1.304 (3)	C9—H9A	0.96
N3—C8	1.355 (2)	C9—H9B	0.96
N3—C7	1.368 (3)	C9—H9C	0.96
N3—N4	1.408 (2)	C10—C11	1.500 (3)
N4—H4A	0.861 (16)	C10—H10A	0.97
N4—H4B	0.876 (17)	C10—H10B	0.97
C1—C6	1.392 (3)	C11—H11A	0.96
C1—C2	1.399 (3)	C11—H11B	0.96
C1—C7	1.473 (3)	C11—H11C	0.96
C8—S1—C9	99.23 (11)	C5—C6—H6	119.4
C2—O1—C10	118.18 (16)	C1—C6—H6	119.4
H2A—O2—H2B	109 (2)	N1—C7—N3	109.20 (17)
C7—N1—N2	107.92 (16)	N1—C7—C1	124.45 (18)
C8—N2—N1	106.79 (15)	N3—C7—C1	126.35 (17)
C8—N3—C7	105.70 (16)	N2—C8—N3	110.37 (18)
C8—N3—N4	122.75 (17)	N2—C8—S1	128.53 (15)
C7—N3—N4	131.50 (16)	N3—C8—S1	121.07 (15)
N3—N4—H4A	106.0 (17)	S1—C9—H9A	109.5
N3—N4—H4B	104.0 (18)	S1—C9—H9B	109.5
H4A—N4—H4B	117 (3)	H9A—C9—H9B	109.5
C6—C1—C2	118.56 (19)	S1—C9—H9C	109.5
C6—C1—C7	118.97 (18)	H9A—C9—H9C	109.5
C2—C1—C7	122.28 (18)	H9B—C9—H9C	109.5
O1—C2—C3	123.40 (18)	O1—C10—C11	106.72 (19)
O1—C2—C1	116.50 (17)	O1—C10—H10A	110.4
C3—C2—C1	120.05 (18)	C11—C10—H10A	110.4
C4—C3—C2	119.88 (19)	O1—C10—H10B	110.4
C4—C3—H3	120.1	C11—C10—H10B	110.4
C2—C3—H3	120.1	H10A—C10—H10B	108.6
C3—C4—C5	121.0 (2)	C10—C11—H11A	109.5
C3—C4—H4	119.5	C10—C11—H11B	109.5
C5—C4—H4	119.5	H11A—C11—H11B	109.5
C6—C5—C4	119.2 (2)	C10—C11—H11C	109.5
C6—C5—H5	120.4	H11A—C11—H11C	109.5
C4—C5—H5	120.4	H11B—C11—H11C	109.5
C5—C6—C1	121.28 (19)
C7—N1—N2—C8	−0.9 (2)	N4—N3—C7—N1	−177.0 (2)
C10—O1—C2—C3	2.5 (3)	C8—N3—C7—C1	−178.92 (18)
C10—O1—C2—C1	−179.99 (18)	N4—N3—C7—C1	3.7 (3)
C6—C1—C2—O1	−177.50 (18)	C6—C1—C7—N1	45.6 (3)
C7—C1—C2—O1	−2.6 (3)	C2—C1—C7—N1	−129.3 (2)
C6—C1—C2—C3	0.1 (3)	C6—C1—C7—N3	−135.1 (2)
C7—C1—C2—C3	174.97 (19)	C2—C1—C7—N3	50.0 (3)
O1—C2—C3—C4	177.55 (19)	N1—N2—C8—N3	1.2 (2)
C1—C2—C3—C4	0.2 (3)	N1—N2—C8—S1	−176.75 (15)
C2—C3—C4—C5	0.2 (3)	C7—N3—C8—N2	−1.1 (2)
C3—C4—C5—C6	−0.7 (4)	N4—N3—C8—N2	176.62 (19)
C4—C5—C6—C1	0.9 (3)	C7—N3—C8—S1	177.08 (14)
C2—C1—C6—C5	−0.6 (3)	N4—N3—C8—S1	−5.2 (3)
C7—C1—C6—C5	−175.68 (19)	C9—S1—C8—N2	11.5 (2)
N2—N1—C7—N3	0.3 (2)	C9—S1—C8—N3	−166.29 (18)
N2—N1—C7—C1	179.67 (17)	C2—O1—C10—C11	177.21 (19)
C8—N3—C7—N1	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O2^i	0.88 (2)	2.13 (2)	3.004 (3)	177 (2)
N4—H4A···O1	0.86 (2)	2.16 (2)	2.886 (3)	141 (2)
O2—H2B···N2^ii	0.85 (2)	2.07 (2)	2.894 (2)	164 (3)
O2—H2A···N1	0.85 (2)	2.05 (2)	2.887 (2)	173 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+2.