3,5-Bis(4-methoxy-phen-yl)-1H-1,2,4-triazole monohydrate.

In the title compound, C(16)H(15)N(3)O(2)·H(2)O, the two benzene rings and the triazole ring lie almost in the same plane, the triazole ring forming dihedral angles of 5.07 (9) and 5.80 (8)° with the benzene rings. In the crystal, there are three relatively strong inter-molecular O-H⋯N and N-H⋯O hydrogen bonds, which lead to the formation of a one-dimensional double chain running parallel to the a axis. Weak π-π inter-actions between the benzene rings of neighboring chains with a centroid-centroid distance of 3.893 (4) Å result in the formation of layers parallel to the ac plane.

Related literature

For the biological activity and pharmaceutical applications of compounds containing triazole subunits, see: Chai et al. (2009 ▶); Nadkarni et al. (2001 ▶); Zhan & Lou (2007 ▶). For triazole ring bond-length data, see; Claramunt et al. (2001 ▶); Zhou et al. (2001 ▶); John (1998 ▶).

Experimental

Crystal data

C16H15N3O2·H2O

M = 299.33

Triclinic,

a = 6.9948 (18) Å

b = 11.125 (3) Å

c = 11.184 (3) Å

α = 110.603 (4)°

β = 107.932 (3)°

γ = 95.690 (4)°

V = 753.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

3854 measured reflections

2651 independent reflections

1993 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.134

S = 1.05

2651 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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/S160053680901695X/zl2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901695X/zl2201Isup2.hkl

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

C16H15N3O2·H2O	Z = 2
Mr = 299.33	F(000) = 316
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9948 (18) Å	Cell parameters from 1120 reflections
b = 11.125 (3) Å	θ = 2.2–24.0°
c = 11.184 (3) Å	µ = 0.09 mm−1
α = 110.603 (4)°	T = 298 K
β = 107.932 (3)°	Block, colourless
γ = 95.690 (4)°	0.40 × 0.20 × 0.19 mm
V = 753.8 (3) Å3

Bruker SMART CCD area-detector diffractometer	1993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
graphite	θmax = 25.1°, θmin = 2.0°
phi and ω scans	h = −4→8
3854 measured reflections	k = −13→11
2651 independent reflections	l = −12→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.0124P] where P = (Fo2 + 2Fc2)/3
2651 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	1.3626 (4)	0.5268 (3)	0.8502 (3)	0.0831 (8)
H1A	1.4171	0.4539	0.8091	0.125*
H1B	1.4672	0.5887	0.9349	0.125*
H1C	1.3199	0.5696	0.7886	0.125*
C2	1.0219 (3)	0.3942 (2)	0.7668 (2)	0.0493 (5)
C3	0.8500 (3)	0.3622 (2)	0.7965 (2)	0.0506 (5)
H3	0.8550	0.3978	0.8864	0.061*
C4	0.6729 (3)	0.27787 (19)	0.6928 (2)	0.0447 (5)
H4	0.5585	0.2571	0.7137	0.054*
C5	0.6599 (3)	0.22255 (18)	0.55736 (19)	0.0394 (5)
C6	0.8338 (3)	0.2549 (2)	0.5307 (2)	0.0524 (6)
H6	0.8292	0.2193	0.4409	0.063*
C7	1.0141 (3)	0.3388 (2)	0.6341 (2)	0.0578 (6)
H7	1.1300	0.3576	0.6138	0.069*
C8	0.4703 (3)	0.13404 (18)	0.44671 (18)	0.0368 (4)
C9	0.2616 (3)	0.00131 (18)	0.24816 (19)	0.0379 (5)
C10	0.1682 (3)	−0.08505 (18)	0.10190 (19)	0.0393 (5)
C11	0.2847 (3)	−0.0918 (2)	0.0197 (2)	0.0519 (6)
H11	0.4199	−0.0417	0.0587	0.062*
C12	0.2030 (3)	−0.1712 (2)	−0.1177 (2)	0.0598 (6)
H12	0.2828	−0.1741	−0.1711	0.072*
C13	0.0040 (3)	−0.2468 (2)	−0.1776 (2)	0.0503 (5)
C14	−0.1137 (3)	−0.2420 (2)	−0.0979 (2)	0.0539 (6)
H14	−0.2481	−0.2932	−0.1372	0.065*
C15	−0.0313 (3)	−0.1610 (2)	0.0403 (2)	0.0499 (5)
H15	−0.1121	−0.1576	0.0932	0.060*
C16	−0.2664 (4)	−0.4015 (2)	−0.3827 (2)	0.0745 (8)
H16A	−0.2851	−0.4629	−0.3425	0.112*
H16B	−0.2915	−0.4491	−0.4783	0.112*
H16C	−0.3617	−0.3455	−0.3735	0.112*
N1	0.2943 (2)	0.10899 (16)	0.46420 (16)	0.0437 (4)
N2	0.1636 (2)	0.02456 (16)	0.33612 (16)	0.0424 (4)
H2	0.0354	−0.0092	0.3148	0.051*
N3	0.4569 (2)	0.06990 (15)	0.31449 (15)	0.0404 (4)
O1	−0.0613 (2)	−0.32325 (16)	−0.31464 (15)	0.0726 (5)
O2	1.1911 (2)	0.48023 (16)	0.87639 (15)	0.0693 (5)
O3	0.2326 (2)	0.08148 (15)	0.69915 (14)	0.0540 (4)
H3A	0.2339	0.1008	0.6215	0.100*
H3B	0.3314	0.0294	0.7142	0.100*

	U11	U22	U33	U12	U13	U23
C1	0.0486 (14)	0.087 (2)	0.079 (2)	−0.0039 (13)	0.0166 (13)	0.0062 (16)
C2	0.0446 (12)	0.0498 (13)	0.0414 (12)	0.0095 (10)	0.0117 (10)	0.0088 (10)
C3	0.0611 (14)	0.0521 (13)	0.0338 (12)	0.0116 (10)	0.0194 (10)	0.0106 (10)
C4	0.0481 (12)	0.0474 (12)	0.0392 (12)	0.0092 (9)	0.0215 (9)	0.0139 (10)
C5	0.0434 (11)	0.0407 (11)	0.0372 (11)	0.0122 (9)	0.0182 (9)	0.0157 (9)
C6	0.0494 (13)	0.0623 (14)	0.0362 (12)	0.0052 (10)	0.0205 (10)	0.0075 (10)
C7	0.0457 (12)	0.0662 (15)	0.0519 (14)	0.0043 (11)	0.0238 (11)	0.0103 (12)
C8	0.0401 (10)	0.0403 (11)	0.0340 (11)	0.0121 (8)	0.0173 (8)	0.0157 (9)
C9	0.0373 (10)	0.0439 (11)	0.0381 (11)	0.0114 (9)	0.0175 (9)	0.0191 (10)
C10	0.0417 (11)	0.0419 (11)	0.0351 (11)	0.0075 (9)	0.0147 (9)	0.0166 (9)
C11	0.0477 (12)	0.0585 (14)	0.0380 (12)	−0.0078 (10)	0.0166 (10)	0.0109 (11)
C12	0.0638 (15)	0.0636 (15)	0.0438 (13)	−0.0072 (12)	0.0258 (11)	0.0130 (12)
C13	0.0615 (14)	0.0427 (12)	0.0346 (12)	0.0000 (10)	0.0095 (10)	0.0123 (10)
C14	0.0437 (12)	0.0563 (14)	0.0495 (14)	−0.0016 (10)	0.0101 (10)	0.0170 (11)
C15	0.0397 (11)	0.0608 (14)	0.0475 (13)	0.0072 (10)	0.0173 (10)	0.0202 (11)
C16	0.0777 (17)	0.0606 (16)	0.0490 (15)	−0.0158 (13)	−0.0073 (12)	0.0160 (13)
N1	0.0420 (9)	0.0526 (10)	0.0366 (10)	0.0123 (8)	0.0178 (8)	0.0148 (8)
N2	0.0329 (8)	0.0539 (10)	0.0385 (10)	0.0071 (7)	0.0147 (7)	0.0160 (8)
N3	0.0370 (9)	0.0472 (10)	0.0338 (9)	0.0064 (7)	0.0148 (7)	0.0124 (8)
O1	0.0834 (12)	0.0678 (11)	0.0387 (10)	−0.0165 (9)	0.0129 (8)	0.0074 (8)
O2	0.0503 (9)	0.0764 (12)	0.0499 (10)	−0.0021 (8)	0.0085 (7)	0.0033 (9)
O3	0.0439 (8)	0.0746 (10)	0.0513 (9)	0.0170 (7)	0.0265 (7)	0.0255 (8)

C1—O2	1.412 (3)	C9—C10	1.462 (3)
C1—H1A	0.9600	C10—C15	1.379 (3)
C1—H1B	0.9600	C10—C11	1.393 (3)
C1—H1C	0.9600	C11—C12	1.368 (3)
C2—O2	1.370 (2)	C11—H11	0.9300
C2—C7	1.373 (3)	C12—C13	1.375 (3)
C2—C3	1.389 (3)	C12—H12	0.9300
C3—C4	1.370 (3)	C13—O1	1.362 (2)
C3—H3	0.9300	C13—C14	1.380 (3)
C4—C5	1.390 (3)	C14—C15	1.379 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.381 (3)	C15—H15	0.9300
C5—C8	1.461 (3)	C16—O1	1.418 (3)
C6—C7	1.381 (3)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C8—N1	1.323 (2)	N1—N2	1.359 (2)
C8—N3	1.365 (2)	N2—H2	0.8600
C9—N3	1.330 (2)	O3—H3A	0.9678
C9—N2	1.333 (2)	O3—H3B	0.9583
O2—C1—H1A	109.5	C15—C10—C9	123.15 (18)
O2—C1—H1B	109.5	C11—C10—C9	119.01 (17)
H1A—C1—H1B	109.5	C12—C11—C10	120.85 (18)
O2—C1—H1C	109.5	C12—C11—H11	119.6
H1A—C1—H1C	109.5	C10—C11—H11	119.6
H1B—C1—H1C	109.5	C11—C12—C13	120.7 (2)
O2—C2—C7	124.66 (19)	C11—C12—H12	119.7
O2—C2—C3	115.73 (19)	C13—C12—H12	119.7
C7—C2—C3	119.61 (19)	O1—C13—C12	115.9 (2)
C4—C3—C2	119.73 (19)	O1—C13—C14	124.71 (19)
C4—C3—H3	120.1	C12—C13—C14	119.4 (2)
C2—C3—H3	120.1	C15—C14—C13	119.77 (19)
C3—C4—C5	121.72 (19)	C15—C14—H14	120.1
C3—C4—H4	119.1	C13—C14—H14	120.1
C5—C4—H4	119.1	C10—C15—C14	121.47 (19)
C6—C5—C4	117.40 (18)	C10—C15—H15	119.3
C6—C5—C8	120.93 (17)	C14—C15—H15	119.3
C4—C5—C8	121.67 (17)	O1—C16—H16A	109.5
C7—C6—C5	121.7 (2)	O1—C16—H16B	109.5
C7—C6—H6	119.2	H16A—C16—H16B	109.5
C5—C6—H6	119.2	O1—C16—H16C	109.5
C2—C7—C6	119.84 (19)	H16A—C16—H16C	109.5
C2—C7—H7	120.1	H16B—C16—H16C	109.5
C6—C7—H7	120.1	C8—N1—N2	102.97 (15)
N1—C8—N3	113.34 (16)	C9—N2—N1	110.53 (15)
N1—C8—C5	123.47 (16)	C9—N2—H2	124.7
N3—C8—C5	123.19 (16)	N1—N2—H2	124.7
N3—C9—N2	109.15 (17)	C9—N3—C8	104.00 (15)
N3—C9—C10	125.62 (17)	C13—O1—C16	118.50 (18)
N2—C9—C10	125.23 (17)	C2—O2—C1	118.09 (18)
C15—C10—C11	117.84 (18)	H3A—O3—H3B	107.8
O2—C2—C3—C4	179.32 (17)	C11—C12—C13—O1	−179.37 (19)
C7—C2—C3—C4	−1.4 (3)	C11—C12—C13—C14	0.1 (3)
C2—C3—C4—C5	0.1 (3)	O1—C13—C14—C15	179.8 (2)
C3—C4—C5—C6	0.5 (3)	C12—C13—C14—C15	0.4 (3)
C3—C4—C5—C8	−179.20 (17)	C11—C10—C15—C14	0.4 (3)
C4—C5—C6—C7	0.1 (3)	C9—C10—C15—C14	−179.59 (18)
C8—C5—C6—C7	179.80 (18)	C13—C14—C15—C10	−0.7 (3)
O2—C2—C7—C6	−178.80 (19)	N3—C8—N1—N2	0.0 (2)
C3—C2—C7—C6	2.0 (3)	C5—C8—N1—N2	179.44 (16)
C5—C6—C7—C2	−1.3 (3)	N3—C9—N2—N1	−0.6 (2)
C6—C5—C8—N1	−173.76 (19)	C10—C9—N2—N1	179.86 (16)
C4—C5—C8—N1	6.0 (3)	C8—N1—N2—C9	0.35 (19)
C6—C5—C8—N3	5.6 (3)	N2—C9—N3—C8	0.6 (2)
C4—C5—C8—N3	−174.69 (17)	C10—C9—N3—C8	−179.88 (17)
N3—C9—C10—C15	175.33 (18)	N1—C8—N3—C9	−0.4 (2)
N2—C9—C10—C15	−5.2 (3)	C5—C8—N3—C9	−179.81 (16)
N3—C9—C10—C11	−4.6 (3)	C12—C13—O1—C16	−178.8 (2)
N2—C9—C10—C11	174.80 (18)	C14—C13—O1—C16	1.8 (3)
C15—C10—C11—C12	0.1 (3)	C7—C2—O2—C1	7.2 (3)
C9—C10—C11—C12	−179.88 (19)	C3—C2—O2—C1	−173.6 (2)
C10—C11—C12—C13	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.97	1.96	2.902 (2)	164
N2—H2···O3i	0.86	1.90	2.753 (2)	170
O3—H3B···N3ii	0.96	1.97	2.885 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1	0.97	1.96	2.902 (2)	164
N2—H2⋯O3i	0.86	1.90	2.753 (2)	170
O3—H3B⋯N3ii	0.96	1.97	2.885 (2)	159

Symmetry codes: (i) ; (ii) .