3,5-Bis(4-hy-droxy-phen-yl)-4H-1,2,4-triazol-4-amine monohydrate.

The triazole ring in the title compound, C(14)H(12)N(4)O(2)·H(2)O, makes dihedral angles of 36.9 (1) and 37.3 (1)° with the two benzene rings. Each hy-droxy group is a hydrogen-bond donor to a two-coordinate N atom of an adjacent mol-ecule; these O-H⋯N hydrogen bonds generate a layer parallel to the ab plane. Adjacent layers are linked by N--H⋯O and O(water)-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For two modifications of 4-amino-3,5-diphenyl-1,2,4-triazole, see: Ikemi et al. (2002 ▶); Zhang et al. (2009 ▶). For comparison structures, see: Wang et al. (2006 ▶); Zachara et al. (2004 ▶); Bentiss et al. (1998 ▶).

Experimental

Crystal data

C14H12N4O2·H2O

M = 286.29

Orthorhombic,

a = 10.6659 (5) Å

b = 15.9790 (8) Å

c = 7.4632 (4) Å

V = 1271.96 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.90 mm−1

T = 100 K

0.30 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction Gemini E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.773, T max = 0.956

2460 measured reflections

1275 independent reflections

1172 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.05

1275 reflections

215 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032915/bt5326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032915/bt5326Isup2.hkl

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

C14H12N4O2·H2O	F(000) = 600
Mr = 286.29	Dx = 1.495 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 1690 reflections
a = 10.6659 (5) Å	θ = 4.1–70.4°
b = 15.9790 (8) Å	µ = 0.90 mm−1
c = 7.4632 (4) Å	T = 100 K
V = 1271.96 (11) Å3	Prism, yellow
Z = 4	0.30 × 0.10 × 0.05 mm

Oxford Diffraction Gemini E diffractometer	1275 independent reflections
Radiation source: fine-focus sealed tube	1172 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 16.1952 pixels mm-1	θmax = 70.0°, θmin = 5.0°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→19
Tmin = 0.773, Tmax = 0.956	l = −9→8
2460 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0762P)2 + 0.0334P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1275 reflections	Δρmax = 0.23 e Å−3
215 parameters	Δρmin = −0.24 e Å−3
8 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (6)

	x	y	z	Uiso*/Ueq
O1	1.05710 (16)	1.15554 (10)	0.5001 (3)	0.0257 (5)
O2	1.07428 (16)	0.33922 (9)	0.5626 (3)	0.0252 (4)
O1W	0.8047 (2)	0.76244 (13)	0.3567 (3)	0.0375 (5)
C1	1.0874 (2)	1.07317 (13)	0.5123 (3)	0.0175 (5)
C2	1.0093 (2)	1.01053 (14)	0.4426 (3)	0.0184 (5)
H2	0.9335	1.0254	0.3839	0.022*
C3	1.0424 (2)	0.92705 (14)	0.4592 (3)	0.0175 (5)
H3	0.9886	0.8848	0.4135	0.021*
C4	1.1546 (2)	0.90481 (12)	0.5428 (3)	0.0157 (5)
C5	1.2323 (2)	0.96757 (13)	0.6105 (3)	0.0166 (5)
H5	1.3087	0.9528	0.6676	0.020*
C6	1.1993 (2)	1.05105 (13)	0.5954 (4)	0.0173 (5)
H6	1.2531	1.0932	0.6418	0.021*
C7	1.19711 (19)	0.81723 (13)	0.5495 (4)	0.0165 (5)
C8	1.20070 (19)	0.68071 (13)	0.5660 (3)	0.0154 (5)
C9	1.1602 (2)	0.59292 (12)	0.5747 (3)	0.0156 (5)
C10	1.0488 (2)	0.56628 (14)	0.4941 (3)	0.0166 (5)
H10	0.9928	0.6063	0.4444	0.020*
C11	1.0195 (2)	0.48188 (13)	0.4864 (3)	0.0177 (5)
H11A	0.9448	0.4640	0.4288	0.021*
C12	1.0998 (2)	0.42316 (13)	0.5633 (4)	0.0176 (5)
C13	1.2108 (2)	0.44890 (13)	0.6442 (3)	0.0187 (5)
H13	1.2658	0.4089	0.6960	0.022*
C14	1.2406 (2)	0.53350 (13)	0.6487 (3)	0.0165 (5)
H14	1.3167	0.5511	0.7029	0.020*
N1	0.9975 (2)	0.74477 (11)	0.6363 (4)	0.0212 (5)
N2	1.1228 (2)	0.74854 (9)	0.5740 (3)	0.0161 (5)
N3	1.31389 (18)	0.79302 (10)	0.5291 (3)	0.0185 (5)
N4	1.31642 (18)	0.70604 (10)	0.5380 (3)	0.0188 (5)
H1O	0.9790 (11)	1.161 (2)	0.508 (5)	0.042 (10)*
H2O	0.9976 (14)	0.331 (3)	0.542 (7)	0.082 (16)*
H11	0.827 (3)	0.7358 (19)	0.264 (3)	0.053 (12)*
H12	0.7286 (15)	0.7500 (18)	0.376 (6)	0.072 (17)*
H1N	0.945 (3)	0.7523 (17)	0.549 (4)	0.046 (11)*
H2N	0.987 (4)	0.7803 (18)	0.722 (4)	0.055 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (8)	0.0142 (7)	0.0455 (13)	0.0051 (6)	0.0026 (8)	0.0015 (8)
O2	0.0207 (8)	0.0137 (7)	0.0412 (12)	−0.0040 (6)	−0.0055 (9)	0.0015 (8)
O1W	0.0296 (11)	0.0460 (11)	0.0368 (13)	−0.0008 (9)	0.0020 (9)	−0.0085 (11)
C1	0.0144 (11)	0.0154 (10)	0.0226 (14)	0.0001 (8)	0.0072 (10)	0.0021 (9)
C2	0.0144 (10)	0.0202 (11)	0.0207 (13)	0.0038 (8)	−0.0007 (9)	0.0006 (10)
C3	0.0147 (11)	0.0166 (10)	0.0212 (13)	−0.0018 (8)	0.0015 (9)	−0.0003 (9)
C4	0.0166 (10)	0.0124 (10)	0.0181 (11)	0.0013 (8)	0.0030 (10)	−0.0009 (9)
C5	0.0129 (10)	0.0187 (10)	0.0182 (12)	−0.0002 (8)	0.0013 (9)	0.0012 (9)
C6	0.0147 (10)	0.0144 (10)	0.0229 (14)	−0.0039 (8)	0.0033 (9)	−0.0023 (10)
C7	0.0154 (10)	0.0154 (10)	0.0186 (13)	−0.0014 (8)	0.0011 (10)	−0.0010 (10)
C8	0.0149 (10)	0.0148 (10)	0.0164 (12)	0.0001 (8)	0.0006 (10)	0.0001 (10)
C9	0.0157 (10)	0.0133 (10)	0.0177 (12)	−0.0008 (8)	0.0025 (10)	−0.0002 (9)
C10	0.0136 (11)	0.0170 (10)	0.0192 (13)	0.0021 (8)	0.0014 (9)	0.0010 (9)
C11	0.0159 (10)	0.0185 (12)	0.0187 (12)	−0.0021 (8)	0.0010 (10)	−0.0004 (10)
C12	0.0158 (11)	0.0142 (9)	0.0229 (12)	−0.0018 (8)	0.0026 (10)	−0.0037 (10)
C13	0.0168 (11)	0.0166 (11)	0.0225 (14)	0.0019 (8)	0.0006 (10)	0.0038 (9)
C14	0.0114 (9)	0.0197 (9)	0.0184 (13)	−0.0007 (9)	0.0004 (9)	−0.0018 (9)
N1	0.0135 (11)	0.0214 (10)	0.0288 (12)	−0.0006 (7)	0.0036 (10)	−0.0013 (9)
N2	0.0129 (9)	0.0121 (9)	0.0234 (11)	−0.0013 (6)	0.0015 (9)	0.0002 (7)
N3	0.0144 (9)	0.0118 (9)	0.0294 (13)	−0.0011 (6)	−0.0004 (8)	0.0010 (9)
N4	0.0148 (9)	0.0108 (9)	0.0307 (13)	−0.0007 (6)	0.0001 (9)	−0.0008 (9)

O1—C1	1.359 (3)	C7—N2	1.366 (3)
O1—H1O	0.84 (3)	C8—N4	1.316 (3)
O2—C12	1.369 (2)	C8—N2	1.367 (3)
O2—H2O	0.84 (3)	C8—C9	1.469 (3)
O1w—H11	0.85 (3)	C9—C14	1.393 (3)
O1w—H12	0.85 (3)	C9—C10	1.399 (3)
C1—C6	1.391 (3)	C10—C11	1.385 (3)
C1—C2	1.402 (3)	C10—H10	0.9500
C2—C3	1.386 (3)	C11—C12	1.393 (3)
C2—H2	0.9500	C11—H11A	0.9500
C3—C4	1.395 (3)	C12—C13	1.392 (3)
C3—H3	0.9500	C13—C14	1.389 (3)
C4—C5	1.396 (3)	C13—H13	0.9500
C4—C7	1.472 (3)	C14—H14	0.9500
C5—C6	1.384 (3)	N1—N2	1.416 (3)
C5—H5	0.9500	N1—H1N	0.87 (3)
C6—H6	0.9500	N1—H2N	0.86 (3)
C7—N3	1.313 (3)	N3—N4	1.392 (3)
C1—O1—H1O	109 (2)	C14—C9—C10	119.06 (19)
C12—O2—H2O	110 (3)	C14—C9—C8	119.2 (2)
H11—O1W—H12	106.8 (17)	C10—C9—C8	121.4 (2)
O1—C1—C6	118.7 (2)	C11—C10—C9	120.4 (2)
O1—C1—C2	121.7 (2)	C11—C10—H10	119.8
C6—C1—C2	119.60 (19)	C9—C10—H10	119.8
C3—C2—C1	120.2 (2)	C10—C11—C12	120.0 (2)
C3—C2—H2	119.9	C10—C11—H11A	120.0
C1—C2—H2	119.9	C12—C11—H11A	120.0
C2—C3—C4	120.2 (2)	O2—C12—C13	117.4 (2)
C2—C3—H3	119.9	O2—C12—C11	122.4 (2)
C4—C3—H3	119.9	C13—C12—C11	120.15 (19)
C3—C4—C5	119.21 (19)	C14—C13—C12	119.5 (2)
C3—C4—C7	121.4 (2)	C14—C13—H13	120.2
C5—C4—C7	119.2 (2)	C12—C13—H13	120.2
C6—C5—C4	120.8 (2)	C13—C14—C9	120.9 (2)
C6—C5—H5	119.6	C13—C14—H14	119.6
C4—C5—H5	119.6	C9—C14—H14	119.6
C5—C6—C1	119.9 (2)	N2—N1—H1N	111 (3)
C5—C6—H6	120.0	N2—N1—H2N	110 (3)
C1—C6—H6	120.0	H1N—N1—H2N	112 (3)
N3—C7—N2	109.22 (19)	C7—N2—C8	106.2 (2)
N3—C7—C4	124.7 (2)	C7—N2—N1	128.73 (17)
N2—C7—C4	126.12 (19)	C8—N2—N1	123.65 (17)
N4—C8—N2	109.47 (19)	C7—N3—N4	107.88 (16)
N4—C8—C9	125.19 (19)	C8—N4—N3	107.25 (16)
N2—C8—C9	125.21 (19)
O1—C1—C2—C3	−179.3 (2)	C10—C11—C12—O2	178.7 (2)
C6—C1—C2—C3	1.1 (4)	C10—C11—C12—C13	−1.5 (4)
C1—C2—C3—C4	−1.0 (4)	O2—C12—C13—C14	−179.8 (2)
C2—C3—C4—C5	0.5 (4)	C11—C12—C13—C14	0.4 (4)
C2—C3—C4—C7	−175.0 (2)	C12—C13—C14—C9	0.6 (4)
C3—C4—C5—C6	0.0 (4)	C10—C9—C14—C13	−0.4 (3)
C7—C4—C5—C6	175.5 (2)	C8—C9—C14—C13	−174.0 (2)
C4—C5—C6—C1	0.1 (4)	N3—C7—N2—C8	−0.5 (3)
O1—C1—C6—C5	179.7 (2)	C4—C7—N2—C8	178.4 (2)
C2—C1—C6—C5	−0.6 (3)	N3—C7—N2—N1	166.0 (2)
C3—C4—C7—N3	140.3 (3)	C4—C7—N2—N1	−15.2 (4)
C5—C4—C7—N3	−35.2 (4)	N4—C8—N2—C7	−0.1 (3)
C3—C4—C7—N2	−38.4 (4)	C9—C8—N2—C7	−176.1 (2)
C5—C4—C7—N2	146.2 (3)	N4—C8—N2—N1	−167.4 (2)
N4—C8—C9—C14	34.9 (4)	C9—C8—N2—N1	16.6 (4)
N2—C8—C9—C14	−149.7 (2)	N2—C7—N3—N4	0.8 (3)
N4—C8—C9—C10	−138.5 (3)	C4—C7—N3—N4	−178.0 (2)
N2—C8—C9—C10	36.9 (4)	N2—C8—N4—N3	0.5 (3)
C14—C9—C10—C11	−0.7 (4)	C9—C8—N4—N3	176.6 (2)
C8—C9—C10—C11	172.7 (2)	C7—N3—N4—C8	−0.8 (2)
C9—C10—C11—C12	1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N3i	0.84 (3)	1.92 (3)	2.730 (2)	163 (3)
O2—H2o···N4ii	0.84 (3)	2.02 (3)	2.850 (2)	168 (4)
O1w—H11···O2iii	0.85 (3)	2.19 (3)	3.020 (3)	166 (4)
O1w—H12···O1i	0.85 (3)	2.55 (3)	3.137 (3)	128 (2)
N1—H1n···O1w	0.87 (3)	2.08 (3)	2.943 (4)	173 (4)
N1—H2n···O1iv	0.86 (3)	2.36 (3)	3.202 (4)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N3i	0.84 (3)	1.92 (3)	2.730 (2)	163 (3)
O2—H2o⋯N4ii	0.84 (3)	2.02 (3)	2.850 (2)	168 (4)
O1w—H11⋯O2iii	0.85 (3)	2.19 (3)	3.020 (3)	166 (4)
N1—H1n⋯O1w	0.87 (3)	2.08 (3)	2.943 (4)	173 (4)
N1—H2n⋯O1iv	0.86 (3)	2.36 (3)	3.202 (4)	164 (3)

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