2,4,5-Tris(pyridin-4-yl)-1H-imidazole monohydrate.

In the crystal structure of the title compound, C(18)H(13)N(5)·H(2)O, adjacent mol-ecules are linked by O-H⋯N and N-H⋯O hydrogen bonds, generating a chain propagating along [001].

Related literature

For the use of 2,4,5-tri(4-pyrid­yl)imidazole in the construction of metal-organic coordination polymers, see: Wang et al. (2009 ▶); Liang et al. (2009 ▶). For related structures, see: Jiang & Hou (2011 ▶); Li (2011 ▶); Li & Xia (2011 ▶). For the preparation, see: Proskurnina et al. (2002 ▶).

Experimental

Crystal data

C18H13N5·H2O

M = 317.35

Triclinic,

a = 8.1510 (16) Å

b = 9.5210 (19) Å

c = 11.506 (2) Å

α = 103.80 (3)°

β = 105.64 (3)°

γ = 101.03 (3)°

V = 803.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.25 × 0.2 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.970, T max = 1.000

7510 measured reflections

2912 independent reflections

1792 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.125

S = 1.02

2876 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053013/zj2036sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053013/zj2036Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053013/zj2036Isup3.cml

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

C18H13N5·H2O	Z = 2
Mr = 317.35	F(000) = 332
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1510 (16) Å	Cell parameters from 3107 reflections
b = 9.5210 (19) Å	θ = 3.0–25.2°
c = 11.506 (2) Å	µ = 0.09 mm−1
α = 103.80 (3)°	T = 293 K
β = 105.64 (3)°	Prism, colourless
γ = 101.03 (3)°	0.35 × 0.25 × 0.2 mm
V = 803.3 (4) Å3

Bruker SMART diffractometer	2912 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 25.2°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.970, Tmax = 1.000	k = −11→11
7510 measured reflections	l = −13→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0171P)2 + 0.605P] where P = (Fo2 + 2Fc2)/3
2876 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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
N1	0.2548 (3)	0.5006 (2)	0.26415 (19)	0.0544 (6)
H1	0.2800	0.5437	0.3469	0.082*
N2	0.1414 (3)	0.3416 (2)	0.06806 (19)	0.0542 (6)
N3	−0.0531 (4)	0.0012 (3)	0.3185 (2)	0.0738 (7)
N4	0.2559 (4)	0.5283 (3)	−0.2901 (2)	0.0749 (7)
N5	0.5288 (4)	1.0560 (3)	0.3379 (3)	0.0764 (8)
C1	0.1603 (3)	0.3582 (3)	0.1895 (2)	0.0518 (6)
C2	0.2265 (3)	0.4798 (3)	0.0649 (2)	0.0523 (6)
C3	0.2960 (3)	0.5811 (3)	0.1858 (2)	0.0530 (7)
C4	0.0870 (3)	0.2404 (3)	0.2365 (2)	0.0520 (6)
C5	0.1271 (4)	0.2521 (3)	0.3637 (3)	0.0671 (8)
H5A	0.2026	0.3399	0.4252	0.080*
C6	0.0536 (4)	0.1317 (3)	0.3987 (3)	0.0739 (9)
H6A	0.0812	0.1433	0.4849	0.089*
C7	−0.0932 (4)	−0.0074 (3)	0.1966 (3)	0.0754 (9)
H7A	−0.1703	−0.0962	0.1374	0.091*
C8	−0.0284 (4)	0.1062 (3)	0.1517 (3)	0.0668 (8)
H8A	−0.0621	0.0926	0.0650	0.080*
C9	0.2386 (3)	0.4986 (3)	−0.0558 (2)	0.0527 (6)
C10	0.1214 (4)	0.4006 (3)	−0.1700 (2)	0.0594 (7)
H10A	0.0342	0.3211	−0.1709	0.071*
C11	0.1334 (4)	0.4203 (3)	−0.2821 (3)	0.0708 (8)
H11A	0.0505	0.3537	−0.3572	0.085*
C12	0.3716 (4)	0.6201 (4)	−0.1801 (3)	0.0775 (9)
H12A	0.4600	0.6962	−0.1826	0.093*
C13	0.3698 (4)	0.6105 (3)	−0.0626 (3)	0.0681 (8)
H13A	0.4552	0.6778	0.0110	0.082*
C14	0.3805 (4)	0.7431 (3)	0.2368 (2)	0.0549 (7)
C15	0.3141 (4)	0.8416 (3)	0.1767 (3)	0.0675 (8)
H15A	0.2185	0.8049	0.1015	0.081*
C16	0.3925 (4)	0.9939 (3)	0.2305 (3)	0.0754 (9)
H16A	0.3470	1.0577	0.1890	0.090*
C17	0.5915 (4)	0.9608 (3)	0.3939 (3)	0.0735 (9)
H17A	0.6879	1.0009	0.4685	0.088*
C18	0.5219 (4)	0.8055 (3)	0.3480 (3)	0.0650 (8)
H18A	0.5701	0.7446	0.3918	0.078*
O1	0.3155 (4)	0.6367 (2)	0.51602 (18)	0.1058 (10)
H1A	0.3597	0.7298	0.5581	0.159*
H1B	0.3044	0.5992	0.5745	0.159*

	U11	U22	U33	U12	U13	U23
N1	0.0703 (14)	0.0475 (12)	0.0430 (12)	0.0090 (10)	0.0198 (10)	0.0139 (9)
N2	0.0711 (15)	0.0475 (12)	0.0439 (12)	0.0088 (10)	0.0215 (11)	0.0167 (9)
N3	0.0983 (19)	0.0555 (14)	0.0683 (17)	0.0082 (13)	0.0323 (15)	0.0249 (13)
N4	0.102 (2)	0.0736 (16)	0.0558 (15)	0.0144 (15)	0.0375 (15)	0.0265 (13)
N5	0.0884 (19)	0.0549 (15)	0.0791 (18)	0.0055 (14)	0.0317 (16)	0.0152 (14)
C1	0.0689 (17)	0.0422 (13)	0.0430 (14)	0.0118 (12)	0.0187 (13)	0.0129 (11)
C2	0.0652 (16)	0.0482 (14)	0.0426 (14)	0.0091 (12)	0.0199 (12)	0.0153 (11)
C3	0.0660 (17)	0.0482 (14)	0.0446 (14)	0.0091 (12)	0.0201 (13)	0.0171 (11)
C4	0.0680 (17)	0.0428 (13)	0.0470 (15)	0.0122 (12)	0.0209 (13)	0.0174 (11)
C5	0.097 (2)	0.0510 (15)	0.0484 (16)	0.0064 (15)	0.0245 (15)	0.0162 (13)
C6	0.111 (3)	0.0599 (18)	0.0564 (18)	0.0163 (17)	0.0360 (18)	0.0236 (15)
C7	0.094 (2)	0.0519 (17)	0.068 (2)	−0.0007 (15)	0.0184 (17)	0.0212 (15)
C8	0.088 (2)	0.0522 (16)	0.0527 (16)	0.0074 (15)	0.0191 (15)	0.0174 (13)
C9	0.0659 (17)	0.0511 (14)	0.0462 (14)	0.0145 (12)	0.0225 (13)	0.0204 (12)
C10	0.0738 (18)	0.0566 (16)	0.0473 (15)	0.0113 (14)	0.0228 (14)	0.0169 (13)
C11	0.090 (2)	0.0732 (19)	0.0474 (17)	0.0160 (17)	0.0259 (16)	0.0173 (14)
C12	0.097 (2)	0.071 (2)	0.068 (2)	0.0054 (17)	0.0402 (19)	0.0273 (17)
C13	0.079 (2)	0.0656 (18)	0.0517 (17)	0.0000 (15)	0.0251 (15)	0.0158 (14)
C14	0.0670 (17)	0.0486 (14)	0.0492 (15)	0.0082 (12)	0.0251 (13)	0.0148 (12)
C15	0.078 (2)	0.0519 (16)	0.0657 (19)	0.0083 (14)	0.0172 (16)	0.0212 (14)
C16	0.087 (2)	0.0536 (17)	0.086 (2)	0.0151 (16)	0.0285 (19)	0.0265 (16)
C17	0.080 (2)	0.0604 (18)	0.0624 (19)	−0.0019 (16)	0.0216 (16)	0.0061 (15)
C18	0.077 (2)	0.0548 (16)	0.0552 (17)	0.0068 (14)	0.0185 (15)	0.0156 (13)
O1	0.187 (3)	0.0597 (13)	0.0500 (12)	−0.0125 (14)	0.0451 (14)	0.0087 (10)

N1—C1	1.363 (3)	C7—H7A	0.9300
N1—C3	1.381 (3)	C8—H8A	0.9300
N1—H1	0.8907	C9—C10	1.381 (3)
N2—C1	1.331 (3)	C9—C13	1.390 (3)
N2—C2	1.379 (3)	C10—C11	1.373 (4)
N3—C6	1.326 (4)	C10—H10A	0.9300
N3—C7	1.329 (4)	C11—H11A	0.9300
N4—C11	1.329 (4)	C12—C13	1.381 (4)
N4—C12	1.330 (4)	C12—H12A	0.9300
N5—C16	1.330 (4)	C13—H13A	0.9300
N5—C17	1.333 (4)	C14—C18	1.378 (4)
C1—C4	1.454 (3)	C14—C15	1.397 (4)
C2—C3	1.383 (3)	C15—C16	1.378 (4)
C2—C9	1.469 (3)	C15—H15A	0.9300
C3—C14	1.463 (3)	C16—H16A	0.9300
C4—C5	1.383 (3)	C17—C18	1.390 (4)
C4—C8	1.385 (3)	C17—H17A	0.9300
C5—C6	1.387 (4)	C18—H18A	0.9300
C5—H5A	0.9300	O1—H1A	0.8543
C6—H6A	0.9300	O1—H1B	0.8500
C7—C8	1.382 (4)
C1—N1—C3	107.5 (2)	C10—C9—C13	116.4 (2)
C1—N1—H1	130.1	C10—C9—C2	120.8 (2)
C3—N1—H1	122.1	C13—C9—C2	122.8 (2)
C1—N2—C2	105.6 (2)	C11—C10—C9	120.2 (3)
C6—N3—C7	115.0 (2)	C11—C10—H10A	119.9
C11—N4—C12	115.6 (2)	C9—C10—H10A	119.9
C16—N5—C17	116.0 (3)	N4—C11—C10	124.1 (3)
N2—C1—N1	111.3 (2)	N4—C11—H11A	117.9
N2—C1—C4	124.4 (2)	C10—C11—H11A	117.9
N1—C1—C4	124.3 (2)	N4—C12—C13	124.6 (3)
N2—C2—C3	110.2 (2)	N4—C12—H12A	117.7
N2—C2—C9	119.8 (2)	C13—C12—H12A	117.7
C3—C2—C9	130.0 (2)	C12—C13—C9	119.1 (3)
N1—C3—C2	105.3 (2)	C12—C13—H13A	120.5
N1—C3—C14	120.4 (2)	C9—C13—H13A	120.5
C2—C3—C14	134.0 (2)	C18—C14—C15	117.3 (2)
C5—C4—C8	116.3 (2)	C18—C14—C3	122.0 (2)
C5—C4—C1	123.8 (2)	C15—C14—C3	120.6 (2)
C8—C4—C1	119.9 (2)	C16—C15—C14	118.9 (3)
C4—C5—C6	119.4 (3)	C16—C15—H15A	120.5
C4—C5—H5A	120.3	C14—C15—H15A	120.5
C6—C5—H5A	120.3	N5—C16—C15	124.5 (3)
N3—C6—C5	124.9 (3)	N5—C16—H16A	117.7
N3—C6—H6A	117.5	C15—C16—H16A	117.7
C5—C6—H6A	117.5	N5—C17—C18	124.1 (3)
N3—C7—C8	124.6 (3)	N5—C17—H17A	117.9
N3—C7—H7A	117.7	C18—C17—H17A	117.9
C8—C7—H7A	117.7	C14—C18—C17	119.1 (3)
C7—C8—C4	119.7 (3)	C14—C18—H18A	120.4
C7—C8—H8A	120.1	C17—C18—H18A	120.4
C4—C8—H8A	120.1	H1A—O1—H1B	100.9
C2—N2—C1—N1	−0.5 (3)	N2—C2—C9—C10	21.5 (4)
C2—N2—C1—C4	178.6 (3)	C3—C2—C9—C10	−161.6 (3)
C3—N1—C1—N2	1.3 (3)	N2—C2—C9—C13	−156.1 (3)
C3—N1—C1—C4	−177.8 (3)	C3—C2—C9—C13	20.8 (5)
C1—N2—C2—C3	−0.5 (3)	C13—C9—C10—C11	−2.7 (4)
C1—N2—C2—C9	176.9 (2)	C2—C9—C10—C11	179.5 (3)
C1—N1—C3—C2	−1.6 (3)	C12—N4—C11—C10	0.2 (5)
C1—N1—C3—C14	173.1 (2)	C9—C10—C11—N4	1.6 (5)
N2—C2—C3—N1	1.3 (3)	C11—N4—C12—C13	−0.8 (5)
C9—C2—C3—N1	−175.8 (3)	N4—C12—C13—C9	−0.5 (5)
N2—C2—C3—C14	−172.3 (3)	C10—C9—C13—C12	2.2 (4)
C9—C2—C3—C14	10.6 (5)	C2—C9—C13—C12	179.9 (3)
N2—C1—C4—C5	170.9 (3)	N1—C3—C14—C18	45.8 (4)
N1—C1—C4—C5	−10.2 (4)	C2—C3—C14—C18	−141.4 (3)
N2—C1—C4—C8	−8.3 (4)	N1—C3—C14—C15	−131.1 (3)
N1—C1—C4—C8	170.7 (3)	C2—C3—C14—C15	41.7 (5)
C8—C4—C5—C6	0.8 (4)	C18—C14—C15—C16	0.2 (4)
C1—C4—C5—C6	−178.4 (3)	C3—C14—C15—C16	177.3 (3)
C7—N3—C6—C5	−2.3 (5)	C17—N5—C16—C15	0.7 (5)
C4—C5—C6—N3	1.1 (5)	C14—C15—C16—N5	−0.3 (5)
C6—N3—C7—C8	1.7 (5)	C16—N5—C17—C18	−0.9 (5)
N3—C7—C8—C4	0.1 (5)	C15—C14—C18—C17	−0.4 (4)
C5—C4—C8—C7	−1.3 (4)	C3—C14—C18—C17	−177.4 (3)
C1—C4—C8—C7	177.9 (3)	N5—C17—C18—C14	0.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N5i	0.85	1.99	2.843 (3)	177.
N1—H1···O1	0.89	1.85	2.741 (3)	176.
O1—H1B···N4ii	0.85	1.94	2.787 (3)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N5i	0.85	1.99	2.843 (3)	177
N1—H1⋯O1	0.89	1.85	2.741 (3)	176
O1—H1B⋯N4ii	0.85	1.94	2.787 (3)	172

Symmetry codes: (i) ; (ii) .