3-Ethyl-4-[3-(1H-imidazol-1-yl)prop-yl]-5-phenyl-4H-1,2,4-triazole dihydrate.

In the title compound, C(16)H(19)N(5)·2H(2)O, the triazole ring makes dihedral angles of 70.61 (6) and 41.89 (8)°, respectively, with the imidazole and benzene rings. The water mol-ecules are involved in inter-molecular O-H⋯N and O-H⋯O hydrogen bonds, which stabilize the crystal packing.

Related literature

For a related structure, see: Rizzoli et al. (2009 ▶); Kalkan et al. (2007 ▶). For bond lengths and angles in triazole rings, see: Thenmozhi et al. (2010 ▶); Rizzoli et al. (2009 ▶); Dolzhenko et al. (2010 ▶); Ocak Ískeleli et al. (2005 ▶); Ünver et al. (2010 ▶). For the biological activity of triazole Schiff bases, see: Thenmozhi et al. (2010 ▶) and of 1,2,4-triazole derivatives, see: Ünver et al. (2010 ▶). For the search for and synthesis of new anti­biotics, see: Köysal et al. (2006 ▶). For the synthesis, see: Ünver et al. (2009 ▶).

Experimental

Crystal data

C16H19N5·2H2O

M = 317.39

Monoclinic,

a = 11.0787 (16) Å

b = 9.8428 (8) Å

c = 16.3289 (18) Å

β = 105.602 (9)°

V = 1715.0 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan North et al. (1968 ▶) T min = 0.821, T max = 0.876

3030 measured reflections

2868 independent reflections

2166 reflections with I > 2σ(I)

R int = 0.029

2 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.08

2868 reflections

226 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ZORTEP (Zsolnai, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003936X/jh2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003936X/jh2213Isup2.hkl

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

C16H19N5·2H2O	F(000) = 680
Mr = 317.39	Dx = 1.229 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
a = 11.0787 (16) Å	Cell parameters from 25 reflections
b = 9.8428 (8) Å	θ = 20–30°
c = 16.3289 (18) Å	µ = 0.68 mm−1
β = 105.602 (9)°	T = 293 K
V = 1715.0 (3) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 Diffractometer	2166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 64.9°, θmin = 4.1°
ω–2τ scan	h = 0→13
Absorption correction: ψ scan North et al. (1968)	k = 0→11
Tmin = 0.821, Tmax = 0.876	l = −19→18
3030 measured reflections	2 standard reflections every 60 min
2868 independent reflections	intensity decay: none

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2868 reflections	Δρmax = 0.19 e Å−3
226 parameters	Δρmin = −0.17 e Å−3
6 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0246 (12)

Experimental. Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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	1.10619 (16)	0.09615 (18)	0.08555 (11)	0.0519 (4)
H1	1.0554	0.0218	0.0878	0.062*
C2	1.23425 (18)	0.0845 (2)	0.11690 (12)	0.0609 (5)
H2	1.2692	0.0026	0.1400	0.073*
C3	1.31051 (18)	0.1935 (2)	0.11417 (12)	0.0655 (6)
H3	1.3970	0.1855	0.1354	0.079*
C4	1.25803 (18)	0.3152 (2)	0.07964 (12)	0.0623 (5)
H4	1.3094	0.3893	0.0779	0.075*
C5	1.13010 (17)	0.32727 (17)	0.04779 (11)	0.0509 (4)
H5	1.0956	0.4092	0.0242	0.061*
C6	1.05207 (15)	0.21742 (16)	0.05067 (10)	0.0429 (4)
C7	0.91650 (15)	0.23322 (16)	0.01343 (10)	0.0430 (4)
C8	0.71432 (16)	0.23090 (19)	−0.00821 (11)	0.0529 (5)
C9	0.58650 (18)	0.2091 (3)	0.00312 (15)	0.0772 (6)
H9A	0.5689	0.1124	0.0005	0.093*
H9B	0.5856	0.2406	0.0592	0.093*
C10	0.4853 (2)	0.2794 (3)	−0.06124 (19)	0.1100 (10)
H10A	0.5027	0.3750	−0.0600	0.165*
H10B	0.4066	0.2646	−0.0486	0.165*
H10C	0.4813	0.2441	−0.1167	0.165*
C11	0.83527 (17)	0.11825 (17)	0.12819 (10)	0.0496 (4)
H11A	0.7754	0.1576	0.1551	0.060*
H11B	0.9185	0.1359	0.1648	0.060*
C12	0.81484 (18)	−0.03413 (18)	0.12166 (11)	0.0571 (5)
H12A	0.8667	−0.0732	0.0884	0.069*
H12B	0.7279	−0.0529	0.0925	0.069*
C13	0.8473 (2)	−0.0997 (2)	0.20926 (13)	0.0658 (5)
H13A	0.7918	−0.0643	0.2411	0.079*
H13B	0.8335	−0.1969	0.2029	0.079*
C14	1.0814 (2)	−0.1225 (2)	0.23923 (13)	0.0618 (5)
H14	1.0804	−0.1814	0.1945	0.074*
C15	1.1436 (2)	0.0064 (2)	0.34639 (14)	0.0700 (6)
H15	1.1959	0.0543	0.3912	0.084*
C16	1.0180 (2)	0.0092 (2)	0.32597 (12)	0.0655 (5)
H16	0.9685	0.0584	0.3532	0.079*
N1	0.86819 (13)	0.29858 (15)	−0.05759 (9)	0.0524 (4)
N2	0.73910 (14)	0.29737 (16)	−0.07142 (10)	0.0572 (4)
N3	0.82282 (12)	0.18678 (13)	0.04670 (8)	0.0455 (4)
N4	0.97689 (15)	−0.07477 (15)	0.25699 (9)	0.0564 (4)
N5	1.18406 (17)	−0.07686 (18)	0.29187 (11)	0.0692 (5)
O1	0.60569 (16)	0.10016 (18)	0.26136 (10)	0.0807 (5)
O2	0.43707 (15)	−0.11055 (19)	0.28415 (13)	0.0920 (6)
H1A	0.554 (2)	0.030 (2)	0.2642 (16)	0.127 (11)*
H1B	0.650 (2)	0.121 (3)	0.3147 (9)	0.134 (11)*
H2A	0.3579 (13)	−0.096 (2)	0.2882 (17)	0.105 (9)*
H2B	0.444 (2)	−0.2016 (12)	0.277 (2)	0.154 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0520 (10)	0.0489 (10)	0.0551 (10)	−0.0035 (8)	0.0146 (8)	0.0050 (8)
C2	0.0562 (11)	0.0673 (12)	0.0575 (11)	0.0090 (9)	0.0124 (8)	0.0122 (9)
C3	0.0467 (11)	0.0881 (15)	0.0583 (11)	−0.0024 (10)	0.0086 (8)	−0.0020 (10)
C4	0.0537 (11)	0.0680 (12)	0.0668 (12)	−0.0186 (9)	0.0190 (9)	−0.0075 (10)
C5	0.0543 (11)	0.0451 (9)	0.0560 (10)	−0.0047 (8)	0.0193 (8)	−0.0015 (8)
C6	0.0464 (10)	0.0417 (8)	0.0423 (8)	−0.0029 (7)	0.0152 (7)	−0.0023 (7)
C7	0.0455 (9)	0.0376 (8)	0.0483 (9)	−0.0039 (7)	0.0169 (7)	−0.0005 (7)
C8	0.0472 (10)	0.0528 (10)	0.0598 (10)	−0.0034 (8)	0.0163 (8)	0.0020 (8)
C9	0.0505 (12)	0.0929 (16)	0.0929 (15)	−0.0052 (11)	0.0271 (11)	0.0124 (13)
C10	0.0514 (14)	0.151 (3)	0.131 (2)	0.0045 (15)	0.0297 (14)	0.031 (2)
C11	0.0578 (10)	0.0464 (9)	0.0489 (9)	−0.0042 (8)	0.0218 (8)	−0.0010 (7)
C12	0.0665 (12)	0.0479 (10)	0.0615 (11)	−0.0122 (8)	0.0252 (9)	−0.0007 (8)
C13	0.0780 (14)	0.0530 (11)	0.0757 (13)	−0.0041 (10)	0.0366 (11)	0.0124 (10)
C14	0.0839 (15)	0.0492 (10)	0.0594 (11)	0.0147 (10)	0.0314 (11)	0.0078 (9)
C15	0.0886 (16)	0.0605 (12)	0.0631 (12)	0.0040 (11)	0.0240 (11)	0.0049 (10)
C16	0.0951 (16)	0.0532 (11)	0.0590 (11)	0.0097 (10)	0.0394 (11)	0.0041 (9)
N1	0.0461 (8)	0.0548 (9)	0.0562 (8)	−0.0011 (7)	0.0137 (6)	0.0098 (7)
N2	0.0439 (9)	0.0624 (9)	0.0638 (9)	−0.0005 (7)	0.0121 (7)	0.0096 (8)
N3	0.0477 (8)	0.0424 (7)	0.0485 (7)	−0.0045 (6)	0.0163 (6)	0.0002 (6)
N4	0.0741 (11)	0.0474 (8)	0.0559 (8)	0.0066 (7)	0.0314 (8)	0.0092 (7)
N5	0.0786 (12)	0.0630 (11)	0.0704 (10)	0.0143 (9)	0.0278 (9)	0.0130 (9)
O1	0.0767 (11)	0.0899 (12)	0.0706 (10)	−0.0057 (9)	0.0114 (8)	0.0019 (8)
O2	0.0619 (10)	0.0805 (12)	0.1268 (15)	0.0036 (8)	0.0135 (9)	−0.0038 (10)

C1—C2	1.377 (2)	C11—N3	1.465 (2)
C1—C6	1.387 (2)	C11—C12	1.516 (2)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.373 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—C13	1.522 (3)
C3—C4	1.384 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.377 (3)	C13—N4	1.459 (2)
C4—H4	0.9300	C13—H13A	0.9700
C5—C6	1.393 (2)	C13—H13B	0.9700
C5—H5	0.9300	C14—N5	1.307 (3)
C6—C7	1.469 (2)	C14—N4	1.352 (2)
C7—N1	1.308 (2)	C14—H14	0.9300
C7—N3	1.373 (2)	C15—C16	1.341 (3)
C8—N2	1.312 (2)	C15—N5	1.371 (3)
C8—N3	1.363 (2)	C15—H15	0.9300
C8—C9	1.492 (3)	C16—N4	1.372 (2)
C9—C10	1.485 (3)	C16—H16	0.9300
C9—H9A	0.9700	N1—N2	1.387 (2)
C9—H9B	0.9700	O1—H1A	0.906 (10)
C10—H10A	0.9600	O1—H1B	0.902 (10)
C10—H10B	0.9600	O2—H2A	0.909 (9)
C10—H10C	0.9600	O2—H2B	0.910 (10)
C2—C1—C6	120.80 (16)	N3—C11—H11A	108.6
C2—C1—H1	119.6	C12—C11—H11A	108.6
C6—C1—H1	119.6	N3—C11—H11B	108.6
C3—C2—C1	120.29 (18)	C12—C11—H11B	108.6
C3—C2—H2	119.9	H11A—C11—H11B	107.6
C1—C2—H2	119.9	C11—C12—C13	111.13 (15)
C2—C3—C4	119.64 (18)	C11—C12—H12A	109.4
C2—C3—H3	120.2	C13—C12—H12A	109.4
C4—C3—H3	120.2	C11—C12—H12B	109.4
C5—C4—C3	120.35 (18)	C13—C12—H12B	109.4
C5—C4—H4	119.8	H12A—C12—H12B	108.0
C3—C4—H4	119.8	N4—C13—C12	112.37 (15)
C4—C5—C6	120.35 (17)	N4—C13—H13A	109.1
C4—C5—H5	119.8	C12—C13—H13A	109.1
C6—C5—H5	119.8	N4—C13—H13B	109.1
C1—C6—C5	118.56 (16)	C12—C13—H13B	109.1
C1—C6—C7	122.80 (14)	H13A—C13—H13B	107.9
C5—C6—C7	118.59 (15)	N5—C14—N4	112.54 (18)
N1—C7—N3	110.00 (14)	N5—C14—H14	123.7
N1—C7—C6	123.22 (14)	N4—C14—H14	123.7
N3—C7—C6	126.76 (14)	C16—C15—N5	110.43 (19)
N2—C8—N3	110.02 (15)	C16—C15—H15	124.8
N2—C8—C9	125.15 (17)	N5—C15—H15	124.8
N3—C8—C9	124.82 (17)	C15—C16—N4	106.56 (17)
C10—C9—C8	113.94 (19)	C15—C16—H16	126.7
C10—C9—H9A	108.8	N4—C16—H16	126.7
C8—C9—H9A	108.8	C7—N1—N2	107.35 (13)
C10—C9—H9B	108.8	C8—N2—N1	107.52 (13)
C8—C9—H9B	108.8	C8—N3—C7	105.09 (14)
H9A—C9—H9B	107.7	C8—N3—C11	126.52 (14)
C9—C10—H10A	109.5	C7—N3—C11	128.05 (14)
C9—C10—H10B	109.5	C14—N4—C16	105.73 (17)
H10A—C10—H10B	109.5	C14—N4—C13	127.14 (17)
C9—C10—H10C	109.5	C16—N4—C13	127.00 (17)
H10A—C10—H10C	109.5	C14—N5—C15	104.73 (18)
H10B—C10—H10C	109.5	H1A—O1—H1B	108.4 (14)
N3—C11—C12	114.56 (14)	H2A—O2—H2B	106.5 (14)
C6—C1—C2—C3	0.1 (3)	C6—C7—N3—C8	177.38 (15)
C1—C2—C3—C4	−0.1 (3)	N1—C7—N3—C11	−174.85 (15)
C2—C3—C4—C5	−0.3 (3)	C6—C7—N3—C11	3.7 (3)
C3—C4—C5—C6	0.6 (3)	C12—C11—N3—C8	84.7 (2)
C2—C1—C6—C5	0.2 (3)	C12—C11—N3—C7	−102.89 (19)
C2—C1—C6—C7	177.55 (16)	N5—C14—N4—C16	0.8 (2)
C4—C5—C6—C1	−0.5 (2)	N5—C14—N4—C13	176.98 (15)
C4—C5—C6—C7	−177.98 (15)	C15—C16—N4—C14	−0.6 (2)
C1—C6—C7—N1	−137.55 (18)	C15—C16—N4—C13	−176.81 (16)
C5—C6—C7—N1	39.8 (2)	C12—C13—N4—C14	−67.3 (2)
C1—C6—C7—N3	44.1 (2)	C12—C13—N4—C16	108.1 (2)
C5—C6—C7—N3	−138.58 (17)	N4—C14—N5—C15	−0.6 (2)
N2—C8—C9—C10	−4.5 (3)	C16—C15—N5—C14	0.2 (2)
N3—C8—C9—C10	174.1 (2)	C7—N3—C11—C12	−102.89 (19)
N3—C11—C12—C13	172.00 (15)	C6—C7—N3—C11	3.7 (3)
C11—C12—C13—N4	−58.7 (2)	C6—C7—N3—C8	177.38 (15)
N5—C15—C16—N4	0.3 (2)	N1—C7—N3—C11	−174.85 (15)
N3—C7—N1—N2	0.85 (18)	N2—C8—N3—C11	174.88 (15)
C6—C7—N1—N2	−177.79 (14)	C9—C8—N3—C11	−3.9 (3)
N3—C8—N2—N1	−0.6 (2)	C5—C6—C7—N1	39.8 (2)
C9—C8—N2—N1	178.21 (19)	N1—C7—C6—C1	−137.55 (18)
C7—N1—N2—C8	−0.15 (19)	N3—C7—C6—C1	44.1 (2)
N2—C8—N3—C7	1.09 (19)	N2—C8—C9—C10	−4.5 (3)
C9—C8—N3—C7	−177.73 (19)	C10—C9—C8—N3	174.1 (2)
N2—C8—N3—C11	174.88 (15)	N4—C13—C12—C11	−58.7 (2)
C9—C8—N3—C11	−3.9 (3)	N3—C11—C12—C13	172.00 (15)
N1—C7—N3—C8	−1.19 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.91 (1)	1.98 (1)	2.882 (3)	172 (3)
O1—H1B···N2i	0.90 (1)	2.02 (1)	2.913 (2)	170 (3)
O2—H2A···N5ii	0.91 (1)	1.95 (1)	2.859 (3)	176 (2)
O2—H2B···O1iii	0.91 (1)	2.08 (2)	2.949 (3)	160 (3)

C7—N1	1.308 (2)
C7—N3	1.373 (2)
C8—N2	1.312 (2)
C8—N3	1.363 (2)
N1—N2	1.387 (2)

C8—N3—C7	105.09 (14)
C8—N3—C11	126.52 (14)
C7—N3—C11	128.05 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.91 (1)	1.98 (1)	2.882 (3)	172 (3)
O1—H1B⋯N2i	0.90 (1)	2.02 (1)	2.913 (2)	170 (3)
O2—H2A⋯N5ii	0.91 (1)	1.95 (1)	2.859 (3)	176 (2)
O2—H2B⋯O1iii	0.91 (1)	2.08 (2)	2.949 (3)	160 (3)

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