Crystal structure of 1-(1-methyl-1H-imidazol-2-yl)-4-phenyl-1H-1,2,3-triazole dihydrate.

The title compound, C12H11N5·2H2O, which crystallizes as a dihydrate, was obtained by Cu(I)-catalysed azide-alkyne cyclo-addition from 2-azido-1-methyl-imidazole and phenyl-ethyne. The dihedral angles between the central triazole ring (r.m.s. deviation = 0.004 Å) and the pendant imidazole (r.m.s. deviation = 0.006 Å) and phenyl rings are 12.3 (2) and 2.54 (19)°, respectively. In the crystal, the water mol-ecules are connected into [010] chains by O-H⋯O hydrogen bonds, while O-H⋯N hydrogen bonds connect the water mol-ecules to the organic mol-ecules, generating corrugated (100) sheets.

Related literature

For the synthesis and thermal cyclo­addition of 2-azido-1-methyl­imidazole, see: Zanirato & Cerini (2005 ▸). For related structures, see: Ramana & Punniyamurthy (2012 ▸). For background to 1,2,3-triazoles as peptidomimetics, see: Angell & Burgess (2007 ▸); Pedersen & Abell (2011 ▸); Tron et al. (2008 ▸). For copper(I)-catalysed azide–alkyne cyclo­additions, see: Haldón et al. (2015 ▸); Meldal & Tornoe (2008 ▸); Rostovtsev et al. (2002 ▸).

Experimental

Crystal data

C12H11N5·2H2O

M = 261.29

Orthorhombic,

a = 18.8585 (9) Å

b = 4.7884 (2) Å

c = 14.4285 (6) Å

V = 1302.92 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 233 K

0.40 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

6624 measured reflections

2277 independent reflections

1878 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.088

S = 1.08

2277 reflections

190 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: COLLECT (Hooft, 1998 ▸); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▸); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020721/hb7534sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020721/hb7534Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020721/hb7534Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020721/hb7534Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020721/hb7534fig1.tif

The mol­ecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. The water mol­ecules are not shown.

Click here for additional data file.

. DOI: 10.1107/S2056989015020721/hb7534fig2.tif

Infinite chains of hydrogen-bonded water mol­ecules link the heterocyclic mol­ecules.

CCDC reference: 1434671

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H11N5·2H2O	Dx = 1.332 Mg m−3
Mr = 261.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 18840 reflections
a = 18.8585 (9) Å	θ = 1.0–25.2°
b = 4.7884 (2) Å	µ = 0.10 mm−1
c = 14.4285 (6) Å	T = 233 K
V = 1302.92 (10) Å3	Prism, colourless
Z = 4	0.40 × 0.05 × 0.05 mm
F(000) = 552

Nonius KappaCCD diffractometer	Rint = 0.050
Detector resolution: 9.4 pixels mm-1	θmax = 25.0°, θmin = 2.2°
phi– and ω–scans	h = −18→22
6624 measured reflections	k = −5→5
2277 independent reflections	l = −17→17
1878 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0315P)2 + 0.2291P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.15 e Å−3
2277 reflections	Δρmin = −0.15 e Å−3
190 parameters	Extinction correction: SHELXL2014 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
5 restraints	Extinction coefficient: 0.018 (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. Hydrogen atoms at water molecules were found and refined isotropically with a bond restraint, d = 0.83 (2) Å.

	x	y	z	Uiso*/Ueq
N1	0.71035 (16)	0.4793 (6)	1.0472 (2)	0.0432 (7)
N2	0.69605 (16)	0.5200 (6)	0.89493 (19)	0.0439 (7)
N3	0.62108 (14)	0.8035 (6)	0.98838 (18)	0.0384 (7)
N4	0.58989 (17)	0.8522 (7)	1.0712 (2)	0.0504 (8)
N5	0.54108 (16)	1.0443 (6)	1.0565 (2)	0.0491 (8)
C1	0.67522 (16)	0.6024 (7)	0.9768 (3)	0.0387 (8)
C2	0.75758 (19)	0.2996 (8)	1.0060 (3)	0.0484 (9)
H2	0.7900	0.1815	1.0361	0.058*
C3	0.74817 (19)	0.3260 (7)	0.9139 (3)	0.0487 (9)
H3	0.7736	0.2260	0.8687	0.058*
C4	0.7052 (2)	0.5242 (10)	1.1475 (3)	0.0698 (13)
H4A	0.6585	0.4685	1.1688	0.105*
H4B	0.7127	0.7203	1.1612	0.105*
H4C	0.7409	0.4133	1.1788	0.105*
C5	0.59235 (19)	0.9645 (7)	0.9213 (3)	0.0404 (9)
H5	0.6047	0.9694	0.8582	0.048*
C6	0.54150 (17)	1.1183 (7)	0.9651 (2)	0.0368 (8)
C7	0.49322 (18)	1.3296 (7)	0.9261 (2)	0.0387 (8)
C8	0.49478 (18)	1.3869 (8)	0.8321 (2)	0.0446 (9)
H8	0.5263	1.2892	0.7935	0.054*
C9	0.4501 (2)	1.5875 (8)	0.7944 (3)	0.0523 (10)
H9	0.4516	1.6260	0.7306	0.063*
C10	0.4035 (2)	1.7299 (8)	0.8506 (3)	0.0525 (10)
H10	0.3732	1.8651	0.8250	0.063*
C11	0.4012 (2)	1.6750 (8)	0.9445 (3)	0.0492 (10)
H11	0.3690	1.7716	0.9826	0.059*
C12	0.44632 (18)	1.4772 (6)	0.9824 (3)	0.0442 (9)
H12	0.4453	1.4423	1.0465	0.053*
O1	0.66022 (15)	0.5304 (6)	0.70215 (18)	0.0527 (8)
O2	0.59225 (17)	1.0282 (6)	0.6683 (2)	0.0566 (8)
H1A	0.675 (3)	0.533 (11)	0.758 (2)	0.12 (2)*
H1B	0.641 (2)	0.371 (7)	0.692 (3)	0.079 (15)*
H2A	0.5546 (17)	1.019 (9)	0.640 (3)	0.077 (16)*
H2B	0.608 (2)	0.869 (7)	0.680 (4)	0.081 (16)*

	U11	U22	U33	U12	U13	U23
N1	0.0357 (16)	0.0487 (17)	0.0453 (18)	−0.0013 (15)	−0.0035 (14)	0.0036 (14)
N2	0.0433 (17)	0.0464 (17)	0.0419 (18)	−0.0012 (14)	0.0035 (15)	−0.0052 (13)
N3	0.0364 (15)	0.0410 (16)	0.0377 (16)	−0.0046 (13)	0.0002 (15)	−0.0002 (14)
N4	0.0510 (18)	0.0620 (19)	0.0384 (17)	0.0082 (17)	0.0022 (15)	0.0006 (15)
N5	0.0471 (18)	0.057 (2)	0.0431 (17)	0.0070 (16)	0.0016 (15)	−0.0006 (15)
C1	0.0302 (17)	0.0374 (18)	0.048 (2)	−0.0061 (15)	0.0008 (16)	0.0014 (17)
C2	0.0373 (19)	0.047 (2)	0.061 (2)	0.0046 (18)	0.0009 (19)	0.0036 (19)
C3	0.040 (2)	0.045 (2)	0.061 (3)	0.0021 (17)	0.0027 (19)	−0.005 (2)
C4	0.059 (3)	0.105 (4)	0.045 (3)	0.014 (3)	−0.003 (2)	0.006 (2)
C5	0.042 (2)	0.0401 (19)	0.0391 (19)	−0.0072 (17)	0.0023 (17)	0.0005 (17)
C6	0.0364 (18)	0.0347 (18)	0.0394 (18)	−0.0070 (15)	0.0018 (16)	−0.0004 (16)
C7	0.0355 (19)	0.0357 (19)	0.0449 (19)	−0.0075 (16)	0.0023 (16)	−0.0023 (17)
C8	0.040 (2)	0.048 (2)	0.045 (2)	0.0015 (18)	0.0019 (18)	−0.0053 (17)
C9	0.050 (2)	0.062 (3)	0.044 (2)	−0.005 (2)	−0.0038 (19)	0.006 (2)
C10	0.049 (2)	0.045 (2)	0.064 (3)	0.0005 (19)	−0.008 (2)	0.004 (2)
C11	0.048 (2)	0.041 (2)	0.059 (3)	0.0023 (19)	0.0046 (17)	−0.0021 (17)
C12	0.050 (2)	0.040 (2)	0.043 (2)	−0.0013 (17)	0.0071 (18)	0.0018 (17)
O1	0.0603 (19)	0.0462 (17)	0.0514 (19)	−0.0029 (14)	−0.0028 (14)	0.0066 (13)
O2	0.062 (2)	0.0472 (17)	0.0608 (18)	0.0040 (15)	−0.0141 (16)	−0.0078 (14)

N1—C1	1.347 (5)	C5—H5	0.9400
N1—C2	1.374 (4)	C6—C7	1.472 (5)
N1—C4	1.467 (5)	C7—C8	1.385 (5)
N2—C1	1.306 (5)	C7—C12	1.393 (5)
N2—C3	1.380 (5)	C8—C9	1.389 (5)
N3—C5	1.350 (4)	C8—H8	0.9400
N3—N4	1.352 (4)	C9—C10	1.376 (5)
N3—C1	1.413 (4)	C9—H9	0.9400
N4—N5	1.318 (4)	C10—C11	1.380 (5)
N5—C6	1.366 (5)	C10—H10	0.9400
C2—C3	1.347 (5)	C11—C12	1.386 (5)
C2—H2	0.9400	C11—H11	0.9400
C3—H3	0.9400	C12—H12	0.9400
C4—H4A	0.9700	O1—H1A	0.85 (3)
C4—H4B	0.9700	O1—H1B	0.86 (3)
C4—H4C	0.9700	O2—H2A	0.82 (3)
C5—C6	1.364 (5)	O2—H2B	0.84 (3)
C1—N1—C2	105.5 (3)	N3—C5—H5	127.5
C1—N1—C4	130.3 (3)	C6—C5—H5	127.5
C2—N1—C4	124.2 (3)	C5—C6—N5	108.1 (3)
C1—N2—C3	103.8 (3)	C5—C6—C7	129.0 (3)
C5—N3—N4	111.1 (3)	N5—C6—C7	122.9 (3)
C5—N3—C1	126.5 (3)	C8—C7—C12	118.9 (3)
N4—N3—C1	122.4 (3)	C8—C7—C6	119.8 (3)
N5—N4—N3	106.4 (3)	C12—C7—C6	121.3 (3)
N4—N5—C6	109.4 (3)	C7—C8—C9	120.5 (3)
N2—C1—N1	113.7 (3)	C7—C8—H8	119.7
N2—C1—N3	122.0 (3)	C9—C8—H8	119.7
N1—C1—N3	124.4 (3)	C10—C9—C8	120.0 (4)
C3—C2—N1	106.4 (3)	C10—C9—H9	120.0
C3—C2—H2	126.8	C8—C9—H9	120.0
N1—C2—H2	126.8	C9—C10—C11	120.3 (4)
C2—C3—N2	110.6 (3)	C9—C10—H10	119.9
C2—C3—H3	124.7	C11—C10—H10	119.9
N2—C3—H3	124.7	C10—C11—C12	119.8 (4)
N1—C4—H4A	109.5	C10—C11—H11	120.1
N1—C4—H4B	109.5	C12—C11—H11	120.1
H4A—C4—H4B	109.5	C11—C12—C7	120.5 (3)
N1—C4—H4C	109.5	C11—C12—H12	119.8
H4A—C4—H4C	109.5	C7—C12—H12	119.8
H4B—C4—H4C	109.5	H1A—O1—H1B	108 (5)
N3—C5—C6	105.0 (3)	H2A—O2—H2B	111 (5)
C5—N3—N4—N5	0.2 (4)	C1—N3—C5—C6	178.4 (3)
C1—N3—N4—N5	−178.3 (3)	N3—C5—C6—N5	−0.3 (4)
N3—N4—N5—C6	−0.4 (4)	N3—C5—C6—C7	180.0 (3)
C3—N2—C1—N1	0.8 (4)	N4—N5—C6—C5	0.4 (4)
C3—N2—C1—N3	−179.6 (3)	N4—N5—C6—C7	−179.8 (3)
C2—N1—C1—N2	−0.6 (4)	C5—C6—C7—C8	2.1 (5)
C4—N1—C1—N2	176.7 (4)	N5—C6—C7—C8	−177.6 (3)
C2—N1—C1—N3	179.8 (3)	C5—C6—C7—C12	−177.0 (3)
C4—N1—C1—N3	−2.9 (6)	N5—C6—C7—C12	3.3 (5)
C5—N3—C1—N2	−10.9 (5)	C12—C7—C8—C9	−0.2 (5)
N4—N3—C1—N2	167.3 (3)	C6—C7—C8—C9	−179.4 (3)
C5—N3—C1—N1	168.6 (3)	C7—C8—C9—C10	−0.4 (5)
N4—N3—C1—N1	−13.2 (5)	C8—C9—C10—C11	0.2 (6)
C1—N1—C2—C3	0.2 (4)	C9—C10—C11—C12	0.5 (6)
C4—N1—C2—C3	−177.4 (4)	C10—C11—C12—C7	−1.1 (5)
N1—C2—C3—N2	0.3 (4)	C8—C7—C12—C11	1.0 (5)
C1—N2—C3—C2	−0.6 (4)	C6—C7—C12—C11	−179.9 (3)
N4—N3—C5—C6	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.85 (3)	2.02 (3)	2.863 (4)	172 (4)
O1—H1B···O2i	0.86 (3)	1.91 (4)	2.768 (4)	176 (4)
O2—H2A···N5ii	0.82 (4)	2.19 (4)	3.007 (4)	174 (4)
O2—H2B···O1	0.84 (4)	1.92 (4)	2.750 (4)	170 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2	0.85 (3)	2.02 (3)	2.863 (4)	172 (4)
O1—H1B⋯O2i	0.86 (3)	1.91 (4)	2.768 (4)	176 (4)
O2—H2A⋯N5ii	0.82 (4)	2.19 (4)	3.007 (4)	174 (4)
O2—H2B⋯O1	0.84 (4)	1.92 (4)	2.750 (4)	170 (4)

Symmetry codes: (i) ; (ii) .