[1-(3-Chloro­phen­yl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate

Boechat, N.; Ferreira, M. de L.G.; Bastos, M.M.; Wardell, J.L.; Wardell, S.M.S.V.; Tiekink, E.R.T.

doi:10.1107/S1600536811041560

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2934-o2935

doi:10.1107/S1600536811041560

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[1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate

Nübia Boechat,^a Maria de Lourdes G. Ferreira,^a Monica M. Bastos,^a James L. Wardell,^b ‡ Solange M. S. V. Wardell ^c and Edward R. T. Tiekink ^d ^*

^aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos, Departamento de Sintese Organica, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, ^bCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, ^cCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 7 October 2011; accepted 10 October 2011; online 12 October 2011)

The asymmetric unit of the title hydrate, C₉H₈ClN₃O·0.5H₂O, comprises two independent 1,2,3-triazole molecules and a water molecule of crystallization. The dihedral angles between the six- and five-membered rings in the 1,2,3-triazole molecules are 12.71 (19) and 17.3 (2)°. The most significant different between them is found in the relative orientations of the terminal CH₂OH groups with one being close to perpendicular to the five-membered ring [N—C—C—O torsion angle = 82.2 (5)°], while in the other molecule, a notable deviation from a perpendicular disposition is found [torsion angle = −60.3 (5)°]. Supramolecular chains feature in the crystal packing sustained by O—H⋯(O,N) interactions along the a-axis direction. The chains are connected via C—H⋯N interactions and the resultant layers stack along the b axis.

Related literature

For background to the synthesis, biological activity and structures of 1,2,3-triazole derivatives, see: Boechat et al. (2010 , 2011 ); Costa et al. (2006a ,b ); Ferreira et al. (2007 ); Jordão et al. (2009 ). For the synthesis, see: Boechat et al. (2011). For additional geometric analysis, see: Spek (2009 ).

Experimental

Crystal data

C₉H₈ClN₃O·0.5H₂O
M_r = 218.64
Triclinic, $[P \overline 1]$
a = 6.0078 (4) Å
b = 7.4897 (4) Å
c = 22.3145 (15) Å
α = 88.818 (4)°
β = 89.901 (2)°
γ = 80.493 (4)°
V = 990.07 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 120 K
0.18 × 0.18 × 0.02 mm

Data collection

Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.843, T_max = 1.000
10830 measured reflections
3909 independent reflections
2948 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.163
S = 1.00
3909 reflections
274 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.84 (4)	1.82 (4)	2.651 (5)	170 (5)
O2—H2o⋯O1w	0.84 (6)	1.80 (5)	2.641 (5)	174 (7)
O1w—H1w⋯N3	0.84 (4)	2.00 (4)	2.837 (5)	172 (4)
O1w—H2w⋯O1ⁱⁱ	0.84 (4)	1.95 (5)	2.663 (5)	142 (4)
C16—H16⋯O1wⁱⁱⁱ	0.95	2.45	3.383 (5)	166
C7—H7⋯N6^iv	0.95	2.28	3.197 (5)	161
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x+1, y, z; (iii) x-1, y, z; (iv) x-1, y+1, z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ), QMol (Gans & Shalloway, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041560/hb6439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041560/hb6439Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041560/hb6439Isup3.cml

checkCIF report

Comment top

Boechat and colleagues have been interested in the synthesis, biological activities and structures of 1,2,3-triazole derivatives for some time (Boechat et al., 2010, 2011; Costa et al., 2006a, 2006b; Ferreira et al., 2007, Jordão et al., 2009). Recently, they reported the synthesis and anti-mycobacterial activities of a number of 4-R-1-(X-phenyl)-triazole derivatives (Boechat et al., 2011). The structure of one of the compounds investigated in that study, i.e. the title compound, (I), is now reported.

Two independent molecules of a 1,2,3-triazole derivative and a water molecule of solvation comprise the asymmetric unit of (I), Fig. 1. Geometrically, the two organic molecules are similar to each other with r.m.s. deviations for bond distances and angles being 0.0092 Å and 0.757°, respectively (Spek, 2009). From the overlay diagram, Fig. 2, it is evident that the independent molecules approximate mirror images. However, small twists between the five- and six-membered rings differ with the dihedral angles between their least-squares being 12.71 (19) and 17.3 (2)°, respectively, for the N1- and N4-containing molecules. More notable are the relative orientations of the terminal CH₂OH groups as seen in the values of the N3—C8—C9—O1 and N6—C17—C18—O2 torsion angles of 82.2 (5) and -60.3 (5)°, respectively.

The presence of a supramolecular chain along the a axis is the most prominent feature of the crystal packing, Fig. 3. These are mediated by O—H···O and O—H···N hydrogen bonds with additional stability afforded by C—H···O interactions, Table 1. Chains are connected into layers via C—H···N interactions, Table 1, and these stack along the b axis. The closest interactions between layers are of the type Cl···Cl, i.e. Cl1···Cl2ⁱ = 3.4117 (15) Å for i: 2 - x, 1 - y, 1 - z.

Related literature top

For background to the synthesis, biological activity and structures of 1,2,3-triazole derivatives, see: Boechat et al. (2010, 2011); Costa et al. (2006a,b); Ferreira et al. (2007); Jordão et al. (2009). For the synthesis, see: Boechat et al. (2011). For additional geometric analysis, see: Spek (2009).

Experimental top

The compound, obtained as published (Boechat et al., 2011), was recrystallized from EtOH as a hemihydrate.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structures of the components comprising the asymmetric unit in (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. An overlay diagram of the two independent molecules in (I). The red and blue images illustrate the N1- and N3-containing molecules, respectively.
	Fig. 3. A view of the supramolecular chain aligned along the a axis in (I) mediated by O—H···O (red dashed lines), O—H···N (blue) hydrogen bonds and C—H···O interactions (green).
	Fig. 4. A view in projection down the a axis of the unit-cell contents in (I) showing the stacking of layers along the b axis. The O—H···O, O—H···N and C—H···O interactions are shown as orange, blue and green dashed lines, respectively.

[1-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate top

Crystal data top

C₉H₈ClN₃O·0.5H₂O	Z = 4
M_r = 218.64	F(000) = 452
Triclinic, P1	D_x = 1.467 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0078 (4) Å	Cell parameters from 19812 reflections
b = 7.4897 (4) Å	θ = 2.9–27.5°
c = 22.3145 (15) Å	µ = 0.36 mm⁻¹
α = 88.818 (4)°	T = 120 K
β = 89.901 (2)°	Plate, colourless
γ = 80.493 (4)°	0.18 × 0.18 × 0.02 mm
V = 990.07 (11) Å³

Data collection top

Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer	3909 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2948 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	R_int = 0.038
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.5°, θ_min = 2.9°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −9→9
T_min = 0.843, T_max = 1.000	l = −28→28
10830 measured reflections

Refinement top

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0446P)² + 2.5602P] where P = (F_o² + 2F_c²)/3
3909 reflections	(Δ/σ)_max = 0.012
274 parameters	Δρ_max = 0.41 e Å⁻³
5 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₉H₈ClN₃O·0.5H₂O	γ = 80.493 (4)°
M_r = 218.64	V = 990.07 (11) Å³
Triclinic, P1	Z = 4
a = 6.0078 (4) Å	Mo Kα radiation
b = 7.4897 (4) Å	µ = 0.36 mm⁻¹
c = 22.3145 (15) Å	T = 120 K
α = 88.818 (4)°	0.18 × 0.18 × 0.02 mm
β = 89.901 (2)°

Data collection top

Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer	3909 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2948 reflections with I > 2σ(I)
T_min = 0.843, T_max = 1.000	R_int = 0.038
10830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	5 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.41 e Å⁻³
3909 reflections	Δρ_min = −0.34 e Å⁻³
274 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.85344 (17)	0.75800 (15)	0.46687 (4)	0.0449 (3)
O1	0.5639 (6)	0.7737 (5)	0.05307 (13)	0.0595 (9)
H1O	0.629 (9)	0.747 (7)	0.0204 (13)	0.089*
N1	0.6411 (5)	0.8503 (4)	0.24523 (13)	0.0297 (6)
N2	0.8433 (5)	0.7528 (4)	0.23011 (14)	0.0386 (7)
N3	0.8614 (6)	0.7674 (4)	0.17193 (14)	0.0424 (8)
C1	0.6580 (6)	0.8250 (5)	0.41004 (15)	0.0304 (7)
C2	0.4384 (6)	0.8954 (5)	0.42488 (16)	0.0343 (8)
H2	0.3932	0.9055	0.4657	0.041*
C3	0.2852 (6)	0.9509 (5)	0.37926 (15)	0.0331 (8)
H3	0.1338	1.0005	0.3889	0.040*
C4	0.3494 (6)	0.9352 (5)	0.31987 (16)	0.0317 (8)
H4	0.2426	0.9724	0.2889	0.038*
C5	0.5708 (6)	0.8647 (4)	0.30588 (15)	0.0280 (7)
C6	0.7280 (6)	0.8092 (5)	0.35095 (15)	0.0314 (8)
H6	0.8801	0.7614	0.3414	0.038*
C7	0.5315 (6)	0.9254 (5)	0.19577 (15)	0.0322 (8)
H7	0.3870	0.9992	0.1940	0.039*
C8	0.6716 (7)	0.8731 (5)	0.14894 (16)	0.0381 (9)
C9	0.6412 (8)	0.9160 (6)	0.08392 (17)	0.0484 (11)
H9A	0.5309	1.0289	0.0784	0.058*
H9B	0.7867	0.9368	0.0665	0.058*
Cl2	0.7137 (2)	0.31120 (15)	0.43211 (4)	0.0519 (3)
O2	1.1922 (7)	0.3320 (5)	0.04279 (18)	0.0843 (14)
H2O	1.219 (12)	0.422 (6)	0.062 (3)	0.126*
N4	0.7744 (5)	0.2978 (4)	0.20400 (13)	0.0306 (6)
N5	0.9702 (5)	0.1798 (5)	0.21008 (15)	0.0433 (8)
N6	1.0590 (6)	0.1604 (5)	0.15647 (16)	0.0485 (9)
C10	0.5956 (6)	0.3531 (5)	0.36144 (16)	0.0348 (8)
C11	0.3706 (6)	0.4305 (5)	0.35577 (16)	0.0359 (8)
H11	0.2793	0.4587	0.3902	0.043*
C12	0.2826 (6)	0.4657 (5)	0.29895 (17)	0.0389 (9)
H12	0.1293	0.5210	0.2943	0.047*
C13	0.4137 (6)	0.4217 (5)	0.24830 (16)	0.0318 (8)
H13	0.3506	0.4445	0.2093	0.038*
C14	0.6367 (6)	0.3444 (4)	0.25557 (16)	0.0309 (8)
C15	0.7315 (6)	0.3090 (5)	0.31195 (16)	0.0323 (8)
H15	0.8855	0.2558	0.3166	0.039*
C16	0.7421 (6)	0.3525 (5)	0.14617 (16)	0.0350 (8)
H16	0.6188	0.4348	0.1298	0.042*
C17	0.9245 (7)	0.2643 (5)	0.11626 (18)	0.0395 (9)
C18	0.9826 (8)	0.2697 (6)	0.05057 (19)	0.0538 (12)
H18A	0.9928	0.1471	0.0339	0.065*
H18B	0.8623	0.3516	0.0287	0.065*
O1W	1.2489 (5)	0.6147 (4)	0.10634 (13)	0.0491 (7)
H1W	1.143 (6)	0.661 (6)	0.1286 (19)	0.074*
H2W	1.293 (8)	0.698 (5)	0.086 (2)	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0387 (5)	0.0620 (7)	0.0332 (5)	−0.0063 (4)	−0.0052 (4)	0.0013 (4)
O1	0.081 (2)	0.077 (2)	0.0334 (15)	−0.0501 (19)	0.0214 (15)	−0.0252 (15)
N1	0.0308 (16)	0.0279 (15)	0.0314 (15)	−0.0076 (12)	0.0057 (12)	−0.0036 (12)
N2	0.0380 (18)	0.0384 (18)	0.0380 (17)	−0.0016 (14)	0.0155 (14)	−0.0037 (13)
N3	0.049 (2)	0.0433 (19)	0.0375 (18)	−0.0135 (15)	0.0174 (16)	−0.0073 (14)
C1	0.0303 (18)	0.0333 (19)	0.0288 (17)	−0.0085 (14)	−0.0026 (14)	−0.0010 (14)
C2	0.037 (2)	0.039 (2)	0.0283 (18)	−0.0112 (16)	0.0055 (16)	−0.0051 (15)
C3	0.0289 (18)	0.039 (2)	0.0310 (18)	−0.0040 (15)	0.0073 (15)	−0.0030 (15)
C4	0.0339 (19)	0.0316 (19)	0.0298 (18)	−0.0061 (14)	0.0050 (15)	−0.0024 (14)
C5	0.0308 (18)	0.0259 (17)	0.0283 (17)	−0.0074 (13)	0.0036 (14)	−0.0025 (13)
C6	0.0280 (18)	0.0317 (19)	0.0348 (19)	−0.0056 (14)	0.0070 (15)	−0.0043 (14)
C7	0.0345 (19)	0.0354 (19)	0.0290 (18)	−0.0120 (15)	0.0024 (15)	−0.0039 (14)
C8	0.048 (2)	0.038 (2)	0.0327 (19)	−0.0193 (17)	0.0104 (17)	−0.0109 (16)
C9	0.070 (3)	0.051 (3)	0.032 (2)	−0.032 (2)	0.014 (2)	−0.0089 (18)
Cl2	0.0633 (7)	0.0630 (7)	0.0319 (5)	−0.0187 (5)	−0.0054 (5)	0.0050 (4)
O2	0.093 (3)	0.094 (3)	0.085 (3)	−0.067 (2)	0.063 (2)	−0.049 (2)
N4	0.0293 (15)	0.0294 (15)	0.0333 (16)	−0.0048 (12)	0.0040 (12)	−0.0042 (12)
N5	0.0298 (17)	0.050 (2)	0.047 (2)	0.0020 (14)	0.0020 (15)	−0.0105 (15)
N6	0.0359 (19)	0.057 (2)	0.053 (2)	−0.0086 (16)	0.0100 (17)	−0.0177 (17)
C10	0.043 (2)	0.034 (2)	0.0289 (18)	−0.0136 (16)	−0.0044 (16)	0.0042 (14)
C11	0.041 (2)	0.036 (2)	0.0318 (19)	−0.0101 (16)	0.0087 (16)	−0.0011 (15)
C12	0.034 (2)	0.036 (2)	0.045 (2)	−0.0018 (16)	0.0087 (17)	−0.0016 (16)
C13	0.0333 (19)	0.0312 (19)	0.0316 (18)	−0.0075 (14)	−0.0006 (15)	−0.0011 (14)
C14	0.0329 (19)	0.0259 (18)	0.0355 (19)	−0.0087 (14)	0.0080 (15)	−0.0039 (14)
C15	0.0308 (19)	0.0333 (19)	0.0340 (19)	−0.0086 (14)	−0.0009 (15)	0.0027 (14)
C16	0.041 (2)	0.034 (2)	0.0316 (19)	−0.0113 (16)	0.0063 (16)	−0.0002 (15)
C17	0.044 (2)	0.038 (2)	0.042 (2)	−0.0190 (17)	0.0149 (18)	−0.0105 (17)
C18	0.061 (3)	0.063 (3)	0.046 (2)	−0.033 (2)	0.026 (2)	−0.019 (2)
O1W	0.0453 (17)	0.065 (2)	0.0381 (16)	−0.0109 (14)	0.0155 (13)	−0.0064 (14)

Geometric parameters (Å, º) top

Cl1—C1	1.739 (4)	O2—C18	1.423 (5)
O1—C9	1.422 (5)	O2—H2O	0.840 (10)
O1—H1O	0.839 (10)	N4—C16	1.350 (4)
N1—C7	1.350 (4)	N4—N5	1.355 (4)
N1—N2	1.356 (4)	N4—C14	1.431 (4)
N1—C5	1.418 (4)	N5—N6	1.310 (5)
N2—N3	1.307 (4)	N6—C17	1.353 (5)
N3—C8	1.370 (5)	C10—C11	1.385 (5)
C1—C2	1.380 (5)	C10—C15	1.385 (5)
C1—C6	1.385 (5)	C11—C12	1.378 (5)
C2—C3	1.384 (5)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.390 (5)
C3—C4	1.382 (5)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.377 (5)
C4—C5	1.385 (5)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.384 (5)
C5—C6	1.390 (5)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.364 (5)
C7—C8	1.363 (5)	C16—H16	0.9500
C7—H7	0.9500	C17—C18	1.507 (5)
C8—C9	1.485 (5)	C18—H18A	0.9900
C9—H9A	0.9900	C18—H18B	0.9900
C9—H9B	0.9900	O1W—H1W	0.840 (10)
Cl2—C10	1.731 (4)	O1W—H2W	0.838 (10)

C9—O1—H1O	115 (4)	C16—N4—N5	110.3 (3)
C7—N1—N2	110.3 (3)	C16—N4—C14	130.2 (3)
C7—N1—C5	128.6 (3)	N5—N4—C14	119.5 (3)
N2—N1—C5	121.1 (3)	N6—N5—N4	106.6 (3)
N3—N2—N1	106.9 (3)	N5—N6—C17	109.9 (3)
N2—N3—C8	109.7 (3)	C11—C10—C15	121.9 (3)
C2—C1—C6	121.7 (3)	C11—C10—Cl2	119.7 (3)
C2—C1—Cl1	119.3 (3)	C15—C10—Cl2	118.5 (3)
C6—C1—Cl1	119.0 (3)	C12—C11—C10	118.3 (3)
C1—C2—C3	118.8 (3)	C12—C11—H11	120.8
C1—C2—H2	120.6	C10—C11—H11	120.8
C3—C2—H2	120.6	C11—C12—C13	121.3 (4)
C4—C3—C2	120.9 (3)	C11—C12—H12	119.4
C4—C3—H3	119.6	C13—C12—H12	119.4
C2—C3—H3	119.6	C14—C13—C12	118.9 (3)
C3—C4—C5	119.5 (3)	C14—C13—H13	120.6
C3—C4—H4	120.3	C12—C13—H13	120.6
C5—C4—H4	120.3	C13—C14—C15	121.4 (3)
C6—C5—C4	120.7 (3)	C13—C14—N4	119.7 (3)
C6—C5—N1	119.0 (3)	C15—C14—N4	118.8 (3)
C4—C5—N1	120.4 (3)	C14—C15—C10	118.2 (3)
C5—C6—C1	118.5 (3)	C14—C15—H15	120.9
C5—C6—H6	120.7	C10—C15—H15	120.9
C1—C6—H6	120.7	N4—C16—C17	105.2 (3)
N1—C7—C8	105.6 (3)	N4—C16—H16	127.4
N1—C7—H7	127.2	C17—C16—H16	127.4
C8—C7—H7	127.2	N6—C17—C16	108.0 (3)
C7—C8—N3	107.5 (3)	N6—C17—C18	122.0 (4)
C7—C8—C9	129.8 (4)	C16—C17—C18	129.9 (4)
N3—C8—C9	122.7 (3)	O2—C18—C17	109.9 (4)
O1—C9—C8	111.6 (3)	O2—C18—H18A	109.7
O1—C9—H9A	109.3	C17—C18—H18A	109.7
C8—C9—H9A	109.3	O2—C18—H18B	109.7
O1—C9—H9B	109.3	C17—C18—H18B	109.7
C8—C9—H9B	109.3	H18A—C18—H18B	108.2
H9A—C9—H9B	108.0	H1W—O1W—H2W	109 (4)
C18—O2—H2O	120 (5)

C7—N1—N2—N3	0.5 (4)	C16—N4—N5—N6	−0.2 (4)
C5—N1—N2—N3	−179.0 (3)	C14—N4—N5—N6	179.2 (3)
N1—N2—N3—C8	−0.3 (4)	N4—N5—N6—C17	0.3 (4)
C6—C1—C2—C3	0.1 (5)	C15—C10—C11—C12	−0.7 (5)
Cl1—C1—C2—C3	179.0 (3)	Cl2—C10—C11—C12	178.7 (3)
C1—C2—C3—C4	0.5 (5)	C10—C11—C12—C13	1.3 (5)
C2—C3—C4—C5	−0.7 (5)	C11—C12—C13—C14	−1.1 (5)
C3—C4—C5—C6	0.3 (5)	C12—C13—C14—C15	0.4 (5)
C3—C4—C5—N1	−178.9 (3)	C12—C13—C14—N4	179.9 (3)
C7—N1—C5—C6	−166.4 (3)	C16—N4—C14—C13	17.2 (5)
N2—N1—C5—C6	12.9 (5)	N5—N4—C14—C13	−162.1 (3)
C7—N1—C5—C4	12.8 (5)	C16—N4—C14—C15	−163.2 (3)
N2—N1—C5—C4	−167.9 (3)	N5—N4—C14—C15	17.4 (5)
C4—C5—C6—C1	0.3 (5)	C13—C14—C15—C10	0.1 (5)
N1—C5—C6—C1	179.5 (3)	N4—C14—C15—C10	−179.4 (3)
C2—C1—C6—C5	−0.5 (5)	C11—C10—C15—C14	0.0 (5)
Cl1—C1—C6—C5	−179.4 (3)	Cl2—C10—C15—C14	−179.4 (3)
N2—N1—C7—C8	−0.4 (4)	N5—N4—C16—C17	0.1 (4)
C5—N1—C7—C8	179.0 (3)	C14—N4—C16—C17	−179.3 (3)
N1—C7—C8—N3	0.2 (4)	N5—N6—C17—C16	−0.3 (4)
N1—C7—C8—C9	−179.4 (3)	N5—N6—C17—C18	−179.8 (3)
N2—N3—C8—C7	0.1 (4)	N4—C16—C17—N6	0.1 (4)
N2—N3—C8—C9	179.7 (3)	N4—C16—C17—C18	179.6 (4)
C7—C8—C9—O1	−98.3 (5)	N6—C17—C18—O2	−60.3 (5)
N3—C8—C9—O1	82.2 (5)	C16—C17—C18—O2	120.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84 (4)	1.82 (4)	2.651 (5)	170 (5)
O2—H2o···O1w	0.84 (6)	1.80 (5)	2.641 (5)	174 (7)
O1w—H1w···N3	0.84 (4)	2.00 (4)	2.837 (5)	172 (4)
O1w—H2w···O1ⁱⁱ	0.84 (4)	1.95 (5)	2.663 (5)	142 (4)
C16—H16···O1wⁱⁱⁱ	0.95	2.45	3.383 (5)	166
C7—H7···N6^iv	0.95	2.28	3.197 (5)	161

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₉H₈ClN₃O·0.5H₂O
M_r	218.64
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	6.0078 (4), 7.4897 (4), 22.3145 (15)
α, β, γ (°)	88.818 (4), 89.901 (2), 80.493 (4)
V (Å³)	990.07 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.18 × 0.18 × 0.02

Data collection
Diffractometer	Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.843, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10830, 3909, 2948
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.163, 1.00
No. of reflections	3909
No. of parameters	274
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.34

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.84 (4)	1.82 (4)	2.651 (5)	170 (5)
O2—H2o···O1w	0.84 (6)	1.80 (5)	2.641 (5)	174 (7)
O1w—H1w···N3	0.84 (4)	2.00 (4)	2.837 (5)	172 (4)
O1w—H2w···O1ⁱⁱ	0.84 (4)	1.95 (5)	2.663 (5)	142 (4)
C16—H16···O1wⁱⁱⁱ	0.95	2.45	3.383 (5)	166
C7—H7···N6^iv	0.95	2.28	3.197 (5)	161

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x+1, y, z; (iii) x−1, y, z; (iv) x−1, y+1, z.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

References

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