7-Chloro-4-[(E)-2-(4-methoxy­benzyl­idene)hydrazin-1-yl]quinoline monohydrate

Lima Ferreira, M. de; Souza, M.V.N. de; Howie, R.A.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536810006598

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o696-o697

doi:10.1107/S1600536810006598

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7-Chloro-4-[(E)-2-(4-methoxybenzylidene)hydrazin-1-yl]quinoline monohydrate

Marcelle de Lima Ferreira,^a Marcus V. N. de Souza,^a R. Alan Howie,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aInstituto de Tecnologia em Farmacos, Fundação Oswaldo Cruz (FIOCRUZ), FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, ^bDepartment of Chemistry, University of Aberdeen, Old Aberdeen AB15 5NY, Scotland, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro 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, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 18 February 2010; accepted 19 February 2010; online 27 February 2010)

The organic molecule in the title hydrate, C₁₇H₁₄ClN₃O·H₂O, has a small but significant twist from planarity, as seen in the dihedral angle of 12.10 (17)° between the quinoline and benzene rings. The conformation about the C=N bond is E. Chains along the b axis are formed in the crystal structure aided by water–quinoline O—H⋯N (× 2) and hydrazone–water N—H⋯O hydrogen bonds. Layers of these chains stack along the a axis via C—H⋯π and π–π interactions [ring centroid–ring centroid distance = 3.674 (2) Å]. C—H⋯O interactions are also present.

Related literature

For background to the pharmacological activity of quinoline derivatives, see: Warshakoon et al. (2006 ). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007 ); de Souza et al. (2005 ). For related structures, see: Kaiser et al. (2009 ); de Souza et al. (2009 , 2010 ).

Experimental

Crystal data

C₁₇H₁₄ClN₃O·H₂O
M_r = 329.78
Triclinic, $[P \overline 1]$
a = 7.0086 (6) Å
b = 9.2384 (8) Å
c = 13.3701 (12) Å
α = 100.026 (4)°
β = 103.903 (5)°
γ = 107.000 (5)°
V = 775.27 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.12 × 0.04 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.686, T_max = 1.000
10514 measured reflections
2702 independent reflections
2037 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.150
S = 1.02
2702 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N1ⁱ	0.85 (5)	2.02 (5)	2.867 (4)	172 (5)
O1w—H2w⋯N1	0.85 (5)	2.20 (5)	3.047 (5)	175 (5)
N2—H2n⋯O1wⁱⁱ	0.88	2.18	3.007 (4)	157
C5—H5⋯O1wⁱⁱ	0.95	2.45	3.380 (5)	165
C17—H17a⋯Cgⁱⁱⁱ	0.98	2.65	3.508 (5)	147
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y, -z+2.

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 ) 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/S1600536810006598/lh5002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006598/lh5002Isup2.hkl

checkCIF report

Comment top

Quinoline derivatives display biological activity (Warshakoon et al., 2006) and in this context attract interest as potential anti-malarial agents (Andrade et al. 2007; de Souza et al., 2005). Complementing biological studies are structural investigations (Kaiser et al., 2009; de Souza et al., 2009; de Souza et al., 2010), and the crystal structure of the title hydrate, (I), was investigated as a part of these on-going studies.

The molecular structure of the organic component of (I), Fig. 1, shows a small twist from planarity with the dihedral angle formed between the quinoline (maximum deviation = 0.039 (4) Å for the C6 atom) and benzene rings being 12.10 (17) °. The major deviation of a torsion angle from 0 or 180 ° is found in the C3–N2–N3–C10 torsion angle of 172.4 (3) °. The conformation about the C10═N3 bond [1.274 (5) Å] is E. The crystal packing is stabilised by a variety of hydrogen bonding interactions, Table 1. The water molecule accepts a hydrogen bond from the hydrazone-N2 atom and forms donor interactions with symmetry related quinoline-N1 atoms, the latter leading to eight-membered {···OHO···N}₂ synthons. The resulting supramolecular chain along the b axis, Fig. 2, is reinforced by a C–H···O contact, Table 1. The chains are arranged in layers in the bc plane with the most significant interactions between the layers being of the type π–π with the closest of these occurring between centrosymmetrically related N1,C1—C4,C9 rings [ring centroid(N1,C1—C4,C9)···ring centroid(N1,C1—C4,C9)ⁱ distance = 3.674 (2) Å for i: -x, 1-y, 1-z], Fig. 3. In addition to these interactions, C–H···π contacts also occur between layers, Table 1.

Related literature top

For background to the pharmacological activity of quinoline derivatives, see: Warshakoon et al. (2006). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007); de Souza et al. (2005). For related structures, see: Kaiser et al. (2009); de Souza et al. (2009, 2010).

Experimental top

A solution of 7-chloro-4-quinolinylhydrazine (0.2 g, 1.03 mmol) and 4-methoxybenzaldehyde (1.24 mmol) in ethanol (5 ml) was stirred at room temperature until TLC indicated complete consumption of the hydrazine. The reaction mixture was rotary evaporated, the residue washed well with cold Et₂O (3 x 10 ml), and recrystallised from moist ethanol, yield 85%, m.pt. 417–418 K. IR [KBr, cm^-1] ν: 3120 (NH), 1565(N═C). MS/ESI: m/z [M—H]⁺: 310.8.

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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the components comprising the asymmetric unit in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. View of the supramolecular chain in (I) showing the O–H···N and N–H···O hydrogen bonding as orange and blue dashed lines, respectively. The C–H···O contacts are represented as green dashed lines. Colour code: Cl, cyan; O, red; N, blue; C, grey; and H, green.
	Fig. 3. A view of the stacking of layers in (I); O–H···N hydrogen bonding is shown as orange dashed lines. The layers are linked by π–π (purple dashed lines) and C–H···π contacts (pink dashed lines). Colour code: Cl, cyan; O, red; N, blue; C, grey; and H, green.

7-Chloro-4-[(E)-2-(4-methoxybenzylidene)hydrazin-1-yl]quinoline monohydrate top

Crystal data top

C₁₇H₁₄ClN₃O·H₂O	Z = 2
M_r = 329.78	F(000) = 344
Triclinic, P1	D_x = 1.413 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0086 (6) Å	Cell parameters from 27436 reflections
b = 9.2384 (8) Å	θ = 2.9–27.5°
c = 13.3701 (12) Å	µ = 0.26 mm⁻¹
α = 100.026 (4)°	T = 120 K
β = 103.903 (5)°	Needle, colourless
γ = 107.000 (5)°	0.12 × 0.04 × 0.02 mm
V = 775.27 (12) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	2702 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2037 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.064
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −10→10
T_min = 0.686, T_max = 1.000	l = −15→15
10514 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0109P)² + 2.93P] where P = (F_o² + 2F_c²)/3
2702 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₇H₁₄ClN₃O·H₂O	γ = 107.000 (5)°
M_r = 329.78	V = 775.27 (12) Å³
Triclinic, P1	Z = 2
a = 7.0086 (6) Å	Mo Kα radiation
b = 9.2384 (8) Å	µ = 0.26 mm⁻¹
c = 13.3701 (12) Å	T = 120 K
α = 100.026 (4)°	0.12 × 0.04 × 0.02 mm
β = 103.903 (5)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2702 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2037 reflections with I > 2σ(I)
T_min = 0.686, T_max = 1.000	R_int = 0.064
10514 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
2702 reflections	Δρ_min = −0.36 e Å⁻³
215 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	0.12492 (19)	0.53097 (12)	0.13214 (8)	0.0337 (3)
O1	0.3226 (4)	0.0839 (3)	1.1296 (2)	0.0268 (7)
N1	0.2963 (5)	0.7665 (4)	0.5289 (2)	0.0233 (7)
N2	0.2484 (5)	0.3358 (4)	0.6035 (2)	0.0226 (7)
H2N	0.2193	0.2506	0.5527	0.027*
N3	0.2774 (5)	0.3291 (4)	0.7081 (2)	0.0220 (7)
C1	0.3251 (6)	0.7500 (4)	0.6279 (3)	0.0247 (9)
H1	0.3611	0.8418	0.6835	0.030*
C2	0.3074 (6)	0.6112 (4)	0.6569 (3)	0.0217 (9)
H2	0.3239	0.6092	0.7292	0.026*
C3	0.2653 (6)	0.4750 (4)	0.5796 (3)	0.0178 (8)
C4	0.2376 (6)	0.4842 (4)	0.4712 (3)	0.0188 (8)
C5	0.2011 (6)	0.3562 (4)	0.3853 (3)	0.0203 (8)
H5	0.1959	0.2576	0.3985	0.024*
C6	0.1728 (6)	0.3715 (4)	0.2828 (3)	0.0215 (8)
H6	0.1518	0.2852	0.2259	0.026*
C7	0.1753 (6)	0.5170 (4)	0.2634 (3)	0.0211 (8)
C8	0.2147 (6)	0.6443 (4)	0.3441 (3)	0.0225 (9)
H8	0.2180	0.7417	0.3292	0.027*
C9	0.2507 (6)	0.6313 (4)	0.4502 (3)	0.0201 (8)
C10	0.2358 (6)	0.1919 (5)	0.7224 (3)	0.0235 (9)
H10	0.1879	0.1044	0.6620	0.028*
C11	0.2591 (6)	0.1642 (4)	0.8281 (3)	0.0199 (8)
C12	0.2046 (6)	0.0122 (4)	0.8385 (3)	0.0222 (9)
H12	0.1524	−0.0724	0.7759	0.027*
C13	0.2235 (6)	−0.0212 (4)	0.9368 (3)	0.0214 (8)
H13	0.1854	−0.1267	0.9415	0.026*
C14	0.2985 (6)	0.1016 (4)	1.0276 (3)	0.0217 (8)
C15	0.3569 (6)	0.2567 (4)	1.0201 (3)	0.0229 (9)
H15	0.4099	0.3408	1.0830	0.027*
C16	0.3379 (6)	0.2878 (4)	0.9220 (3)	0.0227 (9)
H16	0.3781	0.3934	0.9176	0.027*
C17	0.2580 (7)	−0.0735 (4)	1.1403 (3)	0.0268 (9)
H17A	0.1093	−0.1280	1.0997	0.040*
H17B	0.2787	−0.0709	1.2158	0.040*
H17C	0.3418	−0.1291	1.1127	0.040*
O1W	0.7337 (5)	0.9550 (3)	0.5298 (2)	0.0309 (7)
H1W	0.736 (8)	1.039 (6)	0.511 (4)	0.046*
H2W	0.610 (8)	0.908 (6)	0.530 (4)	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0524 (7)	0.0299 (6)	0.0200 (5)	0.0158 (5)	0.0098 (5)	0.0088 (4)
O1	0.0346 (17)	0.0247 (15)	0.0202 (14)	0.0082 (13)	0.0077 (12)	0.0084 (11)
N1	0.0272 (19)	0.0234 (17)	0.0200 (17)	0.0102 (15)	0.0088 (14)	0.0031 (13)
N2	0.0285 (19)	0.0215 (17)	0.0191 (17)	0.0116 (15)	0.0062 (14)	0.0047 (13)
N3	0.0258 (19)	0.0246 (18)	0.0207 (17)	0.0122 (15)	0.0103 (14)	0.0084 (14)
C1	0.025 (2)	0.021 (2)	0.026 (2)	0.0067 (17)	0.0097 (18)	0.0019 (16)
C2	0.025 (2)	0.024 (2)	0.0171 (19)	0.0085 (17)	0.0100 (17)	0.0035 (16)
C3	0.0147 (19)	0.0195 (19)	0.0205 (19)	0.0066 (15)	0.0067 (16)	0.0058 (15)
C4	0.0126 (19)	0.0185 (19)	0.024 (2)	0.0037 (15)	0.0070 (16)	0.0050 (15)
C5	0.020 (2)	0.0164 (19)	0.024 (2)	0.0070 (16)	0.0057 (16)	0.0047 (15)
C6	0.018 (2)	0.020 (2)	0.025 (2)	0.0038 (16)	0.0088 (16)	0.0041 (16)
C7	0.021 (2)	0.023 (2)	0.021 (2)	0.0075 (17)	0.0077 (16)	0.0073 (16)
C8	0.024 (2)	0.0175 (19)	0.027 (2)	0.0078 (16)	0.0077 (17)	0.0071 (16)
C9	0.016 (2)	0.0194 (19)	0.024 (2)	0.0046 (16)	0.0096 (16)	0.0033 (16)
C10	0.024 (2)	0.028 (2)	0.020 (2)	0.0108 (17)	0.0086 (17)	0.0053 (16)
C11	0.018 (2)	0.0199 (19)	0.023 (2)	0.0068 (16)	0.0085 (16)	0.0071 (16)
C12	0.024 (2)	0.022 (2)	0.023 (2)	0.0102 (17)	0.0098 (17)	0.0062 (16)
C13	0.023 (2)	0.0154 (19)	0.028 (2)	0.0066 (16)	0.0109 (17)	0.0061 (16)
C14	0.022 (2)	0.023 (2)	0.022 (2)	0.0076 (17)	0.0093 (17)	0.0085 (16)
C15	0.022 (2)	0.019 (2)	0.024 (2)	0.0066 (17)	0.0041 (17)	0.0036 (16)
C16	0.024 (2)	0.0168 (19)	0.026 (2)	0.0044 (16)	0.0073 (17)	0.0093 (16)
C17	0.032 (2)	0.025 (2)	0.028 (2)	0.0113 (18)	0.0109 (18)	0.0114 (17)
O1W	0.0347 (18)	0.0205 (15)	0.0434 (18)	0.0117 (14)	0.0171 (15)	0.0123 (13)

Geometric parameters (Å, º) top

Cl1—C7	1.740 (4)	C7—C8	1.360 (5)
O1—C14	1.377 (4)	C8—C9	1.413 (5)
O1—C17	1.435 (5)	C8—H8	0.9500
N1—C1	1.332 (5)	C10—C11	1.458 (5)
N1—C9	1.385 (5)	C10—H10	0.9500
N2—C3	1.357 (5)	C11—C12	1.385 (5)
N2—N3	1.380 (4)	C11—C16	1.409 (5)
N2—H2N	0.8800	C12—C13	1.386 (5)
N3—C10	1.274 (5)	C12—H12	0.9500
C1—C2	1.383 (5)	C13—C14	1.379 (5)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.386 (5)	C14—C15	1.400 (5)
C2—H2	0.9500	C15—C16	1.374 (5)
C3—C4	1.435 (5)	C15—H15	0.9500
C4—C9	1.417 (5)	C16—H16	0.9500
C4—C5	1.411 (5)	C17—H17A	0.9800
C5—C6	1.374 (5)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.409 (5)	O1W—H1W	0.85 (5)
C6—H6	0.9500	O1W—H2W	0.85 (5)

C14—O1—C17	117.0 (3)	N1—C9—C8	116.8 (3)
C1—N1—C9	115.5 (3)	C4—C9—C8	119.7 (3)
C3—N2—N3	119.4 (3)	N3—C10—C11	122.5 (3)
C3—N2—H2N	120.3	N3—C10—H10	118.8
N3—N2—H2N	120.3	C11—C10—H10	118.8
C10—N3—N2	115.5 (3)	C12—C11—C16	117.8 (3)
N1—C1—C2	125.9 (4)	C12—C11—C10	119.9 (3)
N1—C1—H1	117.0	C16—C11—C10	122.3 (3)
C2—C1—H1	117.0	C11—C12—C13	122.5 (4)
C1—C2—C3	119.5 (3)	C11—C12—H12	118.8
C1—C2—H2	120.3	C13—C12—H12	118.8
C3—C2—H2	120.3	C14—C13—C12	118.8 (3)
N2—C3—C2	122.1 (3)	C14—C13—H13	120.6
N2—C3—C4	120.0 (3)	C12—C13—H13	120.6
C2—C3—C4	117.9 (3)	O1—C14—C13	124.4 (3)
C9—C4—C5	118.4 (3)	O1—C14—C15	115.4 (3)
C9—C4—C3	117.7 (3)	C13—C14—C15	120.2 (3)
C5—C4—C3	123.9 (3)	C16—C15—C14	120.2 (4)
C6—C5—C4	121.3 (3)	C16—C15—H15	119.9
C6—C5—H5	119.3	C14—C15—H15	119.9
C4—C5—H5	119.3	C15—C16—C11	120.5 (3)
C5—C6—C7	119.0 (3)	C15—C16—H16	119.8
C5—C6—H6	120.5	C11—C16—H16	119.8
C7—C6—H6	120.5	O1—C17—H17A	109.5
C8—C7—C6	121.6 (3)	O1—C17—H17B	109.5
C8—C7—Cl1	120.0 (3)	H17A—C17—H17B	109.5
C6—C7—Cl1	118.3 (3)	O1—C17—H17C	109.5
C7—C8—C9	119.8 (3)	H17A—C17—H17C	109.5
C7—C8—H8	120.1	H17B—C17—H17C	109.5
C9—C8—H8	120.1	H1W—O1W—H2W	108 (5)
N1—C9—C4	123.5 (3)

C3—N2—N3—C10	172.4 (3)	C3—C4—C9—N1	2.5 (5)
C9—N1—C1—C2	−2.0 (6)	C5—C4—C9—C8	3.8 (5)
N1—C1—C2—C3	3.1 (6)	C3—C4—C9—C8	−177.0 (3)
N3—N2—C3—C2	−1.1 (5)	C7—C8—C9—N1	178.1 (3)
N3—N2—C3—C4	179.4 (3)	C7—C8—C9—C4	−2.4 (6)
C1—C2—C3—N2	179.3 (3)	N2—N3—C10—C11	179.7 (3)
C1—C2—C3—C4	−1.2 (5)	N3—C10—C11—C12	177.7 (4)
N2—C3—C4—C9	178.2 (3)	N3—C10—C11—C16	−2.8 (6)
C2—C3—C4—C9	−1.3 (5)	C16—C11—C12—C13	0.5 (6)
N2—C3—C4—C5	−2.7 (5)	C10—C11—C12—C13	180.0 (4)
C2—C3—C4—C5	177.8 (3)	C11—C12—C13—C14	0.3 (6)
C9—C4—C5—C6	−1.8 (5)	C17—O1—C14—C13	−2.2 (5)
C3—C4—C5—C6	179.1 (4)	C17—O1—C14—C15	178.0 (3)
C4—C5—C6—C7	−1.6 (6)	C12—C13—C14—O1	179.4 (4)
C5—C6—C7—C8	3.1 (6)	C12—C13—C14—C15	−0.9 (6)
C5—C6—C7—Cl1	−176.5 (3)	O1—C14—C15—C16	−179.5 (3)
C6—C7—C8—C9	−1.1 (6)	C13—C14—C15—C16	0.7 (6)
Cl1—C7—C8—C9	178.5 (3)	C14—C15—C16—C11	0.1 (6)
C1—N1—C9—C4	−0.9 (5)	C12—C11—C16—C15	−0.7 (6)
C1—N1—C9—C8	178.6 (3)	C10—C11—C16—C15	179.8 (4)
C5—C4—C9—N1	−176.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N1ⁱ	0.85 (5)	2.02 (5)	2.867 (4)	172 (5)
N2—H2n···O1wⁱⁱ	0.88	2.18	3.007 (4)	157
O1w—H2w···N1	0.85 (5)	2.20 (5)	3.047 (5)	175 (5)
C5—H5···O1wⁱⁱ	0.95	2.45	3.380 (5)	165
C17—H17a···Cgⁱⁱⁱ	0.98	2.65	3.508 (5)	147

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄ClN₃O·H₂O
M_r	329.78
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	7.0086 (6), 9.2384 (8), 13.3701 (12)
α, β, γ (°)	100.026 (4), 103.903 (5), 107.000 (5)
V (Å³)	775.27 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.12 × 0.04 × 0.02

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.686, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10514, 2702, 2037
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.150, 1.02
No. of reflections	2702
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.36

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N1ⁱ	0.85 (5)	2.02 (5)	2.867 (4)	172 (5)
N2—H2n···O1wⁱⁱ	0.88	2.18	3.007 (4)	157
O1w—H2w···N1	0.85 (5)	2.20 (5)	3.047 (5)	175 (5)
C5—H5···O1wⁱⁱ	0.95	2.45	3.380 (5)	165
C17—H17a···Cgⁱⁱⁱ	0.98	2.65	3.508 (5)	147

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

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 (Brazil).

References

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Volume 66| Part 3| March 2010| Pages o696-o697

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