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

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

doi:10.1107/S1600536810006586

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o698-o699

doi:10.1107/S1600536810006586

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

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

^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, ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and ^fDepartamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: edward.tiekink@gmail.com

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

In the title hydrate, C₁₇H₁₄ClN₃O·H₂O, the dihedral angle between the quinoline fused-ring system and the benzene ring is 13.4 (2)° and the conformation about the C=N bond is E. In the crystal, N_h—H⋯O_w and O_w—H⋯N_q (h = hydrozone, w = water and q = quinoline) hydrogen bonds generate a two-dimenstional network in the ac plane. A weak C—H⋯O interaction helps to consolidate the packing.

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 ). For the structure of the isomeric 2-methoxy structure, see: de Lima Ferreira et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₄ClN₃O·H₂O
M_r = 329.78
Monoclinic, P 2₁ /c
a = 3.9202 (2) Å
b = 24.5084 (17) Å
c = 16.1212 (11) Å
β = 91.639 (4)°
V = 1548.26 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.62 × 0.03 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.735, T_max = 0.995
11507 measured reflections
2716 independent reflections
1769 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.260
S = 1.04
2716 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1W	0.88	2.08	2.928 (7)	161
O1W—H1W⋯N1ⁱ	0.81 (9)	2.30 (9)	3.030 (8)	150 (8)
O1W—H2W⋯N1ⁱⁱ	0.82 (9)	2.03 (9)	2.820 (7)	163 (8)
C5—H5⋯O1W	0.95	2.43	3.358 (8)	166
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536810006586/hb5340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006586/hb5340Isup2.hkl

checkCIF report

Comment top

Quinoline derivatives are known to display pharmacological potential (Warshakoon et al., 2006) and are being investigated for their anti-malarial activity (Andrade et al. 2007; de Souza et al., 2005). Structural studies on quinoline derivatives augment the biological investigations (Kaiser et al., 2009; de Souza et al., 2009; de Souza et al., 2010; de Lima Ferreira et al., 2010) and as a part of these studies, the crystal structure of the title hydrate, (I), was investigated.

The most significant twist in the quinoline molecule of (I), Fig. 1, occurs around the C10–C11 bond as seen in the N3–C10–C11–C16 torsion angle of 6.9 (9) °. This accounts for the dihedral angle of 13.4 (2) ° formed between the quinoline fused-ring system and the benzene ring. The conformation about the C10═N3 bond [1.282 (8) 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 bridges two symmetry related molecules by forming donor interactions with quinoline-N1 atoms; the water-O atom also participates in a C–H···O contact, Table 1. The result of the hydrogen bonding is the formation of a 2-D supramolecular array in the ac plane, Fig. 2, and these stack along the b axis, Fig. 3.

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). For the structure of the isomeric 2-methoxy structure, see: de Lima Ferreira et al. (2010).

Experimental top

A solution of 7-chloro-4-quinolinylhydrazine(0.2 g, 1.03 mmol) and 2-methoxybenzaldehyde (1.2 mmol) in EtOH (5 ml) was maintained at room temperature overnight and rotary evaporated. The solid residue, was washed with cold Et₂O (3 x 10 ml) and recrystallised from EtOH; m.pt. 459-461 K, yield 82%. The sample for the X-ray study was slowly grown from moist EtOH and was found to be the monohydrate. MS/ESI: [M—H]: 310.8. IR νmax (cm-1; KBr disc): 3190 (N—H), 1578 (C=N).

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. Molecular structures of the asymmetric unit in (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. View of the 2-D supramolecular array in the ac plane of (I) showing the O–H···N and N–H···O hydrogen bonding as orange and blue dashed lines, respectively. Colour code: Cl, cyan; O, red; N, blue; C, grey; and H, green.
	Fig. 3. A view of the stacking of layers in (I). The O–H···N and N–H···O hydrogen bonding as orange and blue dashed lines, respectively. Colour code: Cl, cyan; O, red; N, blue; C, grey; and H, green.

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

Crystal data top

C₁₇H₁₄ClN₃O·H₂O	F(000) = 688
M_r = 329.78	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9260 reflections
a = 3.9202 (2) Å	θ = 2.9–27.5°
b = 24.5084 (17) Å	µ = 0.26 mm⁻¹
c = 16.1212 (11) Å	T = 120 K
β = 91.639 (4)°	Needle, colourless
V = 1548.26 (17) Å³	0.62 × 0.03 × 0.02 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2716 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1769 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.096
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ϕ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −29→29
T_min = 0.735, T_max = 0.995	l = −19→19
11507 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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.260	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1P)² + 10.4045P] where P = (F_o² + 2F_c²)/3
2716 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₇H₁₄ClN₃O·H₂O	V = 1548.26 (17) Å³
M_r = 329.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.9202 (2) Å	µ = 0.26 mm⁻¹
b = 24.5084 (17) Å	T = 120 K
c = 16.1212 (11) Å	0.62 × 0.03 × 0.02 mm
β = 91.639 (4)°

Data collection top

Nonius KappaCCD diffractometer	2716 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1769 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.995	R_int = 0.096
11507 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.260	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1P)² + 10.4045P] where P = (F_o² + 2F_c²)/3
2716 reflections	Δρ_max = 0.40 e Å⁻³
215 parameters	Δρ_min = −0.45 e Å⁻³

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	0.0208 (4)	0.57108 (6)	0.05313 (10)	0.0256 (5)
O1	1.3298 (11)	0.93299 (18)	0.2940 (3)	0.0232 (10)
N1	0.1966 (13)	0.7497 (2)	−0.0985 (3)	0.0201 (12)
N2	0.6619 (13)	0.8261 (2)	0.1080 (3)	0.0214 (12)
H2N	0.6968	0.8080	0.1547	0.026*
N3	0.7680 (12)	0.8795 (2)	0.1015 (3)	0.0195 (12)
C1	0.2920 (16)	0.8018 (3)	−0.0989 (4)	0.0232 (15)
H1	0.2504	0.8220	−0.1484	0.028*
C2	0.4479 (15)	0.8288 (2)	−0.0322 (4)	0.0183 (13)
H2	0.5157	0.8658	−0.0377	0.022*
C3	0.5046 (15)	0.8016 (2)	0.0426 (4)	0.0203 (14)
C4	0.3926 (15)	0.7459 (2)	0.0470 (4)	0.0176 (13)
C5	0.4234 (15)	0.7141 (3)	0.1204 (4)	0.0223 (14)
H5	0.5240	0.7296	0.1692	0.027*
C6	0.3094 (16)	0.6611 (2)	0.1217 (4)	0.0206 (14)
H6	0.3293	0.6402	0.1712	0.025*
C7	0.1640 (15)	0.6384 (2)	0.0496 (4)	0.0176 (13)
C8	0.1307 (16)	0.6672 (3)	−0.0225 (4)	0.0213 (14)
H8	0.0329	0.6504	−0.0707	0.026*
C9	0.2419 (15)	0.7222 (2)	−0.0257 (4)	0.0180 (13)
C10	0.9303 (15)	0.8980 (3)	0.1657 (4)	0.0211 (14)
H10	0.9774	0.8745	0.2115	0.025*
C11	1.0442 (14)	0.9551 (2)	0.1693 (4)	0.0164 (13)
C12	1.2380 (14)	0.9726 (2)	0.2387 (4)	0.0181 (14)
C13	1.3295 (16)	1.0271 (3)	0.2466 (4)	0.0237 (15)
H13	1.4596	1.0391	0.2938	0.028*
C14	1.2299 (16)	1.0641 (3)	0.1851 (4)	0.0222 (14)
H14	1.2908	1.1014	0.1909	0.027*
C15	1.0422 (16)	1.0471 (3)	0.1152 (4)	0.0249 (15)
H15	0.9778	1.0725	0.0731	0.030*
C16	0.9495 (15)	0.9922 (2)	0.1078 (4)	0.0212 (14)
H16	0.8211	0.9802	0.0604	0.025*
C17	1.5235 (16)	0.9495 (3)	0.3666 (4)	0.0242 (15)
H17A	1.7439	0.9642	0.3501	0.036*
H17B	1.5613	0.9179	0.4030	0.036*
H17C	1.3976	0.9777	0.3962	0.036*
O1W	0.7223 (14)	0.7893 (2)	0.2807 (3)	0.0304 (12)
H1W	0.53 (2)	0.785 (3)	0.300 (5)	0.046*
H2W	0.89 (2)	0.780 (3)	0.309 (5)	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0319 (9)	0.0186 (8)	0.0263 (9)	−0.0044 (7)	−0.0002 (7)	0.0044 (7)
O1	0.028 (2)	0.023 (2)	0.018 (2)	0.0005 (19)	−0.0047 (18)	−0.001 (2)
N1	0.027 (3)	0.019 (3)	0.015 (3)	−0.002 (2)	−0.003 (2)	0.002 (2)
N2	0.027 (3)	0.020 (3)	0.017 (3)	−0.002 (2)	−0.003 (2)	0.002 (2)
N3	0.022 (3)	0.015 (3)	0.022 (3)	−0.002 (2)	0.004 (2)	−0.002 (2)
C1	0.026 (3)	0.026 (4)	0.017 (4)	0.000 (3)	−0.005 (3)	0.008 (3)
C2	0.023 (3)	0.015 (3)	0.017 (3)	−0.001 (2)	0.004 (3)	−0.004 (3)
C3	0.018 (3)	0.020 (3)	0.022 (4)	0.002 (3)	−0.003 (3)	−0.004 (3)
C4	0.016 (3)	0.020 (3)	0.017 (3)	0.001 (2)	0.005 (2)	0.001 (3)
C5	0.023 (3)	0.025 (3)	0.019 (4)	0.002 (3)	−0.002 (3)	0.000 (3)
C6	0.029 (3)	0.015 (3)	0.018 (4)	0.002 (3)	0.001 (3)	−0.001 (3)
C7	0.019 (3)	0.017 (3)	0.018 (3)	0.002 (2)	0.008 (2)	−0.002 (3)
C8	0.023 (3)	0.024 (3)	0.017 (4)	−0.004 (3)	−0.004 (3)	−0.001 (3)
C9	0.023 (3)	0.016 (3)	0.015 (3)	0.000 (2)	−0.002 (3)	−0.002 (3)
C10	0.019 (3)	0.021 (3)	0.023 (4)	0.001 (3)	0.002 (3)	0.005 (3)
C11	0.014 (3)	0.016 (3)	0.018 (3)	−0.004 (2)	0.001 (2)	−0.003 (3)
C12	0.014 (3)	0.019 (3)	0.022 (4)	0.001 (2)	0.006 (2)	−0.004 (3)
C13	0.027 (3)	0.026 (3)	0.018 (4)	−0.001 (3)	0.000 (3)	0.001 (3)
C14	0.026 (3)	0.015 (3)	0.026 (4)	−0.007 (3)	0.011 (3)	−0.003 (3)
C15	0.027 (3)	0.019 (3)	0.029 (4)	0.006 (3)	0.003 (3)	0.003 (3)
C16	0.024 (3)	0.018 (3)	0.021 (4)	0.001 (3)	0.004 (3)	−0.004 (3)
C17	0.022 (3)	0.030 (4)	0.021 (4)	−0.002 (3)	−0.002 (3)	−0.005 (3)
O1W	0.028 (3)	0.039 (3)	0.024 (3)	0.000 (2)	−0.005 (2)	0.004 (2)

Geometric parameters (Å, º) top

Cl1—C7	1.744 (6)	C7—C8	1.362 (9)
O1—C12	1.360 (7)	C8—C9	1.419 (9)
O1—C17	1.434 (7)	C8—H8	0.9500
N1—C1	1.330 (8)	C10—C11	1.471 (8)
N1—C9	1.361 (8)	C10—H10	0.9500
N2—C3	1.348 (8)	C11—C16	1.388 (9)
N2—N3	1.379 (7)	C11—C12	1.401 (8)
N2—H2N	0.8800	C12—C13	1.388 (9)
N3—C10	1.282 (8)	C13—C14	1.391 (9)
C1—C2	1.389 (9)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.391 (9)
C2—C3	1.391 (9)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.399 (9)
C3—C4	1.436 (8)	C15—H15	0.9500
C4—C9	1.420 (8)	C16—H16	0.9500
C4—C5	1.420 (9)	C17—H17A	0.9800
C5—C6	1.372 (9)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.396 (9)	O1W—H1W	0.81 (9)
C6—H6	0.9500	O1W—H2W	0.82 (9)

C12—O1—C17	117.2 (5)	N1—C9—C4	123.4 (5)
C1—N1—C9	116.6 (5)	C8—C9—C4	118.6 (6)
C3—N2—N3	119.7 (5)	N3—C10—C11	120.7 (6)
C3—N2—H2N	120.2	N3—C10—H10	119.6
N3—N2—H2N	120.2	C11—C10—H10	119.6
C10—N3—N2	114.6 (5)	C16—C11—C12	119.9 (6)
N1—C1—C2	124.9 (6)	C16—C11—C10	121.4 (5)
N1—C1—H1	117.6	C12—C11—C10	118.7 (5)
C2—C1—H1	117.6	O1—C12—C13	124.3 (6)
C1—C2—C3	119.9 (6)	O1—C12—C11	115.7 (5)
C1—C2—H2	120.1	C13—C12—C11	120.0 (6)
C3—C2—H2	120.1	C12—C13—C14	119.6 (6)
N2—C3—C2	121.6 (6)	C12—C13—H13	120.2
N2—C3—C4	121.2 (6)	C14—C13—H13	120.2
C2—C3—C4	117.2 (5)	C15—C14—C13	120.9 (6)
C9—C4—C5	119.1 (5)	C15—C14—H14	119.5
C9—C4—C3	117.9 (5)	C13—C14—H14	119.5
C5—C4—C3	122.9 (6)	C14—C15—C16	119.1 (6)
C6—C5—C4	120.8 (6)	C14—C15—H15	120.4
C6—C5—H5	119.6	C16—C15—H15	120.4
C4—C5—H5	119.6	C11—C16—C15	120.3 (6)
C5—C6—C7	119.3 (6)	C11—C16—H16	119.8
C5—C6—H6	120.3	C15—C16—H16	119.8
C7—C6—H6	120.3	O1—C17—H17A	109.5
C8—C7—C6	122.0 (6)	O1—C17—H17B	109.5
C8—C7—Cl1	119.7 (5)	H17A—C17—H17B	109.5
C6—C7—Cl1	118.3 (5)	O1—C17—H17C	109.5
C7—C8—C9	120.1 (6)	H17A—C17—H17C	109.5
C7—C8—H8	119.9	H17B—C17—H17C	109.5
C9—C8—H8	119.9	H1W—O1W—H2W	118 (9)
N1—C9—C8	118.0 (5)

C3—N2—N3—C10	−176.6 (6)	C7—C8—C9—C4	1.1 (9)
C9—N1—C1—C2	3.4 (9)	C5—C4—C9—N1	178.9 (6)
N1—C1—C2—C3	−2.1 (10)	C3—C4—C9—N1	−0.4 (9)
N3—N2—C3—C2	0.5 (9)	C5—C4—C9—C8	−0.8 (9)
N3—N2—C3—C4	179.6 (5)	C3—C4—C9—C8	179.9 (6)
C1—C2—C3—N2	178.5 (6)	N2—N3—C10—C11	−177.0 (5)
C1—C2—C3—C4	−0.6 (9)	N3—C10—C11—C16	6.9 (9)
N2—C3—C4—C9	−177.4 (6)	N3—C10—C11—C12	−176.3 (6)
C2—C3—C4—C9	1.7 (8)	C17—O1—C12—C13	2.3 (9)
N2—C3—C4—C5	3.3 (9)	C17—O1—C12—C11	−178.9 (5)
C2—C3—C4—C5	−177.6 (6)	C16—C11—C12—O1	−177.5 (5)
C9—C4—C5—C6	0.0 (9)	C10—C11—C12—O1	5.6 (8)
C3—C4—C5—C6	179.3 (6)	C16—C11—C12—C13	1.3 (9)
C4—C5—C6—C7	0.5 (9)	C10—C11—C12—C13	−175.6 (6)
C5—C6—C7—C8	−0.1 (9)	O1—C12—C13—C14	178.2 (6)
C5—C6—C7—Cl1	−179.9 (5)	C11—C12—C13—C14	−0.5 (9)
C6—C7—C8—C9	−0.7 (10)	C12—C13—C14—C15	−0.6 (10)
Cl1—C7—C8—C9	179.1 (5)	C13—C14—C15—C16	0.9 (10)
C1—N1—C9—C8	177.7 (6)	C12—C11—C16—C15	−1.0 (9)
C1—N1—C9—C4	−2.0 (9)	C10—C11—C16—C15	175.8 (6)
C7—C8—C9—N1	−178.6 (6)	C14—C15—C16—C11	−0.1 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.88	2.08	2.928 (7)	161
O1W—H1W···N1ⁱ	0.81 (9)	2.30 (9)	3.030 (8)	150 (8)
O1W—H2W···N1ⁱⁱ	0.82 (9)	2.03 (9)	2.820 (7)	163 (8)
C5—H5···O1W	0.95	2.43	3.358 (8)	166

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄ClN₃O·H₂O
M_r	329.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	3.9202 (2), 24.5084 (17), 16.1212 (11)
β (°)	91.639 (4)
V (Å³)	1548.26 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.62 × 0.03 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.735, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	11507, 2716, 1769
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.260, 1.04
No. of reflections	2716
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.1P)² + 10.4045P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.45

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

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.88	2.08	2.928 (7)	161
O1W—H1W···N1ⁱ	0.81 (9)	2.30 (9)	3.030 (8)	150 (8)
O1W—H2W···N1ⁱⁱ	0.82 (9)	2.03 (9)	2.820 (7)	163 (8)
C5—H5···O1W	0.95	2.43	3.358 (8)	166

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, −y+3/2, z+1/2.

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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