3-[(E)-(7-Chloro-4-quinol­yl)hydrazono­meth­yl]benzonitrile monohydrate

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

doi:10.1107/S1600536809050120

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3239-o3240

doi:10.1107/S1600536809050120

Open

access

3-[(E)-(7-Chloro-4-quinolyl)hydrazonomethyl]benzonitrile monohydrate

Marcelle L. de 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), Far-Manguinhos, 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 19 November 2009; accepted 21 November 2009; online 28 November 2009)

The title monohydrate, C₁₇H₁₁ClN₄·H₂O, features an essentially planar organic molecule, as seen in the dihedral angle of 2.42 (8)° formed between the quinoline and benzene planes. The conformation about the imine bond is E, and the N—H group is oriented towards the quinoline residue. The major feature of the crystal packing is the formation of supramolecular chains along [100], whereby the water molecule accepts one N—H⋯O hydrogen bond and makes two O—H⋯N hydrogen bonds. A C—H⋯O link is also present.

Related literature

For background information on the pharmacological activity of quinoline derivatives, see: Elslager et al. (1969 ); Font et al. (1997 ); Kaminsky & Meltzer (1968 ); Musiol et al. (2006 ); Nakamura et al. (1999 ); Palmer et al. (1993 ); Ridley (2002 ); Sloboda et al. (1991 ); Tanenbaum & Tuffanelli (1980 ); Warshakoon et al. (2006 ). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007 ); Cunico et al. (2006 ); da Silva et al. (2003 ); de Souza et al. (2005 ). For a related crystallographic study on neutral species related to the title compound, see: Kaiser et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₁ClN₄·H₂O
M_r = 324.76
Triclinic, $[P \overline 1]$
a = 8.7406 (2) Å
b = 9.8587 (3) Å
c = 10.2301 (2) Å
α = 110.8897 (15)°
β = 93.4341 (16)°
γ = 110.6766 (15)°
V = 752.93 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.12 × 0.09 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.901, T_max = 0.990
14600 measured reflections
3425 independent reflections
2902 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 1.10
3425 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N4ⁱ	0.83 (3)	2.21 (3)	2.982 (3)	155 (3)
O1w—H2w⋯N1ⁱⁱ	0.86 (3)	1.99 (3)	2.828 (3)	164 (3)
N2—H2n⋯O1w	0.86 (3)	2.07 (3)	2.917 (2)	167 (3)
C5—H5⋯O1w	0.95	2.39	3.331 (3)	169
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x+1, y, 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: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050120/hb5242sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050120/hb5242Isup2.hkl

checkCIF report

Comment top

The title compound, crystallized as a hydrate, (I), was prepared as part of an on-going investigation aimed at developing anti-malarial compounds based on the quinoline nucleus (Andrade et al.,2007; Cunico et al., 2006; da Silva et al., 2003; de Souza et al., 2005. The motivation for examining quinoline derivatives arises as the majority of anti-malarial drugs, such as chloroquine (Tanenbaum & Tuffanelli, 1980), mefloquine (Palmer et al., 1993), primaquine (Elslager et al., 1969) and amodiaquine (Ridley, 2002), possess a quinoline ring which has been the mainstay of malaria chemotherapy for much of the past 40 years (Font et al., 1997; Kaminsky & Meltzer, 1968; Musiol et al., 2006; Nakamura et al., 1999; Sloboda et al., 1991; Warshakoon et al., 2006).

The molecular structure of (I), Fig. 1, comprises an essentially planar quinoline framework with the maximum deviation from the least-squares plane through the non-hydrogen atoms being -0.012 (2) Å for atom C3. The planarity extends through the azo moiety (the C2–C3–N2–N3 and N2–N3–C10–C11 torsion angles are 2.4 (3) and -179.76 (16) °, respectively) into the terminal benzene; the dihedral angle formed between the quinoline and benzene rings is 2.42 (8) °. The conformation about the C10N3 bond is E. Finally, the amine-N2 group is oriented towards the quinoline nucleus as observed in related structures (Kaiser et al., (2009).

The water molecule of crystallization plays a pivotal role in the crystal packing. The water-H atoms form hydrogen bonds to the the pyridine-N1 and nitrile-N4 atoms, derived from different molecules, and at the same time accepts a hydrogen bond from the amino-N2 atom, Table 1. The tetrahedral environment for the O1w atom is completed by an acceptor interaction from the C5—H atom. The net result of the hydrogen bonding interactions is the formation of a supramolecular chain aligned along the a direction, Fig. 2.

Related literature top

For background information on the pharmacological activity of quinoline derivatives, see: Elslager et al. (1969); Font et al. (1997); Kaminsky & Meltzer (1968); Musiol et al. (2006); Nakamura et al. (1999); Palmer et al. (1993); Ridley (2002); Sloboda et al. (1991); Tanenbaum & Tuffanelli (1980); Warshakoon et al. (2006). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007); Cunico et al. (2006); da Silva et al. (2003); de Souza et al. (2005). For a related crystallographic study on neutral species related to the title compound, see: Kaiser et al. (2009).

Experimental top

A solution of 7-chloro-4-hydrazinoquinoline (0.20 g, 1.0 mmol) and 3-cyanobenzaldehyde (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 recrystallized from EtOH m. pt. 485–487 K, yield 77%. The sample for the X-ray study was slowly grown from moist EtOH and was found to be the monohydrate. MS/ESI: 305 [M—H—H₂O], based on ³⁵Cl. IR [KBr, cm^-1] ν: 3215 (NH), 1577 (CN).

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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. The asymmetric unit in (I) showing displacement ellipsoids at the 70% probability level.
	Fig. 2. Supramolecular 1-D chain in (I) aligned along [100]. The O–H···N (orange) and N–H···O (blue) hydrogen bonds are shown as dashed lines. Colour code: Cl, cyan; O, red; N, blue; C, grey; and H, green.

3-[(E)-(7-Chloro-4-quinolyl)hydrazonomethyl]benzonitrile mono hydrate top

Crystal data top

C₁₇H₁₁ClN₄·H₂O	Z = 2
M_r = 324.76	F(000) = 336
Triclinic, P1	D_x = 1.432 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7406 (2) Å	Cell parameters from 11816 reflections
b = 9.8587 (3) Å	θ = 2.9–27.5°
c = 10.2301 (2) Å	µ = 0.26 mm⁻¹
α = 110.8897 (15)°	T = 120 K
β = 93.4341 (16)°	Plate, yellow
γ = 110.6766 (15)°	0.12 × 0.09 × 0.04 mm
V = 752.93 (3) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	3425 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2902 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.046
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→12
T_min = 0.901, T_max = 0.990	l = −13→13
14600 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.023P)² + 0.7336P] where P = (F_o² + 2F_c²)/3
3425 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₁ClN₄·H₂O	γ = 110.6766 (15)°
M_r = 324.76	V = 752.93 (3) Å³
Triclinic, P1	Z = 2
a = 8.7406 (2) Å	Mo Kα radiation
b = 9.8587 (3) Å	µ = 0.26 mm⁻¹
c = 10.2301 (2) Å	T = 120 K
α = 110.8897 (15)°	0.12 × 0.09 × 0.04 mm
β = 93.4341 (16)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3425 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2902 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.990	R_int = 0.046
14600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.32 e Å⁻³
3425 reflections	Δρ_min = −0.25 e Å⁻³
217 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	0.19140 (6)	0.44486 (6)	−0.08216 (5)	0.02503 (14)
N1	0.0883 (2)	0.39813 (19)	0.38535 (17)	0.0215 (3)
N2	0.49296 (19)	0.27107 (18)	0.43632 (17)	0.0181 (3)
H2N	0.559 (3)	0.270 (3)	0.377 (2)	0.022*
N3	0.52218 (19)	0.23502 (18)	0.55031 (16)	0.0181 (3)
N4	1.1329 (2)	0.0074 (2)	0.7938 (2)	0.0357 (5)
C1	0.1296 (2)	0.3704 (2)	0.4975 (2)	0.0217 (4)
H1	0.0635	0.3806	0.5679	0.026*
C2	0.2613 (2)	0.3278 (2)	0.5209 (2)	0.0204 (4)
H2	0.2816	0.3086	0.6036	0.024*
C3	0.3625 (2)	0.3139 (2)	0.42154 (19)	0.0164 (4)
C4	0.3262 (2)	0.3449 (2)	0.29879 (19)	0.0160 (4)
C5	0.4207 (2)	0.3368 (2)	0.1905 (2)	0.0191 (4)
H5	0.5150	0.3113	0.1983	0.023*
C6	0.3779 (2)	0.3654 (2)	0.0746 (2)	0.0203 (4)
H6	0.4411	0.3583	0.0019	0.024*
C7	0.2398 (2)	0.4052 (2)	0.0646 (2)	0.0194 (4)
C8	0.1449 (2)	0.4147 (2)	0.1657 (2)	0.0193 (4)
H8	0.0515	0.4409	0.1557	0.023*
C9	0.1869 (2)	0.3852 (2)	0.28647 (19)	0.0178 (4)
C10	0.6454 (2)	0.1947 (2)	0.5564 (2)	0.0197 (4)
H10	0.7095	0.1919	0.4844	0.024*
C11	0.6892 (2)	0.1527 (2)	0.67264 (19)	0.0192 (4)
C12	0.8252 (2)	0.1113 (2)	0.6757 (2)	0.0216 (4)
H12	0.8867	0.1086	0.6020	0.026*
C13	0.8715 (2)	0.0735 (2)	0.7873 (2)	0.0231 (4)
C14	0.7821 (3)	0.0759 (2)	0.8950 (2)	0.0286 (5)
H14	0.8144	0.0508	0.9708	0.034*
C15	0.6451 (3)	0.1154 (3)	0.8908 (2)	0.0298 (5)
H15	0.5829	0.1166	0.9640	0.036*
C16	0.5979 (3)	0.1531 (2)	0.7807 (2)	0.0240 (4)
H16	0.5034	0.1792	0.7786	0.029*
C17	1.0162 (3)	0.0351 (2)	0.7902 (2)	0.0275 (5)
O1W	0.74203 (19)	0.2487 (2)	0.26148 (16)	0.0261 (3)
H1W	0.746 (3)	0.160 (3)	0.231 (3)	0.039*
H2W	0.845 (4)	0.311 (3)	0.302 (3)	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0233 (2)	0.0305 (3)	0.0261 (3)	0.0115 (2)	0.00062 (18)	0.0168 (2)
N1	0.0203 (8)	0.0239 (8)	0.0255 (8)	0.0132 (7)	0.0078 (7)	0.0109 (7)
N2	0.0171 (8)	0.0231 (8)	0.0199 (8)	0.0113 (6)	0.0052 (6)	0.0115 (7)
N3	0.0198 (8)	0.0162 (7)	0.0177 (7)	0.0070 (6)	0.0004 (6)	0.0069 (6)
N4	0.0342 (10)	0.0308 (10)	0.0417 (11)	0.0172 (9)	−0.0047 (9)	0.0122 (9)
C1	0.0209 (9)	0.0243 (10)	0.0229 (9)	0.0116 (8)	0.0080 (8)	0.0097 (8)
C2	0.0210 (9)	0.0211 (9)	0.0201 (9)	0.0087 (8)	0.0031 (7)	0.0094 (8)
C3	0.0150 (8)	0.0130 (8)	0.0191 (9)	0.0044 (7)	0.0018 (7)	0.0055 (7)
C4	0.0144 (8)	0.0136 (8)	0.0195 (9)	0.0063 (7)	0.0021 (7)	0.0056 (7)
C5	0.0162 (9)	0.0211 (9)	0.0225 (9)	0.0100 (7)	0.0031 (7)	0.0094 (8)
C6	0.0182 (9)	0.0218 (9)	0.0223 (9)	0.0083 (8)	0.0049 (7)	0.0100 (8)
C7	0.0188 (9)	0.0179 (9)	0.0217 (9)	0.0067 (7)	−0.0013 (7)	0.0097 (7)
C8	0.0147 (8)	0.0189 (9)	0.0250 (9)	0.0084 (7)	0.0012 (7)	0.0085 (8)
C9	0.0153 (8)	0.0155 (8)	0.0212 (9)	0.0068 (7)	0.0020 (7)	0.0055 (7)
C10	0.0192 (9)	0.0211 (9)	0.0206 (9)	0.0089 (7)	0.0036 (7)	0.0095 (8)
C11	0.0207 (9)	0.0156 (8)	0.0191 (9)	0.0061 (7)	−0.0013 (7)	0.0066 (7)
C12	0.0212 (9)	0.0182 (9)	0.0236 (9)	0.0066 (8)	0.0017 (8)	0.0085 (8)
C13	0.0247 (10)	0.0163 (9)	0.0250 (10)	0.0077 (8)	−0.0045 (8)	0.0069 (8)
C14	0.0397 (12)	0.0246 (10)	0.0222 (10)	0.0140 (9)	−0.0016 (9)	0.0107 (8)
C15	0.0408 (12)	0.0311 (11)	0.0229 (10)	0.0172 (10)	0.0082 (9)	0.0138 (9)
C16	0.0272 (10)	0.0246 (10)	0.0230 (10)	0.0134 (8)	0.0045 (8)	0.0101 (8)
C17	0.0321 (11)	0.0200 (10)	0.0266 (10)	0.0093 (9)	−0.0053 (9)	0.0082 (8)
O1W	0.0213 (7)	0.0359 (8)	0.0266 (8)	0.0169 (7)	0.0065 (6)	0.0130 (7)

Geometric parameters (Å, º) top

Cl1—C7	1.7454 (18)	C7—C8	1.362 (3)
N1—C1	1.328 (2)	C8—C9	1.423 (2)
N1—C9	1.368 (2)	C8—H8	0.9500
N2—C3	1.366 (2)	C10—C11	1.462 (2)
N2—N3	1.369 (2)	C10—H10	0.9500
N2—H2N	0.86 (2)	C11—C12	1.388 (3)
N3—C10	1.278 (2)	C11—C16	1.401 (3)
N4—C17	1.147 (3)	C12—C13	1.401 (3)
C1—C2	1.393 (3)	C12—H12	0.9500
C1—H1	0.9500	C13—C14	1.386 (3)
C2—C3	1.389 (3)	C13—C17	1.444 (3)
C2—H2	0.9500	C14—C15	1.387 (3)
C3—C4	1.437 (2)	C14—H14	0.9500
C4—C5	1.417 (3)	C15—C16	1.389 (3)
C4—C9	1.419 (2)	C15—H15	0.9500
C5—C6	1.373 (3)	C16—H16	0.9500
C5—H5	0.9500	O1W—H1W	0.83 (3)
C6—C7	1.403 (3)	O1W—H2W	0.86 (3)
C6—H6	0.9500

C1—N1—C9	116.07 (16)	C9—C8—H8	120.3
C3—N2—N3	119.16 (15)	N1—C9—C4	123.72 (16)
C3—N2—H2N	121.4 (14)	N1—C9—C8	116.93 (16)
N3—N2—H2N	119.4 (14)	C4—C9—C8	119.35 (16)
C10—N3—N2	115.64 (16)	N3—C10—C11	120.96 (17)
N1—C1—C2	125.78 (18)	N3—C10—H10	119.5
N1—C1—H1	117.1	C11—C10—H10	119.5
C2—C1—H1	117.1	C12—C11—C16	119.17 (17)
C3—C2—C1	118.91 (17)	C12—C11—C10	118.91 (17)
C3—C2—H2	120.5	C16—C11—C10	121.92 (17)
C1—C2—H2	120.5	C11—C12—C13	120.01 (18)
N2—C3—C2	122.36 (16)	C11—C12—H12	120.0
N2—C3—C4	119.55 (16)	C13—C12—H12	120.0
C2—C3—C4	118.09 (16)	C14—C13—C12	120.63 (18)
C5—C4—C9	118.81 (16)	C14—C13—C17	120.38 (17)
C5—C4—C3	123.77 (16)	C12—C13—C17	118.98 (19)
C9—C4—C3	117.42 (16)	C13—C14—C15	119.29 (18)
C6—C5—C4	120.96 (17)	C13—C14—H14	120.4
C6—C5—H5	119.5	C15—C14—H14	120.4
C4—C5—H5	119.5	C14—C15—C16	120.6 (2)
C5—C6—C7	119.30 (18)	C14—C15—H15	119.7
C5—C6—H6	120.4	C16—C15—H15	119.7
C7—C6—H6	120.4	C15—C16—C11	120.31 (19)
C8—C7—C6	122.12 (17)	C15—C16—H16	119.8
C8—C7—Cl1	119.72 (14)	C11—C16—H16	119.8
C6—C7—Cl1	118.16 (15)	N4—C17—C13	178.8 (2)
C7—C8—C9	119.46 (16)	H1W—O1W—H2W	102 (2)
C7—C8—H8	120.3

C3—N2—N3—C10	179.41 (16)	C5—C4—C9—N1	−179.23 (17)
C9—N1—C1—C2	−1.0 (3)	C3—C4—C9—N1	1.1 (3)
N1—C1—C2—C3	0.9 (3)	C5—C4—C9—C8	0.6 (3)
N3—N2—C3—C2	2.4 (3)	C3—C4—C9—C8	−179.14 (16)
N3—N2—C3—C4	−177.19 (15)	C7—C8—C9—N1	179.30 (17)
C1—C2—C3—N2	−179.34 (17)	C7—C8—C9—C4	−0.5 (3)
C1—C2—C3—C4	0.2 (3)	N2—N3—C10—C11	−179.76 (16)
N2—C3—C4—C5	−1.2 (3)	N3—C10—C11—C12	−179.33 (17)
C2—C3—C4—C5	179.21 (17)	N3—C10—C11—C16	0.7 (3)
N2—C3—C4—C9	178.48 (16)	C16—C11—C12—C13	−1.2 (3)
C2—C3—C4—C9	−1.1 (2)	C10—C11—C12—C13	178.81 (17)
C9—C4—C5—C6	−0.7 (3)	C11—C12—C13—C14	0.4 (3)
C3—C4—C5—C6	178.94 (17)	C11—C12—C13—C17	−178.30 (17)
C4—C5—C6—C7	0.8 (3)	C12—C13—C14—C15	0.4 (3)
C5—C6—C7—C8	−0.8 (3)	C17—C13—C14—C15	179.10 (19)
C5—C6—C7—Cl1	178.69 (14)	C13—C14—C15—C16	−0.4 (3)
C6—C7—C8—C9	0.6 (3)	C14—C15—C16—C11	−0.4 (3)
Cl1—C7—C8—C9	−178.84 (14)	C12—C11—C16—C15	1.2 (3)
C1—N1—C9—C4	0.0 (3)	C10—C11—C16—C15	−178.82 (19)
C1—N1—C9—C8	−179.86 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N4ⁱ	0.83 (3)	2.21 (3)	2.982 (3)	155 (3)
O1w—H2w···N1ⁱⁱ	0.86 (3)	1.99 (3)	2.828 (3)	164 (3)
N2—H2n···O1w	0.86 (3)	2.07 (3)	2.917 (2)	167 (3)
C5—H5···O1w	0.95	2.39	3.331 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁ClN₄·H₂O
M_r	324.76
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.7406 (2), 9.8587 (3), 10.2301 (2)
α, β, γ (°)	110.8897 (15), 93.4341 (16), 110.6766 (15)
V (Å³)	752.93 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.12 × 0.09 × 0.04

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.901, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	14600, 3425, 2902
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 1.10
No. of reflections	3425
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N4ⁱ	0.83 (3)	2.21 (3)	2.982 (3)	155 (3)
O1w—H2w···N1ⁱⁱ	0.86 (3)	1.99 (3)	2.828 (3)	164 (3)
N2—H2n···O1w	0.86 (3)	2.07 (3)	2.917 (2)	167 (3)
C5—H5···O1w	0.95	2.39	3.331 (3)	169

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

References

Andrade, A. A., Varotti, F. D., de Freitas, I. Q., de Souza, M. V. N., Vasconcelos, T. R. A., Boechat, N. & Krettli, A. U. (2007). Eur. J. Pharm. 558, 194–198. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cunico, W., Cechinel, C. A., Bonacorso, H. G., Martins, G. M. A. P., Zanetta, N., de Souza, M. V. N., Freitas, I. Q., Soares, R. P. P. & Krettli, A. U. (2006). Bioorg. Med. Chem. Lett. 16, 649–653. Web of Science CrossRef PubMed CAS Google Scholar
Elslager, E. F., Tendick, F. H. & Werbel, L. M. (1969). J. Med. Chem. 12, 600–607. CrossRef CAS PubMed Web of Science Google Scholar
Font, M., Monge, A., Ruiz, I. & Heras, B. (1997). Drug Des. Disc. 14, 259–272. CAS Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Kaiser, C. R., Pais, K. C., de Souza, M. V. N., Wardell, J. L., Wardell, S. M. S. V. & Tiekink, E. R. T. (2009). CrystEngComm, 11, 1133–1140. Web of Science CSD CrossRef CAS Google Scholar
Kaminsky, D. & Meltzer, R. I. (1968). J. Med. Chem. 11, 160–163. CrossRef CAS PubMed Web of Science Google Scholar
Musiol, R., Jampilek, J., Buchta, V., Silva, L., Halina, H., Podeszwa, B., Palka, A., Majerz-Maniecka, K., Oleksyn, B. & Polanski, J. (2006). Bioorg. Med. Chem. 14, 3592–3598. Web of Science CrossRef PubMed CAS Google Scholar
Nakamura, T., Oka, M., Aizawa, K., Soda, H., Fukuda, M., Terashi, K., Ikeda, K., Mizuta, Y., Noguchi, Y., Kimura, Y., Tsuruo, T. & Kohno, S. (1999). Biochem. Biophys. Res. Commun. 255, 618–624. Web of Science CrossRef PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Palmer, K. J., Holliday, S. M. & and Brogden, R. N. (1993). Drugs, 45, 430–475. CrossRef CAS PubMed Web of Science Google Scholar
Ridley, R. G. (2002). Nature (London), 415, 686–693. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, A. D. da, de Almeida, M. V., de Souza, M. V. N. & Couri, M. R. C. (2003). Curr. Med. Chem. 10, 21–39. Web of Science PubMed Google Scholar
Sloboda, A. E., Powell, D., Poletto, J. F., Pickett, W. C., Gibbons, J. J., Bell, D. H., Oronsky, A. L. & Kerwar, S. S. (1991). J. Rheumatol. 18, 855–860. PubMed CAS Web of Science Google Scholar
Souza, M. V. N. de (2005). Mini-Rev. Med. Chem. 5, 1009–1017. Google Scholar
Tanenbaum, L. & Tuffanelli, D. L. (1980). Arch. Dermatol. 116, 587–591. CrossRef CAS PubMed Web of Science Google Scholar
Warshakoon, N. C., Sheville, J., Bhatt, R. T., Ji, W., Mendez-Andino, J. L., Meyers, K. M., Kim, N., Wos, J. A., Mitchell, C., Paris, J. L., Pinney, B. B. O., Reizes, O. & Hu, X. E. (2006). Bioorg. Med. Chem. Lett. 16, 5207–5211. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar