4-Chloro­benzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate

Loh, W.-S.; Fun, H.-K.; Kayarmar, R.; Viveka, S.; Nagaraja, G.K.

doi:10.1107/S1600536811001577

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o407-o408

doi:10.1107/S1600536811001577

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4-Chlorobenzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate

Wan-Sin Loh,^a ‡ Hoong-Kun Fun,^a ^*§ Reshma Kayarmar,^b S. Viveka ^b and G. K. Nagaraja ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 27 December 2010; accepted 11 January 2011; online 15 January 2011)

In the title compound, C₂₁H₂₀ClN₅·H₂O, the 1H-imidazo[4,5-c]quinoline ring is approximately planar, with a maximum deviation of 0.0795 (7) Å, and it forms a dihedral angle of 7.65 (3)° with the chlorophenyl ring. In the crystal, the components are linked into chains along the a axis via intermolecular N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds. One of the H atoms of the water molecule is disordered over two positions with a site-occupancy ratio of 0.80 (4):0.20 (4).

Related literature

For background to quinolines and their microbial activity, see: El-Subbagh et al. (2000 ); Atwell et al. (1989 ); Kuo et al. (1993 ); Xia et al. (1998 ). For the biological activity of Schiff base hydrazones, see: Colins & Lyne (1970 ); Ochiai (1977 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see: Loh et al. (2011a ,b ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₀ClN₅·H₂O
M_r = 395.89
Monoclinic, P 2₁ /c
a = 10.4117 (3) Å
b = 18.2365 (6) Å
c = 11.9019 (3) Å
β = 117.809 (2)°
V = 1998.85 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.49 × 0.45 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.904, T_max = 0.963
39468 measured reflections
10411 independent reflections
8351 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.135
S = 1.04
10411 reflections
260 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.19 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯O1Wⁱ	0.874 (19)	2.559 (18)	3.2789 (13)	140.2 (14)
O1W—H1W1⋯N1ⁱⁱ	0.83	2.09	2.9178 (14)	173
C10—H10A⋯O1Wⁱⁱⁱ	0.93	2.52	3.3513 (16)	149
C18—H18B⋯O1Wⁱⁱⁱ	0.97	2.59	3.4776 (14)	153
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y, z+1; (iii) x, y, z-1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001577/is2658sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001577/is2658Isup2.hkl

checkCIF report

Comment top

Quinolines and their derivatives are important constituents of pharmacologically active synthetic compounds as these systems have been associated with a wide spectrum of biological properties (El-Subbagh et al., 2000) such as DNA binding capability (Atwell et al., 1989) and antitumor activities (Kuo et al., 1993; Xia et al., 1998). The study of Schiff base hydrazones has been growing because of their antimicrobial, anti-tuberculosis and anti-tumour activities (Colins & Lyne, 1970; Ochiai, 1977).

The asymmetric unit of the title compound, (Fig. 1), consists of one 4-chlorobenzaldehyde(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl) hydrazone molecule and one water molecule. One of the H atoms attached to the water molecule is disordered over two positions with the site occupancy ratio of 0.80 (4):0.20 (4). The 1H-imidazo[4,5-c]quinoline ring (C1–C6/N1/C7/C8/N3/C10/N2/C9) is approximately planar with a maximum deviation of 0.0795 (7) Å at atom C2 and it forms a dihedral angle of 7.65 (3)° with the chlorophenyl ring (Cl1/C11–C16) with maximum deviation of 0.0286 (3) Å at atom Cl1. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Loh et al., 2011a,b).

In the crystal packing (Fig. 2), the molecules are linked into chains along the a axis by the water molecules via intermolecular N4—H1N4···O1W, O1W—H1W1···N1, C10—H10A···O1W and C18—H18B···O1W hydrogen bonds (Table 1).

Related literature top

For background to quinolines and their microbial activity, see: El-Subbagh et al. (2000); Atwell et al. (1989); Kuo et al. (1993); Xia et al. (1998). For the biological activity of Schiff base hydrazones, see: Colins & Lyne (1970); Ochiai (1977). For bond-length data, see: Allen et al. (1987). For related structures, see: Loh et al. (2011a,b). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 4-hydrazino-1-isobutyl-1H-imidazo[4,5-c]quinoline (2.5 g, 0.0098 mole) and 4-chlorobenzaldehyde (1.38 g, 0.0098 mole) in absolute ethanol was refluxed for 4 h in the presence of acetic acid (1 ml). The product, 4-chlorobenzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone, was obtained after cooling and it was crystallized from absolute ethanol. Yield: 3.4 g (80%). Crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. The open bond indicates the minor component.
	Fig. 2. The crystal packing of the title compound, showing the chains along the a axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity. Only major component is shown.

4-Chlorobenzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate top

Crystal data top

C₂₁H₂₀ClN₅·H₂O	F(000) = 832
M_r = 395.89	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9978 reflections
a = 10.4117 (3) Å	θ = 4.0–37.5°
b = 18.2365 (6) Å	µ = 0.21 mm⁻¹
c = 11.9019 (3) Å	T = 100 K
β = 117.809 (2)°	Plate, yellow
V = 1998.85 (10) Å³	0.49 × 0.45 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	10411 independent reflections
Radiation source: fine-focus sealed tube	8351 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 37.6°, θ_min = 4.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.904, T_max = 0.963	k = −31→30
39468 measured reflections	l = −20→20

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0715P)² + 0.4845P] where P = (F_o² + 2F_c²)/3
10411 reflections	(Δ/σ)_max = 0.001
260 parameters	Δρ_max = 1.19 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₁H₂₀ClN₅·H₂O	V = 1998.85 (10) Å³
M_r = 395.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4117 (3) Å	µ = 0.21 mm⁻¹
b = 18.2365 (6) Å	T = 100 K
c = 11.9019 (3) Å	0.49 × 0.45 × 0.18 mm
β = 117.809 (2)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	10411 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	8351 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.963	R_int = 0.032
39468 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.19 e Å⁻³
10411 reflections	Δρ_min = −0.47 e Å⁻³
260 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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. 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 > σ(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	Occ. (<1)
Cl1	−0.37283 (3)	−0.053039 (16)	0.46655 (3)	0.03357 (7)
N1	0.00417 (7)	0.13498 (4)	0.01185 (6)	0.01373 (11)
N2	0.33923 (7)	0.14996 (4)	−0.08204 (7)	0.01514 (11)
N3	0.35384 (7)	0.06015 (4)	0.05254 (7)	0.01630 (12)
N4	0.13161 (8)	0.03567 (4)	0.13737 (7)	0.01564 (11)
N5	0.02778 (7)	0.02713 (4)	0.17545 (6)	0.01482 (11)
C1	0.09304 (8)	0.20371 (4)	−0.11917 (7)	0.01242 (11)
C2	0.06369 (8)	0.25958 (4)	−0.21028 (7)	0.01464 (12)
H2A	0.1260	0.2664	−0.2455	0.018*
C3	−0.05646 (8)	0.30406 (4)	−0.24743 (7)	0.01589 (12)
H3A	−0.0749	0.3407	−0.3075	0.019*
C4	−0.15108 (8)	0.29408 (4)	−0.19448 (8)	0.01637 (13)
H4A	−0.2297	0.3255	−0.2171	0.020*
C5	−0.12834 (8)	0.23813 (4)	−0.10935 (8)	0.01560 (12)
H5A	−0.1932	0.2314	−0.0768	0.019*
C6	−0.00740 (8)	0.19089 (4)	−0.07104 (7)	0.01287 (11)
C7	0.11700 (8)	0.09093 (4)	0.05390 (7)	0.01293 (11)
C8	0.22740 (8)	0.09992 (4)	0.01609 (7)	0.01314 (11)
C9	0.21572 (8)	0.15557 (4)	−0.06761 (7)	0.01280 (11)
C10	0.41677 (9)	0.09246 (4)	−0.00837 (8)	0.01736 (13)
H10A	0.5054	0.0774	−0.0017	0.021*
C11	0.04705 (9)	−0.02385 (4)	0.25628 (7)	0.01614 (13)
H11A	0.1279	−0.0543	0.2850	0.019*
C12	−0.05978 (9)	−0.03357 (4)	0.30283 (7)	0.01541 (12)
C13	−0.18721 (9)	0.00855 (4)	0.25432 (7)	0.01694 (13)
H13A	−0.2067	0.0415	0.1887	0.020*
C14	−0.28457 (10)	0.00168 (5)	0.30303 (8)	0.01947 (14)
H14A	−0.3690	0.0296	0.2704	0.023*
C15	−0.25383 (10)	−0.04775 (5)	0.40152 (8)	0.02080 (15)
C16	−0.13059 (11)	−0.09132 (5)	0.44958 (8)	0.02182 (15)
H16A	−0.1126	−0.1248	0.5142	0.026*
C17	−0.03391 (10)	−0.08415 (5)	0.39943 (8)	0.01941 (14)
H17A	0.0488	−0.1134	0.4306	0.023*
C18	0.38977 (9)	0.19795 (4)	−0.15243 (8)	0.01655 (13)
H18A	0.3124	0.2040	−0.2385	0.020*
H18B	0.4711	0.1749	−0.1570	0.020*
C19	0.43656 (8)	0.27358 (4)	−0.09030 (8)	0.01657 (13)
H19A	0.3546	0.2959	−0.0839	0.020*
C20	0.56378 (11)	0.26719 (6)	0.04269 (9)	0.02498 (17)
H20A	0.5932	0.3153	0.0784	0.037*
H20B	0.6435	0.2433	0.0383	0.037*
H20C	0.5349	0.2390	0.0952	0.037*
C21	0.47505 (11)	0.32187 (6)	−0.17470 (10)	0.02624 (18)
H21A	0.5008	0.3700	−0.1382	0.039*
H21B	0.3929	0.3253	−0.2576	0.039*
H21C	0.5556	0.3008	−0.1815	0.039*
H1N4	0.2039 (19)	0.0049 (9)	0.1601 (16)	0.035 (4)*
O1W	0.70320 (9)	0.09494 (4)	0.93489 (12)	0.0421 (3)
H1W1	0.7912	0.1025	0.9595	0.063*
H2WA	0.6633	0.0764	0.8603	0.063*	0.80 (4)
H2WB	0.6915	0.0492	0.9405	0.063*	0.20 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03921 (14)	0.03795 (14)	0.03987 (14)	−0.00160 (10)	0.03211 (12)	0.00615 (10)
N1	0.0138 (2)	0.0145 (2)	0.0160 (2)	0.00128 (19)	0.0096 (2)	0.0020 (2)
N2	0.0138 (2)	0.0149 (3)	0.0216 (3)	0.0012 (2)	0.0124 (2)	0.0016 (2)
N3	0.0137 (3)	0.0151 (3)	0.0227 (3)	0.0020 (2)	0.0107 (2)	0.0021 (2)
N4	0.0154 (3)	0.0166 (3)	0.0188 (3)	0.0029 (2)	0.0112 (2)	0.0044 (2)
N5	0.0165 (3)	0.0153 (3)	0.0161 (3)	−0.0005 (2)	0.0104 (2)	0.0009 (2)
C1	0.0114 (3)	0.0139 (3)	0.0136 (3)	0.0000 (2)	0.0072 (2)	0.0001 (2)
C2	0.0139 (3)	0.0168 (3)	0.0152 (3)	0.0000 (2)	0.0085 (2)	0.0017 (2)
C3	0.0142 (3)	0.0177 (3)	0.0162 (3)	0.0010 (2)	0.0074 (2)	0.0034 (2)
C4	0.0134 (3)	0.0168 (3)	0.0196 (3)	0.0019 (2)	0.0083 (2)	0.0032 (2)
C5	0.0134 (3)	0.0169 (3)	0.0197 (3)	0.0020 (2)	0.0103 (2)	0.0029 (2)
C6	0.0122 (3)	0.0142 (3)	0.0147 (3)	0.0002 (2)	0.0084 (2)	0.0004 (2)
C7	0.0132 (3)	0.0136 (3)	0.0141 (3)	−0.0003 (2)	0.0081 (2)	−0.0001 (2)
C8	0.0121 (3)	0.0132 (3)	0.0163 (3)	0.0004 (2)	0.0084 (2)	0.0003 (2)
C9	0.0120 (3)	0.0138 (3)	0.0154 (3)	−0.0003 (2)	0.0087 (2)	−0.0003 (2)
C10	0.0149 (3)	0.0157 (3)	0.0258 (3)	0.0025 (2)	0.0132 (3)	0.0025 (3)
C11	0.0175 (3)	0.0161 (3)	0.0162 (3)	0.0004 (2)	0.0090 (2)	0.0025 (2)
C12	0.0187 (3)	0.0150 (3)	0.0142 (3)	−0.0020 (2)	0.0091 (2)	0.0007 (2)
C13	0.0193 (3)	0.0173 (3)	0.0167 (3)	−0.0005 (2)	0.0105 (3)	0.0020 (2)
C14	0.0211 (3)	0.0198 (3)	0.0218 (3)	−0.0012 (3)	0.0136 (3)	0.0011 (3)
C15	0.0261 (4)	0.0216 (3)	0.0209 (3)	−0.0049 (3)	0.0162 (3)	−0.0001 (3)
C16	0.0277 (4)	0.0224 (4)	0.0189 (3)	−0.0022 (3)	0.0138 (3)	0.0045 (3)
C17	0.0228 (4)	0.0192 (3)	0.0175 (3)	0.0001 (3)	0.0104 (3)	0.0043 (3)
C18	0.0162 (3)	0.0188 (3)	0.0200 (3)	0.0003 (2)	0.0130 (3)	0.0017 (2)
C19	0.0139 (3)	0.0177 (3)	0.0198 (3)	0.0002 (2)	0.0094 (3)	0.0031 (2)
C20	0.0216 (4)	0.0287 (4)	0.0210 (4)	−0.0013 (3)	0.0070 (3)	0.0022 (3)
C21	0.0255 (4)	0.0260 (4)	0.0297 (4)	−0.0023 (3)	0.0150 (4)	0.0094 (3)
O1W	0.0217 (3)	0.0222 (3)	0.0865 (8)	0.0064 (3)	0.0287 (4)	0.0188 (4)

Geometric parameters (Å, º) top

Cl1—C15	1.7430 (9)	C11—H11A	0.9300
N1—C7	1.3143 (10)	C12—C17	1.3985 (11)
N1—C6	1.3842 (9)	C12—C13	1.4032 (12)
N2—C10	1.3638 (10)	C13—C14	1.3884 (11)
N2—C9	1.3782 (9)	C13—H13A	0.9300
N2—C18	1.4684 (10)	C14—C15	1.3924 (12)
N3—C10	1.3210 (10)	C14—H14A	0.9300
N3—C8	1.3836 (10)	C15—C16	1.3857 (14)
N4—N5	1.3622 (9)	C16—C17	1.3955 (12)
N4—C7	1.3728 (10)	C16—H16A	0.9300
N4—H1N4	0.875 (18)	C17—H17A	0.9300
N5—C11	1.2845 (10)	C18—C19	1.5330 (12)
C1—C2	1.4135 (10)	C18—H18A	0.9700
C1—C6	1.4267 (10)	C18—H18B	0.9700
C1—C9	1.4308 (10)	C19—C20	1.5222 (12)
C2—C3	1.3793 (11)	C19—C21	1.5233 (12)
C2—H2A	0.9300	C19—H19A	0.9800
C3—C4	1.4072 (11)	C20—H20A	0.9600
C3—H3A	0.9300	C20—H20B	0.9600
C4—C5	1.3783 (11)	C20—H20C	0.9600
C4—H4A	0.9300	C21—H21A	0.9600
C5—C6	1.4142 (10)	C21—H21B	0.9600
C5—H5A	0.9300	C21—H21C	0.9600
C7—C8	1.4259 (10)	O1W—H1W1	0.8330
C8—C9	1.3872 (10)	O1W—H2WA	0.8554
C10—H10A	0.9300	O1W—H2WB	0.8508
C11—C12	1.4665 (11)

C7—N1—C6	119.13 (6)	C17—C12—C11	120.07 (7)
C10—N2—C9	106.49 (6)	C13—C12—C11	121.10 (7)
C10—N2—C18	124.26 (6)	C14—C13—C12	120.87 (7)
C9—N2—C18	129.08 (6)	C14—C13—H13A	119.6
C10—N3—C8	103.72 (6)	C12—C13—H13A	119.6
N5—N4—C7	119.18 (6)	C13—C14—C15	118.96 (8)
N5—N4—H1N4	121.7 (12)	C13—C14—H14A	120.5
C7—N4—H1N4	119.0 (12)	C15—C14—H14A	120.5
C11—N5—N4	117.46 (7)	C16—C15—C14	121.57 (8)
C2—C1—C6	119.31 (6)	C16—C15—Cl1	119.88 (6)
C2—C1—C9	126.97 (6)	C14—C15—Cl1	118.54 (7)
C6—C1—C9	113.71 (6)	C15—C16—C17	118.91 (8)
C3—C2—C1	120.60 (7)	C15—C16—H16A	120.5
C3—C2—H2A	119.7	C17—C16—H16A	120.5
C1—C2—H2A	119.7	C16—C17—C12	120.84 (8)
C2—C3—C4	120.01 (7)	C16—C17—H17A	119.6
C2—C3—H3A	120.0	C12—C17—H17A	119.6
C4—C3—H3A	120.0	N2—C18—C19	112.26 (6)
C5—C4—C3	120.59 (7)	N2—C18—H18A	109.2
C5—C4—H4A	119.7	C19—C18—H18A	109.2
C3—C4—H4A	119.7	N2—C18—H18B	109.2
C4—C5—C6	120.65 (7)	C19—C18—H18B	109.2
C4—C5—H5A	119.7	H18A—C18—H18B	107.9
C6—C5—H5A	119.7	C20—C19—C21	111.16 (7)
N1—C6—C5	116.55 (6)	C20—C19—C18	111.05 (7)
N1—C6—C1	124.78 (6)	C21—C19—C18	108.91 (7)
C5—C6—C1	118.67 (6)	C20—C19—H19A	108.5
N1—C7—N4	120.12 (6)	C21—C19—H19A	108.5
N1—C7—C8	121.23 (7)	C18—C19—H19A	108.5
N4—C7—C8	118.64 (6)	C19—C20—H20A	109.5
N3—C8—C9	111.13 (6)	C19—C20—H20B	109.5
N3—C8—C7	129.05 (7)	H20A—C20—H20B	109.5
C9—C8—C7	119.81 (6)	C19—C20—H20C	109.5
N2—C9—C8	105.12 (6)	H20A—C20—H20C	109.5
N2—C9—C1	133.65 (7)	H20B—C20—H20C	109.5
C8—C9—C1	121.23 (6)	C19—C21—H21A	109.5
N3—C10—N2	113.54 (7)	C19—C21—H21B	109.5
N3—C10—H10A	123.2	H21A—C21—H21B	109.5
N2—C10—H10A	123.2	C19—C21—H21C	109.5
N5—C11—C12	119.30 (7)	H21A—C21—H21C	109.5
N5—C11—H11A	120.3	H21B—C21—H21C	109.5
C12—C11—H11A	120.3	H1W1—O1W—H2WA	110.7
C17—C12—C13	118.81 (7)	H1W1—O1W—H2WB	107.9

C7—N4—N5—C11	−178.12 (7)	N3—C8—C9—N2	−0.42 (9)
C6—C1—C2—C3	3.55 (11)	C7—C8—C9—N2	178.87 (7)
C9—C1—C2—C3	−177.20 (7)	N3—C8—C9—C1	179.51 (7)
C1—C2—C3—C4	0.05 (12)	C7—C8—C9—C1	−1.21 (11)
C2—C3—C4—C5	−2.71 (12)	C2—C1—C9—N2	3.78 (14)
C3—C4—C5—C6	1.68 (12)	C6—C1—C9—N2	−176.94 (8)
C7—N1—C6—C5	−177.76 (7)	C2—C1—C9—C8	−176.12 (7)
C7—N1—C6—C1	2.14 (11)	C6—C1—C9—C8	3.17 (10)
C4—C5—C6—N1	−178.17 (7)	C8—N3—C10—N2	−0.36 (9)
C4—C5—C6—C1	1.94 (11)	C9—N2—C10—N3	0.12 (10)
C2—C1—C6—N1	175.61 (7)	C18—N2—C10—N3	175.72 (7)
C9—C1—C6—N1	−3.74 (10)	N4—N5—C11—C12	178.17 (7)
C2—C1—C6—C5	−4.50 (11)	N5—C11—C12—C17	−174.05 (8)
C9—C1—C6—C5	176.15 (7)	N5—C11—C12—C13	4.30 (12)
C6—N1—C7—N4	179.21 (7)	C17—C12—C13—C14	1.54 (12)
C6—N1—C7—C8	0.24 (11)	C11—C12—C13—C14	−176.82 (8)
N5—N4—C7—N1	0.18 (11)	C12—C13—C14—C15	0.15 (13)
N5—N4—C7—C8	179.17 (7)	C13—C14—C15—C16	−1.62 (13)
C10—N3—C8—C9	0.48 (9)	C13—C14—C15—Cl1	177.25 (7)
C10—N3—C8—C7	−178.72 (8)	C14—C15—C16—C17	1.32 (14)
N1—C7—C8—N3	178.48 (7)	Cl1—C15—C16—C17	−177.53 (7)
N4—C7—C8—N3	−0.50 (12)	C15—C16—C17—C12	0.44 (13)
N1—C7—C8—C9	−0.66 (11)	C13—C12—C17—C16	−1.84 (12)
N4—C7—C8—C9	−179.64 (7)	C11—C12—C17—C16	176.54 (8)
C10—N2—C9—C8	0.18 (8)	C10—N2—C18—C19	−105.84 (9)
C18—N2—C9—C8	−175.14 (7)	C9—N2—C18—C19	68.72 (10)
C10—N2—C9—C1	−179.73 (8)	N2—C18—C19—C20	62.01 (9)
C18—N2—C9—C1	4.95 (14)	N2—C18—C19—C21	−175.26 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···O1Wⁱ	0.874 (19)	2.559 (18)	3.2789 (13)	140.2 (14)
O1W—H1W1···N1ⁱⁱ	0.83	2.09	2.9178 (14)	173
C10—H10A···O1Wⁱⁱⁱ	0.93	2.52	3.3513 (16)	149
C18—H18B···O1Wⁱⁱⁱ	0.97	2.59	3.4776 (14)	153

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀ClN₅·H₂O
M_r	395.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.4117 (3), 18.2365 (6), 11.9019 (3)
β (°)	117.809 (2)
V (Å³)	1998.85 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.49 × 0.45 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.904, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	39468, 10411, 8351
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.858

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.135, 1.04
No. of reflections	10411
No. of parameters	260
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.19, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···O1Wⁱ	0.874 (19)	2.559 (18)	3.2789 (13)	140.2 (14)
O1W—H1W1···N1ⁱⁱ	0.83	2.09	2.9178 (14)	173
C10—H10A···O1Wⁱⁱⁱ	0.93	2.52	3.3513 (16)	149
C18—H18B···O1Wⁱⁱⁱ	0.97	2.59	3.4776 (14)	153

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

Footnotes

‡Thomson Reuters ResearcherID: C-7581-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a Research Fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Atwell, G. J., Baguley, B. C. & Denny, W. A. (1989). J. Med. Chem. 32, 396–401. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Colins, C. H. & Lyne, P. M. (1970). Microbiological Methods. Baltimore: University Park Press. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A. & Al-Obaid, A. M. (2000). J. Med. Chem. 43, 2915–2921. Web of Science CrossRef PubMed CAS Google Scholar
Kuo, S. C., Lee, H. Z., Juang, J. P., Lin, Y. T., Wu, T. S., Chang, J. J., Lednicer, D., Paull, K. D., Lin, C. M., Hamel, E. & Lee, K. H. (1993). J. Med. Chem. 36, 1146–1156. CrossRef CAS PubMed Web of Science Google Scholar
Loh, W.-S., Fun, H.-K., Kayarmar, R., Viveka, S. & Nagaraja, G. K. (2011a). Acta Cryst. E67, o405. Web of Science CSD CrossRef IUCr Journals Google Scholar
Loh, W.-S., Fun, H.-K., Kayarmar, R., Viveka, S. & Nagaraja, G. K. (2011b). Acta Cryst. E67, o406. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ochiai, E. (1977). In Bioinorganic Chemistry. Boston: Allyn and Bacon. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, Y., Yang, Z. Y., Xia, P., Bastow, K. F., Tachibana, Y., Kuo, S. C., Hamel, E., Hackl, T. & Lee, K. H. (1998). J. Med. Chem. 41, 1155–1162. Web of Science CrossRef CAS PubMed Google Scholar

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