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

In the title compound, C(21)H(20)ClN(5)·H(2)O, 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 chloro-phenyl ring. In the crystal, the components are linked into chains along the a axis via inter-molecular N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds. One of the H atoms of the water mol-ecule 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. (2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H20ClN5·H2O

M = 395.89

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.04

10411 reflections

260 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.19 e Å−3

Δρmin = −0.47 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H20ClN5·H2O	F(000) = 832
Mr = 395.89	Dx = 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

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

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(Fo2) + (0.0715P)2 + 0.4845P] where P = (Fo2 + 2Fc2)/3
10411 reflections	(Δ/σ)max = 0.001
260 parameters	Δρmax = 1.19 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) ; (ii) ; (iii) .