2-(8-Bromo­imidazo[1,2-a]pyridin-2-yl)-N′-[(E)-4-diethyl­amino-2-hy­droxy­benzyl­idene]acetohydrazide dihydrate

Fun, H.-K.; Loh, W.-S.; Shenvi, S.; Isloor, A.M.; Hegde, G.

doi:10.1107/S160053681200685X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o816-o817

doi:10.1107/S160053681200685X

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2-(8-Bromoimidazo[1,2-a]pyridin-2-yl)-N′-[(E)-4-diethylamino-2-hydroxybenzylidene]acetohydrazide dihydrate

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § Seema Shenvi,^b Arun M. Isloor ^b and Gurumurthy Hegde ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Electronics Division, Department of Chemistry, National Institute of Technology - Karnataka, Surathkal, Mangalore 575 025, India, and ^cFaculty of Industrial Science and Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, 26300 Gambang, Kuantan, Pahang Darul Makmur, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 15 February 2012; accepted 15 February 2012; online 24 February 2012)

In the title compound, C₂₀H₂₂BrN₅O₂·2H₂O, the Schiff base molecule exists in an E conformation with respect to the acyclic C=N bond. An S(6) ring motif is formed via an intramolecular O—H⋯N hydrogen bond. The dihedral angle between the imidazo[1,2-a]pyridine system and the benzene ring is 84.62 (5)°. In the crystal, N—H⋯O, O—H⋯O, O—H⋯N, C—H⋯O and C—H⋯Br hydrogen bonds link the molecules into a three-dimensional network. The crystal packing is further stabilized by C—H⋯π and π–π interactions [centroid–centroid distance = 3.5365 (7) Å].

Related literature

For background to and applications of hydrazones, see: Seleem et al. (2011 ); Rollas & Küçükgüzel (2007 ). For background to and applications of imidazopyridine, see: Ertepinarl et al. (1995 ); Liang et al. (2007 ); Hamdouchi et al. (1999 ); Gudmundsson & Johns (2007 ); Biftu et al. (2006 ); Fisher & Lusi (1972 ); Bochis et al. (1981 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₂₂BrN₅O₂·2H₂O
M_r = 480.37
Triclinic, $[P \overline 1]$
a = 8.4370 (4) Å
b = 10.6711 (5) Å
c = 11.7559 (5) Å
α = 92.914 (1)°
β = 96.949 (1)°
γ = 93.978 (1)°
V = 1046.23 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 100 K
0.37 × 0.20 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.529, T_max = 0.869
22937 measured reflections
6491 independent reflections
5841 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.077
S = 1.05
6491 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/N2/C6/C7 ring and Cg3 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O2Wⁱ	0.894 (17)	1.908 (17)	2.7956 (15)	171.7 (17)
O2—H1O2⋯O1Wⁱⁱ	0.87 (3)	2.42 (3)	2.9423 (15)	119 (2)
O2—H1O2⋯N4	0.87 (3)	1.99 (3)	2.7181 (16)	142 (2)
O1W—H1W1⋯N1	0.86 (2)	1.98 (2)	2.8315 (14)	176 (2)
O1W—H2W1⋯O1ⁱⁱⁱ	0.85 (3)	1.92 (2)	2.7361 (14)	162 (2)
O2W—H1W2⋯O1Wⁱ	0.80 (2)	2.08 (2)	2.8311 (15)	157 (2)
O2W—H2W2⋯O1W	0.86 (2)	1.87 (2)	2.7245 (15)	172.9 (17)
C5—H5A⋯O1^iv	0.93	2.50	3.3121 (17)	146
C10—H10A⋯O2Wⁱ	0.93	2.54	3.3256 (17)	142
C17—H17B⋯Br1^v	0.97	2.85	3.6569 (15)	142
C3—H3A⋯Cg3^vi	0.93	2.61	3.4734 (15)	154
C17—H17A⋯Cg1^vii	0.97	2.70	3.5863 (15)	152
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) x+1, y, z; (iv) -x, -y+1, -z+1; (v) -x+1, -y, -z+2; (vi) x+1, y+1, z; (vii) -x, -y, -z+2.

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/S160053681200685X/bq2340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200685X/bq2340Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200685X/bq2340Isup3.cml

checkCIF report

Comment top

Hydrazones constitute an important class of biologically active drug molecules (Seleem et al., 2011) which has attracted attention of medicinal chemists due to their wide range of pharmacological properties. These compounds are being synthesized as drugs by many researchers in order to combat diseases with minimal toxicity and maximal effects. A number of hydrazone derivatives have been reported to exert notably antimicrobial, antihypertensive, anticonvulsant, analgesic, anti-inflammatory, antituberculosis, antitumoral, antiproliferative and antimalarial activities (Rollas & Küçükgüzel, 2007). Imidazopyridine is the fundamental heterocyclic component of principal anthelmintic drugs. In addition, the imidazopyridine ring possesses many anti-infective properties including antibacterial (Ertepinarl et al., 1995; Liang et al., 2007), antiviral (Hamdouchi et al., 1999; Gudmundsson & Johns, 2007), antiprotozoal (Biftu et al., 2006) and especially anthelmintic (Fisher & Lusi, 1972; Bochis et al., 1981) activities. Therefore, the imidazopyridine ring could replace the benzimidazole ring in the design and the development of new anthelmintic agents. In view of its biological importance, we hereby report the crystal structure of (I).

The title compound (Fig. 1) consists of one 2-(8-bromoimidazo[1,2-a]pyridin-3-yl)-N'-{(E)- [4-(diethylamino)-2-hydroxyphenyl]methylidene}acetohydrazide molecule and two water molecules. The Schiff base molecule exists in an E configuration with respect to the acyclic C═N bond. An S(6) ring motif (Bernstein et al., 1995) is formed via the intramolecular O2—H1O2···N4 hydrogen bond. The dihedral angle between the imidazo[1,2-a]pyridine (C1–C5/N2/C6/C7/N1) and the benzene (C11–C16) rings is 84.62 (5)°.

In the crystal packing (Fig. 2), intermolecular N3—H1N3···O2W, O2—H1O2···O1W, O2—H1O2···N4, O1W—H1W1···N1, O1W—H2W1···O1, O2W—H1W2···O1W, O2W—H2W2···O1W, C5—H5A···O1, C10—H10A···O2W and C17—H17B···Br1 hydrogen bonds link the molecules into a three-dimensional network. The crystal packing is further stabilized by C—H···π interactions, involving the 1H-imidazole (N1/C1/N2/C6/C7; Cg1; Table 1) and benzene (Cg3; Table 1) rings. Weak π–π interactions were observed involving 1H-imidazole, pyridine (N2/C1–C5; Cg2) and benzene rings. [Cg1···Cg1 = 3.5365 (7) Å; symmetry code: 1 - x, 1 - y, 1 - z; Cg1···Cg2 = 3.6210 (7) Å; symmetry code: 1 - x, 1 - y, 1 - z; Cg3···Cg3 = 3.6253 (8) Å; symmetry code: -x, -y, 2 - z].

Related literature top

For background to and applications of hydrazones, see: Seleem et al. (2011); Rollas & Küçükgüzel (2007). For background to and applications of imidazopyridine, see: Ertepinarl et al. (1995); Liang et al. (2007); Hamdouchi et al. (1999); Gudmundsson & Johns (2007); Biftu et al. (2006); Fisher & Lusi (1972); Bochis et al. (1981). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The mixture of 2-(8-bromoimidazo[1,2-a]pyridine-3-yl)acetohydrazide (200 mg, 0.00074 mol), 4-(diethylamino)-2-hydroxy benzaldehyde (143.6 mg, 0.00074 mol) and a catalytic quantity of acetic acid (0.1 ml) and ethanol (10 ml) was stirred overnight at 90°C. On cooling, orange plate-shaped crystals of the product begins to separate. It was collected by filtration and recrystallized from ethanol. Yield: 307.7 mg, 93.2%. m.p. 401–402 K.

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. Dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing the three-dimensional network. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

2-(8-Bromoimidazo[1,2-a]pyridin-2-yl)-N'-[(E)- 4-diethylamino-2-hydroxybenzylidene]acetohydrazide dihydrate top

Crystal data top

C₂₀H₂₂BrN₅O₂·2H₂O	Z = 2
M_r = 480.37	F(000) = 496
Triclinic, P1	D_x = 1.525 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4370 (4) Å	Cell parameters from 9983 reflections
b = 10.6711 (5) Å	θ = 2.4–30.9°
c = 11.7559 (5) Å	µ = 2.00 mm⁻¹
α = 92.914 (1)°	T = 100 K
β = 96.949 (1)°	Plate, orange
γ = 93.978 (1)°	0.37 × 0.20 × 0.07 mm
V = 1046.23 (8) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	6491 independent reflections
Radiation source: fine-focus sealed tube	5841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 30.9°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.529, T_max = 0.869	k = −15→15
22937 measured reflections	l = −16→16

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0455P)² + 0.2952P] where P = (F_o² + 2F_c²)/3
6491 reflections	(Δ/σ)_max = 0.002
297 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₂₂BrN₅O₂·2H₂O	γ = 93.978 (1)°
M_r = 480.37	V = 1046.23 (8) Å³
Triclinic, P1	Z = 2
a = 8.4370 (4) Å	Mo Kα radiation
b = 10.6711 (5) Å	µ = 2.00 mm⁻¹
c = 11.7559 (5) Å	T = 100 K
α = 92.914 (1)°	0.37 × 0.20 × 0.07 mm
β = 96.949 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6491 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5841 reflections with I > 2σ(I)
T_min = 0.529, T_max = 0.869	R_int = 0.023
22937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.63 e Å⁻³
6491 reflections	Δρ_min = −0.24 e Å⁻³
297 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
Br1	0.789019 (15)	0.424051 (13)	0.748329 (12)	0.02141 (5)
O1	−0.05933 (11)	0.23815 (10)	0.52050 (9)	0.02047 (19)
O2	−0.26058 (13)	0.04472 (10)	0.79255 (9)	0.0227 (2)
N1	0.44340 (12)	0.35221 (10)	0.59413 (9)	0.01348 (19)
N2	0.35279 (12)	0.54369 (10)	0.61740 (9)	0.01344 (19)
N3	0.10753 (13)	0.09994 (10)	0.60467 (9)	0.01444 (19)
N4	−0.00110 (13)	0.05569 (10)	0.67606 (9)	0.0150 (2)
N5	−0.25929 (13)	−0.22618 (11)	1.10154 (9)	0.0164 (2)
C1	0.47756 (14)	0.46769 (11)	0.64404 (10)	0.0127 (2)
C2	0.61422 (15)	0.52232 (12)	0.71616 (11)	0.0147 (2)
C3	0.62011 (16)	0.64472 (13)	0.75761 (11)	0.0174 (2)
H3A	0.7093	0.6799	0.8059	0.021*
C4	0.48898 (17)	0.71799 (12)	0.72639 (11)	0.0182 (2)
H4A	0.4935	0.8015	0.7542	0.022*
C5	0.35760 (16)	0.66812 (12)	0.65681 (11)	0.0175 (2)
H5A	0.2725	0.7167	0.6361	0.021*
C6	0.23518 (14)	0.47094 (12)	0.54616 (11)	0.0153 (2)
H6A	0.1371	0.4957	0.5135	0.018*
C7	0.29303 (14)	0.35486 (12)	0.53359 (10)	0.0134 (2)
C8	0.20850 (15)	0.23836 (12)	0.46996 (11)	0.0155 (2)
H8A	0.2831	0.1737	0.4649	0.019*
H8B	0.1674	0.2574	0.3926	0.019*
C9	0.07088 (14)	0.19108 (12)	0.53330 (11)	0.0143 (2)
C10	0.05212 (15)	−0.02976 (12)	0.74143 (11)	0.0158 (2)
H10A	0.1519	−0.0582	0.7326	0.019*
C11	−0.03602 (15)	−0.08324 (12)	0.82756 (11)	0.0146 (2)
C12	0.03051 (15)	−0.17581 (13)	0.89465 (12)	0.0175 (2)
H12A	0.1274	−0.2048	0.8788	0.021*
C13	−0.04169 (15)	−0.22574 (12)	0.98328 (11)	0.0173 (2)
H13A	0.0055	−0.2883	1.0247	0.021*
C14	−0.18834 (15)	−0.18158 (12)	1.01136 (10)	0.0144 (2)
C15	−0.25764 (15)	−0.08989 (12)	0.94303 (11)	0.0156 (2)
H15A	−0.3549	−0.0610	0.9582	0.019*
C16	−0.18382 (15)	−0.04205 (12)	0.85370 (11)	0.0147 (2)
C17	−0.19118 (17)	−0.32564 (13)	1.16815 (12)	0.0196 (2)
H17A	−0.2326	−0.3243	1.2416	0.024*
H17B	−0.0760	−0.3076	1.1831	0.024*
C18	−0.2262 (2)	−0.45760 (14)	1.11027 (14)	0.0265 (3)
H18A	−0.1691	−0.5164	1.1555	0.040*
H18B	−0.1926	−0.4586	1.0351	0.040*
H18C	−0.3391	−0.4808	1.1038	0.040*
C19	−0.41481 (16)	−0.18615 (13)	1.12605 (11)	0.0186 (2)
H19A	−0.4149	−0.0958	1.1202	0.022*
H19B	−0.4286	−0.2039	1.2045	0.022*
C20	−0.55683 (17)	−0.25000 (16)	1.04598 (13)	0.0252 (3)
H20A	−0.6542	−0.2176	1.0652	0.038*
H20B	−0.5615	−0.3391	1.0544	0.038*
H20C	−0.5440	−0.2334	0.9680	0.038*
O1W	0.64543 (12)	0.15365 (9)	0.57170 (9)	0.01893 (19)
O2W	0.60246 (12)	0.01353 (10)	0.36855 (10)	0.01989 (19)
H1N3	0.205 (2)	0.0710 (17)	0.6120 (15)	0.018 (4)*
H1O2	−0.209 (3)	0.069 (3)	0.737 (2)	0.058 (8)*
H1W1	0.587 (3)	0.215 (2)	0.582 (2)	0.041 (6)*
H2W1	0.742 (3)	0.181 (2)	0.5720 (18)	0.031 (5)*
H1W2	0.518 (3)	−0.026 (2)	0.369 (2)	0.041 (6)*
H2W2	0.608 (2)	0.060 (2)	0.4315 (18)	0.026 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01455 (7)	0.02522 (8)	0.02311 (8)	0.00475 (5)	−0.00432 (5)	−0.00016 (5)
O1	0.0123 (4)	0.0243 (5)	0.0255 (5)	0.0016 (3)	0.0027 (4)	0.0083 (4)
O2	0.0220 (5)	0.0254 (5)	0.0236 (5)	0.0075 (4)	0.0069 (4)	0.0106 (4)
N1	0.0117 (4)	0.0156 (5)	0.0132 (5)	0.0004 (4)	0.0019 (4)	0.0016 (4)
N2	0.0121 (4)	0.0152 (5)	0.0133 (5)	0.0009 (3)	0.0018 (4)	0.0027 (4)
N3	0.0107 (4)	0.0166 (5)	0.0165 (5)	−0.0009 (4)	0.0041 (4)	0.0021 (4)
N4	0.0126 (4)	0.0178 (5)	0.0147 (5)	−0.0017 (4)	0.0037 (4)	0.0009 (4)
N5	0.0165 (5)	0.0194 (5)	0.0136 (5)	0.0012 (4)	0.0030 (4)	0.0031 (4)
C1	0.0115 (5)	0.0154 (5)	0.0115 (5)	0.0013 (4)	0.0022 (4)	0.0031 (4)
C2	0.0130 (5)	0.0177 (6)	0.0131 (5)	0.0007 (4)	0.0007 (4)	0.0020 (4)
C3	0.0179 (6)	0.0194 (6)	0.0138 (5)	−0.0021 (4)	0.0005 (4)	0.0001 (4)
C4	0.0229 (6)	0.0151 (5)	0.0167 (6)	0.0017 (4)	0.0036 (5)	0.0013 (4)
C5	0.0199 (6)	0.0156 (6)	0.0178 (6)	0.0040 (4)	0.0036 (5)	0.0036 (4)
C6	0.0109 (5)	0.0197 (6)	0.0148 (5)	0.0000 (4)	−0.0001 (4)	0.0026 (4)
C7	0.0118 (5)	0.0171 (5)	0.0115 (5)	−0.0009 (4)	0.0030 (4)	0.0024 (4)
C8	0.0136 (5)	0.0188 (6)	0.0140 (5)	−0.0030 (4)	0.0039 (4)	0.0004 (4)
C9	0.0122 (5)	0.0160 (5)	0.0141 (5)	−0.0030 (4)	0.0017 (4)	0.0001 (4)
C10	0.0129 (5)	0.0173 (6)	0.0169 (6)	−0.0007 (4)	0.0024 (4)	0.0003 (4)
C11	0.0131 (5)	0.0164 (5)	0.0139 (5)	−0.0013 (4)	0.0010 (4)	0.0009 (4)
C12	0.0132 (5)	0.0200 (6)	0.0193 (6)	0.0014 (4)	0.0017 (4)	0.0029 (5)
C13	0.0154 (5)	0.0187 (6)	0.0176 (6)	0.0012 (4)	0.0004 (4)	0.0041 (4)
C14	0.0155 (5)	0.0152 (5)	0.0113 (5)	−0.0022 (4)	−0.0003 (4)	−0.0002 (4)
C15	0.0145 (5)	0.0173 (6)	0.0152 (6)	0.0010 (4)	0.0023 (4)	0.0007 (4)
C16	0.0144 (5)	0.0150 (5)	0.0144 (5)	−0.0004 (4)	0.0008 (4)	0.0007 (4)
C17	0.0227 (6)	0.0207 (6)	0.0158 (6)	0.0017 (5)	0.0024 (5)	0.0040 (5)
C18	0.0312 (8)	0.0201 (7)	0.0288 (8)	0.0007 (5)	0.0058 (6)	0.0029 (5)
C19	0.0193 (6)	0.0230 (6)	0.0145 (6)	0.0023 (5)	0.0055 (5)	0.0016 (5)
C20	0.0177 (6)	0.0342 (8)	0.0235 (7)	−0.0006 (5)	0.0040 (5)	−0.0005 (6)
O1W	0.0137 (4)	0.0173 (4)	0.0263 (5)	0.0007 (3)	0.0043 (4)	0.0026 (4)
O2W	0.0150 (4)	0.0182 (4)	0.0270 (5)	0.0005 (3)	0.0057 (4)	0.0000 (4)

Geometric parameters (Å, º) top

Br1—C2	1.8809 (13)	C8—H8B	0.9700
O1—C9	1.2354 (16)	C10—C11	1.4444 (17)
O2—C16	1.3534 (16)	C10—H10A	0.9300
O2—H1O2	0.87 (3)	C11—C12	1.4007 (18)
N1—C1	1.3350 (16)	C11—C16	1.4134 (17)
N1—C7	1.3804 (16)	C12—C13	1.3804 (18)
N2—C5	1.3802 (16)	C12—H12A	0.9300
N2—C6	1.3837 (16)	C13—C14	1.4232 (18)
N2—C1	1.3887 (15)	C13—H13A	0.9300
N3—C9	1.3443 (17)	C14—C15	1.4108 (17)
N3—N4	1.3906 (14)	C15—C16	1.3856 (18)
N3—H1N3	0.896 (19)	C15—H15A	0.9300
N4—C10	1.2915 (17)	C17—C18	1.526 (2)
N5—C14	1.3690 (16)	C17—H17A	0.9700
N5—C17	1.4594 (17)	C17—H17B	0.9700
N5—C19	1.4642 (17)	C18—H18A	0.9600
C1—C2	1.4170 (17)	C18—H18B	0.9600
C2—C3	1.3662 (18)	C18—H18C	0.9600
C3—C4	1.4216 (19)	C19—C20	1.528 (2)
C3—H3A	0.9300	C19—H19A	0.9700
C4—C5	1.3548 (19)	C19—H19B	0.9700
C4—H4A	0.9300	C20—H20A	0.9600
C5—H5A	0.9300	C20—H20B	0.9600
C6—C7	1.3701 (17)	C20—H20C	0.9600
C6—H6A	0.9300	O1W—H1W1	0.86 (3)
C7—C8	1.5057 (17)	O1W—H2W1	0.84 (2)
C8—C9	1.5242 (17)	O2W—H1W2	0.80 (3)
C8—H8A	0.9700	O2W—H2W2	0.86 (2)

C16—O2—H1O2	111.7 (18)	C12—C11—C16	116.99 (11)
C1—N1—C7	105.16 (10)	C12—C11—C10	119.37 (11)
C5—N2—C6	130.13 (11)	C16—C11—C10	123.53 (12)
C5—N2—C1	123.09 (11)	C13—C12—C11	122.76 (12)
C6—N2—C1	106.77 (10)	C13—C12—H12A	118.6
C9—N3—N4	120.60 (10)	C11—C12—H12A	118.6
C9—N3—H1N3	121.0 (12)	C12—C13—C14	120.09 (12)
N4—N3—H1N3	118.2 (12)	C12—C13—H13A	120.0
C10—N4—N3	113.55 (10)	C14—C13—H13A	120.0
C14—N5—C17	120.87 (11)	N5—C14—C15	121.23 (11)
C14—N5—C19	121.09 (11)	N5—C14—C13	121.24 (12)
C17—N5—C19	117.68 (11)	C15—C14—C13	117.54 (11)
N1—C1—N2	111.09 (10)	C16—C15—C14	121.34 (12)
N1—C1—C2	131.60 (11)	C16—C15—H15A	119.3
N2—C1—C2	117.31 (11)	C14—C15—H15A	119.3
C3—C2—C1	120.47 (12)	O2—C16—C15	116.85 (11)
C3—C2—Br1	121.18 (10)	O2—C16—C11	121.89 (12)
C1—C2—Br1	118.31 (9)	C15—C16—C11	121.25 (12)
C2—C3—C4	119.53 (12)	N5—C17—C18	114.42 (12)
C2—C3—H3A	120.2	N5—C17—H17A	108.7
C4—C3—H3A	120.2	C18—C17—H17A	108.7
C5—C4—C3	121.06 (12)	N5—C17—H17B	108.7
C5—C4—H4A	119.5	C18—C17—H17B	108.7
C3—C4—H4A	119.5	H17A—C17—H17B	107.6
C4—C5—N2	118.52 (12)	C17—C18—H18A	109.5
C4—C5—H5A	120.7	C17—C18—H18B	109.5
N2—C5—H5A	120.7	H18A—C18—H18B	109.5
C7—C6—N2	105.77 (11)	C17—C18—H18C	109.5
C7—C6—H6A	127.1	H18A—C18—H18C	109.5
N2—C6—H6A	127.1	H18B—C18—H18C	109.5
C6—C7—N1	111.22 (11)	N5—C19—C20	113.89 (11)
C6—C7—C8	127.58 (11)	N5—C19—H19A	108.8
N1—C7—C8	121.11 (11)	C20—C19—H19A	108.8
C7—C8—C9	109.35 (10)	N5—C19—H19B	108.8
C7—C8—H8A	109.8	C20—C19—H19B	108.8
C9—C8—H8A	109.8	H19A—C19—H19B	107.7
C7—C8—H8B	109.8	C19—C20—H20A	109.5
C9—C8—H8B	109.8	C19—C20—H20B	109.5
H8A—C8—H8B	108.3	H20A—C20—H20B	109.5
O1—C9—N3	124.94 (11)	C19—C20—H20C	109.5
O1—C9—C8	120.90 (12)	H20A—C20—H20C	109.5
N3—C9—C8	114.12 (11)	H20B—C20—H20C	109.5
N4—C10—C11	123.10 (12)	H1W1—O1W—H2W1	110 (2)
N4—C10—H10A	118.5	H1W2—O2W—H2W2	101 (2)
C11—C10—H10A	118.5

C9—N3—N4—C10	−178.57 (11)	C7—C8—C9—O1	81.70 (15)
C7—N1—C1—N2	0.28 (13)	C7—C8—C9—N3	−95.99 (13)
C7—N1—C1—C2	−179.63 (13)	N3—N4—C10—C11	175.89 (11)
C5—N2—C1—N1	−179.26 (11)	N4—C10—C11—C12	179.87 (12)
C6—N2—C1—N1	−0.44 (13)	N4—C10—C11—C16	−4.1 (2)
C5—N2—C1—C2	0.66 (17)	C16—C11—C12—C13	−0.39 (19)
C6—N2—C1—C2	179.48 (11)	C10—C11—C12—C13	175.88 (12)
N1—C1—C2—C3	−179.62 (13)	C11—C12—C13—C14	−1.3 (2)
N2—C1—C2—C3	0.47 (18)	C17—N5—C14—C15	176.84 (12)
N1—C1—C2—Br1	2.65 (19)	C19—N5—C14—C15	3.84 (18)
N2—C1—C2—Br1	−177.26 (8)	C17—N5—C14—C13	−3.34 (18)
C1—C2—C3—C4	−1.02 (19)	C19—N5—C14—C13	−176.34 (12)
Br1—C2—C3—C4	176.64 (10)	C12—C13—C14—N5	−177.55 (12)
C2—C3—C4—C5	0.5 (2)	C12—C13—C14—C15	2.28 (19)
C3—C4—C5—N2	0.6 (2)	N5—C14—C15—C16	178.18 (12)
C6—N2—C5—C4	−179.72 (12)	C13—C14—C15—C16	−1.64 (18)
C1—N2—C5—C4	−1.20 (19)	C14—C15—C16—O2	179.42 (11)
C5—N2—C6—C7	179.12 (12)	C14—C15—C16—C11	−0.03 (19)
C1—N2—C6—C7	0.41 (13)	C12—C11—C16—O2	−178.35 (12)
N2—C6—C7—N1	−0.25 (14)	C10—C11—C16—O2	5.54 (19)
N2—C6—C7—C8	176.21 (11)	C12—C11—C16—C15	1.06 (18)
C1—N1—C7—C6	−0.01 (14)	C10—C11—C16—C15	−175.04 (12)
C1—N1—C7—C8	−176.73 (11)	C14—N5—C17—C18	−78.07 (16)
C6—C7—C8—C9	−68.28 (16)	C19—N5—C17—C18	95.16 (14)
N1—C7—C8—C9	107.87 (13)	C14—N5—C19—C20	77.22 (16)
N4—N3—C9—O1	−3.51 (19)	C17—N5—C19—C20	−96.00 (14)
N4—N3—C9—C8	174.06 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/N2/C6/C7 ring and Cg3 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2Wⁱ	0.894 (17)	1.908 (17)	2.7956 (15)	171.7 (17)
O2—H1O2···O1Wⁱⁱ	0.87 (3)	2.42 (3)	2.9423 (15)	119 (2)
O2—H1O2···N4	0.87 (3)	1.99 (3)	2.7181 (16)	142 (2)
O1W—H1W1···N1	0.86 (2)	1.98 (2)	2.8315 (14)	176 (2)
O1W—H2W1···O1ⁱⁱⁱ	0.85 (3)	1.92 (2)	2.7361 (14)	162 (2)
O2W—H1W2···O1Wⁱ	0.80 (2)	2.08 (2)	2.8311 (15)	157 (2)
O2W—H2W2···O1W	0.86 (2)	1.87 (2)	2.7245 (15)	172.9 (17)
C5—H5A···O1^iv	0.93	2.50	3.3121 (17)	146
C10—H10A···O2Wⁱ	0.93	2.54	3.3256 (17)	142
C17—H17B···Br1^v	0.97	2.85	3.6569 (15)	142
C3—H3A···Cg3^vi	0.93	2.61	3.4734 (15)	154
C17—H17A···Cg1^vii	0.97	2.70	3.5863 (15)	152

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂BrN₅O₂·2H₂O
M_r	480.37
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.4370 (4), 10.6711 (5), 11.7559 (5)
α, β, γ (°)	92.914 (1), 96.949 (1), 93.978 (1)
V (Å³)	1046.23 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.37 × 0.20 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.529, 0.869
No. of measured, independent and observed [I > 2σ(I)] reflections	22937, 6491, 5841
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.077, 1.05
No. of reflections	6491
No. of parameters	297
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.24

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/N2/C6/C7 ring and Cg3 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2Wⁱ	0.894 (17)	1.908 (17)	2.7956 (15)	171.7 (17)
O2—H1O2···O1Wⁱⁱ	0.87 (3)	2.42 (3)	2.9423 (15)	119 (2)
O2—H1O2···N4	0.87 (3)	1.99 (3)	2.7181 (16)	142 (2)
O1W—H1W1···N1	0.86 (2)	1.98 (2)	2.8315 (14)	176 (2)
O1W—H2W1···O1ⁱⁱⁱ	0.85 (3)	1.92 (2)	2.7361 (14)	162 (2)
O2W—H1W2···O1Wⁱ	0.80 (2)	2.08 (2)	2.8311 (15)	157 (2)
O2W—H2W2···O1W	0.86 (2)	1.87 (2)	2.7245 (15)	172.9 (17)
C5—H5A···O1^iv	0.9300	2.5000	3.3121 (17)	146.00
C10—H10A···O2Wⁱ	0.9300	2.5400	3.3256 (17)	142.00
C17—H17B···Br1^v	0.9700	2.8500	3.6569 (15)	142.00
C3—H3A···Cg3^vi	0.9300	2.61	3.4734 (15)	154
C17—H17A···Cg1^vii	0.9700	2.70	3.5863 (15)	152

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for Research University Grant No. 1001/PFIZIK/811160. WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160. AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist award.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Biftu, T. et al. (2006). Bioorg. Med. Chem. Lett. 16, 2479–2483. Web of Science CrossRef PubMed CAS Google Scholar
Bochis, R. J., Olen, L. E., Waksmunski, F. S., Mrozik, H., Eskola, P., Kulsa, P., Wilks, G., Taylor, J. E., Egerton, J. R., Ostlind, D. A. & Olson, G. (1981). J. Med. Chem. 24, 1518–1521. CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ertepinarl, H., Gök, Y., Geban, Ö. & Özden, S. (1995). Eur. J. Med. Chem. 30, 171–175. Google Scholar
Fisher, M. H. & Lusi, A. (1972). J. Med. Chem. 15, 982–985. CrossRef CAS PubMed Web of Science Google Scholar
Gudmundsson, K. S. & Johns, B. A. (2007). Bioorg. Med. Chem. Lett. 17, 2735–2739. Web of Science CrossRef PubMed CAS Google Scholar
Hamdouchi, C., Ezquerra, J., Vega, J. A., Vaquero, J. J., Alvarez-Builla, J. & Heinz, B. A. (1999). Bioorg. Med. Chem. Lett. 9, 1391–1394. Web of Science CrossRef PubMed CAS Google Scholar
Liang, G.-B., Qian, X., Feng, D., Fisher, M., Brown, C. M., Gurnett, A., Leavitt, P. S., Liberator, P. A., Misura, A. S., Tamas, T., Schmatz, D. M., Wyvratt, M. & Biftu, T. (2007). Bioorg. Med. Chem. Lett. 17, 3558–3561. Web of Science CrossRef PubMed CAS Google Scholar
Rollas, S. & Küçükgüzel, Ş. G. (2007). Molecules, 12, 1910–1939. Web of Science CrossRef PubMed CAS Google Scholar
Seleem, H. S., El-Inany, G. A., El-Shetary, B. A. & Mousa, M. A. (2011). Chem. Cent. J. doi:10.1186/1752-153X-5-2. 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

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Volume 68| Part 3| March 2012| Pages o816-o817

doi:10.1107/S160053681200685X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(8-Bromo­imidazo[1,2-a]pyridin-2-yl)-N′-[(E)-4-di­ethyl­amino-2-hy­dr­oxy­benzyl­­idene]acetohydrazide dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-(8-Bromoimidazo[1,2-a]pyridin-2-yl)-N′-[(E)-4-diethylamino-2-hydroxybenzylidene]acetohydrazide dihydrate