2-Chloro-3-[(E)-(hydrazin-1-yl­idene)meth­yl]-6-meth­oxy­quinoline

Bouacida, S.; Bouraiou, A.; Benhamoud, N.; Roisnel, T.; Belfaitah, A.

doi:10.1107/S1600536812017977

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1548

doi:10.1107/S1600536812017977

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2-Chloro-3-[(E)-(hydrazin-1-ylidene)methyl]-6-methoxyquinoline

Sofiane Bouacida,^a ^* Abdelmalek Bouraiou,^b Nassima Benhamoud,^a Thierry Roisnel ^c and Ali Belfaitah ^b

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Mentouri-Constantine, 25000 Algeria, ^bLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 12 April 2012; accepted 22 April 2012; online 28 April 2012)

In the title compound, C₁₁H₁₀ClN₃O, the quinoline ring system is essentially planar, the r.m.s. deviation for the non-H atoms being 0.014 (2) Å with a maximum deviation from the mean plane of 0.0206 (14) Å for the C atom bonded to the –CH—N=NH₂ group. In the crystal, molecules are linked via N—H⋯O and N—H⋯N hydrogen bonds, forming zigzag layers parallel to (010).

Related literature

For previous work on molecules with a quinolyl moiety, see: Benzerka et al. (2011 ); Belfaitah et al. (2006 ) Bouraiou et al. (2008 , 2011 ); Ladraa et al. (2009 ). For applications of pyrazole and its derivatives, see: Mali et al. (2010 ); Paul et al. (2001 ).

Experimental

Crystal data

C₁₁H₁₀ClN₃O
M_r = 235.67
Orthorhombic, P 2₁ 2₁ 2₁
a = 3.8949 (2) Å
b = 12.0510 (5) Å
c = 21.9910 (9) Å
V = 1032.20 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 150 K
0.28 × 0.15 × 0.14 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.898, T_max = 0.952
15777 measured reflections
2352 independent reflections
2044 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.073
S = 1.06
2352 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 922 Friedel pairs
Flack parameter: 0.00 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯O14ⁱ	0.88	2.34	3.219 (2)	178
N13—H13B⋯N13ⁱⁱ	0.88	2.19	3.058 (2)	169
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017977/fj2545sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017977/fj2545Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017977/fj2545Isup3.cml

checkCIF report

Comment top

Pyrazole and its derivatives are gaining importance in medicinal and organic chemistry. They have displayed broad spectrum of pharmacological and biological activities such as anti-bacterial, anti-depressant, and anti-hyperglycemic (Mali et al., 2010). Pyrazolo[3,4-b]quinolines have displayed bioactivities such as antiviral, antimalarial, lowering of serum cholesterol (Paul et al., 2001), but no metal complexes of such drugs have been reported in the past which might possibly have better pharmaceutical effect. Therefore, studies of the metal complexes are important in the search for new drugs. In previous works, we were interested in the design and synthesis of new molecules that contain a quinolyl moiety (Belfaitah et al., 2006; Bouraiou et al., 2008, 2011; Ladraa et al., 2009 and Benzerka et al., 2011). In this paper, we report the structure determination of compound resulting from an unwanted reaction of the 6-methoxy-1H-pyrazolo[3,4-b]quinoline with RuCl₃ in acidic conditions. Our attempt to synthesis the pyrazolo[3,4-b]quinoline/Ruthenium complex was failed and led to (E)-1-((2-chloro-6-methylquinolin-3-yl)methylene)hydrazine (I).

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. In the asymetric unit of title molecule, (C₁₁ H₁₀ Cl N₃ O), the chloro-quinolyl unit is linked to methoxy and methylenehydrazine group. The quinoline ring system is essentially planar; the r.m.s. deviation for the non-H atoms is 0.014 (2) Å with a maximum deviation from the mean plane of 0.0206 (14) Å for the C atom bonded to the –CH—N═NH₂ group. The crystal packing can be described as layers in zigzag parallel to the (010) plane (Fig. 2). It is stabilized by N—H···O and N—H···N intermolecular hydrogen bonds (Fig. 2). These interaction bonds link the molecules within the layers and also link the layers together, reinforcing the cohesion of the structure. Hydrogen-bonding parameters are listed in table 1.

Related literature top

For previous work on molecules with a quinolyl moiety, see: Benzerka et al. (2011); Belfaitah et al. (2006) Bouraiou et al. (2008, 2011); Ladraa et al. (2009). For applications of pyrazole and its derivatives, see: Mali et al. (2010); Paul et al. (2001).

Experimental top

First, 6-methoxy-1H-pyrazolo[3,4-b]quinoline was prepared from 2-chloro-6-methoxyquinoline-3-carbaldehyde and hydrazine hydrate in refluxing ethanol in a one-pot synthesis. Next, a mixture of 6-methoxy-1H-pyrazolo[3,4-b]quinoline(5 mmol)and RuCl₃(5 mmol) in aqueous HCl(10 ml) was stirred at 50°C for 1 h. Under these conditions, compound I was successfully obtained. Single crystals suitable for X-ray diffraction analysis were obtained by dissolving the corresponding compound in methanol solution and letting it for slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. (Farrugia, 1997) the structure of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level.
	Fig. 2. (Brandenburg & Berndt, 2001) A diagram of the layered crystal packing of (I) viewed down the a axis and showing hydrogen bond [N—H···O and N—H···N] as dashed line.

2-Chloro-3-[(E)-(hydrazin-1-ylidene)methyl]-6-methoxyquinoline top

Crystal data top

C₁₁H₁₀ClN₃O	D_x = 1.517 Mg m⁻³
M_r = 235.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 26476 reflections
a = 3.8949 (2) Å	θ = 2.9–27.5°
b = 12.0510 (5) Å	µ = 0.35 mm⁻¹
c = 21.9910 (9) Å	T = 150 K
V = 1032.20 (8) Å³	Prism, colourless
Z = 4	0.28 × 0.15 × 0.14 mm
F(000) = 488

Data collection top

Bruker APEXII diffractometer	2352 independent reflections
Radiation source: Enraf–Nonius FR590	2044 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
CCD rotation images, thin slices scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −15→15
T_min = 0.898, T_max = 0.952	l = −28→28
15777 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0395P)² + 0.2196P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2352 reflections	Δρ_max = 0.31 e Å⁻³
147 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 922 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (6)

Crystal data top

C₁₁H₁₀ClN₃O	V = 1032.20 (8) Å³
M_r = 235.67	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 3.8949 (2) Å	µ = 0.35 mm⁻¹
b = 12.0510 (5) Å	T = 150 K
c = 21.9910 (9) Å	0.28 × 0.15 × 0.14 mm

Data collection top

Bruker APEXII diffractometer	2352 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	2044 reflections with I > 2σ(I)
T_min = 0.898, T_max = 0.952	R_int = 0.044
15777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.073	Δρ_max = 0.31 e Å⁻³
S = 1.06	Δρ_min = −0.26 e Å⁻³
2352 reflections	Absolute structure: Flack (1983), 922 Friedel pairs
147 parameters	Absolute structure parameter: 0.00 (6)
0 restraints

Special details top

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
C1	0.4493 (5)	0.15128 (15)	0.87535 (8)	0.0170 (4)
C3	0.3425 (5)	0.16948 (14)	0.77399 (8)	0.0168 (4)
C4	0.3615 (5)	0.23375 (14)	0.72037 (8)	0.0187 (4)
H4	0.4634	0.3053	0.7216	0.022*
C5	0.2342 (5)	0.19378 (14)	0.66667 (8)	0.0201 (4)
H5	0.2468	0.2378	0.6309	0.024*
C6	0.0840 (5)	0.08694 (15)	0.66430 (8)	0.0179 (4)
C7	0.0598 (5)	0.02243 (15)	0.71528 (8)	0.0173 (4)
H7	−0.0414	−0.0492	0.7131	0.021*
C8	0.1864 (5)	0.06299 (13)	0.77136 (8)	0.0160 (4)
C9	0.1641 (5)	0.00226 (13)	0.82624 (8)	0.0156 (4)
H9	0.0595	−0.069	0.8261	0.019*
C10	0.2916 (5)	0.04468 (14)	0.87986 (8)	0.0165 (4)
C11	0.2622 (5)	−0.01392 (14)	0.93795 (8)	0.0179 (4)
H11	0.3884	0.0114	0.9722	0.021*
C15	−0.1868 (5)	−0.05136 (14)	0.60289 (8)	0.0219 (4)
H15A	−0.0198	−0.1085	0.6143	0.033*
H15B	−0.2623	−0.0637	0.5609	0.033*
H15C	−0.3852	−0.0552	0.6302	0.033*
N2	0.4745 (4)	0.21203 (13)	0.82682 (6)	0.0176 (3)
N12	0.0681 (4)	−0.09888 (12)	0.94285 (7)	0.0202 (3)
N13	0.0692 (5)	−0.15224 (13)	0.99808 (7)	0.0240 (4)
H13A	0.1995	−0.1275	1.0278	0.029*
H13B	−0.0603	−0.2112	1.0037	0.029*
Cl1	0.62727 (12)	0.20978 (3)	0.941458 (19)	0.02055 (12)
O14	−0.0299 (4)	0.05616 (10)	0.60762 (5)	0.0210 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0146 (10)	0.0199 (9)	0.0167 (8)	0.0006 (7)	0.0013 (8)	−0.0050 (7)
C3	0.0146 (9)	0.0175 (8)	0.0183 (8)	0.0019 (8)	0.0024 (8)	−0.0024 (7)
C4	0.0198 (9)	0.0143 (8)	0.0219 (8)	0.0004 (8)	0.0038 (8)	0.0006 (7)
C5	0.0244 (10)	0.0191 (9)	0.0170 (9)	0.0024 (8)	0.0041 (8)	0.0025 (7)
C6	0.0179 (10)	0.0207 (9)	0.0151 (8)	0.0033 (8)	0.0011 (8)	−0.0031 (7)
C7	0.0193 (10)	0.0138 (8)	0.0189 (9)	−0.0001 (7)	0.0025 (8)	−0.0011 (7)
C8	0.0149 (10)	0.0155 (8)	0.0176 (8)	0.0032 (7)	0.0025 (8)	−0.0012 (7)
C9	0.0158 (10)	0.0121 (8)	0.0188 (8)	−0.0007 (8)	0.0031 (8)	0.0000 (7)
C10	0.0149 (10)	0.0163 (9)	0.0184 (9)	0.0027 (7)	0.0024 (7)	−0.0020 (7)
C11	0.0190 (9)	0.0191 (9)	0.0156 (8)	0.0017 (7)	−0.0014 (8)	−0.0031 (8)
C15	0.0242 (11)	0.0227 (9)	0.0187 (9)	−0.0015 (8)	−0.0010 (9)	−0.0039 (7)
N2	0.0173 (7)	0.0173 (7)	0.0181 (7)	−0.0005 (7)	0.0025 (6)	−0.0021 (7)
N12	0.0224 (8)	0.0201 (7)	0.0181 (7)	0.0014 (6)	0.0024 (8)	0.0018 (7)
N13	0.0339 (10)	0.0203 (8)	0.0177 (7)	−0.0039 (8)	−0.0013 (8)	0.0034 (6)
Cl1	0.0223 (2)	0.0211 (2)	0.01815 (19)	−0.00307 (19)	−0.0007 (2)	−0.00380 (18)
O14	0.0302 (8)	0.0194 (7)	0.0135 (6)	−0.0021 (5)	−0.0012 (6)	−0.0008 (5)

Geometric parameters (Å, º) top

C1—N2	1.298 (2)	C8—C9	1.414 (2)
C1—C10	1.428 (2)	C9—C10	1.378 (2)
C1—Cl1	1.7581 (17)	C9—H9	0.95
C3—N2	1.370 (2)	C10—C11	1.464 (2)
C3—C4	1.413 (2)	C11—N12	1.277 (2)
C3—C8	1.421 (2)	C11—H11	0.95
C4—C5	1.368 (3)	C15—O14	1.436 (2)
C4—H4	0.95	C15—H15A	0.98
C5—C6	1.415 (3)	C15—H15B	0.98
C5—H5	0.95	C15—H15C	0.98
C6—C7	1.368 (2)	N12—N13	1.374 (2)
C6—O14	1.374 (2)	N13—H13A	0.88
C7—C8	1.415 (2)	N13—H13B	0.88
C7—H7	0.95

N2—C1—C10	126.68 (16)	C10—C9—C8	121.08 (15)
N2—C1—Cl1	115.08 (13)	C10—C9—H9	119.5
C10—C1—Cl1	118.23 (13)	C8—C9—H9	119.5
N2—C3—C4	118.87 (16)	C9—C10—C1	115.43 (15)
N2—C3—C8	122.21 (15)	C9—C10—C11	122.66 (15)
C4—C3—C8	118.92 (16)	C1—C10—C11	121.89 (15)
C5—C4—C3	120.56 (16)	N12—C11—C10	120.43 (17)
C5—C4—H4	119.7	N12—C11—H11	119.8
C3—C4—H4	119.7	C10—C11—H11	119.8
C4—C5—C6	120.12 (16)	O14—C15—H15A	109.5
C4—C5—H5	119.9	O14—C15—H15B	109.5
C6—C5—H5	119.9	H15A—C15—H15B	109.5
C7—C6—O14	124.60 (16)	O14—C15—H15C	109.5
C7—C6—C5	121.03 (16)	H15A—C15—H15C	109.5
O14—C6—C5	114.37 (15)	H15B—C15—H15C	109.5
C6—C7—C8	119.60 (16)	C1—N2—C3	117.24 (15)
C6—C7—H7	120.2	C11—N12—N13	116.60 (16)
C8—C7—H7	120.2	N12—N13—H13A	120
C9—C8—C7	122.92 (16)	N12—N13—H13B	120
C9—C8—C3	117.32 (16)	H13A—N13—H13B	120
C7—C8—C3	119.76 (16)	C6—O14—C15	116.53 (14)

N2—C3—C4—C5	179.61 (17)	C8—C9—C10—C1	−1.1 (3)
C8—C3—C4—C5	−0.5 (3)	C8—C9—C10—C11	177.74 (17)
C3—C4—C5—C6	−0.4 (3)	N2—C1—C10—C9	2.1 (3)
C4—C5—C6—C7	0.7 (3)	Cl1—C1—C10—C9	−178.57 (14)
C4—C5—C6—O14	−179.26 (17)	N2—C1—C10—C11	−176.71 (17)
O14—C6—C7—C8	179.99 (18)	Cl1—C1—C10—C11	2.6 (2)
C5—C6—C7—C8	0.1 (3)	C9—C10—C11—N12	−11.3 (3)
C6—C7—C8—C9	178.61 (17)	C1—C10—C11—N12	167.39 (17)
C6—C7—C8—C3	−1.0 (3)	C10—C1—N2—C3	−1.3 (3)
N2—C3—C8—C9	1.4 (3)	Cl1—C1—N2—C3	179.38 (13)
C4—C3—C8—C9	−178.41 (18)	C4—C3—N2—C1	179.25 (17)
N2—C3—C8—C7	−178.88 (17)	C8—C3—N2—C1	−0.6 (3)
C4—C3—C8—C7	1.3 (3)	C10—C11—N12—N13	176.74 (15)
C7—C8—C9—C10	179.82 (18)	C7—C6—O14—C15	0.5 (3)
C3—C8—C9—C10	−0.5 (3)	C5—C6—O14—C15	−179.58 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O14ⁱ	0.88	2.34	3.219 (2)	178
N13—H13B···N13ⁱⁱ	0.88	2.19	3.058 (2)	169
C11—H11···Cl1	0.95	2.65	3.0488 (18)	106

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀ClN₃O
M_r	235.67
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	3.8949 (2), 12.0510 (5), 21.9910 (9)
V (Å³)	1032.20 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.28 × 0.15 × 0.14

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.898, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	15777, 2352, 2044
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.073, 1.06
No. of reflections	2352
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26
Absolute structure	Flack (1983), 922 Friedel pairs
Absolute structure parameter	0.00 (6)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O14ⁱ	0.8800	2.3400	3.219 (2)	178.00
N13—H13B···N13ⁱⁱ	0.8800	2.1900	3.058 (2)	169.00

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

Acknowledgements

We are grateful to the PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria for assistance. Thanks are also due to the Ministére de l'Enseignement Supérieur et de la Recherche Scientifique and the Agence Nationale pour le Développement de la Recherche Universitaire for financial support via the PNR programm.

References

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