2-Chloro-3-[(E)-(hydrazin-1-yl-idene)meth-yl]-6-meth-oxy-quinoline.

In the title compound, C(11)H(10)ClN(3)O, 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=NH(2) 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 = 235.67

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.073

S = 1.06

2352 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 922 Friedel pairs

Flack parameter: 0.00 (6)

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017977/fj2545sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812017977/fj2545Isup3.cml

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

C11H10ClN3O	Dx = 1.517 Mg m−3
Mr = 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

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

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(Fo2) + (0.0395P)2 + 0.2196P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2352 reflections	Δρmax = 0.31 e Å−3
147 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 922 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

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
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)

	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)

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)

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

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) ; (ii) .