7-Chloro-4-[(E)-2-(3,4,5-trimeth-oxy-benzyl-idene)hydrazin-1-yl]quinoline.

In the title compound, C(19)H(18)ClN(3)O(3), the r.m.s. deviation through the 23 non-H and non-meth-oxy atoms is 0.088 Å, indicating a planar mol-ecule with the exception of the meth-oxy groups. One meth-oxy group, surrounded on either side by the other meth-oxy groups, is almost normal to the benzene ring to which it is connected [C-O-C(ar)-C(ar) torsion angle = 81.64 (15)°]. In the crystal, N-H⋯O, C-H⋯O and π-π inter-actions [between quinoline residues; centroid-centroid distance = 3.4375 (8) Å] link mol-ecules into a three-dimensional architecture.

Related literature

For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009 ▶); Candea et al. (2009 ▶); Montenegro et al. (2012 ▶). For related structures, see: Howie et al. (2010 ▶); de Souza et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C19H18ClN3O3

M = 371.81

Orthorhombic,

a = 7.6338 (2) Å

b = 15.5335 (4) Å

c = 28.7960 (7) Å

V = 3414.62 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 120 K

0.45 × 0.40 × 0.30 mm

Data collection

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.652, T max = 0.746

22673 measured reflections

3899 independent reflections

3353 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.02

3899 reflections

241 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012755/bt5858sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012755/bt5858Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012755/bt5858Isup3.cml

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

C19H18ClN3O3	F(000) = 1552
Mr = 371.81	Dx = 1.447 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 24183 reflections
a = 7.6338 (2) Å	θ = 2.9–27.5°
b = 15.5335 (4) Å	µ = 0.25 mm−1
c = 28.7960 (7) Å	T = 120 K
V = 3414.62 (15) Å3	Prism, colourless
Z = 8	0.45 × 0.40 × 0.30 mm

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3899 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3353 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −7→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −19→20
Tmin = 0.652, Tmax = 0.746	l = −26→37
22673 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0576P)2 + 1.3595P] where P = (Fo2 + 2Fc2)/3
3899 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.32570 (5)	0.04598 (2)	0.339654 (12)	0.02558 (12)
O1	−0.29202 (13)	0.51292 (6)	−0.01170 (3)	0.0189 (2)
O2	−0.26948 (13)	0.42177 (6)	−0.09143 (3)	0.0185 (2)
O3	−0.08960 (13)	0.27516 (6)	−0.09550 (3)	0.0185 (2)
N1	0.03404 (15)	0.32333 (7)	0.28807 (4)	0.0185 (2)
N2	0.06914 (15)	0.25871 (7)	0.14639 (4)	0.0166 (2)
H2n	0.123 (2)	0.2115 (8)	0.1386 (5)	0.020*
N3	−0.00092 (14)	0.30964 (7)	0.11233 (4)	0.0160 (2)
C1	−0.02236 (18)	0.37484 (8)	0.25478 (5)	0.0183 (3)
H1	−0.0738	0.4278	0.2641	0.022*
C2	−0.01331 (18)	0.35863 (9)	0.20702 (5)	0.0168 (3)
H2A	−0.0579	0.3991	0.1853	0.020*
C3	0.06177 (17)	0.28249 (8)	0.19210 (4)	0.0144 (3)
C4	0.12967 (17)	0.22434 (8)	0.22641 (4)	0.0141 (3)
C5	0.21216 (17)	0.14533 (9)	0.21567 (5)	0.0167 (3)
H5	0.2271	0.1295	0.1840	0.020*
C6	0.27103 (18)	0.09103 (9)	0.24970 (5)	0.0177 (3)
H6	0.3268	0.0383	0.2419	0.021*
C7	0.24732 (18)	0.11490 (9)	0.29641 (5)	0.0174 (3)
C8	0.16982 (18)	0.19071 (9)	0.30860 (5)	0.0179 (3)
H8	0.1564	0.2052	0.3405	0.021*
C9	0.10938 (17)	0.24777 (9)	0.27378 (4)	0.0152 (3)
C10	0.01112 (17)	0.27774 (9)	0.07136 (5)	0.0157 (3)
H10	0.0656	0.2231	0.0679	0.019*
C11	−0.05455 (17)	0.32096 (9)	0.02980 (4)	0.0152 (3)
C12	−0.14098 (17)	0.40041 (8)	0.03151 (4)	0.0155 (3)
H12	−0.1551	0.4297	0.0602	0.019*
C13	−0.20597 (17)	0.43605 (8)	−0.00934 (5)	0.0153 (3)
C14	−0.18806 (17)	0.39204 (9)	−0.05162 (4)	0.0157 (3)
C15	−0.09928 (17)	0.31355 (8)	−0.05291 (4)	0.0152 (3)
C16	−0.03088 (18)	0.27845 (8)	−0.01241 (4)	0.0160 (3)
H16	0.0318	0.2257	−0.0135	0.019*
C17	−0.31426 (19)	0.55864 (9)	0.03114 (5)	0.0219 (3)
H17A	−0.3887	0.5249	0.0521	0.033*
H17B	−0.3696	0.6144	0.0250	0.033*
H17C	−0.1997	0.5678	0.0456	0.033*
C18	−0.1751 (2)	0.48981 (9)	−0.11456 (5)	0.0225 (3)
H18A	−0.1514	0.5364	−0.0925	0.034*
H18B	−0.2456	0.5120	−0.1404	0.034*
H18C	−0.0641	0.4673	−0.1266	0.034*
C19	−0.0276 (2)	0.18760 (9)	−0.09654 (5)	0.0228 (3)
H19A	0.0954	0.1860	−0.0869	0.034*
H19B	−0.0382	0.1648	−0.1282	0.034*
H19C	−0.0979	0.1524	−0.0753	0.034*

	U11	U22	U33	U12	U13	U23
Cl1	0.0281 (2)	0.0275 (2)	0.02106 (19)	0.00361 (14)	−0.00295 (14)	0.00990 (14)
O1	0.0219 (5)	0.0175 (5)	0.0174 (5)	0.0038 (4)	−0.0027 (4)	0.0002 (4)
O2	0.0205 (5)	0.0199 (5)	0.0151 (5)	−0.0036 (4)	−0.0054 (4)	0.0060 (4)
O3	0.0240 (5)	0.0200 (5)	0.0115 (4)	0.0007 (4)	−0.0005 (4)	−0.0013 (4)
N1	0.0204 (6)	0.0187 (6)	0.0164 (5)	−0.0006 (5)	0.0001 (4)	−0.0014 (5)
N2	0.0216 (6)	0.0163 (5)	0.0120 (5)	0.0049 (5)	−0.0013 (4)	0.0017 (4)
N3	0.0168 (6)	0.0177 (5)	0.0135 (5)	−0.0003 (4)	−0.0015 (4)	0.0039 (4)
C1	0.0193 (7)	0.0155 (6)	0.0201 (7)	0.0008 (5)	0.0019 (5)	−0.0019 (5)
C2	0.0187 (7)	0.0154 (6)	0.0164 (6)	−0.0006 (5)	−0.0004 (5)	0.0022 (5)
C3	0.0133 (6)	0.0161 (6)	0.0139 (6)	−0.0025 (5)	0.0002 (5)	0.0008 (5)
C4	0.0133 (6)	0.0157 (6)	0.0133 (6)	−0.0033 (5)	−0.0001 (5)	0.0013 (5)
C5	0.0168 (6)	0.0185 (6)	0.0148 (6)	−0.0011 (5)	−0.0010 (5)	−0.0010 (5)
C6	0.0172 (7)	0.0151 (6)	0.0209 (7)	−0.0001 (5)	−0.0018 (5)	−0.0004 (5)
C7	0.0161 (6)	0.0191 (6)	0.0169 (6)	−0.0031 (5)	−0.0030 (5)	0.0057 (5)
C8	0.0186 (7)	0.0222 (7)	0.0128 (6)	−0.0024 (5)	0.0001 (5)	0.0005 (5)
C9	0.0139 (6)	0.0166 (6)	0.0151 (6)	−0.0028 (5)	0.0002 (5)	−0.0001 (5)
C10	0.0166 (6)	0.0154 (6)	0.0152 (6)	0.0000 (5)	−0.0006 (5)	0.0009 (5)
C11	0.0134 (6)	0.0184 (6)	0.0139 (6)	−0.0028 (5)	−0.0008 (5)	0.0019 (5)
C12	0.0162 (6)	0.0174 (6)	0.0129 (6)	−0.0025 (5)	−0.0012 (5)	−0.0005 (5)
C13	0.0137 (6)	0.0137 (6)	0.0184 (7)	−0.0018 (5)	−0.0009 (5)	0.0012 (5)
C14	0.0157 (6)	0.0182 (6)	0.0132 (6)	−0.0030 (5)	−0.0034 (5)	0.0035 (5)
C15	0.0165 (6)	0.0169 (6)	0.0123 (6)	−0.0040 (5)	0.0004 (5)	−0.0002 (5)
C16	0.0165 (6)	0.0158 (6)	0.0159 (6)	−0.0009 (5)	−0.0001 (5)	0.0019 (5)
C17	0.0241 (7)	0.0196 (7)	0.0218 (7)	0.0045 (6)	−0.0039 (6)	−0.0038 (6)
C18	0.0281 (8)	0.0202 (7)	0.0190 (7)	−0.0047 (6)	−0.0019 (6)	0.0062 (6)
C19	0.0316 (8)	0.0207 (7)	0.0162 (6)	0.0024 (6)	0.0010 (6)	−0.0032 (6)

Cl1—C7	1.7478 (13)	C6—H6	0.9500
O1—C13	1.3646 (16)	C7—C8	1.364 (2)
O1—C17	1.4335 (17)	C8—C9	1.4156 (18)
O2—C14	1.3836 (15)	C8—H8	0.9500
O2—C18	1.4422 (16)	C10—C11	1.4609 (18)
O3—C15	1.3659 (15)	C10—H10	0.9500
O3—C19	1.4403 (17)	C11—C16	1.3949 (18)
N1—C1	1.3208 (18)	C11—C12	1.4003 (18)
N1—C9	1.3704 (17)	C12—C13	1.3915 (18)
N2—C3	1.3684 (16)	C12—H12	0.9500
N2—N3	1.3687 (15)	C13—C14	1.4030 (18)
N2—H2n	0.871 (9)	C14—C15	1.3954 (19)
N3—C10	1.2829 (17)	C15—C16	1.3893 (18)
C1—C2	1.4001 (19)	C16—H16	0.9500
C1—H1	0.9500	C17—H17A	0.9800
C2—C3	1.3826 (19)	C17—H17B	0.9800
C2—H2A	0.9500	C17—H17C	0.9800
C3—C4	1.4355 (18)	C18—H18A	0.9800
C4—C5	1.4136 (19)	C18—H18B	0.9800
C4—C9	1.4202 (17)	C18—H18C	0.9800
C5—C6	1.3689 (19)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.4068 (19)	C19—H19C	0.9800
C13—O1—C17	116.59 (10)	C11—C10—H10	118.3
C14—O2—C18	113.76 (10)	C16—C11—C12	120.60 (12)
C15—O3—C19	116.66 (10)	C16—C11—C10	116.86 (12)
C1—N1—C9	115.96 (12)	C12—C11—C10	122.53 (12)
C3—N2—N3	121.14 (11)	C13—C12—C11	119.26 (12)
C3—N2—H2n	119.7 (11)	C13—C12—H12	120.4
N3—N2—H2n	119.1 (11)	C11—C12—H12	120.4
C10—N3—N2	114.06 (11)	O1—C13—C12	124.19 (12)
N1—C1—C2	126.01 (13)	O1—C13—C14	115.47 (11)
N1—C1—H1	117.0	C12—C13—C14	120.33 (12)
C2—C1—H1	117.0	O2—C14—C15	119.20 (12)
C3—C2—C1	118.65 (12)	O2—C14—C13	120.84 (12)
C3—C2—H2A	120.7	C15—C14—C13	119.75 (12)
C1—C2—H2A	120.7	O3—C15—C16	124.20 (12)
N2—C3—C2	123.15 (12)	O3—C15—C14	115.58 (11)
N2—C3—C4	118.51 (12)	C16—C15—C14	120.21 (12)
C2—C3—C4	118.30 (12)	C15—C16—C11	119.79 (12)
C5—C4—C9	118.76 (12)	C15—C16—H16	120.1
C5—C4—C3	123.82 (12)	C11—C16—H16	120.1
C9—C4—C3	117.41 (12)	O1—C17—H17A	109.5
C6—C5—C4	121.64 (12)	O1—C17—H17B	109.5
C6—C5—H5	119.2	H17A—C17—H17B	109.5
C4—C5—H5	119.2	O1—C17—H17C	109.5
C5—C6—C7	118.67 (12)	H17A—C17—H17C	109.5
C5—C6—H6	120.7	H17B—C17—H17C	109.5
C7—C6—H6	120.7	O2—C18—H18A	109.5
C8—C7—C6	121.97 (12)	O2—C18—H18B	109.5
C8—C7—Cl1	119.60 (10)	H18A—C18—H18B	109.5
C6—C7—Cl1	118.40 (11)	O2—C18—H18C	109.5
C7—C8—C9	119.98 (12)	H18A—C18—H18C	109.5
C7—C8—H8	120.0	H18B—C18—H18C	109.5
C9—C8—H8	120.0	O3—C19—H19A	109.5
N1—C9—C8	117.41 (12)	O3—C19—H19B	109.5
N1—C9—C4	123.62 (12)	H19A—C19—H19B	109.5
C8—C9—C4	118.97 (12)	O3—C19—H19C	109.5
N3—C10—C11	123.46 (12)	H19A—C19—H19C	109.5
N3—C10—H10	118.3	H19B—C19—H19C	109.5
C3—N2—N3—C10	−177.97 (12)	N2—N3—C10—C11	−179.92 (12)
C9—N1—C1—C2	0.7 (2)	N3—C10—C11—C16	179.59 (12)
N1—C1—C2—C3	−0.4 (2)	N3—C10—C11—C12	−1.8 (2)
N3—N2—C3—C2	−0.9 (2)	C16—C11—C12—C13	1.09 (19)
N3—N2—C3—C4	176.90 (11)	C10—C11—C12—C13	−177.49 (12)
C1—C2—C3—N2	176.69 (12)	C17—O1—C13—C12	0.29 (18)
C1—C2—C3—C4	−1.07 (19)	C17—O1—C13—C14	179.15 (12)
N2—C3—C4—C5	3.29 (19)	C11—C12—C13—O1	−179.96 (12)
C2—C3—C4—C5	−178.84 (12)	C11—C12—C13—C14	1.23 (19)
N2—C3—C4—C9	−175.68 (11)	C18—O2—C14—C15	−103.67 (14)
C2—C3—C4—C9	2.19 (18)	C18—O2—C14—C13	81.64 (15)
C9—C4—C5—C6	0.58 (19)	O1—C13—C14—O2	−6.46 (18)
C3—C4—C5—C6	−178.38 (13)	C12—C13—C14—O2	172.44 (12)
C4—C5—C6—C7	0.3 (2)	O1—C13—C14—C15	178.87 (11)
C5—C6—C7—C8	−0.9 (2)	C12—C13—C14—C15	−2.22 (19)
C5—C6—C7—Cl1	−179.08 (10)	C19—O3—C15—C16	9.53 (19)
C6—C7—C8—C9	0.4 (2)	C19—O3—C15—C14	−169.05 (12)
Cl1—C7—C8—C9	178.63 (10)	O2—C14—C15—O3	4.77 (18)
C1—N1—C9—C8	−179.44 (12)	C13—C14—C15—O3	179.53 (11)
C1—N1—C9—C4	0.65 (19)	O2—C14—C15—C16	−173.87 (12)
C7—C8—C9—N1	−179.42 (12)	C13—C14—C15—C16	0.88 (19)
C7—C8—C9—C4	0.50 (19)	O3—C15—C16—C11	−177.10 (12)
C5—C4—C9—N1	178.92 (12)	C14—C15—C16—C11	1.4 (2)
C3—C4—C9—N1	−2.05 (19)	C12—C11—C16—C15	−2.4 (2)
C5—C4—C9—C8	−0.99 (18)	C10—C11—C16—C15	176.23 (12)
C3—C4—C9—C8	178.03 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O3i	0.87 (1)	2.53 (2)	3.0349 (15)	118 (1)
C19—H19B···N1ii	0.98	2.48	3.3602 (18)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O3i	0.87 (1)	2.53 (2)	3.0349 (15)	118 (1)
C19—H19B⋯N1ii	0.98	2.48	3.3602 (18)	149

Symmetry codes: (i) ; (ii) .