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

In the nearly planar title compound (r.m.s. deviation for the 24 non-H atoms = 0.064 Å), C(18)H(16)ClN(3)O(2), the conformation about the N=C bond is E. Supra-molecular chains propagated by glide symmetry along [001] are found in the crystal packing. These are sustained by N-H⋯N hydrogen bonds with the quinoline N atom being the acceptor. The chains are connected into a three-dimensional architecture by π-π inter-actions involving all three aromatic rings [centroid-centroid distances = 3.5650 (9)-3.6264 (9) Å].

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. (2011 ▶, 2012 ▶). For related structures, see: Howie et al. (2010 ▶); de Souza et al. (2010 ▶); de Lima Ferreira et al. (2010 ▶). For the synthesis, see: Montenegro et al. (2012 ▶).

Experimental

Crystal data

C18H16ClN3O2

M = 341.79

Monoclinic,

a = 10.5183 (2) Å

b = 12.9132 (3) Å

c = 12.9861 (2) Å

β = 112.723 (2)°

V = 1626.93 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 120 K

0.32 × 0.20 × 0.15 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

20405 measured reflections

3723 independent reflections

3067 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.03

3723 reflections

222 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.33 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/S1600536812012871/xu5494sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012871/xu5494Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012871/xu5494Isup3.cml

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

C18H16ClN3O2	F(000) = 712
Mr = 341.79	Dx = 1.395 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8419 reflections
a = 10.5183 (2) Å	θ = 2.9–27.5°
b = 12.9132 (3) Å	µ = 0.25 mm−1
c = 12.9861 (2) Å	T = 120 K
β = 112.723 (2)°	Prism, yellow
V = 1626.93 (5) Å3	0.32 × 0.20 × 0.15 mm
Z = 4

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3723 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3067 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −15→16
Tmin = 0.652, Tmax = 0.746	l = −16→16
20405 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.6611P] where P = (Fo2 + 2Fc2)/3
3723 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.33 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	0.07757 (4)	0.46710 (3)	0.65860 (3)	0.02240 (13)
O1	0.67832 (11)	0.06456 (8)	0.25193 (8)	0.0200 (2)
O2	0.98754 (12)	−0.18234 (9)	0.60966 (10)	0.0273 (3)
N1	0.45113 (13)	0.19900 (10)	0.83352 (10)	0.0169 (3)
N2	0.53424 (13)	0.16602 (10)	0.54269 (10)	0.0169 (3)
H2N	0.4970 (16)	0.2057 (11)	0.4831 (10)	0.020*
N3	0.63038 (13)	0.09359 (10)	0.54186 (10)	0.0174 (3)
C1	0.54351 (15)	0.13277 (12)	0.82563 (12)	0.0173 (3)
H1	0.5927	0.0921	0.8897	0.021*
C2	0.57480 (15)	0.11751 (12)	0.73189 (12)	0.0172 (3)
H2	0.6407	0.0669	0.7327	0.021*
C3	0.50855 (15)	0.17718 (11)	0.63725 (12)	0.0143 (3)
C4	0.40798 (14)	0.25126 (11)	0.64014 (11)	0.0135 (3)
C5	0.33252 (15)	0.31670 (11)	0.54965 (12)	0.0157 (3)
H5	0.3502	0.3143	0.4833	0.019*
C6	0.23425 (15)	0.38355 (11)	0.55596 (12)	0.0168 (3)
H6	0.1850	0.4277	0.4950	0.020*
C7	0.20770 (15)	0.38559 (11)	0.65392 (12)	0.0155 (3)
C8	0.27876 (15)	0.32511 (11)	0.74402 (12)	0.0158 (3)
H8	0.2589	0.3287	0.8094	0.019*
C9	0.38202 (14)	0.25713 (11)	0.73985 (12)	0.0142 (3)
C10	0.64283 (15)	0.08142 (11)	0.44812 (12)	0.0157 (3)
H10	0.5869	0.1209	0.3851	0.019*
C11	0.74242 (15)	0.00736 (11)	0.43720 (12)	0.0145 (3)
C12	0.75975 (15)	−0.00070 (11)	0.33516 (12)	0.0156 (3)
C13	0.85456 (16)	−0.07004 (12)	0.32490 (13)	0.0194 (3)
H13	0.8663	−0.0752	0.2561	0.023*
C14	0.93308 (16)	−0.13246 (12)	0.41476 (13)	0.0203 (3)
H14	0.9977	−0.1800	0.4070	0.024*
C15	0.91658 (15)	−0.12495 (12)	0.51558 (13)	0.0195 (3)
C16	0.82194 (15)	−0.05485 (11)	0.52614 (13)	0.0172 (3)
H16	0.8114	−0.0494	0.5954	0.021*
C17	0.7013 (2)	0.06604 (15)	0.15086 (14)	0.0303 (4)
H17A	0.7981	0.0827	0.1674	0.045*
H17B	0.6421	0.1185	0.1005	0.045*
H17C	0.6796	−0.0021	0.1151	0.045*
C18	1.09064 (17)	−0.25167 (13)	0.60485 (16)	0.0306 (4)
H18A	1.0479	−0.3035	0.5466	0.046*
H18B	1.1349	−0.2864	0.6771	0.046*
H18C	1.1599	−0.2127	0.5876	0.046*

	U11	U22	U33	U12	U13	U23
Cl1	0.0225 (2)	0.0242 (2)	0.0220 (2)	0.00878 (15)	0.01015 (16)	0.00116 (15)
O1	0.0247 (6)	0.0234 (6)	0.0150 (5)	0.0069 (5)	0.0111 (5)	0.0024 (4)
O2	0.0263 (6)	0.0217 (6)	0.0280 (6)	0.0076 (5)	0.0040 (5)	0.0068 (5)
N1	0.0197 (6)	0.0178 (6)	0.0140 (6)	0.0014 (5)	0.0073 (5)	0.0000 (5)
N2	0.0197 (7)	0.0191 (7)	0.0141 (6)	0.0052 (5)	0.0091 (5)	0.0022 (5)
N3	0.0185 (6)	0.0176 (6)	0.0188 (6)	0.0031 (5)	0.0100 (5)	−0.0005 (5)
C1	0.0189 (8)	0.0183 (7)	0.0143 (7)	0.0015 (6)	0.0057 (6)	0.0024 (6)
C2	0.0175 (7)	0.0184 (7)	0.0161 (7)	0.0028 (6)	0.0067 (6)	0.0002 (6)
C3	0.0148 (7)	0.0152 (7)	0.0139 (7)	−0.0041 (5)	0.0068 (6)	−0.0031 (5)
C4	0.0141 (7)	0.0143 (7)	0.0127 (7)	−0.0026 (5)	0.0057 (6)	−0.0017 (5)
C5	0.0183 (7)	0.0174 (7)	0.0128 (7)	−0.0011 (6)	0.0076 (6)	0.0005 (6)
C6	0.0188 (7)	0.0155 (7)	0.0157 (7)	0.0000 (6)	0.0063 (6)	0.0024 (6)
C7	0.0149 (7)	0.0127 (7)	0.0190 (7)	0.0007 (5)	0.0067 (6)	−0.0029 (6)
C8	0.0184 (7)	0.0171 (7)	0.0141 (7)	−0.0010 (6)	0.0085 (6)	−0.0019 (6)
C9	0.0157 (7)	0.0139 (7)	0.0125 (7)	−0.0025 (6)	0.0048 (5)	−0.0021 (5)
C10	0.0163 (7)	0.0164 (7)	0.0150 (7)	−0.0008 (6)	0.0067 (6)	0.0006 (6)
C11	0.0144 (7)	0.0139 (7)	0.0162 (7)	−0.0024 (5)	0.0072 (6)	−0.0017 (5)
C12	0.0166 (7)	0.0152 (7)	0.0154 (7)	−0.0007 (6)	0.0065 (6)	−0.0002 (5)
C13	0.0207 (8)	0.0188 (8)	0.0218 (8)	−0.0006 (6)	0.0113 (6)	−0.0039 (6)
C14	0.0171 (7)	0.0152 (7)	0.0296 (8)	0.0008 (6)	0.0101 (7)	−0.0029 (6)
C15	0.0165 (7)	0.0142 (7)	0.0237 (8)	−0.0015 (6)	0.0031 (6)	0.0012 (6)
C16	0.0179 (7)	0.0162 (7)	0.0176 (7)	−0.0029 (6)	0.0071 (6)	−0.0014 (6)
C17	0.0427 (11)	0.0363 (10)	0.0193 (8)	0.0131 (8)	0.0202 (8)	0.0059 (7)
C18	0.0236 (9)	0.0184 (8)	0.0431 (11)	0.0048 (7)	0.0053 (8)	0.0037 (7)

Cl1—C7	1.7462 (15)	C6—H6	0.9500
O1—C12	1.3773 (18)	C7—C8	1.365 (2)
O1—C17	1.4235 (18)	C8—C9	1.414 (2)
O2—C15	1.3764 (18)	C8—H8	0.9500
O2—C18	1.426 (2)	C10—C11	1.465 (2)
N1—C1	1.3277 (19)	C10—H10	0.9500
N1—C9	1.3742 (18)	C11—C16	1.390 (2)
N2—C3	1.3631 (18)	C11—C12	1.409 (2)
N2—N3	1.3805 (17)	C12—C13	1.384 (2)
N2—H2N	0.884 (9)	C13—C14	1.396 (2)
N3—C10	1.2834 (18)	C13—H13	0.9500
C1—C2	1.392 (2)	C14—C15	1.389 (2)
C1—H1	0.9500	C14—H14	0.9500
C2—C3	1.389 (2)	C15—C16	1.391 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.437 (2)	C17—H17A	0.9800
C4—C5	1.416 (2)	C17—H17B	0.9800
C4—C9	1.4248 (19)	C17—H17C	0.9800
C5—C6	1.373 (2)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.404 (2)	C18—H18C	0.9800
C12—O1—C17	117.14 (12)	N3—C10—C11	120.69 (13)
C15—O2—C18	117.38 (13)	N3—C10—H10	119.7
C1—N1—C9	115.86 (12)	C11—C10—H10	119.7
C3—N2—N3	118.64 (12)	C16—C11—C12	118.92 (13)
C3—N2—H2N	123.5 (11)	C16—C11—C10	121.33 (13)
N3—N2—H2N	117.7 (11)	C12—C11—C10	119.74 (13)
C10—N3—N2	115.71 (12)	O1—C12—C13	124.95 (13)
N1—C1—C2	125.86 (13)	O1—C12—C11	115.19 (13)
N1—C1—H1	117.1	C13—C12—C11	119.85 (14)
C2—C1—H1	117.1	C12—C13—C14	120.57 (14)
C3—C2—C1	119.21 (13)	C12—C13—H13	119.7
C3—C2—H2	120.4	C14—C13—H13	119.7
C1—C2—H2	120.4	C15—C14—C13	119.91 (14)
N2—C3—C2	122.16 (13)	C15—C14—H14	120.0
N2—C3—C4	119.86 (13)	C13—C14—H14	120.0
C2—C3—C4	117.96 (13)	O2—C15—C14	125.22 (14)
C5—C4—C9	118.67 (13)	O2—C15—C16	115.23 (14)
C5—C4—C3	123.90 (13)	C14—C15—C16	119.55 (14)
C9—C4—C3	117.42 (12)	C11—C16—C15	121.20 (14)
C6—C5—C4	121.28 (13)	C11—C16—H16	119.4
C6—C5—H5	119.4	C15—C16—H16	119.4
C4—C5—H5	119.4	O1—C17—H17A	109.5
C5—C6—C7	118.92 (13)	O1—C17—H17B	109.5
C5—C6—H6	120.5	H17A—C17—H17B	109.5
C7—C6—H6	120.5	O1—C17—H17C	109.5
C8—C7—C6	122.10 (13)	H17A—C17—H17C	109.5
C8—C7—Cl1	119.49 (11)	H17B—C17—H17C	109.5
C6—C7—Cl1	118.41 (11)	O2—C18—H18A	109.5
C7—C8—C9	119.80 (13)	O2—C18—H18B	109.5
C7—C8—H8	120.1	H18A—C18—H18B	109.5
C9—C8—H8	120.1	O2—C18—H18C	109.5
N1—C9—C8	117.18 (12)	H18A—C18—H18C	109.5
N1—C9—C4	123.63 (13)	H18B—C18—H18C	109.5
C8—C9—C4	119.18 (13)
C3—N2—N3—C10	175.16 (13)	C3—C4—C9—N1	2.5 (2)
C9—N1—C1—C2	−0.3 (2)	C5—C4—C9—C8	2.2 (2)
N1—C1—C2—C3	1.8 (2)	C3—C4—C9—C8	−176.72 (13)
N3—N2—C3—C2	−0.6 (2)	N2—N3—C10—C11	179.47 (12)
N3—N2—C3—C4	−179.38 (12)	N3—C10—C11—C16	2.7 (2)
C1—C2—C3—N2	−179.88 (14)	N3—C10—C11—C12	−176.54 (14)
C1—C2—C3—C4	−1.1 (2)	C17—O1—C12—C13	−5.0 (2)
N2—C3—C4—C5	−1.0 (2)	C17—O1—C12—C11	174.34 (14)
C2—C3—C4—C5	−179.75 (14)	C16—C11—C12—O1	−179.20 (13)
N2—C3—C4—C9	177.93 (13)	C10—C11—C12—O1	0.1 (2)
C2—C3—C4—C9	−0.9 (2)	C16—C11—C12—C13	0.2 (2)
C9—C4—C5—C6	−1.1 (2)	C10—C11—C12—C13	179.50 (13)
C3—C4—C5—C6	177.74 (13)	O1—C12—C13—C14	179.53 (14)
C4—C5—C6—C7	−0.8 (2)	C11—C12—C13—C14	0.2 (2)
C5—C6—C7—C8	1.6 (2)	C12—C13—C14—C15	−0.2 (2)
C5—C6—C7—Cl1	−177.40 (11)	C18—O2—C15—C14	3.0 (2)
C6—C7—C8—C9	−0.5 (2)	C18—O2—C15—C16	−176.98 (13)
Cl1—C7—C8—C9	178.51 (11)	C13—C14—C15—O2	179.83 (14)
C1—N1—C9—C8	177.32 (13)	C13—C14—C15—C16	−0.2 (2)
C1—N1—C9—C4	−1.9 (2)	C12—C11—C16—C15	−0.6 (2)
C7—C8—C9—N1	179.30 (13)	C10—C11—C16—C15	−179.88 (13)
C7—C8—C9—C4	−1.4 (2)	O2—C15—C16—C11	−179.42 (13)
C5—C4—C9—N1	−178.56 (13)	C14—C15—C16—C11	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N1i	0.88 (1)	2.19 (1)	3.0572 (17)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯N1i	0.88 (1)	2.19 (1)	3.0572 (17)	167 (2)

Symmetry code: (i) .