N,N'-Bis[(E)-(2-chloro-8-methyl-quinolin-3-yl)methyl-idene]ethane-1,2-diamine.

The complete mol-ecule of the title compound, C(24)H(20)Cl(2)N(4), is generated by a crystallographic inversion centre. A kink in the mol-ecule is evident [C-N-C-C torsion angle = -147.0 (3)°] owing to the twist in the central ethyl-ene bridge. Further, there is a small twist between the imine [N=C = 1.267 (3) Å] and quinoline residues [N-C-C-C = -12.4 (4)°]. In the crystal, a combination of π-π [pyridine-benzene centroid-centroid distance = 3.5670 (14) Å] and C-H⋯N contacts leads to supra-molecular chains propagating in [010].

Related literature

For background to the photophysical properties of Schiff base complexes derivativatized with quinoline residues, see: Liu et al. (2010 ▶).

Experimental

Crystal data

C24H20Cl2N4

M = 435.34

Monoclinic,

a = 18.363 (2) Å

b = 3.9494 (5) Å

c = 14.1726 (19) Å

β = 99.056 (2)°

V = 1015.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.30 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.756, T max = 0.862

8859 measured reflections

2324 independent reflections

1863 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.140

S = 1.05

2324 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S160053681004540X/hb5727sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004540X/hb5727Isup2.hkl

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

C24H20Cl2N4	F(000) = 452
Mr = 435.34	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1737 reflections
a = 18.363 (2) Å	θ = 2.9–28.1°
b = 3.9494 (5) Å	µ = 0.34 mm−1
c = 14.1726 (19) Å	T = 100 K
β = 99.056 (2)°	Prism, yellow
V = 1015.0 (2) Å3	0.30 × 0.15 × 0.05 mm
Z = 2

Bruker SMART APEX diffractometer	2324 independent reflections
Radiation source: fine-focus sealed tube	1863 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→21
Tmin = 0.756, Tmax = 0.862	k = −5→5
8859 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.073P)2 + 0.7018P] where P = (Fo2 + 2Fc2)/3
2324 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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
Cl1	0.66489 (3)	0.91685 (16)	0.86511 (4)	0.0207 (2)
N1	0.57606 (11)	0.7565 (5)	0.56683 (14)	0.0198 (4)
N2	0.77325 (10)	1.1953 (5)	0.79768 (12)	0.0146 (4)
C1	0.50497 (13)	0.5852 (7)	0.54853 (16)	0.0193 (5)
H1A	0.4649	0.7516	0.5505	0.023*
H1B	0.5022	0.4137	0.5988	0.023*
C2	0.60887 (13)	0.7696 (6)	0.65240 (16)	0.0182 (5)
H2	0.5878	0.6618	0.7016	0.022*
C3	0.67969 (12)	0.9510 (6)	0.67619 (16)	0.0163 (5)
C4	0.71175 (12)	1.0337 (6)	0.77157 (15)	0.0156 (5)
C5	0.71871 (12)	1.0545 (6)	0.60569 (15)	0.0159 (5)
H5	0.6999	1.0076	0.5407	0.019*
C6	0.78589 (12)	1.2285 (6)	0.62878 (14)	0.0144 (5)
C7	0.82776 (13)	1.3369 (6)	0.55873 (15)	0.0161 (5)
H7	0.8108	1.2934	0.4930	0.019*
C8	0.89247 (13)	1.5042 (6)	0.58613 (15)	0.0176 (5)
H8	0.9209	1.5741	0.5391	0.021*
C9	0.91795 (12)	1.5753 (6)	0.68373 (15)	0.0163 (5)
H9	0.9630	1.6950	0.7008	0.020*
C10	0.87912 (12)	1.4754 (6)	0.75412 (15)	0.0142 (5)
C11	0.81194 (12)	1.2958 (6)	0.72724 (15)	0.0141 (5)
C12	0.90516 (13)	1.5567 (6)	0.85775 (15)	0.0181 (5)
H12A	0.9508	1.6891	0.8637	0.027*
H12B	0.9144	1.3457	0.8941	0.027*
H12C	0.8672	1.6880	0.8829	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0217 (3)	0.0290 (4)	0.0120 (3)	−0.0042 (2)	0.0040 (2)	0.0005 (2)
N1	0.0181 (10)	0.0211 (11)	0.0184 (10)	−0.0028 (8)	−0.0021 (7)	0.0020 (8)
N2	0.0164 (10)	0.0186 (10)	0.0089 (8)	0.0010 (8)	0.0022 (7)	0.0005 (7)
C1	0.0185 (12)	0.0208 (12)	0.0176 (12)	−0.0030 (10)	−0.0003 (9)	−0.0001 (9)
C2	0.0184 (11)	0.0191 (12)	0.0168 (11)	−0.0001 (9)	0.0019 (8)	−0.0006 (9)
C3	0.0178 (11)	0.0160 (12)	0.0144 (10)	0.0022 (9)	−0.0001 (8)	−0.0012 (9)
C4	0.0187 (12)	0.0171 (12)	0.0114 (10)	0.0016 (9)	0.0031 (8)	0.0019 (8)
C5	0.0201 (12)	0.0172 (11)	0.0095 (9)	0.0020 (9)	−0.0009 (8)	−0.0008 (8)
C6	0.0182 (11)	0.0150 (11)	0.0093 (10)	0.0039 (9)	0.0005 (8)	−0.0002 (8)
C7	0.0200 (12)	0.0209 (12)	0.0071 (9)	0.0046 (9)	0.0009 (8)	0.0011 (8)
C8	0.0203 (12)	0.0221 (12)	0.0109 (10)	0.0038 (9)	0.0041 (8)	0.0018 (8)
C9	0.0172 (11)	0.0171 (12)	0.0141 (10)	0.0004 (9)	0.0006 (8)	0.0000 (9)
C10	0.0190 (11)	0.0145 (11)	0.0086 (9)	0.0031 (9)	0.0009 (8)	−0.0006 (8)
C11	0.0159 (11)	0.0163 (11)	0.0097 (10)	0.0029 (9)	0.0012 (8)	0.0007 (8)
C12	0.0194 (11)	0.0252 (13)	0.0088 (10)	−0.0030 (10)	−0.0005 (8)	−0.0018 (9)

Cl1—C4	1.752 (2)	C6—C7	1.414 (3)
N1—C2	1.267 (3)	C6—C11	1.427 (3)
N1—C1	1.457 (3)	C7—C8	1.362 (3)
N2—C4	1.299 (3)	C7—H7	0.9500
N2—C11	1.372 (3)	C8—C9	1.417 (3)
C1—C1i	1.517 (4)	C8—H8	0.9500
C1—H1A	0.9900	C9—C10	1.372 (3)
C1—H1B	0.9900	C9—H9	0.9500
C2—C3	1.477 (3)	C10—C11	1.422 (3)
C2—H2	0.9500	C10—C12	1.506 (3)
C3—C5	1.380 (3)	C12—H12A	0.9800
C3—C4	1.425 (3)	C12—H12B	0.9800
C5—C6	1.405 (3)	C12—H12C	0.9800
C5—H5	0.9500
C2—N1—C1	117.8 (2)	C7—C6—C11	119.6 (2)
C4—N2—C11	117.47 (18)	C8—C7—C6	119.5 (2)
N1—C1—C1i	110.1 (2)	C8—C7—H7	120.2
N1—C1—H1A	109.6	C6—C7—H7	120.2
C1i—C1—H1A	109.6	C7—C8—C9	120.9 (2)
N1—C1—H1B	109.6	C7—C8—H8	119.5
C1i—C1—H1B	109.6	C9—C8—H8	119.5
H1A—C1—H1B	108.1	C10—C9—C8	121.6 (2)
N1—C2—C3	120.5 (2)	C10—C9—H9	119.2
N1—C2—H2	119.8	C8—C9—H9	119.2
C3—C2—H2	119.8	C9—C10—C11	118.47 (19)
C5—C3—C4	115.8 (2)	C9—C10—C12	121.8 (2)
C5—C3—C2	121.2 (2)	C11—C10—C12	119.77 (19)
C4—C3—C2	123.1 (2)	N2—C11—C10	118.43 (19)
N2—C4—C3	126.4 (2)	N2—C11—C6	121.7 (2)
N2—C4—Cl1	114.97 (16)	C10—C11—C6	119.9 (2)
C3—C4—Cl1	118.60 (18)	C10—C12—H12A	109.5
C3—C5—C6	120.9 (2)	C10—C12—H12B	109.5
C3—C5—H5	119.6	H12A—C12—H12B	109.5
C6—C5—H5	119.6	C10—C12—H12C	109.5
C5—C6—C7	122.61 (19)	H12A—C12—H12C	109.5
C5—C6—C11	117.8 (2)	H12B—C12—H12C	109.5
C2—N1—C1—C1i	−147.0 (3)	C11—C6—C7—C8	0.1 (3)
C1—N1—C2—C3	−177.6 (2)	C6—C7—C8—C9	−0.9 (3)
N1—C2—C3—C5	−12.4 (4)	C7—C8—C9—C10	0.8 (4)
N1—C2—C3—C4	167.0 (2)	C8—C9—C10—C11	0.1 (3)
C11—N2—C4—C3	−0.4 (4)	C8—C9—C10—C12	−178.7 (2)
C11—N2—C4—Cl1	−179.41 (16)	C4—N2—C11—C10	179.5 (2)
C5—C3—C4—N2	0.1 (4)	C4—N2—C11—C6	0.4 (3)
C2—C3—C4—N2	−179.3 (2)	C9—C10—C11—N2	179.8 (2)
C5—C3—C4—Cl1	179.03 (17)	C12—C10—C11—N2	−1.3 (3)
C2—C3—C4—Cl1	−0.3 (3)	C9—C10—C11—C6	−1.0 (3)
C4—C3—C5—C6	0.3 (3)	C12—C10—C11—C6	177.9 (2)
C2—C3—C5—C6	179.7 (2)	C5—C6—C11—N2	0.1 (3)
C3—C5—C6—C7	179.6 (2)	C7—C6—C11—N2	−180.0 (2)
C3—C5—C6—C11	−0.4 (3)	C5—C6—C11—C10	−179.1 (2)
C5—C6—C7—C8	−180.0 (2)	C7—C6—C11—C10	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1a···N1ii	0.99	2.59	3.299 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1a⋯N1i	0.99	2.59	3.299 (3)	128

Symmetry code: (i) .