N,N-Bis[(2-chloro-6-methyl-quinolin-3-yl)methyl-idene]ethane-1,2-diamine.

The title mol-ecule, C(24)H(20)Cl(2)N(4), lies on an inversion center in an extended trans conformation. In the crystal, weak C-H⋯Cl inter-actions connect the mol-ecules into chains along [010].

Related literature

For general background to Schiff bases, see: Schiff (1864 ▶); Huiyan et al. (2009 ▶); Kano et al. (2003 ▶); Liu et al. (2010 ▶); Salhi et al. (2009 ▶); Wang et al. (2008 ▶); Yong & Zheng (2009 ▶). For related structures, see: Assey et al. (2010 ▶); Dipesh et al. (2007 ▶).

Experimental

Crystal data

C24H20Cl2N4

M = 435.34

Triclinic,

a = 4.4088 (8) Å

b = 7.2008 (11) Å

c = 16.9383 (18) Å

α = 84.236 (11)°

β = 87.924 (12)°

γ = 78.698 (14)°

V = 524.57 (14) Å3

Z = 1

Cu Kα radiation

μ = 2.93 mm−1

T = 295 K

0.46 × 0.37 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby Gemini detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.378, T max = 1.000

3137 measured reflections

2011 independent reflections

1710 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.168

S = 1.05

2011 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810041309/lh5149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041309/lh5149Isup2.hkl

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

C24H20Cl2N4	Z = 1
Mr = 435.34	F(000) = 226
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 4.4088 (8) Å	Cell parameters from 2032 reflections
b = 7.2008 (11) Å	θ = 5.3–73.4°
c = 16.9383 (18) Å	µ = 2.93 mm−1
α = 84.236 (11)°	T = 295 K
β = 87.924 (12)°	Plate, colorless
γ = 78.698 (14)°	0.46 × 0.37 × 0.15 mm
V = 524.57 (14) Å3

Oxford Diffraction Xcalibur diffractometer with Ruby Gemini detector	2011 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1710 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 73.6°, θmin = 5.3°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −8→8
Tmin = 0.378, Tmax = 1.000	l = −20→21
3137 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1105P)2 + 0.063P] where P = (Fo2 + 2Fc2)/3
2011 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.29 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
Cl	0.37544 (18)	1.10262 (8)	0.15067 (4)	0.0756 (3)
N1	0.7058 (5)	0.8882 (3)	0.25986 (11)	0.0533 (5)
N2	0.2488 (4)	0.5727 (3)	0.07293 (11)	0.0532 (5)
C1	0.5343 (5)	0.8821 (3)	0.20006 (13)	0.0500 (5)
C2	0.4730 (5)	0.7140 (3)	0.17101 (12)	0.0459 (5)
C3	0.6152 (5)	0.5444 (3)	0.21010 (12)	0.0463 (5)
H3A	0.5844	0.4305	0.1934	0.056*
C4	0.8067 (5)	0.5410 (3)	0.27498 (12)	0.0449 (5)
C5	0.9619 (5)	0.3710 (3)	0.31671 (13)	0.0507 (5)
H5A	0.9386	0.2546	0.3009	0.061*
C6	1.1455 (5)	0.3738 (3)	0.37978 (13)	0.0540 (5)
C7	1.1733 (6)	0.5531 (4)	0.40297 (14)	0.0597 (6)
H7A	1.2940	0.5570	0.4464	0.072*
C8	1.0298 (6)	0.7198 (3)	0.36399 (14)	0.0579 (6)
H8A	1.0559	0.8348	0.3806	0.069*
C9	0.8427 (5)	0.7190 (3)	0.29892 (12)	0.0470 (5)
C10	1.3155 (7)	0.1939 (4)	0.42378 (16)	0.0696 (7)
H10A	1.2724	0.0859	0.4004	0.104*
H10B	1.2489	0.1886	0.4784	0.104*
H10C	1.5339	0.1922	0.4206	0.104*
C11	0.2710 (5)	0.7195 (3)	0.10311 (13)	0.0498 (5)
H11A	0.1572	0.8358	0.0823	0.060*
C12	0.0528 (5)	0.5922 (3)	0.00365 (13)	0.0517 (5)
H12A	0.1677	0.6255	−0.0439	0.062*
H12B	−0.1257	0.6933	0.0090	0.062*

	U11	U22	U33	U12	U13	U23
Cl	0.1104 (6)	0.0382 (4)	0.0809 (5)	−0.0165 (3)	−0.0379 (4)	−0.0011 (3)
N1	0.0706 (11)	0.0410 (10)	0.0537 (10)	−0.0204 (8)	−0.0112 (9)	−0.0083 (7)
N2	0.0627 (11)	0.0470 (10)	0.0525 (10)	−0.0123 (8)	−0.0189 (8)	−0.0078 (8)
C1	0.0654 (13)	0.0386 (11)	0.0499 (11)	−0.0168 (9)	−0.0107 (9)	−0.0064 (8)
C2	0.0540 (11)	0.0426 (11)	0.0454 (10)	−0.0174 (8)	−0.0046 (8)	−0.0085 (8)
C3	0.0602 (12)	0.0397 (10)	0.0450 (10)	−0.0212 (9)	−0.0062 (9)	−0.0086 (8)
C4	0.0556 (11)	0.0415 (10)	0.0421 (10)	−0.0185 (8)	−0.0041 (8)	−0.0068 (8)
C5	0.0639 (13)	0.0427 (11)	0.0497 (11)	−0.0183 (9)	−0.0072 (9)	−0.0063 (9)
C6	0.0629 (13)	0.0520 (13)	0.0494 (11)	−0.0170 (10)	−0.0066 (9)	−0.0024 (9)
C7	0.0728 (14)	0.0613 (14)	0.0507 (12)	−0.0221 (11)	−0.0205 (10)	−0.0085 (10)
C8	0.0767 (15)	0.0493 (12)	0.0550 (12)	−0.0235 (10)	−0.0149 (11)	−0.0132 (9)
C9	0.0592 (11)	0.0425 (11)	0.0444 (10)	−0.0190 (8)	−0.0036 (8)	−0.0097 (8)
C10	0.0848 (17)	0.0598 (15)	0.0646 (15)	−0.0155 (13)	−0.0223 (13)	0.0021 (12)
C11	0.0599 (12)	0.0417 (11)	0.0499 (11)	−0.0125 (9)	−0.0124 (9)	−0.0047 (8)
C12	0.0600 (12)	0.0471 (12)	0.0498 (11)	−0.0117 (9)	−0.0158 (9)	−0.0053 (9)

Cl—C1	1.747 (2)	C6—C7	1.415 (3)
N1—C1	1.295 (3)	C6—C10	1.504 (3)
N1—C9	1.366 (3)	C7—C8	1.361 (4)
N2—C11	1.242 (3)	C7—H7A	0.9300
N2—C12	1.462 (3)	C8—C9	1.401 (3)
C1—C2	1.428 (3)	C8—H8A	0.9300
C2—C3	1.375 (3)	C10—H10A	0.9600
C2—C11	1.473 (3)	C10—H10B	0.9600
C3—C4	1.405 (3)	C10—H10C	0.9600
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.414 (3)	C12—C12i	1.508 (4)
C4—C9	1.422 (3)	C12—H12A	0.9700
C5—C6	1.368 (3)	C12—H12B	0.9700
C5—H5A	0.9300
C1—N1—C9	117.53 (17)	C6—C7—H7A	118.8
C11—N2—C12	117.90 (19)	C7—C8—C9	120.3 (2)
N1—C1—C2	126.0 (2)	C7—C8—H8A	119.9
N1—C1—Cl	115.36 (15)	C9—C8—H8A	119.9
C2—C1—Cl	118.65 (16)	N1—C9—C8	119.18 (18)
C3—C2—C1	116.02 (18)	N1—C9—C4	122.22 (19)
C3—C2—C11	121.40 (18)	C8—C9—C4	118.6 (2)
C1—C2—C11	122.6 (2)	C6—C10—H10A	109.5
C2—C3—C4	120.86 (18)	C6—C10—H10B	109.5
C2—C3—H3A	119.6	H10A—C10—H10B	109.5
C4—C3—H3A	119.6	C6—C10—H10C	109.5
C3—C4—C5	123.30 (18)	H10A—C10—H10C	109.5
C3—C4—C9	117.38 (19)	H10B—C10—H10C	109.5
C5—C4—C9	119.33 (18)	N2—C11—C2	121.6 (2)
C6—C5—C4	121.50 (19)	N2—C11—H11A	119.2
C6—C5—H5A	119.3	C2—C11—H11A	119.2
C4—C5—H5A	119.3	N2—C12—C12i	109.9 (2)
C5—C6—C7	117.9 (2)	N2—C12—H12A	109.7
C5—C6—C10	121.9 (2)	C12i—C12—H12A	109.7
C7—C6—C10	120.2 (2)	N2—C12—H12B	109.7
C8—C7—C6	122.4 (2)	C12i—C12—H12B	109.7
C8—C7—H7A	118.8	H12A—C12—H12B	108.2
C9—N1—C1—C2	0.3 (4)	C10—C6—C7—C8	178.5 (2)
C9—N1—C1—Cl	−178.07 (16)	C6—C7—C8—C9	0.9 (4)
N1—C1—C2—C3	−1.1 (4)	C1—N1—C9—C8	−179.9 (2)
Cl—C1—C2—C3	177.21 (16)	C1—N1—C9—C4	1.2 (3)
N1—C1—C2—C11	179.1 (2)	C7—C8—C9—N1	−178.8 (2)
Cl—C1—C2—C11	−2.6 (3)	C7—C8—C9—C4	0.1 (4)
C1—C2—C3—C4	0.4 (3)	C3—C4—C9—N1	−1.8 (3)
C11—C2—C3—C4	−179.78 (19)	C5—C4—C9—N1	178.25 (19)
C2—C3—C4—C5	−179.1 (2)	C3—C4—C9—C8	179.34 (19)
C2—C3—C4—C9	0.9 (3)	C5—C4—C9—C8	−0.6 (3)
C3—C4—C5—C6	−179.8 (2)	C12—N2—C11—C2	−177.51 (19)
C9—C4—C5—C6	0.2 (3)	C3—C2—C11—N2	−8.3 (3)
C4—C5—C6—C7	0.8 (3)	C1—C2—C11—N2	171.5 (2)
C4—C5—C6—C10	−179.0 (2)	C11—N2—C12—C12i	−156.5 (2)
C5—C6—C7—C8	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Clii	0.93	2.86	3.780 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cli	0.93	2.86	3.780 (2)	170

Symmetry code: (i) .