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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2869.
Published online 2010 October 20. doi:  10.1107/S1600536810041309
PMCID: PMC3009292

N 1,N 2-Bis[(2-chloro-6-methyl­quinolin-3-yl)methyl­idene]ethane-1,2-diamine

Abstract

The title mol­ecule, C24H20Cl2N4, lies on an inversion center in an extended trans conformation. In the crystal, weak C—H(...)Cl inter­actions connect the mol­ecules into chains along [010].

Related literature

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

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Object name is e-66-o2869-scheme1.jpg

Experimental

Crystal data

  • C24H20Cl2N4
  • M r = 435.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2869-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

Quinoline Schiff base complexes are important class of compounds owing to their applications in the fields of environmental (Salhi et al., 2009), catalytic (Kano et al., 2003), DNA binding (Yong et al., 2009) and polymeric applications (Huiyan et al., 2009). Quinoline appended Schiff base complexes are also known for their photophysical properties (Liu et al., 2010; Wang et al., 2008). Related structures have already appeared in the literature (Assey et al., 2010; Dipesh et al., 2007). Herein we report the synthesis and crystal structure of the title compound, (I).

In the title compound, C24H20Cl2N4, the molecule is in an extended trans conformation and is located on a center of inversion between C12 and C12(-x, 1-y, -z). In the crystal structure, weak C—H···Cl interactions connect molecules into chains along [010].

Experimental

A mixture of 2-chloro-3-formyl-6-methylquinoline (0.2 g, 1 mM) and ethylenediamine (0.03 ml, 0.5 mM) was stirred in dichloromethane for 3 h at room temperature. The solvent from the reaction mixture was removed under reduced pressure, and the resulting solid was dried and purified by column chromatography using a 1:3 mixture of ethyl acetate and hexane. Recrystallization was by slow evaporation of a dichloromethane solution of (I) which yielded white coloured needle type crystals. M.p. 485–487 K. Yield: 83%.

Refinement

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distances of 0.93, 0.96 and 0.97 Å; Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The molecular structure of the title compound with unique part of molecule labeled. Ellipsoids drawn at 30% probability level. The unlabeled atoms are related by the symmetry operator (-x, 1-y, -z).
Fig. 2.
Part of the crystal structure viewed along the a axis showing the intermolecular C—H···Cl interactions as dashed lines.

Crystal data

C24H20Cl2N4Z = 1
Mr = 435.34F(000) = 226
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 4.4088 (8) ÅCell parameters from 2032 reflections
b = 7.2008 (11) Åθ = 5.3–73.4°
c = 16.9383 (18) ŵ = 2.93 mm1
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

Data collection

Oxford Diffraction Xcalibur diffractometer with Ruby Gemini detector2011 independent reflections
Radiation source: Enhance (Cu) X-ray Source1710 reflections with I > 2σ(I)
graphiteRint = 0.028
Detector resolution: 10.5081 pixels mm-1θmax = 73.6°, θmin = 5.3°
ω scansh = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)k = −8→8
Tmin = 0.378, Tmax = 1.000l = −20→21
3137 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.1105P)2 + 0.063P] where P = (Fo2 + 2Fc2)/3
2011 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl0.37544 (18)1.10262 (8)0.15067 (4)0.0756 (3)
N10.7058 (5)0.8882 (3)0.25986 (11)0.0533 (5)
N20.2488 (4)0.5727 (3)0.07293 (11)0.0532 (5)
C10.5343 (5)0.8821 (3)0.20006 (13)0.0500 (5)
C20.4730 (5)0.7140 (3)0.17101 (12)0.0459 (5)
C30.6152 (5)0.5444 (3)0.21010 (12)0.0463 (5)
H3A0.58440.43050.19340.056*
C40.8067 (5)0.5410 (3)0.27498 (12)0.0449 (5)
C50.9619 (5)0.3710 (3)0.31671 (13)0.0507 (5)
H5A0.93860.25460.30090.061*
C61.1455 (5)0.3738 (3)0.37978 (13)0.0540 (5)
C71.1733 (6)0.5531 (4)0.40297 (14)0.0597 (6)
H7A1.29400.55700.44640.072*
C81.0298 (6)0.7198 (3)0.36399 (14)0.0579 (6)
H8A1.05590.83480.38060.069*
C90.8427 (5)0.7190 (3)0.29892 (12)0.0470 (5)
C101.3155 (7)0.1939 (4)0.42378 (16)0.0696 (7)
H10A1.27240.08590.40040.104*
H10B1.24890.18860.47840.104*
H10C1.53390.19220.42060.104*
C110.2710 (5)0.7195 (3)0.10311 (13)0.0498 (5)
H11A0.15720.83580.08230.060*
C120.0528 (5)0.5922 (3)0.00365 (13)0.0517 (5)
H12A0.16770.6255−0.04390.062*
H12B−0.12570.69330.00900.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl0.1104 (6)0.0382 (4)0.0809 (5)−0.0165 (3)−0.0379 (4)−0.0011 (3)
N10.0706 (11)0.0410 (10)0.0537 (10)−0.0204 (8)−0.0112 (9)−0.0083 (7)
N20.0627 (11)0.0470 (10)0.0525 (10)−0.0123 (8)−0.0189 (8)−0.0078 (8)
C10.0654 (13)0.0386 (11)0.0499 (11)−0.0168 (9)−0.0107 (9)−0.0064 (8)
C20.0540 (11)0.0426 (11)0.0454 (10)−0.0174 (8)−0.0046 (8)−0.0085 (8)
C30.0602 (12)0.0397 (10)0.0450 (10)−0.0212 (9)−0.0062 (9)−0.0086 (8)
C40.0556 (11)0.0415 (10)0.0421 (10)−0.0185 (8)−0.0041 (8)−0.0068 (8)
C50.0639 (13)0.0427 (11)0.0497 (11)−0.0183 (9)−0.0072 (9)−0.0063 (9)
C60.0629 (13)0.0520 (13)0.0494 (11)−0.0170 (10)−0.0066 (9)−0.0024 (9)
C70.0728 (14)0.0613 (14)0.0507 (12)−0.0221 (11)−0.0205 (10)−0.0085 (10)
C80.0767 (15)0.0493 (12)0.0550 (12)−0.0235 (10)−0.0149 (11)−0.0132 (9)
C90.0592 (11)0.0425 (11)0.0444 (10)−0.0190 (8)−0.0036 (8)−0.0097 (8)
C100.0848 (17)0.0598 (15)0.0646 (15)−0.0155 (13)−0.0223 (13)0.0021 (12)
C110.0599 (12)0.0417 (11)0.0499 (11)−0.0125 (9)−0.0124 (9)−0.0047 (8)
C120.0600 (12)0.0471 (12)0.0498 (11)−0.0117 (9)−0.0158 (9)−0.0053 (9)

Geometric parameters (Å, °)

Cl—C11.747 (2)C6—C71.415 (3)
N1—C11.295 (3)C6—C101.504 (3)
N1—C91.366 (3)C7—C81.361 (4)
N2—C111.242 (3)C7—H7A0.9300
N2—C121.462 (3)C8—C91.401 (3)
C1—C21.428 (3)C8—H8A0.9300
C2—C31.375 (3)C10—H10A0.9600
C2—C111.473 (3)C10—H10B0.9600
C3—C41.405 (3)C10—H10C0.9600
C3—H3A0.9300C11—H11A0.9300
C4—C51.414 (3)C12—C12i1.508 (4)
C4—C91.422 (3)C12—H12A0.9700
C5—C61.368 (3)C12—H12B0.9700
C5—H5A0.9300
C1—N1—C9117.53 (17)C6—C7—H7A118.8
C11—N2—C12117.90 (19)C7—C8—C9120.3 (2)
N1—C1—C2126.0 (2)C7—C8—H8A119.9
N1—C1—Cl115.36 (15)C9—C8—H8A119.9
C2—C1—Cl118.65 (16)N1—C9—C8119.18 (18)
C3—C2—C1116.02 (18)N1—C9—C4122.22 (19)
C3—C2—C11121.40 (18)C8—C9—C4118.6 (2)
C1—C2—C11122.6 (2)C6—C10—H10A109.5
C2—C3—C4120.86 (18)C6—C10—H10B109.5
C2—C3—H3A119.6H10A—C10—H10B109.5
C4—C3—H3A119.6C6—C10—H10C109.5
C3—C4—C5123.30 (18)H10A—C10—H10C109.5
C3—C4—C9117.38 (19)H10B—C10—H10C109.5
C5—C4—C9119.33 (18)N2—C11—C2121.6 (2)
C6—C5—C4121.50 (19)N2—C11—H11A119.2
C6—C5—H5A119.3C2—C11—H11A119.2
C4—C5—H5A119.3N2—C12—C12i109.9 (2)
C5—C6—C7117.9 (2)N2—C12—H12A109.7
C5—C6—C10121.9 (2)C12i—C12—H12A109.7
C7—C6—C10120.2 (2)N2—C12—H12B109.7
C8—C7—C6122.4 (2)C12i—C12—H12B109.7
C8—C7—H7A118.8H12A—C12—H12B108.2
C9—N1—C1—C20.3 (4)C10—C6—C7—C8178.5 (2)
C9—N1—C1—Cl−178.07 (16)C6—C7—C8—C90.9 (4)
N1—C1—C2—C3−1.1 (4)C1—N1—C9—C8−179.9 (2)
Cl—C1—C2—C3177.21 (16)C1—N1—C9—C41.2 (3)
N1—C1—C2—C11179.1 (2)C7—C8—C9—N1−178.8 (2)
Cl—C1—C2—C11−2.6 (3)C7—C8—C9—C40.1 (4)
C1—C2—C3—C40.4 (3)C3—C4—C9—N1−1.8 (3)
C11—C2—C3—C4−179.78 (19)C5—C4—C9—N1178.25 (19)
C2—C3—C4—C5−179.1 (2)C3—C4—C9—C8179.34 (19)
C2—C3—C4—C90.9 (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—C60.2 (3)C3—C2—C11—N2−8.3 (3)
C4—C5—C6—C70.8 (3)C1—C2—C11—N2171.5 (2)
C4—C5—C6—C10−179.0 (2)C11—N2—C12—C12i−156.5 (2)
C5—C6—C7—C8−1.3 (4)

Symmetry codes: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···Clii0.932.863.780 (2)170

Symmetry codes: (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5149).

References

  • Assey, G. E., Butcher, R. J. & Gultneh, Y. (2010). Acta Cryst. E66, m620. [PMC free article] [PubMed]
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  • Kano, S., Nakano, H., Kojima, M., Baba, N. & Nakajima, K. (2003). Inorg. Chim. Acta, 349, 6–16.
  • Liu, -C. Z., Wang, -D. B., Yang, -Y. Z., Li, -R. T. & Li, Y. (2010). Inorg. Chem. Commun.13, 606–608.
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Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography