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The title compound, C16H12Cl4N2, contains two chloro-substituted benzyl rings connected through a diimine group. The mol­ecule lies across a center of symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055122/ng2359sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055122/ng2359Isup2.hkl
Contains datablock I

CCDC reference: 663475

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.068
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C2 .. 5.51 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C8 .. 5.59 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In the current study the structure of the title compound, which can be potentially used as tetradentate ligand is investigated (Helldörfer et al., 2003 & Richmond et al., 1988). This structure is isomer with what we have recently reported with different chloro-substituted benzaldehyde derivative (Abbasi et al., 2007). Solvatochromic phenomenon in the mixed-chelates metal complexes with similar structure has received great attention (Asadi et al., 2005).

The moleculare structure of (I) and the atom-numbering scheme are shown in Fig. 1. The asymmetric unit contains one half-molecule in the centrosymmetric title compound with a centre of symmetry between the two central carbon atoms. Relatively weak intermolecular van der Waals interactions between the adjacent molecules are responsible to stabilize the crystal structure. Due to the center of symmetry in the middle of molecule, the two benzyl rings are located in two parallel planes with zero dihedral angle. Also, for the same reason the two carbon and two nitrogen atoms (N1–C8–C8–N1) are in a common plane with torsion angle of 180.0°. The structure of the title compound was corroborated by IR and 1H NMR spectroscopy.

Related literature top

For the structure of another chlorine-substituted compound, see: Abbasi et al. (2007). These compounds are capable of tetradentate coordination to metals; see Helldörfer et al. (2003); Richmond et al. (1988). For related literature, see: Asadi et al. (2005).

Experimental top

The title compound was synthesized by the reaction of 2,3-dichlorobenzaldehyde (100 mmol) in absolute ethanol (30 ml) and ethylenediamine (50 mmol) followed by 24 h stirring. The colorless crystalline solid was obtained (17 mmol, 57%). The precipitates was filtered and washed with ether and hexane. Crystals suitable for crystallography were obtained by recrystallization from dichloromethane.

Refinement top

All H atoms were geometrically positioned and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1997); cell refinement: IPDS Software (Stoe & Cie, 1997); data reduction: IPDS Software (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are shown as circles of arbitrary radii.
N,N'-Bis(2,3-dichlorobenzylidene)ethylenediamine top
Crystal data top
C16H12Cl4N2F(000) = 380
Mr = 374.08Dx = 1.515 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4730 reflections
a = 7.5695 (9) Åθ = 3.5–26.0°
b = 12.0686 (13) ŵ = 0.72 mm1
c = 9.1636 (7) ÅT = 290 K
β = 101.637 (9)°Needle, colorless
V = 819.92 (15) Å30.15 × 0.12 × 0.10 mm
Z = 2
Data collection top
STOE IPDS
diffractometer
1579 independent reflections
Radiation source: fine-focus sealed tube623 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Area detector – phi oscillation scansθmax = 26.0°, θmin = 3.9°
Absorption correction: numerical
(X-RED; Stoe & Cie, 1997)
h = 89
Tmin = 0.892, Tmax = 0.915k = 1414
4730 measured reflectionsl = 911
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 0.83 w = 1/[σ2(Fo2) + (0.025P)2]
where P = (Fo2 + 2Fc2)/3
1579 reflections(Δ/σ)max < 0.001
100 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C16H12Cl4N2V = 819.92 (15) Å3
Mr = 374.08Z = 2
Monoclinic, P21/nMo Kα radiation
a = 7.5695 (9) ŵ = 0.72 mm1
b = 12.0686 (13) ÅT = 290 K
c = 9.1636 (7) Å0.15 × 0.12 × 0.10 mm
β = 101.637 (9)°
Data collection top
STOE IPDS
diffractometer
1579 independent reflections
Absorption correction: numerical
(X-RED; Stoe & Cie, 1997)
623 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.915Rint = 0.058
4730 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.068H-atom parameters constrained
S = 0.83Δρmax = 0.21 e Å3
1579 reflectionsΔρmin = 0.17 e Å3
100 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl10.75551 (12)0.30320 (7)0.46001 (8)0.0687 (3)
Cl20.51851 (12)0.39080 (7)0.16625 (8)0.0716 (3)
N10.9559 (3)0.5420 (2)0.8021 (3)0.0538 (7)
C11.0531 (4)0.4926 (3)0.9400 (2)0.0582 (10)
H1A1.17010.52770.96970.070*
H1B1.07200.41430.92490.070*
C20.8958 (4)0.4790 (3)0.6963 (3)0.0507 (9)
H20.91980.40360.70870.061*
C30.7886 (4)0.5169 (3)0.5524 (3)0.0390 (8)
C40.7535 (4)0.6297 (3)0.5276 (3)0.0485 (8)
H40.80020.68020.60210.058*
C50.6513 (4)0.6679 (3)0.3953 (3)0.0556 (9)
H50.63030.74340.38120.067*
C60.5803 (4)0.5945 (3)0.2843 (3)0.0514 (9)
H60.51120.62010.19510.062*
C70.6123 (4)0.4821 (3)0.3060 (3)0.0453 (8)
C80.7172 (4)0.4445 (2)0.4389 (3)0.0431 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0765 (7)0.0482 (6)0.0776 (6)0.0112 (5)0.0066 (5)0.0045 (5)
Cl20.0668 (6)0.0830 (8)0.0599 (5)0.0036 (5)0.0003 (4)0.0179 (5)
N10.0573 (19)0.064 (2)0.0397 (15)0.0015 (15)0.0085 (14)0.0001 (14)
C10.049 (3)0.081 (3)0.043 (2)0.0091 (19)0.0052 (16)0.0010 (19)
C20.048 (2)0.057 (2)0.050 (2)0.0126 (19)0.0168 (18)0.0082 (18)
C30.036 (2)0.044 (2)0.0385 (17)0.0051 (17)0.0113 (15)0.0012 (17)
C40.050 (2)0.045 (2)0.0524 (19)0.0065 (19)0.0148 (17)0.0030 (17)
C50.058 (2)0.052 (2)0.058 (2)0.0018 (19)0.0143 (19)0.0094 (19)
C60.047 (2)0.064 (3)0.0429 (19)0.0013 (19)0.0075 (16)0.0099 (19)
C70.038 (2)0.054 (2)0.0434 (19)0.0051 (18)0.0072 (16)0.0046 (17)
C80.036 (2)0.043 (2)0.0535 (19)0.0062 (16)0.0153 (16)0.0029 (16)
Geometric parameters (Å, º) top
Cl1—C81.734 (3)C3—C81.383 (3)
Cl2—C71.730 (3)C3—C41.396 (3)
N1—C21.243 (3)C4—C51.380 (3)
N1—C11.456 (3)C4—H40.9300
C1—C1i1.497 (5)C5—C61.373 (4)
C1—H1A0.9700C5—H50.9300
C1—H1B0.9700C6—C71.385 (3)
C2—C31.475 (3)C6—H60.9300
C2—H20.9300C7—C81.389 (3)
C2—N1—C1117.9 (3)C5—C4—H4119.2
N1—C1—C1i109.7 (3)C3—C4—H4119.2
N1—C1—H1A109.7C6—C5—C4120.1 (3)
C1i—C1—H1A109.7C6—C5—H5119.9
N1—C1—H1B109.7C4—C5—H5119.9
C1i—C1—H1B109.7C5—C6—C7119.6 (3)
H1A—C1—H1B108.2C5—C6—H6120.2
N1—C2—C3123.8 (3)C7—C6—H6120.2
N1—C2—H2118.1C6—C7—C8119.9 (3)
C3—C2—H2118.1C6—C7—Cl2118.9 (2)
C8—C3—C4117.5 (2)C8—C7—Cl2121.2 (3)
C8—C3—C2122.5 (3)C3—C8—C7121.4 (3)
C4—C3—C2120.0 (3)C3—C8—Cl1120.4 (2)
C5—C4—C3121.5 (3)C7—C8—Cl1118.2 (2)
C2—N1—C1—C1i112.7 (3)C5—C6—C7—Cl2178.8 (2)
C1—N1—C2—C3177.4 (2)C4—C3—C8—C71.0 (4)
N1—C2—C3—C8177.3 (3)C2—C3—C8—C7178.1 (2)
N1—C2—C3—C41.8 (4)C4—C3—C8—Cl1179.6 (2)
C8—C3—C4—C50.2 (4)C2—C3—C8—Cl11.4 (4)
C2—C3—C4—C5178.9 (3)C6—C7—C8—C31.2 (4)
C3—C4—C5—C60.3 (4)Cl2—C7—C8—C3178.3 (2)
C4—C5—C6—C70.1 (4)C6—C7—C8—Cl1179.3 (2)
C5—C6—C7—C80.7 (4)Cl2—C7—C8—Cl11.2 (3)
Symmetry code: (i) x+2, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC16H12Cl4N2
Mr374.08
Crystal system, space groupMonoclinic, P21/n
Temperature (K)290
a, b, c (Å)7.5695 (9), 12.0686 (13), 9.1636 (7)
β (°) 101.637 (9)
V3)819.92 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.72
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerSTOE IPDS
diffractometer
Absorption correctionNumerical
(X-RED; Stoe & Cie, 1997)
Tmin, Tmax0.892, 0.915
No. of measured, independent and
observed [I > 2σ(I)] reflections
4730, 1579, 623
Rint0.058
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.068, 0.83
No. of reflections1579
No. of parameters100
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.17

Computer programs: IPDS Software (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2001), PLATON (Spek, 2003).

Selected bond lengths (Å) top
Cl1—C81.734 (3)N1—C11.456 (3)
Cl2—C71.730 (3)C1—C1i1.497 (5)
N1—C21.243 (3)C2—C31.475 (3)
Symmetry code: (i) x+2, y+1, z+2.
 

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