Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055122/ng2359sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055122/ng2359Isup2.hkl |
CCDC reference: 663475
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.
All H atoms were geometrically positioned and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
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).
Fig. 1. Molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are shown as circles of arbitrary radii. |
C16H12Cl4N2 | F(000) = 380 |
Mr = 374.08 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4730 reflections |
a = 7.5695 (9) Å | θ = 3.5–26.0° |
b = 12.0686 (13) Å | µ = 0.72 mm−1 |
c = 9.1636 (7) Å | T = 290 K |
β = 101.637 (9)° | Needle, colorless |
V = 819.92 (15) Å3 | 0.15 × 0.12 × 0.10 mm |
Z = 2 |
STOE IPDS diffractometer | 1579 independent reflections |
Radiation source: fine-focus sealed tube | 623 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Area detector – phi oscillation scans | θmax = 26.0°, θmin = 3.9° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | h = −8→9 |
Tmin = 0.892, Tmax = 0.915 | k = −14→14 |
4730 measured reflections | l = −9→11 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.068 | H-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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C16H12Cl4N2 | V = 819.92 (15) Å3 |
Mr = 374.08 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5695 (9) Å | µ = 0.72 mm−1 |
b = 12.0686 (13) Å | T = 290 K |
c = 9.1636 (7) Å | 0.15 × 0.12 × 0.10 mm |
β = 101.637 (9)° |
STOE IPDS diffractometer | 1579 independent reflections |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | 623 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 0.915 | Rint = 0.058 |
4730 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.068 | H-atom parameters constrained |
S = 0.83 | Δρmax = 0.21 e Å−3 |
1579 reflections | Δρmin = −0.17 e Å−3 |
100 parameters |
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 | 0.75551 (12) | 0.30320 (7) | 0.46001 (8) | 0.0687 (3) | |
Cl2 | 0.51851 (12) | 0.39080 (7) | 0.16625 (8) | 0.0716 (3) | |
N1 | 0.9559 (3) | 0.5420 (2) | 0.8021 (3) | 0.0538 (7) | |
C1 | 1.0531 (4) | 0.4926 (3) | 0.9400 (2) | 0.0582 (10) | |
H1A | 1.1701 | 0.5277 | 0.9697 | 0.070* | |
H1B | 1.0720 | 0.4143 | 0.9249 | 0.070* | |
C2 | 0.8958 (4) | 0.4790 (3) | 0.6963 (3) | 0.0507 (9) | |
H2 | 0.9198 | 0.4036 | 0.7087 | 0.061* | |
C3 | 0.7886 (4) | 0.5169 (3) | 0.5524 (3) | 0.0390 (8) | |
C4 | 0.7535 (4) | 0.6297 (3) | 0.5276 (3) | 0.0485 (8) | |
H4 | 0.8002 | 0.6802 | 0.6021 | 0.058* | |
C5 | 0.6513 (4) | 0.6679 (3) | 0.3953 (3) | 0.0556 (9) | |
H5 | 0.6303 | 0.7434 | 0.3812 | 0.067* | |
C6 | 0.5803 (4) | 0.5945 (3) | 0.2843 (3) | 0.0514 (9) | |
H6 | 0.5112 | 0.6201 | 0.1951 | 0.062* | |
C7 | 0.6123 (4) | 0.4821 (3) | 0.3060 (3) | 0.0453 (8) | |
C8 | 0.7172 (4) | 0.4445 (2) | 0.4389 (3) | 0.0431 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0765 (7) | 0.0482 (6) | 0.0776 (6) | 0.0112 (5) | 0.0066 (5) | −0.0045 (5) |
Cl2 | 0.0668 (6) | 0.0830 (8) | 0.0599 (5) | −0.0036 (5) | 0.0003 (4) | −0.0179 (5) |
N1 | 0.0573 (19) | 0.064 (2) | 0.0397 (15) | 0.0015 (15) | 0.0085 (14) | 0.0001 (14) |
C1 | 0.049 (3) | 0.081 (3) | 0.043 (2) | 0.0091 (19) | 0.0052 (16) | 0.0010 (19) |
C2 | 0.048 (2) | 0.057 (2) | 0.050 (2) | 0.0126 (19) | 0.0168 (18) | 0.0082 (18) |
C3 | 0.036 (2) | 0.044 (2) | 0.0385 (17) | −0.0051 (17) | 0.0113 (15) | −0.0012 (17) |
C4 | 0.050 (2) | 0.045 (2) | 0.0524 (19) | −0.0065 (19) | 0.0148 (17) | −0.0030 (17) |
C5 | 0.058 (2) | 0.052 (2) | 0.058 (2) | −0.0018 (19) | 0.0143 (19) | 0.0094 (19) |
C6 | 0.047 (2) | 0.064 (3) | 0.0429 (19) | 0.0013 (19) | 0.0075 (16) | 0.0099 (19) |
C7 | 0.038 (2) | 0.054 (2) | 0.0434 (19) | −0.0051 (18) | 0.0072 (16) | −0.0046 (17) |
C8 | 0.036 (2) | 0.043 (2) | 0.0535 (19) | 0.0062 (16) | 0.0153 (16) | 0.0029 (16) |
Cl1—C8 | 1.734 (3) | C3—C8 | 1.383 (3) |
Cl2—C7 | 1.730 (3) | C3—C4 | 1.396 (3) |
N1—C2 | 1.243 (3) | C4—C5 | 1.380 (3) |
N1—C1 | 1.456 (3) | C4—H4 | 0.9300 |
C1—C1i | 1.497 (5) | C5—C6 | 1.373 (4) |
C1—H1A | 0.9700 | C5—H5 | 0.9300 |
C1—H1B | 0.9700 | C6—C7 | 1.385 (3) |
C2—C3 | 1.475 (3) | C6—H6 | 0.9300 |
C2—H2 | 0.9300 | C7—C8 | 1.389 (3) |
C2—N1—C1 | 117.9 (3) | C5—C4—H4 | 119.2 |
N1—C1—C1i | 109.7 (3) | C3—C4—H4 | 119.2 |
N1—C1—H1A | 109.7 | C6—C5—C4 | 120.1 (3) |
C1i—C1—H1A | 109.7 | C6—C5—H5 | 119.9 |
N1—C1—H1B | 109.7 | C4—C5—H5 | 119.9 |
C1i—C1—H1B | 109.7 | C5—C6—C7 | 119.6 (3) |
H1A—C1—H1B | 108.2 | C5—C6—H6 | 120.2 |
N1—C2—C3 | 123.8 (3) | C7—C6—H6 | 120.2 |
N1—C2—H2 | 118.1 | C6—C7—C8 | 119.9 (3) |
C3—C2—H2 | 118.1 | C6—C7—Cl2 | 118.9 (2) |
C8—C3—C4 | 117.5 (2) | C8—C7—Cl2 | 121.2 (3) |
C8—C3—C2 | 122.5 (3) | C3—C8—C7 | 121.4 (3) |
C4—C3—C2 | 120.0 (3) | C3—C8—Cl1 | 120.4 (2) |
C5—C4—C3 | 121.5 (3) | C7—C8—Cl1 | 118.2 (2) |
C2—N1—C1—C1i | −112.7 (3) | C5—C6—C7—Cl2 | 178.8 (2) |
C1—N1—C2—C3 | 177.4 (2) | C4—C3—C8—C7 | −1.0 (4) |
N1—C2—C3—C8 | −177.3 (3) | C2—C3—C8—C7 | 178.1 (2) |
N1—C2—C3—C4 | 1.8 (4) | C4—C3—C8—Cl1 | 179.6 (2) |
C8—C3—C4—C5 | 0.2 (4) | C2—C3—C8—Cl1 | −1.4 (4) |
C2—C3—C4—C5 | −178.9 (3) | C6—C7—C8—C3 | 1.2 (4) |
C3—C4—C5—C6 | 0.3 (4) | Cl2—C7—C8—C3 | −178.3 (2) |
C4—C5—C6—C7 | −0.1 (4) | C6—C7—C8—Cl1 | −179.3 (2) |
C5—C6—C7—C8 | −0.7 (4) | Cl2—C7—C8—Cl1 | 1.2 (3) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C16H12Cl4N2 |
Mr | 374.08 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 290 |
a, b, c (Å) | 7.5695 (9), 12.0686 (13), 9.1636 (7) |
β (°) | 101.637 (9) |
V (Å3) | 819.92 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | STOE IPDS diffractometer |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1997) |
Tmin, Tmax | 0.892, 0.915 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4730, 1579, 623 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.068, 0.83 |
No. of reflections | 1579 |
No. of parameters | 100 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.17 |
Computer programs: IPDS Software (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2001), PLATON (Spek, 2003).
Cl1—C8 | 1.734 (3) | N1—C1 | 1.456 (3) |
Cl2—C7 | 1.730 (3) | C1—C1i | 1.497 (5) |
N1—C2 | 1.243 (3) | C2—C3 | 1.475 (3) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
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.