N,N′-Bis(5-chloro­salicyl­idene)­ethane-1,2-di­amine

The title compound, C₁₆H₁₄Cl₂N₂O₂, crystallizes in a centrosymmetric space group with one-half mol­ecule in the asymmetric unit. The salicyl­idene­imine moiety is almost planar. An intramolecular O—H...N hydrogen bond is observed [O—H...N = 2.611 (3) Å]. The packing of the mol­ecules in the crystal structure is stabilized by π–π stacking interactions between salicyl­idene­imine moieties.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.132
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

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Computing details

Data collection: WinAFC (Rigaku/MSC, 2003); cell refinement: WinAFC; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2003).

(I)

Crystal data

C16H14Cl2N2O2	F(000) = 348.00
Mr = 337.19	Dx = 1.451 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.379 (2) Å	θ = 15.1–17.1°
b = 11.655 (3) Å	µ = 0.43 mm^−1
c = 7.322 (3) Å	T = 298 K
β = 105.31 (3)°	Prismatic, yellow
V = 772.0 (4) Å^3	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	θmax = 27.5°
ω–2θ scans	h = −6→12
4540 measured reflections	k = 0→15
1776 independent reflections	l = −9→9
1069 reflections with F^2 > 2σ(F^2)	3 standard reflections every 150 reflections
Rint = 0.026	intensity decay: 0.8%

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[0.0031Fo^2 + σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.132	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.33 e Å^−3
1072 reflections	Δρmin = −0.28 e Å^−3
107 parameters

Special details

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl1	0.84953 (8)	0.13759 (7)	0.4783 (1)	0.0651 (3)
O1	0.3779 (2)	−0.1977 (2)	0.1936 (3)	0.0687 (7)
N1	0.2025 (2)	−0.0265 (2)	0.0576 (3)	0.0517 (7)
C1	0.4846 (3)	−0.1184 (2)	0.2567 (4)	0.0450 (7)
C2	0.6239 (3)	−0.1537 (2)	0.3563 (4)	0.0505 (8)
C3	0.7351 (3)	−0.0769 (2)	0.4246 (4)	0.0454 (7)
C4	0.7071 (3)	0.0395 (2)	0.3910 (4)	0.0430 (7)
C5	0.5695 (3)	0.0772 (2)	0.2929 (3)	0.0456 (7)
C6	0.4557 (3)	−0.0000 (2)	0.2237 (3)	0.0405 (7)
C7	0.3090 (3)	0.0408 (3)	0.1221 (4)	0.0489 (7)
C8	0.0593 (3)	0.0206 (3)	−0.0442 (4)	0.0596 (9)
H1	0.2808	−0.1635	0.1477	0.077*
H2	0.6428	−0.2333	0.3778	0.059*
H3	0.8305	−0.1017	0.4943	0.053*
H4	0.5523	0.1571	0.2724	0.054*
H5	0.2934	0.1210	0.1039	0.058*
H6	0.0635	0.1020	−0.0371	0.068*
H7	0.0360	−0.0025	−0.1730	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0446 (4)	0.0643 (5)	0.0787 (6)	−0.0115 (3)	0.0028 (4)	0.0045 (4)
O1	0.041 (1)	0.052 (1)	0.097 (2)	0.0011 (9)	−0.009 (1)	−0.017 (1)
N1	0.032 (1)	0.070 (1)	0.048 (1)	0.009 (1)	0.001 (1)	0.003 (1)
C1	0.036 (1)	0.048 (1)	0.048 (1)	0.004 (1)	0.006 (1)	−0.008 (1)
C2	0.044 (2)	0.045 (1)	0.057 (2)	0.011 (1)	0.003 (1)	−0.002 (1)
C3	0.031 (1)	0.055 (2)	0.046 (1)	0.007 (1)	0.002 (1)	−0.002 (1)
C4	0.035 (1)	0.053 (1)	0.039 (1)	0.000 (1)	0.007 (1)	0.000 (1)
C5	0.042 (1)	0.047 (1)	0.047 (1)	0.006 (1)	0.011 (1)	0.005 (1)
C6	0.032 (1)	0.049 (1)	0.038 (1)	0.008 (1)	0.006 (1)	0.003 (1)
C7	0.035 (1)	0.059 (2)	0.050 (2)	0.011 (1)	0.007 (1)	0.009 (1)
C8	0.032 (1)	0.080 (2)	0.058 (2)	0.015 (1)	−0.005 (1)	0.007 (1)

Geometric parameters (Å, º)

Cl1—C4	1.746 (3)	C3—H3	0.9505
O1—C1	1.351 (3)	C4—C5	1.373 (3)
O1—H1	0.9693	C5—C6	1.386 (3)
N1—C7	1.259 (4)	C5—H4	0.9502
N1—C8	1.460 (3)	C6—C7	1.460 (3)
C1—C2	1.380 (3)	C7—H5	0.9501
C1—C6	1.415 (4)	C8—H6	0.9504
C2—C3	1.365 (4)	C8—H7	0.9491)
C2—H2	0.9498	C8—C8^i	1.505 (4)
C3—C4	1.391 (4)
C1···C4^ii	3.631 (4)	C4···C6^ii	3.574 (4)
C1···C5^ii	3.500 (4)	C4···C7^ii	3.727 (4)
C2···C5^ii	3.626 (4)	C5···C6^ii	3.720 (4)
C3···C6^ii	3.615 (4)	C6···C6^ii	3.910 (3)
C3···C7^ii	3.477 (4)
C1—O1—H1	112.37	C6—C5—H4	119.76
C7—N1—C8	119.3 (3)	C6—C5—C4	120.7 (2)
C2—C1—C6	119.6 (2)	H4—C5—C4	119.55
C2—C1—O1	119.3 (2)	C7—C6—C1	121.2 (2)
C6—C1—O1	121.1 (2)	C7—C6—C5	120.4 (2)
C3—C2—H2	119.25	C1—C6—C5	118.4 (2)
C3—C2—C1	121.5 (3)	H5—C7—N1	118.85
H2—C2—C1	119.21	H5—C7—C6	118.78
C4—C3—H3	119.90	N1—C7—C6	122.4 (3)
C4—C3—C2	119.0 (2)	H6—C8—H7	109.44
H3—C3—C2	121.14	H6—C8—N1	109.15
C5—C4—Cl1	120.3 (2)	H7—C8—N1	109.88
C5—C4—C3	120.8 (2)	N1—C8—C8^i	110.2 (2)
Cl1—C4—C3	118.9 (2)
C8—N1—C7—C6	−179.4 (2)	C2—C3—C4—C5	0.8 (4)
O1—C1—C2—C3	−179.4 (3)	Cl1—C4—C5—C6	−179.8 (2)
C6—C1—C2—C3	0.1 (5)	C3—C4—C5—C6	−0.5 (4)
O1—C1—C6—C5	179.7 (3)	C4—C5—C6—C1	0.0 (4)
O1—C1—C6—C7	0.7 (4)	C4—C5—C6—C7	179.0 (3)
C2—C1—C6—C5	0.2 (4)	C1—C6—C7—N1	−0.7 (4)
C2—C1—C6—C7	−178.8 (3)	C5—C6—C7—N1	−179.7 (3)
C1—C2—C3—C4	−0.6 (4)	C7—N1—C8—C8^i	−125.2 (3)
C2—C3—C4—Cl1	−179.9 (2)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.97	1.80	2.611 (3)	138