N,N'-Bis(4-chloro-3-fluoro-benzyl-idene)ethane-1,2-diamine.

The asymmetric unit of the title Schiff base compound, C(16)H(12)Cl(2)F(2)N(2), contains one half of the centrosymmetric mol-ecule. Mol-ecules related by translation along the a axis form stacks with short inter-molecular C⋯C distances of 3.429 (3) Å. The crystal packing also exhibits short inter-molecular Cl⋯F contacts of 3.087 (1) Å.

Related literature

For a related structure, see Fun & Kia (2008 ▶). For general background, see: Pal et al. (2005 ▶); Calligaris & Randaccio (1987 ▶); Hou et al. (2001 ▶); Ren et al. (2002 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12Cl2F2N2

M = 341.18

Monoclinic,

a = 4.6542 (1) Å

b = 23.1343 (6) Å

c = 6.9961 (2) Å

β = 107.063 (2)°

V = 720.12 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 100.0 (1) K

0.51 × 0.05 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.795, T max = 0.983

17372 measured reflections

2139 independent reflections

1705 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.07

2139 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.99 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033916/cv2465sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033916/cv2465Isup2.hkl

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

C16H12Cl2F2N2	F(000) = 348
Mr = 341.18	Dx = 1.573 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3479 reflections
a = 4.6542 (1) Å	θ = 3.2–30.0°
b = 23.1343 (6) Å	µ = 0.47 mm−1
c = 6.9961 (2) Å	T = 100 K
β = 107.063 (2)°	Needle, colourless
V = 720.12 (3) Å3	0.51 × 0.05 × 0.04 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	2139 independent reflections
Radiation source: fine-focus sealed tube	1705 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 30.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.795, Tmax = 0.983	k = −32→32
17372 measured reflections	l = −9→9

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.6198P] where P = (Fo2 + 2Fc2)/3
2139 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.99 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.77503 (10)	0.17566 (2)	−0.30608 (7)	0.01931 (14)
F1	0.6479 (3)	0.24323 (5)	0.0088 (2)	0.0285 (3)
N1	0.0845 (4)	0.04180 (7)	0.2962 (2)	0.0165 (3)
C1	0.4139 (4)	0.17032 (8)	0.1460 (3)	0.0170 (4)
H1A	0.3865	0.1959	0.2417	0.020*
C2	0.5544 (4)	0.18819 (8)	0.0072 (3)	0.0178 (4)
C3	0.6002 (4)	0.15091 (8)	−0.1355 (3)	0.0162 (4)
C4	0.5045 (4)	0.09402 (8)	−0.1403 (3)	0.0166 (4)
H4A	0.5381	0.0684	−0.2340	0.020*
C5	0.3581 (4)	0.07550 (8)	−0.0045 (3)	0.0158 (4)
H5A	0.2890	0.0376	−0.0100	0.019*
C6	0.3139 (4)	0.11314 (8)	0.1400 (3)	0.0146 (3)
C7	0.1624 (4)	0.09406 (8)	0.2865 (3)	0.0153 (4)
H7A	0.1227	0.1210	0.3742	0.018*
C8	−0.0692 (4)	0.02721 (8)	0.4438 (3)	0.0154 (4)
H8A	−0.2811	0.0208	0.3775	0.019*
H8B	−0.0510	0.0590	0.5372	0.019*

	U11	U22	U33	U12	U13	U23
Cl1	0.0208 (2)	0.0198 (2)	0.0212 (2)	−0.00002 (17)	0.01230 (17)	0.00367 (18)
F1	0.0397 (7)	0.0162 (6)	0.0378 (8)	−0.0075 (5)	0.0242 (6)	−0.0041 (5)
N1	0.0177 (7)	0.0177 (8)	0.0162 (8)	−0.0006 (6)	0.0082 (6)	0.0024 (6)
C1	0.0184 (8)	0.0155 (9)	0.0192 (9)	−0.0001 (7)	0.0088 (7)	−0.0015 (7)
C2	0.0175 (8)	0.0138 (8)	0.0241 (10)	−0.0015 (6)	0.0093 (7)	0.0016 (7)
C3	0.0135 (8)	0.0185 (9)	0.0185 (9)	0.0003 (7)	0.0077 (7)	0.0048 (7)
C4	0.0168 (8)	0.0165 (9)	0.0171 (9)	0.0003 (7)	0.0061 (7)	−0.0004 (7)
C5	0.0173 (8)	0.0131 (8)	0.0185 (9)	−0.0008 (6)	0.0073 (7)	0.0017 (7)
C6	0.0139 (7)	0.0152 (8)	0.0155 (8)	0.0006 (6)	0.0057 (6)	0.0027 (7)
C7	0.0147 (8)	0.0169 (9)	0.0152 (9)	0.0003 (6)	0.0057 (7)	0.0012 (7)
C8	0.0164 (8)	0.0155 (8)	0.0165 (9)	0.0003 (6)	0.0081 (7)	0.0020 (7)

Cl1—C3	1.7274 (19)	C4—C5	1.389 (3)
F1—C2	1.345 (2)	C4—H4A	0.9300
N1—C7	1.270 (2)	C5—C6	1.395 (3)
N1—C8	1.458 (2)	C5—H5A	0.9300
C1—C2	1.383 (3)	C6—C7	1.472 (3)
C1—C6	1.399 (3)	C7—H7A	0.9300
C1—H1A	0.9300	C8—C8i	1.524 (4)
C2—C3	1.383 (3)	C8—H8A	0.9700
C3—C4	1.387 (3)	C8—H8B	0.9700
Cl1···F1ii	3.087 (1)	C3···C6iii	3.429 (3)
C7—N1—C8	117.74 (17)	C4—C5—H5A	119.7
C2—C1—C6	118.90 (18)	C6—C5—H5A	119.7
C2—C1—H1A	120.5	C5—C6—C1	119.56 (17)
C6—C1—H1A	120.5	C5—C6—C7	121.36 (16)
F1—C2—C3	118.59 (17)	C1—C6—C7	119.08 (17)
F1—C2—C1	119.72 (17)	N1—C7—C6	121.70 (18)
C3—C2—C1	121.70 (17)	N1—C7—H7A	119.2
C2—C3—C4	119.55 (17)	C6—C7—H7A	119.2
C2—C3—Cl1	119.73 (14)	N1—C8—C8i	109.64 (18)
C4—C3—Cl1	120.72 (15)	N1—C8—H8A	109.7
C3—C4—C5	119.63 (18)	C8i—C8—H8A	109.7
C3—C4—H4A	120.2	N1—C8—H8B	109.7
C5—C4—H4A	120.2	C8i—C8—H8B	109.7
C4—C5—C6	120.65 (17)	H8A—C8—H8B	108.2
C6—C1—C2—F1	178.99 (16)	C4—C5—C6—C1	1.0 (3)
C6—C1—C2—C3	−0.5 (3)	C4—C5—C6—C7	−179.29 (16)
F1—C2—C3—C4	−179.76 (16)	C2—C1—C6—C5	0.2 (3)
C1—C2—C3—C4	−0.2 (3)	C2—C1—C6—C7	−179.57 (16)
F1—C2—C3—Cl1	0.1 (2)	C8—N1—C7—C6	−178.90 (15)
C1—C2—C3—Cl1	179.65 (14)	C5—C6—C7—N1	4.9 (3)
C2—C3—C4—C5	1.4 (3)	C1—C6—C7—N1	−175.37 (17)
Cl1—C3—C4—C5	−178.50 (14)	C7—N1—C8—C8i	−133.5 (2)
C3—C4—C5—C6	−1.7 (3)

Table 1

Selected interatomic distances (Å)

Cl1⋯F1i	3.087 (1)
C3⋯C6ii	3.429 (3)

Symmetry codes: (i) ; (ii) .