N,N'-Bis[2-chloro-5-(trifluoro-meth-yl)benzyl-idene]ethane-1,2-diamine.

The mol-ecule of the title Schiff base compound, C(18)H(12)Cl(2)F(6)N(2), adopts an E configuration with respect to the azomethine C=N bond. Intra-molecular C-H⋯F (× 2) and C-H⋯Cl (× 2) hydrogen bonds generate S(5) ring motifs. The imino group is coplanar with the aromatic ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the methyl-ene bridge, as indicated by the dihedral angle between the two benzene rings of 3.74 (6)°. The inter-esting features of the crystal structure are weak inter-molecular Cl⋯N and F⋯F inter-actions, with distances of 2.9192 (11) and 3.2714 (10) Å, respectively, which are shorter than the sum of the van der Waals radii of the relevent atoms. These inter-actions link neighbouring mol-ecules into dimers which are stacked down the b axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures see, for example: see, for example: Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶); Fun, Mirkhani et al. (2008 ▶); Calligaris & Randaccio (1987 ▶). For information on Schiff base complexes and their applications, see, for example: Kia, Mirkhani, Kalman & Deak (2007 ▶); Kia, Mirkhani, Harkema & van Hummel (2007 ▶); Pal et al. (2005 ▶); Hou et al. (2001 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C18H12Cl2F6N2

M = 441.20

Monoclinic,

a = 35.7299 (8) Å

b = 4.6663 (1) Å

c = 27.1134 (6) Å

β = 127.851 (2)°

V = 3569.44 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 100.0 (1) K

0.59 × 0.27 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.786, T max = 0.938

61787 measured reflections

7964 independent reflections

6400 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.10

7964 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.40 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/S1600536808024926/at2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024926/at2608Isup2.hkl

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

C18H12Cl2F6N2	F000 = 1776
Mr = 441.20	Dx = 1.642 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9825 reflections
a = 35.7299 (8) Å	θ = 3.0–34.6º
b = 4.6663 (1) Å	µ = 0.43 mm−1
c = 27.1134 (6) Å	T = 100.0 (1) K
β = 127.851 (2)º	Block, colourless
V = 3569.44 (17) Å3	0.59 × 0.27 × 0.15 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	7964 independent reflections
Radiation source: fine-focus sealed tube	6400 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 100.0(1) K	θmax = 35.3º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −57→57
Tmin = 0.786, Tmax = 0.938	k = −7→7
61787 measured reflections	l = −43→43

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0531P)2 + 1.9844P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.002
7964 reflections	Δρmax = 0.49 e Å−3
253 parameters	Δρmin = −0.40 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.551363 (9)	0.32741 (7)	0.739234 (12)	0.02594 (7)
Cl2	0.189897 (9)	1.19679 (7)	0.533622 (12)	0.02472 (7)
F1	0.39316 (3)	−0.30228 (17)	0.46809 (3)	0.02702 (15)
F2	0.41420 (3)	0.04201 (17)	0.43779 (3)	0.03119 (17)
F3	0.45421 (3)	−0.34947 (19)	0.47055 (4)	0.03439 (19)
F4	0.33072 (3)	1.47263 (18)	0.83440 (3)	0.02871 (16)
F5	0.38418 (2)	1.47751 (19)	0.82146 (3)	0.03130 (18)
F6	0.34376 (3)	1.85581 (16)	0.80395 (4)	0.03396 (19)
N1	0.40343 (3)	0.5481 (2)	0.59973 (4)	0.01725 (16)
N2	0.33501 (3)	0.8779 (2)	0.64593 (4)	0.01823 (16)
C1	0.51574 (3)	0.1868 (2)	0.66416 (5)	0.01730 (17)
C2	0.53549 (4)	−0.0190 (2)	0.64928 (5)	0.02017 (19)
H2A	0.5667	−0.0777	0.6791	0.024*
C3	0.50850 (4)	−0.1361 (2)	0.58984 (5)	0.01883 (18)
H3A	0.5214	−0.2733	0.5793	0.023*
C4	0.46179 (3)	−0.0459 (2)	0.54599 (5)	0.01615 (17)
C5	0.44222 (3)	0.1577 (2)	0.56131 (5)	0.01572 (17)
H5A	0.4109	0.2140	0.5315	0.019*
C6	0.46882 (3)	0.2794 (2)	0.62082 (5)	0.01529 (16)
C7	0.44777 (3)	0.5018 (2)	0.63563 (5)	0.01595 (17)
H7A	0.4673	0.6098	0.6719	0.019*
C8	0.38645 (4)	0.7774 (2)	0.61797 (5)	0.01833 (18)
H8A	0.3757	0.9376	0.5894	0.022*
H8B	0.4121	0.8436	0.6597	0.022*
C9	0.34569 (4)	0.6674 (2)	0.61674 (5)	0.01850 (18)
H9A	0.3179	0.6351	0.5739	0.022*
H9B	0.3545	0.4869	0.6391	0.022*
C10	0.29330 (3)	0.9775 (2)	0.61435 (5)	0.01680 (17)
H10A	0.2705	0.9146	0.5736	0.020*
C11	0.28058 (3)	1.1927 (2)	0.64174 (5)	0.01518 (16)
C12	0.23492 (3)	1.3059 (2)	0.60942 (5)	0.01720 (17)
C13	0.22371 (4)	1.5054 (2)	0.63682 (5)	0.02008 (19)
H13A	0.1932	1.5794	0.6144	0.024*
C14	0.25840 (4)	1.5922 (2)	0.69772 (5)	0.01877 (18)
H14A	0.2512	1.7238	0.7166	0.023*
C15	0.30421 (3)	1.4814 (2)	0.73076 (5)	0.01553 (16)
C16	0.31517 (3)	1.2865 (2)	0.70305 (5)	0.01529 (16)
H16A	0.3459	1.2166	0.7254	0.018*
C17	0.43124 (4)	−0.1644 (2)	0.48093 (5)	0.01965 (19)
C18	0.34081 (4)	1.5713 (2)	0.79726 (5)	0.01786 (18)

	U11	U22	U33	U12	U13	U23
Cl1	0.01659 (11)	0.03460 (15)	0.01714 (11)	0.00362 (10)	0.00552 (9)	−0.00367 (10)
Cl2	0.01410 (11)	0.03396 (15)	0.01727 (11)	0.00410 (9)	0.00514 (9)	−0.00528 (10)
F1	0.0227 (3)	0.0324 (4)	0.0215 (3)	−0.0075 (3)	0.0113 (3)	−0.0041 (3)
F2	0.0443 (4)	0.0263 (4)	0.0198 (3)	0.0003 (3)	0.0181 (3)	0.0034 (3)
F3	0.0314 (4)	0.0401 (5)	0.0311 (4)	0.0075 (3)	0.0189 (3)	−0.0113 (3)
F4	0.0281 (4)	0.0420 (4)	0.0175 (3)	−0.0100 (3)	0.0147 (3)	−0.0003 (3)
F5	0.0142 (3)	0.0474 (5)	0.0236 (3)	−0.0012 (3)	0.0072 (3)	−0.0106 (3)
F6	0.0474 (5)	0.0173 (3)	0.0210 (3)	−0.0056 (3)	0.0127 (3)	−0.0035 (3)
N1	0.0159 (4)	0.0195 (4)	0.0181 (4)	0.0028 (3)	0.0113 (3)	0.0004 (3)
N2	0.0155 (4)	0.0207 (4)	0.0203 (4)	0.0015 (3)	0.0119 (3)	−0.0020 (3)
C1	0.0134 (4)	0.0203 (4)	0.0162 (4)	0.0010 (3)	0.0081 (3)	0.0004 (3)
C2	0.0133 (4)	0.0225 (5)	0.0226 (5)	0.0040 (3)	0.0099 (4)	0.0018 (4)
C3	0.0173 (4)	0.0184 (4)	0.0241 (5)	0.0029 (3)	0.0144 (4)	0.0005 (4)
C4	0.0154 (4)	0.0172 (4)	0.0178 (4)	0.0009 (3)	0.0111 (3)	0.0005 (3)
C5	0.0141 (4)	0.0172 (4)	0.0169 (4)	0.0020 (3)	0.0101 (3)	0.0014 (3)
C6	0.0128 (4)	0.0171 (4)	0.0167 (4)	0.0017 (3)	0.0094 (3)	0.0012 (3)
C7	0.0158 (4)	0.0166 (4)	0.0172 (4)	0.0011 (3)	0.0110 (3)	0.0003 (3)
C8	0.0186 (4)	0.0171 (4)	0.0233 (5)	0.0024 (3)	0.0149 (4)	−0.0002 (3)
C9	0.0155 (4)	0.0200 (4)	0.0217 (4)	0.0007 (3)	0.0122 (4)	−0.0031 (4)
C10	0.0145 (4)	0.0192 (4)	0.0167 (4)	0.0002 (3)	0.0096 (3)	−0.0019 (3)
C11	0.0132 (4)	0.0166 (4)	0.0164 (4)	0.0012 (3)	0.0094 (3)	0.0000 (3)
C12	0.0127 (4)	0.0208 (4)	0.0152 (4)	0.0011 (3)	0.0071 (3)	−0.0012 (3)
C13	0.0147 (4)	0.0240 (5)	0.0197 (4)	0.0040 (4)	0.0096 (4)	−0.0012 (4)
C14	0.0174 (4)	0.0199 (4)	0.0202 (4)	0.0022 (4)	0.0122 (4)	−0.0013 (4)
C15	0.0152 (4)	0.0158 (4)	0.0158 (4)	−0.0007 (3)	0.0096 (3)	−0.0002 (3)
C16	0.0131 (4)	0.0168 (4)	0.0163 (4)	0.0005 (3)	0.0091 (3)	0.0002 (3)
C17	0.0212 (4)	0.0203 (5)	0.0195 (4)	0.0018 (4)	0.0135 (4)	−0.0005 (4)
C18	0.0181 (4)	0.0184 (4)	0.0174 (4)	−0.0021 (3)	0.0110 (4)	−0.0008 (3)

Cl1—C1	1.7362 (11)	C5—H5A	0.9300
Cl2—C12	1.7358 (10)	C6—C7	1.4746 (14)
F1—C17	1.3433 (13)	C7—H7A	0.9300
F2—C17	1.3389 (13)	C8—C9	1.5253 (15)
F3—C17	1.3348 (13)	C8—H8A	0.9700
F4—C18	1.3419 (12)	C8—H8B	0.9700
F5—C18	1.3325 (13)	C9—H9A	0.9700
F6—C18	1.3354 (13)	C9—H9B	0.9700
N1—C7	1.2693 (13)	C10—C11	1.4771 (14)
N1—C8	1.4580 (13)	C10—H10A	0.9300
N2—C10	1.2663 (13)	C11—C12	1.3977 (14)
N2—C9	1.4517 (13)	C11—C16	1.4004 (14)
C1—C2	1.3901 (15)	C12—C13	1.3944 (14)
C1—C6	1.4000 (14)	C13—C14	1.3839 (15)
C2—C3	1.3853 (15)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.3963 (14)
C3—C4	1.3933 (14)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.3803 (14)
C4—C5	1.3858 (14)	C15—C18	1.4979 (14)
C4—C17	1.4989 (15)	C16—H16A	0.9300
C5—C6	1.3955 (14)
Cl···Ni	3.2714 (10)	F···Fii	2.9192 (11)
C7—N1—C8	116.62 (9)	H9A—C9—H9B	108.3
C10—N2—C9	118.26 (9)	N2—C10—C11	120.47 (9)
C2—C1—C6	121.96 (9)	N2—C10—H10A	119.8
C2—C1—Cl1	117.63 (8)	C11—C10—H10A	119.8
C6—C1—Cl1	120.41 (8)	C12—C11—C16	117.82 (9)
C3—C2—C1	119.69 (9)	C12—C11—C10	122.86 (9)
C3—C2—H2A	120.2	C16—C11—C10	119.32 (9)
C1—C2—H2A	120.2	C13—C12—C11	121.63 (9)
C2—C3—C4	119.18 (9)	C13—C12—Cl2	117.78 (8)
C2—C3—H3A	120.4	C11—C12—Cl2	120.58 (8)
C4—C3—H3A	120.4	C14—C13—C12	119.43 (9)
C5—C4—C3	120.80 (9)	C14—C13—H13A	120.3
C5—C4—C17	117.96 (9)	C12—C13—H13A	120.3
C3—C4—C17	121.24 (9)	C13—C14—C15	119.74 (9)
C4—C5—C6	120.96 (9)	C13—C14—H14A	120.1
C4—C5—H5A	119.5	C15—C14—H14A	120.1
C6—C5—H5A	119.5	C16—C15—C14	120.47 (9)
C5—C6—C1	117.39 (9)	C16—C15—C18	120.66 (9)
C5—C6—C7	120.12 (9)	C14—C15—C18	118.84 (9)
C1—C6—C7	122.47 (9)	C15—C16—C11	120.89 (9)
N1—C7—C6	121.08 (9)	C15—C16—H16A	119.6
N1—C7—H7A	119.5	C11—C16—H16A	119.6
C6—C7—H7A	119.5	F3—C17—F2	106.87 (9)
N1—C8—C9	109.64 (9)	F3—C17—F1	106.95 (9)
N1—C8—H8A	109.7	F2—C17—F1	105.83 (9)
C9—C8—H8A	109.7	F3—C17—C4	112.89 (9)
N1—C8—H8B	109.7	F2—C17—C4	112.02 (9)
C9—C8—H8B	109.7	F1—C17—C4	111.84 (8)
H8A—C8—H8B	108.2	F5—C18—F6	106.77 (9)
N2—C9—C8	109.09 (9)	F5—C18—F4	106.53 (9)
N2—C9—H9A	109.9	F6—C18—F4	105.93 (9)
C8—C9—H9A	109.9	F5—C18—C15	113.15 (9)
N2—C9—H9B	109.9	F6—C18—C15	112.32 (9)
C8—C9—H9B	109.9	F4—C18—C15	111.66 (9)
C6—C1—C2—C3	0.55 (17)	C16—C11—C12—Cl2	−179.14 (8)
Cl1—C1—C2—C3	−179.64 (9)	C10—C11—C12—Cl2	−0.15 (15)
C1—C2—C3—C4	−0.30 (16)	C11—C12—C13—C14	−0.63 (17)
C2—C3—C4—C5	−0.22 (16)	Cl2—C12—C13—C14	178.44 (9)
C2—C3—C4—C17	179.54 (10)	C12—C13—C14—C15	0.58 (17)
C3—C4—C5—C6	0.51 (15)	C13—C14—C15—C16	0.18 (16)
C17—C4—C5—C6	−179.26 (9)	C13—C14—C15—C18	−178.10 (10)
C4—C5—C6—C1	−0.27 (15)	C14—C15—C16—C11	−0.92 (15)
C4—C5—C6—C7	178.24 (9)	C18—C15—C16—C11	177.33 (9)
C2—C1—C6—C5	−0.26 (15)	C12—C11—C16—C15	0.86 (15)
Cl1—C1—C6—C5	179.93 (8)	C10—C11—C16—C15	−178.16 (9)
C2—C1—C6—C7	−178.73 (10)	C5—C4—C17—F3	177.37 (9)
Cl1—C1—C6—C7	1.46 (14)	C3—C4—C17—F3	−2.39 (15)
C8—N1—C7—C6	−178.56 (9)	C5—C4—C17—F2	56.68 (13)
C5—C6—C7—N1	13.43 (15)	C3—C4—C17—F2	−123.09 (11)
C1—C6—C7—N1	−168.13 (10)	C5—C4—C17—F1	−61.95 (13)
C7—N1—C8—C9	−129.40 (10)	C3—C4—C17—F1	118.28 (11)
C10—N2—C9—C8	122.57 (11)	C16—C15—C18—F5	8.87 (14)
N1—C8—C9—N2	169.41 (8)	C14—C15—C18—F5	−172.85 (10)
C9—N2—C10—C11	−179.84 (9)	C16—C15—C18—F6	129.85 (11)
N2—C10—C11—C12	−178.81 (10)	C14—C15—C18—F6	−51.87 (13)
N2—C10—C11—C16	0.17 (15)	C16—C15—C18—F4	−111.31 (11)
C16—C11—C12—C13	−0.09 (16)	C14—C15—C18—F4	66.97 (13)
C10—C11—C12—C13	178.90 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···F3	0.93	2.43	2.7415 (14)	100
C7—H7A···Cl1	0.93	2.71	3.0811 (12)	105
C10—H10A···Cl2	0.93	2.72	3.0925 (13)	105
C16—H16A···F5	0.93	2.40	2.7325 (13)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯F3	0.93	2.43	2.7415 (14)	100
C7—H7A⋯Cl1	0.93	2.71	3.0811 (12)	105
C10—H10A⋯Cl2	0.93	2.72	3.0925 (13)	105
C16—H16A⋯F5	0.93	2.40	2.7325 (13)	101

Symmetry codes: .