N,N′-Bis[2-chloro-5-(trifluoro­meth­yl)benzyl­idene]ethane-1,2-diamine

Fun, H.-K.; Kia, R.

doi:10.1107/S1600536808024926

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1722-o1723

doi:10.1107/S1600536808024926

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N,N′-Bis[2-chloro-5-(trifluoromethyl)benzylidene]ethane-1,2-diamine

Hoong-Kun Fun ^a ^* and Reza Kia ^a ‡

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 30 July 2008; accepted 3 August 2008; online 9 August 2008)

The molecule of the title Schiff base compound, C₁₈H₁₂Cl₂F₆N₂, adopts an E configuration with respect to the azomethine C=N bond. Intramolecular 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 molecule, the planar units are parallel, but extend in opposite directions from the methylene bridge, as indicated by the dihedral angle between the two benzene rings of 3.74 (6)°. The interesting features of the crystal structure are weak intermolecular Cl⋯N and F⋯F interactions, 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 interactions link neighbouring molecules 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. (2008a ,b ); 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_r = 441.20
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.10
7964 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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: .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024926/at2608sup1.cif

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

checkCIF report

Comment top

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry. There has been growing interest in Schiff base ligands, mainly because of their wide application in the field of biochemistry, synthesis, and catalysis (Kia et al., 2007a,b; Pal et al., 2005; Hou et al., 2001; Ren et al., 2002). Many Schiff base complexes have been structurally characterized, but only a relatively small number of free Schiff bases have been characterized (Calligaris & Randaccio, 1987). As an extension of our work (Fun, Kargar & Kia 2008; Fun, Kia & Kargar 2008; Fun, Mirkhani et al., 2008a,b) on the structural characterization of Schiff base compounds, the title compound (I), is reported here.

The molecule of the title compound, (I), (Fig. 1), adopts an E configuration with respect to the azomethine C═N bond. The bond lengths and angles are within normal ranges (Allen et al., 1987). Intramolecular C—H···F (x 2) and C—H···Cl (x 2) hydrogen bonds generate S(5) ring motifs (Bernstein et al., 1995). The two planar units are parallel but extend in opposite directions from the methylene bridge. The dihedral angle between two benzene rings is 3.74 (6)°. The interesting feature of the crystal structure is weak intermolecular Cl···N and F···F interactions with the distances of 2.9192 (11) and 3.2714 (10) Å, which are shorter than the sum of the van der Waals radii of the relevant atoms, respectively (Table 1). These interactions link neighbouring molecules into dimers which are stacked down the b-axis (Fig. 2).

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structuresm see, for example: see, for example: Fun, Kargar & Kia (2008); Fun, Kia & Kargar (2008); Fun, Mirkhani et al. (2008a,b); 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 top

The synthetic method has been described earlier (Fun, Mirkhani et al., (2008a,b)). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms. Intramolecular interactions are shown as dashed lines.
	Fig. 2. The crystal packing of (I), showing stacks of the molecules viewed down the b-axis. Intramolecular and intermolecular interactions are shown as dashed lines.

N,N'-Bis[2-chloro-5-(trifluoromethyl)benzylidene]ethane- 1,2-diamine top

Crystal data top

C₁₈H₁₂Cl₂F₆N₂	F(000) = 1776
M_r = 441.20	D_x = 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 = 3.0–34.6°
b = 4.6663 (1) Å	µ = 0.43 mm⁻¹
c = 27.1134 (6) Å	T = 100 K
β = 127.851 (2)°	Block, colourless
V = 3569.44 (17) Å³	0.59 × 0.27 × 0.15 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7964 independent reflections
Radiation source: fine-focus sealed tube	6400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 35.3°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −57→57
T_min = 0.786, T_max = 0.938	k = −7→7
61787 measured reflections	l = −43→43

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0531P)² + 1.9844P] where P = (F_o² + 2F_c²)/3
7964 reflections	(Δ/σ)_max = 0.002
253 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₈H₁₂Cl₂F₆N₂	V = 3569.44 (17) Å³
M_r = 441.20	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 35.7299 (8) Å	µ = 0.43 mm⁻¹
b = 4.6663 (1) Å	T = 100 K
c = 27.1134 (6) Å	0.59 × 0.27 × 0.15 mm
β = 127.851 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7964 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6400 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.938	R_int = 0.037
61787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.10	Δρ_max = 0.49 e Å⁻³
7964 reflections	Δρ_min = −0.40 e Å⁻³
253 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y−3/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂Cl₂F₆N₂
M_r	441.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	35.7299 (8), 4.6663 (1), 27.1134 (6)
β (°)	127.851 (2)
V (Å³)	3569.44 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.59 × 0.27 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.786, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	61787, 7964, 6400
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.813

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.10
No. of reflections	7964
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.40

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected interatomic distances (Å) top

Cl···Nⁱ

3.2714 (10)

F···Fⁱⁱ

2.9192 (11)

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y−3/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Footnotes

‡Additional correspondance author, e-mail: zsrkk@yahoo.com.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for the award of a post-doctoral research fellowship.

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