2,3,5,6-Tetra­fluoro-1,4-bis­({[(5-methyl­thio­phen-2-yl)methyl­idene]amino}­meth­yl)benzene

Luo, H.-K.; Qin, R.-R.; He, M.-Y.

doi:10.1107/S1600536814011398

organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o698

doi:10.1107/S1600536814011398

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2,3,5,6-Tetrafluoro-1,4-bis({[(5-methylthiophen-2-yl)methylidene]amino}methyl)benzene

Hai-Kun Luo,^a Rui-Rui Qin ^a and Ming-Yang He ^a ^*

^aSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: hemingyangjpu@yahoo.com

(Received 15 April 2014; accepted 17 May 2014; online 24 May 2014)

The title compound, C₂₀H₁₆F₄N₂S₂, is a flexible bisthiophene-type Schiff base ligand with a perfluorinated backbone. The terminal thiophene rings are almost normal to one another with a dihedral angle of 83.8 (2)°, and they are tilted to the central tetrafluorinated benzene ring with dihedral angles of 61.2 (2) and 77.7 (1)°. In the crystal, there are π–π interactions involving the benzene ring and the thiophene ring of a symmetry-related molecule with a centroid–centroid separation of 3.699 (3) Å.

CCDC reference: 1003658

Related literature

For background information on thiophene-based Schiff base ligands, see: Hee & Soon (2007 ); Fang et al. (2001 ). For related fluorine-functionalized complexes, see: Chen et al. (2012 ). For the synthesis of the title compound, see: Zhang et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₆F₄N₂S₂
M_r = 424.47
Monoclinic, P 2₁
a = 9.472 (2) Å
b = 8.8083 (19) Å
c = 12.335 (3) Å
β = 111.459 (4)°
V = 957.8 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.914, T_max = 0.920
5721 measured reflections
3286 independent reflections
2897 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.129
S = 1.06
3286 reflections
255 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1003658

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814011398/bh2498sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011398/bh2498Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814011398/bh2498Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

The title compound was synthesized and purified according to the method described in Zhang et al. (2011), through a condensation of 2,3,5,6-tetrafluoro-1,4-benzenedimethanamine with 5-methylthiophene-2-carboxaldehyde (yied 86%). ¹H NMR (CDCl₃): δ 2.42 (s, 6H, CH₃), 2.76 (s, 4H, CH₂), 6.73 (s, 2H, CH), 7.15 (s, 2H, CH), 7.90 (s, 2H, CH). HRMS: [M—H]^- calculated: 424.48, measured: 424.13. Colourless needle-like single crystals (m.p. 475.3-475.9 K) suitable for X-ray analysis were obtained by dissolving the compound (20 mg) in dichloromethane (6 ml), which was then slowly evaporated at room temperature over a period of about one week.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms bound to C atoms were assigned to calculated positions, with C—H = 0.97 (methylene), 0.96 (methyl), and 0.93 Å (aromatic), and refined using a riding model, with U_iso(H)=1.5U_eq (carrier C) for the methyl groups and U_iso(H)=1.2U_eq (carrier C) for other H atoms.

Results and discussion top

In the past decade, thiophene based bidentate Schiff base ligands have been utilized intensively to assemble various coordination compounds with intriguing structural features and potential applications (Hee & Soon, 2007; Fang et al., 2001). As part of our ongoing studies of the fluorine-substituted effect on the crystal structures of coordination polymers (Chen et al., 2012), herein, we wish to report the crystal structure of the title compound.

A perspective view of the compound, including the atomic numbering scheme, is shown in Fig. 1. X-ray diffraction study demonstrates that the compound crystallizes in the monoclinic space group P2₁ with the molecule placed in general position. The bond lengths and angles are within normal ranges. The terminal thiophene rings are almost perpendicular to each other, with a dihedral angle of 83.8 (2)°, and they are inclined to the tetrafluorinated benzene ring with dihedral angles of 61.2 (2) and 77.7 (1)°, respectively. The crystal structure (Fig. 2) includes π–π interactions where π systems are separated by 3.699 (3) Å

Related literature top

For background information on thiophene-based Schiff base ligands, see: Hee & Soon (2007); Fang et al. (2001). For related fluorine-functionalized complexes, see: Chen et al. (2012). For the synthesis of the title compound, see: Zhang et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. View of the supramolecular chain structure constructed via intermolecular π–π interactions (hydrogen atoms are omitted for clarity).

2,3,5,6-Tetrafluoro-1,4-bis({[(5-methylthiophen-2-yl)methylidene]amino}methyl)benzene top

Crystal data top

C₂₀H₁₆F₄N₂S₂	D_x = 1.472 Mg m⁻³
M_r = 424.47	Melting point: 475 K
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.472 (2) Å	Cell parameters from 2369 reflections
b = 8.8083 (19) Å	θ = 2.3–24.9°
c = 12.335 (3) Å	µ = 0.32 mm⁻¹
β = 111.459 (4)°	T = 296 K
V = 957.8 (4) Å³	Needle, colourless
Z = 2	0.28 × 0.22 × 0.20 mm
F(000) = 436

Data collection top

Bruker APEXII CCD diffractometer	3286 independent reflections
Radiation source: fine-focus sealed tube	2897 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 26.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.914, T_max = 0.920	k = −10→10
5721 measured reflections	l = −14→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0803P)²] where P = (F_o² + 2F_c²)/3
3286 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.45 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³
0 constraints

Crystal data top

C₂₀H₁₆F₄N₂S₂	V = 957.8 (4) Å³
M_r = 424.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.472 (2) Å	µ = 0.32 mm⁻¹
b = 8.8083 (19) Å	T = 296 K
c = 12.335 (3) Å	0.28 × 0.22 × 0.20 mm
β = 111.459 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3286 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2897 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.920	R_int = 0.039
5721 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	Δρ_max = 0.45 e Å⁻³
3286 reflections	Δρ_min = −0.29 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.3718 (7)	−0.0116 (7)	−0.2492 (5)	0.0715 (16)
H1A	0.4443	−0.0092	−0.2869	0.107*
H1B	0.2720	−0.0269	−0.3064	0.107*
H1C	0.3961	−0.0933	−0.1938	0.107*
C2	0.3765 (5)	0.1358 (6)	−0.1875 (4)	0.0487 (11)
C3	0.4580 (6)	0.2597 (7)	−0.1859 (5)	0.0641 (14)
H3A	0.5235	0.2671	−0.2264	0.077*
C4	0.4360 (6)	0.3784 (6)	−0.1174 (5)	0.0639 (14)
H4A	0.4844	0.4719	−0.1088	0.077*
C5	0.3365 (5)	0.3421 (6)	−0.0649 (4)	0.0456 (10)
C6	0.2812 (5)	0.4377 (6)	0.0058 (3)	0.0444 (9)
H6A	0.3222	0.5341	0.0263	0.053*
C7	0.1268 (7)	0.5008 (6)	0.1089 (4)	0.0572 (12)
H7A	0.0365	0.5530	0.0585	0.069*
H7B	0.2050	0.5759	0.1440	0.069*
C8	−0.4832 (7)	0.6390 (8)	0.6706 (6)	0.0723 (15)
H8A	−0.4703	0.6929	0.7412	0.108*
H8B	−0.5734	0.5782	0.6489	0.108*
H8C	−0.4920	0.7103	0.6096	0.108*
C9	−0.3507 (5)	0.5399 (5)	0.6891 (4)	0.0484 (11)
C10	−0.2339 (6)	0.5088 (6)	0.7870 (4)	0.0540 (12)
H10A	−0.2252	0.5487	0.8590	0.065*
C11	−0.1253 (5)	0.4109 (6)	0.7725 (4)	0.0520 (12)
H11A	−0.0390	0.3779	0.8332	0.062*
C12	−0.1609 (5)	0.3697 (5)	0.6588 (4)	0.0432 (10)
C13	−0.0723 (5)	0.2770 (6)	0.6103 (4)	0.0490 (10)
H13A	0.0170	0.2332	0.6605	0.059*
C14	−0.0123 (7)	0.1595 (8)	0.4638 (5)	0.0677 (15)
H14A	−0.0627	0.0651	0.4311	0.081*
H14B	0.0796	0.1355	0.5294	0.081*
C15	0.0264 (6)	0.2471 (6)	0.3727 (4)	0.0512 (11)
C16	0.1508 (5)	0.3399 (6)	0.4012 (4)	0.0514 (11)
C17	0.1834 (5)	0.4222 (6)	0.3173 (4)	0.0484 (11)
C18	0.0924 (5)	0.4168 (5)	0.2023 (4)	0.0470 (10)
C19	−0.0323 (5)	0.3238 (6)	0.1732 (4)	0.0523 (11)
C20	−0.0650 (6)	0.2415 (6)	0.2566 (5)	0.0540 (12)
F1	0.3086 (3)	0.5090 (4)	0.3519 (3)	0.0717 (9)
F2	0.2454 (4)	0.3518 (5)	0.5127 (2)	0.0799 (10)
F3	−0.1886 (4)	0.1531 (5)	0.2219 (3)	0.0827 (10)
F4	−0.1265 (4)	0.3120 (4)	0.0623 (2)	0.0773 (9)
N1	0.1783 (5)	0.3929 (5)	0.0402 (3)	0.0526 (10)
N2	−0.1121 (5)	0.2535 (5)	0.5023 (3)	0.0544 (10)
S1	0.26914 (13)	0.16095 (14)	−0.10223 (10)	0.0494 (3)
S2	−0.32916 (13)	0.44947 (15)	0.57216 (9)	0.0503 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.080 (4)	0.073 (4)	0.072 (3)	0.005 (3)	0.040 (3)	−0.020 (3)
C2	0.049 (2)	0.057 (3)	0.044 (2)	0.006 (2)	0.0217 (18)	−0.002 (2)
C3	0.072 (3)	0.066 (3)	0.076 (3)	0.001 (3)	0.053 (3)	0.005 (3)
C4	0.066 (3)	0.053 (3)	0.094 (4)	−0.012 (2)	0.054 (3)	−0.002 (3)
C5	0.047 (2)	0.051 (3)	0.043 (2)	0.002 (2)	0.0208 (18)	0.000 (2)
C6	0.048 (2)	0.045 (2)	0.043 (2)	0.0020 (19)	0.0193 (17)	0.000 (2)
C7	0.084 (3)	0.049 (3)	0.053 (3)	0.011 (2)	0.041 (3)	0.004 (2)
C8	0.083 (4)	0.063 (4)	0.092 (4)	0.017 (3)	0.057 (3)	0.009 (3)
C9	0.058 (3)	0.046 (3)	0.054 (3)	−0.005 (2)	0.036 (2)	−0.002 (2)
C10	0.065 (3)	0.064 (3)	0.045 (2)	−0.011 (2)	0.033 (2)	−0.010 (2)
C11	0.050 (2)	0.070 (3)	0.038 (2)	−0.003 (2)	0.0185 (18)	0.001 (2)
C12	0.049 (2)	0.047 (2)	0.043 (2)	−0.0045 (18)	0.0288 (18)	−0.0011 (19)
C13	0.055 (3)	0.048 (3)	0.053 (3)	0.007 (2)	0.031 (2)	0.009 (2)
C14	0.098 (4)	0.055 (3)	0.078 (4)	0.026 (3)	0.065 (3)	0.011 (3)
C15	0.066 (3)	0.047 (3)	0.059 (3)	0.012 (2)	0.043 (2)	0.001 (2)
C16	0.055 (3)	0.060 (3)	0.043 (2)	0.015 (2)	0.024 (2)	−0.001 (2)
C17	0.049 (2)	0.052 (3)	0.054 (2)	0.006 (2)	0.029 (2)	−0.007 (2)
C18	0.054 (2)	0.047 (3)	0.050 (2)	0.0107 (19)	0.031 (2)	−0.002 (2)
C19	0.057 (3)	0.056 (3)	0.047 (2)	0.007 (2)	0.023 (2)	−0.007 (2)
C20	0.057 (3)	0.046 (3)	0.070 (3)	0.000 (2)	0.037 (2)	−0.011 (2)
F1	0.0589 (16)	0.086 (2)	0.074 (2)	−0.0124 (16)	0.0292 (15)	−0.0083 (18)
F2	0.085 (2)	0.105 (3)	0.0476 (16)	0.012 (2)	0.0216 (14)	0.0005 (17)
F3	0.081 (2)	0.080 (2)	0.101 (2)	−0.028 (2)	0.0487 (19)	−0.018 (2)
F4	0.084 (2)	0.089 (2)	0.0508 (16)	−0.0067 (18)	0.0163 (14)	−0.0123 (17)
N1	0.069 (2)	0.052 (2)	0.047 (2)	0.0029 (18)	0.0333 (19)	−0.0021 (18)
N2	0.068 (3)	0.054 (2)	0.059 (2)	0.008 (2)	0.044 (2)	0.005 (2)
S1	0.0526 (6)	0.0510 (6)	0.0553 (6)	−0.0051 (5)	0.0325 (5)	−0.0047 (6)
S2	0.0544 (6)	0.0589 (7)	0.0404 (5)	0.0066 (5)	0.0205 (4)	−0.0004 (5)

Geometric parameters (Å, º) top

C1—C2	1.498 (7)	C9—S2	1.724 (4)
C1—H1A	0.9600	C10—C11	1.403 (7)
C1—H1B	0.9600	C10—H10A	0.9300
C1—H1C	0.9600	C11—C12	1.366 (6)
C2—C3	1.333 (8)	C11—H11A	0.9300
C2—S1	1.724 (4)	C12—C13	1.447 (6)
C3—C4	1.407 (8)	C12—S2	1.712 (5)
C3—H3A	0.9300	C13—N2	1.262 (6)
C4—C5	1.362 (6)	C13—H13A	0.9300
C4—H4A	0.9300	C14—N2	1.461 (6)
C5—C6	1.441 (6)	C14—C15	1.515 (7)
C5—S1	1.718 (5)	C14—H14A	0.9700
C6—N1	1.260 (6)	C14—H14B	0.9700
C6—H6A	0.9300	C15—C16	1.371 (7)
C7—N1	1.470 (6)	C15—C20	1.377 (7)
C7—C18	1.502 (6)	C16—F2	1.343 (6)
C7—H7A	0.9700	C16—C17	1.388 (7)
C7—H7B	0.9700	C17—F1	1.342 (6)
C8—C9	1.476 (8)	C17—C18	1.364 (7)
C8—H8A	0.9600	C18—C19	1.373 (7)
C8—H8B	0.9600	C19—F4	1.336 (6)
C8—H8C	0.9600	C19—C20	1.382 (7)
C9—C10	1.334 (7)	C20—F3	1.339 (6)

C2—C1—H1A	109.5	C11—C10—H10A	122.7
C2—C1—H1B	109.5	C12—C11—C10	112.1 (4)
H1A—C1—H1B	109.5	C12—C11—H11A	123.9
C2—C1—H1C	109.5	C10—C11—H11A	123.9
H1A—C1—H1C	109.5	C11—C12—C13	127.7 (4)
H1B—C1—H1C	109.5	C11—C12—S2	110.8 (3)
C3—C2—C1	128.8 (4)	C13—C12—S2	121.4 (3)
C3—C2—S1	110.7 (4)	N2—C13—C12	122.3 (5)
C1—C2—S1	120.5 (4)	N2—C13—H13A	118.8
C2—C3—C4	113.9 (4)	C12—C13—H13A	118.8
C2—C3—H3A	123.1	N2—C14—C15	108.3 (4)
C4—C3—H3A	123.1	N2—C14—H14A	110.0
C5—C4—C3	113.1 (5)	C15—C14—H14A	110.0
C5—C4—H4A	123.5	N2—C14—H14B	110.0
C3—C4—H4A	123.5	C15—C14—H14B	110.0
C4—C5—C6	128.2 (5)	H14A—C14—H14B	108.4
C4—C5—S1	110.1 (4)	C16—C15—C20	116.3 (4)
C6—C5—S1	121.6 (3)	C16—C15—C14	122.1 (5)
N1—C6—C5	121.2 (4)	C20—C15—C14	121.6 (5)
N1—C6—H6A	119.4	F2—C16—C15	119.9 (4)
C5—C6—H6A	119.4	F2—C16—C17	118.4 (4)
N1—C7—C18	109.6 (4)	C15—C16—C17	121.7 (4)
N1—C7—H7A	109.8	F1—C17—C18	120.0 (4)
C18—C7—H7A	109.8	F1—C17—C16	118.1 (4)
N1—C7—H7B	109.8	C18—C17—C16	121.9 (4)
C18—C7—H7B	109.8	C17—C18—C19	116.6 (4)
H7A—C7—H7B	108.2	C17—C18—C7	123.3 (5)
C9—C8—H8A	109.5	C19—C18—C7	120.1 (4)
C9—C8—H8B	109.5	F4—C19—C18	120.1 (4)
H8A—C8—H8B	109.5	F4—C19—C20	118.3 (5)
C9—C8—H8C	109.5	C18—C19—C20	121.6 (4)
H8A—C8—H8C	109.5	F3—C20—C15	119.7 (5)
H8B—C8—H8C	109.5	F3—C20—C19	118.4 (5)
C10—C9—C8	129.6 (5)	C15—C20—C19	121.9 (5)
C10—C9—S2	110.5 (4)	C6—N1—C7	116.9 (4)
C8—C9—S2	119.9 (4)	C13—N2—C14	117.2 (4)
C9—C10—C11	114.5 (4)	C5—S1—C2	92.2 (2)
C9—C10—H10A	122.7	C12—S2—C9	92.0 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆F₄N₂S₂
M_r	424.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.472 (2), 8.8083 (19), 12.335 (3)
β (°)	111.459 (4)
V (Å³)	957.8 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.914, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	5721, 3286, 2897
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.620

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.129, 1.06
No. of reflections	3286
No. of parameters	255
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.29

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005), SHELXTL (Sheldrick, 2008).

Acknowledgements

We gratefully acknowledge financial support from the Open Foundation of Jiangsu Province Key Laboratory of Fine Petrochemical Technology (KF1005) and the Analysis Center of Changzhou University.

References

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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Volume 70| Part 6| June 2014| Page o698

doi:10.1107/S1600536814011398

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,3,5,6-Tetra­fluoro-1,4-bis­­({[(5-methyl­thio­phen-2-yl)methyl­­idene]amino}­meth­yl)benzene

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,3,5,6-Tetrafluoro-1,4-bis({[(5-methylthiophen-2-yl)methylidene]amino}methyl)benzene