N,N′-Bis[1-(thiophen-2-yl)ethylidene]ethane-1,2-diamine

Abstract

Mol­ecules of the title compound, C₁₄H₁₆N₂S₂, have a centre of inversion in the middle of the –CH₂–CH₂– bond; the (C₄H₃S)(CH₃)C=N–CH₂– moiety is almost planar (r.m.s. deviation for non-H atoms 0.027 Å).

Related literature

For a related transition metal adduct, see: Modder et al. (1995 ▶).

Experimental

Crystal data

• C₁₄H₁₆N₂S₂

• M _r = 276.41

• Monoclinic,

• a = 5.5831 (3) Å

• b = 9.3939 (4) Å

• c = 12.9202 (5) Å

• β = 95.342 (4)°

• V = 674.68 (5) ų

• Z = 2

• Mo Kα radiation

• μ = 0.38 mm⁻¹

• T = 100 K

• 0.25 × 0.20 × 0.15 mm

Data collection

• Agilent SuperNova Dual diffractometer with Atlas detector

• Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.912, T _max = 0.946

• 3036 measured reflections

• 1495 independent reflections

• 1244 reflections with I > 2σ(I)

• R _int = 0.028

Refinement

• R[F ² > 2σ(F ²)] = 0.035

• wR(F ²) = 0.090

• S = 1.04

• 1495 reflections

• 83 parameters

• H-atom parameters constrained

• Δρ_max = 0.44 e Å⁻³

• Δρ_min = −0.40 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811033691/bt5618Isup3.cml

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

supplementary crystallographic information

Comment

A large number of transition metal adducts of Schiff bases derived by condensing ethylenediamine with a ketone have been reported; in these adducts, the ligand typically functions in a chelating mode. However, there are few studies on the title Schiff base (Scheme I), and only one crystal structure study has been reported (Modder et al., 1995). The C₁₄H₁₆N₂S₂ molecule lies on a center-of-inversion (Fig. 1); the (C₄H₃S)(CH₃)C═ N–CH₂– moiety is planar, and the chain connecting the two aromatic rings adopts an extended zigzag conformation [C═N–C–C 88.1 (2)°].

Experimental

Ethylenediamine (0.6 g, 10 mmol) and 2-acetylthiophene (0.7 g, 10 mmol) in dry benzene (50 ml) were refluxed in a Dean–Stark apparatus until no more water was collected (in about 2 h). The solvent was removed and the solid that separated was collected and recystallized from ethanol.

Refinement

H-atoms were placed in calculated positions [C—H 0.95–0.98 Å, U_iso(H) = 1.2–1.5U_eq(C)] and were included in the refinement in the riding model approximation.

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of C14H16N2S2 at the 70% probability level; H atoms are drawn as spheres of arbitrary radius. The molecule lies on a center-of-inversion.

Crystal data

C14H16N2S2	F(000) = 292
Mr = 276.41	Dx = 1.361 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1562 reflections
a = 5.5831 (3) Å	θ = 2.7–29.1°
b = 9.3939 (4) Å	µ = 0.38 mm−1
c = 12.9202 (5) Å	T = 100 K
β = 95.342 (4)°	Prism, colourless
V = 674.68 (5) Å3	0.25 × 0.20 × 0.15 mm
Z = 2

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector	1495 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1244 reflections with I > 2σ(I)
mirror	Rint = 0.028
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −5→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→9
Tmin = 0.912, Tmax = 0.946	l = −16→16
3036 measured reflections

Refinement

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.5515P] where P = (Fo2 + 2Fc2)/3
1495 reflections	(Δ/σ)max = 0.001
83 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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

	x	y	z	Uiso*/Ueq
S1	0.66665 (8)	0.89024 (5)	0.29153 (3)	0.01547 (15)
N1	0.5827 (3)	0.68042 (16)	0.45253 (11)	0.0141 (3)
C1	0.5756 (4)	0.56063 (19)	0.52477 (14)	0.0163 (4)
H1A	0.5065	0.5926	0.5887	0.020*
H1B	0.7412	0.5264	0.5446	0.020*
C2	0.4204 (3)	0.77676 (19)	0.44907 (13)	0.0122 (4)
C3	0.2062 (3)	0.7852 (2)	0.51239 (14)	0.0168 (4)
H3A	0.0574	0.7795	0.4659	0.025*
H3B	0.2102	0.8756	0.5503	0.025*
H3C	0.2120	0.7060	0.5619	0.025*
C4	0.4397 (3)	0.89283 (18)	0.37376 (13)	0.0113 (4)
C5	0.2995 (3)	1.0123 (2)	0.35677 (14)	0.0144 (4)
H5	0.1648	1.0330	0.3940	0.017*
C6	0.3775 (3)	1.1021 (2)	0.27724 (14)	0.0163 (4)
H6	0.3017	1.1893	0.2561	0.020*
C7	0.5731 (4)	1.0482 (2)	0.23535 (13)	0.0171 (4)
H7	0.6491	1.0930	0.1812	0.021*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0182 (3)	0.0134 (3)	0.0156 (2)	0.00002 (19)	0.00604 (18)	0.00080 (18)
N1	0.0170 (8)	0.0116 (7)	0.0135 (7)	−0.0028 (7)	0.0004 (6)	0.0025 (6)
C1	0.0195 (10)	0.0134 (9)	0.0154 (8)	−0.0006 (8)	−0.0007 (7)	0.0034 (8)
C2	0.0132 (9)	0.0120 (9)	0.0111 (8)	−0.0033 (7)	−0.0008 (7)	−0.0025 (7)
C3	0.0148 (9)	0.0213 (10)	0.0147 (8)	−0.0010 (8)	0.0030 (7)	0.0010 (8)
C4	0.0118 (8)	0.0118 (9)	0.0102 (8)	−0.0018 (7)	0.0006 (6)	−0.0013 (7)
C5	0.0131 (9)	0.0150 (9)	0.0151 (8)	0.0000 (8)	0.0007 (7)	−0.0015 (7)
C6	0.0185 (10)	0.0134 (9)	0.0156 (8)	0.0012 (8)	−0.0055 (7)	0.0013 (7)
C7	0.0239 (10)	0.0146 (9)	0.0123 (8)	−0.0052 (8)	−0.0006 (7)	0.0019 (7)

Geometric parameters (Å, °)

S1—C7	1.712 (2)	C3—H3A	0.9800
S1—C4	1.7278 (17)	C3—H3B	0.9800
N1—C2	1.279 (2)	C3—H3C	0.9800
N1—C1	1.465 (2)	C4—C5	1.375 (2)
C1—C1i	1.523 (4)	C5—C6	1.428 (3)
C1—H1A	0.9900	C5—H5	0.9500
C1—H1B	0.9900	C6—C7	1.361 (3)
C2—C4	1.472 (2)	C6—H6	0.9500
C2—C3	1.513 (2)	C7—H7	0.9500
C7—S1—C4	92.09 (9)	H3A—C3—H3C	109.5
C2—N1—C1	120.31 (15)	H3B—C3—H3C	109.5
N1—C1—C1i	110.72 (18)	C5—C4—C2	129.41 (16)
N1—C1—H1A	109.5	C5—C4—S1	110.65 (13)
C1i—C1—H1A	109.5	C2—C4—S1	119.94 (13)
N1—C1—H1B	109.5	C4—C5—C6	112.95 (16)
C1i—C1—H1B	109.5	C4—C5—H5	123.5
H1A—C1—H1B	108.1	C6—C5—H5	123.5
N1—C2—C4	116.88 (15)	C7—C6—C5	112.08 (17)
N1—C2—C3	127.72 (16)	C7—C6—H6	124.0
C4—C2—C3	115.39 (16)	C5—C6—H6	124.0
C2—C3—H3A	109.5	C6—C7—S1	112.24 (14)
C2—C3—H3B	109.5	C6—C7—H7	123.9
H3A—C3—H3B	109.5	S1—C7—H7	123.9
C2—C3—H3C	109.5
C2—N1—C1—C1i	88.1 (2)	C7—S1—C4—C5	0.05 (14)
C1—N1—C2—C4	−179.53 (15)	C7—S1—C4—C2	−179.44 (14)
C1—N1—C2—C3	−0.6 (3)	C2—C4—C5—C6	179.10 (17)
N1—C2—C4—C5	−176.62 (18)	S1—C4—C5—C6	−0.3 (2)
C3—C2—C4—C5	4.3 (3)	C4—C5—C6—C7	0.5 (2)
N1—C2—C4—S1	2.8 (2)	C5—C6—C7—S1	−0.5 (2)
C3—C2—C4—S1	−176.34 (13)	C4—S1—C7—C6	0.25 (15)

Symmetry codes: (i) −x+1, −y+1, −z+1.