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accessN,N′-Bis[1-(thiophen-2-yl)ethylidene]ethane-1,2-diamine
aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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).
![[Scheme 1]](bt5618scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2010![[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]](../../../../../../logos/arrows/e_arr.gif "Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.")
); cell 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).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536811033691/bt5618sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811033691/bt5618Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811033691/bt5618Isup3.cml
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.
H-atoms were placed in calculated positions [C—H 0.95–0.98 Å, Uiso(H) = 1.2–1.5Ueq(C)] and were included in the in the riding model approximation.
Data collection: CrysAlis PRO (Agilent, 2010); cell CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).
![[Figure 1]](./bt5618fig1thm.gif) | 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. |
| 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 |
| Agilent SuperNova Dual diffractometer with Atlas detector | 1495 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 1244 reflections with I > 2σ(I) |
| Mirror monochromator | 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 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 |
| C14H16N2S2 | V = 674.68 (5) Å3 |
| Mr = 276.41 | Z = 2 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 5.5831 (3) Å | µ = 0.38 mm−1 |
| b = 9.3939 (4) Å | T = 100 K |
| c = 12.9202 (5) Å | 0.25 × 0.20 × 0.15 mm |
| β = 95.342 (4)° |
| Agilent SuperNova Dual diffractometer with Atlas detector | 1495 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | 1244 reflections with I > 2σ(I) |
| Tmin = 0.912, Tmax = 0.946 | Rint = 0.028 |
| 3036 measured reflections |
| R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
| wR(F2) = 0.090 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.44 e Å−3 |
| 1495 reflections | Δρmin = −0.40 e Å−3 |
| 83 parameters |
| 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* |
| 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) |
| 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 code: (i) −x+1, −y+1, −z+1. |
Experimental details
| Crystal data | |
| Chemical formula | C14H16N2S2 |
| Mr | 276.41 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 100 |
| a, b, c (Å) | 5.5831 (3), 9.3939 (4), 12.9202 (5) |
| β (°) | 95.342 (4) |
| V (Å3) | 674.68 (5) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.38 |
| Crystal size (mm) | 0.25 × 0.20 × 0.15 |
| Data collection | |
| Diffractometer | Agilent SuperNova Dual diffractometer with Atlas detector |
| Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2010) |
| Tmin, Tmax | 0.912, 0.946 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 3036, 1495, 1244 |
| Rint | 0.028 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.090, 1.04 |
| No. of reflections | 1495 |
| No. of parameters | 83 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.44, −0.40 |
Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
The authors thank King Abdulaziz University and the University of Malaya for supporting this study.
References
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Modder, J. F., Leijen, R. J., Vrieze, K., Smeets, W. J. J., Spek, A. L. & van Koten, G. (1995). J. Chem. Soc. Dalton Trans. pp. 4021–4028. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
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)°].