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access(E)-4-Methyl-N-[(5-nitrothiophen-2-yl)methylidene]aniline
aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Giresun University, 28100 Giresun, Turkey
*Correspondence e-mail: uceylan@omu.edu.tr
In the of the title compound, C12H10N2O2S, the benzene and the 2-nitrothiophene rings make a dihedral angle of 7.47 (12)°. The dihedral angle between the nitro group and the attached ring is 1.9 (6)°.
![[Scheme 1]](nc2283scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Oxford Diffraction, 2009![[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]](../../../../../../logos/arrows/e_arr.gif "Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.")
); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al. 2009) and ORTEP-3 for Windows (Farrugia, 1997);; software used to prepare material for publication: OLEX2 (Dolomanov et al. 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supporting information
contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536812026062/nc2283sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026062/nc2283Isup2.hkl
A mixture of 5-nitrothiophene-2-carboxaldehyde (0.011 g 0.066 mmol) in 20 ml e thanol and of p-Toluidine (0.007 g 0.066 mmol) in 20 ml ethanol was refluxed for 1 h. Single crystals suitable for X-ray analysis were obtained from a solution of the title compound in ethanol by slow evaporation of the solvent (yield % 78; m.p 101–103 °C).
All hydrogen atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip and were refined with Uiso(H)= 1.2Ueq(C) (1.5 for methyl H atoms using a riding model with C—H = 0.930 for aromatic and and 0.960 for methyl H atoms.
The title compound was by the reaction between 5-nitrothiophene-2-carboxaldehyde and p-Toluidine. For the identification of this compound a single analysis was performed. It is noted that some 2-nitrothiophene structures have already been reported in literature (Demirtaş et al. 2009; Ceylan et al. 2011). In the the dihedral angle between the 6-membered and the 2-nitrothiophene rings amount to 7.47 (12)° and the torsion angle along C5—N1—C8—C9 is 179.7 (3)°. Both rings are in a trans arrangement with respect to the C-N double bond and the nitro group is oriented almost coplanar to the 2-nitrothiophene plane (Fig. 1).
For related structures, see: Demirtaş et al. (2009); Ceylan et al. (2011).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al. 2009) and ORTEP-3 for Windows (Farrugia, 1997);; software used to prepare material for publication: OLEX2 (Dolomanov et al. 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./nc2283fig1thm.gif) | Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
| C12H10N2O2S | F(000) = 512 |
| Mr = 246.28 | Dx = 1.397 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1442 reflections |
| a = 4.7661 (4) Å | θ = 3.3–27.6° |
| b = 22.8201 (18) Å | µ = 0.26 mm−1 |
| c = 10.7793 (7) Å | T = 296 K |
| β = 92.704 (7)° | Prism, brown |
| V = 1171.08 (15) Å3 | 0.17 × 0.15 × 0.12 mm |
| Z = 4 |
| Oxford Diffraction SuperNova Eos diffractometer | 2211 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 1549 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.064 |
| Detector resolution: 16.0454 pixels mm-1 | θmax = 26.0°, θmin = 3.3° |
| ω scans | h = −5→5 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −27→26 |
| Tmin = 0.771, Tmax = 1.000 | l = −13→8 |
| 3997 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.177 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0778P)2] where P = (Fo2 + 2Fc2)/3 |
| 2211 reflections | (Δ/σ)max < 0.001 |
| 155 parameters | Δρmax = 0.26 e Å−3 |
| 0 restraints | Δρmin = −0.28 e Å−3 |
| C12H10N2O2S | V = 1171.08 (15) Å3 |
| Mr = 246.28 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 4.7661 (4) Å | µ = 0.26 mm−1 |
| b = 22.8201 (18) Å | T = 296 K |
| c = 10.7793 (7) Å | 0.17 × 0.15 × 0.12 mm |
| β = 92.704 (7)° |
| Oxford Diffraction SuperNova Eos diffractometer | 2211 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 1549 reflections with I > 2σ(I) |
| Tmin = 0.771, Tmax = 1.000 | Rint = 0.064 |
| 3997 measured reflections |
| R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
| wR(F2) = 0.177 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.26 e Å−3 |
| 2211 reflections | Δρmin = −0.28 e Å−3 |
| 155 parameters |
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 | ||
| C1 | 1.8771 (9) | 0.51221 (18) | 0.2226 (4) | 0.0792 (14) | |
| H1A | 2.0022 | 0.5083 | 0.1558 | 0.119* | |
| H1B | 1.9835 | 0.5118 | 0.3005 | 0.119* | |
| H1C | 1.7765 | 0.5485 | 0.2141 | 0.119* | |
| C2 | 1.6709 (7) | 0.46177 (17) | 0.2185 (4) | 0.0576 (11) | |
| C3 | 1.5819 (8) | 0.43632 (17) | 0.1076 (4) | 0.0586 (11) | |
| H3 | 1.6539 | 0.4500 | 0.0343 | 0.070* | |
| C4 | 1.3897 (7) | 0.39125 (16) | 0.1021 (3) | 0.0498 (9) | |
| H4 | 1.3321 | 0.3754 | 0.0256 | 0.060* | |
| C5 | 1.2814 (7) | 0.36934 (15) | 0.2103 (3) | 0.0409 (8) | |
| C6 | 1.3763 (8) | 0.39378 (17) | 0.3217 (3) | 0.0498 (9) | |
| H6 | 1.3103 | 0.3794 | 0.3956 | 0.060* | |
| C7 | 1.5673 (8) | 0.43920 (17) | 0.3253 (4) | 0.0623 (11) | |
| H7 | 1.6273 | 0.4549 | 0.4017 | 0.075* | |
| C8 | 0.9566 (7) | 0.30543 (15) | 0.1167 (3) | 0.0436 (8) | |
| H8 | 0.9950 | 0.3238 | 0.0424 | 0.052* | |
| C9 | 0.7549 (7) | 0.25849 (15) | 0.1140 (3) | 0.0407 (8) | |
| C10 | 0.6197 (7) | 0.23554 (16) | 0.0104 (3) | 0.0501 (10) | |
| H10 | 0.6498 | 0.2486 | −0.0696 | 0.060* | |
| C11 | 0.4313 (7) | 0.19048 (16) | 0.0363 (3) | 0.0479 (9) | |
| H11 | 0.3243 | 0.1699 | −0.0236 | 0.057* | |
| C12 | 0.4260 (7) | 0.18089 (14) | 0.1598 (3) | 0.0379 (8) | |
| N1 | 1.0843 (6) | 0.32285 (12) | 0.2158 (2) | 0.0413 (7) | |
| N2 | 0.2502 (6) | 0.13966 (14) | 0.2189 (3) | 0.0488 (8) | |
| O1 | 0.2643 (6) | 0.13733 (12) | 0.3329 (2) | 0.0663 (8) | |
| O2 | 0.0953 (6) | 0.10886 (13) | 0.1531 (3) | 0.0692 (8) | |
| S1 | 0.64676 (18) | 0.22535 (4) | 0.24745 (7) | 0.0417 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.058 (3) | 0.047 (2) | 0.133 (4) | −0.009 (2) | 0.009 (3) | −0.004 (3) |
| C2 | 0.036 (2) | 0.042 (2) | 0.095 (3) | 0.0044 (17) | 0.008 (2) | 0.003 (2) |
| C3 | 0.052 (2) | 0.050 (2) | 0.074 (3) | 0.000 (2) | 0.010 (2) | 0.013 (2) |
| C4 | 0.049 (2) | 0.051 (2) | 0.050 (2) | 0.0003 (19) | 0.0058 (17) | 0.0034 (18) |
| C5 | 0.0348 (19) | 0.0387 (19) | 0.0492 (19) | 0.0028 (15) | 0.0013 (15) | 0.0042 (16) |
| C6 | 0.048 (2) | 0.052 (2) | 0.049 (2) | −0.0071 (19) | −0.0010 (16) | 0.0026 (18) |
| C7 | 0.055 (2) | 0.058 (3) | 0.073 (3) | −0.008 (2) | −0.005 (2) | −0.008 (2) |
| C8 | 0.042 (2) | 0.050 (2) | 0.0386 (17) | 0.0005 (17) | 0.0031 (15) | 0.0093 (16) |
| C9 | 0.041 (2) | 0.044 (2) | 0.0360 (17) | 0.0019 (16) | −0.0023 (14) | 0.0015 (15) |
| C10 | 0.051 (2) | 0.065 (2) | 0.0339 (17) | −0.006 (2) | −0.0021 (16) | 0.0042 (17) |
| C11 | 0.049 (2) | 0.058 (2) | 0.0354 (17) | −0.0040 (19) | −0.0052 (15) | −0.0093 (17) |
| C12 | 0.0331 (18) | 0.0394 (19) | 0.0413 (16) | 0.0046 (15) | 0.0039 (14) | −0.0025 (15) |
| N1 | 0.0417 (16) | 0.0423 (16) | 0.0393 (14) | 0.0015 (14) | −0.0032 (12) | 0.0033 (13) |
| N2 | 0.0507 (19) | 0.0464 (19) | 0.0493 (17) | 0.0056 (16) | 0.0041 (15) | 0.0033 (15) |
| O1 | 0.085 (2) | 0.0671 (18) | 0.0480 (15) | −0.0064 (16) | 0.0113 (14) | 0.0092 (14) |
| O2 | 0.0684 (19) | 0.0685 (18) | 0.0704 (17) | −0.0220 (16) | 0.0005 (15) | −0.0036 (16) |
| S1 | 0.0472 (6) | 0.0464 (6) | 0.0313 (4) | 0.0021 (4) | −0.0015 (4) | −0.0003 (4) |
| C1—C2 | 1.513 (5) | C7—H7 | 0.9300 |
| C1—H1A | 0.9600 | C8—N1 | 1.269 (4) |
| C1—H1B | 0.9600 | C8—C9 | 1.439 (5) |
| C1—H1C | 0.9600 | C8—H8 | 0.9300 |
| C2—C7 | 1.374 (5) | C9—C10 | 1.366 (4) |
| C2—C3 | 1.378 (5) | C9—S1 | 1.725 (3) |
| C3—C4 | 1.377 (5) | C10—C11 | 1.402 (4) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.391 (4) | C11—C12 | 1.351 (4) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.381 (5) | C12—N2 | 1.430 (4) |
| C5—N1 | 1.420 (4) | C12—S1 | 1.713 (3) |
| C6—C7 | 1.379 (5) | N2—O2 | 1.222 (4) |
| C6—H6 | 0.9300 | N2—O1 | 1.228 (4) |
| C2—C1—H1A | 109.5 | C2—C7—H7 | 119.3 |
| C2—C1—H1B | 109.5 | C6—C7—H7 | 119.3 |
| H1A—C1—H1B | 109.5 | N1—C8—C9 | 123.0 (3) |
| C2—C1—H1C | 109.5 | N1—C8—H8 | 118.5 |
| H1A—C1—H1C | 109.5 | C9—C8—H8 | 118.5 |
| H1B—C1—H1C | 109.5 | C10—C9—C8 | 126.2 (3) |
| C7—C2—C3 | 117.4 (4) | C10—C9—S1 | 111.4 (3) |
| C7—C2—C1 | 121.3 (4) | C8—C9—S1 | 122.4 (2) |
| C3—C2—C1 | 121.3 (4) | C9—C10—C11 | 113.6 (3) |
| C4—C3—C2 | 122.0 (4) | C9—C10—H10 | 123.2 |
| C4—C3—H3 | 119.0 | C11—C10—H10 | 123.2 |
| C2—C3—H3 | 119.0 | C12—C11—C10 | 110.9 (3) |
| C3—C4—C5 | 120.3 (4) | C12—C11—H11 | 124.6 |
| C3—C4—H4 | 119.8 | C10—C11—H11 | 124.6 |
| C5—C4—H4 | 119.8 | C11—C12—N2 | 125.8 (3) |
| C6—C5—C4 | 117.7 (3) | C11—C12—S1 | 114.1 (3) |
| C6—C5—N1 | 117.1 (3) | N2—C12—S1 | 120.1 (2) |
| C4—C5—N1 | 125.2 (3) | C8—N1—C5 | 119.4 (3) |
| C7—C6—C5 | 121.1 (3) | O2—N2—O1 | 124.0 (3) |
| C7—C6—H6 | 119.4 | O2—N2—C12 | 118.1 (3) |
| C5—C6—H6 | 119.4 | O1—N2—C12 | 118.0 (3) |
| C2—C7—C6 | 121.4 (4) | C12—S1—C9 | 89.98 (15) |
| C7—C2—C3—C4 | 2.1 (6) | C9—C10—C11—C12 | 0.8 (4) |
| C1—C2—C3—C4 | −178.5 (3) | C10—C11—C12—N2 | 177.6 (3) |
| C2—C3—C4—C5 | −0.9 (6) | C10—C11—C12—S1 | −0.2 (4) |
| C3—C4—C5—C6 | −0.9 (5) | C9—C8—N1—C5 | 179.7 (3) |
| C3—C4—C5—N1 | −179.5 (3) | C6—C5—N1—C8 | 168.5 (3) |
| C4—C5—C6—C7 | 1.4 (5) | C4—C5—N1—C8 | −12.8 (5) |
| N1—C5—C6—C7 | −179.9 (3) | C11—C12—N2—O2 | 2.2 (5) |
| C3—C2—C7—C6 | −1.6 (6) | S1—C12—N2—O2 | 179.8 (3) |
| C1—C2—C7—C6 | 179.1 (4) | C11—C12—N2—O1 | −177.9 (3) |
| C5—C6—C7—C2 | −0.2 (6) | S1—C12—N2—O1 | −0.2 (4) |
| N1—C8—C9—C10 | −176.6 (3) | C11—C12—S1—C9 | −0.3 (3) |
| N1—C8—C9—S1 | 5.4 (5) | N2—C12—S1—C9 | −178.2 (3) |
| C8—C9—C10—C11 | −179.2 (3) | C10—C9—S1—C12 | 0.7 (3) |
| S1—C9—C10—C11 | −1.0 (4) | C8—C9—S1—C12 | 179.0 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C12H10N2O2S |
| Mr | 246.28 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 296 |
| a, b, c (Å) | 4.7661 (4), 22.8201 (18), 10.7793 (7) |
| β (°) | 92.704 (7) |
| V (Å3) | 1171.08 (15) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.26 |
| Crystal size (mm) | 0.17 × 0.15 × 0.12 |
| Data collection | |
| Diffractometer | Oxford Diffraction SuperNova Eos |
| Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
| Tmin, Tmax | 0.771, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 3997, 2211, 1549 |
| Rint | 0.064 |
| (sin θ/λ)max (Å−1) | 0.616 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.177, 1.05 |
| No. of reflections | 2211 |
| No. of parameters | 155 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.26, −0.28 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al. 2009) and ORTEP-3 for Windows (Farrugia, 1997);, OLEX2 (Dolomanov et al. 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Acknowledgements
The authors thank the Giresun University Research Fund for financial support of this study.
References
Ceylan, Ü., Tanak, H., Gümüş, S. & Ağar, E. (2011). Acta Cryst. E67, o2004. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The title compound was by the reaction between 5-nitrothiophene-2-carboxaldehyde and p-Toluidine. For the identification of this compound a single crystal structure analysis was performed. It is noted that some 2-nitrothiophene structures have already been reported in literature (Demirtaş et al. 2009; Ceylan et al. 2011). In the crystal structure the dihedral angle between the 6-membered and the 2-nitrothiophene rings amount to 7.47 (12)° and the torsion angle along C5—N1—C8—C9 is 179.7 (3)°. Both rings are in a trans arrangement with respect to the C-N double bond and the nitro group is oriented almost coplanar to the 2-nitrothiophene plane (Fig. 1).