 | Acta Crystallographica Section E Acta Crystallographica Section E CRYSTALLOGRAPHIC COMMUNICATIONS |
journal menu
organic compounds
| CRYSTALLOGRAPHIC COMMUNICATIONS |
accessA monoclinic modification of 2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol
aChemistry Department, Faculty of Science, King Abdul Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the title Schiff base, C14H10N2OS, the azomethine double bond is in an E configuration; the benzothiazolyl ring (r.m.s. deviation = 0.007 Å) is coplanar with the phenylene ring (r.m.s. deviation = 0.007 Å), the two rings being slightly bent at 2.6 (1)°. The hydroxy H atom forms an intramolecular hydrogen bond to the imino group. The bond dimensions of the monoclinic modification are similar to those of the orthorhombic modification [Liu et al. (2009![[Liu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738.]](../../../../../../logos/arrows/e_arr.gif "Liu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738.")
). Acta Cryst. E65, o738].
![[Scheme 1]](nk2043scheme1.gif)
Experimental
Crystal data
|
| |||||||||||||||||
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; 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/S1600536810023755/nk2043sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536810023755/nk2043Isup2.hkl
2-Aminobenzothiazole (0.50 g, 4.4 mol) and salicyladehyde (0.66 g, 4.4 mol) were heated in methanol (15 ml) for 5 h. Yellowish-orange crystals deposited when the solution was set aside for a day.
Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 Å, U(H) 1.2Ueq(C)] and were included in the in the riding model approximation. The hydroxy H-atom was located in a difference Fourier map, but attempts to refine it even with a distance restraint led to a small temperature factor. The position and temperature factor were not refined. The structure is a racemic twin, the explicit of the from 1242 Friedel pairs gave a value of 0.27 (8).
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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]](./nk2043fig1thm.gif) | Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H10N2OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
| C14H10N2OS | F(000) = 264 |
| Mr = 254.30 | Dx = 1.449 Mg m−3 |
| Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P -2yac | Cell parameters from 3896 reflections |
| a = 8.6391 (4) Å | θ = 2.6–28.3° |
| b = 6.2313 (4) Å | µ = 0.26 mm−1 |
| c = 11.4459 (8) Å | T = 100 K |
| β = 108.893 (1)° | Prism, orange |
| V = 582.97 (6) Å3 | 0.14 × 0.13 × 0.08 mm |
| Z = 2 |
| Bruker SMART APEX diffractometer | 2599 independent reflections |
| Radiation source: fine-focus sealed tube | 2512 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.029 |
| ω scans | θmax = 27.5°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
| Tmin = 0.964, Tmax = 0.979 | k = −8→8 |
| 5307 measured reflections | l = −14→14 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0831P)2 + 0.0645P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max = 0.001 |
| 2599 reflections | Δρmax = 0.40 e Å−3 |
| 164 parameters | Δρmin = −0.25 e Å−3 |
| 2 restraints | Absolute structure: Flack (1983), 1242 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.27 (8) |
| C14H10N2OS | V = 582.97 (6) Å3 |
| Mr = 254.30 | Z = 2 |
| Monoclinic, Pn | Mo Kα radiation |
| a = 8.6391 (4) Å | µ = 0.26 mm−1 |
| b = 6.2313 (4) Å | T = 100 K |
| c = 11.4459 (8) Å | 0.14 × 0.13 × 0.08 mm |
| β = 108.893 (1)° |
| Bruker SMART APEX diffractometer | 2599 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2512 reflections with I > 2σ(I) |
| Tmin = 0.964, Tmax = 0.979 | Rint = 0.029 |
| 5307 measured reflections |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.110 | Δρmax = 0.40 e Å−3 |
| S = 1.05 | Δρmin = −0.25 e Å−3 |
| 2599 reflections | Absolute structure: Flack (1983), 1242 Friedel pairs |
| 164 parameters | Absolute structure parameter: 0.27 (8) |
| 2 restraints |
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.50007 (6) | 0.06429 (7) | 0.49993 (5) | 0.01864 (15) | |
| O1 | 0.7048 (2) | 0.5684 (3) | 0.89741 (16) | 0.0277 (4) | |
| H1 | 0.6924 | 0.4623 | 0.8462 | 0.042* | |
| N1 | 0.6095 (2) | 0.3254 (3) | 0.70823 (16) | 0.0186 (4) | |
| N2 | 0.7613 (2) | 0.0261 (3) | 0.69409 (17) | 0.0193 (4) | |
| C1 | 0.5700 (3) | 0.6867 (4) | 0.84466 (19) | 0.0195 (4) | |
| C2 | 0.5445 (3) | 0.8696 (4) | 0.9059 (2) | 0.0222 (4) | |
| H2 | 0.6227 | 0.9096 | 0.9825 | 0.027* | |
| C3 | 0.4058 (3) | 0.9936 (4) | 0.8561 (2) | 0.0226 (5) | |
| H3 | 0.3895 | 1.1183 | 0.8985 | 0.027* | |
| C4 | 0.2898 (3) | 0.9363 (3) | 0.7441 (2) | 0.0228 (5) | |
| H4 | 0.1937 | 1.0201 | 0.7108 | 0.027* | |
| C5 | 0.3153 (3) | 0.7571 (4) | 0.68168 (19) | 0.0214 (4) | |
| H5 | 0.2366 | 0.7193 | 0.6049 | 0.026* | |
| C6 | 0.4554 (3) | 0.6303 (3) | 0.72981 (19) | 0.0175 (4) | |
| C7 | 0.4806 (3) | 0.4437 (3) | 0.6638 (2) | 0.0188 (4) | |
| H7 | 0.4019 | 0.4071 | 0.5868 | 0.023* | |
| C8 | 0.6349 (3) | 0.1448 (3) | 0.64566 (19) | 0.0184 (4) | |
| C9 | 0.7588 (3) | −0.1475 (3) | 0.61665 (18) | 0.0178 (4) | |
| C10 | 0.8777 (3) | −0.3090 (4) | 0.6428 (2) | 0.0228 (4) | |
| H10 | 0.9681 | −0.3056 | 0.7170 | 0.027* | |
| C11 | 0.8612 (3) | −0.4729 (4) | 0.5589 (2) | 0.0249 (5) | |
| H11 | 0.9414 | −0.5832 | 0.5757 | 0.030* | |
| C12 | 0.7290 (3) | −0.4798 (4) | 0.4498 (2) | 0.0229 (5) | |
| H12 | 0.7212 | −0.5939 | 0.3931 | 0.027* | |
| C13 | 0.6081 (3) | −0.3219 (4) | 0.4225 (2) | 0.0213 (4) | |
| H13 | 0.5170 | −0.3277 | 0.3488 | 0.026* | |
| C14 | 0.6257 (3) | −0.1556 (3) | 0.5070 (2) | 0.0190 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0181 (2) | 0.0172 (2) | 0.0187 (2) | −0.0003 (2) | 0.00322 (17) | −0.00262 (19) |
| O1 | 0.0216 (9) | 0.0314 (10) | 0.0232 (9) | 0.0063 (7) | −0.0024 (7) | −0.0064 (6) |
| N1 | 0.0193 (8) | 0.0166 (8) | 0.0183 (8) | −0.0016 (7) | 0.0040 (7) | −0.0015 (7) |
| N2 | 0.0222 (10) | 0.0148 (8) | 0.0191 (9) | −0.0020 (7) | 0.0042 (7) | −0.0008 (7) |
| C1 | 0.0181 (10) | 0.0220 (10) | 0.0181 (9) | −0.0008 (8) | 0.0051 (8) | −0.0004 (8) |
| C2 | 0.0235 (11) | 0.0215 (10) | 0.0211 (10) | −0.0032 (9) | 0.0066 (9) | −0.0052 (8) |
| C3 | 0.0265 (12) | 0.0193 (10) | 0.0263 (11) | −0.0017 (9) | 0.0144 (9) | −0.0023 (8) |
| C4 | 0.0228 (12) | 0.0211 (11) | 0.0255 (11) | 0.0054 (8) | 0.0095 (9) | 0.0051 (8) |
| C5 | 0.0197 (10) | 0.0245 (10) | 0.0190 (9) | 0.0002 (9) | 0.0048 (8) | 0.0025 (8) |
| C6 | 0.0179 (10) | 0.0178 (9) | 0.0164 (9) | −0.0011 (8) | 0.0050 (8) | −0.0012 (8) |
| C7 | 0.0173 (10) | 0.0200 (11) | 0.0177 (10) | −0.0029 (8) | 0.0035 (8) | −0.0002 (7) |
| C8 | 0.0196 (10) | 0.0168 (10) | 0.0182 (9) | −0.0025 (8) | 0.0051 (8) | 0.0001 (7) |
| C9 | 0.0221 (10) | 0.0148 (9) | 0.0175 (9) | −0.0025 (8) | 0.0077 (8) | −0.0021 (8) |
| C10 | 0.0228 (11) | 0.0209 (10) | 0.0249 (10) | 0.0016 (9) | 0.0081 (8) | 0.0032 (8) |
| C11 | 0.0245 (12) | 0.0224 (11) | 0.0311 (12) | 0.0032 (9) | 0.0136 (10) | 0.0047 (9) |
| C12 | 0.0282 (13) | 0.0182 (10) | 0.0276 (12) | −0.0036 (9) | 0.0166 (10) | −0.0058 (9) |
| C13 | 0.0205 (10) | 0.0224 (11) | 0.0208 (10) | −0.0043 (9) | 0.0063 (8) | −0.0018 (8) |
| C14 | 0.0178 (10) | 0.0156 (9) | 0.0249 (10) | 0.0012 (8) | 0.0088 (8) | 0.0022 (8) |
| S1—C14 | 1.733 (2) | C4—H4 | 0.9500 |
| S1—C8 | 1.770 (2) | C5—C6 | 1.400 (3) |
| O1—C1 | 1.345 (3) | C5—H5 | 0.9500 |
| O1—H1 | 0.8672 | C6—C7 | 1.442 (3) |
| N1—C7 | 1.294 (3) | C7—H7 | 0.9500 |
| N1—C8 | 1.389 (3) | C9—C10 | 1.399 (3) |
| N2—C8 | 1.286 (3) | C9—C14 | 1.402 (3) |
| N2—C9 | 1.394 (3) | C10—C11 | 1.378 (3) |
| C1—C2 | 1.393 (3) | C10—H10 | 0.9500 |
| C1—C6 | 1.410 (3) | C11—C12 | 1.393 (4) |
| C2—C3 | 1.383 (4) | C11—H11 | 0.9500 |
| C2—H2 | 0.9500 | C12—C13 | 1.395 (3) |
| C3—C4 | 1.394 (4) | C12—H12 | 0.9500 |
| C3—H3 | 0.9500 | C13—C14 | 1.392 (3) |
| C4—C5 | 1.381 (3) | C13—H13 | 0.9500 |
| C14—S1—C8 | 88.21 (11) | N1—C7—H7 | 119.7 |
| C1—O1—H1 | 102.4 | C6—C7—H7 | 119.7 |
| C7—N1—C8 | 121.20 (18) | N2—C8—N1 | 119.83 (19) |
| C8—N2—C9 | 109.65 (18) | N2—C8—S1 | 116.81 (16) |
| O1—C1—C2 | 118.56 (19) | N1—C8—S1 | 123.36 (17) |
| O1—C1—C6 | 121.8 (2) | N2—C9—C10 | 124.3 (2) |
| C2—C1—C6 | 119.7 (2) | N2—C9—C14 | 115.84 (19) |
| C3—C2—C1 | 120.4 (2) | C10—C9—C14 | 119.9 (2) |
| C3—C2—H2 | 119.8 | C11—C10—C9 | 118.8 (2) |
| C1—C2—H2 | 119.8 | C11—C10—H10 | 120.6 |
| C2—C3—C4 | 120.3 (2) | C9—C10—H10 | 120.6 |
| C2—C3—H3 | 119.8 | C10—C11—C12 | 121.1 (2) |
| C4—C3—H3 | 119.8 | C10—C11—H11 | 119.4 |
| C5—C4—C3 | 119.7 (2) | C12—C11—H11 | 119.4 |
| C5—C4—H4 | 120.2 | C13—C12—C11 | 121.1 (2) |
| C3—C4—H4 | 120.2 | C13—C12—H12 | 119.5 |
| C4—C5—C6 | 121.0 (2) | C11—C12—H12 | 119.5 |
| C4—C5—H5 | 119.5 | C14—C13—C12 | 117.7 (2) |
| C6—C5—H5 | 119.5 | C14—C13—H13 | 121.2 |
| C5—C6—C1 | 118.87 (19) | C12—C13—H13 | 121.2 |
| C5—C6—C7 | 120.47 (19) | C13—C14—C9 | 121.5 (2) |
| C1—C6—C7 | 120.7 (2) | C13—C14—S1 | 129.07 (18) |
| N1—C7—C6 | 120.7 (2) | C9—C14—S1 | 109.47 (16) |
| O1—C1—C2—C3 | −178.7 (2) | C14—S1—C8—N2 | 1.30 (18) |
| C6—C1—C2—C3 | 1.4 (3) | C14—S1—C8—N1 | −178.28 (18) |
| C1—C2—C3—C4 | 0.2 (4) | C8—N2—C9—C10 | −179.1 (2) |
| C2—C3—C4—C5 | −1.2 (4) | C8—N2—C9—C14 | 0.2 (3) |
| C3—C4—C5—C6 | 0.6 (3) | N2—C9—C10—C11 | 179.7 (2) |
| C4—C5—C6—C1 | 0.9 (3) | C14—C9—C10—C11 | 0.4 (3) |
| C4—C5—C6—C7 | −180.0 (2) | C9—C10—C11—C12 | −0.1 (3) |
| O1—C1—C6—C5 | 178.2 (2) | C10—C11—C12—C13 | −0.6 (4) |
| C2—C1—C6—C5 | −1.9 (3) | C11—C12—C13—C14 | 1.1 (3) |
| O1—C1—C6—C7 | −0.9 (3) | C12—C13—C14—C9 | −0.8 (3) |
| C2—C1—C6—C7 | 179.0 (2) | C12—C13—C14—S1 | 179.15 (17) |
| C8—N1—C7—C6 | 179.8 (2) | N2—C9—C14—C13 | −179.33 (19) |
| C5—C6—C7—N1 | −179.6 (2) | C10—C9—C14—C13 | 0.0 (3) |
| C1—C6—C7—N1 | −0.5 (3) | N2—C9—C14—S1 | 0.7 (2) |
| C9—N2—C8—N1 | 178.51 (18) | C10—C9—C14—S1 | −179.89 (17) |
| C9—N2—C8—S1 | −1.1 (2) | C8—S1—C14—C13 | 179.0 (2) |
| C7—N1—C8—N2 | −177.6 (2) | C8—S1—C14—C9 | −1.04 (16) |
| C7—N1—C8—S1 | 2.0 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C14H10N2OS |
| Mr | 254.30 |
| Crystal system, space group | Monoclinic, Pn |
| Temperature (K) | 100 |
| a, b, c (Å) | 8.6391 (4), 6.2313 (4), 11.4459 (8) |
| β (°) | 108.893 (1) |
| V (Å3) | 582.97 (6) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.26 |
| Crystal size (mm) | 0.14 × 0.13 × 0.08 |
| Data collection | |
| Diffractometer | Bruker SMART APEX diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.964, 0.979 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 5307, 2599, 2512 |
| Rint | 0.029 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.110, 1.05 |
| No. of reflections | 2599 |
| No. of parameters | 164 |
| No. of restraints | 2 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.40, −0.25 |
| Absolute structure | Flack (1983), 1242 Friedel pairs |
| Absolute structure parameter | 0.27 (8) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank King Abdul Aziz University and the University of Malaya for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, S.-Q., Bi, C.-F., Chen, L.-Y. & Fan, Y.-H. (2009). Acta Cryst. E65, o738. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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. Submitted. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
| CRYSTALLOGRAPHIC COMMUNICATIONS |
The orthorhombic modification of 2-[(1,3-benzothiazol-2-yl)iminomethyl]phenol (Scheme I) is a flat molecule having a (calculated) density of 1.409 g ml-1 (Liu et al., 2009). In the monoclinic modification, the packing is more compact (calculated density 1.449 g ml-1). The benzisotholyl ring [r.m.s. deviation 0.007 Å] is co-planar with the phenylene ring [r.m.s. deviation 0.007 Å], the two rings being slightly bent by 2.6 (1) ° only. The hydroxy H-atom forms an intramolecular hydrogen bond to the imino group (Fig. 1). The r.m.s. deviation of the non-hydrogen atoms for the least-squares plane is 0.034 Å, and all deviations deviate by 0.002 Å only.