organic compounds
3-(4-Hexyloxyphenyl)-1,2,4-triazolo[3,4-b]benzothiazole
aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: detert@uni-mainz.de
The title compound, C20H21N3OS, was prepared by Huisgen reaction of 5-(4-hexyloxyphenyl)tetrazole and chlorobenzothiazole. The essentially planar benzothiazolotriazole framework [maximum deviation from the mean plane of 0.077 (1) Å for the bridgehead N atom] and the phenyl ring form a dihedral angle of 53.34 (5)°. The hexyloxy chain adopts a gauche–all-anti conformation. The intracentroid separation of 3.7258 (8) Å between the triazole and benzene rings is the closest contact between individual molecules in the crystal.
CCDC reference: 984210
Related literature
For related benzothiazolotriazoles, see: Butler et al. (1972); Reynolds & van Allan (1959). For triazolo-annulation via tetrazoles, see: Christiano et al. (2008). For the Huisgen reaction, see: Huisgen et al. (1960,1961). For the structures of related triazolo-annulated heterocycles, see: Preis et al. (2011a,b); Herget et al. (2013); Puviarasnan et al. (1999).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2011); cell X-AREA; data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supporting information
CCDC reference: 984210
10.1107/S1600536814002153/nc2323sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002153/nc2323Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002153/nc2323Isup3.cml
The title compound was prepared by adding chlorobenzothiazole (0.49 g, 2.75 mmol) to a stirred solution of 5-(4-hexyloxyphenyl)tetrazole (0.67 g, 2.75 mmol) and collidine (0.5 ml) in xylenes (12 ml). The mixture was stirred for 15 h at ambient temperature and heated to 392 K for 24 h. The cooled solution was filtered, washed with water (30 ml), dried (CaCl2) and concentrated.
on silica gel using toluene / ethyl acetate 3 / 7 (Rf = 0.15) as an yielded 0.66 g of the pure title compound (68%). Recrystallization from methanol / dichloromethane gave off-white crystals with m.p. = 400 KHydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.98–0.99 Å (sp3 C-atom). All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom).
Data collection: X-AREA (Stoe & Cie, 2011); cell
X-AREA (Stoe & Cie, 2011); data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. |
C20H21N3OS | Dx = 1.329 Mg m−3 |
Mr = 351.46 | Melting point: 400 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 32877 reflections |
a = 10.7369 (4) Å | θ = 2.2–33.7° |
b = 9.1770 (3) Å | µ = 0.20 mm−1 |
c = 35.6567 (11) Å | T = 193 K |
V = 3513.3 (2) Å3 | Needle, colourless |
Z = 8 | 0.50 × 0.20 × 0.20 mm |
F(000) = 1488 |
Stoe IPDS 2T diffractometer | 3441 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.074 |
Graphite monochromator | θmax = 28.0°, θmin = 2.9° |
Detector resolution: 6.67 pixels mm-1 | h = −14→14 |
rotation method scans | k = −8→12 |
26869 measured reflections | l = −47→38 |
4225 independent 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.9425P] where P = (Fo2 + 2Fc2)/3 |
4225 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C20H21N3OS | V = 3513.3 (2) Å3 |
Mr = 351.46 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 10.7369 (4) Å | µ = 0.20 mm−1 |
b = 9.1770 (3) Å | T = 193 K |
c = 35.6567 (11) Å | 0.50 × 0.20 × 0.20 mm |
Stoe IPDS 2T diffractometer | 3441 reflections with I > 2σ(I) |
26869 measured reflections | Rint = 0.074 |
4225 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.30 e Å−3 |
4225 reflections | Δρmin = −0.23 e Å−3 |
227 parameters |
Experimental. 1H-NMR (CDCl3): δ = 7.66 (m, 3 H); 7.51 (d, 1 H, J = 7.5 Hz), 7.35 ("t", 1 H), 7.29 ("t", 1H), 7.06 (d, 2 H, J = 8 Hz), 4.05, t, 2 H), 1.83 (qui, 2 H), 1.48 (qui, 2 H), 1.33 (m, 4 H), 0.90 ("t", 3H). 13C-NMR(CDCl3): δ = 156.0, 150.7, 154.3, 127.5, 125.5 (2c), 125.0, 121.2, 121.1, 119.7, 113.5, 109.9, 109.2, 63.2, 26.5, 24.1, 20.6, 17.5, 8.9. FD—MS:351.4 (M+H+). UV-Vis: dichloromethane: λmax = 260 nm (log ε = 4.11), λmax = 298 nm (log ε = 3.85); cyclohexane: λmax = 261 nm, λmax = 298 nm; λmax = 298 nm; ethanol: λmax = 258 nm, λmax = 295 nm; fluorescence: dichloromethane: λmax = 356 nm; cyclohexane: λmax = 333 nm; ethanol: λmax = 358 nm. |
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 | ||
S1 | 0.41618 (4) | 0.26300 (4) | 0.696695 (10) | 0.03581 (13) | |
C2 | 0.40821 (12) | 0.43744 (15) | 0.67607 (4) | 0.0304 (3) | |
C3 | 0.41068 (14) | 0.57003 (18) | 0.69481 (4) | 0.0364 (3) | |
H3 | 0.4124 | 0.5737 | 0.7214 | 0.044* | |
C4 | 0.41053 (13) | 0.69677 (17) | 0.67376 (5) | 0.0374 (3) | |
H4 | 0.4115 | 0.7884 | 0.6861 | 0.045* | |
C5 | 0.40897 (13) | 0.69200 (16) | 0.63482 (5) | 0.0340 (3) | |
H5 | 0.4109 | 0.7804 | 0.6210 | 0.041* | |
C6 | 0.40465 (12) | 0.55988 (15) | 0.61587 (4) | 0.0299 (3) | |
H6 | 0.4030 | 0.5564 | 0.5892 | 0.036* | |
C7 | 0.40282 (11) | 0.43353 (14) | 0.63696 (4) | 0.0260 (3) | |
N8 | 0.40149 (10) | 0.28738 (12) | 0.62443 (3) | 0.0263 (2) | |
C9 | 0.40200 (12) | 0.20746 (15) | 0.59169 (4) | 0.0280 (3) | |
N10 | 0.41399 (11) | 0.06852 (13) | 0.60013 (4) | 0.0348 (3) | |
N11 | 0.42111 (12) | 0.05377 (13) | 0.63912 (4) | 0.0361 (3) | |
C12 | 0.41293 (12) | 0.18574 (15) | 0.65223 (4) | 0.0304 (3) | |
C13 | 0.38612 (12) | 0.26957 (15) | 0.55412 (4) | 0.0280 (3) | |
C14 | 0.46740 (13) | 0.23437 (15) | 0.52481 (4) | 0.0311 (3) | |
H14 | 0.5331 | 0.1670 | 0.5291 | 0.037* | |
C15 | 0.45328 (13) | 0.29627 (16) | 0.48985 (4) | 0.0323 (3) | |
H15 | 0.5089 | 0.2710 | 0.4702 | 0.039* | |
C16 | 0.35734 (12) | 0.39615 (15) | 0.48326 (4) | 0.0289 (3) | |
C17 | 0.27419 (12) | 0.42904 (15) | 0.51209 (4) | 0.0307 (3) | |
H17 | 0.2073 | 0.4947 | 0.5077 | 0.037* | |
C18 | 0.28918 (12) | 0.36596 (15) | 0.54696 (4) | 0.0304 (3) | |
H18 | 0.2321 | 0.3889 | 0.5664 | 0.036* | |
O19 | 0.35160 (9) | 0.45394 (11) | 0.44817 (3) | 0.0345 (2) | |
C20 | 0.25760 (14) | 0.56334 (16) | 0.44224 (4) | 0.0354 (3) | |
H20A | 0.2658 | 0.6407 | 0.4614 | 0.043* | |
H20B | 0.1739 | 0.5191 | 0.4448 | 0.043* | |
C21 | 0.27167 (14) | 0.62833 (16) | 0.40378 (4) | 0.0367 (3) | |
H21A | 0.3565 | 0.6698 | 0.4016 | 0.044* | |
H21B | 0.2118 | 0.7098 | 0.4013 | 0.044* | |
C22 | 0.25134 (13) | 0.52382 (17) | 0.37123 (4) | 0.0349 (3) | |
H22A | 0.3231 | 0.4564 | 0.3695 | 0.042* | |
H22B | 0.1757 | 0.4650 | 0.3760 | 0.042* | |
C23 | 0.23673 (14) | 0.60407 (17) | 0.33430 (4) | 0.0368 (3) | |
H23A | 0.1652 | 0.6716 | 0.3364 | 0.044* | |
H23B | 0.3123 | 0.6635 | 0.3299 | 0.044* | |
C24 | 0.21655 (17) | 0.50588 (19) | 0.30070 (5) | 0.0451 (4) | |
H24A | 0.2927 | 0.4472 | 0.2965 | 0.054* | |
H24B | 0.1475 | 0.4377 | 0.3063 | 0.054* | |
C25 | 0.1863 (2) | 0.5888 (2) | 0.26520 (5) | 0.0612 (5) | |
H25A | 0.1085 | 0.6430 | 0.2687 | 0.092* | |
H25B | 0.1768 | 0.5200 | 0.2444 | 0.092* | |
H25C | 0.2540 | 0.6570 | 0.2596 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0409 (2) | 0.0353 (2) | 0.0313 (2) | 0.00007 (15) | −0.00034 (14) | 0.00440 (14) |
C2 | 0.0281 (6) | 0.0311 (7) | 0.0319 (7) | 0.0002 (5) | −0.0004 (5) | −0.0004 (6) |
C3 | 0.0350 (7) | 0.0393 (8) | 0.0350 (8) | −0.0002 (6) | −0.0015 (6) | −0.0103 (6) |
C4 | 0.0349 (7) | 0.0303 (7) | 0.0471 (9) | 0.0004 (6) | −0.0036 (6) | −0.0129 (7) |
C5 | 0.0333 (7) | 0.0239 (7) | 0.0449 (8) | −0.0005 (5) | −0.0033 (6) | −0.0039 (6) |
C6 | 0.0291 (6) | 0.0258 (7) | 0.0348 (7) | −0.0019 (5) | −0.0016 (5) | −0.0013 (6) |
C7 | 0.0228 (6) | 0.0231 (6) | 0.0322 (7) | −0.0009 (5) | 0.0001 (5) | −0.0043 (5) |
N8 | 0.0271 (5) | 0.0215 (5) | 0.0302 (6) | −0.0011 (4) | 0.0003 (4) | −0.0009 (4) |
C9 | 0.0250 (6) | 0.0237 (6) | 0.0353 (7) | −0.0015 (5) | −0.0006 (5) | −0.0060 (5) |
N10 | 0.0345 (6) | 0.0243 (6) | 0.0455 (7) | −0.0005 (5) | −0.0050 (5) | −0.0035 (5) |
N11 | 0.0385 (6) | 0.0255 (6) | 0.0443 (7) | −0.0007 (5) | −0.0040 (5) | 0.0030 (5) |
C12 | 0.0283 (6) | 0.0267 (7) | 0.0360 (7) | −0.0010 (5) | −0.0005 (5) | 0.0041 (6) |
C13 | 0.0275 (6) | 0.0249 (6) | 0.0315 (7) | −0.0025 (5) | −0.0028 (5) | −0.0063 (5) |
C14 | 0.0270 (6) | 0.0281 (7) | 0.0382 (7) | 0.0043 (5) | −0.0008 (6) | −0.0067 (6) |
C15 | 0.0304 (7) | 0.0306 (7) | 0.0358 (7) | 0.0030 (5) | 0.0038 (6) | −0.0060 (6) |
C16 | 0.0286 (6) | 0.0257 (6) | 0.0324 (7) | −0.0016 (5) | −0.0025 (5) | −0.0061 (5) |
C17 | 0.0267 (6) | 0.0292 (7) | 0.0361 (7) | 0.0037 (5) | −0.0033 (5) | −0.0085 (6) |
C18 | 0.0264 (6) | 0.0314 (7) | 0.0334 (7) | 0.0008 (5) | 0.0008 (5) | −0.0077 (6) |
O19 | 0.0360 (5) | 0.0331 (5) | 0.0343 (5) | 0.0066 (4) | 0.0009 (4) | −0.0016 (4) |
C20 | 0.0336 (7) | 0.0292 (7) | 0.0435 (8) | 0.0034 (5) | 0.0009 (6) | 0.0006 (6) |
C21 | 0.0346 (7) | 0.0274 (7) | 0.0482 (8) | −0.0013 (6) | 0.0007 (6) | 0.0057 (6) |
C22 | 0.0319 (7) | 0.0290 (7) | 0.0437 (8) | −0.0024 (5) | −0.0040 (6) | 0.0081 (6) |
C23 | 0.0369 (7) | 0.0303 (7) | 0.0431 (8) | 0.0024 (6) | 0.0039 (6) | 0.0081 (6) |
C24 | 0.0515 (9) | 0.0386 (9) | 0.0452 (9) | −0.0031 (7) | 0.0014 (7) | 0.0053 (7) |
C25 | 0.0812 (14) | 0.0626 (12) | 0.0398 (9) | 0.0116 (11) | 0.0092 (9) | 0.0047 (9) |
S1—C12 | 1.7370 (15) | C16—O19 | 1.3605 (17) |
S1—C2 | 1.7638 (15) | C16—C17 | 1.395 (2) |
C2—C3 | 1.388 (2) | C17—C18 | 1.381 (2) |
C2—C7 | 1.396 (2) | C17—H17 | 0.9500 |
C3—C4 | 1.384 (2) | C18—H18 | 0.9500 |
C3—H3 | 0.9500 | O19—C20 | 1.4392 (17) |
C4—C5 | 1.389 (2) | C20—C21 | 1.503 (2) |
C4—H4 | 0.9500 | C20—H20A | 0.9900 |
C5—C6 | 1.389 (2) | C20—H20B | 0.9900 |
C5—H5 | 0.9500 | C21—C22 | 1.521 (2) |
C6—C7 | 1.382 (2) | C21—H21A | 0.9900 |
C6—H6 | 0.9500 | C21—H21B | 0.9900 |
C7—N8 | 1.4137 (17) | C22—C23 | 1.517 (2) |
N8—C12 | 1.3667 (18) | C22—H22A | 0.9900 |
N8—C9 | 1.3787 (18) | C22—H22B | 0.9900 |
C9—N10 | 1.3164 (18) | C23—C24 | 1.515 (2) |
C9—C13 | 1.466 (2) | C23—H23A | 0.9900 |
N10—N11 | 1.399 (2) | C23—H23B | 0.9900 |
N11—C12 | 1.3012 (19) | C24—C25 | 1.512 (2) |
C13—C18 | 1.3897 (19) | C24—H24A | 0.9900 |
C13—C14 | 1.399 (2) | C24—H24B | 0.9900 |
C14—C15 | 1.378 (2) | C25—H25A | 0.9800 |
C14—H14 | 0.9500 | C25—H25B | 0.9800 |
C15—C16 | 1.399 (2) | C25—H25C | 0.9800 |
C15—H15 | 0.9500 | ||
C12—S1—C2 | 89.37 (7) | C18—C17—H17 | 120.1 |
C3—C2—C7 | 120.26 (13) | C16—C17—H17 | 120.1 |
C3—C2—S1 | 126.43 (12) | C17—C18—C13 | 121.31 (13) |
C7—C2—S1 | 113.28 (11) | C17—C18—H18 | 119.3 |
C4—C3—C2 | 118.38 (14) | C13—C18—H18 | 119.3 |
C4—C3—H3 | 120.8 | C16—O19—C20 | 116.03 (11) |
C2—C3—H3 | 120.8 | O19—C20—C21 | 109.90 (12) |
C3—C4—C5 | 121.03 (14) | O19—C20—H20A | 109.7 |
C3—C4—H4 | 119.5 | C21—C20—H20A | 109.7 |
C5—C4—H4 | 119.5 | O19—C20—H20B | 109.7 |
C6—C5—C4 | 120.94 (14) | C21—C20—H20B | 109.7 |
C6—C5—H5 | 119.5 | H20A—C20—H20B | 108.2 |
C4—C5—H5 | 119.5 | C20—C21—C22 | 115.56 (12) |
C7—C6—C5 | 117.91 (14) | C20—C21—H21A | 108.4 |
C7—C6—H6 | 121.0 | C22—C21—H21A | 108.4 |
C5—C6—H6 | 121.0 | C20—C21—H21B | 108.4 |
C6—C7—C2 | 121.42 (13) | C22—C21—H21B | 108.4 |
C6—C7—N8 | 128.61 (13) | H21A—C21—H21B | 107.5 |
C2—C7—N8 | 109.90 (12) | C23—C22—C21 | 111.77 (13) |
C12—N8—C9 | 104.52 (12) | C23—C22—H22A | 109.3 |
C12—N8—C7 | 114.67 (12) | C21—C22—H22A | 109.3 |
C9—N8—C7 | 140.56 (12) | C23—C22—H22B | 109.3 |
N10—C9—N8 | 108.80 (13) | C21—C22—H22B | 109.3 |
N10—C9—C13 | 126.64 (13) | H22A—C22—H22B | 107.9 |
N8—C9—C13 | 124.51 (12) | C24—C23—C22 | 114.37 (13) |
C9—N10—N11 | 109.03 (12) | C24—C23—H23A | 108.7 |
C12—N11—N10 | 105.28 (12) | C22—C23—H23A | 108.7 |
N11—C12—N8 | 112.37 (13) | C24—C23—H23B | 108.7 |
N11—C12—S1 | 134.96 (12) | C22—C23—H23B | 108.7 |
N8—C12—S1 | 112.65 (10) | H23A—C23—H23B | 107.6 |
C18—C13—C14 | 118.47 (13) | C25—C24—C23 | 113.19 (15) |
C18—C13—C9 | 120.17 (12) | C25—C24—H24A | 108.9 |
C14—C13—C9 | 121.35 (12) | C23—C24—H24A | 108.9 |
C15—C14—C13 | 120.78 (13) | C25—C24—H24B | 108.9 |
C15—C14—H14 | 119.6 | C23—C24—H24B | 108.9 |
C13—C14—H14 | 119.6 | H24A—C24—H24B | 107.8 |
C14—C15—C16 | 120.21 (13) | C24—C25—H25A | 109.5 |
C14—C15—H15 | 119.9 | C24—C25—H25B | 109.5 |
C16—C15—H15 | 119.9 | H25A—C25—H25B | 109.5 |
O19—C16—C17 | 124.37 (12) | C24—C25—H25C | 109.5 |
O19—C16—C15 | 116.32 (12) | H25A—C25—H25C | 109.5 |
C17—C16—C15 | 119.31 (13) | H25B—C25—H25C | 109.5 |
C18—C17—C16 | 119.89 (12) | ||
C12—S1—C2—C3 | −177.71 (13) | C7—N8—C12—N11 | −174.91 (11) |
C12—S1—C2—C7 | 0.27 (10) | C9—N8—C12—S1 | 179.33 (9) |
C7—C2—C3—C4 | −1.4 (2) | C7—N8—C12—S1 | 3.92 (14) |
S1—C2—C3—C4 | 176.40 (11) | C2—S1—C12—N11 | 176.13 (15) |
C2—C3—C4—C5 | −0.5 (2) | C2—S1—C12—N8 | −2.34 (10) |
C3—C4—C5—C6 | 1.5 (2) | N10—C9—C13—C18 | 128.50 (15) |
C4—C5—C6—C7 | −0.4 (2) | N8—C9—C13—C18 | −48.64 (19) |
C5—C6—C7—C2 | −1.54 (19) | N10—C9—C13—C14 | −51.7 (2) |
C5—C6—C7—N8 | −178.36 (12) | N8—C9—C13—C14 | 131.13 (14) |
C3—C2—C7—C6 | 2.5 (2) | C18—C13—C14—C15 | 1.4 (2) |
S1—C2—C7—C6 | −175.59 (10) | C9—C13—C14—C15 | −178.40 (13) |
C3—C2—C7—N8 | 179.88 (12) | C13—C14—C15—C16 | 0.3 (2) |
S1—C2—C7—N8 | 1.76 (13) | C14—C15—C16—O19 | 178.83 (13) |
C6—C7—N8—C12 | 173.48 (13) | C14—C15—C16—C17 | −1.9 (2) |
C2—C7—N8—C12 | −3.63 (15) | O19—C16—C17—C18 | −179.06 (12) |
C6—C7—N8—C9 | 0.5 (2) | C15—C16—C17—C18 | 1.7 (2) |
C2—C7—N8—C9 | −176.62 (14) | C16—C17—C18—C13 | 0.0 (2) |
C12—N8—C9—N10 | −0.47 (14) | C14—C13—C18—C17 | −1.6 (2) |
C7—N8—C9—N10 | 172.96 (14) | C9—C13—C18—C17 | 178.22 (12) |
C12—N8—C9—C13 | 177.11 (12) | C17—C16—O19—C20 | 4.47 (19) |
C7—N8—C9—C13 | −9.5 (2) | C15—C16—O19—C20 | −176.25 (12) |
N8—C9—N10—N11 | 0.29 (15) | C16—O19—C20—C21 | 173.79 (12) |
C13—C9—N10—N11 | −177.22 (12) | O19—C20—C21—C22 | 63.84 (16) |
C9—N10—N11—C12 | 0.02 (15) | C20—C21—C22—C23 | 166.39 (12) |
N10—N11—C12—N8 | −0.33 (15) | C21—C22—C23—C24 | 179.82 (13) |
N10—N11—C12—S1 | −178.80 (12) | C22—C23—C24—C25 | 172.79 (15) |
C9—N8—C12—N11 | 0.50 (15) |
Experimental details
Crystal data | |
Chemical formula | C20H21N3OS |
Mr | 351.46 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 193 |
a, b, c (Å) | 10.7369 (4), 9.1770 (3), 35.6567 (11) |
V (Å3) | 3513.3 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.50 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDS 2T diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26869, 4225, 3441 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.119, 1.04 |
No. of reflections | 4225 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.23 |
Computer programs: X-AREA (Stoe & Cie, 2011), X-RED (Stoe & Cie, 2011), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
References
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The Huisgen reaction of tetrazoles and 2-chloroazines is a versatile method for the synthesis of 1,2,4-triazolo-annulated azines see: Preis et al. (2011a, 2011b), Herget et al. (2013), and Christiano et al. (2008). This method is also applicable to azoles with active chlorine and this structure confirms the corresponding [3,4-b]- annulation. The essentially planar benzothiazolotriazole framework of title compound C20H21N3OS (max. deviation 0.077 Å from mean plane at N(8) and the planar phenyl ring open a dihedral angle of 53.34 (5)°. The structural features of the π-system are very similar to a derivative lacking the hexyloxy group, see Puviarasnan et al. (1999). The O19—C20 bond is nearly coplanar with the mean plane of the phenyl ring (torsion angle: 6.6°) and the hexyl chain shows a gauche-all-anti konformation. A minimal distance of 3.73 Å between neighbouring molecules was found for the centroids of the triazole and the benzo-ring.