organic compounds
Methyl 2-(2-hydroxybenzylideneamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bChemistry Department, Faculty of Science, King Abdul-Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title compound, C17H17NO3S, the cyclohexene ring is essentially planar, with a maximum deviation of 0.006 (1) Å. The cyclohexene ring adopts a half-chair conformation. The dihedral angle between the thiophene and benzene rings is 29.7 (1)°. The molecular structure exhibits intramolecular O—H⋯O, O—H⋯N and C—H⋯S hydrogen bonds, which generate one S(5) and two S(6) motifs. There is also a C—H⋯π interaction between the cyclohexene ring system and the π-system of the benzene ring.
Related literature
For related literature, see: Akkurt et al. (2008); Allen et al. (1987); Asiri & Badahdah (2007); Bernstein et al. (1995); Cremer & Pople (1975); Etter (1990).
Experimental
Crystal data
|
Refinement
|
Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808010489/is2289sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010489/is2289Isup2.hkl
A solution of 2-amino-3-methoxycarbonyl-3,4,5,6-tetrahydrobenzo[d]thieophene (2.0 g, 6.35 mmol) in pure ethanol was heated to its boiling temperature, and then 2-hydroxynaphthaldehyde (0.77 g, 6.35 mmol) dissolved in hot ethanol was added to the amine solution and the resulting mixture was then refluxed for 5 h. Cooling the mixture, filtering the precipitates and recrystalization from ethanol gave the pure product (Asiri & Badahdah, 2007). IR (KBr) ν (cm-1); 1697 (C═O), 1604 (C═N), 1443 (C═C), 1323 (C—O) and 1136 (C—N) [yield 98%, m.p. 417 K].
The H atoms were positioned geometrically and allowed to ride on their parent atoms, with the C—H distances in the range of 0.93 - 0.97 Å and O—H = 0.82 Å, and Uiso(H) = 1.2Ueq (Caromatic, Cmethylene) and 1.5Ueq (Cmethyl, O).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C17H17NO3S | F(000) = 664 |
Mr = 315.39 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10365 reflections |
a = 7.6107 (4) Å | θ = 1.9–27.2° |
b = 21.2154 (9) Å | µ = 0.23 mm−1 |
c = 11.1827 (7) Å | T = 293 K |
β = 123.342 (4)° | Plate, yellow |
V = 1508.41 (16) Å3 | 0.60 × 0.47 × 0.23 mm |
Z = 4 |
Stoe IPDS2 diffractometer | 3086 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2361 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.078 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.5°, θmin = 1.9° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −23→26 |
Tmin = 0.876, Tmax = 0.950 | l = −14→13 |
8036 measured reflections |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3086 reflections | Δρmax = 0.34 e Å−3 |
200 parameters | Δρmin = −0.41 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=KFc[1 + 0.001×Fc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (3) |
C17H17NO3S | V = 1508.41 (16) Å3 |
Mr = 315.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6107 (4) Å | µ = 0.23 mm−1 |
b = 21.2154 (9) Å | T = 293 K |
c = 11.1827 (7) Å | 0.60 × 0.47 × 0.23 mm |
β = 123.342 (4)° |
Stoe IPDS2 diffractometer | 3086 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2361 reflections with I > 2σ(I) |
Tmin = 0.876, Tmax = 0.950 | Rint = 0.078 |
8036 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.34 e Å−3 |
3086 reflections | Δρmin = −0.41 e Å−3 |
200 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.38087 (8) | 0.27490 (2) | 0.37886 (5) | 0.0508 (2) | |
O1 | 0.7763 (2) | 0.43178 (7) | 0.81861 (15) | 0.0586 (5) | |
O2 | 0.8121 (3) | 0.28677 (7) | 0.86144 (15) | 0.0639 (5) | |
O3 | 0.8298 (3) | 0.18228 (7) | 0.85862 (16) | 0.0662 (5) | |
N1 | 0.6317 (2) | 0.34975 (7) | 0.61166 (15) | 0.0436 (4) | |
C1 | 0.7315 (3) | 0.45323 (8) | 0.59125 (18) | 0.0411 (5) | |
C2 | 0.7924 (3) | 0.47139 (9) | 0.7303 (2) | 0.0450 (5) | |
C3 | 0.8752 (3) | 0.53085 (10) | 0.7805 (2) | 0.0540 (7) | |
C4 | 0.9000 (3) | 0.57192 (9) | 0.6957 (3) | 0.0576 (7) | |
C5 | 0.8421 (3) | 0.55480 (10) | 0.5586 (2) | 0.0577 (7) | |
C6 | 0.7586 (3) | 0.49630 (9) | 0.5079 (2) | 0.0515 (6) | |
C7 | 0.6487 (3) | 0.39169 (8) | 0.53568 (19) | 0.0442 (5) | |
C8 | 0.5536 (3) | 0.29018 (8) | 0.55994 (19) | 0.0425 (5) | |
C9 | 0.6016 (3) | 0.23555 (8) | 0.63921 (19) | 0.0416 (5) | |
C10 | 0.7575 (3) | 0.23103 (9) | 0.7957 (2) | 0.0452 (6) | |
C11 | 0.9685 (4) | 0.28619 (13) | 1.0126 (2) | 0.0705 (8) | |
C12 | 0.4984 (3) | 0.18131 (8) | 0.55199 (19) | 0.0438 (5) | |
C13 | 0.5079 (3) | 0.11475 (9) | 0.6026 (2) | 0.0549 (6) | |
C14 | 0.3347 (3) | 0.07392 (9) | 0.4836 (2) | 0.0572 (7) | |
C15 | 0.3173 (3) | 0.08294 (10) | 0.3430 (2) | 0.0588 (7) | |
C16 | 0.2502 (4) | 0.14989 (10) | 0.2891 (2) | 0.0593 (7) | |
C17 | 0.3767 (3) | 0.19544 (9) | 0.41006 (19) | 0.0457 (6) | |
H1 | 0.72540 | 0.39820 | 0.77740 | 0.0880* | |
H3 | 0.91420 | 0.54310 | 0.87180 | 0.0650* | |
H4 | 0.95640 | 0.61170 | 0.73060 | 0.0690* | |
H5 | 0.85980 | 0.58280 | 0.50200 | 0.0690* | |
H6 | 0.71910 | 0.48490 | 0.41600 | 0.0620* | |
H7 | 0.60630 | 0.38190 | 0.44240 | 0.0530* | |
H11A | 1.09630 | 0.26820 | 1.02990 | 0.0850* | |
H11B | 0.91900 | 0.26140 | 1.06020 | 0.0850* | |
H11C | 0.99470 | 0.32850 | 1.04870 | 0.0850* | |
H13A | 0.49300 | 0.11530 | 0.68330 | 0.0660* | |
H13B | 0.64390 | 0.09660 | 0.63460 | 0.0660* | |
H14A | 0.36400 | 0.03000 | 0.51150 | 0.0690* | |
H14B | 0.20130 | 0.08450 | 0.47070 | 0.0690* | |
H15A | 0.21520 | 0.05350 | 0.27260 | 0.0700* | |
H15B | 0.45220 | 0.07430 | 0.35630 | 0.0700* | |
H16A | 0.27210 | 0.15830 | 0.21290 | 0.0710* | |
H16B | 0.10170 | 0.15510 | 0.25090 | 0.0710* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0565 (3) | 0.0466 (3) | 0.0366 (3) | −0.0026 (2) | 0.0176 (2) | 0.0017 (2) |
O1 | 0.0796 (9) | 0.0573 (8) | 0.0470 (8) | −0.0121 (7) | 0.0400 (7) | −0.0047 (7) |
O2 | 0.0802 (10) | 0.0530 (8) | 0.0349 (7) | −0.0107 (7) | 0.0166 (7) | 0.0015 (6) |
O3 | 0.0735 (9) | 0.0563 (9) | 0.0482 (8) | 0.0110 (7) | 0.0204 (7) | 0.0089 (7) |
N1 | 0.0454 (7) | 0.0411 (8) | 0.0389 (8) | 0.0005 (6) | 0.0197 (6) | 0.0023 (6) |
C1 | 0.0400 (8) | 0.0424 (9) | 0.0416 (9) | 0.0054 (7) | 0.0228 (7) | 0.0039 (7) |
C2 | 0.0482 (9) | 0.0446 (9) | 0.0475 (10) | 0.0020 (7) | 0.0297 (8) | 0.0005 (8) |
C3 | 0.0593 (11) | 0.0515 (11) | 0.0558 (12) | −0.0004 (9) | 0.0345 (10) | −0.0085 (9) |
C4 | 0.0577 (11) | 0.0404 (10) | 0.0765 (15) | −0.0011 (8) | 0.0381 (11) | −0.0031 (10) |
C5 | 0.0647 (12) | 0.0488 (11) | 0.0647 (13) | 0.0010 (9) | 0.0388 (11) | 0.0115 (10) |
C6 | 0.0574 (10) | 0.0532 (11) | 0.0470 (10) | 0.0011 (9) | 0.0306 (9) | 0.0049 (9) |
C7 | 0.0461 (9) | 0.0475 (10) | 0.0373 (9) | 0.0035 (7) | 0.0219 (7) | 0.0011 (8) |
C8 | 0.0427 (8) | 0.0432 (9) | 0.0385 (9) | 0.0007 (7) | 0.0204 (7) | −0.0008 (8) |
C9 | 0.0423 (8) | 0.0429 (9) | 0.0384 (9) | 0.0001 (7) | 0.0215 (7) | 0.0026 (7) |
C10 | 0.0448 (9) | 0.0482 (10) | 0.0414 (10) | −0.0014 (7) | 0.0230 (8) | 0.0022 (8) |
C11 | 0.0794 (15) | 0.0785 (15) | 0.0361 (10) | −0.0213 (12) | 0.0207 (10) | −0.0009 (10) |
C12 | 0.0417 (8) | 0.0435 (9) | 0.0443 (9) | −0.0005 (7) | 0.0225 (8) | 0.0007 (8) |
C13 | 0.0586 (11) | 0.0464 (10) | 0.0527 (11) | −0.0021 (8) | 0.0262 (9) | 0.0054 (9) |
C14 | 0.0635 (11) | 0.0457 (10) | 0.0665 (13) | −0.0071 (9) | 0.0384 (11) | −0.0037 (10) |
C15 | 0.0636 (11) | 0.0529 (11) | 0.0619 (13) | −0.0089 (9) | 0.0358 (10) | −0.0117 (10) |
C16 | 0.0657 (12) | 0.0575 (12) | 0.0460 (11) | −0.0116 (9) | 0.0251 (10) | −0.0100 (9) |
C17 | 0.0474 (9) | 0.0446 (10) | 0.0423 (10) | −0.0034 (7) | 0.0229 (8) | −0.0017 (8) |
S1—C8 | 1.7342 (18) | C13—C14 | 1.527 (3) |
S1—C17 | 1.725 (2) | C14—C15 | 1.516 (3) |
O1—C2 | 1.353 (3) | C15—C16 | 1.518 (3) |
O2—C10 | 1.333 (2) | C16—C17 | 1.503 (3) |
O2—C11 | 1.436 (2) | C3—H3 | 0.9300 |
O3—C10 | 1.201 (2) | C4—H4 | 0.9300 |
O1—H1 | 0.8200 | C5—H5 | 0.9300 |
N1—C8 | 1.381 (2) | C6—H6 | 0.9300 |
N1—C7 | 1.285 (2) | C7—H7 | 0.9300 |
C1—C2 | 1.410 (3) | C11—H11A | 0.9600 |
C1—C7 | 1.434 (2) | C11—H11B | 0.9600 |
C1—C6 | 1.399 (3) | C11—H11C | 0.9600 |
C2—C3 | 1.384 (3) | C13—H13A | 0.9700 |
C3—C4 | 1.375 (3) | C13—H13B | 0.9700 |
C4—C5 | 1.391 (3) | C14—H14A | 0.9700 |
C5—C6 | 1.367 (3) | C14—H14B | 0.9700 |
C8—C9 | 1.381 (2) | C15—H15A | 0.9700 |
C9—C10 | 1.482 (3) | C15—H15B | 0.9700 |
C9—C12 | 1.432 (2) | C16—H16A | 0.9700 |
C12—C17 | 1.361 (3) | C16—H16B | 0.9700 |
C12—C13 | 1.508 (3) | ||
S1···C11i | 3.543 (2) | C7···H16Bv | 3.0900 |
S1···C10ii | 3.468 (3) | C8···H11Bii | 2.9900 |
S1···H7 | 2.6900 | C8···H1 | 3.0600 |
O1···O2 | 3.102 (2) | C9···H11Bii | 2.9900 |
O1···N1 | 2.607 (2) | C10···H13A | 2.9800 |
O2···N1 | 2.694 (2) | C12···H15B | 3.0400 |
O2···O1 | 3.102 (2) | C17···H14B | 2.9600 |
O3···C4iii | 3.384 (3) | H1···O2 | 2.5000 |
O3···C7iv | 3.359 (3) | H1···N1 | 1.8800 |
O3···C13 | 2.923 (3) | H1···C7 | 2.4400 |
O1···H15Biv | 2.7200 | H1···C8 | 3.0600 |
O1···H14Bv | 2.7300 | H3···H14Bix | 2.5200 |
O2···H1 | 2.5000 | H4···O3vii | 2.7700 |
O3···H13A | 2.6300 | H4···H13Bvii | 2.5700 |
O3···H13B | 2.7700 | H5···O3vii | 2.9000 |
O3···H11B | 2.5800 | H5···H16Ax | 2.5900 |
O3···H4iii | 2.7700 | H6···H7 | 2.4200 |
O3···H5iii | 2.9000 | H7···S1 | 2.6900 |
O3···H11A | 2.6100 | H7···H6 | 2.4200 |
O3···H7iv | 2.7200 | H7···O3ii | 2.7200 |
N1···O1 | 2.607 (2) | H7···H13Aii | 2.5300 |
N1···O2 | 2.694 (2) | H11A···O3 | 2.6100 |
N1···H1 | 1.8800 | H11B···O3 | 2.5800 |
C1···C1vi | 3.552 (3) | H11B···C8iv | 2.9900 |
C1···C6vi | 3.427 (3) | H11B···C9iv | 2.9900 |
C2···C6vi | 3.588 (3) | H13A···O3 | 2.6300 |
C4···C7vi | 3.585 (4) | H13A···C10 | 2.9800 |
C4···O3vii | 3.384 (3) | H13A···H7iv | 2.5300 |
C5···C7vi | 3.468 (4) | H13B···O3 | 2.7700 |
C6···C2vi | 3.588 (3) | H13B···C4iii | 2.9500 |
C6···C1vi | 3.427 (3) | H13B···H4iii | 2.5700 |
C7···O3ii | 3.359 (3) | H14A···H14Axi | 2.5600 |
C7···C5vi | 3.468 (4) | H14B···C17 | 2.9600 |
C7···C4vi | 3.585 (4) | H14B···H3xii | 2.5200 |
C10···S1iv | 3.468 (3) | H14B···O1xiii | 2.7300 |
C11···S1viii | 3.543 (2) | H14B···C2xiii | 3.0200 |
C13···O3 | 2.923 (3) | H15A···C1xiii | 3.0800 |
C1···H15Av | 3.0800 | H15A···C2xiii | 3.0300 |
C2···H15Av | 3.0300 | H15B···C12 | 3.0400 |
C2···H14Bv | 3.0200 | H15B···O1ii | 2.7200 |
C4···H13Bvii | 2.9500 | H16A···H5xiv | 2.5900 |
C7···H1 | 2.4400 | H16B···C7xiii | 3.0900 |
C8—S1—C17 | 91.89 (9) | C4—C3—H3 | 120.00 |
C10—O2—C11 | 116.56 (17) | C3—C4—H4 | 119.00 |
C2—O1—H1 | 109.00 | C5—C4—H4 | 120.00 |
C7—N1—C8 | 122.23 (16) | C4—C5—H5 | 120.00 |
C2—C1—C7 | 121.75 (18) | C6—C5—H5 | 120.00 |
C6—C1—C7 | 119.76 (17) | C1—C6—H6 | 119.00 |
C2—C1—C6 | 118.47 (17) | C5—C6—H6 | 119.00 |
O1—C2—C1 | 121.91 (17) | N1—C7—H7 | 119.00 |
O1—C2—C3 | 118.30 (17) | C1—C7—H7 | 119.00 |
C1—C2—C3 | 119.79 (19) | O2—C11—H11A | 109.00 |
C2—C3—C4 | 120.16 (19) | O2—C11—H11B | 109.00 |
C3—C4—C5 | 121.0 (2) | O2—C11—H11C | 109.00 |
C4—C5—C6 | 119.2 (2) | H11A—C11—H11B | 109.00 |
C1—C6—C5 | 121.44 (18) | H11A—C11—H11C | 110.00 |
N1—C7—C1 | 121.58 (17) | H11B—C11—H11C | 109.00 |
S1—C8—N1 | 122.39 (13) | C12—C13—H13A | 109.00 |
N1—C8—C9 | 126.74 (16) | C12—C13—H13B | 109.00 |
S1—C8—C9 | 110.86 (13) | C14—C13—H13A | 109.00 |
C8—C9—C10 | 124.74 (17) | C14—C13—H13B | 109.00 |
C10—C9—C12 | 122.39 (16) | H13A—C13—H13B | 108.00 |
C8—C9—C12 | 112.63 (16) | C13—C14—H14A | 109.00 |
O2—C10—C9 | 113.48 (16) | C13—C14—H14B | 109.00 |
O3—C10—C9 | 124.00 (17) | C15—C14—H14A | 109.00 |
O2—C10—O3 | 122.52 (18) | C15—C14—H14B | 109.00 |
C9—C12—C17 | 112.61 (16) | H14A—C14—H14B | 108.00 |
C13—C12—C17 | 120.37 (16) | C14—C15—H15A | 110.00 |
C9—C12—C13 | 126.99 (16) | C14—C15—H15B | 110.00 |
C12—C13—C14 | 111.34 (16) | C16—C15—H15A | 110.00 |
C13—C14—C15 | 111.96 (19) | C16—C15—H15B | 110.00 |
C14—C15—C16 | 110.40 (18) | H15A—C15—H15B | 108.00 |
C15—C16—C17 | 109.58 (16) | C15—C16—H16A | 110.00 |
S1—C17—C16 | 121.34 (14) | C15—C16—H16B | 110.00 |
C12—C17—C16 | 126.65 (17) | C17—C16—H16A | 110.00 |
S1—C17—C12 | 112.01 (14) | C17—C16—H16B | 110.00 |
C2—C3—H3 | 120.00 | H16A—C16—H16B | 108.00 |
C17—S1—C8—C9 | −0.8 (2) | N1—C8—C9—C10 | −3.6 (4) |
C17—S1—C8—N1 | 177.8 (2) | S1—C8—C9—C10 | 174.9 (2) |
C8—S1—C17—C12 | 1.0 (2) | N1—C8—C9—C12 | −178.1 (2) |
C8—S1—C17—C16 | −178.8 (2) | C8—C9—C12—C13 | −177.4 (2) |
C11—O2—C10—C9 | −177.8 (2) | C8—C9—C12—C17 | 0.4 (3) |
C11—O2—C10—O3 | 1.9 (4) | C12—C9—C10—O3 | 10.0 (4) |
C7—N1—C8—C9 | 152.2 (3) | C8—C9—C10—O2 | 15.7 (4) |
C7—N1—C8—S1 | −26.2 (3) | C8—C9—C10—O3 | −164.0 (3) |
C8—N1—C7—C1 | −179.6 (2) | C12—C9—C10—O2 | −170.3 (2) |
C2—C1—C6—C5 | 0.1 (4) | C10—C9—C12—C13 | 7.9 (4) |
C7—C1—C2—O1 | 0.1 (4) | C10—C9—C12—C17 | −174.3 (2) |
C6—C1—C7—N1 | 176.4 (2) | C9—C12—C13—C14 | 164.9 (2) |
C7—C1—C2—C3 | 178.8 (2) | C9—C12—C17—C16 | 178.9 (3) |
C2—C1—C7—N1 | −1.9 (4) | C17—C12—C13—C14 | −12.7 (3) |
C6—C1—C2—O1 | −178.2 (2) | C9—C12—C17—S1 | −1.0 (3) |
C7—C1—C6—C5 | −178.3 (2) | C13—C12—C17—C16 | −3.2 (4) |
C6—C1—C2—C3 | 0.5 (4) | C13—C12—C17—S1 | 177.03 (19) |
C1—C2—C3—C4 | −0.6 (4) | C12—C13—C14—C15 | 45.8 (3) |
O1—C2—C3—C4 | 178.1 (2) | C13—C14—C15—C16 | −64.5 (3) |
C2—C3—C4—C5 | 0.3 (4) | C14—C15—C16—C17 | 45.7 (3) |
C3—C4—C5—C6 | 0.3 (4) | C15—C16—C17—C12 | −13.8 (4) |
C4—C5—C6—C1 | −0.4 (4) | C15—C16—C17—S1 | 166.03 (19) |
S1—C8—C9—C12 | 0.4 (3) |
Symmetry codes: (i) x−1, y, z−1; (ii) x, −y+1/2, z−1/2; (iii) −x+2, y−1/2, −z+3/2; (iv) x, −y+1/2, z+1/2; (v) x+1, −y+1/2, z+1/2; (vi) −x+1, −y+1, −z+1; (vii) −x+2, y+1/2, −z+3/2; (viii) x+1, y, z+1; (ix) −x+1, y+1/2, −z+3/2; (x) −x+1, y+1/2, −z+1/2; (xi) −x+1, −y, −z+1; (xii) −x+1, y−1/2, −z+3/2; (xiii) x−1, −y+1/2, z−1/2; (xiv) −x+1, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 2.50 | 3.102 (2) | 132 |
O1—H1···N1 | 0.82 | 1.88 | 2.607 (2) | 146 |
C7—H7···S1 | 0.93 | 2.69 | 3.0725 (19) | 105 |
C15—H15A···Cgxiii | 0.97 | 2.92 | 3.782 (3) | 150 |
Symmetry code: (xiii) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H17NO3S |
Mr | 315.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.6107 (4), 21.2154 (9), 11.1827 (7) |
β (°) | 123.342 (4) |
V (Å3) | 1508.41 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.60 × 0.47 × 0.23 |
Data collection | |
Diffractometer | Stoe IPDS2 diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.876, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8036, 3086, 2361 |
Rint | 0.078 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.121, 0.99 |
No. of reflections | 3086 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.41 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 2.50 | 3.102 (2) | 132 |
O1—H1···N1 | 0.82 | 1.88 | 2.607 (2) | 146 |
C7—H7···S1 | 0.93 | 2.69 | 3.0725 (19) | 105 |
C15—H15A···Cgi | 0.97 | 2.92 | 3.782 (3) | 150 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant F.279 of the University Research Fund).
References
Akkurt, M., Yıldırım, S. Ö., Asiri, A. M. & McKee, V. (2008). Acta Cryst. E64, o682. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Asiri, A. M. & Badahdah, K. O. (2007). Molecules, 12, 1796-1804. Web of Science CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. 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.
In a previous paper, we reported the structure of 4-[(2-hydroxy-1-naphthyl)methylideneamino]benzoic acid (Akkurt et al., 2008). The present work is part of an ongoing investigation in the development of anil derivatives. Here, we report the structure of the title compound 2-[(2-hydroxybenzylidene)amino]-3-methoxycarbonyl-3,4,5,6- tetrahydrobenzo[d]thiophene, (I).
In the title compound (I) (Fig. 1), all bond lengths and angles are in normal range (Allen et al., 1987). The thiophene ring is essentially planar, with maximum deviations of 0.006 (1) Å for S1 and 0.006 (3) Å for C17. The cyclohexene ring adopts a half-chair conformation, with the puckering parameters QT = 0.502 (2) Å, θ = 52.1 (2)° and ϕ = 151.4 (3)° (Cremer & Pople, 1975). The dihedral angle between the thiophene ring and the benzene ring is 29.7 (1)°.
In the molecular structure, the intramolecular O1—H1···O2, and O1—H1···N1 hydrogen bonds form two pseudo-six membered rings [S(6) motifs (Bernstein et al., 1995; Etter, 1990)] and C7—H7···S1 forms a pseudo five membered ring [S(5) motif], thus locking the molecular conformation and eliminating flexibility (Fig. 1 and Table 1). There are also interactions of the C—H···π type [C15—H15A···π (-1 + x, 1/2 - y, -1/2 + z), H15···π = 2.91 Å, C15···π = 3.782 (3) Å] observed between the cyclohexene ring system and the π system of the benzene ring. A view of the packing of the title compound in the unit cell is shown in Fig. 2.