Methyl 2-(2-hydroxy­benzyl­ideneamino)-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carboxyl­ate

Akkurt, M.; Karaca, S.; Asiri, A.M.; Büyükgüngör, O.

doi:10.1107/S1600536808010489

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o869

doi:10.1107/S1600536808010489

Open

access

Methyl 2-(2-hydroxybenzylideneamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Mehmet Akkurt,^a ^* Selvi Karaca,^a Abdullah Mohamed Asiri ^b and Orhan Büyükgüngör ^c

^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

(Received 15 April 2008; accepted 16 April 2008; online 18 April 2008)

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

C₁₇H₁₇NO₃S
M_r = 315.39
Monoclinic, P 2₁ /c
a = 7.6107 (4) Å
b = 21.2154 (9) Å
c = 11.1827 (7) Å
β = 123.342 (4)°
V = 1508.41 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 (2) K
0.60 × 0.47 × 0.23 mm

Data collection

Stoe IPDS2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.876, T_max = 0.950
8036 measured reflections
3086 independent reflections
2361 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 0.99
3086 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the benzene ring.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010489/is2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010489/is2289Isup2.hkl

checkCIF report

Comment top

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 Q_T = 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.

Related literature top

For related literature, see: Akkurt et al. (2008); Allen et al. (1987); Asiri & Badahdah (2007); Bernstein et al. (1995); Cremer & Pople (1975); Etter (1990). Cg is the centroid of the benzene ring.

Experimental top

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].

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

Figures top

	Fig. 1. An ORTEP-3 view of the title compound (I), with the atom-numbering scheme, intramolecular H-bonds and 30% probability displacement ellipsoids.
	Fig. 2. A view of the packing of (I) in the unit cell.

Methyl 2-(2-hydroxybenzylideneamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate top

Crystal data top

C₁₇H₁₇NO₃S	F(000) = 664
M_r = 315.39	D_x = 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

Data collection top

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	R_int = 0.078
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.9°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −23→26
T_min = 0.876, T_max = 0.950	l = −14→13
8036 measured reflections

Refinement top

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(F_o²) + (0.072P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
3086 reflections	Δρ_max = 0.34 e Å⁻³
200 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₇NO₃S	V = 1508.41 (16) Å³
M_r = 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)°

Data collection top

Stoe IPDS2 diffractometer	3086 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2361 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.950	R_int = 0.078
8036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 0.99	Δρ_max = 0.34 e Å⁻³
3086 reflections	Δρ_min = −0.41 e Å⁻³
200 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···H16B^v	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···C7^iv	3.359 (3)	H1···N1	1.8800
O3···C13	2.923 (3)	H1···C7	2.4400
O1···H15B^iv	2.7200	H1···C8	3.0600
O1···H14B^v	2.7300	H3···H14B^ix	2.5200
O2···H1	2.5000	H4···O3^vii	2.7700
O3···H13A	2.6300	H4···H13B^vii	2.5700
O3···H13B	2.7700	H5···O3^vii	2.9000
O3···H11B	2.5800	H5···H16A^x	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···H7^iv	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···C1^vi	3.552 (3)	H11B···C8^iv	2.9900
C1···C6^vi	3.427 (3)	H11B···C9^iv	2.9900
C2···C6^vi	3.588 (3)	H13A···O3	2.6300
C4···C7^vi	3.585 (4)	H13A···C10	2.9800
C4···O3^vii	3.384 (3)	H13A···H7^iv	2.5300
C5···C7^vi	3.468 (4)	H13B···O3	2.7700
C6···C2^vi	3.588 (3)	H13B···C4ⁱⁱⁱ	2.9500
C6···C1^vi	3.427 (3)	H13B···H4ⁱⁱⁱ	2.5700
C7···O3ⁱⁱ	3.359 (3)	H14A···H14A^xi	2.5600
C7···C5^vi	3.468 (4)	H14B···C17	2.9600
C7···C4^vi	3.585 (4)	H14B···H3^xii	2.5200
C10···S1^iv	3.468 (3)	H14B···O1^xiii	2.7300
C11···S1^viii	3.543 (2)	H14B···C2^xiii	3.0200
C13···O3	2.923 (3)	H15A···C1^xiii	3.0800
C1···H15A^v	3.0800	H15A···C2^xiii	3.0300
C2···H15A^v	3.0300	H15B···C12	3.0400
C2···H14B^v	3.0200	H15B···O1ⁱⁱ	2.7200
C4···H13B^vii	2.9500	H16A···H5^xiv	2.5900
C7···H1	2.4400	H16B···C7^xiii	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.

Hydrogen-bond geometry (Å, º) top

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···Cg^xiii	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
M_r	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)
T_min, T_max	0.876, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	8036, 3086, 2361
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o869

doi:10.1107/S1600536808010489

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 2-(2-hy­droxy­benzyl­­idene­amino)-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-(2-hydroxybenzylideneamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate