2-(6-Benzoyl-2-oxo-1,3-benzothia­zol-3-yl)acetic acid

Aydın, A.; Akkurt, M.; Önkol, T.; Büyükgüngör, O.; Şahin, M.F.

doi:10.1107/S160053680905329X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o168

doi:10.1107/S160053680905329X

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2-(6-Benzoyl-2-oxo-1,3-benzothiazol-3-yl)acetic acid

Abdullah Aydın,^a ^* Mehmet Akkurt,^b ‡ Tijen Önkol,^c Orhan Büyükgüngör ^d and M. Fethi Şahin ^c

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: aaydin@kastamonu.edu.tr

(Received 7 December 2009; accepted 10 December 2009; online 16 December 2009)

In the title compound, C₁₆H₁₁NO₄S, the nine-membered fused ring is nearly planar, with maximum deviations from the mean plane of −0.022 (1) Å for the N atom and 0.011 (1) Å for the S atom, and makes a dihedral angle of 53.56 (7)° with the phenyl ring. The crystal structure is stabilized by O—H⋯O and C—H⋯O hydrogen-bonding interactions.

Related literature

For the pharmacological effects of 2-benzoxazolinone/benzothiazolinone derivatives, see: Ünlü et al. (2003 ); Petrov et al. (1994 ). For the quantum-chemical calculations, see: Pople & Beveridge (1970 ).

Experimental

Crystal data

C₁₆H₁₁NO₄S
M_r = 313.33
Orthorhombic, P b c a
a = 11.4248 (3) Å
b = 8.9155 (2) Å
c = 27.6280 (8) Å
V = 2814.13 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.59 × 0.38 × 0.17 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.868, T_max = 0.959
31503 measured reflections
3006 independent reflections
2363 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.04
3006 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1ⁱ	0.82	1.86	2.6315 (18)	157
C9—H9⋯O2ⁱⁱ	0.93	2.43	3.1233 (19)	131
C15—H15B⋯O3ⁱⁱⁱ	0.97	2.54	3.416 (2)	150
Symmetry codes: (i) x-1, y, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); 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/S160053680905329X/hg2616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905329X/hg2616Isup2.hkl

checkCIF report

Comment top

2-Benzoxazolinone / benzothiazolinone derivatives exhibit a variety of pharmacological effects, including anlgesic and anti-inflammatory activity (Ünlü et al., 2003). It was studied analgesic and anti-inflammatory activity of the title compound which was synthesized by (Petrov et al., 1994) previously. Based on this study, the title compound, (I), showed close anlgesic activity that of aspirin at 100 mg/kg dose, but in terms of anti-inflammatory activity, inactive (Ünlü et al., 2003). In this study, the structure of the title compound (I) has been determined by single-crystal X-ray diffraction.

In (I) (Fig. 1), the nine-membered ring S1/N1/C8–C14 is nearly planar with maximum deviations of -0.022 (1) Å for N1 and 0.011 (1) Å for S1 from the mean plane. The dihedral angle between the nine-membered ring and the phenyl ring C1–C6 is 53.56 (7)° [the calculated value is 74.47°, using the CNDO (Pople et al., 1970) aproximation]. The N1—C15—C16—O3 and N1—C15—C16—O4 torsion angles related with the carboxyl group are 0.7 (3) and -177.21 (15)° [the calculated values are 114.5° and -65.95°].

In the crystal structure of (I), there exist intermolecular O—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2).

The quantum-chemical calculation of (I) was carried out by using the CNDO aproximation. The HOMO and LUMO energy levels of (I) are -10.4385 and 2.0553 eV, respectively. Its calculated molecule dipole moment is 8.206 Debye (1 D = 3.33564 × 10 ^-30 C.m.). Due to the intermolecular interactions in the crystal structure of (I), the spatial configurations obtained by the theoretical CNDO and experimental X-rays for (I) are almost different (see Figs. 1 & 3). But the geometric parameters in (I) are almost comparable within the experimental error interval in the results of both methods.

Related literature top

For the pharmacological effects of 2-benzoxazolinone/benzothiazolinone derivatives, see: Ünlü et al. (2003); Petrov et al. (1994). For the quantum-chemical calculations, see: Pople & Beveridge (1970).

Experimental top

Methyl (6-benzoyl-2-oxo-1,3-benzothiazol-3-yl)acetate (2 mmol) and sodium hydroxide (2 mmol) in 30 ml e thanol/water (25:5) was refluxed for 4 h. After cooling to room temperature, the mixture was acidified with 1 N HCl (30 ml) to give a solid precipitate.The product was collected by suction filtration, washed with water, dried, and crystallized from ethanol/water to yield % 73 [m.p.: 524 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: SIR97 (Altomare et al., 1999); 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 view of the title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing and hydrogen bonding of the title compound viewed down b axis.Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. The spatial view of the title molecule (I), calculated by the CNDO aproximation.

2-(6-Benzoyl-2-oxo-1,3-benzothiazol-3-yl)acetic acid top

Crystal data top

C₁₆H₁₁NO₄S	F(000) = 1296
M_r = 313.33	D_x = 1.479 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 31743 reflections
a = 11.4248 (3) Å	θ = 1.5–27.3°
b = 8.9155 (2) Å	µ = 0.25 mm⁻¹
c = 27.6280 (8) Å	T = 296 K
V = 2814.13 (13) Å³	Prismatic stick, colourless
Z = 8	0.59 × 0.38 × 0.17 mm

Data collection top

Stoe IPDS 2 diffractometer	3006 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2363 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.034
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.8°, θ_min = 1.5°
ω scans	h = −14→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
T_min = 0.868, T_max = 0.959	l = −34→34
31503 measured reflections

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0454P)² + 0.2486P] where P = (F_o² + 2F_c²)/3
3006 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₁NO₄S	V = 2814.13 (13) Å³
M_r = 313.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.4248 (3) Å	µ = 0.25 mm⁻¹
b = 8.9155 (2) Å	T = 296 K
c = 27.6280 (8) Å	0.59 × 0.38 × 0.17 mm

Data collection top

Stoe IPDS 2 diffractometer	3006 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2363 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.959	R_int = 0.034
31503 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
3006 reflections	Δρ_min = −0.22 e Å⁻³
199 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	0.57030 (3)	0.23072 (5)	0.52487 (1)	0.0462 (1)
O1	0.92276 (8)	0.45469 (15)	0.63203 (5)	0.0573 (4)
O2	0.35095 (10)	0.25597 (15)	0.49337 (5)	0.0616 (4)
O3	0.22769 (11)	0.33284 (18)	0.61382 (5)	0.0748 (5)
O4	0.11738 (11)	0.5146 (2)	0.58490 (7)	0.1006 (7)
N1	0.41141 (9)	0.41838 (15)	0.55272 (5)	0.0415 (4)
C1	0.85487 (12)	0.61124 (17)	0.69378 (6)	0.0431 (5)
C2	0.78137 (14)	0.6046 (2)	0.73373 (6)	0.0551 (6)
C3	0.80669 (18)	0.6877 (3)	0.77475 (7)	0.0681 (7)
C4	0.90272 (18)	0.7800 (3)	0.77570 (8)	0.0700 (8)
C5	0.97516 (18)	0.7884 (2)	0.73637 (8)	0.0683 (7)
C6	0.95280 (14)	0.7034 (2)	0.69545 (7)	0.0536 (6)
C7	0.83707 (12)	0.51557 (17)	0.65028 (6)	0.0413 (5)
C8	0.71999 (11)	0.49170 (17)	0.62847 (5)	0.0377 (4)
C9	0.71055 (11)	0.38169 (17)	0.59286 (5)	0.0381 (4)
C10	0.60499 (11)	0.36100 (17)	0.56983 (5)	0.0369 (4)
C11	0.50840 (11)	0.45213 (17)	0.58098 (5)	0.0368 (4)
C12	0.51704 (12)	0.56159 (18)	0.61601 (6)	0.0439 (5)
C13	0.62268 (12)	0.58068 (18)	0.63966 (6)	0.0421 (5)
C14	0.42573 (13)	0.30165 (19)	0.52075 (6)	0.0450 (5)
C15	0.30209 (11)	0.5004 (2)	0.55357 (6)	0.0467 (5)
C16	0.21427 (12)	0.4378 (2)	0.58824 (6)	0.0474 (5)
H2	0.71500	0.54420	0.73290	0.0660*
H3	0.75840	0.68090	0.80180	0.0820*
H4	0.91860	0.83690	0.80310	0.0840*
H4A	0.06890	0.48070	0.60390	0.1510*
H5	1.03990	0.85160	0.73710	0.0820*
H6	1.00330	0.70810	0.66910	0.0640*
H9	0.77490	0.32290	0.58480	0.0460*
H12	0.45300	0.62150	0.62360	0.0530*
H13	0.62920	0.65400	0.66350	0.0500*
H15A	0.26860	0.49990	0.52130	0.0560*
H15B	0.31800	0.60390	0.56220	0.0560*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0364 (2)	0.0550 (2)	0.0471 (2)	−0.0031 (2)	0.0034 (2)	−0.0099 (2)
O1	0.0299 (5)	0.0725 (8)	0.0696 (8)	0.0023 (5)	0.0037 (5)	−0.0135 (7)
O2	0.0450 (6)	0.0859 (9)	0.0539 (7)	−0.0120 (6)	−0.0099 (5)	−0.0088 (7)
O3	0.0626 (8)	0.0835 (10)	0.0784 (9)	0.0153 (7)	0.0236 (7)	0.0317 (8)
O4	0.0414 (7)	0.1141 (13)	0.1464 (15)	0.0268 (8)	0.0339 (8)	0.0644 (12)
N1	0.0271 (5)	0.0520 (8)	0.0453 (7)	−0.0015 (5)	0.0000 (5)	0.0024 (6)
C1	0.0366 (7)	0.0452 (9)	0.0474 (8)	0.0017 (6)	−0.0073 (6)	0.0022 (7)
C2	0.0472 (9)	0.0682 (12)	0.0500 (10)	0.0000 (8)	−0.0019 (7)	0.0012 (9)
C3	0.0670 (11)	0.0905 (15)	0.0468 (10)	0.0117 (11)	−0.0050 (8)	−0.0069 (10)
C4	0.0698 (12)	0.0787 (15)	0.0614 (12)	0.0119 (10)	−0.0237 (10)	−0.0187 (11)
C5	0.0575 (10)	0.0647 (13)	0.0827 (15)	−0.0073 (9)	−0.0250 (10)	−0.0094 (11)
C6	0.0413 (8)	0.0592 (10)	0.0604 (11)	−0.0045 (7)	−0.0089 (7)	−0.0012 (9)
C7	0.0323 (7)	0.0457 (9)	0.0460 (8)	−0.0017 (6)	0.0014 (6)	0.0029 (7)
C8	0.0308 (6)	0.0420 (8)	0.0402 (8)	−0.0007 (6)	0.0016 (5)	0.0008 (7)
C9	0.0294 (6)	0.0442 (8)	0.0408 (8)	0.0031 (6)	0.0041 (5)	0.0007 (7)
C10	0.0307 (6)	0.0420 (8)	0.0379 (7)	−0.0018 (5)	0.0048 (5)	0.0011 (6)
C11	0.0269 (6)	0.0431 (8)	0.0405 (8)	−0.0010 (5)	0.0019 (5)	0.0046 (7)
C12	0.0313 (7)	0.0473 (9)	0.0532 (9)	0.0070 (6)	0.0031 (6)	−0.0044 (8)
C13	0.0365 (7)	0.0422 (8)	0.0476 (9)	0.0014 (6)	0.0014 (6)	−0.0064 (7)
C14	0.0359 (7)	0.0580 (10)	0.0410 (8)	−0.0095 (7)	0.0021 (6)	0.0037 (7)
C15	0.0290 (6)	0.0546 (9)	0.0564 (9)	0.0015 (6)	−0.0007 (6)	0.0095 (8)
C16	0.0340 (7)	0.0529 (10)	0.0552 (10)	0.0027 (6)	0.0037 (6)	0.0047 (8)

Geometric parameters (Å, º) top

S1—C10	1.7462 (15)	C8—C13	1.400 (2)
S1—C14	1.7723 (16)	C8—C9	1.393 (2)
O1—C7	1.2277 (18)	C9—C10	1.3760 (18)
O2—C14	1.212 (2)	C10—C11	1.4046 (19)
O3—C16	1.183 (2)	C11—C12	1.378 (2)
O4—C16	1.305 (2)	C12—C13	1.383 (2)
O4—H4A	0.8200	C15—C16	1.495 (2)
N1—C14	1.375 (2)	C2—H2	0.9300
N1—C15	1.4475 (18)	C3—H3	0.9300
N1—C11	1.3885 (18)	C4—H4	0.9300
C1—C6	1.389 (2)	C5—H5	0.9300
C1—C7	1.488 (2)	C6—H6	0.9300
C1—C2	1.388 (2)	C9—H9	0.9300
C2—C3	1.385 (3)	C12—H12	0.9300
C3—C4	1.372 (3)	C13—H13	0.9300
C4—C5	1.368 (3)	C15—H15A	0.9700
C5—C6	1.385 (3)	C15—H15B	0.9700
C7—C8	1.4824 (19)

S1···N1	2.5858 (13)	C15···O3^viii	3.416 (2)
S1···O2ⁱ	3.2479 (12)	C15···O2^viii	3.319 (2)
S1···C15ⁱⁱ	3.5452 (17)	C1···H13	2.7400
S1···O4ⁱⁱⁱ	3.3258 (17)	C2···H13	2.6400
S1···H15Bⁱⁱ	3.1000	C4···H2^xii	2.9600
O1···O4^iv	2.6315 (18)	C7···H4A^iv	2.9600
O1···C13^v	3.381 (2)	C8···H2	2.9200
O2···S1^vi	3.2479 (12)	C12···H15B	2.7400
O2···C15ⁱⁱⁱ	3.319 (2)	C13···H9^xii	2.8900
O2···C9^vi	3.1233 (19)	C13···H2	2.8000
O3···N1	2.7994 (18)	C15···H12	2.8100
O3···C15ⁱⁱⁱ	3.416 (2)	C16···H15Bⁱⁱⁱ	3.0800
O3···C3^vii	3.363 (3)	H2···C8	2.9200
O4···C14^viii	3.152 (2)	H2···C13	2.8000
O4···S1^viii	3.3258 (17)	H2···H13	2.3700
O4···O1^ix	2.6315 (18)	H2···C4^v	2.9600
O1···H9	2.4400	H3···O3^xi	2.7000
O1···H13^v	2.8800	H4···O1^xiii	2.7600
O1···H6	2.6500	H4···O3^xi	2.8400
O1···H4A^iv	1.8600	H4A···O1^ix	1.8600
O1···H4^x	2.7600	H4A···C7^ix	2.9600
O2···H15Aⁱⁱⁱ	2.7700	H6···O1	2.6500
O2···H15A	2.4900	H9···O1	2.4400
O2···H9^vi	2.4300	H9···O2ⁱ	2.4300
O3···H4^vii	2.8400	H9···C13^v	2.8900
O3···H15Bⁱⁱⁱ	2.5400	H12···C15	2.8100
O3···H12ⁱⁱⁱ	2.8100	H12···H15B	2.3000
O3···H3^vii	2.7000	H12···O3^viii	2.8100
N1···S1	2.5858 (13)	H13···C1	2.7400
N1···O3	2.7994 (18)	H13···C2	2.6400
C2···C13	3.176 (2)	H13···H2	2.3700
C3···O3^xi	3.363 (3)	H13···O1^xii	2.8800
C9···C13^v	3.536 (2)	H15A···O2	2.4900
C9···O2ⁱ	3.1233 (19)	H15A···O2^viii	2.7700
C13···C2	3.176 (2)	H15B···C12	2.7400
C13···O1^xii	3.381 (2)	H15B···H12	2.3000
C13···C9^xii	3.536 (2)	H15B···S1ⁱⁱ	3.1000
C14···O4ⁱⁱⁱ	3.152 (2)	H15B···O3^viii	2.5400
C15···S1ⁱⁱ	3.5452 (17)	H15B···C16^viii	3.0800

C10—S1—C14	91.14 (7)	S1—C14—N1	109.86 (11)
C16—O4—H4A	110.00	O2—C14—N1	124.87 (14)
C11—N1—C14	115.49 (12)	S1—C14—O2	125.26 (13)
C11—N1—C15	124.75 (13)	N1—C15—C16	113.63 (14)
C14—N1—C15	119.71 (12)	O3—C16—C15	126.24 (14)
C2—C1—C7	122.36 (13)	O4—C16—C15	109.15 (15)
C6—C1—C7	118.43 (14)	O3—C16—O4	124.57 (16)
C2—C1—C6	119.09 (16)	C1—C2—H2	120.00
C1—C2—C3	120.11 (16)	C3—C2—H2	120.00
C2—C3—C4	120.25 (18)	C2—C3—H3	120.00
C3—C4—C5	120.1 (2)	C4—C3—H3	120.00
C4—C5—C6	120.46 (19)	C3—C4—H4	120.00
C1—C6—C5	119.97 (17)	C5—C4—H4	120.00
O1—C7—C8	119.28 (14)	C4—C5—H5	120.00
C1—C7—C8	122.28 (12)	C6—C5—H5	120.00
O1—C7—C1	118.44 (13)	C1—C6—H6	120.00
C7—C8—C9	117.25 (12)	C5—C6—H6	120.00
C9—C8—C13	119.55 (12)	C8—C9—H9	120.00
C7—C8—C13	123.05 (13)	C10—C9—H9	120.00
C8—C9—C10	119.26 (13)	C11—C12—H12	121.00
S1—C10—C11	111.25 (10)	C13—C12—H12	121.00
C9—C10—C11	120.64 (13)	C8—C13—H13	119.00
S1—C10—C9	128.10 (11)	C12—C13—H13	119.00
N1—C11—C10	112.23 (13)	N1—C15—H15A	109.00
N1—C11—C12	127.27 (13)	N1—C15—H15B	109.00
C10—C11—C12	120.49 (12)	C16—C15—H15A	109.00
C11—C12—C13	118.78 (13)	C16—C15—H15B	109.00
C8—C13—C12	121.25 (15)	H15A—C15—H15B	108.00

C14—S1—C10—C9	−178.35 (15)	C2—C3—C4—C5	−1.1 (4)
C14—S1—C10—C11	0.72 (12)	C3—C4—C5—C6	−0.4 (3)
C10—S1—C14—N1	0.32 (12)	C4—C5—C6—C1	1.4 (3)
C10—S1—C14—O2	179.26 (16)	O1—C7—C8—C13	−165.40 (15)
C11—N1—C15—C16	−92.11 (18)	C1—C7—C8—C9	−169.92 (14)
C15—N1—C14—O2	−2.9 (2)	C1—C7—C8—C13	14.6 (2)
C11—N1—C14—S1	−1.33 (17)	O1—C7—C8—C9	10.1 (2)
C15—N1—C11—C12	3.7 (2)	C9—C8—C13—C12	0.0 (2)
C14—N1—C11—C12	−179.09 (15)	C7—C8—C13—C12	175.37 (15)
C11—N1—C14—O2	179.73 (16)	C7—C8—C9—C10	−176.64 (13)
C14—N1—C11—C10	1.91 (19)	C13—C8—C9—C10	−1.0 (2)
C14—N1—C15—C16	90.74 (18)	C8—C9—C10—C11	1.8 (2)
C15—N1—C14—S1	176.08 (11)	C8—C9—C10—S1	−179.27 (11)
C15—N1—C11—C10	−175.35 (14)	S1—C10—C11—C12	179.35 (12)
C7—C1—C6—C5	−176.84 (16)	C9—C10—C11—N1	177.56 (13)
C2—C1—C7—C8	43.9 (2)	S1—C10—C11—N1	−1.58 (16)
C2—C1—C6—C5	−0.8 (2)	C9—C10—C11—C12	−1.5 (2)
C6—C1—C7—C8	−140.18 (16)	C10—C11—C12—C13	0.5 (2)
C6—C1—C7—O1	39.8 (2)	N1—C11—C12—C13	−178.44 (15)
C7—C1—C2—C3	175.14 (17)	C11—C12—C13—C8	0.3 (2)
C2—C1—C7—O1	−136.10 (17)	N1—C15—C16—O3	0.7 (3)
C6—C1—C2—C3	−0.8 (3)	N1—C15—C16—O4	−177.21 (15)
C1—C2—C3—C4	1.7 (3)

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y−1/2, z; (iv) x+1, y, z; (v) −x+3/2, y−1/2, z; (vi) x−1/2, −y+1/2, −z+1; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+1/2, y+1/2, z; (ix) x−1, y, z; (x) −x+2, y−1/2, −z+3/2; (xi) −x+1, y+1/2, −z+3/2; (xii) −x+3/2, y+1/2, z; (xiii) −x+2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1^ix	0.82	1.86	2.6315 (18)	157
C9—H9···O2ⁱ	0.93	2.43	3.1233 (19)	131
C15—H15B···O3^viii	0.97	2.54	3.416 (2)	150

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (viii) −x+1/2, y+1/2, z; (ix) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁NO₄S
M_r	313.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.4248 (3), 8.9155 (2), 27.6280 (8)
V (Å³)	2814.13 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.59 × 0.38 × 0.17

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.868, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	31503, 3006, 2363
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.04
No. of reflections	3006
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), 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
O4—H4A···O1ⁱ	0.82	1.86	2.6315 (18)	157
C9—H9···O2ⁱⁱ	0.93	2.43	3.1233 (19)	131
C15—H15B···O3ⁱⁱⁱ	0.97	2.54	3.416 (2)	150

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, z.

Footnotes

‡Additional corresponding author, e-mail: akkurt@erciyes.edu.tr.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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