3-(6-Benzoyl-2-oxo-2,3-di­hydro-2-benzo­thia­zol-3-yl)­propanoic acid

The mol­ecule of the title compound, C₁₇H₁₃NO₄S, is non-planar. In the propanoic acid group, the average C-C bond length and the average C-C-C bond angle are 1.501 (1) Å and 110.9 (3)°, respectively.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.190
• Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.29
         From the CIF: _reflns_number_total               2818
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3067
         Completeness (_total/calc)             91.88%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The title compound, (I), showed higher analgesic activity than aspirin and has an anti-inflamatory activity as well as indometacin (Dündar et al., 2003). In this study, the crystal structure of (I) has been determined by X-ray diffraction.

The atom-numbering scheme of (I) is shown in Fig 2. Selected bond lengths and angles are listed in Table 1. The lengtening of the S1—C14 bond distance [1.781 (4) Å] versus the S1—C10 bond distance [1.743 (4) Å] is 0.034 (3) Å [S1—C7 = 1.776 (3) Å and S1—C6 = 1.742 (3) Å in methyl 3-(5-chloro-2-oxo-1.3-benzothiazol-3(2H)-yl)propanoate (Aydın, 2002)]. This case may be described in term of the steric interaction.

Maximum deviations from the mean plane through benzothiazole (N1/C11/C12/C13/C8/C9/C10/S1/C14, which is almost planar) are −0.016 (3) and 0.017 (3) Å for N1 and C12, respectively. The dihedral angle between the benzothiazole and the phenyl ring (C1–C6) is 49.2 (1)°.

The quantum-chemical calculation was performed by using the PM3 method and it was calculated that the charges at the N1, S1, O1, O2, O3 and O4 atoms are 0.0353, 0.1836, −0.2321, −0.2989, −0.2958 and −0.2186 e-, respectively. Final heat of formation of the title compound is −61.49 kcal and its total energy is −3735.42 eV. The values of the HOMO and LUMO energies are −9.19104 and −0.83799 eV, respectively. The molecule dipole moment calculated is 4.641 Debye.

Hydrogen-bonding contacts are summarized in Table 2. The crystal structure is stabilized by by C—H···O and O—H···O type of intermolecular hydrogen-bond networks.

S2. Experimental

3-(6-Benzoyl-2-benzothiazolinon-3-yl)propanenitrile (10.0 mmol) was added to N,N-dimethylformamide–water–sulfuric acid (1:1:2) mixture (50 ml). After stirring at room temperature for 2 h, the mixture was refluxed for 4 h. The mixture cooled to the room temperature was poured into ice water (100 g). The precipitate formed was filtered by suction filtration, washed with water, dried and crystallized from ethanol–water (yield 75%, m.p. 456–457 K).

S3. Refinement

All H atoms were placed in geometrically idealized positions, but not refined. The three-dimensional Bragg reflections of the title compound were collected on an Enraf–Nonius CAD-4 diffractometer using Mo Kα radiation. Due to the low quality of the crystal, the reflections from the planes with the high indices of the crystal measured were very weak in intensity. Therefore, data collection was stopped at θ_max = 26.29°.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Figures

	Fig. 1. A displacement ellipsoid plot (SHELXL97; Sheldrick, 1997) of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the crystal packing and hydrogen-bond contacts (dotted lines)) along the b axis.

3-(6-Benzoyl-2-oxo-2,3-dihydro-2-benzothiazol-3-yl)propanoic acid

Crystal data

C17H13NO4S	F(000) = 680
Mr = 327.35	Dx = 1.439 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 37 reflections
a = 9.352 (5) Å	θ = 9.4–32.3°
b = 12.921 (5) Å	µ = 0.23 mm^−1
c = 12.908 (5) Å	T = 293 K
β = 104.370 (5)°	Prism, yellow
V = 1511.0 (12) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.002
ω/2θ scans	θmax = 26.3°, θmin = 2.3°
Absorption correction: part of the refinement model (ΔF) (Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters	h = −11→11
Tmin = 0.944, Tmax = 0.966	k = −16→0
4283 measured reflections	l = 0→16
2818 independent reflections	3 standard reflections every 120 min
1906 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.190	H-atom parameters not refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1078P)^2 + 0.8574P] where P = (Fo^2 + 2Fc^2)/3
2818 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.16141 (10)	0.07368 (6)	0.52484 (8)	0.0525 (3)
O1	−0.0988 (3)	0.08710 (17)	0.0959 (2)	0.0551 (9)
O2	0.3058 (3)	0.17629 (19)	0.6990 (2)	0.0577 (9)
O3	0.3897 (3)	0.5280 (2)	0.7265 (2)	0.0606 (9)
O4	0.5923 (3)	0.5152 (2)	0.6670 (3)	0.0680 (10)
N1	0.1975 (3)	0.27124 (19)	0.5482 (2)	0.0421 (9)
C1	−0.3210 (3)	0.3116 (2)	0.1052 (3)	0.0400 (10)
C2	−0.4365 (4)	0.3652 (3)	0.0392 (3)	0.0494 (11)
C3	−0.4752 (4)	0.3461 (3)	−0.0677 (3)	0.0584 (14)
C4	−0.3995 (4)	0.2728 (3)	−0.1126 (3)	0.0644 (14)
C5	−0.2839 (4)	0.2192 (3)	−0.0472 (3)	0.0531 (12)
C6	−0.2432 (3)	0.2377 (2)	0.0625 (3)	0.0394 (10)
C7	−0.1266 (3)	0.1711 (2)	0.1305 (3)	0.0396 (10)
C8	−0.0450 (3)	0.2041 (2)	0.2392 (3)	0.0403 (10)
C9	0.0066 (3)	0.1270 (2)	0.3153 (3)	0.0417 (10)
C10	0.0868 (3)	0.1544 (2)	0.4168 (3)	0.0398 (10)
C11	0.1177 (3)	0.2589 (2)	0.4433 (3)	0.0374 (10)
C12	0.0697 (3)	0.3351 (2)	0.3679 (3)	0.0433 (10)
C13	−0.0118 (3)	0.3075 (2)	0.2676 (3)	0.0422 (10)
C14	0.2349 (3)	0.1816 (3)	0.6067 (3)	0.0445 (10)
C15	0.2440 (3)	0.3710 (3)	0.6008 (3)	0.0454 (11)
C16	0.3968 (4)	0.4018 (3)	0.5933 (3)	0.0515 (11)
C17	0.4557 (4)	0.4880 (3)	0.6686 (3)	0.0434 (11)
H1	−0.29523	0.32495	0.17832	0.0480*
H2	−0.48784	0.41452	0.06807	0.0592*
H3	−0.55316	0.38237	−0.11134	0.0701*
H4	−0.42643	0.26004	−0.18578	0.0773*
H5	−0.23273	0.17028	−0.07677	0.0637*
H9	−0.01291	0.05774	0.29793	0.0501*
H12	0.09204	0.40424	0.38455	0.0520*
H13	−0.04577	0.35907	0.21723	0.0507*
H15A	0.24253	0.36624	0.67556	0.0545*
H15B	0.17436	0.42416	0.56785	0.0545*
H16A	0.46232	0.34258	0.61005	0.0621*
H16B	0.39341	0.42337	0.52076	0.0621*
H40	0.61961	0.56319	0.70884	0.1021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0494 (5)	0.0362 (5)	0.0651 (7)	−0.0012 (3)	0.0015 (4)	0.0117 (4)
O1	0.0592 (15)	0.0370 (13)	0.0674 (18)	0.0052 (10)	0.0127 (13)	−0.0118 (11)
O2	0.0506 (14)	0.0572 (15)	0.0599 (19)	0.0056 (12)	0.0035 (13)	0.0097 (12)
O3	0.0667 (16)	0.0562 (15)	0.0648 (18)	−0.0068 (13)	0.0277 (14)	−0.0197 (13)
O4	0.0545 (15)	0.0770 (19)	0.076 (2)	−0.0221 (14)	0.0229 (14)	−0.0319 (15)
N1	0.0371 (13)	0.0365 (14)	0.0501 (18)	0.0005 (11)	0.0060 (12)	0.0027 (12)
C1	0.0441 (17)	0.0364 (16)	0.0406 (19)	−0.0025 (13)	0.0126 (14)	−0.0037 (13)
C2	0.0491 (19)	0.0402 (18)	0.062 (2)	0.0049 (14)	0.0196 (17)	0.0028 (16)
C3	0.055 (2)	0.058 (2)	0.057 (3)	0.0084 (17)	0.0041 (18)	0.0060 (18)
C4	0.065 (2)	0.079 (3)	0.046 (2)	0.007 (2)	0.0077 (19)	−0.0056 (19)
C5	0.052 (2)	0.056 (2)	0.053 (2)	0.0032 (16)	0.0161 (17)	−0.0107 (17)
C6	0.0382 (15)	0.0359 (15)	0.046 (2)	−0.0057 (13)	0.0140 (14)	−0.0026 (13)
C7	0.0370 (15)	0.0351 (16)	0.049 (2)	−0.0034 (12)	0.0148 (14)	−0.0035 (14)
C8	0.0370 (15)	0.0310 (15)	0.055 (2)	−0.0001 (12)	0.0152 (14)	−0.0017 (14)
C9	0.0406 (17)	0.0276 (15)	0.055 (2)	−0.0020 (12)	0.0085 (15)	−0.0032 (14)
C10	0.0375 (15)	0.0293 (15)	0.051 (2)	0.0014 (12)	0.0081 (14)	0.0065 (14)
C11	0.0329 (14)	0.0339 (15)	0.045 (2)	−0.0014 (12)	0.0089 (13)	−0.0008 (13)
C12	0.0461 (17)	0.0283 (15)	0.055 (2)	−0.0037 (13)	0.0116 (16)	−0.0018 (14)
C13	0.0430 (17)	0.0301 (15)	0.052 (2)	−0.0005 (13)	0.0092 (15)	0.0039 (14)
C14	0.0319 (15)	0.0482 (19)	0.051 (2)	0.0030 (14)	0.0055 (15)	0.0095 (15)
C15	0.0424 (17)	0.0417 (18)	0.051 (2)	0.0016 (14)	0.0095 (15)	−0.0077 (14)
C16	0.051 (2)	0.0479 (19)	0.060 (2)	−0.0068 (16)	0.0220 (18)	−0.0155 (17)
C17	0.0460 (17)	0.0422 (18)	0.041 (2)	−0.0026 (14)	0.0089 (15)	−0.0006 (14)

Geometric parameters (Å, º)

S1—C10	1.743 (4)	C8—C13	1.400 (4)
S1—C14	1.781 (4)	C9—C10	1.384 (5)
O1—C7	1.226 (4)	C10—C11	1.405 (4)
O2—C14	1.213 (5)	C11—C12	1.379 (5)
O3—C17	1.198 (5)	C12—C13	1.376 (5)
O4—C17	1.330 (5)	C15—C16	1.509 (5)
O4—H40	0.8203	C16—C17	1.491 (5)
N1—C11	1.384 (5)	C1—H1	0.9305
N1—C15	1.471 (5)	C2—H2	0.9297
N1—C14	1.379 (5)	C3—H3	0.9299
C1—C2	1.384 (5)	C4—H4	0.9300
C1—C6	1.394 (4)	C5—H5	0.9300
C2—C3	1.359 (5)	C9—H9	0.9296
C3—C4	1.392 (5)	C12—H12	0.9304
C4—C5	1.381 (5)	C13—H13	0.9301
C5—C6	1.393 (5)	C15—H15A	0.9705
C6—C7	1.492 (4)	C15—H15B	0.9692
C7—C8	1.484 (5)	C16—H16A	0.9705
C8—C9	1.398 (5)	C16—H16B	0.9699
S1···S1^i	3.491 (2)	C2···H16A^xii	3.0609
S1···H2^ii	3.1915	C6···H13	2.8332
O1···C15^iii	3.236 (4)	C8···H1	2.7603
O1···C12^iv	3.291 (4)	C12···H15B	2.7730
O2···C16	3.414 (5)	C12···H5^vi	3.0850
O2···O4^v	2.723 (4)	C13···H1	2.6246
O2···C13^vi	3.310 (5)	C14···H2^ii	3.0259
O3···C1^vii	3.181 (4)	C14···H40^v	2.8729
O3···C5^viii	3.362 (5)	C14···H16A	2.9675
O3···C2^vii	3.254 (5)	C15···H12	2.8331
O4···O2^ix	2.723 (4)	H1···C8	2.7603
O1···H15B^iii	2.6716	H1···C13	2.6246
O1···H9	2.5593	H1···H13	2.3038
O1···H5	2.5112	H1···O3^vii	2.5375
O1···H12^iv	2.3753	H2···O3^vii	2.6865
O2···H4^x	2.7938	H2···S1^xii	3.1915
O2···H15A	2.5252	H2···C14^xii	3.0259
O2···H40^v	1.9041	H3···O3^xiii	2.7663
O3···H15A	2.4992	H4···O2^xiii	2.7938
O3···H5^viii	2.8039	H5···O1	2.5112
O3···H3^x	2.7663	H5···O3^iv	2.8039
O3···H1^vii	2.5375	H5···C12^iii	3.0850
O3···H2^vii	2.6865	H9···O1	2.5593
O3···H15B	2.8289	H12···C15	2.8331
O4···H16B^xi	2.5851	H12···H15B	2.3136
C1···C13	3.122 (5)	H12···O1^viii	2.3753
C1···O3^vii	3.181 (4)	H13···C1	2.6917
C2···O3^vii	3.254 (5)	H13···C6	2.8332
C2···C14^xii	3.449 (5)	H13···H1	2.3038
C5···C17^iv	3.565 (6)	H15A···O2	2.5252
C5···O3^iv	3.362 (5)	H15A···O3	2.4992
C12···O1^viii	3.291 (4)	H15B···O3	2.8289
C13···C14^iii	3.469 (5)	H15B···C12	2.7730
C13···O2^iii	3.310 (5)	H15B···H12	2.3136
C13···C1	3.122 (5)	H15B···O1^vi	2.6716
C14···C13^vi	3.469 (5)	H16A···C14	2.9675
C14···C2^ii	3.449 (5)	H16A···C1^ii	2.8534
C15···O1^vi	3.236 (4)	H16A···C2^ii	3.0609
C16···O2	3.414 (5)	H16B···O4^xi	2.5851
C17···C5^viii	3.565 (6)	H40···O2^ix	1.9041
C1···H13	2.6917	H40···C14^ix	2.8728
C1···H16A^xii	2.8534
C10—S1—C14	91.44 (16)	N1—C15—C16	112.2 (3)
C17—O4—H40	109.44	C15—C16—C17	111.0 (3)
C11—N1—C15	125.3 (3)	O3—C17—C16	124.4 (4)
C14—N1—C15	118.5 (3)	O4—C17—C16	112.8 (3)
C11—N1—C14	116.2 (3)	O3—C17—O4	122.8 (4)
C2—C1—C6	120.2 (3)	C2—C1—H1	119.85
C1—C2—C3	120.3 (4)	C6—C1—H1	119.92
C2—C3—C4	120.8 (4)	C1—C2—H2	119.87
C3—C4—C5	119.2 (3)	C3—C2—H2	119.83
C4—C5—C6	120.7 (3)	C2—C3—H3	119.64
C1—C6—C5	118.8 (3)	C4—C3—H3	119.60
C5—C6—C7	118.3 (3)	C3—C4—H4	120.40
C1—C6—C7	122.6 (3)	C5—C4—H4	120.36
O1—C7—C6	119.1 (3)	C4—C5—H5	119.63
C6—C7—C8	121.3 (2)	C6—C5—H5	119.69
O1—C7—C8	119.5 (3)	C8—C9—H9	120.24
C7—C8—C9	117.8 (2)	C10—C9—H9	120.15
C7—C8—C13	123.4 (3)	C11—C12—H12	120.50
C9—C8—C13	118.7 (3)	C13—C12—H12	120.41
C8—C9—C10	119.6 (3)	C8—C13—H13	119.05
S1—C10—C9	128.3 (2)	C12—C13—H13	119.03
C9—C10—C11	120.4 (3)	N1—C15—H15A	109.14
S1—C10—C11	111.3 (3)	N1—C15—H15B	109.20
N1—C11—C12	127.6 (3)	C16—C15—H15A	109.13
C10—C11—C12	120.2 (3)	C16—C15—H15B	109.19
N1—C11—C10	112.2 (3)	H15A—C15—H15B	107.91
C11—C12—C13	119.1 (3)	C15—C16—H16A	109.47
C8—C13—C12	121.9 (3)	C15—C16—H16B	109.45
S1—C14—O2	125.1 (3)	C17—C16—H16A	109.45
O2—C14—N1	126.0 (3)	C17—C16—H16B	109.45
S1—C14—N1	108.9 (2)	H16A—C16—H16B	108.01
C14—S1—C10—C9	179.9 (3)	C1—C6—C7—O1	155.0 (3)
C14—S1—C10—C11	0.0 (2)	C5—C6—C7—O1	−19.6 (4)
C10—S1—C14—O2	−179.6 (3)	C5—C6—C7—C8	161.0 (3)
C10—S1—C14—N1	0.6 (2)	O1—C7—C8—C9	−29.1 (4)
C14—N1—C11—C10	1.3 (4)	C6—C7—C8—C13	−32.6 (4)
C15—N1—C11—C12	1.6 (5)	O1—C7—C8—C13	148.0 (3)
C14—N1—C11—C12	−178.5 (3)	C6—C7—C8—C9	150.3 (3)
C15—N1—C11—C10	−178.5 (3)	C7—C8—C9—C10	178.2 (3)
C15—N1—C14—S1	178.6 (2)	C7—C8—C13—C12	−177.1 (3)
C15—N1—C14—O2	−1.1 (5)	C9—C8—C13—C12	−0.1 (5)
C11—N1—C15—C16	−92.9 (4)	C13—C8—C9—C10	1.0 (4)
C14—N1—C15—C16	87.2 (4)	C8—C9—C10—C11	−0.6 (5)
C11—N1—C14—S1	−1.2 (3)	C8—C9—C10—S1	179.6 (2)
C11—N1—C14—O2	179.0 (3)	C9—C10—C11—N1	179.4 (3)
C6—C1—C2—C3	0.1 (5)	S1—C10—C11—C12	179.1 (2)
C2—C1—C6—C5	0.0 (5)	S1—C10—C11—N1	−0.7 (3)
C2—C1—C6—C7	−174.5 (3)	C9—C10—C11—C12	−0.7 (5)
C1—C2—C3—C4	−0.2 (6)	C10—C11—C12—C13	1.6 (5)
C2—C3—C4—C5	0.0 (6)	N1—C11—C12—C13	−178.5 (3)
C3—C4—C5—C6	0.2 (6)	C11—C12—C13—C8	−1.3 (5)
C4—C5—C6—C1	−0.2 (5)	N1—C15—C16—C17	−166.1 (3)
C4—C5—C6—C7	174.6 (3)	C15—C16—C17—O4	177.9 (3)
C1—C6—C7—C8	−24.4 (4)	C15—C16—C17—O3	−0.7 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H40···O2^ix	0.82	1.90	2.723 (4)	176
C1—H1···O3^vii	0.93	2.54	3.181 (4)	127
C12—H12···O1^viii	0.93	2.38	3.291 (4)	168
C16—H16B···O4^xi	0.97	2.59	3.552 (6)	175

Symmetry codes: (vii) −x, −y+1, −z+1; (viii) −x, y+1/2, −z+1/2; (ix) −x+1, y+1/2, −z+3/2; (xi) −x+1, −y+1, −z+1.