Methyl 3-(2-oxobenzo­thia­zolin-3-yl)­propanoate

In the title compound, C₆H₄SC(O)NCH₂CH₂COOCH₃, the bicyclic benzo­thia­zole system is planar within 0.025 Å; the displacements of the carbonyl oxy­gen and the β-carbon atom of the methyl­propionate substituent from the benzo­thia­zole mean plane are −0.028 (2) and 0.002 (2) Å, respectively. There is a short intermolecular C—H...O contact between the α atom of the methyl ­propionate substituent and the carbonyl oxy­gen of the oxobenzo­thia­zole group [C...O 3.241 (2) Å]. These contacts link the mol­ecules into infinite chains, running along the b axis of the crystal.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.126
• Data-to-parameter ratio = 21.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.90 mm

Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.287
            Value of mu given      =     0.290

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Methyl 3-(2-oxobenzothiazoline-3-yl)propanoate

Crystal data

C11H11NO3S	F(000) = 496
Mr = 237.27	Dx = 1.443 Mg m^−3
Monoclinic, P21/c	Melting point: 330 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 7.9109 (13) Å	Cell parameters from 3603 reflections
b = 8.386 (3) Å	θ = 20.1–26.4°
c = 16.4898 (16) Å	µ = 0.29 mm^−1
β = 93.645 (12)°	T = 293 K
V = 1091.8 (4) Å^3	Prism, yellow
Z = 4	0.90 × 0.60 × 0.25 mm

Data collection

Rigaku AFC-7S diffractometer	2039 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.040
Graphite monochromator	θmax = 30.0°, θmin = 2.5°
ω–2θ scans	h = 0→11
Absorption correction: ψ scan North et al., 1968	k = 0→11
Tmin = 0.812, Tmax = 0.930	l = −23→23
3383 measured reflections	3 standard reflections every 150 reflections
3176 independent reflections	intensity decay: 0.6%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0588P)^2 + 0.2099P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3176 reflections	Δρmax = 0.25 e Å^−3
146 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.085 (5)

Special details

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.

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

	x	y	z	Uiso*/Ueq
S1	0.25538 (7)	0.17569 (5)	0.51309 (3)	0.05439 (17)
N1	0.12490 (17)	0.34196 (16)	0.39321 (8)	0.0440 (3)
O1	0.09372 (19)	0.07022 (16)	0.37773 (9)	0.0651 (4)
O2	0.2970 (2)	0.57779 (17)	0.25554 (11)	0.0741 (5)
O3	0.40718 (17)	0.36035 (16)	0.20159 (9)	0.0575 (3)
C1	0.2695 (2)	0.3827 (2)	0.51872 (10)	0.0431 (3)
C2	0.3463 (2)	0.4725 (2)	0.58099 (11)	0.0528 (4)
H2	0.4011	0.4238	0.6260	0.063*
C3	0.3391 (3)	0.6368 (2)	0.57438 (13)	0.0620 (5)
H3	0.3888	0.6999	0.6157	0.074*
C4	0.2590 (3)	0.7079 (2)	0.50711 (14)	0.0632 (5)
H4	0.2544	0.8186	0.5042	0.076*
C5	0.1846 (2)	0.6183 (2)	0.44327 (12)	0.0540 (4)
H5	0.1325	0.6674	0.3977	0.065*
C6	0.19077 (19)	0.45405 (18)	0.44985 (10)	0.0412 (3)
C7	0.1437 (2)	0.1859 (2)	0.41688 (11)	0.0480 (4)
C8	0.0318 (2)	0.3775 (2)	0.31570 (11)	0.0531 (4)
H8A	0.0025	0.4898	0.3141	0.064*
H8B	−0.0728	0.3168	0.3121	0.064*
C9	0.1322 (2)	0.3383 (2)	0.24330 (11)	0.0501 (4)
H9A	0.1677	0.2277	0.2472	0.060*
H9B	0.0586	0.3494	0.1943	0.060*
C10	0.2851 (2)	0.4405 (2)	0.23563 (10)	0.0460 (4)
C11	0.5593 (3)	0.4465 (3)	0.18529 (14)	0.0659 (5)
H11A	0.6369	0.3760	0.1608	0.099*
H11B	0.6108	0.4875	0.2353	0.099*
H11C	0.5312	0.5333	0.1490	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0777 (3)	0.0335 (2)	0.0507 (3)	0.00051 (19)	−0.0062 (2)	0.00419 (18)
N1	0.0468 (7)	0.0374 (7)	0.0474 (7)	0.0014 (5)	−0.0014 (6)	0.0025 (6)
O1	0.0793 (9)	0.0440 (7)	0.0701 (9)	−0.0111 (6)	−0.0093 (7)	−0.0088 (6)
O2	0.0823 (10)	0.0469 (8)	0.0947 (12)	−0.0122 (7)	0.0174 (8)	−0.0172 (7)
O3	0.0594 (7)	0.0477 (7)	0.0652 (8)	−0.0022 (6)	0.0035 (6)	−0.0053 (6)
C1	0.0493 (8)	0.0356 (7)	0.0448 (8)	−0.0005 (6)	0.0060 (7)	−0.0005 (6)
C2	0.0649 (11)	0.0470 (9)	0.0467 (9)	−0.0057 (8)	0.0051 (8)	−0.0050 (7)
C3	0.0781 (13)	0.0484 (10)	0.0608 (12)	−0.0133 (9)	0.0146 (10)	−0.0165 (9)
C4	0.0791 (13)	0.0324 (8)	0.0799 (14)	−0.0047 (8)	0.0199 (11)	−0.0063 (8)
C5	0.0618 (11)	0.0354 (8)	0.0657 (12)	0.0057 (8)	0.0110 (9)	0.0056 (8)
C6	0.0430 (8)	0.0350 (7)	0.0464 (9)	0.0008 (6)	0.0081 (6)	−0.0006 (6)
C7	0.0530 (9)	0.0389 (8)	0.0520 (9)	−0.0010 (7)	0.0022 (7)	0.0004 (7)
C8	0.0435 (9)	0.0571 (10)	0.0572 (10)	0.0040 (8)	−0.0092 (7)	0.0049 (8)
C9	0.0550 (10)	0.0459 (9)	0.0474 (9)	−0.0029 (7)	−0.0119 (7)	0.0008 (7)
C10	0.0576 (10)	0.0416 (8)	0.0373 (8)	0.0002 (7)	−0.0082 (7)	0.0014 (6)
C11	0.0635 (12)	0.0653 (13)	0.0695 (13)	−0.0073 (10)	0.0084 (10)	0.0000 (10)

Geometric parameters (Å, º)

S1—C1	1.742 (2)	C3—H3	0.9300
S1—C7	1.768 (2)	C4—C5	1.393 (3)
N1—C6	1.402 (2)	C4—H4	0.9300
N1—C7	1.371 (2)	C5—C6	1.382 (2)
N1—C8	1.465 (2)	C5—H5	0.9300
O1—C7	1.217 (2)	C8—C9	1.511 (3)
O2—C10	1.200 (2)	C8—H8A	0.9700
O3—C10	1.330 (2)	C8—H8B	0.9700
O3—C11	1.443 (2)	C9—C10	1.495 (2)
C1—C2	1.382 (2)	C9—H9A	0.9700
C1—C6	1.395 (2)	C9—H9B	0.9700
C2—C3	1.384 (3)	C11—H11A	0.9600
C2—H2	0.9300	C11—H11B	0.9600
C3—C4	1.378 (3)	C11—H11C	0.9600
C1—S1—C7	91.50 (8)	O1—C7—S1	124.4 (2)
C7—N1—C6	114.9 (2)	N1—C7—S1	109.9 (2)
C7—N1—C8	118.8 (2)	N1—C8—C9	112.6 (2)
C6—N1—C8	126.2 (2)	N1—C8—H8A	109.1
C10—O3—C11	117.5 (2)	C9—C8—H8A	109.1
C2—C1—C6	121.58 (16)	N1—C8—H8B	109.1
C2—C1—S1	127.30 (14)	C9—C8—H8B	109.1
C6—C1—S1	111.12 (13)	H8A—C8—H8B	107.8
C1—C2—C3	118.04 (18)	C10—C9—C8	114.28 (15)
C1—C2—H2	121.0	C10—C9—H9A	108.7
C3—C2—H2	121.0	C8—C9—H9A	108.7
C4—C3—C2	120.60 (19)	C10—C9—H9B	108.7
C4—C3—H3	119.7	C8—C9—H9B	108.7
C2—C3—H3	119.7	H9A—C9—H9B	107.6
C3—C4—C5	121.68 (18)	O2—C10—O3	123.7 (2)
C3—C4—H4	119.2	O2—C10—C9	125.3 (2)
C5—C4—H4	119.2	O3—C10—C9	111.1 (2)
C6—C5—C4	117.87 (19)	O3—C11—H11A	109.5
C6—C5—H5	121.1	O3—C11—H11B	109.5
C4—C5—H5	121.1	H11A—C11—H11B	109.5
C5—C6—C1	120.20 (16)	O3—C11—H11C	109.5
C5—C6—N1	127.3 (2)	H11A—C11—H11C	109.5
C1—C6—N1	112.5 (2)	H11B—C11—H11C	109.5
O1—C7—N1	125.7 (2)
C7—S1—C1—C2	−179.64 (17)	C7—N1—C6—C1	2.4 (2)
C7—S1—C1—C6	0.35 (13)	C8—N1—C6—C1	178.54 (15)
C6—C1—C2—C3	1.8 (3)	C6—N1—C7—O1	178.82 (18)
S1—C1—C2—C3	−178.25 (15)	C8—N1—C7—O1	2.4 (3)
C1—C2—C3—C4	−0.6 (3)	C6—N1—C7—S1	−2.08 (18)
C2—C3—C4—C5	−0.8 (3)	C8—N1—C7—S1	−178.51 (12)
C3—C4—C5—C6	1.1 (3)	C1—S1—C7—O1	−179.92 (18)
C4—C5—C6—C1	0.0 (3)	C1—S1—C7—N1	0.96 (13)
C4—C5—C6—N1	−179.86 (16)	C7—N1—C8—C9	−74.1 (2)
C2—C1—C6—C5	−1.5 (3)	C6—N1—C8—C9	109.87 (19)
S1—C1—C6—C5	178.55 (13)	N1—C8—C9—C10	−66.7 (2)
C2—C1—C6—N1	178.42 (15)	C11—O3—C10—O2	−2.4 (3)
S1—C1—C6—N1	−1.57 (17)	C11—O3—C10—C9	176.09 (16)
C7—N1—C6—C5	−177.71 (17)	C8—C9—C10—O2	−32.8 (3)
C8—N1—C6—C5	−1.6 (3)	C8—C9—C10—O3	148.80 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1^i	0.97	2.47	3.241 (2)	136

Symmetry code: (i) −x, y+1/2, −z+1/2.