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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021147/ya6174sup1.cif
Contains datablocks I, data1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021147/ya6174Isup2.hkl
Contains datablock I

CCDC reference: 226936

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 top

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 top
Crystal data top
C11H11NO3SF(000) = 496
Mr = 237.27Dx = 1.443 Mg m3
Monoclinic, P21/cMelting point: 330 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 7.9109 (13) ÅCell parameters from 3603 reflections
b = 8.386 (3) Åθ = 20.1–26.4°
c = 16.4898 (16) ŵ = 0.29 mm1
β = 93.645 (12)°T = 293 K
V = 1091.8 (4) Å3Prism, yellow
Z = 40.90 × 0.60 × 0.25 mm
Data collection top
Rigaku AFC-7S
diffractometer
2039 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.040
Graphite monochromatorθmax = 30.0°, θmin = 2.5°
ω–2θ scansh = 011
Absorption correction: ψ scan
North et al., 1968
k = 011
Tmin = 0.812, Tmax = 0.930l = 2323
3383 measured reflections3 standard reflections every 150 reflections
3176 independent reflections intensity decay: 0.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2099P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3176 reflectionsΔρmax = 0.25 e Å3
146 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.085 (5)
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.25538 (7)0.17569 (5)0.51309 (3)0.05439 (17)
N10.12490 (17)0.34196 (16)0.39321 (8)0.0440 (3)
O10.09372 (19)0.07022 (16)0.37773 (9)0.0651 (4)
O20.2970 (2)0.57779 (17)0.25554 (11)0.0741 (5)
O30.40718 (17)0.36035 (16)0.20159 (9)0.0575 (3)
C10.2695 (2)0.3827 (2)0.51872 (10)0.0431 (3)
C20.3463 (2)0.4725 (2)0.58099 (11)0.0528 (4)
H20.40110.42380.62600.063*
C30.3391 (3)0.6368 (2)0.57438 (13)0.0620 (5)
H30.38880.69990.61570.074*
C40.2590 (3)0.7079 (2)0.50711 (14)0.0632 (5)
H40.25440.81860.50420.076*
C50.1846 (2)0.6183 (2)0.44327 (12)0.0540 (4)
H50.13250.66740.39770.065*
C60.19077 (19)0.45405 (18)0.44985 (10)0.0412 (3)
C70.1437 (2)0.1859 (2)0.41688 (11)0.0480 (4)
C80.0318 (2)0.3775 (2)0.31570 (11)0.0531 (4)
H8A0.00250.48980.31410.064*
H8B0.07280.31680.31210.064*
C90.1322 (2)0.3383 (2)0.24330 (11)0.0501 (4)
H9A0.16770.22770.24720.060*
H9B0.05860.34940.19430.060*
C100.2851 (2)0.4405 (2)0.23563 (10)0.0460 (4)
C110.5593 (3)0.4465 (3)0.18529 (14)0.0659 (5)
H11A0.63690.37600.16080.099*
H11B0.61080.48750.23530.099*
H11C0.53120.53330.14900.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0777 (3)0.0335 (2)0.0507 (3)0.00051 (19)0.0062 (2)0.00419 (18)
N10.0468 (7)0.0374 (7)0.0474 (7)0.0014 (5)0.0014 (6)0.0025 (6)
O10.0793 (9)0.0440 (7)0.0701 (9)0.0111 (6)0.0093 (7)0.0088 (6)
O20.0823 (10)0.0469 (8)0.0947 (12)0.0122 (7)0.0174 (8)0.0172 (7)
O30.0594 (7)0.0477 (7)0.0652 (8)0.0022 (6)0.0035 (6)0.0053 (6)
C10.0493 (8)0.0356 (7)0.0448 (8)0.0005 (6)0.0060 (7)0.0005 (6)
C20.0649 (11)0.0470 (9)0.0467 (9)0.0057 (8)0.0051 (8)0.0050 (7)
C30.0781 (13)0.0484 (10)0.0608 (12)0.0133 (9)0.0146 (10)0.0165 (9)
C40.0791 (13)0.0324 (8)0.0799 (14)0.0047 (8)0.0199 (11)0.0063 (8)
C50.0618 (11)0.0354 (8)0.0657 (12)0.0057 (8)0.0110 (9)0.0056 (8)
C60.0430 (8)0.0350 (7)0.0464 (9)0.0008 (6)0.0081 (6)0.0006 (6)
C70.0530 (9)0.0389 (8)0.0520 (9)0.0010 (7)0.0022 (7)0.0004 (7)
C80.0435 (9)0.0571 (10)0.0572 (10)0.0040 (8)0.0092 (7)0.0049 (8)
C90.0550 (10)0.0459 (9)0.0474 (9)0.0029 (7)0.0119 (7)0.0008 (7)
C100.0576 (10)0.0416 (8)0.0373 (8)0.0002 (7)0.0082 (7)0.0014 (6)
C110.0635 (12)0.0653 (13)0.0695 (13)0.0073 (10)0.0084 (10)0.0000 (10)
Geometric parameters (Å, º) top
S1—C11.742 (2)C3—H30.9300
S1—C71.768 (2)C4—C51.393 (3)
N1—C61.402 (2)C4—H40.9300
N1—C71.371 (2)C5—C61.382 (2)
N1—C81.465 (2)C5—H50.9300
O1—C71.217 (2)C8—C91.511 (3)
O2—C101.200 (2)C8—H8A0.9700
O3—C101.330 (2)C8—H8B0.9700
O3—C111.443 (2)C9—C101.495 (2)
C1—C21.382 (2)C9—H9A0.9700
C1—C61.395 (2)C9—H9B0.9700
C2—C31.384 (3)C11—H11A0.9600
C2—H20.9300C11—H11B0.9600
C3—C41.378 (3)C11—H11C0.9600
C1—S1—C791.50 (8)O1—C7—S1124.4 (2)
C7—N1—C6114.9 (2)N1—C7—S1109.9 (2)
C7—N1—C8118.8 (2)N1—C8—C9112.6 (2)
C6—N1—C8126.2 (2)N1—C8—H8A109.1
C10—O3—C11117.5 (2)C9—C8—H8A109.1
C2—C1—C6121.58 (16)N1—C8—H8B109.1
C2—C1—S1127.30 (14)C9—C8—H8B109.1
C6—C1—S1111.12 (13)H8A—C8—H8B107.8
C1—C2—C3118.04 (18)C10—C9—C8114.28 (15)
C1—C2—H2121.0C10—C9—H9A108.7
C3—C2—H2121.0C8—C9—H9A108.7
C4—C3—C2120.60 (19)C10—C9—H9B108.7
C4—C3—H3119.7C8—C9—H9B108.7
C2—C3—H3119.7H9A—C9—H9B107.6
C3—C4—C5121.68 (18)O2—C10—O3123.7 (2)
C3—C4—H4119.2O2—C10—C9125.3 (2)
C5—C4—H4119.2O3—C10—C9111.1 (2)
C6—C5—C4117.87 (19)O3—C11—H11A109.5
C6—C5—H5121.1O3—C11—H11B109.5
C4—C5—H5121.1H11A—C11—H11B109.5
C5—C6—C1120.20 (16)O3—C11—H11C109.5
C5—C6—N1127.3 (2)H11A—C11—H11C109.5
C1—C6—N1112.5 (2)H11B—C11—H11C109.5
O1—C7—N1125.7 (2)
C7—S1—C1—C2179.64 (17)C7—N1—C6—C12.4 (2)
C7—S1—C1—C60.35 (13)C8—N1—C6—C1178.54 (15)
C6—C1—C2—C31.8 (3)C6—N1—C7—O1178.82 (18)
S1—C1—C2—C3178.25 (15)C8—N1—C7—O12.4 (3)
C1—C2—C3—C40.6 (3)C6—N1—C7—S12.08 (18)
C2—C3—C4—C50.8 (3)C8—N1—C7—S1178.51 (12)
C3—C4—C5—C61.1 (3)C1—S1—C7—O1179.92 (18)
C4—C5—C6—C10.0 (3)C1—S1—C7—N10.96 (13)
C4—C5—C6—N1179.86 (16)C7—N1—C8—C974.1 (2)
C2—C1—C6—C51.5 (3)C6—N1—C8—C9109.87 (19)
S1—C1—C6—C5178.55 (13)N1—C8—C9—C1066.7 (2)
C2—C1—C6—N1178.42 (15)C11—O3—C10—O22.4 (3)
S1—C1—C6—N11.57 (17)C11—O3—C10—C9176.09 (16)
C7—N1—C6—C5177.71 (17)C8—C9—C10—O232.8 (3)
C8—N1—C6—C51.6 (3)C8—C9—C10—O3148.80 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O1i0.972.473.241 (2)136
Symmetry code: (i) x, y+1/2, z+1/2.
 

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