In the title compound, C
6H
4SC(O)NCH
2CH
2COOCH
3, 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
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O contact between the α atom of the methyl propionate substituent and the carbonyl oxygen of the oxobenzothiazole group [C
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O 3.241 (2) Å]. These contacts link the molecules into infinite chains, running along the
b axis of the crystal.
Supporting information
CCDC reference: 226936
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(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
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
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) Å3 | Prism, yellow |
Z = 4 | 0.90 × 0.60 × 0.25 mm |
Data collection top
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 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)] = 0.039 | H-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 reflections | Δρmax = 0.25 e Å−3 |
146 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O1i | 0.97 | 2.47 | 3.241 (2) | 136 |
Symmetry code: (i) −x, y+1/2, −z+1/2. |