Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004846/cf6057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004846/cf6057Isup2.hkl |
CCDC reference: 162831
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.001 Å
- R factor = 0.045
- wR factor = 0.048
- Data-to-parameter ratio = 11.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_731 Alert C Bond Calc 1.4185(9), Rep 1.4184(4) .... 2.25 s.u-Ratio O18 -C3 1.555 1.555 PLAT_731 Alert C Bond Calc 1.4482(17), Rep 1.4482(5) .... 3.40 s.u-Ratio O23 -C24 1.555 1.555 PLAT_731 Alert C Bond Calc 1.5449(14), Rep 1.5450(5) .... 2.80 s.u-Ratio C2 -C3 1.555 1.555 PLAT_731 Alert C Bond Calc 1.3928(14), Rep 1.3929(5) .... 2.80 s.u-Ratio C6 -C11 1.555 1.555 PLAT_731 Alert C Bond Calc 1.381(2), Rep 1.3809(7) .... 2.86 s.u-Ratio C8 -C9 1.555 1.555 PLAT_731 Alert C Bond Calc 1.5122(15), Rep 1.5121(6) .... 2.50 s.u-Ratio C20 -C21 1.555 1.555 PLAT_732 Alert C Angle Calc 112.89(8), Rep 112.89(3) .... 2.67 s.u-Ratio C3 -C2 -C12 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 107.81(7), Rep 107.82(3) .... 2.33 s.u-Ratio O18 -C3 -C4 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 119.01(9), Rep 119.01(4) .... 2.25 s.u-Ratio N5 -C6 -C7 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 120.15(10), Rep 120.15(4) .... 2.50 s.u-Ratio C6 -C7 -C8 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 120.35(10), Rep 120.35(4) .... 2.50 s.u-Ratio C8 -C9 -C10 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 120.56(11), Rep 120.56(4) .... 2.75 s.u-Ratio C9 -C10 -C11 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 118.48(8), Rep 118.47(3) .... 2.67 s.u-Ratio S1 -C11 -C10 1.555 1.555 1.555 PLAT_732 Alert C Angle Calc 125.12(10), Rep 125.12(4) .... 2.50 s.u-Ratio O22 -C21 -O23 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
14 Alert Level C = Please check
A mixture of 2-aminothiophenol (110 mmol, 13.75 g) with ethyl 3-phenylglycidate (110 mmol, 21.12 g) was heated with stirring at 393 K for 1 h under a nitrogen atmosphere and then at 433 K for 16 h. The cooled mixture was dissolved in ethanol (30 ml) and allowed to stand at 278 K overnight. The precipitated needles were filtered off, washed with ethanol and recrystallized from ethanol to give 7.4 g (25%) of 3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one. To a solution of this compound (5 mmol, 1.36 g) in acetone (40 ml) was added K2CO3 (20 mmol, 2.76 g) and methyl chloroacetate (40 mmol, 4.34 g). The mixture was refluxed and the reaction was monitored by thin-layer chromatography (ether/CHCl3). After filtration, the solvent was evaporated in vacuo to give 1.20 g (70%) of methyl (3-hydroxy-4-oxo-2-phenyl-1,5-benzothiazepin-5-yl) acetate, (I), m.p. 429 K. Analysis calculated for C18H17NO2S: C 62.96, H 4.99, N 4.08%; found C 62.88, H 5.10, N 4.21%. Mass FAB+ (NBA): 344 (M + 1).
Data collection: KappaCCD Reference Manual (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: maXus (Mackay et al., 1999); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: maXus.
Fig. 1. Perspective view of the title molecule showing the labelling of the atoms, with displacement ellipsoids at the 50% probability level. |
C18H17NO4S | F(000) = 720 |
Mr = 343.40 | Dx = 1.416 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.6308 (8) Å | Cell parameters from 10319 reflections |
b = 15.1336 (9) Å | θ = 1–26.4° |
c = 16.154 (1) Å | µ = 0.22 mm−1 |
β = 151.086 (3)° | T = 298 K |
V = 1611.2 (2) Å3 | Prism, violet |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
KappaCCD diffractometer | Rint = 0.046 |
Radiation source: fine-focus sealed tube | θmax = 26.4° |
ϕ scans | h = −16→16 |
3302 measured reflections | k = −18→0 |
3156 independent reflections | l = −20→16 |
2569 reflections with I > 3σ(I) |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom, diff |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters not refined |
wR(F2) = 0.048 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2) + 0.03Fo2] |
S = 1.51 | (Δ/σ)max = 0.015 |
2569 reflections | Δρmax = 0.24 e Å−3 |
217 parameters | Δρmin = −0.30 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C18H17NO4S | V = 1611.2 (2) Å3 |
Mr = 343.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.6308 (8) Å | µ = 0.22 mm−1 |
b = 15.1336 (9) Å | T = 298 K |
c = 16.154 (1) Å | 0.40 × 0.30 × 0.20 mm |
β = 151.086 (3)° |
KappaCCD diffractometer | 2569 reflections with I > 3σ(I) |
3302 measured reflections | Rint = 0.046 |
3156 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 217 parameters |
wR(F2) = 0.048 | H-atom parameters not refined |
S = 1.51 | Δρmax = 0.24 e Å−3 |
2569 reflections | Δρmin = −0.30 e Å−3 |
Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. |
Refinement. Refinement on F2 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.043323 (18) | 0.376328 (8) | −0.016113 (15) | 0.09284 (7) | |
O18 | −0.01596 (4) | 0.32975 (2) | −0.30649 (4) | 0.08259 (17) | |
O19 | 0.29436 (5) | 0.43419 (2) | −0.05234 (4) | 0.09537 (18) | |
O22 | 0.67789 (5) | 0.30762 (2) | 0.20966 (4) | 0.1256 (2) | |
O23 | 0.84397 (5) | 0.43524 (2) | 0.34720 (4) | 0.1122 (2) | |
N5 | 0.41618 (5) | 0.35605 (2) | 0.14507 (4) | 0.06322 (19) | |
C2 | −0.07943 (6) | 0.36288 (3) | −0.20796 (5) | 0.0685 (2) | |
C3 | 0.07045 (6) | 0.32628 (3) | −0.16231 (5) | 0.0662 (2) | |
C4 | 0.26885 (6) | 0.37712 (3) | −0.01795 (5) | 0.0697 (2) | |
C6 | 0.39450 (6) | 0.29014 (3) | 0.19221 (5) | 0.0694 (2) | |
C7 | 0.54413 (7) | 0.22635 (3) | 0.31138 (6) | 0.0874 (3) | |
C8 | 0.53301 (8) | 0.16520 (3) | 0.36676 (6) | 0.1089 (3) | |
C9 | 0.37105 (9) | 0.16700 (3) | 0.30134 (7) | 0.1261 (3) | |
C10 | 0.21874 (7) | 0.22834 (3) | 0.17918 (6) | 0.1045 (3) | |
C11 | 0.22828 (6) | 0.29122 (3) | 0.12267 (5) | 0.0748 (2) | |
C12 | −0.17461 (6) | 0.44937 (3) | −0.30402 (5) | 0.0689 (2) | |
C13 | −0.08121 (7) | 0.53048 (3) | −0.22189 (6) | 0.0922 (3) | |
C14 | −0.17508 (9) | 0.60806 (3) | −0.31654 (8) | 0.1468 (3) | |
C15 | −0.36056 (9) | 0.60541 (4) | −0.49229 (8) | 0.1517 (4) | |
C16 | −0.45319 (7) | 0.52573 (4) | −0.57519 (6) | 0.1052 (3) | |
C17 | −0.36203 (6) | 0.44790 (3) | −0.48200 (6) | 0.0810 (3) | |
C20 | 0.61013 (6) | 0.40095 (3) | 0.27691 (5) | 0.0745 (2) | |
C21 | 0.71033 (6) | 0.37427 (3) | 0.27050 (5) | 0.0656 (2) | |
C24 | 0.95452 (8) | 0.41952 (3) | 0.35279 (7) | 0.1240 (3) | |
H2 | −0.18663 | 0.32026 | −0.28222 | 0.05276* | |
H3 | 0.09793 | 0.26565 | −0.12860 | 0.05190* | |
H7 | 0.65520 | 0.22464 | 0.35500 | 0.06208* | |
H8 | 0.63868 | 0.12210 | 0.45140 | 0.07114* | |
H9 | 0.36277 | 0.12497 | 0.33961 | 0.07850* | |
H10 | 0.10540 | 0.22851 | 0.13281 | 0.07015* | |
H13 | 0.04919 | 0.53296 | −0.09917 | 0.06338* | |
H14 | −0.11036 | 0.66396 | −0.25939 | 0.08474* | |
H15 | −0.42640 | 0.65904 | −0.55783 | 0.09155* | |
H16 | −0.58180 | 0.52358 | −0.69803 | 0.07708* | |
H17 | −0.42749 | 0.39217 | −0.53998 | 0.06170* | |
H18 | 0.04986 | 0.38758 | −0.28624 | 0.06267* | |
H20A | 0.69835 | 0.38557 | 0.38711 | 0.05748* | |
H20B | 0.58802 | 0.46365 | 0.26043 | 0.05748* | |
H24A | 1.04642 | 0.46750 | 0.41072 | 0.08136* | |
H24B | 0.86042 | 0.41502 | 0.23810 | 0.08136* | |
H24C | 1.02972 | 0.36540 | 0.41302 | 0.08136* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.04872 (7) | 0.04516 (7) | 0.04300 (7) | 0.00509 (6) | 0.04246 (7) | 0.00202 (6) |
O18 | 0.04275 (18) | 0.0538 (2) | 0.03141 (17) | 0.00596 (15) | 0.03293 (16) | −0.00048 (14) |
O19 | 0.04561 (19) | 0.04791 (19) | 0.04614 (19) | 0.00379 (15) | 0.04120 (18) | 0.00991 (15) |
O22 | 0.0573 (2) | 0.0458 (2) | 0.0696 (2) | −0.00760 (17) | 0.0565 (2) | −0.01519 (18) |
O23 | 0.0495 (2) | 0.0456 (2) | 0.0631 (2) | −0.01029 (16) | 0.0509 (2) | −0.01049 (17) |
N5 | 0.02961 (19) | 0.0412 (2) | 0.02628 (19) | −0.00350 (15) | 0.02420 (18) | −0.00141 (15) |
C2 | 0.0335 (2) | 0.0326 (2) | 0.0329 (2) | −0.00331 (18) | 0.0297 (2) | −0.00450 (18) |
C3 | 0.0343 (2) | 0.0335 (2) | 0.0288 (2) | 0.00331 (18) | 0.0279 (2) | 0.00090 (18) |
C4 | 0.0338 (2) | 0.0346 (2) | 0.0340 (2) | 0.00502 (19) | 0.0309 (2) | 0.00359 (19) |
C6 | 0.0387 (2) | 0.0336 (2) | 0.0277 (2) | −0.00261 (19) | 0.0292 (2) | −0.00270 (18) |
C7 | 0.0434 (3) | 0.0486 (3) | 0.0361 (3) | 0.0060 (2) | 0.0338 (3) | 0.0060 (2) |
C8 | 0.0613 (3) | 0.0502 (3) | 0.0411 (3) | 0.0117 (3) | 0.0431 (3) | 0.0134 (2) |
C9 | 0.0744 (4) | 0.0492 (3) | 0.0514 (3) | −0.0061 (3) | 0.0558 (3) | 0.0029 (3) |
C10 | 0.0580 (3) | 0.0466 (3) | 0.0460 (3) | −0.0086 (2) | 0.0475 (3) | −0.0050 (2) |
C11 | 0.0404 (3) | 0.0353 (2) | 0.0324 (2) | −0.0042 (2) | 0.0326 (2) | −0.00441 (19) |
C12 | 0.0322 (2) | 0.0336 (2) | 0.0354 (2) | 0.00140 (19) | 0.0310 (2) | −0.00038 (19) |
C13 | 0.0468 (3) | 0.0372 (3) | 0.0462 (3) | 0.0000 (2) | 0.0424 (3) | 0.0002 (2) |
C14 | 0.0792 (4) | 0.0359 (3) | 0.0813 (4) | 0.0035 (3) | 0.0753 (4) | 0.0039 (3) |
C15 | 0.0791 (4) | 0.0572 (4) | 0.0790 (4) | 0.0314 (3) | 0.0744 (4) | 0.0326 (3) |
C16 | 0.0472 (3) | 0.0783 (4) | 0.0441 (3) | 0.0229 (3) | 0.0410 (3) | 0.0200 (3) |
C17 | 0.0364 (3) | 0.0512 (3) | 0.0375 (3) | 0.0035 (2) | 0.0331 (3) | 0.0002 (2) |
C20 | 0.0339 (2) | 0.0454 (3) | 0.0330 (3) | −0.0064 (2) | 0.0288 (2) | −0.0070 (2) |
C21 | 0.0295 (2) | 0.0366 (2) | 0.0296 (2) | 0.0014 (2) | 0.0248 (2) | 0.0017 (2) |
C24 | 0.0546 (3) | 0.0633 (3) | 0.0663 (4) | 0.0043 (3) | 0.0556 (3) | 0.0085 (3) |
S1—C2 | 1.8350 (4) | C6—C7 | 1.3870 (6) |
S1—C11 | 1.7738 (4) | C6—C11 | 1.3929 (5) |
O18—C3 | 1.4184 (4) | C7—C8 | 1.3847 (7) |
O19—C4 | 1.2304 (5) | C8—C9 | 1.3809 (7) |
O22—C21 | 1.1908 (5) | C9—C10 | 1.3761 (7) |
O23—C21 | 1.3243 (5) | C10—C11 | 1.4013 (6) |
O23—C24 | 1.4482 (5) | C12—C13 | 1.3896 (6) |
N5—C4 | 1.3457 (5) | C12—C17 | 1.3908 (6) |
N5—C6 | 1.4339 (5) | C13—C14 | 1.3887 (6) |
N5—C20 | 1.4594 (5) | C14—C15 | 1.3739 (7) |
C2—C3 | 1.5450 (5) | C15—C16 | 1.3718 (8) |
C2—C12 | 1.5098 (6) | C16—C17 | 1.3867 (7) |
C3—C4 | 1.5176 (6) | C20—C21 | 1.5121 (6) |
C2—S1—C11 | 103.89 (2) | C7—C8—C9 | 119.88 (5) |
C21—O23—C24 | 116.62 (4) | C8—C9—C10 | 120.35 (4) |
C4—N5—C6 | 123.77 (4) | C9—C10—C11 | 120.56 (4) |
C4—N5—C20 | 116.07 (3) | S1—C11—C6 | 122.47 (3) |
C6—N5—C20 | 120.07 (3) | S1—C11—C10 | 118.47 (3) |
S1—C2—C3 | 111.33 (3) | C6—C11—C10 | 118.67 (4) |
S1—C2—C12 | 109.42 (3) | C2—C12—C13 | 122.66 (4) |
C3—C2—C12 | 112.89 (3) | C2—C12—C17 | 118.80 (4) |
O18—C3—C2 | 110.64 (3) | C13—C12—C17 | 118.53 (4) |
O18—C3—C4 | 107.82 (3) | C12—C13—C14 | 120.30 (4) |
C2—C3—C4 | 112.63 (3) | C13—C14—C15 | 120.39 (5) |
O19—C4—N5 | 121.50 (4) | C14—C15—C16 | 119.95 (5) |
O19—C4—C3 | 119.33 (4) | C15—C16—C17 | 120.17 (5) |
N5—C4—C3 | 119.11 (3) | C12—C17—C16 | 120.64 (5) |
N5—C6—C7 | 119.01 (4) | N5—C20—C21 | 111.51 (3) |
N5—C6—C11 | 120.63 (4) | O22—C21—O23 | 125.12 (4) |
C7—C6—C11 | 120.34 (4) | O22—C21—C20 | 125.28 (4) |
C6—C7—C8 | 120.15 (4) | O23—C21—C20 | 109.57 (4) |
Experimental details
Crystal data | |
Chemical formula | C18H17NO4S |
Mr | 343.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.6308 (8), 15.1336 (9), 16.154 (1) |
β (°) | 151.086 (3) |
V (Å3) | 1611.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 3σ(I)] reflections | 3302, 3156, 2569 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.048, 1.51 |
No. of reflections | 2569 |
No. of parameters | 217 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.30 |
Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), maXus (Mackay et al., 1999), ORTEPII (Johnson, 1976), maXus.
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A number of 1,5-benzothiazepine derivatives have been shown to exhibit pharmacological propeties as calcium antagonists (Akiyoshi et al., 1992), coronary vasodilators (Hirozumi et al., 1991), antihypertensives (Hiroshi et al., 1992) and blood-platelet aggregation inhibitors (Hirozumi et al., 1990). The success of this class of products has stimulated significant activity in related chemical synthesis, directed at the synthesis of both analogous and enantiomerically pure compounds.
The thiazepine ring in the title compound, (I), is fused with the benzo ring and has four substituents: phenyl in position 2, hydroxy in position 3, oxo in position 4 and acetate in position 5. The seven-membered ring contains a planar N5—C6—C11—S1 fragment (r.m.s. deviation: 0.014 Å), almost coplanar with the adjacent benzo ring [angle 5.3 (3)°]. The three other atoms of the benzothiazepine system (C2, C3 and C4) are on the same side of the N5—C6—C11—S1 fragment.