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In the title compound, C15H17NO5S2, an analogue of the anti­biotic sparsomycin, the chiral S atom is in an R configuration and the chiral C atom is in an S configuration. Mol­ecules translated by one unit along the b axis are linked into chains by inter­molecular O—H...O and C—H...O hydrogen bonds. Adjacent screw-related chains are inter­linked via C—H...O hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600208X/ci6749sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600208X/ci6749Isup2.hkl
Contains datablock I

CCDC reference: 298399

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.029
  • wR factor = 0.072
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.38 From the CIF: _reflns_number_total 2740 Count of symmetry unique reflns 1891 Completeness (_total/calc) 144.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 849 Fraction of Friedel pairs measured 0.449 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N-[1-Hydroxy-3-(methylsulfanylmethylsulfinyl)propan-2-yl]-2-oxo- 2H-chromene-3-carboxamide top
Crystal data top
C15H17NO5S2F(000) = 372
Mr = 355.42Dx = 1.434 Mg m3
Monoclinic, P21Melting point: 428 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 10.3234 (17) ÅCell parameters from 2819 reflections
b = 5.2159 (9) Åθ = 2.6–26.4°
c = 15.448 (3) ŵ = 0.35 mm1
β = 98.341 (2)°T = 294 K
V = 823.0 (3) Å3Plate, colourless
Z = 20.38 × 0.22 × 0.18 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2740 independent reflections
Radiation source: fine-focus sealed tube2521 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 26.4°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1012
Tmin = 0.816, Tmax = 0.939k = 65
4696 measured reflectionsl = 1918
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)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0372P)2 + 0.0863P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
2740 reflectionsΔρmax = 0.15 e Å3
215 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack (1983), with 859 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (7)
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
S10.69535 (4)0.22678 (10)0.67731 (3)0.03173 (13)
S20.98103 (5)0.27297 (14)0.66801 (4)0.0536 (2)
O10.36544 (17)0.4664 (3)0.98699 (10)0.0492 (4)
O20.47392 (19)0.5564 (4)0.87850 (11)0.0655 (6)
O30.29312 (18)0.0557 (3)0.73008 (10)0.0504 (5)
O40.31550 (16)0.6686 (3)0.57659 (10)0.0412 (4)
H40.303 (3)0.708 (6)0.6228 (17)0.062*
O50.69014 (15)0.0475 (3)0.64834 (10)0.0415 (4)
N10.41612 (17)0.3013 (4)0.72424 (11)0.0334 (4)
H1A0.444 (2)0.427 (5)0.7470 (16)0.040*
C10.2795 (2)0.3204 (5)1.02592 (14)0.0398 (5)
C20.2590 (3)0.3881 (6)1.10956 (15)0.0549 (7)
H20.30260.52751.13780.066*
C30.1738 (3)0.2474 (7)1.14992 (14)0.0593 (7)
H30.15860.29351.20570.071*
C40.1092 (3)0.0364 (7)1.10907 (16)0.0605 (8)
H4A0.05240.05921.13780.073*
C50.1298 (3)0.0312 (6)1.02529 (15)0.0511 (6)
H50.08670.17190.99750.061*
C60.2158 (2)0.1136 (5)0.98282 (13)0.0387 (5)
C70.2427 (2)0.0605 (5)0.89574 (13)0.0389 (5)
H70.20040.07640.86510.047*
C80.32696 (19)0.2023 (5)0.85727 (12)0.0337 (4)
C90.3952 (2)0.4165 (5)0.90456 (14)0.0421 (6)
C100.3451 (2)0.1378 (4)0.76487 (13)0.0346 (5)
C110.42959 (18)0.2723 (4)0.63170 (12)0.0308 (4)
H110.43000.08880.61810.037*
C120.3144 (2)0.3968 (5)0.57295 (14)0.0361 (5)
H12A0.31610.34340.51300.043*
H12B0.23330.33500.59020.043*
C130.55854 (19)0.3872 (4)0.61373 (13)0.0323 (5)
H13A0.56090.56820.62830.039*
H13B0.56520.37100.55200.039*
C140.8196 (2)0.3843 (4)0.62552 (15)0.0384 (5)
H14A0.80300.35280.56300.046*
H14B0.81480.56780.63470.046*
C150.9963 (2)0.0077 (5)0.5961 (2)0.0595 (7)
H15A1.00420.07100.53870.089*
H15B0.92020.09930.59300.089*
H15C1.07280.09030.61800.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0353 (2)0.0301 (3)0.0308 (2)0.0003 (2)0.00782 (17)0.0004 (2)
S20.0343 (3)0.0680 (5)0.0579 (4)0.0006 (3)0.0043 (2)0.0123 (4)
O10.0627 (11)0.0498 (11)0.0352 (8)0.0108 (9)0.0074 (7)0.0130 (8)
O20.0747 (12)0.0728 (14)0.0513 (10)0.0413 (11)0.0176 (9)0.0216 (11)
O30.0750 (12)0.0438 (10)0.0366 (8)0.0250 (9)0.0222 (8)0.0126 (8)
O40.0512 (9)0.0394 (10)0.0338 (8)0.0071 (7)0.0090 (7)0.0011 (7)
O50.0482 (9)0.0269 (9)0.0505 (9)0.0004 (7)0.0108 (7)0.0031 (7)
N10.0385 (9)0.0304 (11)0.0325 (9)0.0070 (8)0.0096 (7)0.0049 (8)
C10.0481 (13)0.0419 (13)0.0292 (10)0.0069 (10)0.0052 (9)0.0012 (10)
C20.0745 (18)0.0578 (18)0.0319 (12)0.0078 (14)0.0058 (12)0.0091 (12)
C30.0799 (17)0.072 (2)0.0277 (10)0.0170 (17)0.0136 (11)0.0006 (15)
C40.0716 (18)0.077 (2)0.0369 (13)0.0093 (16)0.0209 (12)0.0130 (15)
C50.0613 (16)0.0566 (17)0.0379 (12)0.0024 (13)0.0156 (11)0.0023 (12)
C60.0470 (12)0.0417 (14)0.0279 (10)0.0046 (10)0.0070 (9)0.0018 (10)
C70.0494 (12)0.0375 (13)0.0308 (11)0.0035 (11)0.0086 (9)0.0051 (10)
C80.0380 (10)0.0338 (12)0.0293 (9)0.0003 (9)0.0051 (7)0.0029 (10)
C90.0460 (13)0.0463 (14)0.0336 (11)0.0037 (11)0.0041 (9)0.0107 (11)
C100.0379 (11)0.0351 (13)0.0316 (10)0.0013 (9)0.0074 (8)0.0032 (9)
C110.0371 (10)0.0277 (12)0.0289 (9)0.0053 (9)0.0088 (8)0.0028 (9)
C120.0367 (11)0.0391 (13)0.0329 (11)0.0055 (9)0.0061 (9)0.0040 (10)
C130.0345 (11)0.0275 (11)0.0361 (11)0.0003 (8)0.0096 (8)0.0037 (9)
C140.0342 (11)0.0308 (12)0.0518 (13)0.0024 (9)0.0119 (10)0.0009 (10)
C150.0437 (14)0.0431 (16)0.095 (2)0.0021 (12)0.0198 (13)0.0053 (15)
Geometric parameters (Å, º) top
S1—O51.4976 (17)C4—H4A0.93
S1—C131.805 (2)C5—C61.400 (3)
S1—C141.805 (2)C5—H50.93
S2—C151.796 (3)C6—C71.439 (3)
S2—C141.797 (2)C7—C81.344 (3)
O1—C11.372 (3)C7—H70.93
O1—C91.377 (3)C8—C91.459 (3)
O2—C91.204 (3)C8—C101.504 (3)
O3—C101.229 (3)C11—C131.522 (3)
O4—C121.419 (3)C11—C121.532 (3)
O4—H40.77 (3)C11—H110.98
N1—C101.339 (3)C12—H12A0.97
N1—C111.464 (2)C12—H12B0.97
N1—H1A0.78 (3)C13—H13A0.97
C1—C61.383 (3)C13—H13B0.97
C1—C21.385 (3)C14—H14A0.97
C2—C31.364 (4)C14—H14B0.97
C2—H20.93C15—H15A0.96
C3—C41.390 (5)C15—H15B0.96
C3—H30.93C15—H15C0.96
C4—C51.387 (3)
O5—S1—C13106.79 (10)O1—C9—C8116.8 (2)
O5—S1—C14107.42 (10)O3—C10—N1123.5 (2)
C13—S1—C1495.62 (10)O3—C10—C8119.5 (2)
C15—S2—C14100.56 (12)N1—C10—C8117.01 (19)
C1—O1—C9123.04 (19)N1—C11—C13110.30 (16)
C12—O4—H4107 (2)N1—C11—C12111.05 (16)
C10—N1—C11121.87 (18)C13—C11—C12110.48 (17)
C10—N1—H1A121.3 (18)N1—C11—H11108.3
C11—N1—H1A116.3 (18)C13—C11—H11108.3
O1—C1—C6120.96 (19)C12—C11—H11108.3
O1—C1—C2117.6 (2)O4—C12—C11113.49 (18)
C6—C1—C2121.4 (2)O4—C12—H12A108.9
C3—C2—C1119.1 (3)C11—C12—H12A108.9
C3—C2—H2120.5O4—C12—H12B108.9
C1—C2—H2120.5C11—C12—H12B108.9
C2—C3—C4121.1 (2)H12A—C12—H12B107.7
C2—C3—H3119.4C11—C13—S1110.76 (14)
C4—C3—H3119.4C11—C13—H13A109.5
C5—C4—C3119.8 (3)S1—C13—H13A109.5
C5—C4—H4A120.1C11—C13—H13B109.5
C3—C4—H4A120.1S1—C13—H13B109.5
C4—C5—C6119.6 (3)H13A—C13—H13B108.1
C4—C5—H5120.2S2—C14—S1111.84 (12)
C6—C5—H5120.2S2—C14—H14A109.2
C1—C6—C5119.0 (2)S1—C14—H14A109.2
C1—C6—C7117.2 (2)S2—C14—H14B109.2
C5—C6—C7123.8 (2)S1—C14—H14B109.2
C8—C7—C6122.2 (2)H14A—C14—H14B107.9
C8—C7—H7118.9S2—C15—H15A109.5
C6—C7—H7118.9S2—C15—H15B109.5
C7—C8—C9119.75 (18)H15A—C15—H15B109.5
C7—C8—C10118.3 (2)S2—C15—H15C109.5
C9—C8—C10121.94 (19)H15A—C15—H15C109.5
O2—C9—O1116.5 (2)H15B—C15—H15C109.5
O2—C9—C8126.6 (2)
C9—O1—C1—C60.9 (3)C10—C8—C9—O22.7 (4)
C9—O1—C1—C2179.2 (2)C7—C8—C9—O11.9 (3)
O1—C1—C2—C3179.7 (2)C10—C8—C9—O1176.5 (2)
C6—C1—C2—C30.1 (4)C11—N1—C10—O34.7 (3)
C1—C2—C3—C40.9 (4)C11—N1—C10—C8173.84 (18)
C2—C3—C4—C51.0 (5)C7—C8—C10—O37.0 (3)
C3—C4—C5—C60.2 (4)C9—C8—C10—O3174.6 (2)
O1—C1—C6—C5179.5 (2)C7—C8—C10—N1171.6 (2)
C2—C1—C6—C50.6 (3)C9—C8—C10—N16.8 (3)
O1—C1—C6—C70.5 (3)C10—N1—C11—C13152.47 (19)
C2—C1—C6—C7179.3 (2)C10—N1—C11—C1284.7 (2)
C4—C5—C6—C10.6 (4)N1—C11—C12—O470.7 (2)
C4—C5—C6—C7179.4 (2)C13—C11—C12—O452.1 (2)
C1—C6—C7—C80.7 (3)N1—C11—C13—S160.7 (2)
C5—C6—C7—C8179.3 (2)C12—C11—C13—S1176.12 (14)
C6—C7—C8—C90.5 (3)O5—S1—C13—C1162.13 (16)
C6—C7—C8—C10177.9 (2)C14—S1—C13—C11172.25 (15)
C1—O1—C9—O2178.7 (2)C15—S2—C14—S189.21 (15)
C1—O1—C9—C82.1 (3)O5—S1—C14—S268.83 (14)
C7—C8—C9—O2179.0 (3)C13—S1—C14—S2178.41 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.78 (3)2.12 (2)2.719 (2)134 (2)
O4—H4···O3i0.77 (3)2.08 (3)2.811 (2)158 (3)
C13—H13A···O5i0.972.403.258 (3)147
C14—H14A···O4ii0.972.513.420 (3)156
C14—H14B···O5i0.972.413.291 (3)151
C7—H7···O30.932.422.752 (3)101
C11—H11···O4iii0.982.533.426 (3)152
C12—H12A···O5iv0.972.553.424 (3)150
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1/2, z+1; (iii) x, y1, z; (iv) x+1, y+1/2, z+1.
 

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