In the title compound, C
15H
17NO
5S
2, 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
CCDC reference: 298399
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.072
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
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
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-
2
H-chromene-3-carboxamide
top
Crystal data top
C15H17NO5S2 | F(000) = 372 |
Mr = 355.42 | Dx = 1.434 Mg m−3 |
Monoclinic, P21 | Melting point: 428 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3234 (17) Å | Cell parameters from 2819 reflections |
b = 5.2159 (9) Å | θ = 2.6–26.4° |
c = 15.448 (3) Å | µ = 0.35 mm−1 |
β = 98.341 (2)° | T = 294 K |
V = 823.0 (3) Å3 | Plate, colourless |
Z = 2 | 0.38 × 0.22 × 0.18 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 2740 independent reflections |
Radiation source: fine-focus sealed tube | 2521 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 26.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→12 |
Tmin = 0.816, Tmax = 0.939 | k = −6→5 |
4696 measured reflections | l = −19→18 |
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)] = 0.029 | H 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 reflections | Δρmax = 0.15 e Å−3 |
215 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 859 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.69535 (4) | 0.22678 (10) | 0.67731 (3) | 0.03173 (13) | |
S2 | 0.98103 (5) | 0.27297 (14) | 0.66801 (4) | 0.0536 (2) | |
O1 | 0.36544 (17) | 0.4664 (3) | 0.98699 (10) | 0.0492 (4) | |
O2 | 0.47392 (19) | 0.5564 (4) | 0.87850 (11) | 0.0655 (6) | |
O3 | 0.29312 (18) | −0.0557 (3) | 0.73008 (10) | 0.0504 (5) | |
O4 | 0.31550 (16) | 0.6686 (3) | 0.57659 (10) | 0.0412 (4) | |
H4 | 0.303 (3) | 0.708 (6) | 0.6228 (17) | 0.062* | |
O5 | 0.69014 (15) | −0.0475 (3) | 0.64834 (10) | 0.0415 (4) | |
N1 | 0.41612 (17) | 0.3013 (4) | 0.72424 (11) | 0.0334 (4) | |
H1A | 0.444 (2) | 0.427 (5) | 0.7470 (16) | 0.040* | |
C1 | 0.2795 (2) | 0.3204 (5) | 1.02592 (14) | 0.0398 (5) | |
C2 | 0.2590 (3) | 0.3881 (6) | 1.10956 (15) | 0.0549 (7) | |
H2 | 0.3026 | 0.5275 | 1.1378 | 0.066* | |
C3 | 0.1738 (3) | 0.2474 (7) | 1.14992 (14) | 0.0593 (7) | |
H3 | 0.1586 | 0.2935 | 1.2057 | 0.071* | |
C4 | 0.1092 (3) | 0.0364 (7) | 1.10907 (16) | 0.0605 (8) | |
H4A | 0.0524 | −0.0592 | 1.1378 | 0.073* | |
C5 | 0.1298 (3) | −0.0312 (6) | 1.02529 (15) | 0.0511 (6) | |
H5 | 0.0867 | −0.1719 | 0.9975 | 0.061* | |
C6 | 0.2158 (2) | 0.1136 (5) | 0.98282 (13) | 0.0387 (5) | |
C7 | 0.2427 (2) | 0.0605 (5) | 0.89574 (13) | 0.0389 (5) | |
H7 | 0.2004 | −0.0764 | 0.8651 | 0.047* | |
C8 | 0.32696 (19) | 0.2023 (5) | 0.85727 (12) | 0.0337 (4) | |
C9 | 0.3952 (2) | 0.4165 (5) | 0.90456 (14) | 0.0421 (6) | |
C10 | 0.3451 (2) | 0.1378 (4) | 0.76487 (13) | 0.0346 (5) | |
C11 | 0.42959 (18) | 0.2723 (4) | 0.63170 (12) | 0.0308 (4) | |
H11 | 0.4300 | 0.0888 | 0.6181 | 0.037* | |
C12 | 0.3144 (2) | 0.3968 (5) | 0.57295 (14) | 0.0361 (5) | |
H12A | 0.3161 | 0.3434 | 0.5130 | 0.043* | |
H12B | 0.2333 | 0.3350 | 0.5902 | 0.043* | |
C13 | 0.55854 (19) | 0.3872 (4) | 0.61373 (13) | 0.0323 (5) | |
H13A | 0.5609 | 0.5682 | 0.6283 | 0.039* | |
H13B | 0.5652 | 0.3710 | 0.5520 | 0.039* | |
C14 | 0.8196 (2) | 0.3843 (4) | 0.62552 (15) | 0.0384 (5) | |
H14A | 0.8030 | 0.3528 | 0.5630 | 0.046* | |
H14B | 0.8148 | 0.5678 | 0.6347 | 0.046* | |
C15 | 0.9963 (2) | 0.0077 (5) | 0.5961 (2) | 0.0595 (7) | |
H15A | 1.0042 | 0.0710 | 0.5387 | 0.089* | |
H15B | 0.9202 | −0.0993 | 0.5930 | 0.089* | |
H15C | 1.0728 | −0.0903 | 0.6180 | 0.089* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0353 (2) | 0.0301 (3) | 0.0308 (2) | 0.0003 (2) | 0.00782 (17) | 0.0004 (2) |
S2 | 0.0343 (3) | 0.0680 (5) | 0.0579 (4) | −0.0006 (3) | 0.0043 (2) | −0.0123 (4) |
O1 | 0.0627 (11) | 0.0498 (11) | 0.0352 (8) | −0.0108 (9) | 0.0074 (7) | −0.0130 (8) |
O2 | 0.0747 (12) | 0.0728 (14) | 0.0513 (10) | −0.0413 (11) | 0.0176 (9) | −0.0216 (11) |
O3 | 0.0750 (12) | 0.0438 (10) | 0.0366 (8) | −0.0250 (9) | 0.0222 (8) | −0.0126 (8) |
O4 | 0.0512 (9) | 0.0394 (10) | 0.0338 (8) | 0.0071 (7) | 0.0090 (7) | −0.0011 (7) |
O5 | 0.0482 (9) | 0.0269 (9) | 0.0505 (9) | 0.0004 (7) | 0.0108 (7) | 0.0031 (7) |
N1 | 0.0385 (9) | 0.0304 (11) | 0.0325 (9) | −0.0070 (8) | 0.0096 (7) | −0.0049 (8) |
C1 | 0.0481 (13) | 0.0419 (13) | 0.0292 (10) | 0.0069 (10) | 0.0052 (9) | −0.0012 (10) |
C2 | 0.0745 (18) | 0.0578 (18) | 0.0319 (12) | 0.0078 (14) | 0.0058 (12) | −0.0091 (12) |
C3 | 0.0799 (17) | 0.072 (2) | 0.0277 (10) | 0.0170 (17) | 0.0136 (11) | −0.0006 (15) |
C4 | 0.0716 (18) | 0.077 (2) | 0.0369 (13) | 0.0093 (16) | 0.0209 (12) | 0.0130 (15) |
C5 | 0.0613 (16) | 0.0566 (17) | 0.0379 (12) | −0.0024 (13) | 0.0156 (11) | 0.0023 (12) |
C6 | 0.0470 (12) | 0.0417 (14) | 0.0279 (10) | 0.0046 (10) | 0.0070 (9) | 0.0018 (10) |
C7 | 0.0494 (12) | 0.0375 (13) | 0.0308 (11) | −0.0035 (11) | 0.0086 (9) | −0.0051 (10) |
C8 | 0.0380 (10) | 0.0338 (12) | 0.0293 (9) | −0.0003 (9) | 0.0051 (7) | −0.0029 (10) |
C9 | 0.0460 (13) | 0.0463 (14) | 0.0336 (11) | −0.0037 (11) | 0.0041 (9) | −0.0107 (11) |
C10 | 0.0379 (11) | 0.0351 (13) | 0.0316 (10) | −0.0013 (9) | 0.0074 (8) | −0.0032 (9) |
C11 | 0.0371 (10) | 0.0277 (12) | 0.0289 (9) | −0.0053 (9) | 0.0088 (8) | −0.0028 (9) |
C12 | 0.0367 (11) | 0.0391 (13) | 0.0329 (11) | −0.0055 (9) | 0.0061 (9) | −0.0040 (10) |
C13 | 0.0345 (11) | 0.0275 (11) | 0.0361 (11) | −0.0003 (8) | 0.0096 (8) | 0.0037 (9) |
C14 | 0.0342 (11) | 0.0308 (12) | 0.0518 (13) | −0.0024 (9) | 0.0119 (10) | −0.0009 (10) |
C15 | 0.0437 (14) | 0.0431 (16) | 0.095 (2) | 0.0021 (12) | 0.0198 (13) | −0.0053 (15) |
Geometric parameters (Å, º) top
S1—O5 | 1.4976 (17) | C4—H4A | 0.93 |
S1—C13 | 1.805 (2) | C5—C6 | 1.400 (3) |
S1—C14 | 1.805 (2) | C5—H5 | 0.93 |
S2—C15 | 1.796 (3) | C6—C7 | 1.439 (3) |
S2—C14 | 1.797 (2) | C7—C8 | 1.344 (3) |
O1—C1 | 1.372 (3) | C7—H7 | 0.93 |
O1—C9 | 1.377 (3) | C8—C9 | 1.459 (3) |
O2—C9 | 1.204 (3) | C8—C10 | 1.504 (3) |
O3—C10 | 1.229 (3) | C11—C13 | 1.522 (3) |
O4—C12 | 1.419 (3) | C11—C12 | 1.532 (3) |
O4—H4 | 0.77 (3) | C11—H11 | 0.98 |
N1—C10 | 1.339 (3) | C12—H12A | 0.97 |
N1—C11 | 1.464 (2) | C12—H12B | 0.97 |
N1—H1A | 0.78 (3) | C13—H13A | 0.97 |
C1—C6 | 1.383 (3) | C13—H13B | 0.97 |
C1—C2 | 1.385 (3) | C14—H14A | 0.97 |
C2—C3 | 1.364 (4) | C14—H14B | 0.97 |
C2—H2 | 0.93 | C15—H15A | 0.96 |
C3—C4 | 1.390 (5) | C15—H15B | 0.96 |
C3—H3 | 0.93 | C15—H15C | 0.96 |
C4—C5 | 1.387 (3) | | |
| | | |
O5—S1—C13 | 106.79 (10) | O1—C9—C8 | 116.8 (2) |
O5—S1—C14 | 107.42 (10) | O3—C10—N1 | 123.5 (2) |
C13—S1—C14 | 95.62 (10) | O3—C10—C8 | 119.5 (2) |
C15—S2—C14 | 100.56 (12) | N1—C10—C8 | 117.01 (19) |
C1—O1—C9 | 123.04 (19) | N1—C11—C13 | 110.30 (16) |
C12—O4—H4 | 107 (2) | N1—C11—C12 | 111.05 (16) |
C10—N1—C11 | 121.87 (18) | C13—C11—C12 | 110.48 (17) |
C10—N1—H1A | 121.3 (18) | N1—C11—H11 | 108.3 |
C11—N1—H1A | 116.3 (18) | C13—C11—H11 | 108.3 |
O1—C1—C6 | 120.96 (19) | C12—C11—H11 | 108.3 |
O1—C1—C2 | 117.6 (2) | O4—C12—C11 | 113.49 (18) |
C6—C1—C2 | 121.4 (2) | O4—C12—H12A | 108.9 |
C3—C2—C1 | 119.1 (3) | C11—C12—H12A | 108.9 |
C3—C2—H2 | 120.5 | O4—C12—H12B | 108.9 |
C1—C2—H2 | 120.5 | C11—C12—H12B | 108.9 |
C2—C3—C4 | 121.1 (2) | H12A—C12—H12B | 107.7 |
C2—C3—H3 | 119.4 | C11—C13—S1 | 110.76 (14) |
C4—C3—H3 | 119.4 | C11—C13—H13A | 109.5 |
C5—C4—C3 | 119.8 (3) | S1—C13—H13A | 109.5 |
C5—C4—H4A | 120.1 | C11—C13—H13B | 109.5 |
C3—C4—H4A | 120.1 | S1—C13—H13B | 109.5 |
C4—C5—C6 | 119.6 (3) | H13A—C13—H13B | 108.1 |
C4—C5—H5 | 120.2 | S2—C14—S1 | 111.84 (12) |
C6—C5—H5 | 120.2 | S2—C14—H14A | 109.2 |
C1—C6—C5 | 119.0 (2) | S1—C14—H14A | 109.2 |
C1—C6—C7 | 117.2 (2) | S2—C14—H14B | 109.2 |
C5—C6—C7 | 123.8 (2) | S1—C14—H14B | 109.2 |
C8—C7—C6 | 122.2 (2) | H14A—C14—H14B | 107.9 |
C8—C7—H7 | 118.9 | S2—C15—H15A | 109.5 |
C6—C7—H7 | 118.9 | S2—C15—H15B | 109.5 |
C7—C8—C9 | 119.75 (18) | H15A—C15—H15B | 109.5 |
C7—C8—C10 | 118.3 (2) | S2—C15—H15C | 109.5 |
C9—C8—C10 | 121.94 (19) | H15A—C15—H15C | 109.5 |
O2—C9—O1 | 116.5 (2) | H15B—C15—H15C | 109.5 |
O2—C9—C8 | 126.6 (2) | | |
| | | |
C9—O1—C1—C6 | −0.9 (3) | C10—C8—C9—O2 | −2.7 (4) |
C9—O1—C1—C2 | 179.2 (2) | C7—C8—C9—O1 | −1.9 (3) |
O1—C1—C2—C3 | 179.7 (2) | C10—C8—C9—O1 | 176.5 (2) |
C6—C1—C2—C3 | −0.1 (4) | C11—N1—C10—O3 | 4.7 (3) |
C1—C2—C3—C4 | 0.9 (4) | C11—N1—C10—C8 | −173.84 (18) |
C2—C3—C4—C5 | −1.0 (5) | C7—C8—C10—O3 | −7.0 (3) |
C3—C4—C5—C6 | 0.2 (4) | C9—C8—C10—O3 | 174.6 (2) |
O1—C1—C6—C5 | 179.5 (2) | C7—C8—C10—N1 | 171.6 (2) |
C2—C1—C6—C5 | −0.6 (3) | C9—C8—C10—N1 | −6.8 (3) |
O1—C1—C6—C7 | −0.5 (3) | C10—N1—C11—C13 | −152.47 (19) |
C2—C1—C6—C7 | 179.3 (2) | C10—N1—C11—C12 | 84.7 (2) |
C4—C5—C6—C1 | 0.6 (4) | N1—C11—C12—O4 | 70.7 (2) |
C4—C5—C6—C7 | −179.4 (2) | C13—C11—C12—O4 | −52.1 (2) |
C1—C6—C7—C8 | 0.7 (3) | N1—C11—C13—S1 | 60.7 (2) |
C5—C6—C7—C8 | −179.3 (2) | C12—C11—C13—S1 | −176.12 (14) |
C6—C7—C8—C9 | 0.5 (3) | O5—S1—C13—C11 | 62.13 (16) |
C6—C7—C8—C10 | −177.9 (2) | C14—S1—C13—C11 | 172.25 (15) |
C1—O1—C9—O2 | −178.7 (2) | C15—S2—C14—S1 | 89.21 (15) |
C1—O1—C9—C8 | 2.1 (3) | O5—S1—C14—S2 | −68.83 (14) |
C7—C8—C9—O2 | 179.0 (3) | C13—S1—C14—S2 | −178.41 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.78 (3) | 2.12 (2) | 2.719 (2) | 134 (2) |
O4—H4···O3i | 0.77 (3) | 2.08 (3) | 2.811 (2) | 158 (3) |
C13—H13A···O5i | 0.97 | 2.40 | 3.258 (3) | 147 |
C14—H14A···O4ii | 0.97 | 2.51 | 3.420 (3) | 156 |
C14—H14B···O5i | 0.97 | 2.41 | 3.291 (3) | 151 |
C7—H7···O3 | 0.93 | 2.42 | 2.752 (3) | 101 |
C11—H11···O4iii | 0.98 | 2.53 | 3.426 (3) | 152 |
C12—H12A···O5iv | 0.97 | 2.55 | 3.424 (3) | 150 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+1; (iii) x, y−1, z; (iv) −x+1, y+1/2, −z+1. |