organic compounds
Triclinic modification of N-[(1,1-dimethylethoxy)carbonyl]-3-[(R)-prop-2-en-1-ylsulfinyl]-(R)-alanine ethyl ester at 120 (1) K
aDepartment of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1, and bDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6
*Correspondence e-mail: alough@chem.utoronto.ca
There are two independent molecules in the 13H23NO5S. In the intermolecular N—H⋯O hydrogen bonds link molecules into two independent one-dimensional chains along [100]. The crystal studied was found to be a non-merohedral twin with a ratio of 0.615 (6):0.385 (1) for the refined components. At 200 (1) K [Singh et al. (2009). Acta Cryst. E65, o1385–o1386] the of the title compound contains one disordered molecule in the of a monoclinic unit cell.
of the title compound, CRelated literature
of the monlinic modification of the title compound at 200 (1) K and background information, see the preceding paper: SinghExperimental
Crystal data
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Data collection: COLLECT (Nonius, 2002); cell DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809019011/hb2979sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809019011/hb2979Isup2.hkl
Hydrogen atoms were placed in calculated positions with C—H = 0.95–0.99; N—H = 0.88 Å and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C). The crystal is a non-merohedral twin: an analysis using PLATON (Spek, 2009) gave the
-1 0 0, -0.205 1 - 0.023, 0 0 - 1 with the ratio of twin components being 0.615 (6):0.385 (1).Data collection: COLLECT (Nonius, 2002); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C13H23NO5S | Z = 2 |
Mr = 305.38 | F(000) = 328 |
Triclinic, P1 | Dx = 1.249 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1483 (5) Å | Cell parameters from 4279 reflections |
b = 11.6600 (15) Å | θ = 3.0–25.0° |
c = 13.6510 (19) Å | µ = 0.22 mm−1 |
α = 88.884 (6)° | T = 120 K |
β = 82.681 (8)° | Needle, colourless |
γ = 87.306 (8)° | 0.38 × 0.12 × 0.12 mm |
V = 811.81 (17) Å3 |
Nonius KappaCCD diffractometer | 4279 independent reflections |
Radiation source: fine-focus sealed tube | 3526 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.12 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ϕ scans and ω scans with κ offsets | h = −6→6 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −13→13 |
Tmin = 0.561, Tmax = 0.975 | l = −15→16 |
4279 measured reflections |
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)] = 0.093 | H-atom parameters constrained |
wR(F2) = 0.261 | w = 1/[σ2(Fo2) + (0.1506P)2 + 0.8783P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.003 |
4279 reflections | Δρmax = 0.76 e Å−3 |
362 parameters | Δρmin = −0.50 e Å−3 |
3 restraints | Absolute structure: Flack (1983), 1709 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.12 (18) |
C13H23NO5S | γ = 87.306 (8)° |
Mr = 305.38 | V = 811.81 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.1483 (5) Å | Mo Kα radiation |
b = 11.6600 (15) Å | µ = 0.22 mm−1 |
c = 13.6510 (19) Å | T = 120 K |
α = 88.884 (6)° | 0.38 × 0.12 × 0.12 mm |
β = 82.681 (8)° |
Nonius KappaCCD diffractometer | 4279 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 3526 reflections with I > 2σ(I) |
Tmin = 0.561, Tmax = 0.975 | Rint = 0.12 |
4279 measured reflections |
R[F2 > 2σ(F2)] = 0.093 | H-atom parameters constrained |
wR(F2) = 0.261 | Δρmax = 0.76 e Å−3 |
S = 1.08 | Δρmin = −0.50 e Å−3 |
4279 reflections | Absolute structure: Flack (1983), 1709 Friedel pairs |
362 parameters | Absolute structure parameter: −0.12 (18) |
3 restraints |
Experimental. Absorption correction: multi-scan from symmetry-related measurements (SORTAV; Blessing, 1995) |
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. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.2491 (4) | 0.89719 (19) | 0.70483 (18) | 0.0441 (7) | |
O1A | 0.5083 (12) | 0.9001 (5) | 0.7397 (6) | 0.050 (2) | |
O2A | −0.046 (3) | 0.6226 (7) | 0.9264 (8) | 0.115 (4) | |
O3A | 0.1256 (13) | 0.4856 (5) | 0.8249 (6) | 0.0507 (17) | |
O4A | 0.7047 (11) | 0.5997 (5) | 0.6652 (5) | 0.0413 (15) | |
O5A | 0.4606 (12) | 0.5281 (6) | 0.5530 (5) | 0.0463 (16) | |
N1A | 0.2589 (14) | 0.6302 (6) | 0.6753 (6) | 0.0383 (18) | |
H1AC | 0.1245 | 0.6303 | 0.6415 | 0.046* | |
C1A | 0.0703 (18) | 0.7904 (8) | 0.7809 (8) | 0.042 (2) | |
H1AA | 0.0412 | 0.8158 | 0.8504 | 0.051* | |
H1AB | −0.1031 | 0.7821 | 0.7583 | 0.051* | |
C2A | 0.2212 (19) | 0.6762 (8) | 0.7748 (8) | 0.042 (2) | |
H2AA | 0.3990 | 0.6892 | 0.7934 | 0.051* | |
C3A | 0.088 (2) | 0.5935 (8) | 0.8518 (9) | 0.051 (3) | |
C4A | −0.010 (2) | 0.3966 (9) | 0.8887 (8) | 0.045 (2) | |
H4AA | 0.1043 | 0.3259 | 0.8886 | 0.054* | |
H4AB | −0.0465 | 0.4243 | 0.9574 | 0.054* | |
C5A | −0.256 (2) | 0.3713 (10) | 0.8523 (8) | 0.052 (3) | |
H5AA | −0.3435 | 0.3120 | 0.8943 | 0.078* | |
H5AB | −0.2186 | 0.3438 | 0.7843 | 0.078* | |
H5AC | −0.3694 | 0.4412 | 0.8537 | 0.078* | |
C6A | 0.058 (2) | 1.0212 (9) | 0.7578 (10) | 0.053 (3) | |
H6AA | −0.1303 | 1.0101 | 0.7560 | 0.063* | |
H6AB | 0.0870 | 1.0286 | 0.8277 | 0.063* | |
C7A | 0.135 (2) | 1.1285 (9) | 0.7021 (10) | 0.060 (3) | |
H7A | 0.0429 | 1.1508 | 0.6483 | 0.072* | |
C8A | 0.317 (3) | 1.1927 (11) | 0.7218 (13) | 0.081 (4) | |
H8A1 | 0.4137 | 1.1730 | 0.7750 | 0.097* | |
H8A2 | 0.3554 | 1.2598 | 0.6831 | 0.097* | |
C9A | 0.4911 (15) | 0.5880 (7) | 0.6343 (7) | 0.0332 (19) | |
C10A | 0.6878 (18) | 0.4846 (8) | 0.4849 (7) | 0.045 (2) | |
C11A | 0.558 (2) | 0.4260 (10) | 0.4071 (9) | 0.057 (3) | |
H11A | 0.4571 | 0.4832 | 0.3723 | 0.086* | |
H11B | 0.4412 | 0.3685 | 0.4387 | 0.086* | |
H11C | 0.6933 | 0.3882 | 0.3598 | 0.086* | |
C12A | 0.849 (2) | 0.5805 (8) | 0.4435 (8) | 0.051 (3) | |
H12A | 0.7395 | 0.6356 | 0.4098 | 0.077* | |
H12B | 0.9941 | 0.5504 | 0.3964 | 0.077* | |
H12C | 0.9183 | 0.6190 | 0.4971 | 0.077* | |
C13A | 0.846 (2) | 0.3923 (9) | 0.5393 (9) | 0.052 (3) | |
H13A | 0.9297 | 0.4291 | 0.5904 | 0.077* | |
H13B | 0.9812 | 0.3550 | 0.4918 | 0.077* | |
H13C | 0.7277 | 0.3348 | 0.5700 | 0.077* | |
S1B | 0.1520 (4) | 0.40207 (18) | 0.18589 (17) | 0.0407 (6) | |
O1B | −0.1088 (12) | 0.4057 (5) | 0.1524 (5) | 0.0425 (17) | |
O2B | 0.467 (2) | 0.1249 (6) | −0.0308 (7) | 0.084 (3) | |
O3B | 0.3134 (13) | −0.0110 (5) | 0.0748 (5) | 0.0487 (17) | |
O4B | −0.2688 (11) | 0.1054 (5) | 0.2279 (5) | 0.0411 (15) | |
O5B | −0.0182 (11) | 0.0315 (6) | 0.3428 (5) | 0.0444 (16) | |
N1B | 0.1704 (14) | 0.1343 (6) | 0.2209 (6) | 0.0372 (18) | |
H1BC | 0.3029 | 0.1340 | 0.2557 | 0.045* | |
C1B | 0.3469 (17) | 0.2925 (8) | 0.1143 (8) | 0.041 (2) | |
H1BA | 0.3831 | 0.3186 | 0.0447 | 0.050* | |
H1BB | 0.5167 | 0.2789 | 0.1404 | 0.050* | |
C2B | 0.2017 (18) | 0.1810 (8) | 0.1194 (8) | 0.041 (2) | |
H2BA | 0.0231 | 0.1986 | 0.1000 | 0.050* | |
C3B | 0.342 (2) | 0.0972 (8) | 0.0474 (8) | 0.047 (2) | |
C4B | 0.455 (2) | −0.1020 (9) | 0.0122 (10) | 0.054 (3) | |
H4BA | 0.4769 | −0.0765 | −0.0579 | 0.065* | |
H4BB | 0.3548 | −0.1727 | 0.0179 | 0.065* | |
C5B | 0.718 (2) | −0.1254 (10) | 0.0464 (9) | 0.059 (3) | |
H5BA | 0.8162 | −0.1850 | 0.0055 | 0.089* | |
H5BB | 0.6947 | −0.1515 | 0.1155 | 0.089* | |
H5BC | 0.8158 | −0.0549 | 0.0407 | 0.089* | |
C6B | 0.322 (2) | 0.5239 (8) | 0.1283 (9) | 0.045 (2) | |
H6BA | 0.5068 | 0.5193 | 0.1414 | 0.054* | |
H6BB | 0.3198 | 0.5224 | 0.0559 | 0.054* | |
C7B | 0.190 (2) | 0.6333 (9) | 0.1687 (10) | 0.056 (3) | |
H7B | 0.0191 | 0.6528 | 0.1529 | 0.067* | |
C8B | 0.293 (3) | 0.7024 (11) | 0.2231 (11) | 0.071 (4) | |
H8B1 | 0.4639 | 0.6856 | 0.2403 | 0.086* | |
H8B2 | 0.1980 | 0.7705 | 0.2462 | 0.086* | |
C9B | −0.0584 (16) | 0.0921 (7) | 0.2610 (7) | 0.035 (2) | |
C10B | −0.2460 (17) | −0.0139 (8) | 0.4090 (8) | 0.044 (2) | |
C11B | −0.107 (2) | −0.0749 (11) | 0.4897 (9) | 0.061 (3) | |
H11D | −0.0214 | −0.0182 | 0.5253 | 0.092* | |
H11E | 0.0257 | −0.1310 | 0.4593 | 0.092* | |
H11F | −0.2352 | −0.1145 | 0.5359 | 0.092* | |
C12B | −0.4219 (18) | 0.0843 (9) | 0.4501 (8) | 0.052 (3) | |
H12D | −0.5083 | 0.1214 | 0.3971 | 0.078* | |
H12E | −0.3177 | 0.1402 | 0.4787 | 0.078* | |
H12F | −0.5547 | 0.0557 | 0.5014 | 0.078* | |
C13B | −0.3820 (19) | −0.1009 (8) | 0.3539 (8) | 0.047 (3) | |
H13D | −0.4722 | −0.0611 | 0.3031 | 0.070* | |
H13E | −0.5098 | −0.1404 | 0.4004 | 0.070* | |
H13F | −0.2514 | −0.1571 | 0.3226 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0443 (15) | 0.0370 (13) | 0.0497 (18) | 0.0002 (10) | −0.0016 (12) | −0.0016 (11) |
O1A | 0.034 (4) | 0.035 (4) | 0.078 (6) | 0.003 (3) | 0.000 (4) | −0.011 (3) |
O2A | 0.223 (12) | 0.033 (4) | 0.065 (7) | 0.014 (5) | 0.062 (8) | 0.006 (4) |
O3A | 0.055 (4) | 0.038 (4) | 0.058 (5) | −0.005 (3) | −0.003 (3) | −0.007 (3) |
O4A | 0.035 (3) | 0.040 (3) | 0.049 (4) | −0.001 (3) | −0.006 (3) | −0.003 (3) |
O5A | 0.041 (4) | 0.055 (4) | 0.043 (4) | −0.004 (3) | −0.003 (3) | −0.015 (3) |
N1A | 0.034 (4) | 0.046 (4) | 0.036 (5) | 0.002 (3) | −0.011 (3) | 0.001 (4) |
C1A | 0.036 (5) | 0.045 (5) | 0.045 (6) | 0.000 (4) | −0.003 (4) | 0.002 (5) |
C2A | 0.050 (6) | 0.034 (5) | 0.043 (6) | 0.001 (4) | −0.008 (4) | −0.003 (4) |
C3A | 0.058 (6) | 0.043 (6) | 0.049 (7) | 0.003 (4) | −0.003 (5) | 0.008 (5) |
C4A | 0.046 (6) | 0.050 (6) | 0.040 (6) | −0.002 (4) | −0.004 (5) | 0.005 (5) |
C5A | 0.060 (7) | 0.059 (6) | 0.039 (6) | −0.019 (5) | −0.010 (5) | 0.019 (5) |
C6A | 0.055 (6) | 0.038 (5) | 0.064 (8) | −0.004 (4) | −0.003 (5) | −0.001 (5) |
C7A | 0.057 (7) | 0.051 (7) | 0.071 (9) | −0.007 (5) | 0.001 (6) | −0.012 (6) |
C8A | 0.073 (8) | 0.061 (8) | 0.105 (12) | −0.016 (6) | 0.016 (8) | −0.019 (8) |
C9A | 0.029 (5) | 0.028 (4) | 0.043 (6) | −0.001 (3) | −0.009 (4) | 0.006 (4) |
C10A | 0.043 (5) | 0.045 (5) | 0.044 (6) | 0.002 (4) | −0.001 (4) | −0.001 (4) |
C11A | 0.044 (6) | 0.083 (8) | 0.044 (7) | 0.004 (5) | −0.004 (5) | −0.021 (6) |
C12A | 0.054 (6) | 0.043 (5) | 0.056 (7) | 0.001 (4) | −0.001 (5) | 0.003 (5) |
C13A | 0.046 (6) | 0.045 (6) | 0.061 (8) | −0.001 (4) | 0.006 (5) | −0.004 (5) |
S1B | 0.0410 (14) | 0.0346 (13) | 0.0462 (17) | −0.0050 (9) | −0.0031 (11) | 0.0014 (10) |
O1B | 0.039 (4) | 0.035 (4) | 0.053 (5) | −0.005 (3) | −0.004 (3) | 0.002 (3) |
O2B | 0.151 (9) | 0.035 (4) | 0.057 (6) | −0.020 (4) | 0.034 (6) | 0.001 (4) |
O3B | 0.056 (4) | 0.035 (4) | 0.053 (5) | 0.002 (3) | −0.001 (3) | −0.002 (3) |
O4B | 0.033 (3) | 0.043 (4) | 0.047 (4) | −0.003 (3) | −0.006 (3) | 0.008 (3) |
O5B | 0.038 (4) | 0.051 (4) | 0.045 (4) | −0.008 (3) | −0.006 (3) | 0.009 (3) |
N1B | 0.032 (4) | 0.045 (4) | 0.036 (5) | −0.009 (3) | −0.008 (3) | −0.002 (4) |
C1B | 0.031 (5) | 0.042 (5) | 0.051 (7) | −0.002 (4) | −0.003 (4) | −0.004 (5) |
C2B | 0.035 (5) | 0.035 (5) | 0.055 (7) | −0.005 (4) | −0.007 (4) | 0.003 (4) |
C3B | 0.054 (6) | 0.035 (5) | 0.052 (7) | −0.006 (4) | −0.011 (5) | 0.004 (5) |
C4B | 0.074 (7) | 0.027 (5) | 0.059 (8) | −0.003 (4) | 0.005 (6) | 0.000 (5) |
C5B | 0.060 (7) | 0.054 (6) | 0.061 (8) | 0.010 (5) | −0.002 (5) | −0.015 (6) |
C6B | 0.040 (5) | 0.040 (5) | 0.054 (7) | −0.006 (4) | −0.002 (4) | −0.002 (4) |
C7B | 0.049 (6) | 0.045 (6) | 0.073 (9) | −0.006 (5) | −0.003 (6) | −0.001 (6) |
C8B | 0.066 (7) | 0.050 (7) | 0.094 (11) | −0.009 (5) | 0.008 (7) | −0.009 (7) |
C9B | 0.034 (5) | 0.031 (4) | 0.039 (6) | −0.005 (3) | −0.001 (4) | 0.003 (4) |
C10B | 0.042 (5) | 0.044 (5) | 0.044 (6) | −0.005 (4) | −0.002 (4) | 0.005 (4) |
C11B | 0.054 (6) | 0.077 (8) | 0.050 (7) | −0.013 (5) | 0.002 (5) | 0.017 (6) |
C12B | 0.042 (5) | 0.063 (7) | 0.049 (7) | −0.011 (5) | 0.003 (5) | −0.013 (5) |
C13B | 0.048 (6) | 0.043 (6) | 0.048 (7) | −0.006 (4) | 0.000 (5) | 0.005 (5) |
S1A—O1A | 1.475 (7) | S1B—O1B | 1.471 (7) |
S1A—C1A | 1.814 (10) | S1B—C1B | 1.809 (10) |
S1A—C6A | 1.818 (11) | S1B—C6B | 1.816 (11) |
O2A—C3A | 1.200 (14) | O2B—C3B | 1.220 (13) |
O3A—C3A | 1.316 (12) | O3B—C3B | 1.319 (12) |
O3A—C4A | 1.483 (13) | O3B—C4B | 1.481 (13) |
O4A—C9A | 1.241 (10) | O4B—C9B | 1.228 (10) |
O5A—C9A | 1.353 (11) | O5B—C9B | 1.344 (11) |
O5A—C10A | 1.475 (11) | O5B—C10B | 1.497 (11) |
N1A—C9A | 1.330 (11) | N1B—C9B | 1.345 (11) |
N1A—C2A | 1.456 (13) | N1B—C2B | 1.471 (13) |
N1A—H1AC | 0.8800 | N1B—H1BC | 0.8800 |
C1A—C2A | 1.508 (12) | C1B—C2B | 1.526 (13) |
C1A—H1AA | 0.9900 | C1B—H1BA | 0.9900 |
C1A—H1AB | 0.9900 | C1B—H1BB | 0.9900 |
C2A—C3A | 1.532 (15) | C2B—C3B | 1.495 (14) |
C2A—H2AA | 1.0000 | C2B—H2BA | 1.0000 |
C4A—C5A | 1.461 (14) | C4B—C5B | 1.500 (16) |
C4A—H4AA | 0.9900 | C4B—H4BA | 0.9900 |
C4A—H4AB | 0.9900 | C4B—H4BB | 0.9900 |
C5A—H5AA | 0.9800 | C5B—H5BA | 0.9800 |
C5A—H5AB | 0.9800 | C5B—H5BB | 0.9800 |
C5A—H5AC | 0.9800 | C5B—H5BC | 0.9800 |
C6A—C7A | 1.494 (17) | C6B—C7B | 1.497 (14) |
C6A—H6AA | 0.9900 | C6B—H6BA | 0.9900 |
C6A—H6AB | 0.9900 | C6B—H6BB | 0.9900 |
C7A—C8A | 1.283 (17) | C7B—C8B | 1.282 (17) |
C7A—H7A | 0.9500 | C7B—H7B | 0.9500 |
C8A—H8A1 | 0.9500 | C8B—H8B1 | 0.9500 |
C8A—H8A2 | 0.9500 | C8B—H8B2 | 0.9500 |
C10A—C12A | 1.483 (14) | C10B—C12B | 1.498 (13) |
C10A—C11A | 1.513 (14) | C10B—C13B | 1.521 (14) |
C10A—C13A | 1.554 (14) | C10B—C11B | 1.535 (15) |
C11A—H11A | 0.9800 | C11B—H11D | 0.9800 |
C11A—H11B | 0.9800 | C11B—H11E | 0.9800 |
C11A—H11C | 0.9800 | C11B—H11F | 0.9800 |
C12A—H12A | 0.9800 | C12B—H12D | 0.9800 |
C12A—H12B | 0.9800 | C12B—H12E | 0.9800 |
C12A—H12C | 0.9800 | C12B—H12F | 0.9800 |
C13A—H13A | 0.9800 | C13B—H13D | 0.9800 |
C13A—H13B | 0.9800 | C13B—H13E | 0.9800 |
C13A—H13C | 0.9800 | C13B—H13F | 0.9800 |
O1A—S1A—C1A | 106.2 (4) | O1B—S1B—C1B | 106.4 (4) |
O1A—S1A—C6A | 106.3 (5) | O1B—S1B—C6B | 106.8 (4) |
C1A—S1A—C6A | 96.2 (5) | C1B—S1B—C6B | 96.5 (5) |
C3A—O3A—C4A | 118.2 (8) | C3B—O3B—C4B | 118.7 (8) |
C9A—O5A—C10A | 121.6 (7) | C9B—O5B—C10B | 120.0 (6) |
C9A—N1A—C2A | 121.8 (8) | C9B—N1B—C2B | 120.8 (8) |
C9A—N1A—H1AC | 119.1 | C9B—N1B—H1BC | 119.6 |
C2A—N1A—H1AC | 119.1 | C2B—N1B—H1BC | 119.6 |
C2A—C1A—S1A | 110.4 (7) | C2B—C1B—S1B | 110.2 (6) |
C2A—C1A—H1AA | 109.6 | C2B—C1B—H1BA | 109.6 |
S1A—C1A—H1AA | 109.6 | S1B—C1B—H1BA | 109.6 |
C2A—C1A—H1AB | 109.6 | C2B—C1B—H1BB | 109.6 |
S1A—C1A—H1AB | 109.6 | S1B—C1B—H1BB | 109.6 |
H1AA—C1A—H1AB | 108.1 | H1BA—C1B—H1BB | 108.1 |
N1A—C2A—C1A | 112.7 (8) | N1B—C2B—C3B | 112.1 (8) |
N1A—C2A—C3A | 113.1 (8) | N1B—C2B—C1B | 110.4 (8) |
C1A—C2A—C3A | 109.1 (8) | C3B—C2B—C1B | 109.9 (8) |
N1A—C2A—H2AA | 107.2 | N1B—C2B—H2BA | 108.1 |
C1A—C2A—H2AA | 107.2 | C3B—C2B—H2BA | 108.1 |
C3A—C2A—H2AA | 107.2 | C1B—C2B—H2BA | 108.1 |
O2A—C3A—O3A | 123.0 (10) | O2B—C3B—O3B | 122.5 (10) |
O2A—C3A—C2A | 124.6 (9) | O2B—C3B—C2B | 123.8 (9) |
O3A—C3A—C2A | 112.3 (9) | O3B—C3B—C2B | 113.6 (9) |
C5A—C4A—O3A | 109.9 (8) | O3B—C4B—C5B | 108.1 (9) |
C5A—C4A—H4AA | 109.7 | O3B—C4B—H4BA | 110.1 |
O3A—C4A—H4AA | 109.7 | C5B—C4B—H4BA | 110.1 |
C5A—C4A—H4AB | 109.7 | O3B—C4B—H4BB | 110.1 |
O3A—C4A—H4AB | 109.7 | C5B—C4B—H4BB | 110.1 |
H4AA—C4A—H4AB | 108.2 | H4BA—C4B—H4BB | 108.4 |
C4A—C5A—H5AA | 109.5 | C4B—C5B—H5BA | 109.5 |
C4A—C5A—H5AB | 109.5 | C4B—C5B—H5BB | 109.5 |
H5AA—C5A—H5AB | 109.5 | H5BA—C5B—H5BB | 109.5 |
C4A—C5A—H5AC | 109.5 | C4B—C5B—H5BC | 109.5 |
H5AA—C5A—H5AC | 109.5 | H5BA—C5B—H5BC | 109.5 |
H5AB—C5A—H5AC | 109.5 | H5BB—C5B—H5BC | 109.5 |
C7A—C6A—S1A | 110.9 (8) | C7B—C6B—S1B | 109.7 (8) |
C7A—C6A—H6AA | 109.5 | C7B—C6B—H6BA | 109.7 |
S1A—C6A—H6AA | 109.5 | S1B—C6B—H6BA | 109.7 |
C7A—C6A—H6AB | 109.5 | C7B—C6B—H6BB | 109.7 |
S1A—C6A—H6AB | 109.5 | S1B—C6B—H6BB | 109.7 |
H6AA—C6A—H6AB | 108.1 | H6BA—C6B—H6BB | 108.2 |
C8A—C7A—C6A | 124.6 (14) | C8B—C7B—C6B | 124.5 (11) |
C8A—C7A—H7A | 117.7 | C8B—C7B—H7B | 117.8 |
C6A—C7A—H7A | 117.7 | C6B—C7B—H7B | 117.8 |
C7A—C8A—H8A1 | 120.0 | C7B—C8B—H8B1 | 120.0 |
C7A—C8A—H8A2 | 120.0 | C7B—C8B—H8B2 | 120.0 |
H8A1—C8A—H8A2 | 120.0 | H8B1—C8B—H8B2 | 120.0 |
O4A—C9A—N1A | 126.2 (8) | O4B—C9B—O5B | 125.5 (7) |
O4A—C9A—O5A | 124.3 (7) | O4B—C9B—N1B | 125.9 (8) |
N1A—C9A—O5A | 109.5 (7) | O5B—C9B—N1B | 108.7 (7) |
O5A—C10A—C12A | 110.6 (7) | O5B—C10B—C12B | 109.5 (7) |
O5A—C10A—C11A | 102.4 (7) | O5B—C10B—C13B | 109.9 (8) |
C12A—C10A—C11A | 112.5 (9) | C12B—C10B—C13B | 114.2 (8) |
O5A—C10A—C13A | 109.3 (8) | O5B—C10B—C11B | 101.2 (7) |
C12A—C10A—C13A | 113.0 (8) | C12B—C10B—C11B | 111.3 (9) |
C11A—C10A—C13A | 108.6 (9) | C13B—C10B—C11B | 110.0 (9) |
C10A—C11A—H11A | 109.5 | C10B—C11B—H11D | 109.5 |
C10A—C11A—H11B | 109.5 | C10B—C11B—H11E | 109.5 |
H11A—C11A—H11B | 109.5 | H11D—C11B—H11E | 109.5 |
C10A—C11A—H11C | 109.5 | C10B—C11B—H11F | 109.5 |
H11A—C11A—H11C | 109.5 | H11D—C11B—H11F | 109.5 |
H11B—C11A—H11C | 109.5 | H11E—C11B—H11F | 109.5 |
C10A—C12A—H12A | 109.5 | C10B—C12B—H12D | 109.5 |
C10A—C12A—H12B | 109.5 | C10B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
C10A—C12A—H12C | 109.5 | C10B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
C10A—C13A—H13A | 109.5 | C10B—C13B—H13D | 109.5 |
C10A—C13A—H13B | 109.5 | C10B—C13B—H13E | 109.5 |
H13A—C13A—H13B | 109.5 | H13D—C13B—H13E | 109.5 |
C10A—C13A—H13C | 109.5 | C10B—C13B—H13F | 109.5 |
H13A—C13A—H13C | 109.5 | H13D—C13B—H13F | 109.5 |
H13B—C13A—H13C | 109.5 | H13E—C13B—H13F | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AC···O4Ai | 0.88 | 2.19 | 2.913 (9) | 139 |
N1B—H1BC···O4Bii | 0.88 | 2.20 | 2.904 (9) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H23NO5S |
Mr | 305.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 5.1483 (5), 11.6600 (15), 13.6510 (19) |
α, β, γ (°) | 88.884 (6), 82.681 (8), 87.306 (8) |
V (Å3) | 811.81 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.38 × 0.12 × 0.12 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.561, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4279, 4279, 3526 |
Rint | 0.12 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.093, 0.261, 1.08 |
No. of reflections | 4279 |
No. of parameters | 362 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.76, −0.50 |
Absolute structure | Flack (1983), 1709 Friedel pairs |
Absolute structure parameter | −0.12 (18) |
Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AC···O4Ai | 0.88 | 2.19 | 2.913 (9) | 139 |
N1B—H1BC···O4Bii | 0.88 | 2.20 | 2.904 (9) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Acknowledgements
The authors wish to acknowledge NSERC Canada and the University of Toronto for funding and the donors of the American Chemical Society Petroleum Research Fund for support of this research.
References
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
For background information on the title compound see the previous paper (Singh et al., 2009).
The asymmetric unit of the title compound is shown in Fig. 1. It contains two indpendent moleclues [A and B] which have essentially the same conformation apart from the orientation of the propenyl groups (see Fig. 3). This difference is reflected in the the values of the S1—C6—C7—C8 torsion angles for molecules A and B which are -89.5 (13) and 112.2 (13)°, respectively. Data for the title compound were also collected at 200 (1) K and the crystal structure solves and refines in the monoclinic space group P21 (Singh et al., 2009) with one molecule in the asymmetric unit and a disordered propenyl group. The torsion angles for the S1—C6—C7—C8 sequence of atoms in the major and minor components of the disorder are -99 (1) and 107 (3). The same crystal was used for both determinations. In the crystal structure, intermolecular hydrogen bonds link molecules into two independent one-dimensional chains along [100] (Table 1, Fig. 2).