Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031388/hb2449sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031388/hb2449Isup2.hkl |
CCDC reference: 658981
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.006 Å
- R factor = 0.029
- wR factor = 0.079
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc. PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C14 PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl - C8 .. 5.99 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N - C13 .. 5.84 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT420_ALERT_2_C D-H Without Acceptor N - H0 ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.79 From the CIF: _reflns_number_total 3280 Count of symmetry unique reflns 1967 Completeness (_total/calc) 166.75% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1313 Fraction of Friedel pairs measured 0.668 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Erdsack & Krause (2007); Erdsack et al. (2007); Flack (1983); Hoffmann-Röder & Krause (2001).
In a Schlenk tube equipped with a magnetic stirrer bar, 47 mg (0.15 mmol) of tert-butyl-(1R,2S)-[2-hydroxy-1-(3-phenyl-2,5-dihydrofuran-2-yl)-ethyl]-carbamate (synthesis of this compound will be described elsewhere; Erdsack & Krause 2007) was dissolved in dry dichloromethane (1.5 ml) under argon and cooled to 273 K. With stirring, 87 mg (0.23 mmol) of Dess-Martin periodinane was added in one portion. After 2 h, the mixture was diluted with diethyl ether (3 ml), quenched with sat. aq. NaHCO3 and sat. aq. Na2S2O3 1:1 (5 ml) and diluted with additional 3 ml of diethyl ether. After a few minutes with stirring at r.t., the biphasic mixture came clear. The organic phase was separated and the residue was extracted with diethyl ether (3 × 10 ml). The combined organic layers were washed with aq. sat. NaHCO3 and brine and dried with MgSO4. The solution was filtered and the solvent was evaporated. The crude aldehyde was dissolved in a 1:1 mixture of t-BuOH/THF (5 ml). The flask was sealed with a rubber septum and was cooled to 273 K. With vigorous stirring, a solution of NaClO2 (80%, technical grade, 52 mg, 0.46 mmol) and NaH2PO4*H2O (82 mg, 0.46 mmol) in 1 ml water was slowly added dropwise via syringe over 30 min. The reaction mixture came yellow and was allowed to stir at r.t. overnight. The mixture was diluted with water (15 ml) and extracted with diethyl ether (3 × 15 ml). The combined organic layers were dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography on silica gel (iso-hexane/EtOAc 4:1 v/v) to give 28 mg (53%) of the lactone (I) as a solid, which was suspended in a few drops of iso-hexane. Ethyl acetate was added dropwise until the compound was completely dissolved, and colourless needles of (I) were obtained by slow evaporation at ambient temperature; mp 432 K; [α]D21 - 44.0 (c 1.40, CHCl3); IR (KBr pellet), cm-1: 3419 (m), 3323 (m), 3062 (w), 2979 (m), 2932 (m), 2885 (w), 1801 (s), 1712 (s), 1510 (m), 1451 (m), 1393 (m), 1368 (m), 1253 (m), 1163 (s), 1104 (m), 1062 (m), 942 (s), 865 (m), 751 (m), 734 (m), 699 (m), 665 (w), 577 (w), 514 (w); 1H NMR (400 MHz, CDCl3): δ (p.p.m.): 7.48 - 7.43 (m, 5 H), 5.22 (dd, J = 6.3, 13.6 Hz, 1 H), 4.69 (dd, J = 4.0, 8.6 Hz, 1 H), 4.62 (d, J = 3.4 Hz, 1 H), 4.51 (dd, J = 3.9, 10.5 Hz, 1 H), 4.32 (d, J = 10.5 Hz, 1 H), 1.46 (m, 9 H); 13C NMR (100.6 MHz, CDCl3): δ (p.p.m.) 172.0, 155.2, 132.1, 129.8, 128.7, 127.0, 94.8, 81.0, 80.1, 76.9, 63.3, 54.1, 28.2 HRMS (ESI): m/z calculated for C17H21O5N35Cl: [M + H]+ = 354.11028, found 354.11002
The H atoms were placed in calculated positions, with C—H = 0.93–0.98 and N—H = 0.86 Å and were refined as riding, with Uiso(H) = 1.5Ueq; the methyl groups were allowed to rotate but not to tip.
The title compound, (I), is a side product in the preparation of novel furanomycin derivatives using the gold-catalyzed cyclization of α-hydroxyallenes (Hoffmann-Röder & Krause, 2001). It was obtained after an aldehyde oxidation in the presence of NaClO2 and chlorolactonization of the resulted boc-protected amino acid intermediate by hypochloric acid, a degradation product of the oxidant (Erdsack & Krause, 2007). A crystal structure determination of (I) has now been carried out to establish the relative configuration of the stereogenic centers at the bicyclic core. Fig. 1 shows that the relative configuration of C6 and C6a is consistent with the stereospecific halolactonization step. The torsion angle O3—C7—C10—O1 is -88.3 (3)°. The configurations of the stereogenic C atoms in (I) (C3 R, C3a S, C6 R and C6a R) were established by refining the Flack (1983) absolute structure parameter; they are consistent with those of the equivalent atoms in the starting material (Erdsack et al., 2007).
For related literature, see: Erdsack & Krause (2007); Erdsack et al. (2007); Flack (1983); Hoffmann-Röder & Krause (2001).
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
Fig. 1. : The molecular structure of (I) with displacement ellipsoids shown at the 30% probability level (arbitrary spheres for the H atoms). |
C17H20ClNO5 | F(000) = 744 |
Mr = 353.79 | Dx = 1.342 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 14042 reflections |
a = 6.1519 (7) Å | θ = 3.1–25.8° |
b = 12.029 (2) Å | µ = 0.24 mm−1 |
c = 23.655 (4) Å | T = 291 K |
V = 1750.5 (5) Å3 | Needle, colourless |
Z = 4 | 0.44 × 0.08 × 0.08 mm |
Nonius KappaCCD diffractometer | 1085 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 25.8°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −7→7 |
309 frames via ω–rotation (Δω=1%) and two times 120 s per frame (three sets at different κ–angles) scans | k = 0→14 |
14042 measured reflections | l = 0→28 |
3280 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | [1.0exp(7.10(sinθ/λ)2)]/[σ2(Fo2)] |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.10 e Å−3 |
3280 reflections | Δρmin = −0.11 e Å−3 |
221 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0215 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1313 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.08 (10) |
C17H20ClNO5 | V = 1750.5 (5) Å3 |
Mr = 353.79 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.1519 (7) Å | µ = 0.24 mm−1 |
b = 12.029 (2) Å | T = 291 K |
c = 23.655 (4) Å | 0.44 × 0.08 × 0.08 mm |
Nonius KappaCCD diffractometer | 1085 reflections with I > 2σ(I) |
14042 measured reflections | Rint = 0.036 |
3280 independent reflections |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.079 | Δρmax = 0.10 e Å−3 |
S = 1.01 | Δρmin = −0.11 e Å−3 |
3280 reflections | Absolute structure: Flack (1983), 1313 Friedel pairs |
221 parameters | Absolute structure parameter: 0.08 (10) |
0 restraints |
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 | ||
Cl | 0.6643 (2) | 0.59959 (10) | 0.85442 (5) | 0.1028 (4) | |
O1 | 0.5371 (4) | 0.6930 (2) | 0.97543 (10) | 0.0741 (7) | |
O2 | 0.0232 (4) | 0.5437 (2) | 1.04297 (11) | 0.0772 (8) | |
O3 | 0.1997 (4) | 0.5179 (2) | 0.96171 (11) | 0.0702 (7) | |
O4 | 0.5678 (5) | 0.4974 (2) | 1.14730 (11) | 0.0925 (9) | |
O5 | 0.5498 (4) | 0.6773 (2) | 1.17002 (11) | 0.0832 (8) | |
N | 0.4380 (4) | 0.6243 (2) | 1.08588 (12) | 0.0678 (8) | |
H0 | 0.3938 | 0.6917 | 1.0822 | 0.102* | |
C1 | 0.4893 (6) | 0.4053 (3) | 0.92572 (15) | 0.0687 (10) | |
C2 | 0.3421 (8) | 0.3404 (4) | 0.89794 (16) | 0.0938 (14) | |
H2 | 0.2048 | 0.3681 | 0.8894 | 0.141* | |
C3 | 0.3975 (9) | 0.2339 (4) | 0.88258 (19) | 0.1040 (17) | |
H3 | 0.2977 | 0.1897 | 0.8635 | 0.156* | |
C4 | 0.5945 (10) | 0.1938 (4) | 0.8950 (2) | 0.1002 (16) | |
H4 | 0.6314 | 0.1219 | 0.8843 | 0.150* | |
C5 | 0.7399 (9) | 0.2570 (4) | 0.9230 (2) | 0.1152 (18) | |
H5 | 0.8761 | 0.2281 | 0.9317 | 0.173* | |
C6 | 0.6885 (8) | 0.3633 (4) | 0.93866 (18) | 0.0982 (14) | |
H6 | 0.7891 | 0.4066 | 0.9581 | 0.147* | |
C7 | 0.4274 (6) | 0.5205 (3) | 0.94081 (14) | 0.0601 (10) | |
C8 | 0.4180 (6) | 0.6041 (3) | 0.89390 (14) | 0.0701 (10) | |
H8 | 0.2905 | 0.5928 | 0.8697 | 0.105* | |
C9 | 0.4034 (6) | 0.7103 (3) | 0.92654 (15) | 0.0781 (12) | |
H9A | 0.4570 | 0.7721 | 0.9042 | 0.117* | |
H9B | 0.2543 | 0.7254 | 0.9375 | 0.117* | |
C10 | 0.5502 (5) | 0.5787 (3) | 0.98781 (15) | 0.0626 (10) | |
H10 | 0.7011 | 0.5530 | 0.9906 | 0.094* | |
C11 | 0.4212 (5) | 0.5507 (3) | 1.03969 (15) | 0.0649 (10) | |
H11 | 0.4684 | 0.4772 | 1.0527 | 0.097* | |
C12 | 0.1912 (7) | 0.5391 (3) | 1.01752 (18) | 0.0662 (10) | |
C13 | 0.5233 (6) | 0.5907 (4) | 1.13647 (18) | 0.0727 (11) | |
C14 | 0.6347 (7) | 0.6647 (4) | 1.22849 (16) | 0.0861 (13) | |
C15 | 0.8603 (6) | 0.6207 (5) | 1.22662 (17) | 0.132 (2) | |
H15A | 0.9223 | 0.6230 | 1.2638 | 0.199* | |
H15B | 0.9462 | 0.6653 | 1.2015 | 0.199* | |
H15C | 0.8581 | 0.5453 | 1.2133 | 0.199* | |
C16 | 0.6267 (10) | 0.7804 (4) | 1.24998 (17) | 0.156 (3) | |
H16A | 0.4821 | 0.8091 | 1.2458 | 0.234* | |
H16B | 0.7263 | 0.8257 | 1.2289 | 0.234* | |
H16C | 0.6667 | 0.7813 | 1.2892 | 0.234* | |
C17 | 0.4855 (7) | 0.5924 (4) | 1.26134 (17) | 0.1118 (15) | |
H17A | 0.3408 | 0.6221 | 1.2596 | 0.168* | |
H17B | 0.5325 | 0.5896 | 1.3000 | 0.168* | |
H17C | 0.4866 | 0.5188 | 1.2456 | 0.168* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.1244 (9) | 0.0872 (8) | 0.0967 (8) | 0.0053 (8) | 0.0295 (7) | 0.0076 (7) |
O1 | 0.0901 (18) | 0.0578 (18) | 0.0744 (18) | −0.0033 (16) | −0.0172 (15) | 0.0027 (13) |
O2 | 0.0676 (17) | 0.0769 (19) | 0.0872 (19) | 0.0014 (16) | −0.0038 (15) | 0.0033 (15) |
O3 | 0.0584 (16) | 0.0840 (19) | 0.0682 (17) | 0.0018 (16) | −0.0079 (14) | −0.0048 (14) |
O4 | 0.126 (2) | 0.0707 (19) | 0.0810 (19) | 0.0217 (19) | −0.0200 (18) | 0.0004 (17) |
O5 | 0.112 (2) | 0.0692 (19) | 0.0681 (17) | −0.0006 (18) | −0.0191 (16) | 0.0014 (15) |
N | 0.080 (2) | 0.059 (2) | 0.0639 (19) | 0.0043 (18) | −0.0168 (17) | 0.0010 (17) |
C1 | 0.069 (3) | 0.065 (3) | 0.073 (3) | 0.001 (3) | −0.002 (2) | 0.000 (2) |
C2 | 0.107 (4) | 0.085 (3) | 0.089 (3) | 0.003 (3) | −0.019 (3) | −0.018 (3) |
C3 | 0.130 (5) | 0.085 (4) | 0.096 (3) | −0.016 (3) | −0.008 (3) | −0.017 (3) |
C4 | 0.143 (5) | 0.059 (3) | 0.099 (4) | 0.003 (4) | 0.015 (4) | 0.003 (3) |
C5 | 0.111 (5) | 0.071 (4) | 0.163 (5) | 0.015 (3) | −0.013 (4) | 0.013 (4) |
C6 | 0.093 (3) | 0.058 (3) | 0.144 (4) | 0.007 (3) | −0.016 (3) | −0.009 (3) |
C7 | 0.054 (2) | 0.056 (3) | 0.070 (3) | 0.003 (2) | −0.004 (2) | −0.001 (2) |
C8 | 0.074 (2) | 0.069 (3) | 0.067 (2) | 0.007 (3) | −0.004 (2) | 0.004 (2) |
C9 | 0.091 (3) | 0.068 (3) | 0.076 (3) | 0.006 (2) | −0.016 (3) | 0.004 (2) |
C10 | 0.059 (2) | 0.058 (3) | 0.070 (2) | 0.000 (2) | −0.004 (2) | −0.001 (2) |
C11 | 0.064 (2) | 0.061 (3) | 0.070 (2) | −0.002 (2) | −0.016 (2) | −0.006 (2) |
C12 | 0.062 (3) | 0.057 (3) | 0.079 (3) | 0.000 (2) | −0.008 (3) | 0.000 (2) |
C13 | 0.068 (3) | 0.075 (3) | 0.075 (3) | 0.001 (3) | −0.001 (2) | −0.002 (3) |
C14 | 0.107 (4) | 0.099 (4) | 0.053 (3) | −0.004 (3) | −0.018 (3) | 0.010 (2) |
C15 | 0.085 (3) | 0.220 (6) | 0.092 (3) | 0.000 (4) | −0.021 (3) | 0.021 (4) |
C16 | 0.279 (8) | 0.100 (4) | 0.088 (4) | −0.015 (5) | −0.055 (5) | −0.023 (3) |
C17 | 0.112 (3) | 0.146 (4) | 0.078 (3) | 0.005 (4) | 0.009 (3) | 0.010 (3) |
Cl—C8 | 1.781 (3) | C6—H6 | 0.9300 |
O1—C10 | 1.409 (4) | C7—C8 | 1.499 (4) |
O1—C9 | 1.434 (4) | C7—C10 | 1.516 (4) |
O2—C12 | 1.197 (4) | C8—C9 | 1.496 (5) |
O3—C12 | 1.346 (4) | C8—H8 | 0.9800 |
O3—C7 | 1.486 (4) | C9—H9A | 0.9700 |
O4—C13 | 1.183 (4) | C9—H9B | 0.9700 |
O5—C13 | 1.320 (4) | C10—C11 | 1.500 (4) |
O5—C14 | 1.486 (4) | C10—H10 | 0.9800 |
N—C13 | 1.368 (4) | C11—C12 | 1.516 (5) |
N—C11 | 1.410 (4) | C11—H11 | 0.9800 |
N—H0 | 0.8600 | C14—C16 | 1.483 (5) |
C1—C6 | 1.360 (5) | C14—C17 | 1.484 (5) |
C1—C2 | 1.364 (5) | C14—C15 | 1.486 (5) |
C1—C7 | 1.481 (5) | C15—H15A | 0.9600 |
C2—C3 | 1.374 (6) | C15—H15B | 0.9600 |
C2—H2 | 0.9300 | C15—H15C | 0.9600 |
C3—C4 | 1.337 (6) | C16—H16A | 0.9600 |
C3—H3 | 0.9300 | C16—H16B | 0.9600 |
C4—C5 | 1.347 (6) | C16—H16C | 0.9600 |
C4—H4 | 0.9300 | C17—H17A | 0.9600 |
C5—C6 | 1.369 (5) | C17—H17B | 0.9600 |
C5—H5 | 0.9300 | C17—H17C | 0.9600 |
C10—O1—C9 | 110.0 (3) | O1—C10—C11 | 111.0 (3) |
C12—O3—C7 | 111.0 (3) | O1—C10—C7 | 105.6 (3) |
C13—O5—C14 | 121.5 (3) | C11—C10—C7 | 103.5 (3) |
C13—N—C11 | 121.4 (3) | O1—C10—H10 | 112.1 |
C13—N—H0 | 119.3 | C11—C10—H10 | 112.1 |
C11—N—H0 | 119.3 | C7—C10—H10 | 112.1 |
C6—C1—C2 | 119.6 (4) | N—C11—C10 | 117.0 (3) |
C6—C1—C7 | 121.6 (4) | N—C11—C12 | 113.2 (3) |
C2—C1—C7 | 118.7 (4) | C10—C11—C12 | 103.4 (3) |
C1—C2—C3 | 119.7 (5) | N—C11—H11 | 107.6 |
C1—C2—H2 | 120.1 | C10—C11—H11 | 107.6 |
C3—C2—H2 | 120.1 | C12—C11—H11 | 107.6 |
C4—C3—C2 | 120.2 (5) | O2—C12—O3 | 122.4 (3) |
C4—C3—H3 | 119.9 | O2—C12—C11 | 128.9 (4) |
C2—C3—H3 | 119.9 | O3—C12—C11 | 108.7 (4) |
C3—C4—C5 | 120.4 (5) | O4—C13—O5 | 126.2 (4) |
C3—C4—H4 | 119.8 | O4—C13—N | 123.9 (4) |
C5—C4—H4 | 119.8 | O5—C13—N | 109.9 (4) |
C4—C5—C6 | 120.4 (5) | C16—C14—C17 | 110.5 (4) |
C4—C5—H5 | 119.8 | C16—C14—O5 | 102.2 (3) |
C6—C5—H5 | 119.8 | C17—C14—O5 | 109.3 (3) |
C1—C6—C5 | 119.6 (5) | C16—C14—C15 | 112.0 (4) |
C1—C6—H6 | 120.2 | C17—C14—C15 | 112.6 (4) |
C5—C6—H6 | 120.2 | O5—C14—C15 | 109.7 (3) |
C1—C7—O3 | 107.6 (3) | C14—C15—H15A | 109.5 |
C1—C7—C8 | 117.4 (3) | C14—C15—H15B | 109.5 |
O3—C7—C8 | 102.9 (3) | H15A—C15—H15B | 109.5 |
C1—C7—C10 | 118.7 (3) | C14—C15—H15C | 109.5 |
O3—C7—C10 | 103.6 (3) | H15A—C15—H15C | 109.5 |
C8—C7—C10 | 104.6 (3) | H15B—C15—H15C | 109.5 |
C7—C8—C9 | 101.1 (3) | C14—C16—H16A | 109.5 |
C7—C8—Cl | 109.6 (3) | C14—C16—H16B | 109.5 |
C9—C8—Cl | 110.3 (3) | H16A—C16—H16B | 109.5 |
C7—C8—H8 | 111.8 | C14—C16—H16C | 109.5 |
C9—C8—H8 | 111.8 | H16A—C16—H16C | 109.5 |
Cl—C8—H8 | 111.8 | H16B—C16—H16C | 109.5 |
O1—C9—C8 | 105.0 (3) | C14—C17—H17A | 109.5 |
O1—C9—H9A | 110.8 | C14—C17—H17B | 109.5 |
C8—C9—H9A | 110.8 | H17A—C17—H17B | 109.5 |
O1—C9—H9B | 110.8 | C14—C17—H17C | 109.5 |
C8—C9—H9B | 110.8 | H17A—C17—H17C | 109.5 |
H9A—C9—H9B | 108.8 | H17B—C17—H17C | 109.5 |
C6—C1—C2—C3 | −0.9 (6) | C9—O1—C10—C7 | 3.9 (4) |
C7—C1—C2—C3 | 178.8 (4) | C1—C7—C10—O1 | 152.5 (3) |
C1—C2—C3—C4 | 0.3 (7) | O3—C7—C10—O1 | −88.3 (3) |
C2—C3—C4—C5 | 0.4 (8) | C8—C7—C10—O1 | 19.3 (4) |
C3—C4—C5—C6 | −0.5 (8) | C1—C7—C10—C11 | −90.8 (4) |
C2—C1—C6—C5 | 0.9 (7) | O3—C7—C10—C11 | 28.5 (3) |
C7—C1—C6—C5 | −178.8 (4) | C8—C7—C10—C11 | 136.0 (3) |
C4—C5—C6—C1 | −0.2 (8) | C13—N—C11—C10 | −116.8 (4) |
C6—C1—C7—O3 | −138.5 (4) | C13—N—C11—C12 | 123.1 (4) |
C2—C1—C7—O3 | 41.8 (4) | O1—C10—C11—N | −42.8 (4) |
C6—C1—C7—C8 | 106.1 (5) | C7—C10—C11—N | −155.7 (3) |
C2—C1—C7—C8 | −73.6 (5) | O1—C10—C11—C12 | 82.5 (4) |
C6—C1—C7—C10 | −21.4 (5) | C7—C10—C11—C12 | −30.4 (4) |
C2—C1—C7—C10 | 158.9 (4) | C7—O3—C12—O2 | 178.3 (3) |
C12—O3—C7—C1 | 110.8 (3) | C7—O3—C12—C11 | −3.7 (4) |
C12—O3—C7—C8 | −124.7 (3) | N—C11—C12—O2 | −32.6 (6) |
C12—O3—C7—C10 | −15.9 (4) | C10—C11—C12—O2 | −160.2 (4) |
C1—C7—C8—C9 | −167.4 (3) | N—C11—C12—O3 | 149.5 (3) |
O3—C7—C8—C9 | 74.6 (3) | C10—C11—C12—O3 | 21.9 (4) |
C10—C7—C8—C9 | −33.4 (4) | C14—O5—C13—O4 | −2.5 (7) |
C1—C7—C8—Cl | −50.9 (4) | C14—O5—C13—N | 178.3 (3) |
O3—C7—C8—Cl | −168.9 (2) | C11—N—C13—O4 | −7.9 (6) |
C10—C7—C8—Cl | 83.1 (3) | C11—N—C13—O5 | 171.3 (3) |
C10—O1—C9—C8 | −25.6 (4) | C13—O5—C14—C16 | −177.6 (4) |
C7—C8—C9—O1 | 36.0 (4) | C13—O5—C14—C17 | −60.5 (5) |
Cl—C8—C9—O1 | −79.9 (3) | C13—O5—C14—C15 | 63.4 (5) |
C9—O1—C10—C11 | −107.7 (3) |
Experimental details
Crystal data | |
Chemical formula | C17H20ClNO5 |
Mr | 353.79 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 291 |
a, b, c (Å) | 6.1519 (7), 12.029 (2), 23.655 (4) |
V (Å3) | 1750.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.44 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14042, 3280, 1085 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.612 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.079, 1.01 |
No. of reflections | 3280 |
No. of parameters | 221 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.10, −0.11 |
Absolute structure | Flack (1983), 1313 Friedel pairs |
Absolute structure parameter | 0.08 (10) |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).
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The title compound, (I), is a side product in the preparation of novel furanomycin derivatives using the gold-catalyzed cyclization of α-hydroxyallenes (Hoffmann-Röder & Krause, 2001). It was obtained after an aldehyde oxidation in the presence of NaClO2 and chlorolactonization of the resulted boc-protected amino acid intermediate by hypochloric acid, a degradation product of the oxidant (Erdsack & Krause, 2007). A crystal structure determination of (I) has now been carried out to establish the relative configuration of the stereogenic centers at the bicyclic core. Fig. 1 shows that the relative configuration of C6 and C6a is consistent with the stereospecific halolactonization step. The torsion angle O3—C7—C10—O1 is -88.3 (3)°. The configurations of the stereogenic C atoms in (I) (C3 R, C3a S, C6 R and C6a R) were established by refining the Flack (1983) absolute structure parameter; they are consistent with those of the equivalent atoms in the starting material (Erdsack et al., 2007).