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The enantiopure title compound, C16H15NO5, was obtained, together with its hydro­lysed (3S,4R)-enantiomer, by resolution of racemic cis-3-acetoxy-1-(4-methoxy­phenyl)-4-(2-furan­yl)­azetidin-2-one using a native enzyme MTCC 5125. The two H atoms on the azetidinone ring are sited in a cis configuration above the plane of the β-lactam ring, as indicated by 1H NMR.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014540/bt6472sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014540/bt6472Isup2.hkl
Contains datablock I

CCDC reference: 245308

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.105
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



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 27.49 From the CIF: _reflns_number_total 1833 Count of symmetry unique reflns 1841 Completeness (_total/calc) 99.57% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
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: R3m/V User's Guide (Siemens, 1989); cell refinement: R3m/V User's Guide; data reduction: XDISK in R3m/V User's Guide; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C16H15NO5F(000) = 316
Mr = 301.29Dx = 1.337 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 15 reflections
a = 5.459 (3) Åθ = 7.5–15°
b = 8.011 (3) ŵ = 0.10 mm1
c = 17.205 (5) ÅT = 293 K
β = 96.00 (3)°Prism, colourless
V = 748.3 (5) Å30.52 × 0.51 × 0.40 mm
Z = 2
Data collection top
Siemens P4 4-circle
diffractometer
1592 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Profile fitted ω scansh = 70
Absorption correction: ψ scan
(XPREP in SHELXTL-Plus; Sheldrick, 1995)
k = 010
Tmin = 0.930, Tmax = 0.962l = 2222
2019 measured reflections3 standard reflections every 100 reflections
1833 independent reflections intensity decay: 2%
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0627P)2 + 0.0621P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1833 reflectionsΔρmax = 0.17 e Å3
202 parametersΔρmin = 0.17 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (6)
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
N10.0086 (3)0.1929 (2)0.74792 (11)0.0470 (5)
C20.1948 (4)0.2496 (3)0.79359 (14)0.0467 (5)
O20.3737 (3)0.3284 (2)0.77931 (11)0.0574 (4)
C30.1045 (4)0.1774 (3)0.86735 (13)0.0459 (5)
H30.04750.26340.90180.055*
C40.1108 (4)0.0989 (3)0.81158 (13)0.0442 (5)
H40.27230.14130.82230.053*
C110.0925 (4)0.2061 (3)0.66739 (13)0.0470 (5)
C120.0383 (5)0.2997 (4)0.61847 (16)0.0609 (7)
H120.18130.35510.63810.073*
C130.0463 (6)0.3104 (4)0.53907 (16)0.0672 (7)
H130.04060.37370.50590.081*
C140.2568 (5)0.2282 (4)0.50946 (14)0.0601 (7)
O140.3212 (5)0.2442 (4)0.43025 (11)0.0851 (7)
C1410.5337 (7)0.1633 (6)0.39644 (18)0.0942 (12)
H1410.67530.20770.41800.127*
H1420.52110.04590.40720.127*
H1430.55030.18090.34100.127*
C150.3886 (5)0.1355 (4)0.55858 (15)0.0585 (6)
H150.53180.08050.53890.070*
C160.3052 (5)0.1252 (4)0.63786 (15)0.0556 (6)
H160.39370.06320.67110.067*
O310.2765 (3)0.0658 (2)0.90717 (9)0.0483 (4)
C320.2084 (4)0.0031 (4)0.97364 (14)0.0540 (6)
O320.0144 (4)0.0262 (4)0.99705 (14)0.0769 (6)
C330.4010 (5)0.1167 (5)1.0111 (2)0.0779 (10)
H3310.36010.22990.99690.105*
H3320.41000.10491.06680.105*
H3330.55730.08850.99380.105*
C410.1107 (4)0.0856 (3)0.80191 (14)0.0459 (5)
C420.2704 (5)0.2040 (4)0.81785 (15)0.0617 (7)
H420.42050.18820.83790.074*
C430.1653 (7)0.3589 (4)0.79810 (19)0.0733 (9)
H430.23370.46430.80260.088*
C440.0473 (7)0.3239 (4)0.7723 (2)0.0806 (9)
H440.15480.40270.75520.097*
O450.0881 (4)0.1548 (3)0.77412 (15)0.0740 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0479 (10)0.0450 (10)0.0468 (10)0.0025 (8)0.0010 (7)0.0046 (8)
C20.0473 (11)0.0361 (10)0.0553 (12)0.0083 (9)0.0017 (9)0.0029 (10)
O20.0502 (9)0.0506 (10)0.0729 (11)0.0057 (8)0.0005 (8)0.0043 (9)
C30.0450 (10)0.0436 (12)0.0480 (11)0.0081 (10)0.0002 (8)0.0035 (10)
C40.0386 (10)0.0476 (12)0.0459 (11)0.0065 (9)0.0019 (8)0.0001 (10)
C110.0493 (11)0.0443 (12)0.0464 (11)0.0085 (10)0.0009 (9)0.0011 (10)
C120.0592 (14)0.0640 (17)0.0590 (13)0.0054 (13)0.0042 (11)0.0037 (13)
C130.0760 (17)0.0704 (19)0.0569 (14)0.0024 (15)0.0147 (12)0.0108 (14)
C140.0723 (15)0.0631 (16)0.0442 (12)0.0141 (13)0.0023 (10)0.0029 (12)
O140.1039 (16)0.1034 (18)0.0464 (9)0.0050 (15)0.0001 (10)0.0081 (12)
C1410.114 (3)0.114 (3)0.0507 (16)0.017 (3)0.0106 (17)0.003 (2)
C150.0580 (13)0.0644 (16)0.0507 (13)0.0003 (12)0.0050 (10)0.0011 (13)
C160.0554 (13)0.0587 (15)0.0515 (12)0.0021 (12)0.0002 (10)0.0074 (11)
O310.0437 (8)0.0545 (9)0.0456 (8)0.0061 (7)0.0003 (6)0.0040 (7)
C320.0457 (11)0.0640 (15)0.0514 (12)0.0039 (12)0.0005 (9)0.0006 (12)
O320.0666 (10)0.1023 (18)0.0642 (10)0.0111 (12)0.0188 (8)0.0120 (12)
C330.0644 (15)0.093 (3)0.0756 (18)0.0085 (16)0.0029 (14)0.0332 (19)
C410.0407 (10)0.0490 (12)0.0467 (12)0.0046 (10)0.0022 (9)0.0015 (10)
C420.0641 (15)0.0673 (18)0.0541 (13)0.0098 (13)0.0076 (11)0.0054 (13)
C430.095 (2)0.0486 (15)0.0731 (19)0.0131 (15)0.0065 (16)0.0067 (14)
C440.083 (2)0.0493 (16)0.108 (3)0.0115 (16)0.0047 (19)0.0104 (18)
O450.0627 (11)0.0486 (10)0.1137 (18)0.0038 (9)0.0235 (11)0.0113 (12)
Geometric parameters (Å, º) top
N1—C21.369 (3)C141—H1420.9600
N1—C111.417 (3)C141—H1430.9600
N1—C41.485 (3)C15—C161.394 (3)
C2—O21.209 (3)C15—H150.9300
C2—C31.523 (3)C16—H160.9300
C3—O311.420 (3)O31—C321.356 (3)
C3—C41.569 (3)C32—O321.195 (3)
C3—H30.9800C32—C331.486 (4)
C4—C411.487 (3)C33—H3310.9600
C4—H40.9800C33—H3320.9600
C11—C161.379 (4)C33—H3330.9600
C11—C121.381 (4)C41—C421.336 (4)
C12—C131.398 (4)C41—O451.350 (3)
C12—H120.9300C42—C431.423 (5)
C13—C141.375 (4)C42—H420.9300
C13—H130.9300C43—C441.316 (5)
C14—O141.377 (3)C43—H430.9300
C14—C151.382 (4)C44—O451.373 (4)
O14—C1411.401 (5)C44—H440.9300
C141—H1410.9600
C2—N1—C11134.1 (2)H141—C141—H142109.5
C2—N1—C495.14 (18)O14—C141—H143109.5
C11—N1—C4130.60 (19)H141—C141—H143109.5
O2—C2—N1132.9 (2)H142—C141—H143109.5
O2—C2—C3134.9 (2)C14—C15—C16119.5 (2)
N1—C2—C392.20 (18)C14—C15—H15120.2
O31—C3—C2112.69 (18)C16—C15—H15120.2
O31—C3—C4117.2 (2)C11—C16—C15120.6 (2)
C2—C3—C485.97 (17)C11—C16—H16119.7
O31—C3—H3112.8C15—C16—H16119.7
C2—C3—H3112.8C32—O31—C3115.93 (18)
C4—C3—H3112.8O32—C32—O31122.4 (2)
N1—C4—C41114.7 (2)O32—C32—C33125.9 (3)
N1—C4—C386.13 (17)O31—C32—C33111.8 (2)
C41—C4—C3117.25 (19)C32—C33—H331109.5
N1—C4—H4112.1C32—C33—H332109.5
C41—C4—H4112.1H331—C33—H332109.5
C3—C4—H4112.1C32—C33—H333109.5
C16—C11—C12120.0 (2)H331—C33—H333109.5
C16—C11—N1119.9 (2)H332—C33—H333109.5
C12—C11—N1120.1 (2)C42—C41—O45110.3 (2)
C11—C12—C13119.3 (3)C42—C41—C4132.4 (2)
C11—C12—H12120.4O45—C41—C4117.2 (2)
C13—C12—H12120.4C41—C42—C43106.3 (3)
C14—C13—C12120.7 (3)C41—C42—H42126.8
C14—C13—H13119.6C43—C42—H42126.8
C12—C13—H13119.6C44—C43—C42106.7 (3)
C13—C14—O14116.0 (3)C44—C43—H43126.7
C13—C14—C15119.9 (2)C42—C43—H43126.7
O14—C14—C15124.0 (3)C43—C44—O45110.4 (3)
C14—O14—C141118.8 (3)C43—C44—H44124.8
O14—C141—H141109.5O45—C44—H44124.8
O14—C141—H142109.5C41—O45—C44106.2 (3)
 

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