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In the title compound, C10H15NO3, the central six-membered ring has a chair conformation. The conformations of the fused furan and oxopyrrolidine rings are close to envelopes. Molecules form chains parallel to the b axis, via O—H...O intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027515/rz6013sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027515/rz6013Isup2.hkl
Contains datablock I

CCDC reference: 259108

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.067
  • wR factor = 0.166
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 33.00 From the CIF: _reflns_number_total 1748 Count of symmetry unique reflns 1834 Completeness (_total/calc) 95.31% 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 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 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 (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(3aS,8aS,9R,9aS)-9-Hydroxy-2,3,3a,7,8,8a,9,9a-octahydrofuro[3,2-f]indolizin- 6(4H)-one top
Crystal data top
C10H15NO3F(000) = 212
Mr = 197.23Dx = 1.410 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3686 reflections
a = 5.3003 (3) Åθ = 2.4–33.0°
b = 10.3540 (5) ŵ = 0.10 mm1
c = 8.5137 (4) ÅT = 183 K
β = 96.127 (1)°Thin plate, colourless
V = 464.56 (4) Å30.35 × 0.12 × 0.02 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
1748 independent reflections
Radiation source: fine-focus sealed tube1377 reflections with F2 > 2σ(F2)
Graphite monochromatorRint = 0.085
ω scansθmax = 33.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 87
Tmin = 0.965, Tmax = 0.998k = 1515
7003 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.088P)2 + 0.2047P]
where P = (Fo2 + 2Fc2)/3
1748 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.47 e Å3
1 restraintΔρmin = 0.39 e Å3
Special details top

Experimental. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped with a Siemens LT-2 A low temperature device. A sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). Exposure time was 30 sec per frame. The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 3686 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2002) based on the multiscan method of Blessing (Blessing, R. H. (1995). Acta Cryst. A51, 33–38). The structure was solved by direct method (Bruker, 1997) and refined by full-matrix least squares on all F2 data using SHELXL97 (Sheldrick, 1997).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2012 (5)0.0583 (2)0.4452 (3)0.0317 (6)
C20.4231 (7)0.1246 (4)0.5192 (4)0.0288 (7)
H2A0.57930.08370.48830.035*
H2B0.42730.12060.63560.035*
C30.4068 (7)0.2650 (3)0.4634 (4)0.0237 (6)
H3A0.51930.28080.37980.028*
H3B0.45240.32530.55210.028*
C40.0601 (6)0.3882 (3)0.2801 (4)0.0196 (6)
H4A0.12190.41030.27830.024*
H4B0.16050.46600.31340.024*
N50.1140 (5)0.3497 (2)0.1211 (3)0.0178 (5)
C60.2926 (6)0.4018 (3)0.0411 (3)0.0180 (6)
C70.3042 (6)0.3250 (3)0.1108 (4)0.0230 (6)
H7A0.46970.28070.11050.028*
H7B0.27880.38230.20430.028*
C80.0876 (7)0.2267 (3)0.1118 (4)0.0257 (7)
H8A0.14480.13990.14140.031*
H8B0.05850.25290.18730.031*
C90.1393 (6)0.1203 (3)0.1656 (4)0.0218 (6)
H90.07320.03450.12630.026*
C100.0657 (6)0.1427 (3)0.3336 (4)0.0222 (6)
H100.12020.12630.33370.027*
C110.1259 (6)0.2791 (3)0.3987 (4)0.0206 (6)
H110.02610.29300.49050.025*
C120.0152 (6)0.2271 (3)0.0592 (4)0.0197 (6)
H120.17350.22440.05890.024*
O130.4067 (4)0.1229 (2)0.1648 (3)0.0228 (5)
H130.432 (8)0.100 (5)0.072 (5)0.023 (10)*
O140.4247 (5)0.4971 (2)0.0825 (3)0.0267 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0407 (15)0.0137 (11)0.0405 (14)0.0040 (10)0.0039 (11)0.0100 (10)
C20.0329 (18)0.0242 (15)0.0295 (16)0.0098 (15)0.0045 (13)0.0082 (13)
C30.0276 (16)0.0213 (14)0.0220 (14)0.0038 (13)0.0017 (11)0.0000 (11)
C40.0237 (15)0.0118 (11)0.0236 (13)0.0015 (11)0.0035 (11)0.0011 (10)
N50.0200 (12)0.0113 (10)0.0223 (11)0.0001 (9)0.0031 (9)0.0011 (8)
C60.0199 (14)0.0109 (11)0.0229 (13)0.0008 (10)0.0009 (10)0.0022 (10)
C70.0231 (15)0.0231 (15)0.0231 (14)0.0005 (12)0.0047 (11)0.0004 (11)
C80.0279 (17)0.0217 (14)0.0272 (16)0.0019 (13)0.0017 (13)0.0054 (12)
C90.0232 (15)0.0096 (11)0.0324 (15)0.0023 (11)0.0019 (12)0.0028 (11)
C100.0240 (15)0.0119 (13)0.0315 (15)0.0010 (11)0.0063 (12)0.0049 (11)
C110.0237 (15)0.0149 (13)0.0240 (14)0.0001 (11)0.0068 (11)0.0014 (10)
C120.0175 (13)0.0134 (12)0.0273 (15)0.0016 (11)0.0011 (11)0.0026 (11)
O130.0234 (11)0.0148 (10)0.0305 (12)0.0018 (9)0.0035 (9)0.0039 (9)
O140.0358 (14)0.0143 (10)0.0304 (12)0.0111 (10)0.0050 (10)0.0020 (9)
Geometric parameters (Å, º) top
O1—C101.427 (4)C7—C81.533 (5)
O1—C21.446 (5)C7—H7A0.9900
C2—C31.529 (5)C7—H7B0.9900
C2—H2A0.9900C8—C121.545 (5)
C2—H2B0.9900C8—H8A0.9900
C3—C111.538 (5)C8—H8B0.9900
C3—H3A0.9900C9—O131.418 (4)
C3—H3B0.9900C9—C121.533 (4)
C4—N51.468 (4)C9—C101.540 (5)
C4—C111.531 (4)C9—H91.0000
C4—H4A0.9900C10—C111.538 (4)
C4—H4B0.9900C10—H101.0000
N5—C61.338 (4)C11—H111.0000
N5—C121.451 (4)C12—H121.0000
C6—O141.239 (4)O13—H130.85 (5)
C6—C71.524 (4)
C10—O1—C2109.1 (2)C7—C8—C12104.7 (3)
O1—C2—C3107.4 (3)C7—C8—H8A110.8
O1—C2—H2A110.2C12—C8—H8A110.8
C3—C2—H2A110.2C7—C8—H8B110.8
O1—C2—H2B110.2C12—C8—H8B110.8
C3—C2—H2B110.2H8A—C8—H8B108.9
H2A—C2—H2B108.5O13—C9—C12110.5 (2)
C2—C3—C11102.8 (3)O13—C9—C10110.7 (3)
C2—C3—H3A111.2C12—C9—C10107.8 (2)
C11—C3—H3A111.2O13—C9—H9109.3
C2—C3—H3B111.2C12—C9—H9109.3
C11—C3—H3B111.2C10—C9—H9109.3
H3A—C3—H3B109.1O1—C10—C11104.6 (3)
N5—C4—C11110.8 (2)O1—C10—C9111.5 (3)
N5—C4—H4A109.5C11—C10—C9114.2 (3)
C11—C4—H4A109.5O1—C10—H10108.8
N5—C4—H4B109.5C11—C10—H10108.8
C11—C4—H4B109.5C9—C10—H10108.8
H4A—C4—H4B108.1C4—C11—C10114.6 (3)
C6—N5—C12114.5 (3)C4—C11—C3116.7 (3)
C6—N5—C4125.3 (3)C10—C11—C3101.4 (3)
C12—N5—C4118.3 (3)C4—C11—H11107.9
O14—C6—N5125.8 (3)C10—C11—H11107.9
O14—C6—C7125.7 (3)C3—C11—H11107.9
N5—C6—C7108.4 (3)N5—C12—C9107.5 (2)
C6—C7—C8104.7 (3)N5—C12—C8103.2 (2)
C6—C7—H7A110.8C9—C12—C8114.9 (3)
C8—C7—H7A110.8N5—C12—H12110.3
C6—C7—H7B110.8C9—C12—H12110.3
C8—C7—H7B110.8C8—C12—H12110.3
H7A—C7—H7B108.9C9—O13—H13105 (3)
C10—O1—C2—C37.0 (4)N5—C4—C11—C380.9 (3)
O1—C2—C3—C1117.3 (3)O1—C10—C11—C4164.9 (3)
C11—C4—N5—C6113.5 (3)C9—C10—C11—C442.7 (4)
C11—C4—N5—C1250.2 (4)O1—C10—C11—C338.2 (3)
C12—N5—C6—O14170.8 (3)C9—C10—C11—C383.9 (3)
C4—N5—C6—O146.6 (5)C2—C3—C11—C4158.1 (3)
C12—N5—C6—C79.9 (3)C2—C3—C11—C1032.9 (3)
C4—N5—C6—C7174.1 (3)C6—N5—C12—C9102.2 (3)
O14—C6—C7—C8174.9 (3)C4—N5—C12—C963.2 (3)
N5—C6—C7—C84.5 (3)C6—N5—C12—C819.6 (3)
C6—C7—C8—C1215.5 (3)C4—N5—C12—C8175.0 (3)
C2—O1—C10—C1128.6 (3)O13—C9—C12—N560.3 (3)
C2—O1—C10—C995.2 (3)C10—C9—C12—N560.8 (3)
O13—C9—C10—O151.0 (3)O13—C9—C12—C853.9 (3)
C12—C9—C10—O1172.0 (3)C10—C9—C12—C8175.0 (3)
O13—C9—C10—C1167.3 (3)C7—C8—C12—N520.5 (3)
C12—C9—C10—C1153.7 (3)C7—C8—C12—C996.2 (3)
N5—C4—C11—C1037.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O14i0.85 (5)1.92 (5)2.708 (3)155 (4)
C3—H3A···O130.992.482.937 (4)108
C4—H4B···O140.992.552.920 (4)102
Symmetry code: (i) x+1, y1/2, z.
 

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