In the title compound, C
10H
15NO
3, 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
CCDC reference: 259108
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (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
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,9
R,9aS)-9-Hydroxy-2,3,3a,7,8,8a,9,9a-octahydrofuro[3,2-
f]indolizin- 6(4
H)-one
top
Crystal data top
C10H15NO3 | F(000) = 212 |
Mr = 197.23 | Dx = 1.410 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 3686 reflections |
a = 5.3003 (3) Å | θ = 2.4–33.0° |
b = 10.3540 (5) Å | µ = 0.10 mm−1 |
c = 8.5137 (4) Å | T = 183 K |
β = 96.127 (1)° | Thin plate, colourless |
V = 464.56 (4) Å3 | 0.35 × 0.12 × 0.02 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1748 independent reflections |
Radiation source: fine-focus sealed tube | 1377 reflections with F2 > 2σ(F2) |
Graphite monochromator | Rint = 0.085 |
ω scans | θmax = 33.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −8→7 |
Tmin = 0.965, Tmax = 0.998 | k = −15→15 |
7003 measured reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H 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 parameters | Δρmax = 0.47 e Å−3 |
1 restraint | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2012 (5) | 0.0583 (2) | 0.4452 (3) | 0.0317 (6) | |
C2 | 0.4231 (7) | 0.1246 (4) | 0.5192 (4) | 0.0288 (7) | |
H2A | 0.5793 | 0.0837 | 0.4883 | 0.035* | |
H2B | 0.4273 | 0.1206 | 0.6356 | 0.035* | |
C3 | 0.4068 (7) | 0.2650 (3) | 0.4634 (4) | 0.0237 (6) | |
H3A | 0.5193 | 0.2808 | 0.3798 | 0.028* | |
H3B | 0.4524 | 0.3253 | 0.5521 | 0.028* | |
C4 | 0.0601 (6) | 0.3882 (3) | 0.2801 (4) | 0.0196 (6) | |
H4A | −0.1219 | 0.4103 | 0.2783 | 0.024* | |
H4B | 0.1605 | 0.4660 | 0.3134 | 0.024* | |
N5 | 0.1140 (5) | 0.3497 (2) | 0.1211 (3) | 0.0178 (5) | |
C6 | 0.2926 (6) | 0.4018 (3) | 0.0411 (3) | 0.0180 (6) | |
C7 | 0.3042 (6) | 0.3250 (3) | −0.1108 (4) | 0.0230 (6) | |
H7A | 0.4697 | 0.2807 | −0.1105 | 0.028* | |
H7B | 0.2788 | 0.3823 | −0.2043 | 0.028* | |
C8 | 0.0876 (7) | 0.2267 (3) | −0.1118 (4) | 0.0257 (7) | |
H8A | 0.1448 | 0.1399 | −0.1414 | 0.031* | |
H8B | −0.0585 | 0.2529 | −0.1873 | 0.031* | |
C9 | 0.1393 (6) | 0.1203 (3) | 0.1656 (4) | 0.0218 (6) | |
H9 | 0.0732 | 0.0345 | 0.1263 | 0.026* | |
C10 | 0.0657 (6) | 0.1427 (3) | 0.3336 (4) | 0.0222 (6) | |
H10 | −0.1202 | 0.1263 | 0.3337 | 0.027* | |
C11 | 0.1259 (6) | 0.2791 (3) | 0.3987 (4) | 0.0206 (6) | |
H11 | 0.0261 | 0.2930 | 0.4905 | 0.025* | |
C12 | 0.0152 (6) | 0.2271 (3) | 0.0592 (4) | 0.0197 (6) | |
H12 | −0.1735 | 0.2244 | 0.0589 | 0.024* | |
O13 | 0.4067 (4) | 0.1229 (2) | 0.1648 (3) | 0.0228 (5) | |
H13 | 0.432 (8) | 0.100 (5) | 0.072 (5) | 0.023 (10)* | |
O14 | 0.4247 (5) | 0.4971 (2) | 0.0825 (3) | 0.0267 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0407 (15) | 0.0137 (11) | 0.0405 (14) | 0.0040 (10) | 0.0039 (11) | 0.0100 (10) |
C2 | 0.0329 (18) | 0.0242 (15) | 0.0295 (16) | 0.0098 (15) | 0.0045 (13) | 0.0082 (13) |
C3 | 0.0276 (16) | 0.0213 (14) | 0.0220 (14) | 0.0038 (13) | 0.0017 (11) | 0.0000 (11) |
C4 | 0.0237 (15) | 0.0118 (11) | 0.0236 (13) | 0.0015 (11) | 0.0035 (11) | −0.0011 (10) |
N5 | 0.0200 (12) | 0.0113 (10) | 0.0223 (11) | 0.0001 (9) | 0.0031 (9) | −0.0011 (8) |
C6 | 0.0199 (14) | 0.0109 (11) | 0.0229 (13) | −0.0008 (10) | 0.0009 (10) | 0.0022 (10) |
C7 | 0.0231 (15) | 0.0231 (15) | 0.0231 (14) | 0.0005 (12) | 0.0047 (11) | −0.0004 (11) |
C8 | 0.0279 (17) | 0.0217 (14) | 0.0272 (16) | −0.0019 (13) | 0.0017 (13) | −0.0054 (12) |
C9 | 0.0232 (15) | 0.0096 (11) | 0.0324 (15) | −0.0023 (11) | 0.0019 (12) | −0.0028 (11) |
C10 | 0.0240 (15) | 0.0119 (13) | 0.0315 (15) | 0.0010 (11) | 0.0063 (12) | 0.0049 (11) |
C11 | 0.0237 (15) | 0.0149 (13) | 0.0240 (14) | 0.0001 (11) | 0.0068 (11) | 0.0014 (10) |
C12 | 0.0175 (13) | 0.0134 (12) | 0.0273 (15) | −0.0016 (11) | −0.0011 (11) | −0.0026 (11) |
O13 | 0.0234 (11) | 0.0148 (10) | 0.0305 (12) | 0.0018 (9) | 0.0035 (9) | −0.0039 (9) |
O14 | 0.0358 (14) | 0.0143 (10) | 0.0304 (12) | −0.0111 (10) | 0.0050 (10) | 0.0020 (9) |
Geometric parameters (Å, º) top
O1—C10 | 1.427 (4) | C7—C8 | 1.533 (5) |
O1—C2 | 1.446 (5) | C7—H7A | 0.9900 |
C2—C3 | 1.529 (5) | C7—H7B | 0.9900 |
C2—H2A | 0.9900 | C8—C12 | 1.545 (5) |
C2—H2B | 0.9900 | C8—H8A | 0.9900 |
C3—C11 | 1.538 (5) | C8—H8B | 0.9900 |
C3—H3A | 0.9900 | C9—O13 | 1.418 (4) |
C3—H3B | 0.9900 | C9—C12 | 1.533 (4) |
C4—N5 | 1.468 (4) | C9—C10 | 1.540 (5) |
C4—C11 | 1.531 (4) | C9—H9 | 1.0000 |
C4—H4A | 0.9900 | C10—C11 | 1.538 (4) |
C4—H4B | 0.9900 | C10—H10 | 1.0000 |
N5—C6 | 1.338 (4) | C11—H11 | 1.0000 |
N5—C12 | 1.451 (4) | C12—H12 | 1.0000 |
C6—O14 | 1.239 (4) | O13—H13 | 0.85 (5) |
C6—C7 | 1.524 (4) | | |
| | | |
C10—O1—C2 | 109.1 (2) | C7—C8—C12 | 104.7 (3) |
O1—C2—C3 | 107.4 (3) | C7—C8—H8A | 110.8 |
O1—C2—H2A | 110.2 | C12—C8—H8A | 110.8 |
C3—C2—H2A | 110.2 | C7—C8—H8B | 110.8 |
O1—C2—H2B | 110.2 | C12—C8—H8B | 110.8 |
C3—C2—H2B | 110.2 | H8A—C8—H8B | 108.9 |
H2A—C2—H2B | 108.5 | O13—C9—C12 | 110.5 (2) |
C2—C3—C11 | 102.8 (3) | O13—C9—C10 | 110.7 (3) |
C2—C3—H3A | 111.2 | C12—C9—C10 | 107.8 (2) |
C11—C3—H3A | 111.2 | O13—C9—H9 | 109.3 |
C2—C3—H3B | 111.2 | C12—C9—H9 | 109.3 |
C11—C3—H3B | 111.2 | C10—C9—H9 | 109.3 |
H3A—C3—H3B | 109.1 | O1—C10—C11 | 104.6 (3) |
N5—C4—C11 | 110.8 (2) | O1—C10—C9 | 111.5 (3) |
N5—C4—H4A | 109.5 | C11—C10—C9 | 114.2 (3) |
C11—C4—H4A | 109.5 | O1—C10—H10 | 108.8 |
N5—C4—H4B | 109.5 | C11—C10—H10 | 108.8 |
C11—C4—H4B | 109.5 | C9—C10—H10 | 108.8 |
H4A—C4—H4B | 108.1 | C4—C11—C10 | 114.6 (3) |
C6—N5—C12 | 114.5 (3) | C4—C11—C3 | 116.7 (3) |
C6—N5—C4 | 125.3 (3) | C10—C11—C3 | 101.4 (3) |
C12—N5—C4 | 118.3 (3) | C4—C11—H11 | 107.9 |
O14—C6—N5 | 125.8 (3) | C10—C11—H11 | 107.9 |
O14—C6—C7 | 125.7 (3) | C3—C11—H11 | 107.9 |
N5—C6—C7 | 108.4 (3) | N5—C12—C9 | 107.5 (2) |
C6—C7—C8 | 104.7 (3) | N5—C12—C8 | 103.2 (2) |
C6—C7—H7A | 110.8 | C9—C12—C8 | 114.9 (3) |
C8—C7—H7A | 110.8 | N5—C12—H12 | 110.3 |
C6—C7—H7B | 110.8 | C9—C12—H12 | 110.3 |
C8—C7—H7B | 110.8 | C8—C12—H12 | 110.3 |
H7A—C7—H7B | 108.9 | C9—O13—H13 | 105 (3) |
| | | |
C10—O1—C2—C3 | 7.0 (4) | N5—C4—C11—C3 | 80.9 (3) |
O1—C2—C3—C11 | 17.3 (3) | O1—C10—C11—C4 | 164.9 (3) |
C11—C4—N5—C6 | −113.5 (3) | C9—C10—C11—C4 | 42.7 (4) |
C11—C4—N5—C12 | 50.2 (4) | O1—C10—C11—C3 | 38.2 (3) |
C12—N5—C6—O14 | −170.8 (3) | C9—C10—C11—C3 | −83.9 (3) |
C4—N5—C6—O14 | −6.6 (5) | C2—C3—C11—C4 | −158.1 (3) |
C12—N5—C6—C7 | 9.9 (3) | C2—C3—C11—C10 | −32.9 (3) |
C4—N5—C6—C7 | 174.1 (3) | C6—N5—C12—C9 | 102.2 (3) |
O14—C6—C7—C8 | −174.9 (3) | C4—N5—C12—C9 | −63.2 (3) |
N5—C6—C7—C8 | 4.5 (3) | C6—N5—C12—C8 | −19.6 (3) |
C6—C7—C8—C12 | −15.5 (3) | C4—N5—C12—C8 | 175.0 (3) |
C2—O1—C10—C11 | −28.6 (3) | O13—C9—C12—N5 | −60.3 (3) |
C2—O1—C10—C9 | 95.2 (3) | C10—C9—C12—N5 | 60.8 (3) |
O13—C9—C10—O1 | −51.0 (3) | O13—C9—C12—C8 | 53.9 (3) |
C12—C9—C10—O1 | −172.0 (3) | C10—C9—C12—C8 | 175.0 (3) |
O13—C9—C10—C11 | 67.3 (3) | C7—C8—C12—N5 | 20.5 (3) |
C12—C9—C10—C11 | −53.7 (3) | C7—C8—C12—C9 | −96.2 (3) |
N5—C4—C11—C10 | −37.3 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O14i | 0.85 (5) | 1.92 (5) | 2.708 (3) | 155 (4) |
C3—H3A···O13 | 0.99 | 2.48 | 2.937 (4) | 108 |
C4—H4B···O14 | 0.99 | 2.55 | 2.920 (4) | 102 |
Symmetry code: (i) −x+1, y−1/2, −z. |