(3aR,4R,4aS,9aR)-4-Hydroxy­perhydro­furo[2,3-f]indolizin-7(2H)-one

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 a axis via O—H...O inter­molecular hydrogen bonds, which help to stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.091
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H15 N O3

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           29.04
           From the CIF: _reflns_number_total               1491
           Count of symmetry unique reflns         1547
           Completeness (_total/calc)             96.38%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97.

(3aR,4R,4aS,9aR)-4-Hydroxyperhydrofuro[2,3-f]indolizin-7(2H)-one

Crystal data

C10H15NO3	F(000) = 424
Mr = 197.23	Dx = 1.311 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8947 reflections
a = 8.3423 (2) Å	θ = 3.4–28.9°
b = 8.6807 (2) Å	µ = 0.10 mm^−1
c = 13.7985 (3) Å	T = 293 K
V = 999.25 (4) Å^3	Prism, colourless
Z = 4	0.6 × 0.5 × 0.4 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	1491 independent reflections
Radiation source: fine-focus sealed tube	935 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.4340 pixels mm^-1	θmax = 29.0°, θmin = 3.4°
Rotation method data acquisition using ω and φ scans	h = −10→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002)	k = −11→11
Tmin = 0.955, Tmax = 0.971	l = −18→18
23008 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0546P)^2] where P = (Fo^2 + 2Fc^2)/3
1491 reflections	(Δ/σ)max = 0.001
132 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N8	−0.07367 (18)	−0.06371 (17)	−0.77831 (9)	0.0436 (4)
C10	0.2044 (2)	−0.0465 (2)	−0.83184 (14)	0.0501 (5)
H10	0.3080	−0.0965	−0.8204	0.060*
C4	−0.0277 (2)	−0.0551 (2)	−0.95070 (12)	0.0440 (4)
H4	−0.0449	0.0565	−0.9539	0.053*
C7	−0.1879 (2)	−0.0192 (2)	−0.71723 (13)	0.0467 (5)
C11	0.1484 (2)	−0.0853 (2)	−0.93397 (13)	0.0459 (5)
H11	0.1737	−0.1929	−0.9491	0.055*
C12	−0.1320 (2)	−0.1208 (2)	−0.87143 (12)	0.0466 (5)
H12	−0.1264	−0.2335	−0.8726	0.056*
C9	0.0916 (2)	−0.0901 (2)	−0.75169 (12)	0.0504 (5)
H9A	0.1062	−0.1981	−0.7360	0.060*
H9B	0.1169	−0.0303	−0.6943	0.060*
C6	−0.3465 (3)	−0.0331 (3)	−0.76714 (14)	0.0634 (6)
H6A	−0.4061	0.0625	−0.7623	0.076*
H6B	−0.4097	−0.1152	−0.7386	0.076*
C5	−0.3072 (2)	−0.0691 (3)	−0.87200 (14)	0.0660 (6)
H5A	−0.3209	0.0215	−0.9123	0.079*
H5B	−0.3759	−0.1505	−0.8964	0.079*
C3	0.2539 (3)	0.0215 (3)	−0.99330 (15)	0.0676 (6)
H3A	0.3567	−0.0258	−1.0073	0.081*
H3B	0.2024	0.0496	−1.0538	0.081*
C2	0.2731 (3)	0.1598 (3)	−0.92791 (17)	0.0839 (8)
H2A	0.3837	0.1943	−0.9282	0.101*
H2B	0.2060	0.2437	−0.9506	0.101*
O3	−0.16378 (18)	0.02292 (17)	−0.63290 (9)	0.0625 (4)
O2	−0.06689 (19)	−0.12052 (18)	−1.04207 (9)	0.0644 (4)
H2	−0.167 (3)	−0.079 (3)	−1.0655 (19)	0.101 (9)*
O1	0.22707 (18)	0.11594 (17)	−0.83249 (11)	0.0709 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N8	0.0417 (9)	0.0588 (9)	0.0303 (7)	0.0001 (8)	−0.0024 (6)	−0.0046 (7)
C10	0.0427 (11)	0.0656 (13)	0.0422 (10)	0.0045 (10)	−0.0053 (9)	−0.0071 (10)
C4	0.0482 (11)	0.0538 (10)	0.0299 (8)	0.0082 (9)	−0.0042 (8)	−0.0022 (8)
C7	0.0523 (12)	0.0497 (10)	0.0381 (10)	−0.0040 (9)	0.0046 (9)	−0.0038 (8)
C11	0.0478 (11)	0.0548 (11)	0.0352 (9)	0.0086 (9)	0.0011 (9)	−0.0047 (9)
C12	0.0487 (11)	0.0566 (11)	0.0346 (9)	−0.0038 (10)	−0.0046 (8)	−0.0100 (8)
C9	0.0492 (12)	0.0673 (11)	0.0346 (9)	0.0061 (9)	−0.0095 (9)	−0.0031 (9)
C6	0.0478 (12)	0.0884 (15)	0.0540 (12)	−0.0010 (12)	0.0007 (10)	−0.0089 (12)
C5	0.0432 (12)	0.1051 (17)	0.0497 (12)	−0.0015 (11)	−0.0027 (9)	−0.0139 (12)
C3	0.0599 (14)	0.0910 (15)	0.0517 (12)	−0.0012 (13)	0.0129 (11)	−0.0033 (13)
C2	0.0955 (19)	0.0801 (15)	0.0761 (16)	−0.0249 (15)	0.0214 (16)	−0.0015 (14)
O3	0.0638 (9)	0.0850 (10)	0.0388 (7)	−0.0056 (8)	0.0088 (7)	−0.0159 (7)
O2	0.0633 (9)	0.0971 (11)	0.0328 (7)	0.0108 (9)	−0.0093 (7)	−0.0138 (7)
O1	0.0823 (10)	0.0694 (10)	0.0610 (9)	−0.0243 (8)	0.0105 (9)	−0.0170 (8)

Geometric parameters (Å, º)

N8—C7	1.330 (2)	C12—H12	0.9800
N8—C9	1.445 (2)	C9—H9A	0.9700
N8—C12	1.460 (2)	C9—H9B	0.9700
C10—O1	1.423 (3)	C6—C5	1.516 (3)
C10—C9	1.500 (3)	C6—H6A	0.9700
C10—C11	1.522 (3)	C6—H6B	0.9700
C10—H10	0.9800	C5—H5A	0.9700
C4—O2	1.421 (2)	C5—H5B	0.9700
C4—C12	1.510 (3)	C3—C2	1.511 (3)
C4—C11	1.510 (3)	C3—H3A	0.9700
C4—H4	0.9800	C3—H3B	0.9700
C7—O3	1.236 (2)	C2—O1	1.423 (3)
C7—C6	1.496 (3)	C2—H2A	0.9700
C11—C3	1.518 (3)	C2—H2B	0.9700
C11—H11	0.9800	O2—H2	0.97 (3)
C12—C5	1.529 (3)
C7—N8—C9	124.7 (2)	N8—C9—H9A	109.3
C7—N8—C12	114.7 (2)	C10—C9—H9A	109.3
C9—N8—C12	119.2 (2)	N8—C9—H9B	109.3
O1—C10—C9	109.8 (2)	C10—C9—H9B	109.3
O1—C10—C11	104.73 (17)	H9A—C9—H9B	107.9
C9—C10—C11	115.73 (16)	C7—C6—C5	105.35 (17)
O1—C10—H10	108.8	C7—C6—H6A	110.7
C9—C10—H10	108.8	C5—C6—H6A	110.7
C11—C10—H10	108.8	C7—C6—H6B	110.7
O2—C4—C12	111.1 (2)	C5—C6—H6B	110.7
O2—C4—C11	106.86 (16)	H6A—C6—H6B	108.8
C12—C4—C11	112.60 (15)	C6—C5—C12	105.21 (16)
O2—C4—H4	108.7	C6—C5—H5A	110.7
C12—C4—H4	108.7	C12—C5—H5A	110.7
C11—C4—H4	108.7	C6—C5—H5B	110.7
O3—C7—N8	124.5 (3)	C12—C5—H5B	110.7
O3—C7—C6	126.94 (18)	H5A—C5—H5B	108.8
N8—C7—C6	108.57 (15)	C2—C3—C11	103.00 (16)
C4—C11—C3	112.03 (16)	C2—C3—H3A	111.2
C4—C11—C10	113.7 (2)	C11—C3—H3A	111.2
C3—C11—C10	100.74 (16)	C2—C3—H3B	111.2
C4—C11—H11	110.0	C11—C3—H3B	111.2
C3—C11—H11	110.0	H3A—C3—H3B	109.1
C10—C11—H11	110.0	O1—C2—C3	108.13 (18)
N8—C12—C4	108.5 (2)	O1—C2—H2A	110.1
N8—C12—C5	102.91 (15)	C3—C2—H2A	110.1
C4—C12—C5	115.9 (2)	O1—C2—H2B	110.1
N8—C12—H12	109.8	C3—C2—H2B	110.1
C4—C12—H12	109.8	H2A—C2—H2B	108.4
C5—C12—H12	109.8	C4—O2—H2	110.4 (16)
N8—C9—C10	111.76 (14)	C10—O1—C2	107.9 (2)
C9—N8—C7—O3	9.1 (3)	O2—C4—C12—C5	−71.7 (2)
C12—N8—C7—O3	175.07 (17)	C11—C4—C12—C5	168.55 (17)
C9—N8—C7—C6	−169.49 (18)	C7—N8—C9—C10	−145.88 (18)
C12—N8—C7—C6	−3.5 (2)	C12—N8—C9—C10	48.7 (2)
O2—C4—C11—C3	76.3 (2)	O1—C10—C9—N8	79.6 (2)
C12—C4—C11—C3	−161.49 (15)	C11—C10—C9—N8	−38.6 (2)
O2—C4—C11—C10	−170.30 (15)	O3—C7—C6—C5	173.0 (2)
C12—C4—C11—C10	−48.1 (2)	N8—C7—C6—C5	−8.5 (2)
O1—C10—C11—C4	−80.50 (19)	C7—C6—C5—C12	16.2 (3)
C9—C10—C11—C4	40.5 (2)	N8—C12—C5—C6	−17.7 (2)
O1—C10—C11—C3	39.50 (18)	C4—C12—C5—C6	−135.9 (2)
C9—C10—C11—C3	160.47 (17)	C4—C11—C3—C2	88.2 (2)
C7—N8—C12—C4	136.99 (17)	C10—C11—C3—C2	−32.9 (2)
C9—N8—C12—C4	−56.2 (2)	C11—C3—C2—O1	16.3 (3)
C7—N8—C12—C5	13.7 (2)	C9—C10—O1—C2	−155.4 (2)
C9—N8—C12—C5	−179.50 (17)	C11—C10—O1—C2	−30.6 (2)
O2—C4—C12—N8	173.23 (15)	C3—C2—O1—C10	8.8 (3)
C11—C4—C12—N8	53.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3^i	0.97 (3)	1.76 (3)	2.709 (2)	167 (2)

Symmetry code: (i) −x−1/2, −y, z−1/2.