2,4,4a,5,6,7,9,9a-Octa­hydro­furo­[2,3-f]­indolizin-7-one

In the title compound, C₁₀H₁₃NO₂, the conformation of the oxopyrrolidine ring is close to that of an envelope. The central six-membered ring has a chair conformation. The nearly planar furan ring attached to the indolizine ring system is slightly buckled, with a mean deviation of 0.037 Å.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.115
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.094
            Value of mu given      =     0.090
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT032_ALERT_4_C Std Uncertainty in Flack Parameter too High ....      10.00
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C7
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..      10.00

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           32.90
           From the CIF: _reflns_number_total               1854
           Count of symmetry unique reflns         1902
           Completeness (_total/calc)             97.48%
           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
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995) and SADABS (Sheldrick, 2002); program(s) used to solve structure: Bruker, SHELXTL; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXS97.

2,4,4a,5,6,7,9,9a-Octahydrofuro[2,3-f]indolizin-7-one

Crystal data

C10H13NO2	Dx = 1.345 Mg m^−3
Mr = 179.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8192 reflections
a = 6.6561 (2) Å	θ = 3.5–31.3°
b = 11.1986 (3) Å	µ = 0.09 mm^−1
c = 11.8739 (3) Å	T = 183 K
V = 885.07 (4) Å^3	Block, colorless
Z = 4	0.26 × 0.25 × 0.10 mm
F(000) = 384

Data collection

Siemens SMART CCD diffractometer	1854 independent reflections
Radiation source: fine-focus sealed tube	1611 reflections with F^2 > 2σ(F^2)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 32.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
Tmin = 0.976, Tmax = 0.991	k = −17→17
15853 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0663P)^2 + 0.14P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.010
1854 reflections	Δρmax = 0.29 e Å^−3
118 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Special details

Refinement. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped witha 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 20 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 8192 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 (1995). 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.39618 (18)	0.75038 (11)	0.11274 (10)	0.0327 (3)
C2	0.2399 (3)	0.66340 (17)	0.09652 (14)	0.0327 (3)
H2A	0.2503	0.6266	0.0209	0.039*
H2B	0.1058	0.7009	0.1041	0.039*
C3	0.2716 (2)	0.57184 (14)	0.18662 (14)	0.0301 (3)
H3	0.1990	0.4992	0.1932	0.036*
C4	0.4170 (2)	0.60737 (13)	0.25620 (12)	0.0254 (3)
C5	0.5189 (3)	0.54894 (13)	0.35435 (13)	0.0285 (3)
H5A	0.4660	0.4671	0.3650	0.034*
H5B	0.4932	0.5952	0.4239	0.034*
C6	0.7460 (3)	0.54432 (14)	0.33031 (15)	0.0312 (3)
H6	0.7733	0.4854	0.2689	0.037*
C7	0.8790 (4)	0.51595 (19)	0.4326 (2)	0.0543 (6)
H7A	0.7971	0.4830	0.4949	0.065*
H7B	0.9836	0.4569	0.4123	0.065*
C8	0.9739 (3)	0.63293 (17)	0.46703 (15)	0.0397 (4)
H8A	1.1192	0.6222	0.4816	0.048*
H8B	0.9095	0.6643	0.5361	0.048*
C9	0.9409 (2)	0.71731 (14)	0.36935 (13)	0.0283 (3)
N10	0.8156 (2)	0.66315 (12)	0.29566 (12)	0.0292 (3)
C11	0.7250 (2)	0.72000 (14)	0.19825 (13)	0.0277 (3)
H11A	0.7551	0.6733	0.1295	0.033*
H11B	0.7804	0.8014	0.1886	0.033*
C12	0.4967 (2)	0.72641 (13)	0.21673 (12)	0.0252 (3)
H12	0.4640	0.7898	0.2731	0.030*
O13	1.0101 (2)	0.81856 (11)	0.35866 (12)	0.0405 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0304 (5)	0.0366 (6)	0.0311 (5)	−0.0048 (5)	−0.0075 (5)	0.0099 (5)
C2	0.0237 (7)	0.0409 (8)	0.0336 (7)	−0.0018 (7)	−0.0036 (6)	0.0028 (7)
C3	0.0261 (7)	0.0306 (7)	0.0336 (7)	−0.0025 (6)	0.0009 (6)	0.0003 (6)
C4	0.0258 (6)	0.0239 (6)	0.0265 (6)	0.0000 (5)	0.0030 (5)	0.0005 (5)
C5	0.0348 (8)	0.0218 (6)	0.0289 (7)	−0.0016 (6)	−0.0001 (6)	0.0035 (5)
C6	0.0338 (8)	0.0219 (6)	0.0380 (8)	−0.0007 (6)	−0.0077 (7)	0.0038 (6)
C7	0.0543 (12)	0.0394 (10)	0.0693 (14)	−0.0067 (9)	−0.0313 (11)	0.0219 (10)
C8	0.0494 (11)	0.0383 (9)	0.0314 (7)	0.0006 (8)	−0.0111 (8)	0.0015 (6)
C9	0.0281 (7)	0.0273 (6)	0.0296 (7)	0.0015 (5)	−0.0025 (6)	−0.0031 (6)
N10	0.0290 (6)	0.0240 (5)	0.0346 (7)	−0.0020 (5)	−0.0081 (5)	0.0043 (5)
C11	0.0275 (7)	0.0284 (7)	0.0272 (6)	−0.0030 (6)	−0.0028 (6)	0.0029 (6)
C12	0.0286 (6)	0.0230 (6)	0.0239 (6)	0.0008 (5)	−0.0015 (5)	0.0014 (5)
O13	0.0444 (7)	0.0295 (6)	0.0476 (7)	−0.0074 (5)	−0.0121 (6)	−0.0015 (5)

Geometric parameters (Å, º)

O1—C12	1.4296 (18)	C6—H6	1.0000
O1—C2	1.438 (2)	C7—C8	1.511 (3)
C2—C3	1.497 (2)	C7—H7A	0.9900
C2—H2A	0.9900	C7—H7B	0.9900
C2—H2B	0.9900	C8—C9	1.512 (2)
C3—C4	1.333 (2)	C8—H8A	0.9900
C3—H3	0.9500	C8—H8B	0.9900
C4—C5	1.499 (2)	C9—O13	1.230 (2)
C4—C12	1.509 (2)	C9—N10	1.353 (2)
C5—C6	1.539 (2)	N10—C11	1.451 (2)
C5—H5A	0.9900	C11—C12	1.538 (2)
C5—H5B	0.9900	C11—H11A	0.9900
C6—N10	1.468 (2)	C11—H11B	0.9900
C6—C7	1.536 (3)	C12—H12	1.0000
C12—O1—C2	109.09 (11)	C8—C7—H7B	110.5
O1—C2—C3	105.43 (13)	C6—C7—H7B	110.5
O1—C2—H2A	110.7	H7A—C7—H7B	108.7
C3—C2—H2A	110.7	C7—C8—C9	105.88 (15)
O1—C2—H2B	110.7	C7—C8—H8A	110.6
C3—C2—H2B	110.7	C9—C8—H8A	110.6
H2A—C2—H2B	108.8	C7—C8—H8B	110.6
C4—C3—C2	109.94 (14)	C9—C8—H8B	110.6
C4—C3—H3	125.0	H8A—C8—H8B	108.7
C2—C3—H3	125.0	O13—C9—N10	125.26 (15)
C3—C4—C5	132.86 (14)	O13—C9—C8	126.93 (15)
C3—C4—C12	109.04 (13)	N10—C9—C8	107.78 (14)
C5—C4—C12	117.89 (13)	C9—N10—C11	125.09 (13)
C4—C5—C6	108.37 (13)	C9—N10—C6	114.81 (13)
C4—C5—H5A	110.0	C11—N10—C6	119.36 (13)
C6—C5—H5A	110.0	N10—C11—C12	108.50 (12)
C4—C5—H5B	110.0	N10—C11—H11A	110.0
C6—C5—H5B	110.0	C12—C11—H11A	110.0
H5A—C5—H5B	108.4	N10—C11—H11B	110.0
N10—C6—C7	103.16 (14)	C12—C11—H11B	110.0
N10—C6—C5	109.34 (13)	H11A—C11—H11B	108.4
C7—C6—C5	115.22 (17)	O1—C12—C4	105.64 (12)
N10—C6—H6	109.6	O1—C12—C11	110.37 (12)
C7—C6—H6	109.6	C4—C12—C11	110.53 (13)
C5—C6—H6	109.6	O1—C12—H12	110.1
C8—C7—C6	106.00 (14)	C4—C12—H12	110.1
C8—C7—H7A	110.5	C11—C12—H12	110.1
C6—C7—H7A	110.5
C12—O1—C2—C3	−9.32 (17)	C8—C9—N10—C6	1.2 (2)
O1—C2—C3—C4	6.16 (19)	C7—C6—N10—C9	−10.3 (2)
C2—C3—C4—C5	−175.19 (16)	C5—C6—N10—C9	112.80 (16)
C2—C3—C4—C12	−0.70 (18)	C7—C6—N10—C11	179.03 (17)
C3—C4—C5—C6	122.46 (19)	C5—C6—N10—C11	−57.90 (19)
C12—C4—C5—C6	−51.64 (18)	C9—N10—C11—C12	−113.89 (17)
C4—C5—C6—N10	50.02 (17)	C6—N10—C11—C12	55.77 (19)
C4—C5—C6—C7	165.62 (14)	C2—O1—C12—C4	8.94 (16)
N10—C6—C7—C8	14.8 (2)	C2—O1—C12—C11	128.43 (14)
C5—C6—C7—C8	−104.2 (2)	C3—C4—C12—O1	−5.06 (17)
C6—C7—C8—C9	−14.6 (2)	C5—C4—C12—O1	170.37 (13)
C7—C8—C9—O13	−173.1 (2)	C3—C4—C12—C11	−124.44 (15)
C7—C8—C9—N10	8.7 (2)	C5—C4—C12—C11	50.99 (17)
O13—C9—N10—C11	−7.0 (3)	N10—C11—C12—O1	−163.97 (12)
C8—C9—N10—C11	171.29 (15)	N10—C11—C12—C4	−47.48 (16)
O13—C9—N10—C6	−177.09 (17)