(1S,2E,6R,7aR)-2-Benzyl­idene-1,6-dihy­droxy-2,3,5,6,7,7a-hexa­hydro-1H-pyrrolizin-3-one

Oliveira, F.L.; Freire, K.R.L.; Aparicio, R.; Coelho, F.

doi:10.1107/S1600536812018223

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1572

doi:10.1107/S1600536812018223

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(1S,2E,6R,7aR)-2-Benzylidene-1,6-dihydroxy-2,3,5,6,7,7a-hexahydro-1H-pyrrolizin-3-one

F. L. Oliveira,^a K. R. L. Freire,^b R. Aparicio ^a ^* and F. Coelho ^b

^aLaboratory of Structural Biology and Crystallography, Institute of Chemistry, University of Campinas, CP6154, CEP13083-970, Campinas, SP, Brazil, and ^bLaboratory of Synthesis of Natural Products and Drugs, Institute of Chemistry, University of Campinas, CP6154, CEP13083-970, Campinas, SP, Brazil
^*Correspondence e-mail: aparicio@iqm.unicamp.br

(Received 17 March 2012; accepted 23 April 2012; online 28 April 2012)

In the title compound, C₁₄H₁₅NO₃, the conformation of the double bond was determined to be E, confirming the result obtained from two-dimensional NMR data. The five-membered rings of the pyrrolizine unit exhibit C-envelope conformations, with C atoms displaced from the mean planes formed by the remaining rings atoms by 0.1468 (15) and 0.5405 (17) Å. The mean planes of these rings (through all ring atoms) have a dihedral angle of 49.03 (10)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds. The absolute configuration of the molecule was established, as judged by the, as judged by the obtained values for the Hooft and Flack parameters.

Related literature

For the preparation of the title compound, see: Freire et al. (2011 ). For the use of this type of compound as LFA-1 (Lymphocyte Function-Associated Antigen-1) inhibitors, see: Baumann (2007 ). For related structures, see: Oliveira et al. (2012a ,b ).

Experimental

Crystal data

C₁₄H₁₅NO₃
M_r = 245.27
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.5007 (3) Å
b = 13.6783 (7) Å
c = 13.8382 (7) Å
V = 1230.47 (11) Å³
Z = 4
Cu Kα radiation
μ = 0.77 mm⁻¹
T = 100 K
0.31 × 0.13 × 0.13 mm

Data collection

Bruker Kappa APEXII DUO diffractometer
Absorption correction: numerical (SADABS; Bruker, 2010 ) T_min = 0.924, T_max = 1.000
32528 measured reflections
2219 independent reflections
2203 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.06
2219 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ) and Hooft et al. (2008 ); Hooft parameter = 0.01(2), 905 Bijvoet pairs
Flack parameter: 0.1 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.84	2.04	2.776 (2)	147
O3—H3⋯O2ⁱⁱ	0.84	1.85	2.6810 (17)	168
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018223/pv2526sup1.cif

Supporting information file. DOI: 10.1107/S1600536812018223/pv2526Isup2.cml

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018223/pv2526Isup3.hkl

checkCIF report

Comment top

The title compound (Fig. 1) is a new asymmetric benzyl-pyrrolizidinone which has been synthesized from a chiral Morita-Baylis-Hillman adduct. It belongs to a class of compounds with potential pharmacological properties as mediators of the LFA-1 (lymphocyte function-associated antigen 1) function, particularly as anti-inflammatory agents and for the treatment of autoimmune diseases (Baumann, 2007). It has three defined stereocenters and a double bond with E configuration. The five membered rings N1/C3/C2/C1/C7A and N1/C5/C6/C7/C7A of the pyrrolizine moiety exhibit C2- and C5-envelope conformations, respectively, with C2 and C5 atoms displaced from the mean-planes formed by the remaining rings atoms by 0.1468 (15) and 0.5405 (17) Å, respectively. The mean planes of these rings have a dihedral angle of 49.03 (10)°. The configuration of the double bond determined by X-ray crystallography confirms the two-dimensional-NOESY NMR analysis. The crystal structure is stabilized by intermolecular hydrogen bonds (Tab. 1 and Fig. 2).

Related literature top

For the preparation of the title compound, see: Freire et al. (2011). For the use of this type of compound as LFA-1 (Lymphocyte Function-Associated Antigen-1) inhibitors, see: Baumann (2007). For related structures, see: Oliveira et al. (2012a,b).

Experimental top

The title compound was prepared using a synthetic sequence previously described (Freire et al., 2011) and purified by flash silica gel column chromatography (CH₂Cl₂:MeOH – solvent gradient: 100:0 to 95:05) to afford 0.14 g (as a white solid) in 76% yield, followed by recrystallization using the liquid-vapor saturation method. Subsequently, it was dissolved in ethanol and crystallized under the vapor pressure of ethyl ether (a less polar liquid), in a closed camera, thus allowing for the slow formation of good diffracting crystals.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

(1S,2E,6R,7aR)-2-Benzylidene-1,6-dihydroxy- 2,3,5,6,7,7a-hexahydro-1H-pyrrolizin-3-one top

Crystal data top

C₁₄H₁₅NO₃	D_x = 1.324 Mg m⁻³
M_r = 245.27	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2219 reflections
a = 6.5007 (3) Å	θ = 4.6–68.1°
b = 13.6783 (7) Å	µ = 0.77 mm⁻¹
c = 13.8382 (7) Å	T = 100 K
V = 1230.47 (11) Å³	Rectangular, colourless
Z = 4	0.31 × 0.13 × 0.13 mm
F(000) = 520

Data collection top

Bruker Kappa APEXII DUO diffractometer	2219 independent reflections
Radiation source: fine-focus sealed tube	2203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Bruker APEX CCD area–detector scans	θ_max = 68.1°, θ_min = 4.6°
Absorption correction: numerical (SADABS; Bruker, 2010)	h = −7→5
T_min = 0.924, T_max = 1.000	k = −16→16
32528 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0574P)² + 0.2433P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2219 reflections	Δρ_max = 0.27 e Å⁻³
165 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983) and Hooft et al. (2008); Hooft parameter = 0.01(2), 905 Bijvoet pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (3)

Crystal data top

C₁₄H₁₅NO₃	V = 1230.47 (11) Å³
M_r = 245.27	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.5007 (3) Å	µ = 0.77 mm⁻¹
b = 13.6783 (7) Å	T = 100 K
c = 13.8382 (7) Å	0.31 × 0.13 × 0.13 mm

Data collection top

Bruker Kappa APEXII DUO diffractometer	2219 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2010)	2203 reflections with I > 2σ(I)
T_min = 0.924, T_max = 1.000	R_int = 0.034
32528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.098	Δρ_max = 0.27 e Å⁻³
S = 1.06	Δρ_min = −0.23 e Å⁻³
2219 reflections	Absolute structure: Flack (1983) and Hooft et al. (2008); Hooft parameter = 0.01(2), 905 Bijvoet pairs
165 parameters	Absolute structure parameter: 0.1 (3)
0 restraints

Special details top

Experimental. [α]D²⁰ + 40 (c 1, MeOH); IR (Film, ν_max): 3427, 3195, 2940, 2855, 1668, 1634, 1493, 1424, 1268, 1156, 1067 cm^-1; ¹H NMR (400 MHz, CD3CN) δ 1.30 (m, J = 13.8, 9.1, 5.4 Hz, 1H, H-14 A), 2.38 (m, J = 13.8, 6.8 Hz, 1H, H-14B), 3.27 (dd, J = 12.3, 6.1 Hz, 1H, H-2 A), 3.56 (dd, J = 12.3, 3.3 Hz, 1H, H-2B), 3.69 (ddd, J = 9.1, 7.4, 1.8 Hz, 1H, H-10), 4.47 (qd, J = 6.1, 3.3 Hz, 1H, H-1 A), 4.91 (dd, J = 1.8 Hz, 1H, H-11), 7.35 (d, J = 2.1 Hz, 1H, H-5), 7.41 (m, 3H, Ph), 7.79 (m, 2H, Ph); ¹³C NMR (62.5 MHz, (CD₃)₂CO) δ 38.1, 52.1, 68.2, 70.1, 72.0, 129.2, 130.3, 131.3, 134.1, 134.2, 137.1, 172.1; HRMS (ESI-TOF) Calcd. for C₁₄H₁₆NO₃ [M + H]⁺ 246.1130. Found 246.1168.

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

	x	y	z	U_iso*/U_eq
O1	0.2407 (3)	0.95636 (13)	0.17238 (19)	0.1020 (7)
H1	0.1725	1.0026	0.1962	0.153*
O2	0.52812 (19)	0.71064 (10)	0.18954 (10)	0.0546 (3)
O3	−0.14247 (18)	0.65007 (11)	0.28956 (12)	0.0615 (4)
H3	−0.2555	0.6653	0.2643	0.092*
N1	0.2098 (2)	0.75095 (9)	0.13314 (9)	0.0364 (3)
C6	0.1266 (3)	0.91174 (13)	0.09912 (14)	0.0478 (4)
H1A	0.0930	0.9587	0.0460	0.057*
C5	0.2537 (3)	0.82646 (13)	0.06255 (12)	0.0465 (4)
H2A	0.2099	0.8063	−0.0030	0.056*
H2B	0.4021	0.8428	0.0614	0.056*
C3	0.3405 (2)	0.71615 (11)	0.20026 (12)	0.0364 (3)
C2	0.2186 (2)	0.68831 (11)	0.28681 (11)	0.0336 (3)
C4	0.3095 (2)	0.64180 (11)	0.36077 (11)	0.0381 (3)
H5	0.4483	0.6237	0.3490	0.046*
C8	0.2326 (3)	0.61406 (11)	0.45626 (11)	0.0389 (4)
C13	0.3573 (3)	0.55253 (13)	0.51150 (13)	0.0498 (4)
H7	0.4864	0.5321	0.4864	0.060*
C12	0.2964 (4)	0.52072 (15)	0.60216 (14)	0.0635 (6)
H8	0.3822	0.4779	0.6382	0.076*
C11	0.1114 (4)	0.55125 (15)	0.63990 (13)	0.0631 (6)
H9	0.0687	0.5294	0.7019	0.076*
C7A	−0.0026 (2)	0.75856 (12)	0.16618 (11)	0.0378 (3)
H10	−0.0881	0.7114	0.1283	0.045*
C1	0.0020 (2)	0.72470 (11)	0.27237 (11)	0.0364 (3)
H11	−0.0253	0.7814	0.3162	0.044*
C10	−0.0113 (4)	0.61354 (15)	0.58734 (13)	0.0603 (5)
H12	−0.1380	0.6353	0.6140	0.072*
C9	0.0468 (3)	0.64509 (14)	0.49607 (13)	0.0498 (4)
H13	−0.0401	0.6879	0.4607	0.060*
C7	−0.0656 (3)	0.86200 (15)	0.13809 (16)	0.0584 (5)
H14A	−0.1744	0.8603	0.0880	0.070*
H14B	−0.1189	0.8977	0.1951	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0789 (13)	0.0675 (10)	0.159 (2)	0.0143 (9)	−0.0431 (13)	−0.0432 (12)
O2	0.0280 (6)	0.0762 (9)	0.0597 (7)	0.0084 (6)	0.0039 (5)	0.0184 (7)
O3	0.0281 (6)	0.0713 (9)	0.0852 (10)	−0.0097 (6)	−0.0096 (6)	0.0430 (8)
N1	0.0322 (6)	0.0392 (6)	0.0379 (6)	0.0041 (5)	−0.0002 (5)	0.0048 (5)
C6	0.0442 (9)	0.0423 (8)	0.0570 (10)	0.0035 (7)	−0.0013 (8)	0.0138 (8)
C5	0.0410 (10)	0.0574 (10)	0.0411 (8)	0.0042 (7)	0.0057 (7)	0.0141 (7)
C3	0.0278 (8)	0.0392 (8)	0.0421 (8)	0.0037 (6)	−0.0011 (6)	0.0029 (6)
C2	0.0292 (7)	0.0355 (7)	0.0361 (7)	−0.0007 (6)	−0.0034 (6)	0.0018 (6)
C4	0.0309 (7)	0.0418 (8)	0.0418 (8)	−0.0003 (6)	−0.0042 (6)	0.0033 (7)
C8	0.0451 (9)	0.0348 (7)	0.0367 (8)	−0.0039 (7)	−0.0068 (7)	−0.0012 (6)
C13	0.0540 (11)	0.0485 (10)	0.0469 (9)	0.0012 (8)	−0.0085 (8)	0.0047 (8)
C12	0.0888 (16)	0.0570 (11)	0.0448 (10)	−0.0003 (11)	−0.0128 (11)	0.0131 (9)
C11	0.0951 (16)	0.0564 (11)	0.0377 (9)	−0.0114 (11)	0.0023 (10)	0.0015 (8)
C7A	0.0255 (7)	0.0454 (8)	0.0425 (8)	−0.0020 (6)	−0.0051 (6)	0.0094 (6)
C1	0.0283 (7)	0.0387 (7)	0.0420 (8)	0.0030 (6)	0.0001 (6)	0.0077 (6)
C10	0.0782 (14)	0.0562 (10)	0.0464 (9)	0.0000 (11)	0.0177 (10)	−0.0107 (8)
C9	0.0599 (11)	0.0458 (9)	0.0437 (9)	0.0058 (8)	0.0036 (8)	−0.0026 (7)
C7	0.0440 (10)	0.0594 (11)	0.0717 (12)	0.0174 (8)	0.0097 (9)	0.0263 (10)

Geometric parameters (Å, º) top

O1—C6	1.397 (3)	C8—C9	1.393 (3)
O1—H1	0.8400	C8—C13	1.397 (2)
O2—C3	1.231 (2)	C13—C12	1.386 (3)
O3—C1	1.4074 (19)	C13—H7	0.9500
O3—H3	0.8400	C12—C11	1.376 (4)
N1—C3	1.346 (2)	C12—H8	0.9500
N1—C5	1.450 (2)	C11—C10	1.375 (3)
N1—C7A	1.458 (2)	C11—H9	0.9500
C6—C5	1.517 (2)	C7A—C7	1.524 (2)
C6—C7	1.521 (3)	C7A—C1	1.541 (2)
C6—H1A	1.0000	C7A—H10	1.0000
C5—H2A	0.9900	C1—H11	1.0000
C5—H2B	0.9900	C10—C9	1.387 (3)
C3—C2	1.486 (2)	C10—H12	0.9500
C2—C4	1.342 (2)	C9—H13	0.9500
C2—C1	1.507 (2)	C7—H14A	0.9900
C4—C8	1.463 (2)	C7—H14B	0.9900
C4—H5	0.9500

C6—O1—H1	109.5	C8—C13—H7	119.4
C1—O3—H3	109.5	C11—C12—C13	119.9 (2)
C3—N1—C5	126.33 (14)	C11—C12—H8	120.1
C3—N1—C7A	113.99 (12)	C13—C12—H8	120.1
C5—N1—C7A	110.30 (12)	C10—C11—C12	119.62 (18)
O1—C6—C5	106.77 (16)	C10—C11—H9	120.2
O1—C6—C7	111.99 (19)	C12—C11—H9	120.2
C5—C6—C7	102.82 (14)	N1—C7A—C7	103.95 (13)
O1—C6—H1A	111.6	N1—C7A—C1	105.03 (12)
C5—C6—H1A	111.6	C7—C7A—C1	121.85 (16)
C7—C6—H1A	111.6	N1—C7A—H10	108.4
N1—C5—C6	102.46 (13)	C7—C7A—H10	108.4
N1—C5—H2A	111.3	C1—C7A—H10	108.4
C6—C5—H2A	111.3	O3—C1—C2	111.20 (12)
N1—C5—H2B	111.3	O3—C1—C7A	111.48 (13)
C6—C5—H2B	111.3	C2—C1—C7A	104.12 (12)
H2A—C5—H2B	109.2	O3—C1—H11	110.0
O2—C3—N1	124.34 (16)	C2—C1—H11	110.0
O2—C3—C2	127.58 (15)	C7A—C1—H11	110.0
N1—C3—C2	108.08 (12)	C11—C10—C9	121.1 (2)
C4—C2—C3	120.10 (14)	C11—C10—H12	119.5
C4—C2—C1	132.00 (14)	C9—C10—H12	119.5
C3—C2—C1	107.86 (12)	C10—C9—C8	120.10 (19)
C2—C4—C8	131.40 (15)	C10—C9—H13	120.0
C2—C4—H5	114.3	C8—C9—H13	120.0
C8—C4—H5	114.3	C6—C7—C7A	106.55 (14)
C9—C8—C13	118.05 (16)	C6—C7—H14A	110.4
C9—C8—C4	125.05 (15)	C7A—C7—H14A	110.4
C13—C8—C4	116.90 (16)	C6—C7—H14B	110.4
C12—C13—C8	121.3 (2)	C7A—C7—H14B	110.4
C12—C13—H7	119.4	H14A—C7—H14B	108.6

C3—N1—C5—C6	−109.15 (17)	C3—N1—C7A—C7	130.55 (16)
C7A—N1—C5—C6	34.96 (17)	C5—N1—C7A—C7	−18.33 (18)
O1—C6—C5—N1	81.68 (19)	C3—N1—C7A—C1	1.52 (18)
C7—C6—C5—N1	−36.33 (18)	C5—N1—C7A—C1	−147.35 (13)
C5—N1—C3—O2	−31.5 (3)	C4—C2—C1—O3	−52.6 (2)
C7A—N1—C3—O2	−174.55 (16)	C3—C2—C1—O3	129.73 (14)
C5—N1—C3—C2	147.63 (14)	C4—C2—C1—C7A	−172.77 (17)
C7A—N1—C3—C2	4.63 (18)	C3—C2—C1—C7A	9.56 (16)
O2—C3—C2—C4	−7.9 (3)	N1—C7A—C1—O3	−126.78 (14)
N1—C3—C2—C4	172.96 (14)	C7—C7A—C1—O3	115.79 (17)
O2—C3—C2—C1	170.10 (17)	N1—C7A—C1—C2	−6.80 (16)
N1—C3—C2—C1	−9.04 (17)	C7—C7A—C1—C2	−124.23 (16)
C3—C2—C4—C8	173.90 (15)	C12—C11—C10—C9	1.0 (3)
C1—C2—C4—C8	−3.5 (3)	C11—C10—C9—C8	−0.3 (3)
C2—C4—C8—C9	−10.3 (3)	C13—C8—C9—C10	−1.1 (3)
C2—C4—C8—C13	170.38 (17)	C4—C8—C9—C10	179.60 (17)
C9—C8—C13—C12	1.8 (3)	O1—C6—C7—C7A	−88.1 (2)
C4—C8—C13—C12	−178.83 (17)	C5—C6—C7—C7A	26.1 (2)
C8—C13—C12—C11	−1.1 (3)	N1—C7A—C7—C6	−5.9 (2)
C13—C12—C11—C10	−0.3 (3)	C1—C7A—C7—C6	112.09 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.84	2.04	2.776 (2)	147
O3—H3···O2ⁱⁱ	0.84	1.85	2.6810 (17)	168

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₃
M_r	245.27
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.5007 (3), 13.6783 (7), 13.8382 (7)
V (Å³)	1230.47 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.31 × 0.13 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII DUO diffractometer
Absorption correction	Numerical (SADABS; Bruker, 2010)
T_min, T_max	0.924, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	32528, 2219, 2203
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.06
No. of reflections	2219
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23
Absolute structure	Flack (1983) and Hooft et al. (2008); Hooft parameter = 0.01(2), 905 Bijvoet pairs
Absolute structure parameter	0.1 (3)

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.84	2.04	2.776 (2)	146.6
O3—H3···O2ⁱⁱ	0.84	1.85	2.6810 (17)	168.4

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z.

Acknowledgements

The authors acknowledge the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial support. FLO and KRLF were supported by bursaries from CAPES and CNPq, respectively. KRLF is currently a FAPESP post-doctoral fellow. RA and FC are recipients of research grants from CNPq.

References

Baumann, K. O. (2007). WO Patent 2007039286; Chem. Abstr. 146, 421836. Google Scholar
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Freire, K. R. L., Tormena, C. F. & Coelho, F. (2011). Synlett, 14, 2059–2063. Google Scholar
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96–103. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oliveira, F. L., Freire, K. R. L., Aparicio, R. & Coelho, F. (2012a). Acta Cryst. E68, o586. CSD CrossRef IUCr Journals Google Scholar
Oliveira, F. L., Freire, K. R. L., Aparicio, R. & Coelho, F. (2012b). Acta Cryst. E68, o587. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1572

doi:10.1107/S1600536812018223

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1S,2E,6R,7aR)-2-Benzyl­­idene-1,6-dihy­dr­oxy-2,3,5,6,7,7a-hexa­hydro-1H-pyrrolizin-3-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1S,2E,6R,7aR)-2-Benzylidene-1,6-dihydroxy-2,3,5,6,7,7a-hexahydro-1H-pyrrolizin-3-one