(+)-(5S)-5-[(1S)-2-Benzoyl-1-hydroxy­ethyl]-1,2,3,4-tetra­hydro­furan-2-one

The title compound, C₁₃H₁₄O₄, displays a kinked conformation in which the hydr­oxy group is orientated over the furan­one ring. Mol­ecules aggregate into linear supra­molecular chains via O—H...O inter­actions, and C—H...O contacts link these chains into two-dimensional arrays.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.857     1.000
            Tmin(prime) and Tmax expected:      0.954     0.984
            RR(prime) =      0.884
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C15    = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound (I) was investigated during studies of intramolecular cyclizations of 1,2-dioxines containing tethered hydroxyl groups (Avery et al., 2005). The molecular structure (Fig. 1) shows the O1-hydroxyl group to lie over the five-membered furanone ring; the latter is twisted about the C13—C14 bond. Overall the molecule adopts a kinked shape. The C₆H₅C(=O)CH₂CH residue has an open or extended configuration as seen in the values of the C1/C2/C3/C31 and C2/C3/C31/C32 torsion angles of 164.79 (12) and 165.98 (13) °, respectively. The kink in the molecule occurs about the C1—C15 bond as reflected in the C2/C1/C15/O11 torsion angle of -55.15 (14)°. The dihedral angle formed between the six- and five-membered rings is 18.52 (8)°. Molecules aggregate in the crystal structure via O—H···O contacts involving the hydroxyl group and O12-carbonyl to form a linear supramolecular chain aligned along the b axis (Fig. 2 & Table 1); reinforcing this chain are C14—H···O12 contacts. The chains are connected into double-chains via additional phenyl C36—H···O1 and methylene-C14—H···O3 interactions (Table 1); the lactone-O11 atom is involved in an intramolecular C—H···O contact with a methylene C2—H atom. Double chains stack along the (1 0 - 1) plane being separated by hydrophobic interactions (Fig. 3).

Related literature

For related literature, see: Avery et al. (2005); Jung et al. (2002); Yates & Anderson (1963).

S2. Experimental

The title compound was prepared in 27% yield following literature procedures (Avery et al., 2005; Jung et al., 2002; Yates & Anderson, 1963). Solid (I) was recrystallized heptane/dichloromethane to give white needles with m.p. 366–367 K. R_f 0.28 (3:2 ethyl acetate:hexanes). Elemental analysis found: C 66.73, H, 5.99%; C₁₃H₁₄O₄ requires: C 66.66, H, 6.02%. IR (nujol) 3144–3650, 2253 (w), 1780, 1769, 1747, 1732, 1689, 1682, 1671, 1597, 1580 cm^{-1. 1}H NMR (600 MHz, p.p.m.) δ 2.30–2.41 (m, 3H), 2.50 (ddd, J = 17.4, 10.2, 6.0 Hz, 1H), 2.73 (ddd, J = 17.4, 9.6, 7.2 Hz, 1H), 3.25 (dd, J = 18.0, 3.0 Hz, 1H), 3.41 (dd, J = 18.0, 9.0 Hz, 1H), 4.32 (ddd, J = 9.0, 3.0, 3.0 Hz, 1H), 4.58 (ddd, J = 8.4, 6.0, 3.0 Hz, 1H), 7.47–7.50 (m, 2H), 7.96–7.98 (m, 2H), 7.59–7.62 (m, 1H). ¹³C NMR (75 MHz, p.p.m.) δ 23.9, 28.4, 41.6, 69.3, 81.6, 128.1, 128.8, 133.8, 136.4, 177.5, 199.7. MS (EI) m/z (%): 235 ([M+H]⁺, 20), 217 (35), 157 (37), 149 (58), 120 (14), 105 (100), 77 (88), 51 (52).

S3. Refinement

All C-bound H atoms were included in the riding-model approximation, with C—H = 0.94 to 0.99 Å, and with U_iso(H) = 1.2U_eq(C). The hydroxyl-H atoms were located from a difference map and included so that O—H = 0.84 Å and U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. View of the supramolecular chain in (I) mediated by hydrogen bonds, shown as orange-dashed lines. Colour code: red (oxygen), grey (carbon) and green (hydrogen).
	Fig. 3. View of the unit-cell contents of (I) highlighting the stacking of double layers along the (1 0 - 1) plane. Hydrogen bonding contacts are shown as orange- (O—H···O) and blue- (C—H···O) dashed lines.

(+)-(5S)-5-[(1S)-2-Benzoyl-1-hydroxyethyl]-1,2,3,4-tetrahydrofuran-2-one

Crystal data

C13H14O4	F(000) = 496
Mr = 234.24	Dx = 1.352 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 2654 reflections
a = 14.6504 (16) Å	θ = 2.3–29.0°
b = 5.5565 (6) Å	µ = 0.10 mm^−1
c = 14.7565 (15) Å	T = 223 K
β = 106.628 (2)°	Block, colourless
V = 1151.0 (2) Å^3	0.47 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2635 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −19→18
Tmin = 0.857, Tmax = 1	k = −7→7
7754 measured reflections	l = −11→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.2723P] where P = (Fo^2 + 2Fc^2)/3
2635 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.27 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.39803 (7)	0.15817 (19)	0.47990 (7)	0.0425 (3)
H1O	0.3653	0.0391	0.4868	0.058*
O3	0.41520 (8)	0.2218 (2)	0.20524 (7)	0.0477 (3)
O11	0.30843 (7)	0.58579 (17)	0.38984 (7)	0.0375 (3)
O12	0.27976 (8)	0.77243 (19)	0.51112 (8)	0.0473 (3)
C1	0.38118 (10)	0.1995 (2)	0.38123 (9)	0.0355 (3)
H1	0.3724	0.0431	0.3477	0.043*
C2	0.46917 (10)	0.3235 (3)	0.36818 (10)	0.0391 (3)
H2A	0.4735	0.4856	0.3953	0.047*
H2B	0.5258	0.2339	0.4035	0.047*
C3	0.46945 (10)	0.3429 (3)	0.26603 (10)	0.0367 (3)
C12	0.26556 (10)	0.6016 (2)	0.45865 (10)	0.0369 (3)
C13	0.20198 (10)	0.3884 (3)	0.45679 (11)	0.0410 (3)
H13A	0.1371	0.4401	0.4534	0.049*
H13B	0.2265	0.2884	0.5132	0.049*
C14	0.20369 (10)	0.2517 (3)	0.36801 (10)	0.0389 (3)
H14A	0.1457	0.2826	0.3164	0.047*
H14B	0.2096	0.0781	0.3801	0.047*
C15	0.29174 (10)	0.3504 (2)	0.34409 (9)	0.0345 (3)
H15	0.2776	0.3701	0.2748	0.041*
C31	0.53744 (9)	0.5110 (3)	0.24057 (10)	0.0369 (3)
C32	0.55196 (12)	0.4892 (3)	0.15187 (11)	0.0505 (4)
H32	0.5200	0.3685	0.1101	0.061*
C33	0.61305 (13)	0.6438 (4)	0.12478 (13)	0.0596 (5)
H33	0.6232	0.6269	0.0650	0.071*
C34	0.65933 (13)	0.8236 (4)	0.18532 (13)	0.0571 (5)
H34	0.7007	0.9292	0.1666	0.069*
C35	0.64510 (12)	0.8480 (3)	0.27262 (13)	0.0538 (4)
H35	0.6762	0.9715	0.3134	0.065*
C36	0.58489 (11)	0.6910 (3)	0.30106 (11)	0.0451 (4)
H36	0.5762	0.7067	0.3615	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0462 (6)	0.0428 (6)	0.0341 (5)	−0.0025 (5)	0.0043 (4)	0.0065 (4)
O3	0.0490 (6)	0.0508 (6)	0.0414 (6)	−0.0100 (5)	0.0098 (5)	−0.0109 (5)
O11	0.0423 (5)	0.0283 (5)	0.0437 (5)	−0.0019 (4)	0.0149 (4)	0.0028 (4)
O12	0.0564 (6)	0.0373 (6)	0.0507 (6)	−0.0020 (5)	0.0193 (5)	−0.0053 (5)
C1	0.0394 (7)	0.0322 (7)	0.0313 (7)	0.0001 (5)	0.0044 (5)	−0.0001 (5)
C2	0.0343 (7)	0.0434 (8)	0.0355 (7)	0.0002 (6)	0.0034 (6)	−0.0010 (6)
C3	0.0332 (6)	0.0358 (7)	0.0384 (7)	0.0041 (5)	0.0058 (5)	−0.0036 (6)
C12	0.0373 (7)	0.0322 (7)	0.0402 (7)	0.0035 (5)	0.0097 (6)	0.0057 (6)
C13	0.0407 (7)	0.0385 (8)	0.0450 (8)	−0.0017 (6)	0.0142 (6)	0.0071 (6)
C14	0.0354 (7)	0.0340 (7)	0.0433 (8)	−0.0041 (5)	0.0049 (6)	0.0030 (6)
C15	0.0386 (7)	0.0311 (6)	0.0307 (6)	−0.0021 (5)	0.0049 (5)	0.0009 (5)
C31	0.0314 (6)	0.0399 (7)	0.0373 (7)	0.0040 (6)	0.0062 (5)	−0.0002 (6)
C32	0.0486 (9)	0.0595 (10)	0.0434 (8)	−0.0045 (8)	0.0134 (7)	−0.0072 (7)
C33	0.0581 (10)	0.0759 (13)	0.0493 (10)	−0.0048 (9)	0.0230 (8)	0.0004 (9)
C34	0.0487 (9)	0.0627 (11)	0.0619 (11)	−0.0070 (8)	0.0190 (8)	0.0097 (9)
C35	0.0497 (9)	0.0521 (10)	0.0567 (10)	−0.0106 (8)	0.0107 (8)	−0.0037 (8)
C36	0.0439 (8)	0.0483 (9)	0.0417 (8)	−0.0041 (7)	0.0101 (6)	−0.0035 (7)

Geometric parameters (Å, º)

O1—C1	1.4241 (16)	C13—H13B	0.9800
O1—H1O	0.8401	C14—C15	1.533 (2)
O3—C3	1.2169 (17)	C14—H14A	0.9800
O11—C12	1.3409 (17)	C14—H14B	0.9800
O11—C15	1.4600 (16)	C15—H15	0.9900
O12—C12	1.2047 (18)	C31—C32	1.390 (2)
C1—C15	1.5196 (19)	C31—C36	1.388 (2)
C1—C2	1.522 (2)	C32—C33	1.380 (3)
C1—H1	0.9900	C32—H32	0.9400
C2—C3	1.5123 (19)	C33—C34	1.381 (3)
C2—H2A	0.9800	C33—H33	0.9400
C2—H2B	0.9800	C34—C35	1.369 (3)
C3—C31	1.490 (2)	C34—H34	0.9400
C12—C13	1.503 (2)	C35—C36	1.388 (2)
C13—C14	1.521 (2)	C35—H35	0.9400
C13—H13A	0.9800	C36—H36	0.9400
C1—O1—H1O	108.3	C15—C14—H14A	111.0
C12—O11—C15	110.87 (10)	C13—C14—H14B	111.0
O1—C1—C15	109.70 (11)	C15—C14—H14B	111.0
O1—C1—C2	107.29 (11)	H14A—C14—H14B	109.0
C15—C1—C2	112.27 (12)	O11—C15—C1	108.32 (10)
O1—C1—H1	109.2	O11—C15—C14	104.76 (11)
C15—C1—H1	109.2	C1—C15—C14	114.52 (11)
C2—C1—H1	109.2	O11—C15—H15	109.7
C3—C2—C1	113.73 (11)	C1—C15—H15	109.7
C3—C2—H2A	108.8	C14—C15—H15	109.7
C1—C2—H2A	108.8	C32—C31—C36	119.00 (14)
C3—C2—H2B	108.8	C32—C31—C3	118.46 (13)
C1—C2—H2B	108.8	C36—C31—C3	122.53 (13)
H2A—C2—H2B	107.7	C33—C32—C31	120.36 (16)
O3—C3—C31	120.22 (13)	C33—C32—H32	119.8
O3—C3—C2	120.52 (13)	C31—C32—H32	119.8
C31—C3—C2	119.26 (12)	C32—C33—C34	120.11 (16)
O12—C12—O11	120.42 (13)	C32—C33—H33	119.9
O12—C12—C13	128.68 (13)	C34—C33—H33	119.9
O11—C12—C13	110.90 (12)	C35—C34—C33	120.09 (16)
C12—C13—C14	104.28 (11)	C35—C34—H34	120.0
C12—C13—H13A	110.9	C33—C34—H34	120.0
C14—C13—H13A	110.9	C34—C35—C36	120.20 (16)
C12—C13—H13B	110.9	C34—C35—H35	119.9
C14—C13—H13B	110.9	C36—C35—H35	119.9
H13A—C13—H13B	108.9	C35—C36—C31	120.22 (15)
C13—C14—C15	104.01 (11)	C35—C36—H36	119.9
C13—C14—H14A	111.0	C31—C36—H36	119.9
O1—C1—C2—C3	170.38 (11)	C13—C14—C15—O11	−22.70 (13)
C15—C1—C2—C3	−69.02 (16)	C13—C14—C15—C1	95.83 (13)
C1—C2—C3—O3	−15.6 (2)	O3—C3—C31—C32	−13.6 (2)
C1—C2—C3—C31	164.79 (12)	C2—C3—C31—C32	165.98 (13)
C15—O11—C12—O12	171.93 (12)	O3—C3—C31—C36	164.87 (14)
C15—O11—C12—C13	−8.76 (15)	C2—C3—C31—C36	−15.5 (2)
O12—C12—C13—C14	172.88 (14)	C36—C31—C32—C33	0.3 (2)
O11—C12—C13—C14	−6.36 (15)	C3—C31—C32—C33	178.88 (16)
C12—C13—C14—C15	17.70 (14)	C31—C32—C33—C34	−0.8 (3)
C12—O11—C15—C1	−102.61 (13)	C32—C33—C34—C35	0.3 (3)
C12—O11—C15—C14	20.04 (14)	C33—C34—C35—C36	0.6 (3)
O1—C1—C15—O11	64.04 (13)	C34—C35—C36—C31	−1.1 (3)
C2—C1—C15—O11	−55.15 (14)	C32—C31—C36—C35	0.7 (2)
O1—C1—C15—C14	−52.45 (15)	C3—C31—C36—C35	−177.84 (14)
C2—C1—C15—C14	−171.64 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O12^i	0.84	2.04	2.8750 (16)	174
C2—H2A···O11	0.98	2.46	2.8640 (19)	104
C14—H14A···O3^ii	0.98	2.59	3.154 (2)	117
C14—H14B···O12^i	0.98	2.56	3.383 (2)	142
C36—H36···O1^iii	0.94	2.38	3.2787 (19)	159

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