(2S*)-2-Hydro­xy-2-[(2S*,5R*)-5-(1-hydroxy-1-methyl­ethyl)­tetra­hydro­furan-2-yl]-1-phenyl­ethano­ne

The mol­ecules of the title compound, C₁₅H₂₀O₄, link via a single intermolecular hydrogen bond to form chains running along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.146
• Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.02
         From the CIF: _reflns_number_total               2254
         Count of symmetry unique reflns         1447
         Completeness (_total/calc)            155.77%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       807
         Fraction of Friedel pairs measured     0.558
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997), COLLECT and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

2-Hydroxy-2-[5-(1-hydroxy-1-methyl-ethyl)-tetrahydro-furan-2-yl]-1-phenyl- ethanone

Crystal data

C15H20O4	Dx = 1.258 Mg m^−3
Mr = 264.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4487 reflections
a = 7.5556 (3) Å	θ = 3.2–25.0°
b = 8.0446 (3) Å	µ = 0.09 mm^−1
c = 22.9549 (8) Å	T = 150 K
V = 1395.24 (9) Å^3	Block, colourless
Z = 4	0.25 × 0.10 × 0.08 mm
F(000) = 568

Data collection

Nonius KappaCCD area-detector diffractometer	2254 independent reflections
Radiation source: Nonius FR591 Rotating anode	1917 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 9.091 pixels mm^1 pixels mm^-1	θmax = 25.0°, θmin = 3.2°
φ and ω scans to fill the Ewald sphere	h = −7→8
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	k = −9→7
Tmin = 0.978, Tmax = 0.993	l = −26→22
4487 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0959P)^2] where P = (Fo^2 + 2Fc^2)/3
2254 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.24 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
C1	0.7265 (3)	0.3088 (3)	0.89577 (11)	0.0364 (6)
C2	0.8244 (3)	0.3590 (4)	0.94465 (11)	0.0435 (6)
H2	0.8537	0.4729	0.9497	0.052*
C3	0.8783 (4)	0.2435 (4)	0.98544 (13)	0.0512 (8)
H3	0.9453	0.2785	1.0182	0.061*
C4	0.8357 (4)	0.0782 (4)	0.97901 (13)	0.0488 (7)
H4	0.8714	0.0000	1.0077	0.059*
C5	0.7405 (4)	0.0257 (4)	0.93061 (12)	0.0451 (7)
H5	0.7125	−0.0887	0.9260	0.054*
C6	0.6867 (3)	0.1399 (3)	0.88922 (11)	0.0390 (6)
H6	0.6223	0.1035	0.8561	0.047*
C7	0.6666 (3)	0.4387 (3)	0.85403 (11)	0.0370 (6)
C8	0.5324 (3)	0.3935 (3)	0.80714 (10)	0.0372 (6)
H8	0.5639	0.2831	0.7900	0.045*
C9	0.3489 (4)	0.3819 (3)	0.83639 (11)	0.0376 (6)
H9	0.3422	0.2765	0.8594	0.045*
C10	0.1930 (4)	0.3880 (3)	0.79365 (13)	0.0456 (7)
H10A	0.2290	0.3502	0.7543	0.055*
H10B	0.0931	0.3188	0.8074	0.055*
C11	0.1443 (4)	0.5721 (4)	0.79354 (13)	0.0429 (7)
H11A	0.2170	0.6347	0.7651	0.051*
H11B	0.0176	0.5882	0.7841	0.051*
C12	0.1844 (3)	0.6261 (3)	0.85529 (12)	0.0382 (6)
H12	0.0778	0.6048	0.8800	0.046*
C13	0.2429 (4)	0.8045 (3)	0.86423 (11)	0.0393 (6)
C14	0.1094 (4)	0.9239 (4)	0.83689 (14)	0.0512 (8)
H14A	0.1486	1.0387	0.8430	0.077*
H14B	−0.0067	0.9079	0.8551	0.077*
H14C	0.1006	0.9018	0.7950	0.077*
C15	0.2691 (5)	0.8429 (4)	0.92893 (12)	0.0528 (7)
H15A	0.3069	0.9587	0.9335	0.079*
H15B	0.3597	0.7689	0.9450	0.079*
H15C	0.1573	0.8258	0.9497	0.079*
O1	0.7172 (2)	0.5827 (3)	0.85810 (9)	0.0489 (5)
O2	0.5341 (3)	0.5156 (2)	0.76291 (7)	0.0457 (5)
H2A	0.5500	0.4697	0.7305	0.069*
O3	0.3264 (2)	0.5208 (2)	0.87512 (7)	0.0379 (4)
O4	0.4087 (2)	0.8337 (2)	0.83451 (8)	0.0399 (5)
H4A	0.4733	0.7491	0.8375	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0292 (13)	0.0453 (14)	0.0348 (13)	−0.0003 (11)	0.0008 (9)	−0.0016 (11)
C2	0.0364 (13)	0.0527 (16)	0.0414 (14)	−0.0028 (13)	−0.0020 (11)	−0.0047 (13)
C3	0.0437 (17)	0.068 (2)	0.0415 (16)	0.0005 (16)	−0.0060 (12)	−0.0022 (15)
C4	0.0442 (15)	0.0602 (18)	0.0419 (15)	0.0067 (15)	−0.0003 (12)	0.0073 (14)
C5	0.0392 (14)	0.0465 (15)	0.0497 (14)	0.0038 (13)	0.0023 (12)	0.0003 (13)
C6	0.0359 (13)	0.0447 (14)	0.0365 (13)	0.0040 (12)	−0.0003 (10)	−0.0017 (11)
C7	0.0304 (12)	0.0401 (13)	0.0403 (14)	0.0008 (12)	0.0056 (10)	−0.0027 (11)
C8	0.0416 (14)	0.0392 (14)	0.0309 (12)	0.0057 (12)	−0.0009 (10)	−0.0034 (11)
C9	0.0377 (13)	0.0359 (13)	0.0392 (14)	−0.0035 (11)	−0.0040 (10)	0.0000 (11)
C10	0.0413 (15)	0.0427 (15)	0.0530 (16)	−0.0034 (12)	−0.0150 (12)	0.0005 (13)
C11	0.0357 (14)	0.0434 (14)	0.0496 (15)	−0.0040 (12)	−0.0096 (11)	0.0032 (12)
C12	0.0291 (12)	0.0417 (14)	0.0439 (14)	0.0010 (11)	0.0026 (10)	0.0051 (11)
C13	0.0400 (13)	0.0424 (14)	0.0356 (13)	−0.0005 (12)	0.0045 (12)	0.0024 (11)
C14	0.0498 (17)	0.0432 (15)	0.0606 (19)	0.0065 (14)	0.0043 (13)	0.0036 (14)
C15	0.0659 (18)	0.0500 (16)	0.0424 (15)	−0.0027 (15)	0.0073 (14)	−0.0058 (14)
O1	0.0418 (11)	0.0471 (11)	0.0578 (12)	−0.0067 (9)	−0.0070 (9)	0.0048 (10)
O2	0.0565 (12)	0.0472 (11)	0.0335 (9)	0.0081 (10)	0.0042 (8)	0.0019 (8)
O3	0.0353 (9)	0.0425 (10)	0.0357 (9)	0.0031 (8)	−0.0013 (7)	0.0002 (8)
O4	0.0378 (10)	0.0409 (10)	0.0410 (9)	−0.0051 (8)	0.0035 (7)	0.0026 (9)

Geometric parameters (Å, º)

C1—C6	1.399 (4)	C10—C11	1.526 (4)
C1—C2	1.403 (4)	C10—H10A	0.9900
C1—C7	1.488 (4)	C10—H10B	0.9900
C2—C3	1.380 (4)	C11—C12	1.513 (4)
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.376 (5)	C11—H11B	0.9900
C3—H3	0.9500	C12—O3	1.441 (3)
C4—C5	1.389 (4)	C12—C13	1.516 (4)
C4—H4	0.9500	C12—H12	1.0000
C5—C6	1.383 (4)	C13—O4	1.446 (3)
C5—H5	0.9500	C13—C14	1.528 (4)
C6—H6	0.9500	C13—C15	1.530 (4)
C7—O1	1.223 (4)	C14—H14A	0.9800
C7—C8	1.523 (4)	C14—H14B	0.9800
C8—O2	1.413 (3)	C14—H14C	0.9800
C8—C9	1.543 (4)	C15—H15A	0.9800
C8—H8	1.0000	C15—H15B	0.9800
C9—O3	1.438 (3)	C15—H15C	0.9800
C9—C10	1.533 (4)	O2—H2A	0.8400
C9—H9	1.0000	O4—H4A	0.8400
C6—C1—C2	118.6 (3)	C11—C10—H10B	111.3
C6—C1—C7	123.2 (2)	C9—C10—H10B	111.3
C2—C1—C7	118.2 (3)	H10A—C10—H10B	109.2
C3—C2—C1	120.3 (3)	C12—C11—C10	103.2 (2)
C3—C2—H2	119.8	C12—C11—H11A	111.1
C1—C2—H2	119.8	C10—C11—H11A	111.1
C4—C3—C2	120.6 (3)	C12—C11—H11B	111.1
C4—C3—H3	119.7	C10—C11—H11B	111.1
C2—C3—H3	119.7	H11A—C11—H11B	109.1
C3—C4—C5	120.1 (3)	O3—C12—C11	106.0 (2)
C3—C4—H4	120.0	O3—C12—C13	107.3 (2)
C5—C4—H4	120.0	C11—C12—C13	117.2 (2)
C6—C5—C4	119.9 (3)	O3—C12—H12	108.7
C6—C5—H5	120.0	C11—C12—H12	108.7
C4—C5—H5	120.0	C13—C12—H12	108.7
C5—C6—C1	120.6 (3)	O4—C13—C12	110.0 (2)
C5—C6—H6	119.7	O4—C13—C14	106.0 (2)
C1—C6—H6	119.7	C12—C13—C14	110.3 (2)
O1—C7—C1	121.4 (2)	O4—C13—C15	108.3 (2)
O1—C7—C8	119.2 (2)	C12—C13—C15	111.1 (2)
C1—C7—C8	119.3 (2)	C14—C13—C15	110.9 (2)
O2—C8—C7	109.6 (2)	C13—C14—H14A	109.5
O2—C8—C9	111.3 (2)	C13—C14—H14B	109.5
C7—C8—C9	107.8 (2)	H14A—C14—H14B	109.5
O2—C8—H8	109.4	C13—C14—H14C	109.5
C7—C8—H8	109.4	H14A—C14—H14C	109.5
C9—C8—H8	109.4	H14B—C14—H14C	109.5
O3—C9—C10	106.3 (2)	C13—C15—H15A	109.5
O3—C9—C8	109.1 (2)	C13—C15—H15B	109.5
C10—C9—C8	114.2 (2)	H15A—C15—H15B	109.5
O3—C9—H9	109.1	C13—C15—H15C	109.5
C10—C9—H9	109.1	H15A—C15—H15C	109.5
C8—C9—H9	109.1	H15B—C15—H15C	109.5
C11—C10—C9	102.6 (2)	C8—O2—H2A	109.5
C11—C10—H10A	111.3	C9—O3—C12	110.46 (19)
C9—C10—H10A	111.3	C13—O4—H4A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4^i	0.84	1.88	2.707 (3)	170
O4—H4A···O3	0.84	2.31	2.756 (3)	113
O4—H4A···O1	0.84	2.33	3.131 (3)	161
O4—H4A···O2	0.84	2.58	3.186 (3)	130

Symmetry code: (i) −x+1, y−1/2, −z+3/2.