(3S,6R)-3-Benzyl­oxymeth­yl-6-meth­yl-1,4-dioxane-2,5-dione

The chiral centres in the dilactone moiety of the title compound, C₁₃H₁₄O₅, are in the configuration 3S,6R. The ring itself has a somewhat flattened twist-boat conformation. C—H...O inter­actions join the mol­ecules into a two-dimensional network running parallel to the (101) plane.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.076
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C4      ..       2.92 Ang.

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           27.46
           From the CIF: _reflns_number_total               1464
           Count of symmetry unique reflns         1463
           Completeness (_total/calc)            100.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: Collect (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(3S,6R)-3-benzyloxymethyl-6-methyl-1,4-dioxane-2,5-dione

Crystal data

C13H14O5	F(000) = 264
Mr = 250.24	Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set.
Monoclinic, P21	Dx = 1.383 Mg m^−3
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 5.289 (2) Å	Cell parameters from 156 reflections
b = 8.678 (2) Å	θ = 2.0–25.0°
c = 13.178 (5) Å	µ = 0.11 mm^−1
β = 96.748 (12)°	T = 150 K
V = 600.7 (4) Å^3	Block, colourless
Z = 2	0.25 × 0.10 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1308 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.056
Graphite monochromator	θmax = 27.5°, θmin = 1.6°
Detector resolution: 18.4 pixels mm^-1	h = −6→6
φ scans and ω scans with κ offsets	k = −11→11
16381 measured reflections	l = −17→17
1464 independent 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.02P] where P = (Fo^2 + 2Fc^2)/3
1464 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	0.0433 (3)	0.3918 (2)	0.55044 (12)	0.0499 (5)
O2	−0.0853 (2)	0.26166 (17)	0.41155 (10)	0.0320 (4)
O3	0.3935 (2)	0.12549 (14)	0.41167 (9)	0.0283 (4)
O4	0.2809 (3)	0.02090 (16)	0.26179 (10)	0.0355 (4)
O5	0.1666 (2)	0.41016 (16)	0.26347 (10)	0.0324 (4)
C1	0.0976 (3)	0.3082 (2)	0.48358 (15)	0.0307 (5)
C2	0.3661 (3)	0.2508 (2)	0.48232 (14)	0.0259 (5)
C3	0.4773 (4)	0.1942 (3)	0.58649 (15)	0.0390 (6)
C4	0.2279 (3)	0.10510 (19)	0.32909 (14)	0.0253 (5)
C5	−0.0252 (3)	0.1870 (2)	0.31980 (14)	0.0276 (5)
C6	−0.0353 (3)	0.3049 (2)	0.23501 (15)	0.0313 (5)
C7	0.2317 (4)	0.5033 (2)	0.17992 (15)	0.0313 (6)
C8	0.0097 (3)	0.59612 (19)	0.13024 (13)	0.0258 (5)
C9	−0.0951 (4)	0.7136 (2)	0.18390 (14)	0.0309 (5)
C10	−0.3081 (4)	0.7930 (2)	0.14051 (16)	0.0364 (6)
C11	−0.4171 (4)	0.7560 (2)	0.04274 (15)	0.0355 (6)
C12	−0.3108 (4)	0.6417 (2)	−0.01218 (14)	0.0344 (6)
C13	−0.0981 (4)	0.5627 (2)	0.03144 (14)	0.0304 (6)
H2	0.47250	0.33900	0.46300	0.0310*
H3A	0.37080	0.11120	0.60860	0.0580*
H3B	0.48320	0.27940	0.63550	0.0580*
H3C	0.65000	0.15540	0.58290	0.0580*
H5	−0.16070	0.10870	0.29990	0.0330*
H6A	−0.01260	0.25450	0.16930	0.0380*
H6B	−0.20110	0.35920	0.22750	0.0380*
H7A	0.29500	0.43560	0.12800	0.0380*
H7B	0.37130	0.57440	0.20540	0.0380*
H9	−0.01990	0.73950	0.25080	0.0370*
H10	−0.37930	0.87260	0.17770	0.0440*
H11	−0.56490	0.80910	0.01330	0.0430*
H12	−0.38380	0.61770	−0.07970	0.0410*
H13	−0.02510	0.48470	−0.00650	0.0360*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0400 (8)	0.0517 (10)	0.0596 (10)	0.0048 (8)	0.0132 (7)	−0.0264 (9)
O2	0.0243 (6)	0.0341 (7)	0.0387 (7)	0.0017 (6)	0.0085 (5)	−0.0033 (6)
O3	0.0251 (6)	0.0273 (7)	0.0327 (7)	0.0041 (5)	0.0043 (5)	−0.0059 (6)
O4	0.0449 (8)	0.0316 (7)	0.0307 (7)	0.0065 (6)	0.0080 (6)	−0.0029 (6)
O5	0.0328 (7)	0.0265 (6)	0.0360 (7)	−0.0058 (6)	−0.0038 (6)	0.0056 (6)
C1	0.0291 (9)	0.0262 (9)	0.0380 (10)	−0.0012 (8)	0.0095 (8)	−0.0034 (8)
C2	0.0273 (8)	0.0212 (8)	0.0301 (9)	−0.0011 (7)	0.0078 (7)	−0.0041 (7)
C3	0.0430 (11)	0.0399 (11)	0.0334 (10)	0.0028 (10)	0.0022 (9)	−0.0038 (9)
C4	0.0295 (9)	0.0201 (8)	0.0272 (9)	−0.0001 (7)	0.0074 (7)	0.0024 (7)
C5	0.0250 (8)	0.0256 (9)	0.0324 (10)	−0.0030 (7)	0.0046 (7)	−0.0012 (8)
C6	0.0278 (9)	0.0258 (9)	0.0389 (10)	−0.0029 (8)	−0.0019 (7)	0.0029 (8)
C7	0.0288 (10)	0.0277 (9)	0.0377 (10)	−0.0028 (8)	0.0051 (8)	0.0046 (8)
C8	0.0283 (9)	0.0217 (9)	0.0283 (9)	−0.0036 (7)	0.0072 (7)	0.0026 (7)
C9	0.0396 (10)	0.0254 (9)	0.0284 (9)	−0.0040 (8)	0.0075 (8)	−0.0005 (8)
C10	0.0447 (11)	0.0241 (10)	0.0434 (11)	0.0037 (8)	0.0175 (9)	0.0030 (8)
C11	0.0336 (9)	0.0302 (9)	0.0429 (11)	0.0002 (8)	0.0057 (8)	0.0118 (9)
C12	0.0395 (11)	0.0315 (10)	0.0309 (10)	−0.0046 (8)	−0.0007 (8)	0.0030 (8)
C13	0.0346 (10)	0.0254 (9)	0.0321 (10)	−0.0030 (8)	0.0081 (8)	−0.0017 (8)

Geometric parameters (Å, º)

O1—C1	1.202 (3)	C11—C12	1.385 (3)
O2—C1	1.336 (2)	C12—C13	1.384 (3)
O2—C5	1.440 (2)	C2—H2	1.0000
O3—C2	1.450 (2)	C3—H3A	0.9800
O3—C4	1.326 (2)	C3—H3B	0.9800
O4—C4	1.207 (2)	C3—H3C	0.9800
O5—C6	1.422 (2)	C5—H5	1.0000
O5—C7	1.440 (2)	C6—H6A	0.9900
C1—C2	1.507 (2)	C6—H6B	0.9900
C2—C3	1.511 (3)	C7—H7A	0.9900
C4—C5	1.508 (2)	C7—H7B	0.9900
C5—C6	1.511 (3)	C9—H9	0.9500
C7—C8	1.509 (3)	C10—H10	0.9500
C8—C9	1.392 (3)	C11—H11	0.9500
C8—C13	1.389 (3)	C12—H12	0.9500
C9—C10	1.385 (3)	C13—H13	0.9500
C10—C11	1.386 (3)
O1···C5^i	3.088 (3)	C13···C6	3.479 (3)
O1···O3^i	3.158 (2)	C3···H7B^viii	2.9500
O1···C4^i	2.922 (3)	C8···H6A	3.0100
O2···O5	2.803 (2)	C8···H6B	2.7300
O2···O3^ii	2.9994 (19)	C10···H7B^ii	2.7500
O2···O3	2.7943 (19)	C11···H7B^ii	2.9800
O2···C2^ii	3.152 (2)	C11···H7A^x	2.8700
O3···O2^iii	2.9994 (19)	C12···H7A^x	2.9800
O3···O2	2.7943 (19)	C12···H11^xi	2.9600
O3···O1^iv	3.158 (2)	C12···H6A^x	3.0000
O4···C9^v	3.412 (3)	C13···H11^xi	2.8500
O5···O2	2.803 (2)	H2···O2^iii	2.6000
O5···C2	3.260 (3)	H3B···O1	2.6500
O5···C1	3.095 (3)	H3B···O4^xii	2.7200
O1···H5^i	2.7400	H5···O1^iv	2.7400
O1···H3B	2.6500	H6A···O4	2.7500
O2···H2^ii	2.6000	H6A···C8	3.0100
O4···H9^v	2.9100	H6A···H7A	2.3700
O4···H12^vi	2.6600	H6A···C12^vi	3.0000
O4···H10^vii	2.5700	H6B···C8	2.7300
O4···H3B^viii	2.7200	H7A···H6A	2.3700
O4···H6A	2.7500	H7A···H13	2.3400
C1···O5	3.095 (3)	H7A···C11^vi	2.8700
C2···O2^iii	3.152 (2)	H7A···C12^vi	2.9800
C2···O5	3.260 (3)	H7B···C10^iii	2.7500
C4···O1^iv	2.922 (3)	H7B···C11^iii	2.9800
C5···O1^iv	3.088 (3)	H7B···C3^xii	2.9500
C6···C13	3.479 (3)	H9···O4^ix	2.9100
C7···C10^iii	3.579 (3)	H10···O4^xiii	2.5700
C7···C11^iii	3.510 (3)	H11···C12^xiv	2.9600
C9···O4^ix	3.412 (3)	H11···C13^xiv	2.8500
C10···C7^ii	3.579 (3)	H12···O4^x	2.6600
C11···C7^ii	3.510 (3)	H13···H7A	2.3400
C1—O2—C5	121.33 (13)	C2—C3—H3B	109.00
C2—O3—C4	121.39 (13)	C2—C3—H3C	109.00
C6—O5—C7	113.49 (14)	H3A—C3—H3B	109.00
O1—C1—O2	119.21 (16)	H3A—C3—H3C	109.00
O1—C1—C2	120.95 (17)	H3B—C3—H3C	109.00
O2—C1—C2	119.80 (16)	O2—C5—H5	108.00
O3—C2—C1	114.86 (14)	C4—C5—H5	108.00
O3—C2—C3	106.38 (15)	C6—C5—H5	108.00
C1—C2—C3	111.36 (16)	O5—C6—H6A	110.00
O3—C4—O4	119.71 (15)	O5—C6—H6B	110.00
O3—C4—C5	119.88 (15)	C5—C6—H6A	111.00
O4—C4—C5	120.41 (16)	C5—C6—H6B	110.00
O2—C5—C4	115.18 (14)	H6A—C6—H6B	109.00
O2—C5—C6	108.91 (14)	O5—C7—H7A	109.00
C4—C5—C6	109.45 (14)	O5—C7—H7B	109.00
O5—C6—C5	106.24 (14)	C8—C7—H7A	109.00
O5—C7—C8	112.82 (16)	C8—C7—H7B	109.00
C7—C8—C9	120.44 (16)	H7A—C7—H7B	108.00
C7—C8—C13	120.54 (16)	C8—C9—H9	120.00
C9—C8—C13	119.00 (16)	C10—C9—H9	120.00
C8—C9—C10	120.50 (17)	C9—C10—H10	120.00
C9—C10—C11	119.85 (18)	C11—C10—H10	120.00
C10—C11—C12	120.10 (18)	C10—C11—H11	120.00
C11—C12—C13	119.86 (17)	C12—C11—H11	120.00
C8—C13—C12	120.67 (17)	C11—C12—H12	120.00
O3—C2—H2	108.00	C13—C12—H12	120.00
C1—C2—H2	108.00	C8—C13—H13	120.00
C3—C2—H2	108.00	C12—C13—H13	120.00
C2—C3—H3A	109.00
C5—O2—C1—O1	167.84 (17)	O4—C4—C5—O2	169.39 (16)
C5—O2—C1—C2	−14.5 (2)	O4—C4—C5—C6	−67.5 (2)
C1—O2—C5—C4	25.4 (2)	O3—C4—C5—C6	112.51 (17)
C1—O2—C5—C6	−97.96 (18)	C4—C5—C6—O5	−60.64 (18)
C4—O3—C2—C1	25.7 (2)	O2—C5—C6—O5	66.08 (16)
C4—O3—C2—C3	149.34 (15)	O5—C7—C8—C9	66.3 (2)
C2—O3—C4—O4	165.23 (15)	O5—C7—C8—C13	−111.72 (19)
C2—O3—C4—C5	−14.8 (2)	C7—C8—C9—C10	−176.25 (17)
C7—O5—C6—C5	163.22 (14)	C9—C8—C13—C12	−1.8 (3)
C6—O5—C7—C8	57.98 (19)	C13—C8—C9—C10	1.8 (3)
O1—C1—C2—O3	166.86 (17)	C7—C8—C13—C12	176.25 (17)
O2—C1—C2—C3	−131.79 (19)	C8—C9—C10—C11	−0.4 (3)
O1—C1—C2—C3	45.9 (2)	C9—C10—C11—C12	−1.1 (3)
O2—C1—C2—O3	−10.8 (2)	C10—C11—C12—C13	1.1 (3)
O3—C4—C5—O2	−10.6 (2)	C11—C12—C13—C8	0.4 (3)

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x, y−1/2, −z+1; (v) x, y−1, z; (vi) −x, y−1/2, −z; (vii) x+1, y−1, z; (viii) −x+1, y−1/2, −z+1; (ix) x, y+1, z; (x) −x, y+1/2, −z; (xi) −x−1, y−1/2, −z; (xii) −x+1, y+1/2, −z+1; (xiii) x−1, y+1, z; (xiv) −x−1, y+1/2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2^iii	1.00	2.60	3.152 (2)	115
C10—H10···O4^xiii	0.95	2.57	3.465 (3)	158

Symmetry codes: (iii) x+1, y, z; (xiii) x−1, y+1, z.