Crystal packing and melting temperatures of small oxalate esters: the role of C—H...O hydrogen bonding

The simple dialkyl oxalates are generally liquids at room temperature except for dimethyl and di-tert-butyl oxalate which melt at 327 and 343 K. The crystal structures of diethyl, di-iso-propyl, di-n-butyl, di-tert-butyl and methyl ethyl oxalates were determined. The liquid esters were crystallized using the cryocrystallization technique. A comparison of the intermolecular interactions and packing features in these crystal structures was carried out. The crystal structure of dimethyl oxalate was redetermined at various temperatures. The other compounds were also studied at several temperatures in order to assess the attractive nature of the hydrogen bonds therein. A number of moderate to well defined C—H...O interactions account for the higher melting points of the two solid esters. Additionally, a diminished entropic contribution ΔS_m in di-tert-butyl oxalate possibly increases the melting point of this compound further.

Computing details

Data collection: Bruker SMART V5.628, (Bruker, 2004) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; CrysAlis PRO CCD (Oxford Diffraction, 2009) for DMO323, DMO273, DMO200, DMO150, DMO100; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) for DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125. Cell refinement: Bruker SMART V5.628, (Bruker, 2004) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; CrysAlis PRO CCD (Oxford Diffraction, 2009) for DMO323, DMO273, DMO200, DMO150, DMO100; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) for DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125. Data reduction: Bruker SAINT V6.45a, (Bruker, 2004) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; CrysAlis PRO RED (Oxford Diffraction, 2009) for DMO323, DMO273, DMO200, DMO150, DMO100; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) for DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125. Program(s) used to solve structure: SHELXTL V6.14 (Bruker, 2000) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; SHELXS97 (Sheldrick, 2008) for DMO323, DMO273, DMO200, DMO150, DMO100. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, MEO170, MEO90; ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993) for DMO323, DMO273, DMO200, DMO150, DMO100. Software used to prepare material for publication: PLATON (Spek, 2003) for DEO90, DEO170, DiPO210, DiPO90, DnBO210, DnBO90, DtBO250, DtBO225, DtBO200, DtBO175, DtBO150, DtBO125, MEO170, MEO90; WinGX (Farrugia, 1999) for DMO323, DMO273, DMO200, DMO150, DMO100.

Figures

(DEO90)

Crystal data

C6H10O4	F(000) = 312
Mr = 146.14	Dx = 1.326 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 894 reflections
a = 11.581 (4) Å	θ = 5.8–47.6°
b = 4.2812 (15) Å	µ = 0.11 mm^−1
c = 15.282 (5) Å	T = 90 K
β = 104.938 (6)°	Block, colourless
V = 732.1 (4) Å^3	0.50 × 0.50 × 0.35 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	817 reflections with > 2σ(i)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 25.4°, θmin = 1.8°
ϕ and ω scans	h = −13→13
6617 measured reflections	k = −5→5
1345 independent reflections	l = −18→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0552P)^2] where P = (Fo^2 + 2Fc^2)/3
1345 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.19 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.30789 (14)	0.9206 (4)	0.48973 (10)	0.0178 (6)
O2	0.19468 (14)	1.0568 (4)	0.25823 (11)	0.0181 (6)
O3	0.35363 (16)	0.6918 (4)	0.36993 (13)	0.0250 (7)
O4	0.13725 (16)	1.2547 (4)	0.37700 (13)	0.0252 (7)
C1	0.4042 (3)	0.8256 (8)	0.6463 (2)	0.0261 (10)
C2	0.3976 (3)	0.7243 (6)	0.5515 (2)	0.0201 (10)
C3	0.2966 (2)	0.8724 (6)	0.40214 (16)	0.0159 (8)
C4	0.1994 (2)	1.0889 (6)	0.34525 (16)	0.0164 (8)
C5	0.1057 (3)	1.2529 (6)	0.1966 (2)	0.0208 (10)
C6	0.1078 (3)	1.1725 (8)	0.1014 (2)	0.0264 (10)
H1A	0.462 (2)	0.693 (6)	0.6857 (19)	0.028 (8)*
H1B	0.325 (3)	0.794 (6)	0.6629 (19)	0.024 (8)*
H1C	0.431 (2)	1.056 (7)	0.6574 (18)	0.034 (8)*
H2A	0.476 (2)	0.751 (5)	0.5343 (17)	0.018 (8)*
H2B	0.367 (2)	0.505 (7)	0.5349 (17)	0.030 (8)*
H5A	0.028 (3)	1.211 (6)	0.208 (2)	0.032 (9)*
H5B	0.124 (2)	1.461 (6)	0.2114 (17)	0.019 (7)*
H6A	0.181 (3)	1.228 (7)	0.091 (2)	0.041 (10)*
H6B	0.086 (2)	0.950 (7)	0.0867 (16)	0.027 (7)*
H6C	0.041 (3)	1.300 (7)	0.057 (2)	0.039 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0201 (10)	0.0165 (10)	0.0139 (10)	0.0038 (7)	−0.0006 (7)	0.0007 (7)
O2	0.0195 (10)	0.0179 (10)	0.0138 (9)	0.0013 (7)	−0.0015 (7)	0.0002 (7)
O3	0.0252 (11)	0.0269 (11)	0.0209 (13)	0.0088 (9)	0.0024 (10)	−0.0023 (9)
O4	0.0225 (12)	0.0316 (12)	0.0193 (13)	0.0099 (8)	0.0017 (10)	−0.0007 (8)
C1	0.0313 (18)	0.0249 (16)	0.0178 (17)	0.0049 (15)	−0.0013 (14)	0.0023 (13)
C2	0.0220 (17)	0.0168 (15)	0.0173 (18)	0.0025 (11)	−0.0025 (13)	0.0045 (10)
C3	0.0133 (13)	0.0162 (14)	0.0175 (14)	−0.0038 (11)	0.0026 (11)	−0.0028 (11)
C4	0.0159 (13)	0.0163 (14)	0.0156 (14)	−0.0041 (11)	0.0013 (11)	−0.0015 (11)
C5	0.0194 (17)	0.0148 (15)	0.025 (2)	0.0022 (11)	−0.0003 (14)	0.0046 (11)
C6	0.0342 (19)	0.0218 (16)	0.0191 (17)	−0.0042 (15)	−0.0007 (14)	0.0012 (13)

Geometric parameters (Å, º)

O1—C2	1.474 (3)	C1—H1B	1.02 (4)
O1—C3	1.327 (3)	C1—H1C	1.04 (3)
O2—C4	1.324 (3)	C2—H2A	1.02 (2)
O2—C5	1.467 (3)	C2—H2B	1.01 (3)
O3—C3	1.202 (3)	C5—H5A	0.98 (4)
O4—C4	1.199 (3)	C5—H5B	0.93 (3)
C1—C2	1.495 (4)	C6—H6A	0.93 (4)
C3—C4	1.542 (4)	C6—H6B	1.00 (3)
C5—C6	1.501 (4)	C6—H6C	1.04 (3)
C1—H1A	0.96 (3)
O1···O4	2.677 (3)	C4···H5A^ix	3.02 (3)
O2···O3	2.669 (3)	C5···H5A^vii	3.09 (3)
O3···C4^i	3.106 (3)	H1A···C1^x	3.07 (3)
O3···C2^ii	3.337 (4)	H1A···H1C^x	2.47 (4)
O3···O2	2.669 (3)	H1B···O2^xi	2.79 (3)
O3···O4^i	3.152 (3)	H1C···H1A^viii	2.47 (4)
O4···C3^iii	3.191 (3)	H1C···O3^vi	2.85 (3)
O4···O1	2.677 (3)	H2A···O3	2.56 (3)
O4···O3^iii	3.152 (3)	H2A···O3^ii	2.85 (2)
O1···H6A^iv	2.83 (3)	H2A···C2^ii	3.00 (2)
O1···H2B^iii	2.64 (3)	H2A···C3^vi	3.03 (2)
O2···H1B^v	2.79 (3)	H2A···H2A^ii	2.52 (3)
O2···H5B^i	2.72 (3)	H2A···H2A^vi	2.50 (3)
O3···H2B	2.61 (3)	H2A···H2B^ii	2.57 (3)
O3···H2A^ii	2.85 (2)	H2B···O1^i	2.64 (3)
O3···H1C^vi	2.85 (3)	H2B···O3	2.61 (3)
O3···H2A	2.56 (3)	H2B···H2A^ii	2.57 (3)
O4···H5A	2.57 (3)	H5A···O4	2.57 (3)
O4···H5B	2.65 (3)	H5A···O4^ix	2.81 (3)
O4···H5A^vii	2.81 (3)	H5A···C4^vii	3.02 (3)
O4···H6B^vii	2.90 (2)	H5A···C5^ix	3.09 (3)
C2···O3^ii	3.337 (4)	H5B···O2^iii	2.72 (3)
C3···O4^i	3.191 (3)	H5B···O4	2.65 (3)
C3···C4^i	3.574 (4)	H6A···O1^xii	2.83 (3)
C4···C3^iii	3.574 (4)	H6B···O4^ix	2.90 (2)
C4···O3^iii	3.106 (3)	H6B···H6C^xiii	2.54 (4)
C1···H1A^viii	3.07 (3)	H6C···H6B^xiii	2.54 (4)
C2···H2A^ii	3.00 (2)	H6C···H6C^xiv	2.45 (4)
C3···H2A^vi	3.03 (2)
C2—O1—C3	115.3 (2)	O1—C2—H2A	107.5 (14)
C4—O2—C5	115.2 (2)	O1—C2—H2B	103.0 (15)
O1—C2—C1	107.9 (2)	C1—C2—H2A	113.1 (14)
O1—C3—O3	126.3 (2)	C1—C2—H2B	116.0 (15)
O1—C3—C4	110.1 (2)	H2A—C2—H2B	108.6 (19)
O3—C3—C4	123.7 (2)	O2—C5—H5A	107.9 (17)
O2—C4—O4	126.5 (2)	O2—C5—H5B	108.3 (15)
O2—C4—C3	109.8 (2)	C6—C5—H5A	112.1 (17)
O4—C4—C3	123.7 (2)	C6—C5—H5B	113.3 (16)
O2—C5—C6	107.9 (2)	H5A—C5—H5B	107 (2)
C2—C1—H1A	106.8 (16)	C5—C6—H6A	110.4 (19)
C2—C1—H1B	112.2 (16)	C5—C6—H6B	111.8 (14)
C2—C1—H1C	111.9 (15)	C5—C6—H6C	108.4 (18)
H1A—C1—H1B	107 (2)	H6A—C6—H6B	113 (2)
H1A—C1—H1C	109 (2)	H6A—C6—H6C	108 (3)
H1B—C1—H1C	110 (2)	H6B—C6—H6C	105 (2)
C3—O1—C2—C1	176.0 (2)	C4—O2—C5—C6	−176.7 (2)
C2—O1—C3—O3	−1.7 (4)	O1—C3—C4—O2	175.4 (2)
C2—O1—C3—C4	179.4 (2)	O1—C3—C4—O4	−5.9 (3)
C5—O2—C4—O4	1.7 (4)	O3—C3—C4—O2	−3.7 (3)
C5—O2—C4—C3	−179.6 (2)	O3—C3—C4—O4	175.1 (3)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x, −y+5/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) −x+1, −y+2, −z+1; (vii) −x, y+1/2, −z+1/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x, y−1/2, −z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) x, −y+3/2, z+1/2; (xii) x, −y+5/2, z−1/2; (xiii) −x, −y+2, −z; (xiv) −x, −y+3, −z.

(DEO170)

Crystal data

C6H10O4	F(000) = 312
Mr = 146.14	Dx = 1.304 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 749 reflections
a = 11.734 (4) Å	θ = 5.7–47.6°
b = 4.3096 (15) Å	µ = 0.11 mm^−1
c = 15.276 (5) Å	T = 170 K
β = 105.525 (6)°	Block, colourless
V = 744.3 (4) Å^3	0.50 × 0.50 × 0.35 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	757 reflections with > 2σ(i)
Radiation source: fine-focus sealed tube	Rint = 0.070
Graphite monochromator	θmax = 25.4°, θmin = 1.8°
ϕ and ω scans	h = −14→14
6823 measured reflections	k = −5→5
1373 independent reflections	l = −18→18

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0545P)^2 + 0.0265P] where P = (Fo^2 + 2Fc^2)/3
1373 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.20 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.30851 (15)	0.9188 (4)	0.48954 (10)	0.0328 (6)
O2	0.19415 (15)	1.0558 (4)	0.25811 (11)	0.0345 (6)
O3	0.35192 (17)	0.6924 (5)	0.37013 (13)	0.0447 (8)
O4	0.13894 (18)	1.2487 (5)	0.37703 (14)	0.0470 (8)
C1	0.4056 (4)	0.8231 (9)	0.6464 (2)	0.0486 (12)
C2	0.3969 (3)	0.7231 (7)	0.5509 (2)	0.0386 (11)
C3	0.2963 (2)	0.8712 (6)	0.40207 (16)	0.0285 (8)
C4	0.1996 (2)	1.0869 (6)	0.34521 (16)	0.0294 (9)
C5	0.1054 (3)	1.2512 (7)	0.1964 (2)	0.0362 (11)
C6	0.1078 (4)	1.1749 (10)	0.1019 (2)	0.0500 (14)
H1A	0.466 (3)	0.689 (8)	0.686 (2)	0.074 (11)*
H1B	0.332 (3)	0.785 (7)	0.660 (2)	0.056 (11)*
H1C	0.434 (3)	1.041 (8)	0.660 (2)	0.058 (9)*
H2A	0.474 (2)	0.754 (6)	0.5347 (18)	0.041 (9)*
H2B	0.368 (2)	0.508 (7)	0.5350 (18)	0.051 (9)*
H5A	0.030 (3)	1.203 (7)	0.209 (2)	0.074 (12)*
H5B	0.129 (3)	1.455 (7)	0.214 (2)	0.054 (9)*
H6A	0.177 (3)	1.235 (8)	0.089 (3)	0.093 (16)*
H6B	0.091 (3)	0.949 (8)	0.0890 (19)	0.066 (10)*
H6C	0.043 (3)	1.298 (8)	0.059 (2)	0.076 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (11)	0.0343 (11)	0.0221 (10)	0.0053 (9)	−0.0005 (8)	−0.0008 (8)
O2	0.0381 (11)	0.0365 (11)	0.0243 (10)	0.0035 (9)	0.0004 (8)	0.0016 (8)
O3	0.0449 (13)	0.0536 (14)	0.0326 (13)	0.0163 (10)	0.0053 (11)	−0.0049 (10)
O4	0.0452 (15)	0.0613 (15)	0.0321 (14)	0.0201 (10)	0.0063 (12)	−0.0005 (9)
C1	0.061 (2)	0.047 (2)	0.031 (2)	0.002 (2)	0.0006 (18)	0.0006 (16)
C2	0.043 (2)	0.0369 (19)	0.031 (2)	0.0044 (14)	0.0013 (16)	0.0048 (12)
C3	0.0261 (14)	0.0310 (15)	0.0267 (15)	−0.0046 (13)	0.0042 (12)	−0.0059 (12)
C4	0.0289 (15)	0.0322 (16)	0.0262 (15)	−0.0048 (13)	0.0060 (12)	−0.0028 (12)
C5	0.037 (2)	0.0342 (19)	0.031 (2)	0.0025 (13)	−0.0021 (16)	0.0076 (12)
C6	0.065 (3)	0.048 (2)	0.0290 (19)	−0.002 (2)	−0.0012 (17)	0.0042 (16)

Geometric parameters (Å, º)

O1—C2	1.465 (4)	C1—H1B	0.96 (4)
O1—C3	1.321 (3)	C1—H1C	1.00 (3)
O2—C4	1.322 (3)	C2—H2A	1.01 (2)
O2—C5	1.469 (4)	C2—H2B	1.00 (3)
O3—C3	1.195 (3)	C5—H5A	0.98 (4)
O4—C4	1.189 (3)	C5—H5B	0.94 (3)
C1—C2	1.498 (4)	C6—H6A	0.92 (4)
C3—C4	1.542 (4)	C6—H6B	1.00 (3)
C5—C6	1.488 (4)	C6—H6C	1.01 (3)
C1—H1A	0.99 (3)
O1···O4	2.665 (3)	C1···H1A^viii	3.04 (3)
O2···O3	2.667 (3)	C2···H2A^ii	3.05 (3)
O3···C4^i	3.128 (3)	C3···H2A^vi	3.07 (3)
O3···C2^ii	3.383 (4)	C4···H5A^ix	3.08 (3)
O3···O2	2.667 (3)	H1A···C1^x	3.04 (3)
O3···O4^i	3.171 (3)	H1A···H1C^x	2.42 (4)
O4···C3^iii	3.221 (4)	H1B···O2^xi	2.88 (3)
O4···O1	2.665 (3)	H1C···H1A^viii	2.42 (4)
O4···O3^iii	3.171 (3)	H1C···O3^vi	2.91 (4)
O1···H6A^iv	2.86 (4)	H2A···O3	2.55 (3)
O1···H2B^iii	2.68 (3)	H2A···O3^ii	2.90 (3)
O2···H1B^v	2.88 (3)	H2A···C2^ii	3.05 (3)
O2···H5B^i	2.73 (3)	H2A···C3^vi	3.07 (3)
O3···H2B	2.60 (3)	H2A···H2A^ii	2.58 (4)
O3···H2A^ii	2.90 (3)	H2A···H2A^vi	2.52 (4)
O3···H1C^vi	2.91 (4)	H2B···O1^i	2.68 (3)
O3···H2A	2.55 (3)	H2B···O3	2.60 (3)
O4···H5A	2.55 (3)	H5A···O4	2.55 (3)
O4···H5B	2.62 (3)	H5A···O4^ix	2.85 (3)
O4···H5A^vii	2.85 (3)	H5A···C4^vii	3.08 (3)
C2···O3^ii	3.383 (4)	H5B···O2^iii	2.73 (3)
C3···O4^i	3.221 (4)	H5B···O4	2.62 (3)
C3···C4^i	3.597 (4)	H6A···O1^xii	2.86 (4)
C4···C3^iii	3.597 (4)	H6C···H6C^xiii	2.52 (5)
C4···O3^iii	3.128 (3)
C2—O1—C3	115.1 (2)	O1—C2—H2A	107.2 (15)
C4—O2—C5	115.0 (2)	O1—C2—H2B	104.1 (15)
O1—C2—C1	108.0 (3)	C1—C2—H2A	111.7 (15)
O1—C3—O3	126.1 (2)	C1—C2—H2B	115.8 (16)
O1—C3—C4	109.9 (2)	H2A—C2—H2B	109 (2)
O3—C3—C4	124.0 (2)	O2—C5—H5A	106.0 (18)
O2—C4—O4	126.7 (2)	O2—C5—H5B	104 (2)
O2—C4—C3	109.6 (2)	C6—C5—H5A	113.4 (18)
O4—C4—C3	123.6 (2)	C6—C5—H5B	113.8 (19)
O2—C5—C6	107.6 (3)	H5A—C5—H5B	111 (3)
C2—C1—H1A	106.2 (18)	C5—C6—H6A	113 (3)
C2—C1—H1B	109.4 (18)	C5—C6—H6B	110.6 (17)
C2—C1—H1C	113.9 (18)	C5—C6—H6C	107.9 (19)
H1A—C1—H1B	108 (3)	H6A—C6—H6B	112 (3)
H1A—C1—H1C	106 (3)	H6A—C6—H6C	106 (3)
H1B—C1—H1C	113 (3)	H6B—C6—H6C	108 (3)
C3—O1—C2—C1	175.9 (3)	C4—O2—C5—C6	−177.3 (3)
C2—O1—C3—O3	−1.9 (4)	O1—C3—C4—O2	175.1 (2)
C2—O1—C3—C4	179.1 (2)	O1—C3—C4—O4	−6.4 (4)
C5—O2—C4—O4	1.9 (4)	O3—C3—C4—O2	−3.9 (4)
C5—O2—C4—C3	−179.7 (2)	O3—C3—C4—O4	174.6 (3)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x, −y+5/2, z+1/2; (v) x, −y+3/2, z−1/2; (vi) −x+1, −y+2, −z+1; (vii) −x, y+1/2, −z+1/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x, y−1/2, −z+1/2; (x) −x+1, y−1/2, −z+3/2; (xi) x, −y+3/2, z+1/2; (xii) x, −y+5/2, z−1/2; (xiii) −x, −y+3, −z.

(DMO323)

Crystal data

C4H6O4	F(000) = 124
Mr = 118.09	Dx = 1.390 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 524 reflections
a = 3.9101 (19) Å	θ = 3.4–25.4°
b = 11.907 (5) Å	µ = 0.13 mm^−1
c = 6.221 (3) Å	T = 323 K
β = 103.10 (5)°	Plate, colourless
V = 282.1 (2) Å^3	0.25 × 0.20 × 0.17 mm
Z = 2

Data collection

Oxford Xcalibur,Eos(Nova) CCD detector diffractometer	275 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.052
Graphite monochromator	θmax = 25.4°, θmin = 3.4°
ω scans	h = −4→4
2421 measured reflections	k = −14→14
524 independent reflections	l = −7→7

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0915P)^2] where P = (Fo^2 + 2Fc^2)/3
524 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.13 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2490 (6)	0.11750 (19)	0.4716 (3)	0.0933 (10)
O2	0.0903 (5)	0.05077 (16)	0.7691 (3)	0.0764 (9)
C1	0.0973 (8)	0.0498 (2)	0.5571 (5)	0.0660 (11)
C2	0.2701 (12)	0.1423 (4)	0.9008 (7)	0.0909 (17)
H1	0.265 (15)	0.129 (4)	1.038 (12)	0.18 (3)*
H2	0.192 (11)	0.219 (5)	0.832 (7)	0.147 (18)*
H3	0.512 (11)	0.150 (3)	0.870 (7)	0.121 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.125 (2)	0.0870 (17)	0.0756 (16)	−0.0261 (14)	0.0391 (15)	−0.0003 (12)
O2	0.0897 (17)	0.0874 (18)	0.0572 (14)	−0.0065 (11)	0.0272 (11)	−0.0041 (10)
C1	0.075 (2)	0.0659 (18)	0.0617 (19)	0.0066 (14)	0.0251 (15)	0.0072 (14)
C2	0.104 (3)	0.100 (3)	0.072 (3)	−0.018 (2)	0.027 (2)	−0.019 (2)

Geometric parameters (Å, º)

O1—C1	1.195 (4)	C2—H1	0.87 (7)
O2—C1	1.325 (4)	C2—H2	1.03 (6)
O2—C2	1.446 (5)	C2—H3	1.01 (4)
C1—C1^i	1.498 (4)
O1···C1^ii	3.337 (4)	C1···O1^iii	3.277 (4)
O1···O2^i	2.668 (3)	C1···C1^iii	3.584 (5)
O1···C1^iii	3.277 (4)	C2···O1^viii	3.392 (6)
O1···C2^iv	3.392 (6)	C2···H3^vii	2.93 (4)
O2···O1^i	2.668 (3)	H1···O1^ix	2.72 (7)
O1···H1^v	2.72 (7)	H2···O1	2.60 (5)
O1···H2	2.60 (5)	H2···O1^x	2.87 (5)
O1···H2^iv	2.90 (5)	H2···O1^viii	2.90 (5)
O1···H2^vi	2.87 (5)	H3···O1	2.49 (4)
O1···H3	2.49 (4)	H3···O2^ii	2.75 (4)
O2···H3^vii	2.75 (4)	H3···C2^ii	2.93 (4)
C1···O1^vii	3.337 (4)
C1—O2—C2	117.0 (3)	O2—C2—H2	112 (3)
O1—C1—O2	124.2 (3)	O2—C2—H3	109 (2)
O1—C1—C1^i	125.0 (3)	H1—C2—H2	120 (4)
O2—C1—C1^i	110.9 (2)	H1—C2—H3	116 (5)
O2—C2—H1	108 (3)	H2—C2—H3	93 (3)
C2—O2—C1—O1	2.0 (5)	O1—C1—C1^i—O2^i	−2.3 (4)
C2—O2—C1—C1^i	179.7 (3)	O2—C1—C1^i—O1^i	2.3 (4)
O1—C1—C1^i—O1^i	180.0 (3)	O2—C1—C1^i—O2^i	180.0 (2)

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

(DMO273)

Crystal data

C4H6O4	F(000) = 124
Mr = 118.09	Dx = 1.412 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 515 reflections
a = 3.873 (2) Å	θ = 3.4–25.4°
b = 11.875 (4) Å	µ = 0.13 mm^−1
c = 6.205 (2) Å	T = 273 K
β = 103.37 (4)°	Plate, colourless
V = 277.7 (2) Å^3	0.25 × 0.20 × 0.17 mm
Z = 2

Data collection

Oxford Xcalibur,Eos(Nova) CCD detector diffractometer	319 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.063
Graphite monochromator	θmax = 25.4°, θmin = 3.4°
ω scans	h = −4→4
3942 measured reflections	k = −14→14
515 independent reflections	l = −7→7

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.097P)^2] where P = (Fo^2 + 2Fc^2)/3
515 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.21 e Å^−3
0 restraints	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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2512 (6)	0.11841 (16)	0.4725 (3)	0.0767 (9)
O2	0.0900 (5)	0.05049 (14)	0.7699 (3)	0.0624 (8)
C1	0.1014 (7)	0.05032 (19)	0.5591 (4)	0.0542 (9)
C2	0.2749 (10)	0.1419 (3)	0.9043 (6)	0.0732 (12)
H1	0.235 (9)	0.127 (2)	1.052 (7)	0.089 (11)*
H2	0.192 (10)	0.210 (4)	0.834 (6)	0.112 (15)*
H3	0.546 (11)	0.136 (3)	0.911 (6)	0.105 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1048 (19)	0.0662 (13)	0.0654 (14)	−0.0197 (11)	0.0325 (13)	0.0018 (10)
O2	0.0739 (15)	0.0647 (13)	0.0510 (13)	−0.0051 (8)	0.0193 (10)	−0.0031 (7)
C1	0.0613 (17)	0.0526 (14)	0.0509 (16)	0.0092 (11)	0.0177 (13)	0.0057 (11)
C2	0.082 (2)	0.076 (2)	0.062 (2)	−0.0086 (18)	0.0172 (18)	−0.0126 (17)

Geometric parameters (Å, º)

O1—C1	1.193 (3)	C2—H1	0.98 (4)
O2—C1	1.319 (3)	C2—H2	0.94 (5)
O2—C2	1.453 (4)	C2—H3	1.04 (4)
C1—C1^i	1.522 (3)
O1···C1^ii	3.312 (4)	C1···O1^iii	3.251 (4)
O1···O2^i	2.667 (3)	C1···C1^iii	3.542 (4)
O1···C1^iii	3.251 (4)	C2···O1^ix	3.365 (5)
O1···C2^iv	3.365 (5)	C2···H3^vii	2.83 (4)
O2···O1^i	2.667 (3)	H1···O1^x	2.60 (4)
O1···H1^v	2.60 (4)	H1···O2^viii	2.81 (3)
O1···H3	2.70 (4)	H2···O1	2.55 (4)
O1···H2^vi	2.91 (4)	H2···O1^xi	2.91 (4)
O1···H2	2.55 (4)	H3···O1	2.70 (4)
O2···H3^vii	2.66 (4)	H3···O2^ii	2.66 (4)
O2···H1^viii	2.81 (3)	H3···C2^ii	2.83 (4)
C1···O1^vii	3.312 (4)
C1—O2—C2	116.5 (2)	O2—C2—H2	108 (2)
O1—C1—O2	125.2 (2)	O2—C2—H3	109 (2)
O1—C1—C1^i	124.5 (2)	H1—C2—H2	119 (3)
O2—C1—C1^i	110.3 (2)	H1—C2—H3	109 (3)
O2—C2—H1	103.8 (17)	H2—C2—H3	108 (3)
C2—O2—C1—O1	0.3 (4)	O1—C1—C1^i—O2^i	−0.6 (4)
C2—O2—C1—C1^i	179.7 (2)	O2—C1—C1^i—O1^i	0.6 (4)
O1—C1—C1^i—O1^i	180.0 (3)	O2—C1—C1^i—O2^i	−180.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H1···O1^x	0.98 (4)	2.60 (4)	3.559 (4)	167 (2)

Symmetry code: (x) x, y, z+1.

(DMO200)

Crystal data

C4H6O4	F(000) = 124
Mr = 118.09	Dx = 1.426 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 508 reflections
a = 3.851 (2) Å	θ = 3.4–25.4°
b = 11.840 (6) Å	µ = 0.13 mm^−1
c = 6.227 (3) Å	T = 200 K
β = 104.31 (5)°	Plate, colourless
V = 275.1 (2) Å^3	0.25 × 0.20 × 0.17 mm
Z = 2

Data collection

Oxford Xcalibur,Eos(Nova) CCD detector diffractometer	390 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.074
Graphite monochromator	θmax = 25.4°, θmin = 3.4°
ω scans	h = −4→4
4697 measured reflections	k = −14→14
508 independent reflections	l = −7→7

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0792P)^2 + 0.1169P] where P = (Fo^2 + 2Fc^2)/3
508 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.23 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2569 (5)	0.11916 (15)	0.4753 (3)	0.0532 (8)
O2	0.0908 (5)	0.04940 (14)	0.7725 (3)	0.0429 (7)
C1	0.1044 (7)	0.05054 (19)	0.5606 (4)	0.0374 (8)
C2	0.2765 (8)	0.1420 (3)	0.9076 (5)	0.0504 (10)
H1	0.236 (10)	0.129 (3)	1.058 (7)	0.075 (11)*
H2	0.171 (9)	0.216 (3)	0.847 (5)	0.063 (9)*
H3	0.532 (9)	0.140 (2)	0.908 (5)	0.062 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0696 (16)	0.0505 (12)	0.0416 (11)	−0.0140 (9)	0.0180 (11)	−0.0006 (8)
O2	0.0480 (12)	0.0500 (12)	0.0303 (10)	−0.0039 (8)	0.0090 (8)	−0.0019 (7)
C1	0.0383 (14)	0.0400 (14)	0.0329 (13)	0.0055 (10)	0.0072 (11)	0.0032 (10)
C2	0.0506 (19)	0.0580 (19)	0.0415 (16)	−0.0051 (14)	0.0093 (14)	−0.0093 (13)

Geometric parameters (Å, º)

O1—C1	1.201 (3)	C2—H1	1.00 (4)
O2—C1	1.334 (3)	C2—H2	1.00 (3)
O2—C2	1.457 (4)	C2—H3	0.98 (4)
C1—C1^i	1.533 (3)
O1···C1^ii	3.277 (4)	C1···O1^iii	3.226 (4)
O1···O2^i	2.671 (3)	C1···C1^iii	3.525 (4)
O1···C1^iii	3.226 (4)	C2···O1^ix	3.348 (4)
O1···C2^iv	3.348 (4)	C2···H3^vii	2.87 (4)
O2···O1^i	2.671 (3)	H1···O1^x	2.58 (4)
O1···H1^v	2.58 (4)	H1···O2^viii	2.80 (4)
O1···H3	2.65 (3)	H2···O1	2.68 (3)
O1···H2^vi	2.76 (4)	H2···O1^xi	2.76 (4)
O1···H2	2.68 (3)	H3···O1	2.65 (3)
O2···H3^vii	2.72 (3)	H3···O2^ii	2.72 (3)
O2···H1^viii	2.80 (4)	H3···C2^ii	2.87 (4)
C1···O1^vii	3.277 (4)
C1—O2—C2	115.5 (2)	O2—C2—H2	110.2 (19)
O1—C1—O2	126.0 (2)	O2—C2—H3	109.3 (15)
O1—C1—C1^i	124.4 (2)	H1—C2—H2	110 (3)
O2—C1—C1^i	109.6 (2)	H1—C2—H3	113 (3)
O2—C2—H1	105 (2)	H2—C2—H3	110 (3)
C2—O2—C1—O1	0.9 (4)	O1—C1—C1^i—O2^i	−0.3 (4)
C2—O2—C1—C1^i	−179.4 (2)	O2—C1—C1^i—O1^i	0.3 (4)
O1—C1—C1^i—O1^i	180.0 (3)	O2—C1—C1^i—O2^i	−180.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H1···O1^x	1.00 (4)	2.58 (4)	3.565 (4)	168 (3)

Symmetry code: (x) x, y, z+1.

(DMO150)

Crystal data

C4H6O4	F(000) = 124
Mr = 118.09	Dx = 1.466 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 491 reflections
a = 3.8083 (15) Å	θ = 3.5–25.4°
b = 11.742 (4) Å	µ = 0.13 mm^−1
c = 6.1664 (18) Å	T = 150 K
β = 104.06 (3)°	Plate, colourless
V = 267.48 (16) Å^3	0.25 × 0.20 × 0.17 mm
Z = 2

Data collection

Oxford Xcalibur,Eos(Nova) CCD detector diffractometer	372 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.046
Graphite monochromator	θmax = 25.4°, θmin = 3.5°
ω scans	h = −4→4
2457 measured reflections	k = −14→14
491 independent reflections	l = −7→7

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.074P)^2] where P = (Fo^2 + 2Fc^2)/3
491 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.21 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2596 (4)	0.11989 (12)	0.4776 (2)	0.0386 (6)
O2	0.0918 (4)	0.04901 (11)	0.7740 (2)	0.0318 (5)
C1	0.1056 (5)	0.05067 (16)	0.5621 (3)	0.0277 (7)
C2	0.2793 (7)	0.1420 (2)	0.9107 (4)	0.0364 (8)
H1	0.244 (7)	0.1257 (19)	1.057 (5)	0.046 (7)*
H2	0.180 (7)	0.215 (2)	0.848 (4)	0.056 (8)*
H3	0.537 (7)	0.1392 (19)	0.909 (4)	0.048 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0509 (12)	0.0383 (10)	0.0296 (9)	−0.0098 (7)	0.0157 (8)	−0.0002 (7)
O2	0.0379 (10)	0.0370 (9)	0.0217 (9)	−0.0028 (6)	0.0098 (7)	−0.0014 (5)
C1	0.0287 (12)	0.0329 (11)	0.0226 (11)	0.0063 (9)	0.0083 (9)	0.0023 (8)
C2	0.0406 (16)	0.0432 (14)	0.0261 (13)	−0.0047 (11)	0.0093 (11)	−0.0059 (10)

Geometric parameters (Å, º)

O1—C1	1.194 (2)	C2—H1	0.96 (3)
O2—C1	1.321 (2)	C2—H2	0.98 (2)
O2—C2	1.456 (3)	C2—H3	0.99 (3)
C1—C1^i	1.533 (3)
O1···C1^ii	3.240 (3)	C1···O1^iii	3.194 (3)
O1···O2^i	2.669 (2)	C1···C1^iii	3.485 (3)
O1···C1^iii	3.194 (3)	C2···O1^ix	3.312 (3)
O1···C2^iv	3.312 (3)	C2···H3^vii	2.83 (3)
O2···O1^i	2.669 (2)	H1···O1^x	2.58 (3)
O1···H1^v	2.58 (3)	H1···O2^viii	2.75 (3)
O1···H2	2.63 (2)	H2···O1	2.63 (2)
O1···H2^iv	2.90 (3)	H2···O1^xi	2.75 (3)
O1···H2^vi	2.75 (3)	H2···O1^ix	2.90 (3)
O1···H3	2.62 (2)	H3···O1	2.62 (2)
O2···H3^vii	2.67 (3)	H3···O2^ii	2.67 (3)
O2···H1^viii	2.75 (3)	H3···C2^ii	2.83 (3)
C1···O1^vii	3.240 (3)
C1—O2—C2	115.46 (16)	O2—C2—H2	109.9 (15)
O1—C1—O2	125.73 (18)	O2—C2—H3	108.6 (13)
O1—C1—C1^i	124.35 (17)	H1—C2—H2	115 (2)
O2—C1—C1^i	109.92 (16)	H1—C2—H3	112 (2)
O2—C2—H1	103.5 (15)	H2—C2—H3	108 (2)
C2—O2—C1—O1	1.0 (3)	O1—C1—C1^i—O2^i	−0.3 (3)
C2—O2—C1—C1^i	−179.31 (17)	O2—C1—C1^i—O1^i	0.3 (3)
O1—C1—C1^i—O1^i	−180.0 (2)	O2—C1—C1^i—O2^i	179.98 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H1···O1^x	0.96 (3)	2.58 (3)	3.524 (3)	166.5 (19)

Symmetry code: (x) x, y, z+1.

(DMO100)

Crystal data

C4H6O4	F(000) = 124
Mr = 118.09	Dx = 1.476 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 489 reflections
a = 3.7844 (10) Å	θ = 3.5–25.4°
b = 11.751 (2) Å	µ = 0.14 mm^−1
c = 6.1753 (14) Å	T = 100 K
β = 104.59 (2)°	Plate, colourless
V = 265.76 (11) Å^3	0.25 × 0.20 × 0.17 mm
Z = 2

Data collection

Oxford Xcalibur,Eos(Nova) CCD detector diffractometer	394 reflections with > 2σ(i)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.042
Graphite monochromator	θmax = 25.4°, θmin = 3.5°
ω scans	h = −4→4
2188 measured reflections	k = −14→14
489 independent reflections	l = −7→7

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.2505P] where P = (Fo^2 + 2Fc^2)/3
489 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.23 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2613 (5)	0.12031 (15)	0.4794 (3)	0.0264 (6)
O2	0.0917 (5)	0.04868 (14)	0.7755 (3)	0.0212 (6)
C1	0.1059 (7)	0.0507 (2)	0.5639 (4)	0.0189 (8)
C2	0.2791 (8)	0.1417 (2)	0.9129 (4)	0.0235 (9)
H1	0.236 (8)	0.127 (2)	1.062 (5)	0.025 (7)*
H2	0.169 (8)	0.214 (3)	0.860 (5)	0.027 (7)*
H3	0.545 (9)	0.139 (2)	0.914 (5)	0.030 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0339 (12)	0.0268 (11)	0.0205 (10)	−0.0042 (8)	0.0104 (9)	0.0005 (8)
O2	0.0246 (10)	0.0254 (10)	0.0145 (10)	−0.0018 (8)	0.0064 (7)	−0.0015 (7)
C1	0.0177 (13)	0.0235 (14)	0.0164 (13)	0.0055 (10)	0.0062 (10)	0.0030 (10)
C2	0.0246 (16)	0.0280 (15)	0.0186 (14)	−0.0017 (12)	0.0069 (12)	−0.0051 (11)

Geometric parameters (Å, º)

O1—C1	1.201 (3)	C2—H1	0.99 (3)
O2—C1	1.322 (3)	C2—H2	0.97 (3)
O2—C2	1.454 (3)	C2—H3	1.01 (4)
C1—C1^i	1.538 (3)
O1···C1^ii	3.212 (3)	C1···O1^iii	3.189 (3)
O1···O2^i	2.673 (3)	C1···C1^iii	3.482 (4)
O1···C1^iii	3.189 (3)	C2···O1^ix	3.308 (3)
O1···C2^iv	3.308 (3)	C2···H3^viii	2.78 (4)
O2···O2^v	3.232 (3)	H1···O1^x	2.56 (3)
O2···O1^i	2.673 (3)	H1···H3^viii	2.55 (5)
O1···H1^vi	2.56 (3)	H1···O2^v	2.73 (3)
O1···H2^iv	2.92 (3)	H2···O1	2.70 (3)
O1···H2	2.70 (3)	H2···O1^xi	2.70 (3)
O1···H3	2.64 (3)	H2···O1^ix	2.92 (3)
O1···H2^vii	2.70 (3)	H3···O1	2.64 (3)
O2···H3^viii	2.65 (3)	H3···O2^ii	2.65 (3)
O2···H1^v	2.73 (3)	H3···C2^ii	2.78 (4)
C1···O1^viii	3.212 (3)	H3···H1^ii	2.55 (5)
C1—O2—C2	115.35 (19)	O2—C2—H2	111.0 (19)
O1—C1—O2	126.0 (2)	O2—C2—H3	108.7 (15)
O1—C1—C1^i	123.6 (2)	H1—C2—H2	108 (2)
O2—C1—C1^i	110.3 (2)	H1—C2—H3	113 (2)
O2—C2—H1	104.0 (15)	H2—C2—H3	112 (2)
C2—O2—C1—O1	1.1 (4)	O1—C1—C1^i—O2^i	−0.3 (4)
C2—O2—C1—C1^i	−179.2 (2)	O2—C1—C1^i—O1^i	0.3 (4)
O1—C1—C1^i—O1^i	180.0 (3)	O2—C1—C1^i—O2^i	180.0 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H1···O1^x	0.99 (3)	2.56 (3)	3.525 (3)	166 (2)

Symmetry code: (x) x, y, z+1.

(DiPO210)

Crystal data

C8H14O4	F(000) = 188
Mr = 174.19	Dx = 1.173 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1370 reflections
a = 4.3575 (12) Å	θ = 5.4–48.2°
b = 9.949 (3) Å	µ = 0.09 mm^−1
c = 11.384 (3) Å	T = 210 K
β = 92.483 (5)°	Block, colourless
V = 493.1 (2) Å^3	0.50 × 0.50 × 0.35 mm
Z = 2

Data collection

Bruker SMART CCD area detector diffractometer	676 reflections with > 2σ(i)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 25.4°, θmin = 2.7°
ϕ and ω scans	h = −5→5
4599 measured reflections	k = −12→12
909 independent reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0396P)^2 + 0.131P] where P = (Fo^2 + 2Fc^2)/3
909 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.13 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2924 (3)	0.54776 (12)	0.10101 (11)	0.0491 (4)
O2	0.0904 (3)	0.34389 (12)	0.06104 (10)	0.0382 (4)
C1	0.1168 (4)	0.47524 (16)	0.04781 (13)	0.0320 (5)
C2	0.3049 (5)	0.27882 (18)	0.14751 (16)	0.0422 (6)
C3	0.3363 (10)	0.1372 (3)	0.1064 (3)	0.0813 (13)
C4	0.1794 (7)	0.2909 (3)	0.2674 (2)	0.0611 (9)
H2	0.497 (5)	0.3308 (19)	0.1440 (16)	0.047 (5)*
H3A	0.136 (9)	0.100 (3)	0.096 (3)	0.116 (13)*
H3B	0.460 (6)	0.091 (3)	0.163 (2)	0.080 (7)*
H3C	0.431 (7)	0.134 (3)	0.031 (3)	0.109 (11)*
H4A	−0.014 (6)	0.236 (3)	0.270 (2)	0.080 (8)*
H4B	0.153 (6)	0.386 (3)	0.288 (2)	0.078 (8)*
H4C	0.317 (5)	0.248 (2)	0.324 (2)	0.071 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0515 (8)	0.0400 (7)	0.0541 (8)	−0.0039 (6)	−0.0177 (6)	−0.0009 (6)
O2	0.0412 (7)	0.0332 (7)	0.0395 (7)	0.0002 (5)	−0.0049 (5)	0.0068 (5)
C1	0.0329 (9)	0.0313 (9)	0.0319 (9)	0.0009 (8)	0.0038 (7)	0.0000 (7)
C2	0.0428 (11)	0.0410 (11)	0.0421 (11)	0.0037 (9)	−0.0063 (8)	0.0102 (8)
C3	0.119 (3)	0.0514 (15)	0.0710 (19)	0.0351 (17)	−0.0243 (19)	0.0030 (12)
C4	0.0704 (17)	0.0681 (16)	0.0445 (12)	0.0078 (14)	−0.0013 (11)	0.0166 (11)

Geometric parameters (Å, º)

O1—C1	1.197 (2)	C3—H3A	0.95 (4)
O2—C1	1.321 (2)	C3—H3B	0.94 (3)
O2—C2	1.477 (2)	C3—H3C	0.97 (3)
C1—C1^i	1.539 (2)	C4—H4A	1.01 (3)
C2—C3	1.493 (4)	C4—H4B	0.98 (3)
C2—C4	1.497 (3)	C4—H4C	0.96 (2)
C2—H2	0.99 (2)
O1···C4	3.231 (3)	C4···O1	3.231 (3)
O1···C1^ii	3.151 (2)	C1···H4B	2.87 (2)
O1···O1^ii	3.135 (2)	H2···O1	2.378 (19)
O1···O2^i	2.6610 (19)	H2···O2^vi	2.79 (2)
O2···O1^i	2.6610 (19)	H3A···H4A	2.51 (4)
O1···H4B	2.76 (3)	H3B···H4C	2.51 (3)
O1···H4C^iii	2.73 (2)	H3B···O1^vii	2.88 (2)
O1···H4A^iv	2.70 (3)	H4A···H3A	2.51 (4)
O1···H2	2.378 (19)	H4A···O1^viii	2.70 (3)
O1···H3B^iii	2.88 (2)	H4B···O1	2.76 (3)
O2···H2^v	2.79 (2)	H4B···C1	2.87 (2)
C1···O1^ii	3.151 (2)	H4C···H3B	2.51 (3)
C1···C1^ii	3.591 (3)	H4C···O1^vii	2.73 (2)
C1—O2—C2	116.99 (13)	C2—C3—H3B	107.7 (17)
O1—C1—O2	126.55 (15)	C2—C3—H3C	110.9 (18)
O1—C1—C1^i	123.62 (15)	H3A—C3—H3B	113 (3)
O2—C1—C1^i	109.83 (13)	H3A—C3—H3C	108 (3)
O2—C2—C3	105.59 (19)	H3B—C3—H3C	110 (2)
O2—C2—C4	109.07 (18)	C2—C4—H4A	108.8 (14)
C3—C2—C4	113.8 (2)	C2—C4—H4B	110.2 (14)
O2—C2—H2	104.9 (11)	C2—C4—H4C	109.5 (13)
C3—C2—H2	113.1 (11)	H4A—C4—H4B	114 (2)
C4—C2—H2	109.8 (11)	H4A—C4—H4C	104 (2)
C2—C3—H3A	108 (2)	H4B—C4—H4C	110.1 (19)
C2—O2—C1—O1	−2.0 (2)	O1—C1—C1^i—O1^i	179.98 (19)
C2—O2—C1—C1^i	178.29 (14)	O2—C1—C1^i—O2^i	180.00 (13)
C1—O2—C2—C3	−153.2 (2)	O1—C1—C1^i—O2^i	0.3 (2)
C1—O2—C2—C4	84.1 (2)	O2—C1—C1^i—O1^i	−0.3 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.99 (2)	2.378 (19)	2.728 (2)	100.0 (14)

(DiPO90)

Crystal data

C8H14O4	F(000) = 188
Mr = 174.19	Dx = 1.210 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1802 reflections
a = 4.2679 (17) Å	θ = 5.5–55.5°
b = 9.947 (4) Å	µ = 0.10 mm^−1
c = 11.272 (5) Å	T = 90 K
β = 92.444 (7)°	Block, colourless
V = 478.1 (3) Å^3	0.50 × 0.50 × 0.35 mm
Z = 2

Data collection

Bruker SMART CCD area detector diffractometer	705 reflections with > 2σ(i)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 25.4°, θmin = 2.7°
ϕ and ω scans	h = −5→5
4124 measured reflections	k = −12→12
864 independent reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.347P] where P = (Fo^2 + 2Fc^2)/3
864 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.22 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2984 (4)	0.54623 (16)	0.10350 (13)	0.0218 (5)
O2	0.0889 (4)	0.34285 (15)	0.06043 (13)	0.0174 (5)
C1	0.1187 (5)	0.4745 (2)	0.04856 (17)	0.0146 (6)
C2	0.3045 (5)	0.2772 (2)	0.14859 (19)	0.0197 (7)
C3	0.3345 (9)	0.1343 (3)	0.1077 (3)	0.0366 (10)
C4	0.1764 (6)	0.2899 (3)	0.2700 (2)	0.0255 (8)
H2	0.496 (7)	0.322 (3)	0.145 (2)	0.020 (6)*
H3A	0.134 (10)	0.096 (4)	0.099 (3)	0.060 (11)*
H3B	0.457 (7)	0.080 (3)	0.165 (2)	0.034 (7)*
H3C	0.420 (9)	0.131 (3)	0.029 (3)	0.058 (10)*
H4A	−0.032 (8)	0.242 (3)	0.278 (3)	0.046 (9)*
H4B	0.138 (6)	0.382 (3)	0.290 (2)	0.025 (7)*
H4C	0.323 (7)	0.250 (3)	0.328 (3)	0.042 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0208 (9)	0.0194 (8)	0.0245 (8)	−0.0015 (6)	−0.0058 (6)	−0.0004 (6)
O2	0.0171 (8)	0.0160 (9)	0.0188 (8)	0.0004 (6)	−0.0028 (6)	0.0030 (6)
C1	0.0132 (11)	0.0155 (11)	0.0153 (10)	0.0014 (9)	0.0035 (8)	0.0003 (8)
C2	0.0188 (12)	0.0201 (12)	0.0197 (11)	0.0023 (9)	−0.0038 (9)	0.0056 (9)
C3	0.056 (2)	0.0256 (15)	0.0274 (14)	0.0140 (13)	−0.0090 (14)	0.0017 (11)
C4	0.0280 (14)	0.0269 (14)	0.0215 (12)	0.0036 (11)	−0.0009 (10)	0.0050 (10)

Geometric parameters (Å, º)

O1—C1	1.200 (3)	C3—H3A	0.94 (4)
O2—C1	1.323 (3)	C3—H3B	0.98 (3)
O2—C2	1.477 (3)	C3—H3C	0.97 (3)
C1—C1^i	1.545 (3)	C4—H4A	1.02 (3)
C2—C3	1.501 (4)	C4—H4B	0.96 (3)
C2—C4	1.501 (3)	C4—H4C	0.97 (3)
C2—H2	0.93 (3)
O1···C4	3.222 (3)	C1···H4B	2.87 (2)
O1···C1^ii	3.088 (3)	H2···O1	2.42 (3)
O1···O1^ii	3.097 (3)	H2···O2^vi	2.75 (3)
O1···O2^i	2.665 (3)	H2···H4A^vi	2.59 (4)
O2···O1^i	2.665 (3)	H3B···H4C	2.58 (4)
O1···H4B	2.77 (3)	H3B···O1^vii	2.79 (2)
O1···H4C^iii	2.69 (3)	H3C···H4C^viii	2.57 (5)
O1···H4A^iv	2.65 (3)	H4A···H2^v	2.59 (4)
O1···H2	2.42 (3)	H4A···O1^ix	2.65 (3)
O1···H3B^iii	2.79 (2)	H4B···O1	2.77 (3)
O2···H2^v	2.75 (3)	H4B···C1	2.87 (2)
C1···O1^ii	3.088 (3)	H4C···H3B	2.58 (4)
C1···C1^ii	3.515 (3)	H4C···O1^vii	2.69 (3)
C4···O1	3.222 (3)	H4C···H3C^x	2.57 (5)
C1—O2—C2	116.47 (16)	C2—C3—H3B	111.8 (17)
O1—C1—O2	126.75 (19)	C2—C3—H3C	110.6 (18)
O1—C1—C1^i	123.76 (18)	H3A—C3—H3B	108 (3)
O2—C1—C1^i	109.49 (17)	H3A—C3—H3C	106 (3)
O2—C2—C3	105.7 (2)	H3B—C3—H3C	112 (3)
O2—C2—C4	109.61 (18)	C2—C4—H4A	113.3 (19)
C3—C2—C4	113.5 (2)	C2—C4—H4B	111.6 (14)
O2—C2—H2	106.3 (16)	C2—C4—H4C	109.3 (19)
C3—C2—H2	110.6 (18)	H4A—C4—H4B	106 (2)
C4—C2—H2	110.7 (14)	H4A—C4—H4C	107 (3)
C2—C3—H3A	109 (3)	H4B—C4—H4C	110 (2)
C2—O2—C1—O1	−1.5 (3)	O1—C1—C1^i—O1^i	180.0 (2)
C2—O2—C1—C1^i	178.80 (16)	O2—C1—C1^i—O2^i	180.00 (17)
C1—O2—C2—C3	−154.2 (2)	O1—C1—C1^i—O2^i	0.3 (3)
C1—O2—C2—C4	83.2 (2)	O2—C1—C1^i—O1^i	−0.3 (3)

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

(DnBO210)

Crystal data

C10H18O4	Z = 1
Mr = 202.24	F(000) = 110
Triclinic, P1	Dx = 1.135 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.593 (4) Å	Cell parameters from 1094 reflections
b = 4.702 (4) Å	θ = 5.9–56.4°
c = 14.030 (11) Å	µ = 0.09 mm^−1
α = 95.896 (12)°	T = 210 K
β = 97.964 (12)°	Cylindrical, colourless
γ = 96.656 (13)°	0.50 × 0.50 × 0.35 mm
V = 295.9 (4) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	1197 independent reflections
Radiation source: fine-focus sealed tube	898 reflections with > 2σ(i)
Graphite monochromator	Rint = 0.047
ϕ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.958, Tmax = 0.970	k = −5→5
2968 measured reflections	l = −17→17

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)] = 0.115	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.320	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1477P)^2 + 0.5941P] where P = (Fo^2 + 2Fc^2)/3
1197 reflections	(Δ/σ)max < 0.001
73 parameters	Δρmax = 0.86 e Å^−3
0 restraints	Δρmin = −0.34 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2744 (7)	0.2455 (7)	0.0435 (2)	0.0424 (10)
O2	0.3295 (6)	0.0887 (6)	−0.1096 (2)	0.0381 (10)
C1	0.3835 (8)	0.1004 (8)	−0.0150 (3)	0.0290 (11)
C2	0.1077 (12)	0.2648 (13)	−0.1494 (4)	0.0486 (17)
C3	0.1898 (16)	0.3694 (16)	−0.2379 (4)	0.076 (3)
C4	0.2328 (19)	0.1651 (16)	−0.3185 (4)	0.084 (3)
C5	0.310 (2)	0.295 (2)	−0.4069 (5)	0.102 (4)
H2A	0.126 (16)	0.395 (16)	−0.102 (5)	0.09 (2)*
H2B	−0.086 (16)	0.137 (14)	−0.165 (4)	0.076 (19)*
H3A	0.03650	0.48320	−0.26250	0.0910*
H3B	0.37430	0.50250	−0.21920	0.0910*
H4A	0.05060	0.02910	−0.33760	0.1000*
H4B	0.39120	0.05440	−0.29560	0.1000*
H5A	0.15400	0.40260	−0.43120	0.1530*
H5B	0.33100	0.14200	−0.45650	0.1530*
H5C	0.49570	0.42300	−0.38990	0.1530*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0467 (18)	0.0433 (18)	0.0421 (18)	0.0265 (14)	0.0107 (13)	0.0004 (13)
O2	0.0418 (17)	0.0423 (17)	0.0380 (17)	0.0260 (13)	0.0114 (12)	0.0114 (12)
C1	0.0272 (19)	0.0242 (18)	0.038 (2)	0.0075 (15)	0.0092 (15)	0.0049 (15)
C2	0.050 (3)	0.056 (3)	0.048 (3)	0.033 (3)	0.007 (2)	0.016 (2)
C3	0.094 (5)	0.094 (5)	0.062 (4)	0.065 (4)	0.025 (3)	0.035 (3)
C4	0.117 (6)	0.090 (5)	0.057 (4)	0.056 (4)	0.015 (4)	0.021 (3)
C5	0.127 (7)	0.143 (7)	0.060 (4)	0.064 (6)	0.037 (4)	0.044 (4)

Geometric parameters (Å, º)

O1—C1	1.212 (5)	C2—H2B	1.00 (7)
O2—C1	1.310 (5)	C3—H3A	0.9800
O2—C2	1.473 (7)	C3—H3B	0.9800
C1—C1^i	1.551 (6)	C4—H4A	0.9800
C2—C3	1.462 (8)	C4—H4B	0.9800
C3—C4	1.457 (9)	C5—H5A	0.9700
C4—C5	1.505 (10)	C5—H5B	0.9700
C2—H2A	0.84 (7)	C5—H5C	0.9700
O1···C1^ii	3.214 (6)	C2···O1^iii	3.398 (7)
O1···O1^ii	3.224 (5)	H2A···O1	2.27 (7)
O1···O2^i	2.671 (5)	H2A···O1^iii	2.79 (7)
O1···C2^iii	3.398 (7)	H2B···O2^vi	2.89 (7)
O1···C1^iv	3.376 (6)	H2B···H4A	2.6000
O1···C2^ii	3.395 (7)	H2B···O1^ii	2.75 (6)
O2···O1^i	2.671 (5)	H3A···H5A	2.5000
O1···H2A^iii	2.79 (7)	H3B···H5C	2.5300
O1···H2B^ii	2.75 (6)	H3B···O1^iv	2.8200
O1···H2A	2.27 (7)	H4A···H2B	2.6000
O1···H3B^iv	2.8200	H4B···O2	2.6500
O2···H2B^v	2.89 (7)	H5A···H3A	2.5000
O2···H4B	2.6500	H5A···H5A^vii	2.5400
C1···O1^ii	3.214 (6)	H5B···H5B^viii	2.5200
C1···O1^iv	3.376 (6)	H5C···H3B	2.5300
C2···O1^ii	3.395 (7)
C1—O2—C2	116.8 (3)	C4—C3—H3A	107.00
O1—C1—O2	126.9 (4)	C4—C3—H3B	107.00
O1—C1—C1^i	122.8 (4)	H3A—C3—H3B	107.00
O2—C1—C1^i	110.4 (3)	C3—C4—H4A	108.00
O2—C2—C3	109.7 (5)	C3—C4—H4B	108.00
C2—C3—C4	120.0 (6)	C5—C4—H4A	108.00
C3—C4—C5	115.7 (7)	C5—C4—H4B	108.00
O2—C2—H2A	99 (5)	H4A—C4—H4B	107.00
O2—C2—H2B	107 (4)	C4—C5—H5A	110.00
C3—C2—H2A	114 (5)	C4—C5—H5B	109.00
C3—C2—H2B	110 (3)	C4—C5—H5C	109.00
H2A—C2—H2B	117 (6)	H5A—C5—H5B	110.00
C2—C3—H3A	107.00	H5A—C5—H5C	110.00
C2—C3—H3B	107.00	H5B—C5—H5C	109.00
C2—O2—C1—O1	−1.6 (6)	O2—C1—C1^i—O2^i	−180.0 (3)
C2—O2—C1—C1^i	179.0 (4)	O1—C1—C1^i—O2^i	0.5 (5)
C1—O2—C2—C3	146.3 (4)	O2—C2—C3—C4	56.6 (8)
O1—C1—C1^i—O1^i	180.0 (4)	C2—C3—C4—C5	178.7 (7)
O2—C1—C1^i—O1^i	−0.5 (5)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z; (v) x+1, y, z; (vi) x−1, y, z; (vii) −x, −y+1, −z−1; (viii) −x+1, −y, −z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.84 (7)	2.27 (7)	2.722 (7)	114 (6)

(DnBO90)

Crystal data

C10H18O4	Z = 1
Mr = 202.24	F(000) = 110
Triclinic, P1	Dx = 1.237 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.360 (2) Å	Cell parameters from 1713 reflections
b = 4.611 (2) Å	θ = 6.0–55.6°
c = 13.954 (7) Å	µ = 0.09 mm^−1
α = 81.486 (11)°	T = 90 K
β = 81.175 (8)°	Cylindrical, colourless
γ = 81.044 (8)°	0.50 × 0.50 × 0.35 mm
V = 271.6 (2) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	1204 independent reflections
Radiation source: fine-focus sealed tube	1046 reflections with > 2σ(i)
Graphite monochromator	Rint = 0.045
ϕ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.954, Tmax = 0.968	k = −5→5
2826 measured reflections	l = −17→17

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)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.252	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 1.1393P] where P = (Fo^2 + 2Fc^2)/3
1204 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −0.32 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.2350 (6)	0.2506 (6)	0.0423 (2)	0.0163 (8)
O2	0.4300 (6)	0.4178 (6)	−0.1108 (2)	0.0156 (8)
C1	0.3970 (8)	0.3974 (8)	−0.0158 (3)	0.0131 (10)
C2	0.2408 (10)	0.2474 (10)	−0.1526 (3)	0.0195 (11)
C3	0.4370 (10)	0.1191 (9)	−0.2384 (3)	0.0188 (11)
C4	0.5364 (11)	0.3461 (9)	−0.3231 (3)	0.0224 (12)
C5	0.7258 (13)	0.2039 (12)	−0.4085 (4)	0.0318 (16)
H2A	0.181 (12)	0.104 (12)	−0.099 (4)	0.027 (13)*
H2B	0.061 (15)	0.383 (14)	−0.177 (4)	0.043 (16)*
H3A	0.312 (13)	−0.006 (12)	−0.260 (4)	0.030 (14)*
H3B	0.626 (12)	−0.002 (11)	−0.218 (3)	0.021 (12)*
H4A	0.674 (11)	0.476 (11)	−0.298 (3)	0.020 (12)*
H4B	0.354 (14)	0.469 (13)	−0.343 (4)	0.038 (15)*
H5A	0.908 (13)	0.094 (12)	−0.389 (4)	0.029 (14)*
H5B	0.796 (13)	0.350 (13)	−0.468 (4)	0.038 (15)*
H5C	0.612 (15)	0.084 (15)	−0.433 (4)	0.048 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0110 (13)	0.0139 (13)	0.0248 (15)	−0.0033 (10)	−0.0021 (10)	−0.0040 (10)
O2	0.0104 (13)	0.0145 (13)	0.0247 (15)	−0.0058 (10)	−0.0044 (10)	−0.0053 (10)
C1	0.0061 (16)	0.0079 (16)	0.0234 (19)	0.0032 (13)	−0.0007 (13)	−0.0020 (13)
C2	0.0160 (19)	0.025 (2)	0.022 (2)	−0.0099 (16)	−0.0048 (15)	−0.0078 (16)
C3	0.019 (2)	0.0173 (19)	0.022 (2)	−0.0034 (16)	−0.0051 (15)	−0.0056 (15)
C4	0.026 (2)	0.020 (2)	0.022 (2)	−0.0047 (17)	−0.0022 (16)	−0.0045 (15)
C5	0.029 (3)	0.040 (3)	0.027 (2)	−0.005 (2)	0.0003 (19)	−0.010 (2)

Geometric parameters (Å, º)

O1—C1	1.194 (5)	C2—H2B	0.99 (6)
O2—C1	1.302 (5)	C3—H3A	0.96 (6)
O2—C2	1.457 (5)	C3—H3B	0.98 (5)
C1—C1^i	1.551 (5)	C4—H4A	1.04 (5)
C2—C3	1.501 (6)	C4—H4B	0.96 (6)
C3—C4	1.516 (6)	C5—H5A	0.93 (6)
C4—C5	1.514 (7)	C5—H5B	1.03 (6)
C2—H2A	0.96 (5)	C5—H5C	0.93 (6)
O1···C2^ii	3.377 (5)	C2···O1^ii	3.377 (5)
O1···O1^iii	3.222 (4)	C2···O1^iii	3.356 (5)
O1···O1^iv	3.058 (4)	C2···O1^iv	3.257 (5)
O1···O2^iv	3.140 (4)	C3···O1^iii	3.391 (5)
O1···O2^i	2.635 (4)	H2A···O1	2.23 (5)
O1···C1^iii	3.208 (5)	H2A···O1^ii	2.59 (5)
O1···C1^iv	3.018 (5)	H2B···O2^vi	2.75 (7)
O1···C3^iii	3.391 (5)	H2B···H4A^vi	2.51 (8)
O1···C2^iii	3.356 (5)	H2B···H4B	2.48 (8)
O1···C2^iv	3.257 (5)	H2B···O1^iv	2.75 (6)
O2···O1^iv	3.140 (4)	H3A···H5C	2.57 (8)
O2···O1^i	2.635 (4)	H3B···H5A	2.52 (7)
O1···H2B^iv	2.75 (6)	H3B···O1^iii	2.67 (4)
O1···H2A	2.23 (5)	H4A···O2	2.66 (4)
O1···H2A^ii	2.59 (5)	H4A···H2B^v	2.51 (8)
O1···H3B^iii	2.67 (4)	H4B···H2B	2.48 (8)
O2···H4A	2.66 (4)	H5A···H3B	2.52 (7)
O2···H2B^v	2.75 (7)	H5B···H5B^vii	2.41 (8)
C1···O1^iii	3.208 (5)	H5C···H3A	2.57 (8)
C1···O1^iv	3.018 (5)	H5C···H5C^viii	2.51 (9)
C1···C1^iv	3.422 (5)
C1—O2—C2	116.7 (3)	C4—C3—H3A	109 (3)
O1—C1—O2	128.1 (4)	C4—C3—H3B	108 (3)
O1—C1—C1^i	122.1 (4)	H3A—C3—H3B	109 (5)
O2—C1—C1^i	109.8 (3)	C3—C4—H4A	108 (2)
O2—C2—C3	108.5 (3)	C3—C4—H4B	109 (4)
C2—C3—C4	114.7 (4)	C5—C4—H4A	109 (2)
C3—C4—C5	112.3 (4)	C5—C4—H4B	111 (3)
O2—C2—H2A	103 (3)	H4A—C4—H4B	109 (4)
O2—C2—H2B	109 (4)	C4—C5—H5A	110 (3)
C3—C2—H2A	115 (3)	C4—C5—H5B	115 (3)
C3—C2—H2B	108 (3)	C4—C5—H5C	112 (4)
H2A—C2—H2B	114 (5)	H5A—C5—H5B	106 (5)
C2—C3—H3A	106 (3)	H5A—C5—H5C	110 (6)
C2—C3—H3B	110 (3)	H5B—C5—H5C	104 (5)
C2—O2—C1—O1	1.8 (6)	O2—C1—C1^i—O2^i	180.0 (3)
C2—O2—C1—C1^i	−177.5 (3)	O1—C1—C1^i—O2^i	0.7 (5)
C1—O2—C2—C3	−140.3 (3)	O2—C2—C3—C4	−64.7 (5)
O1—C1—C1^i—O1^i	−180.0 (4)	C2—C3—C4—C5	−178.4 (4)
O2—C1—C1^i—O1^i	−0.7 (5)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z; (iii) −x+1, −y, −z; (iv) −x, −y+1, −z; (v) x+1, y, z; (vi) x−1, y, z; (vii) −x+2, −y+1, −z−1; (viii) −x+1, −y, −z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.96 (5)	2.23 (5)	2.718 (5)	110 (4)
C2—H2A···O1^ii	0.96 (5)	2.59 (5)	3.377 (5)	140 (4)

Symmetry code: (ii) −x, −y, −z.

(DtBO250)

Crystal data

C10H18O4	F(000) = 440
Mr = 202.24	Dx = 1.114 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2677 reflections
a = 11.197 (2) Å	θ = 2.1–27.5°
b = 10.778 (2) Å	µ = 0.09 mm^−1
c = 11.454 (2) Å	T = 250 K
β = 119.23 (3)°	Block, colourless
V = 1206.3 (5) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2209 independent reflections
Radiation source: Sealed Tube	1879 reflections with > 2σ(i)
Graphite Monochromator monochromator	Rint = 0.057
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −13→13
Tmin = 0.959, Tmax = 0.971	l = −13→13
10513 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0711P)^2 + 0.1826P] where P = (Fo^2 + 2Fc^2)/3
2209 reflections	(Δ/σ)max = 0.003
199 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.17 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.74953 (12)	0.24565 (10)	−0.00548 (12)	0.0608 (4)
O2	0.89740 (11)	0.11559 (9)	0.15385 (10)	0.0476 (3)
O3	0.78985 (13)	−0.06663 (12)	−0.03178 (14)	0.0745 (5)
O4	0.59455 (11)	0.04471 (10)	−0.12350 (11)	0.0515 (4)
C1	0.79156 (15)	0.14441 (13)	0.03759 (14)	0.0415 (4)
C2	0.72578 (15)	0.02541 (14)	−0.04276 (15)	0.0440 (5)
C3	0.98492 (15)	0.21401 (15)	0.24924 (15)	0.0466 (5)
C4	0.8998 (2)	0.2939 (2)	0.2892 (2)	0.0603 (6)
C5	1.0521 (2)	0.2880 (2)	0.1849 (2)	0.0639 (7)
C6	1.0884 (3)	0.1386 (2)	0.3658 (2)	0.0748 (7)
C7	0.50502 (16)	−0.05381 (15)	−0.21702 (17)	0.0519 (5)
C8	0.3653 (2)	0.0084 (2)	−0.2803 (3)	0.0887 (9)
C9	0.5539 (3)	−0.0843 (4)	−0.3143 (3)	0.0899 (10)
C10	0.5028 (3)	−0.1651 (2)	−0.1383 (3)	0.0727 (8)
H4A	0.963 (2)	0.3476 (19)	0.364 (2)	0.069 (6)*
H4B	0.833 (2)	0.344 (2)	0.215 (2)	0.070 (6)*
H4C	0.851 (3)	0.244 (2)	0.320 (2)	0.085 (7)*
H5A	1.101 (2)	0.234 (2)	0.155 (2)	0.081 (7)*
H5B	1.119 (3)	0.338 (2)	0.247 (3)	0.090 (7)*
H5C	0.983 (3)	0.336 (2)	0.105 (2)	0.080 (7)*
H6A	1.037 (3)	0.094 (2)	0.400 (3)	0.096 (8)*
H6B	1.153 (2)	0.1934 (19)	0.436 (2)	0.069 (6)*
H6C	1.135 (3)	0.091 (2)	0.330 (3)	0.098 (9)*
H8A	0.297 (3)	−0.050 (2)	−0.349 (3)	0.092 (7)*
H8B	0.342 (5)	0.047 (4)	−0.217 (5)	0.20 (2)*
H8C	0.393 (3)	0.053 (2)	−0.344 (3)	0.093 (8)*
H9A	0.493 (3)	−0.141 (2)	−0.379 (3)	0.095 (8)*
H9B	0.638 (4)	−0.121 (2)	−0.275 (3)	0.109 (11)*
H9C	0.567 (3)	−0.004 (3)	−0.353 (3)	0.128 (11)*
H10A	0.432 (3)	−0.222 (2)	−0.202 (3)	0.097 (8)*
H10B	0.598 (3)	−0.203 (2)	−0.092 (3)	0.104 (9)*
H10C	0.479 (3)	−0.138 (2)	−0.072 (3)	0.104 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0596 (8)	0.0432 (7)	0.0551 (7)	0.0027 (5)	0.0088 (6)	0.0031 (5)
O2	0.0454 (6)	0.0402 (6)	0.0393 (6)	−0.0028 (4)	0.0067 (5)	−0.0025 (4)
O3	0.0523 (7)	0.0572 (8)	0.0768 (9)	0.0129 (6)	0.0026 (7)	−0.0204 (6)
O4	0.0378 (6)	0.0436 (6)	0.0542 (7)	0.0000 (4)	0.0077 (5)	−0.0079 (5)
C1	0.0381 (8)	0.0419 (8)	0.0386 (7)	0.0007 (6)	0.0142 (6)	0.0010 (6)
C2	0.0386 (8)	0.0438 (8)	0.0389 (8)	0.0025 (6)	0.0106 (6)	−0.0011 (6)
C3	0.0426 (8)	0.0444 (8)	0.0419 (8)	−0.0089 (6)	0.0121 (7)	−0.0084 (6)
C4	0.0569 (11)	0.0653 (11)	0.0582 (11)	−0.0125 (10)	0.0277 (10)	−0.0186 (10)
C5	0.0561 (11)	0.0706 (13)	0.0682 (12)	−0.0199 (10)	0.0329 (10)	−0.0158 (10)
C6	0.0683 (13)	0.0632 (12)	0.0528 (11)	−0.0059 (11)	−0.0018 (11)	−0.0061 (9)
C7	0.0394 (8)	0.0476 (9)	0.0515 (9)	−0.0056 (7)	0.0088 (7)	−0.0108 (7)
C8	0.0447 (11)	0.0686 (14)	0.106 (2)	−0.0042 (10)	0.0003 (12)	−0.0099 (14)
C9	0.0754 (16)	0.131 (2)	0.0579 (13)	−0.0378 (17)	0.0283 (12)	−0.0397 (15)
C10	0.0706 (14)	0.0589 (12)	0.0802 (14)	−0.0163 (11)	0.0303 (12)	−0.0079 (10)

Geometric parameters (Å, º)

O1—C1	1.1953 (18)	C5—H5A	0.97 (2)
O2—C1	1.3164 (18)	C5—H5B	0.92 (3)
O2—C3	1.4945 (19)	C5—H5C	1.01 (2)
O3—C2	1.194 (2)	C6—H6A	0.97 (3)
O4—C2	1.316 (2)	C6—H6B	0.98 (2)
O4—C7	1.494 (2)	C6—H6C	0.96 (3)
C1—C2	1.540 (2)	C8—H8A	1.01 (3)
C3—C4	1.512 (3)	C8—H8B	0.98 (5)
C3—C5	1.512 (3)	C8—H8C	1.04 (3)
C3—C6	1.508 (3)	C9—H9A	0.95 (3)
C7—C8	1.522 (3)	C9—H9B	0.91 (4)
C7—C9	1.498 (4)	C9—H9C	1.02 (3)
C7—C10	1.508 (3)	C10—H10A	0.99 (3)
C4—H4A	0.99 (2)	C10—H10B	1.02 (3)
C4—H4B	0.98 (2)	C10—H10C	0.97 (3)
C4—H4C	0.95 (3)
O1···O4	2.6904 (17)	H4C···O1^vii	2.74 (3)
O1···C4	2.991 (2)	H5A···H6C	2.41 (3)
O1···C5	3.037 (3)	H5A···O3^iv	2.90 (2)
O2···O3	2.7069 (17)	H5B···H6B	2.54 (3)
O3···C9	3.023 (3)	H5C···O1	2.48 (3)
O3···C10	3.019 (4)	H5C···C1	2.80 (3)
O3···O2	2.7069 (17)	H5C···H4B	2.55 (4)
O4···O1	2.6904 (17)	H6A···H4C	2.44 (4)
O1···H8A^i	2.66 (2)	H6B···H4A	2.50 (3)
O1···H9A^i	2.67 (3)	H6B···H5B	2.54 (3)
O1···H4C^ii	2.74 (3)	H6B···O3^vi	2.76 (2)
O1···H5C	2.48 (3)	H6C···H5A	2.41 (3)
O1···H4B	2.46 (2)	H8A···H9A	2.58 (5)
O3···H9B	2.52 (3)	H8A···H10A	2.46 (4)
O3···H10B	2.41 (3)	H8A···O1^viii	2.66 (2)
O3···H6B^iii	2.76 (2)	H8B···H10C	2.57 (5)
O3···H5A^iv	2.90 (2)	H8C···H9A	2.50 (4)
O3···H4A^iii	2.65 (2)	H8C···H9C	2.09 (5)
O4···H10C^v	2.92 (3)	H9A···H8A	2.58 (5)
C4···O1	2.991 (2)	H9A···H8C	2.50 (4)
C5···O1	3.037 (3)	H9A···H10A	2.59 (5)
C9···O3	3.023 (3)	H9A···O1^viii	2.67 (3)
C10···O3	3.019 (4)	H9B···O3	2.52 (3)
C1···H5C	2.80 (3)	H9B···C2	2.83 (3)
C1···H4B	2.84 (2)	H9B···H10B	2.51 (5)
C2···H9B	2.83 (3)	H9C···H8C	2.09 (5)
C2···H10B	2.76 (3)	H10A···H8A	2.46 (4)
H4A···H6B	2.50 (3)	H10A···H9A	2.59 (5)
H4A···O3^vi	2.65 (2)	H10B···O3	2.41 (3)
H4B···O1	2.46 (2)	H10B···C2	2.76 (3)
H4B···C1	2.84 (2)	H10B···H9B	2.51 (5)
H4B···H5C	2.55 (4)	H10C···H8B	2.57 (5)
H4C···H6A	2.44 (4)	H10C···O4^v	2.92 (3)
C1—O2—C3	121.14 (11)	C3—C5—H5C	111.7 (19)
C2—O4—C7	121.32 (13)	H5A—C5—H5B	104 (3)
O1—C1—O2	127.69 (14)	H5A—C5—H5C	108 (2)
O1—C1—C2	122.45 (14)	H5B—C5—H5C	112 (2)
O2—C1—C2	109.85 (12)	C3—C6—H6A	105.9 (19)
O3—C2—O4	127.78 (15)	C3—C6—H6B	110.1 (12)
O3—C2—C1	122.77 (16)	C3—C6—H6C	104.7 (18)
O4—C2—C1	109.42 (13)	H6A—C6—H6B	108 (2)
O2—C3—C4	109.90 (15)	H6A—C6—H6C	118 (2)
O2—C3—C5	108.83 (14)	H6B—C6—H6C	110 (2)
O2—C3—C6	102.16 (14)	C7—C8—H8A	108.0 (18)
C4—C3—C5	112.61 (16)	C7—C8—H8B	115 (3)
C4—C3—C6	111.37 (17)	C7—C8—H8C	87.0 (18)
C5—C3—C6	111.45 (19)	H8A—C8—H8B	118 (4)
O4—C7—C8	101.67 (15)	H8A—C8—H8C	97 (2)
O4—C7—C9	109.2 (2)	H8B—C8—H8C	127 (3)
O4—C7—C10	109.75 (16)	C7—C9—H9A	110 (2)
C8—C7—C9	114.0 (2)	C7—C9—H9B	113 (2)
C8—C7—C10	108.8 (2)	C7—C9—H9C	108.7 (19)
C9—C7—C10	112.9 (2)	H9A—C9—H9B	106 (3)
C3—C4—H4A	107.8 (14)	H9A—C9—H9C	114 (2)
C3—C4—H4B	112.3 (14)	H9B—C9—H9C	105 (3)
C3—C4—H4C	110.6 (16)	C7—C10—H10A	107.1 (16)
H4A—C4—H4B	110.5 (17)	C7—C10—H10B	108.2 (16)
H4A—C4—H4C	107.9 (18)	C7—C10—H10C	108.8 (14)
H4B—C4—H4C	108 (2)	H10A—C10—H10B	113 (2)
C3—C5—H5A	110.9 (13)	H10A—C10—H10C	110 (3)
C3—C5—H5B	110 (2)	H10B—C10—H10C	110 (3)
C3—O2—C1—O1	−2.1 (3)	C7—O4—C2—C1	178.17 (14)
C3—O2—C1—C2	176.73 (14)	C2—O4—C7—C9	−62.6 (2)
C1—O2—C3—C5	−63.0 (2)	C2—O4—C7—C10	61.6 (2)
C1—O2—C3—C6	179.06 (19)	O1—C1—C2—O3	148.73 (19)
C1—O2—C3—C4	60.7 (2)	O2—C1—C2—O3	−30.1 (2)
C2—O4—C7—C8	176.62 (17)	O2—C1—C2—O4	151.60 (15)
C7—O4—C2—O3	0.0 (3)	O1—C1—C2—O4	−29.6 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.98 (2)	2.46 (2)	2.991 (2)	113.6 (16)
C5—H5C···O1	1.01 (2)	2.48 (3)	3.037 (3)	114.4 (19)
C9—H9B···O3	0.91 (4)	2.52 (3)	3.023 (3)	115 (2)
C10—H10B···O3	1.02 (3)	2.41 (3)	3.019 (4)	117.8 (16)

(DtBO225)

Crystal data

C10H18O4	F(000) = 440
Mr = 202.24	Dx = 1.120 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2852 reflections
a = 11.183 (2) Å	θ = 2.0–27.5°
b = 10.752 (2) Å	µ = 0.09 mm^−1
c = 11.405 (2) Å	T = 225 K
β = 118.95 (3)°	Block, colourless
V = 1200.0 (5) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2199 independent reflections
Radiation source: Sealed Tube	1919 reflections with > 2σ(i)
Graphite Monochromator monochromator	Rint = 0.059
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −12→12
Tmin = 0.959, Tmax = 0.971	l = −13→13
10476 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 0.2264P] where P = (Fo^2 + 2Fc^2)/3
2199 reflections	(Δ/σ)max = 0.003
199 parameters	Δρmax = 0.23 e Å^−3
0 restraints	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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.74906 (12)	0.24539 (10)	−0.00466 (11)	0.0534 (4)
O2	0.89782 (11)	0.11453 (9)	0.15395 (10)	0.0424 (3)
O3	0.78962 (13)	−0.06819 (12)	−0.03207 (13)	0.0657 (4)
O4	0.59444 (10)	0.04393 (9)	−0.12298 (11)	0.0455 (3)
C1	0.79154 (15)	0.14367 (13)	0.03804 (14)	0.0370 (4)
C2	0.72576 (15)	0.02457 (13)	−0.04267 (14)	0.0392 (4)
C3	0.98525 (15)	0.21342 (14)	0.24916 (14)	0.0420 (5)
C4	0.9002 (2)	0.29288 (19)	0.29075 (19)	0.0534 (6)
C5	1.0521 (2)	0.2880 (2)	0.1843 (2)	0.0562 (6)
C6	1.0891 (2)	0.13784 (19)	0.3660 (2)	0.0653 (6)
C7	0.50479 (16)	−0.05489 (15)	−0.21667 (16)	0.0463 (5)
C8	0.3656 (2)	0.0077 (2)	−0.2803 (3)	0.0785 (8)
C9	0.5539 (3)	−0.0856 (3)	−0.3149 (2)	0.0790 (9)
C10	0.5027 (2)	−0.1666 (2)	−0.1376 (2)	0.0633 (7)
H4A	0.964 (2)	0.3482 (18)	0.366 (2)	0.061 (5)*
H4B	0.834 (2)	0.3451 (18)	0.218 (2)	0.060 (5)*
H4C	0.851 (2)	0.240 (2)	0.321 (2)	0.075 (6)*
H5A	1.102 (2)	0.233 (2)	0.154 (2)	0.070 (6)*
H5B	1.117 (3)	0.340 (2)	0.247 (2)	0.077 (6)*
H5C	0.986 (2)	0.3371 (19)	0.107 (2)	0.067 (6)*
H6A	1.040 (3)	0.092 (2)	0.400 (2)	0.085 (8)*
H6B	1.156 (2)	0.1943 (18)	0.437 (2)	0.062 (5)*
H6C	1.140 (2)	0.087 (2)	0.336 (2)	0.078 (7)*
H8A	0.298 (3)	−0.050 (2)	−0.348 (2)	0.084 (7)*
H8B	0.339 (5)	0.040 (4)	−0.215 (5)	0.185 (18)*
H8C	0.383 (3)	0.063 (3)	−0.341 (3)	0.095 (8)*
H9A	0.490 (3)	−0.140 (2)	−0.382 (2)	0.084 (7)*
H9B	0.641 (3)	−0.125 (2)	−0.273 (3)	0.095 (9)*
H9C	0.564 (3)	−0.008 (3)	−0.358 (3)	0.107 (9)*
H10A	0.434 (3)	−0.223 (2)	−0.199 (2)	0.087 (7)*
H10B	0.598 (3)	−0.207 (2)	−0.090 (3)	0.094 (8)*
H10C	0.478 (3)	−0.138 (2)	−0.070 (3)	0.093 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0527 (7)	0.0389 (6)	0.0487 (7)	0.0022 (5)	0.0087 (6)	0.0030 (5)
O2	0.0405 (6)	0.0355 (5)	0.0358 (5)	−0.0027 (4)	0.0062 (5)	−0.0025 (4)
O3	0.0466 (7)	0.0512 (7)	0.0685 (8)	0.0110 (6)	0.0035 (6)	−0.0175 (6)
O4	0.0332 (6)	0.0392 (6)	0.0487 (6)	−0.0001 (4)	0.0076 (5)	−0.0073 (5)
C1	0.0335 (7)	0.0381 (8)	0.0352 (7)	0.0009 (6)	0.0132 (6)	0.0010 (6)
C2	0.0352 (7)	0.0395 (8)	0.0345 (7)	0.0022 (6)	0.0102 (6)	−0.0007 (6)
C3	0.0384 (8)	0.0398 (8)	0.0383 (8)	−0.0085 (6)	0.0111 (7)	−0.0076 (6)
C4	0.0505 (10)	0.0584 (11)	0.0513 (10)	−0.0101 (9)	0.0247 (9)	−0.0158 (9)
C5	0.0500 (10)	0.0612 (11)	0.0600 (11)	−0.0165 (9)	0.0287 (9)	−0.0130 (9)
C6	0.0588 (12)	0.0547 (11)	0.0486 (10)	−0.0032 (10)	−0.0008 (10)	−0.0058 (9)
C7	0.0352 (8)	0.0434 (8)	0.0463 (9)	−0.0054 (6)	0.0086 (7)	−0.0104 (7)
C8	0.0404 (10)	0.0591 (12)	0.0939 (17)	−0.0030 (9)	−0.0007 (11)	−0.0064 (13)
C9	0.0679 (15)	0.114 (2)	0.0510 (12)	−0.0340 (15)	0.0256 (11)	−0.0331 (13)
C10	0.0619 (12)	0.0516 (11)	0.0701 (13)	−0.0142 (10)	0.0270 (11)	−0.0066 (9)

Geometric parameters (Å, º)

O1—C1	1.1979 (18)	C5—H5A	0.98 (2)
O2—C1	1.3181 (18)	C5—H5B	0.92 (2)
O2—C3	1.4959 (18)	C5—H5C	0.99 (2)
O3—C2	1.198 (2)	C6—H6A	0.95 (3)
O4—C2	1.318 (2)	C6—H6B	1.00 (2)
O4—C7	1.496 (2)	C6—H6C	0.96 (2)
C1—C2	1.540 (2)	C8—H8A	0.99 (2)
C3—C4	1.515 (3)	C8—H8B	0.99 (5)
C3—C5	1.511 (3)	C8—H8C	1.00 (3)
C3—C6	1.512 (3)	C9—H9A	0.95 (2)
C7—C8	1.520 (3)	C9—H9B	0.95 (3)
C7—C9	1.504 (3)	C9—H9C	1.00 (3)
C7—C10	1.509 (3)	C10—H10A	0.96 (2)
C4—H4A	1.00 (2)	C10—H10B	1.03 (3)
C4—H4B	0.98 (2)	C10—H10C	0.99 (3)
C4—H4C	0.96 (2)
O1···O4	2.6915 (16)	H4B···H5C	2.57 (3)
O1···C4	2.993 (2)	H4C···H6A	2.44 (4)
O1···C5	3.044 (3)	H4C···O1^vii	2.73 (2)
O2···O3	2.7092 (17)	H5A···H6C	2.47 (3)
O3···C9	3.026 (3)	H5A···O3^iv	2.86 (2)
O3···C10	3.021 (3)	H5B···H6B	2.54 (3)
O3···O2	2.7092 (17)	H5C···O1	2.52 (2)
O4···O1	2.6915 (16)	H5C···C1	2.83 (2)
O1···H8A^i	2.66 (2)	H5C···H4B	2.57 (3)
O1···H9A^i	2.64 (3)	H6A···H4C	2.44 (4)
O1···H4C^ii	2.73 (2)	H6B···H4A	2.51 (3)
O1···H5C	2.52 (2)	H6B···H5B	2.54 (3)
O1···H4B	2.48 (2)	H6B···O3^vi	2.726 (19)
O3···H9B	2.50 (3)	H6C···H5A	2.47 (3)
O3···H10B	2.43 (3)	H8A···H9A	2.55 (5)
O3···H6B^iii	2.73 (2)	H8A···H10A	2.48 (3)
O3···H5A^iv	2.86 (2)	H8A···O1^viii	2.66 (2)
O3···H4A^iii	2.63 (2)	H8B···H10C	2.52 (5)
O4···H10C^v	2.87 (3)	H8C···H9C	2.26 (5)
C4···O1	2.993 (2)	H9A···H8A	2.55 (5)
C5···O1	3.044 (3)	H9A···O1^viii	2.64 (3)
C9···O3	3.026 (3)	H9B···O3	2.50 (3)
C10···O3	3.021 (3)	H9B···C2	2.82 (3)
C1···H5C	2.83 (2)	H9B···H10B	2.52 (5)
C1···H4B	2.86 (2)	H9C···H8C	2.26 (5)
C2···H9B	2.82 (3)	H10A···H8A	2.48 (3)
C2···H10B	2.79 (3)	H10B···O3	2.43 (3)
H4A···H6B	2.51 (3)	H10B···C2	2.79 (3)
H4A···O3^vi	2.63 (2)	H10B···H9B	2.52 (5)
H4B···O1	2.48 (2)	H10C···H8B	2.52 (5)
H4B···C1	2.86 (2)	H10C···O4^v	2.87 (3)
C1—O2—C3	120.95 (11)	C3—C5—H5C	112.8 (14)
C2—O4—C7	121.35 (12)	H5A—C5—H5B	106 (2)
O1—C1—O2	127.76 (14)	H5A—C5—H5C	108.4 (18)
O1—C1—C2	122.37 (14)	H5B—C5—H5C	109.7 (18)
O2—C1—C2	109.86 (12)	C3—C6—H6A	106.8 (16)
O3—C2—O4	127.65 (15)	C3—C6—H6B	110.0 (11)
O3—C2—C1	122.87 (16)	C3—C6—H6C	109.0 (12)
O4—C2—C1	109.46 (13)	H6A—C6—H6B	109.8 (18)
O2—C3—C4	109.83 (15)	H6A—C6—H6C	114 (2)
O2—C3—C5	109.04 (13)	H6B—C6—H6C	107.1 (19)
O2—C3—C6	102.18 (13)	C7—C8—H8A	108.2 (17)
C4—C3—C5	112.84 (15)	C7—C8—H8B	114 (3)
C4—C3—C6	110.97 (15)	C7—C8—H8C	96 (2)
C5—C3—C6	111.44 (17)	H8A—C8—H8B	114 (4)
O4—C7—C8	101.77 (15)	H8A—C8—H8C	99 (2)
O4—C7—C9	109.14 (18)	H8B—C8—H8C	123 (3)
O4—C7—C10	109.71 (14)	C7—C9—H9A	109 (2)
C8—C7—C9	113.61 (19)	C7—C9—H9B	112.2 (19)
C8—C7—C10	109.23 (18)	C7—C9—H9C	110.6 (19)
C9—C7—C10	112.79 (18)	H9A—C9—H9B	109 (2)
C3—C4—H4A	107.9 (14)	H9A—C9—H9C	110 (2)
C3—C4—H4B	113.0 (13)	H9B—C9—H9C	107 (3)
C3—C4—H4C	109.5 (14)	C7—C10—H10A	107.7 (13)
H4A—C4—H4B	108.6 (16)	C7—C10—H10B	109.9 (16)
H4A—C4—H4C	109.7 (18)	C7—C10—H10C	108.1 (13)
H4B—C4—H4C	108 (2)	H10A—C10—H10B	112 (2)
C3—C5—H5A	110.6 (13)	H10A—C10—H10C	110 (3)
C3—C5—H5B	109.4 (17)	H10B—C10—H10C	109 (3)
C3—O2—C1—O1	−2.1 (3)	C7—O4—C2—C1	178.26 (13)
C3—O2—C1—C2	176.65 (14)	C2—O4—C7—C9	−62.4 (2)
C1—O2—C3—C5	−63.2 (2)	C2—O4—C7—C10	61.6 (2)
C1—O2—C3—C6	178.73 (16)	O1—C1—C2—O3	149.32 (19)
C1—O2—C3—C4	60.89 (19)	O2—C1—C2—O3	−29.5 (2)
C2—O4—C7—C8	177.21 (16)	O2—C1—C2—O4	151.85 (14)
C7—O4—C2—O3	−0.3 (3)	O1—C1—C2—O4	−29.3 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.98 (2)	2.48 (2)	2.993 (2)	112.2 (14)
C5—H5C···O1	0.99 (2)	2.52 (2)	3.044 (3)	113.1 (16)
C9—H9B···O3	0.95 (3)	2.50 (3)	3.026 (3)	115 (2)
C10—H10B···O3	1.03 (3)	2.43 (3)	3.021 (3)	115.9 (16)

(DtBO200)

Crystal data

C10H18O4	F(000) = 440
Mr = 202.24	Dx = 1.127 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2805 reflections
a = 11.163 (2) Å	θ = 2.0–27.5°
b = 10.720 (2) Å	µ = 0.09 mm^−1
c = 11.359 (2) Å	T = 200 K
β = 118.75 (3)°	Block, colourless
V = 1191.7 (5) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2186 independent reflections
Radiation source: Sealed Tube	1936 reflections with > 2σ(i)
Graphite Monochromator monochromator	Rint = 0.054
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −12→12
Tmin = 0.958, Tmax = 0.970	l = −13→13
10415 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 0.2014P] where P = (Fo^2 + 2Fc^2)/3
2186 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.17 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.74860 (11)	0.24511 (9)	−0.00396 (10)	0.0471 (3)
O2	0.89823 (10)	0.11367 (8)	0.15401 (9)	0.0378 (3)
O3	0.78955 (11)	−0.06945 (10)	−0.03216 (12)	0.0576 (4)
O4	0.59422 (9)	0.04314 (9)	−0.12252 (10)	0.0405 (3)
C1	0.79147 (13)	0.14320 (12)	0.03836 (12)	0.0329 (4)
C2	0.72576 (13)	0.02352 (12)	−0.04253 (13)	0.0347 (4)
C3	0.98561 (13)	0.21279 (13)	0.24950 (13)	0.0372 (4)
C4	0.90048 (17)	0.29225 (16)	0.29184 (17)	0.0471 (5)
C5	1.05224 (18)	0.28823 (17)	0.18378 (18)	0.0497 (5)
C6	1.0899 (2)	0.13700 (17)	0.36607 (17)	0.0571 (5)
C7	0.50461 (14)	−0.05586 (13)	−0.21632 (14)	0.0412 (4)
C8	0.36546 (18)	0.00700 (19)	−0.2805 (3)	0.0690 (6)
C9	0.5539 (2)	−0.0865 (3)	−0.31552 (19)	0.0688 (7)
C10	0.5026 (2)	−0.16828 (17)	−0.1373 (2)	0.0559 (6)
H4A	0.9645 (19)	0.3482 (16)	0.3666 (19)	0.058 (5)*
H4B	0.831 (2)	0.3448 (17)	0.2165 (19)	0.059 (5)*
H4C	0.852 (2)	0.2393 (18)	0.324 (2)	0.069 (6)*
H5A	1.103 (2)	0.2334 (17)	0.1539 (19)	0.065 (5)*
H5B	1.117 (2)	0.3405 (19)	0.248 (2)	0.071 (6)*
H5C	0.9854 (19)	0.3362 (17)	0.1063 (19)	0.055 (5)*
H6A	1.041 (2)	0.0897 (19)	0.402 (2)	0.071 (6)*
H6B	1.1541 (19)	0.1962 (17)	0.4359 (18)	0.058 (5)*
H6C	1.140 (2)	0.0850 (19)	0.334 (2)	0.071 (6)*
H8A	0.297 (2)	−0.0518 (19)	−0.350 (2)	0.071 (6)*
H8B	0.339 (4)	0.036 (3)	−0.210 (4)	0.149 (13)*
H8C	0.381 (2)	0.067 (2)	−0.336 (2)	0.086 (7)*
H9A	0.487 (2)	−0.1398 (19)	−0.383 (2)	0.079 (6)*
H9B	0.645 (3)	−0.129 (2)	−0.271 (2)	0.085 (7)*
H9C	0.562 (3)	−0.007 (2)	−0.359 (2)	0.096 (8)*
H10A	0.432 (2)	−0.226 (2)	−0.199 (2)	0.078 (6)*
H10B	0.596 (2)	−0.207 (2)	−0.090 (2)	0.080 (6)*
H10C	0.474 (2)	−0.140 (2)	−0.072 (2)	0.082 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0468 (6)	0.0345 (5)	0.0438 (6)	0.0026 (4)	0.0089 (5)	0.0032 (4)
O2	0.0364 (5)	0.0315 (5)	0.0322 (5)	−0.0020 (4)	0.0058 (4)	−0.0025 (4)
O3	0.0416 (6)	0.0453 (6)	0.0606 (7)	0.0097 (5)	0.0043 (5)	−0.0160 (5)
O4	0.0294 (5)	0.0354 (5)	0.0429 (6)	−0.0003 (4)	0.0063 (4)	−0.0064 (4)
C1	0.0303 (6)	0.0343 (7)	0.0308 (6)	0.0005 (5)	0.0120 (5)	0.0009 (5)
C2	0.0316 (7)	0.0363 (7)	0.0298 (6)	0.0015 (5)	0.0096 (5)	−0.0004 (5)
C3	0.0336 (7)	0.0353 (7)	0.0343 (7)	−0.0070 (5)	0.0096 (6)	−0.0069 (5)
C4	0.0452 (9)	0.0512 (9)	0.0458 (9)	−0.0088 (8)	0.0227 (8)	−0.0139 (7)
C5	0.0439 (9)	0.0541 (10)	0.0531 (9)	−0.0141 (8)	0.0250 (8)	−0.0113 (8)
C6	0.0525 (10)	0.0479 (9)	0.0429 (9)	−0.0021 (8)	0.0006 (8)	−0.0054 (7)
C7	0.0316 (7)	0.0389 (7)	0.0410 (8)	−0.0053 (6)	0.0077 (6)	−0.0087 (6)
C8	0.0367 (9)	0.0519 (10)	0.0825 (14)	−0.0027 (8)	0.0000 (9)	−0.0047 (10)
C9	0.0593 (12)	0.0998 (16)	0.0433 (10)	−0.0295 (12)	0.0216 (9)	−0.0279 (10)
C10	0.0553 (10)	0.0451 (9)	0.0630 (11)	−0.0108 (8)	0.0250 (9)	−0.0048 (8)

Geometric parameters (Å, º)

O1—C1	1.1968 (16)	C5—H5A	0.98 (2)
O2—C1	1.3192 (16)	C5—H5B	0.93 (2)
O2—C3	1.4964 (17)	C5—H5C	0.982 (19)
O3—C2	1.1973 (18)	C6—H6A	0.97 (2)
O4—C2	1.3200 (19)	C6—H6B	0.999 (19)
O4—C7	1.4956 (18)	C6—H6C	0.98 (2)
C1—C2	1.5427 (18)	C8—H8A	1.01 (2)
C3—C4	1.517 (3)	C8—H8B	1.03 (4)
C3—C5	1.516 (3)	C8—H8C	0.97 (2)
C3—C6	1.512 (2)	C9—H9A	0.96 (2)
C7—C8	1.520 (3)	C9—H9B	1.00 (3)
C7—C9	1.509 (3)	C9—H9C	1.01 (2)
C7—C10	1.509 (2)	C10—H10A	0.98 (2)
C4—H4A	1.004 (19)	C10—H10B	1.01 (2)
C4—H4B	1.01 (2)	C10—H10C	0.99 (2)
C4—H4C	0.97 (2)
O1···O4	2.6905 (15)	H4B···H5C	2.57 (3)
O1···C4	2.990 (2)	H4C···H6A	2.45 (3)
O1···C5	3.049 (2)	H4C···O1^vii	2.71 (2)
O2···O3	2.7073 (15)	H4C···C1^vii	3.09 (2)
O3···C9	3.028 (2)	H5A···H6C	2.46 (3)
O3···C10	3.022 (3)	H5A···O3^iv	2.84 (2)
O3···O2	2.7073 (15)	H5B···H6B	2.50 (3)
O4···O1	2.6905 (15)	H5C···O1	2.52 (2)
O1···H8A^i	2.63 (2)	H5C···C1	2.82 (2)
O1···H9A^i	2.62 (2)	H5C···H4B	2.57 (3)
O1···H4C^ii	2.71 (2)	H6A···H4C	2.45 (3)
O1···H5C	2.52 (2)	H6B···H4A	2.48 (3)
O1···H4B	2.458 (19)	H6B···H5B	2.50 (3)
O3···H9B	2.48 (2)	H6B···O3^vi	2.691 (18)
O3···H10B	2.43 (2)	H6C···H5A	2.46 (3)
O3···H6B^iii	2.691 (18)	H8A···H9A	2.51 (3)
O3···H5A^iv	2.84 (2)	H8A···H10A	2.49 (3)
O3···H4A^iii	2.62 (2)	H8A···O1^viii	2.63 (2)
O4···H10C^v	2.86 (2)	H8B···H10C	2.45 (4)
C4···O1	2.990 (2)	H8C···H9C	2.30 (4)
C5···O1	3.049 (2)	H9A···H8A	2.51 (3)
C9···O3	3.028 (2)	H9A···O1^viii	2.62 (2)
C10···O3	3.022 (3)	H9B···O3	2.48 (2)
C1···H4B	2.846 (19)	H9B···C2	2.82 (2)
C1···H4C^ii	3.09 (2)	H9B···H10B	2.51 (3)
C1···H5C	2.82 (2)	H9C···H8C	2.30 (4)
C2···H9B	2.82 (2)	H10A···H8A	2.49 (3)
C2···H10B	2.78 (2)	H10B···O3	2.43 (2)
H4A···H6B	2.48 (3)	H10B···C2	2.78 (2)
H4A···O3^vi	2.62 (2)	H10B···H9B	2.51 (3)
H4B···O1	2.458 (19)	H10C···H8B	2.45 (4)
H4B···C1	2.846 (19)	H10C···O4^v	2.86 (2)
C1—O2—C3	120.87 (10)	C3—C5—H5C	112.3 (14)
C2—O4—C7	121.25 (11)	H5A—C5—H5B	105.8 (19)
O1—C1—O2	127.90 (13)	H5A—C5—H5C	108.6 (17)
O1—C1—C2	122.43 (12)	H5B—C5—H5C	110.9 (17)
O2—C1—C2	109.67 (11)	C3—C6—H6A	107.3 (13)
O3—C2—O4	127.76 (13)	C3—C6—H6B	108.1 (11)
O3—C2—C1	122.94 (14)	C3—C6—H6C	108.6 (12)
O4—C2—C1	109.29 (12)	H6A—C6—H6B	109.4 (17)
O2—C3—C4	109.84 (13)	H6A—C6—H6C	113.5 (18)
O2—C3—C5	108.96 (12)	H6B—C6—H6C	109.8 (18)
O2—C3—C6	102.25 (12)	C7—C8—H8A	108.2 (13)
C4—C3—C5	112.78 (14)	C7—C8—H8B	112 (2)
C4—C3—C6	111.11 (14)	C7—C8—H8C	98.3 (14)
C5—C3—C6	111.37 (16)	H8A—C8—H8B	114 (3)
O4—C7—C8	101.90 (13)	H8A—C8—H8C	102.1 (17)
O4—C7—C9	109.10 (16)	H8B—C8—H8C	121 (2)
O4—C7—C10	109.82 (12)	C7—C9—H9A	107.6 (15)
C8—C7—C9	113.21 (17)	C7—C9—H9B	111.6 (14)
C8—C7—C10	109.59 (17)	C7—C9—H9C	109.4 (16)
C9—C7—C10	112.67 (17)	H9A—C9—H9B	110.1 (19)
C3—C4—H4A	107.7 (13)	H9A—C9—H9C	109.3 (18)
C3—C4—H4B	112.9 (13)	H9B—C9—H9C	109 (2)
C3—C4—H4C	109.8 (13)	C7—C10—H10A	108.4 (12)
H4A—C4—H4B	109.2 (15)	C7—C10—H10B	109.9 (13)
H4A—C4—H4C	109.3 (17)	C7—C10—H10C	107.7 (12)
H4B—C4—H4C	107.9 (19)	H10A—C10—H10B	113.1 (18)
C3—C5—H5A	110.6 (12)	H10A—C10—H10C	107.0 (19)
C3—C5—H5B	108.4 (14)	H10B—C10—H10C	110.7 (17)
C3—O2—C1—O1	−2.0 (2)	C7—O4—C2—C1	178.21 (12)
C3—O2—C1—C2	176.79 (13)	C2—O4—C7—C9	−62.35 (18)
C1—O2—C3—C5	−63.44 (18)	C2—O4—C7—C10	61.59 (19)
C1—O2—C3—C6	178.60 (15)	O1—C1—C2—O3	149.73 (17)
C1—O2—C3—C4	60.56 (17)	O2—C1—C2—O3	−29.1 (2)
C2—O4—C7—C8	177.70 (15)	O2—C1—C2—O4	152.11 (13)
C7—O4—C2—O3	−0.5 (2)	O1—C1—C2—O4	−29.1 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	1.01 (2)	2.458 (19)	2.990 (2)	112.4 (13)
C5—H5C···O1	0.982 (19)	2.52 (2)	3.049 (2)	114.0 (15)
C9—H9B···O3	1.00 (3)	2.48 (2)	3.028 (2)	113.8 (17)
C10—H10B···O3	1.01 (2)	2.43 (2)	3.022 (3)	116.9 (15)

(DtBO175)

Crystal data

C10H18O4	F(000) = 440
Mr = 202.24	Dx = 1.135 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2819 reflections
a = 11.138 (2) Å	θ = 2.0–27.5°
b = 10.686 (2) Å	µ = 0.09 mm^−1
c = 11.324 (2) Å	T = 175 K
β = 118.61 (3)°	Block, colourless
V = 1183.2 (5) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2174 independent reflections
Radiation source: Sealed Tube	1948 reflections with > 2σ(i)
Graphite Monochromator monochromator	Rint = 0.054
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −12→12
Tmin = 0.958, Tmax = 0.970	l = −13→13
10363 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0423P)^2 + 0.2299P] where P = (Fo^2 + 2Fc^2)/3
2174 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.20 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.74816 (10)	0.24503 (8)	−0.00325 (9)	0.0415 (3)
O2	0.89860 (9)	0.11286 (8)	0.15415 (8)	0.0335 (3)
O3	0.78946 (10)	−0.07049 (10)	−0.03216 (11)	0.0502 (3)
O4	0.59402 (9)	0.04245 (8)	−0.12220 (9)	0.0363 (3)
C1	0.79156 (12)	0.14260 (11)	0.03887 (12)	0.0298 (4)
C2	0.72565 (13)	0.02267 (12)	−0.04242 (12)	0.0311 (4)
C3	0.98587 (13)	0.21236 (12)	0.24968 (12)	0.0332 (4)
C4	0.90068 (16)	0.29162 (15)	0.29296 (16)	0.0418 (5)
C5	1.05211 (16)	0.28845 (16)	0.18334 (17)	0.0436 (5)
C6	1.09053 (18)	0.13644 (16)	0.36595 (16)	0.0503 (5)
C7	0.50458 (13)	−0.05674 (13)	−0.21600 (13)	0.0366 (4)
C8	0.36559 (17)	0.00644 (18)	−0.2805 (2)	0.0607 (6)
C9	0.5540 (2)	−0.0871 (2)	−0.31596 (18)	0.0606 (6)
C10	0.50248 (18)	−0.16945 (15)	−0.13655 (18)	0.0491 (5)
H4A	0.9643 (17)	0.3487 (15)	0.3665 (16)	0.047 (4)*
H4B	0.8343 (18)	0.3432 (16)	0.2194 (18)	0.053 (5)*
H4C	0.8545 (19)	0.2391 (17)	0.3281 (18)	0.061 (5)*
H5A	1.1031 (18)	0.2332 (17)	0.1539 (17)	0.060 (5)*
H5B	1.1186 (19)	0.3417 (17)	0.2506 (18)	0.060 (5)*
H5C	0.9847 (18)	0.3355 (16)	0.1060 (18)	0.051 (5)*
H6A	1.0428 (19)	0.0874 (17)	0.4040 (18)	0.061 (5)*
H6B	1.1565 (17)	0.1948 (16)	0.4366 (17)	0.050 (4)*
H6C	1.143 (2)	0.0842 (18)	0.3349 (19)	0.067 (6)*
H8A	0.298 (2)	−0.0526 (19)	−0.3503 (19)	0.068 (5)*
H8B	0.338 (3)	0.035 (3)	−0.211 (3)	0.126 (10)*
H8C	0.376 (2)	0.072 (2)	−0.333 (2)	0.076 (6)*
H9A	0.487 (2)	−0.1407 (17)	−0.3827 (19)	0.065 (5)*
H9B	0.644 (2)	−0.1292 (18)	−0.272 (2)	0.074 (6)*
H9C	0.560 (2)	−0.007 (2)	−0.361 (2)	0.094 (7)*
H10A	0.433 (2)	−0.2282 (18)	−0.1992 (19)	0.064 (5)*
H10B	0.595 (2)	−0.2094 (17)	−0.0885 (18)	0.064 (5)*
H10C	0.474 (2)	−0.1421 (19)	−0.071 (2)	0.077 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0416 (5)	0.0306 (5)	0.0393 (5)	0.0024 (4)	0.0089 (5)	0.0024 (4)
O2	0.0321 (5)	0.0282 (5)	0.0284 (5)	−0.0020 (4)	0.0051 (4)	−0.0020 (3)
O3	0.0371 (5)	0.0401 (6)	0.0526 (6)	0.0079 (5)	0.0048 (5)	−0.0132 (5)
O4	0.0270 (5)	0.0317 (5)	0.0387 (5)	−0.0004 (4)	0.0066 (4)	−0.0055 (4)
C1	0.0273 (6)	0.0315 (7)	0.0287 (6)	0.0000 (5)	0.0120 (5)	0.0005 (5)
C2	0.0286 (6)	0.0324 (7)	0.0271 (6)	0.0014 (5)	0.0091 (5)	−0.0005 (5)
C3	0.0305 (6)	0.0318 (7)	0.0305 (6)	−0.0067 (5)	0.0091 (6)	−0.0068 (5)
C4	0.0410 (8)	0.0452 (8)	0.0401 (8)	−0.0078 (7)	0.0201 (7)	−0.0118 (7)
C5	0.0394 (8)	0.0467 (9)	0.0467 (9)	−0.0115 (7)	0.0223 (7)	−0.0094 (7)
C6	0.0460 (9)	0.0431 (9)	0.0378 (8)	−0.0020 (7)	0.0008 (7)	−0.0046 (7)
C7	0.0283 (6)	0.0356 (7)	0.0359 (7)	−0.0052 (5)	0.0074 (6)	−0.0079 (6)
C8	0.0329 (8)	0.0455 (9)	0.0737 (13)	−0.0021 (7)	0.0015 (9)	−0.0034 (9)
C9	0.0523 (10)	0.0868 (14)	0.0387 (9)	−0.0246 (10)	0.0187 (8)	−0.0232 (9)
C10	0.0470 (9)	0.0396 (8)	0.0559 (10)	−0.0084 (7)	0.0208 (8)	−0.0043 (7)

Geometric parameters (Å, º)

O1—C1	1.1994 (15)	C5—H5A	0.98 (2)
O2—C1	1.3176 (15)	C5—H5B	0.955 (19)
O2—C3	1.4962 (16)	C5—H5C	0.977 (18)
O3—C2	1.1961 (18)	C6—H6A	0.98 (2)
O4—C2	1.3198 (18)	C6—H6B	1.003 (18)
O4—C7	1.4936 (17)	C6—H6C	0.99 (2)
C1—C2	1.5432 (18)	C8—H8A	1.01 (2)
C3—C4	1.518 (2)	C8—H8B	1.02 (3)
C3—C5	1.517 (2)	C8—H8C	0.96 (2)
C3—C6	1.510 (2)	C9—H9A	0.96 (2)
C7—C8	1.518 (3)	C9—H9B	0.99 (2)
C7—C9	1.512 (3)	C9—H9C	1.02 (2)
C7—C10	1.510 (2)	C10—H10A	0.99 (2)
C4—H4A	1.001 (17)	C10—H10B	1.00 (2)
C4—H4B	0.977 (18)	C10—H10C	0.98 (2)
C4—H4C	0.97 (2)
O1···O4	2.6895 (14)	H4C···O1^vii	2.69 (2)
O1···C4	2.9880 (19)	H4C···C1^vii	3.06 (2)
O1···C5	3.048 (2)	H5A···H6C	2.46 (3)
O2···O3	2.7040 (15)	H5A···O3^iv	2.82 (2)
O3···C9	3.028 (2)	H5B···H6B	2.50 (3)
O3···C10	3.019 (3)	H5C···O1	2.51 (2)
O3···O2	2.7040 (15)	H5C···C1	2.81 (2)
O4···O1	2.6895 (14)	H5C···H4B	2.55 (3)
O1···H8A^i	2.62 (2)	H6A···H4C	2.46 (3)
O1···H9A^i	2.60 (2)	H6B···H4A	2.51 (3)
O1···H4C^ii	2.69 (2)	H6B···H5B	2.50 (3)
O1···H5C	2.51 (2)	H6B···O3^vi	2.683 (17)
O1···H4B	2.462 (18)	H6C···H5A	2.46 (3)
O3···H9B	2.49 (2)	H8A···H9A	2.49 (3)
O3···H10B	2.45 (2)	H8A···H10A	2.50 (3)
O3···H6B^iii	2.683 (17)	H8A···O1^viii	2.62 (2)
O3···H5A^iv	2.82 (2)	H8B···H10C	2.47 (4)
O3···H4A^iii	2.619 (19)	H8C···H9C	2.37 (3)
O4···H10C^v	2.84 (2)	H8C···H10B^i	2.57 (3)
C4···O1	2.9880 (19)	H9A···H8A	2.49 (3)
C5···O1	3.048 (2)	H9A···H10A	2.60 (3)
C9···O3	3.028 (2)	H9A···O1^viii	2.60 (2)
C10···O3	3.019 (3)	H9B···O3	2.49 (2)
C1···H4B	2.841 (18)	H9B···C2	2.82 (2)
C1···H4C^ii	3.06 (2)	H9B···H10B	2.54 (3)
C1···H5C	2.81 (2)	H9C···H8C	2.37 (3)
C2···H9B	2.82 (2)	H10A···H8A	2.50 (3)
C2···H10B	2.795 (19)	H10A···H9A	2.60 (3)
H4A···H6B	2.51 (3)	H10B···O3	2.45 (2)
H4A···O3^vi	2.619 (19)	H10B···C2	2.795 (19)
H4B···O1	2.462 (18)	H10B···H9B	2.54 (3)
H4B···C1	2.841 (18)	H10B···H8C^viii	2.57 (3)
H4B···H5C	2.55 (3)	H10C···H8B	2.47 (4)
H4C···H6A	2.46 (3)	H10C···O4^v	2.84 (2)
C1—O2—C3	120.75 (10)	C3—C5—H5C	111.9 (13)
C2—O4—C7	121.14 (11)	H5A—C5—H5B	106.0 (17)
O1—C1—O2	127.98 (12)	H5A—C5—H5C	109.1 (16)
O1—C1—C2	122.32 (12)	H5B—C5—H5C	112.2 (15)
O2—C1—C2	109.69 (10)	C3—C6—H6A	108.4 (12)
O3—C2—O4	127.84 (13)	C3—C6—H6B	109.0 (10)
O3—C2—C1	122.85 (13)	C3—C6—H6C	109.6 (11)
O4—C2—C1	109.30 (11)	H6A—C6—H6B	109.0 (15)
O2—C3—C4	109.87 (13)	H6A—C6—H6C	113.1 (17)
O2—C3—C5	108.94 (11)	H6B—C6—H6C	107.7 (17)
O2—C3—C6	102.22 (11)	C7—C8—H8A	107.8 (13)
C4—C3—C5	112.85 (13)	C7—C8—H8B	112.1 (18)
C4—C3—C6	111.05 (13)	C7—C8—H8C	103.0 (14)
C5—C3—C6	111.37 (15)	H8A—C8—H8B	114 (2)
O4—C7—C8	101.88 (12)	H8A—C8—H8C	103.7 (17)
O4—C7—C9	109.07 (14)	H8B—C8—H8C	116 (2)
O4—C7—C10	109.73 (11)	C7—C9—H9A	107.1 (14)
C8—C7—C9	112.85 (14)	C7—C9—H9B	111.4 (12)
C8—C7—C10	109.77 (15)	C7—C9—H9C	109.3 (13)
C9—C7—C10	112.95 (14)	H9A—C9—H9B	110.2 (17)
C3—C4—H4A	107.8 (12)	H9A—C9—H9C	108.8 (16)
C3—C4—H4B	112.0 (12)	H9B—C9—H9C	110.0 (19)
C3—C4—H4C	110.3 (12)	C7—C10—H10A	108.1 (11)
H4A—C4—H4B	108.1 (14)	C7—C10—H10B	111.0 (12)
H4A—C4—H4C	108.4 (15)	C7—C10—H10C	108.4 (12)
H4B—C4—H4C	110.1 (18)	H10A—C10—H10B	111.6 (17)
C3—C5—H5A	110.1 (11)	H10A—C10—H10C	107.9 (19)
C3—C5—H5B	107.4 (12)	H10B—C10—H10C	109.7 (17)
C3—O2—C1—O1	−2.0 (2)	C7—O4—C2—C1	178.24 (11)
C3—O2—C1—C2	176.87 (12)	C2—O4—C7—C9	−62.45 (16)
C1—O2—C3—C5	−63.56 (17)	C2—O4—C7—C10	61.77 (18)
C1—O2—C3—C6	178.51 (14)	O1—C1—C2—O3	150.16 (15)
C1—O2—C3—C4	60.54 (16)	O2—C1—C2—O3	−28.75 (19)
C2—O4—C7—C8	178.04 (13)	O2—C1—C2—O4	152.34 (12)
C7—O4—C2—O3	−0.6 (2)	O1—C1—C2—O4	−28.76 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.977 (18)	2.462 (18)	2.9880 (19)	113.4 (13)
C5—H5C···O1	0.977 (18)	2.51 (2)	3.048 (2)	114.8 (14)
C9—H9B···O3	0.99 (2)	2.49 (2)	3.028 (2)	114.1 (15)
C10—H10B···O3	1.00 (2)	2.45 (2)	3.019 (3)	115.8 (13)

(DtBO150)

Crystal data

C10H18O4	F(000) = 440
Mr = 202.24	Dx = 1.143 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2923 reflections
a = 11.120 (2) Å	θ = 2.1–27.5°
b = 10.650 (2) Å	µ = 0.09 mm^−1
c = 11.277 (2) Å	T = 150 K
β = 118.35 (3)°	Block, colourless
V = 1175.3 (5) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2157 independent reflections
Radiation source: Sealed Tube	1947 reflections with > 2σ(i)
Graphite Monochromator monochromator	Rint = 0.054
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −12→12
Tmin = 0.958, Tmax = 0.970	l = −13→13
10287 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 0.2312P] where P = (Fo^2 + 2Fc^2)/3
2157 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.20 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.74774 (9)	0.24501 (8)	−0.00265 (9)	0.0360 (3)
O2	0.89892 (9)	0.11222 (8)	0.15422 (8)	0.0295 (3)
O3	0.78947 (10)	−0.07157 (9)	−0.03240 (10)	0.0435 (3)
O4	0.59394 (8)	0.04190 (8)	−0.12170 (9)	0.0316 (3)
C1	0.79158 (12)	0.14207 (11)	0.03922 (12)	0.0263 (3)
C2	0.72568 (12)	0.02187 (11)	−0.04219 (12)	0.0272 (3)
C3	0.98620 (12)	0.21197 (11)	0.24990 (12)	0.0291 (3)
C4	0.90108 (15)	0.29138 (14)	0.29388 (15)	0.0364 (4)
C5	1.05216 (15)	0.28863 (15)	0.18294 (15)	0.0377 (4)
C6	1.09115 (16)	0.13569 (14)	0.36614 (15)	0.0436 (4)
C7	0.50436 (13)	−0.05755 (12)	−0.21575 (13)	0.0322 (4)
C8	0.36552 (15)	0.00577 (16)	−0.2804 (2)	0.0520 (5)
C9	0.55381 (18)	−0.0880 (2)	−0.31620 (16)	0.0519 (6)
C10	0.50238 (17)	−0.17071 (14)	−0.13598 (16)	0.0425 (5)
H4A	0.9633 (16)	0.3489 (14)	0.3664 (16)	0.040 (4)*
H4B	0.8328 (17)	0.3424 (15)	0.2201 (17)	0.044 (4)*
H4C	0.8531 (18)	0.2398 (17)	0.3286 (18)	0.056 (5)*
H5A	1.1023 (17)	0.2323 (16)	0.1518 (17)	0.053 (5)*
H5B	1.1165 (19)	0.3431 (17)	0.2487 (18)	0.056 (5)*
H5C	0.9830 (17)	0.3361 (15)	0.1050 (16)	0.042 (4)*
H6A	1.0436 (18)	0.0842 (17)	0.4039 (18)	0.056 (5)*
H6B	1.1562 (16)	0.1939 (15)	0.4357 (16)	0.042 (4)*
H6C	1.1443 (18)	0.0841 (17)	0.3342 (17)	0.054 (5)*
H8A	0.2963 (18)	−0.0527 (16)	−0.3501 (17)	0.050 (4)*
H8B	0.334 (3)	0.030 (2)	−0.210 (3)	0.104 (8)*
H8C	0.373 (2)	0.072 (2)	−0.330 (2)	0.065 (6)*
H9A	0.486 (2)	−0.1446 (17)	−0.3845 (19)	0.061 (5)*
H9B	0.644 (2)	−0.1328 (17)	−0.2736 (19)	0.065 (6)*
H9C	0.559 (2)	−0.010 (2)	−0.361 (2)	0.078 (6)*
H10A	0.4318 (19)	−0.2320 (18)	−0.1991 (19)	0.061 (5)*
H10B	0.594 (2)	−0.2107 (17)	−0.0895 (18)	0.060 (5)*
H10C	0.474 (2)	−0.1426 (18)	−0.068 (2)	0.068 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0358 (5)	0.0270 (5)	0.0350 (5)	0.0016 (4)	0.0084 (4)	0.0019 (4)
O2	0.0286 (5)	0.0247 (4)	0.0258 (4)	−0.0017 (3)	0.0052 (4)	−0.0019 (3)
O3	0.0327 (5)	0.0353 (5)	0.0463 (6)	0.0065 (4)	0.0055 (5)	−0.0115 (4)
O4	0.0233 (4)	0.0278 (5)	0.0339 (5)	−0.0002 (3)	0.0056 (4)	−0.0047 (4)
C1	0.0240 (6)	0.0287 (6)	0.0255 (6)	0.0005 (5)	0.0111 (5)	0.0004 (5)
C2	0.0255 (6)	0.0287 (6)	0.0241 (6)	0.0013 (5)	0.0090 (5)	−0.0002 (5)
C3	0.0272 (6)	0.0277 (6)	0.0274 (6)	−0.0063 (5)	0.0088 (5)	−0.0064 (5)
C4	0.0354 (7)	0.0396 (8)	0.0355 (7)	−0.0066 (6)	0.0178 (6)	−0.0106 (6)
C5	0.0338 (7)	0.0407 (8)	0.0409 (8)	−0.0102 (6)	0.0196 (7)	−0.0086 (6)
C6	0.0394 (8)	0.0377 (8)	0.0339 (7)	−0.0020 (7)	0.0012 (7)	−0.0046 (6)
C7	0.0252 (6)	0.0314 (7)	0.0316 (7)	−0.0051 (5)	0.0067 (5)	−0.0072 (5)
C8	0.0288 (7)	0.0385 (8)	0.0639 (11)	−0.0023 (7)	0.0018 (8)	−0.0015 (8)
C9	0.0449 (9)	0.0744 (12)	0.0341 (8)	−0.0206 (9)	0.0168 (7)	−0.0195 (8)
C10	0.0405 (8)	0.0343 (7)	0.0492 (9)	−0.0063 (7)	0.0184 (7)	−0.0031 (6)

Geometric parameters (Å, º)

O1—C1	1.2016 (15)	C5—H5A	0.990 (19)
O2—C1	1.3182 (15)	C5—H5B	0.946 (19)
O2—C3	1.4967 (15)	C5—H5C	0.989 (17)
O3—C2	1.1964 (17)	C6—H6A	0.99 (2)
O4—C2	1.3221 (17)	C6—H6B	0.992 (17)
O4—C7	1.4952 (16)	C6—H6C	0.99 (2)
C1—C2	1.5426 (17)	C8—H8A	1.012 (18)
C3—C4	1.518 (2)	C8—H8B	1.04 (3)
C3—C5	1.517 (2)	C8—H8C	0.93 (2)
C3—C6	1.512 (2)	C9—H9A	0.987 (19)
C7—C8	1.517 (2)	C9—H9B	1.00 (2)
C7—C9	1.511 (2)	C9—H9C	0.99 (2)
C7—C10	1.510 (2)	C10—H10A	1.01 (2)
C4—H4A	0.993 (16)	C10—H10B	0.99 (2)
C4—H4B	0.982 (17)	C10—H10C	1.00 (2)
C4—H4C	0.97 (2)
O1···O4	2.6881 (14)	H4B···H5C	2.56 (3)
O1···C4	2.9864 (18)	H4C···H6A	2.50 (3)
O1···C5	3.054 (2)	H4C···O1^vi	2.67 (2)
O2···O3	2.7035 (14)	H4C···C1^vi	3.04 (2)
O3···C9	3.029 (2)	H5A···H6C	2.46 (2)
O3···C10	3.022 (2)	H5A···O3^iv	2.780 (19)
O3···O2	2.7035 (14)	H5B···H6B	2.51 (2)
O4···O1	2.6881 (14)	H5C···O1	2.499 (19)
O1···H8A^i	2.620 (17)	H5C···C1	2.802 (18)
O1···H9A^i	2.57 (2)	H5C···H4B	2.56 (3)
O1···H4C^ii	2.67 (2)	H6A···H4C	2.50 (3)
O1···H5C	2.499 (19)	H6B···H4A	2.52 (3)
O1···H4B	2.454 (17)	H6B···H5B	2.51 (2)
O3···H9B	2.502 (19)	H6B···O3^vii	2.677 (16)
O3···H10B	2.45 (2)	H6C···H5A	2.46 (2)
O3···H6B^iii	2.677 (16)	H8A···H9A	2.52 (3)
O3···H5A^iv	2.780 (19)	H8A···H10A	2.53 (3)
O3···H4A^iii	2.625 (18)	H8A···O1^viii	2.620 (17)
O4···H10C^v	2.80 (2)	H8B···H10C	2.45 (3)
C1···C4^ii	3.583 (2)	H8C···H9C	2.42 (3)
C4···C1^vi	3.583 (2)	H8C···H10B^i	2.58 (3)
C4···O1	2.9864 (18)	H9A···H8A	2.52 (3)
C5···O1	3.054 (2)	H9A···O1^viii	2.57 (2)
C9···O3	3.029 (2)	H9B···O3	2.502 (19)
C10···O3	3.022 (2)	H9B···C2	2.846 (19)
C1···H4B	2.835 (17)	H9B···H10B	2.53 (3)
C1···H5C	2.802 (18)	H9C···H8C	2.42 (3)
C1···H4C^ii	3.04 (2)	H10A···H8A	2.53 (3)
C2···H10B	2.797 (19)	H10B···O3	2.45 (2)
C2···H9B	2.846 (19)	H10B···C2	2.797 (19)
H4A···H6B	2.52 (3)	H10B···H9B	2.53 (3)
H4A···O3^vii	2.625 (18)	H10B···H8C^viii	2.58 (3)
H4B···O1	2.454 (17)	H10C···H8B	2.45 (3)
H4B···C1	2.835 (17)	H10C···O4^v	2.80 (2)
C1—O2—C3	120.82 (10)	C3—C5—H5C	111.2 (12)
C2—O4—C7	121.14 (10)	H5A—C5—H5B	107.8 (17)
O1—C1—O2	127.99 (12)	H5A—C5—H5C	109.0 (15)
O1—C1—C2	122.27 (12)	H5B—C5—H5C	111.3 (15)
O2—C1—C2	109.74 (10)	C3—C6—H6A	108.7 (12)
O3—C2—O4	127.90 (12)	C3—C6—H6B	108.8 (9)
O3—C2—C1	122.82 (13)	C3—C6—H6C	109.3 (10)
O4—C2—C1	109.27 (11)	H6A—C6—H6B	110.2 (15)
O2—C3—C4	109.85 (12)	H6A—C6—H6C	112.5 (16)
O2—C3—C5	108.93 (11)	H6B—C6—H6C	107.3 (16)
O2—C3—C6	102.29 (10)	C7—C8—H8A	109.0 (11)
C4—C3—C5	112.76 (12)	C7—C8—H8B	112.2 (17)
C4—C3—C6	111.13 (12)	C7—C8—H8C	105.4 (15)
C5—C3—C6	111.35 (14)	H8A—C8—H8B	110 (2)
O4—C7—C8	102.08 (11)	H8A—C8—H8C	104.6 (16)
O4—C7—C9	109.08 (13)	H8B—C8—H8C	115.5 (18)
O4—C7—C10	109.63 (11)	C7—C9—H9A	107.5 (14)
C8—C7—C9	112.63 (13)	C7—C9—H9B	112.3 (11)
C8—C7—C10	109.98 (15)	C7—C9—H9C	109.5 (13)
C9—C7—C10	112.88 (14)	H9A—C9—H9B	107.6 (17)
C3—C4—H4A	108.3 (11)	H9A—C9—H9C	108.9 (16)
C3—C4—H4B	112.5 (11)	H9B—C9—H9C	110.9 (18)
C3—C4—H4C	111.4 (12)	C7—C10—H10A	108.8 (11)
H4A—C4—H4B	108.2 (13)	C7—C10—H10B	110.8 (12)
H4A—C4—H4C	108.6 (15)	C7—C10—H10C	108.4 (11)
H4B—C4—H4C	107.7 (17)	H10A—C10—H10B	110.7 (16)
C3—C5—H5A	109.7 (11)	H10A—C10—H10C	108.1 (18)
C3—C5—H5B	107.7 (12)	H10B—C10—H10C	109.9 (17)
C3—O2—C1—O1	−2.0 (2)	C7—O4—C2—C1	178.20 (11)
C3—O2—C1—C2	176.94 (11)	C2—O4—C7—C9	−62.32 (16)
C1—O2—C3—C5	−63.71 (16)	C2—O4—C7—C10	61.75 (17)
C1—O2—C3—C6	178.34 (13)	O1—C1—C2—O3	150.41 (15)
C1—O2—C3—C4	60.25 (15)	O2—C1—C2—O3	−28.57 (19)
C2—O4—C7—C8	178.31 (13)	O2—C1—C2—O4	152.59 (12)
C7—O4—C2—O3	−0.6 (2)	O1—C1—C2—O4	−28.43 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.982 (17)	2.454 (17)	2.9864 (18)	113.6 (12)
C5—H5C···O1	0.989 (17)	2.499 (19)	3.054 (2)	115.2 (13)
C9—H9A···O1^viii	0.987 (19)	2.57 (2)	3.475 (2)	152.1 (18)
C9—H9B···O3	1.00 (2)	2.502 (19)	3.029 (2)	112.3 (14)
C10—H10B···O3	0.99 (2)	2.45 (2)	3.022 (2)	116.0 (13)

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

(DtBO125)

Crystal data

C10H18O4	F(000) = 440
Mr = 202.24	Dx = 1.149 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3081 reflections
a = 11.100 (2) Å	θ = 2.1–27.5°
b = 10.635 (2) Å	µ = 0.09 mm^−1
c = 11.243 (2) Å	T = 125 K
β = 118.22 (3)°	Block, colourless
V = 1169.5 (5) Å^3	0.50 × 0.35 × 0.35 mm
Z = 4

Data collection

Rigaku Mercury375R (2x2 bin mode) diffractometer	2149 independent reflections
Radiation source: Sealed Tube	1960 reflections with > 2σ(i)
Graphite Monochromator monochromator	Rint = 0.056
Detector resolution: 13.6612 pixels mm^-1	θmax = 25.4°, θmin = 2.8°
profile data from ω–scans	h = −13→13
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −12→12
Tmin = 0.957, Tmax = 0.970	l = −13→13
10238 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.1928P] where P = (Fo^2 + 2Fc^2)/3
2149 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.19 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.74746 (8)	0.24502 (8)	−0.00212 (8)	0.0310 (3)
O2	0.89925 (8)	0.11177 (7)	0.15438 (8)	0.0259 (2)
O3	0.78950 (9)	−0.07247 (9)	−0.03244 (9)	0.0373 (3)
O4	0.59382 (8)	0.04147 (8)	−0.12127 (8)	0.0275 (3)
C1	0.79149 (11)	0.14186 (11)	0.03964 (11)	0.0230 (3)
C2	0.72565 (11)	0.02128 (11)	−0.04197 (11)	0.0238 (3)
C3	0.98654 (11)	0.21173 (11)	0.25007 (11)	0.0256 (3)
C4	0.90124 (13)	0.29111 (13)	0.29492 (14)	0.0313 (4)
C5	1.05220 (14)	0.28877 (14)	0.18268 (14)	0.0326 (4)
C6	1.09176 (15)	0.13555 (13)	0.36626 (14)	0.0372 (4)
C7	0.50440 (12)	−0.05845 (12)	−0.21531 (12)	0.0281 (3)
C8	0.36548 (14)	0.00534 (15)	−0.28044 (18)	0.0440 (5)
C9	0.55382 (16)	−0.08861 (18)	−0.31652 (15)	0.0448 (5)
C10	0.50235 (15)	−0.17181 (13)	−0.13540 (15)	0.0364 (4)
H4A	0.9637 (15)	0.3472 (14)	0.3676 (15)	0.035 (4)*
H4B	0.8342 (16)	0.3429 (15)	0.2209 (16)	0.039 (4)*
H4C	0.8548 (18)	0.2393 (16)	0.3301 (17)	0.052 (5)*
H5A	1.1023 (17)	0.2323 (16)	0.1519 (16)	0.047 (4)*
H5B	1.1159 (17)	0.3451 (16)	0.2489 (17)	0.047 (4)*
H5C	0.9838 (16)	0.3363 (15)	0.1043 (16)	0.038 (4)*
H6A	1.0460 (16)	0.0843 (15)	0.4044 (16)	0.043 (4)*
H6B	1.1575 (15)	0.1937 (14)	0.4366 (15)	0.038 (4)*
H6C	1.1453 (17)	0.0837 (16)	0.3352 (17)	0.048 (4)*
H8A	0.2985 (17)	−0.0532 (16)	−0.3487 (17)	0.046 (4)*
H8B	0.337 (2)	0.027 (2)	−0.207 (2)	0.077 (6)*
H8C	0.3716 (18)	0.0755 (18)	−0.3279 (18)	0.053 (5)*
H9A	0.4860 (19)	−0.1435 (16)	−0.3844 (18)	0.054 (5)*
H9B	0.644 (2)	−0.1333 (16)	−0.2738 (18)	0.055 (5)*
H9C	0.5594 (19)	−0.0097 (19)	−0.3622 (19)	0.064 (6)*
H10A	0.4327 (17)	−0.2315 (16)	−0.1982 (17)	0.047 (4)*
H10B	0.5946 (18)	−0.2124 (16)	−0.0887 (17)	0.054 (5)*
H10C	0.4741 (19)	−0.1445 (17)	−0.067 (2)	0.061 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0307 (5)	0.0240 (5)	0.0306 (5)	0.0014 (4)	0.0082 (4)	0.0018 (4)
O2	0.0252 (4)	0.0219 (4)	0.0230 (4)	−0.0017 (3)	0.0052 (4)	−0.0018 (3)
O3	0.0279 (5)	0.0313 (5)	0.0396 (5)	0.0056 (4)	0.0051 (4)	−0.0098 (4)
O4	0.0203 (4)	0.0247 (4)	0.0298 (5)	−0.0006 (3)	0.0056 (4)	−0.0038 (3)
C1	0.0212 (5)	0.0255 (6)	0.0225 (6)	−0.0003 (5)	0.0104 (5)	−0.0003 (5)
C2	0.0223 (6)	0.0254 (6)	0.0213 (6)	0.0011 (5)	0.0084 (5)	0.0001 (4)
C3	0.0239 (6)	0.0247 (6)	0.0241 (6)	−0.0052 (5)	0.0081 (5)	−0.0051 (5)
C4	0.0310 (7)	0.0340 (7)	0.0307 (7)	−0.0048 (6)	0.0161 (6)	−0.0079 (6)
C5	0.0295 (7)	0.0349 (7)	0.0356 (7)	−0.0083 (6)	0.0172 (6)	−0.0068 (6)
C6	0.0340 (7)	0.0320 (7)	0.0298 (7)	−0.0008 (6)	0.0022 (6)	−0.0032 (6)
C7	0.0224 (6)	0.0274 (6)	0.0279 (6)	−0.0050 (5)	0.0064 (5)	−0.0066 (5)
C8	0.0254 (7)	0.0339 (8)	0.0538 (9)	−0.0024 (6)	0.0031 (7)	−0.0012 (7)
C9	0.0383 (8)	0.0645 (11)	0.0301 (7)	−0.0180 (8)	0.0149 (7)	−0.0164 (7)
C10	0.0351 (7)	0.0301 (7)	0.0421 (8)	−0.0053 (6)	0.0167 (7)	−0.0028 (6)

Geometric parameters (Å, º)

O1—C1	1.2025 (15)	C5—H5A	0.986 (19)
O2—C1	1.3183 (14)	C5—H5B	0.957 (18)
O2—C3	1.4969 (14)	C5—H5C	0.988 (16)
O3—C2	1.1984 (16)	C6—H6A	0.972 (18)
O4—C2	1.3223 (16)	C6—H6B	0.997 (16)
O4—C7	1.4966 (15)	C6—H6C	0.988 (19)
C1—C2	1.5448 (17)	C8—H8A	0.995 (17)
C3—C4	1.522 (2)	C8—H8B	1.04 (2)
C3—C5	1.516 (2)	C8—H8C	0.938 (19)
C3—C6	1.5113 (19)	C9—H9A	0.973 (18)
C7—C8	1.519 (2)	C9—H9B	1.00 (2)
C7—C9	1.513 (2)	C9—H9C	1.00 (2)
C7—C10	1.510 (2)	C10—H10A	0.991 (18)
C4—H4A	0.984 (15)	C10—H10B	1.00 (2)
C4—H4B	0.982 (16)	C10—H10C	1.00 (2)
C4—H4C	0.96 (2)
O1···O4	2.6886 (13)	H4B···H5C	2.56 (3)
O1···C4	2.9860 (17)	H4C···H6A	2.50 (3)
O1···C5	3.0543 (19)	H4C···O1^vi	2.67 (2)
O2···O3	2.7047 (13)	H4C···C1^vi	3.034 (19)
O3···C9	3.0286 (19)	H5A···H6C	2.46 (2)
O3···C10	3.021 (2)	H5A···O3^iv	2.768 (19)
O3···O2	2.7047 (13)	H5B···H6B	2.52 (2)
O4···O1	2.6886 (13)	H5C···O1	2.508 (19)
O1···H8A^i	2.621 (17)	H5C···C1	2.810 (18)
O1···H9A^i	2.57 (2)	H5C···H4B	2.56 (3)
O1···H4C^ii	2.67 (2)	H6A···H4C	2.50 (3)
O1···H5C	2.508 (19)	H6B···H4A	2.51 (2)
O1···H4B	2.453 (16)	H6B···H5B	2.52 (2)
O3···H9B	2.499 (18)	H6B···O3^vii	2.663 (15)
O3···H10B	2.45 (2)	H6C···H5A	2.46 (2)
O3···H6B^iii	2.663 (15)	H8A···H9A	2.49 (3)
O3···H5A^iv	2.768 (19)	H8A···H10A	2.51 (2)
O3···H4A^iii	2.621 (17)	H8A···O1^viii	2.621 (17)
O4···H10C^v	2.79 (2)	H8B···H10C	2.42 (3)
C1···C4^ii	3.568 (2)	H8C···H9C	2.47 (3)
C4···C1^vi	3.568 (2)	H8C···H10B^i	2.54 (3)
C4···O1	2.9860 (17)	H9A···H8A	2.49 (3)
C5···O1	3.0543 (19)	H9A···O1^viii	2.57 (2)
C9···O3	3.0286 (19)	H9B···O3	2.499 (18)
C10···O3	3.021 (2)	H9B···C2	2.843 (18)
C1···H4B	2.835 (16)	H9B···H10B	2.53 (3)
C1···H5C	2.810 (18)	H9C···H8C	2.47 (3)
C1···H4C^ii	3.034 (19)	H10A···H8A	2.51 (2)
C2···H10B	2.801 (18)	H10B···O3	2.45 (2)
C2···H9B	2.843 (18)	H10B···C2	2.801 (18)
H4A···H6B	2.51 (2)	H10B···H9B	2.53 (3)
H4A···O3^vii	2.621 (17)	H10B···H8C^viii	2.54 (3)
H4B···O1	2.453 (16)	H10C···H8B	2.42 (3)
H4B···C1	2.835 (16)	H10C···O4^v	2.79 (2)
C1—O2—C3	120.69 (9)	C3—C5—H5C	112.0 (11)
C2—O4—C7	120.92 (10)	H5A—C5—H5B	108.8 (16)
O1—C1—O2	128.08 (11)	H5A—C5—H5C	108.8 (14)
O1—C1—C2	122.32 (11)	H5B—C5—H5C	110.3 (14)
O2—C1—C2	109.59 (10)	C3—C6—H6A	109.3 (11)
O3—C2—O4	127.92 (12)	C3—C6—H6B	109.3 (9)
O3—C2—C1	122.95 (12)	C3—C6—H6C	110.0 (10)
O4—C2—C1	109.12 (10)	H6A—C6—H6B	109.7 (13)
O2—C3—C4	109.85 (11)	H6A—C6—H6C	111.7 (15)
O2—C3—C5	108.99 (10)	H6B—C6—H6C	106.8 (15)
O2—C3—C6	102.33 (10)	C7—C8—H8A	108.1 (11)
C4—C3—C5	112.79 (11)	C7—C8—H8B	109.7 (12)
C4—C3—C6	111.02 (11)	C7—C8—H8C	107.4 (13)
C5—C3—C6	111.35 (13)	H8A—C8—H8B	110.8 (17)
O4—C7—C8	101.92 (11)	H8A—C8—H8C	106.7 (15)
O4—C7—C9	109.07 (12)	H8B—C8—H8C	114.0 (17)
O4—C7—C10	109.76 (10)	C7—C9—H9A	107.2 (13)
C8—C7—C9	112.25 (12)	C7—C9—H9B	112.1 (11)
C8—C7—C10	110.24 (13)	C7—C9—H9C	109.9 (12)
C9—C7—C10	113.02 (13)	H9A—C9—H9B	108.6 (16)
C3—C4—H4A	107.9 (10)	H9A—C9—H9C	108.3 (15)
C3—C4—H4B	111.8 (11)	H9B—C9—H9C	110.7 (17)
C3—C4—H4C	111.0 (11)	C7—C10—H10A	108.3 (10)
H4A—C4—H4B	108.5 (13)	C7—C10—H10B	110.9 (11)
H4A—C4—H4C	108.1 (14)	C7—C10—H10C	108.9 (10)
H4B—C4—H4C	109.4 (16)	H10A—C10—H10B	110.9 (15)
C3—C5—H5A	109.3 (10)	H10A—C10—H10C	108.1 (17)
C3—C5—H5B	107.6 (11)	H10B—C10—H10C	109.7 (16)
C3—O2—C1—O1	−1.7 (2)	C7—O4—C2—C1	178.26 (10)
C3—O2—C1—C2	176.93 (11)	C2—O4—C7—C9	−62.50 (15)
C1—O2—C3—C5	−63.87 (15)	C2—O4—C7—C10	61.82 (16)
C1—O2—C3—C6	178.14 (12)	O1—C1—C2—O3	150.50 (14)
C1—O2—C3—C4	60.16 (14)	O2—C1—C2—O3	−28.26 (17)
C2—O4—C7—C8	178.66 (12)	O2—C1—C2—O4	152.86 (11)
C7—O4—C2—O3	−0.55 (19)	O1—C1—C2—O4	−28.38 (17)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1	0.982 (16)	2.453 (16)	2.9860 (17)	113.7 (12)
C5—H5C···O1	0.988 (16)	2.508 (19)	3.0543 (19)	114.6 (12)
C9—H9A···O1^viii	0.973 (18)	2.57 (2)	3.467 (2)	152.8 (17)
C9—H9B···O3	1.00 (2)	2.499 (18)	3.0286 (19)	112.6 (13)
C10—H10B···O3	1.00 (2)	2.45 (2)	3.021 (2)	115.7 (12)

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

(MEO170)

Crystal data

C5H8O4	F(000) = 280
Mr = 132.11	Dx = 1.308 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1466 reflections
a = 16.317 (8) Å	θ = 5.0–52.8°
b = 4.461 (2) Å	µ = 0.12 mm^−1
c = 9.254 (4) Å	T = 170 K
β = 95.045 (7)°	Cylindrical, colourless
V = 671.0 (5) Å^3	0.50 × 0.50 × 0.35 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	1237 independent reflections
Radiation source: fine-focus sealed tube	930 reflections with > 2σ(i)
Graphite monochromator	Rint = 0.052
ϕ and ω scans	θmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.945, Tmax = 0.961	k = −5→5
5803 measured reflections	l = −11→11

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)] = 0.108	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.246	H atoms treated by a mixture of independent and constrained refinement
S = 1.25	w = 1/[σ^2(Fo^2) + (0.0517P)^2 + 2.9201P] where P = (Fo^2 + 2Fc^2)/3
1237 reflections	(Δ/σ)max < 0.001
95 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.29 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.0957 (2)	0.3977 (9)	0.5514 (4)	0.0324 (12)
O2	0.2212 (2)	0.2168 (9)	0.6298 (4)	0.0368 (12)
O3	0.1646 (2)	0.7790 (9)	0.3769 (4)	0.0375 (12)
O4	0.2894 (2)	0.5972 (10)	0.4523 (4)	0.0391 (12)
C1	0.0579 (4)	0.1983 (15)	0.6480 (7)	0.0361 (17)
C2	0.1771 (3)	0.3820 (12)	0.5556 (5)	0.0262 (17)
C3	0.2084 (3)	0.6114 (13)	0.4501 (6)	0.0324 (17)
C4	0.3271 (4)	0.8020 (16)	0.3546 (7)	0.048 (2)
C5	0.4143 (5)	0.744 (3)	0.3667 (12)	0.104 (4)
H1A	−0.002 (4)	0.243 (14)	0.625 (6)	0.038 (16)*
H1B	0.074 (3)	−0.009 (14)	0.617 (6)	0.036 (16)*
H1C	0.079 (3)	0.250 (13)	0.744 (6)	0.030 (15)*
H4A	0.30360	0.76940	0.25350	0.0580*
H4B	0.31650	1.01230	0.38160	0.0580*
H5A	0.43460	0.73110	0.46940	0.1560*
H5B	0.44270	0.90630	0.32040	0.1560*
H5C	0.42490	0.55340	0.31870	0.1560*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.034 (2)	0.030 (2)	0.033 (2)	0.0019 (17)	0.0021 (16)	0.0027 (17)
O2	0.039 (2)	0.032 (2)	0.038 (2)	0.0089 (18)	−0.0041 (18)	0.0036 (19)
O3	0.035 (2)	0.033 (2)	0.044 (2)	0.0044 (18)	0.0007 (18)	0.006 (2)
O4	0.033 (2)	0.040 (2)	0.044 (2)	0.0061 (19)	0.0021 (17)	0.004 (2)
C1	0.040 (3)	0.034 (3)	0.034 (3)	0.002 (3)	0.002 (3)	−0.004 (3)
C2	0.032 (3)	0.022 (3)	0.024 (3)	0.002 (2)	0.000 (2)	−0.008 (2)
C3	0.030 (3)	0.030 (3)	0.036 (3)	0.006 (2)	−0.003 (2)	−0.010 (3)
C4	0.046 (4)	0.047 (4)	0.054 (4)	0.003 (3)	0.014 (3)	0.015 (3)
C5	0.043 (4)	0.122 (9)	0.149 (9)	0.012 (5)	0.023 (5)	0.085 (8)

Geometric parameters (Å, º)

O1—C1	1.438 (8)	C1—H1A	1.00 (7)
O1—C2	1.327 (6)	C1—H1B	1.01 (6)
O2—C2	1.202 (6)	C1—H1C	0.95 (6)
O3—C3	1.202 (7)	C4—H4A	0.9900
O4—C3	1.322 (6)	C4—H4B	0.9900
O4—C4	1.459 (8)	C5—H5A	0.9800
C2—C3	1.533 (8)	C5—H5B	0.9800
C4—C5	1.441 (11)	C5—H5C	0.9800
O1···O3	2.662 (5)	O4···H4A^iii	2.8400
O2···O3^i	3.125 (6)	C1···C1^viii	3.569 (9)
O2···C3^ii	3.329 (7)	C1···C1^ix	3.569 (9)
O2···C4^iii	3.360 (8)	C1···O3^ii	3.377 (8)
O2···O4	2.672 (6)	C2···O3^i	3.155 (7)
O2···C3^i	3.169 (7)	C2···O3^iii	3.358 (6)
O3···C2^iv	3.155 (7)	C3···O2^iv	3.169 (7)
O3···O2^iv	3.125 (6)	C3···O2^vi	3.329 (7)
O3···C2^v	3.358 (6)	C4···O2^v	3.360 (8)
O3···C1^vi	3.377 (8)	C2···H4A^iii	3.0600
O3···O1	2.662 (5)	H1A···O1^vii	2.67 (6)
O4···O2	2.672 (6)	H1A···O3^vii	2.65 (7)
O1···H1A^vii	2.67 (6)	H1B···O1^i	2.75 (6)
O1···H1C^vi	2.91 (6)	H1B···O2	2.60 (5)
O1···H1B^iv	2.75 (6)	H1C···O2	2.64 (5)
O2···H1C	2.64 (5)	H1C···O1^ii	2.91 (6)
O2···H4A^iii	2.8500	H1C···O3^iii	2.75 (6)
O2···H4A^ii	2.7500	H4A···O3	2.6300
O2···H1B	2.60 (5)	H4A···O2^vi	2.7500
O3···H1A^vii	2.65 (7)	H4A···O2^v	2.8500
O3···H4B	2.6900	H4A···O4^v	2.8400
O3···H1C^v	2.75 (6)	H4A···C2^v	3.0600
O3···H4A	2.6300	H4B···O3	2.6900
O4···H4B^i	2.7400	H4B···O4^iv	2.7400
C1—O1—C2	115.6 (4)	H1A—C1—H1C	115 (4)
C3—O4—C4	115.9 (5)	H1B—C1—H1C	114 (5)
O1—C2—O2	126.6 (5)	O4—C4—H4A	110.00
O1—C2—C3	109.6 (4)	O4—C4—H4B	110.00
O2—C2—C3	123.8 (4)	C5—C4—H4A	110.00
O3—C3—O4	125.7 (5)	C5—C4—H4B	110.00
O3—C3—C2	124.0 (4)	H4A—C4—H4B	108.00
O4—C3—C2	110.3 (4)	C4—C5—H5A	109.00
O4—C4—C5	107.9 (7)	C4—C5—H5B	110.00
O1—C1—H1A	102 (3)	C4—C5—H5C	109.00
O1—C1—H1B	105 (3)	H5A—C5—H5B	110.00
O1—C1—H1C	107 (3)	H5A—C5—H5C	109.00
H1A—C1—H1B	113 (5)	H5B—C5—H5C	109.00
C1—O1—C2—O2	1.1 (8)	O1—C2—C3—O3	0.6 (7)
C1—O1—C2—C3	−178.7 (4)	O1—C2—C3—O4	−179.6 (4)
C3—O4—C4—C5	−177.2 (7)	O2—C2—C3—O3	−179.2 (5)
C4—O4—C3—O3	−1.0 (8)	O2—C2—C3—O4	0.7 (7)
C4—O4—C3—C2	179.1 (5)

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x, y+1, z; (v) x, −y+3/2, z−1/2; (vi) x, −y+1/2, z−1/2; (vii) −x, −y+1, −z+1; (viii) −x, y−1/2, −z+3/2; (ix) −x, y+1/2, −z+3/2.

(MEO90)

Crystal data

C5H8O4	F(000) = 280
Mr = 132.11	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1965 reflections
a = 16.321 (8) Å	θ = 5.0–55.4°
b = 4.425 (2) Å	µ = 0.12 mm^−1
c = 9.127 (4) Å	T = 90 K
β = 95.092 (8)°	Cylindrical, colourless
V = 656.6 (5) Å^3	0.50 × 0.50 × 0.35 mm
Z = 4

Data collection

Bruker SMART CCD area detector diffractometer	1207 independent reflections
Radiation source: fine-focus sealed tube	918 reflections with > 2σ(i)
Graphite monochromator	Rint = 0.054
ϕ and ω scans	θmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.944, Tmax = 0.960	k = −5→5
5453 measured reflections	l = −11→11

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.280	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ^2(Fo^2) + (0.1139P)^2 + 1.8164P] where P = (Fo^2 + 2Fc^2)/3
1207 reflections	(Δ/σ)max < 0.001
114 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.45 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.0949 (2)	0.3973 (8)	0.5517 (4)	0.0197 (10)
O2	0.2200 (2)	0.2146 (8)	0.6321 (4)	0.0208 (10)
O3	0.1636 (2)	0.7827 (8)	0.3760 (4)	0.0214 (10)
O4	0.2882 (2)	0.5957 (8)	0.4523 (4)	0.0212 (11)
C1	0.0569 (3)	0.1949 (13)	0.6497 (6)	0.0230 (17)
C2	0.1759 (3)	0.3794 (11)	0.5571 (5)	0.0171 (12)
C3	0.2079 (3)	0.6147 (11)	0.4492 (5)	0.0186 (14)
C4	0.3257 (4)	0.8025 (14)	0.3519 (6)	0.0279 (17)
C5	0.4159 (4)	0.743 (2)	0.3714 (12)	0.060 (3)
H1A	−0.004 (3)	0.228 (12)	0.640 (5)	0.015 (12)*
H1B	0.081 (4)	0.002 (16)	0.624 (7)	0.035 (16)*
H1C	0.075 (3)	0.262 (13)	0.745 (6)	0.023 (14)*
H4A	0.305 (4)	0.780 (19)	0.244 (8)	0.06 (2)*
H4B	0.319 (4)	0.996 (17)	0.380 (7)	0.038 (18)*
H5A	0.432 (7)	0.81 (3)	0.491 (14)	0.12 (4)*
H5B	0.437 (4)	0.845 (18)	0.287 (9)	0.06 (2)*
H5C	0.436 (5)	0.536 (19)	0.350 (8)	0.05 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0247 (19)	0.0137 (17)	0.0204 (17)	0.0008 (13)	0.0001 (13)	0.0014 (13)
O2	0.0246 (18)	0.0130 (18)	0.0241 (17)	0.0049 (14)	−0.0013 (14)	0.0005 (14)
O3	0.0240 (18)	0.0161 (19)	0.0235 (17)	0.0001 (14)	−0.0006 (14)	0.0038 (14)
O4	0.0199 (18)	0.0179 (19)	0.0258 (18)	0.0026 (14)	0.0016 (13)	0.0025 (14)
C1	0.025 (3)	0.020 (3)	0.024 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C2	0.021 (2)	0.012 (2)	0.018 (2)	0.0033 (19)	0.0000 (18)	−0.0054 (19)
C3	0.025 (3)	0.012 (2)	0.018 (2)	0.003 (2)	−0.0032 (19)	−0.0095 (19)
C4	0.034 (3)	0.022 (3)	0.028 (3)	−0.001 (2)	0.005 (2)	0.010 (2)
C5	0.033 (3)	0.062 (5)	0.089 (6)	0.008 (4)	0.022 (4)	0.045 (5)

Geometric parameters (Å, º)

O1—C1	1.444 (7)	C1—H1A	1.00 (5)
O1—C2	1.321 (6)	C1—H1B	0.98 (7)
O2—C2	1.196 (6)	C1—H1C	0.94 (6)
O3—C3	1.198 (6)	C4—H4A	1.02 (7)
O4—C3	1.311 (6)	C4—H4B	0.90 (7)
O4—C4	1.467 (7)	C5—H5A	1.14 (13)
C2—C3	1.555 (7)	C5—H5B	0.98 (8)
C4—C5	1.491 (9)	C5—H5C	1.00 (8)
O1···O3	2.656 (5)	C2···O3^i	3.112 (6)
O2···O3^i	3.095 (5)	C2···C3^i	3.576 (7)
O2···C3^ii	3.262 (6)	C2···O3^iii	3.294 (6)
O2···C4^ii	3.409 (7)	C3···O2^iv	3.133 (6)
O2···O4	2.665 (5)	C3···C2^iv	3.576 (7)
O2···C3^i	3.133 (6)	C3···O2^vi	3.262 (6)
O2···C4^iii	3.309 (7)	C4···O2^vi	3.409 (7)
O3···C2^iv	3.112 (6)	C4···O2^v	3.309 (7)
O3···C2^v	3.294 (6)	C1···H1A^viii	3.00 (5)
O3···C1^vi	3.336 (7)	C1···H1C^viii	3.10 (5)
O3···O2^iv	3.095 (5)	C2···H4A^iii	3.00 (7)
O3···O1	2.656 (5)	C3···H4A^iii	3.04 (7)
O4···O2	2.665 (5)	H1A···C1^ix	3.00 (5)
O1···H1C^vi	2.88 (5)	H1A···O1^vii	2.75 (5)
O1···H1B^iv	2.77 (7)	H1A···O3^vii	2.60 (5)
O1···H1A^vii	2.75 (5)	H1B···O1^i	2.77 (7)
O2···H4A^iii	2.78 (8)	H1B···O2	2.45 (7)
O2···H4A^ii	2.74 (8)	H1B···O3^i	2.90 (7)
O2···H1B	2.45 (7)	H1B···O3^ii	2.85 (7)
O2···H1C	2.67 (5)	H1C···O2	2.67 (5)
O3···H1B^iv	2.90 (7)	H1C···C1^ix	3.10 (5)
O3···H1A^vii	2.60 (5)	H1C···O1^ii	2.88 (5)
O3···H4B	2.70 (7)	H1C···O3^iii	2.70 (5)
O3···H1B^vi	2.85 (6)	H4A···O3	2.70 (7)
O3···H1C^v	2.70 (5)	H4A···O2^vi	2.74 (8)
O3···H4A	2.70 (7)	H4A···O2^v	2.78 (8)
O4···H4B^i	2.79 (7)	H4A···O4^v	2.71 (7)
O4···H4A^iii	2.71 (7)	H4A···C2^v	3.00 (7)
C1···C1^viii	3.507 (8)	H4A···C3^v	3.04 (7)
C1···C1^ix	3.507 (8)	H4B···O3	2.70 (7)
C1···O3^ii	3.336 (7)	H4B···O4^iv	2.79 (7)
C1—O1—C2	115.0 (4)	H1A—C1—H1C	105 (4)
C3—O4—C4	114.7 (4)	H1B—C1—H1C	113 (5)
O1—C2—O2	127.4 (5)	O4—C4—H4A	115 (4)
O1—C2—C3	109.1 (4)	O4—C4—H4B	110 (4)
O2—C2—C3	123.5 (4)	C5—C4—H4A	110 (4)
O3—C3—O4	127.2 (5)	C5—C4—H4B	106 (4)
O3—C3—C2	123.3 (4)	H4A—C4—H4B	109 (6)
O4—C3—C2	109.6 (4)	C4—C5—H5A	102 (6)
O4—C4—C5	106.1 (5)	C4—C5—H5B	104 (4)
O1—C1—H1A	109 (3)	C4—C5—H5C	119 (5)
O1—C1—H1B	101 (4)	H5A—C5—H5B	124 (8)
O1—C1—H1C	105 (3)	H5A—C5—H5C	112 (8)
H1A—C1—H1B	122 (5)	H5B—C5—H5C	97 (6)
C1—O1—C2—O2	0.7 (7)	O1—C2—C3—O3	0.6 (6)
C1—O1—C2—C3	−178.6 (4)	O1—C2—C3—O4	−179.1 (4)
C3—O4—C4—C5	−179.5 (5)	O2—C2—C3—O3	−178.8 (5)
C4—O4—C3—O3	−1.1 (7)	O2—C2—C3—O4	1.5 (7)
C4—O4—C3—C2	178.6 (4)

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x, y+1, z; (v) x, −y+3/2, z−1/2; (vi) x, −y+1/2, z−1/2; (vii) −x, −y+1, −z+1; (viii) −x, y−1/2, −z+3/2; (ix) −x, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3^vii	1.00 (5)	2.60 (5)	3.587 (6)	170 (4)

Symmetry code: (vii) −x, −y+1, −z+1.