3,5-Di-C-methyl-5,6-O-isopropyl­idene-L-mannono-1,4-lactone

The relative configuration at position C-2 of the title lactone, C₁₁H₁₈O₆, which exists in the five-membered ring form, was unequivocally established by X-ray crystallographic analysis. The absolute configuration was determined by the use of 2,4-di-C-methyl-L-arabinose as the starting material.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.075
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.860     0.990
            Tmin(prime) and Tmax expected:      0.978     0.994
            RR(prime) =      0.884
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               1570
           Count of symmetry unique reflns         1589
           Completeness (_total/calc)             98.80%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

3,5-Di-C-methyl-5,6-O-isopropylidene-L-mannono-1,4-lactone

Crystal data

C11H18O6	F(000) = 528
Mr = 246.26	Dx = 1.376 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1542 reflections
a = 7.1286 (2) Å	θ = 5–27°
b = 9.7360 (3) Å	µ = 0.11 mm^−1
c = 17.1314 (6) Å	T = 150 K
V = 1188.99 (6) Å^3	Plate, colourless
Z = 4	0.20 × 0.05 × 0.05 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	1327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan (DENZO andSCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.86, Tmax = 0.99	k = −12→12
7431 measured reflections	l = −22→22
1570 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.075	w = 1/[σ^2(F^2) + (0.03P)^2 + 0.26P], where P = [max(Fo^2,0) + 2Fc^2]/3
S = 0.93	(Δ/σ)max = 0.000412
1570 reflections	Δρmax = 0.26 e Å^−3
154 parameters	Δρmin = −0.25 e Å^−3
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6785 (3)	0.42375 (18)	0.81786 (10)	0.0194
C2	0.6098 (3)	0.34715 (19)	0.74448 (10)	0.0192
C3	0.5047 (3)	0.42343 (19)	0.67936 (10)	0.0207
C4	0.5473 (3)	0.32753 (19)	0.61044 (10)	0.0237
C5	0.7451 (3)	0.27984 (19)	0.62838 (10)	0.0242
O6	0.77545 (19)	0.28812 (13)	0.70600 (7)	0.0237
O7	0.8641 (2)	0.23780 (15)	0.58470 (8)	0.0363
O8	0.5329 (2)	0.39598 (14)	0.53817 (7)	0.0311
O9	0.5959 (2)	0.55127 (13)	0.66597 (7)	0.0248
C10	0.2965 (3)	0.4425 (2)	0.69378 (11)	0.0273
O11	0.51304 (19)	0.48324 (13)	0.85324 (7)	0.0204
C12	0.4562 (3)	0.40079 (18)	0.91915 (10)	0.0204
O13	0.56739 (18)	0.27822 (13)	0.91505 (7)	0.0215
C14	0.7392 (3)	0.31852 (19)	0.87928 (10)	0.0219
C15	0.2519 (3)	0.3614 (2)	0.91058 (12)	0.0279
C16	0.4963 (3)	0.4794 (2)	0.99398 (10)	0.0285
C17	0.8260 (3)	0.5331 (2)	0.80469 (11)	0.0265
H21	0.5275	0.2698	0.7627	0.0250*
H41	0.4614	0.2453	0.6115	0.0294*
H101	0.2421	0.4743	0.6443	0.0433*
H102	0.2813	0.5100	0.7354	0.0439*
H103	0.2417	0.3568	0.7087	0.0433*
H141	0.8207	0.3614	0.9183	0.0274*
H142	0.8002	0.2369	0.8557	0.0276*
H151	0.2161	0.3056	0.9558	0.0440*
H152	0.1768	0.4466	0.9088	0.0445*
H153	0.2341	0.3114	0.8611	0.0441*
H161	0.4650	0.4221	1.0391	0.0450*
H162	0.6325	0.5018	0.9950	0.0454*
H163	0.4181	0.5629	0.9936	0.0452*
H171	0.8593	0.5751	0.8553	0.0414*
H172	0.9393	0.4883	0.7845	0.0416*
H173	0.7828	0.6037	0.7679	0.0415*
H12	0.5549	0.5966	0.6276	0.0404*
H13	0.4678	0.3418	0.5108	0.0505*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0192 (9)	0.0213 (9)	0.0177 (8)	0.0011 (9)	0.0015 (8)	−0.0006 (7)
C2	0.0221 (10)	0.0183 (9)	0.0172 (8)	0.0036 (8)	0.0028 (8)	0.0005 (7)
C3	0.0271 (10)	0.0179 (8)	0.0173 (9)	0.0013 (9)	−0.0011 (8)	−0.0007 (7)
C4	0.0364 (11)	0.0183 (9)	0.0162 (8)	−0.0020 (9)	−0.0022 (9)	0.0006 (7)
C5	0.0369 (11)	0.0168 (9)	0.0190 (8)	0.0004 (10)	0.0061 (9)	−0.0008 (7)
O6	0.0282 (7)	0.0243 (6)	0.0186 (6)	0.0073 (7)	0.0035 (6)	−0.0005 (5)
O7	0.0513 (10)	0.0316 (8)	0.0261 (7)	0.0110 (8)	0.0140 (7)	−0.0011 (6)
O8	0.0474 (9)	0.0300 (7)	0.0159 (6)	−0.0083 (8)	−0.0074 (7)	0.0014 (6)
O9	0.0368 (8)	0.0162 (6)	0.0213 (6)	−0.0020 (6)	−0.0052 (6)	0.0034 (5)
C10	0.0266 (11)	0.0296 (10)	0.0259 (10)	0.0020 (9)	−0.0054 (9)	−0.0012 (8)
O11	0.0232 (7)	0.0209 (6)	0.0170 (6)	0.0031 (6)	0.0024 (5)	0.0021 (5)
C12	0.0270 (10)	0.0184 (9)	0.0158 (8)	0.0010 (9)	0.0011 (8)	0.0007 (7)
O13	0.0252 (7)	0.0196 (6)	0.0198 (6)	−0.0003 (6)	0.0001 (6)	0.0012 (5)
C14	0.0232 (9)	0.0238 (9)	0.0188 (8)	0.0014 (9)	−0.0017 (8)	0.0015 (8)
C15	0.0269 (10)	0.0296 (10)	0.0272 (10)	−0.0019 (10)	0.0029 (9)	0.0018 (9)
C16	0.0382 (12)	0.0292 (10)	0.0182 (9)	0.0002 (10)	0.0026 (9)	−0.0024 (8)
C17	0.0253 (10)	0.0276 (10)	0.0267 (9)	−0.0046 (9)	−0.0040 (9)	0.0020 (8)

Geometric parameters (Å, º)

C1—C2	1.541 (2)	C10—H102	0.975
C1—O11	1.447 (2)	C10—H103	0.956
C1—C14	1.531 (2)	O11—C12	1.443 (2)
C1—C17	1.513 (3)	C12—O13	1.434 (2)
C2—C3	1.535 (3)	C12—C15	1.513 (3)
C2—O6	1.469 (2)	C12—C16	1.520 (3)
C2—H21	1.004	O13—C14	1.424 (2)
C3—C4	1.536 (2)	C14—H141	0.979
C3—O9	1.423 (2)	C14—H142	0.992
C3—C10	1.516 (3)	C15—H151	0.980
C4—C5	1.516 (3)	C15—H152	0.988
C4—O8	1.410 (2)	C15—H153	0.986
C4—H41	1.008	C16—H161	0.978
C5—O6	1.350 (2)	C16—H162	0.995
C5—O7	1.203 (2)	C16—H163	0.986
O8—H13	0.845	C17—H171	0.987
O9—H12	0.843	C17—H172	0.981
C10—H101	0.983	C17—H173	0.982
C2—C1—O11	106.04 (14)	H101—C10—H103	110.1
C2—C1—C14	109.05 (14)	H102—C10—H103	110.3
O11—C1—C14	102.13 (13)	C1—O11—C12	109.51 (13)
C2—C1—C17	116.08 (15)	O11—C12—O13	105.62 (14)
O11—C1—C17	110.32 (14)	O11—C12—C15	109.59 (15)
C14—C1—C17	112.15 (15)	O13—C12—C15	108.44 (15)
C1—C2—C3	120.89 (15)	O11—C12—C16	109.08 (14)
C1—C2—O6	107.45 (15)	O13—C12—C16	110.85 (15)
C3—C2—O6	104.80 (14)	C15—C12—C16	112.99 (17)
C1—C2—H21	107.1	C12—O13—C14	105.49 (13)
C3—C2—H21	107.7	C1—C14—O13	103.72 (15)
O6—C2—H21	108.4	C1—C14—H141	110.5
C2—C3—C4	99.67 (15)	O13—C14—H141	109.5
C2—C3—O9	108.50 (15)	C1—C14—H142	112.3
C4—C3—O9	108.51 (14)	O13—C14—H142	109.4
C2—C3—C10	114.75 (17)	H141—C14—H142	111.1
C4—C3—C10	113.16 (16)	C12—C15—H151	108.3
O9—C3—C10	111.50 (16)	C12—C15—H152	108.2
C3—C4—C5	102.38 (16)	H151—C15—H152	110.4
C3—C4—O8	111.92 (15)	C12—C15—H153	109.4
C5—C4—O8	113.00 (16)	H151—C15—H153	111.8
C3—C4—H41	110.4	H152—C15—H153	108.6
C5—C4—H41	108.6	C12—C16—H161	109.7
O8—C4—H41	110.3	C12—C16—H162	108.0
C4—C5—O6	109.30 (16)	H161—C16—H162	109.5
C4—C5—O7	129.34 (17)	C12—C16—H163	107.6
O6—C5—O7	121.35 (19)	H161—C16—H163	110.2
C2—O6—C5	109.67 (15)	H162—C16—H163	111.8
C4—O8—H13	103.5	C1—C17—H171	109.2
C3—O9—H12	115.1	C1—C17—H172	108.2
C3—C10—H101	106.5	H171—C17—H172	107.1
C3—C10—H102	108.1	C1—C17—H173	111.7
H101—C10—H102	112.0	H171—C17—H173	110.4
C3—C10—H103	109.7	H172—C17—H173	110.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H12···O13^i	0.84	2.10	2.857 (2)	149
O8—H13···O7^ii	0.84	1.95	2.752 (2)	157

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