2,3:5,6-Di-O-isopropyl­idene-3,5-di-C-methyl-l-mannono-1,4-lactone

Booth, K.V.; Jenkinson, S.F.; Fleet, G.W.J.; Watkin, D.J.

doi:10.1107/S1600536807014584

2,3:5,6-Di-O-isopropylidene-3,5-di-C-methyl-L-mannono-1,4-lactone

K. V. Booth, S. F. Jenkinson, G. W. J. Fleet and D. J. Watkin

The relative configuration at C-2 of the title lactone, C₁₄H₂₂O₆, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014584/lh2351sup1.cif Contains datablocks 3, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014584/lh23513sup2.hkl Contains datablock 3

CCDC reference: 647277

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R factor = 0.038
wR factor = 0.106
Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.500     1.000
            Tmin(prime) and Tmax expected:      0.950     0.996
            RR(prime) =      0.524
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.52

Alert level C
PLAT602_ALERT_4_C VERY LARGE Solvent Accessible VOID(S) in Structure        !

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               2078
           From the CIF: _diffrn_reflns_limit_ max hkl    0.   20.   16.
           From the CIF: _diffrn_reflns_limit_ min hkl  -17.    0.    0.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   20.   20.   16.
           Calculated minimum hkl  -20.  -20.  -16.
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           27.47
           From the CIF: _reflns_number_total               2078
           Count of symmetry unique reflns         2092
           Completeness (_total/calc)             99.33%
           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     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R

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

   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/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.

2,3:5,6-Di-O-isopropylidene-3,5-di-C-methyl-L-mannono-1,4- lactone top

Crystal data top

C₁₄H₂₂O₆	D_x = 1.087 Mg m⁻³
M_r = 286.33	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P6₅	Cell parameters from 2079 reflections
Hall symbol: P 65	θ = 5–27°
a = 15.6104 (3) Å	µ = 0.09 mm⁻¹
c = 12.4340 (3) Å	T = 150 K
V = 2624.03 (10) Å³	Plate, colourless
Z = 6	0.60 × 0.10 × 0.05 mm
F(000) = 924

Data collection top

Bruker–Nonius KappaCCD diffractometer	1777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω scans	θ_max = 27.5°, θ_min = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −17→0
T_min = 0.50, T_max = 1.00	k = 0→20
18890 measured reflections	l = 0→16
2078 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F²) + (0.08P)² + 0.05P], where P = [max(F_o²,0) + 2F_c²]/3
S = 0.97	(Δ/σ)_max = 0.019
2078 reflections	Δρ_max = 0.26 e Å⁻³
181 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.52862 (15)	0.70492 (15)	0.6157 (2)	0.0258
C2	0.45506 (15)	0.59201 (15)	0.6198 (2)	0.0264
C3	0.49461 (16)	0.52260 (16)	0.5919 (2)	0.0281
O4	0.41240 (11)	0.42364 (11)	0.60692 (15)	0.0308
C5	0.40360 (16)	0.36401 (16)	0.5145 (2)	0.0305
O6	0.49116 (11)	0.42071 (11)	0.45314 (15)	0.0311
C7	0.52147 (17)	0.52263 (16)	0.4731 (2)	0.0297
C8	0.4022 (2)	0.27094 (18)	0.5503 (2)	0.0390
C9	0.31198 (17)	0.34378 (18)	0.4518 (2)	0.0376
C10	0.57739 (19)	0.53762 (19)	0.6674 (2)	0.0362
O11	0.37730 (11)	0.57465 (10)	0.54273 (15)	0.0287
C12	0.38233 (15)	0.66020 (16)	0.5118 (2)	0.0294
C13	0.46748 (15)	0.74744 (15)	0.5694 (2)	0.0270
O14	0.53119 (11)	0.82388 (11)	0.49895 (15)	0.0308
C15	0.60291 (15)	0.79997 (16)	0.4590 (2)	0.0315
O16	0.60032 (11)	0.72638 (11)	0.53116 (15)	0.0289
C17	0.70331 (19)	0.89353 (19)	0.4634 (3)	0.0479
C18	0.57661 (19)	0.7564 (2)	0.3467 (2)	0.0383
O19	0.32558 (13)	0.66156 (13)	0.4474 (2)	0.0405
C20	0.57951 (19)	0.75069 (18)	0.7212 (2)	0.0360
H21	0.4259	0.5760	0.6939	0.0313*
H71	0.5920	0.5632	0.4619	0.0370*
H72	0.4845	0.5450	0.4258	0.0372*
H81	0.3937	0.2305	0.4868	0.0582*
H82	0.4647	0.2897	0.5876	0.0579*
H83	0.3456	0.2325	0.5976	0.0581*
H91	0.3036	0.3018	0.3895	0.0586*
H92	0.3181	0.4053	0.4275	0.0592*
H93	0.2547	0.3090	0.4989	0.0591*
H101	0.5925	0.4846	0.6536	0.0582*
H102	0.6370	0.6022	0.6559	0.0583*
H103	0.5532	0.5319	0.7412	0.0581*
H131	0.4419	0.7740	0.6271	0.0327*
H171	0.7518	0.8778	0.4362	0.0657*
H172	0.7154	0.9119	0.5395	0.0662*
H173	0.7046	0.9466	0.4203	0.0662*
H181	0.6252	0.7384	0.3244	0.0679*
H182	0.5778	0.8058	0.2994	0.0685*
H183	0.5105	0.6977	0.3494	0.0679*
H201	0.6203	0.8230	0.7120	0.0562*
H202	0.5320	0.7348	0.7773	0.0563*
H203	0.6244	0.7256	0.7382	0.0564*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0290 (9)	0.0258 (9)	0.0250 (10)	0.0154 (8)	0.0032 (9)	0.0025 (9)
C2	0.0292 (10)	0.0279 (9)	0.0250 (11)	0.0165 (8)	0.0012 (9)	0.0029 (9)
C3	0.0301 (10)	0.0290 (10)	0.0279 (12)	0.0168 (9)	0.0028 (9)	0.0041 (9)
O4	0.0363 (8)	0.0275 (7)	0.0284 (9)	0.0159 (6)	0.0089 (7)	0.0038 (7)
C5	0.0359 (11)	0.0313 (10)	0.0283 (12)	0.0199 (9)	0.0039 (10)	0.0006 (10)
O6	0.0363 (8)	0.0295 (7)	0.0335 (9)	0.0209 (6)	0.0062 (7)	0.0000 (7)
C7	0.0358 (11)	0.0302 (11)	0.0290 (12)	0.0208 (9)	0.0065 (10)	0.0020 (9)
C8	0.0512 (14)	0.0312 (11)	0.0397 (15)	0.0245 (11)	0.0032 (12)	0.0016 (11)
C9	0.0361 (12)	0.0433 (12)	0.0355 (13)	0.0216 (10)	−0.0003 (11)	−0.0051 (12)
C10	0.0417 (12)	0.0423 (12)	0.0335 (13)	0.0276 (11)	−0.0017 (11)	0.0025 (11)
O11	0.0290 (7)	0.0281 (7)	0.0323 (9)	0.0168 (6)	−0.0003 (7)	0.0008 (7)
C12	0.0309 (10)	0.0295 (10)	0.0323 (12)	0.0185 (9)	0.0033 (10)	0.0045 (9)
C13	0.0299 (10)	0.0278 (10)	0.0260 (11)	0.0164 (8)	0.0035 (9)	0.0031 (9)
O14	0.0344 (8)	0.0279 (7)	0.0333 (9)	0.0180 (7)	0.0062 (7)	0.0066 (7)
C15	0.0325 (11)	0.0316 (11)	0.0339 (13)	0.0187 (9)	0.0061 (10)	0.0067 (10)
O16	0.0296 (7)	0.0322 (7)	0.0285 (8)	0.0183 (6)	0.0047 (7)	0.0048 (7)
C17	0.0387 (12)	0.0375 (12)	0.064 (2)	0.0163 (11)	0.0079 (14)	0.0108 (14)
C18	0.0489 (14)	0.0491 (14)	0.0291 (13)	0.0336 (12)	0.0063 (11)	0.0037 (11)
O19	0.0361 (8)	0.0395 (9)	0.0485 (10)	0.0208 (8)	−0.0109 (8)	0.0012 (9)
C20	0.0409 (12)	0.0371 (12)	0.0305 (12)	0.0199 (10)	−0.0044 (11)	−0.0024 (10)

Geometric parameters (Å, º) top

C1—C2	1.550 (3)	C9—H93	0.975
C1—C13	1.522 (3)	C10—H101	0.983
C1—O16	1.447 (3)	C10—H102	0.982
C1—C20	1.515 (3)	C10—H103	0.979
C2—C3	1.531 (3)	O11—C12	1.354 (2)
C2—O11	1.462 (3)	C12—C13	1.524 (3)
C2—H21	1.002	C12—O19	1.202 (3)
C3—O4	1.444 (2)	C13—O14	1.412 (3)
C3—C7	1.535 (3)	C13—H131	1.005
C3—C10	1.518 (3)	O14—C15	1.434 (3)
O4—C5	1.441 (3)	C15—O16	1.442 (3)
C5—O6	1.423 (3)	C15—C17	1.518 (3)
C5—C8	1.509 (3)	C15—C18	1.516 (4)
C5—C9	1.517 (3)	C17—H171	0.965
O6—C7	1.437 (3)	C17—H172	0.979
C7—H71	0.967	C17—H173	0.979
C7—H72	1.002	C18—H181	0.971
C8—H81	0.977	C18—H182	0.963
C8—H82	0.984	C18—H183	0.980
C8—H83	0.979	C20—H201	0.987
C9—H91	0.981	C20—H202	0.957
C9—H92	0.964	C20—H203	0.981

C2—C1—C13	103.82 (16)	H92—C9—H93	110.5
C2—C1—O16	109.57 (17)	C3—C10—H101	107.9
C13—C1—O16	101.88 (17)	C3—C10—H102	111.4
C2—C1—C20	115.01 (19)	H101—C10—H102	109.7
C13—C1—C20	114.64 (19)	C3—C10—H103	107.8
O16—C1—C20	110.93 (17)	H101—C10—H103	109.2
C1—C2—C3	117.73 (17)	H102—C10—H103	110.8
C1—C2—O11	105.26 (16)	C2—O11—C12	111.71 (16)
C3—C2—O11	108.14 (18)	O11—C12—C13	110.04 (18)
C1—C2—H21	107.5	O11—C12—O19	121.8 (2)
C3—C2—H21	109.0	C13—C12—O19	128.18 (19)
O11—C2—H21	109.0	C12—C13—C1	104.16 (17)
C2—C3—O4	105.70 (16)	C12—C13—O14	113.2 (2)
C2—C3—C7	115.12 (19)	C1—C13—O14	105.82 (16)
O4—C3—C7	102.78 (18)	C12—C13—H131	110.8
C2—C3—C10	111.34 (19)	C1—C13—H131	112.0
O4—C3—C10	108.54 (18)	O14—C13—H131	110.5
C7—C3—C10	112.56 (19)	C13—O14—C15	107.86 (15)
C3—O4—C5	109.54 (17)	O14—C15—O16	106.08 (17)
O4—C5—O6	105.91 (17)	O14—C15—C17	107.56 (18)
O4—C5—C8	109.7 (2)	O16—C15—C17	110.4 (2)
O6—C5—C8	107.68 (18)	O14—C15—C18	111.34 (18)
O4—C5—C9	108.64 (17)	O16—C15—C18	108.79 (18)
O6—C5—C9	111.5 (2)	C17—C15—C18	112.5 (2)
C8—C5—C9	113.1 (2)	C1—O16—C15	110.27 (15)
C5—O6—C7	106.15 (16)	C15—C17—H171	107.8
C3—C7—O6	103.15 (18)	C15—C17—H172	105.8
C3—C7—H71	111.1	H171—C17—H172	110.6
O6—C7—H71	109.7	C15—C17—H173	111.7
C3—C7—H72	111.2	H171—C17—H173	109.6
O6—C7—H72	110.8	H172—C17—H173	111.2
H71—C7—H72	110.6	C15—C18—H181	108.5
C5—C8—H81	108.4	C15—C18—H182	108.1
C5—C8—H82	108.6	H181—C18—H182	110.6
H81—C8—H82	111.6	C15—C18—H183	108.1
C5—C8—H83	109.9	H181—C18—H183	110.5
H81—C8—H83	107.5	H182—C18—H183	111.0
H82—C8—H83	110.9	C1—C20—H201	109.0
C5—C9—H91	110.0	C1—C20—H202	110.7
C5—C9—H92	109.9	H201—C20—H202	110.8
H91—C9—H92	109.4	C1—C20—H203	108.0
C5—C9—H93	108.3	H201—C20—H203	107.5
H91—C9—H93	108.9	H202—C20—H203	110.8

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2,3:5,6-Di-O-isopropyl­idene-3,5-di-C-methyl-L-mannono-1,4-lactone

Supporting information

Key indicators

checkCIF/PLATON results

2,3:5,6-Di-O-isopropylidene-3,5-di-C-methyl-L-mannono-1,4-lactone