3,5-Di-C-methyl-5,6-O-isopropyl­idene-L-glucono-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. There are two mol­ecules present in the asymmetric unit (Z' = 2). 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 = 0.033
• wR factor = 0.070
• Data-to-parameter ratio = 9.7

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:      0.670     0.990
            Tmin(prime) and Tmax expected:      0.899     0.990
            RR(prime) =      0.745
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.74
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       1.00 mm

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       5.22 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         16

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               2992
           Count of symmetry unique reflns         3052
           Completeness (_total/calc)             98.03%
           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     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C101   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C102   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C103   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C104   = .          S

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

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

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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-glucono-1,4-lactone

Crystal data

C11H18O6	F(000) = 528
Mr = 246.26	Dx = 1.296 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2612 reflections
a = 8.7635 (3) Å	θ = 5–27°
b = 10.6004 (3) Å	µ = 0.11 mm^−1
c = 13.7678 (4) Å	T = 150 K
β = 99.4044 (14)°	Plate, colourless
V = 1261.79 (7) Å^3	1.00 × 0.40 × 0.10 mm
Z = 4

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2521 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 5.1°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	h = −11→11
Tmin = 0.67, Tmax = 0.99	k = −13→12
10042 measured reflections	l = −17→17
2992 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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.070	w = 1/[σ^2(F^2) + (0.03P)^2 + 0.19P], where P = [max(Fo^2,0) + 2Fc^2]/3
S = 0.93	(Δ/σ)max = 0.000310
2992 reflections	Δρmax = 0.27 e Å^−3
307 parameters	Δρmin = −0.23 e Å^−3
1 restraint

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

	x	y	z	Uiso*/Ueq
C101	0.2441 (2)	0.20876 (18)	0.67526 (14)	0.0234
C102	0.1053 (2)	0.26581 (19)	0.60772 (14)	0.0220
C103	0.0135 (2)	0.36915 (19)	0.65041 (14)	0.0231
C104	−0.0387 (2)	0.45366 (19)	0.56115 (14)	0.0229
C105	0.0871 (2)	0.4344 (2)	0.49914 (14)	0.0236
O106	0.16175 (15)	0.32475 (13)	0.52394 (10)	0.0248
O107	0.11683 (17)	0.49882 (15)	0.43276 (11)	0.0341
O108	−0.17984 (15)	0.40958 (15)	0.50590 (10)	0.0325
O109	0.12542 (16)	0.43865 (14)	0.71639 (10)	0.0291
C110	−0.1182 (2)	0.3210 (2)	0.69928 (16)	0.0319
O111	0.30272 (15)	0.10938 (15)	0.61893 (11)	0.0295
C112	0.4697 (2)	0.1145 (2)	0.63216 (15)	0.0295
O113	0.51159 (16)	0.20758 (15)	0.70649 (10)	0.0301
C114	0.3850 (2)	0.2944 (2)	0.70071 (16)	0.0274
C115	0.5174 (3)	0.1533 (3)	0.53616 (16)	0.0418
C116	0.5364 (3)	−0.0100 (2)	0.6702 (2)	0.0422
C117	0.1959 (3)	0.1502 (2)	0.76652 (17)	0.0373
H1021	0.0337	0.1977	0.5834	0.0244*
H1041	−0.0437	0.5402	0.5807	0.0270*
H1101	−0.1793	0.3915	0.7164	0.0481*
H1102	−0.0751	0.2753	0.7586	0.0480*
H1103	−0.1830	0.2653	0.6534	0.0483*
H1141	0.3888	0.3334	0.7664	0.0328*
H1142	0.3877	0.3582	0.6493	0.0317*
H1151	0.6304	0.1579	0.5432	0.0604*
H1152	0.4774	0.0902	0.4875	0.0607*
H1153	0.4719	0.2346	0.5165	0.0606*
H1161	0.6492	−0.0074	0.6801	0.0608*
H1162	0.5036	−0.0271	0.7322	0.0604*
H1163	0.4996	−0.0761	0.6233	0.0613*
H1171	0.2821	0.1022	0.8020	0.0557*
H1172	0.1684	0.2169	0.8095	0.0554*
H1173	0.1075	0.0946	0.7477	0.0561*
H10	−0.2097	0.4614	0.4612	0.0474*
H16	0.0832	0.4983	0.7434	0.0452*
C1	0.9306 (2)	0.25399 (19)	0.18967 (14)	0.0230
C2	0.8470 (2)	0.24421 (19)	0.08284 (14)	0.0246
C3	0.7548 (2)	0.1265 (2)	0.04486 (14)	0.0278
C4	0.6476 (3)	0.1825 (3)	−0.04345 (16)	0.0404
C5	0.6161 (3)	0.3113 (3)	−0.00555 (18)	0.0472
O6	0.73454 (18)	0.34734 (15)	0.06539 (12)	0.0385
O7	0.5085 (2)	0.3808 (2)	−0.03287 (16)	0.0733
O8	0.72902 (19)	0.1989 (2)	−0.12367 (11)	0.0593
O9	0.65989 (16)	0.09305 (15)	0.11524 (10)	0.0301
C10	0.8491 (3)	0.0152 (2)	0.01850 (18)	0.0416
O11	1.03055 (15)	0.14528 (13)	0.20633 (10)	0.0226
C12	1.1882 (2)	0.1823 (2)	0.19788 (15)	0.0274
O13	1.17613 (17)	0.30814 (14)	0.16286 (11)	0.0312
C14	1.0473 (3)	0.3618 (2)	0.19846 (16)	0.0307
C15	1.2484 (3)	0.1021 (3)	0.12217 (18)	0.0388
C16	1.2862 (3)	0.1747 (2)	0.29937 (17)	0.0388
C17	0.8256 (3)	0.2616 (2)	0.26746 (16)	0.0314
H21	0.9264	0.2569	0.0406	0.0298*
H41	0.5517	0.1330	−0.0609	0.0490*
H101	0.7807	−0.0473	−0.0159	0.0605*
H102	0.9192	0.0448	−0.0244	0.0607*
H103	0.9049	−0.0187	0.0793	0.0612*
H141	1.0075	0.4346	0.1582	0.0364*
H142	1.0748	0.3868	0.2682	0.0365*
H151	1.3547	0.1271	0.1200	0.0599*
H152	1.1824	0.1154	0.0584	0.0595*
H153	1.2460	0.0145	0.1413	0.0607*
H161	1.3892	0.1977	0.2914	0.0555*
H162	1.2852	0.0884	0.3221	0.0560*
H163	1.2455	0.2317	0.3444	0.0560*
H171	0.8886	0.2704	0.3331	0.0469*
H172	0.7635	0.1852	0.2648	0.0465*
H173	0.7567	0.3336	0.2541	0.0475*
H37	0.6140	0.0288	0.0945	0.0451*
H38	0.6646	0.2060	−0.1757	0.0861*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C101	0.0247 (10)	0.0185 (9)	0.0250 (10)	0.0016 (8)	−0.0021 (8)	−0.0005 (9)
C102	0.0213 (9)	0.0197 (9)	0.0240 (10)	−0.0016 (8)	0.0011 (8)	−0.0019 (9)
C103	0.0237 (10)	0.0212 (9)	0.0236 (10)	−0.0001 (8)	0.0017 (8)	−0.0038 (9)
C104	0.0226 (10)	0.0188 (9)	0.0266 (10)	0.0026 (8)	0.0020 (8)	0.0003 (8)
C105	0.0217 (10)	0.0238 (10)	0.0236 (10)	0.0009 (8)	−0.0015 (8)	−0.0010 (9)
O106	0.0259 (7)	0.0266 (8)	0.0215 (7)	0.0053 (6)	0.0027 (6)	−0.0001 (6)
O107	0.0361 (8)	0.0368 (9)	0.0306 (8)	0.0038 (7)	0.0089 (7)	0.0091 (8)
O108	0.0238 (8)	0.0355 (8)	0.0352 (8)	0.0001 (7)	−0.0042 (6)	0.0094 (7)
O109	0.0322 (8)	0.0250 (7)	0.0288 (7)	0.0003 (6)	0.0005 (6)	−0.0101 (6)
C110	0.0302 (11)	0.0330 (12)	0.0347 (11)	0.0022 (10)	0.0120 (9)	0.0035 (10)
O111	0.0207 (7)	0.0231 (7)	0.0416 (8)	0.0047 (6)	−0.0040 (6)	−0.0069 (7)
C112	0.0211 (10)	0.0323 (11)	0.0318 (12)	0.0031 (9)	−0.0052 (8)	−0.0034 (10)
O113	0.0233 (7)	0.0345 (8)	0.0289 (8)	0.0016 (7)	−0.0069 (6)	−0.0008 (7)
C114	0.0250 (10)	0.0250 (10)	0.0291 (10)	0.0011 (9)	−0.0048 (8)	−0.0008 (9)
C115	0.0316 (12)	0.0588 (16)	0.0330 (12)	0.0014 (12)	−0.0003 (10)	−0.0036 (12)
C116	0.0286 (12)	0.0386 (13)	0.0558 (15)	0.0126 (11)	−0.0035 (11)	0.0015 (12)
C117	0.0416 (13)	0.0320 (11)	0.0370 (12)	0.0027 (11)	0.0025 (10)	0.0132 (11)
C1	0.0304 (10)	0.0175 (9)	0.0214 (10)	0.0021 (9)	0.0052 (8)	−0.0002 (8)
C2	0.0246 (10)	0.0255 (10)	0.0247 (10)	0.0072 (9)	0.0066 (8)	0.0073 (9)
C3	0.0234 (10)	0.0390 (12)	0.0201 (10)	0.0023 (9)	0.0012 (8)	0.0008 (9)
C4	0.0240 (11)	0.0674 (18)	0.0277 (11)	−0.0032 (12)	−0.0014 (9)	0.0133 (12)
C5	0.0300 (12)	0.0653 (17)	0.0470 (14)	0.0075 (13)	0.0080 (11)	0.0356 (15)
O6	0.0346 (9)	0.0346 (9)	0.0465 (10)	0.0119 (7)	0.0067 (8)	0.0186 (8)
O7	0.0382 (10)	0.0826 (16)	0.0973 (17)	0.0241 (11)	0.0056 (10)	0.0556 (14)
O8	0.0335 (9)	0.1222 (18)	0.0198 (8)	−0.0126 (11)	−0.0025 (7)	0.0165 (10)
O9	0.0363 (8)	0.0291 (7)	0.0252 (7)	−0.0045 (7)	0.0055 (6)	0.0008 (7)
C10	0.0392 (13)	0.0482 (15)	0.0347 (12)	0.0013 (12)	−0.0017 (10)	−0.0207 (12)
O11	0.0221 (7)	0.0200 (7)	0.0250 (7)	−0.0004 (6)	0.0015 (6)	0.0022 (6)
C12	0.0242 (10)	0.0267 (11)	0.0307 (11)	−0.0052 (9)	0.0024 (8)	0.0042 (9)
O13	0.0339 (8)	0.0275 (7)	0.0333 (8)	−0.0055 (7)	0.0084 (7)	0.0050 (7)
C14	0.0407 (13)	0.0225 (10)	0.0304 (11)	−0.0029 (10)	0.0101 (10)	0.0000 (9)
C15	0.0333 (12)	0.0399 (12)	0.0459 (14)	−0.0022 (12)	0.0144 (11)	−0.0010 (12)
C16	0.0320 (12)	0.0397 (13)	0.0401 (13)	−0.0120 (11)	−0.0077 (10)	0.0059 (11)
C17	0.0423 (13)	0.0266 (10)	0.0277 (11)	0.0001 (10)	0.0125 (10)	−0.0033 (9)

Geometric parameters (Å, º)

C101—C102	1.530 (3)	C1—C2	1.536 (3)
C101—O111	1.451 (2)	C1—O11	1.443 (2)
C101—C114	1.526 (3)	C1—C14	1.525 (3)
C101—C117	1.522 (3)	C1—C17	1.524 (3)
C102—C103	1.532 (3)	C2—C3	1.531 (3)
C102—O106	1.467 (2)	C2—O6	1.465 (2)
C102—H1021	0.979	C2—H21	0.986
C103—C104	1.529 (3)	C3—C4	1.530 (3)
C103—O109	1.428 (2)	C3—O9	1.421 (2)
C103—C110	1.516 (3)	C3—C10	1.518 (3)
C104—C105	1.514 (3)	C4—C5	1.504 (4)
C104—O108	1.421 (2)	C4—O8	1.420 (3)
C104—H1041	0.960	C4—H41	0.987
C105—O106	1.350 (2)	C5—O6	1.359 (3)
C105—O107	1.203 (2)	C5—O7	1.207 (3)
O108—H10	0.834	O8—H38	0.840
O109—H16	0.848	O9—H37	0.819
C110—H1101	0.971	C10—H101	0.964
C110—H1102	0.971	C10—H102	0.971
C110—H1103	0.976	C10—H103	0.967
O111—C112	1.446 (2)	O11—C12	1.459 (2)
C112—O113	1.426 (3)	C12—O13	1.417 (3)
C112—C115	1.507 (3)	C12—C15	1.506 (3)
C112—C116	1.503 (3)	C12—C16	1.518 (3)
O113—C114	1.434 (2)	O13—C14	1.421 (3)
C114—H1141	0.990	C14—H141	0.980
C114—H1142	0.982	C14—H142	0.987
C115—H1151	0.980	C15—H151	0.974
C115—H1152	0.971	C15—H152	0.980
C115—H1153	0.969	C15—H153	0.966
C116—H1161	0.976	C16—H161	0.959
C116—H1162	0.962	C16—H162	0.967
C116—H1163	0.972	C16—H163	0.974
C117—H1171	0.973	C17—H171	0.984
C117—H1172	0.978	C17—H172	0.973
C117—H1173	0.974	C17—H173	0.973
C102—C101—O111	106.13 (15)	C2—C1—O11	106.29 (15)
C102—C101—C114	115.93 (16)	C2—C1—C14	109.59 (16)
O111—C101—C114	102.19 (15)	O11—C1—C14	101.78 (15)
C102—C101—C117	111.25 (16)	C2—C1—C17	115.37 (17)
O111—C101—C117	108.37 (17)	O11—C1—C17	110.54 (16)
C114—C101—C117	112.13 (17)	C14—C1—C17	112.25 (17)
C101—C102—C103	117.70 (16)	C1—C2—C3	121.63 (16)
C101—C102—O106	108.04 (14)	C1—C2—O6	108.03 (16)
C103—C102—O106	105.23 (15)	C3—C2—O6	104.40 (15)
C101—C102—H1021	108.6	C1—C2—H21	106.5
C103—C102—H1021	108.1	C3—C2—H21	107.1
O106—C102—H1021	108.9	O6—C2—H21	108.8
C102—C103—C104	102.56 (14)	C2—C3—C4	100.16 (18)
C102—C103—O109	105.28 (15)	C2—C3—O9	107.78 (16)
C104—C103—O109	107.05 (15)	C4—C3—O9	106.66 (16)
C102—C103—C110	114.54 (17)	C2—C3—C10	115.95 (17)
C104—C103—C110	113.86 (17)	C4—C3—C10	113.53 (19)
O109—C103—C110	112.63 (16)	O9—C3—C10	111.79 (18)
C103—C104—C105	102.96 (16)	C3—C4—C5	101.57 (19)
C103—C104—O108	110.94 (15)	C3—C4—O8	110.14 (18)
C105—C104—O108	107.70 (16)	C5—C4—O8	107.6 (2)
C103—C104—H1041	110.9	C3—C4—H41	112.0
C105—C104—H1041	111.0	C5—C4—H41	111.7
O108—C104—H1041	112.9	O8—C4—H41	113.1
C104—C105—O106	109.95 (17)	C4—C5—O6	110.0 (2)
C104—C105—O107	128.26 (19)	C4—C5—O7	128.7 (3)
O106—C105—O107	121.66 (17)	O6—C5—O7	121.3 (3)
C102—O106—C105	110.73 (14)	C2—O6—C5	108.83 (19)
C104—O108—H10	108.6	C4—O8—H38	108.8
C103—O109—H16	111.1	C3—O9—H37	106.2
C103—C110—H1101	109.8	C3—C10—H101	109.4
C103—C110—H1102	108.7	C3—C10—H102	108.5
H1101—C110—H1102	109.6	H101—C10—H102	109.1
C103—C110—H1103	108.7	C3—C10—H103	107.4
H1101—C110—H1103	109.7	H101—C10—H103	110.8
H1102—C110—H1103	110.3	H102—C10—H103	111.5
C101—O111—C112	110.16 (15)	C1—O11—C12	109.32 (14)
O111—C112—O113	104.65 (15)	O11—C12—O13	105.15 (16)
O111—C112—C115	108.65 (17)	O11—C12—C15	110.30 (17)
O113—C112—C115	111.42 (19)	O13—C12—C15	108.13 (17)
O111—C112—C116	109.81 (18)	O11—C12—C16	108.25 (16)
O113—C112—C116	108.54 (17)	O13—C12—C16	111.25 (18)
C115—C112—C116	113.4 (2)	C15—C12—C16	113.4 (2)
C112—O113—C114	107.35 (14)	C12—O13—C14	106.18 (15)
C101—C114—O113	102.74 (16)	C1—C14—O13	103.48 (16)
C101—C114—H1141	111.3	C1—C14—H141	111.9
O113—C114—H1141	107.9	O13—C14—H141	110.5
C101—C114—H1142	111.0	C1—C14—H142	109.4
O113—C114—H1142	111.9	O13—C14—H142	111.2
H1141—C114—H1142	111.7	H141—C14—H142	110.2
C112—C115—H1151	110.3	C12—C15—H151	108.2
C112—C115—H1152	107.3	C12—C15—H152	108.5
H1151—C115—H1152	110.3	H151—C15—H152	111.1
C112—C115—H1153	109.1	C12—C15—H153	109.2
H1151—C115—H1153	110.3	H151—C15—H153	109.5
H1152—C115—H1153	109.5	H152—C15—H153	110.3
C112—C116—H1161	110.6	C12—C16—H161	106.4
C112—C116—H1162	108.6	C12—C16—H162	108.3
H1161—C116—H1162	108.9	H161—C16—H162	109.6
C112—C116—H1163	109.5	C12—C16—H163	110.0
H1161—C116—H1163	109.5	H161—C16—H163	111.4
H1162—C116—H1163	109.8	H162—C16—H163	110.9
C101—C117—H1171	109.3	C1—C17—H171	109.8
C101—C117—H1172	109.5	C1—C17—H172	109.1
H1171—C117—H1172	108.8	H171—C17—H172	109.9
C101—C117—H1173	110.1	C1—C17—H173	109.6
H1171—C117—H1173	109.6	H171—C17—H173	109.7
H1172—C117—H1173	109.6	H172—C17—H173	108.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O108—H10···O111^i	0.83	2.01	2.827 (2)	165
O109—H16···O11^ii	0.85	2.03	2.876 (2)	174
O9—H37···O7^iii	0.82	2.01	2.825 (2)	175
O8—H38···O113^iv	0.84	1.93	2.766 (2)	175

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