D-Galactono-1,4-lactone: a case of wrong absolute configuration surviving three decades

The title compound, C₆H₁₀O₆, had been previously characterized by X-ray analysis but was reported with the wrong absolute configuration [Jeffrey, Rosenstein & Vlasse (1967). Acta Cryst. 22, 725-733]. This structure has now been redetermined at higher resolution and including precise positions for H atoms.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.027
• wR factor = 0.076
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



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           34.99
           From the CIF: _reflns_number_total               1925
           Count of symmetry unique reflns         1926
           Completeness (_total/calc)             99.95%
           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

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

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

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS"; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (CCDC, 2004); software used to prepare material for publication: SHELXTL-Plus.

D-Galactonic 1,4-lactone

Crystal data

C6H10O6	Dx = 1.558 Mg m^−3
Mr = 178.14	Melting point: 410.32 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 78 reflections
a = 6.4818 (6) Å	θ = 4.9–13.8°
b = 10.6714 (8) Å	µ = 0.14 mm^−1
c = 10.9799 (11) Å	T = 296 K
V = 759.48 (12) Å^3	Irregular, colorless
Z = 4	0.60 × 0.44 × 0.40 mm
F(000) = 376

Data collection

Bruker P4 diffractometer	Rint = 0.032
Radiation source: fine-focus sealed tube, FN4	θmax = 35.0°, θmin = 2.7°
Graphite monochromator	h = −10→10
ω scans	k = −17→17
13164 measured reflections	l = −17→17
1925 independent reflections	3 standard reflections every 97 reflections
1826 reflections with I > 2σ(I)	intensity decay: 3.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	All H-atom parameters refined
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.0364P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1925 reflections	Δρmax = 0.25 e Å^−3
150 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (5)

Special details

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
C1	0.27602 (14)	0.26430 (8)	0.52894 (8)	0.02697 (15)
O1	0.29712 (15)	0.20628 (8)	0.43583 (7)	0.03785 (18)
C2	0.27228 (14)	0.40649 (8)	0.54496 (7)	0.02506 (14)
H2A	0.132 (3)	0.4328 (15)	0.5344 (14)	0.032 (3)*
O2	0.40508 (13)	0.46966 (7)	0.46469 (6)	0.03151 (15)
H2	0.357 (4)	0.4631 (17)	0.3893 (17)	0.054 (5)*
C3	0.33387 (13)	0.41905 (8)	0.67820 (7)	0.02390 (14)
H3A	0.481 (2)	0.4080 (13)	0.6844 (13)	0.025 (3)*
O3	0.26256 (13)	0.52813 (6)	0.73765 (6)	0.03167 (15)
H3	0.342 (3)	0.5914 (15)	0.7190 (14)	0.036 (4)*
C4	0.22801 (14)	0.30374 (7)	0.73193 (8)	0.02469 (14)
H4A	0.086 (2)	0.3214 (14)	0.7409 (14)	0.032 (3)*
O4	0.25384 (13)	0.20820 (6)	0.63823 (6)	0.03028 (14)
C5	0.31170 (14)	0.25503 (8)	0.85223 (8)	0.02512 (15)
H5A	0.291 (3)	0.3218 (12)	0.9088 (14)	0.028 (3)*
O5	0.52572 (12)	0.22701 (7)	0.84374 (7)	0.03124 (15)
H5	0.597 (4)	0.285 (2)	0.8777 (19)	0.064 (6)*
C6	0.19322 (18)	0.13917 (10)	0.89266 (10)	0.03350 (19)
H6A	0.239 (3)	0.0688 (14)	0.8425 (14)	0.035 (4)*
H6B	0.043 (3)	0.1557 (16)	0.8824 (17)	0.046 (5)*
O6	0.23177 (17)	0.10913 (8)	1.01678 (8)	0.0421 (2)
H6	0.344 (4)	0.065 (2)	1.0261 (19)	0.062 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0261 (3)	0.0287 (3)	0.0261 (3)	−0.0007 (3)	−0.0029 (3)	−0.0035 (3)
O1	0.0418 (4)	0.0404 (4)	0.0313 (3)	−0.0027 (3)	0.0003 (3)	−0.0124 (3)
C2	0.0260 (3)	0.0266 (3)	0.0227 (3)	0.0003 (3)	−0.0015 (3)	0.0004 (3)
O2	0.0377 (3)	0.0355 (3)	0.0214 (2)	−0.0070 (3)	−0.0015 (3)	0.0029 (2)
C3	0.0277 (3)	0.0225 (3)	0.0215 (3)	−0.0002 (3)	0.0008 (3)	−0.0004 (2)
O3	0.0433 (4)	0.0228 (2)	0.0289 (3)	−0.0021 (3)	0.0095 (3)	−0.0025 (2)
C4	0.0267 (3)	0.0231 (3)	0.0243 (3)	−0.0008 (3)	−0.0010 (3)	0.0001 (2)
O4	0.0396 (4)	0.0236 (2)	0.0276 (3)	−0.0024 (3)	−0.0045 (3)	−0.0025 (2)
C5	0.0288 (3)	0.0222 (3)	0.0244 (3)	0.0016 (3)	−0.0001 (3)	0.0002 (3)
O5	0.0288 (3)	0.0281 (3)	0.0367 (3)	0.0025 (2)	−0.0051 (3)	−0.0044 (3)
C6	0.0352 (4)	0.0311 (4)	0.0342 (4)	−0.0014 (4)	0.0029 (4)	0.0073 (3)
O6	0.0525 (5)	0.0400 (4)	0.0337 (4)	0.0194 (4)	0.0146 (3)	0.0120 (3)

Geometric parameters (Å, º)

C1—O1	1.2031 (11)	C4—O4	1.4581 (10)
C1—O4	1.3487 (11)	C4—C5	1.5196 (12)
C1—C2	1.5278 (12)	C4—H4A	0.946 (16)
C2—O2	1.4043 (11)	C5—O5	1.4221 (12)
C2—C3	1.5223 (12)	C5—C6	1.5217 (13)
C2—H2A	0.957 (16)	C5—H5A	0.955 (14)
O2—H2	0.89 (2)	O5—H5	0.86 (2)
C3—O3	1.4124 (10)	C6—O6	1.4221 (14)
C3—C4	1.5274 (12)	C6—H6A	0.978 (15)
C3—H3A	0.966 (15)	C6—H6B	0.99 (2)
O3—H3	0.872 (17)	O6—H6	0.88 (2)
O1—C1—O4	122.67 (8)	C5—C4—C3	116.80 (7)
O1—C1—C2	127.65 (9)	O4—C4—H4A	108.9 (9)
O4—C1—C2	109.68 (7)	C5—C4—H4A	109.0 (9)
O2—C2—C3	113.59 (7)	C3—C4—H4A	108.5 (9)
O2—C2—C1	113.25 (7)	C1—O4—C4	109.25 (6)
C3—C2—C1	101.18 (6)	O5—C5—C4	111.30 (8)
O2—C2—H2A	111.3 (9)	O5—C5—C6	109.91 (8)
C3—C2—H2A	109.8 (9)	C4—C5—C6	110.57 (8)
C1—C2—H2A	107.0 (10)	O5—C5—H5A	109.7 (10)
C2—O2—H2	109.5 (14)	C4—C5—H5A	105.1 (9)
O3—C3—C2	115.52 (7)	C6—C5—H5A	110.2 (9)
O3—C3—C4	109.79 (7)	C5—O5—H5	110.4 (16)
C2—C3—C4	100.51 (7)	O6—C6—C5	111.97 (9)
O3—C3—H3A	113.1 (8)	O6—C6—H6A	108.3 (9)
C2—C3—H3A	108.5 (8)	C5—C6—H6A	107.8 (9)
C4—C3—H3A	108.6 (8)	O6—C6—H6B	108.7 (11)
C3—O3—H3	109.6 (10)	C5—C6—H6B	108.4 (10)
O4—C4—C5	109.46 (7)	H6A—C6—H6B	111.6 (14)
O4—C4—C3	103.84 (7)	C6—O6—H6	112.4 (13)
O1—C1—C2—O2	−34.82 (14)	C2—C3—C4—C5	158.50 (7)
O4—C1—C2—O2	144.45 (8)	O1—C1—O4—C4	−178.98 (9)
O1—C1—C2—C3	−156.76 (10)	C2—C1—O4—C4	1.70 (10)
O4—C1—C2—C3	22.52 (9)	C5—C4—O4—C1	−150.84 (8)
O2—C2—C3—O3	84.63 (9)	C3—C4—O4—C1	−25.42 (10)
C1—C2—C3—O3	−153.67 (7)	O4—C4—C5—O5	60.97 (9)
O2—C2—C3—C4	−157.33 (7)	C3—C4—C5—O5	−56.59 (9)
C1—C2—C3—C4	−35.63 (8)	O4—C4—C5—C6	−61.48 (10)
O3—C3—C4—O4	160.09 (7)	C3—C4—C5—C6	−179.05 (8)
C2—C3—C4—O4	37.92 (8)	O5—C5—C6—O6	71.04 (10)
O3—C3—C4—C5	−79.32 (9)	C4—C5—C6—O6	−165.70 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3^i	0.89 (2)	1.84 (2)	2.7195 (10)	171.4 (18)
O3—H3···O5^ii	0.872 (17)	1.818 (17)	2.6807 (10)	169.3 (16)
O5—H5···O6^iii	0.86 (2)	1.84 (2)	2.6809 (11)	167 (2)
O6—H6···O2^iv	0.88 (2)	1.92 (2)	2.7923 (12)	176 (2)

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