(2S,3S)-2,3-Dihydroxy­succinic acid monohydrate

The crystal structure of the title compound, C₄H₆O₆·H₂O, displays a two-dimensional network formed by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.126
• Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.76 Ratio
PLAT395_ALERT_2_B Deviating  X-O-Y  Angle from 120 Deg for      O7     161.10 Deg.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1     ..  H6      ..       1.28 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.779     1.000
            Tmin(prime) and Tmax expected:      0.916     0.930
            RR(prime) =      0.791
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.60
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT731_ALERT_1_C Bond    Calc     0.90(6), Rep     0.90(2) ......       3.00 su-Rat
              O2   -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.92(5), Rep     0.92(2) ......       2.50 su-Rat
              O7   -H7B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.92(5), Rep     0.92(2) ......       2.50 su-Rat
              O7   -H7B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.90(6), Rep     0.90(2) ......       3.00 su-Rat
              O2   -H1      1.555   1.555

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.930
            Tmax scaled      0.930 Tmin scaled      0.724
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           26.98
           From the CIF: _reflns_number_total                852
           Count of symmetry unique reflns          853
           Completeness (_total/calc)             99.88%
           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

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

   7 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
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT; data reduction: SAINT (Bruker, 2000) and SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(2S,3S)-2,3-Dihydroxysuccinic acid monohydrate

Crystal data

C4H6O6·H2O	Dx = 1.691 Mg m^−3
Mr = 168.10	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2998 reflections
a = 7.6377 (7) Å	θ = 6.4–56.5°
b = 7.8268 (7) Å	µ = 0.17 mm^−1
c = 11.0427 (10) Å	T = 293 K
V = 660.12 (10) Å^3	Prism, colorless
Z = 4	0.51 × 0.44 × 0.43 mm
F(000) = 352

Data collection

Bruker SMART CCD area-detector diffractometer	852 independent reflections
Radiation source: fine-focus sealed tube	818 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 27.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.779, Tmax = 1.000	k = −9→7
3853 measured reflections	l = −13→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0774P)^2 + 0.2665P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
852 reflections	Δρmax = 0.32 e Å^−3
129 parameters	Δρmin = −0.32 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.13 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
O1	0.5179 (3)	0.7021 (3)	0.3254 (2)	0.0303 (6)
O2	0.5451 (3)	0.6213 (3)	0.13332 (19)	0.0280 (6)
O3	0.1882 (3)	0.5774 (3)	0.33957 (18)	0.0230 (6)
O4	0.1825 (3)	0.8620 (2)	0.1670 (2)	0.0249 (5)
O5	−0.0441 (3)	0.4696 (3)	0.11010 (19)	0.0259 (6)
O6	−0.1416 (3)	0.7311 (3)	0.1493 (2)	0.0278 (6)
H6	−0.2369	0.6834	0.1445	0.042*
O7	0.8342 (3)	0.6784 (4)	0.4668 (2)	0.0392 (7)
C1	0.4581 (4)	0.6397 (3)	0.2344 (2)	0.0196 (6)
C2	0.2706 (4)	0.5758 (3)	0.2247 (2)	0.0172 (6)
C3	0.1683 (3)	0.6872 (4)	0.1361 (2)	0.0182 (6)
C4	−0.0210 (4)	0.6235 (4)	0.1310 (2)	0.0192 (6)
H1	0.607 (9)	0.711 (7)	0.107 (7)	0.10 (3)*
H2	0.274 (5)	0.470 (5)	0.199 (3)	0.021 (8)*
H3	0.239 (5)	0.662 (5)	0.063 (4)	0.039 (11)*
H4	0.129 (5)	0.865 (5)	0.239 (2)	0.036 (11)*
H5	0.147 (5)	0.472 (3)	0.352 (3)	0.032 (10)*
H7B	0.759 (6)	0.668 (8)	0.402 (4)	0.09 (2)*
H7A	0.906 (6)	0.650 (6)	0.532 (4)	0.082 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0235 (10)	0.0433 (13)	0.0242 (10)	−0.0052 (10)	−0.0027 (8)	−0.0115 (9)
O2	0.0206 (10)	0.0389 (13)	0.0244 (11)	−0.0039 (10)	0.0014 (8)	−0.0068 (9)
O3	0.0270 (11)	0.0221 (10)	0.0197 (9)	−0.0036 (8)	0.0037 (8)	0.0020 (8)
O4	0.0263 (10)	0.0161 (10)	0.0323 (10)	−0.0032 (8)	0.0015 (9)	0.0024 (8)
O5	0.0250 (10)	0.0208 (10)	0.0320 (11)	−0.0010 (9)	−0.0041 (9)	−0.0061 (8)
O6	0.0171 (10)	0.0236 (11)	0.0426 (13)	0.0007 (8)	0.0014 (9)	−0.0034 (9)
O7	0.0385 (14)	0.0428 (14)	0.0362 (13)	−0.0043 (12)	−0.0017 (11)	−0.0008 (11)
C1	0.0192 (13)	0.0183 (12)	0.0211 (12)	0.0020 (11)	0.0012 (10)	−0.0007 (9)
C2	0.0195 (13)	0.0146 (12)	0.0176 (12)	0.0010 (10)	−0.0002 (10)	−0.0017 (9)
C3	0.0192 (13)	0.0192 (13)	0.0163 (11)	0.0002 (11)	0.0009 (9)	0.0007 (10)
C4	0.0200 (13)	0.0222 (14)	0.0153 (11)	0.0008 (11)	0.0010 (10)	0.0001 (9)

Geometric parameters (Å, º)

O1—C1	1.208 (4)	O6—H6	0.8200
O2—C1	1.306 (4)	O7—H7B	0.92 (2)
O2—H1	0.90 (2)	O7—H7A	0.93 (2)
O3—C2	1.416 (3)	C1—C2	1.521 (4)
O3—H5	0.90 (2)	C2—C3	1.526 (4)
O4—C3	1.414 (3)	C2—H2	0.88 (4)
O4—H4	0.888 (19)	C3—C4	1.531 (4)
O5—C4	1.238 (3)	C3—H3	0.99 (4)
O6—C4	1.264 (3)
C1—O1—H7B	129.4 (15)	O3—C2—H2	108 (2)
C1—O2—H1	118 (5)	C1—C2—H2	108 (2)
C2—O3—H5	107 (2)	C3—C2—H2	111 (2)
C3—O4—H4	102 (3)	O4—C3—C2	111.0 (2)
C4—O6—H6	109.5	O4—C3—C4	113.4 (2)
H7B—O7—H7A	161 (5)	C2—C3—C4	108.7 (2)
O1—C1—O2	124.3 (3)	O4—C3—H3	110 (2)
O1—C1—C2	123.2 (3)	C2—C3—H3	97 (2)
O2—C1—C2	112.5 (2)	C4—C3—H3	115 (2)
O3—C2—C1	110.7 (2)	O5—C4—O6	125.0 (3)
O3—C2—C3	110.0 (2)	O5—C4—C3	117.3 (2)
C1—C2—C3	109.8 (2)	O6—C4—C3	117.7 (2)
H7B—O1—C1—O2	−42 (2)	C1—C2—C3—O4	−53.0 (3)
H7B—O1—C1—C2	139 (2)	O3—C2—C3—C4	−56.3 (3)
O1—C1—C2—O3	−8.4 (3)	C1—C2—C3—C4	−178.4 (2)
O2—C1—C2—O3	172.5 (2)	O4—C3—C4—O5	−176.7 (2)
O1—C1—C2—C3	113.2 (3)	C2—C3—C4—O5	−52.7 (3)
O2—C1—C2—C3	−65.9 (3)	O4—C3—C4—O6	2.8 (3)
O3—C2—C3—O4	69.1 (3)	C2—C3—C4—O6	126.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O1	0.92 (2)	2.04 (3)	2.882 (3)	151 (5)
O7—H7A···O2^i	0.93 (2)	2.43 (4)	3.120 (4)	131 (4)
O7—H7A···O1^ii	0.93 (2)	2.13 (4)	2.848 (3)	133 (4)
O3—H5···O6^iii	0.90 (2)	1.88 (2)	2.737 (3)	158 (4)
O4—H4···O5^iv	0.89 (2)	1.97 (2)	2.808 (3)	156 (4)
O2—H1···O6^v	0.90 (2)	1.98 (7)	2.549 (3)	120 (6)
O6—H6···O2^vi	0.82	1.74	2.549 (3)	169

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