(R*)-Methyl 3-carb­oxy-2-hydroxy­propanoate

The crystal structure of the title compound, C₅H₈O₅, was determined at 173 K. The compound is a monomethyl ester of butane­dioic acid and was isolated from fresh cranberries (Vaccinium macrocarpon). The crystal structure is stabilized by intermolecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.031
• wR factor = 0.084
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94

Author Response: Not applicable for our equipment and software

Alert level C
REFLT03_ALERT_1_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           34.31
           From the CIF: _diffrn_reflns_theta_full          34.31
           From the CIF: _reflns_number_total               1421
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         1518
           Completeness (_total/calc)             93.61%
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       5.80 su

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           34.31
           From the CIF: _reflns_number_total               1421
           Count of symmetry unique reflns         1518
           Completeness (_total/calc)             93.61%
           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
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Methyl 3-carboxy-2-hydroxypropanoate

Crystal data

C5H8O5	F(000) = 312
Mr = 148.11	Dx = 1.509 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 22.699 (5) Å	Cell parameters from 4381 reflections
b = 4.1854 (9) Å	θ = 3.0–34.3°
c = 6.9782 (15) Å	µ = 0.14 mm^−1
β = 100.415 (18)°	T = 173 K
V = 652.0 (2) Å^3	Block, colourless
Z = 4	0.50 × 0.40 × 0.30 mm

Data collection

Bruker X8 APEX II diffractometer	1421 independent reflections
Radiation source: fine-focus sealed tube	1323 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 34.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→36
Tmin = 0.934, Tmax = 0.960	k = −6→5
6931 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: difference Fourier map
wR(F^2) = 0.084	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0589P)^2] where P = (Fo^2 + 2Fc^2)/3
1421 reflections	(Δ/σ)max = 0.013
123 parameters	Δρmax = 0.24 e Å^−3
1 restraint	Δρmin = −0.19 e Å^−3

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	0.25707 (3)	0.9660 (3)	0.24422 (10)	0.03445 (19)
H1	0.2392 (8)	1.024 (6)	0.117 (3)	0.062 (6)*
O2	0.30772 (3)	0.6119 (2)	0.10029 (10)	0.03145 (18)
O3	0.42670 (3)	0.81550 (17)	0.38465 (10)	0.02544 (15)
H3	0.4604 (7)	0.745 (4)	0.361 (2)	0.038 (4)*
O4	0.47584 (3)	0.5139 (2)	0.72298 (10)	0.03141 (18)
O5	0.38839 (3)	0.28696 (18)	0.73931 (9)	0.02445 (15)
C1	0.29831 (3)	0.7457 (2)	0.24497 (11)	0.02159 (17)
C2	0.33131 (4)	0.6772 (2)	0.44659 (11)	0.02098 (16)
H2A	0.3302 (6)	0.868 (4)	0.529 (2)	0.032 (4)*
H2B	0.3112 (6)	0.506 (4)	0.502 (2)	0.029 (3)*
C3	0.39473 (4)	0.5632 (2)	0.44873 (12)	0.01953 (15)
H3A	0.3960 (6)	0.372 (4)	0.3703 (19)	0.020 (3)*
C4	0.42474 (3)	0.4564 (2)	0.65146 (11)	0.02063 (16)
C5	0.41331 (5)	0.1663 (3)	0.93099 (13)	0.0298 (2)
H5A	0.4446 (8)	0.013 (5)	0.923 (2)	0.045 (4)*
H5B	0.3819 (7)	0.062 (5)	0.973 (2)	0.041 (4)*
H5C	0.4271 (8)	0.341 (6)	1.004 (3)	0.049 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0340 (3)	0.0493 (5)	0.0185 (3)	0.0170 (4)	0.0006 (2)	0.0034 (3)
O2	0.0304 (3)	0.0423 (5)	0.0197 (3)	0.0009 (3)	−0.0007 (2)	−0.0074 (3)
O3	0.0214 (3)	0.0247 (3)	0.0319 (3)	0.0025 (2)	0.0093 (2)	0.0084 (3)
O4	0.0205 (3)	0.0448 (5)	0.0270 (3)	−0.0052 (3)	−0.0011 (2)	0.0066 (3)
O5	0.0230 (3)	0.0318 (4)	0.0174 (2)	−0.0045 (3)	0.0007 (2)	0.0049 (2)
C1	0.0172 (3)	0.0284 (5)	0.0187 (3)	−0.0031 (3)	0.0022 (2)	0.0011 (3)
C2	0.0178 (3)	0.0285 (4)	0.0160 (3)	0.0008 (3)	0.0013 (2)	0.0009 (3)
C3	0.0200 (3)	0.0215 (4)	0.0171 (3)	0.0008 (3)	0.0036 (3)	0.0008 (3)
C4	0.0192 (3)	0.0231 (4)	0.0194 (3)	0.0001 (3)	0.0031 (3)	0.0008 (3)
C5	0.0317 (4)	0.0374 (6)	0.0193 (3)	−0.0009 (4)	0.0022 (3)	0.0070 (4)

Geometric parameters (Å, º)

O1—C1	1.3133 (12)	C2—C3	1.5142 (12)
O1—H1	0.94 (2)	C2—H2A	0.986 (18)
O2—C1	1.2069 (11)	C2—H2B	0.966 (15)
O3—C3	1.3996 (11)	C3—C4	1.5221 (11)
O3—H3	0.864 (16)	C3—H3A	0.973 (15)
O4—C4	1.2014 (11)	C5—H5A	0.966 (18)
O5—C4	1.3199 (11)	C5—H5B	0.926 (17)
O5—C5	1.4459 (11)	C5—H5C	0.91 (2)
C1—C2	1.4973 (12)
C1—O1—H1	111.8 (13)	C2—C3—C4	111.51 (7)
C3—O3—H3	109.3 (11)	O3—C3—H3A	111.8 (8)
C4—O5—C5	116.39 (7)	C2—C3—H3A	112.3 (8)
O2—C1—O1	123.81 (8)	C4—C3—H3A	103.1 (8)
O2—C1—C2	124.26 (9)	O4—C4—O5	123.54 (8)
O1—C1—C2	111.92 (7)	O4—C4—C3	124.29 (8)
C1—C2—C3	112.51 (7)	O5—C4—C3	112.16 (7)
C1—C2—H2A	109.3 (9)	O5—C5—H5A	110.5 (10)
C3—C2—H2A	111.9 (8)	O5—C5—H5B	105.1 (10)
C1—C2—H2B	108.9 (9)	H5A—C5—H5B	108.7 (16)
C3—C2—H2B	106.2 (9)	O5—C5—H5C	106.0 (13)
H2A—C2—H2B	107.9 (11)	H5A—C5—H5C	112.3 (17)
O3—C3—C2	107.82 (7)	H5B—C5—H5C	113.9 (17)
O3—C3—C4	110.35 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.94 (2)	1.73 (2)	2.6527 (11)	167.8 (17)
O3—H3···O4^ii	0.864 (16)	1.917 (16)	2.7663 (11)	167.3 (16)

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