Literature DB >> 21577751

Disodium (2RS,3SR)-tartrate.

William Arbuckle, Stuart Cartner, Alan R Kennedy, Catriona A Morrison.   

Abstract

The asymmetric unit of the anhydrous title compound, 2Na(+)·C(4)H(4)O(6) (2-), contains two sodium cations and one tartrate anion. Each sodium ion is six coordinate, with bonding to six O atoms from both the carboxyl-ate and hydroxyl groups of the anion. A three-dimensional coordination network is formed with sodium ions stacking in layers along the c-axis direction. This network is supported by additional O-H⋯O hydrogen bonds.

Entities:  

Year:  2009        PMID: 21577751      PMCID: PMC2970502          DOI: 10.1107/S1600536809037155

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the preparation and structure of the equivalent anhydrous meso-tartrate salt, see: Blankensteyn & Kroon (1985 ▶). For similar hydrated tartrate salt examples using sodium or mixed sodium with lithium, potassium, rubidium or ammonium cations, see: Ambady & Kartha (1968 ▶); Suzuki et al. (1996 ▶); Buschmann & Luger (1985 ▶); Görbitz & Sagstuen (2008 ▶); Hinazumi & Mitsui (1972 ▶). For the use of tartrates as food additives, see: Vickers et al. (2007 ▶).

Experimental

Crystal data

2Na+·C4H4O6 2− M = 194.06 Orthorhombic, a = 10.1160 (4) Å b = 10.0049 (5) Å c = 13.0821 (5) Å V = 1324.03 (10) Å3 Z = 8 Mo Kα radiation μ = 0.29 mm−1 T = 123 K 0.24 × 0.15 × 0.09 mm

Data collection

Oxford Diffraction Gemini S CCD diffractometer Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2007 ▶) T min = 0.894, T max = 1.000 7156 measured reflections 1934 independent reflections 1566 reflections with I > 2/s(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.072 S = 1.05 1934 reflections 117 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.39 e Å−3 Δρmin = −0.31 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037155/tk2539sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037155/tk2539Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
2Na+·C4H4O62F(000) = 784
Mr = 194.06Dx = 1.947 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3917 reflections
a = 10.1160 (4) Åθ = 2.5–30.8°
b = 10.0049 (5) ŵ = 0.29 mm1
c = 13.0821 (5) ÅT = 123 K
V = 1324.03 (10) Å3Block, colourless
Z = 80.24 × 0.15 × 0.09 mm
Oxford Diffraction Gemini S CCD diffractometer1934 independent reflections
Radiation source: fine-focus sealed tube1566 reflections with I > 2/s(I)
graphiteRint = 0.024
ω scansθmax = 30.8°, θmin = 3.1°
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2007)h = −14→8
Tmin = 0.894, Tmax = 1.000k = −14→14
7156 measured reflectionsl = −17→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
1934 reflections(Δ/σ)max = 0.001
117 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = −0.31 e Å3
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.
xyzUiso*/Ueq
Na10.55185 (4)−0.03963 (5)−0.37266 (3)0.01008 (12)
Na20.52569 (5)−0.03323 (5)0.12690 (3)0.01163 (12)
O10.53147 (9)−0.24500 (8)−0.29356 (7)0.0149 (2)
O20.61519 (8)−0.40740 (8)−0.19771 (6)0.01028 (18)
O30.66678 (8)−0.05364 (8)−0.20387 (6)0.00958 (17)
O40.73339 (8)−0.01137 (9)0.05789 (6)0.01434 (19)
O50.89689 (8)−0.12972 (8)−0.01024 (6)0.01052 (18)
O60.54400 (8)−0.15557 (9)−0.02943 (6)0.00950 (17)
C10.60624 (11)−0.28543 (11)−0.22473 (8)0.0082 (2)
C20.69680 (11)−0.18581 (11)−0.16939 (8)0.0078 (2)
H10.7910−0.2069−0.18590.009*
C30.67622 (11)−0.19485 (12)−0.05305 (8)0.0082 (2)
H30.6900−0.2894−0.03060.010*
C40.77515 (10)−0.10399 (12)0.00307 (8)0.0087 (2)
H20.7378 (17)0.0000 (17)−0.1980 (13)0.033 (5)*
H40.4958 (17)−0.2286 (16)−0.0224 (14)0.026 (5)*
U11U22U33U12U13U23
Na10.0103 (2)0.0103 (2)0.0096 (2)−0.00008 (18)0.00033 (16)0.00102 (17)
Na20.0123 (2)0.0126 (2)0.0100 (2)0.0033 (2)0.00156 (16)0.00156 (17)
O10.0174 (4)0.0114 (4)0.0158 (4)−0.0023 (4)−0.0085 (3)0.0021 (3)
O20.0111 (4)0.0073 (4)0.0124 (4)0.0000 (3)0.0002 (3)0.0005 (3)
O30.0109 (4)0.0069 (4)0.0109 (4)−0.0012 (3)−0.0008 (3)0.0019 (3)
O40.0116 (4)0.0154 (4)0.0161 (4)−0.0004 (4)0.0013 (3)−0.0077 (3)
O50.0078 (3)0.0112 (4)0.0125 (4)0.0004 (3)0.0002 (3)0.0009 (3)
O60.0074 (4)0.0097 (4)0.0114 (4)−0.0004 (3)0.0017 (3)0.0003 (3)
C10.0085 (5)0.0086 (5)0.0075 (4)0.0003 (4)0.0019 (4)−0.0012 (4)
C20.0087 (5)0.0066 (5)0.0082 (4)0.0002 (4)−0.0003 (4)0.0002 (4)
C30.0073 (5)0.0081 (5)0.0092 (4)0.0009 (4)0.0000 (4)0.0001 (4)
C40.0100 (5)0.0092 (5)0.0069 (5)−0.0004 (4)−0.0004 (4)0.0020 (4)
Na1—O12.3097 (10)O2—C11.2737 (14)
Na1—O2i2.3352 (9)O2—Na1viii2.3352 (9)
Na1—O5ii2.3699 (9)O2—Na2vii2.5370 (9)
Na1—O4iii2.4095 (9)O3—C21.4298 (14)
Na1—O32.4994 (9)O3—Na2iv2.3580 (9)
Na1—O5iii2.5257 (9)O3—H20.900 (17)
Na1—C4iii2.7875 (12)O4—C41.2457 (13)
Na1—Na2iv3.3886 (6)O4—Na1ix2.4095 (9)
Na1—Na1v3.5820 (8)O5—C41.2701 (13)
Na2—O42.2973 (9)O5—Na1x2.3699 (9)
Na2—O3iv2.3580 (9)O5—Na1ix2.5257 (9)
Na2—O6iv2.3856 (9)O6—C31.4279 (13)
Na2—O62.3907 (9)O6—Na2iv2.3856 (9)
Na2—O1vi2.4513 (10)O6—H40.883 (17)
Na2—O2vi2.5370 (9)C1—C21.5352 (16)
Na2—C1vi2.7790 (12)C1—Na2vii2.7790 (12)
Na2—C43.0813 (12)C2—C31.5389 (14)
Na2—Na1iv3.3886 (6)C2—H11.0000
Na2—Na2iv3.4259 (9)C3—C41.5385 (15)
O1—C11.2435 (13)C3—H31.0000
O1—Na2vii2.4513 (10)C4—Na1ix2.7875 (12)
O1—Na1—O2i105.24 (3)O6—Na2—Na1iv160.01 (3)
O1—Na1—O5ii83.81 (3)O1vi—Na2—Na1iv78.32 (2)
O2i—Na1—O5ii89.52 (3)O2vi—Na2—Na1iv43.53 (2)
O1—Na1—O4iii115.96 (4)C1vi—Na2—Na1iv62.98 (3)
O2i—Na1—O4iii132.93 (4)C4—Na2—Na1iv137.55 (3)
O5ii—Na1—O4iii115.67 (3)O4—Na2—Na2iv74.89 (3)
O1—Na1—O366.16 (3)O3iv—Na2—Na2iv102.54 (3)
O2i—Na1—O391.15 (3)O6iv—Na2—Na2iv44.23 (2)
O5ii—Na1—O3149.03 (3)O6—Na2—Na2iv44.11 (2)
O4iii—Na1—O385.73 (3)O1vi—Na2—Na2iv126.20 (3)
O1—Na1—O5iii159.12 (4)O2vi—Na2—Na2iv167.44 (3)
O2i—Na1—O5iii92.83 (3)C1vi—Na2—Na2iv148.01 (3)
O5ii—Na1—O5iii86.00 (3)C4—Na2—Na2iv70.08 (2)
O4iii—Na1—O5iii53.42 (3)Na1iv—Na2—Na2iv147.42 (2)
O3—Na1—O5iii124.87 (3)C1—O1—Na1124.02 (7)
O1—Na1—C4iii140.88 (4)C1—O1—Na2vii91.57 (7)
O2i—Na1—C4iii113.09 (4)Na1—O1—Na2vii128.11 (4)
O5ii—Na1—C4iii103.55 (3)C1—O2—Na1viii126.92 (7)
O4iii—Na1—C4iii26.47 (3)C1—O2—Na2vii87.02 (6)
O3—Na1—C4iii104.60 (3)Na1viii—O2—Na2vii88.03 (3)
O5iii—Na1—C4iii27.09 (3)C2—O3—Na2iv112.43 (6)
O1—Na1—Na2iv75.27 (3)C2—O3—Na1115.43 (6)
O2i—Na1—Na2iv48.44 (2)Na2iv—O3—Na188.42 (3)
O5ii—Na1—Na2iv122.82 (3)C2—O3—H2110.8 (11)
O4iii—Na1—Na2iv121.39 (3)Na2iv—O3—H2113.8 (11)
O3—Na1—Na2iv44.07 (2)Na1—O3—H2114.4 (11)
O5iii—Na1—Na2iv125.40 (3)C4—O4—Na2117.75 (7)
C4iii—Na1—Na2iv126.00 (3)C4—O4—Na1ix93.95 (7)
O1—Na1—Na1v125.98 (3)Na2—O4—Na1ix134.16 (4)
O2i—Na1—Na1v91.68 (3)C4—O5—Na1x130.76 (7)
O5ii—Na1—Na1v44.70 (2)C4—O5—Na1ix88.02 (7)
O4iii—Na1—Na1v82.32 (2)Na1x—O5—Na1ix94.00 (3)
O3—Na1—Na1v166.03 (3)C3—O6—Na2iv112.27 (6)
O5iii—Na1—Na1v41.30 (2)C3—O6—Na2113.49 (6)
C4iii—Na1—Na1v61.79 (2)Na2iv—O6—Na291.66 (3)
Na2iv—Na1—Na1v140.09 (2)C3—O6—H4108.1 (11)
O4—Na2—O3iv152.61 (4)Na2iv—O6—H4123.2 (11)
O4—Na2—O6iv89.13 (3)Na2—O6—H4107.0 (12)
O3iv—Na2—O6iv72.09 (3)O1—C1—O2123.77 (10)
O4—Na2—O669.00 (3)O1—C1—C2119.55 (10)
O3iv—Na2—O6128.17 (3)O2—C1—C2116.66 (9)
O6iv—Na2—O688.34 (3)O1—C1—Na2vii61.86 (6)
O4—Na2—O1vi103.37 (3)O2—C1—Na2vii65.74 (6)
O3iv—Na2—O1vi99.91 (3)C2—C1—Na2vii158.15 (7)
O6iv—Na2—O1vi161.92 (4)O3—C2—C1108.96 (9)
O6—Na2—O1vi84.14 (3)O3—C2—C3109.73 (9)
O4—Na2—O2vi92.94 (3)C1—C2—C3110.33 (9)
O3iv—Na2—O2vi89.70 (3)O3—C2—H1109.3
O6iv—Na2—O2vi140.73 (3)C1—C2—H1109.3
O6—Na2—O2vi128.77 (3)C3—C2—H1109.3
O1vi—Na2—O2vi52.82 (3)O6—C3—C4110.09 (9)
O4—Na2—C1vi93.93 (3)O6—C3—C2108.94 (8)
O3iv—Na2—C1vi100.63 (3)C4—C3—C2110.44 (9)
O6iv—Na2—C1vi167.66 (4)O6—C3—H3109.1
O6—Na2—C1vi103.92 (4)C4—C3—H3109.1
O1vi—Na2—C1vi26.57 (3)C2—C3—H3109.1
O2vi—Na2—C1vi27.24 (3)O4—C4—O5123.96 (10)
O4—Na2—C420.96 (3)O4—C4—C3119.58 (10)
O3iv—Na2—C4170.22 (3)O5—C4—C3116.46 (10)
O6iv—Na2—C498.22 (3)O4—C4—Na1ix59.58 (6)
O6—Na2—C450.89 (3)O5—C4—Na1ix64.89 (6)
O1vi—Na2—C489.75 (3)C3—C4—Na1ix172.43 (7)
O2vi—Na2—C497.44 (3)O4—C4—Na241.28 (5)
C1vi—Na2—C488.69 (3)O5—C4—Na2155.89 (7)
O4—Na2—Na1iv124.34 (3)C3—C4—Na281.60 (6)
O3iv—Na2—Na1iv47.50 (2)Na1ix—C4—Na295.11 (3)
O6iv—Na2—Na1iv105.57 (3)
O2i—Na1—O1—C1−103.88 (9)Na2iv—O3—C2—C178.38 (8)
O5ii—Na1—O1—C1168.31 (9)Na1—O3—C2—C1−21.02 (10)
O4iii—Na1—O1—C152.72 (10)Na2iv—O3—C2—C3−42.52 (10)
O3—Na1—O1—C1−19.48 (9)Na1—O3—C2—C3−141.92 (7)
O5iii—Na1—O1—C1107.05 (12)O1—C1—C2—O35.65 (14)
C4iii—Na1—O1—C164.41 (11)O2—C1—C2—O3−175.83 (9)
Na2iv—Na1—O1—C1−65.38 (9)Na2vii—C1—C2—O393.2 (2)
Na1v—Na1—O1—C1152.51 (8)O1—C1—C2—C3126.19 (11)
O2i—Na1—O1—Na2vii131.26 (5)O2—C1—C2—C3−55.30 (13)
O5ii—Na1—O1—Na2vii43.45 (5)Na2vii—C1—C2—C3−146.27 (17)
O4iii—Na1—O1—Na2vii−72.13 (6)Na2iv—O6—C3—C480.01 (8)
O3—Na1—O1—Na2vii−144.34 (6)Na2—O6—C3—C4−22.24 (10)
O5iii—Na1—O1—Na2vii−17.81 (13)Na2iv—O6—C3—C2−41.23 (10)
C4iii—Na1—O1—Na2vii−60.45 (7)Na2—O6—C3—C2−143.48 (7)
Na2iv—Na1—O1—Na2vii169.76 (5)O3—C2—C3—O656.23 (12)
Na1v—Na1—O1—Na2vii27.65 (7)C1—C2—C3—O6−63.83 (12)
O1—Na1—O3—C220.93 (7)O3—C2—C3—C4−64.79 (11)
O2i—Na1—O3—C2127.10 (7)C1—C2—C3—C4175.14 (9)
O5ii—Na1—O3—C236.12 (11)Na2—O4—C4—O5−154.27 (9)
O4iii—Na1—O3—C2−99.92 (7)Na1ix—O4—C4—O5−8.65 (11)
O5iii—Na1—O3—C2−138.64 (7)Na2—O4—C4—C325.69 (12)
C4iii—Na1—O3—C2−118.66 (7)Na1ix—O4—C4—C3171.31 (8)
Na2iv—Na1—O3—C2114.18 (8)Na2—O4—C4—Na1ix−145.62 (7)
Na1v—Na1—O3—C2−131.23 (13)Na1ix—O4—C4—Na2145.62 (7)
O1—Na1—O3—Na2iv−93.25 (4)Na1x—O5—C4—O4−85.34 (13)
O2i—Na1—O3—Na2iv12.92 (3)Na1ix—O5—C4—O48.23 (11)
O5ii—Na1—O3—Na2iv−78.06 (7)Na1x—O5—C4—C394.70 (11)
O4iii—Na1—O3—Na2iv145.90 (3)Na1ix—O5—C4—C3−171.72 (8)
O5iii—Na1—O3—Na2iv107.18 (4)Na1x—O5—C4—Na1ix−93.57 (8)
C4iii—Na1—O3—Na2iv127.16 (3)Na1x—O5—C4—Na2−129.86 (16)
Na1v—Na1—O3—Na2iv114.59 (13)Na1ix—O5—C4—Na2−36.3 (2)
O3iv—Na2—O4—C4−161.78 (8)O6—C3—C4—O4−1.01 (13)
O6iv—Na2—O4—C4−116.05 (8)C2—C3—C4—O4119.33 (11)
O6—Na2—O4—C4−27.50 (7)O6—C3—C4—O5178.95 (9)
O1vi—Na2—O4—C450.75 (8)C2—C3—C4—O5−60.71 (13)
O2vi—Na2—O4—C4103.18 (8)O6—C3—C4—Na1ix80.5 (6)
C1vi—Na2—O4—C475.91 (8)C2—C3—C4—Na1ix−159.2 (5)
Na1iv—Na2—O4—C4135.61 (7)O6—C3—C4—Na215.80 (7)
Na2iv—Na2—O4—C4−73.63 (7)C2—C3—C4—Na2136.14 (8)
O3iv—Na2—O4—Na1ix69.96 (10)O3iv—Na2—C4—O457.9 (2)
O6iv—Na2—O4—Na1ix115.68 (6)O6iv—Na2—C4—O465.18 (8)
O6—Na2—O4—Na1ix−155.76 (6)O6—Na2—C4—O4146.25 (9)
O1vi—Na2—O4—Na1ix−77.51 (6)O1vi—Na2—C4—O4−131.11 (8)
O2vi—Na2—O4—Na1ix−25.08 (6)O2vi—Na2—C4—O4−78.70 (8)
C1vi—Na2—O4—Na1ix−52.35 (6)C1vi—Na2—C4—O4−104.56 (8)
C4—Na2—O4—Na1ix−128.26 (11)Na1iv—Na2—C4—O4−58.85 (9)
Na1iv—Na2—O4—Na1ix7.34 (7)Na2iv—Na2—C4—O499.85 (8)
Na2iv—Na2—O4—Na1ix158.11 (6)O4—Na2—C4—O561.8 (2)
O4—Na2—O6—C325.51 (7)O3iv—Na2—C4—O5119.7 (2)
O3iv—Na2—O6—C3−179.25 (7)O6iv—Na2—C4—O5127.0 (2)
O6iv—Na2—O6—C3115.22 (8)O6—Na2—C4—O5−151.9 (2)
O1vi—Na2—O6—C3−81.24 (7)O1vi—Na2—C4—O5−69.3 (2)
O2vi—Na2—O6—C3−50.74 (9)O2vi—Na2—C4—O5−16.9 (2)
C1vi—Na2—O6—C3−63.37 (8)C1vi—Na2—C4—O5−42.7 (2)
C4—Na2—O6—C313.22 (7)Na1iv—Na2—C4—O53.0 (2)
Na1iv—Na2—O6—C3−109.91 (9)Na2iv—Na2—C4—O5161.7 (2)
Na2iv—Na2—O6—C3115.22 (8)O4—Na2—C4—C3−157.60 (11)
O4—Na2—O6—Na2iv−89.70 (3)O3iv—Na2—C4—C3−99.7 (2)
O3iv—Na2—O6—Na2iv65.53 (4)O6iv—Na2—C4—C3−92.43 (6)
O6iv—Na2—O6—Na2iv0.0O6—Na2—C4—C3−11.35 (6)
O1vi—Na2—O6—Na2iv163.54 (4)O1vi—Na2—C4—C371.29 (6)
O2vi—Na2—O6—Na2iv−165.95 (4)O2vi—Na2—C4—C3123.70 (6)
C1vi—Na2—O6—Na2iv−178.59 (4)C1vi—Na2—C4—C397.84 (6)
C4—Na2—O6—Na2iv−102.00 (4)Na1iv—Na2—C4—C3143.55 (5)
Na1iv—Na2—O6—Na2iv134.88 (8)Na2iv—Na2—C4—C3−57.75 (5)
Na1—O1—C1—O2−163.11 (8)O4—Na2—C4—Na1ix29.27 (7)
Na2vii—O1—C1—O2−23.34 (11)O3iv—Na2—C4—Na1ix87.1 (2)
Na1—O1—C1—C215.30 (14)O6iv—Na2—C4—Na1ix94.44 (4)
Na2vii—O1—C1—C2155.06 (9)O6—Na2—C4—Na1ix175.52 (5)
Na1—O1—C1—Na2vii−139.77 (8)O1vi—Na2—C4—Na1ix−101.84 (3)
Na1viii—O2—C1—O1−62.75 (14)O2vi—Na2—C4—Na1ix−49.43 (4)
Na2vii—O2—C1—O122.53 (11)C1vi—Na2—C4—Na1ix−75.29 (4)
Na1viii—O2—C1—C2118.80 (9)Na1iv—Na2—C4—Na1ix−29.59 (5)
Na2vii—O2—C1—C2−155.91 (9)Na2iv—Na2—C4—Na1ix129.12 (3)
Na1viii—O2—C1—Na2vii−85.29 (7)
D—H···AD—HH···AD···AD—H···A
O3—H2···O2xi0.900 (17)1.752 (18)2.6480 (12)173.2 (17)
O6—H4···O5xii0.883 (17)1.787 (17)2.6643 (12)172.0 (18)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O3—H2⋯O2i0.900 (17)1.752 (18)2.6480 (12)173.2 (17)
O6—H4⋯O5ii0.883 (17)1.787 (17)2.6643 (12)172.0 (18)

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Potassium sodium (2R,3R)-tartrate tetra-hydrate: the paraelectric phase of Rochelle salt at 105 K.

Authors:  Carl Henrik Görbitz; Einar Sagstuen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-05
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.