In the structure of sodium
D-
glycero-
D-
gulo-heptonate dihydrate, Na
+·C
7H
13O
8−·2H
2O, the glucoheptonate anion has a bent carbon chain conformation. There are extensive intermolecular hydrogen bonds involving all the hydroxy and water H atoms. The Na
+ cation has a distorted octahedral coordination to six O atoms, with Na
+O distances ranging from 2.316 (2) to 2.645 (2) Å.
Supporting information
CCDC reference: 158224
Crystals of (I) (m.p. 437 K) were obtained from Aldrich Chemical Company, Inc.
and no further recrystallization was carried out.
The coordinates and isotropic displacement parameters of all H atoms were
refined. We did not determine the absolute configuration but assumed the
D-form, corresponding to the configuration as supplied by Aldrich Chemical
Company, Inc. The C—H and O—H bond distances range from 0.92 (4) to 1.00 (4) Å and from 0.73 (5) to 0.85 (4) Å, respectively.
Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: SET4 and CELDIM in CAD-4-PC Software; data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
Sodium D-
glycero-D-
gulo-heptonate dihydrate
top
Crystal data top
[Na(C7H13O8)]·2H2O | Dx = 1.593 Mg m−3 |
Mr = 284.20 | Melting point: 437 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
a = 6.181 (1) Å | Cell parameters from 25 reflections |
b = 9.200 (1) Å | θ = 15.7–24.7° |
c = 10.691 (1) Å | µ = 0.18 mm−1 |
β = 102.94 (1)° | T = 292 K |
V = 592.4 (1) Å3 | Prism, colourless |
Z = 2 | 0.65 × 0.50 × 0.28 mm |
F(000) = 300 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.0° |
Graphite monochromator | h = 0→7 |
ω/2θ scans | k = 0→11 |
1359 measured reflections | l = −13→12 |
1243 independent reflections | 3 standard reflections every 60 min |
1206 reflections with I > 2σ(I) | intensity decay: 2.2% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.090 | All H-atom parameters refined |
S = 1.28 | Calculated w = 1/[σ2(Fo2) + (0.0568P)2 + 0.0911P] where P = (Fo2 + 2Fc2)/3 |
1243 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
Crystal data top
[Na(C7H13O8)]·2H2O | V = 592.4 (1) Å3 |
Mr = 284.20 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.181 (1) Å | µ = 0.18 mm−1 |
b = 9.200 (1) Å | T = 292 K |
c = 10.691 (1) Å | 0.65 × 0.50 × 0.28 mm |
β = 102.94 (1)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.024 |
1359 measured reflections | 3 standard reflections every 60 min |
1243 independent reflections | intensity decay: 2.2% |
1206 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
wR(F2) = 0.090 | All H-atom parameters refined |
S = 1.28 | Δρmax = 0.32 e Å−3 |
1243 reflections | Δρmin = −0.25 e Å−3 |
231 parameters | |
Special details top
Experimental. ω/2θ scan width (1.20 + 0.35tanθ)°, background counts for 2 s on each side
of every scan. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Na | 0.50300 (17) | −0.82914 (14) | 0.30397 (11) | 0.0284 (3) | |
C1 | 0.8619 (4) | −0.7430 (3) | 0.5456 (2) | 0.0193 (5) | |
O11 | 0.9570 (3) | −0.6907 (2) | 0.65415 (19) | 0.0268 (5) | |
O12 | 0.7452 (3) | −0.6739 (2) | 0.45629 (19) | 0.0250 (4) | |
C2 | 0.8989 (4) | −0.9062 (3) | 0.5270 (2) | 0.0179 (5) | |
O2 | 0.8659 (3) | −0.9316 (2) | 0.39176 (18) | 0.0219 (4) | |
C3 | 0.7325 (4) | −0.9961 (3) | 0.5813 (2) | 0.0194 (5) | |
O3 | 0.5194 (3) | −0.9323 (2) | 0.53688 (19) | 0.0255 (5) | |
C4 | 0.7964 (4) | −1.0098 (3) | 0.7290 (2) | 0.0194 (5) | |
O4 | 0.6066 (4) | −1.0484 (3) | 0.7767 (2) | 0.0260 (4) | |
C5 | 0.9674 (4) | −1.1298 (3) | 0.7684 (2) | 0.0196 (5) | |
O5 | 0.8656 (3) | −1.2633 (2) | 0.7196 (2) | 0.0249 (4) | |
C6 | 1.0565 (5) | −1.1453 (3) | 0.9139 (2) | 0.0235 (6) | |
O6 | 1.1765 (4) | −1.0152 (3) | 0.9563 (2) | 0.0325 (5) | |
C7 | 1.2053 (5) | −1.2773 (4) | 0.9474 (3) | 0.0272 (6) | |
O7 | 1.3955 (3) | −1.2710 (3) | 0.8923 (2) | 0.0331 (5) | |
OW1 | 0.3615 (5) | −1.0636 (3) | 0.2207 (2) | 0.0345 (5) | |
OW2 | 1.3424 (4) | −0.7989 (3) | 0.8050 (3) | 0.0412 (6) | |
H2 | 1.046 (5) | −0.936 (4) | 0.568 (3) | 0.016 (7)* | |
H3 | 0.739 (5) | −1.093 (4) | 0.547 (3) | 0.017 (7)* | |
H4 | 0.854 (5) | −0.920 (4) | 0.763 (3) | 0.011 (6)* | |
H5 | 1.092 (5) | −1.109 (4) | 0.729 (3) | 0.017 (7)* | |
H6 | 0.929 (5) | −1.159 (4) | 0.954 (3) | 0.017 (7)* | |
H71 | 1.254 (6) | −1.290 (5) | 1.043 (4) | 0.037 (10)* | |
H72 | 1.121 (6) | −1.357 (5) | 0.918 (4) | 0.037 (11)* | |
H2O | 0.922 (8) | −1.007 (6) | 0.385 (4) | 0.047 (12)* | |
H3O | 0.440 (7) | −0.991 (6) | 0.536 (4) | 0.041 (12)* | |
H4O | 0.522 (6) | −0.984 (5) | 0.771 (4) | 0.022 (9)* | |
H5O | 0.946 (7) | −1.303 (5) | 0.692 (4) | 0.032 (11)* | |
H6O | 1.232 (7) | −1.025 (6) | 1.032 (5) | 0.045 (12)* | |
H7O | 1.450 (7) | −1.187 (5) | 0.914 (4) | 0.031 (9)* | |
H11W | 0.268 (10) | −1.084 (7) | 0.257 (6) | 0.074 (18)* | |
H12W | 0.440 (12) | −1.135 (9) | 0.212 (7) | 0.09 (2)* | |
H21W | 1.221 (7) | −0.768 (5) | 0.759 (4) | 0.038 (10)* | |
H22W | 1.312 (8) | −0.840 (6) | 0.856 (5) | 0.047 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na | 0.0229 (5) | 0.0321 (6) | 0.0288 (6) | 0.0010 (5) | 0.0026 (4) | −0.0036 (5) |
C1 | 0.0161 (10) | 0.0199 (13) | 0.0224 (12) | −0.0018 (10) | 0.0056 (9) | 0.0017 (10) |
O11 | 0.0321 (10) | 0.0213 (10) | 0.0247 (10) | −0.0029 (8) | 0.0016 (8) | −0.0010 (8) |
O12 | 0.0282 (9) | 0.0160 (9) | 0.0290 (10) | 0.0034 (8) | 0.0025 (8) | 0.0007 (8) |
C2 | 0.0167 (11) | 0.0187 (12) | 0.0176 (11) | 0.0014 (10) | 0.0022 (9) | 0.0010 (10) |
O2 | 0.0296 (10) | 0.0162 (9) | 0.0209 (9) | 0.0036 (8) | 0.0078 (7) | 0.0013 (7) |
C3 | 0.0196 (12) | 0.0168 (12) | 0.0202 (12) | 0.0004 (10) | 0.0012 (9) | 0.0014 (10) |
O3 | 0.0174 (9) | 0.0250 (10) | 0.0323 (10) | −0.0035 (9) | 0.0014 (8) | 0.0059 (8) |
C4 | 0.0201 (11) | 0.0189 (13) | 0.0196 (12) | −0.0012 (10) | 0.0053 (9) | 0.0010 (10) |
O4 | 0.0226 (9) | 0.0291 (11) | 0.0288 (10) | 0.0034 (9) | 0.0110 (8) | 0.0060 (9) |
C5 | 0.0187 (11) | 0.0202 (13) | 0.0192 (11) | 0.0001 (10) | 0.0030 (9) | 0.0019 (11) |
O5 | 0.0232 (9) | 0.0207 (10) | 0.0305 (10) | 0.0013 (8) | 0.0056 (8) | −0.0038 (9) |
C6 | 0.0249 (12) | 0.0266 (14) | 0.0185 (11) | −0.0012 (11) | 0.0042 (10) | 0.0030 (11) |
O6 | 0.0426 (12) | 0.0279 (11) | 0.0219 (11) | −0.0032 (10) | −0.0036 (9) | −0.0010 (9) |
C7 | 0.0287 (14) | 0.0282 (15) | 0.0235 (13) | 0.0011 (13) | 0.0030 (11) | 0.0070 (12) |
O7 | 0.0298 (10) | 0.0303 (12) | 0.0396 (12) | 0.0027 (10) | 0.0086 (9) | 0.0006 (10) |
OW1 | 0.0396 (13) | 0.0327 (13) | 0.0312 (12) | −0.0002 (11) | 0.0082 (10) | 0.0009 (10) |
OW2 | 0.0292 (12) | 0.0514 (16) | 0.0403 (13) | 0.0014 (12) | 0.0024 (10) | 0.0120 (13) |
Geometric parameters (Å, º) top
Na—O5i | 2.316 (2) | C2—C3 | 1.532 (3) |
Na—O7ii | 2.382 (3) | C3—O3 | 1.423 (3) |
Na—O12 | 2.416 (2) | C3—C4 | 1.545 (4) |
Na—O2 | 2.420 (2) | C4—O4 | 1.425 (3) |
Na—OW1 | 2.421 (3) | C4—C5 | 1.521 (4) |
Na—O3 | 2.645 (2) | O4—Naiii | 2.759 (3) |
Na—O4i | 2.759 (3) | C5—O5 | 1.425 (3) |
Na—C2 | 3.093 (3) | C5—C6 | 1.537 (3) |
Na—C1 | 3.107 (3) | O5—Naiii | 2.316 (2) |
C1—O12 | 1.235 (3) | C6—O6 | 1.428 (4) |
C1—O11 | 1.272 (3) | C6—C7 | 1.517 (4) |
C1—C2 | 1.538 (4) | C7—O7 | 1.429 (4) |
C2—O2 | 1.434 (3) | O7—Naiv | 2.382 (3) |
| | | |
O5i—Na—O7ii | 106.99 (9) | O4i—Na—C1 | 95.77 (8) |
O5i—Na—O12 | 111.38 (8) | C2—Na—C1 | 28.73 (7) |
O7ii—Na—O12 | 102.43 (8) | O12—C1—O11 | 125.5 (3) |
O5i—Na—O2 | 161.39 (9) | O12—C1—C2 | 118.7 (2) |
O7ii—Na—O2 | 91.43 (8) | O11—C1—C2 | 115.8 (2) |
O12—Na—O2 | 65.68 (7) | O12—C1—Na | 45.92 (14) |
O5i—Na—OW1 | 85.84 (9) | O11—C1—Na | 162.32 (18) |
O7ii—Na—OW1 | 91.21 (9) | C2—C1—Na | 75.12 (15) |
O12—Na—OW1 | 153.18 (9) | C1—O12—Na | 112.53 (18) |
O2—Na—OW1 | 91.31 (9) | O2—C2—C3 | 109.7 (2) |
O5i—Na—O3 | 91.47 (8) | O2—C2—C1 | 107.3 (2) |
O7ii—Na—O3 | 161.39 (9) | C3—C2—C1 | 110.3 (2) |
O12—Na—O3 | 71.95 (8) | O2—C2—Na | 49.47 (11) |
O2—Na—O3 | 70.02 (7) | C3—C2—Na | 86.16 (14) |
OW1—Na—O3 | 87.76 (9) | C1—C2—Na | 76.16 (15) |
O5i—Na—O4i | 63.54 (8) | C2—O2—Na | 103.77 (14) |
O7ii—Na—O4i | 66.99 (8) | O3—C3—C2 | 107.5 (2) |
O12—Na—O4i | 74.28 (7) | O3—C3—C4 | 112.4 (2) |
O2—Na—O4i | 128.83 (8) | C2—C3—C4 | 113.0 (2) |
OW1—Na—O4i | 132.54 (8) | C3—O3—Na | 107.44 (15) |
O3—Na—O4i | 125.80 (8) | O4—C4—C5 | 107.3 (2) |
O5i—Na—C2 | 137.14 (8) | O4—C4—C3 | 110.1 (2) |
O7ii—Na—C2 | 114.31 (8) | C5—C4—C3 | 110.1 (2) |
O12—Na—C2 | 49.60 (7) | C4—O4—Naiii | 106.62 (16) |
O2—Na—C2 | 26.76 (6) | O5—C5—C4 | 107.6 (2) |
OW1—Na—C2 | 103.75 (9) | O5—C5—C6 | 108.6 (2) |
O3—Na—C2 | 48.32 (6) | C4—C5—C6 | 114.6 (2) |
O4i—Na—C2 | 123.50 (8) | C5—O5—Naiii | 127.48 (17) |
O5i—Na—C1 | 121.70 (8) | O6—C6—C7 | 110.6 (2) |
O7ii—Na—C1 | 113.27 (8) | O6—C6—C5 | 106.6 (2) |
O12—Na—C1 | 21.55 (7) | C7—C6—C5 | 112.0 (2) |
O2—Na—C1 | 49.44 (7) | O7—C7—C6 | 112.5 (2) |
OW1—Na—C1 | 131.66 (9) | C7—O7—Naiv | 139.22 (19) |
O3—Na—C1 | 55.90 (7) | | |
| | | |
O5i—Na—C1—O12 | −66.6 (2) | C1—Na—C2—C3 | 112.0 (2) |
O7ii—Na—C1—O12 | 63.18 (19) | O5i—Na—C2—C1 | −68.97 (17) |
O2—Na—C1—O12 | 133.8 (2) | O7ii—Na—C2—C1 | 94.45 (15) |
OW1—Na—C1—O12 | 177.61 (19) | O12—Na—C2—C1 | 8.71 (12) |
O3—Na—C1—O12 | −134.1 (2) | O2—Na—C2—C1 | 127.8 (2) |
O4i—Na—C1—O12 | −4.22 (18) | OW1—Na—C2—C1 | −167.82 (14) |
C2—Na—C1—O12 | 161.7 (3) | O3—Na—C2—C1 | −93.59 (15) |
O5i—Na—C1—O11 | 1.4 (7) | O4i—Na—C2—C1 | 16.89 (16) |
O7ii—Na—C1—O11 | 131.1 (6) | C3—C2—O2—Na | 66.4 (2) |
O12—Na—C1—O11 | 67.9 (6) | C1—C2—O2—Na | −53.4 (2) |
O2—Na—C1—O11 | −158.3 (7) | O5i—Na—O2—C2 | −38.0 (3) |
OW1—Na—C1—O11 | −114.5 (6) | O7ii—Na—O2—C2 | 149.89 (15) |
O3—Na—C1—O11 | −66.2 (6) | O12—Na—O2—C2 | 46.89 (15) |
O4i—Na—C1—O11 | 63.7 (6) | OW1—Na—O2—C2 | −118.86 (15) |
C2—Na—C1—O11 | −130.4 (7) | O3—Na—O2—C2 | −31.72 (15) |
O5i—Na—C1—C2 | 131.74 (14) | O4i—Na—O2—C2 | 88.70 (16) |
O7ii—Na—C1—C2 | −98.50 (15) | C1—Na—O2—C2 | 29.98 (14) |
O12—Na—C1—C2 | −161.7 (3) | O2—C2—C3—O3 | −71.6 (3) |
O2—Na—C1—C2 | −27.91 (12) | C1—C2—C3—O3 | 46.3 (3) |
OW1—Na—C1—C2 | 15.92 (18) | Na—C2—C3—O3 | −27.37 (18) |
O3—Na—C1—C2 | 64.18 (13) | O2—C2—C3—C4 | 163.8 (2) |
O4i—Na—C1—C2 | −165.91 (13) | C1—C2—C3—C4 | −78.2 (3) |
O11—C1—O12—Na | −159.8 (2) | Na—C2—C3—C4 | −151.9 (2) |
C2—C1—O12—Na | 20.3 (3) | C2—C3—O3—Na | 34.2 (2) |
O5i—Na—O12—C1 | 123.03 (18) | C4—C3—O3—Na | 159.15 (17) |
O7ii—Na—O12—C1 | −122.91 (18) | O5i—Na—O3—C3 | 175.64 (17) |
O2—Na—O12—C1 | −37.01 (17) | O7ii—Na—O3—C3 | 2.7 (4) |
OW1—Na—O12—C1 | −4.0 (3) | O12—Na—O3—C3 | −72.33 (17) |
O3—Na—O12—C1 | 38.69 (17) | O2—Na—O3—C3 | −2.35 (16) |
O4i—Na—O12—C1 | 175.64 (19) | OW1—Na—O3—C3 | 89.86 (18) |
C2—Na—O12—C1 | −11.44 (16) | O4i—Na—O3—C3 | −126.44 (17) |
O12—C1—C2—O2 | 24.0 (3) | C2—Na—O3—C3 | −20.83 (15) |
O11—C1—C2—O2 | −155.9 (2) | C1—Na—O3—C3 | −56.23 (16) |
Na—C1—C2—O2 | 38.95 (15) | O3—C3—C4—O4 | 38.2 (3) |
O12—C1—C2—C3 | −95.4 (3) | C2—C3—C4—O4 | 160.0 (2) |
O11—C1—C2—C3 | 84.6 (3) | O3—C3—C4—C5 | 156.3 (2) |
Na—C1—C2—C3 | −80.52 (17) | C2—C3—C4—C5 | −81.9 (3) |
O12—C1—C2—Na | −14.9 (2) | C5—C4—O4—Naiii | −51.4 (2) |
O11—C1—C2—Na | 165.1 (2) | C3—C4—O4—Naiii | 68.5 (2) |
O5i—Na—C2—O2 | 163.19 (16) | O4—C4—C5—O5 | 56.3 (3) |
O7ii—Na—C2—O2 | −33.39 (17) | C3—C4—C5—O5 | −63.5 (3) |
O12—Na—C2—O2 | −119.12 (17) | O4—C4—C5—C6 | −64.6 (3) |
OW1—Na—C2—O2 | 64.34 (16) | C3—C4—C5—C6 | 175.6 (2) |
O3—Na—C2—O2 | 138.57 (19) | C4—C5—O5—Naiii | −33.7 (3) |
O4i—Na—C2—O2 | −110.95 (16) | C6—C5—O5—Naiii | 90.9 (2) |
C1—Na—C2—O2 | −127.8 (2) | O5—C5—C6—O6 | 174.1 (2) |
O5i—Na—C2—C3 | 43.0 (2) | C4—C5—C6—O6 | −65.6 (3) |
O7ii—Na—C2—C3 | −153.56 (15) | O5—C5—C6—C7 | 53.1 (3) |
O12—Na—C2—C3 | 120.71 (17) | C4—C5—C6—C7 | 173.4 (2) |
O2—Na—C2—C3 | −120.2 (2) | O6—C6—C7—O7 | −58.3 (3) |
OW1—Na—C2—C3 | −55.83 (16) | C5—C6—C7—O7 | 60.4 (3) |
O3—Na—C2—C3 | 18.40 (14) | C6—C7—O7—Naiv | −85.1 (4) |
O4i—Na—C2—C3 | 128.88 (14) | | |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1; (iv) −x+2, y−1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O11iv | 0.79 (5) | 1.93 (5) | 2.714 (4) | 173 (4) |
O3—H3O···O12iii | 0.73 (5) | 2.04 (5) | 2.771 (4) | 172 (5) |
O4—H4O···OW2v | 0.78 (5) | 2.11 (5) | 2.872 (4) | 165 (4) |
O5—H5O···O2iv | 0.73 (3) | 2.01 (3) | 2.730 (3) | 172 (4) |
O6—H6O···OW1vi | 0.82 (4) | 2.02 (4) | 2.837 (3) | 176 (3) |
O7—H7O···O4vii | 0.85 (6) | 2.31 (5) | 2.854 (4) | 122 (4) |
OW1—H11W···O11iii | 0.79 (4) | 2.09 (4) | 2.865 (3) | 166 (4) |
OW1—H12W···OW2iv | 0.83 (5) | 2.06 (5) | 2.887 (3) | 175 (4) |
OW2—H21W···O11 | 0.85 (4) | 1.90 (5) | 2.747 (3) | 177 (5) |
OW2—H22W···O6 | 0.73 (5) | 2.20 (5) | 2.893 (4) | 160 (5) |
Symmetry codes: (iii) −x+1, y−1/2, −z+1; (iv) −x+2, y−1/2, −z+1; (v) x−1, y, z; (vi) x+1, y, z+1; (vii) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | [Na(C7H13O8)]·2H2O |
Mr | 284.20 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 292 |
a, b, c (Å) | 6.181 (1), 9.200 (1), 10.691 (1) |
β (°) | 102.94 (1) |
V (Å3) | 592.4 (1) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.65 × 0.50 × 0.28 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1359, 1243, 1206 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.616 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.090, 1.28 |
No. of reflections | 1243 |
No. of parameters | 231 |
No. of restraints | 1 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.32, −0.25 |
Selected geometric parameters (Å, º) topNa—O5i | 2.316 (2) | C2—C3 | 1.532 (3) |
Na—O7ii | 2.382 (3) | C3—O3 | 1.423 (3) |
Na—O12 | 2.416 (2) | C3—C4 | 1.545 (4) |
Na—O2 | 2.420 (2) | C4—O4 | 1.425 (3) |
Na—OW1 | 2.421 (3) | C4—C5 | 1.521 (4) |
Na—O3 | 2.645 (2) | C5—O5 | 1.425 (3) |
C1—O12 | 1.235 (3) | C5—C6 | 1.537 (3) |
C1—O11 | 1.272 (3) | C6—O6 | 1.428 (4) |
C1—C2 | 1.538 (4) | C6—C7 | 1.517 (4) |
C2—O2 | 1.434 (3) | C7—O7 | 1.429 (4) |
| | | |
O12—C1—O11 | 125.5 (3) | O4—C4—C3 | 110.1 (2) |
O12—C1—C2 | 118.7 (2) | C5—C4—C3 | 110.1 (2) |
O11—C1—C2 | 115.8 (2) | O5—C5—C4 | 107.6 (2) |
O2—C2—C3 | 109.7 (2) | O5—C5—C6 | 108.6 (2) |
O2—C2—C1 | 107.3 (2) | C4—C5—C6 | 114.6 (2) |
C3—C2—C1 | 110.3 (2) | O6—C6—C7 | 110.6 (2) |
O3—C3—C2 | 107.5 (2) | O6—C6—C5 | 106.6 (2) |
O3—C3—C4 | 112.4 (2) | C7—C6—C5 | 112.0 (2) |
C2—C3—C4 | 113.0 (2) | O7—C7—C6 | 112.5 (2) |
O4—C4—C5 | 107.3 (2) | | |
| | | |
O12—C1—C2—C3 | −95.4 (3) | C3—C4—C5—C6 | 175.6 (2) |
O11—C1—C2—C3 | 84.6 (3) | C4—C5—C6—C7 | 173.4 (2) |
C1—C2—C3—C4 | −78.2 (3) | C5—C6—C7—O7 | 60.4 (3) |
C2—C3—C4—C5 | −81.9 (3) | | |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O11iii | 0.79 (5) | 1.93 (5) | 2.714 (4) | 173 (4) |
O3—H3O···O12iv | 0.73 (5) | 2.04 (5) | 2.771 (4) | 172 (5) |
O4—H4O···OW2v | 0.78 (5) | 2.11 (5) | 2.872 (4) | 165 (4) |
O5—H5O···O2iii | 0.73 (3) | 2.01 (3) | 2.730 (3) | 172 (4) |
O6—H6O···OW1vi | 0.82 (4) | 2.02 (4) | 2.837 (3) | 176 (3) |
O7—H7O···O4vii | 0.85 (6) | 2.31 (5) | 2.854 (4) | 122 (4) |
OW1—H11W···O11iv | 0.79 (4) | 2.09 (4) | 2.865 (3) | 166 (4) |
OW1—H12W···OW2iii | 0.83 (5) | 2.06 (5) | 2.887 (3) | 175 (4) |
OW2—H21W···O11 | 0.85 (4) | 1.90 (5) | 2.747 (3) | 177 (5) |
OW2—H22W···O6 | 0.73 (5) | 2.20 (5) | 2.893 (4) | 160 (5) |
Symmetry codes: (iii) −x+2, y−1/2, −z+1; (iv) −x+1, y−1/2, −z+1; (v) x−1, y, z; (vi) x+1, y, z+1; (vii) x+1, y, z. |
The primary aim of this study was to examine the acyclic carbon chain conformation in the D-glycero-D-gulo-heptonate anion of the title compound, (I). Crystal structure studies of meso-L-glycero-L-gulo-heptitol (Nimgirawath et al., 1976) and of other alditols (Park et al., 1971, 1989; Panagiotopoulos et al., 1974) led to the expectation that, because of its DDLDD configuration, the D-glycero-D-gulo-heptonate anion should exist as the bent conformer. This conformational preference has its origin in the repulsion of syn-axially related hydroxyl groups, parallel to C3—OH and C5—OH, in the straight-chain conformer. \sch
The anion of (I) has a bent-chain conformation. This conformation can be derived from the zigzag planar conformation by two consecutive rotations around the C3—C4 and C2—C3 bonds. This bent-chain conformation was predicted for the polyhydroxy alkyl chain of D-glycero-D-gulo-heptitol by Jeffrey & Kim (1970). In the bent conformer of (I) the C atoms lie in two planes, C1—C3 and C3—C7, with an interplanar angle of 71.2 (2)°.
The Na+ cations occupy the voids between the hydrogen-bonded anions. The sixfold coordination of each Na+ cation consists of O2, O3, O5, O7, O12 and OW1, with Na+···O distances ranging from 2.316 (2) to 2.645 (2) Å, making a distorted octahedral geometry.
The molecular packing in the crystal of (I) appears to be determined mainly by hydrogen bonds, since there are ten hydrogen bonds per asymmetric unit. The hydrogen bond distances and angles are listed in Table 2. The molecular packing projected down the b axis is shown in Fig. 2. A l l six hydroxy groups and the water molecules act as hydrogen-bond donors. Atoms O2, O4 and O6 are hydrogen-bond acceptors; O3, O5 and O7 do not accept any hydrogen bonds. Atom OW2 accepts two hydrogen bonds, while OW1 accepts one. The O11 carboxylate accepts three hydrogen bonds and O12 one. This may account for the small difference in bond length of 0.037 Å by which the C1—O11 distance is longer than C1—O12. Each molecule is linked by two kinds of hydrogen bonds, one donor-acceptor hydrogen bond and one branched hydrogen bond.