Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039220/bt2469sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039220/bt2469Isup2.hkl |
CCDC reference: 660091
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.101
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.80 Ratio
Author Response: There are nine water molecules, three of which are connected to Cd and two to Na. The large non-solvent H atoms refer to the two connected to Na. The U(iso) of O4w and O5w are large (0.091 and 0.136). The ALERT seems to be an artifact as the O4w and O5w atoms form a connected set. |
Alert level B PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.24 Ratio PLAT417_ALERT_2_B Short Inter D-H..H-D H4W2 .. H9W1 .. 1.25 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H5W1 .. H8W2 .. 2.02 Ang. PLAT731_ALERT_1_B Bond Calc 0.86(6), Rep 0.860(10) ...... 6.00 su-Ra O5W -H5W1 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.86(8), Rep 0.860(10) ...... 8.00 su-Ra O5W -H5W2 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.85(7), Rep 0.850(10) ...... 7.00 su-Ra O8W -H8W1 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.85(6), Rep 0.850(10) ...... 6.00 su-Ra O8W -H8W2 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.85(5), Rep 0.850(10) ...... 5.00 su-Ra O9W -H9W2 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(6), Rep 0.860(10) ...... 6.00 su-Ra O5W -H9# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(8), Rep 0.860(10) ...... 8.00 su-Ra O5W -H10# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.85(7), Rep 0.850(10) ...... 7.00 su-Ra O8W -H15# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.85(6), Rep 0.850(10) ...... 6.00 su-Ra O8W -H16# 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.85(5), Rep 0.850(10) ...... 5.00 su-Ra O9W -H18# 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Na1 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 18 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.840(10) ...... 4.00 su-Ra O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Ra O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O2W -H2W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O3W -H3W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O3W -H3W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Ra O4W -H4W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Ra O4W -H4W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O6W -H6W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O6W -H6W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Ra O7W -H7W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O7W -H7W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Ra O9W -H9W1 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 108(7), Rep 108(2) ...... 3.50 su-Ra H5W1 -O5W -H5W2 1.555 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 110(7), Rep 110(2) ...... 3.50 su-Ra H8W1 -O8W -H8W2 1.555 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 109(6), Rep 109(2) ...... 3.00 su-Ra H9W1 -O9W -H9W2 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.840(10) ...... 4.00 su-Ra O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.850(10) ...... 4.00 su-Ra O1W -H2# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O2W -H4# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O3W -H5# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O3W -H6# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Ra O4W -H7# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Ra O4W -H8# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O6W -H11# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O6W -H12# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Ra O7W -H13# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra O7W -H14# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.860(10) ...... 3.00 su-Ra O9W -H17# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.93(3), Rep 1.920(10) ...... 3.00 su-Ra H2# -O7W 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.91(3), Rep 1.910(10) ...... 3.00 su-Ra H5# -O7W 1.555 1.655 PLAT736_ALERT_1_C H...A Calc 1.89(3), Rep 1.890(10) ...... 3.00 su-Ra H6# -O5 1.555 2.767 PLAT736_ALERT_1_C H...A Calc 2.05(7), Rep 2.04(3) ...... 2.33 su-Ra H15# -O3W 1.555 1.455 PLAT736_ALERT_1_C H...A Calc 1.96(6), Rep 1.96(2) ...... 3.00 su-Ra H18# -O1 1.555 2.667
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... S PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1 (2) 2.16 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 32
1 ALERT level A = In general: serious problem 13 ALERT level B = Potentially serious problem 37 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 45 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For the crystal structures of metal derivatives of 3-carboxyphenoxyacetic acids, see Gao & Ng (2006); Gao, Huo, Deng et al. (2005); Zhao, Huo, Gao et al. (2005); Li et al. (2004); Zhao, Gu, Gao et al. (2005); Gao, Gu, Huo et al. (2004a); Gao, Gu, Huo et al. (2004b); Gao, Gu, Zhao et al. (2004); Gao, Huo, Cheng et al. (2005); Gu et al. (2005); Gao, Huo, Liu et al. (2005); Zhao, Gu, Huo et al. (2005). For the sole reference to 5-carboxy-1,3-diphenoxyacetic acid, see the patent for antibaterial properties by Leslie et al. (2004).
Sodium hydroxide was added to an aqueous soluiton consisting of 3 molar equivalents of chloroacetic acid and one equivalent of 3,5-dihydroxybenzoic acid until the solution was basic (pH approximately 11). The solution was heated for 3 h. The cool solution was neutralized with concentrated hydrochloric acid to a pH of about 3. The light-yellow solid that was precipitated was collected and dried.
5-Carboxy-1,3-diphenoxyacetic acid (0.282 g, 1 mol) and cadmium acetate dihydrate (0.266 g, 1 mol) were mixed in 20 ml e thanol-water (1:1, v/v) solution. The pH value was adjusted to 7 by sodium carbonate solution. The filtered solution was set aside for the growth of crystals after a week.
The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.85±0.01 Å and H..H 1.39 + 00.01 Å); their displacement parameters were freely refined. The carbon-bound H-atoms were generated geometrically (C–H 0.93 to 0.97 Å); they were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).
There is a number of metal derivatives of 3-carboxyphenoxyacetic acid, a carboxylic acid whose deprotonated dianion is regarded as a flexible dianion. The phenoxy linkage in the dianion is also capable of bonding, and this feature is noted in some of the calcium (Gao & Ng, 2006), cadmium (Gao, Huo, Deng & Ng, 2005; Zhao, Gu, Gao, Huo & Liu, 2005), cobalt (Li et al., 2004; Zhao, Gu, Huo et al., 2005), copper (Gao, Gu, Huo et al., 2004a, Gao, Gu, Huo et al., 2004b; Gao, Gu, Zhao et al., 2004), manganese (Gao, Huo, Cheng et al., 2005), nickel (Gu et al., 2005) and zinc (Gao, Huo, Liu et al., 2005; Zhao, Gu, Huo et al., 2005) derivatives. There is a similar number of divalent metal derivatives of the "two-armed" (and much more flexible) acid, benzene-1,3-dioxyacetic acid in the crystallographic literature (CSD Version 5.28, May 2007). Curiously, there is almost no crystallographic mention of the related tricarboxylic acid, 5-carboxy-1,3-diphenoxyacetic acid, the sole mention possibly being a patent claim for antibaterial properties (Leslie et al., 2004) only.
In the crystal structure of pentaaqua(5-carboxy-1,3-phenoxydiacetato)cadmiumsodium tetrahydrate, the carboxylate trianion binds to a triaquacadmium unit through one oxygen atom of its 5-carboxyl group. It also chelates through two oxygen atoms of the 5-oxyacetate group to an adjacent triaquacadmium unit to form a linear chain. Meanwhile, the diaquasodium unit is chelated by the 1-oxyacetate [–O–CH2–C(O)O–] group of one trianion and as well as by the 3-oxyacetate group of another trianion. Both cadmium and sodium sites exist six-coordinate octahedral geometries in the ribbon structure. The ribbons are linked into a three-dimensional network by extensive hydrogen bonds.
The lattice water molecules occupy the space within the ribbon; however, their contribution to the total volume is small as their exclusion is not seen in any significant voids in the unit cell.
For the crystal structures of metal derivatives of 3-carboxyphenoxyacetic acids, see Gao & Ng (2006); Gao, Huo, Deng et al. (2005); Zhao, Huo, Gao et al. (2005); Li et al. (2004); Zhao, Gu, Gao et al. (2005); Gao, Gu, Huo et al. (2004a); Gao, Gu, Huo et al. (2004b); Gao, Gu, Zhao et al. (2004); Gao, Huo, Cheng et al. (2005); Gu et al. (2005); Gao, Huo, Liu et al. (2005); Zhao, Gu, Huo et al. (2005). For the sole reference to 5-carboxy-1,3-diphenoxyacetic acid, see the patent for antibaterial properties by Leslie et al. (2004).
Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).
[CdNa(C11H7O8)(H2O)5]·4H2O | Z = 2 |
Mr = 564.70 | F(000) = 572 |
Triclinic, P1 | Dx = 1.820 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2853 (2) Å | Cell parameters from 3652 reflections |
b = 11.1525 (3) Å | θ = 2.7–26.2° |
c = 14.0096 (3) Å | µ = 1.16 mm−1 |
α = 70.123 (1)° | T = 295 K |
β = 78.582 (1)° | Block, colourless |
γ = 75.987 (1)° | 0.18 × 0.08 × 0.05 mm |
V = 1030.23 (5) Å3 |
Bruker APEXII area-detector diffractometer | 4627 independent reflections |
Radiation source: fine-focus sealed tube | 3861 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 27.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.832, Tmax = 0.944 | k = −14→14 |
12790 measured reflections | l = −18→18 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3078P] where P = (Fo2 + 2Fc2)/3 |
4627 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.76 e Å−3 |
32 restraints | Δρmin = −0.55 e Å−3 |
[CdNa(C11H7O8)(H2O)5]·4H2O | γ = 75.987 (1)° |
Mr = 564.70 | V = 1030.23 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2853 (2) Å | Mo Kα radiation |
b = 11.1525 (3) Å | µ = 1.16 mm−1 |
c = 14.0096 (3) Å | T = 295 K |
α = 70.123 (1)° | 0.18 × 0.08 × 0.05 mm |
β = 78.582 (1)° |
Bruker APEXII area-detector diffractometer | 4627 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3861 reflections with I > 2σ(I) |
Tmin = 0.832, Tmax = 0.944 | Rint = 0.032 |
12790 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 32 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.76 e Å−3 |
4627 reflections | Δρmin = −0.55 e Å−3 |
325 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 1.28299 (4) | 0.23883 (2) | 0.62583 (2) | 0.0322 (1) | |
Na1 | 0.2853 (3) | 0.8385 (2) | 0.8649 (1) | 0.0524 (4) | |
O1 | 1.1165 (4) | 0.2998 (2) | 0.75921 (18) | 0.0397 (6) | |
O2 | 0.9974 (4) | 0.4538 (2) | 0.62858 (16) | 0.0334 (5) | |
O3 | 0.5501 (4) | 1.0908 (2) | 0.58968 (18) | 0.0408 (6) | |
O4 | 0.3957 (4) | 1.0247 (2) | 0.74276 (19) | 0.0385 (6) | |
O5 | 0.6126 (4) | 0.4270 (2) | 1.31888 (17) | 0.0352 (5) | |
O6 | 0.7003 (5) | 0.2613 (2) | 1.25572 (19) | 0.0490 (7) | |
O7 | 0.6542 (4) | 0.8090 (2) | 0.79807 (17) | 0.0355 (6) | |
O8 | 0.7473 (4) | 0.4093 (2) | 1.06632 (16) | 0.0320 (5) | |
O1w | 1.0518 (4) | 0.1510 (3) | 0.6042 (2) | 0.0460 (7) | |
O2w | 1.3042 (4) | 0.3643 (3) | 0.46121 (18) | 0.0437 (7) | |
O3w | 1.5094 (4) | 0.3321 (2) | 0.6562 (2) | 0.0400 (6) | |
O4w | 0.3611 (7) | 0.8572 (5) | 1.0106 (3) | 0.0911 (13) | |
O5w | −0.0312 (9) | 0.8991 (6) | 0.8870 (6) | 0.136 (2) | |
O6w | 1.1643 (4) | −0.0793 (3) | 0.5740 (2) | 0.0481 (7) | |
O7w | 0.7948 (4) | 0.3467 (3) | 0.49288 (19) | 0.0388 (6) | |
O8w | 0.7747 (7) | 0.1473 (6) | 0.7873 (3) | 0.1127 (17) | |
O9w | −0.2894 (7) | 0.8524 (4) | 1.0663 (3) | 0.0920 (13) | |
C1 | 0.9022 (4) | 0.4805 (3) | 0.7950 (2) | 0.0244 (6) | |
C2 | 0.8351 (5) | 0.6139 (3) | 0.7571 (2) | 0.0248 (6) | |
C3 | 0.7358 (5) | 0.6791 (3) | 0.8258 (2) | 0.0256 (7) | |
C4 | 0.7065 (5) | 0.6153 (3) | 0.9298 (2) | 0.0263 (7) | |
C5 | 0.7738 (5) | 0.4826 (3) | 0.9658 (2) | 0.0243 (6) | |
C6 | 0.8721 (5) | 0.4156 (3) | 0.8980 (2) | 0.0256 (6) | |
C7 | 1.0108 (5) | 0.4069 (3) | 0.7223 (2) | 0.0268 (7) | |
C8 | 0.6719 (5) | 0.8809 (3) | 0.6921 (3) | 0.0330 (8) | |
C9 | 0.5281 (5) | 1.0077 (3) | 0.6758 (2) | 0.0288 (7) | |
C10 | 0.6691 (5) | 0.4765 (3) | 1.1399 (2) | 0.0263 (7) | |
C11 | 0.6619 (5) | 0.3788 (3) | 1.2460 (2) | 0.0291 (7) | |
H1w1 | 1.101 (5) | 0.085 (3) | 0.586 (3) | 0.069* | |
H1w2 | 0.985 (5) | 0.207 (2) | 0.561 (3) | 0.069* | |
H2w1 | 1.4081 (18) | 0.379 (4) | 0.4243 (19) | 0.066* | |
H2w2 | 1.212 (2) | 0.421 (3) | 0.4350 (19) | 0.066* | |
H3w1 | 1.604 (4) | 0.340 (3) | 0.609 (2) | 0.060* | |
H3w2 | 1.463 (4) | 0.405 (2) | 0.666 (3) | 0.060* | |
H4w1 | 0.291 (5) | 0.838 (8) | 1.0682 (15) | 0.137* | |
H4w2 | 0.477 (2) | 0.844 (8) | 1.022 (3) | 0.137* | |
H5w1 | −0.045 (12) | 0.966 (6) | 0.834 (4) | 0.204* | |
H5w2 | −0.043 (12) | 0.926 (9) | 0.939 (4) | 0.204* | |
H6w1 | 1.238 (5) | −0.070 (5) | 0.5176 (17) | 0.072* | |
H6w2 | 1.226 (5) | −0.132 (4) | 0.622 (2) | 0.072* | |
H7w1 | 0.841 (6) | 0.415 (3) | 0.475 (3) | 0.058* | |
H7w2 | 0.743 (6) | 0.345 (4) | 0.444 (2) | 0.058* | |
H8w1 | 0.680 (7) | 0.195 (8) | 0.757 (5) | 0.169* | |
H8w2 | 0.877 (6) | 0.151 (9) | 0.746 (5) | 0.169* | |
H9w1 | −0.410 (2) | 0.862 (8) | 1.070 (5) | 0.138* | |
H9w2 | −0.256 (10) | 0.807 (7) | 1.125 (3) | 0.138* | |
H2 | 0.8565 | 0.6580 | 0.6876 | 0.030* | |
H4 | 0.6423 | 0.6610 | 0.9750 | 0.032* | |
H6 | 0.9175 | 0.3267 | 0.9222 | 0.031* | |
H8a | 0.6486 | 0.8309 | 0.6525 | 0.040* | |
H8b | 0.8001 | 0.8986 | 0.6695 | 0.040* | |
H10a | 0.5416 | 0.5242 | 1.1268 | 0.032* | |
H10b | 0.7474 | 0.5379 | 1.1348 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.03883 (16) | 0.02743 (14) | 0.02517 (14) | 0.00241 (10) | −0.00134 (10) | −0.00911 (10) |
Na1 | 0.0671 (11) | 0.0479 (9) | 0.0390 (8) | −0.0109 (8) | 0.0015 (8) | −0.0138 (7) |
O1 | 0.0479 (15) | 0.0292 (12) | 0.0302 (12) | 0.0144 (11) | 0.0000 (11) | −0.0119 (10) |
O2 | 0.0450 (14) | 0.0313 (12) | 0.0192 (11) | −0.0005 (10) | 0.0011 (10) | −0.0095 (9) |
O3 | 0.0540 (16) | 0.0247 (12) | 0.0284 (12) | 0.0046 (11) | 0.0006 (11) | −0.0003 (10) |
O4 | 0.0446 (15) | 0.0265 (12) | 0.0347 (13) | 0.0042 (10) | 0.0004 (11) | −0.0076 (10) |
O5 | 0.0476 (15) | 0.0379 (13) | 0.0206 (11) | −0.0089 (11) | −0.0005 (10) | −0.0110 (10) |
O6 | 0.090 (2) | 0.0276 (13) | 0.0242 (12) | −0.0078 (13) | −0.0079 (13) | −0.0036 (10) |
O7 | 0.0548 (16) | 0.0202 (11) | 0.0235 (11) | 0.0070 (10) | −0.0038 (11) | −0.0072 (9) |
O8 | 0.0479 (15) | 0.0248 (11) | 0.0153 (10) | 0.0017 (10) | 0.0019 (10) | −0.0050 (8) |
O1w | 0.0441 (16) | 0.0383 (14) | 0.0569 (17) | −0.0003 (12) | −0.0147 (14) | −0.0169 (13) |
O2w | 0.0364 (14) | 0.0544 (17) | 0.0240 (12) | 0.0018 (13) | −0.0015 (11) | 0.0001 (11) |
O3w | 0.0438 (15) | 0.0390 (14) | 0.0390 (14) | −0.0078 (12) | 0.0015 (12) | −0.0181 (12) |
O4w | 0.106 (3) | 0.115 (3) | 0.072 (3) | −0.032 (3) | 0.002 (2) | −0.054 (3) |
O5w | 0.089 (4) | 0.140 (5) | 0.146 (5) | −0.001 (4) | −0.004 (4) | −0.023 (4) |
O6w | 0.0618 (19) | 0.0391 (15) | 0.0342 (14) | 0.0004 (13) | −0.0062 (13) | −0.0063 (12) |
O7w | 0.0451 (16) | 0.0401 (14) | 0.0340 (13) | −0.0101 (12) | −0.0102 (12) | −0.0107 (11) |
O8w | 0.077 (3) | 0.159 (5) | 0.068 (3) | −0.014 (3) | −0.008 (2) | 0.003 (3) |
O9w | 0.113 (4) | 0.074 (3) | 0.079 (3) | 0.016 (3) | −0.044 (3) | −0.017 (2) |
C1 | 0.0245 (15) | 0.0221 (14) | 0.0240 (15) | 0.0008 (12) | −0.0011 (12) | −0.0086 (12) |
C2 | 0.0301 (16) | 0.0234 (15) | 0.0171 (14) | −0.0008 (12) | −0.0015 (12) | −0.0053 (11) |
C3 | 0.0304 (17) | 0.0195 (14) | 0.0240 (15) | 0.0015 (12) | −0.0045 (13) | −0.0066 (12) |
C4 | 0.0317 (17) | 0.0235 (15) | 0.0219 (14) | 0.0032 (13) | −0.0036 (13) | −0.0107 (12) |
C5 | 0.0280 (16) | 0.0241 (15) | 0.0169 (14) | −0.0002 (12) | −0.0035 (12) | −0.0046 (11) |
C6 | 0.0285 (16) | 0.0216 (14) | 0.0212 (14) | 0.0035 (12) | −0.0036 (12) | −0.0051 (11) |
C7 | 0.0298 (17) | 0.0250 (15) | 0.0242 (15) | −0.0041 (13) | 0.0014 (13) | −0.0095 (12) |
C8 | 0.041 (2) | 0.0202 (15) | 0.0286 (16) | 0.0027 (14) | −0.0032 (15) | −0.0027 (13) |
C9 | 0.0374 (19) | 0.0195 (14) | 0.0272 (16) | −0.0010 (13) | −0.0061 (14) | −0.0061 (12) |
C10 | 0.0293 (16) | 0.0279 (16) | 0.0208 (14) | −0.0017 (13) | −0.0018 (12) | −0.0096 (12) |
C11 | 0.0343 (18) | 0.0325 (17) | 0.0187 (14) | −0.0076 (14) | −0.0026 (13) | −0.0052 (13) |
Cd1—O1 | 2.234 (2) | O4w—H4w1 | 0.86 (1) |
Cd1—O3i | 2.322 (2) | O4w—H4w2 | 0.86 (1) |
Cd1—O4i | 2.446 (2) | O5w—H5w1 | 0.86 (1) |
Cd1—O1w | 2.256 (3) | O5w—H5w2 | 0.86 (1) |
Cd1—O2w | 2.251 (2) | O6w—H6w1 | 0.85 (1) |
Cd1—O3w | 2.323 (3) | O6w—H6w2 | 0.85 (1) |
Na1—O4 | 2.395 (3) | O7w—H7w1 | 0.85 (1) |
Na1—O6ii | 2.292 (3) | O7w—H7w2 | 0.85 (1) |
Na1—O7 | 2.645 (3) | O8w—H8w1 | 0.85 (1) |
Na1—O8ii | 2.653 (3) | O8w—H8w2 | 0.85 (1) |
Na1—O4w | 2.304 (4) | O9w—H9w1 | 0.86 (1) |
Na1—O5w | 2.230 (7) | O9w—H9w2 | 0.85 (1) |
O1—C7 | 1.257 (4) | C1—C6 | 1.376 (4) |
O2—C7 | 1.251 (4) | C1—C2 | 1.396 (4) |
O3—C9 | 1.256 (4) | C1—C7 | 1.508 (4) |
O4—C9 | 1.233 (4) | C2—C3 | 1.388 (4) |
O5—C11 | 1.263 (4) | C3—C4 | 1.385 (4) |
O6—C11 | 1.237 (4) | C4—C5 | 1.387 (4) |
O7—C3 | 1.376 (4) | C5—C6 | 1.389 (4) |
O7—C8 | 1.424 (4) | C8—C9 | 1.519 (4) |
O8—C5 | 1.369 (4) | C10—C11 | 1.515 (4) |
O8—C10 | 1.426 (4) | C2—H2 | 0.93 |
O1w—H1w1 | 0.84 (1) | C4—H4 | 0.93 |
O1w—H1w2 | 0.85 (1) | C6—H6 | 0.93 |
O2w—H2w1 | 0.85 (1) | C8—H8a | 0.97 |
O2w—H2w2 | 0.85 (1) | C8—H8b | 0.97 |
O3w—H3w1 | 0.85 (1) | C10—H10a | 0.97 |
O3w—H3w2 | 0.85 (1) | C10—H10b | 0.97 |
O1—Cd1—O3i | 139.6 (1) | O8—C5—C4 | 124.2 (3) |
O1—Cd1—O4i | 89.5 (1) | O8—C5—C6 | 115.9 (3) |
O1—Cd1—O1w | 94.8 (1) | C4—C5—C6 | 120.0 (3) |
O1—Cd1—O2w | 126.1 (1) | C1—C6—C5 | 120.1 (3) |
O1—Cd1—O3w | 81.9 (1) | O2—C7—O1 | 122.2 (3) |
O3i—Cd1—O4i | 54.5 (1) | O2—C7—C1 | 120.2 (3) |
O3i—Cd1—O1w | 100.0 (1) | O1—C7—C1 | 117.5 (3) |
O3i—Cd1—O2w | 91.0 (1) | O7—C8—C9 | 109.0 (3) |
O3i—Cd1—O3w | 82.7 (1) | O4—C9—O3 | 122.9 (3) |
O4i—Cd1—O1w | 86.4 (1) | O4—C9—C8 | 121.3 (3) |
O4i—Cd1—O2w | 144.4 (1) | O3—C9—C8 | 115.8 (3) |
O4i—Cd1—O3w | 93.5 (1) | O8—C10—C11 | 109.1 (2) |
O1w—Cd1—O2w | 91.7 (1) | O6—C11—O5 | 125.1 (3) |
O1w—Cd1—O3w | 176.7 (1) | O6—C11—C10 | 119.6 (3) |
O2w—Cd1—O3w | 90.3 (1) | O5—C11—C10 | 115.3 (3) |
O4—Na1—O6ii | 93.7 (1) | Cd1—O1w—H1w1 | 110 (2) |
O4—Na1—O7 | 63.4 (1) | Cd1—O1w—H1w2 | 109 (2) |
O4—Na1—O8ii | 154.1 (1) | H1w1—O1w—H1w2 | 112 (2) |
O4—Na1—O4w | 98.7 (2) | Cd1—O2w—H2w1 | 124 (1) |
O4—Na1—O5w | 104.7 (2) | Cd1—O2w—H2w2 | 123 (1) |
O6ii—Na1—O7 | 79.3 (1) | H2w1—O2w—H2w2 | 110 (2) |
O6ii—Na1—O8ii | 63.3 (1) | Cd1—O3w—H3w1 | 113 (2) |
O6ii—Na1—O4w | 155.4 (2) | Cd1—O3w—H3w2 | 113 (2) |
O6ii—Na1—O5w | 96.8 (2) | H3w1—O3w—H3w2 | 110 (2) |
O7—Na1—O8ii | 98.9 (1) | Na1—O4w—H4w1 | 122 (2) |
O7—Na1—O4w | 87.3 (2) | Na1—O4w—H4w2 | 122 (2) |
O7—Na1—O5w | 166.9 (2) | H4w1—O4w—H4w2 | 108 (2) |
O8ii—Na1—O4w | 99.1 (2) | Na1—O5w—H5w1 | 100 (6) |
O8ii—Na1—O5w | 90.4 (2) | Na1—O5w—H5w2 | 99 (6) |
O4w—Na1—O5w | 100.4 (2) | H5w1—O5w—H5w2 | 108 (2) |
C7—O1—Cd1 | 106.1 (2) | H6w1—O6w—H6w2 | 109 (2) |
C9—O3—Cd1iii | 93.9 (2) | H7w1—O7w—H7w2 | 110 (2) |
C9—O4—Na1 | 118.4 (2) | H8w1—O8w—H8w2 | 110 (2) |
C9—O4—Cd1iii | 88.7 (2) | H9w1—O9w—H9w2 | 109 (2) |
Na1—O4—Cd1iii | 142.2 (1) | C3—C2—H2 | 120.9 |
C11—O6—Na1ii | 128.3 (2) | C1—C2—H2 | 120.9 |
C3—O7—C8 | 118.0 (2) | C3—C4—H4 | 120.3 |
C3—O7—Na1 | 109.8 (2) | C5—C4—H4 | 120.3 |
C8—O7—Na1 | 106.7 (2) | C1—C6—H6 | 119.9 |
C5—O8—C10 | 117.5 (2) | C5—C6—H6 | 119.9 |
C5—O8—Na1ii | 126.2 (2) | O7—C8—H8a | 109.9 |
C10—O8—Na1ii | 113.1 (2) | C9—C8—H8a | 109.9 |
C6—C1—C2 | 120.9 (3) | O7—C8—H8b | 109.9 |
C6—C1—C7 | 119.6 (3) | C9—C8—H8b | 109.9 |
C2—C1—C7 | 119.5 (3) | H8a—C8—H8b | 108.3 |
C3—C2—C1 | 118.2 (3) | O8—C10—H10a | 109.9 |
O7—C3—C4 | 114.4 (3) | C11—C10—H10a | 109.9 |
O7—C3—C2 | 124.1 (3) | O8—C10—H10b | 109.9 |
C4—C3—C2 | 121.5 (3) | C11—C10—H10b | 109.9 |
C3—C4—C5 | 119.3 (3) | H10a—C10—H10b | 108.3 |
O2w—Cd1—O1—C7 | 12.3 (3) | C2—C3—C4—C5 | −1.6 (5) |
O1w—Cd1—O1—C7 | −83.4 (2) | C10—O8—C5—C4 | −9.0 (5) |
O3i—Cd1—O1—C7 | 165.2 (2) | Na1ii—O8—C5—C4 | 149.0 (3) |
O3w—Cd1—O1—C7 | 96.7 (2) | C10—O8—C5—C6 | 172.2 (3) |
O4i—Cd1—O1—C7 | −169.8 (2) | Na1ii—O8—C5—C6 | −29.8 (4) |
O5w—Na1—O4—C9 | −140.2 (3) | C3—C4—C5—O8 | −177.7 (3) |
O6ii—Na1—O4—C9 | −42.1 (3) | C3—C4—C5—C6 | 1.0 (5) |
O4w—Na1—O4—C9 | 116.5 (3) | C2—C1—C6—C5 | 0.0 (5) |
O7—Na1—O4—C9 | 34.0 (2) | C7—C1—C6—C5 | 179.4 (3) |
O8ii—Na1—O4—C9 | −16.4 (4) | O8—C5—C6—C1 | 178.7 (3) |
O5w—Na1—O4—Cd1iii | −9.4 (3) | C4—C5—C6—C1 | −0.2 (5) |
O6ii—Na1—O4—Cd1iii | 88.7 (2) | Cd1—O1—C7—O2 | 7.0 (4) |
O4w—Na1—O4—Cd1iii | −112.7 (2) | Cd1—O1—C7—C1 | −171.4 (2) |
O7—Na1—O4—Cd1iii | 164.8 (2) | C6—C1—C7—O2 | 161.1 (3) |
O8ii—Na1—O4—Cd1iii | 114.5 (3) | C2—C1—C7—O2 | −19.4 (5) |
O5w—Na1—O7—C3 | −141.6 (9) | C6—C1—C7—O1 | −20.4 (5) |
O6ii—Na1—O7—C3 | −67.5 (2) | C2—C1—C7—O1 | 159.0 (3) |
O4w—Na1—O7—C3 | 91.7 (2) | C3—O7—C8—C9 | 164.0 (3) |
O4—Na1—O7—C3 | −167.1 (2) | Na1—O7—C8—C9 | 39.9 (3) |
O8ii—Na1—O7—C3 | −7.0 (2) | Na1—O4—C9—O3 | 152.2 (3) |
O5w—Na1—O7—C8 | −12.6 (9) | Cd1iii—O4—C9—O3 | −0.1 (4) |
O6ii—Na1—O7—C8 | 61.5 (2) | Na1—O4—C9—C8 | −25.5 (4) |
O4w—Na1—O7—C8 | −139.3 (2) | Cd1iii—O4—C9—C8 | −177.8 (3) |
O4—Na1—O7—C8 | −38.1 (2) | Cd1iii—O3—C9—O4 | 0.1 (4) |
O8ii—Na1—O7—C8 | 122.0 (2) | Cd1iii—O3—C9—C8 | 178.0 (3) |
C6—C1—C2—C3 | −0.5 (5) | O7—C8—C9—O4 | −14.3 (5) |
C7—C1—C2—C3 | −180.0 (3) | O7—C8—C9—O3 | 167.8 (3) |
C8—O7—C3—C4 | −177.9 (3) | C5—O8—C10—C11 | −176.8 (3) |
Na1—O7—C3—C4 | −55.4 (3) | Na1ii—O8—C10—C11 | 22.3 (3) |
C8—O7—C3—C2 | 0.3 (5) | Na1ii—O6—C11—O5 | 162.4 (3) |
Na1—O7—C3—C2 | 122.8 (3) | Na1ii—O6—C11—C10 | −16.3 (5) |
C1—C2—C3—O7 | −176.7 (3) | O8—C10—C11—O6 | −7.7 (5) |
C1—C2—C3—C4 | 1.4 (5) | O8—C10—C11—O5 | 173.4 (3) |
O7—C3—C4—C5 | 176.6 (3) |
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O6w | 0.84 (1) | 1.83 (2) | 2.651 (4) | 165 (5) |
O1w—H1w2···O7w | 0.85 (1) | 1.92 (1) | 2.750 (4) | 165 (4) |
O2w—H2w1···O5iv | 0.85 (1) | 1.92 (1) | 2.748 (4) | 168 (2) |
O2w—H2w2···O2v | 0.85 (1) | 1.93 (1) | 2.780 (3) | 178 (5) |
O3w—H3w1···O7wvi | 0.85 (1) | 1.91 (1) | 2.759 (4) | 171 (3) |
O3w—H3w2···O5vii | 0.85 (1) | 1.89 (1) | 2.736 (4) | 173 (3) |
O4w—H4w1···O8wii | 0.86 (1) | 2.04 (3) | 2.796 (6) | 147 (4) |
O4w—H4w2···O9wvi | 0.86 (1) | 1.96 (2) | 2.790 (7) | 164 (6) |
O5w—H5w1···O8wiii | 0.86 (1) | 2.09 (5) | 2.805 (8) | 140 (7) |
O5w—H5w2···O9w | 0.86 (1) | 2.35 (9) | 2.798 (9) | 113 (8) |
O6w—H6w1···O3v | 0.85 (1) | 1.96 (2) | 2.790 (4) | 165 (4) |
O6w—H6w2···O6viii | 0.85 (1) | 1.90 (2) | 2.730 (4) | 165 (4) |
O7w—H7w1···O2v | 0.85 (1) | 2.09 (2) | 2.859 (4) | 152 (4) |
O7w—H7w2···O5ix | 0.85 (1) | 1.99 (2) | 2.780 (3) | 154 (4) |
O8w—H8w1···O3wx | 0.85 (1) | 2.04 (3) | 2.874 (5) | 165 (8) |
O8w—H8w2···O1w | 0.85 (1) | 2.13 (4) | 2.929 (6) | 155 (8) |
O9w—H9w1···O4wx | 0.86 (1) | 2.02 (4) | 2.790 (7) | 150 (7) |
O9w—H9w2···O1ii | 0.85 (1) | 1.96 (2) | 2.794 (4) | 166 (7) |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) x−1, y+1, z; (iv) x+1, y, z−1; (v) −x+2, −y+1, −z+1; (vi) x+1, y, z; (vii) −x+2, −y+1, −z+2; (viii) −x+2, −y, −z+2; (ix) x, y, z−1; (x) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [CdNa(C11H7O8)(H2O)5]·4H2O |
Mr | 564.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.2853 (2), 11.1525 (3), 14.0096 (3) |
α, β, γ (°) | 70.123 (1), 78.582 (1), 75.987 (1) |
V (Å3) | 1030.23 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.16 |
Crystal size (mm) | 0.18 × 0.08 × 0.05 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.832, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12790, 4627, 3861 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.647 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.03 |
No. of reflections | 4627 |
No. of parameters | 325 |
No. of restraints | 32 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.76, −0.55 |
Computer programs: SMART (Bruker, 2006), SAINT (Bruker, 2006), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O6w | 0.84 (1) | 1.83 (2) | 2.651 (4) | 165 (5) |
O1w—H1w2···O7w | 0.85 (1) | 1.92 (1) | 2.750 (4) | 165 (4) |
O2w—H2w1···O5i | 0.85 (1) | 1.92 (1) | 2.748 (4) | 168 (2) |
O2w—H2w2···O2ii | 0.85 (1) | 1.93 (1) | 2.780 (3) | 178 (5) |
O3w—H3w1···O7wiii | 0.85 (1) | 1.91 (1) | 2.759 (4) | 171 (3) |
O3w—H3w2···O5iv | 0.85 (1) | 1.89 (1) | 2.736 (4) | 173 (3) |
O4w—H4w1···O8wv | 0.86 (1) | 2.04 (3) | 2.796 (6) | 147 (4) |
O4w—H4w2···O9wiii | 0.86 (1) | 1.96 (2) | 2.790 (7) | 164 (6) |
O5w—H5w1···O8wvi | 0.86 (1) | 2.09 (5) | 2.805 (8) | 140 (7) |
O5w—H5w2···O9w | 0.86 (1) | 2.35 (9) | 2.798 (9) | 113 (8) |
O6w—H6w1···O3ii | 0.85 (1) | 1.96 (2) | 2.790 (4) | 165 (4) |
O6w—H6w2···O6vii | 0.85 (1) | 1.90 (2) | 2.730 (4) | 165 (4) |
O7w—H7w1···O2ii | 0.85 (1) | 2.09 (2) | 2.859 (4) | 152 (4) |
O7w—H7w2···O5viii | 0.85 (1) | 1.99 (2) | 2.780 (3) | 154 (4) |
O8w—H8w1···O3wix | 0.85 (1) | 2.04 (3) | 2.874 (5) | 165 (8) |
O8w—H8w2···O1w | 0.85 (1) | 2.13 (4) | 2.929 (6) | 155 (8) |
O9w—H9w1···O4wix | 0.86 (1) | 2.02 (4) | 2.790 (7) | 150 (7) |
O9w—H9w2···O1v | 0.85 (1) | 1.96 (2) | 2.794 (4) | 166 (7) |
Symmetry codes: (i) x+1, y, z−1; (ii) −x+2, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+2; (v) −x+1, −y+1, −z+2; (vi) x−1, y+1, z; (vii) −x+2, −y, −z+2; (viii) x, y, z−1; (ix) x−1, y, z. |
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There is a number of metal derivatives of 3-carboxyphenoxyacetic acid, a carboxylic acid whose deprotonated dianion is regarded as a flexible dianion. The phenoxy linkage in the dianion is also capable of bonding, and this feature is noted in some of the calcium (Gao & Ng, 2006), cadmium (Gao, Huo, Deng & Ng, 2005; Zhao, Gu, Gao, Huo & Liu, 2005), cobalt (Li et al., 2004; Zhao, Gu, Huo et al., 2005), copper (Gao, Gu, Huo et al., 2004a, Gao, Gu, Huo et al., 2004b; Gao, Gu, Zhao et al., 2004), manganese (Gao, Huo, Cheng et al., 2005), nickel (Gu et al., 2005) and zinc (Gao, Huo, Liu et al., 2005; Zhao, Gu, Huo et al., 2005) derivatives. There is a similar number of divalent metal derivatives of the "two-armed" (and much more flexible) acid, benzene-1,3-dioxyacetic acid in the crystallographic literature (CSD Version 5.28, May 2007). Curiously, there is almost no crystallographic mention of the related tricarboxylic acid, 5-carboxy-1,3-diphenoxyacetic acid, the sole mention possibly being a patent claim for antibaterial properties (Leslie et al., 2004) only.
In the crystal structure of pentaaqua(5-carboxy-1,3-phenoxydiacetato)cadmiumsodium tetrahydrate, the carboxylate trianion binds to a triaquacadmium unit through one oxygen atom of its 5-carboxyl group. It also chelates through two oxygen atoms of the 5-oxyacetate group to an adjacent triaquacadmium unit to form a linear chain. Meanwhile, the diaquasodium unit is chelated by the 1-oxyacetate [–O–CH2–C(O)O–] group of one trianion and as well as by the 3-oxyacetate group of another trianion. Both cadmium and sodium sites exist six-coordinate octahedral geometries in the ribbon structure. The ribbons are linked into a three-dimensional network by extensive hydrogen bonds.
The lattice water molecules occupy the space within the ribbon; however, their contribution to the total volume is small as their exclusion is not seen in any significant voids in the unit cell.