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
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. |
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.