Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013230/ya6165sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013230/ya6165Isup2.hkl |
CCDC reference: 202766
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.025
- wR factor = 0.056
- Data-to-parameter ratio = 15.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.20 From the CIF: _reflns_number_total 3750 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4037 Completeness (_total/calc) 92.89% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
A 1/1 water–ethanol solution (8 ml) of cadmium nitrate tetrahydrate (0.15 g, 0.5 mmol), the monosodium salt of 5-sulfoisophthalic acid (0.13 g, 0.5 mmol) and diazabicyclo[2.2.2]octane (0.22 g, 2.0 mmol) was placed in a 23 ml Teflon-lined stainless vessel. The vessel was sealed and then heated at 433 K for 60 h, after which it was allowed to cool to room temperature. The crystals that deposited from the solution were collected and washed with water. CHN analysis for C14H18CdN2O8S: found C 34.22, H 3.79, N 6.02%; calculated C 34.54, H 3.73, N 5.75%. IR: 2983 (m), 2882 (w), 2808 (w), 2659 (m), 1683 (w), 1598 (s), 1555 (s), 1465 (m), 1434 (s), 1360 (s), 1240 (s), 1170 (s), 1092 (m), 1037 (s), 924 (w), 839 (m), 800 (m), 776 (s), 730 (s), 671 (m), 621 (s), 578 (m), 519 (w), 461 (w), 449 (w) cm−1.
The water and ammonium H atoms were located and refined subject to constraints of O—H = N—H = 0.85±0.01 and H···H = 1.39±0.01 Å. The C-bound H atoms were generated geometrically (C—H = 0.95 Å for the aromatic H atoms and 0.97 Å for the aliphatic H atoms) and were included in the refinement in the riding-model approximation; their displacement parameters were set at 1.2 times those of the equivalent isotropic displacement parameters of the parent C atoms.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
[Cd(C8H3O7S)(C6H13N2)(H2O)] | F(000) = 1952 |
Mr = 486.76 | Dx = 1.974 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.5885 (8) Å | Cell parameters from 6969 reflections |
b = 8.8265 (4) Å | θ = 2.0–28.2° |
c = 21.7607 (9) Å | µ = 1.51 mm−1 |
β = 113.408 (1)° | T = 298 K |
V = 3276.5 (2) Å3 | Plate, colorless |
Z = 8 | 0.40 × 0.08 × 0.04 mm |
Bruker AXS area-detector diffractometer | 3750 independent reflections |
Radiation source: fine-focus sealed tube | 3207 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→24 |
Tmin = 0.689, Tmax = 0.941 | k = −11→11 |
9529 measured reflections | l = −19→28 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0278P)2] where P = (Fo2 + 2Fc2)/3 |
3750 reflections | (Δ/σ)max = 0.001 |
247 parameters | Δρmax = 0.63 e Å−3 |
4 restraints | Δρmin = −0.42 e Å−3 |
[Cd(C8H3O7S)(C6H13N2)(H2O)] | V = 3276.5 (2) Å3 |
Mr = 486.76 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.5885 (8) Å | µ = 1.51 mm−1 |
b = 8.8265 (4) Å | T = 298 K |
c = 21.7607 (9) Å | 0.40 × 0.08 × 0.04 mm |
β = 113.408 (1)° |
Bruker AXS area-detector diffractometer | 3750 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3207 reflections with I > 2σ(I) |
Tmin = 0.689, Tmax = 0.941 | Rint = 0.024 |
9529 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 4 restraints |
wR(F2) = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | Δρmax = 0.63 e Å−3 |
3750 reflections | Δρmin = −0.42 e Å−3 |
247 parameters |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.632505 (9) | 0.53351 (2) | 0.360303 (8) | 0.02357 (6) | |
S1 | 0.99060 (3) | 0.28780 (7) | 0.63378 (3) | 0.0249 (1) | |
O1 | 0.7530 (1) | 0.4692 (2) | 0.4242 (1) | 0.0372 (4) | |
O2 | 0.7544 (1) | 0.3492 (2) | 0.3350 (1) | 0.0348 (4) | |
O3 | 1.0194 (1) | 0.1558 (2) | 0.3560 (1) | 0.0295 (4) | |
O4 | 1.1077 (1) | 0.1047 (2) | 0.4565 (1) | 0.0357 (4) | |
O5 | 1.0671 (1) | 0.2185 (2) | 0.6640 (1) | 0.0341 (4) | |
O6 | 0.9296 (1) | 0.2006 (2) | 0.6446 (1) | 0.0338 (4) | |
O7 | 0.9888 (1) | 0.4447 (2) | 0.6507 (1) | 0.0370 (4) | |
O1w | 0.5949 (1) | 0.5180 (2) | 0.2491 (1) | 0.0326 (4) | |
N1 | 0.6818 (1) | 0.7819 (2) | 0.3470 (1) | 0.0252 (4) | |
N2 | 0.7300 (1) | 1.0435 (2) | 0.3346 (1) | 0.0268 (4) | |
C1 | 0.7862 (1) | 0.3909 (3) | 0.3946 (1) | 0.0261 (5) | |
C2 | 0.8675 (1) | 0.3353 (3) | 0.4372 (1) | 0.0245 (5) | |
C3 | 0.9159 (1) | 0.2746 (3) | 0.4088 (1) | 0.0259 (5) | |
C4 | 0.9889 (1) | 0.2183 (3) | 0.4494 (1) | 0.0244 (5) | |
C5 | 1.0129 (1) | 0.2203 (3) | 0.5182 (1) | 0.0264 (5) | |
C6 | 0.9647 (1) | 0.2815 (3) | 0.5463 (1) | 0.0239 (5) | |
C7 | 0.8927 (1) | 0.3403 (3) | 0.5056 (1) | 0.0273 (5) | |
C8 | 1.0423 (1) | 0.1545 (3) | 0.4190 (1) | 0.0256 (5) | |
C9 | 0.7527 (2) | 0.7727 (3) | 0.3325 (2) | 0.0448 (8) | |
C10 | 0.7820 (2) | 0.9292 (3) | 0.3233 (2) | 0.0351 (6) | |
C11 | 0.6211 (2) | 0.8659 (3) | 0.2923 (1) | 0.0365 (6) | |
C12 | 0.6479 (2) | 1.0242 (3) | 0.2840 (1) | 0.0363 (6) | |
C13 | 0.7016 (2) | 0.8702 (3) | 0.4091 (1) | 0.0402 (7) | |
C14 | 0.7322 (2) | 1.0263 (3) | 0.4034 (1) | 0.0366 (6) | |
H1w1 | 0.589 (2) | 0.429 (1) | 0.233 (1) | 0.05 (1)* | |
H1w2 | 0.560 (1) | 0.574 (2) | 0.221 (1) | 0.06 (1)* | |
H2n | 0.746 (1) | 1.134 (2) | 0.332 (1) | 0.03 (1)* | |
H3 | 0.8993 | 0.2716 | 0.3624 | 0.031* | |
H5 | 1.0614 | 0.1804 | 0.5456 | 0.032* | |
H7 | 0.8609 | 0.3838 | 0.5247 | 0.033* | |
H9a | 0.7412 | 0.7136 | 0.2921 | 0.054* | |
H9b | 0.7937 | 0.7209 | 0.3691 | 0.054* | |
H10a | 0.8356 | 0.9438 | 0.3550 | 0.042* | |
H10b | 0.7804 | 0.9392 | 0.2784 | 0.042* | |
H11a | 0.5742 | 0.8729 | 0.3014 | 0.044* | |
H11b | 0.6079 | 0.8104 | 0.2507 | 0.044* | |
H12a | 0.6461 | 1.0370 | 0.2392 | 0.044* | |
H12b | 0.6138 | 1.0993 | 0.2911 | 0.044* | |
H13a | 0.7410 | 0.8161 | 0.4460 | 0.048* | |
H13b | 0.6552 | 0.8803 | 0.4189 | 0.048* | |
H14a | 0.7000 | 1.1034 | 0.4117 | 0.044* | |
H14b | 0.7856 | 1.0378 | 0.4362 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0195 (1) | 0.0277 (1) | 0.0247 (1) | 0.0044 (1) | 0.0100 (1) | −0.0003 (1) |
S1 | 0.0257 (3) | 0.0268 (3) | 0.0238 (3) | 0.0030 (2) | 0.0115 (2) | 0.0009 (2) |
O1 | 0.025 (1) | 0.044 (1) | 0.040 (1) | 0.014 (1) | 0.011 (1) | 0.000 (1) |
O2 | 0.031 (1) | 0.035 (1) | 0.031 (1) | 0.003 (1) | 0.003 (1) | 0.005 (1) |
O3 | 0.026 (1) | 0.038 (1) | 0.027 (1) | 0.002 (1) | 0.013 (1) | −0.004 (1) |
O4 | 0.025 (1) | 0.052 (1) | 0.033 (1) | 0.013 (1) | 0.014 (1) | 0.000 (1) |
O5 | 0.029 (1) | 0.044 (1) | 0.027 (1) | 0.011 (1) | 0.009 (1) | 0.007 (1) |
O6 | 0.037 (1) | 0.035 (1) | 0.036 (1) | −0.005 (1) | 0.022 (1) | 0.000 (1) |
O7 | 0.048 (1) | 0.028 (1) | 0.038 (1) | 0.002 (1) | 0.020 (1) | −0.006 (1) |
O1w | 0.035 (1) | 0.032 (1) | 0.027 (1) | 0.006 (1) | 0.008 (1) | −0.003 (1) |
N1 | 0.024 (1) | 0.026 (1) | 0.028 (1) | 0.003 (1) | 0.013 (1) | −0.001 (1) |
N2 | 0.029 (1) | 0.023 (1) | 0.033 (1) | 0.001 (1) | 0.016 (1) | 0.001 (1) |
C1 | 0.021 (1) | 0.025 (1) | 0.031 (1) | 0.006 (1) | 0.009 (1) | 0.006 (1) |
C2 | 0.021 (1) | 0.026 (1) | 0.027 (1) | 0.004 (1) | 0.010 (1) | 0.002 (1) |
C3 | 0.025 (1) | 0.032 (1) | 0.021 (1) | 0.002 (1) | 0.010 (1) | −0.001 (1) |
C4 | 0.023 (1) | 0.026 (1) | 0.028 (1) | 0.002 (1) | 0.014 (1) | −0.002 (1) |
C5 | 0.020 (1) | 0.032 (1) | 0.027 (1) | 0.006 (1) | 0.009 (1) | 0.001 (1) |
C6 | 0.023 (1) | 0.028 (1) | 0.022 (1) | 0.002 (1) | 0.010 (1) | 0.000 (1) |
C7 | 0.023 (1) | 0.032 (2) | 0.030 (1) | 0.006 (1) | 0.014 (1) | −0.001 (1) |
C8 | 0.023 (1) | 0.027 (1) | 0.030 (1) | −0.001 (1) | 0.015 (1) | −0.004 (1) |
C9 | 0.040 (2) | 0.034 (2) | 0.076 (2) | 0.006 (1) | 0.039 (2) | 0.001 (2) |
C10 | 0.033 (1) | 0.032 (2) | 0.050 (2) | 0.004 (1) | 0.027 (1) | −0.001 (1) |
C11 | 0.033 (1) | 0.032 (2) | 0.037 (2) | 0.000 (1) | 0.004 (1) | 0.004 (1) |
C12 | 0.031 (1) | 0.035 (2) | 0.039 (2) | 0.005 (1) | 0.009 (1) | 0.008 (1) |
C13 | 0.055 (2) | 0.040 (2) | 0.029 (2) | −0.014 (1) | 0.019 (1) | −0.005 (1) |
C14 | 0.052 (2) | 0.033 (2) | 0.032 (2) | −0.005 (1) | 0.024 (1) | −0.005 (1) |
Cd1—O1 | 2.190 (2) | C4—C8 | 1.503 (3) |
Cd1—O3i | 2.331 (2) | C5—C6 | 1.379 (3) |
Cd1—O4i | 2.399 (2) | C6—C7 | 1.380 (3) |
Cd1—O6ii | 2.349 (2) | C9—C10 | 1.527 (4) |
Cd1—O1w | 2.241 (2) | C11—C12 | 1.518 (4) |
Cd1—N1 | 2.437 (2) | C13—C14 | 1.515 (4) |
S1—O7 | 1.437 (2) | O1w—H1w1 | 0.85 (1) |
S1—O5 | 1.445 (2) | O1w—H1w2 | 0.85 (1) |
S1—O6 | 1.465 (2) | N2—H2n | 0.86 (1) |
S1—C6 | 1.769 (2) | C3—H3 | 0.93 |
O1—C1 | 1.261 (3) | C5—H5 | 0.93 |
O2—C1 | 1.248 (3) | C7—H7 | 0.93 |
O3—C8 | 1.265 (3) | C9—H9a | 0.97 |
O4—C8 | 1.244 (3) | C9—H9b | 0.97 |
N1—C11 | 1.474 (3) | C10—H10a | 0.97 |
N1—C9 | 1.474 (3) | C10—H10b | 0.97 |
N1—C13 | 1.475 (3) | C11—H11a | 0.97 |
N2—C10 | 1.484 (3) | C11—H11b | 0.97 |
N2—C14 | 1.488 (3) | C12—H12a | 0.97 |
N2—C12 | 1.495 (3) | C12—H12b | 0.97 |
C1—C2 | 1.506 (3) | C13—H13a | 0.97 |
C2—C7 | 1.372 (3) | C13—H13b | 0.97 |
C2—C3 | 1.386 (3) | C14—H14a | 0.97 |
C3—C4 | 1.384 (3) | C14—H14b | 0.97 |
C4—C5 | 1.384 (3) | ||
O1—Cd1—O3i | 145.5 (1) | O4—C8—C4 | 119.2 (2) |
O1—Cd1—O4i | 91.0 (1) | O3—C8—C4 | 118.5 (2) |
O1—Cd1—O6ii | 99.3 (1) | N1—C9—C10 | 112.0 (2) |
O1—Cd1—O1w | 118.1 (1 | N2—C10—C9 | 107.7 (2) |
O1—Cd1—N1 | 88.3 (1) | N1—C11—C12 | 112.1 (2) |
O3i—Cd1—O4i | 55.3 (1) | N2—C12—C11 | 107.7 (2) |
O3i—Cd1—O6ii | 89.2 (1) | N1—C13—C14 | 111.7 (2) |
O3i—Cd1—O1w | 95.5 (1) | N2—C14—C13 | 108.4 (2) |
O3i—Cd1—N1 | 87.4 (1) | Cd1—O1w—H1w1 | 116 (2) |
O4i—Cd1—O6ii | 90.5 (1) | Cd1—O1w—H1w2 | 124 (2) |
O4i—Cd1—O1w | 150.8 (1) | H1w1—O1w—H1w2 | 108 (2) |
O4i—Cd1—N1 | 94.6 (1) | C10—N2—H2n | 111 (2) |
O6ii—Cd1—O1w | 87.7 (1) | C14—N2—H2n | 106 (2) |
O6ii—Cd1—N1 | 170.8 (1) | C12—N2—H2n | 110 (2) |
O1w—Cd1—N1 | 84.1 (1) | C4—C3—H3 | 120.0 |
O7—S1—O5 | 114.2 (1) | C2—C3—H3 | 120.0 |
O7—S1—O6 | 111.6 (1) | C6—C5—H5 | 120.1 |
O5—S1—O6 | 112.9 (1) | C4—C5—H5 | 120.1 |
O7—S1—C6 | 106.4 (1) | C2—C7—H7 | 119.6 |
O5—S1—C6 | 106.0 (1) | C6—C7—H7 | 119.6 |
O6—S1—C6 | 105.0 (1) | N1—C9—H9a | 109.2 |
C1—O1—Cd1 | 113.7 (2) | C10—C9—H9a | 109.2 |
C8—O3—Cd1iii | 92.5 (1) | N1—C9—H9b | 109.2 |
C8—O4—Cd1iii | 89.9 (1) | C10—C9—H9b | 109.2 |
S1—O6—Cd1ii | 148.5 (1) | H9a—C9—H9b | 107.9 |
C11—N1—C9 | 108.5 (2) | N2—C10—H10a | 110.2 |
C11—N1—C13 | 107.9 (2) | C9—C10—H10a | 110.2 |
C9—N1—C13 | 107.9 (2) | N2—C10—H10b | 110.2 |
C11—N1—Cd1 | 110.2 (1) | C9—C10—H10b | 110.2 |
C9—N1—Cd1 | 112.7 (2) | H10a—C10—H10b | 108.5 |
C13—N1—Cd1 | 109.5 (2) | N1—C11—H11a | 109.2 |
C10—N2—C14 | 109.7 (2) | C12—C11—H11a | 109.2 |
C10—N2—C12 | 110.0 (2) | N1—C11—H11b | 109.2 |
C14—N2—C12 | 110.0 (2) | C12—C11—H11b | 109.2 |
O2—C1—O1 | 124.5 (2) | H11a—C11—H11b | 107.9 |
O2—C1—C2 | 119.2 (2) | N2—C12—H12a | 110.2 |
O1—C1—C2 | 116.0 (2) | C11—C12—H12a | 110.2 |
C7—C2—C3 | 119.6 (2) | N2—C12—H12b | 110.2 |
C7—C2—C1 | 118.9 (2) | C11—C12—H12b | 110.2 |
C3—C2—C1 | 121.4 (2) | H12a—C12—H12b | 108.5 |
C4—C3—C2 | 120.0 (2) | N1—C13—H13a | 109.3 |
C5—C4—C3 | 120.0 (2) | C14—C13—H13a | 109.3 |
C5—C4—C8 | 119.7 (2) | N1—C13—H13b | 109.3 |
C3—C4—C8 | 120.3 (2) | C14—C13—H13b | 109.3 |
C6—C5—C4 | 119.9 (2) | H13a—C13—H13b | 107.9 |
C5—C6—C7 | 119.9 (2) | N2—C14—H14a | 110.0 |
C5—C6—S1 | 122.8 (2) | C13—C14—H14a | 110.0 |
C7—C6—S1 | 117.4 (2) | N2—C14—H14b | 110.0 |
C2—C7—C6 | 120.7 (2) | C13—C14—H14b | 110.0 |
O4—C8—O3 | 122.2 (2) | H14a—C14—H14b | 108.4 |
O1w—Cd1—O1—C1 | −17.7 (2) | C4—C5—C6—S1 | 179.7 (2) |
O3i—Cd1—O1—C1 | 177.0 (2) | O7—S1—C6—C5 | 121.7 (2) |
O6ii—Cd1—O1—C1 | 74.7 (2) | O5—S1—C6—C5 | −0.2 (2) |
O4i—Cd1—O1—C1 | 165.3 (2) | O6—S1—C6—C5 | −119.9 (2) |
N1—Cd1—O1—C1 | −100.1 (2) | O7—S1—C6—C7 | −58.7 (2) |
C8i—Cd1—O1—C1 | 168.6 (2) | O5—S1—C6—C7 | 179.4 (2) |
O7—S1—O6—Cd1ii | 179.4 (2) | O6—S1—C6—C7 | 59.6 (2) |
O5—S1—O6—Cd1ii | −50.4 (2) | C3—C2—C7—C6 | −1.9 (4) |
C6—S1—O6—Cd1ii | 64.6 (2) | C1—C2—C7—C6 | 175.8 (2) |
O1—Cd1—N1—C11 | 167.1 (2) | C5—C6—C7—C2 | 1.6 (4) |
O1w—Cd1—N1—C11 | 48.7 (2) | S1—C6—C7—C2 | −178.0 (2) |
O3i—Cd1—N1—C11 | −47.1 (2) | Cd1iii—O4—C8—O3 | −3.2 (3) |
O4i—Cd1—N1—C11 | −102.0 (2) | Cd1iii—O4—C8—C4 | 178.0 (2) |
C8i—Cd1—N1—C11 | −74.7 (2) | Cd1iii—O3—C8—O4 | 3.3 (3) |
O1—Cd1—N1—C9 | 45.8 (2) | Cd1iii—O3—C8—C4 | −177.9 (2) |
O1w—Cd1—N1—C9 | −72.7 (2) | C5—C4—C8—O4 | −0.2 (4) |
O3i—Cd1—N1—C9 | −168.5 (2) | C3—C4—C8—O4 | 179.9 (2) |
O4i—Cd1—N1—C9 | 136.6 (2) | C5—C4—C8—O3 | −179.1 (2) |
C8i—Cd1—N1—C9 | 164.0 (2) | C3—C4—C8—O3 | 1.1 (4) |
O1—Cd1—N1—C13 | −74.3 (2) | C11—N1—C9—C10 | 56.8 (3) |
O1w—Cd1—N1—C13 | 167.2 (2) | C13—N1—C9—C10 | −59.8 (3) |
O3i—Cd1—N1—C13 | 71.4 (2) | Cd1—N1—C9—C10 | 179.1 (2) |
O4i—Cd1—N1—C13 | 16.5 (2) | C14—N2—C10—C9 | 59.3 (3) |
C8i—Cd1—N1—C13 | 43.9 (2) | C12—N2—C10—C9 | −61.9 (3) |
Cd1—O1—C1—O2 | −1.5 (3) | N1—C9—C10—N2 | 2.1 (3) |
Cd1—O1—C1—C2 | −176.4 (2) | C9—N1—C11—C12 | −58.6 (3) |
O2—C1—C2—C7 | −159.9 (2) | C13—N1—C11—C12 | 58.0 (3) |
O1—C1—C2—C7 | 15.3 (4) | Cd1—N1—C11—C12 | 177.5 (2) |
O2—C1—C2—C3 | 17.7 (4) | C10—N2—C12—C11 | 60.3 (3) |
O1—C1—C2—C3 | −167.1 (2) | C14—N2—C12—C11 | −60.7 (3) |
C7—C2—C3—C4 | 0.5 (4) | N1—C11—C12—N2 | 1.0 (3) |
C1—C2—C3—C4 | −177.1 (2) | C11—N1—C13—C14 | −59.8 (3) |
C2—C3—C4—C5 | 1.1 (4) | C9—N1—C13—C14 | 57.3 (3) |
C2—C3—C4—C8 | −179.0 (2) | Cd1—N1—C13—C14 | −179.7 (2) |
C3—C4—C5—C6 | −1.5 (4) | C10—N2—C14—C13 | −62.0 (3) |
C8—C4—C5—C6 | 178.7 (2) | C12—N2—C14—C13 | 59.1 (3) |
C4—C5—C6—C7 | 0.1 (4) | N1—C13—C14—N2 | 2.0 (3) |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+3/2, −y+1/2, −z+1; (iii) x+1/2, y−1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O5iv | 0.85 (1) | 1.91 (2) | 2.700 (3) | 155 (3) |
O1w—H1w2···O3v | 0.85 (1) | 1.88 (1) | 2.714 (2) | 165 (3) |
N2—H2n···O2vi | 0.86 (1) | 1.91 (1) | 2.736 (3) | 161 (3) |
Symmetry codes: (iv) x−1/2, −y+1/2, z−1/2; (v) −x+3/2, y+1/2, −z+1/2; (vi) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C8H3O7S)(C6H13N2)(H2O)] |
Mr | 486.76 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 18.5885 (8), 8.8265 (4), 21.7607 (9) |
β (°) | 113.408 (1) |
V (Å3) | 3276.5 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.51 |
Crystal size (mm) | 0.40 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Bruker AXS area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.689, 0.941 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9529, 3750, 3207 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.056, 0.93 |
No. of reflections | 3750 |
No. of parameters | 247 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.63, −0.42 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Cd1—O1 | 2.190 (2) | Cd1—O6ii | 2.349 (2) |
Cd1—O3i | 2.331 (2) | Cd1—O1w | 2.241 (2) |
Cd1—O4i | 2.399 (2) | Cd1—N1 | 2.437 (2) |
O1—Cd1—O3i | 145.5 (1) | O3i—Cd1—N1 | 87.4 (1) |
O1—Cd1—O4i | 91.0 (1) | O4i—Cd1—O6ii | 90.5 (1) |
O1—Cd1—O6ii | 99.3 (1) | O4i—Cd1—O1w | 150.8 (1) |
O1—Cd1—O1w | 118.1 (1 | O4i—Cd1—N1 | 94.6 (1) |
O1—Cd1—N1 | 88.3 (1) | O6ii—Cd1—O1w | 87.7 (1) |
O3i—Cd1—O4i | 55.3 (1) | O6ii—Cd1—N1 | 170.8 (1) |
O3i—Cd1—O6ii | 89.2 (1) | O1w—Cd1—N1 | 84.1 (1) |
O3i—Cd1—O1w | 95.5 (1) |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+3/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O5iii | 0.85 (1) | 1.91 (2) | 2.700 (3) | 155 (3) |
O1w—H1w2···O3iv | 0.85 (1) | 1.88 (1) | 2.714 (2) | 165 (3) |
N2—H2n···O2v | 0.86 (1) | 1.91 (1) | 2.736 (3) | 161 (3) |
Symmetry codes: (iii) x−1/2, −y+1/2, z−1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) x, y+1, z. |
The 5-sulfoisophthalato monoanion, [C6H3-1,3-(CO2H)2-5-SO3]−, reacts with copper nitrate in the presence of hexamine to form C6H3-1,3-(CO2)2-5-SO3H](H2O)3Cu·6H2O·0.5(CH2)6N4. In the crystal structure, the [C6H3-1,3-(CO2)2-5-SO3H]2− dianion links adjacent Cu atoms through both monodentate –CO2 groups into a linear chain, and adjacent chains are linked by hydrogen bonds to the water and hexamine molecules into a network motif. The piperazine guest-host analog, [C6H3-1,3-(CO2)2-5-SO3H](H2O)2Cu·6H2O·0.5 N(CH2)4N, follows the similar pattern (Sun et al., 2003). The other known metal complex of 5-sulfoisophthalic acid is also a copper derivative, [C6H3(CO2)2(SO3)]2Cu3, whose Cu atoms are coordinated by pyridine ligands (Kulynych & Shimizu, 2002).
We have employed the anion to react with Cd2+ in the presence of 1,4-diazabicyclo[2.2.2]octane in the hope of synthesizing a similar guest–host hydrate, i.e. [C6H3-1,3-(CO2)2-5-SO3H]Cd–N(CH2CH2)3N.nH2O, (I), using a hydrothermal synthetic procedure. However, in the water-coordinated product, the H atom of the sulfonate group has protonated one of the N atoms of the 1,4-diazabicyclo[2.2.2]octane; the resulting 1-aza-4-azoniabicyclo[2.2.2]octane cation then engages its free N atom to coordinate to the Cd atom, and a zwitterionic compound results (Fig. 1).
The [C6H3-1,3-(CO2)2-5-SO3]3− trianion uses both –CO2 groups to link to adjacent Cd atoms to form a chain, but one of them is monodentate [Cd—O = 2.190 (2) Å] whereas the other is chelating [Cd—O = 2.331 (2) and 2.399 (2) Å]. Two chains are then linked by a sulfonate bridge [Cd—O = 2.349 (2) Å] to furnish a ribbon motif (Fig. 2). The ribbons are further linked by hydrogen-bonding interactions (Table 2) to give rise to a three-dimensional network structure. Protonation of one of the two N atoms of the 1,4-diazabicyclo[2.2.2]octane probably raises the Lewis basicity of the other N atom to permit it to bind to Cd [Cd1—N1 = 2.437 (2) Å]; a Cd← N interaction of a similar length [Cd← N 2.446 (3) Å] is also found in {[NH(CH2CH2)N]2Cd}{Ni(CN)4}2·4C6H5NH2 (Yuge & Iwamoto, 1995).