metal-organic compounds
catena-Poly[[bis(2,2′-bipyridine-κ2N,N′)cadmium(II)]-μ-9,10-dioxoanthracene-1,5-disulfonato-κ2O1:O5]
aDepartment of Chemistry, Baicheng Normal College, Baicheng, Jilin 137000, People's Republic of China, bCollege of Chemistry, Northeast Normal University, Changchun, Jilin 130024, People's Republic of China, and cCollege of Chemistry, Jilin Normal University, Siping, Jilin 136000, People's Republic of China
*Correspondence e-mail: jj_zhx@126.com
The title complex, [Cd(C14H6O8S2)(C10H8N2)2]n, exhibits a chain-like polymeric structure with 9,10-dioxoanthracene-1,5-disulfonate anions bridging CdII atoms in a bis-monodentate mode. The CdII atom shows a distorted octahedral environment, with four N atoms from two chelating 2,2′-bipyridine ligands forming the equatorial plane and two sulfonate O atoms from two 9,10-dioxoanthracene-1,5-disulfonate anions occupying the apical positions. Weak C—H⋯O hydrogen-bonding contacts and π–π interactions [centroid–centroid distances = 3.6920 (12) and 3.7095 (12) Å] connect the complex molecules into a three-dimensional supramolecular framework.
Related literature
For applications of organosulfonate-based metal complexes, see: Vaira et al. (2003). For a review on structural chemistry and properties of metal arenesulfonates, see: Cai (2004). For self-assembled structural motifs in coordination chemistry, see: Cai et al. (2001); Sun & Lees (2001); Swiegers & Malefetse (2000). For the synthetic procedure, see: Zhao et al. (2007).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2003); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809046881/si2219sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809046881/si2219Isup2.hkl
A mixture of disodium 9,10-dioxoanthracene-1,5-disulfonate (41.2 mg, 0.1 mmol), Cd(OAc)2.2H2O(26.7 mg, 0.1 mmol), 2,2'-bipyridine(15.6 mg, 0.1 mmol), and H2O (10 ml) was sealed in a 23 ml teflonlined stainlesssteel vessel. The vessel was heated to 413 K for 2 days under autogenous pressure and then cooled to room temperature at a rate of 2.4 K / h. Pink block-shaped crystals suitable for X-ray analysis were obtained in a 39% yield. Analysis calculated for C34H22CdN4O8S2: C 51.62, H 2.80, N 7.08%; found: C 51.53, H 2.84, N 6.99%.
H atoms were located in difference maps, but were subsequently placed in calculated positions and treated as riding, with C–H = 0.93 Å and O–H = 0.85 Å. All H atoms were allocated displacement parameters related to those of their parent atoms [Uiso(H) = Ueq(C, O)].
Data collection: APEX2 (Bruker, 2003); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[Cd(C14H6O8S2)(C10H8N2)2] | Z = 2 |
Mr = 791.08 | F(000) = 796 |
Triclinic, P1 | Dx = 1.813 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3807 (7) Å | Cell parameters from 6497 reflections |
b = 10.7406 (8) Å | θ = 2.5–27.9° |
c = 13.1289 (9) Å | µ = 0.96 mm−1 |
α = 94.044 (1)° | T = 296 K |
β = 90.239 (1)° | BLOCK, pink |
γ = 97.025 (1)° | 0.24 × 0.23 × 0.22 mm |
V = 1449.08 (18) Å3 |
Bruker APEXII CCD area-detector diffractometer | 5078 independent reflections |
Radiation source: fine-focus sealed tube | 4773 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→10 |
Tmin = 0.802, Tmax = 0.816 | k = −12→12 |
7435 measured reflections | l = −14→15 |
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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0345P)2 + 0.8688P] where P = (Fo2 + 2Fc2)/3 |
5078 reflections | (Δ/σ)max = 0.001 |
442 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
[Cd(C14H6O8S2)(C10H8N2)2] | γ = 97.025 (1)° |
Mr = 791.08 | V = 1449.08 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.3807 (7) Å | Mo Kα radiation |
b = 10.7406 (8) Å | µ = 0.96 mm−1 |
c = 13.1289 (9) Å | T = 296 K |
α = 94.044 (1)° | 0.24 × 0.23 × 0.22 mm |
β = 90.239 (1)° |
Bruker APEXII CCD area-detector diffractometer | 5078 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4773 reflections with I > 2σ(I) |
Tmin = 0.802, Tmax = 0.816 | Rint = 0.010 |
7435 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.29 e Å−3 |
5078 reflections | Δρmin = −0.47 e Å−3 |
442 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.739498 (14) | −0.019562 (14) | 0.758892 (11) | 0.02811 (7) | |
S1 | 0.98757 (5) | 0.25760 (5) | 0.82102 (4) | 0.03023 (12) | |
S2 | 0.49276 (5) | 0.76753 (5) | 0.66792 (4) | 0.03213 (13) | |
O1 | 1.06004 (17) | 0.33125 (16) | 0.74831 (15) | 0.0487 (4) | |
O2 | 0.92846 (15) | 0.13520 (14) | 0.77782 (13) | 0.0374 (4) | |
O3 | 1.06023 (18) | 0.24621 (18) | 0.91345 (14) | 0.0515 (5) | |
O4 | 0.56626 (15) | 0.81750 (15) | 0.76110 (13) | 0.0416 (4) | |
O5 | 0.36219 (14) | 0.71481 (15) | 0.68755 (13) | 0.0399 (4) | |
O6 | 0.50253 (18) | 0.85773 (17) | 0.59052 (15) | 0.0529 (5) | |
O7 | 0.8128 (2) | 0.29015 (19) | 0.64176 (13) | 0.0602 (6) | |
O8 | 0.49447 (18) | 0.5670 (2) | 0.82193 (14) | 0.0557 (5) | |
N1 | 0.73658 (17) | 0.02158 (16) | 0.93351 (13) | 0.0282 (4) | |
N2 | 0.57917 (17) | 0.11075 (16) | 0.79681 (13) | 0.0288 (4) | |
N3 | 0.79152 (17) | −0.03642 (17) | 0.59157 (13) | 0.0287 (4) | |
N4 | 0.87250 (17) | −0.18502 (17) | 0.73225 (14) | 0.0304 (4) | |
C1 | 0.6531 (2) | 0.09907 (19) | 0.97055 (15) | 0.0267 (4) | |
C2 | 0.8247 (2) | −0.0124 (2) | 0.99750 (17) | 0.0348 (5) | |
H2 | 0.8824 | −0.0662 | 0.9718 | 0.042* | |
C3 | 0.8343 (2) | 0.0280 (2) | 1.09904 (17) | 0.0377 (5) | |
H3 | 0.8970 | 0.0026 | 1.1410 | 0.045* | |
C4 | 0.7489 (2) | 0.1070 (2) | 1.13697 (17) | 0.0397 (5) | |
H4 | 0.7529 | 0.1361 | 1.2054 | 0.048* | |
C5 | 0.6570 (2) | 0.1427 (2) | 1.07233 (17) | 0.0365 (5) | |
H5 | 0.5981 | 0.1957 | 1.0971 | 0.044* | |
C6 | 0.5603 (2) | 0.14002 (19) | 0.89629 (16) | 0.0272 (4) | |
C7 | 0.4978 (2) | 0.1472 (2) | 0.72820 (18) | 0.0366 (5) | |
H7 | 0.5097 | 0.1257 | 0.6593 | 0.044* | |
C8 | 0.3976 (2) | 0.2151 (2) | 0.75536 (19) | 0.0396 (5) | |
H8 | 0.3445 | 0.2410 | 0.7058 | 0.048* | |
C9 | 0.3776 (2) | 0.2439 (2) | 0.8570 (2) | 0.0415 (6) | |
H9 | 0.3095 | 0.2884 | 0.8775 | 0.050* | |
C10 | 0.4594 (2) | 0.2061 (2) | 0.92850 (18) | 0.0369 (5) | |
H10 | 0.4471 | 0.2247 | 0.9978 | 0.044* | |
C11 | 0.86840 (19) | −0.12295 (19) | 0.55847 (16) | 0.0272 (4) | |
C12 | 0.7463 (2) | 0.0352 (2) | 0.52407 (17) | 0.0343 (5) | |
H12 | 0.6919 | 0.0936 | 0.5471 | 0.041* | |
C13 | 0.7761 (2) | 0.0268 (2) | 0.42227 (17) | 0.0386 (5) | |
H13 | 0.7431 | 0.0785 | 0.3773 | 0.046* | |
C14 | 0.8560 (2) | −0.0599 (2) | 0.38872 (17) | 0.0382 (5) | |
H14 | 0.8791 | −0.0669 | 0.3204 | 0.046* | |
C15 | 0.9019 (2) | −0.1368 (2) | 0.45681 (17) | 0.0345 (5) | |
H15 | 0.9547 | −0.1970 | 0.4346 | 0.041* | |
C16 | 0.9134 (2) | −0.2036 (2) | 0.63649 (16) | 0.0286 (4) | |
C17 | 0.9074 (2) | −0.2606 (2) | 0.80218 (18) | 0.0378 (5) | |
H17 | 0.8783 | −0.2487 | 0.8686 | 0.045* | |
C18 | 0.9840 (2) | −0.3544 (2) | 0.7803 (2) | 0.0414 (6) | |
H18 | 1.0055 | −0.4053 | 0.8307 | 0.050* | |
C19 | 1.0281 (3) | −0.3716 (2) | 0.6829 (2) | 0.0479 (6) | |
H19 | 1.0814 | −0.4334 | 0.6662 | 0.058* | |
C20 | 0.9924 (2) | −0.2958 (2) | 0.6098 (2) | 0.0453 (6) | |
H20 | 1.0210 | −0.3064 | 0.5431 | 0.054* | |
C21 | 0.8573 (2) | 0.34568 (19) | 0.86396 (16) | 0.0279 (4) | |
C22 | 0.77142 (19) | 0.39712 (18) | 0.79997 (16) | 0.0261 (4) | |
C23 | 0.7662 (2) | 0.3762 (2) | 0.68705 (17) | 0.0328 (5) | |
C24 | 0.70328 (19) | 0.46704 (19) | 0.62757 (16) | 0.0275 (4) | |
C25 | 0.7262 (2) | 0.4667 (2) | 0.52374 (17) | 0.0356 (5) | |
H25 | 0.7732 | 0.4067 | 0.4923 | 0.043* | |
C26 | 0.6798 (2) | 0.5545 (2) | 0.46681 (17) | 0.0385 (5) | |
H26 | 0.6954 | 0.5543 | 0.3971 | 0.046* | |
C27 | 0.6094 (2) | 0.6439 (2) | 0.51434 (17) | 0.0344 (5) | |
H27 | 0.5816 | 0.7057 | 0.4764 | 0.041* | |
C28 | 0.58020 (19) | 0.64261 (19) | 0.61615 (16) | 0.0269 (4) | |
C29 | 0.62537 (19) | 0.55178 (19) | 0.67490 (16) | 0.0262 (4) | |
C30 | 0.5920 (2) | 0.5344 (2) | 0.78358 (17) | 0.0308 (5) | |
C31 | 0.6830 (2) | 0.47193 (19) | 0.84556 (16) | 0.0279 (4) | |
C32 | 0.6774 (2) | 0.4918 (2) | 0.95107 (17) | 0.0358 (5) | |
H32 | 0.6160 | 0.5393 | 0.9801 | 0.043* | |
C33 | 0.7620 (3) | 0.4417 (2) | 1.01259 (18) | 0.0436 (6) | |
H33 | 0.7591 | 0.4558 | 1.0832 | 0.052* | |
C34 | 0.8518 (2) | 0.3697 (2) | 0.96818 (17) | 0.0372 (5) | |
H34 | 0.9099 | 0.3367 | 1.0099 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.03081 (10) | 0.03273 (10) | 0.02167 (9) | 0.00993 (6) | 0.00363 (6) | −0.00262 (6) |
S1 | 0.0275 (3) | 0.0272 (3) | 0.0373 (3) | 0.0088 (2) | 0.0022 (2) | 0.0019 (2) |
S2 | 0.0279 (3) | 0.0281 (3) | 0.0418 (3) | 0.0109 (2) | 0.0022 (2) | −0.0007 (2) |
O1 | 0.0451 (10) | 0.0372 (9) | 0.0651 (12) | 0.0067 (8) | 0.0230 (9) | 0.0077 (8) |
O2 | 0.0375 (9) | 0.0279 (8) | 0.0473 (10) | 0.0077 (7) | 0.0068 (7) | −0.0008 (7) |
O3 | 0.0477 (10) | 0.0599 (12) | 0.0507 (11) | 0.0287 (9) | −0.0136 (8) | −0.0065 (9) |
O4 | 0.0343 (9) | 0.0393 (9) | 0.0485 (10) | 0.0036 (7) | 0.0039 (7) | −0.0134 (8) |
O5 | 0.0265 (8) | 0.0432 (9) | 0.0504 (10) | 0.0110 (7) | 0.0016 (7) | −0.0048 (8) |
O6 | 0.0564 (11) | 0.0424 (10) | 0.0667 (12) | 0.0250 (9) | 0.0120 (9) | 0.0186 (9) |
O7 | 0.0969 (16) | 0.0589 (12) | 0.0339 (9) | 0.0549 (12) | −0.0067 (10) | −0.0112 (9) |
O8 | 0.0515 (11) | 0.0800 (14) | 0.0464 (11) | 0.0417 (10) | 0.0220 (9) | 0.0206 (10) |
N1 | 0.0290 (9) | 0.0311 (9) | 0.0250 (9) | 0.0072 (7) | 0.0027 (7) | 0.0002 (7) |
N2 | 0.0295 (9) | 0.0299 (9) | 0.0274 (9) | 0.0069 (7) | 0.0019 (7) | −0.0001 (7) |
N3 | 0.0308 (9) | 0.0317 (9) | 0.0248 (9) | 0.0101 (7) | 0.0034 (7) | −0.0003 (7) |
N4 | 0.0336 (10) | 0.0285 (9) | 0.0295 (10) | 0.0059 (7) | −0.0007 (8) | 0.0007 (7) |
C1 | 0.0289 (10) | 0.0265 (10) | 0.0250 (10) | 0.0037 (8) | 0.0072 (8) | 0.0024 (8) |
C2 | 0.0358 (12) | 0.0398 (13) | 0.0305 (11) | 0.0133 (10) | 0.0011 (9) | 0.0002 (10) |
C3 | 0.0445 (13) | 0.0423 (13) | 0.0275 (11) | 0.0094 (11) | −0.0034 (10) | 0.0051 (10) |
C4 | 0.0572 (15) | 0.0431 (13) | 0.0197 (11) | 0.0107 (11) | 0.0026 (10) | 0.0005 (9) |
C5 | 0.0453 (13) | 0.0377 (12) | 0.0281 (11) | 0.0126 (10) | 0.0082 (10) | 0.0007 (10) |
C6 | 0.0279 (10) | 0.0231 (10) | 0.0301 (11) | 0.0026 (8) | 0.0040 (9) | −0.0005 (8) |
C7 | 0.0379 (12) | 0.0421 (13) | 0.0306 (12) | 0.0098 (10) | −0.0025 (10) | 0.0004 (10) |
C8 | 0.0348 (12) | 0.0384 (13) | 0.0465 (14) | 0.0091 (10) | −0.0090 (10) | 0.0022 (11) |
C9 | 0.0314 (12) | 0.0394 (13) | 0.0546 (15) | 0.0138 (10) | 0.0000 (11) | −0.0060 (11) |
C10 | 0.0358 (12) | 0.0382 (12) | 0.0372 (13) | 0.0099 (10) | 0.0061 (10) | −0.0040 (10) |
C11 | 0.0252 (10) | 0.0275 (10) | 0.0289 (11) | 0.0039 (8) | 0.0031 (8) | −0.0003 (9) |
C12 | 0.0364 (12) | 0.0382 (12) | 0.0307 (12) | 0.0141 (10) | 0.0035 (9) | 0.0033 (10) |
C13 | 0.0379 (13) | 0.0499 (14) | 0.0307 (12) | 0.0121 (11) | −0.0001 (10) | 0.0091 (10) |
C14 | 0.0409 (13) | 0.0504 (14) | 0.0233 (11) | 0.0062 (11) | 0.0050 (10) | 0.0010 (10) |
C15 | 0.0361 (12) | 0.0370 (12) | 0.0308 (12) | 0.0093 (10) | 0.0069 (9) | −0.0040 (10) |
C16 | 0.0252 (10) | 0.0284 (11) | 0.0324 (11) | 0.0040 (8) | 0.0034 (9) | 0.0008 (9) |
C17 | 0.0479 (14) | 0.0351 (12) | 0.0296 (12) | 0.0025 (10) | −0.0046 (10) | 0.0028 (10) |
C18 | 0.0426 (13) | 0.0315 (12) | 0.0507 (15) | 0.0031 (10) | −0.0137 (11) | 0.0100 (11) |
C19 | 0.0462 (15) | 0.0433 (14) | 0.0590 (17) | 0.0209 (12) | 0.0053 (12) | 0.0102 (12) |
C20 | 0.0475 (14) | 0.0459 (14) | 0.0477 (15) | 0.0226 (12) | 0.0161 (12) | 0.0090 (12) |
C21 | 0.0288 (11) | 0.0253 (10) | 0.0302 (11) | 0.0063 (8) | 0.0022 (9) | 0.0002 (8) |
C22 | 0.0271 (10) | 0.0222 (10) | 0.0291 (11) | 0.0047 (8) | 0.0022 (8) | 0.0001 (8) |
C23 | 0.0364 (12) | 0.0311 (11) | 0.0323 (12) | 0.0140 (9) | 0.0003 (9) | −0.0055 (9) |
C24 | 0.0261 (10) | 0.0295 (11) | 0.0271 (11) | 0.0075 (8) | −0.0017 (8) | −0.0034 (8) |
C25 | 0.0370 (12) | 0.0433 (13) | 0.0280 (11) | 0.0167 (10) | 0.0010 (9) | −0.0073 (10) |
C26 | 0.0417 (13) | 0.0506 (14) | 0.0249 (11) | 0.0139 (11) | 0.0027 (10) | 0.0010 (10) |
C27 | 0.0332 (12) | 0.0387 (12) | 0.0333 (12) | 0.0101 (10) | −0.0007 (9) | 0.0057 (10) |
C28 | 0.0222 (10) | 0.0276 (10) | 0.0310 (11) | 0.0060 (8) | −0.0008 (8) | −0.0021 (9) |
C29 | 0.0230 (10) | 0.0268 (10) | 0.0287 (11) | 0.0047 (8) | −0.0002 (8) | −0.0025 (8) |
C30 | 0.0327 (11) | 0.0281 (11) | 0.0330 (11) | 0.0105 (9) | 0.0057 (9) | 0.0001 (9) |
C31 | 0.0291 (11) | 0.0255 (10) | 0.0293 (11) | 0.0053 (8) | 0.0039 (9) | −0.0001 (8) |
C32 | 0.0406 (13) | 0.0355 (12) | 0.0329 (12) | 0.0138 (10) | 0.0080 (10) | −0.0031 (10) |
C33 | 0.0538 (15) | 0.0522 (15) | 0.0266 (12) | 0.0178 (12) | 0.0011 (11) | −0.0035 (11) |
C34 | 0.0423 (13) | 0.0407 (13) | 0.0304 (12) | 0.0130 (10) | −0.0032 (10) | 0.0016 (10) |
Cd1—N3 | 2.2645 (17) | C10—H10 | 0.9300 |
Cd1—N1 | 2.3050 (17) | C11—C15 | 1.383 (3) |
Cd1—N2 | 2.3356 (17) | C11—C16 | 1.496 (3) |
Cd1—O4i | 2.3527 (16) | C12—C13 | 1.373 (3) |
Cd1—N4 | 2.3882 (17) | C12—H12 | 0.9300 |
Cd1—O2 | 2.4109 (16) | C13—C14 | 1.373 (3) |
S1—O1 | 1.4387 (18) | C13—H13 | 0.9300 |
S1—O3 | 1.4465 (18) | C14—C15 | 1.380 (3) |
S1—O2 | 1.4564 (16) | C14—H14 | 0.9300 |
S1—C21 | 1.813 (2) | C15—H15 | 0.9300 |
S2—O5 | 1.4353 (17) | C16—C20 | 1.389 (3) |
S2—O6 | 1.4481 (19) | C17—C18 | 1.374 (3) |
S2—O4 | 1.4719 (18) | C17—H17 | 0.9300 |
S2—C28 | 1.806 (2) | C18—C19 | 1.368 (4) |
O4—Cd1ii | 2.3527 (16) | C18—H18 | 0.9300 |
O7—C23 | 1.215 (3) | C19—C20 | 1.379 (4) |
O8—C30 | 1.211 (3) | C19—H19 | 0.9300 |
N1—C2 | 1.340 (3) | C20—H20 | 0.9300 |
N1—C1 | 1.343 (3) | C21—C34 | 1.377 (3) |
N2—C6 | 1.342 (3) | C21—C22 | 1.409 (3) |
N2—C7 | 1.343 (3) | C22—C31 | 1.402 (3) |
N3—C12 | 1.334 (3) | C22—C23 | 1.483 (3) |
N3—C11 | 1.348 (3) | C23—C24 | 1.499 (3) |
N4—C16 | 1.338 (3) | C24—C25 | 1.385 (3) |
N4—C17 | 1.344 (3) | C24—C29 | 1.405 (3) |
C1—C5 | 1.383 (3) | C25—C26 | 1.374 (3) |
C1—C6 | 1.492 (3) | C25—H25 | 0.9300 |
C2—C3 | 1.372 (3) | C26—C27 | 1.391 (3) |
C2—H2 | 0.9300 | C26—H26 | 0.9300 |
C3—C4 | 1.371 (3) | C27—C28 | 1.373 (3) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C5 | 1.381 (3) | C28—C29 | 1.408 (3) |
C4—H4 | 0.9300 | C29—C30 | 1.489 (3) |
C5—H5 | 0.9300 | C30—C31 | 1.494 (3) |
C6—C10 | 1.387 (3) | C31—C32 | 1.389 (3) |
C7—C8 | 1.376 (3) | C32—C33 | 1.373 (3) |
C7—H7 | 0.9300 | C32—H32 | 0.9300 |
C8—C9 | 1.371 (4) | C33—C34 | 1.388 (3) |
C8—H8 | 0.9300 | C33—H33 | 0.9300 |
C9—C10 | 1.378 (3) | C34—H34 | 0.9300 |
C9—H9 | 0.9300 | ||
N3—Cd1—N1 | 166.26 (6) | N3—C11—C16 | 116.78 (18) |
N3—Cd1—N2 | 114.20 (6) | C15—C11—C16 | 122.14 (19) |
N1—Cd1—N2 | 71.82 (6) | N3—C12—C13 | 123.1 (2) |
N3—Cd1—O4i | 100.05 (6) | N3—C12—H12 | 118.4 |
N1—Cd1—O4i | 92.77 (6) | C13—C12—H12 | 118.4 |
N2—Cd1—O4i | 84.02 (6) | C12—C13—C14 | 118.1 (2) |
N3—Cd1—N4 | 71.49 (6) | C12—C13—H13 | 120.9 |
N1—Cd1—N4 | 105.00 (6) | C14—C13—H13 | 120.9 |
N2—Cd1—N4 | 168.49 (6) | C13—C14—C15 | 119.7 (2) |
O4i—Cd1—N4 | 85.11 (6) | C13—C14—H14 | 120.1 |
N3—Cd1—O2 | 85.54 (6) | C15—C14—H14 | 120.1 |
N1—Cd1—O2 | 81.21 (6) | C14—C15—C11 | 119.1 (2) |
N2—Cd1—O2 | 99.17 (6) | C14—C15—H15 | 120.4 |
O4i—Cd1—O2 | 171.85 (6) | C11—C15—H15 | 120.4 |
N4—Cd1—O2 | 91.13 (6) | N4—C16—C20 | 121.5 (2) |
O1—S1—O3 | 113.39 (12) | N4—C16—C11 | 117.42 (18) |
O1—S1—O2 | 113.56 (10) | C20—C16—C11 | 121.1 (2) |
O3—S1—O2 | 111.31 (11) | N4—C17—C18 | 123.2 (2) |
O1—S1—C21 | 106.45 (10) | N4—C17—H17 | 118.4 |
O3—S1—C21 | 103.90 (10) | C18—C17—H17 | 118.4 |
O2—S1—C21 | 107.45 (9) | C19—C18—C17 | 118.7 (2) |
O5—S2—O6 | 113.97 (11) | C19—C18—H18 | 120.7 |
O5—S2—O4 | 113.30 (10) | C17—C18—H18 | 120.7 |
O6—S2—O4 | 111.62 (12) | C18—C19—C20 | 119.0 (2) |
O5—S2—C28 | 108.28 (10) | C18—C19—H19 | 120.5 |
O6—S2—C28 | 104.48 (10) | C20—C19—H19 | 120.5 |
O4—S2—C28 | 104.26 (9) | C19—C20—C16 | 119.6 (2) |
S1—O2—Cd1 | 148.54 (9) | C19—C20—H20 | 120.2 |
S2—O4—Cd1ii | 122.01 (10) | C16—C20—H20 | 120.2 |
C2—N1—C1 | 118.40 (18) | C34—C21—C22 | 119.58 (19) |
C2—N1—Cd1 | 123.63 (14) | C34—C21—S1 | 114.81 (16) |
C1—N1—Cd1 | 117.25 (13) | C22—C21—S1 | 125.42 (16) |
C6—N2—C7 | 118.44 (18) | C31—C22—C21 | 118.18 (19) |
C6—N2—Cd1 | 116.16 (13) | C31—C22—C23 | 117.20 (18) |
C7—N2—Cd1 | 125.05 (14) | C21—C22—C23 | 124.61 (18) |
C12—N3—C11 | 118.79 (18) | O7—C23—C22 | 122.5 (2) |
C12—N3—Cd1 | 121.94 (14) | O7—C23—C24 | 119.4 (2) |
C11—N3—Cd1 | 119.26 (14) | C22—C23—C24 | 118.09 (17) |
C16—N4—C17 | 118.06 (19) | C25—C24—C29 | 120.49 (19) |
C16—N4—Cd1 | 115.03 (14) | C25—C24—C23 | 117.80 (18) |
C17—N4—Cd1 | 126.90 (15) | C29—C24—C23 | 121.70 (19) |
N1—C1—C5 | 121.1 (2) | C26—C25—C24 | 120.4 (2) |
N1—C1—C6 | 117.06 (18) | C26—C25—H25 | 119.8 |
C5—C1—C6 | 121.76 (19) | C24—C25—H25 | 119.8 |
N1—C2—C3 | 123.4 (2) | C25—C26—C27 | 119.4 (2) |
N1—C2—H2 | 118.3 | C25—C26—H26 | 120.3 |
C3—C2—H2 | 118.3 | C27—C26—H26 | 120.3 |
C4—C3—C2 | 118.3 (2) | C28—C27—C26 | 121.3 (2) |
C4—C3—H3 | 120.9 | C28—C27—H27 | 119.4 |
C2—C3—H3 | 120.9 | C26—C27—H27 | 119.4 |
C3—C4—C5 | 119.2 (2) | C27—C28—C29 | 119.72 (19) |
C3—C4—H4 | 120.4 | C27—C28—S2 | 116.19 (16) |
C5—C4—H4 | 120.4 | C29—C28—S2 | 123.97 (16) |
C4—C5—C1 | 119.6 (2) | C24—C29—C28 | 118.45 (19) |
C4—C5—H5 | 120.2 | C24—C29—C30 | 116.71 (18) |
C1—C5—H5 | 120.2 | C28—C29—C30 | 124.78 (18) |
N2—C6—C10 | 121.4 (2) | O8—C30—C29 | 122.7 (2) |
N2—C6—C1 | 117.14 (17) | O8—C30—C31 | 119.8 (2) |
C10—C6—C1 | 121.50 (19) | C29—C30—C31 | 117.46 (17) |
N2—C7—C8 | 122.9 (2) | C32—C31—C22 | 121.0 (2) |
N2—C7—H7 | 118.6 | C32—C31—C30 | 117.17 (18) |
C8—C7—H7 | 118.6 | C22—C31—C30 | 121.86 (19) |
C9—C8—C7 | 118.7 (2) | C33—C32—C31 | 120.3 (2) |
C9—C8—H8 | 120.7 | C33—C32—H32 | 119.9 |
C7—C8—H8 | 120.7 | C31—C32—H32 | 119.9 |
C8—C9—C10 | 119.2 (2) | C32—C33—C34 | 119.2 (2) |
C8—C9—H9 | 120.4 | C32—C33—H33 | 120.4 |
C10—C9—H9 | 120.4 | C34—C33—H33 | 120.4 |
C9—C10—C6 | 119.4 (2) | C21—C34—C33 | 121.7 (2) |
C9—C10—H10 | 120.3 | C21—C34—H34 | 119.1 |
C6—C10—H10 | 120.3 | C33—C34—H34 | 119.1 |
N3—C11—C15 | 121.1 (2) | ||
O1—S1—O2—Cd1 | −133.06 (19) | Cd1—N3—C11—C16 | 0.5 (2) |
O3—S1—O2—Cd1 | 97.5 (2) | C11—N3—C12—C13 | −1.3 (3) |
C21—S1—O2—Cd1 | −15.6 (2) | Cd1—N3—C12—C13 | −179.92 (18) |
N3—Cd1—O2—S1 | 135.7 (2) | N3—C12—C13—C14 | 0.3 (4) |
N1—Cd1—O2—S1 | −47.93 (19) | C12—C13—C14—C15 | 1.0 (4) |
N2—Cd1—O2—S1 | 21.9 (2) | C13—C14—C15—C11 | −1.3 (4) |
O4i—Cd1—O2—S1 | −90.6 (4) | N3—C11—C15—C14 | 0.3 (3) |
N4—Cd1—O2—S1 | −152.9 (2) | C16—C11—C15—C14 | 179.4 (2) |
O5—S2—O4—Cd1ii | −153.24 (9) | C17—N4—C16—C20 | −1.6 (3) |
O6—S2—O4—Cd1ii | −22.97 (14) | Cd1—N4—C16—C20 | 179.43 (18) |
C28—S2—O4—Cd1ii | 89.25 (12) | C17—N4—C16—C11 | 177.09 (19) |
N3—Cd1—N1—C2 | −54.1 (3) | Cd1—N4—C16—C11 | −1.9 (2) |
N2—Cd1—N1—C2 | −172.37 (19) | N3—C11—C16—N4 | 1.0 (3) |
O4i—Cd1—N1—C2 | 104.84 (18) | C15—C11—C16—N4 | −178.1 (2) |
N4—Cd1—N1—C2 | 19.17 (19) | N3—C11—C16—C20 | 179.7 (2) |
O2—Cd1—N1—C2 | −69.64 (17) | C15—C11—C16—C20 | 0.6 (3) |
N3—Cd1—N1—C1 | 116.1 (3) | C16—N4—C17—C18 | 0.8 (3) |
N2—Cd1—N1—C1 | −2.19 (14) | Cd1—N4—C17—C18 | 179.62 (17) |
O4i—Cd1—N1—C1 | −84.98 (15) | N4—C17—C18—C19 | 0.6 (4) |
N4—Cd1—N1—C1 | −170.65 (14) | C17—C18—C19—C20 | −1.2 (4) |
O2—Cd1—N1—C1 | 100.54 (15) | C18—C19—C20—C16 | 0.4 (4) |
N3—Cd1—N2—C6 | −169.45 (14) | N4—C16—C20—C19 | 1.1 (4) |
N1—Cd1—N2—C6 | −2.71 (14) | C11—C16—C20—C19 | −177.6 (2) |
O4i—Cd1—N2—C6 | 92.20 (15) | O1—S1—C21—C34 | −125.08 (19) |
N4—Cd1—N2—C6 | 73.0 (3) | O3—S1—C21—C34 | −5.1 (2) |
O2—Cd1—N2—C6 | −80.24 (15) | O2—S1—C21—C34 | 112.94 (18) |
N3—Cd1—N2—C7 | 17.4 (2) | O1—S1—C21—C22 | 49.9 (2) |
N1—Cd1—N2—C7 | −175.85 (19) | O3—S1—C21—C22 | 169.90 (19) |
O4i—Cd1—N2—C7 | −80.94 (18) | O2—S1—C21—C22 | −72.0 (2) |
N4—Cd1—N2—C7 | −100.1 (3) | C34—C21—C22—C31 | 0.2 (3) |
O2—Cd1—N2—C7 | 106.62 (18) | S1—C21—C22—C31 | −174.63 (16) |
N1—Cd1—N3—C12 | −105.1 (3) | C34—C21—C22—C23 | −178.8 (2) |
N2—Cd1—N3—C12 | 8.35 (19) | S1—C21—C22—C23 | 6.4 (3) |
O4i—Cd1—N3—C12 | 96.27 (17) | C31—C22—C23—O7 | −160.9 (2) |
N4—Cd1—N3—C12 | 177.60 (19) | C21—C22—C23—O7 | 18.1 (4) |
O2—Cd1—N3—C12 | −89.71 (17) | C31—C22—C23—C24 | 20.5 (3) |
N1—Cd1—N3—C11 | 76.2 (3) | C21—C22—C23—C24 | −160.5 (2) |
N2—Cd1—N3—C11 | −170.32 (15) | O7—C23—C24—C25 | −14.3 (3) |
O4i—Cd1—N3—C11 | −82.40 (16) | C22—C23—C24—C25 | 164.3 (2) |
N4—Cd1—N3—C11 | −1.07 (15) | O7—C23—C24—C29 | 166.8 (2) |
O2—Cd1—N3—C11 | 91.62 (16) | C22—C23—C24—C29 | −14.5 (3) |
N3—Cd1—N4—C16 | 1.55 (14) | C29—C24—C25—C26 | 4.1 (3) |
N1—Cd1—N4—C16 | −164.57 (14) | C23—C24—C25—C26 | −174.7 (2) |
N2—Cd1—N4—C16 | 123.0 (3) | C24—C25—C26—C27 | −0.1 (4) |
O4i—Cd1—N4—C16 | 103.87 (15) | C25—C26—C27—C28 | −3.0 (4) |
O2—Cd1—N4—C16 | −83.37 (15) | C26—C27—C28—C29 | 2.0 (3) |
N3—Cd1—N4—C17 | −177.3 (2) | C26—C27—C28—S2 | 178.08 (18) |
N1—Cd1—N4—C17 | 16.59 (19) | O5—S2—C28—C27 | 108.37 (18) |
N2—Cd1—N4—C17 | −55.8 (4) | O6—S2—C28—C27 | −13.4 (2) |
O4i—Cd1—N4—C17 | −74.98 (19) | O4—S2—C28—C27 | −130.72 (17) |
O2—Cd1—N4—C17 | 97.79 (19) | O5—S2—C28—C29 | −75.71 (19) |
C2—N1—C1—C5 | −0.3 (3) | O6—S2—C28—C29 | 162.48 (18) |
Cd1—N1—C1—C5 | −171.01 (16) | O4—S2—C28—C29 | 45.2 (2) |
C2—N1—C1—C6 | 177.15 (19) | C25—C24—C29—C28 | −5.1 (3) |
Cd1—N1—C1—C6 | 6.4 (2) | C23—C24—C29—C28 | 173.74 (19) |
C1—N1—C2—C3 | −0.1 (3) | C25—C24—C29—C30 | 172.3 (2) |
Cd1—N1—C2—C3 | 169.98 (18) | C23—C24—C29—C30 | −8.9 (3) |
N1—C2—C3—C4 | 0.2 (4) | C27—C28—C29—C24 | 2.0 (3) |
C2—C3—C4—C5 | 0.1 (4) | S2—C28—C29—C24 | −173.74 (15) |
C3—C4—C5—C1 | −0.5 (4) | C27—C28—C29—C30 | −175.1 (2) |
N1—C1—C5—C4 | 0.6 (3) | S2—C28—C29—C30 | 9.1 (3) |
C6—C1—C5—C4 | −176.8 (2) | C24—C29—C30—O8 | −153.2 (2) |
C7—N2—C6—C10 | 0.2 (3) | C28—C29—C30—O8 | 24.0 (3) |
Cd1—N2—C6—C10 | −173.46 (16) | C24—C29—C30—C31 | 25.7 (3) |
C7—N2—C6—C1 | −179.50 (19) | C28—C29—C30—C31 | −157.10 (19) |
Cd1—N2—C6—C1 | 6.9 (2) | C21—C22—C31—C32 | −1.9 (3) |
N1—C1—C6—N2 | −9.0 (3) | C23—C22—C31—C32 | 177.2 (2) |
C5—C1—C6—N2 | 168.4 (2) | C21—C22—C31—C30 | 177.53 (19) |
N1—C1—C6—C10 | 171.4 (2) | C23—C22—C31—C30 | −3.4 (3) |
C5—C1—C6—C10 | −11.2 (3) | O8—C30—C31—C32 | −21.7 (3) |
C6—N2—C7—C8 | 1.2 (3) | C29—C30—C31—C32 | 159.4 (2) |
Cd1—N2—C7—C8 | 174.19 (18) | O8—C30—C31—C22 | 158.9 (2) |
N2—C7—C8—C9 | −1.9 (4) | C29—C30—C31—C22 | −20.1 (3) |
C7—C8—C9—C10 | 1.2 (4) | C22—C31—C32—C33 | 2.2 (4) |
C8—C9—C10—C6 | 0.1 (4) | C30—C31—C32—C33 | −177.2 (2) |
N2—C6—C10—C9 | −0.8 (3) | C31—C32—C33—C34 | −0.8 (4) |
C1—C6—C10—C9 | 178.8 (2) | C22—C21—C34—C33 | 1.2 (4) |
C12—N3—C11—C15 | 0.9 (3) | S1—C21—C34—C33 | 176.5 (2) |
Cd1—N3—C11—C15 | 179.65 (16) | C32—C33—C34—C21 | −0.9 (4) |
C12—N3—C11—C16 | −178.19 (19) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O5iii | 0.93 | 2.48 | 3.200 (3) | 135 |
C5—H5···O4iii | 0.93 | 2.53 | 3.239 (3) | 133 |
C14—H14···O2iv | 0.93 | 2.54 | 3.267 (3) | 136 |
Symmetry codes: (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C14H6O8S2)(C10H8N2)2] |
Mr | 791.08 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 10.3807 (7), 10.7406 (8), 13.1289 (9) |
α, β, γ (°) | 94.044 (1), 90.239 (1), 97.025 (1) |
V (Å3) | 1449.08 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.24 × 0.23 × 0.22 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.802, 0.816 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7435, 5078, 4773 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.061, 1.01 |
No. of reflections | 5078 |
No. of parameters | 442 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.47 |
Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999), SHELXL97 (Sheldrick, 2008).
Cd1—N3 | 2.2645 (17) | Cd1—O4i | 2.3527 (16) |
Cd1—N1 | 2.3050 (17) | Cd1—N4 | 2.3882 (17) |
Cd1—N2 | 2.3356 (17) | Cd1—O2 | 2.4109 (16) |
Symmetry code: (i) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O5ii | 0.93 | 2.48 | 3.200 (3) | 134.9 |
C5—H5···O4ii | 0.93 | 2.53 | 3.239 (3) | 133.2 |
C14—H14···O2iii | 0.93 | 2.54 | 3.267 (3) | 135.6 |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y, −z+1. |
Acknowledgements
The authors gratefully acknowledge financial support from the Youth Fund of Baicheng Normal University.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The chemistry of metal sulfonate compounds has been a research field of rapid expansion in recent years, mainly due to their adjustable coordination ability and interesting applications as functional materials [Cai, 2004; Vaira et al., 2003; Zhao et al., 2007]. Coordination interaction, H-bonding and π–π interaction usually play important roles in constructing, tuning, modifying, controlling, and modulating such coordination architectures [Cai et al., 2001; Sun & Lees, 2001; Swiegers & Malefetse, 2000]. We herein report the crystal structure of a Cd II complex with 2,2'-bipyridine and 9,10-dioxoanthracene-1,5-disulfonate ligands (I).
The local coordination environment of CdII atom in I is shown in Fig.1. The unique CdII atom is six-coordinated by four N atoms from two unsymmetric bi-chelating 2,2'-bipyridine ligands and two sulfonate O atoms from two independent anthraquinone-1,5-disulfonate anions, exhibiting a slightly distorted octahedral coordination mode (Table 1). The anthraquinone-1,5-disulfonate anion adopts a bis-monodentate mode, linking the adjacent Cd II atoms into a one-dimentional infinite chain along the b-axis (Fig.2). The π–π stacking interactions between the adjacent 2,2'-bipyridine rings as well as weak C—H···O hydrogen-bonding interactions (Table 2) were observed (Fig. 2), which further extend the chains into a two-dimensional plane. Cg5···Cg5iii distance is 3.6920 (12) Å, the perpendicular distance between the inversion-related planes (therefore the dihedral angle is zero) is 3.291 Å, and the slippage (offset) is 1.674 Å. Cg5 is the centroid of the ring (N3, C11, C15, C14, C13, C12), and the symmetry code iii = 2 - x, -y, 1 - z. Additionally, the adjacent two-dimensional planes are extended into a three-dimensional supramolecular network by π–π stacking interactions between the anthraquinone rings. Cg9···Cg9iv distance is 3.7095 (12) Å, the plane-to-plane (perpendicular) distance between inversion related planes is 3.340 Å, the slippage is 1.615 Å, Cg9 is the centroid of the ring (C24, C25, C26, C27, C28, C29) and the symmetry code iv = 1 - x, 1 - y, 1 - z.