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Acta Cryst. (2008). E64, m396-m397    [ doi:10.1107/S1600536807067918 ]

Aqua(4,5-dihydroxybenzene-1,3-disulfonato-[kappa]O)bis(1,10-phenanthroline-[kappa]2N,N')cadmium(II) monohydrate

X. Zhang, C. Ge, L. Guan and Z. Sun

Abstract top

In the title compound, [Cd(C6H4O8S2)(C12H8N2)2(H2O)]·H2O, each CdII ion is coordinated by four N atoms [Cd-N = 2.310 (7)-2.341 (7) Å] from two 1,10-phenanthroline ligands, one O atom [Cd-O = 2.300 (6) Å] from a 4,5-dihydroxybenzene-1,3-disulfonate ligand and one aqua O atom [Cd-O = 2.288 (7) Å] in a distorted octahedral geometry. The crystal packing exhibits intermolecular O-H...O and C-H...O hydrogen bonds and [pi]-[pi] interactions evidenced by relatively short distances [3.525 (5)-3.937 (6) Å] between the centroids of the six-membered rings of neighbouring molecules.

Comment top

As a multi-group compound, 4,5-dihydroxybenzene-1,3-disulfonic acid (H2dhds) is a good candidate for investigation of supramolecular assemblies (Haddad & Raymond, 1986; Riley et al., 1983; Sheriff et al., 2003; Sun et al., 1995). Herewith we present the title compound, (I), containing dhds anion as a coordinating ligand.

In (I) (Fig. 1), the dhds anion undoubtedly plays an important role in the formation and stabilization of the three dimesional supramolecular network (Fig.1). Each complex connects with six other complexes by inter-molecular O—H···O and C—H···O hydrogen bonds (Table 2). Significant π···π interactions between pairs of dhds and 1,10-phenanthroline or pairs of 1,10-phenanthrolines exist in (I) (Table 1).

Related literature top

For related literature, see: Haddad & Raymond (1986); Riley et al. (1983); Sheriff et al. (2003); Sun et al. (1995).

Experimental top

In a typical synthesis, hydrated nitrate (0.5 mmol), phen (1 mmol), 4,5-dihydroxybenzene-1,3-disulfonic acid (0.5 mmol) and NaOH (1 mmol) were mixed in ethanol:H2O (v: v = 1:1, 20 ml) solution. The resulting mixture was stirred for 4 h and the solution was filtered. By slow evaporation of the solvent, block-shape single crystals suitable for X-ray analysis were obtained after several weeks.

Refinement top

C-bound H atoms were placed in geometrically idealized positions (Csp2—H = 0.93 Å) and refined with Uiso(H) =1.2Ueq(C). H atoms attached to O were located from difference Fourier maps, but placed in idealized positions (O—H = 0.82 Å) and refined as riding with Uiso(H) =1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures top
[Figure 1] Fig. 1. View of (I), showing atomic labels and displacement ellipsoids drawn at the 30% probability level. Uncoordinated water and H atoms are omitted for clarity.
Aqua(4,5-dihydroxybenzene-1,3-disulfonato-κO)bis(1,10-phenanthroline- κ2N,N')cadmium(II) monohydrate top
Crystal data top
[Cd(C6H4O8S2)(C12H8N2)2(H2O)]·H2OF000 = 1568
Mr = 777.05Dx = 1.705 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 672 reflections
a = 16.570 (5) Åθ = 2.4–22.8º
b = 9.330 (3) ŵ = 0.93 mm−1
c = 24.585 (6) ÅT = 293 (2) K
β = 127.199 (16)ºBlock, colourless
V = 3027.5 (15) Å30.30 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		5155 independent reflections
Radiation source: fine-focus sealed tube3318 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 293(2) Kθmax = 25.0º
φ and ω scansθmin = 2.5º
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −1→19
Tmin = 0.816, Tmax = 0.851k = −11→1
6494 measured reflectionsl = −29→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.223  w = 1/[σ2(Fo2) + (0.084P)2 + 19.1074P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
5155 reflectionsΔρmax = 1.32 e Å−3
426 parametersΔρmin = −2.31 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cd(C6H4O8S2)(C12H8N2)2(H2O)]·H2OV = 3027.5 (15) Å3
Mr = 777.05Z = 4
Monoclinic, P21/cMo Kα
a = 16.570 (5) ŵ = 0.93 mm−1
b = 9.330 (3) ÅT = 293 (2) K
c = 24.585 (6) Å0.30 × 0.20 × 0.18 mm
β = 127.199 (16)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		5155 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3318 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.851Rint = 0.031
6494 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.223  w = 1/[σ2(Fo2) + (0.084P)2 + 19.1074P]
where P = (Fo2 + 2Fc2)/3
S = 1.16Δρmax = 1.32 e Å−3
5155 reflectionsΔρmin = −2.31 e Å−3
426 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.78090 (4)0.74745 (7)0.54487 (3)0.0437 (2)
S10.87188 (16)0.4361 (3)0.64067 (11)0.0466 (5)
S20.59688 (16)0.4432 (3)0.69352 (12)0.0534 (6)
O10.6654 (5)0.5671 (8)0.4872 (4)0.090 (3)
H1A0.68170.48230.49530.135*
H1B0.60630.56690.45280.135*
O20.8517 (5)0.5903 (7)0.6349 (3)0.0574 (17)
O30.8155 (5)0.3681 (8)0.5744 (3)0.0665 (19)
O40.9804 (5)0.4051 (8)0.6832 (4)0.0633 (19)
O50.5308 (5)0.4812 (11)0.6236 (4)0.084 (3)
O60.6305 (7)0.5630 (14)0.7383 (6)0.149 (6)
O70.5553 (7)0.3294 (12)0.7104 (6)0.123 (4)
O80.7292 (6)0.1973 (10)0.7903 (4)0.072 (2)
H80.67460.23200.77700.108*
O90.8930 (5)0.0926 (8)0.8130 (3)0.0590 (18)
H90.92840.04690.80620.088*
N10.6745 (5)0.9283 (9)0.4689 (4)0.0518 (19)
N20.7183 (5)0.8708 (9)0.5940 (4)0.0498 (18)
N30.9266 (5)0.8882 (9)0.5947 (3)0.0489 (18)
N40.8570 (5)0.6863 (9)0.4945 (4)0.0472 (17)
C10.6530 (7)0.9512 (13)0.4087 (5)0.064 (3)
H10.67330.88470.39100.077*
C20.6005 (8)1.0726 (15)0.3710 (6)0.076 (3)
H20.58791.08850.32920.092*
C30.5669 (8)1.1702 (14)0.3957 (6)0.072 (3)
H30.53201.25200.37070.086*
C40.5858 (7)1.1449 (11)0.4582 (5)0.057 (2)
C50.6410 (6)1.0214 (10)0.4939 (5)0.049 (2)
C60.6605 (6)0.9861 (10)0.5582 (5)0.048 (2)
C70.5465 (8)1.2313 (11)0.4849 (7)0.066 (3)
H70.51011.31360.46140.079*
C80.5600 (7)1.1980 (13)0.5419 (6)0.069 (3)
H8A0.53271.25690.55760.082*
C90.6166 (7)1.0715 (11)0.5808 (5)0.054 (2)
C100.6308 (8)1.0324 (13)0.6411 (6)0.067 (3)
H100.60201.08620.65720.080*
C110.6879 (8)0.9133 (14)0.6760 (6)0.066 (3)
H110.69710.88390.71550.080*
C120.7314 (8)0.8380 (12)0.6515 (5)0.062 (3)
H120.77220.75980.67660.074*
C130.9588 (7)0.9896 (11)0.6411 (5)0.057 (2)
H130.91991.00910.65590.069*
C141.0458 (8)1.0686 (12)0.6690 (5)0.071 (3)
H141.06461.13920.70140.086*
C151.1042 (7)1.0399 (12)0.6476 (6)0.071 (3)
H151.16381.09050.66560.085*
C161.0720 (7)0.9326 (12)0.5979 (5)0.062 (3)
C170.9822 (6)0.8634 (9)0.5726 (4)0.0409 (19)
C180.9451 (6)0.7565 (9)0.5191 (4)0.045 (2)
C191.1266 (7)0.9027 (14)0.5705 (6)0.072 (3)
H191.18690.95050.58780.087*
C201.0910 (9)0.8066 (17)0.5204 (7)0.080 (4)
H201.12720.78830.50350.096*
C210.9986 (8)0.7317 (11)0.4924 (5)0.058 (3)
C220.9556 (9)0.6364 (14)0.4378 (6)0.074 (4)
H220.98760.62060.41770.089*
C230.8671 (10)0.5656 (12)0.4130 (6)0.069 (3)
H230.83980.49960.37760.083*
C240.8199 (8)0.5964 (11)0.4429 (5)0.060 (3)
H240.75870.55120.42570.072*
C250.7074 (5)0.3669 (9)0.7078 (4)0.0366 (17)
C260.7595 (6)0.2558 (9)0.7554 (4)0.0394 (18)
C270.8460 (6)0.1997 (10)0.7667 (4)0.044 (2)
C280.8808 (6)0.2563 (9)0.7321 (4)0.0389 (18)
H280.93990.22090.74050.047*
C290.8279 (6)0.3649 (9)0.6853 (4)0.0371 (18)
C300.7408 (6)0.4223 (10)0.6727 (4)0.0425 (19)
H300.70590.49630.64140.051*
O100.3768 (9)0.3091 (18)0.7042 (7)0.171 (6)
H10A0.40040.28210.74290.257*
H10B0.41590.27820.69710.257*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0384 (4)0.0485 (4)0.0461 (4)0.0018 (3)0.0264 (3)0.0014 (3)
S10.0409 (11)0.0553 (14)0.0491 (12)0.0034 (10)0.0300 (10)0.0058 (11)
S20.0349 (11)0.0722 (17)0.0523 (13)0.0129 (11)0.0259 (10)0.0076 (12)
O10.054 (4)0.060 (5)0.088 (6)−0.013 (4)0.007 (4)0.008 (4)
O20.055 (4)0.063 (4)0.054 (4)0.008 (3)0.033 (3)0.008 (3)
O30.075 (5)0.076 (5)0.059 (4)0.005 (4)0.046 (4)−0.004 (4)
O40.041 (3)0.065 (5)0.092 (5)0.009 (3)0.044 (4)0.013 (4)
O50.042 (4)0.130 (8)0.071 (5)0.031 (4)0.029 (4)0.031 (5)
O60.056 (5)0.181 (12)0.154 (9)0.017 (6)0.034 (6)−0.089 (9)
O70.078 (6)0.142 (9)0.194 (11)0.045 (6)0.107 (7)0.087 (9)
O80.062 (4)0.098 (6)0.073 (5)0.017 (4)0.050 (4)0.029 (4)
O90.054 (4)0.074 (5)0.058 (4)0.027 (3)0.039 (3)0.025 (4)
N10.034 (4)0.075 (6)0.044 (4)0.002 (4)0.022 (3)0.000 (4)
N20.041 (4)0.063 (5)0.049 (4)−0.001 (4)0.029 (3)−0.004 (4)
N30.036 (4)0.059 (5)0.039 (4)−0.002 (3)0.016 (3)−0.001 (4)
N40.047 (4)0.049 (4)0.044 (4)−0.003 (4)0.027 (3)−0.002 (4)
C10.051 (5)0.087 (8)0.063 (6)0.002 (6)0.038 (5)0.005 (6)
C20.058 (6)0.104 (10)0.067 (7)0.019 (7)0.038 (6)0.025 (7)
C30.052 (6)0.073 (8)0.071 (7)0.008 (6)0.027 (5)0.014 (6)
C40.043 (5)0.054 (6)0.069 (6)0.002 (4)0.031 (5)−0.001 (5)
C50.032 (4)0.050 (6)0.060 (5)−0.004 (4)0.025 (4)−0.002 (4)
C60.032 (4)0.053 (6)0.057 (5)−0.003 (4)0.026 (4)−0.001 (4)
C70.050 (6)0.046 (6)0.084 (8)0.006 (4)0.032 (6)−0.009 (5)
C80.044 (5)0.064 (7)0.087 (8)−0.005 (5)0.034 (6)−0.026 (6)
C90.040 (5)0.059 (6)0.057 (5)−0.017 (4)0.026 (4)−0.017 (5)
C100.054 (6)0.084 (8)0.073 (7)−0.019 (6)0.044 (6)−0.034 (6)
C110.067 (6)0.090 (9)0.061 (6)−0.014 (6)0.048 (6)−0.017 (6)
C120.057 (6)0.066 (7)0.058 (6)0.000 (5)0.033 (5)0.004 (5)
C130.055 (5)0.057 (6)0.046 (5)−0.004 (5)0.024 (4)−0.011 (5)
C140.056 (6)0.052 (6)0.060 (6)−0.007 (5)0.011 (5)−0.007 (5)
C150.039 (5)0.061 (7)0.069 (7)−0.009 (5)0.010 (5)0.005 (6)
C160.034 (5)0.070 (7)0.057 (6)0.014 (5)0.016 (4)0.017 (5)
C170.029 (4)0.034 (4)0.044 (5)0.005 (3)0.015 (4)0.012 (4)
C180.043 (4)0.049 (5)0.044 (4)0.008 (4)0.027 (4)0.014 (4)
C190.042 (5)0.087 (9)0.090 (8)−0.001 (5)0.041 (6)0.039 (7)
C200.054 (6)0.110 (10)0.092 (9)0.017 (7)0.052 (7)0.023 (8)
C210.058 (5)0.068 (7)0.061 (6)0.018 (5)0.043 (5)0.032 (5)
C220.094 (9)0.094 (9)0.064 (7)0.040 (7)0.063 (7)0.024 (7)
C230.092 (8)0.058 (7)0.065 (7)0.006 (6)0.052 (7)0.006 (5)
C240.065 (6)0.057 (6)0.054 (6)0.003 (5)0.034 (5)−0.004 (5)
C250.028 (4)0.042 (5)0.035 (4)0.005 (3)0.016 (3)−0.003 (4)
C260.037 (4)0.051 (5)0.034 (4)0.001 (4)0.023 (3)−0.007 (4)
C270.033 (4)0.054 (5)0.037 (4)0.008 (4)0.017 (4)0.004 (4)
C280.031 (4)0.047 (5)0.040 (4)0.010 (4)0.021 (3)−0.006 (4)
C290.032 (4)0.044 (5)0.032 (4)−0.003 (3)0.018 (3)0.000 (4)
C300.033 (4)0.051 (5)0.039 (4)0.007 (4)0.020 (4)0.007 (4)
O100.119 (10)0.232 (16)0.159 (12)0.043 (11)0.082 (9)0.040 (12)
Geometric parameters (Å, °) top
Cd1—O12.285 (7)C7—H70.9300
Cd1—O22.299 (6)C8—C91.450 (16)
Cd1—N42.310 (7)C8—H8A0.9300
Cd1—N22.319 (7)C9—C101.400 (15)
Cd1—N12.337 (8)C10—C111.372 (16)
Cd1—N32.341 (7)C10—H100.9300
S1—O31.446 (7)C11—C121.378 (14)
S1—O41.461 (6)C11—H110.9300
S1—O21.464 (7)C12—H120.9300
S1—C291.772 (8)C13—C141.376 (15)
S2—O51.415 (7)C13—H130.9300
S2—O61.425 (10)C14—C151.380 (17)
S2—O71.455 (9)C14—H140.9300
S2—C251.791 (7)C15—C161.411 (16)
O1—H1A0.8205C15—H150.9300
O1—H1B0.8202C16—C171.377 (13)
O8—C261.343 (11)C16—C191.445 (15)
O8—H80.8200C17—C181.457 (12)
O9—C271.352 (11)C18—C211.406 (13)
O9—H90.8200C19—C201.337 (18)
N1—C11.312 (12)C19—H190.9300
N1—C51.363 (12)C20—C211.425 (16)
N2—C121.330 (12)C20—H200.9300
N2—C61.353 (12)C21—C221.394 (16)
N3—C131.320 (12)C22—C231.370 (17)
N3—C171.343 (11)C22—H220.9300
N4—C241.322 (12)C23—C241.390 (15)
N4—C181.362 (11)C23—H230.9300
C1—C21.387 (16)C24—H240.9300
C1—H10.9300C25—C301.377 (11)
C2—C31.385 (16)C25—C261.403 (11)
C2—H20.9300C26—C271.387 (11)
C3—C41.390 (15)C27—C281.389 (12)
C3—H30.9300C28—C291.378 (11)
C4—C51.402 (14)C28—H280.9300
C4—C71.422 (15)C29—C301.388 (11)
C5—C61.445 (13)C30—H300.9300
C6—C91.402 (13)O10—H10A0.8197
C7—C81.315 (17)O10—H10B0.8197
Cg1···Cg4i3.734 (7)Cg3···Cg3iv3.900 (7)
Cg1···Cg6ii3.937 (6)Cg4···Cg4i3.533 (7)
Cg2···Cg6iii3.525 (5)Cg5···Cg5v3.606 (7)
O1—Cd1—O282.9 (3)C9—C8—H8A119.3
O1—Cd1—N490.6 (3)C10—C9—C6118.4 (10)
O2—Cd1—N4103.4 (3)C10—C9—C8122.6 (10)
O1—Cd1—N2102.6 (3)C6—C9—C8118.9 (9)
O2—Cd1—N286.8 (3)C11—C10—C9119.0 (10)
N4—Cd1—N2164.4 (3)C11—C10—H10120.5
O1—Cd1—N195.3 (3)C9—C10—H10120.5
O2—Cd1—N1158.3 (2)C10—C11—C12119.0 (10)
N4—Cd1—N198.2 (3)C10—C11—H11120.5
N2—Cd1—N172.5 (3)C12—C11—H11120.5
O1—Cd1—N3161.8 (3)N2—C12—C11123.6 (11)
O2—Cd1—N395.1 (2)N2—C12—H12118.2
N4—Cd1—N372.2 (3)C11—C12—H12118.2
N2—Cd1—N395.4 (3)N3—C13—C14124.7 (10)
N1—Cd1—N393.1 (3)N3—C13—H13117.7
O3—S1—O4113.4 (4)C14—C13—H13117.7
O3—S1—O2111.6 (4)C13—C14—C15118.1 (10)
O4—S1—O2112.0 (4)C13—C14—H14121.0
O3—S1—C29107.9 (4)C15—C14—H14121.0
O4—S1—C29105.7 (4)C14—C15—C16118.8 (10)
O2—S1—C29105.9 (4)C14—C15—H15120.6
O5—S2—O6113.4 (7)C16—C15—H15120.6
O5—S2—O7112.1 (6)C17—C16—C15117.6 (10)
O6—S2—O7112.6 (8)C17—C16—C19120.6 (10)
O5—S2—C25106.7 (4)C15—C16—C19121.6 (11)
O6—S2—C25106.5 (5)N3—C17—C16123.7 (9)
O7—S2—C25104.9 (5)N3—C17—C18117.6 (7)
Cd1—O1—H1A122.0C16—C17—C18118.7 (8)
Cd1—O1—H1B132.2N4—C18—C21121.5 (9)
H1A—O1—H1B105.1N4—C18—C17119.0 (7)
S1—O2—Cd1132.3 (4)C21—C18—C17119.5 (8)
C26—O8—H8109.5C20—C19—C16120.4 (10)
C27—O9—H9109.5C20—C19—H19119.8
C1—N1—C5119.9 (9)C16—C19—H19119.8
C1—N1—Cd1125.3 (7)C19—C20—C21121.5 (11)
C5—N1—Cd1114.5 (6)C19—C20—H20119.3
C12—N2—C6118.2 (8)C21—C20—H20119.3
C12—N2—Cd1127.0 (7)C22—C21—C18117.1 (10)
C6—N2—Cd1114.8 (6)C22—C21—C20123.6 (10)
C13—N3—C17117.1 (8)C18—C21—C20119.3 (11)
C13—N3—Cd1127.2 (7)C23—C22—C21121.5 (10)
C17—N3—Cd1115.7 (6)C23—C22—H22119.3
C24—N4—C18118.9 (8)C21—C22—H22119.3
C24—N4—Cd1125.6 (7)C22—C23—C24117.3 (11)
C18—N4—Cd1115.4 (6)C22—C23—H23121.4
N1—C1—C2121.3 (11)C24—C23—H23121.4
N1—C1—H1119.4N4—C24—C23123.7 (10)
C2—C1—H1119.4N4—C24—H24118.2
C3—C2—C1120.0 (11)C23—C24—H24118.2
C3—C2—H2120.0C30—C25—C26121.5 (7)
C1—C2—H2120.0C30—C25—S2118.6 (6)
C2—C3—C4119.5 (11)C26—C25—S2119.8 (6)
C2—C3—H3120.3O8—C26—C27117.3 (8)
C4—C3—H3120.3O8—C26—C25123.7 (7)
C3—C4—C5117.2 (10)C27—C26—C25119.0 (7)
C3—C4—C7123.7 (10)O9—C27—C26116.5 (8)
C5—C4—C7119.0 (10)O9—C27—C28123.7 (7)
N1—C5—C4122.0 (9)C26—C27—C28119.7 (8)
N1—C5—C6117.8 (8)C29—C28—C27120.1 (7)
C4—C5—C6120.1 (9)C29—C28—H28120.0
N2—C6—C9121.8 (9)C27—C28—H28120.0
N2—C6—C5119.7 (8)C28—C29—C30121.3 (7)
C9—C6—C5118.5 (9)C28—C29—S1120.1 (6)
C8—C7—C4121.8 (11)C30—C29—S1118.6 (6)
C8—C7—H7119.1C25—C30—C29118.3 (8)
C4—C7—H7119.1C25—C30—H30120.9
C7—C8—C9121.4 (10)C29—C30—H30120.9
C7—C8—H8A119.3H10A—O10—H10B104.8
O3—S1—O2—Cd1−16.4 (7)N2—C6—C9—C8176.7 (8)
O4—S1—O2—Cd1111.8 (5)C5—C6—C9—C8−4.7 (12)
C29—S1—O2—Cd1−133.5 (5)C7—C8—C9—C10−179.0 (10)
O1—Cd1—O2—S144.5 (6)C7—C8—C9—C62.2 (15)
N4—Cd1—O2—S1−44.4 (6)C6—C9—C10—C110.7 (14)
N2—Cd1—O2—S1147.6 (5)C8—C9—C10—C11−178.1 (9)
N1—Cd1—O2—S1130.8 (7)C9—C10—C11—C121.5 (15)
N3—Cd1—O2—S1−117.3 (5)C6—N2—C12—C111.2 (15)
O1—Cd1—N1—C1−76.7 (8)Cd1—N2—C12—C11−177.0 (8)
O2—Cd1—N1—C1−160.6 (8)C10—C11—C12—N2−2.6 (16)
N4—Cd1—N1—C114.7 (8)C17—N3—C13—C14−1.5 (15)
N2—Cd1—N1—C1−178.2 (9)Cd1—N3—C13—C14179.5 (8)
N3—Cd1—N1—C187.1 (8)N3—C13—C14—C15−0.3 (17)
O1—Cd1—N1—C5108.9 (6)C13—C14—C15—C160.6 (16)
O2—Cd1—N1—C525.0 (11)C14—C15—C16—C171.0 (15)
N4—Cd1—N1—C5−159.7 (6)C14—C15—C16—C19176.5 (10)
N2—Cd1—N1—C57.4 (6)C13—N3—C17—C163.3 (13)
N3—Cd1—N1—C5−87.3 (6)Cd1—N3—C17—C16−177.7 (7)
O1—Cd1—N2—C1282.3 (8)C13—N3—C17—C18−177.2 (8)
O2—Cd1—N2—C120.3 (8)Cd1—N3—C17—C181.9 (9)
N4—Cd1—N2—C12−131.1 (10)C15—C16—C17—N3−3.0 (14)
N1—Cd1—N2—C12173.9 (8)C19—C16—C17—N3−178.6 (8)
N3—Cd1—N2—C12−94.5 (8)C15—C16—C17—C18177.4 (8)
O1—Cd1—N2—C6−96.0 (6)C19—C16—C17—C181.8 (13)
O2—Cd1—N2—C6−178.0 (6)C24—N4—C18—C21−2.1 (13)
N4—Cd1—N2—C650.6 (12)Cd1—N4—C18—C21−178.9 (6)
N1—Cd1—N2—C6−4.4 (6)C24—N4—C18—C17175.5 (8)
N3—Cd1—N2—C687.2 (6)Cd1—N4—C18—C17−1.2 (10)
O1—Cd1—N3—C13−163.2 (9)N3—C17—C18—N4−0.5 (11)
O2—Cd1—N3—C13−80.4 (8)C16—C17—C18—N4179.1 (8)
N4—Cd1—N3—C13177.1 (8)N3—C17—C18—C21177.2 (8)
N2—Cd1—N3—C136.8 (8)C16—C17—C18—C21−3.2 (12)
N1—Cd1—N3—C1379.5 (8)C17—C16—C19—C20−0.4 (16)
O1—Cd1—N3—C1717.8 (12)C15—C16—C19—C20−175.8 (11)
O2—Cd1—N3—C17100.6 (6)C16—C19—C20—C210.3 (18)
N4—Cd1—N3—C17−1.8 (6)N4—C18—C21—C222.5 (13)
N2—Cd1—N3—C17−172.1 (6)C17—C18—C21—C22−175.2 (8)
N1—Cd1—N3—C17−99.4 (6)N4—C18—C21—C20−179.3 (9)
O1—Cd1—N4—C2411.1 (8)C17—C18—C21—C203.1 (13)
O2—Cd1—N4—C2493.9 (8)C19—C20—C21—C22176.4 (11)
N2—Cd1—N4—C24−136.4 (10)C19—C20—C21—C18−1.7 (17)
N1—Cd1—N4—C24−84.3 (8)C18—C21—C22—C23−2.6 (15)
N3—Cd1—N4—C24−174.9 (8)C20—C21—C22—C23179.3 (11)
O1—Cd1—N4—C18−172.4 (6)C21—C22—C23—C242.3 (16)
O2—Cd1—N4—C18−89.6 (6)C18—N4—C24—C231.8 (15)
N2—Cd1—N4—C1840.1 (12)Cd1—N4—C24—C23178.2 (8)
N1—Cd1—N4—C1892.2 (6)C22—C23—C24—N4−1.9 (16)
N3—Cd1—N4—C181.6 (6)O5—S2—C25—C3035.7 (8)
C5—N1—C1—C23.1 (15)O6—S2—C25—C30−85.7 (9)
Cd1—N1—C1—C2−171.0 (8)O7—S2—C25—C30154.8 (8)
N1—C1—C2—C3−2.1 (17)O5—S2—C25—C26−146.1 (7)
C1—C2—C3—C4−0.3 (17)O6—S2—C25—C2692.5 (9)
C2—C3—C4—C51.5 (15)O7—S2—C25—C26−27.0 (9)
C2—C3—C4—C7−173.9 (10)C30—C25—C26—O8−179.2 (8)
C1—N1—C5—C4−1.8 (13)S2—C25—C26—O82.6 (12)
Cd1—N1—C5—C4172.9 (7)C30—C25—C26—C27−0.7 (12)
C1—N1—C5—C6175.7 (8)S2—C25—C26—C27−178.9 (6)
Cd1—N1—C5—C6−9.6 (10)O8—C26—C27—O9−1.2 (12)
C3—C4—C5—N1−0.5 (14)C25—C26—C27—O9−179.8 (8)
C7—C4—C5—N1175.2 (9)O8—C26—C27—C28−179.9 (8)
C3—C4—C5—C6−178.0 (9)C25—C26—C27—C281.5 (13)
C7—C4—C5—C6−2.3 (13)O9—C27—C28—C29179.5 (8)
C12—N2—C6—C91.2 (13)C26—C27—C28—C29−1.9 (13)
Cd1—N2—C6—C9179.7 (6)C27—C28—C29—C301.5 (12)
C12—N2—C6—C5−177.3 (8)C27—C28—C29—S1−179.5 (6)
Cd1—N2—C6—C51.1 (10)O3—S1—C29—C2898.1 (7)
N1—C5—C6—N25.9 (12)O4—S1—C29—C28−23.4 (8)
C4—C5—C6—N2−176.6 (8)O2—S1—C29—C28−142.3 (7)
N1—C5—C6—C9−172.7 (8)O3—S1—C29—C30−82.8 (8)
C4—C5—C6—C94.9 (13)O4—S1—C29—C30155.6 (7)
C3—C4—C7—C8175.0 (11)O2—S1—C29—C3036.7 (8)
C5—C4—C7—C8−0.4 (15)C26—C25—C30—C290.3 (12)
C4—C7—C8—C90.4 (16)S2—C25—C30—C29178.5 (6)
N2—C6—C9—C10−2.2 (13)C28—C29—C30—C25−0.7 (12)
C5—C6—C9—C10176.4 (8)S1—C29—C30—C25−179.7 (6)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) −x, −y, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.822.152.790 (10)135
O1—H1B···O5vi0.821.932.735 (10)167
O10—H10A···O6vii0.822.222.737 (19)121
O10—H10B···O70.822.182.876 (15)143
O8—H8···O70.821.872.614 (11)150
O9—H9···O4viii0.821.902.690 (9)160
C23—H23···O8ix0.932.573.465 (15)163
C23—H23···O9ix0.932.403.112 (17)134
Symmetry codes: (vi) −x+1, −y+1, −z+1; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+2, y−1/2, −z+3/2; (ix) x, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å) top
Cg1···Cg4i3.734 (7)Cg3···Cg3iv3.900 (7)
Cg1···Cg6ii3.937 (6)Cg4···Cg4i3.533 (7)
Cg2···Cg6iii3.525 (5)Cg5···Cg5v3.606 (7)
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+1, −z+1; (v) −x, −y, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.822.152.790 (10)135
O1—H1B···O5vi0.821.932.735 (10)167
O10—H10A···O6vii0.822.222.737 (19)121
O10—H10B···O70.822.182.876 (15)143
O8—H8···O70.821.872.614 (11)150
O9—H9···O4viii0.821.902.690 (9)160
C23—H23···O8ix0.932.573.465 (15)163
C23—H23···O9ix0.932.403.112 (17)134
Symmetry codes: (vi) −x+1, −y+1, −z+1; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+2, y−1/2, −z+3/2; (ix) x, −y+1/2, z−1/2.
Acknowledgements top

This project was supported by the Natural Science Foundation of the Education Bureau of Liaoning Province (grant No. 05 L159).

references
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