catena-Poly[[bis-(2,2'-bipyridine-κN,N')cadmium(II)]-μ-9,10-dioxo-anthracene-1,5-disulfonato-κO:O].

The title complex, [Cd(C(14)H(6)O(8)S(2))(C(10)H(8)N(2))(2)](n), exhibits a chain-like polymeric structure with 9,10-dioxoanthracene-1,5-disulfonate anions bridging Cd(II) atoms in a bis-monodentate mode. The Cd(II) atom shows a distorted octa-hedral 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 inter-actions [centroid-centroid distances = 3.6920 (12) and 3.7095 (12) Å] connect the complex mol-ecules into a three-dimensional supra-molecular framework.

Related literature

For applications of organosulfonate-based n class="Chemical">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

[Cd(C14H6O8S2)(C10n class="Species">H8N2)2]

M = 791.08

Triclinic,

a = 10.3807 (7) Å

b = 10.7406 (8) Å

c = 13.1289 (9) Å

α = 94.044 (1)°

β = 90.239 (1)°

γ = 97.025 (1)°

V = 1449.08 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.96 mm−1

T = 296 K

0.24 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.802, T max = 0.816

7435 measured reflections

5078 independent reflections

4773 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.061

S = 1.01

5078 reflections

442 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046881/si2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046881/si2219Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[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	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

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)

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

Table 1

Selected bond lengths (Å)

Cd1—N3	2.2645 (17)
Cd1—N1	2.3050 (17)
Cd1—N2	2.3356 (17)
Cd1—O4i	2.3527 (16)
Cd1—N4	2.3882 (17)
Cd1—O2	2.4109 (16)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O5ii	0.93	2.48	3.200 (3)	135
C5—H5⋯O4ii	0.93	2.53	3.239 (3)	133
C14—H14⋯O2iii	0.93	2.54	3.267 (3)	136

Symmetry codes: (ii) ; (iii) .