Bis{4-phenyl-1-[1-(pyridin-2-yl-κN)ethyl-idene]thio-semicarbazidato-κ(2)N(1),S}cadmium.

The reaction of cadmium acetate dihydrate with 2-acetyl-pyridine (4-phenyl-thio-semicarbazone) yielded the title compound, [Cd(C(14)H(13)N(4)S)(2)]. The Cd(II) atom is six-coordin-ated in a distorted octa-hedral environment by two deproton-ated thio-semicarbazone ligands acting in a tridentate chelating mode through two N and one S atoms, forming metalla-rings. In the crystal, mol-ecules are connected through inversion centers via pairs of N-H⋯S inter-actions, building a one-dimensional hydrogen-bonded polymer along [0-1-1].

Related literature

For the synthesis of 2-acetyl­pyridine-(4-phenyl­thio­semi­carbazone), see: Offiong & Martelli (1997 ▶). For thio­semi­carbazone complexes with similar coordination environments, see: Ali et al. (2002 ▶); Kovala-Demertzi et al. (2005 ▶). For the anti­bacterial and anti­fungal activity of CdII thio­semicarbazone complexes, see: Alomar et al. (2010 ▶). For the bioinorganic chemistry of the CdII ion and its relation to biologically important ions, namely ZnII and CaII, see: Kaim & Schwederski (1995 ▶).

Experimental

Crystal data

[Cd(C14H13N4S)2]

M = 651.09

Triclinic,

a = 9.8452 (2) Å

b = 13.0116 (3) Å

c = 13.1736 (5) Å

α = 116.495 (1)°

β = 105.757 (1)°

γ = 96.122 (1)°

V = 1401.81 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.96 mm−1

T = 296 K

0.22 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.816, T max = 0.902

29421 measured reflections

8199 independent reflections

5975 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.080

S = 1.06

8199 reflections

362 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016558/bt5877sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016558/bt5877Isup2.hkl

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

[Cd(C14H13N4S)2]	Z = 2
Mr = 651.09	F(000) = 660
Triclinic, P1	Dx = 1.543 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8452 (2) Å	Cell parameters from 5467 reflections
b = 13.0116 (3) Å	θ = 2.3–23.9°
c = 13.1736 (5) Å	µ = 0.96 mm−1
α = 116.495 (1)°	T = 296 K
β = 105.757 (1)°	Block, yellow
γ = 96.122 (1)°	0.22 × 0.14 × 0.11 mm
V = 1401.81 (7) Å3

Bruker APEXII CCD diffractometer	8199 independent reflections
Radiation source: fine-focus sealed tube	5975 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 30.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.816, Tmax = 0.902	k = −18→17
29421 measured reflections	l = −16→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0314P)2 + 0.0548P] where P = (Fo2 + 2Fc2)/3
8199 reflections	(Δ/σ)max = 0.001
362 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.49 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	0.226151 (19)	0.208486 (15)	0.431225 (15)	0.03261 (6)
S1	0.04751 (7)	0.34127 (6)	0.45863 (5)	0.03845 (15)
S2	0.11139 (7)	0.07311 (6)	0.19832 (6)	0.04311 (16)
C1	0.2081 (3)	0.0380 (2)	0.5482 (2)	0.0349 (5)
C5	0.3030 (3)	−0.0431 (2)	0.3973 (3)	0.0542 (7)
H4	0.3389	−0.0363	0.3415	0.065*
C2	0.1985 (3)	−0.0638 (2)	0.5583 (3)	0.0468 (7)
H1	0.1624	−0.0695	0.6145	0.056*
C3	0.2432 (4)	−0.1567 (3)	0.4838 (3)	0.0582 (8)
H2	0.2360	−0.2261	0.4886	0.070*
C4	0.2977 (4)	−0.1462 (3)	0.4035 (3)	0.0622 (9)
H3	0.3306	−0.2071	0.3541	0.075*
C8	0.0828 (3)	0.3844 (2)	0.6114 (2)	0.0319 (5)
C6	0.1612 (3)	0.1410 (2)	0.6249 (2)	0.0334 (5)
C9	0.0826 (3)	0.5625 (2)	0.8007 (2)	0.0356 (5)
C10	0.0613 (3)	0.6755 (2)	0.8373 (2)	0.0436 (6)
H9	0.0400	0.7026	0.7818	0.052*
C14	0.1168 (4)	0.5245 (3)	0.8844 (2)	0.0536 (8)
H13	0.1325	0.4495	0.8618	0.064*
C7	0.1277 (4)	0.1484 (3)	0.7318 (3)	0.0550 (8)
H5	0.2132	0.1489	0.7887	0.083*
H6	0.0495	0.0807	0.7050	0.083*
H7	0.0989	0.2201	0.7704	0.083*
C12	0.1050 (3)	0.7096 (3)	1.0382 (2)	0.0526 (7)
H11	0.1124	0.7584	1.1179	0.063*
C11	0.0713 (3)	0.7478 (2)	0.9550 (2)	0.0521 (7)
H10	0.0551	0.8229	0.9782	0.063*
C13	0.1275 (4)	0.5989 (3)	1.0025 (3)	0.0610 (8)
H12	0.1505	0.5730	1.0589	0.073*
N2	0.1521 (2)	0.22010 (16)	0.59191 (17)	0.0324 (4)
N4	0.0634 (3)	0.49398 (19)	0.67666 (19)	0.0402 (5)
N3	0.1191 (2)	0.32216 (17)	0.66504 (17)	0.0348 (4)
N1	0.2593 (2)	0.04738 (17)	0.46709 (19)	0.0399 (5)
C22	0.2505 (3)	0.1299 (2)	0.1648 (2)	0.0337 (5)
C20	0.5236 (3)	0.3367 (2)	0.4314 (2)	0.0334 (5)
C15	0.5532 (3)	0.3897 (2)	0.5636 (2)	0.0340 (5)
C23	0.3274 (3)	0.0925 (2)	−0.0112 (2)	0.0405 (6)
C24	0.3295 (3)	−0.0091 (3)	−0.1097 (2)	0.0503 (7)
H22	0.2653	−0.0818	−0.1376	0.060*
C16	0.6781 (3)	0.4789 (2)	0.6492 (2)	0.0489 (7)
H14	0.7463	0.5080	0.6250	0.059*
C28	0.4211 (3)	0.1993 (3)	0.0278 (3)	0.0581 (8)
H26	0.4193	0.2683	0.0927	0.070*
C19	0.4774 (3)	0.3928 (2)	0.7153 (2)	0.0489 (7)
H17	0.4083	0.3634	0.7385	0.059*
C18	0.5999 (3)	0.4811 (3)	0.8043 (3)	0.0600 (8)
H16	0.6133	0.5106	0.8860	0.072*
C17	0.7008 (3)	0.5246 (3)	0.7713 (3)	0.0642 (9)
H15	0.7845	0.5845	0.8300	0.077*
C25	0.4256 (4)	−0.0030 (4)	−0.1660 (3)	0.0688 (10)
H23	0.4262	−0.0715	−0.2320	0.083*
C27	0.5184 (4)	0.2041 (4)	−0.0295 (3)	0.0795 (11)
H25	0.5827	0.2764	−0.0026	0.095*
C26	0.5200 (4)	0.1022 (4)	−0.1263 (3)	0.0835 (12)
H24	0.5858	0.1054	−0.1644	0.100*
N6	0.3994 (2)	0.25909 (17)	0.35954 (17)	0.0327 (4)
N5	0.4528 (2)	0.34715 (18)	0.59691 (18)	0.0389 (5)
N7	0.3738 (2)	0.21135 (18)	0.23768 (18)	0.0374 (5)
N8	0.2265 (3)	0.0800 (2)	0.0431 (2)	0.0429 (5)
C21	0.6341 (3)	0.3730 (2)	0.3876 (3)	0.0480 (7)
H18	0.6029	0.3237	0.3010	0.072*
H19	0.7266	0.3639	0.4253	0.072*
H20	0.6440	0.4548	0.4081	0.072*
H8	0.041 (3)	0.531 (2)	0.639 (2)	0.035 (7)*
H21	0.152 (3)	0.024 (2)	−0.002 (2)	0.042 (8)*

	U11	U22	U33	U12	U13	U23
Cd1	0.03545 (10)	0.03298 (10)	0.03154 (10)	0.00908 (7)	0.01550 (7)	0.01576 (8)
S1	0.0509 (4)	0.0407 (3)	0.0317 (3)	0.0229 (3)	0.0181 (3)	0.0201 (3)
S2	0.0417 (4)	0.0439 (4)	0.0312 (3)	−0.0027 (3)	0.0145 (3)	0.0108 (3)
C1	0.0361 (13)	0.0341 (13)	0.0347 (13)	0.0098 (10)	0.0081 (11)	0.0196 (11)
C5	0.071 (2)	0.0504 (17)	0.0535 (18)	0.0301 (15)	0.0326 (16)	0.0266 (15)
C2	0.0517 (17)	0.0423 (15)	0.0526 (17)	0.0155 (13)	0.0159 (14)	0.0295 (14)
C3	0.070 (2)	0.0413 (16)	0.067 (2)	0.0229 (15)	0.0158 (17)	0.0325 (16)
C4	0.076 (2)	0.0465 (17)	0.065 (2)	0.0355 (17)	0.0270 (18)	0.0236 (16)
C8	0.0342 (13)	0.0356 (12)	0.0323 (12)	0.0132 (10)	0.0161 (10)	0.0190 (11)
C6	0.0325 (13)	0.0377 (13)	0.0355 (13)	0.0118 (10)	0.0128 (10)	0.0217 (11)
C9	0.0387 (14)	0.0384 (13)	0.0318 (13)	0.0139 (11)	0.0160 (11)	0.0164 (11)
C10	0.0548 (17)	0.0375 (14)	0.0387 (15)	0.0139 (12)	0.0167 (13)	0.0188 (12)
C14	0.083 (2)	0.0494 (17)	0.0436 (16)	0.0323 (16)	0.0317 (16)	0.0268 (14)
C7	0.077 (2)	0.0605 (18)	0.0552 (18)	0.0314 (16)	0.0366 (17)	0.0407 (16)
C12	0.0600 (19)	0.0539 (18)	0.0330 (15)	0.0100 (15)	0.0200 (14)	0.0120 (14)
C11	0.0620 (19)	0.0373 (15)	0.0437 (16)	0.0114 (13)	0.0199 (14)	0.0092 (13)
C13	0.089 (3)	0.066 (2)	0.0376 (16)	0.0265 (18)	0.0281 (16)	0.0293 (16)
N2	0.0367 (11)	0.0310 (10)	0.0342 (11)	0.0130 (9)	0.0156 (9)	0.0176 (9)
N4	0.0582 (15)	0.0395 (12)	0.0352 (12)	0.0258 (11)	0.0220 (11)	0.0227 (11)
N3	0.0424 (12)	0.0341 (11)	0.0337 (11)	0.0164 (9)	0.0181 (9)	0.0177 (9)
N1	0.0485 (13)	0.0358 (11)	0.0429 (12)	0.0161 (10)	0.0226 (10)	0.0210 (10)
C22	0.0372 (13)	0.0355 (13)	0.0295 (12)	0.0119 (11)	0.0142 (10)	0.0151 (11)
C20	0.0298 (12)	0.0322 (12)	0.0374 (13)	0.0096 (10)	0.0113 (10)	0.0167 (11)
C15	0.0286 (12)	0.0319 (12)	0.0383 (14)	0.0100 (10)	0.0085 (10)	0.0164 (11)
C23	0.0376 (14)	0.0546 (16)	0.0310 (13)	0.0150 (12)	0.0143 (11)	0.0208 (12)
C24	0.0570 (18)	0.0598 (18)	0.0364 (15)	0.0242 (15)	0.0189 (13)	0.0225 (14)
C16	0.0342 (14)	0.0499 (16)	0.0455 (16)	0.0017 (12)	0.0088 (12)	0.0151 (14)
C28	0.066 (2)	0.0600 (19)	0.0418 (16)	0.0029 (16)	0.0255 (15)	0.0190 (15)
C19	0.0475 (17)	0.0543 (17)	0.0359 (15)	0.0064 (13)	0.0106 (13)	0.0193 (13)
C18	0.0511 (18)	0.070 (2)	0.0342 (15)	0.0070 (16)	0.0053 (14)	0.0136 (15)
C17	0.0414 (17)	0.068 (2)	0.0418 (17)	−0.0061 (15)	−0.0007 (14)	0.0074 (16)
C25	0.062 (2)	0.103 (3)	0.0435 (18)	0.043 (2)	0.0279 (17)	0.0286 (19)
C27	0.067 (2)	0.099 (3)	0.058 (2)	−0.012 (2)	0.0248 (18)	0.034 (2)
C26	0.062 (2)	0.142 (4)	0.050 (2)	0.024 (3)	0.0331 (19)	0.043 (2)
N6	0.0313 (11)	0.0344 (10)	0.0318 (11)	0.0082 (9)	0.0121 (9)	0.0156 (9)
N5	0.0353 (11)	0.0407 (12)	0.0343 (12)	0.0056 (9)	0.0088 (9)	0.0164 (10)
N7	0.0334 (11)	0.0444 (12)	0.0315 (11)	0.0061 (9)	0.0134 (9)	0.0164 (10)
N8	0.0394 (13)	0.0470 (13)	0.0313 (12)	0.0009 (11)	0.0133 (10)	0.0124 (11)
C21	0.0370 (15)	0.0528 (17)	0.0535 (17)	0.0046 (12)	0.0173 (13)	0.0268 (14)

Cd1—N6	2.3288 (19)	C11—H10	0.9300
Cd1—N2	2.3691 (18)	C13—H12	0.9300
Cd1—N1	2.381 (2)	N2—N3	1.385 (2)
Cd1—N5	2.446 (2)	N4—H8	0.84 (2)
Cd1—S1	2.5778 (6)	C22—N7	1.305 (3)
Cd1—S2	2.5814 (7)	C22—N8	1.371 (3)
S1—C8	1.748 (2)	C20—N6	1.291 (3)
S2—C22	1.738 (2)	C20—C15	1.484 (3)
C1—N1	1.344 (3)	C20—C21	1.489 (3)
C1—C2	1.385 (3)	C15—N5	1.346 (3)
C1—C6	1.487 (3)	C15—C16	1.380 (3)
C5—N1	1.332 (3)	C23—C28	1.371 (4)
C5—C4	1.376 (4)	C23—C24	1.386 (3)
C5—H4	0.9300	C23—N8	1.407 (3)
C2—C3	1.381 (4)	C24—C25	1.367 (4)
C2—H1	0.9300	C24—H22	0.9300
C3—C4	1.360 (4)	C16—C17	1.383 (4)
C3—H2	0.9300	C16—H14	0.9300
C4—H3	0.9300	C28—C27	1.383 (4)
C8—N3	1.311 (3)	C28—H26	0.9300
C8—N4	1.365 (3)	C19—N5	1.335 (3)
C6—N2	1.285 (3)	C19—C18	1.373 (4)
C6—C7	1.498 (3)	C19—H17	0.9300
C9—C14	1.377 (4)	C18—C17	1.353 (4)
C9—C10	1.387 (3)	C18—H16	0.9300
C9—N4	1.413 (3)	C17—H15	0.9300
C10—C11	1.376 (3)	C25—C26	1.355 (5)
C10—H9	0.9300	C25—H23	0.9300
C14—C13	1.383 (4)	C27—C26	1.375 (5)
C14—H13	0.9300	C27—H25	0.9300
C7—H5	0.9600	C26—H24	0.9300
C7—H6	0.9600	N6—N7	1.373 (3)
C7—H7	0.9600	N8—H21	0.83 (3)
C12—C13	1.365 (4)	C21—H18	0.9600
C12—C11	1.373 (4)	C21—H19	0.9600
C12—H11	0.9300	C21—H20	0.9600
N6—Cd1—N2	151.43 (7)	N3—N2—Cd1	120.07 (13)
N6—Cd1—N1	111.91 (7)	C8—N4—C9	132.0 (2)
N2—Cd1—N1	67.80 (6)	C8—N4—H8	116.0 (16)
N6—Cd1—N5	68.06 (7)	C9—N4—H8	111.9 (16)
N2—Cd1—N5	83.38 (7)	C8—N3—N2	112.35 (18)
N1—Cd1—N5	94.00 (7)	C5—N1—C1	118.4 (2)
N6—Cd1—S1	113.46 (5)	C5—N1—Cd1	122.97 (18)
N2—Cd1—S1	71.90 (5)	C1—N1—Cd1	117.63 (15)
N1—Cd1—S1	134.61 (5)	N7—C22—N8	115.7 (2)
N5—Cd1—S1	101.36 (5)	N7—C22—S2	129.77 (18)
N6—Cd1—S2	75.54 (5)	N8—C22—S2	114.48 (18)
N2—Cd1—S2	132.65 (5)	N6—C20—C15	116.4 (2)
N1—Cd1—S2	93.71 (5)	N6—C20—C21	123.3 (2)
N5—Cd1—S2	143.06 (5)	C15—C20—C21	120.3 (2)
S1—Cd1—S2	98.58 (2)	N5—C15—C16	121.1 (2)
C8—S1—Cd1	95.23 (8)	N5—C15—C20	117.2 (2)
C22—S2—Cd1	96.70 (8)	C16—C15—C20	121.7 (2)
N1—C1—C2	121.2 (2)	C28—C23—C24	119.2 (3)
N1—C1—C6	116.9 (2)	C28—C23—N8	123.3 (2)
C2—C1—C6	121.9 (2)	C24—C23—N8	117.5 (2)
N1—C5—C4	123.3 (3)	C25—C24—C23	120.3 (3)
N1—C5—H4	118.3	C25—C24—H22	119.9
C4—C5—H4	118.3	C23—C24—H22	119.9
C3—C2—C1	119.0 (3)	C15—C16—C17	119.3 (3)
C3—C2—H1	120.5	C15—C16—H14	120.3
C1—C2—H1	120.5	C17—C16—H14	120.3
C4—C3—C2	119.8 (3)	C23—C28—C27	119.9 (3)
C4—C3—H2	120.1	C23—C28—H26	120.1
C2—C3—H2	120.1	C27—C28—H26	120.1
C3—C4—C5	118.2 (3)	N5—C19—C18	123.1 (3)
C3—C4—H3	120.9	N5—C19—H17	118.5
C5—C4—H3	120.9	C18—C19—H17	118.5
N3—C8—N4	119.1 (2)	C17—C18—C19	118.8 (3)
N3—C8—S1	127.34 (17)	C17—C18—H16	120.6
N4—C8—S1	113.48 (17)	C19—C18—H16	120.6
N2—C6—C1	115.1 (2)	C18—C17—C16	119.3 (3)
N2—C6—C7	124.1 (2)	C18—C17—H15	120.3
C1—C6—C7	120.7 (2)	C16—C17—H15	120.3
C14—C9—C10	119.0 (2)	C26—C25—C24	120.6 (3)
C14—C9—N4	125.1 (2)	C26—C25—H23	119.7
C10—C9—N4	115.9 (2)	C24—C25—H23	119.7
C11—C10—C9	120.7 (3)	C26—C27—C28	120.0 (3)
C11—C10—H9	119.7	C26—C27—H25	120.0
C9—C10—H9	119.7	C28—C27—H25	120.0
C9—C14—C13	119.5 (3)	C25—C26—C27	120.0 (3)
C9—C14—H13	120.3	C25—C26—H24	120.0
C13—C14—H13	120.3	C27—C26—H24	120.0
C6—C7—H5	109.5	C20—N6—N7	115.53 (19)
C6—C7—H6	109.5	C20—N6—Cd1	122.35 (16)
H5—C7—H6	109.5	N7—N6—Cd1	122.07 (14)
C6—C7—H7	109.5	C19—N5—C15	118.3 (2)
H5—C7—H7	109.5	C19—N5—Cd1	125.71 (18)
H6—C7—H7	109.5	C15—N5—Cd1	115.53 (15)
C13—C12—C11	119.2 (3)	C22—N7—N6	115.70 (19)
C13—C12—H11	120.4	C22—N8—C23	127.6 (2)
C11—C12—H11	120.4	C22—N8—H21	114.8 (18)
C12—C11—C10	120.2 (3)	C23—N8—H21	115.6 (18)
C12—C11—H10	119.9	C20—C21—H18	109.5
C10—C11—H10	119.9	C20—C21—H19	109.5
C12—C13—C14	121.5 (3)	H18—C21—H19	109.5
C12—C13—H12	119.3	C20—C21—H20	109.5
C14—C13—H12	119.3	H18—C21—H20	109.5
C6—N2—N3	117.64 (19)	H19—C21—H20	109.5
C6—N2—Cd1	121.55 (15)
N6—Cd1—S1—C8	−124.64 (10)	N6—Cd1—N1—C1	155.39 (17)
N2—Cd1—S1—C8	25.28 (9)	N2—Cd1—N1—C1	6.27 (17)
N1—Cd1—S1—C8	53.53 (11)	N5—Cd1—N1—C1	87.45 (18)
N5—Cd1—S1—C8	−53.81 (10)	S1—Cd1—N1—C1	−22.8 (2)
S2—Cd1—S1—C8	157.47 (8)	S2—Cd1—N1—C1	−128.71 (17)
N6—Cd1—S2—C22	−2.87 (9)	Cd1—S2—C22—N7	2.4 (2)
N2—Cd1—S2—C22	−177.49 (10)	Cd1—S2—C22—N8	−178.32 (17)
N1—Cd1—S2—C22	−114.55 (10)	N6—C20—C15—N5	4.1 (3)
N5—Cd1—S2—C22	−12.87 (12)	C21—C20—C15—N5	−175.7 (2)
S1—Cd1—S2—C22	109.27 (8)	N6—C20—C15—C16	−176.0 (2)
N1—C1—C2—C3	0.3 (4)	C21—C20—C15—C16	4.3 (4)
C6—C1—C2—C3	179.7 (2)	C28—C23—C24—C25	1.0 (4)
C1—C2—C3—C4	1.0 (4)	N8—C23—C24—C25	−179.6 (3)
C2—C3—C4—C5	−1.6 (5)	N5—C15—C16—C17	0.4 (4)
N1—C5—C4—C3	1.0 (5)	C20—C15—C16—C17	−179.6 (2)
Cd1—S1—C8—N3	−31.2 (2)	C24—C23—C28—C27	−1.3 (5)
Cd1—S1—C8—N4	151.43 (17)	N8—C23—C28—C27	179.3 (3)
N1—C1—C6—N2	11.0 (3)	N5—C19—C18—C17	0.2 (5)
C2—C1—C6—N2	−168.4 (2)	C19—C18—C17—C16	−0.1 (5)
N1—C1—C6—C7	−169.2 (2)	C15—C16—C17—C18	−0.1 (5)
C2—C1—C6—C7	11.4 (4)	C23—C24—C25—C26	0.1 (5)
C14—C9—C10—C11	−1.3 (4)	C23—C28—C27—C26	0.7 (5)
N4—C9—C10—C11	177.3 (3)	C24—C25—C26—C27	−0.8 (6)
C10—C9—C14—C13	0.7 (4)	C28—C27—C26—C25	0.4 (6)
N4—C9—C14—C13	−177.7 (3)	C15—C20—N6—N7	179.82 (18)
C13—C12—C11—C10	−0.4 (5)	C21—C20—N6—N7	−0.4 (3)
C9—C10—C11—C12	1.1 (4)	C15—C20—N6—Cd1	2.1 (3)
C11—C12—C13—C14	−0.1 (5)	C21—C20—N6—Cd1	−178.17 (17)
C9—C14—C13—C12	0.0 (5)	N2—Cd1—N6—C20	−6.2 (3)
C1—C6—N2—N3	−175.47 (19)	N1—Cd1—N6—C20	−89.70 (19)
C7—C6—N2—N3	4.7 (4)	N5—Cd1—N6—C20	−4.35 (17)
C1—C6—N2—Cd1	−5.3 (3)	S1—Cd1—N6—C20	88.90 (18)
C7—C6—N2—Cd1	174.9 (2)	S2—Cd1—N6—C20	−177.89 (19)
N6—Cd1—N2—C6	−95.5 (2)	N2—Cd1—N6—N7	176.23 (14)
N1—Cd1—N2—C6	−0.13 (18)	N1—Cd1—N6—N7	92.71 (17)
N5—Cd1—N2—C6	−97.20 (19)	N5—Cd1—N6—N7	178.06 (18)
S1—Cd1—N2—C6	158.52 (19)	S1—Cd1—N6—N7	−88.69 (16)
S2—Cd1—N2—C6	73.6 (2)	S2—Cd1—N6—N7	4.52 (15)
N6—Cd1—N2—N3	74.4 (2)	C18—C19—N5—C15	0.1 (4)
N1—Cd1—N2—N3	169.78 (18)	C18—C19—N5—Cd1	−171.9 (2)
N5—Cd1—N2—N3	72.71 (16)	C16—C15—N5—C19	−0.4 (4)
S1—Cd1—N2—N3	−31.57 (15)	C20—C15—N5—C19	179.6 (2)
S2—Cd1—N2—N3	−116.53 (15)	C16—C15—N5—Cd1	172.36 (19)
N3—C8—N4—C9	4.0 (4)	C20—C15—N5—Cd1	−7.6 (3)
S1—C8—N4—C9	−178.4 (2)	N6—Cd1—N5—C19	178.4 (2)
C14—C9—N4—C8	−5.7 (5)	N2—Cd1—N5—C19	−2.5 (2)
C10—C9—N4—C8	175.8 (3)	N1—Cd1—N5—C19	−69.6 (2)
N4—C8—N3—N2	−172.7 (2)	S1—Cd1—N5—C19	67.5 (2)
S1—C8—N3—N2	10.1 (3)	S2—Cd1—N5—C19	−171.19 (17)
C6—N2—N3—C8	−166.8 (2)	N6—Cd1—N5—C15	6.18 (15)
Cd1—N2—N3—C8	23.0 (2)	N2—Cd1—N5—C15	−174.70 (17)
C4—C5—N1—C1	0.4 (4)	N1—Cd1—N5—C15	118.22 (17)
C4—C5—N1—Cd1	−168.1 (2)	S1—Cd1—N5—C15	−104.72 (16)
C2—C1—N1—C5	−1.0 (4)	S2—Cd1—N5—C15	16.6 (2)
C6—C1—N1—C5	179.6 (2)	N8—C22—N7—N6	−178.4 (2)
C2—C1—N1—Cd1	168.07 (19)	S2—C22—N7—N6	0.8 (3)
C6—C1—N1—Cd1	−11.3 (3)	C20—N6—N7—C22	177.8 (2)
N6—Cd1—N1—C5	−36.1 (2)	Cd1—N6—N7—C22	−4.5 (3)
N2—Cd1—N1—C5	174.8 (2)	N7—C22—N8—C23	10.8 (4)
N5—Cd1—N1—C5	−104.0 (2)	S2—C22—N8—C23	−168.6 (2)
S1—Cd1—N1—C5	145.7 (2)	C28—C23—N8—C22	−44.0 (4)
S2—Cd1—N1—C5	39.8 (2)	C24—C23—N8—C22	136.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H8···S1i	0.84 (2)	2.60 (3)	3.437 (2)	172 (2)
N8—H21···S2ii	0.83 (3)	2.79 (3)	3.513 (2)	147 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H8⋯S1i	0.84 (2)	2.60 (3)	3.437 (2)	172 (2)
N8—H21⋯S2ii	0.83 (3)	2.79 (3)	3.513 (2)	147 (2)

Symmetry codes: (i) ; (ii) .