Iodido{4-phenyl-1-[1-(1,3-thia-zol-2-yl-κN)ethyl-idene]thio-semicarbazidato-κ(2) N',S}{4-phenyl-1-[1-(1,3-thia-zol-2-yl)ethyl-idene]thio-semicarbazide-κS}cadmium(II).

In the title complex, [Cd(C12H11N4S2)I(C12H12N4S2)], the Cd(II) ion is penta-coordinated by two thio-semicarbazone ligands (one neutral and the other anionic) and one iodide ion in a distorted square pyramidal (τ = 0.35) geometry. The central ion is coordinated by the thia-zole N atom, the thio-ureido N and the S atom of the deprotonated thio-semicarbazone ligand. The other ligand is linked with the central ion through the C=S group. The deprotonated ligand intra-molecularly hydrogen bonds to the thia-zole ring N atom, while the ligand forms an inter-molecular hydrogen bond to the thiol-ate S atom of the second ligand. The deprotonation of the tridentate ligand and its coordination to the Cd(II) ion via the S atom strikingly affects the C-S bond lengths. The C-S bond lengths in the neutral and deprotonated ligands in the metal complex are 1.709 (3) and 1.748 (2) Å, respectively, whereas it is 1.671 (3) Å in the free ligand. In the metal complex, the Cd-S distances are 2.6449 (6) and 2.5510 (6) Å. The Cd-I bond length is 2.7860 (2) Å.

Related literature

For properties of thio­semicarbazones and Cd complexes, see: Casas et al. (2000 ▶); Milczarska et al. (1998 ▶); Venkatraman et al. (2009 ▶); Dasary et al. (2011 ▶); Viñuelas-Zahínos et al. (2011 ▶); Arumugam et al. (2011 ▶). For a description of the geometry of complexes with five-coordinate n class="Chemical">metal atoms, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Cd(C12n class="Species">H11N4S2)I(C12H12N4S2)]

M = 791.04

Triclinic,

a = 8.6685 (4) Å

b = 10.1323 (5) Å

c = 16.7220 (8) Å

α = 76.607 (2)°

β = 79.481 (2)°

γ = 77.910 (2)°

V = 1383.15 (11) Å3

Z = 2

Mo Kα radiation

μ = 2.24 mm−1

T = 90 K

0.13 × 0.06 × 0.05 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.760, T max = 0.896

14913 measured reflections

8142 independent reflections

6715 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.060

S = 1.02

8142 reflections

354 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.92 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300915X/bv2219sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300915X/bv2219Isup2.hkl

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

[Cd(C12H11N4S2)I(C12H12N4S2)]	Z = 2
Mr = 791.04	F(000) = 776
Triclinic, P1	Dx = 1.899 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6685 (4) Å	Cell parameters from 6604 reflections
b = 10.1323 (5) Å	θ = 2.5–30.9°
c = 16.7220 (8) Å	µ = 2.24 mm−1
α = 76.607 (2)°	T = 90 K
β = 79.481 (2)°	Needle, yellow
γ = 77.910 (2)°	0.13 × 0.06 × 0.05 mm
V = 1383.15 (11) Å3

Bruker Kappa APEXII DUO CCD diffractometer	8142 independent reflections
Radiation source: fine-focus sealed tube	6715 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 31.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −12→12
Tmin = 0.760, Tmax = 0.896	k = −14→14
14913 measured reflections	l = −23→23

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0252P)2 + 0.1767P] where P = (Fo2 + 2Fc2)/3
8142 reflections	(Δ/σ)max = 0.002
354 parameters	Δρmax = 0.92 e Å−3
3 restraints	Δρmin = −0.60 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	0.330279 (19)	0.896637 (16)	0.264500 (10)	0.01247 (4)
I1	0.213720 (18)	1.080081 (15)	0.128204 (9)	0.01602 (4)
S1	0.89644 (7)	0.80381 (6)	0.20293 (4)	0.01885 (12)
S2	0.16206 (7)	0.96342 (6)	0.39576 (4)	0.01535 (11)
S3	0.98373 (7)	0.36995 (6)	0.41505 (4)	0.01949 (12)
S4	0.27226 (7)	0.64947 (6)	0.26713 (4)	0.01495 (11)
N1	0.5972 (2)	0.86012 (19)	0.19861 (12)	0.0142 (4)
N2	0.5065 (2)	0.85083 (19)	0.36308 (12)	0.0128 (4)
N3	0.4565 (2)	0.84714 (19)	0.44586 (12)	0.0140 (4)
N4	0.2430 (2)	0.8941 (2)	0.54478 (12)	0.0133 (4)
H4N	0.144 (2)	0.921 (3)	0.5524 (17)	0.016*
N5	0.6877 (2)	0.4726 (2)	0.41015 (13)	0.0158 (4)
N6	0.7257 (2)	0.49547 (19)	0.22678 (13)	0.0151 (4)
N7	0.5761 (2)	0.5403 (2)	0.26598 (13)	0.0147 (4)
H7N	0.570 (3)	0.534 (3)	0.3188 (13)	0.018*
N8	0.4803 (2)	0.5489 (2)	0.14662 (13)	0.0174 (4)
H8N	0.571 (3)	0.504 (3)	0.1322 (18)	0.021*
C1	0.6688 (3)	0.8655 (2)	0.11853 (15)	0.0186 (5)
H1	0.6100	0.8870	0.0731	0.022*
C2	0.8309 (3)	0.8379 (3)	0.10863 (16)	0.0207 (5)
H2	0.8978	0.8375	0.0569	0.025*
C3	0.7028 (3)	0.8282 (2)	0.25083 (15)	0.0133 (4)
C4	0.6581 (3)	0.8217 (2)	0.34029 (15)	0.0136 (4)
C5	0.7822 (3)	0.7869 (2)	0.39688 (16)	0.0174 (5)
H5A	0.7525	0.8454	0.4384	0.026*
H5B	0.8853	0.8026	0.3644	0.026*
H5C	0.7902	0.6899	0.4249	0.026*
C6	0.3038 (3)	0.8948 (2)	0.46333 (14)	0.0136 (4)
C7	0.3157 (3)	0.8592 (2)	0.61768 (14)	0.0137 (4)
C8	0.4782 (3)	0.8135 (2)	0.62054 (15)	0.0175 (5)
H8	0.5490	0.7996	0.5715	0.021*
C9	0.5353 (3)	0.7884 (2)	0.69633 (16)	0.0208 (5)
H9	0.6462	0.7581	0.6983	0.025*
C10	0.4341 (3)	0.8066 (2)	0.76886 (16)	0.0201 (5)
H10	0.4751	0.7900	0.8199	0.024*
C11	0.2714 (3)	0.8496 (2)	0.76577 (15)	0.0175 (5)
H11	0.2004	0.8610	0.8151	0.021*
C12	0.2133 (3)	0.8755 (2)	0.69095 (15)	0.0154 (4)
H12	0.1022	0.9049	0.6893	0.018*
C13	0.7108 (3)	0.4442 (2)	0.49162 (15)	0.0181 (5)
H13	0.6268	0.4618	0.5351	0.022*
C14	0.8628 (3)	0.3890 (3)	0.50580 (16)	0.0200 (5)
H14	0.8969	0.3644	0.5590	0.024*
C15	0.8225 (3)	0.4389 (2)	0.36162 (15)	0.0152 (5)
C16	0.8407 (3)	0.4521 (2)	0.27193 (15)	0.0151 (4)
C17	1.0016 (3)	0.4115 (3)	0.22704 (16)	0.0172 (5)
H17A	0.9970	0.4318	0.1672	0.026*
H17B	1.0384	0.3126	0.2456	0.026*
H17C	1.0758	0.4633	0.2387	0.026*
C18	0.4532 (3)	0.5759 (2)	0.22228 (14)	0.0135 (4)
C19	0.3685 (3)	0.5824 (2)	0.08851 (15)	0.0163 (5)
C20	0.3172 (3)	0.7197 (2)	0.05317 (15)	0.0180 (5)
H20	0.3514	0.7913	0.0696	0.022*
C21	0.2159 (3)	0.7507 (3)	−0.00614 (15)	0.0186 (5)
H21	0.1800	0.8441	−0.0305	0.022*
C22	0.1664 (3)	0.6454 (3)	−0.03024 (15)	0.0186 (5)
H22	0.0967	0.6669	−0.0710	0.022*
C23	0.2185 (3)	0.5100 (3)	0.00503 (16)	0.0186 (5)
H23	0.1848	0.4383	−0.0116	0.022*
C24	0.3201 (3)	0.4775 (2)	0.06488 (15)	0.0166 (5)
H24	0.3559	0.3841	0.0892	0.020*

	U11	U22	U33	U12	U13	U23
Cd1	0.01077 (8)	0.01618 (8)	0.01024 (8)	−0.00112 (6)	−0.00187 (6)	−0.00305 (6)
I1	0.01858 (8)	0.01534 (7)	0.01276 (8)	0.00038 (6)	−0.00397 (6)	−0.00170 (6)
S1	0.0111 (3)	0.0200 (3)	0.0233 (3)	−0.0016 (2)	0.0015 (2)	−0.0041 (2)
S2	0.0130 (3)	0.0212 (3)	0.0106 (3)	0.0018 (2)	−0.0028 (2)	−0.0042 (2)
S3	0.0147 (3)	0.0227 (3)	0.0211 (3)	−0.0013 (2)	−0.0068 (2)	−0.0030 (2)
S4	0.0135 (3)	0.0173 (3)	0.0147 (3)	−0.0032 (2)	−0.0017 (2)	−0.0042 (2)
N1	0.0121 (9)	0.0148 (9)	0.0151 (10)	−0.0030 (7)	−0.0001 (7)	−0.0022 (7)
N2	0.0131 (9)	0.0128 (9)	0.0126 (9)	−0.0025 (7)	−0.0012 (7)	−0.0030 (7)
N3	0.0142 (9)	0.0157 (9)	0.0125 (9)	−0.0031 (7)	−0.0036 (7)	−0.0015 (7)
N4	0.0121 (9)	0.0188 (9)	0.0099 (9)	−0.0030 (7)	−0.0021 (7)	−0.0039 (7)
N5	0.0152 (10)	0.0151 (9)	0.0185 (10)	−0.0040 (7)	−0.0035 (8)	−0.0038 (8)
N6	0.0140 (9)	0.0147 (9)	0.0182 (10)	−0.0036 (7)	−0.0006 (8)	−0.0067 (8)
N7	0.0130 (9)	0.0180 (9)	0.0136 (10)	−0.0012 (7)	−0.0025 (8)	−0.0048 (8)
N8	0.0161 (10)	0.0201 (10)	0.0163 (10)	0.0027 (8)	−0.0053 (8)	−0.0072 (8)
C1	0.0194 (12)	0.0217 (12)	0.0143 (11)	−0.0045 (9)	0.0015 (9)	−0.0051 (9)
C2	0.0192 (12)	0.0238 (12)	0.0169 (12)	−0.0030 (10)	0.0041 (10)	−0.0053 (10)
C3	0.0104 (10)	0.0115 (10)	0.0182 (11)	−0.0035 (8)	0.0006 (9)	−0.0043 (9)
C4	0.0138 (11)	0.0101 (10)	0.0165 (11)	−0.0032 (8)	−0.0031 (9)	−0.0004 (8)
C5	0.0148 (11)	0.0185 (11)	0.0193 (12)	−0.0016 (9)	−0.0073 (9)	−0.0020 (9)
C6	0.0162 (11)	0.0143 (10)	0.0116 (10)	−0.0038 (8)	−0.0033 (9)	−0.0032 (8)
C7	0.0197 (11)	0.0106 (10)	0.0125 (11)	−0.0054 (8)	−0.0055 (9)	−0.0007 (8)
C8	0.0193 (12)	0.0186 (11)	0.0152 (11)	−0.0031 (9)	−0.0050 (9)	−0.0029 (9)
C9	0.0219 (13)	0.0197 (12)	0.0220 (13)	−0.0048 (10)	−0.0090 (10)	−0.0013 (10)
C10	0.0302 (14)	0.0158 (11)	0.0173 (12)	−0.0049 (10)	−0.0125 (10)	−0.0017 (9)
C11	0.0283 (13)	0.0129 (10)	0.0114 (11)	−0.0042 (9)	−0.0051 (10)	−0.0004 (9)
C12	0.0187 (12)	0.0130 (10)	0.0152 (11)	−0.0038 (9)	−0.0041 (9)	−0.0021 (9)
C13	0.0195 (12)	0.0203 (12)	0.0151 (12)	−0.0052 (9)	−0.0039 (9)	−0.0018 (9)
C14	0.0218 (13)	0.0222 (12)	0.0169 (12)	−0.0057 (10)	−0.0073 (10)	−0.0006 (10)
C15	0.0174 (11)	0.0111 (10)	0.0189 (12)	−0.0035 (8)	−0.0071 (9)	−0.0025 (9)
C16	0.0171 (11)	0.0125 (10)	0.0171 (12)	−0.0033 (8)	−0.0044 (9)	−0.0036 (9)
C17	0.0115 (11)	0.0228 (12)	0.0192 (12)	−0.0024 (9)	−0.0010 (9)	−0.0094 (10)
C18	0.0131 (10)	0.0132 (10)	0.0139 (11)	−0.0034 (8)	−0.0017 (8)	−0.0015 (8)
C19	0.0132 (11)	0.0214 (12)	0.0140 (11)	0.0000 (9)	−0.0042 (9)	−0.0039 (9)
C20	0.0197 (12)	0.0182 (11)	0.0174 (12)	−0.0034 (9)	−0.0033 (10)	−0.0055 (9)
C21	0.0207 (12)	0.0183 (11)	0.0144 (11)	−0.0007 (9)	−0.0015 (9)	−0.0014 (9)
C22	0.0146 (11)	0.0285 (13)	0.0128 (11)	−0.0033 (9)	−0.0038 (9)	−0.0035 (10)
C23	0.0200 (12)	0.0213 (12)	0.0170 (12)	−0.0070 (10)	−0.0010 (10)	−0.0070 (10)
C24	0.0176 (12)	0.0137 (10)	0.0175 (12)	−0.0028 (9)	−0.0022 (9)	−0.0012 (9)

Cd1—N2	2.3524 (19)	C5—H5A	0.9800
Cd1—N1	2.3673 (19)	C5—H5B	0.9800
Cd1—S2	2.5510 (6)	C5—H5C	0.9800
Cd1—S4	2.6449 (6)	C7—C8	1.393 (3)
Cd1—I1	2.7860 (2)	C7—C12	1.397 (3)
S1—C2	1.709 (3)	C8—C9	1.394 (3)
S1—C3	1.716 (2)	C8—H8	0.9500
S2—C6	1.748 (2)	C9—C10	1.386 (4)
S3—C14	1.706 (3)	C9—H9	0.9500
S3—C15	1.731 (2)	C10—C11	1.393 (4)
S4—C18	1.708 (2)	C10—H10	0.9500
N1—C3	1.320 (3)	C11—C12	1.382 (3)
N1—C1	1.363 (3)	C11—H11	0.9500
N2—C4	1.291 (3)	C12—H12	0.9500
N2—N3	1.367 (3)	C13—C14	1.360 (3)
N3—C6	1.314 (3)	C13—H13	0.9500
N4—C6	1.367 (3)	C14—H14	0.9500
N4—C7	1.413 (3)	C15—C16	1.457 (3)
N4—H4N	0.842 (19)	C16—C17	1.483 (3)
N5—C15	1.325 (3)	C17—H17A	0.9800
N5—C13	1.368 (3)	C17—H17B	0.9800
N6—C16	1.302 (3)	C17—H17C	0.9800
N6—N7	1.378 (3)	C19—C24	1.379 (3)
N7—C18	1.342 (3)	C19—C20	1.392 (3)
N7—H7N	0.864 (19)	C20—C21	1.382 (3)
N8—C18	1.325 (3)	C20—H20	0.9500
N8—C19	1.432 (3)	C21—C22	1.393 (3)
N8—H8N	0.85 (2)	C21—H21	0.9500
C1—C2	1.360 (3)	C22—C23	1.377 (3)
C1—H1	0.9500	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.391 (3)
C3—C4	1.465 (3)	C23—H23	0.9500
C4—C5	1.495 (3)	C24—H24	0.9500
N2—Cd1—N1	69.91 (7)	C12—C7—N4	115.6 (2)
N2—Cd1—S2	74.23 (5)	C7—C8—C9	119.1 (2)
N1—Cd1—S2	141.74 (5)	C7—C8—H8	120.5
N2—Cd1—S4	102.87 (5)	C9—C8—H8	120.5
N1—Cd1—S4	96.47 (5)	C10—C9—C8	121.5 (2)
S2—Cd1—S4	104.16 (2)	C10—C9—H9	119.2
N2—Cd1—I1	146.34 (5)	C8—C9—H9	119.2
N1—Cd1—I1	94.99 (5)	C9—C10—C11	119.0 (2)
S2—Cd1—I1	107.969 (15)	C9—C10—H10	120.5
S4—Cd1—I1	108.767 (14)	C11—C10—H10	120.5
C2—S1—C3	90.02 (12)	C12—C11—C10	120.0 (2)
C6—S2—Cd1	97.99 (8)	C12—C11—H11	120.0
C14—S3—C15	89.54 (12)	C10—C11—H11	120.0
C18—S4—Cd1	100.32 (8)	C11—C12—C7	120.9 (2)
C3—N1—C1	111.6 (2)	C11—C12—H12	119.6
C3—N1—Cd1	113.40 (15)	C7—C12—H12	119.6
C1—N1—Cd1	134.96 (16)	C14—C13—N5	115.1 (2)
C4—N2—N3	116.89 (19)	C14—C13—H13	122.5
C4—N2—Cd1	119.85 (16)	N5—C13—H13	122.5
N3—N2—Cd1	123.19 (14)	C13—C14—S3	110.70 (19)
C6—N3—N2	113.65 (19)	C13—C14—H14	124.7
C6—N4—C7	132.1 (2)	S3—C14—H14	124.7
C6—N4—H4N	113.3 (19)	N5—C15—C16	125.7 (2)
C7—N4—H4N	114.6 (19)	N5—C15—S3	113.64 (18)
C15—N5—C13	111.0 (2)	C16—C15—S3	120.61 (18)
C16—N6—N7	117.6 (2)	N6—C16—C15	125.3 (2)
C18—N7—N6	118.8 (2)	N6—C16—C17	116.1 (2)
C18—N7—H7N	126.0 (19)	C15—C16—C17	118.5 (2)
N6—N7—H7N	114.9 (19)	C16—C17—H17A	109.5
C18—N8—C19	126.4 (2)	C16—C17—H17B	109.5
C18—N8—H8N	117 (2)	H17A—C17—H17B	109.5
C19—N8—H8N	117 (2)	C16—C17—H17C	109.5
C2—C1—N1	114.9 (2)	H17A—C17—H17C	109.5
C2—C1—H1	122.6	H17B—C17—H17C	109.5
N1—C1—H1	122.6	N8—C18—N7	117.1 (2)
C1—C2—S1	110.05 (19)	N8—C18—S4	124.02 (18)
C1—C2—H2	125.0	N7—C18—S4	118.89 (18)
S1—C2—H2	125.0	C24—C19—C20	120.9 (2)
N1—C3—C4	122.9 (2)	C24—C19—N8	119.3 (2)
N1—C3—S1	113.40 (18)	C20—C19—N8	119.7 (2)
C4—C3—S1	123.67 (17)	C21—C20—C19	119.3 (2)
N2—C4—C3	113.9 (2)	C21—C20—H20	120.4
N2—C4—C5	125.2 (2)	C19—C20—H20	120.4
C3—C4—C5	120.9 (2)	C20—C21—C22	120.2 (2)
C4—C5—H5A	109.5	C20—C21—H21	119.9
C4—C5—H5B	109.5	C22—C21—H21	119.9
H5A—C5—H5B	109.5	C23—C22—C21	119.9 (2)
C4—C5—H5C	109.5	C23—C22—H22	120.0
H5A—C5—H5C	109.5	C21—C22—H22	120.0
H5B—C5—H5C	109.5	C22—C23—C24	120.4 (2)
N3—C6—N4	117.7 (2)	C22—C23—H23	119.8
N3—C6—S2	128.92 (18)	C24—C23—H23	119.8
N4—C6—S2	113.34 (17)	C19—C24—C23	119.3 (2)
C8—C7—C12	119.4 (2)	C19—C24—H24	120.3
C8—C7—N4	125.0 (2)	C23—C24—H24	120.3
N2—Cd1—S2—C6	−9.65 (9)	N2—N3—C6—N4	179.49 (18)
N1—Cd1—S2—C6	−30.51 (11)	N2—N3—C6—S2	−1.4 (3)
S4—Cd1—S2—C6	89.99 (8)	C7—N4—C6—N3	5.1 (4)
I1—Cd1—S2—C6	−154.51 (7)	C7—N4—C6—S2	−174.19 (19)
N2—Cd1—S4—C18	−69.76 (10)	Cd1—S2—C6—N3	10.5 (2)
N1—Cd1—S4—C18	1.05 (10)	Cd1—S2—C6—N4	−170.29 (15)
S2—Cd1—S4—C18	−146.47 (8)	C6—N4—C7—C8	−0.7 (4)
I1—Cd1—S4—C18	98.58 (8)	C6—N4—C7—C12	178.1 (2)
N2—Cd1—N1—C3	2.61 (15)	C12—C7—C8—C9	−1.6 (3)
S2—Cd1—N1—C3	24.0 (2)	N4—C7—C8—C9	177.2 (2)
S4—Cd1—N1—C3	−98.76 (15)	C7—C8—C9—C10	0.7 (4)
I1—Cd1—N1—C3	151.67 (15)	C8—C9—C10—C11	0.7 (4)
N2—Cd1—N1—C1	−176.6 (2)	C9—C10—C11—C12	−1.0 (3)
S2—Cd1—N1—C1	−155.22 (18)	C10—C11—C12—C7	0.0 (3)
S4—Cd1—N1—C1	82.0 (2)	C8—C7—C12—C11	1.3 (3)
I1—Cd1—N1—C1	−27.6 (2)	N4—C7—C12—C11	−177.6 (2)
N1—Cd1—N2—C4	−3.14 (16)	C15—N5—C13—C14	0.1 (3)
S2—Cd1—N2—C4	−169.57 (17)	N5—C13—C14—S3	−0.3 (3)
S4—Cd1—N2—C4	89.12 (16)	C15—S3—C14—C13	0.33 (19)
I1—Cd1—N2—C4	−70.69 (19)	C13—N5—C15—C16	178.5 (2)
N1—Cd1—N2—N3	179.88 (17)	C13—N5—C15—S3	0.2 (2)
S2—Cd1—N2—N3	13.46 (14)	C14—S3—C15—N5	−0.31 (18)
S4—Cd1—N2—N3	−87.86 (15)	C14—S3—C15—C16	−178.66 (19)
I1—Cd1—N2—N3	112.34 (15)	N7—N6—C16—C15	4.1 (3)
C4—N2—N3—C6	171.65 (19)	N7—N6—C16—C17	−176.95 (18)
Cd1—N2—N3—C6	−11.3 (2)	N5—C15—C16—N6	−2.1 (4)
C16—N6—N7—C18	−175.2 (2)	S3—C15—C16—N6	176.07 (18)
C3—N1—C1—C2	−0.1 (3)	N5—C15—C16—C17	179.0 (2)
Cd1—N1—C1—C2	179.13 (16)	S3—C15—C16—C17	−2.9 (3)
N1—C1—C2—S1	0.0 (3)	C19—N8—C18—N7	−177.6 (2)
C3—S1—C2—C1	0.08 (19)	C19—N8—C18—S4	3.7 (3)
C1—N1—C3—C4	177.1 (2)	N6—N7—C18—N8	8.5 (3)
Cd1—N1—C3—C4	−2.3 (3)	N6—N7—C18—S4	−172.77 (15)
C1—N1—C3—S1	0.2 (2)	Cd1—S4—C18—N8	−108.70 (19)
Cd1—N1—C3—S1	−179.24 (9)	Cd1—S4—C18—N7	72.63 (18)
C2—S1—C3—N1	−0.15 (18)	C18—N8—C19—C24	−115.4 (3)
C2—S1—C3—C4	−177.1 (2)	C18—N8—C19—C20	68.2 (3)
N3—N2—C4—C3	−179.80 (18)	C24—C19—C20—C21	0.3 (4)
Cd1—N2—C4—C3	3.0 (2)	N8—C19—C20—C21	176.6 (2)
N3—N2—C4—C5	−1.1 (3)	C19—C20—C21—C22	−0.2 (4)
Cd1—N2—C4—C5	−178.23 (16)	C20—C21—C22—C23	−0.1 (4)
N1—C3—C4—N2	−0.4 (3)	C21—C22—C23—C24	0.2 (4)
S1—C3—C4—N2	176.24 (16)	C20—C19—C24—C23	−0.1 (4)
N1—C3—C4—C5	−179.2 (2)	N8—C19—C24—C23	−176.4 (2)
S1—C3—C4—C5	−2.6 (3)	C22—C23—C24—C19	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···S2i	0.84 (2)	2.74 (2)	3.559 (2)	166 (2)
N7—H7N···N5	0.86 (2)	1.90 (2)	2.651 (3)	144 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯S2i	0.84 (2)	2.74 (2)	3.559 (2)	166 (2)
N7—H7N⋯N5	0.86 (2)	1.90 (2)	2.651 (3)	144 (3)

Symmetry code: (i) .