(2-Ethyl-2-oxazoline-κN)bis(N-ethyl-N-phenyl-dithio-carbamato-κ(2)S,S')cadmium.

In the title compound, [Cd(C(9)H(10)NS(2))(2)(C(5)H(9)NO)], the Cd(II) atom is five-coordinated in a distorted square-pyramidal geometry by four S atoms from two chelating N-ethyl-N-phenyl dithio-carbamate ligands and one N atom from a 2-ethyl-2-oxazoline ligand. Inter-molecular C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For background to and applications of dithio­carbamates, see: Green et al. (2004 ▶); Pickett & O’Brien (2001 ▶); Tiekink (2003 ▶); Valarmathi et al. (2011 ▶). For the synthesis of the parent dithio­carbamate, see: Onwudiwe & Ajibade (2010 ▶). For information regarding dithio­carbanate adducts, see: Green & O’Brien (1997 ▶); Ivanov et al. (2007 ▶); Onwudiwe et al. (2011 ▶). For the synthesis and structures of dithio­carbamates incorporating oxazoline mol­ecules, see: Decken et al. (2006 ▶); Gossage & Jenkins (2008 ▶).

Experimental

Crystal data

[Cd(C9H10NS2)2(C5H9NO)]

M = 604.18

Triclinic,

a = 10.3119 (2) Å

b = 11.4395 (2) Å

c = 12.2432 (3) Å

α = 84.756 (1)°

β = 77.395 (1)°

γ = 70.290 (1)°

V = 1326.61 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.16 mm−1

T = 200 K

0.37 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.75, T max = 0.82

23482 measured reflections

6626 independent reflections

5934 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.054

S = 1.06

6626 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038433/hy2583sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038433/hy2583Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038433/hy2583Isup3.cdx

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

[Cd(C9H10NS2)2(C5H9NO)]	Z = 2
Mr = 604.18	F(000) = 616
Triclinic, P1	Dx = 1.513 Mg m−3
Hall symbol: -P 1	Melting point: 562.15 K
a = 10.3119 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4395 (2) Å	Cell parameters from 192 reflections
c = 12.2432 (3) Å	θ = 1.7–25.5°
α = 84.756 (1)°	µ = 1.16 mm−1
β = 77.395 (1)°	T = 200 K
γ = 70.290 (1)°	Block, colourless
V = 1326.61 (5) Å3	0.37 × 0.23 × 0.18 mm

Bruker APEXII CCD diffractometer	6626 independent reflections
Radiation source: sealed tube	5934 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.75, Tmax = 0.82	k = −15→15
23482 measured reflections	l = −16→16

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) = 0.054	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0233P)2 + 0.6233P] where P = (Fo2 + 2Fc2)/3
6626 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.41 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	0.497101 (12)	0.297575 (11)	0.710351 (10)	0.02896 (4)
S11	0.70543 (5)	0.08672 (4)	0.66862 (3)	0.03257 (9)
S12	0.55149 (5)	0.24235 (4)	0.49921 (3)	0.03339 (9)
S21	0.42738 (4)	0.25089 (4)	0.93305 (3)	0.03282 (9)
S22	0.23016 (4)	0.35727 (4)	0.77674 (3)	0.03088 (9)
O3	0.70297 (14)	0.58511 (12)	0.68191 (11)	0.0403 (3)
N1	0.75835 (14)	0.02943 (12)	0.45349 (11)	0.0269 (3)
N2	0.16026 (15)	0.25674 (15)	0.97431 (11)	0.0316 (3)
N3	0.56806 (15)	0.46441 (12)	0.70659 (11)	0.0293 (3)
C11	0.73383 (17)	0.04933 (14)	0.34024 (13)	0.0263 (3)
C12	0.81004 (19)	0.11050 (16)	0.26380 (14)	0.0325 (4)
H12	0.8768	0.1391	0.2858	0.039*
C13	0.7883 (2)	0.12968 (16)	0.15508 (15)	0.0369 (4)
H13	0.8394	0.1725	0.1024	0.044*
C14	0.6923 (2)	0.08674 (16)	0.12285 (15)	0.0357 (4)
H14	0.6777	0.1001	0.0481	0.043*
C15	0.61753 (19)	0.02427 (15)	0.19940 (15)	0.0341 (4)
H15	0.552	−0.0056	0.177	0.041*
C16	0.63808 (18)	0.00527 (15)	0.30856 (14)	0.0303 (3)
H16	0.587	−0.0376	0.3612	0.036*
C17	0.67929 (17)	0.11157 (14)	0.53306 (13)	0.0256 (3)
C18	0.86741 (19)	−0.08783 (16)	0.47616 (15)	0.0336 (4)
H18A	0.9061	−0.0765	0.5402	0.04*
H18B	0.9452	−0.1084	0.41	0.04*
C19	0.8089 (2)	−0.19382 (18)	0.5024 (2)	0.0489 (5)
H19A	0.7793	−0.2108	0.4364	0.073*
H19B	0.7279	−0.1714	0.5649	0.073*
H19C	0.8815	−0.2681	0.5231	0.073*
C21	0.02419 (16)	0.28275 (15)	0.94601 (13)	0.0262 (3)
C22	−0.08658 (19)	0.38602 (16)	0.98745 (15)	0.0345 (4)
H22	−0.0734	0.4425	1.0328	0.041*
C23	−0.2169 (2)	0.40647 (19)	0.96237 (17)	0.0430 (5)
H23	−0.2931	0.4784	0.9889	0.052*
C24	−0.2363 (2)	0.3226 (2)	0.89888 (17)	0.0453 (5)
H24	−0.3266	0.3357	0.8835	0.054*
C25	−0.1251 (2)	0.2200 (2)	0.85763 (16)	0.0434 (5)
H25	−0.1387	0.1631	0.813	0.052*
C26	0.00623 (19)	0.19937 (17)	0.88082 (14)	0.0335 (4)
H26	0.0831	0.1287	0.8523	0.04*
C27	0.26380 (16)	0.28540 (15)	0.90230 (13)	0.0258 (3)
C28	0.1801 (2)	0.1855 (2)	1.08128 (16)	0.0456 (5)
H28A	0.2819	0.1458	1.0796	0.055*
H28B	0.1375	0.1189	1.0878	0.055*
C29	0.1152 (3)	0.2663 (3)	1.18189 (18)	0.0654 (7)
H29A	0.1547	0.3341	1.1747	0.098*
H29B	0.1352	0.2166	1.2495	0.098*
H29C	0.0132	0.3009	1.1871	0.098*
C31	0.4824 (2)	0.57458 (17)	0.77370 (17)	0.0422 (4)
H31A	0.4604	0.5516	0.8539	0.051*
H31B	0.3933	0.6169	0.7476	0.051*
C32	0.5742 (2)	0.65695 (17)	0.75524 (16)	0.0389 (4)
H32A	0.5287	0.737	0.7191	0.047*
H32B	0.5935	0.6736	0.827	0.047*
C33	0.68437 (18)	0.47990 (15)	0.66044 (14)	0.0292 (3)
C34	0.80295 (19)	0.39458 (17)	0.58279 (15)	0.0366 (4)
H34A	0.7899	0.3124	0.586	0.044*
H34B	0.8922	0.3833	0.6067	0.044*
C35	0.8113 (3)	0.4459 (2)	0.46306 (18)	0.0601 (6)
H35A	0.8927	0.39	0.4141	0.09*
H35B	0.8214	0.5283	0.4603	0.09*
H35C	0.7253	0.4523	0.4378	0.09*

	U11	U22	U33	U12	U13	U23
Cd1	0.02741 (7)	0.03168 (7)	0.02647 (6)	−0.01143 (5)	0.00288 (4)	−0.00717 (4)
S11	0.0394 (2)	0.0327 (2)	0.02396 (19)	−0.00906 (18)	−0.00617 (17)	−0.00305 (15)
S12	0.0342 (2)	0.0327 (2)	0.02624 (19)	−0.00064 (17)	−0.00540 (17)	−0.00694 (16)
S21	0.0250 (2)	0.0492 (2)	0.0274 (2)	−0.01531 (18)	−0.00557 (16)	−0.00294 (17)
S22	0.0253 (2)	0.0397 (2)	0.02583 (19)	−0.01067 (17)	−0.00322 (15)	0.00416 (16)
O3	0.0424 (7)	0.0316 (6)	0.0481 (8)	−0.0174 (6)	−0.0010 (6)	−0.0048 (5)
N1	0.0295 (7)	0.0242 (6)	0.0247 (6)	−0.0070 (5)	−0.0023 (5)	−0.0033 (5)
N2	0.0252 (7)	0.0490 (9)	0.0226 (6)	−0.0160 (6)	−0.0039 (5)	0.0016 (6)
N3	0.0298 (7)	0.0258 (6)	0.0285 (7)	−0.0071 (6)	0.0002 (6)	−0.0040 (5)
C11	0.0304 (8)	0.0216 (7)	0.0232 (7)	−0.0062 (6)	0.0009 (6)	−0.0054 (6)
C12	0.0361 (9)	0.0307 (8)	0.0315 (8)	−0.0155 (7)	0.0008 (7)	−0.0044 (7)
C13	0.0431 (10)	0.0317 (8)	0.0304 (9)	−0.0121 (8)	0.0024 (7)	0.0024 (7)
C14	0.0423 (10)	0.0307 (8)	0.0276 (8)	−0.0035 (7)	−0.0060 (7)	−0.0036 (7)
C15	0.0368 (9)	0.0277 (8)	0.0374 (9)	−0.0069 (7)	−0.0096 (7)	−0.0083 (7)
C16	0.0318 (9)	0.0257 (7)	0.0322 (8)	−0.0109 (7)	−0.0006 (7)	−0.0035 (6)
C17	0.0271 (8)	0.0268 (7)	0.0239 (7)	−0.0123 (6)	−0.0006 (6)	−0.0034 (6)
C18	0.0313 (9)	0.0306 (8)	0.0329 (9)	−0.0040 (7)	−0.0024 (7)	−0.0046 (7)
C19	0.0559 (13)	0.0295 (9)	0.0625 (13)	−0.0110 (9)	−0.0224 (11)	0.0062 (9)
C21	0.0241 (8)	0.0348 (8)	0.0213 (7)	−0.0136 (6)	−0.0017 (6)	0.0006 (6)
C22	0.0343 (9)	0.0313 (8)	0.0367 (9)	−0.0160 (7)	0.0046 (7)	−0.0029 (7)
C23	0.0279 (9)	0.0395 (10)	0.0506 (11)	−0.0070 (8)	0.0029 (8)	0.0120 (8)
C24	0.0294 (9)	0.0681 (14)	0.0429 (11)	−0.0235 (9)	−0.0141 (8)	0.0231 (10)
C25	0.0487 (12)	0.0616 (13)	0.0332 (9)	−0.0317 (10)	−0.0142 (8)	0.0010 (9)
C26	0.0340 (9)	0.0377 (9)	0.0282 (8)	−0.0115 (7)	−0.0034 (7)	−0.0058 (7)
C27	0.0242 (8)	0.0301 (8)	0.0231 (7)	−0.0095 (6)	−0.0014 (6)	−0.0062 (6)
C28	0.0390 (11)	0.0690 (14)	0.0330 (10)	−0.0249 (10)	−0.0093 (8)	0.0121 (9)
C29	0.0788 (18)	0.099 (2)	0.0295 (10)	−0.0434 (16)	−0.0114 (11)	0.0008 (11)
C31	0.0410 (10)	0.0313 (9)	0.0446 (11)	−0.0061 (8)	0.0069 (8)	−0.0124 (8)
C32	0.0496 (11)	0.0295 (8)	0.0354 (9)	−0.0090 (8)	−0.0069 (8)	−0.0077 (7)
C33	0.0328 (9)	0.0259 (7)	0.0281 (8)	−0.0102 (7)	−0.0048 (7)	0.0030 (6)
C34	0.0323 (9)	0.0337 (9)	0.0373 (9)	−0.0091 (7)	0.0042 (7)	−0.0010 (7)
C35	0.0701 (16)	0.0582 (14)	0.0361 (11)	−0.0131 (12)	0.0092 (10)	−0.0006 (10)

Cd1—N3	2.2563 (14)	C19—H19A	0.98
Cd1—S22	2.5615 (4)	C19—H19B	0.98
Cd1—S12	2.6121 (4)	C19—H19C	0.98
Cd1—S11	2.6354 (5)	C21—C26	1.380 (2)
Cd1—S21	2.7154 (4)	C21—C22	1.380 (2)
S11—C17	1.7221 (16)	C22—C23	1.382 (3)
S12—C17	1.7152 (17)	C22—H22	0.95
S21—C27	1.7157 (16)	C23—C24	1.378 (3)
S22—C27	1.7230 (16)	C23—H23	0.95
O3—C33	1.338 (2)	C24—C25	1.377 (3)
O3—C32	1.457 (2)	C24—H24	0.95
N1—C17	1.342 (2)	C25—C26	1.382 (3)
N1—C11	1.447 (2)	C25—H25	0.95
N1—C18	1.481 (2)	C26—H26	0.95
N2—C27	1.341 (2)	C28—C29	1.500 (3)
N2—C21	1.445 (2)	C28—H28A	0.99
N2—C28	1.493 (2)	C28—H28B	0.99
N3—C33	1.272 (2)	C29—H29A	0.98
N3—C31	1.472 (2)	C29—H29B	0.98
C11—C12	1.383 (2)	C29—H29C	0.98
C11—C16	1.385 (2)	C31—C32	1.518 (3)
C12—C13	1.384 (3)	C31—H31A	0.99
C12—H12	0.95	C31—H31B	0.99
C13—C14	1.382 (3)	C32—H32A	0.99
C13—H13	0.95	C32—H32B	0.99
C14—C15	1.385 (3)	C33—C34	1.486 (2)
C14—H14	0.95	C34—C35	1.524 (3)
C15—C16	1.385 (2)	C34—H34A	0.99
C15—H15	0.95	C34—H34B	0.99
C16—H16	0.95	C35—H35A	0.98
C18—C19	1.508 (3)	C35—H35B	0.98
C18—H18A	0.99	C35—H35C	0.98
C18—H18B	0.99
N3—Cd1—S22	110.83 (4)	C22—C21—N2	120.50 (15)
N3—Cd1—S12	103.12 (4)	C21—C22—C23	119.38 (17)
S22—Cd1—S12	106.646 (14)	C21—C22—H22	120.3
N3—Cd1—S11	113.83 (4)	C23—C22—H22	120.3
S22—Cd1—S11	134.900 (15)	C24—C23—C22	120.08 (18)
S12—Cd1—S11	69.059 (13)	C24—C23—H23	120.0
N3—Cd1—S21	102.68 (4)	C22—C23—H23	120.0
S22—Cd1—S21	68.706 (13)	C25—C24—C23	120.13 (17)
S12—Cd1—S21	153.616 (15)	C25—C24—H24	119.9
S11—Cd1—S21	95.366 (14)	C23—C24—H24	119.9
C17—S11—Cd1	85.11 (6)	C24—C25—C26	120.36 (18)
C17—S12—Cd1	85.98 (5)	C24—C25—H25	119.8
C27—S21—Cd1	82.05 (5)	C26—C25—H25	119.8
C27—S22—Cd1	86.74 (5)	C21—C26—C25	119.11 (17)
C33—O3—C32	106.82 (13)	C21—C26—H26	120.4
C17—N1—C11	120.28 (13)	C25—C26—H26	120.4
C17—N1—C18	123.19 (14)	N2—C27—S21	121.16 (12)
C11—N1—C18	116.43 (13)	N2—C27—S22	118.67 (12)
C27—N2—C21	120.66 (13)	S21—C27—S22	120.16 (9)
C27—N2—C28	123.45 (14)	N2—C28—C29	112.39 (19)
C21—N2—C28	115.58 (13)	N2—C28—H28A	109.1
C33—N3—C31	107.76 (14)	C29—C28—H28A	109.1
C33—N3—Cd1	130.29 (11)	N2—C28—H28B	109.1
C31—N3—Cd1	121.64 (11)	C29—C28—H28B	109.1
C12—C11—C16	120.73 (15)	H28A—C28—H28B	107.9
C12—C11—N1	118.80 (15)	C28—C29—H29A	109.5
C16—C11—N1	120.45 (14)	C28—C29—H29B	109.5
C11—C12—C13	119.47 (16)	H29A—C29—H29B	109.5
C11—C12—H12	120.3	C28—C29—H29C	109.5
C13—C12—H12	120.3	H29A—C29—H29C	109.5
C14—C13—C12	120.22 (16)	H29B—C29—H29C	109.5
C14—C13—H13	119.9	N3—C31—C32	104.14 (15)
C12—C13—H13	119.9	N3—C31—H31A	110.9
C13—C14—C15	120.05 (16)	C32—C31—H31A	110.9
C13—C14—H14	120.0	N3—C31—H31B	110.9
C15—C14—H14	120.0	C32—C31—H31B	110.9
C16—C15—C14	120.12 (16)	H31A—C31—H31B	108.9
C16—C15—H15	119.9	O3—C32—C31	103.97 (13)
C14—C15—H15	119.9	O3—C32—H32A	111.0
C15—C16—C11	119.40 (15)	C31—C32—H32A	111.0
C15—C16—H16	120.3	O3—C32—H32B	111.0
C11—C16—H16	120.3	C31—C32—H32B	111.0
N1—C17—S12	119.65 (12)	H32A—C32—H32B	109.0
N1—C17—S11	120.50 (12)	N3—C33—O3	117.29 (15)
S12—C17—S11	119.85 (9)	N3—C33—C34	127.25 (15)
N1—C18—C19	111.61 (15)	O3—C33—C34	115.45 (15)
N1—C18—H18A	109.3	C33—C34—C35	110.98 (16)
C19—C18—H18A	109.3	C33—C34—H34A	109.4
N1—C18—H18B	109.3	C35—C34—H34A	109.4
C19—C18—H18B	109.3	C33—C34—H34B	109.4
H18A—C18—H18B	108.0	C35—C34—H34B	109.4
C18—C19—H19A	109.5	H34A—C34—H34B	108.0
C18—C19—H19B	109.5	C34—C35—H35A	109.5
H19A—C19—H19B	109.5	C34—C35—H35B	109.5
C18—C19—H19C	109.5	H35A—C35—H35B	109.5
H19A—C19—H19C	109.5	C34—C35—H35C	109.5
H19B—C19—H19C	109.5	H35A—C35—H35C	109.5
C26—C21—C22	120.92 (16)	H35B—C35—H35C	109.5
C26—C21—N2	118.52 (15)
N3—Cd1—S11—C17	−95.97 (6)	Cd1—S12—C17—N1	179.40 (12)
S22—Cd1—S11—C17	92.53 (5)	Cd1—S12—C17—S11	−0.71 (9)
S12—Cd1—S11—C17	−0.43 (5)	Cd1—S11—C17—N1	−179.41 (13)
S21—Cd1—S11—C17	157.62 (5)	Cd1—S11—C17—S12	0.70 (8)
N3—Cd1—S12—C17	111.22 (6)	C17—N1—C18—C19	91.8 (2)
S22—Cd1—S12—C17	−131.98 (5)	C11—N1—C18—C19	−84.61 (19)
S11—Cd1—S12—C17	0.43 (5)	C27—N2—C21—C26	82.5 (2)
S21—Cd1—S12—C17	−56.47 (6)	C28—N2—C21—C26	−91.38 (19)
N3—Cd1—S21—C27	116.69 (6)	C27—N2—C21—C22	−100.24 (19)
S22—Cd1—S21—C27	9.02 (5)	C28—N2—C21—C22	85.9 (2)
S12—Cd1—S21—C27	−75.59 (6)	C26—C21—C22—C23	−0.5 (3)
S11—Cd1—S21—C27	−127.39 (5)	N2—C21—C22—C23	−177.74 (15)
N3—Cd1—S22—C27	−104.87 (6)	C21—C22—C23—C24	1.6 (3)
S12—Cd1—S22—C27	143.59 (5)	C22—C23—C24—C25	−1.8 (3)
S11—Cd1—S22—C27	66.81 (6)	C23—C24—C25—C26	0.9 (3)
S21—Cd1—S22—C27	−8.91 (5)	C22—C21—C26—C25	−0.3 (3)
S22—Cd1—N3—C33	−165.44 (14)	N2—C21—C26—C25	176.91 (15)
S12—Cd1—N3—C33	−51.65 (16)	C24—C25—C26—C21	0.2 (3)
S11—Cd1—N3—C33	21.00 (16)	C21—N2—C27—S21	−178.05 (12)
S21—Cd1—N3—C33	122.78 (15)	C28—N2—C27—S21	−4.7 (2)
S22—Cd1—N3—C31	21.83 (15)	C21—N2—C27—S22	1.6 (2)
S12—Cd1—N3—C31	135.62 (13)	C28—N2—C27—S22	174.93 (14)
S11—Cd1—N3—C31	−151.73 (13)	Cd1—S21—C27—N2	165.05 (14)
S21—Cd1—N3—C31	−49.95 (14)	Cd1—S21—C27—S22	−14.54 (8)
C17—N1—C11—C12	92.93 (19)	Cd1—S22—C27—N2	−164.30 (13)
C18—N1—C11—C12	−90.55 (18)	Cd1—S22—C27—S21	15.31 (9)
C17—N1—C11—C16	−88.54 (19)	C27—N2—C28—C29	106.4 (2)
C18—N1—C11—C16	87.97 (19)	C21—N2—C28—C29	−79.9 (2)
C16—C11—C12—C13	1.2 (3)	C33—N3—C31—C32	0.5 (2)
N1—C11—C12—C13	179.69 (15)	Cd1—N3—C31—C32	174.66 (11)
C11—C12—C13—C14	−0.8 (3)	C33—O3—C32—C31	1.35 (19)
C12—C13—C14—C15	0.0 (3)	N3—C31—C32—O3	−1.1 (2)
C13—C14—C15—C16	0.4 (3)	C31—N3—C33—O3	0.4 (2)
C14—C15—C16—C11	0.0 (3)	Cd1—N3—C33—O3	−173.07 (11)
C12—C11—C16—C15	−0.8 (2)	C31—N3—C33—C34	−178.45 (18)
N1—C11—C16—C15	−179.31 (14)	Cd1—N3—C33—C34	8.1 (3)
C11—N1—C17—S12	−1.5 (2)	C32—O3—C33—N3	−1.2 (2)
C18—N1—C17—S12	−177.80 (12)	C32—O3—C33—C34	177.82 (15)
C11—N1—C17—S11	178.59 (11)	N3—C33—C34—C35	106.5 (2)
C18—N1—C17—S11	2.3 (2)	O3—C33—C34—C35	−72.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···Cg1i	0.95	2.61	3.558 (2)	177
C32—H32A···Cg1ii	0.99	2.72	3.511 (2)	137
C13—H13···Cg2iii	0.95	2.61	3.510 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯Cg1i	0.95	2.61	3.558 (2)	177
C32—H32A⋯Cg1ii	0.99	2.72	3.511 (2)	137
C13—H13⋯Cg2iii	0.95	2.61	3.510 (2)	157

Symmetry codes: (i) ; (ii) ; (iii) .