Tris[2-(2-thienyl-methyl-amino)-eth-yl]ammonium triiodide.

In the title compound, C(21)H(33)N(4)S(3) (3+)·3I(-), three secondary amines are protonated, while the central amine remains unprotonated. One thio-phene is disordered with an occupancy ratio of 0.868 (6)/0.132 (6). Each protonated amine is involved in N-H⋯I hydrogen-bonding inter-actions with the iodide anions.

Related literature

For general background to anion hosts, see: Bianchi et al. (1997 ▶); Kang et al. (2005 ▶); Hossain (2008 ▶); For related structures, see: Bazzicalupi et al. (2009 ▶); Hossain et al. (2002 ▶, 2004 ▶); Burgess et al. (1991 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C21H33N4S3 3+·3I−

M = 818.42

Orthorhombic,

a = 10.5433 (5) Å

b = 11.4203 (6) Å

c = 24.5107 (15) Å

V = 2951.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.41 mm−1

T = 90 K

0.20 × 0.17 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

Absorption correction: multi-scan (HKL ; Otwinowski & Minor, 1997 ▶) T min = 0.549, T max = 0.629

90447 measured reflections

10653 independent reflections

9446 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.04

10653 reflections

277 parameters

30 restraints

H-atom parameters constrained

Δρmax = 2.96 e Å−3

Δρmin = −2.18 e Å−3

Absolute structure: Flack (1983 ▶), 4708 Friedel pairs

Flack parameter: 0.02 (2)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP–3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039462/rk2235sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039462/rk2235Isup2.hkl

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

C21H33N4S33+·3I−	F(000) = 1576
Mr = 818.42	Dx = 1.842 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5918 reflections
a = 10.5433 (5) Å	θ = 2.5–32.6°
b = 11.4203 (6) Å	µ = 3.41 mm−1
c = 24.5107 (15) Å	T = 90 K
V = 2951.3 (3) Å3	Block, colourless
Z = 4	0.20 × 0.17 × 0.15 mm

Nonius KappaCCD diffractometer with Oxford Cryostream	10653 independent reflections
Radiation source: fine–focus sealed tube	9446 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω– and φ–scans	θmax = 32.6°, θmin = 2.6°
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997)	h = −15→15
Tmin = 0.549, Tmax = 0.629	k = −17→17
90447 measured reflections	l = −36→36

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0425P)2 + 8.7643P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.003
10653 reflections	Δρmax = 2.96 e Å−3
277 parameters	Δρmin = −2.18 e Å−3
30 restraints	Absolute structure: Flack (1983), 4708 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (2)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
I1	0.66009 (2)	0.80566 (2)	0.512489 (10)	0.01937 (5)
I2	0.28784 (4)	0.15756 (3)	0.526628 (15)	0.03742 (9)
I3	0.69376 (3)	0.78787 (3)	0.708662 (14)	0.03409 (8)
S2	0.31359 (12)	1.01963 (11)	0.68942 (5)	0.0312 (2)
N1	0.4937 (3)	0.5219 (3)	0.59749 (14)	0.0169 (6)
N2	0.3384 (4)	0.4343 (3)	0.46508 (14)	0.0209 (6)
H21N	0.2630	0.4723	0.4718	0.025*
H22N	0.3266	0.3558	0.4717	0.025*
N3	0.4390 (3)	0.7677 (3)	0.62014 (14)	0.0179 (6)
H31N	0.4863	0.7388	0.5916	0.021*
H32N	0.4946	0.7922	0.6467	0.021*
N4	0.7721 (4)	0.5480 (4)	0.57790 (16)	0.0247 (7)
H41N	0.7136	0.6020	0.5660	0.030*
H42N	0.7851	0.4954	0.5500	0.030*
C1	0.3954 (4)	0.4734 (4)	0.56157 (18)	0.0210 (8)
H1A	0.3155	0.5180	0.5662	0.025*
H1B	0.3789	0.3907	0.5713	0.025*
C2	0.4394 (4)	0.4811 (4)	0.50268 (17)	0.0225 (8)
H2A	0.4580	0.5637	0.4933	0.027*
H2B	0.5183	0.4352	0.4980	0.027*
C3	0.3761 (5)	0.4522 (4)	0.40606 (18)	0.0273 (9)
H3A	0.3702	0.5367	0.3973	0.033*
H3B	0.4657	0.4283	0.4015	0.033*
S1	0.13415 (11)	0.40416 (11)	0.36040 (5)	0.0283 (2)
C4	0.2957 (4)	0.3848 (4)	0.36614 (18)	0.0251 (8)
C5	0.3416 (5)	0.3115 (4)	0.32588 (17)	0.0267 (8)
H5	0.4283	0.2907	0.3217	0.032*
C6	0.2417 (5)	0.2710 (4)	0.29130 (19)	0.0315 (10)
H6	0.2547	0.2187	0.2617	0.038*
C7	0.1270 (5)	0.3147 (4)	0.30498 (19)	0.0296 (9)
H7	0.0509	0.2974	0.2858	0.036*
C8	0.4383 (4)	0.5616 (4)	0.64961 (17)	0.0205 (7)
H8A	0.5074	0.5772	0.6760	0.025*
H8B	0.3845	0.4985	0.6648	0.025*
C9	0.3594 (4)	0.6709 (4)	0.64269 (16)	0.0196 (7)
H9A	0.2878	0.6549	0.6177	0.024*
H9B	0.3240	0.6948	0.6784	0.024*
C10	0.3644 (4)	0.8723 (4)	0.60019 (17)	0.0202 (8)
H10A	0.4240	0.9363	0.5908	0.024*
H10B	0.3179	0.8505	0.5666	0.024*
C11	0.2721 (4)	0.9156 (4)	0.64173 (17)	0.0209 (8)
C12	0.1429 (5)	0.8797 (5)	0.64632 (19)	0.0309 (11)
H12	0.1017	0.8239	0.6237	0.037*
C13	0.0854 (5)	0.9420 (5)	0.6908 (2)	0.0340 (11)
H13	−0.0005	0.9312	0.7013	0.041*
C14	0.1650 (5)	1.0182 (5)	0.7170 (2)	0.0336 (10)
H14	0.1403	1.0651	0.7472	0.040*
C15	0.5898 (4)	0.4310 (4)	0.6089 (2)	0.0243 (8)
H15A	0.6016	0.3819	0.5760	0.029*
H15B	0.5590	0.3798	0.6387	0.029*
C16	0.7168 (4)	0.4837 (4)	0.62527 (18)	0.0235 (8)
H16A	0.7049	0.5382	0.6563	0.028*
H16B	0.7755	0.4208	0.6370	0.028*
C17	0.8947 (4)	0.6105 (5)	0.5889 (2)	0.0337 (11)
H17A	0.8785	0.6789	0.6127	0.040*	0.868 (6)
H17B	0.9304	0.6396	0.5541	0.040*	0.868 (6)
H17C	0.8735	0.6876	0.6050	0.040*	0.132 (6)
H17D	0.9355	0.6258	0.5532	0.040*	0.132 (6)
S3A	1.04963 (14)	0.40627 (17)	0.58903 (9)	0.0441 (6)	0.868 (6)
C18A	0.9893 (7)	0.5305 (6)	0.6160 (3)	0.0322 (13)*	0.868 (6)
C19A	1.0385 (6)	0.5521 (6)	0.6685 (3)	0.0331 (12)*	0.868 (6)
H19A	1.0177	0.6178	0.6905	0.040*	0.868 (6)
C20A	1.1234 (8)	0.4622 (7)	0.6835 (3)	0.0493 (18)*	0.868 (6)
H20A	1.1680	0.4617	0.7172	0.059*	0.868 (6)
C21A	1.1351 (8)	0.3783 (7)	0.6464 (3)	0.0448 (17)*	0.868 (6)
H21A	1.1856	0.3103	0.6513	0.054*	0.868 (6)
S3B	1.0412 (10)	0.6016 (10)	0.6856 (4)	0.033 (3)*	0.132 (6)
C18B	0.993 (4)	0.554 (3)	0.6254 (12)	0.033 (3)*	0.132 (6)
C19B	1.054 (4)	0.447 (3)	0.6152 (12)	0.033 (3)*	0.132 (6)
H19B	1.0474	0.4043	0.5819	0.040*	0.132 (6)
C20B	1.128 (4)	0.408 (2)	0.6616 (14)	0.033 (3)*	0.132 (6)
H20B	1.1692	0.3344	0.6640	0.040*	0.132 (6)
C21B	1.132 (3)	0.489 (3)	0.7001 (13)	0.033 (3)*	0.132 (6)
H21B	1.1821	0.4833	0.7323	0.040*	0.132 (6)

	U11	U22	U33	U12	U13	U23
I1	0.01816 (10)	0.02106 (11)	0.01888 (10)	0.00339 (9)	0.00220 (9)	0.00444 (9)
I2	0.0504 (2)	0.02224 (13)	0.03961 (17)	−0.01073 (13)	−0.01876 (15)	0.00445 (12)
I3	0.03868 (16)	0.02779 (14)	0.03580 (15)	−0.00952 (12)	−0.01948 (13)	0.00415 (12)
S2	0.0324 (6)	0.0314 (6)	0.0298 (5)	0.0004 (5)	0.0018 (5)	−0.0100 (4)
N1	0.0152 (14)	0.0155 (14)	0.0200 (15)	0.0018 (12)	−0.0020 (12)	−0.0027 (12)
N2	0.0193 (14)	0.0213 (15)	0.0221 (15)	−0.0023 (13)	−0.0029 (13)	−0.0018 (12)
N3	0.0152 (14)	0.0196 (15)	0.0189 (15)	−0.0007 (11)	−0.0005 (12)	−0.0024 (12)
N4	0.0216 (17)	0.0277 (18)	0.0248 (17)	0.0067 (14)	0.0015 (14)	0.0108 (14)
C1	0.0190 (18)	0.0216 (19)	0.0223 (18)	−0.0027 (15)	−0.0032 (15)	0.0002 (15)
C2	0.0193 (17)	0.0244 (19)	0.024 (2)	−0.0032 (15)	0.0001 (14)	−0.0034 (15)
C3	0.034 (2)	0.030 (2)	0.0179 (18)	−0.0056 (18)	0.0019 (17)	0.0004 (16)
S1	0.0268 (6)	0.0249 (5)	0.0334 (6)	0.0016 (4)	−0.0023 (4)	−0.0020 (4)
C4	0.0248 (19)	0.0242 (19)	0.026 (2)	−0.0003 (17)	−0.0041 (17)	0.0008 (16)
C5	0.033 (2)	0.026 (2)	0.0215 (17)	−0.0029 (19)	−0.0073 (16)	0.0021 (16)
C6	0.047 (3)	0.028 (2)	0.0199 (19)	0.0038 (19)	−0.0049 (19)	0.0035 (17)
C7	0.035 (2)	0.027 (2)	0.027 (2)	−0.0053 (18)	−0.0090 (17)	0.0038 (17)
C8	0.0180 (17)	0.0239 (19)	0.0196 (18)	−0.0032 (14)	−0.0006 (14)	0.0003 (15)
C9	0.0171 (17)	0.0211 (18)	0.0208 (17)	−0.0004 (13)	0.0043 (13)	−0.0005 (14)
C10	0.023 (2)	0.0185 (17)	0.0191 (17)	0.0024 (14)	0.0001 (14)	−0.0026 (13)
C11	0.0221 (19)	0.0207 (18)	0.0200 (18)	0.0051 (15)	−0.0031 (15)	−0.0042 (14)
C12	0.030 (2)	0.040 (3)	0.0221 (19)	0.024 (2)	0.0050 (17)	−0.0012 (18)
C13	0.025 (2)	0.044 (3)	0.034 (2)	0.010 (2)	−0.0009 (19)	−0.008 (2)
C14	0.032 (2)	0.042 (3)	0.027 (2)	0.012 (2)	0.0066 (19)	−0.0079 (19)
C15	0.0193 (19)	0.023 (2)	0.030 (2)	0.0009 (15)	0.0007 (15)	0.0011 (17)
C16	0.0158 (18)	0.027 (2)	0.027 (2)	0.0045 (15)	0.0024 (15)	0.0129 (16)
C17	0.0174 (19)	0.043 (3)	0.041 (3)	0.0009 (18)	−0.0022 (19)	0.024 (2)
S3A	0.0175 (6)	0.0484 (11)	0.0664 (13)	0.0046 (6)	0.0020 (7)	0.0329 (9)

S2—C14	1.706 (5)	C9—H9B	0.9900
S2—C11	1.723 (4)	C10—C11	1.493 (6)
N1—C1	1.468 (5)	C10—H10A	0.9900
N1—C8	1.476 (5)	C10—H10B	0.9900
N1—C15	1.477 (6)	C11—C12	1.427 (7)
N2—C2	1.506 (5)	C12—C13	1.436 (7)
N2—C3	1.514 (6)	C12—H12	0.9500
N2—H21N	0.9200	C13—C14	1.368 (8)
N2—H22N	0.9200	C13—H13	0.9500
N3—C9	1.493 (5)	C14—H14	0.9500
N3—C10	1.512 (5)	C15—C16	1.522 (6)
N3—H31N	0.9200	C15—H15A	0.9900
N3—H32N	0.9200	C15—H15B	0.9900
N4—C16	1.492 (5)	C16—H16A	0.9900
N4—C17	1.501 (6)	C16—H16B	0.9900
N4—H41N	0.9200	C17—C18A	1.507 (8)
N4—H42N	0.9200	C17—C18B	1.51 (2)
C1—C2	1.519 (6)	C17—H17A	0.9900
C1—H1A	0.9900	C17—H17B	0.9900
C1—H1B	0.9900	C17—H17C	0.9900
C2—H2A	0.9900	C17—H17D	0.9900
C2—H2B	0.9900	S3A—C18A	1.690 (6)
C3—C4	1.506 (6)	S3A—C21A	1.700 (7)
C3—H3A	0.9900	C18A—C19A	1.409 (8)
C3—H3B	0.9900	C19A—C20A	1.411 (9)
S1—C7	1.702 (5)	C19A—H19A	0.9500
S1—C4	1.724 (5)	C20A—C21A	1.327 (10)
C4—C5	1.382 (6)	C20A—H20A	0.9500
C5—C6	1.429 (6)	C21A—H21A	0.9500
C5—H5	0.9500	S3B—C21B	1.641 (16)
C6—C7	1.350 (7)	S3B—C18B	1.655 (16)
C6—H6	0.9500	C18B—C19B	1.406 (17)
C7—H7	0.9500	C19B—C20B	1.448 (17)
C8—C9	1.510 (6)	C19B—H19B	0.9500
C8—H8A	0.9900	C20B—C21B	1.322 (17)
C8—H8B	0.9900	C20B—H20B	0.9500
C9—H9A	0.9900	C21B—H21B	0.9500
C14—S2—C11	91.7 (2)	H10A—C10—H10B	107.9
C1—N1—C8	110.8 (3)	C12—C11—C10	125.5 (4)
C1—N1—C15	109.5 (3)	C12—C11—S2	112.8 (3)
C8—N1—C15	108.9 (3)	C10—C11—S2	121.7 (3)
C2—N2—C3	110.6 (3)	C11—C12—C13	108.7 (5)
C2—N2—H21N	109.5	C11—C12—H12	125.7
C3—N2—H21N	109.5	C13—C12—H12	125.7
C2—N2—H22N	109.5	C14—C13—C12	114.3 (5)
C3—N2—H22N	109.5	C14—C13—H13	122.8
H21N—N2—H22N	108.1	C12—C13—H13	122.8
C9—N3—C10	114.3 (3)	C13—C14—S2	112.6 (4)
C9—N3—H31N	108.7	C13—C14—H14	123.7
C10—N3—H31N	108.7	S2—C14—H14	123.7
C9—N3—H32N	108.7	N1—C15—C16	112.1 (4)
C10—N3—H32N	108.7	N1—C15—H15A	109.2
H31N—N3—H32N	107.6	C16—C15—H15A	109.2
C16—N4—C17	115.5 (4)	N1—C15—H15B	109.2
C16—N4—H41N	108.4	C16—C15—H15B	109.2
C17—N4—H41N	108.4	H15A—C15—H15B	107.9
C16—N4—H42N	108.4	N4—C16—C15	109.5 (4)
C17—N4—H42N	108.4	N4—C16—H16A	109.8
H41N—N4—H42N	107.5	C15—C16—H16A	109.8
N1—C1—C2	109.4 (3)	N4—C16—H16B	109.8
N1—C1—H1A	109.8	C15—C16—H16B	109.8
C2—C1—H1A	109.8	H16A—C16—H16B	108.2
N1—C1—H1B	109.8	N4—C17—C18A	111.1 (5)
C2—C1—H1B	109.8	N4—C17—C18B	119.4 (19)
H1A—C1—H1B	108.2	N4—C17—H17A	109.4
N2—C2—C1	110.2 (3)	C18A—C17—H17A	109.4
N2—C2—H2A	109.6	C18B—C17—H17A	96.2
C1—C2—H2A	109.6	N4—C17—H17B	109.4
N2—C2—H2B	109.6	C18A—C17—H17B	109.4
C1—C2—H2B	109.6	C18B—C17—H17B	113.2
H2A—C2—H2B	108.1	H17A—C17—H17B	108.0
C4—C3—N2	113.8 (4)	N4—C17—H17C	107.5
C4—C3—H3A	108.8	C18A—C17—H17C	120.9
N2—C3—H3A	108.8	C18B—C17—H17C	107.5
C4—C3—H3B	108.8	H17B—C17—H17C	97.5
N2—C3—H3B	108.8	N4—C17—H17D	107.5
H3A—C3—H3B	107.7	C18A—C17—H17D	102.1
C7—S1—C4	91.8 (2)	C18B—C17—H17D	107.5
C5—C4—C3	125.2 (4)	H17A—C17—H17D	117.2
C5—C4—S1	111.5 (3)	H17C—C17—H17D	107.0
C3—C4—S1	122.9 (4)	C18A—S3A—C21A	91.9 (3)
C4—C5—C6	111.2 (4)	C19A—C18A—C17	122.7 (6)
C4—C5—H5	124.4	C19A—C18A—S3A	111.4 (5)
C6—C5—H5	124.4	C17—C18A—S3A	125.8 (5)
C7—C6—C5	113.2 (4)	C18A—C19A—C20A	110.2 (6)
C7—C6—H6	123.4	C18A—C19A—H19A	124.9
C5—C6—H6	123.4	C20A—C19A—H19A	124.9
C6—C7—S1	112.3 (4)	C21A—C20A—C19A	113.9 (7)
C6—C7—H7	123.8	C21A—C20A—H20A	123.0
S1—C7—H7	123.8	C19A—C20A—H20A	123.0
N1—C8—C9	112.0 (3)	C20A—C21A—S3A	112.5 (6)
N1—C8—H8A	109.2	C20A—C21A—H21A	123.8
C9—C8—H8A	109.2	S3A—C21A—H21A	123.8
N1—C8—H8B	109.2	C21B—S3B—C18B	96.6 (11)
C9—C8—H8B	109.2	C19B—C18B—C17	125.6 (18)
H8A—C8—H8B	107.9	C19B—C18B—S3B	107.7 (14)
N3—C9—C8	110.1 (3)	C17—C18B—S3B	126.6 (17)
N3—C9—H9A	109.6	C18B—C19B—C20B	111.8 (16)
C8—C9—H9A	109.6	C18B—C19B—H19B	124.1
N3—C9—H9B	109.6	C20B—C19B—H19B	124.1
C8—C9—H9B	109.6	C21B—C20B—C19B	111.5 (17)
H9A—C9—H9B	108.1	C21B—C20B—H20B	124.2
C11—C10—N3	112.3 (3)	C19B—C20B—H20B	124.2
C11—C10—H10A	109.1	C20B—C21B—S3B	111.9 (15)
N3—C10—H10A	109.1	C20B—C21B—H21B	124.0
C11—C10—H10B	109.1	S3B—C21B—H21B	124.0
N3—C10—H10B	109.1
C8—N1—C1—C2	156.4 (4)	C1—N1—C15—C16	156.8 (4)
C15—N1—C1—C2	−83.5 (4)	C8—N1—C15—C16	−82.0 (4)
C3—N2—C2—C1	174.6 (4)	C17—N4—C16—C15	176.8 (4)
N1—C1—C2—N2	−178.7 (3)	N1—C15—C16—N4	−66.4 (5)
C2—N2—C3—C4	167.0 (4)	C16—N4—C17—C18A	50.2 (6)
N2—C3—C4—C5	−128.0 (5)	C16—N4—C17—C18B	38.5 (15)
N2—C3—C4—S1	60.0 (5)	N4—C17—C18A—C19A	−118.1 (7)
C7—S1—C4—C5	0.3 (4)	C18B—C17—C18A—C19A	12 (9)
C7—S1—C4—C3	173.3 (4)	N4—C17—C18A—S3A	61.9 (7)
C3—C4—C5—C6	−173.7 (4)	C18B—C17—C18A—S3A	−168 (10)
S1—C4—C5—C6	−0.9 (5)	C21A—S3A—C18A—C19A	2.0 (6)
C4—C5—C6—C7	1.1 (6)	C21A—S3A—C18A—C17	−178.0 (7)
C5—C6—C7—S1	−0.9 (6)	C17—C18A—C19A—C20A	179.3 (7)
C4—S1—C7—C6	0.3 (4)	S3A—C18A—C19A—C20A	−0.7 (8)
C1—N1—C8—C9	−71.3 (4)	C18A—C19A—C20A—C21A	−1.4 (10)
C15—N1—C8—C9	168.2 (3)	C19A—C20A—C21A—S3A	3.0 (10)
C10—N3—C9—C8	167.4 (3)	C18A—S3A—C21A—C20A	−2.9 (7)
N1—C8—C9—N3	−59.3 (4)	N4—C17—C18B—C19B	62 (5)
C9—N3—C10—C11	51.0 (4)	C18A—C17—C18B—C19B	7(6)
N3—C10—C11—C12	−91.8 (5)	N4—C17—C18B—S3B	−114 (3)
N3—C10—C11—S2	89.5 (4)	C18A—C17—C18B—S3B	−169 (13)
C14—S2—C11—C12	0.6 (4)	C21B—S3B—C18B—C19B	−2(4)
C14—S2—C11—C10	179.4 (4)	C21B—S3B—C18B—C17	175 (4)
C10—C11—C12—C13	−179.4 (4)	C17—C18B—C19B—C20B	−172 (4)
S2—C11—C12—C13	−0.6 (5)	S3B—C18B—C19B—C20B	5(5)
C11—C12—C13—C14	0.3 (6)	C18B—C19B—C20B—C21B	−7(6)
C12—C13—C14—S2	0.1 (6)	C19B—C20B—C21B—S3B	5(5)
C11—S2—C14—C13	−0.4 (4)	C18B—S3B—C21B—C20B	−2(4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21N···I1i	0.92	2.79	3.557 (4)	142
N2—H22N···I2	0.92	2.67	3.543 (4)	160
N3—H31N···I1	0.92	2.78	3.547 (3)	142
N3—H32N···I3	0.92	2.59	3.460 (3)	158
N4—H41N···I1	0.92	2.73	3.553 (4)	150
N4—H42N···I2ii	0.92	2.57	3.479 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21N⋯I1i	0.92	2.79	3.557 (4)	142
N2—H22N⋯I2	0.92	2.67	3.543 (4)	160
N3—H31N⋯I1	0.92	2.78	3.547 (3)	142
N3—H32N⋯I3	0.92	2.59	3.460 (3)	158
N4—H41N⋯I1	0.92	2.73	3.553 (4)	150
N4—H42N⋯I2ii	0.92	2.57	3.479 (4)	172

Symmetry codes: (i) ; (ii) .