Cucurbit[6]uril p-xylylenediammonium diiodide deca-hydrate inclusion complex.

The title inclusion complex, C(36)H(36)N(24)O(12)·C(8)H(14)N(2) (2+)·2I(-)·10H(2)O, displays a large ellipsoidal deformation of the cucurbit[6]uril (CB[6]) skeleton upon complex formation. The benzene ring of the cation is rotationally disordered between two orientations in a ratio of 3:1. The solvent H(2)O mol-ecules form a hydrogen-bonded network by inter-action with the carbonyl groups of CB[6] and the I(-) counterions. The crystal studied exhibited non-merohedral twinning. Both CB[6] and the cation are centrosymmetric.

Related literature

For related literature, see: Bush et al. (2005 ▶); Freeman et al. (1981 ▶); Freeman (1984 ▶); Henning et al. (2007 ▶); Huang et al. (2007 ▶); Ko et al. (2007 ▶); Lagona et al. (2005 ▶); Liu et al. (2005 ▶); Marquez et al. (2004 ▶); Moon & Kaifer (2004 ▶); Rauwald & Scherman (2008 ▶); Rekharsky et al. (2008 ▶); Samsonenko et al. (2002 ▶); Wheate et al. (2006 ▶).

Experimental

Crystal data

C36H36N24O12·C8H14N2 2+·2I−·10H2O

M = 1569.06

Monoclinic,

a = 11.9987 (9) Å

b = 15.9520 (12) Å

c = 15.0517 (11) Å

β = 92.8520 (10)°

V = 2877.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.20 mm−1

T = 220 (2) K

0.20 × 0.10 × 0.07 mm

Data collection

Bruker SMART 1000 three-circle diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.798, T max = 0.914

19804 measured reflections

6606 independent reflections

5363 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.083

S = 1.00

6606 reflections

475 parameters

33 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.68 e Å−3

Δρmin = −0.83 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018412/cv2420sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018412/cv2420Isup2.hkl

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

C36H36N24O12·C8H14N22+·2I–·10H2O	F000 = 1596
Mr = 1569.06	Dx = 1.811 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6752 reflections
a = 11.9987 (9) Å	θ = 2.1–25.0º
b = 15.9520 (12) Å	µ = 1.20 mm−1
c = 15.0517 (11) Å	T = 220 (2) K
β = 92.8520 (10)º	Prism, colourless
V = 2877.4 (4) Å3	0.21 × 0.10 × 0.08 mm
Z = 2

Bruker SMART1000 three-circle diffractometer	6606 independent reflections
Radiation source: fine-focus sealed tube	5363 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
Detector resolution: 8.33 pixels mm-1	θmax = 25.0º
T = 220(2) K	θmin = 2.6º
ω scans	h = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = 0→18
Tmin = 0.798, Tmax = 0.914	l = 0→17
19804 measured reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.01P)2 + 9.45P], P = (max(Fo2,0) + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
6606 reflections	Δρmax = 1.68 e Å−3
475 parameters	Δρmin = −0.83 e Å−3
33 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.The crystal is non-merohedral twin in about 7:1 ratio with 180° rotation around 100 reciprocal axis.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.7930 (3)	0.5633 (2)	0.5760 (2)	0.0507 (10)
H1A	0.7603	0.5953	0.6166	0.076*
H1B	0.8618	0.5832	0.5673	0.076*
H1C	0.7979	0.5101	0.5958	0.076*
C1	0.7258 (3)	0.5656 (3)	0.4919 (3)	0.0443 (10)
H1D	0.7641	0.5331	0.4473	0.053*
H1E	0.7210	0.6237	0.4710	0.053*
C2	0.6097 (3)	0.5316 (2)	0.4984 (3)	0.0338 (8)	0.75 (2)
C3	0.5731 (6)	0.4915 (8)	0.5724 (4)	0.042 (2)	0.75 (2)
H3	0.6213	0.4862	0.6232	0.050*	0.75 (2)
C4	0.4658 (7)	0.4587 (8)	0.5731 (4)	0.042 (2)	0.75 (2)
H4	0.4440	0.4293	0.6235	0.051*	0.75 (2)
C2A	0.6097 (3)	0.5316 (2)	0.4984 (3)	0.0338 (8)	0.25 (2)
C3A	0.5490 (14)	0.538 (3)	0.5730 (11)	0.048 (7)	0.25 (2)
H3A	0.5817	0.5623	0.6248	0.058*	0.25 (2)
C4A	0.4395 (15)	0.509 (3)	0.5729 (14)	0.055 (8)	0.25 (2)
H4A	0.3983	0.5175	0.6236	0.065*	0.25 (2)
N10	0.3002 (3)	0.7278 (2)	0.4134 (2)	0.0404 (8)
C11	0.3824 (3)	0.7816 (3)	0.3748 (3)	0.0419 (10)
H11	0.3561	0.8402	0.3694	0.050*
N12	0.4926 (3)	0.7764 (2)	0.4189 (3)	0.0514 (10)
C13	0.2665 (3)	0.6641 (3)	0.3575 (3)	0.0378 (9)
O13	0.1943 (2)	0.61228 (18)	0.3720 (2)	0.0477 (7)
C14	0.5705 (4)	0.7472 (3)	0.3620 (3)	0.0492 (11)
O14	0.6714 (2)	0.7448 (2)	0.3790 (2)	0.0597 (9)
N15	0.3242 (3)	0.6691 (2)	0.2818 (2)	0.0410 (8)
C16	0.3977 (3)	0.7412 (3)	0.2827 (3)	0.0417 (10)
H16	0.3776	0.7804	0.2335	0.050*
N17	0.5157 (3)	0.7200 (2)	0.2855 (2)	0.0443 (9)
C18	0.3017 (3)	0.6167 (3)	0.2047 (3)	0.0424 (10)
H18A	0.3035	0.6515	0.1510	0.051*
H18B	0.2264	0.5934	0.2072	0.051*
C19	0.5726 (4)	0.6914 (3)	0.2075 (3)	0.0525 (12)
H19A	0.6504	0.7101	0.2134	0.063*
H19B	0.5381	0.7189	0.1549	0.063*
N20	0.3804 (2)	0.5487 (2)	0.1978 (2)	0.0369 (8)
C21	0.4813 (3)	0.5542 (2)	0.1478 (3)	0.0382 (9)
H21	0.4651	0.5740	0.0862	0.046*
N22	0.5717 (3)	0.6010 (2)	0.1919 (2)	0.0421 (8)
C23	0.3496 (3)	0.4674 (3)	0.2112 (3)	0.0393 (10)
O23	0.2621 (2)	0.44348 (18)	0.2413 (2)	0.0458 (7)
C24	0.6548 (3)	0.5501 (3)	0.2251 (3)	0.0414 (10)
O24	0.7409 (2)	0.57396 (19)	0.2638 (2)	0.0554 (8)
N25	0.4334 (3)	0.4166 (2)	0.1863 (2)	0.0410 (8)
C26	0.5247 (3)	0.4628 (3)	0.1501 (3)	0.0395 (10)
H26	0.5425	0.4424	0.0903	0.047*
N27	0.6246 (3)	0.4686 (2)	0.2104 (2)	0.0414 (8)
C28	0.4310 (3)	0.3270 (3)	0.1997 (3)	0.0471 (11)
H28A	0.4655	0.2999	0.1494	0.056*
H28B	0.3530	0.3088	0.1988	0.056*
C29	0.7032 (3)	0.3999 (3)	0.2238 (3)	0.0474 (11)
H29A	0.7030	0.3663	0.1693	0.057*
H29B	0.7783	0.4232	0.2341	0.057*
N30	0.4870 (3)	0.2973 (2)	0.2816 (2)	0.0429 (9)
C31	0.6038 (3)	0.2749 (3)	0.2874 (3)	0.0438 (10)
H31	0.6236	0.2381	0.2376	0.053*
N32	0.6791 (3)	0.3455 (2)	0.2977 (2)	0.0453 (9)
C33	0.4323 (3)	0.2741 (3)	0.3553 (3)	0.0439 (10)
O33	0.3330 (2)	0.28222 (19)	0.3662 (2)	0.0543 (8)
C34	0.7397 (3)	0.3437 (3)	0.3768 (3)	0.0417 (10)
O34	0.8151 (2)	0.39229 (19)	0.4000 (2)	0.0512 (8)
N35	0.5085 (3)	0.2381 (2)	0.4152 (3)	0.0455 (9)
C36	0.6176 (3)	0.2293 (3)	0.3780 (3)	0.0435 (10)
H36	0.6383	0.1698	0.3708	0.052*
N37	0.7055 (3)	0.2765 (2)	0.4248 (2)	0.0437 (9)
C38	0.4791 (4)	0.1889 (3)	0.4935 (4)	0.0598 (13)
H38A	0.3984	0.1791	0.4892	0.072*
H38B	0.5154	0.1340	0.4899	0.072*
C39	0.7588 (3)	0.2502 (3)	0.5088 (3)	0.0442 (10)
H39A	0.7680	0.1891	0.5076	0.053*
H39B	0.8335	0.2751	0.5142	0.053*
I1	0.78087 (2)	0.50257 (2)	0.010322 (19)	0.05174 (9)
O1W	0.9837 (3)	0.6263 (3)	0.4947 (3)	0.0760 (11)
H11W	1.035 (3)	0.593 (3)	0.512 (3)	0.114*
H12W	0.978 (5)	0.619 (4)	0.4385 (14)	0.114*
O2W	0.9547 (3)	0.6070 (3)	0.3199 (3)	0.0937 (14)
H21W	0.994 (4)	0.571 (3)	0.291 (4)	0.141*
H22W	0.891 (3)	0.584 (4)	0.310 (5)	0.141*
O3W	1.0139 (4)	0.3995 (3)	0.3046 (3)	0.0880 (12)
H31W	1.019 (6)	0.427 (3)	0.255 (2)	0.132*
H32W	0.969 (4)	0.433 (3)	0.334 (4)	0.132*
O4W	0.8962 (3)	0.7906 (3)	0.4916 (3)	0.0839 (11)
H41W	0.8269 (16)	0.790 (4)	0.486 (5)	0.126*
H42W	0.914 (5)	0.746 (3)	0.467 (4)	0.126*
O5W	1.0206 (3)	0.5122 (4)	0.1607 (3)	0.0947 (14)
H51W	1.073 (3)	0.507 (5)	0.129 (4)	0.142*
H52W	0.965 (3)	0.495 (5)	0.133 (4)	0.142*

	U11	U22	U33	U12	U13	U23
N1	0.0256 (18)	0.070 (3)	0.056 (2)	−0.0157 (17)	−0.0027 (16)	0.012 (2)
C1	0.031 (2)	0.054 (2)	0.048 (3)	−0.0075 (19)	0.0007 (18)	0.005 (2)
C2	0.0290 (19)	0.038 (2)	0.034 (2)	−0.0021 (15)	0.0010 (16)	0.0013 (17)
C3	0.032 (3)	0.056 (6)	0.037 (3)	−0.004 (3)	−0.008 (2)	0.006 (3)
C4	0.036 (4)	0.054 (6)	0.037 (4)	−0.007 (4)	0.005 (3)	0.010 (3)
C2A	0.0290 (19)	0.038 (2)	0.034 (2)	−0.0021 (15)	0.0010 (16)	0.0013 (17)
C3A	0.041 (9)	0.06 (2)	0.043 (11)	0.002 (11)	0.005 (7)	−0.008 (11)
C4A	0.042 (9)	0.07 (2)	0.048 (12)	0.008 (11)	0.021 (8)	−0.007 (13)
N10	0.0284 (18)	0.048 (2)	0.045 (2)	−0.0041 (15)	0.0042 (15)	−0.0011 (17)
C11	0.029 (2)	0.042 (2)	0.054 (3)	−0.0006 (18)	0.0004 (18)	0.000 (2)
N12	0.0265 (19)	0.064 (3)	0.063 (3)	−0.0022 (17)	−0.0015 (17)	−0.022 (2)
C13	0.024 (2)	0.043 (2)	0.045 (3)	0.0019 (18)	−0.0013 (17)	0.002 (2)
O13	0.0295 (15)	0.0550 (19)	0.059 (2)	−0.0099 (14)	0.0055 (13)	0.0007 (15)
C14	0.031 (2)	0.046 (3)	0.072 (3)	−0.005 (2)	0.009 (2)	−0.004 (2)
O14	0.0255 (17)	0.066 (2)	0.088 (3)	−0.0058 (14)	0.0051 (15)	−0.0152 (18)
N15	0.0326 (19)	0.046 (2)	0.045 (2)	−0.0062 (15)	0.0072 (15)	−0.0025 (17)
C16	0.029 (2)	0.043 (2)	0.052 (3)	0.0002 (18)	0.0034 (18)	0.004 (2)
N17	0.0298 (19)	0.054 (2)	0.049 (2)	−0.0009 (16)	0.0088 (16)	−0.0014 (18)
C18	0.030 (2)	0.049 (3)	0.048 (3)	0.0032 (18)	−0.0029 (18)	0.001 (2)
C19	0.037 (2)	0.059 (3)	0.062 (3)	−0.010 (2)	0.010 (2)	0.005 (2)
N20	0.0228 (17)	0.041 (2)	0.046 (2)	0.0025 (14)	−0.0010 (14)	0.0019 (16)
C21	0.033 (2)	0.045 (2)	0.037 (2)	−0.0002 (18)	−0.0022 (18)	0.0046 (19)
N22	0.0252 (18)	0.044 (2)	0.057 (2)	−0.0023 (15)	0.0012 (15)	−0.0032 (17)
C23	0.026 (2)	0.049 (2)	0.042 (2)	0.0013 (18)	−0.0089 (18)	0.0041 (19)
O23	0.0231 (15)	0.0559 (18)	0.0581 (19)	−0.0046 (13)	0.0003 (13)	0.0063 (15)
C24	0.029 (2)	0.052 (3)	0.044 (3)	−0.0023 (19)	0.0068 (19)	−0.006 (2)
O24	0.0262 (16)	0.066 (2)	0.073 (2)	−0.0050 (14)	−0.0053 (14)	−0.0117 (17)
N25	0.0227 (17)	0.040 (2)	0.059 (2)	−0.0004 (14)	−0.0019 (15)	0.0022 (17)
C26	0.030 (2)	0.049 (2)	0.040 (2)	0.0006 (18)	−0.0002 (18)	−0.0031 (19)
N27	0.0227 (17)	0.051 (2)	0.051 (2)	0.0043 (15)	−0.0018 (15)	0.0001 (17)
C28	0.029 (2)	0.054 (3)	0.057 (3)	−0.0015 (19)	−0.0060 (19)	−0.004 (2)
C29	0.033 (2)	0.058 (3)	0.050 (3)	0.002 (2)	−0.0011 (19)	0.004 (2)
N30	0.0276 (18)	0.046 (2)	0.054 (2)	0.0014 (15)	−0.0057 (16)	0.0062 (18)
C31	0.031 (2)	0.050 (3)	0.050 (3)	0.0072 (19)	−0.0032 (18)	0.002 (2)
N32	0.0306 (19)	0.054 (2)	0.050 (2)	−0.0072 (16)	−0.0067 (16)	0.0113 (18)
C33	0.028 (2)	0.037 (2)	0.066 (3)	−0.0050 (18)	−0.003 (2)	−0.007 (2)
O33	0.0269 (17)	0.0540 (19)	0.082 (2)	−0.0067 (14)	0.0009 (15)	−0.0034 (17)
C34	0.029 (2)	0.048 (3)	0.048 (3)	0.0038 (19)	0.0001 (19)	0.006 (2)
O34	0.0310 (16)	0.061 (2)	0.061 (2)	−0.0100 (14)	−0.0080 (14)	0.0086 (16)
N35	0.0333 (19)	0.051 (2)	0.053 (2)	−0.0046 (16)	0.0019 (17)	0.0059 (18)
C36	0.033 (2)	0.047 (3)	0.051 (3)	0.0008 (19)	−0.0011 (19)	0.000 (2)
N37	0.0318 (18)	0.053 (2)	0.045 (2)	−0.0039 (16)	−0.0063 (15)	0.0077 (17)
C38	0.039 (3)	0.056 (3)	0.084 (4)	−0.005 (2)	0.002 (3)	−0.003 (3)
C39	0.033 (2)	0.051 (3)	0.048 (3)	0.0045 (18)	−0.0021 (19)	0.004 (2)
I1	0.05282 (17)	0.05554 (18)	0.04705 (16)	−0.01189 (15)	0.00454 (12)	0.00013 (16)
O1W	0.0357 (19)	0.103 (3)	0.089 (3)	−0.0053 (18)	0.0004 (19)	0.021 (3)
O2W	0.041 (2)	0.119 (4)	0.119 (4)	−0.004 (2)	−0.005 (2)	−0.004 (3)
O3W	0.074 (3)	0.091 (3)	0.099 (3)	0.006 (2)	0.010 (2)	0.002 (2)
O4W	0.071 (2)	0.082 (3)	0.100 (3)	−0.002 (2)	0.005 (2)	−0.008 (2)
O5W	0.050 (2)	0.168 (4)	0.066 (2)	0.003 (3)	0.0075 (18)	0.000 (3)

N1—C1	1.467 (5)	C23—N25	1.359 (5)
N1—H1A	0.9000	C24—O24	1.222 (5)
N1—H1B	0.9000	C24—N27	1.364 (5)
N1—H1C	0.9000	N25—C28	1.445 (5)
C1—C2	1.503 (5)	N25—C26	1.449 (5)
C1—H1D	0.9800	C26—N27	1.470 (5)
C1—H1E	0.9800	C26—H26	0.9900
C2—C3	1.375 (6)	N27—C29	1.453 (5)
C2—C4i	1.380 (8)	C28—N30	1.453 (5)
C3—C4	1.391 (7)	C28—H28A	0.9800
C3—H3	0.9400	C28—H28B	0.9800
C4—C2i	1.380 (8)	C29—N32	1.452 (5)
C4—H4	0.9400	C29—H29A	0.9800
C3A—C4A	1.393 (11)	C29—H29B	0.9800
C3A—H3A	0.9400	N30—C33	1.368 (5)
C4A—C2Ai	1.36 (2)	N30—C31	1.444 (5)
C4A—H4A	0.9400	C31—N32	1.447 (5)
N10—C13	1.368 (5)	C31—C36	1.547 (6)
N10—C39i	1.441 (5)	C31—H31	0.9900
N10—C11	1.451 (5)	N32—C34	1.364 (5)
C11—N12	1.452 (5)	C33—O33	1.218 (5)
C11—C16	1.549 (6)	C33—N35	1.377 (5)
C11—H11	0.9900	C34—O34	1.228 (5)
N12—C14	1.379 (5)	C34—N37	1.367 (5)
N12—C38i	1.455 (6)	N35—C36	1.455 (5)
C13—O13	1.225 (4)	N35—C38	1.474 (6)
C13—N15	1.365 (5)	C36—N37	1.449 (5)
C14—O14	1.225 (5)	C36—H36	0.9900
C14—N17	1.367 (6)	N37—C39	1.450 (5)
N15—C18	1.445 (5)	C38—N12i	1.455 (6)
N15—C16	1.449 (5)	C38—H38A	0.9800
C16—N17	1.453 (5)	C38—H38B	0.9800
C16—H16	0.9900	C39—N10i	1.441 (5)
N17—C19	1.460 (5)	C39—H39A	0.9800
C18—N20	1.446 (5)	C39—H39B	0.9800
C18—H18A	0.9800	I1—H52W	2.80 (4)
C18—H18B	0.9800	O1W—H11W	0.843 (19)
C19—N22	1.461 (5)	O1W—H12W	0.852 (19)
C19—H19A	0.9800	O2W—H21W	0.870 (18)
C19—H19B	0.9800	O2W—H22W	0.85 (2)
N20—C23	1.366 (5)	O3W—H31W	0.870 (18)
N20—C21	1.460 (5)	O3W—H32W	0.892 (19)
C21—N22	1.450 (5)	O4W—H41W	0.831 (19)
C21—C26	1.547 (5)	O4W—H42W	0.835 (19)
C21—H21	0.9900	O5W—H51W	0.82 (2)
N22—C24	1.361 (5)	O5W—H52W	0.824 (19)
C23—O23	1.225 (5)
C1—N1—H1A	109.5	C24—O24—H22W	164.0 (18)
C1—N1—H1B	109.5	C23—N25—C28	122.1 (3)
H1A—N1—H1B	109.5	C23—N25—C26	112.6 (3)
C1—N1—H1C	109.5	C28—N25—C26	125.2 (3)
H1A—N1—H1C	109.5	N25—C26—N27	114.1 (3)
H1B—N1—H1C	109.5	N25—C26—C21	103.2 (3)
N1—C1—C2	113.9 (3)	N27—C26—C21	102.6 (3)
N1—C1—H1D	108.8	N25—C26—H26	112.1
C2—C1—H1D	108.8	N27—C26—H26	112.1
N1—C1—H1E	108.8	C21—C26—H26	112.1
C2—C1—H1E	108.8	C24—N27—C29	122.1 (3)
H1D—C1—H1E	107.7	C24—N27—C26	111.1 (3)
C3—C2—C4i	117.4 (4)	C29—N27—C26	122.8 (3)
C3—C2—C1	123.7 (4)	N25—C28—N30	115.4 (3)
C4i—C2—C1	118.9 (4)	N25—C28—H28A	108.4
C2—C3—C4	121.0 (5)	N30—C28—H28A	108.4
C2—C3—H3	119.5	N25—C28—H28B	108.4
C4—C3—H3	119.5	N30—C28—H28B	108.4
C2i—C4—C3	121.6 (5)	H28A—C28—H28B	107.5
C2i—C4—H4	119.2	N32—C29—N27	113.8 (3)
C3—C4—H4	119.2	N32—C29—H29A	108.8
C4A—C3A—H3A	119.6	N27—C29—H29A	108.8
C2Ai—C4A—C3A	122.1 (13)	N32—C29—H29B	108.8
C2Ai—C4A—H4A	119.0	N27—C29—H29B	108.8
C3A—C4A—H4A	119.0	H29A—C29—H29B	107.7
C13—N10—C39i	122.7 (3)	C33—N30—C31	112.8 (3)
C13—N10—C11	112.2 (3)	C33—N30—C28	123.8 (3)
C39i—N10—C11	123.5 (3)	C31—N30—C28	122.6 (4)
N10—C11—N12	113.9 (3)	N30—C31—N32	114.3 (3)
N10—C11—C16	103.1 (3)	N30—C31—C36	103.3 (3)
N12—C11—C16	103.8 (3)	N32—C31—C36	103.4 (3)
N10—C11—H11	111.8	N30—C31—H31	111.7
N12—C11—H11	111.8	N32—C31—H31	111.7
C16—C11—H11	111.8	C36—C31—H31	111.7
C14—N12—C11	111.5 (4)	C34—N32—C31	112.4 (3)
C14—N12—C38i	123.8 (4)	C34—N32—C29	124.3 (4)
C11—N12—C38i	123.9 (3)	C31—N32—C29	122.0 (3)
O13—C13—N15	125.5 (4)	O33—C33—N30	126.4 (4)
O13—C13—N10	125.5 (4)	O33—C33—N35	125.3 (4)
N15—C13—N10	108.9 (3)	N30—C33—N35	108.3 (3)
O14—C14—N17	126.5 (4)	O34—C34—N32	126.0 (4)
O14—C14—N12	125.0 (4)	O34—C34—N37	125.5 (4)
N17—C14—N12	108.5 (4)	N32—C34—N37	108.4 (4)
C14—O14—H41W	145.2 (12)	C34—O34—H32W	132.1 (14)
C13—N15—C18	123.7 (3)	C33—N35—C36	111.6 (4)
C13—N15—C16	111.9 (3)	C33—N35—C38	124.6 (4)
C18—N15—C16	123.7 (3)	C36—N35—C38	120.8 (3)
N15—C16—N17	114.0 (3)	N37—C36—N35	114.2 (4)
N15—C16—C11	103.8 (3)	N37—C36—C31	103.2 (3)
N17—C16—C11	103.2 (3)	N35—C36—C31	103.6 (3)
N15—C16—H16	111.7	N37—C36—H36	111.8
N17—C16—H16	111.7	N35—C36—H36	111.8
C11—C16—H16	111.7	C31—C36—H36	111.8
C14—N17—C16	112.2 (3)	C34—N37—C36	112.4 (3)
C14—N17—C19	123.4 (4)	C34—N37—C39	123.8 (3)
C16—N17—C19	122.8 (4)	C36—N37—C39	123.5 (3)
N15—C18—N20	113.2 (3)	N12i—C38—N35	117.8 (4)
N15—C18—H18A	108.9	N12i—C38—H38A	107.8
N20—C18—H18A	108.9	N35—C38—H38A	107.8
N15—C18—H18B	108.9	N12i—C38—H38B	107.8
N20—C18—H18B	108.9	N35—C38—H38B	107.8
H18A—C18—H18B	107.7	H38A—C38—H38B	107.2
N17—C19—N22	116.0 (4)	N10i—C39—N37	115.1 (3)
N17—C19—H19A	108.3	N10i—C39—H39A	108.5
N22—C19—H19A	108.3	N37—C39—H39A	108.5
N17—C19—H19B	108.3	N10i—C39—H39B	108.5
N22—C19—H19B	108.3	N37—C39—H39B	108.5
H19A—C19—H19B	107.4	H39A—C39—H39B	107.5
C23—N20—C18	121.3 (3)	H1B—O1W—H42W	97.1
C23—N20—C21	111.8 (3)	H1B—O1W—H11W	99.4
C18—N20—C21	123.6 (3)	H42W—O1W—H11W	154 (4)
N22—C21—N20	114.5 (3)	H1B—O1W—H12W	118.7
N22—C21—C26	103.4 (3)	H42W—O1W—H12W	85 (4)
N20—C21—C26	102.6 (3)	H11W—O1W—H12W	104 (3)
N22—C21—H21	111.9	H12W—O2W—H21W	120 (4)
N20—C21—H21	111.9	H12W—O2W—H22W	109 (5)
C26—C21—H21	111.9	H21W—O2W—H22W	97 (3)
C24—N22—C21	112.2 (3)	H31W—O3W—H32W	101 (3)
C24—N22—C19	122.1 (4)	H41W—O4W—H42W	103 (4)
C21—N22—C19	125.5 (3)	H31W—O5W—H21W	69.1 (15)
O23—C23—N25	125.2 (4)	H31W—O5W—H51W	113 (6)
O23—C23—N20	126.4 (4)	H21W—O5W—H51W	136 (5)
N25—C23—N20	108.4 (3)	H31W—O5W—H52W	96 (6)
O24—C24—N22	125.1 (4)	H21W—O5W—H52W	116 (5)
O24—C24—N27	125.8 (4)	H51W—O5W—H52W	107 (4)
N22—C24—N27	109.0 (3)
N1—C1—C2—C3	−8.4 (9)	O23—C23—N25—C26	177.8 (4)
N1—C1—C2—C4i	171.1 (7)	N20—C23—N25—C26	−2.8 (5)
C4i—C2—C3—C4	2.9 (10)	C23—N25—C26—N27	105.7 (4)
C1—C2—C3—C4	−177.6 (5)	C28—N25—C26—N27	−71.4 (5)
C2—C3—C4—C2i	−3.0 (10)	C23—N25—C26—C21	−4.8 (4)
C13—N10—C11—N12	−112.2 (4)	C28—N25—C26—C21	178.1 (4)
C39i—N10—C11—N12	81.8 (5)	N22—C21—C26—N25	129.2 (3)
C13—N10—C11—C16	−0.4 (4)	N20—C21—C26—N25	9.8 (4)
C39i—N10—C11—C16	−166.4 (3)	N22—C21—C26—N27	10.4 (4)
N10—C11—N12—C14	117.8 (4)	N20—C21—C26—N27	−108.9 (3)
C16—C11—N12—C14	6.4 (5)	O24—C24—N27—C29	−13.1 (7)
N10—C11—N12—C38i	−72.2 (5)	N22—C24—N27—C29	168.9 (3)
C16—C11—N12—C38i	176.4 (4)	O24—C24—N27—C26	−171.2 (4)
C39i—N10—C13—O13	−10.4 (6)	N22—C24—N27—C26	10.7 (5)
C11—N10—C13—O13	−176.5 (4)	N25—C26—N27—C24	−124.0 (4)
C39i—N10—C13—N15	168.0 (3)	C21—C26—N27—C24	−13.2 (4)
C11—N10—C13—N15	1.9 (4)	N25—C26—N27—C29	78.1 (5)
C11—N12—C14—O14	172.2 (4)	C21—C26—N27—C29	−171.1 (3)
C38i—N12—C14—O14	2.2 (7)	C23—N25—C28—N30	−93.7 (5)
C11—N12—C14—N17	−9.3 (5)	C26—N25—C28—N30	83.1 (5)
C38i—N12—C14—N17	−179.3 (4)	C24—N27—C29—N32	112.2 (4)
O13—C13—N15—C18	4.8 (6)	C26—N27—C29—N32	−92.2 (5)
N10—C13—N15—C18	−173.5 (3)	N25—C28—N30—C33	102.0 (5)
O13—C13—N15—C16	175.6 (4)	N25—C28—N30—C31	−89.8 (5)
N10—C13—N15—C16	−2.7 (5)	C33—N30—C31—N32	−109.9 (4)
C13—N15—C16—N17	114.0 (4)	C28—N30—C31—N32	80.7 (5)
C18—N15—C16—N17	−75.2 (5)	C33—N30—C31—C36	1.7 (5)
C13—N15—C16—C11	2.4 (4)	C28—N30—C31—C36	−167.6 (4)
C18—N15—C16—C11	173.2 (3)	N30—C31—N32—C34	116.4 (4)
N10—C11—C16—N15	−1.1 (4)	C36—C31—N32—C34	4.8 (5)
N12—C11—C16—N15	117.9 (3)	N30—C31—N32—C29	−76.3 (5)
N10—C11—C16—N17	−120.4 (3)	C36—C31—N32—C29	172.1 (3)
N12—C11—C16—N17	−1.3 (4)	N27—C29—N32—C34	−107.2 (5)
O14—C14—N17—C16	−173.1 (4)	N27—C29—N32—C31	87.1 (5)
N12—C14—N17—C16	8.4 (5)	C31—N30—C33—O33	−176.7 (4)
O14—C14—N17—C19	−6.7 (7)	C28—N30—C33—O33	−7.5 (7)
N12—C14—N17—C19	174.8 (4)	C31—N30—C33—N35	2.1 (5)
N15—C16—N17—C14	−116.1 (4)	C28—N30—C33—N35	171.3 (4)
C11—C16—N17—C14	−4.2 (5)	C31—N32—C34—O34	174.4 (4)
N15—C16—N17—C19	77.4 (5)	C29—N32—C34—O34	7.5 (7)
C11—C16—N17—C19	−170.7 (4)	C31—N32—C34—N37	−3.2 (5)
C13—N15—C18—N20	−101.9 (4)	C29—N32—C34—N37	−170.2 (4)
C16—N15—C18—N20	88.4 (5)	O33—C33—N35—C36	173.4 (4)
C14—N17—C19—N22	106.0 (5)	N30—C33—N35—C36	−5.4 (5)
C16—N17—C19—N22	−89.0 (5)	O33—C33—N35—C38	12.9 (7)
N15—C18—N20—C23	109.8 (4)	N30—C33—N35—C38	−166.0 (4)
N15—C18—N20—C21	−92.6 (4)	C33—N35—C36—N37	117.7 (4)
C23—N20—C21—N22	−123.7 (4)	C38—N35—C36—N37	−80.9 (5)
C18—N20—C21—N22	76.8 (5)	C33—N35—C36—C31	6.2 (4)
C23—N20—C21—C26	−12.4 (4)	C38—N35—C36—C31	167.6 (4)
C18—N20—C21—C26	−171.9 (3)	N30—C31—C36—N37	−123.9 (3)
N20—C21—N22—C24	105.8 (4)	N32—C31—C36—N37	−4.5 (4)
C26—C21—N22—C24	−5.0 (4)	N30—C31—C36—N35	−4.6 (4)
N20—C21—N22—C19	−69.0 (5)	N32—C31—C36—N35	114.9 (3)
C26—C21—N22—C19	−179.8 (4)	O34—C34—N37—C36	−177.7 (4)
N17—C19—N22—C24	−91.7 (5)	N32—C34—N37—C36	−0.1 (5)
N17—C19—N22—C21	82.6 (5)	O34—C34—N37—C39	−3.8 (7)
C18—N20—C23—O23	−10.6 (7)	N32—C34—N37—C39	173.8 (4)
C21—N20—C23—O23	−170.6 (4)	N35—C36—N37—C34	−108.8 (4)
C18—N20—C23—N25	170.0 (3)	C31—C36—N37—C34	3.0 (4)
C21—N20—C23—N25	10.0 (5)	N35—C36—N37—C39	77.3 (5)
C21—N22—C24—O24	178.8 (4)	C31—C36—N37—C39	−171.0 (4)
C19—N22—C24—O24	−6.3 (7)	C33—N35—C38—N12i	−113.2 (5)
C21—N22—C24—N27	−3.2 (5)	C36—N35—C38—N12i	87.9 (5)
C19—N22—C24—N27	171.8 (4)	C34—N37—C39—N10i	103.4 (4)
O23—C23—N25—C28	−5.0 (6)	C36—N37—C39—N10i	−83.3 (5)
N20—C23—N25—C28	174.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O23i	0.90	2.25	2.861 (5)	124
N1—H1A···O33i	0.90	2.27	3.040 (5)	143
N1—H1B···O1W	0.90	1.99	2.833 (5)	155
N1—H1B···O3Wii	0.90	2.39	2.922 (6)	118
N1—H1C···O13i	0.90	2.01	2.910 (5)	175
O1W—H11W···O34ii	0.843 (19)	2.19 (3)	2.837 (4)	133 (4)
O1W—H12W···O2W	0.852 (19)	1.80 (2)	2.655 (6)	175 (6)
O2W—H21W···O5W	0.870 (18)	2.21 (3)	2.973 (6)	146 (5)
O2W—H22W···O24	0.85 (2)	1.91 (3)	2.712 (5)	157 (7)
O3W—H31W···O5W	0.870 (18)	1.97 (2)	2.820 (7)	167 (4)
O3W—H32W···O34	0.892 (19)	2.23 (4)	2.847 (5)	126 (4)
O4W—H41W···O14	0.831 (19)	2.51 (5)	3.198 (5)	141 (6)
O4W—H42W···O1W	0.835 (19)	2.11 (5)	2.823 (6)	143 (7)
O5W—H51W···I1iii	0.82 (2)	2.80 (3)	3.601 (4)	167 (6)
O5W—H52W···I1	0.824 (19)	2.80 (4)	3.573 (4)	157 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O23i	0.90	2.25	2.861 (5)	124
N1—H1A⋯O33i	0.90	2.27	3.040 (5)	143
N1—H1B⋯O1W	0.90	1.99	2.833 (5)	155
N1—H1B⋯O3Wii	0.90	2.39	2.922 (6)	118
N1—H1C⋯O13i	0.90	2.01	2.910 (5)	175
O1W—H11W⋯O34ii	0.843 (19)	2.19 (3)	2.837 (4)	133 (4)
O1W—H12W⋯O2W	0.852 (19)	1.80 (2)	2.655 (6)	175 (6)
O2W—H21W⋯O5W	0.870 (18)	2.21 (3)	2.973 (6)	146 (5)
O2W—H22W⋯O24	0.85 (2)	1.91 (3)	2.712 (5)	157 (7)
O3W—H31W⋯O5W	0.870 (18)	1.97 (2)	2.820 (7)	167 (4)
O3W—H32W⋯O34	0.892 (19)	2.23 (4)	2.847 (5)	126 (4)
O4W—H41W⋯O14	0.831 (19)	2.51 (5)	3.198 (5)	141 (6)
O4W—H42W⋯O1W	0.835 (19)	2.11 (5)	2.823 (6)	143 (7)
O5W—H51W⋯I1iii	0.82 (2)	2.80 (3)	3.601 (4)	167 (6)
O5W—H52W⋯I1	0.824 (19)	2.80 (4)	3.573 (4)	157 (7)

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