2,5-Bis[2-({bis-[3-(dimethyl-aza-nium-yl)prop-yl]aza-nium-yl}meth-yl)phen-yl]-1,3,4-oxadiazole hexa-kis-(perchlorate) sesquihydrate.

In the title hydrated salt, C36H66N8O(6+)·6ClO4(-)·1.5H2O, the asymmetric unit consists of a hexa-protonated [H6L](6+) cation, five perchlorate anions in general positions, two on twofold rotation axes (one of which is disordered), and two water mol-ecules of crystallization in general positions, one of them disordered around a twofold crystallographic axis. In the [H6L](6+) cation, two strong intra-molecular N-H⋯N hydrogen bonds occur, involving the N atoms of the oxadiazole ring as acceptors and the closest NH(+) groups of each dipropyl-enetriamine unit. In the crystal, the [H6L](6+) cations form channels along the a-axis direction, in which the perchlorate counter-ions and the water mol-ecules are lodged. The crystal packing features a network of N-H⋯O and O-H⋯O hydrogen bonds involving the NH(+) groups of the [H6L](6+) cation, the perchlorate anions and the water mol-ecules.

Related literature

For 2,5 bis­[2 (chloro­meth­yl)phen­yl][1,3,4]oxadiazole, see: Formica et al. (2012 ▶); Wang et al. (1998 ▶). For systems able to recognise and signal metal cations and anions, see: Ambrosi et al. (2006 ▶, 2011 ▶); Ambrosi, Formica, Fusi, Giorgi, Macedi, Micheloni, Paoli et al. (2010 ▶); Ambrosi, Formica, Fusi, Giorgi, Macedi, Micheloni, Piersanti et al. (2010 ▶); Bencini et al. (1994 ▶); Formica et al. (2008 ▶); Terenzi et al. (2012 ▶).

Experimental

Crystal data

C36H66N8O6+·6ClO4 −·1.5H2O

M = 1250.69

Monoclinic,

a = 19.5601 (7) Å

b = 25.0825 (8) Å

c = 24.2277 (9) Å

β = 113.695 (5)°

V = 10884.4 (7) Å3

Z = 8

Cu Kα radiation

μ = 3.69 mm−1

T = 150 K

0.10 × 0.08 × 0.03 mm

Data collection

Oxford XcaliburPX diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.728, T max = 0.895

30246 measured reflections

10465 independent reflections

6531 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.219

S = 1.06

10465 reflections

692 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.48 e Å−3

Δρmin = −0.86 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PARST97 (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047484/lr2084sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047484/lr2084Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047484/lr2084Isup3.cml

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

C36H66N8O6+·6ClO4−·1.5H2O	F(000) = 5240
Mr = 1250.69	Dx = 1.526 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 7461 reflections
a = 19.5601 (7) Å	θ = 4.1–72.6°
b = 25.0825 (8) Å	µ = 3.69 mm−1
c = 24.2277 (9) Å	T = 150 K
β = 113.695 (5)°	Prismatic, colourless
V = 10884.4 (7) Å3	0.10 × 0.08 × 0.03 mm
Z = 8

Oxford XcaliburPX diffractometer	10465 independent reflections
Radiation source: Enhance (Cu) X-ray Source	6531 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 8.1241 pixels mm-1	θmax = 72.7°, θmin = 4.1°
ω scans	h = −23→22
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −30→28
Tmin = 0.728, Tmax = 0.895	l = −29→22
30246 measured reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1066P)2 + 23.0322P] where P = (Fo2 + 2Fc2)/3
10465 reflections	(Δ/σ)max < 0.001
692 parameters	Δρmax = 1.48 e Å−3
3 restraints	Δρmin = −0.86 e Å−3

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 > 2σ(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)
O1	0.79278 (16)	0.14810 (13)	0.50045 (13)	0.0335 (7)
N1	0.7899 (2)	0.17588 (15)	0.41311 (16)	0.0332 (8)
N2	0.7645 (2)	0.12311 (16)	0.40659 (16)	0.0345 (8)
N3	0.7397 (2)	0.03182 (15)	0.34130 (16)	0.0332 (8)
H3	0.7656	0.0624	0.3599	0.040*
N4	0.9862 (2)	−0.0271 (2)	0.34900 (19)	0.0498 (11)
H4	0.9682	−0.0158	0.3091	0.060*
N5	0.5784 (2)	−0.02129 (16)	0.12725 (16)	0.0337 (8)
H5	0.5848	−0.0548	0.1451	0.040*
N6	0.85293 (19)	0.25580 (15)	0.36920 (15)	0.0321 (8)
H6	0.8450	0.2197	0.3731	0.038*
N7	1.1101 (2)	0.20308 (16)	0.39186 (17)	0.0356 (9)
H7	1.1038	0.2162	0.3542	0.043*
N8	0.6293 (2)	0.26003 (19)	0.17438 (19)	0.0502 (11)
H8	0.6090	0.2784	0.1976	0.060*
C1	0.7668 (2)	0.10832 (19)	0.4587 (2)	0.0336 (10)
C2	0.7505 (2)	0.0563 (2)	0.4773 (2)	0.0356 (10)
C3	0.7733 (3)	0.0468 (2)	0.5391 (2)	0.0400 (11)
H3A	0.7957	0.0747	0.5670	0.048*
C4	0.7636 (3)	−0.0024 (2)	0.5597 (2)	0.0434 (12)
H4A	0.7800	−0.0085	0.6018	0.052*
C5	0.7299 (3)	−0.0430 (2)	0.5193 (2)	0.0472 (12)
H5A	0.7232	−0.0771	0.5334	0.057*
C6	0.7061 (3)	−0.0335 (2)	0.4580 (2)	0.0428 (12)
H6A	0.6831	−0.0617	0.4307	0.051*
C7	0.7147 (2)	0.0154 (2)	0.4350 (2)	0.0362 (10)
C8	0.6825 (2)	0.0227 (2)	0.3679 (2)	0.0382 (11)
H8A	0.6480	0.0536	0.3575	0.046*
H8B	0.6528	−0.0093	0.3488	0.046*
C9	0.7970 (2)	−0.0116 (2)	0.3574 (2)	0.0378 (11)
H9A	0.7736	−0.0446	0.3355	0.045*
H9B	0.8157	−0.0191	0.4011	0.045*
C10	0.8619 (3)	0.0038 (2)	0.3417 (2)	0.0379 (11)
H10A	0.8449	0.0066	0.2974	0.045*
H10B	0.8819	0.0390	0.3596	0.045*
C11	0.9218 (3)	−0.0377 (2)	0.3657 (2)	0.0391 (11)
H11A	0.9399	−0.0389	0.4102	0.047*
H11B	0.9002	−0.0730	0.3498	0.047*
C12	1.0350 (3)	0.0172 (3)	0.3898 (3)	0.0658 (17)
H12A	1.0046	0.0492	0.3857	0.099*
H12B	1.0761	0.0254	0.3780	0.099*
H12C	1.0552	0.0052	0.4319	0.099*
C13	1.0323 (4)	−0.0754 (3)	0.3559 (4)	0.0716 (19)
H13A	1.0739	−0.0672	0.3446	0.107*
H13B	1.0016	−0.1037	0.3297	0.107*
H13C	1.0519	−0.0873	0.3979	0.107*
C14	0.7033 (2)	0.04488 (19)	0.27488 (19)	0.0349 (10)
H14A	0.7428	0.0529	0.2605	0.042*
H14B	0.6728	0.0775	0.2696	0.042*
C15	0.6538 (2)	0.00103 (19)	0.2357 (2)	0.0352 (10)
H15A	0.6070	−0.0015	0.2420	0.042*
H15B	0.6799	−0.0337	0.2460	0.042*
C16	0.6368 (3)	0.01537 (19)	0.1703 (2)	0.0369 (10)
H16A	0.6189	0.0526	0.1626	0.044*
H16B	0.6832	0.0128	0.1632	0.044*
C17	0.5015 (3)	−0.0028 (2)	0.1154 (2)	0.0443 (12)
H17A	0.4960	0.0008	0.1537	0.067*
H17B	0.4652	−0.0288	0.0898	0.067*
H17C	0.4926	0.0318	0.0949	0.067*
C18	0.5882 (3)	−0.0270 (2)	0.0694 (2)	0.0437 (12)
H18A	0.6391	−0.0391	0.0779	0.066*
H18B	0.5796	0.0075	0.0488	0.066*
H18C	0.5523	−0.0531	0.0436	0.066*
C19	0.8059 (2)	0.18881 (18)	0.46899 (19)	0.0313 (10)
C20	0.8367 (2)	0.23840 (19)	0.4998 (2)	0.0333 (10)
C21	0.8611 (2)	0.2408 (2)	0.5631 (2)	0.0381 (11)
H21	0.8579	0.2101	0.5849	0.046*
C22	0.8898 (3)	0.2879 (2)	0.5932 (2)	0.0425 (12)
H22	0.9054	0.2896	0.6357	0.051*
C23	0.8960 (3)	0.3325 (2)	0.5619 (2)	0.0418 (12)
H23	0.9156	0.3648	0.5827	0.050*
C24	0.8732 (3)	0.3296 (2)	0.5002 (2)	0.0402 (11)
H24	0.8788	0.3601	0.4792	0.048*
C25	0.8426 (2)	0.28395 (19)	0.4679 (2)	0.0327 (10)
C26	0.8118 (3)	0.2870 (2)	0.4003 (2)	0.0367 (10)
H26A	0.8108	0.3250	0.3888	0.044*
H26B	0.7595	0.2743	0.3843	0.044*
C27	0.9356 (2)	0.26593 (19)	0.39840 (19)	0.0328 (10)
H27A	0.9541	0.2559	0.4415	0.039*
H27B	0.9447	0.3045	0.3963	0.039*
C28	0.9796 (2)	0.2354 (2)	0.36957 (19)	0.0349 (10)
H28A	0.9744	0.2529	0.3314	0.042*
H28B	0.9605	0.1985	0.3604	0.042*
C29	1.0611 (3)	0.2350 (2)	0.4138 (2)	0.0374 (11)
H29A	1.0797	0.2722	0.4212	0.045*
H29B	1.0647	0.2201	0.4527	0.045*
C30	1.0909 (3)	0.1453 (2)	0.3851 (2)	0.0449 (12)
H30A	1.0381	0.1410	0.3582	0.067*
H30B	1.0998	0.1301	0.4246	0.067*
H30C	1.1220	0.1269	0.3679	0.067*
C31	1.1903 (3)	0.2099 (3)	0.4332 (3)	0.0569 (15)
H31A	1.2028	0.2479	0.4377	0.085*
H31B	1.2218	0.1915	0.4163	0.085*
H31C	1.1990	0.1947	0.4727	0.085*
C32	0.8204 (2)	0.26915 (19)	0.30314 (19)	0.0330 (10)
H32A	0.8493	0.2506	0.2835	0.040*
H32B	0.8249	0.3080	0.2981	0.040*
C33	0.7386 (3)	0.2530 (2)	0.2723 (2)	0.0386 (11)
H33A	0.7330	0.2144	0.2782	0.046*
H33B	0.7084	0.2731	0.2897	0.046*
C34	0.7122 (3)	0.2653 (2)	0.2056 (2)	0.0441 (12)
H34A	0.7271	0.3021	0.2005	0.053*
H34B	0.7364	0.2405	0.1872	0.053*
C35	0.6006 (4)	0.2856 (3)	0.1148 (3)	0.0702 (19)
H35A	0.6184	0.3225	0.1189	0.105*
H35B	0.5459	0.2854	0.0977	0.105*
H35C	0.6182	0.2660	0.0881	0.105*
C36	0.6051 (3)	0.2038 (3)	0.1718 (2)	0.0585 (16)
H36A	0.6255	0.1886	0.2125	0.088*
H36B	0.6233	0.1834	0.1460	0.088*
H36C	0.5504	0.2022	0.1551	0.088*
O1W	0.5627 (2)	−0.11798 (16)	0.17412 (17)	0.0506 (9)
H1WA	0.5186 (13)	−0.125 (2)	0.168 (2)	0.061*
H1WB	0.589 (2)	−0.123 (3)	0.2102 (12)	0.061*
O2W	0.9681 (5)	0.0252 (4)	0.2408 (5)	0.082 (3)*	0.50
Cl1	0.97380 (6)	0.11096 (5)	0.48216 (5)	0.0437 (3)
O11	1.0522 (2)	0.1008 (2)	0.50440 (19)	0.0709 (13)
O12	0.9601 (3)	0.1515 (2)	0.5173 (2)	0.0907 (17)
O13	0.9445 (2)	0.12648 (19)	0.42027 (17)	0.0638 (12)
O14	0.9353 (3)	0.0636 (2)	0.4864 (2)	0.0781 (14)
Cl2	1.14130 (7)	0.34632 (5)	0.33606 (6)	0.0476 (3)
O21	1.1708 (3)	0.36700 (18)	0.29556 (19)	0.0667 (12)
O22	1.1055 (3)	0.29673 (17)	0.3134 (2)	0.0767 (14)
O23	1.0892 (3)	0.3846 (2)	0.3400 (2)	0.0851 (16)
O24	1.2018 (3)	0.3390 (2)	0.3932 (2)	0.0857 (15)
Cl3	0.80344 (7)	−0.09755 (5)	0.20105 (5)	0.0429 (3)
O31	0.7242 (3)	−0.0925 (2)	0.1759 (3)	0.0855 (16)
O32	0.8267 (3)	−0.1218 (2)	0.25926 (18)	0.0835 (16)
O33	0.8382 (3)	−0.04650 (17)	0.2075 (2)	0.0853 (17)
O34	0.8237 (2)	−0.13032 (15)	0.16220 (16)	0.0512 (9)
Cl4	0.5000	0.28569 (11)	0.2500	0.0731 (6)
O41	0.4355 (4)	0.2570 (4)	0.2281 (3)	0.165 (4)
O42	0.5038 (5)	0.3126 (3)	0.2020 (5)	0.189 (4)
Cl5	0.41888 (7)	−0.14088 (5)	−0.02396 (6)	0.0463 (3)
O51	0.3437 (3)	−0.1463 (3)	−0.0591 (4)	0.180 (5)
O52	0.4489 (4)	−0.1046 (2)	−0.0536 (3)	0.113 (2)
O53	0.4347 (4)	−0.1202 (3)	0.0338 (2)	0.1028 (19)
O54	0.4543 (3)	−0.19040 (17)	−0.02144 (18)	0.0673 (12)
Cl6	0.5000	0.09905 (7)	0.2500	0.0434 (4)
O61	0.5000	0.0423 (2)	0.2500	0.0626 (15)*
O62	0.5722 (4)	0.1244 (3)	0.2816 (3)	0.0475 (17)*	0.50
O63	0.4696 (5)	0.1094 (4)	0.2973 (4)	0.075 (3)*	0.50
O64	0.4592 (7)	0.1181 (5)	0.1966 (5)	0.091 (3)*	0.50
Cl7	1.14682 (7)	0.13151 (5)	0.25946 (5)	0.0441 (3)
O71	1.0715 (3)	0.1145 (4)	0.2315 (3)	0.163 (4)
O72	1.1825 (4)	0.0908 (2)	0.2980 (3)	0.110 (2)
O73	1.1453 (5)	0.17912 (19)	0.2873 (3)	0.143 (3)
O74	1.1737 (2)	0.13856 (15)	0.21346 (16)	0.0516 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0320 (16)	0.0381 (18)	0.0291 (15)	−0.0032 (13)	0.0110 (12)	−0.0035 (13)
N1	0.0297 (18)	0.035 (2)	0.0334 (19)	−0.0025 (16)	0.0106 (15)	−0.0022 (16)
N2	0.037 (2)	0.034 (2)	0.0306 (18)	−0.0044 (17)	0.0115 (15)	−0.0022 (16)
N3	0.0320 (19)	0.032 (2)	0.0334 (19)	−0.0056 (16)	0.0104 (15)	−0.0039 (16)
N4	0.045 (2)	0.066 (3)	0.042 (2)	0.015 (2)	0.0214 (19)	0.008 (2)
N5	0.0316 (19)	0.035 (2)	0.0317 (19)	−0.0001 (16)	0.0094 (15)	−0.0021 (16)
N6	0.0325 (19)	0.031 (2)	0.0316 (18)	−0.0017 (16)	0.0120 (15)	−0.0049 (15)
N7	0.032 (2)	0.037 (2)	0.039 (2)	0.0019 (17)	0.0151 (16)	0.0031 (17)
N8	0.040 (2)	0.054 (3)	0.045 (2)	0.002 (2)	0.0059 (19)	0.002 (2)
C1	0.029 (2)	0.035 (3)	0.034 (2)	0.0008 (19)	0.0103 (18)	−0.0058 (19)
C2	0.024 (2)	0.040 (3)	0.041 (2)	0.0010 (19)	0.0108 (18)	0.000 (2)
C3	0.032 (2)	0.049 (3)	0.038 (2)	−0.005 (2)	0.0141 (19)	0.001 (2)
C4	0.036 (3)	0.055 (3)	0.040 (3)	−0.002 (2)	0.017 (2)	0.007 (2)
C5	0.040 (3)	0.047 (3)	0.060 (3)	−0.002 (2)	0.026 (2)	0.009 (3)
C6	0.039 (3)	0.037 (3)	0.054 (3)	−0.005 (2)	0.020 (2)	−0.005 (2)
C7	0.026 (2)	0.044 (3)	0.037 (2)	−0.003 (2)	0.0104 (18)	−0.004 (2)
C8	0.030 (2)	0.044 (3)	0.042 (3)	−0.004 (2)	0.0154 (19)	−0.005 (2)
C9	0.034 (2)	0.036 (3)	0.037 (2)	0.002 (2)	0.0080 (19)	−0.001 (2)
C10	0.036 (2)	0.044 (3)	0.035 (2)	−0.001 (2)	0.0150 (19)	−0.001 (2)
C11	0.038 (2)	0.038 (3)	0.043 (3)	−0.001 (2)	0.017 (2)	0.001 (2)
C12	0.054 (3)	0.057 (4)	0.089 (5)	−0.008 (3)	0.030 (3)	−0.008 (3)
C13	0.068 (4)	0.049 (4)	0.106 (5)	0.011 (3)	0.043 (4)	−0.019 (4)
C14	0.032 (2)	0.035 (3)	0.034 (2)	−0.003 (2)	0.0097 (18)	−0.0017 (19)
C15	0.032 (2)	0.032 (2)	0.039 (2)	−0.0014 (19)	0.0115 (19)	−0.005 (2)
C16	0.036 (2)	0.030 (2)	0.039 (2)	−0.007 (2)	0.0094 (19)	−0.007 (2)
C17	0.032 (2)	0.057 (3)	0.041 (3)	−0.002 (2)	0.012 (2)	−0.012 (2)
C18	0.043 (3)	0.050 (3)	0.038 (3)	−0.003 (2)	0.016 (2)	−0.005 (2)
C19	0.027 (2)	0.034 (3)	0.034 (2)	−0.0027 (18)	0.0125 (17)	−0.0071 (19)
C20	0.025 (2)	0.036 (3)	0.038 (2)	0.0005 (18)	0.0114 (18)	−0.010 (2)
C21	0.032 (2)	0.047 (3)	0.032 (2)	−0.001 (2)	0.0091 (18)	−0.007 (2)
C22	0.032 (2)	0.057 (3)	0.034 (2)	−0.001 (2)	0.0087 (19)	−0.017 (2)
C23	0.030 (2)	0.044 (3)	0.047 (3)	−0.001 (2)	0.011 (2)	−0.017 (2)
C24	0.038 (3)	0.040 (3)	0.046 (3)	−0.002 (2)	0.021 (2)	−0.005 (2)
C25	0.026 (2)	0.034 (3)	0.037 (2)	0.0032 (19)	0.0117 (18)	−0.0041 (19)
C26	0.036 (2)	0.037 (3)	0.039 (2)	0.000 (2)	0.017 (2)	−0.007 (2)
C27	0.032 (2)	0.033 (2)	0.031 (2)	−0.0028 (19)	0.0102 (18)	−0.0024 (18)
C28	0.031 (2)	0.042 (3)	0.029 (2)	−0.002 (2)	0.0085 (17)	−0.0052 (19)
C29	0.036 (2)	0.042 (3)	0.036 (2)	−0.001 (2)	0.0152 (19)	−0.004 (2)
C30	0.050 (3)	0.036 (3)	0.054 (3)	0.006 (2)	0.027 (2)	0.004 (2)
C31	0.035 (3)	0.070 (4)	0.059 (3)	0.003 (3)	0.012 (2)	0.005 (3)
C32	0.036 (2)	0.033 (3)	0.030 (2)	−0.0010 (19)	0.0126 (18)	0.0032 (18)
C33	0.036 (2)	0.041 (3)	0.036 (2)	−0.004 (2)	0.0113 (19)	0.000 (2)
C34	0.038 (3)	0.052 (3)	0.040 (3)	−0.003 (2)	0.012 (2)	0.006 (2)
C35	0.068 (4)	0.072 (5)	0.045 (3)	0.007 (3)	−0.003 (3)	0.013 (3)
C36	0.049 (3)	0.063 (4)	0.045 (3)	−0.012 (3)	0.000 (2)	−0.003 (3)
O1W	0.047 (2)	0.046 (2)	0.060 (2)	−0.0051 (18)	0.0228 (18)	0.0028 (19)
Cl1	0.0394 (6)	0.0536 (8)	0.0401 (6)	0.0062 (5)	0.0179 (5)	0.0096 (5)
O11	0.044 (2)	0.107 (4)	0.062 (3)	0.021 (2)	0.0223 (19)	0.028 (2)
O12	0.074 (3)	0.096 (4)	0.076 (3)	0.025 (3)	0.004 (2)	−0.035 (3)
O13	0.056 (2)	0.089 (3)	0.048 (2)	0.013 (2)	0.0230 (18)	0.026 (2)
O14	0.085 (3)	0.074 (3)	0.071 (3)	−0.022 (3)	0.027 (2)	0.020 (2)
Cl2	0.0554 (7)	0.0435 (7)	0.0517 (7)	−0.0006 (6)	0.0295 (6)	−0.0031 (6)
O21	0.078 (3)	0.064 (3)	0.072 (3)	−0.004 (2)	0.045 (2)	0.011 (2)
O22	0.109 (4)	0.046 (3)	0.071 (3)	−0.025 (3)	0.032 (3)	−0.001 (2)
O23	0.060 (3)	0.093 (4)	0.111 (4)	0.005 (3)	0.044 (3)	−0.037 (3)
O24	0.091 (4)	0.083 (4)	0.062 (3)	−0.001 (3)	0.010 (2)	0.008 (3)
Cl3	0.0525 (7)	0.0393 (7)	0.0397 (6)	−0.0092 (5)	0.0214 (5)	−0.0057 (5)
O31	0.055 (3)	0.083 (4)	0.114 (4)	0.017 (2)	0.030 (3)	−0.023 (3)
O32	0.130 (4)	0.078 (3)	0.041 (2)	−0.028 (3)	0.032 (2)	0.000 (2)
O33	0.157 (5)	0.045 (3)	0.077 (3)	−0.048 (3)	0.071 (3)	−0.023 (2)
O34	0.053 (2)	0.055 (2)	0.054 (2)	−0.0083 (18)	0.0308 (18)	−0.0141 (18)
Cl4	0.0630 (14)	0.0767 (17)	0.0780 (15)	0.000	0.0266 (12)	0.000
O41	0.129 (6)	0.282 (11)	0.123 (5)	−0.123 (7)	0.091 (5)	−0.102 (6)
O42	0.147 (7)	0.145 (7)	0.283 (11)	0.043 (6)	0.096 (7)	0.147 (8)
Cl5	0.0354 (6)	0.0448 (7)	0.0524 (7)	−0.0001 (5)	0.0111 (5)	−0.0112 (6)
O51	0.035 (3)	0.192 (8)	0.273 (9)	−0.001 (4)	0.019 (4)	−0.169 (7)
O52	0.206 (7)	0.046 (3)	0.086 (4)	−0.015 (4)	0.058 (4)	0.011 (3)
O53	0.133 (5)	0.113 (5)	0.074 (3)	−0.015 (4)	0.054 (3)	−0.047 (3)
O54	0.087 (3)	0.051 (3)	0.058 (2)	0.023 (2)	0.024 (2)	0.013 (2)
Cl6	0.0347 (8)	0.0388 (9)	0.0529 (10)	0.000	0.0138 (7)	0.000
Cl7	0.0518 (7)	0.0391 (7)	0.0441 (6)	0.0056 (5)	0.0218 (5)	0.0014 (5)
O71	0.065 (4)	0.335 (12)	0.090 (4)	−0.041 (5)	0.032 (3)	0.011 (6)
O72	0.152 (5)	0.112 (5)	0.095 (4)	0.084 (4)	0.079 (4)	0.062 (3)
O73	0.336 (11)	0.038 (3)	0.147 (5)	−0.007 (4)	0.195 (7)	−0.008 (3)
O74	0.071 (3)	0.048 (2)	0.047 (2)	0.0028 (19)	0.0356 (18)	−0.0017 (17)

O1—C19	1.359 (5)	C19—C20	1.451 (6)
O1—C1	1.365 (5)	C20—C25	1.410 (7)
N1—C19	1.302 (5)	C20—C21	1.411 (6)
N1—N2	1.400 (5)	C21—C22	1.383 (7)
N2—C1	1.299 (6)	C21—H21	0.9500
N3—C9	1.498 (6)	C22—C23	1.384 (8)
N3—C14	1.511 (6)	C22—H22	0.9500
N3—C8	1.517 (6)	C23—C24	1.379 (7)
N3—H3	0.9300	C23—H23	0.9500
N4—C13	1.479 (7)	C24—C25	1.380 (7)
N4—C11	1.494 (6)	C24—H24	0.9500
N4—C12	1.537 (8)	C25—C26	1.502 (6)
N4—H4	0.9300	C26—H26A	0.9900
N5—C17	1.489 (6)	C26—H26B	0.9900
N5—C18	1.495 (6)	C27—C28	1.515 (6)
N5—C16	1.510 (5)	C27—H27A	0.9900
N5—H5	0.9300	C27—H27B	0.9900
N6—C27	1.503 (5)	C28—C29	1.524 (6)
N6—C32	1.503 (5)	C28—H28A	0.9900
N6—C26	1.522 (6)	C28—H28B	0.9900
N6—H6	0.9300	C29—H29A	0.9900
N7—C30	1.490 (6)	C29—H29B	0.9900
N7—C31	1.494 (6)	C30—H30A	0.9800
N7—C29	1.501 (6)	C30—H30B	0.9800
N7—H7	0.9300	C30—H30C	0.9800
N8—C35	1.469 (7)	C31—H31A	0.9800
N8—C36	1.481 (7)	C31—H31B	0.9800
N8—C34	1.495 (6)	C31—H31C	0.9800
N8—H8	0.9300	C32—C33	1.524 (6)
C1—C2	1.458 (7)	C32—H32A	0.9900
C2—C3	1.399 (6)	C32—H32B	0.9900
C2—C7	1.421 (7)	C33—C34	1.516 (6)
C3—C4	1.372 (7)	C33—H33A	0.9900
C3—H3A	0.9500	C33—H33B	0.9900
C4—C5	1.383 (8)	C34—H34A	0.9900
C4—H4A	0.9500	C34—H34B	0.9900
C5—C6	1.387 (7)	C35—H35A	0.9800
C5—H5A	0.9500	C35—H35B	0.9800
C6—C7	1.385 (7)	C35—H35C	0.9800
C6—H6A	0.9500	C36—H36A	0.9800
C7—C8	1.499 (6)	C36—H36B	0.9800
C8—H8A	0.9900	C36—H36C	0.9800
C8—H8B	0.9900	O1W—H1WA	0.836 (19)
C9—C10	1.516 (7)	O1W—H1WB	0.828 (19)
C9—H9A	0.9900	Cl1—O12	1.419 (5)
C9—H9B	0.9900	Cl1—O13	1.427 (4)
C10—C11	1.498 (7)	Cl1—O11	1.429 (4)
C10—H10A	0.9900	Cl1—O14	1.431 (5)
C10—H10B	0.9900	Cl2—O21	1.421 (4)
C11—H11A	0.9900	Cl2—O22	1.425 (4)
C11—H11B	0.9900	Cl2—O24	1.427 (5)
C12—H12A	0.9800	Cl2—O23	1.430 (5)
C12—H12B	0.9800	Cl3—O34	1.421 (4)
C12—H12C	0.9800	Cl3—O31	1.425 (5)
C13—H13A	0.9800	Cl3—O33	1.429 (4)
C13—H13B	0.9800	Cl3—O32	1.432 (4)
C13—H13C	0.9800	Cl4—O41	1.361 (6)
C14—C15	1.519 (6)	Cl4—O42	1.371 (8)
C14—H14A	0.9900	Cl5—O51	1.378 (5)
C14—H14B	0.9900	Cl5—O53	1.406 (5)
C15—C16	1.525 (6)	Cl5—O54	1.411 (4)
C15—H15A	0.9900	Cl5—O52	1.423 (6)
C15—H15B	0.9900	Cl6—O64	1.308 (11)
C16—H16A	0.9900	Cl6—O61	1.423 (6)
C16—H16B	0.9900	Cl6—O62	1.455 (7)
C17—H17A	0.9800	Cl6—O63	1.512 (10)
C17—H17B	0.9800	Cl7—O72	1.370 (5)
C17—H17C	0.9800	Cl7—O73	1.377 (5)
C18—H18A	0.9800	Cl7—O71	1.417 (6)
C18—H18B	0.9800	Cl7—O74	1.421 (4)
C18—H18C	0.9800
C19—O1—C1	103.4 (3)	O1—C19—C20	119.2 (4)
C19—N1—N2	106.2 (4)	C25—C20—C21	119.6 (4)
C1—N2—N1	106.8 (4)	C25—C20—C19	121.4 (4)
C9—N3—C14	114.8 (3)	C21—C20—C19	119.0 (4)
C9—N3—C8	112.5 (4)	C22—C21—C20	119.9 (5)
C14—N3—C8	111.8 (3)	C22—C21—H21	120.0
C9—N3—H3	105.6	C20—C21—H21	120.0
C14—N3—H3	105.6	C21—C22—C23	120.5 (4)
C8—N3—H3	105.6	C21—C22—H22	119.8
C13—N4—C11	111.5 (5)	C23—C22—H22	119.8
C13—N4—C12	109.1 (5)	C24—C23—C22	119.3 (5)
C11—N4—C12	109.1 (4)	C24—C23—H23	120.3
C13—N4—H4	109.0	C22—C23—H23	120.3
C11—N4—H4	109.0	C23—C24—C25	122.4 (5)
C12—N4—H4	109.0	C23—C24—H24	118.8
C17—N5—C18	110.4 (3)	C25—C24—H24	118.8
C17—N5—C16	111.7 (4)	C24—C25—C20	118.3 (4)
C18—N5—C16	111.1 (4)	C24—C25—C26	117.9 (4)
C17—N5—H5	107.8	C20—C25—C26	123.6 (4)
C18—N5—H5	107.8	C25—C26—N6	117.0 (4)
C16—N5—H5	107.8	C25—C26—H26A	108.1
C27—N6—C32	112.2 (3)	N6—C26—H26A	108.1
C27—N6—C26	111.2 (3)	C25—C26—H26B	108.1
C32—N6—C26	109.4 (3)	N6—C26—H26B	108.1
C27—N6—H6	107.9	H26A—C26—H26B	107.3
C32—N6—H6	107.9	N6—C27—C28	113.6 (3)
C26—N6—H6	107.9	N6—C27—H27A	108.8
C30—N7—C31	109.6 (4)	C28—C27—H27A	108.8
C30—N7—C29	112.9 (4)	N6—C27—H27B	108.8
C31—N7—C29	110.4 (4)	C28—C27—H27B	108.8
C30—N7—H7	107.9	H27A—C27—H27B	107.7
C31—N7—H7	107.9	C27—C28—C29	107.9 (4)
C29—N7—H7	107.9	C27—C28—H28A	110.1
C35—N8—C36	112.6 (5)	C29—C28—H28A	110.1
C35—N8—C34	111.6 (5)	C27—C28—H28B	110.1
C36—N8—C34	111.7 (4)	C29—C28—H28B	110.1
C35—N8—H8	106.9	H28A—C28—H28B	108.4
C36—N8—H8	106.9	N7—C29—C28	113.0 (4)
C34—N8—H8	106.9	N7—C29—H29A	109.0
N2—C1—O1	111.6 (4)	C28—C29—H29A	109.0
N2—C1—C2	129.1 (4)	N7—C29—H29B	109.0
O1—C1—C2	119.2 (4)	C28—C29—H29B	109.0
C3—C2—C7	120.2 (5)	H29A—C29—H29B	107.8
C3—C2—C1	117.9 (4)	N7—C30—H30A	109.5
C7—C2—C1	121.9 (4)	N7—C30—H30B	109.5
C4—C3—C2	120.8 (5)	H30A—C30—H30B	109.5
C4—C3—H3A	119.6	N7—C30—H30C	109.5
C2—C3—H3A	119.6	H30A—C30—H30C	109.5
C3—C4—C5	120.0 (5)	H30B—C30—H30C	109.5
C3—C4—H4A	120.0	N7—C31—H31A	109.5
C5—C4—H4A	120.0	N7—C31—H31B	109.5
C4—C5—C6	119.5 (5)	H31A—C31—H31B	109.5
C4—C5—H5A	120.2	N7—C31—H31C	109.5
C6—C5—H5A	120.2	H31A—C31—H31C	109.5
C7—C6—C5	122.7 (5)	H31B—C31—H31C	109.5
C7—C6—H6A	118.7	N6—C32—C33	112.0 (4)
C5—C6—H6A	118.7	N6—C32—H32A	109.2
C6—C7—C2	116.9 (4)	C33—C32—H32A	109.2
C6—C7—C8	118.6 (4)	N6—C32—H32B	109.2
C2—C7—C8	124.4 (5)	C33—C32—H32B	109.2
C7—C8—N3	114.8 (4)	H32A—C32—H32B	107.9
C7—C8—H8A	108.6	C34—C33—C32	108.0 (4)
N3—C8—H8A	108.6	C34—C33—H33A	110.1
C7—C8—H8B	108.6	C32—C33—H33A	110.1
N3—C8—H8B	108.6	C34—C33—H33B	110.1
H8A—C8—H8B	107.6	C32—C33—H33B	110.1
N3—C9—C10	111.3 (4)	H33A—C33—H33B	108.4
N3—C9—H9A	109.4	N8—C34—C33	110.9 (4)
C10—C9—H9A	109.4	N8—C34—H34A	109.5
N3—C9—H9B	109.4	C33—C34—H34A	109.5
C10—C9—H9B	109.4	N8—C34—H34B	109.5
H9A—C9—H9B	108.0	C33—C34—H34B	109.5
C11—C10—C9	109.1 (4)	H34A—C34—H34B	108.0
C11—C10—H10A	109.9	N8—C35—H35A	109.5
C9—C10—H10A	109.9	N8—C35—H35B	109.5
C11—C10—H10B	109.9	H35A—C35—H35B	109.5
C9—C10—H10B	109.9	N8—C35—H35C	109.5
H10A—C10—H10B	108.3	H35A—C35—H35C	109.5
N4—C11—C10	112.6 (4)	H35B—C35—H35C	109.5
N4—C11—H11A	109.1	N8—C36—H36A	109.5
C10—C11—H11A	109.1	N8—C36—H36B	109.5
N4—C11—H11B	109.1	H36A—C36—H36B	109.5
C10—C11—H11B	109.1	N8—C36—H36C	109.5
H11A—C11—H11B	107.8	H36A—C36—H36C	109.5
N4—C12—H12A	109.5	H36B—C36—H36C	109.5
N4—C12—H12B	109.5	H1WA—O1W—H1WB	108 (3)
H12A—C12—H12B	109.5	O12—Cl1—O13	109.9 (3)
N4—C12—H12C	109.5	O12—Cl1—O11	109.5 (3)
H12A—C12—H12C	109.5	O13—Cl1—O11	111.2 (2)
H12B—C12—H12C	109.5	O12—Cl1—O14	108.7 (4)
N4—C13—H13A	109.5	O13—Cl1—O14	107.5 (3)
N4—C13—H13B	109.5	O11—Cl1—O14	109.9 (3)
H13A—C13—H13B	109.5	O21—Cl2—O22	109.0 (3)
N4—C13—H13C	109.5	O21—Cl2—O24	108.0 (3)
H13A—C13—H13C	109.5	O22—Cl2—O24	110.4 (3)
H13B—C13—H13C	109.5	O21—Cl2—O23	107.4 (3)
N3—C14—C15	114.7 (4)	O22—Cl2—O23	111.0 (3)
N3—C14—H14A	108.6	O24—Cl2—O23	110.9 (3)
C15—C14—H14A	108.6	O34—Cl3—O31	108.3 (3)
N3—C14—H14B	108.6	O34—Cl3—O33	110.1 (2)
C15—C14—H14B	108.6	O31—Cl3—O33	110.8 (3)
H14A—C14—H14B	107.6	O34—Cl3—O32	110.1 (3)
C14—C15—C16	107.3 (4)	O31—Cl3—O32	108.6 (3)
C14—C15—H15A	110.3	O33—Cl3—O32	108.9 (3)
C16—C15—H15A	110.3	O41i—Cl4—O41	116.1 (9)
C14—C15—H15B	110.3	O41i—Cl4—O42	103.5 (4)
C16—C15—H15B	110.3	O41—Cl4—O42	106.7 (6)
H15A—C15—H15B	108.5	O41i—Cl4—O42i	106.7 (6)
N5—C16—C15	111.2 (4)	O41—Cl4—O42i	103.5 (4)
N5—C16—H16A	109.4	O42—Cl4—O42i	121.0 (10)
C15—C16—H16A	109.4	O51—Cl5—O53	113.9 (4)
N5—C16—H16B	109.4	O51—Cl5—O54	108.8 (4)
C15—C16—H16B	109.4	O53—Cl5—O54	111.9 (3)
H16A—C16—H16B	108.0	O51—Cl5—O52	107.8 (6)
N5—C17—H17A	109.5	O53—Cl5—O52	107.2 (4)
N5—C17—H17B	109.5	O54—Cl5—O52	106.8 (3)
H17A—C17—H17B	109.5	O64—Cl6—O61	111.4 (5)
N5—C17—H17C	109.5	O64—Cl6—O62	116.0 (5)
H17A—C17—H17C	109.5	O61—Cl6—O62	115.9 (3)
H17B—C17—H17C	109.5	O64—Cl6—O63	114.8 (6)
N5—C18—H18A	109.5	O61—Cl6—O63	99.9 (4)
N5—C18—H18B	109.5	O62—Cl6—O63	97.0 (5)
H18A—C18—H18B	109.5	O72—Cl7—O73	114.7 (4)
N5—C18—H18C	109.5	O72—Cl7—O71	104.3 (5)
H18A—C18—H18C	109.5	O73—Cl7—O71	105.9 (6)
H18B—C18—H18C	109.5	O72—Cl7—O74	112.3 (3)
N1—C19—O1	112.0 (4)	O73—Cl7—O74	111.3 (3)
N1—C19—C20	128.7 (4)	O71—Cl7—O74	107.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2	0.93	1.90	2.714 (5)	145
N6—H6···N1	0.93	2.04	2.779 (6)	136
N5—H5···O1W	0.93	1.85	2.747 (6)	160
N4—H4···O2W	0.93	1.95	2.83 (1)	156
N4—H4···O2Wii	0.93	2.30	2.97 (1)	129
O1W—H1WA···O23iii	0.84 (3)	2.05 (3)	2.852 (7)	160 (3)
O1W—H1WB···O21iv	0.83 (3)	2.06 (3)	2.876 (5)	169 (3)
N7—H7···O22	0.93	2.26	3.000 (6)	137
N7—H7···O73	0.93	2.28	2.94 (1)	127
N8—H8···O42	0.93	2.27	3.09 (1)	146
N8—H8···O41i	0.93	2.36	3.10 (1)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2	0.93	1.90	2.714 (5)	145
N6—H6⋯N1	0.93	2.04	2.779 (6)	136
N5—H5⋯O1W	0.93	1.85	2.747 (6)	160
N4—H4⋯O2W	0.93	1.95	2.83 (1)	156
N4—H4⋯O2W i	0.93	2.30	2.97 (1)	129
O1W—H1WA⋯O23ii	0.84 (3)	2.05 (3)	2.852 (7)	160 (3)
O1W—H1WB⋯O21iii	0.83 (3)	2.06 (3)	2.876 (5)	169 (3)
N7—H7⋯O22	0.93	2.26	3.000 (6)	137
N7—H7⋯O73	0.93	2.28	2.94 (1)	127
N8—H8⋯O42	0.93	2.27	3.09 (1)	146
N8—H8⋯O41iv	0.93	2.36	3.10 (1)	137

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