Supramolecular structure, in vivo biological activities and molecular-docking-based potential cardiotoxic exploration of aconine hydro­chloride monohydrate as a novel salt form

Despite the high profile of aconine in WuTou injection, there has been no preparative technology or structural studies of its salt as the pharmaceutical product. The lack of any halide salt forms is surprising as aconine contains a tertiary nitro­gen atom. In this work, aconine was prepared from the degradation of aconitine in Aconiti kusnezoffii radix (CaoWu). A green chemistry technique was applied to enrich the lipophilic-poor aconine. Reaction of aconine with hydro­chloride acid resulted in protonation of the nitro­gen atom and gave a novel salt form (C₂₅H₄₂NO₉⁺·Cl⁻·H₂O; aconine hydrochloride monohydrate, AHM), whose cation in the crystal structure was elucidated based on extensive spectroscopic and X-ray crystallographic analyses. The AHM crystal had a Z′ = 3 structure with three independent cation–anion pairs, with profound conformational differences among the aconine cations. The central framework of each aconine cation was compared with that of previously reported aconitine, proving that protonation of the nitro­gen atom induced the structure rearrangement. In the crystal of AHM, aconine cations, chloride anions and water molecules interacted through inter-species O—H...Cl and O—H...O hydrogen bonds; this complex hydrogen-bonding network stabilizes the supramolecular structure. The seriously disordered solvent molecules were treated using the PLATON SQUEEZE procedure [Spek (2015). Acta Cryst. C71, 9–18] and their atoms were therefore omitted from the refinement. Bioactivity studies indicated that AHM promoted in vitro proliferative activities of RAW264.7 cells. Molecular docking suggested AHM could target cardiotoxic protein through the hydrogen-bonding interactions. The structural confirmation of AHM offers a rational approach for improving the pharmaceutical technology of WuTou injection.

Computing details

Data collection: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); cell refinement: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); data reduction: CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(1S,3R,4S,6R,6aS,7R, 7aR,8R,9S,10S,11S,11aR, 12R,12aR,13R,14S)-1-ethyl-4,8,9,11,11a-pentahydroxy -6,10,13-trimethoxy-3-(methoxymethyl)tetradecahydro-2H-3,6a,12- (epiethane[1,1,2]triyl)-7, 9-methanonaphtho[2,3-b]azocin-1-ium chloride monohydrate

Crystal data

C25H42NO9^+·Cl^−·H2O	Dx = 1.327 Mg m^−3
Mr = 554.06	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 10762 reflections
a = 16.3296 (2) Å	θ = 3.4–29.0°
b = 16.3759 (4) Å	µ = 0.19 mm^−1
c = 31.1186 (5) Å	T = 293 K
V = 8321.5 (3) Å^3	Block
Z = 12	0.35 × 0.3 × 0.25 mm
F(000) = 3576

Data collection

Xcalibur, Eos diffractometer	16991 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	14265 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.0874 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −15→20
Absorption correction: multi-scan CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −20→17
Tmin = 0.798, Tmax = 1.000	l = −38→38
38668 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 1.2397P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.103	(Δ/σ)max = 0.028
S = 1.03	Δρmax = 0.65 e Å^−3
16991 reflections	Δρmin = −0.54 e Å^−3
1080 parameters	Absolute structure: Flack x determined using 5283 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraints	Absolute structure parameter: 0.003 (15)
Primary atom site location: iterative

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The solvent molecules contained in the unit cell have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.59637 (5)	0.21880 (7)	0.42532 (3)	0.0546 (2)
Cl2	0.38804 (6)	0.74330 (7)	0.40938 (3)	0.0557 (3)
Cl3	0.61360 (7)	0.29421 (10)	0.76109 (4)	0.0893 (5)
O1	0.76633 (13)	0.36883 (14)	0.51806 (7)	0.0405 (5)
O2	0.92107 (15)	0.29274 (17)	0.53136 (8)	0.0450 (6)
H2	0.961 (3)	0.292 (3)	0.5440 (15)	0.077 (16)*
O3	0.86816 (16)	0.05293 (16)	0.56272 (9)	0.0545 (7)
O4	0.75541 (13)	0.13388 (14)	0.65421 (7)	0.0397 (5)
O5	0.56710 (12)	0.21873 (14)	0.67003 (6)	0.0372 (5)
H5	0.5809	0.2376	0.6933	0.056*
O6	0.62375 (16)	0.40667 (16)	0.66833 (8)	0.0524 (6)
H6	0.6227	0.3947	0.6939	0.079*
O7	0.46778 (14)	0.45955 (16)	0.62249 (8)	0.0492 (6)
O8	0.44689 (14)	0.40660 (16)	0.54446 (7)	0.0454 (6)
H8	0.4079	0.4172	0.5601	0.068*
O9	0.41690 (12)	0.27489 (16)	0.61405 (7)	0.0443 (6)
H9	0.3780	0.3036	0.6070	0.066*
N1	0.81342 (14)	0.33358 (16)	0.60060 (8)	0.0319 (6)
H1	0.8307	0.3517	0.5720	0.038*
C1	0.73972 (17)	0.2858 (2)	0.51435 (9)	0.0331 (7)
H1A	0.6947	0.2838	0.4936	0.040*
C2	0.80675 (18)	0.2288 (2)	0.49902 (9)	0.0375 (7)
H2A	0.7829	0.1758	0.4929	0.045*
H2B	0.8294	0.2499	0.4724	0.045*
C3	0.87541 (18)	0.2178 (2)	0.53105 (9)	0.0352 (7)
H3	0.9114	0.1742	0.5207	0.042*
C4	0.84279 (17)	0.19317 (19)	0.57678 (9)	0.0310 (7)
C5	0.74791 (16)	0.17950 (18)	0.57625 (9)	0.0284 (6)
H5A	0.7333	0.1320	0.5587	0.034*
C6	0.70900 (17)	0.17384 (19)	0.62166 (9)	0.0293 (6)
H6A	0.6569	0.1447	0.6188	0.035*
C7	0.68927 (16)	0.26332 (19)	0.63400 (9)	0.0278 (6)
H7	0.7149	0.2783	0.6614	0.033*
C8	0.59478 (16)	0.27183 (19)	0.63622 (8)	0.0276 (6)
C9	0.56420 (18)	0.3598 (2)	0.64586 (9)	0.0332 (7)
H9A	0.5171	0.3542	0.6652	0.040*
C10	0.53530 (18)	0.4105 (2)	0.60782 (10)	0.0336 (7)
H10	0.5799	0.4469	0.5991	0.040*
C11	0.50634 (17)	0.3617 (2)	0.56796 (9)	0.0323 (7)
C12	0.57656 (17)	0.3388 (2)	0.53763 (9)	0.0307 (7)
H12A	0.6190	0.3802	0.5383	0.037*
H12B	0.5567	0.3335	0.5084	0.037*
C13	0.61073 (16)	0.25523 (18)	0.55420 (8)	0.0272 (6)
H13	0.5978	0.2138	0.5325	0.033*
C14	0.70616 (16)	0.25859 (18)	0.55888 (8)	0.0258 (6)
C15	0.72244 (16)	0.31524 (19)	0.59710 (8)	0.0263 (6)
H15	0.6909	0.3659	0.5943	0.032*
C16	0.86228 (17)	0.2586 (2)	0.61016 (10)	0.0335 (7)
H16A	0.8489	0.2386	0.6387	0.040*
H16B	0.9203	0.2714	0.6094	0.040*
C17	0.55767 (16)	0.23689 (19)	0.59452 (8)	0.0273 (6)
H17	0.5500	0.1778	0.5975	0.033*
C18	0.47694 (17)	0.2770 (2)	0.58158 (9)	0.0337 (7)
H18	0.4555	0.2487	0.5562	0.040*
C19	0.7867 (3)	0.4063 (3)	0.47852 (14)	0.0732 (13)
H19A	0.8032	0.4617	0.4836	0.110*
H19B	0.7399	0.4056	0.4599	0.110*
H19C	0.8309	0.3770	0.4653	0.110*
C20	0.89141 (19)	0.1167 (2)	0.58996 (11)	0.0418 (8)
H20A	0.9497	0.1269	0.5873	0.050*
H20B	0.8796	0.1026	0.6196	0.050*
C21	0.9228 (3)	−0.0144 (3)	0.5652 (2)	0.0946 (18)
H21A	0.9162	−0.0413	0.5924	0.142*
H21B	0.9782	0.0048	0.5625	0.142*
H21C	0.9111	−0.0521	0.5424	0.142*
C22	0.7420 (3)	0.0476 (2)	0.65441 (13)	0.0587 (10)
H22A	0.7740	0.0231	0.6768	0.088*
H22B	0.7579	0.0252	0.6272	0.088*
H22C	0.6850	0.0367	0.6594	0.088*
C23	0.4883 (7)	0.5398 (7)	0.6374 (4)	0.063 (2)	0.583 (12)
H23A	0.5159	0.5359	0.6645	0.095*	0.583 (12)
H23B	0.4392	0.5713	0.6407	0.095*	0.583 (12)
H23C	0.5235	0.5659	0.6169	0.095*	0.583 (12)
C24	0.8326 (2)	0.4027 (2)	0.63064 (12)	0.0486 (9)
H24A	0.7926	0.4039	0.6537	0.058*
H24B	0.8863	0.3945	0.6433	0.058*
C25	0.8310 (4)	0.4820 (3)	0.60706 (19)	0.0926 (17)
H25A	0.8507	0.5247	0.6255	0.139*
H25B	0.7759	0.4940	0.5984	0.139*
H25C	0.8654	0.4783	0.5821	0.139*
C23A	0.4731 (11)	0.5396 (10)	0.6155 (5)	0.063 (2)	0.417 (12)
H23D	0.5178	0.5616	0.6319	0.095*	0.417 (12)
H23E	0.4230	0.5654	0.6242	0.095*	0.417 (12)
H23F	0.4823	0.5493	0.5855	0.095*	0.417 (12)
O10	0.77197 (15)	0.34088 (18)	0.20358 (8)	0.0548 (7)
O11	0.93110 (17)	0.2616 (2)	0.21411 (10)	0.0640 (8)
H11	0.977 (3)	0.253 (3)	0.2173 (13)	0.060 (14)*
O12	0.87890 (16)	0.01921 (17)	0.23372 (8)	0.0570 (7)
O13	0.75085 (14)	0.07605 (14)	0.32010 (7)	0.0387 (5)
O14	0.55296 (13)	0.14777 (14)	0.33210 (7)	0.0358 (5)
H14	0.5629 (19)	0.160 (2)	0.3562 (10)	0.027 (9)*
O15	0.41233 (13)	0.20848 (16)	0.27556 (8)	0.0478 (6)
H15A	0.3714	0.2341	0.2683	0.072*
O16	0.60050 (14)	0.33700 (14)	0.34476 (7)	0.0384 (5)
H16	0.6017	0.3142	0.3682	0.058*
O17	0.45482 (13)	0.39670 (15)	0.29547 (8)	0.0467 (6)
O18	0.44286 (15)	0.35603 (18)	0.21425 (8)	0.0517 (7)
H18A	0.402 (3)	0.364 (3)	0.2320 (15)	0.081 (16)*
N2	0.80190 (14)	0.29001 (16)	0.28361 (8)	0.0325 (6)
H2C	0.8219	0.3211	0.2588	0.039*
C26	0.7480 (2)	0.2600 (3)	0.19140 (10)	0.0456 (9)
H26	0.7061	0.2642	0.1689	0.055*
C27	0.8180 (2)	0.2087 (3)	0.17426 (11)	0.0525 (10)
H27A	0.7962	0.1577	0.1633	0.063*
H27B	0.8434	0.2374	0.1504	0.063*
C28	0.8829 (2)	0.1900 (3)	0.20765 (11)	0.0471 (9)
H28	0.9188	0.1475	0.1960	0.056*
C29	0.84549 (17)	0.1573 (2)	0.25084 (10)	0.0353 (7)
C30	0.75212 (17)	0.1392 (2)	0.24532 (9)	0.0323 (7)
H30	0.7430	0.0958	0.2241	0.039*
C31	0.70697 (17)	0.12019 (19)	0.28800 (9)	0.0305 (6)
H31	0.6577	0.0888	0.2809	0.037*
C32	0.67886 (16)	0.20483 (18)	0.30518 (8)	0.0254 (6)
H32	0.6988	0.2143	0.3345	0.031*
C33	0.58413 (17)	0.20868 (18)	0.30317 (9)	0.0277 (6)
C34	0.54840 (17)	0.29270 (19)	0.31646 (9)	0.0297 (6)
H34	0.4982	0.2811	0.3326	0.036*
C35	0.52394 (18)	0.3517 (2)	0.28041 (10)	0.0346 (7)
H35	0.5693	0.3896	0.2752	0.041*
C36	0.50138 (18)	0.3088 (2)	0.23729 (10)	0.0376 (8)
C37	0.57675 (18)	0.2968 (2)	0.20859 (10)	0.0400 (8)
H37A	0.6160	0.3405	0.2132	0.048*
H37B	0.5611	0.2965	0.1785	0.048*
C38	0.61446 (17)	0.2126 (2)	0.22172 (9)	0.0346 (7)
H38	0.6081	0.1755	0.1972	0.041*
C39	0.70839 (17)	0.2196 (2)	0.23162 (9)	0.0325 (7)
C40	0.71416 (16)	0.26697 (19)	0.27390 (9)	0.0281 (6)
H40	0.6796	0.3158	0.2728	0.034*
C41	0.85635 (17)	0.2170 (2)	0.28795 (10)	0.0339 (7)
H41A	0.8442	0.1894	0.3148	0.041*
H41B	0.9130	0.2349	0.2890	0.041*
C42	0.55636 (17)	0.1823 (2)	0.25794 (9)	0.0316 (7)
H42	0.5515	0.1227	0.2567	0.038*
C43	0.47556 (17)	0.2215 (2)	0.24510 (10)	0.0403 (8)
H43	0.4582	0.1979	0.2176	0.048*
C44	0.8034 (4)	0.3890 (4)	0.16901 (17)	0.102 (2)
H44A	0.7669	0.3856	0.1449	0.153*
H44B	0.8564	0.3689	0.1608	0.153*
H44C	0.8080	0.4449	0.1781	0.153*
C45	0.89662 (19)	0.0820 (2)	0.26317 (11)	0.0425 (8)
H45A	0.9545	0.0951	0.2622	0.051*
H45B	0.8831	0.0646	0.2921	0.051*
C46	0.9272 (11)	−0.0538 (11)	0.2433 (5)	0.077 (4)	0.583 (12)
H46A	0.9837	−0.0390	0.2466	0.116*	0.583 (12)
H46B	0.9218	−0.0922	0.2202	0.116*	0.583 (12)
H46C	0.9077	−0.0781	0.2695	0.116*	0.583 (12)
C47	0.7458 (3)	−0.0106 (2)	0.31439 (13)	0.0575 (10)
H47A	0.7698	−0.0252	0.2873	0.086*
H47B	0.6894	−0.0271	0.3148	0.086*
H47C	0.7748	−0.0374	0.3372	0.086*
C48	0.4678 (3)	0.4781 (3)	0.3036 (2)	0.0933 (18)
H48A	0.4943	0.5028	0.2793	0.140*
H48B	0.5019	0.4838	0.3285	0.140*
H48C	0.4162	0.5046	0.3086	0.140*
C49	0.80699 (19)	0.3459 (2)	0.32189 (12)	0.0442 (8)
H49A	0.7615	0.3840	0.3210	0.053*
H49B	0.8018	0.3138	0.3479	0.053*
C50	0.8855 (2)	0.3928 (3)	0.32348 (16)	0.0700 (12)
H50A	0.8898	0.4268	0.2984	0.105*
H50B	0.9307	0.3555	0.3243	0.105*
H50C	0.8863	0.4264	0.3488	0.105*
C46A	0.9449 (16)	−0.0347 (17)	0.2275 (8)	0.077 (4)	0.417 (12)
H46D	0.9954	−0.0068	0.2334	0.116*	0.417 (12)
H46E	0.9449	−0.0537	0.1984	0.116*	0.417 (12)
H46F	0.9395	−0.0804	0.2467	0.116*	0.417 (12)
O19	0.71910 (14)	0.57932 (15)	0.39042 (8)	0.0492 (6)
O20	0.56302 (17)	0.66709 (19)	0.39411 (11)	0.0591 (8)
H20	0.522 (3)	0.679 (3)	0.3967 (14)	0.053 (14)*
O21	0.62689 (16)	0.91271 (16)	0.39136 (8)	0.0534 (7)
O22	0.75312 (13)	0.87586 (13)	0.47993 (7)	0.0359 (5)
O23	0.95088 (12)	0.80309 (13)	0.49466 (7)	0.0352 (5)
H23	0.9385	0.7985	0.5201	0.053*
O24	0.90186 (14)	0.61754 (14)	0.52032 (7)	0.0403 (5)
H24	0.8995	0.6467	0.5417	0.060*
O25	1.04589 (14)	0.54745 (16)	0.47416 (8)	0.0510 (6)
O26	1.05261 (15)	0.56689 (19)	0.39015 (8)	0.0567 (7)
H26A	1.0940	0.5631	0.4049	0.085*
O27	1.08641 (13)	0.72881 (17)	0.43900 (8)	0.0484 (6)
H27	1.1269	0.7015	0.4330	0.073*
N3	0.69615 (14)	0.65836 (16)	0.46332 (8)	0.0304 (5)
H3A	0.6732	0.6195	0.4426	0.036*
C51	0.74381 (19)	0.6531 (2)	0.36930 (10)	0.0438 (9)
H51	0.7837	0.6389	0.3470	0.053*
C52	0.6749 (2)	0.6995 (3)	0.34858 (11)	0.0502 (10)
H52A	0.6466	0.6635	0.3288	0.060*
H52B	0.6977	0.7442	0.3320	0.060*
C53	0.61324 (19)	0.7338 (2)	0.38030 (11)	0.0437 (8)
H53	0.5784	0.7730	0.3650	0.052*
C54	0.65413 (16)	0.77902 (19)	0.41912 (9)	0.0308 (6)
C55	0.74716 (17)	0.79196 (19)	0.41112 (9)	0.0298 (6)
H55	0.7564	0.8281	0.3865	0.036*
C56	0.79525 (17)	0.82213 (19)	0.45125 (9)	0.0291 (6)
H56	0.8445	0.8504	0.4411	0.035*
C57	0.82293 (16)	0.74353 (18)	0.47461 (9)	0.0258 (6)
H57	0.8054	0.7436	0.5047	0.031*
C58	0.91686 (16)	0.73635 (18)	0.47084 (9)	0.0271 (6)
C59	0.95280 (18)	0.6553 (2)	0.48874 (9)	0.0314 (7)
H59	1.0036	0.6701	0.5035	0.038*
C60	0.97578 (19)	0.5881 (2)	0.45664 (10)	0.0371 (7)
H60	0.9305	0.5489	0.4549	0.044*
C61	0.99543 (18)	0.6192 (2)	0.41088 (10)	0.0383 (8)
C62	0.91735 (19)	0.6235 (2)	0.38349 (10)	0.0393 (8)
H62A	0.8789	0.5815	0.3922	0.047*
H62B	0.9303	0.6160	0.3533	0.047*
C63	0.88031 (17)	0.7101 (2)	0.39126 (9)	0.0338 (7)
H63	0.8844	0.7402	0.3641	0.041*
C64	0.78785 (17)	0.7068 (2)	0.40376 (9)	0.0295 (6)
C65	0.78362 (16)	0.67415 (18)	0.44980 (9)	0.0258 (6)
H65	0.8164	0.6243	0.4526	0.031*
C66	0.64391 (17)	0.7332 (2)	0.46151 (9)	0.0320 (7)
H66A	0.6584	0.7691	0.4851	0.038*
H66B	0.5869	0.7178	0.4650	0.038*
C67	0.94179 (16)	0.7502 (2)	0.42359 (9)	0.0316 (7)
H67	0.9463	0.8088	0.4178	0.038*
C68	1.02108 (18)	0.7075 (2)	0.41123 (10)	0.0387 (8)
H68	1.0357	0.7235	0.3819	0.046*
C69	0.6830 (3)	0.5187 (3)	0.36299 (18)	0.0920 (18)
H69A	0.7132	0.5157	0.3366	0.138*
H69B	0.6272	0.5333	0.3570	0.138*
H69C	0.6844	0.4665	0.3771	0.138*
C70	0.60657 (18)	0.8590 (2)	0.42506 (10)	0.0373 (7)
H70A	0.5482	0.8481	0.4248	0.045*
H70B	0.6206	0.8835	0.4525	0.045*
C71	0.5869 (10)	0.9883 (12)	0.3970 (5)	0.075 (4)	0.583 (12)
H71A	0.5294	0.9817	0.3916	0.112*	0.583 (12)
H71B	0.6091	1.0276	0.3773	0.112*	0.583 (12)
H71C	0.5949	1.0070	0.4259	0.112*	0.583 (12)
C72	0.7656 (3)	0.9597 (2)	0.47007 (14)	0.0570 (10)
H72A	0.7471	0.9705	0.4413	0.086*
H72B	0.8228	0.9724	0.4723	0.086*
H72C	0.7353	0.9929	0.4899	0.086*
C73	1.0348 (4)	0.4640 (3)	0.4824 (2)	0.0985 (19)
H73A	1.0238	0.4360	0.4559	0.148*
H73B	0.9896	0.4568	0.5017	0.148*
H73C	1.0836	0.4421	0.4952	0.148*
C74	0.6913 (2)	0.6182 (2)	0.50710 (11)	0.0420 (8)
H74A	0.7383	0.5827	0.5110	0.050*
H74B	0.6931	0.6599	0.5292	0.050*
C75	0.6140 (2)	0.5693 (3)	0.51176 (17)	0.0752 (14)
H75A	0.6108	0.5300	0.4889	0.113*
H75B	0.5676	0.6051	0.5104	0.113*
H75C	0.6144	0.5415	0.5389	0.113*
C71A	0.5625 (14)	0.9709 (18)	0.3830 (8)	0.075 (4)	0.417 (12)
H71D	0.5238	0.9477	0.3632	0.112*	0.417 (12)
H71E	0.5856	1.0195	0.3707	0.112*	0.417 (12)
H71F	0.5353	0.9842	0.4094	0.112*	0.417 (12)
O28	0.27584 (18)	0.3665 (2)	0.59570 (9)	0.0549 (7)
H28A	0.2596	0.3827	0.6202	0.082*
H28B	0.236 (3)	0.355 (3)	0.5841 (15)	0.074 (17)*
O29	0.22583 (18)	0.6364 (2)	0.42915 (10)	0.0643 (8)
H29A	0.2409	0.6304	0.4551	0.096*
H29B	0.266 (3)	0.661 (3)	0.4209 (15)	0.077 (17)*
O30	0.27928 (19)	0.3099 (2)	0.25932 (11)	0.0645 (9)
H30A	0.261 (4)	0.334 (4)	0.283 (2)	0.12 (2)*
H30B	0.240 (4)	0.290 (4)	0.250 (2)	0.12 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0446 (4)	0.0828 (7)	0.0362 (4)	0.0043 (5)	−0.0013 (4)	−0.0021 (4)
Cl2	0.0442 (5)	0.0858 (8)	0.0371 (4)	0.0009 (5)	−0.0039 (4)	−0.0036 (4)
Cl3	0.0507 (6)	0.1574 (14)	0.0599 (6)	−0.0005 (7)	−0.0007 (5)	−0.0354 (8)
O1	0.0397 (12)	0.0400 (14)	0.0419 (12)	−0.0014 (11)	0.0052 (10)	0.0100 (10)
O2	0.0287 (11)	0.0567 (17)	0.0495 (14)	−0.0054 (11)	0.0007 (11)	0.0073 (12)
O3	0.0523 (14)	0.0403 (15)	0.0709 (17)	0.0115 (12)	0.0002 (13)	−0.0100 (13)
O4	0.0400 (12)	0.0416 (14)	0.0375 (11)	0.0104 (11)	−0.0015 (10)	0.0103 (10)
O5	0.0345 (11)	0.0484 (14)	0.0286 (10)	−0.0011 (10)	0.0042 (9)	0.0071 (10)
O6	0.0592 (15)	0.0489 (16)	0.0492 (13)	0.0073 (13)	−0.0226 (13)	−0.0192 (12)
O7	0.0402 (13)	0.0453 (16)	0.0621 (15)	0.0159 (11)	−0.0001 (11)	−0.0122 (12)
O8	0.0356 (12)	0.0580 (16)	0.0425 (12)	0.0158 (12)	−0.0105 (10)	0.0032 (12)
O9	0.0253 (10)	0.0643 (17)	0.0434 (12)	0.0042 (11)	0.0066 (10)	0.0041 (12)
N1	0.0248 (12)	0.0372 (15)	0.0337 (13)	−0.0038 (11)	−0.0038 (10)	−0.0033 (11)
C1	0.0255 (13)	0.046 (2)	0.0273 (14)	−0.0008 (14)	0.0006 (12)	0.0011 (14)
C2	0.0345 (15)	0.049 (2)	0.0286 (14)	0.0018 (15)	0.0055 (13)	0.0002 (14)
C3	0.0288 (14)	0.0412 (19)	0.0355 (15)	0.0036 (14)	0.0061 (13)	−0.0017 (14)
C4	0.0260 (13)	0.0351 (18)	0.0319 (15)	0.0023 (13)	−0.0013 (12)	−0.0016 (13)
C5	0.0265 (13)	0.0267 (16)	0.0320 (14)	0.0015 (12)	−0.0011 (12)	−0.0032 (12)
C6	0.0260 (14)	0.0325 (17)	0.0295 (14)	0.0021 (13)	0.0000 (12)	0.0036 (12)
C7	0.0253 (13)	0.0348 (17)	0.0233 (13)	0.0020 (12)	−0.0039 (11)	−0.0005 (12)
C8	0.0253 (13)	0.0344 (17)	0.0230 (12)	0.0023 (13)	0.0003 (11)	0.0018 (12)
C9	0.0305 (14)	0.0416 (19)	0.0275 (14)	0.0054 (14)	−0.0038 (12)	−0.0051 (13)
C10	0.0298 (15)	0.0341 (18)	0.0369 (16)	0.0053 (13)	0.0003 (13)	−0.0014 (14)
C11	0.0263 (13)	0.0387 (19)	0.0320 (15)	0.0070 (13)	−0.0057 (12)	0.0016 (13)
C12	0.0280 (14)	0.0409 (19)	0.0232 (13)	0.0016 (13)	−0.0047 (11)	0.0048 (13)
C13	0.0237 (13)	0.0324 (16)	0.0254 (13)	−0.0011 (12)	−0.0031 (11)	−0.0057 (12)
C14	0.0228 (12)	0.0296 (16)	0.0251 (13)	−0.0021 (12)	0.0004 (11)	−0.0010 (12)
C15	0.0213 (12)	0.0307 (16)	0.0268 (14)	0.0002 (12)	−0.0023 (11)	−0.0013 (12)
C16	0.0238 (13)	0.0413 (19)	0.0355 (15)	0.0017 (13)	−0.0013 (12)	0.0017 (14)
C17	0.0232 (13)	0.0302 (17)	0.0286 (14)	−0.0003 (12)	0.0013 (11)	0.0002 (12)
C18	0.0223 (13)	0.047 (2)	0.0312 (15)	0.0003 (13)	−0.0015 (12)	−0.0016 (14)
C19	0.080 (3)	0.074 (3)	0.065 (3)	0.007 (3)	0.027 (2)	0.031 (2)
C20	0.0309 (15)	0.047 (2)	0.0472 (18)	0.0108 (15)	0.0029 (14)	−0.0003 (16)
C21	0.092 (4)	0.057 (3)	0.135 (5)	0.037 (3)	−0.011 (3)	−0.024 (3)
C22	0.066 (2)	0.041 (2)	0.069 (3)	0.010 (2)	0.006 (2)	0.0191 (19)
C23	0.072 (5)	0.043 (3)	0.074 (7)	0.014 (3)	0.008 (6)	−0.012 (6)
C24	0.0439 (19)	0.047 (2)	0.055 (2)	−0.0055 (17)	−0.0096 (17)	−0.0159 (18)
C25	0.110 (4)	0.049 (3)	0.118 (4)	−0.013 (3)	−0.009 (4)	−0.016 (3)
C23A	0.072 (5)	0.043 (3)	0.074 (7)	0.014 (3)	0.008 (6)	−0.012 (6)
O10	0.0447 (13)	0.0641 (19)	0.0555 (15)	0.0004 (13)	0.0090 (12)	0.0273 (13)
O11	0.0349 (14)	0.085 (2)	0.0718 (19)	−0.0057 (15)	0.0021 (13)	0.0212 (16)
O12	0.0536 (15)	0.0548 (17)	0.0628 (16)	0.0160 (13)	−0.0043 (13)	−0.0247 (13)
O13	0.0467 (12)	0.0325 (13)	0.0368 (11)	0.0084 (10)	−0.0009 (10)	0.0027 (9)
O14	0.0390 (12)	0.0353 (13)	0.0332 (12)	−0.0052 (10)	0.0058 (10)	0.0023 (10)
O15	0.0262 (10)	0.0617 (17)	0.0555 (14)	−0.0034 (11)	0.0039 (11)	−0.0023 (12)
O16	0.0425 (12)	0.0370 (13)	0.0359 (11)	0.0013 (11)	−0.0065 (10)	−0.0086 (10)
O17	0.0352 (12)	0.0421 (15)	0.0629 (15)	0.0103 (11)	0.0025 (11)	−0.0043 (12)
O18	0.0323 (12)	0.076 (2)	0.0465 (14)	0.0134 (13)	−0.0075 (11)	0.0124 (13)
N2	0.0238 (11)	0.0362 (15)	0.0374 (13)	−0.0015 (11)	−0.0012 (10)	−0.0011 (11)
C26	0.0339 (16)	0.075 (3)	0.0284 (15)	0.0039 (17)	0.0035 (13)	0.0104 (16)
C27	0.0362 (17)	0.092 (3)	0.0297 (16)	0.0085 (19)	0.0084 (14)	0.0031 (18)
C28	0.0312 (16)	0.065 (3)	0.0454 (18)	0.0053 (17)	0.0063 (15)	0.0001 (17)
C29	0.0244 (14)	0.048 (2)	0.0331 (15)	0.0045 (14)	−0.0005 (12)	−0.0084 (15)
C30	0.0276 (14)	0.0405 (19)	0.0289 (14)	0.0038 (13)	−0.0015 (12)	−0.0103 (13)
C31	0.0280 (14)	0.0303 (17)	0.0332 (15)	−0.0004 (13)	−0.0039 (12)	−0.0027 (13)
C32	0.0252 (13)	0.0281 (16)	0.0230 (13)	−0.0003 (12)	−0.0029 (11)	−0.0039 (11)
C33	0.0269 (13)	0.0276 (16)	0.0285 (14)	−0.0012 (12)	0.0032 (12)	0.0006 (12)
C34	0.0238 (12)	0.0354 (18)	0.0298 (14)	−0.0016 (12)	0.0013 (12)	−0.0029 (13)
C35	0.0255 (14)	0.0360 (19)	0.0422 (17)	0.0042 (13)	0.0026 (13)	0.0019 (14)
C36	0.0269 (14)	0.050 (2)	0.0360 (16)	0.0063 (14)	−0.0073 (13)	0.0042 (15)
C37	0.0301 (15)	0.062 (2)	0.0284 (15)	0.0051 (16)	−0.0006 (13)	0.0075 (15)
C38	0.0275 (14)	0.051 (2)	0.0248 (13)	0.0009 (14)	−0.0030 (12)	−0.0053 (14)
C39	0.0248 (13)	0.045 (2)	0.0272 (14)	0.0028 (14)	−0.0004 (12)	−0.0026 (13)
C40	0.0206 (13)	0.0319 (17)	0.0319 (14)	0.0021 (12)	−0.0009 (11)	0.0023 (13)
C41	0.0268 (14)	0.0372 (18)	0.0377 (16)	0.0044 (13)	−0.0036 (13)	−0.0038 (14)
C42	0.0280 (14)	0.0325 (17)	0.0343 (15)	−0.0036 (13)	−0.0025 (13)	−0.0079 (13)
C43	0.0260 (14)	0.059 (2)	0.0364 (16)	−0.0016 (15)	−0.0028 (13)	−0.0079 (16)
C44	0.107 (4)	0.108 (5)	0.090 (4)	−0.007 (4)	0.029 (3)	0.058 (3)
C45	0.0308 (16)	0.053 (2)	0.0435 (17)	0.0096 (15)	−0.0044 (14)	−0.0116 (16)
C46	0.067 (8)	0.067 (9)	0.098 (11)	0.025 (6)	0.013 (6)	−0.030 (8)
C47	0.064 (2)	0.033 (2)	0.075 (3)	0.0128 (19)	0.008 (2)	0.0040 (18)
C48	0.085 (3)	0.054 (3)	0.141 (5)	0.015 (3)	0.051 (3)	0.004 (3)
C49	0.0367 (16)	0.034 (2)	0.062 (2)	0.0002 (15)	−0.0056 (16)	−0.0120 (16)
C50	0.047 (2)	0.057 (3)	0.106 (3)	−0.010 (2)	−0.012 (2)	−0.017 (3)
C46A	0.067 (8)	0.067 (9)	0.098 (11)	0.025 (6)	0.013 (6)	−0.030 (8)
O19	0.0434 (13)	0.0430 (15)	0.0612 (15)	−0.0020 (12)	−0.0104 (12)	−0.0210 (12)
O20	0.0326 (14)	0.0571 (19)	0.088 (2)	−0.0045 (13)	−0.0034 (14)	−0.0179 (16)
O21	0.0561 (15)	0.0490 (15)	0.0552 (14)	0.0191 (13)	0.0136 (12)	0.0227 (12)
O22	0.0398 (11)	0.0269 (12)	0.0412 (11)	0.0021 (10)	0.0059 (10)	−0.0027 (10)
O23	0.0308 (10)	0.0365 (13)	0.0382 (11)	−0.0075 (10)	−0.0018 (10)	−0.0048 (10)
O24	0.0437 (12)	0.0425 (14)	0.0346 (11)	0.0029 (11)	0.0056 (10)	0.0092 (10)
O25	0.0401 (13)	0.0504 (16)	0.0624 (15)	0.0162 (12)	−0.0074 (12)	0.0008 (13)
O26	0.0371 (13)	0.081 (2)	0.0522 (15)	0.0209 (14)	0.0030 (11)	−0.0174 (14)
O27	0.0245 (10)	0.0696 (18)	0.0511 (13)	−0.0014 (12)	0.0008 (10)	−0.0064 (13)
N3	0.0230 (11)	0.0304 (14)	0.0378 (13)	−0.0013 (10)	0.0032 (10)	0.0015 (11)
C51	0.0317 (16)	0.062 (3)	0.0380 (17)	0.0097 (16)	−0.0068 (14)	−0.0165 (17)
C52	0.0400 (17)	0.074 (3)	0.0367 (17)	0.0085 (18)	−0.0141 (15)	−0.0124 (17)
C53	0.0303 (15)	0.055 (2)	0.0462 (18)	0.0067 (16)	−0.0069 (14)	−0.0050 (16)
C54	0.0239 (13)	0.0341 (17)	0.0343 (15)	0.0014 (13)	0.0005 (12)	0.0027 (13)
C55	0.0263 (13)	0.0363 (18)	0.0266 (13)	−0.0001 (13)	0.0014 (12)	0.0053 (12)
C56	0.0261 (13)	0.0311 (16)	0.0300 (14)	0.0010 (12)	0.0045 (12)	0.0009 (12)
C57	0.0223 (12)	0.0289 (16)	0.0263 (13)	−0.0002 (12)	0.0009 (11)	0.0005 (12)
C58	0.0228 (12)	0.0298 (16)	0.0288 (13)	−0.0018 (12)	−0.0004 (11)	−0.0016 (12)
C59	0.0271 (14)	0.0389 (19)	0.0282 (14)	0.0009 (13)	−0.0008 (12)	0.0023 (13)
C60	0.0281 (15)	0.0401 (19)	0.0430 (17)	0.0063 (14)	−0.0043 (14)	−0.0009 (15)
C61	0.0287 (15)	0.050 (2)	0.0360 (16)	0.0101 (15)	0.0033 (13)	−0.0071 (15)
C62	0.0323 (15)	0.053 (2)	0.0328 (15)	0.0073 (15)	0.0015 (13)	−0.0144 (15)
C63	0.0276 (14)	0.049 (2)	0.0246 (13)	0.0014 (14)	0.0019 (12)	0.0010 (13)
C64	0.0243 (13)	0.0398 (18)	0.0243 (13)	0.0022 (13)	0.0010 (11)	−0.0018 (12)
C65	0.0199 (12)	0.0271 (16)	0.0303 (14)	0.0006 (12)	0.0019 (11)	−0.0021 (12)
C66	0.0232 (13)	0.0359 (18)	0.0369 (16)	0.0022 (13)	0.0056 (12)	0.0051 (13)
C67	0.0232 (13)	0.0393 (18)	0.0322 (14)	−0.0029 (13)	0.0046 (12)	0.0031 (13)
C68	0.0243 (14)	0.060 (2)	0.0319 (15)	0.0001 (15)	0.0042 (13)	0.0007 (15)
C69	0.088 (3)	0.083 (4)	0.106 (4)	0.003 (3)	−0.031 (3)	−0.056 (3)
C70	0.0285 (14)	0.0427 (19)	0.0406 (16)	0.0083 (14)	0.0039 (14)	0.0080 (14)
C71	0.072 (10)	0.061 (9)	0.091 (11)	0.027 (7)	0.000 (6)	0.033 (7)
C72	0.067 (2)	0.029 (2)	0.075 (3)	0.0062 (18)	0.004 (2)	−0.0019 (18)
C73	0.110 (4)	0.048 (3)	0.137 (5)	0.028 (3)	−0.050 (4)	−0.004 (3)
C74	0.0395 (17)	0.040 (2)	0.0464 (18)	0.0046 (15)	0.0115 (15)	0.0174 (15)
C75	0.046 (2)	0.065 (3)	0.114 (4)	0.000 (2)	0.023 (2)	0.044 (3)
C71A	0.072 (10)	0.061 (9)	0.091 (11)	0.027 (7)	0.000 (6)	0.033 (7)
O28	0.0444 (15)	0.076 (2)	0.0446 (15)	0.0100 (15)	0.0008 (13)	−0.0055 (14)
O29	0.0428 (15)	0.096 (3)	0.0541 (17)	0.0093 (17)	−0.0077 (14)	0.0009 (17)
O30	0.0445 (16)	0.091 (3)	0.0578 (18)	0.0104 (16)	0.0048 (15)	−0.0053 (17)

Geometric parameters (Å, º)

O1—C1	1.432 (4)	C29—C30	1.563 (4)
O1—C19	1.415 (4)	C29—C41	1.523 (4)
O2—C3	1.436 (4)	C29—C45	1.539 (5)
O3—C20	1.398 (4)	C30—C31	1.550 (4)
O3—C21	1.420 (5)	C30—C39	1.558 (4)
O4—C6	1.424 (3)	C31—C32	1.555 (4)
O4—C22	1.429 (5)	C32—C33	1.549 (4)
O5—C8	1.438 (3)	C32—C40	1.522 (4)
O6—C9	1.423 (4)	C33—C34	1.551 (4)
O7—C10	1.439 (4)	C33—C42	1.541 (4)
O7—C23	1.433 (11)	C34—C35	1.533 (4)
O7—C23A	1.331 (17)	C35—C36	1.558 (4)
O8—C11	1.421 (3)	C36—C37	1.533 (4)
O9—C18	1.408 (4)	C36—C43	1.511 (5)
N1—C15	1.520 (3)	C37—C38	1.565 (5)
N1—C16	1.494 (4)	C38—C39	1.569 (4)
N1—C24	1.501 (4)	C38—C42	1.554 (4)
C1—C2	1.516 (4)	C39—C40	1.530 (4)
C1—C14	1.556 (4)	C42—C43	1.521 (4)
C2—C3	1.511 (4)	C49—C50	1.495 (5)
C3—C4	1.572 (4)	O19—C51	1.433 (5)
C4—C5	1.565 (4)	O19—C69	1.436 (5)
C4—C16	1.526 (4)	O20—C53	1.432 (5)
C4—C20	1.539 (4)	O21—C70	1.408 (4)
C5—C6	1.552 (4)	O21—C71	1.411 (19)
C5—C14	1.560 (4)	O21—C71A	1.44 (3)
C6—C7	1.549 (4)	O22—C56	1.430 (3)
C7—C8	1.551 (4)	O22—C72	1.422 (4)
C7—C15	1.528 (4)	O23—C58	1.433 (3)
C8—C9	1.553 (4)	O24—C59	1.428 (3)
C8—C17	1.542 (4)	O25—C60	1.432 (4)
C9—C10	1.521 (4)	O25—C73	1.402 (6)
C10—C11	1.549 (4)	O26—C61	1.422 (4)
C11—C12	1.532 (4)	O27—C68	1.417 (4)
C11—C18	1.528 (5)	N3—C65	1.511 (3)
C12—C13	1.565 (4)	N3—C66	1.495 (4)
C13—C14	1.566 (4)	N3—C74	1.514 (4)
C13—C17	1.554 (4)	C51—C52	1.504 (5)
C14—C15	1.531 (4)	C51—C64	1.562 (4)
C17—C18	1.527 (4)	C52—C53	1.517 (5)
C24—C25	1.491 (6)	C53—C54	1.566 (4)
O10—C26	1.433 (5)	C54—C55	1.554 (4)
O10—C44	1.429 (5)	C54—C66	1.527 (4)
O11—C28	1.426 (5)	C54—C70	1.534 (4)
O12—C45	1.407 (4)	C55—C56	1.556 (4)
O12—C46	1.463 (18)	C55—C64	1.562 (4)
O12—C46A	1.41 (3)	C56—C57	1.546 (4)
O13—C31	1.426 (3)	C57—C58	1.543 (4)
O13—C47	1.432 (4)	C57—C65	1.516 (4)
O14—C33	1.437 (3)	C58—C59	1.555 (4)
O15—C43	1.418 (4)	C58—C67	1.543 (4)
O16—C34	1.423 (3)	C59—C60	1.533 (4)
O17—C35	1.427 (4)	C60—C61	1.546 (5)
O17—C48	1.373 (6)	C61—C62	1.535 (4)
O18—C36	1.423 (4)	C61—C68	1.505 (5)
N2—C40	1.512 (3)	C62—C63	1.560 (5)
N2—C41	1.496 (4)	C63—C64	1.560 (4)
N2—C49	1.505 (4)	C63—C67	1.566 (4)
C26—C27	1.516 (5)	C64—C65	1.531 (4)
C26—C39	1.556 (4)	C67—C68	1.521 (4)
C27—C28	1.515 (5)	C74—C75	1.502 (5)
C28—C29	1.570 (5)
C19—O1—C1	114.4 (3)	C42—C33—C34	112.4 (2)
C20—O3—C21	112.1 (3)	O16—C34—C33	113.1 (2)
C6—O4—C22	112.0 (3)	O16—C34—C35	106.7 (2)
C23—O7—C10	115.8 (5)	C35—C34—C33	117.5 (2)
C23A—O7—C10	116.6 (8)	O17—C35—C34	106.9 (2)
C16—N1—C15	112.0 (2)	O17—C35—C36	109.2 (2)
C16—N1—C24	112.6 (2)	C34—C35—C36	114.1 (3)
C24—N1—C15	113.4 (2)	O18—C36—C35	110.4 (3)
O1—C1—C2	113.0 (2)	O18—C36—C37	108.3 (3)
O1—C1—C14	107.9 (2)	O18—C36—C43	114.1 (3)
C2—C1—C14	111.0 (3)	C37—C36—C35	111.7 (2)
C3—C2—C1	113.7 (3)	C43—C36—C35	110.7 (3)
O2—C3—C2	106.8 (3)	C43—C36—C37	101.3 (3)
O2—C3—C4	112.9 (2)	C36—C37—C38	106.0 (3)
C2—C3—C4	112.1 (2)	C37—C38—C39	111.8 (3)
C5—C4—C3	111.3 (2)	C42—C38—C37	103.3 (2)
C16—C4—C3	111.4 (3)	C42—C38—C39	118.5 (2)
C16—C4—C5	108.3 (2)	C26—C39—C30	112.9 (2)
C16—C4—C20	106.4 (2)	C26—C39—C38	106.2 (2)
C20—C4—C3	106.0 (2)	C30—C39—C38	116.1 (3)
C20—C4—C5	113.4 (3)	C40—C39—C26	116.8 (3)
C6—C5—C4	113.8 (2)	C40—C39—C30	99.5 (2)
C6—C5—C14	100.7 (2)	C40—C39—C38	105.4 (2)
C14—C5—C4	108.5 (2)	N2—C40—C32	113.5 (2)
O4—C6—C5	117.2 (2)	N2—C40—C39	110.9 (2)
O4—C6—C7	111.7 (2)	C32—C40—C39	100.8 (2)
C7—C6—C5	104.7 (2)	N2—C41—C29	112.0 (2)
C6—C7—C8	107.6 (2)	C33—C42—C38	113.2 (2)
C15—C7—C6	105.4 (2)	C43—C42—C33	112.2 (2)
C15—C7—C8	109.6 (2)	C43—C42—C38	101.8 (2)
O5—C8—C7	106.9 (2)	O15—C43—C36	116.9 (3)
O5—C8—C9	108.6 (2)	O15—C43—C42	113.1 (3)
O5—C8—C17	105.5 (2)	C36—C43—C42	101.5 (2)
C7—C8—C9	114.3 (2)	O12—C45—C29	108.2 (2)
C17—C8—C7	108.7 (2)	C50—C49—N2	112.7 (3)
C17—C8—C9	112.3 (2)	C51—O19—C69	115.2 (3)
O6—C9—C8	112.1 (2)	C70—O21—C71	110.3 (8)
O6—C9—C10	107.4 (3)	C70—O21—C71A	112.1 (12)
C10—C9—C8	117.1 (2)	C72—O22—C56	113.0 (3)
O7—C10—C9	107.2 (2)	C73—O25—C60	114.8 (3)
O7—C10—C11	108.0 (2)	C65—N3—C74	112.0 (2)
C9—C10—C11	115.8 (3)	C66—N3—C65	112.9 (2)
O8—C11—C10	110.7 (3)	C66—N3—C74	111.1 (2)
O8—C11—C12	108.7 (2)	O19—C51—C52	114.3 (3)
O8—C11—C18	113.5 (2)	O19—C51—C64	106.8 (3)
C12—C11—C10	113.0 (2)	C52—C51—C64	110.7 (3)
C18—C11—C10	110.0 (2)	C51—C52—C53	113.9 (3)
C18—C11—C12	100.6 (2)	O20—C53—C52	107.0 (3)
C11—C12—C13	106.1 (2)	O20—C53—C54	111.9 (3)
C12—C13—C14	110.8 (2)	C52—C53—C54	113.2 (3)
C17—C13—C12	103.7 (2)	C55—C54—C53	111.0 (2)
C17—C13—C14	119.1 (2)	C66—C54—C53	112.8 (3)
C1—C14—C5	113.1 (2)	C66—C54—C55	108.2 (2)
C1—C14—C13	106.1 (2)	C66—C54—C70	105.1 (2)
C5—C14—C13	116.0 (2)	C70—C54—C53	106.3 (2)
C15—C14—C1	117.2 (2)	C70—C54—C55	113.4 (3)
C15—C14—C5	99.1 (2)	C54—C55—C56	114.1 (2)
C15—C14—C13	105.4 (2)	C54—C55—C64	108.5 (2)
N1—C15—C7	113.7 (2)	C56—C55—C64	100.8 (2)
N1—C15—C14	110.2 (2)	O22—C56—C55	117.0 (2)
C7—C15—C14	100.7 (2)	O22—C56—C57	111.1 (2)
N1—C16—C4	109.3 (2)	C57—C56—C55	105.1 (2)
C8—C17—C13	112.9 (2)	C58—C57—C56	108.6 (2)
C18—C17—C8	113.7 (2)	C65—C57—C56	105.1 (2)
C18—C17—C13	100.7 (2)	C65—C57—C58	109.0 (2)
O9—C18—C11	116.1 (3)	O23—C58—C57	106.7 (2)
O9—C18—C17	113.7 (2)	O23—C58—C59	108.6 (2)
C17—C18—C11	101.1 (2)	O23—C58—C67	106.2 (2)
O3—C20—C4	107.8 (3)	C57—C58—C59	114.4 (2)
C25—C24—N1	110.3 (3)	C67—C58—C57	108.9 (2)
C44—O10—C26	114.2 (4)	C67—C58—C59	111.6 (2)
C45—O12—C46	110.7 (9)	O24—C59—C58	113.3 (2)
C46A—O12—C45	113.0 (13)	O24—C59—C60	106.3 (3)
C31—O13—C47	112.7 (3)	C60—C59—C58	118.2 (2)
C48—O17—C35	116.1 (3)	O25—C60—C59	106.3 (2)
C41—N2—C40	112.5 (2)	O25—C60—C61	109.8 (2)
C41—N2—C49	112.4 (2)	C59—C60—C61	114.5 (3)
C49—N2—C40	111.2 (2)	O26—C61—C60	110.8 (3)
O10—C26—C27	113.5 (3)	O26—C61—C62	108.7 (2)
O10—C26—C39	107.1 (3)	O26—C61—C68	113.5 (3)
C27—C26—C39	111.2 (3)	C62—C61—C60	110.7 (3)
C28—C27—C26	113.5 (3)	C68—C61—C60	111.6 (3)
O11—C28—C27	108.4 (3)	C68—C61—C62	101.0 (3)
O11—C28—C29	112.0 (3)	C61—C62—C63	106.1 (3)
C27—C28—C29	112.6 (3)	C62—C63—C64	112.5 (3)
C30—C29—C28	110.5 (2)	C62—C63—C67	103.4 (2)
C41—C29—C28	112.6 (3)	C64—C63—C67	118.4 (2)
C41—C29—C30	108.6 (2)	C51—C64—C55	114.1 (2)
C41—C29—C45	105.2 (2)	C63—C64—C51	107.1 (2)
C45—C29—C28	106.0 (3)	C63—C64—C55	114.7 (3)
C45—C29—C30	113.8 (3)	C65—C64—C51	115.2 (3)
C31—C30—C29	114.1 (2)	C65—C64—C55	98.9 (2)
C31—C30—C39	100.7 (2)	C65—C64—C63	106.8 (2)
C39—C30—C29	108.4 (3)	N3—C65—C57	112.7 (2)
O13—C31—C30	117.6 (2)	N3—C65—C64	111.3 (2)
O13—C31—C32	111.1 (2)	C57—C65—C64	101.3 (2)
C30—C31—C32	104.9 (2)	N3—C66—C54	111.9 (2)
C33—C32—C31	108.5 (2)	C58—C67—C63	112.4 (2)
C40—C32—C31	105.3 (2)	C68—C67—C58	113.4 (2)
C40—C32—C33	109.0 (2)	C68—C67—C63	101.0 (2)
O14—C33—C32	107.5 (2)	O27—C68—C61	116.8 (3)
O14—C33—C34	108.4 (2)	O27—C68—C67	111.9 (3)
O14—C33—C42	105.9 (2)	C61—C68—C67	101.9 (2)
C32—C33—C34	113.6 (2)	O21—C70—C54	108.9 (2)
C42—C33—C32	108.6 (2)	C75—C74—N3	111.2 (3)
O1—C1—C2—C3	67.5 (3)	C33—C34—C35—O17	146.7 (2)
O1—C1—C14—C5	−125.4 (2)	C33—C34—C35—C36	25.9 (4)
O1—C1—C14—C13	106.4 (2)	C33—C42—C43—O15	−53.8 (4)
O1—C1—C14—C15	−11.0 (3)	C33—C42—C43—C36	72.3 (3)
O2—C3—C4—C5	125.2 (3)	C34—C33—C42—C38	89.3 (3)
O2—C3—C4—C16	4.2 (3)	C34—C33—C42—C43	−25.2 (3)
O2—C3—C4—C20	−111.1 (3)	C34—C35—C36—O18	150.4 (3)
O4—C6—C7—C8	−118.8 (2)	C34—C35—C36—C37	−89.1 (3)
O4—C6—C7—C15	124.2 (2)	C34—C35—C36—C43	23.1 (3)
O5—C8—C9—O6	94.1 (3)	C35—C36—C37—C38	88.5 (3)
O5—C8—C9—C10	−141.1 (3)	C35—C36—C43—O15	53.5 (3)
O5—C8—C17—C13	−151.3 (2)	C35—C36—C43—C42	−70.1 (3)
O5—C8—C17—C18	94.8 (3)	C36—C37—C38—C39	−128.7 (3)
O6—C9—C10—O7	−88.6 (3)	C36—C37—C38—C42	−0.2 (3)
O6—C9—C10—C11	150.8 (2)	C37—C36—C43—O15	172.1 (2)
O7—C10—C11—O8	31.5 (3)	C37—C36—C43—C42	48.5 (3)
O7—C10—C11—C12	153.8 (3)	C37—C38—C39—C26	−54.0 (3)
O7—C10—C11—C18	−94.7 (3)	C37—C38—C39—C30	179.6 (2)
O8—C11—C12—C13	−148.6 (2)	C37—C38—C39—C40	70.7 (3)
O8—C11—C18—O9	−71.0 (3)	C37—C38—C42—C33	−91.1 (3)
O8—C11—C18—C17	165.6 (2)	C37—C38—C42—C43	29.5 (3)
C1—C2—C3—O2	−72.1 (3)	C38—C39—C40—N2	−170.9 (2)
C1—C2—C3—C4	52.0 (4)	C38—C39—C40—C32	68.7 (3)
C1—C14—C15—N1	−53.6 (3)	C38—C42—C43—O15	−175.1 (3)
C1—C14—C15—C7	−174.0 (2)	C38—C42—C43—C36	−49.0 (3)
C2—C1—C14—C5	−1.1 (3)	C39—C26—C27—C28	−54.9 (4)
C2—C1—C14—C13	−129.3 (3)	C39—C30—C31—O13	−151.4 (2)
C2—C1—C14—C15	113.3 (3)	C39—C30—C31—C32	−27.5 (3)
C2—C3—C4—C5	4.6 (4)	C39—C38—C42—C33	33.2 (4)
C2—C3—C4—C16	−116.4 (3)	C39—C38—C42—C43	153.8 (3)
C2—C3—C4—C20	128.3 (3)	C40—N2—C41—C29	48.7 (3)
C3—C4—C5—C6	−167.3 (3)	C40—N2—C49—C50	−159.8 (3)
C3—C4—C5—C14	−56.0 (3)	C40—C32—C33—O14	178.4 (2)
C3—C4—C16—N1	67.9 (3)	C40—C32—C33—C34	−61.7 (3)
C3—C4—C20—O3	−67.5 (3)	C40—C32—C33—C42	64.3 (3)
C4—C5—C6—O4	−36.6 (4)	C41—N2—C40—C32	52.3 (3)
C4—C5—C6—C7	87.7 (3)	C41—N2—C40—C39	−60.4 (3)
C4—C5—C14—C1	54.6 (3)	C41—N2—C49—C50	73.0 (4)
C4—C5—C14—C13	177.6 (2)	C41—C29—C30—C31	−46.5 (4)
C4—C5—C14—C15	−70.2 (3)	C41—C29—C30—C39	64.8 (3)
C5—C4—C16—N1	−54.8 (3)	C41—C29—C45—O12	170.6 (3)
C5—C4—C20—O3	54.8 (3)	C42—C33—C34—O16	−149.7 (2)
C5—C6—C7—C8	113.4 (2)	C42—C33—C34—C35	−24.7 (3)
C5—C6—C7—C15	−3.6 (3)	C42—C38—C39—C26	−174.0 (3)
C5—C14—C15—N1	68.3 (3)	C42—C38—C39—C30	59.6 (4)
C5—C14—C15—C7	−52.1 (2)	C42—C38—C39—C40	−49.4 (4)
C6—C5—C14—C1	174.4 (2)	C43—C36—C37—C38	−29.4 (3)
C6—C5—C14—C13	−62.6 (3)	C44—O10—C26—C27	62.0 (4)
C6—C5—C14—C15	49.6 (2)	C44—O10—C26—C39	−175.0 (3)
C6—C7—C8—O5	63.0 (3)	C45—C29—C30—C31	70.3 (3)
C6—C7—C8—C9	−176.8 (2)	C45—C29—C30—C39	−178.4 (2)
C6—C7—C8—C17	−50.4 (3)	C45—C29—C41—N2	−172.9 (2)
C6—C7—C15—N1	−83.1 (3)	C46—O12—C45—C29	178.8 (6)
C6—C7—C15—C14	34.7 (3)	C47—O13—C31—C30	−85.8 (3)
C7—C8—C9—O6	−25.2 (3)	C47—O13—C31—C32	153.4 (3)
C7—C8—C9—C10	99.6 (3)	C48—O17—C35—C34	111.0 (4)
C7—C8—C17—C13	−36.9 (3)	C48—O17—C35—C36	−125.1 (4)
C7—C8—C17—C18	−150.8 (3)	C49—N2—C40—C32	−74.9 (3)
C8—C7—C15—N1	161.3 (2)	C49—N2—C40—C39	172.5 (3)
C8—C7—C15—C14	−80.9 (3)	C49—N2—C41—C29	175.2 (3)
C8—C9—C10—O7	144.3 (3)	C46A—O12—C45—C29	150.8 (10)
C8—C9—C10—C11	23.7 (4)	O19—C51—C52—C53	65.9 (4)
C8—C17—C18—O9	−54.9 (4)	O19—C51—C64—C55	−120.8 (3)
C8—C17—C18—C11	70.2 (3)	O19—C51—C64—C63	111.2 (3)
C9—C8—C17—C13	90.6 (3)	O19—C51—C64—C65	−7.4 (3)
C9—C8—C17—C18	−23.3 (3)	O20—C53—C54—C55	131.9 (3)
C9—C10—C11—O8	151.7 (3)	O20—C53—C54—C66	10.3 (4)
C9—C10—C11—C12	−86.1 (3)	O20—C53—C54—C70	−104.3 (3)
C9—C10—C11—C18	25.5 (3)	O22—C56—C57—C58	−121.2 (2)
C10—C11—C12—C13	88.0 (3)	O22—C56—C57—C65	122.3 (2)
C10—C11—C18—O9	53.7 (3)	O23—C58—C59—O24	94.8 (3)
C10—C11—C18—C17	−69.8 (3)	O23—C58—C59—C60	−139.9 (3)
C11—C12—C13—C14	−130.3 (2)	O23—C58—C67—C63	−153.6 (2)
C11—C12—C13—C17	−1.4 (3)	O23—C58—C67—C68	92.7 (3)
C12—C11—C18—O9	173.1 (2)	O24—C59—C60—O25	−85.3 (3)
C12—C11—C18—C17	49.7 (3)	O24—C59—C60—C61	153.4 (2)
C12—C13—C14—C1	−54.9 (3)	O25—C60—C61—O26	31.2 (4)
C12—C13—C14—C5	178.6 (2)	O25—C60—C61—C62	152.0 (3)
C12—C13—C14—C15	70.1 (3)	O25—C60—C61—C68	−96.3 (3)
C12—C13—C17—C8	−90.1 (3)	O26—C61—C62—C63	−149.4 (3)
C12—C13—C17—C18	31.5 (3)	O26—C61—C68—O27	−72.3 (4)
C13—C14—C15—N1	−171.4 (2)	O26—C61—C68—C67	165.4 (2)
C13—C14—C15—C7	68.2 (3)	C51—C52—C53—O20	−76.5 (4)
C13—C17—C18—O9	−175.8 (3)	C51—C52—C53—C54	47.3 (4)
C13—C17—C18—C11	−50.7 (3)	C51—C64—C65—N3	−54.1 (3)
C14—C1—C2—C3	−53.9 (4)	C51—C64—C65—C57	−174.1 (2)
C14—C5—C6—O4	−152.5 (2)	C52—C51—C64—C55	4.3 (4)
C14—C5—C6—C7	−28.2 (3)	C52—C51—C64—C63	−123.7 (3)
C14—C13—C17—C8	33.5 (4)	C52—C51—C64—C65	117.7 (3)
C14—C13—C17—C18	155.1 (3)	C52—C53—C54—C55	10.8 (4)
C15—N1—C16—C4	54.0 (3)	C52—C53—C54—C66	−110.7 (3)
C15—N1—C24—C25	−88.8 (4)	C52—C53—C54—C70	134.6 (3)
C15—C7—C8—O5	177.2 (2)	C53—C54—C55—C56	−169.6 (3)
C15—C7—C8—C9	−62.6 (3)	C53—C54—C55—C64	−58.1 (3)
C15—C7—C8—C17	63.8 (3)	C53—C54—C66—N3	72.3 (3)
C16—N1—C15—C7	48.0 (3)	C53—C54—C70—O21	−72.7 (3)
C16—N1—C15—C14	−64.2 (3)	C54—C55—C56—O22	−34.3 (4)
C16—N1—C24—C25	142.7 (3)	C54—C55—C56—C57	89.4 (3)
C16—C4—C5—C6	−44.5 (3)	C54—C55—C64—C51	50.9 (3)
C16—C4—C5—C14	66.7 (3)	C54—C55—C64—C63	174.9 (2)
C16—C4—C20—O3	173.7 (2)	C54—C55—C64—C65	−71.9 (3)
C17—C8—C9—O6	−149.6 (2)	C55—C54—C66—N3	−50.8 (3)
C17—C8—C9—C10	−24.8 (3)	C55—C54—C70—O21	49.5 (3)
C17—C13—C14—C1	−174.9 (3)	C55—C56—C57—C58	111.4 (2)
C17—C13—C14—C5	58.6 (3)	C55—C56—C57—C65	−5.1 (3)
C17—C13—C14—C15	−49.9 (3)	C55—C64—C65—N3	67.9 (3)
C18—C11—C12—C13	−29.2 (3)	C55—C64—C65—C57	−52.2 (2)
C19—O1—C1—C2	66.2 (4)	C56—C55—C64—C51	171.0 (2)
C19—O1—C1—C14	−170.7 (3)	C56—C55—C64—C63	−65.0 (3)
C20—C4—C5—C6	73.4 (3)	C56—C55—C64—C65	48.2 (2)
C20—C4—C5—C14	−175.4 (2)	C56—C57—C58—O23	65.9 (3)
C20—C4—C16—N1	−177.0 (2)	C56—C57—C58—C59	−173.9 (2)
C21—O3—C20—C4	165.9 (3)	C56—C57—C58—C67	−48.3 (3)
C22—O4—C6—C5	−86.8 (3)	C56—C57—C65—N3	−83.3 (3)
C22—O4—C6—C7	152.4 (3)	C56—C57—C65—C64	35.7 (3)
C23—O7—C10—C9	93.2 (6)	C57—C58—C59—O24	−24.3 (3)
C23—O7—C10—C11	−141.4 (6)	C57—C58—C59—C60	101.0 (3)
C24—N1—C15—C7	−80.8 (3)	C57—C58—C67—C63	−39.0 (3)
C24—N1—C15—C14	167.1 (3)	C57—C58—C67—C68	−152.7 (3)
C24—N1—C16—C4	−176.8 (3)	C58—C57—C65—N3	160.5 (2)
C23A—O7—C10—C9	126.8 (9)	C58—C57—C65—C64	−80.5 (3)
C23A—O7—C10—C11	−107.7 (9)	C58—C59—C60—O25	146.1 (3)
O10—C26—C27—C28	65.8 (4)	C58—C59—C60—C61	24.8 (4)
O10—C26—C39—C30	−122.3 (3)	C58—C67—C68—O27	−54.4 (4)
O10—C26—C39—C38	109.4 (3)	C58—C67—C68—C61	71.1 (3)
O10—C26—C39—C40	−7.8 (4)	C59—C58—C67—C63	88.2 (3)
O11—C28—C29—C30	131.8 (3)	C59—C58—C67—C68	−25.5 (3)
O11—C28—C29—C41	10.2 (4)	C59—C60—C61—O26	150.7 (3)
O11—C28—C29—C45	−104.4 (3)	C59—C60—C61—C62	−88.6 (3)
O13—C31—C32—C33	−119.5 (2)	C59—C60—C61—C68	23.1 (4)
O13—C31—C32—C40	123.9 (2)	C60—C61—C62—C63	88.6 (3)
O14—C33—C34—O16	93.6 (3)	C60—C61—C68—O27	53.8 (3)
O14—C33—C34—C35	−141.4 (3)	C60—C61—C68—C67	−68.5 (3)
O14—C33—C42—C38	−152.5 (2)	C61—C62—C63—C64	−128.9 (3)
O14—C33—C42—C43	93.0 (3)	C61—C62—C63—C67	−0.1 (3)
O16—C34—C35—O17	−85.1 (3)	C62—C61—C68—O27	171.5 (2)
O16—C34—C35—C36	154.0 (2)	C62—C61—C68—C67	49.2 (3)
O17—C35—C36—O18	30.8 (3)	C62—C63—C64—C51	−51.3 (3)
O17—C35—C36—C37	151.4 (3)	C62—C63—C64—C55	−179.0 (2)
O17—C35—C36—C43	−96.5 (3)	C62—C63—C64—C65	72.6 (3)
O18—C36—C37—C38	−149.7 (3)	C62—C63—C67—C58	−91.8 (3)
O18—C36—C43—O15	−71.7 (4)	C62—C63—C67—C68	29.5 (3)
O18—C36—C43—C42	164.7 (3)	C63—C64—C65—N3	−172.8 (2)
C26—C27—C28—O11	−75.8 (4)	C63—C64—C65—C57	67.1 (3)
C26—C27—C28—C29	48.7 (5)	C63—C67—C68—O27	−174.9 (3)
C26—C39—C40—N2	−53.2 (3)	C63—C67—C68—C61	−49.4 (3)
C26—C39—C40—C32	−173.6 (2)	C64—C51—C52—C53	−54.8 (4)
C27—C26—C39—C30	2.2 (4)	C64—C55—C56—O22	−150.4 (2)
C27—C26—C39—C38	−126.1 (3)	C64—C55—C56—C57	−26.6 (3)
C27—C26—C39—C40	116.7 (3)	C64—C63—C67—C58	33.4 (4)
C27—C28—C29—C30	9.3 (4)	C64—C63—C67—C68	154.6 (3)
C27—C28—C29—C41	−112.3 (3)	C65—N3—C66—C54	47.9 (3)
C27—C28—C29—C45	133.1 (3)	C65—N3—C74—C75	−154.0 (3)
C28—C29—C30—C31	−170.5 (3)	C65—C57—C58—O23	179.9 (2)
C28—C29—C30—C39	−59.2 (3)	C65—C57—C58—C59	−59.9 (3)
C28—C29—C41—N2	72.1 (3)	C65—C57—C58—C67	65.7 (3)
C28—C29—C45—O12	−69.9 (3)	C66—N3—C65—C57	53.6 (3)
C29—C30—C31—O13	−35.5 (4)	C66—N3—C65—C64	−59.4 (3)
C29—C30—C31—C32	88.4 (3)	C66—N3—C74—C75	78.8 (4)
C29—C30—C39—C26	53.4 (3)	C66—C54—C55—C56	−45.3 (3)
C29—C30—C39—C38	176.4 (2)	C66—C54—C55—C64	66.1 (3)
C29—C30—C39—C40	−71.1 (3)	C66—C54—C70—O21	167.5 (2)
C30—C29—C41—N2	−50.6 (3)	C67—C58—C59—O24	−148.5 (2)
C30—C29—C45—O12	51.8 (3)	C67—C58—C59—C60	−23.2 (3)
C30—C31—C32—C33	112.5 (2)	C67—C63—C64—C51	−171.9 (3)
C30—C31—C32—C40	−4.1 (3)	C67—C63—C64—C55	60.4 (3)
C30—C39—C40—N2	68.6 (3)	C67—C63—C64—C65	−48.0 (4)
C30—C39—C40—C32	−51.9 (2)	C68—C61—C62—C63	−29.7 (3)
C31—C30—C39—C26	173.5 (2)	C69—O19—C51—C52	61.9 (4)
C31—C30—C39—C38	−63.5 (3)	C69—O19—C51—C64	−175.2 (3)
C31—C30—C39—C40	48.9 (3)	C70—C54—C55—C56	70.8 (3)
C31—C32—C33—O14	64.2 (3)	C70—C54—C55—C64	−177.7 (2)
C31—C32—C33—C34	−175.9 (2)	C70—C54—C66—N3	−172.3 (2)
C31—C32—C33—C42	−49.9 (3)	C71—O21—C70—C54	−177.4 (7)
C31—C32—C40—N2	−83.9 (3)	C72—O22—C56—C55	−92.0 (3)
C31—C32—C40—C39	34.7 (3)	C72—O22—C56—C57	147.4 (3)
C32—C33—C34—O16	−25.8 (3)	C73—O25—C60—C59	119.7 (4)
C32—C33—C34—C35	99.2 (3)	C73—O25—C60—C61	−116.0 (4)
C32—C33—C42—C38	−37.3 (3)	C74—N3—C65—C57	−72.6 (3)
C32—C33—C42—C43	−151.8 (3)	C74—N3—C65—C64	174.3 (3)
C33—C32—C40—N2	159.9 (2)	C74—N3—C66—C54	174.6 (2)
C33—C32—C40—C39	−81.5 (3)	C71A—O21—C70—C54	154.2 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.98	2	2.743 (3)	131
N1—H1···O2	0.98	2.17	2.860 (3)	126
N2—H2C···O10	0.98	1.93	2.671 (4)	130
N2—H2C···O11	0.98	2.46	3.057 (4)	119
N3—H3A···O19	0.98	1.91	2.639 (4)	129
N3—H3A···O20	0.98	2.47	3.064 (4)	118
O2—H2···Cl1^i	0.76 (5)	2.41 (5)	3.170 (3)	172 (5)
O5—H5···Cl3	0.82	2.37	3.183 (2)	177
O6—H6···Cl3	0.82	2.66	3.428 (3)	156
O8—H8···O7	0.82	2.28	2.601 (3)	104
O8—H8···O28	0.82	2.56	3.283 (4)	147
O9—H9···O28	0.82	1.99	2.808 (4)	173
O11—H11···Cl3^i	0.77 (5)	2.46 (5)	3.211 (3)	168 (4)
O14—H14···Cl1	0.79 (3)	2.42 (3)	3.205 (2)	171 (3)
O15—H15A···O30	0.82	1.97	2.781 (4)	169
O16—H16···Cl1	0.82	2.37	3.168 (2)	165
O18—H18A···O17	0.88 (5)	2.22 (5)	2.621 (4)	108 (4)
O18—H18A···O30	0.88 (5)	2.35 (5)	3.110 (4)	145 (4)
O20—H20···Cl2	0.70 (5)	2.46 (5)	3.154 (3)	170 (5)
O23—H23···Cl2^ii	0.82	2.44	3.248 (2)	167
O24—H24···Cl2^ii	0.82	2.37	3.167 (2)	166
O26—H26A···O25	0.82	2.31	2.636 (4)	105
O26—H26A···O29^iii	0.82	2.58	3.282 (4)	145
O27—H27···O29^iii	0.82	1.94	2.751 (4)	170
O28—H28A···O13^iv	0.85	1.98	2.814 (4)	166
O28—H28B···Cl1^iv	0.77 (5)	2.60 (5)	3.312 (3)	156 (5)
O29—H29A···O22^v	0.85	2.03	2.871 (4)	168
O29—H29B···Cl2	0.81 (5)	2.43 (5)	3.234 (3)	170 (4)
O30—H30A···O4^iv	0.89 (6)	2.03 (6)	2.871 (4)	159 (6)
O30—H30B···Cl3^iv	0.78 (6)	2.51 (7)	3.260 (3)	165 (6)
C3—H3···O3	0.98	2.48	2.877 (4)	104
C3—H3···O8^i	0.98	2.49	3.322 (4)	143
C6—H6A···O5	0.98	2.48	2.859 (3)	103
C12—H12A···O1	0.97	2.49	3.196 (4)	129
C16—H16A···O4	0.97	2.35	3.016 (4)	126
C20—H20B···O4	0.97	2.35	3.002 (4)	124
C28—H28···O12	0.98	2.49	2.913 (6)	106
C31—H31···O14	0.98	2.53	2.900 (4)	102
C34—H34···O15	0.98	2.56	2.909 (4)	101
C37—H37A···O10	0.97	2.56	3.272 (4)	130
C41—H41A···O13	0.97	2.41	3.049 (4)	123
C41—H41A···O9^i	0.97	2.58	3.209 (4)	123
C45—H45B···O13	0.97	2.34	2.969 (4)	122
C47—H47A···O12	0.96	2.55	3.356 (5)	142
C50—H50B···O5^i	0.96	2.54	3.489 (4)	169
C53—H53···O21	0.98	2.56	2.958 (4)	104
C56—H56···O23	0.98	2.53	2.895 (3)	102
C65—H65···O24	0.98	2.53	3.067 (4)	114
C66—H66A···O22	0.97	2.34	2.994 (4)	124
C66—H66B···O23^v	0.97	2.57	3.486 (3)	156
C70—H70B···O22	0.97	2.33	2.953 (4)	121
C71—H71B···O14^vi	0.96	2.59	3.348 (18)	136
C75—H75B···O23^v	0.96	2.43	3.392 (4)	179

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x+1, y, z; (iv) x−1/2, −y+1/2, −z+1; (v) x−1/2, −y+3/2, −z+1; (vi) x, y+1, z.