Crystal structure and hydrogen bonding in the hydrated cocrystalline salt tryptaminium–3,5-di­nitro­benzoate–quinoline–water (3/3/2/2)

The study of ternary systems is inter­esting because it introduces the concept of mol­ecular preference/competition into the system where one mol­ecule may be displaced because the association between the other two is significantly stronger. Current definitions of a tertiary system indicate that solvent mol­ecules are excluded from the mol­ecule count of the system and some of the latest definitions state that any mol­ecule that is not a solid in the parent form at room temperature should also be excluded from the mol­ecule count. In the structure of the quinoline adduct hydrate of tryptaminium 3,5-di­nitro­benzoate, 3C₁₀H₁₃N₂⁺·3C₇H₃N₂O₆⁻·2C₉H₇N·2H₂O, the asymmetric unit comprises multiple cation and anion species which are conformationally similar among each type set. In the crystal, a one-dimensional hydrogen-bonded supra­molecular structure is generated through extensive intra- and inter-unit aminium N—H...O and N—H...N, and water O—H...O hydrogen bonds. Within the central-core hydrogen-bonding associations, conjoined cyclic R₄⁴(10), R₅³(10) and R₄⁴(12) motifs are generated. The unit is expanded into a one-dimensional column-like polymer extending along [010]. Present also in the crystal packing of the structure are a total of 19 π–π inter­actions involving both cation, anion and quinoline species [ring-centroid separation range = 3.395 (3)–3.797 (3) Å], as well as a number of weak C—H...O hydrogen-bonding associations. The presence of the two water mol­ecules in the crystal structure is considered to be the principal causative factor in the low symmetry of the asymmetric unit.

Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2013); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b), and SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Tryptaminium–3,5-dinitrobenzoate–quinoline–water (3/3/2/2)

Crystal data

3C10H13N2^+·3C7H3N2O6^−·2C9H7N·2H2O	Z = 2
Mr = 1411.36	F(000) = 1476
Triclinic, P1	Dx = 1.435 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 14.5210 (8) Å	Cell parameters from 8180 reflections
b = 15.5102 (9) Å	θ = 1.9–25.0°
c = 15.6438 (9) Å	µ = 0.11 mm^−1
α = 80.506 (5)°	T = 100 K
β = 88.951 (5)°	Needle, yellow
γ = 70.168 (5)°	0.18 × 0.09 × 0.01 mm
V = 3266.3 (3) Å^3

Data collection

Rigaku AFC12 (Right) diffractometer	11548 independent reflections
Radiation source: rotating anode, rotating anode	4825 reflections with I > 2σ(I)
Confocal mirrors, HF Varimax monochromator	Rint = 0.152
Detector resolution: 28.5714 pixels mm^-1	θmax = 25.0°, θmin = 1.8°
profile data from ω–scans	h = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −18→18
Tmin = 0.771, Tmax = 0.990	l = −17→18
48646 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.191	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0627P)^2] where P = (Fo^2 + 2Fc^2)/3
11548 reflections	(Δ/σ)max < 0.001
937 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
O11D	0.2630 (2)	0.4171 (2)	0.4201 (2)	0.0295 (12)
O12D	0.2005 (3)	0.5610 (2)	0.4510 (2)	0.0343 (12)
O31D	−0.0038 (3)	0.6034 (2)	0.7049 (2)	0.0475 (16)
O32D	−0.0947 (3)	0.5180 (2)	0.7359 (2)	0.0365 (12)
O51D	0.0135 (3)	0.2133 (2)	0.6439 (2)	0.0361 (12)
O52D	0.1317 (3)	0.1830 (2)	0.5555 (2)	0.0437 (16)
N3D	−0.0271 (3)	0.5360 (3)	0.6980 (3)	0.0323 (17)
N5D	0.0725 (3)	0.2358 (3)	0.5972 (3)	0.0293 (17)
C1D	0.1426 (3)	0.4462 (3)	0.5254 (3)	0.0212 (17)
C2D	0.0885 (3)	0.5035 (3)	0.5813 (3)	0.0238 (17)
C3D	0.0289 (3)	0.4734 (3)	0.6390 (3)	0.0210 (17)
C4D	0.0189 (3)	0.3877 (3)	0.6449 (3)	0.0228 (17)
C5D	0.0739 (4)	0.3313 (3)	0.5899 (3)	0.0239 (17)
C6D	0.1356 (3)	0.3584 (3)	0.5316 (3)	0.0248 (17)
C11D	0.2075 (4)	0.4775 (4)	0.4607 (3)	0.0263 (19)
O11E	0.4491 (2)	0.5854 (2)	0.2405 (2)	0.0295 (12)
O12E	0.3773 (2)	0.7292 (2)	0.2706 (2)	0.0340 (12)
O31E	0.5161 (3)	0.9664 (2)	0.1527 (2)	0.0371 (14)
O32E	0.6033 (3)	0.9527 (2)	0.0392 (2)	0.0374 (12)
O51E	0.7418 (3)	0.6468 (2)	−0.0416 (2)	0.0345 (12)
O52E	0.6836 (3)	0.5384 (2)	0.0133 (2)	0.0354 (14)
N3E	0.5601 (3)	0.9215 (3)	0.0975 (3)	0.0307 (17)
N5E	0.6860 (3)	0.6182 (3)	0.0058 (3)	0.0274 (17)
C1E	0.5006 (3)	0.7062 (3)	0.1674 (3)	0.0215 (17)
C2E	0.4995 (4)	0.7964 (3)	0.1601 (3)	0.0220 (17)
C3E	0.5598 (4)	0.8267 (3)	0.1023 (3)	0.0215 (17)
C4E	0.6205 (3)	0.7705 (3)	0.0495 (3)	0.0225 (17)
C5E	0.6202 (3)	0.6808 (3)	0.0585 (3)	0.0213 (17)
C6E	0.5617 (3)	0.6480 (3)	0.1156 (3)	0.0221 (17)
C11E	0.4369 (4)	0.6710 (4)	0.2308 (3)	0.0258 (19)
O11F	0.6132 (2)	0.0189 (2)	0.3902 (2)	0.0326 (12)
O12F	0.5468 (2)	0.1632 (2)	0.4179 (2)	0.0271 (12)
O31F	0.6962 (3)	0.3911 (2)	0.2930 (2)	0.0452 (16)
O32F	0.8016 (3)	0.3635 (2)	0.1936 (2)	0.0393 (14)
O51F	0.9090 (3)	0.0585 (2)	0.1061 (2)	0.0373 (14)
O52F	0.8184 (3)	−0.0275 (2)	0.1390 (2)	0.0451 (16)
N3F	0.7472 (3)	0.3402 (3)	0.2452 (3)	0.0282 (17)
N5F	0.8426 (3)	0.0404 (3)	0.1453 (3)	0.0304 (17)
C1F	0.6724 (4)	0.1327 (3)	0.3153 (3)	0.0229 (17)
C2F	0.6785 (3)	0.2212 (3)	0.3089 (3)	0.0219 (17)
C3F	0.7411 (3)	0.2471 (3)	0.2503 (3)	0.0202 (17)
C4F	0.7972 (3)	0.1888 (3)	0.1962 (3)	0.0225 (17)
C5F	0.7865 (3)	0.1035 (3)	0.2037 (3)	0.0215 (17)
C6F	0.7272 (4)	0.0735 (3)	0.2613 (3)	0.0234 (17)
C11F	0.6048 (4)	0.1026 (4)	0.3791 (3)	0.0264 (17)
N1A	0.1262 (3)	0.9952 (3)	0.5451 (3)	0.0290 (16)
N33A	0.3430 (3)	0.6392 (3)	0.4294 (2)	0.0297 (17)
C2A	0.1777 (4)	0.9433 (3)	0.4846 (3)	0.0292 (19)
C3A	0.1639 (4)	0.8596 (3)	0.4954 (3)	0.0219 (17)
C4A	0.0578 (4)	0.7947 (3)	0.6088 (3)	0.0311 (17)
C5A	−0.0035 (4)	0.8193 (4)	0.6765 (3)	0.0323 (19)
C6A	−0.0236 (4)	0.9052 (4)	0.7032 (3)	0.0319 (19)
C7A	0.0159 (4)	0.9692 (4)	0.6630 (3)	0.0293 (17)
C8A	0.0775 (4)	0.9450 (3)	0.5951 (3)	0.0273 (17)
C9A	0.0994 (3)	0.8591 (3)	0.5664 (3)	0.0233 (17)
C31A	0.2060 (4)	0.7852 (3)	0.4434 (3)	0.0298 (17)
C32A	0.3024 (4)	0.7128 (3)	0.4840 (3)	0.0298 (17)
N1B	0.5247 (3)	0.1555 (3)	0.1319 (3)	0.0279 (16)
N33B	0.3030 (3)	0.5079 (2)	0.2583 (2)	0.0275 (14)
C2B	0.4677 (4)	0.2067 (3)	0.1894 (3)	0.0285 (17)
C3B	0.4772 (4)	0.2916 (3)	0.1804 (3)	0.0261 (17)
C4B	0.5875 (4)	0.3603 (3)	0.0747 (3)	0.0325 (19)
C5B	0.6559 (4)	0.3369 (4)	0.0130 (3)	0.0329 (19)
C6B	0.6841 (4)	0.2495 (3)	−0.0130 (3)	0.0291 (17)
C7B	0.6426 (3)	0.1842 (3)	0.0217 (3)	0.0248 (17)
C8B	0.5739 (3)	0.2076 (3)	0.0848 (3)	0.0234 (17)
C9B	0.5446 (4)	0.2953 (3)	0.1124 (3)	0.0249 (17)
C31B	0.4327 (3)	0.3633 (3)	0.2366 (3)	0.0285 (17)
C32B	0.3397 (4)	0.4391 (3)	0.1987 (3)	0.0297 (17)
N1C	0.6993 (3)	0.5798 (3)	0.3012 (2)	0.0250 (16)
N33C	0.4815 (3)	0.9295 (2)	0.4241 (2)	0.0234 (14)
C2C	0.6474 (4)	0.6349 (3)	0.3584 (3)	0.0255 (17)
C3C	0.6633 (4)	0.7181 (3)	0.3456 (3)	0.0228 (17)
C4C	0.7740 (3)	0.7750 (3)	0.2323 (3)	0.0266 (17)
C5C	0.8373 (4)	0.7479 (4)	0.1677 (3)	0.033 (2)
C6C	0.8582 (4)	0.6594 (4)	0.1451 (3)	0.0293 (19)
C7C	0.8154 (4)	0.5980 (3)	0.1854 (3)	0.0276 (17)
C8C	0.7510 (3)	0.6259 (3)	0.2501 (3)	0.0213 (17)
C9C	0.7300 (3)	0.7137 (3)	0.2753 (3)	0.0237 (17)
C31C	0.6237 (4)	0.7959 (3)	0.3967 (3)	0.0265 (17)
C32C	0.5195 (3)	0.8569 (3)	0.3683 (3)	0.0227 (17)
N1G	0.1452 (3)	0.6674 (3)	0.1750 (3)	0.0303 (17)
C2G	0.1344 (4)	0.7463 (4)	0.2017 (3)	0.032 (2)
C3G	0.0842 (4)	0.8341 (4)	0.1546 (4)	0.037 (2)
C4G	0.0455 (4)	0.8406 (4)	0.0741 (4)	0.036 (2)
C5G	0.0188 (4)	0.7579 (4)	−0.0415 (3)	0.036 (2)
C6G	0.0290 (4)	0.6760 (4)	−0.0691 (3)	0.0367 (19)
C7G	0.0762 (4)	0.5912 (4)	−0.0145 (3)	0.038 (2)
C8G	0.1139 (4)	0.5892 (3)	0.0656 (3)	0.0292 (17)
C9G	0.1044 (4)	0.6725 (3)	0.0947 (3)	0.0273 (17)
C10G	0.0559 (4)	0.7588 (3)	0.0415 (3)	0.0298 (17)
N1H	0.3016 (3)	1.0712 (3)	0.3476 (3)	0.0289 (17)
C2H	0.2852 (4)	1.1530 (4)	0.3693 (3)	0.0323 (19)
C3H	0.2437 (4)	1.2387 (3)	0.3145 (3)	0.0286 (17)
C4H	0.2202 (3)	1.2373 (4)	0.2307 (3)	0.0300 (17)
C5H	0.2128 (4)	1.1448 (4)	0.1172 (3)	0.0318 (19)
C6H	0.2255 (4)	1.0592 (4)	0.0957 (3)	0.0368 (19)
C7H	0.2611 (4)	0.9784 (4)	0.1575 (4)	0.034 (2)
C8H	0.2873 (3)	0.9817 (3)	0.2402 (3)	0.0296 (17)
C9H	0.2754 (4)	1.0683 (4)	0.2643 (3)	0.0277 (19)
C10H	0.2367 (4)	1.1505 (3)	0.2033 (3)	0.0275 (17)
O1W	0.5266 (3)	0.4905 (3)	0.4079 (2)	0.0451 (16)
O2W	0.4685 (3)	0.3403 (2)	0.4569 (2)	0.0396 (12)
H2D	0.09270	0.56360	0.57960	0.0290*
H4D	−0.02350	0.36850	0.68450	0.0280*
H6D	0.17320	0.31670	0.49550	0.0300*
H2E	0.45760	0.83740	0.19440	0.0270*
H4E	0.66030	0.79260	0.00900	0.0270*
H6E	0.56300	0.58580	0.11950	0.0260*
H2F	0.64030	0.26330	0.34420	0.0260*
H4F	0.84020	0.20690	0.15650	0.0270*
H6F	0.72370	0.01310	0.26420	0.0280*
H1A	0.12500	1.05110	0.55050	0.0340*
H2A	0.21690	0.96320	0.44180	0.0350*
H4A	0.07130	0.73580	0.59150	0.0380*
H5A	−0.03240	0.77670	0.70540	0.0380*
H6A	−0.06550	0.91950	0.75000	0.0380*
H7A	0.00190	1.02790	0.68080	0.0350*
H30A	0.15800	0.75380	0.43740	0.0360*
H31A	0.21790	0.81340	0.38450	0.0360*
H32A	0.29080	0.68390	0.54250	0.0360*
H33A	0.35060	0.74390	0.49010	0.0360*
H34A	0.30210	0.60590	0.42910	0.0360*
H35A	0.40310	0.60070	0.45150	0.0360*
H36A	0.34850	0.66620	0.37420	0.0360*
H30B	0.48140	0.39230	0.24790	0.0340*
H31B	0.41850	0.33180	0.29310	0.0340*
H32B	0.35260	0.47080	0.14180	0.0360*
H33B	0.28920	0.41140	0.18930	0.0360*
H34B	0.34860	0.53470	0.26530	0.0330*
H35B	0.29180	0.47850	0.31070	0.0330*
H36B	0.24630	0.55250	0.23540	0.0330*
H2B	0.42710	0.18550	0.22980	0.0340*
H1B	0.52900	0.09880	0.12630	0.0340*
H7B	0.66030	0.12560	0.00320	0.0300*
H6B	0.73250	0.23510	−0.05510	0.0350*
H5B	0.68470	0.38100	−0.01270	0.0400*
H4B	0.56950	0.41970	0.09170	0.0390*
H1C	0.69930	0.52370	0.29800	0.0300*
H2C	0.60630	0.61760	0.40080	0.0310*
H4C	0.76030	0.83480	0.24760	0.0320*
H5C	0.86730	0.78940	0.13800	0.0400*
H6C	0.90310	0.64170	0.10090	0.0350*
H7C	0.82940	0.53840	0.16960	0.0330*
H30C	0.66620	0.83460	0.38970	0.0320*
H31C	0.62570	0.76930	0.45890	0.0320*
H32C	0.51770	0.88700	0.30710	0.0270*
H33C	0.47720	0.81810	0.37220	0.0270*
H34C	0.52240	0.96290	0.42290	0.0280*
H35C	0.47820	0.90180	0.47950	0.0280*
H36C	0.42060	0.96800	0.40380	0.0280*
H2G	0.16280	0.74330	0.25690	0.0390*
H3G	0.07700	0.88850	0.17820	0.0450*
H4G	0.01200	0.89970	0.04040	0.0430*
H5G	−0.01370	0.81510	−0.07860	0.0420*
H6G	0.00410	0.67660	−0.12500	0.0440*
H7G	0.08200	0.53450	−0.03340	0.0460*
H8G	0.14660	0.53120	0.10150	0.0350*
H2H	0.30290	1.15440	0.42710	0.0390*
H3H	0.23230	1.29580	0.33480	0.0340*
H4H	0.19300	1.29380	0.19110	0.0360*
H5H	0.18830	1.19960	0.07500	0.0380*
H6H	0.20990	1.05500	0.03820	0.0440*
H7H	0.26740	0.92010	0.14190	0.0400*
H8H	0.31320	0.92600	0.28110	0.0360*
H11W	0.51830	0.50880	0.35340	0.0680*
H12W	0.51230	0.44130	0.42130	0.0680*
H21W	0.48680	0.28870	0.43860	0.0590*
H22W	0.40830	0.36930	0.44300	0.0590*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11D	0.025 (2)	0.034 (2)	0.032 (2)	−0.0118 (18)	0.0024 (18)	−0.0088 (18)
O12D	0.031 (2)	0.034 (2)	0.045 (2)	−0.0204 (19)	0.0079 (19)	−0.0072 (19)
O31D	0.049 (3)	0.040 (2)	0.068 (3)	−0.029 (2)	0.016 (2)	−0.021 (2)
O32D	0.028 (2)	0.041 (2)	0.043 (2)	−0.013 (2)	0.008 (2)	−0.0117 (19)
O51D	0.032 (2)	0.038 (2)	0.048 (2)	−0.025 (2)	0.005 (2)	−0.0062 (19)
O52D	0.043 (3)	0.033 (2)	0.064 (3)	−0.018 (2)	0.023 (2)	−0.024 (2)
N3D	0.022 (3)	0.036 (3)	0.036 (3)	−0.008 (2)	0.002 (2)	−0.002 (2)
N5D	0.022 (3)	0.036 (3)	0.035 (3)	−0.019 (2)	−0.006 (2)	0.000 (2)
C1D	0.015 (3)	0.024 (3)	0.026 (3)	−0.008 (2)	−0.008 (2)	−0.004 (2)
C2D	0.021 (3)	0.023 (3)	0.030 (3)	−0.012 (3)	−0.008 (3)	−0.001 (3)
C3D	0.014 (3)	0.022 (3)	0.026 (3)	−0.004 (2)	−0.008 (2)	−0.005 (2)
C4D	0.013 (3)	0.028 (3)	0.026 (3)	−0.006 (2)	−0.004 (2)	−0.002 (3)
C5D	0.027 (3)	0.026 (3)	0.023 (3)	−0.016 (3)	−0.009 (3)	0.000 (3)
C6D	0.017 (3)	0.036 (3)	0.023 (3)	−0.010 (3)	−0.005 (2)	−0.007 (3)
C11D	0.019 (3)	0.039 (4)	0.025 (3)	−0.016 (3)	−0.006 (3)	−0.003 (3)
O11E	0.028 (2)	0.031 (2)	0.035 (2)	−0.0182 (18)	−0.0008 (18)	−0.0027 (18)
O12E	0.025 (2)	0.038 (2)	0.042 (2)	−0.0125 (19)	0.0081 (19)	−0.0119 (19)
O31E	0.044 (3)	0.034 (2)	0.041 (2)	−0.019 (2)	0.011 (2)	−0.0164 (19)
O32E	0.038 (2)	0.040 (2)	0.044 (2)	−0.027 (2)	0.012 (2)	−0.0056 (19)
O51E	0.029 (2)	0.045 (2)	0.035 (2)	−0.018 (2)	0.0101 (19)	−0.0112 (18)
O52E	0.041 (3)	0.029 (2)	0.040 (2)	−0.0121 (19)	0.0063 (19)	−0.0162 (19)
N3E	0.021 (3)	0.034 (3)	0.041 (3)	−0.013 (2)	0.001 (2)	−0.009 (2)
N5E	0.019 (3)	0.031 (3)	0.032 (3)	−0.006 (2)	−0.005 (2)	−0.010 (2)
C1E	0.017 (3)	0.025 (3)	0.025 (3)	−0.009 (2)	−0.003 (2)	−0.007 (2)
C2E	0.022 (3)	0.026 (3)	0.022 (3)	−0.012 (3)	−0.002 (2)	−0.007 (2)
C3E	0.022 (3)	0.021 (3)	0.026 (3)	−0.012 (2)	−0.006 (3)	−0.006 (2)
C4E	0.018 (3)	0.037 (3)	0.018 (3)	−0.015 (3)	−0.005 (2)	−0.007 (3)
C5E	0.018 (3)	0.026 (3)	0.021 (3)	−0.009 (2)	−0.006 (2)	−0.003 (2)
C6E	0.013 (3)	0.025 (3)	0.030 (3)	−0.007 (2)	−0.007 (2)	−0.007 (3)
C11E	0.016 (3)	0.037 (4)	0.028 (3)	−0.015 (3)	−0.005 (3)	−0.002 (3)
O11F	0.032 (2)	0.031 (2)	0.042 (2)	−0.0170 (19)	0.0079 (19)	−0.0136 (19)
O12F	0.023 (2)	0.026 (2)	0.032 (2)	−0.0087 (17)	0.0013 (17)	−0.0033 (17)
O31F	0.055 (3)	0.033 (2)	0.057 (3)	−0.021 (2)	0.026 (2)	−0.023 (2)
O32F	0.043 (3)	0.040 (2)	0.047 (2)	−0.028 (2)	0.018 (2)	−0.0124 (19)
O51F	0.036 (3)	0.040 (2)	0.043 (2)	−0.021 (2)	0.019 (2)	−0.0113 (19)
O52F	0.056 (3)	0.041 (2)	0.053 (3)	−0.030 (2)	0.014 (2)	−0.021 (2)
N3F	0.028 (3)	0.028 (3)	0.035 (3)	−0.016 (2)	−0.001 (2)	−0.009 (2)
N5F	0.028 (3)	0.032 (3)	0.033 (3)	−0.013 (2)	0.002 (2)	−0.005 (2)
C1F	0.021 (3)	0.026 (3)	0.024 (3)	−0.010 (3)	−0.004 (2)	−0.006 (3)
C2F	0.017 (3)	0.023 (3)	0.024 (3)	−0.004 (2)	−0.006 (2)	−0.005 (2)
C3F	0.019 (3)	0.020 (3)	0.022 (3)	−0.010 (2)	−0.005 (2)	0.003 (2)
C4F	0.019 (3)	0.026 (3)	0.024 (3)	−0.011 (3)	0.000 (2)	−0.001 (3)
C5F	0.013 (3)	0.026 (3)	0.026 (3)	−0.007 (2)	−0.001 (2)	−0.005 (3)
C6F	0.023 (3)	0.020 (3)	0.030 (3)	−0.010 (3)	−0.005 (3)	−0.006 (3)
C11F	0.025 (3)	0.030 (3)	0.028 (3)	−0.013 (3)	0.002 (3)	−0.008 (3)
N1A	0.028 (3)	0.027 (2)	0.037 (3)	−0.015 (2)	−0.003 (2)	−0.007 (2)
N33A	0.026 (3)	0.037 (3)	0.033 (3)	−0.017 (2)	0.004 (2)	−0.012 (2)
C2A	0.020 (3)	0.042 (4)	0.029 (3)	−0.015 (3)	−0.005 (3)	−0.005 (3)
C3A	0.021 (3)	0.024 (3)	0.023 (3)	−0.007 (2)	−0.008 (2)	−0.011 (2)
C4A	0.026 (3)	0.035 (3)	0.038 (3)	−0.018 (3)	−0.005 (3)	−0.005 (3)
C5A	0.023 (3)	0.041 (4)	0.036 (3)	−0.019 (3)	−0.005 (3)	0.003 (3)
C6A	0.020 (3)	0.044 (4)	0.035 (3)	−0.012 (3)	−0.001 (3)	−0.013 (3)
C7A	0.019 (3)	0.038 (3)	0.031 (3)	−0.009 (3)	−0.006 (3)	−0.007 (3)
C8A	0.019 (3)	0.028 (3)	0.036 (3)	−0.010 (3)	−0.008 (3)	−0.003 (3)
C9A	0.013 (3)	0.027 (3)	0.030 (3)	−0.009 (2)	−0.011 (2)	0.001 (3)
C31A	0.025 (3)	0.041 (3)	0.026 (3)	−0.016 (3)	−0.004 (3)	−0.002 (3)
C32A	0.028 (3)	0.035 (3)	0.031 (3)	−0.016 (3)	−0.005 (3)	−0.006 (3)
N1B	0.025 (3)	0.023 (2)	0.042 (3)	−0.015 (2)	−0.004 (2)	−0.008 (2)
N33B	0.019 (3)	0.034 (2)	0.031 (2)	−0.012 (2)	−0.004 (2)	−0.003 (2)
C2B	0.014 (3)	0.038 (3)	0.035 (3)	−0.011 (3)	0.000 (3)	−0.006 (3)
C3B	0.017 (3)	0.028 (3)	0.032 (3)	−0.006 (3)	−0.008 (3)	−0.004 (3)
C4B	0.031 (4)	0.032 (3)	0.039 (3)	−0.017 (3)	−0.008 (3)	−0.004 (3)
C5B	0.022 (3)	0.046 (4)	0.037 (3)	−0.020 (3)	0.001 (3)	−0.006 (3)
C6B	0.022 (3)	0.040 (3)	0.025 (3)	−0.011 (3)	−0.004 (3)	−0.003 (3)
C7B	0.020 (3)	0.030 (3)	0.024 (3)	−0.006 (3)	−0.009 (3)	−0.008 (2)
C8B	0.017 (3)	0.031 (3)	0.026 (3)	−0.011 (3)	−0.008 (3)	−0.008 (3)
C9B	0.019 (3)	0.027 (3)	0.030 (3)	−0.009 (3)	−0.008 (3)	−0.005 (3)
C31B	0.016 (3)	0.026 (3)	0.042 (3)	−0.004 (3)	−0.001 (3)	−0.008 (3)
C32B	0.026 (3)	0.032 (3)	0.035 (3)	−0.011 (3)	0.003 (3)	−0.014 (3)
N1C	0.022 (3)	0.027 (2)	0.029 (3)	−0.011 (2)	0.000 (2)	−0.007 (2)
N33C	0.020 (3)	0.028 (2)	0.025 (2)	−0.009 (2)	−0.003 (2)	−0.0098 (19)
C2C	0.023 (3)	0.031 (3)	0.023 (3)	−0.009 (3)	−0.001 (3)	−0.006 (3)
C3C	0.018 (3)	0.025 (3)	0.026 (3)	−0.007 (3)	−0.007 (2)	−0.006 (3)
C4C	0.014 (3)	0.038 (3)	0.033 (3)	−0.013 (3)	−0.004 (3)	−0.011 (3)
C5C	0.031 (4)	0.042 (4)	0.033 (3)	−0.020 (3)	−0.006 (3)	−0.006 (3)
C6C	0.020 (3)	0.045 (4)	0.023 (3)	−0.011 (3)	0.001 (2)	−0.006 (3)
C7C	0.023 (3)	0.032 (3)	0.031 (3)	−0.010 (3)	−0.007 (3)	−0.012 (3)
C8C	0.013 (3)	0.029 (3)	0.025 (3)	−0.011 (3)	−0.005 (2)	−0.004 (3)
C9C	0.016 (3)	0.034 (3)	0.023 (3)	−0.011 (3)	−0.006 (2)	−0.004 (3)
C31C	0.027 (3)	0.024 (3)	0.034 (3)	−0.013 (3)	−0.005 (3)	−0.010 (3)
C32C	0.017 (3)	0.021 (3)	0.032 (3)	−0.006 (2)	−0.004 (2)	−0.010 (2)
N1G	0.022 (3)	0.037 (3)	0.034 (3)	−0.014 (2)	−0.001 (2)	−0.003 (2)
C2G	0.028 (4)	0.039 (4)	0.035 (3)	−0.016 (3)	0.006 (3)	−0.011 (3)
C3G	0.026 (4)	0.037 (4)	0.052 (4)	−0.017 (3)	0.007 (3)	−0.007 (3)
C4G	0.018 (3)	0.037 (4)	0.050 (4)	−0.009 (3)	0.007 (3)	−0.001 (3)
C5G	0.014 (3)	0.051 (4)	0.039 (4)	−0.011 (3)	0.003 (3)	0.001 (3)
C6G	0.020 (3)	0.062 (4)	0.031 (3)	−0.018 (3)	−0.005 (3)	−0.007 (3)
C7G	0.030 (4)	0.055 (4)	0.037 (3)	−0.019 (3)	0.008 (3)	−0.018 (3)
C8G	0.019 (3)	0.034 (3)	0.035 (3)	−0.008 (3)	0.003 (3)	−0.009 (3)
C9G	0.018 (3)	0.033 (3)	0.033 (3)	−0.011 (3)	0.003 (3)	−0.007 (3)
C10G	0.016 (3)	0.033 (3)	0.035 (3)	−0.005 (3)	0.006 (3)	0.001 (3)
N1H	0.024 (3)	0.029 (3)	0.036 (3)	−0.009 (2)	−0.001 (2)	−0.012 (2)
C2H	0.020 (3)	0.046 (4)	0.036 (3)	−0.013 (3)	−0.001 (3)	−0.017 (3)
C3H	0.022 (3)	0.031 (3)	0.035 (3)	−0.011 (3)	−0.003 (3)	−0.007 (3)
C4H	0.012 (3)	0.039 (3)	0.040 (3)	−0.012 (3)	0.000 (3)	−0.002 (3)
C5H	0.018 (3)	0.041 (4)	0.038 (3)	−0.012 (3)	−0.001 (3)	−0.007 (3)
C6H	0.021 (3)	0.058 (4)	0.033 (3)	−0.015 (3)	0.000 (3)	−0.009 (3)
C7H	0.013 (3)	0.044 (4)	0.050 (4)	−0.011 (3)	0.000 (3)	−0.022 (3)
C8H	0.014 (3)	0.035 (3)	0.041 (3)	−0.010 (3)	−0.003 (3)	−0.006 (3)
C9H	0.017 (3)	0.046 (4)	0.026 (3)	−0.017 (3)	0.004 (3)	−0.009 (3)
C10H	0.015 (3)	0.036 (3)	0.037 (3)	−0.014 (3)	0.002 (3)	−0.010 (3)
O1W	0.040 (3)	0.053 (3)	0.045 (2)	−0.018 (2)	−0.007 (2)	−0.010 (2)
O2W	0.031 (2)	0.038 (2)	0.046 (2)	−0.0048 (19)	−0.005 (2)	−0.011 (2)

Geometric parameters (Å, º)

O11D—C11D	1.263 (6)	C4A—C5A	1.389 (7)
O12D—C11D	1.248 (7)	C4A—C9A	1.407 (7)
O31D—N3D	1.224 (6)	C5A—C6A	1.396 (8)
O32D—N3D	1.226 (6)	C6A—C7A	1.370 (8)
O51D—N5D	1.219 (6)	C7A—C8A	1.392 (7)
O52D—N5D	1.230 (6)	C8A—C9A	1.408 (6)
O11E—C11E	1.262 (7)	C31A—C32A	1.535 (7)
O12E—C11E	1.260 (6)	C2A—H2A	0.9500
O31E—N3E	1.231 (6)	C4A—H4A	0.9500
O32E—N3E	1.224 (6)	C5A—H5A	0.9500
O51E—N5E	1.232 (6)	C6A—H6A	0.9500
O52E—N5E	1.236 (6)	C7A—H7A	0.9500
O11F—C11F	1.245 (7)	C31A—H30A	0.9900
O12F—C11F	1.262 (6)	C31A—H31A	0.9900
O31F—N3F	1.228 (6)	C32A—H32A	0.9900
O32F—N3F	1.217 (6)	C32A—H33A	0.9900
O51F—N5F	1.221 (6)	C2B—C3B	1.354 (7)
O52F—N5F	1.237 (6)	C3B—C31B	1.497 (6)
N3D—C3D	1.479 (6)	C3B—C9B	1.440 (8)
N5D—C5D	1.474 (6)	C4B—C5B	1.373 (8)
N3E—C3E	1.461 (6)	C4B—C9B	1.403 (7)
N5E—C5E	1.463 (6)	C5B—C6B	1.404 (7)
N3F—C3F	1.466 (6)	C6B—C7B	1.380 (7)
N5F—C5F	1.478 (6)	C7B—C8B	1.392 (7)
N1A—C8A	1.368 (7)	C8B—C9B	1.419 (6)
N1A—C2A	1.386 (7)	C31B—C32B	1.510 (7)
N33A—C32A	1.492 (6)	C2B—H2B	0.9500
N1A—H1A	0.8800	C4B—H4B	0.9500
O1W—H11W	0.8500	C5B—H5B	0.9500
O1W—H12W	0.8500	C6B—H6B	0.9500
N33A—H35A	0.9100	C7B—H7B	0.9500
N33A—H36A	0.9100	C31B—H30B	0.9900
N33A—H34A	0.9100	C31B—H31B	0.9900
N1B—C2B	1.374 (7)	C32B—H32B	0.9900
N1B—C8B	1.372 (6)	C32B—H33B	0.9900
N33B—C32B	1.489 (5)	C2C—C3C	1.369 (7)
N1B—H1B	0.8800	C3C—C9C	1.447 (7)
O2W—H21W	0.8500	C3C—C31C	1.502 (6)
O2W—H22W	0.8500	C4C—C9C	1.397 (6)
N33B—H34B	0.9100	C4C—C5C	1.374 (7)
N33B—H35B	0.9100	C5C—C6C	1.405 (8)
N33B—H36B	0.9100	C6C—C7C	1.371 (8)
N1C—C2C	1.375 (6)	C7C—C8C	1.386 (7)
N1C—C8C	1.367 (6)	C8C—C9C	1.412 (6)
C1D—C11D	1.504 (7)	C31C—C32C	1.515 (7)
C1D—C2D	1.389 (6)	C2C—H2C	0.9500
C1D—C6D	1.387 (6)	C4C—H4C	0.9500
C2D—C3D	1.374 (7)	C5C—H5C	0.9500
C3D—C4D	1.374 (6)	C6C—H6C	0.9500
C4D—C5D	1.376 (7)	C7C—H7C	0.9500
C5D—C6D	1.382 (7)	C31C—H30C	0.9900
N33C—C32C	1.490 (5)	C31C—H31C	0.9900
N1C—H1C	0.8800	C32C—H32C	0.9900
C2D—H2D	0.9500	C32C—H33C	0.9900
C4D—H4D	0.9500	C2G—C3G	1.394 (8)
C6D—H6D	0.9500	C3G—C4G	1.363 (9)
N33C—H34C	0.9100	C4G—C10G	1.405 (8)
N33C—H35C	0.9100	C5G—C10G	1.419 (7)
N33C—H36C	0.9100	C5G—C6G	1.369 (8)
C1E—C11E	1.506 (7)	C6G—C7G	1.403 (8)
C1E—C2E	1.379 (6)	C7G—C8G	1.368 (7)
C1E—C6E	1.389 (6)	C8G—C9G	1.402 (6)
N1G—C2G	1.316 (7)	C9G—C10G	1.412 (6)
N1G—C9G	1.378 (7)	C2G—H2G	0.9500
C2E—C3E	1.384 (8)	C3G—H3G	0.9500
C3E—C4E	1.382 (7)	C4G—H4G	0.9500
C4E—C5E	1.377 (6)	C5G—H5G	0.9500
C5E—C6E	1.376 (7)	C6G—H6G	0.9500
C2E—H2E	0.9500	C7G—H7G	0.9500
C4E—H4E	0.9500	C8G—H8G	0.9500
C6E—H6E	0.9500	C2H—C3H	1.402 (7)
C1F—C6F	1.388 (7)	C3H—C4H	1.366 (7)
C1F—C2F	1.392 (7)	C4H—C10H	1.422 (7)
C1F—C11F	1.516 (8)	C5H—C10H	1.421 (7)
N1H—C2H	1.310 (7)	C5H—C6H	1.374 (8)
N1H—C9H	1.376 (7)	C6H—C7H	1.397 (8)
C2F—C3F	1.387 (7)	C7H—C8H	1.369 (8)
C3F—C4F	1.387 (6)	C8H—C9H	1.408 (7)
C4F—C5F	1.370 (6)	C9H—C10H	1.409 (7)
C5F—C6F	1.369 (7)	C2H—H2H	0.9500
C2F—H2F	0.9500	C3H—H3H	0.9500
C4F—H4F	0.9500	C4H—H4H	0.9500
C6F—H6F	0.9500	C5H—H5H	0.9500
C2A—C3A	1.363 (7)	C6H—H6H	0.9500
C3A—C9A	1.441 (7)	C7H—H7H	0.9500
C3A—C31A	1.476 (6)	C8H—H8H	0.9500
O31D—N3D—O32D	124.1 (4)	C8A—C7A—H7A	121.00
O31D—N3D—C3D	117.8 (4)	C3A—C31A—H31A	109.00
O32D—N3D—C3D	118.1 (4)	C32A—C31A—H31A	109.00
O51D—N5D—O52D	123.6 (4)	H30A—C31A—H31A	108.00
O51D—N5D—C5D	118.7 (4)	C3A—C31A—H30A	109.00
O52D—N5D—C5D	117.6 (4)	C32A—C31A—H30A	109.00
O31E—N3E—C3E	117.9 (4)	N33A—C32A—H32A	109.00
O32E—N3E—C3E	119.0 (4)	C31A—C32A—H33A	109.00
O31E—N3E—O32E	123.1 (4)	N33A—C32A—H33A	109.00
O51E—N5E—O52E	123.8 (4)	H32A—C32A—H33A	108.00
O52E—N5E—C5E	117.5 (4)	C31A—C32A—H32A	109.00
O51E—N5E—C5E	118.7 (4)	N1B—C2B—C3B	110.6 (5)
O32F—N3F—C3F	118.6 (4)	C9B—C3B—C31B	127.3 (4)
O31F—N3F—C3F	118.0 (4)	C2B—C3B—C31B	125.7 (5)
O31F—N3F—O32F	123.3 (4)	C2B—C3B—C9B	106.8 (4)
O51F—N5F—O52F	124.2 (4)	C5B—C4B—C9B	119.1 (4)
O52F—N5F—C5F	117.3 (4)	C4B—C5B—C6B	121.6 (5)
O51F—N5F—C5F	118.5 (4)	C5B—C6B—C7B	121.0 (5)
C2A—N1A—C8A	108.7 (4)	C6B—C7B—C8B	117.4 (4)
C8A—N1A—H1A	126.00	C7B—C8B—C9B	122.6 (4)
C2A—N1A—H1A	126.00	N1B—C8B—C9B	107.8 (4)
H11W—O1W—H12W	109.00	N1B—C8B—C7B	129.6 (4)
C32A—N33A—H35A	109.00	C3B—C9B—C8B	106.3 (4)
C32A—N33A—H36A	109.00	C3B—C9B—C4B	135.3 (4)
H34A—N33A—H35A	110.00	C4B—C9B—C8B	118.3 (5)
H35A—N33A—H36A	109.00	C3B—C31B—C32B	114.5 (4)
H34A—N33A—H36A	109.00	N33B—C32B—C31B	110.3 (4)
C32A—N33A—H34A	109.00	C3B—C2B—H2B	125.00
C2B—N1B—C8B	108.6 (4)	N1B—C2B—H2B	125.00
C8B—N1B—H1B	126.00	C9B—C4B—H4B	120.00
C2B—N1B—H1B	126.00	C5B—C4B—H4B	120.00
H21W—O2W—H22W	110.00	C4B—C5B—H5B	119.00
C32B—N33B—H34B	109.00	C6B—C5B—H5B	119.00
H34B—N33B—H35B	109.00	C7B—C6B—H6B	120.00
C32B—N33B—H36B	110.00	C5B—C6B—H6B	119.00
H34B—N33B—H36B	109.00	C6B—C7B—H7B	121.00
H35B—N33B—H36B	110.00	C8B—C7B—H7B	121.00
C32B—N33B—H35B	109.00	C3B—C31B—H30B	109.00
C2C—N1C—C8C	109.2 (4)	H30B—C31B—H31B	108.00
C2D—C1D—C6D	117.8 (4)	C3B—C31B—H31B	109.00
C6D—C1D—C11D	120.8 (4)	C32B—C31B—H31B	109.00
C2D—C1D—C11D	121.4 (4)	C32B—C31B—H30B	109.00
C1D—C2D—C3D	120.1 (4)	C31B—C32B—H33B	110.00
C2D—C3D—C4D	123.2 (4)	N33B—C32B—H33B	110.00
N3D—C3D—C2D	118.6 (4)	C31B—C32B—H32B	110.00
N3D—C3D—C4D	118.2 (4)	H32B—C32B—H33B	108.00
C3D—C4D—C5D	116.0 (4)	N33B—C32B—H32B	110.00
N5D—C5D—C4D	119.0 (5)	N1C—C2C—C3C	110.4 (5)
N5D—C5D—C6D	118.3 (4)	C2C—C3C—C31C	127.2 (5)
C4D—C5D—C6D	122.6 (4)	C9C—C3C—C31C	127.1 (4)
C1D—C6D—C5D	120.2 (4)	C2C—C3C—C9C	105.7 (4)
O11D—C11D—O12D	126.0 (5)	C5C—C4C—C9C	119.3 (4)
O11D—C11D—C1D	116.9 (5)	C4C—C5C—C6C	120.6 (5)
O12D—C11D—C1D	117.1 (5)	C5C—C6C—C7C	121.5 (5)
C8C—N1C—H1C	125.00	C6C—C7C—C8C	117.6 (4)
C2C—N1C—H1C	125.00	N1C—C8C—C9C	107.5 (4)
C1D—C2D—H2D	120.00	C7C—C8C—C9C	122.1 (4)
C3D—C2D—H2D	120.00	N1C—C8C—C7C	130.4 (4)
C5D—C4D—H4D	122.00	C3C—C9C—C8C	107.3 (4)
C3D—C4D—H4D	122.00	C3C—C9C—C4C	133.9 (4)
C1D—C6D—H6D	120.00	C4C—C9C—C8C	118.8 (4)
C5D—C6D—H6D	120.00	C3C—C31C—C32C	112.5 (4)
H34C—N33C—H35C	110.00	N33C—C32C—C31C	110.5 (4)
C32C—N33C—H36C	109.00	C3C—C2C—H2C	125.00
H35C—N33C—H36C	109.00	N1C—C2C—H2C	125.00
C32C—N33C—H35C	109.00	C9C—C4C—H4C	120.00
H34C—N33C—H36C	110.00	C5C—C4C—H4C	120.00
C32C—N33C—H34C	109.00	C4C—C5C—H5C	120.00
C2E—C1E—C6E	119.0 (4)	C6C—C5C—H5C	120.00
C6E—C1E—C11E	120.4 (4)	C7C—C6C—H6C	119.00
C2E—C1E—C11E	120.6 (4)	C5C—C6C—H6C	119.00
C2G—N1G—C9G	117.4 (4)	C8C—C7C—H7C	121.00
C1E—C2E—C3E	119.5 (4)	C6C—C7C—H7C	121.00
C2E—C3E—C4E	122.6 (4)	C32C—C31C—H30C	109.00
N3E—C3E—C4E	118.7 (5)	H30C—C31C—H31C	108.00
N3E—C3E—C2E	118.8 (4)	C32C—C31C—H31C	109.00
C3E—C4E—C5E	116.5 (4)	C3C—C31C—H31C	109.00
N5E—C5E—C6E	119.3 (4)	C3C—C31C—H30C	109.00
C4E—C5E—C6E	122.6 (4)	C31C—C32C—H33C	110.00
N5E—C5E—C4E	118.2 (4)	H32C—C32C—H33C	108.00
C1E—C6E—C5E	119.8 (4)	N33C—C32C—H32C	110.00
O11E—C11E—O12E	125.7 (5)	N33C—C32C—H33C	110.00
O12E—C11E—C1E	117.2 (5)	C31C—C32C—H32C	110.00
O11E—C11E—C1E	117.1 (5)	N1G—C2G—C3G	124.5 (5)
C3E—C2E—H2E	120.00	C2G—C3G—C4G	118.9 (5)
C1E—C2E—H2E	120.00	C3G—C4G—C10G	119.2 (5)
C3E—C4E—H4E	122.00	C6G—C5G—C10G	121.1 (5)
C5E—C4E—H4E	122.00	C5G—C6G—C7G	119.8 (5)
C5E—C6E—H6E	120.00	C6G—C7G—C8G	120.8 (5)
C1E—C6E—H6E	120.00	C7G—C8G—C9G	120.1 (5)
C6F—C1F—C11F	120.6 (4)	N1G—C9G—C10G	121.5 (4)
C2F—C1F—C11F	120.2 (4)	N1G—C9G—C8G	118.3 (4)
C2F—C1F—C6F	119.2 (5)	C8G—C9G—C10G	120.2 (4)
C2H—N1H—C9H	117.8 (5)	C5G—C10G—C9G	118.0 (4)
C1F—C2F—C3F	119.2 (4)	C4G—C10G—C9G	118.4 (5)
N3F—C3F—C4F	119.0 (4)	C4G—C10G—C5G	123.6 (5)
N3F—C3F—C2F	118.3 (4)	C3G—C2G—H2G	118.00
C2F—C3F—C4F	122.7 (4)	N1G—C2G—H2G	118.00
C3F—C4F—C5F	115.7 (4)	C4G—C3G—H3G	120.00
N5F—C5F—C4F	117.4 (4)	C2G—C3G—H3G	121.00
N5F—C5F—C6F	118.3 (4)	C10G—C4G—H4G	120.00
C4F—C5F—C6F	124.3 (4)	C3G—C4G—H4G	120.00
C1F—C6F—C5F	119.0 (4)	C6G—C5G—H5G	119.00
O12F—C11F—C1F	117.9 (5)	C10G—C5G—H5G	119.00
O11F—C11F—C1F	116.6 (5)	C7G—C6G—H6G	120.00
O11F—C11F—O12F	125.5 (5)	C5G—C6G—H6G	120.00
C1F—C2F—H2F	120.00	C6G—C7G—H7G	120.00
C3F—C2F—H2F	120.00	C8G—C7G—H7G	120.00
C5F—C4F—H4F	122.00	C7G—C8G—H8G	120.00
C3F—C4F—H4F	122.00	C9G—C8G—H8G	120.00
C1F—C6F—H6F	121.00	N1H—C2H—C3H	125.5 (5)
C5F—C6F—H6F	120.00	C2H—C3H—C4H	117.6 (5)
N1A—C2A—C3A	110.0 (5)	C3H—C4H—C10H	119.4 (5)
C2A—C3A—C31A	126.4 (5)	C6H—C5H—C10H	119.3 (5)
C9A—C3A—C31A	127.2 (4)	C5H—C6H—C7H	120.7 (5)
C2A—C3A—C9A	106.4 (4)	C6H—C7H—C8H	121.2 (5)
C5A—C4A—C9A	118.3 (4)	C7H—C8H—C9H	119.5 (5)
C4A—C5A—C6A	121.6 (5)	N1H—C9H—C10H	121.0 (5)
C5A—C6A—C7A	121.2 (5)	N1H—C9H—C8H	119.2 (5)
C6A—C7A—C8A	117.5 (5)	C8H—C9H—C10H	119.8 (4)
N1A—C8A—C7A	129.2 (5)	C4H—C10H—C9H	118.6 (4)
N1A—C8A—C9A	107.9 (4)	C4H—C10H—C5H	121.9 (4)
C7A—C8A—C9A	122.9 (5)	C5H—C10H—C9H	119.5 (5)
C3A—C9A—C4A	134.6 (4)	N1H—C2H—H2H	117.00
C3A—C9A—C8A	107.0 (4)	C3H—C2H—H2H	117.00
C4A—C9A—C8A	118.4 (4)	C4H—C3H—H3H	121.00
C3A—C31A—C32A	112.6 (4)	C2H—C3H—H3H	121.00
N33A—C32A—C31A	111.0 (4)	C3H—C4H—H4H	120.00
N1A—C2A—H2A	125.00	C10H—C4H—H4H	120.00
C3A—C2A—H2A	125.00	C6H—C5H—H5H	120.00
C9A—C4A—H4A	121.00	C10H—C5H—H5H	120.00
C5A—C4A—H4A	121.00	C7H—C6H—H6H	120.00
C6A—C5A—H5A	119.00	C5H—C6H—H6H	120.00
C4A—C5A—H5A	119.00	C6H—C7H—H7H	119.00
C5A—C6A—H6A	119.00	C8H—C7H—H7H	119.00
C7A—C6A—H6A	119.00	C9H—C8H—H8H	120.00
C6A—C7A—H7A	121.00	C7H—C8H—H8H	120.00
O31D—N3D—C3D—C2D	−14.1 (7)	C2A—C3A—C9A—C4A	180.0 (6)
O31D—N3D—C3D—C4D	165.7 (4)	C9A—C3A—C31A—C32A	−87.2 (7)
O32D—N3D—C3D—C2D	164.9 (4)	C31A—C3A—C9A—C4A	0.8 (9)
O32D—N3D—C3D—C4D	−15.3 (7)	C31A—C3A—C9A—C8A	−179.2 (5)
O51D—N5D—C5D—C4D	9.2 (7)	C2A—C3A—C31A—C32A	93.8 (6)
O51D—N5D—C5D—C6D	−174.9 (5)	C2A—C3A—C9A—C8A	0.0 (6)
O52D—N5D—C5D—C4D	−170.7 (5)	C5A—C4A—C9A—C3A	−179.5 (5)
O52D—N5D—C5D—C6D	5.2 (7)	C9A—C4A—C5A—C6A	−0.5 (8)
O32E—N3E—C3E—C2E	−170.7 (5)	C5A—C4A—C9A—C8A	0.5 (7)
O31E—N3E—C3E—C2E	9.0 (7)	C4A—C5A—C6A—C7A	0.6 (9)
O31E—N3E—C3E—C4E	−170.4 (5)	C5A—C6A—C7A—C8A	−0.6 (8)
O32E—N3E—C3E—C4E	9.9 (7)	C6A—C7A—C8A—N1A	−179.6 (5)
O52E—N5E—C5E—C4E	−178.6 (4)	C6A—C7A—C8A—C9A	0.6 (8)
O51E—N5E—C5E—C4E	3.0 (7)	C7A—C8A—C9A—C3A	179.4 (5)
O51E—N5E—C5E—C6E	−176.1 (4)	C7A—C8A—C9A—C4A	−0.6 (8)
O52E—N5E—C5E—C6E	2.2 (7)	N1A—C8A—C9A—C3A	−0.4 (6)
O31F—N3F—C3F—C4F	179.3 (4)	N1A—C8A—C9A—C4A	179.6 (5)
O31F—N3F—C3F—C2F	−0.2 (7)	C3A—C31A—C32A—N33A	−179.6 (4)
O32F—N3F—C3F—C2F	−179.6 (4)	N1B—C2B—C3B—C31B	−174.8 (5)
O32F—N3F—C3F—C4F	−0.1 (7)	N1B—C2B—C3B—C9B	0.2 (6)
O52F—N5F—C5F—C4F	−165.4 (4)	C31B—C3B—C9B—C4B	−2.2 (10)
O51F—N5F—C5F—C4F	14.2 (7)	C2B—C3B—C9B—C8B	−1.1 (6)
O51F—N5F—C5F—C6F	−166.1 (5)	C2B—C3B—C9B—C4B	−177.0 (6)
O52F—N5F—C5F—C6F	14.4 (7)	C31B—C3B—C9B—C8B	173.8 (5)
C2A—N1A—C8A—C9A	0.7 (6)	C9B—C3B—C31B—C32B	86.7 (7)
C8A—N1A—C2A—C3A	−0.7 (6)	C2B—C3B—C31B—C32B	−99.4 (6)
C2A—N1A—C8A—C7A	−179.2 (6)	C5B—C4B—C9B—C3B	175.5 (6)
C8B—N1B—C2B—C3B	0.9 (6)	C5B—C4B—C9B—C8B	−0.1 (8)
C2B—N1B—C8B—C7B	177.2 (5)	C9B—C4B—C5B—C6B	−0.2 (8)
C2B—N1B—C8B—C9B	−1.5 (6)	C4B—C5B—C6B—C7B	1.1 (8)
C2C—N1C—C8C—C7C	178.0 (5)	C5B—C6B—C7B—C8B	−1.6 (7)
C8C—N1C—C2C—C3C	0.5 (6)	C6B—C7B—C8B—C9B	1.3 (7)
C2C—N1C—C8C—C9C	−0.7 (5)	C6B—C7B—C8B—N1B	−177.2 (5)
C6D—C1D—C2D—C3D	−1.4 (7)	C7B—C8B—C9B—C4B	−0.5 (7)
C6D—C1D—C11D—O12D	171.0 (5)	N1B—C8B—C9B—C4B	178.4 (5)
C6D—C1D—C11D—O11D	−7.9 (7)	C7B—C8B—C9B—C3B	−177.3 (5)
C11D—C1D—C6D—C5D	−178.5 (5)	N1B—C8B—C9B—C3B	1.6 (6)
C2D—C1D—C6D—C5D	2.1 (7)	C3B—C31B—C32B—N33B	−178.5 (4)
C2D—C1D—C11D—O12D	−9.6 (7)	N1C—C2C—C3C—C9C	0.0 (6)
C11D—C1D—C2D—C3D	179.2 (4)	N1C—C2C—C3C—C31C	−177.3 (5)
C2D—C1D—C11D—O11D	171.5 (4)	C31C—C3C—C9C—C4C	−2.5 (9)
C1D—C2D—C3D—C4D	−0.2 (7)	C2C—C3C—C9C—C8C	−0.4 (6)
C1D—C2D—C3D—N3D	179.6 (4)	C31C—C3C—C9C—C8C	176.9 (5)
N3D—C3D—C4D—C5D	−178.8 (4)	C2C—C3C—C31C—C32C	−81.3 (6)
C2D—C3D—C4D—C5D	1.0 (7)	C2C—C3C—C9C—C4C	−179.8 (5)
C3D—C4D—C5D—C6D	−0.2 (7)	C9C—C3C—C31C—C32C	101.9 (6)
C3D—C4D—C5D—N5D	175.5 (4)	C5C—C4C—C9C—C3C	178.5 (5)
C4D—C5D—C6D—C1D	−1.3 (8)	C5C—C4C—C9C—C8C	−0.9 (7)
N5D—C5D—C6D—C1D	−177.1 (4)	C9C—C4C—C5C—C6C	−0.3 (8)
C2E—C1E—C11E—O12E	6.0 (7)	C4C—C5C—C6C—C7C	1.0 (8)
C6E—C1E—C11E—O11E	6.9 (7)	C5C—C6C—C7C—C8C	−0.5 (8)
C2E—C1E—C11E—O11E	−172.8 (5)	C6C—C7C—C8C—N1C	−179.2 (5)
C2E—C1E—C6E—C5E	0.3 (7)	C6C—C7C—C8C—C9C	−0.7 (8)
C6E—C1E—C11E—O12E	−174.3 (4)	N1C—C8C—C9C—C3C	0.7 (5)
C11E—C1E—C6E—C5E	−179.4 (4)	C7C—C8C—C9C—C4C	1.4 (7)
C11E—C1E—C2E—C3E	179.0 (5)	N1C—C8C—C9C—C4C	−179.8 (4)
C6E—C1E—C2E—C3E	−0.7 (7)	C7C—C8C—C9C—C3C	−178.1 (5)
C2G—N1G—C9G—C10G	2.3 (8)	C3C—C31C—C32C—N33C	176.7 (4)
C9G—N1G—C2G—C3G	0.4 (9)	N1G—C2G—C3G—C4G	−2.1 (9)
C2G—N1G—C9G—C8G	−179.1 (5)	C2G—C3G—C4G—C10G	1.0 (9)
C1E—C2E—C3E—C4E	1.4 (8)	C3G—C4G—C10G—C5G	−179.7 (6)
C1E—C2E—C3E—N3E	−178.0 (5)	C3G—C4G—C10G—C9G	1.5 (9)
C2E—C3E—C4E—C5E	−1.6 (8)	C10G—C5G—C6G—C7G	0.5 (9)
N3E—C3E—C4E—C5E	177.8 (4)	C6G—C5G—C10G—C4G	−178.4 (6)
C3E—C4E—C5E—N5E	−178.0 (4)	C6G—C5G—C10G—C9G	0.4 (9)
C3E—C4E—C5E—C6E	1.2 (7)	C5G—C6G—C7G—C8G	−1.2 (9)
N5E—C5E—C6E—C1E	178.5 (4)	C6G—C7G—C8G—C9G	1.0 (9)
C4E—C5E—C6E—C1E	−0.6 (7)	C7G—C8G—C9G—C10G	0.0 (9)
C6F—C1F—C11F—O11F	11.3 (7)	C7G—C8G—C9G—N1G	−178.7 (5)
C2F—C1F—C11F—O11F	−170.1 (5)	N1G—C9G—C10G—C4G	−3.2 (9)
C2F—C1F—C11F—O12F	8.2 (7)	N1G—C9G—C10G—C5G	177.9 (5)
C11F—C1F—C2F—C3F	179.8 (5)	C8G—C9G—C10G—C4G	178.2 (6)
C2F—C1F—C6F—C5F	0.6 (8)	C8G—C9G—C10G—C5G	−0.7 (8)
C11F—C1F—C6F—C5F	179.2 (5)	N1H—C2H—C3H—C4H	−1.6 (9)
C6F—C1F—C11F—O12F	−170.4 (5)	C2H—C3H—C4H—C10H	1.2 (8)
C6F—C1F—C2F—C3F	−1.7 (7)	C3H—C4H—C10H—C5H	179.4 (5)
C2H—N1H—C9H—C8H	−176.7 (5)	C3H—C4H—C10H—C9H	1.1 (8)
C9H—N1H—C2H—C3H	−0.6 (9)	C10H—C5H—C6H—C7H	0.3 (9)
C2H—N1H—C9H—C10H	3.1 (8)	C6H—C5H—C10H—C4H	−176.5 (5)
C1F—C2F—C3F—C4F	1.1 (7)	C6H—C5H—C10H—C9H	1.7 (9)
C1F—C2F—C3F—N3F	−179.4 (4)	C5H—C6H—C7H—C8H	−2.1 (9)
C2F—C3F—C4F—C5F	0.5 (7)	C6H—C7H—C8H—C9H	2.0 (8)
N3F—C3F—C4F—C5F	−179.0 (4)	C7H—C8H—C9H—N1H	179.8 (5)
C3F—C4F—C5F—N5F	178.1 (4)	C7H—C8H—C9H—C10H	0.0 (8)
C3F—C4F—C5F—C6F	−1.6 (7)	N1H—C9H—C10H—C4H	−3.3 (9)
C4F—C5F—C6F—C1F	1.1 (8)	N1H—C9H—C10H—C5H	178.4 (5)
N5F—C5F—C6F—C1F	−178.6 (5)	C8H—C9H—C10H—C4H	176.4 (5)
N1A—C2A—C3A—C31A	179.7 (5)	C8H—C9H—C10H—C5H	−1.9 (9)
N1A—C2A—C3A—C9A	0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O52D^i	0.88	2.09	2.972 (6)	175
N1B—H1B···O31E^ii	0.88	2.10	2.942 (6)	161
N1C—H1C···O31F	0.88	2.09	2.966 (5)	178
N33A—H34A···O12D	0.91	1.84	2.722 (6)	163
N33B—H34B···O11E	0.91	1.89	2.761 (5)	161
N33C—H34C···O11F^i	0.91	1.83	2.717 (5)	163
N33A—H35A···O1W	0.91	2.21	2.931 (6)	136
N33A—H35A···O1W^iii	0.91	2.44	3.164 (5)	137
N33B—H35B···O11D	0.91	1.93	2.838 (5)	178
N33C—H35C···O12F^iii	0.91	1.85	2.745 (4)	168
N33A—H36A···O12E	0.91	1.87	2.766 (5)	169
N33B—H36B···N1G	0.91	1.99	2.876 (6)	165
N33C—H36C···N1H	0.91	2.01	2.905 (6)	168
O1W—H11W···O11E	0.85	2.03	2.829 (5)	157
O1W—H12W···O2W	0.85	1.88	2.729 (6)	174
O2W—H21W···O12F	0.85	1.92	2.760 (4)	168
O2W—H22W···O11D	0.85	2.00	2.843 (5)	170
C2C—H2C···O1W	0.95	2.59	3.277 (7)	129
C2C—H2C···O2W^iii	0.95	2.54	3.328 (6)	140
C5A—H5A···O31D	0.95	2.58	3.306 (7)	134
C32B—H32B···O52E^iv	0.99	2.53	3.289 (6)	133
C32C—H32C···O31E	0.99	2.52	3.510 (6)	178
C32A—H33A···O2W^iii	0.99	2.59	3.256 (7)	125
C5B—H5B···O52E	0.95	2.54	3.284 (7)	136

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z.