cyclo{[(6-Amino-6-de­oxy-2,3:4,5-di-O-isopropyl­idene-d-galactonic acid)-(d-Phe)]2}

Bream, R.; Watkin, D.; Soengas, R.; Fleet, G.W.J.; Edwards, A.A.; Hunter, S.J.; Tranter, G.E.

doi:10.1107/S1600536806012487

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 5| May 2006| Pages o1851-o1853

https://doi.org/10.1107/S1600536806012487

cyclo{[(6-Amino-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid)-(D-Phe)]₂}

Richard Bream,^a ^* David Watkin,^a Raquel Soengas,^b George W. J. Fleet,^b Alison A. Edwards,^c Stuart J. Hunter ^b and George E. Tranter ^c

^aChemical Crystallography, Central Chemistry Laboratory, University of Oxford, Oxford OX1 3TA, England, ^bDepartment of Organic Chemistry, Chemical Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, and ^cBiological Chemistry, Division of Biomedical Sciences, Imperial College, London SW7 2AZ, England
^*Correspondence e-mail: richard.bream@pmb.ox.ac.uk

(Received 3 April 2006; accepted 5 April 2006; online 13 April 2006)

Determination of the crystal structure of the title compound [systematic name: 9,25-dibenzyl-4,4,15,15,20,20,31,31-octamethyl-3,5,14,16,19,21,30,32-octaoxa-8,11,24,27-tetraazapentacyclo[27.3.0.0^2,6.0^13,17.0^18,22]dotriacontane-7,10,23,26-tetrone], C₄₂H₅₆N₄O₁₂, a cyclic tetramer, established the relative stereochemistry of its ten stereogenic C atoms; an interesting saddle-like conformation is adopted. There are two molecules in the asymmetric unit. With the exception of the phenyl and isopropylidene groups, the molecules are related by a non-crystallographic twofold rotation axis. There are varying degrees of disorder in the isopropylidene groups.

Comment

Carbohydrates which contain amine and acid groups are commonly referred to as sugar amino acids (SAAs) (Chakraborty et al., 2004 ; Gruner et al., 2002 ; Smith & Fleet, 1999 ). They have been the focus of much interest as dipeptide isosteres and library scaffolds, and their linear oligomers as foldamers (Jensen & Brask, 2005 , Trabocchi et al., 2005 ). SAAs and α-amino acids have been combined in cyclic peptides (Stockle et al., 2002 ; van Well et al., 2000 ) to create mimics of biologically active cyclic peptides (van Well, Overkleeft et al., 2003 ; Gruner et al., 2001 ). Several cyclic homooligomers have now been prepared using oxetane, furanose and pyranose SAAs (Johnson et al., 2006 ; van Well, Marinelli et al., 2003 ; Chakraborty et al., 2003 ); a cyclic hexamer of pyranose SAAs was found to form inclusion complexes akin to those of cyclodextrins (Locardi et al., 2001 ). A new family of cyclic SAA oligomers, based on acyclic SAAs, has been established (Mayes, Stetz et al., 2004 ; Mayes, Simon et al., 2004 ; Mayes, Cowley et al., 2004 ) and a cyclic dimer of galactose stereochemistry found to interact with probe compounds (Edwards et al., 2005 ). This family has now been expanded to include heterooligomers which incorporate phenylalanine (Phe).

The X-ray crystal structure confirms the structural integrity of the title compound, (3), and the absolute stereochemistry is determined by the use of D-galactonolactone as the starting material for the synthesis of (1). The saddle-like conformation adopted by (3) is of particular interest (Fig. 1).

The material crystallizes in P1, with two molecules in the asymmetric unit (Fig. 2). The ring atoms in both molecules adopt the same conformation, the only differences being in the phenyl groups, which adopt different conformations in each molecule. The methyl groups on the isopropylidene rings show elongated displacement ellipsoids, and as such are probably disordered. Only two of the eight groups, one on each ring, are actually disordered enough to be modelled as such. The remaining groups were best modelled by large ADP. One of the isopropylidene rings also shows a disordered O atom, suggesting that it is the O atom on the ring, rather than the C atom with the methyl groups attached, that is flipping. Indeed, the dimethyl C atom has a small, well shaped displacement ellipsoid, suggesting that it does not move to any great degree, and the ring flips about it.

When the phenyl groups, the hydrogen and the isopropylidene methyl groups are removed, it is found that the skeletons of the two rings map on to each other, related by a pseudo-twofold rotation axis (r.m.s. deviation in atomic position = 0.137 Å; r.m.s. deviation in bond length = 0.012 Å; r.m.s. deviation in torsion angles = 5.78°).

The structure consists of ribbons of hydrogen-bonded molecules, with alternating inter- and intramolecular hydrogen bonds, parallel to the a axis (Table 1, and Figs. 3 and 4).

Figure 1
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radii. The bonds in the 20-membered ring are black.

Figure 2
The asymmetric unit, viewed parallel to a, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radii.

Figure 3
Packing diagram, viewed along the a axis, showing the hydrogen-bonded ribbons end on.

Figure 4
Packing diagram, viewed along the c axis, showing the hydrogen-bonded ribbons parallel to the a axis. Hydrogen bonds are drawn as dotted lines.

Experimental

Compound (3) was prepared by hydrogenation of the pentafluorophenyl ester of the linear SAA-Phe dimer (2) with palladized carbon in dioxane; no cyclic dimer was observed. The linear dimer (2) was prepared by coupling of the free acid of SAA (1) (Long et al., 1999 ) with the methyl ester of D-phenylalanine using standard peptide coupling reagents (O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate and triethylamine). The sample for X-ray analysis was crystallized from methanol.

Crystal data

C₄₂H₅₆N₄O₁₂
M_r = 808.93
Triclinic, P 1
a = 9.1755 (1) Å
b = 15.4193 (2) Å
c = 15.5475 (2) Å
α = 77.2624 (5)°
β = 82.0270 (5)°
γ = 78.2560 (7)°
V = 2090.45 (4) Å³
Z = 2
D_x = 1.285 Mg m⁻³
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
Needle, colourless
0.60 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
ω scans
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.621, T_max = 0.981
17594 measured reflections
9415 independent reflections
9411 reflections with I > −3σ(I)
R_int = 0.017
θ_max = 27.5°

Refinement

Refinement on F²
R[F²> 2σ(F²)] = 0.048
wR(F²) = 0.089
S = 1.00
9411 reflections
1090 parameters
H-atom parameters constrained
w = 1/[σ²(F²) + (0.04P)² + 0.37P], where P = [max(F_o²,0) + 2F_c²]/3
(Δ/σ)_max = 0.001
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N119—H1⋯O161	0.89	1.89	2.776 (2)	174
N16—H2⋯O40	0.88	1.95	2.813 (2)	170
N116—H3⋯O141ⁱ	0.86	2.08	2.883 (2)	155
N132—H4⋯O156ⁱⁱ	0.85	2.09	2.916 (2)	163
N19—H5⋯O60ⁱⁱ	0.85	2.15	2.966 (2)	160
N3—H7⋯O45ⁱ	0.85	2.08	2.897 (2)	159
N32—H8⋯O53	0.85	1.92	2.753 (2)	167
N102—H9⋯O148	0.85	1.96	2.798 (2)	167
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

In the absence of significant anomalous scattering, Friedel pairs were merged. To model the disorder, those atoms with unusually elongated displacement ellipsoids were split, and each atom given an occupancy of 0.5. Coordinates, U^ij values and site occupancies of these atoms were then refined. No geometric restraints were applied. The isopropylidene ring containing C56–C59 showed significant deviation from equal occupancies, ending up at 0.581 (4):0.419 (4). The isopropylidene ring containing C144–C157 showed no deviation from equal occupancies, with the occupancies converging to 0.500 (3):0.500 (3). The H atoms were all located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98 Å, N—H in the range 0.86–0.89 Å and O—H = 0.82 Å) and displacement parameters [U_iso(H) in the range 1.2–1.5 times U_eq of the parent atom], after which they were refined with riding constraints.

Data collection: COLLECT (Nonius, 2001 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, 3. DOI: https://doi.org/10.1107/S1600536806012487/sj2038sup1.cif

Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S1600536806012487/sj20383sup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

9,25-Dibenzyl-4,4,15,15,20,20,31,31-octamethyl-3,5,14,16,19,21,30,32- octaoxa-8,11,24,27- tetraazapentacyclo[27.3.0.0^2,6.0^13,17.0^18,22]dotriacontane- 7,10,23,26-tetrone top

Crystal data top

C₄₂H₅₆N₄O₁₂	Z = 2
M_r = 808.93	F(000) = 864
Triclinic, P1	D_x = 1.285 Mg m⁻³
a = 9.1755 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.4193 (2) Å	Cell parameters from 8903 reflections
c = 15.5475 (2) Å	θ = 5–27°
α = 77.2624 (5)°	µ = 0.09 mm⁻¹
β = 82.0270 (5)°	T = 150 K
γ = 78.2560 (7)°	Plate, colourless
V = 2090.45 (4) Å³	0.60 × 0.20 × 0.20 mm

Data collection top

Nonius KappaCCD diffractometer	9411 reflections with I > −3σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 27.5°, θ_min = 5.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −11→11
T_min = 0.621, T_max = 0.981	k = −19→19
17594 measured reflections	l = −20→20
9415 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F²) + (0.04P)² + 0.37P], where P = [max(F_o²,0) + 2F_c²]/3
S = 1.00	(Δ/σ)_max = 0.001
9411 reflections	Δρ_max = 0.47 e Å⁻³
1090 parameters	Δρ_min = −0.26 e Å⁻³
3 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.1602 (2)	0.71407 (18)	0.51070 (16)	0.0262
C2	0.2449 (2)	0.62211 (18)	0.55200 (16)	0.0258
N3	0.1838 (2)	0.54939 (15)	0.55504 (14)	0.0288
C4	0.2577 (3)	0.45965 (18)	0.59511 (17)	0.0307
C5	0.3559 (3)	0.40664 (18)	0.53017 (17)	0.0287
O6	0.2602 (2)	0.38501 (17)	0.47648 (14)	0.0466
C7	0.3260 (3)	0.39140 (19)	0.38814 (18)	0.0335
O8	0.4540 (2)	0.43120 (18)	0.38066 (13)	0.0509
C9	0.4679 (3)	0.45482 (19)	0.46271 (16)	0.0281
C10	0.6315 (3)	0.42641 (17)	0.48008 (17)	0.0273
O11	0.67032 (18)	0.33075 (12)	0.50355 (12)	0.0303
C12	0.7937 (3)	0.31125 (19)	0.55580 (18)	0.0309
O13	0.7620 (2)	0.38134 (12)	0.60731 (12)	0.0337
C14	0.6749 (3)	0.45836 (17)	0.56006 (16)	0.0256
C15	0.7611 (3)	0.53791 (17)	0.52759 (16)	0.0257
N16	0.6693 (2)	0.61835 (14)	0.51277 (15)	0.0287
C17	0.7232 (3)	0.70397 (17)	0.47718 (17)	0.0257
C18	0.6423 (3)	0.74983 (17)	0.39455 (17)	0.0266
N19	0.7226 (2)	0.75454 (15)	0.31638 (14)	0.0280
C20	0.6547 (3)	0.80035 (18)	0.23479 (17)	0.0299
C21	0.6079 (3)	0.73727 (18)	0.18491 (17)	0.0278
O22	0.73851 (19)	0.68299 (13)	0.15021 (13)	0.0361
C23	0.7245 (3)	0.5896 (2)	0.17420 (19)	0.0359
O24	0.5734 (2)	0.58864 (13)	0.20294 (15)	0.0427
C25	0.5102 (3)	0.66950 (17)	0.23612 (17)	0.0278
C26	0.3464 (3)	0.68978 (18)	0.21992 (17)	0.0277
O27	0.33149 (19)	0.71847 (13)	0.12721 (12)	0.0329
C28	0.1969 (3)	0.7806 (2)	0.11569 (18)	0.0398
O29	0.1471 (2)	0.81080 (15)	0.19512 (13)	0.0474
C30	0.2486 (3)	0.76843 (18)	0.25930 (16)	0.0282
C31	0.1598 (2)	0.73525 (18)	0.34743 (17)	0.0276
N32	0.2239 (2)	0.73839 (15)	0.41860 (13)	0.0281
C33	0.1771 (3)	0.78708 (19)	0.55960 (17)	0.0304
C34	0.1098 (3)	0.77502 (19)	0.65504 (17)	0.0310
C35	−0.0334 (3)	0.82065 (19)	0.67619 (19)	0.0343
C36	−0.0963 (3)	0.8128 (2)	0.76376 (19)	0.0415
C37	−0.0152 (3)	0.7599 (2)	0.8311 (2)	0.0457
C38	0.1263 (3)	0.7138 (2)	0.8109 (2)	0.0482
C39	0.1893 (3)	0.7211 (2)	0.72352 (18)	0.0391
O40	0.36836 (18)	0.61550 (13)	0.57846 (12)	0.0314
C41	0.2153 (4)	0.4520 (4)	0.3287 (3)	0.0858
C42	0.3741 (6)	0.2998 (3)	0.3679 (4)	0.0916
C43	0.7901 (3)	0.2217 (2)	0.6183 (2)	0.0415
C44	0.9399 (3)	0.3142 (2)	0.4985 (2)	0.0428
O45	0.89684 (19)	0.52718 (13)	0.51393 (15)	0.0386
C46	0.6856 (3)	0.76367 (18)	0.54684 (17)	0.0306
C47	0.7132 (3)	0.85939 (18)	0.51639 (17)	0.0300
C48	0.8247 (3)	0.88328 (19)	0.45017 (17)	0.0315
C49	0.8535 (4)	0.9711 (2)	0.4280 (2)	0.0412
C50	0.7693 (4)	1.0361 (2)	0.4722 (2)	0.0549
C51	0.6581 (4)	1.0144 (2)	0.5367 (2)	0.0555
C52	0.6289 (3)	0.9268 (2)	0.5588 (2)	0.0413
O53	0.50621 (18)	0.77882 (12)	0.40329 (12)	0.0310
C54	0.8256 (4)	0.5421 (2)	0.2462 (2)	0.0551
C55	0.7630 (5)	0.5481 (3)	0.0924 (2)	0.0613
C56	0.2695 (8)	0.8740 (5)	0.0700 (5)	0.0473	0.4187
C57	0.1954 (6)	0.8451 (4)	0.0331 (3)	0.0494	0.5813
C58	0.0911 (8)	0.7720 (8)	0.0633 (6)	0.0547	0.4187
C59	0.0779 (6)	0.7142 (5)	0.1204 (5)	0.0536	0.5813
O60	0.04183 (19)	0.70884 (16)	0.35092 (13)	0.0420
C101	1.0124 (2)	0.10326 (17)	0.91125 (17)	0.0265
N102	0.9168 (2)	0.18806 (14)	0.87479 (14)	0.0268
C103	0.9547 (3)	0.26958 (18)	0.86707 (17)	0.0281
C104	0.8363 (3)	0.35031 (18)	0.83034 (17)	0.0288
O105	0.9059 (2)	0.42168 (13)	0.77952 (13)	0.0353
C106	0.8625 (3)	0.49951 (19)	0.81951 (19)	0.0341
O107	0.7271 (2)	0.48608 (13)	0.87359 (13)	0.0358
C108	0.7391 (3)	0.39131 (17)	0.90704 (17)	0.0287
C109	0.5858 (3)	0.3661 (2)	0.93319 (17)	0.0335
O110	0.5329 (13)	0.4113 (5)	1.0096 (7)	0.0352	0.4999
O111	0.5254 (12)	0.3760 (5)	1.0195 (8)	0.0405	0.5001
C112	0.3777 (3)	0.4341 (2)	1.01408 (18)	0.0349
O113	0.3364 (2)	0.4376 (2)	0.92944 (16)	0.0646
C114	0.4632 (3)	0.4128 (2)	0.87110 (19)	0.0346
C115	0.4192 (3)	0.35751 (19)	0.81228 (18)	0.0340
N116	0.3927 (2)	0.26731 (16)	0.85571 (15)	0.0326
C117	0.5019 (3)	0.19650 (19)	0.85376 (16)	0.0289
C118	0.4674 (3)	0.10127 (19)	0.89230 (16)	0.0278
N119	0.5115 (2)	0.07369 (15)	0.98252 (13)	0.0271
C120	0.4147 (2)	0.07579 (16)	1.05509 (16)	0.0228
C121	0.4919 (2)	0.04838 (17)	1.14107 (15)	0.0242
O122	0.4019 (2)	0.00516 (13)	1.21258 (11)	0.0317
C123	0.3687 (3)	0.05793 (19)	1.28157 (17)	0.0301
O124	0.48327 (17)	0.11051 (13)	1.26527 (11)	0.0296
C125	0.5194 (3)	0.13188 (17)	1.17195 (16)	0.0262
C126	0.6781 (3)	0.15074 (17)	1.15177 (17)	0.0264
O127	0.6740 (2)	0.23383 (13)	1.17970 (15)	0.0417
C128	0.8143 (3)	0.23237 (18)	1.20760 (18)	0.0314
O129	0.87966 (19)	0.13960 (13)	1.23320 (13)	0.0340
C130	0.7977 (2)	0.08318 (17)	1.20512 (16)	0.0249
C131	0.9065 (3)	0.01718 (18)	1.15686 (17)	0.0293
N132	0.9784 (2)	0.05931 (15)	1.07287 (14)	0.0289
C133	0.9294 (2)	0.05959 (17)	0.99621 (17)	0.0268
C134	1.0479 (3)	0.03790 (19)	0.84773 (18)	0.0323
C135	1.1189 (3)	0.06999 (18)	0.75547 (17)	0.0286
C136	1.1159 (4)	0.0210 (2)	0.6911 (2)	0.0447
C137	1.1836 (5)	0.0436 (3)	0.6064 (2)	0.0593
C138	1.2539 (4)	0.1180 (2)	0.5838 (2)	0.0527
C139	1.2575 (3)	0.1679 (2)	0.6461 (2)	0.0405
C140	1.1907 (3)	0.14407 (18)	0.73208 (18)	0.0299
O141	1.07266 (19)	0.28003 (13)	0.88842 (14)	0.0385
C142	0.9834 (3)	0.5056 (2)	0.8739 (2)	0.0424
C143	0.8277 (4)	0.5815 (2)	0.7472 (2)	0.0498
C144	0.3882 (12)	0.5275 (7)	1.0146 (7)	0.0604	0.5001
C145	0.3314 (10)	0.5252 (7)	1.0470 (6)	0.0487	0.4999
C146	0.2763 (15)	0.3907 (10)	1.0917 (9)	0.0639	0.5001
C147	0.2963 (15)	0.3632 (8)	1.0670 (9)	0.0582	0.4999
O148	0.63080 (18)	0.20509 (13)	0.82270 (13)	0.0350
C149	0.5583 (3)	0.0377 (2)	0.83273 (17)	0.0325
C150	0.5412 (3)	−0.0596 (2)	0.85827 (17)	0.0329
C151	0.4569 (3)	−0.0944 (3)	0.8107 (2)	0.0493
C152	0.4525 (4)	−0.1863 (3)	0.8291 (3)	0.0708
C153	0.5298 (5)	−0.2437 (3)	0.8948 (3)	0.0701
C154	0.6130 (4)	−0.2102 (2)	0.9435 (2)	0.0559
C155	0.6186 (3)	−0.1195 (2)	0.92491 (18)	0.0407
O156	0.27963 (18)	0.09948 (14)	1.05416 (12)	0.0348
C157	0.2166 (3)	0.1165 (2)	1.2744 (2)	0.0451
C158	0.3852 (4)	−0.0053 (2)	1.36983 (18)	0.0454
C159	0.7884 (5)	0.2776 (3)	1.2867 (3)	0.0631
C160	0.9138 (4)	0.2775 (2)	1.1327 (3)	0.0599
O161	0.81821 (18)	0.02636 (13)	0.99201 (12)	0.0333
H11	0.0546	0.7106	0.5126	0.0304*
H41	0.3240	0.4653	0.6370	0.0364*
H42	0.1831	0.4241	0.6254	0.0359*
H51	0.4078	0.3499	0.5622	0.0351*
H91	0.4388	0.5209	0.4561	0.0347*
H101	0.6943	0.4487	0.4266	0.0334*
H141	0.5838	0.4770	0.5980	0.0317*
H171	0.8306	0.6914	0.4612	0.0295*
H201	0.7282	0.8320	0.1954	0.0357*
H202	0.5662	0.8445	0.2490	0.0359*
H211	0.5571	0.7728	0.1325	0.0313*
H251	0.5165	0.6597	0.2999	0.0311*
H261	0.3045	0.6343	0.2429	0.0327*
H301	0.3100	0.8100	0.2697	0.0323*
H331	0.2852	0.7868	0.5578	0.0360*
H332	0.1258	0.8455	0.5270	0.0364*
H351	−0.0854	0.8581	0.6298	0.0442*
H361	−0.1956	0.8438	0.7772	0.0515*
H371	−0.0544	0.7544	0.8898	0.0574*
H381	0.1811	0.6784	0.8577	0.0598*
H391	0.2867	0.6901	0.7100	0.0478*
H411	0.2644	0.4696	0.2695	0.1193*
H412	0.1759	0.5043	0.3534	0.1202*
H413	0.1357	0.4204	0.3271	0.1201*
H421	0.4165	0.3057	0.3065	0.1395*
H422	0.4485	0.2689	0.4067	0.1402*
H423	0.2882	0.2689	0.3800	0.1398*
H431	0.8665	0.2101	0.6585	0.0619*
H432	0.6933	0.2242	0.6518	0.0616*
H433	0.8096	0.1742	0.5838	0.0616*
H441	1.0218	0.3024	0.5329	0.0634*
H442	0.9351	0.3715	0.4596	0.0640*
H443	0.9560	0.2670	0.4643	0.0632*
H461	0.7418	0.7341	0.5971	0.0373*
H462	0.5793	0.7664	0.5675	0.0360*
H481	0.8809	0.8403	0.4189	0.0395*
H491	0.9293	0.9853	0.3836	0.0511*
H501	0.7869	1.0959	0.4583	0.0694*
H511	0.6011	1.0586	0.5665	0.0671*
H521	0.5512	0.9120	0.6030	0.0501*
H541	0.8136	0.4794	0.2641	0.0766*
H542	0.9296	0.5434	0.2241	0.0770*
H543	0.7966	0.5727	0.2961	0.0771*
H551	0.7413	0.4869	0.1047	0.0887*
H552	0.8701	0.5474	0.0722	0.0892*
H553	0.7018	0.5843	0.0457	0.0883*
H1011	1.1034	0.1179	0.9241	0.0308*
H1041	0.7723	0.3329	0.7929	0.0345*
H1081	0.7956	0.3750	0.9578	0.0339*
H1141	0.4930	0.4672	0.8317	0.0406*
H1151	0.3261	0.3909	0.7904	0.0408*
H1152	0.4971	0.3531	0.7634	0.0398*
H1181	0.3586	0.1030	0.8956	0.0313*
H1211	0.5878	0.0069	1.1323	0.0275*
H1251	0.4493	0.1845	1.1463	0.0311*
H1261	0.7061	0.1558	1.0879	0.0306*
H1301	0.7446	0.0482	1.2580	0.0295*
H1311	0.9859	−0.0123	1.1951	0.0332*
H1312	0.8542	−0.0263	1.1454	0.0338*
H1341	1.1150	−0.0129	0.8738	0.0391*
H1342	0.9531	0.0222	0.8416	0.0384*
H1361	1.0663	−0.0289	0.7041	0.0559*
H1371	1.1815	0.0084	0.5646	0.0740*
H1381	1.2989	0.1343	0.5259	0.0613*
H1391	1.3059	0.2198	0.6298	0.0475*
H1401	1.1940	0.1802	0.7742	0.0359*
H1421	0.9494	0.5580	0.9020	0.0659*
H1422	1.0006	0.4504	0.9183	0.0649*
H1423	1.0763	0.5141	0.8376	0.0658*
H1431	0.7968	0.6346	0.7734	0.0749*
H1432	0.9132	0.5876	0.7068	0.0748*
H1433	0.7493	0.5749	0.7170	0.0746*
H1491	0.6633	0.0418	0.8325	0.0385*
H1492	0.5289	0.0625	0.7719	0.0383*
H1511	0.4021	−0.0557	0.7661	0.0629*
H1521	0.3962	−0.2077	0.7963	0.0941*
H1531	0.5253	−0.3048	0.9060	0.0843*
H1541	0.6674	−0.2506	0.9904	0.0639*
H1551	0.6782	−0.0979	0.9579	0.0481*
H1571	0.1966	0.1517	1.3202	0.0675*
H1572	0.1436	0.0780	1.2824	0.0682*
H1573	0.2154	0.1546	1.2164	0.0678*
H1581	0.3663	0.0274	1.4170	0.0669*
H1582	0.4851	−0.0402	1.3725	0.0666*
H1583	0.3136	−0.0468	1.3817	0.0666*
H1591	0.8886	0.2752	1.3046	0.0978*
H1592	0.7285	0.2443	1.3326	0.0975*
H1593	0.7364	0.3398	1.2702	0.0976*
H1601	1.0081	0.2761	1.1526	0.0838*
H1602	0.8707	0.3400	1.1129	0.0838*
H1603	0.9311	0.2476	1.0811	0.0844*
H1	0.6084	0.0563	0.9894	0.0312*
H2	0.5729	0.6205	0.5264	0.0345*
H3	0.3051	0.2604	0.8804	0.0388*
H4	1.0576	0.0793	1.0738	0.0335*
H5	0.8167	0.7367	0.3141	0.0322*
H7	0.1004	0.5558	0.5338	0.0356*
H8	0.3057	0.7582	0.4083	0.0344*
H9	0.8344	0.1853	0.8571	0.0319*
H561	0.3453	0.8803	0.1076	0.0554*	0.4187
H562	0.1878	0.9283	0.0660	0.0554*	0.4187
H563	0.3185	0.8690	0.0092	0.0554*	0.4187
H571	0.2689	0.8855	0.0310	0.0548*	0.5813
H572	0.0929	0.8822	0.0280	0.0548*	0.5813
H573	0.2232	0.8122	−0.0172	0.0548*	0.5813
H581	0.0481	0.7165	0.0906	0.0703*	0.4187
H582	0.0093	0.8262	0.0594	0.0703*	0.4187
H583	0.1400	0.7670	0.0026	0.0703*	0.4187
H591	0.0800	0.6699	0.1780	0.0665*	0.5813
H592	−0.0249	0.7510	0.1156	0.0665*	0.5813
H593	0.1054	0.6809	0.0704	0.0665*	0.5813
H1471	0.3300	0.3065	1.0430	0.0676*	0.4999
H1472	0.3178	0.3513	1.1302	0.0676*	0.4999
H1473	0.1863	0.3838	1.0632	0.0676*	0.4999
H1461	0.2755	0.3274	1.0862	0.0720*	0.5001
H1462	0.3151	0.3899	1.1489	0.0720*	0.5001
H1463	0.1722	0.4263	1.0904	0.0720*	0.5001
H1451	0.3891	0.5707	1.0093	0.0591*	0.4999
H1452	0.3534	0.5154	1.1100	0.0591*	0.4999
H1453	0.2219	0.5479	1.0429	0.0591*	0.4999
H1441	0.4560	0.5508	0.9622	0.0751*	0.5001
H1442	0.4294	0.5295	1.0703	0.0751*	0.5001
H1443	0.2865	0.5660	1.0118	0.0751*	0.5001
H1091	0.5905	0.2992	0.9500	0.0410*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0169 (10)	0.0375 (14)	0.0243 (12)	−0.0067 (9)	0.0009 (9)	−0.0064 (11)
C2	0.0187 (10)	0.0362 (15)	0.0234 (12)	−0.0074 (9)	0.0008 (9)	−0.0076 (11)
N3	0.0209 (9)	0.0360 (13)	0.0313 (11)	−0.0082 (9)	−0.0035 (8)	−0.0071 (10)
C4	0.0271 (12)	0.0357 (15)	0.0284 (13)	−0.0125 (10)	−0.0002 (10)	0.0004 (11)
C5	0.0249 (11)	0.0342 (15)	0.0296 (13)	−0.0129 (10)	−0.0022 (10)	−0.0048 (11)
O6	0.0349 (10)	0.0762 (16)	0.0428 (12)	−0.0335 (10)	0.0054 (9)	−0.0254 (11)
C7	0.0301 (13)	0.0373 (16)	0.0375 (15)	−0.0132 (11)	−0.0072 (11)	−0.0077 (12)
O8	0.0426 (11)	0.0959 (18)	0.0295 (10)	−0.0405 (11)	0.0025 (8)	−0.0229 (11)
C9	0.0264 (12)	0.0376 (15)	0.0241 (12)	−0.0149 (10)	−0.0010 (9)	−0.0063 (11)
C10	0.0248 (11)	0.0306 (15)	0.0291 (13)	−0.0109 (10)	−0.0011 (9)	−0.0068 (11)
O11	0.0279 (9)	0.0305 (10)	0.0367 (10)	−0.0081 (7)	−0.0034 (7)	−0.0125 (8)
C12	0.0297 (12)	0.0315 (15)	0.0345 (14)	−0.0062 (10)	−0.0053 (10)	−0.0110 (12)
O13	0.0426 (10)	0.0266 (10)	0.0348 (10)	−0.0043 (8)	−0.0128 (8)	−0.0083 (8)
C14	0.0260 (11)	0.0274 (14)	0.0256 (12)	−0.0092 (10)	−0.0028 (9)	−0.0056 (10)
C15	0.0239 (11)	0.0285 (14)	0.0282 (13)	−0.0079 (10)	−0.0056 (9)	−0.0083 (10)
N16	0.0184 (9)	0.0289 (12)	0.0390 (13)	−0.0083 (8)	−0.0019 (8)	−0.0044 (10)
C17	0.0193 (10)	0.0275 (13)	0.0318 (13)	−0.0085 (9)	−0.0012 (9)	−0.0057 (11)
C18	0.0242 (11)	0.0246 (13)	0.0346 (14)	−0.0106 (10)	−0.0014 (10)	−0.0084 (11)
N19	0.0220 (9)	0.0310 (12)	0.0306 (11)	−0.0044 (8)	−0.0011 (8)	−0.0065 (9)
C20	0.0319 (13)	0.0268 (14)	0.0299 (14)	−0.0068 (10)	−0.0008 (10)	−0.0031 (11)
C21	0.0242 (11)	0.0297 (14)	0.0259 (13)	0.0002 (10)	−0.0004 (9)	−0.0039 (11)
O22	0.0251 (8)	0.0380 (12)	0.0431 (11)	0.0007 (7)	0.0037 (8)	−0.0134 (9)
C23	0.0346 (13)	0.0321 (15)	0.0371 (15)	0.0056 (11)	−0.0010 (11)	−0.0108 (12)
O24	0.0371 (10)	0.0301 (11)	0.0606 (14)	0.0013 (8)	0.0043 (9)	−0.0203 (10)
C25	0.0272 (12)	0.0230 (13)	0.0310 (13)	−0.0008 (10)	−0.0014 (10)	−0.0051 (11)
C26	0.0286 (12)	0.0282 (14)	0.0278 (13)	−0.0048 (10)	−0.0007 (10)	−0.0100 (11)
O27	0.0297 (9)	0.0439 (11)	0.0260 (9)	0.0013 (8)	−0.0019 (7)	−0.0166 (8)
C28	0.0280 (13)	0.061 (2)	0.0259 (14)	0.0056 (12)	0.0001 (10)	−0.0142 (13)
O29	0.0451 (11)	0.0609 (14)	0.0309 (10)	0.0221 (10)	−0.0126 (8)	−0.0215 (10)
C30	0.0245 (11)	0.0363 (15)	0.0230 (12)	−0.0002 (10)	−0.0033 (9)	−0.0088 (11)
C31	0.0184 (11)	0.0345 (15)	0.0315 (14)	−0.0015 (9)	−0.0017 (9)	−0.0131 (11)
N32	0.0209 (9)	0.0398 (13)	0.0252 (11)	−0.0100 (8)	−0.0002 (8)	−0.0069 (10)
C33	0.0262 (12)	0.0366 (15)	0.0304 (13)	−0.0092 (10)	−0.0005 (10)	−0.0090 (12)
C34	0.0290 (12)	0.0392 (15)	0.0302 (13)	−0.0140 (11)	−0.0001 (10)	−0.0128 (12)
C35	0.0309 (13)	0.0384 (16)	0.0377 (15)	−0.0116 (11)	0.0001 (11)	−0.0136 (13)
C36	0.0351 (14)	0.0544 (19)	0.0403 (16)	−0.0167 (13)	0.0065 (12)	−0.0189 (15)
C37	0.0490 (17)	0.067 (2)	0.0306 (15)	−0.0268 (16)	0.0043 (13)	−0.0190 (15)
C38	0.0458 (17)	0.068 (2)	0.0350 (16)	−0.0184 (15)	−0.0111 (13)	−0.0082 (15)
C39	0.0336 (14)	0.0558 (19)	0.0320 (14)	−0.0123 (13)	−0.0061 (11)	−0.0111 (13)
O40	0.0207 (8)	0.0376 (11)	0.0377 (10)	−0.0074 (7)	−0.0054 (7)	−0.0080 (8)
C41	0.0428 (19)	0.116 (4)	0.081 (3)	−0.024 (2)	−0.0212 (19)	0.037 (3)
C42	0.119 (4)	0.061 (3)	0.098 (3)	−0.038 (3)	0.053 (3)	−0.043 (3)
C43	0.0515 (17)	0.0300 (16)	0.0426 (17)	−0.0067 (12)	−0.0001 (13)	−0.0100 (13)
C44	0.0240 (12)	0.0462 (19)	0.0583 (19)	−0.0052 (12)	−0.0009 (12)	−0.0137 (15)
O45	0.0201 (8)	0.0353 (11)	0.0639 (13)	−0.0084 (7)	−0.0060 (8)	−0.0130 (10)
C46	0.0298 (12)	0.0343 (15)	0.0277 (13)	−0.0108 (11)	−0.0012 (10)	−0.0025 (11)
C47	0.0290 (12)	0.0338 (15)	0.0298 (13)	−0.0072 (10)	−0.0072 (10)	−0.0078 (11)
C48	0.0344 (13)	0.0330 (15)	0.0309 (14)	−0.0103 (11)	−0.0062 (11)	−0.0088 (11)
C49	0.0573 (18)	0.0366 (17)	0.0340 (15)	−0.0210 (14)	−0.0134 (13)	0.0013 (13)
C50	0.085 (2)	0.0296 (17)	0.057 (2)	−0.0166 (16)	−0.0249 (19)	−0.0065 (15)
C51	0.071 (2)	0.0372 (19)	0.061 (2)	0.0014 (16)	−0.0120 (18)	−0.0206 (16)
C52	0.0416 (15)	0.0414 (18)	0.0415 (17)	−0.0014 (13)	−0.0046 (12)	−0.0148 (14)
O53	0.0208 (8)	0.0361 (10)	0.0374 (10)	−0.0066 (7)	−0.0030 (7)	−0.0087 (8)
C54	0.0492 (18)	0.052 (2)	0.054 (2)	0.0068 (15)	−0.0125 (15)	0.0011 (16)
C55	0.078 (2)	0.048 (2)	0.053 (2)	0.0056 (18)	0.0029 (18)	−0.0214 (17)
C56	0.043 (4)	0.042 (4)	0.049 (4)	−0.002 (3)	0.006 (3)	−0.005 (4)
C57	0.043 (3)	0.068 (4)	0.028 (3)	0.002 (3)	−0.002 (2)	−0.001 (3)
C58	0.036 (4)	0.098 (7)	0.037 (4)	−0.017 (4)	−0.006 (3)	−0.022 (5)
C59	0.028 (3)	0.077 (5)	0.064 (4)	−0.012 (3)	0.000 (3)	−0.032 (4)
O60	0.0217 (9)	0.0726 (15)	0.0403 (11)	−0.0154 (9)	0.0027 (8)	−0.0265 (11)
C101	0.0176 (10)	0.0281 (14)	0.0329 (14)	−0.0047 (9)	−0.0024 (9)	−0.0038 (11)
N102	0.0176 (9)	0.0294 (12)	0.0340 (11)	−0.0028 (8)	−0.0042 (8)	−0.0077 (9)
C103	0.0205 (11)	0.0315 (15)	0.0336 (14)	−0.0050 (10)	0.0023 (10)	−0.0122 (11)
C104	0.0232 (11)	0.0297 (14)	0.0339 (14)	−0.0046 (10)	−0.0010 (10)	−0.0082 (11)
O105	0.0412 (10)	0.0293 (10)	0.0364 (10)	−0.0105 (8)	0.0044 (8)	−0.0098 (8)
C106	0.0359 (14)	0.0284 (15)	0.0407 (15)	−0.0052 (11)	−0.0035 (11)	−0.0133 (12)
O107	0.0320 (9)	0.0295 (11)	0.0454 (11)	0.0001 (7)	−0.0042 (8)	−0.0115 (9)
C108	0.0251 (12)	0.0289 (14)	0.0324 (13)	0.0017 (10)	−0.0067 (10)	−0.0103 (11)
C109	0.0245 (12)	0.0460 (17)	0.0280 (13)	0.0016 (11)	−0.0047 (10)	−0.0090 (12)
O110	0.034 (3)	0.044 (5)	0.029 (4)	0.000 (4)	0.000 (2)	−0.017 (4)
O111	0.026 (2)	0.061 (6)	0.024 (3)	0.004 (4)	−0.0019 (18)	0.002 (4)
C112	0.0298 (13)	0.0374 (16)	0.0355 (15)	−0.0001 (11)	0.0004 (11)	−0.0107 (12)
O113	0.0260 (10)	0.115 (2)	0.0546 (14)	0.0188 (11)	−0.0112 (9)	−0.0444 (15)
C114	0.0226 (12)	0.0417 (16)	0.0379 (15)	0.0020 (11)	−0.0079 (10)	−0.0082 (12)
C115	0.0297 (13)	0.0388 (16)	0.0312 (14)	0.0015 (11)	−0.0099 (10)	−0.0047 (12)
N116	0.0197 (9)	0.0454 (14)	0.0320 (12)	−0.0060 (9)	−0.0039 (8)	−0.0053 (10)
C117	0.0198 (11)	0.0434 (16)	0.0232 (12)	−0.0060 (10)	−0.0049 (9)	−0.0042 (11)
C118	0.0197 (10)	0.0434 (16)	0.0205 (12)	−0.0068 (10)	−0.0042 (9)	−0.0044 (11)
N119	0.0171 (9)	0.0394 (13)	0.0248 (10)	−0.0063 (8)	−0.0031 (8)	−0.0048 (9)
C120	0.0205 (11)	0.0254 (13)	0.0246 (12)	−0.0078 (9)	−0.0008 (9)	−0.0070 (10)
C121	0.0228 (11)	0.0273 (13)	0.0235 (12)	−0.0053 (9)	−0.0012 (9)	−0.0071 (10)
O122	0.0411 (10)	0.0330 (10)	0.0240 (9)	−0.0153 (8)	0.0027 (7)	−0.0079 (8)
C123	0.0270 (12)	0.0383 (15)	0.0277 (13)	−0.0080 (11)	−0.0005 (10)	−0.0113 (11)
O124	0.0221 (8)	0.0426 (11)	0.0288 (9)	−0.0061 (7)	−0.0009 (7)	−0.0177 (8)
C125	0.0232 (11)	0.0281 (14)	0.0290 (13)	−0.0019 (9)	−0.0068 (9)	−0.0092 (10)
C126	0.0243 (11)	0.0253 (13)	0.0311 (13)	−0.0052 (9)	−0.0081 (10)	−0.0048 (10)
O127	0.0382 (10)	0.0250 (10)	0.0680 (14)	−0.0050 (8)	−0.0249 (9)	−0.0108 (9)
C128	0.0269 (12)	0.0328 (15)	0.0375 (14)	−0.0087 (10)	−0.0089 (10)	−0.0067 (12)
O129	0.0289 (9)	0.0320 (11)	0.0446 (11)	−0.0078 (7)	−0.0160 (8)	−0.0049 (9)
C130	0.0207 (10)	0.0270 (13)	0.0273 (12)	−0.0058 (9)	−0.0034 (9)	−0.0038 (10)
C131	0.0225 (11)	0.0326 (15)	0.0305 (13)	−0.0043 (10)	−0.0021 (10)	−0.0023 (11)
N132	0.0177 (9)	0.0392 (13)	0.0296 (11)	−0.0076 (8)	−0.0011 (8)	−0.0051 (10)
C133	0.0149 (10)	0.0317 (14)	0.0335 (13)	−0.0027 (9)	−0.0007 (9)	−0.0081 (11)
C134	0.0294 (12)	0.0308 (15)	0.0342 (14)	−0.0045 (10)	0.0028 (10)	−0.0054 (11)
C135	0.0244 (11)	0.0288 (14)	0.0312 (14)	−0.0004 (10)	−0.0017 (10)	−0.0076 (11)
C136	0.0563 (18)	0.0398 (17)	0.0431 (17)	−0.0185 (14)	0.0031 (14)	−0.0147 (14)
C137	0.088 (3)	0.058 (2)	0.0393 (18)	−0.0235 (19)	0.0081 (17)	−0.0258 (17)
C138	0.069 (2)	0.049 (2)	0.0354 (17)	−0.0126 (16)	0.0139 (15)	−0.0080 (15)
C139	0.0408 (15)	0.0345 (16)	0.0433 (17)	−0.0111 (12)	0.0060 (12)	−0.0034 (13)
C140	0.0251 (11)	0.0299 (14)	0.0351 (14)	−0.0045 (10)	−0.0027 (10)	−0.0080 (11)
O141	0.0222 (8)	0.0362 (11)	0.0616 (13)	−0.0045 (7)	−0.0091 (8)	−0.0171 (10)
C142	0.0375 (15)	0.0427 (18)	0.0525 (18)	−0.0111 (12)	−0.0077 (13)	−0.0155 (14)
C143	0.0601 (19)	0.0342 (17)	0.055 (2)	−0.0091 (14)	−0.0131 (15)	−0.0037 (15)
C144	0.066 (7)	0.052 (5)	0.071 (7)	−0.008 (5)	−0.001 (5)	−0.036 (5)
C145	0.051 (5)	0.040 (4)	0.056 (6)	0.001 (4)	0.006 (4)	−0.026 (4)
C146	0.046 (5)	0.073 (10)	0.065 (7)	−0.003 (5)	0.007 (4)	−0.013 (5)
C147	0.047 (5)	0.037 (6)	0.082 (10)	−0.014 (4)	0.011 (5)	0.001 (5)
O148	0.0224 (8)	0.0419 (11)	0.0380 (11)	−0.0088 (7)	−0.0011 (7)	−0.0002 (9)
C149	0.0295 (12)	0.0456 (17)	0.0235 (13)	−0.0108 (11)	0.0001 (10)	−0.0071 (12)
C150	0.0259 (12)	0.0471 (17)	0.0281 (13)	−0.0129 (11)	0.0062 (10)	−0.0120 (12)
C151	0.0338 (14)	0.069 (2)	0.056 (2)	−0.0166 (14)	0.0005 (13)	−0.0314 (17)
C152	0.059 (2)	0.087 (3)	0.088 (3)	−0.040 (2)	0.018 (2)	−0.054 (3)
C153	0.082 (3)	0.052 (2)	0.075 (3)	−0.031 (2)	0.035 (2)	−0.020 (2)
C154	0.075 (2)	0.048 (2)	0.0371 (17)	−0.0131 (17)	0.0220 (16)	−0.0071 (15)
C155	0.0486 (16)	0.0467 (19)	0.0263 (14)	−0.0124 (13)	0.0074 (12)	−0.0095 (13)
O156	0.0176 (8)	0.0575 (13)	0.0308 (10)	−0.0075 (8)	−0.0017 (7)	−0.0117 (9)
C157	0.0217 (12)	0.061 (2)	0.0536 (19)	−0.0039 (12)	0.0015 (12)	−0.0188 (16)
C158	0.0547 (18)	0.053 (2)	0.0264 (15)	−0.0054 (15)	−0.0007 (13)	−0.0100 (14)
C159	0.076 (2)	0.063 (2)	0.057 (2)	0.0010 (19)	−0.0230 (19)	−0.0269 (19)
C160	0.0434 (17)	0.048 (2)	0.075 (3)	−0.0137 (15)	−0.0019 (16)	0.0166 (18)
O161	0.0220 (8)	0.0443 (12)	0.0355 (10)	−0.0115 (8)	−0.0005 (7)	−0.0081 (8)

Geometric parameters (Å, º) top

C1—C2	1.522 (4)	C101—C134	1.521 (4)
C1—N32	1.467 (3)	C101—H1011	0.966
C1—C33	1.533 (4)	N102—C103	1.347 (3)
C1—H11	0.978	N102—H9	0.853
C2—N3	1.341 (3)	C103—C104	1.538 (4)
C2—O40	1.235 (3)	C103—O141	1.225 (3)
N3—C4	1.455 (4)	C104—O105	1.416 (3)
N3—H7	0.854	C104—C108	1.557 (3)
C4—C5	1.520 (4)	C104—H1041	0.991
C4—H41	0.978	O105—C106	1.432 (3)
C4—H42	0.970	C106—O107	1.425 (3)
C5—O6	1.423 (3)	C106—C142	1.514 (4)
C5—C9	1.542 (3)	C106—C143	1.508 (4)
C5—H51	0.972	O107—C108	1.426 (3)
O6—C7	1.413 (3)	C108—C109	1.514 (4)
C7—O8	1.412 (3)	C108—H1081	0.963
C7—C41	1.502 (5)	C109—O110	1.484 (11)
C7—C42	1.481 (5)	C109—C114	1.543 (3)
O8—C9	1.430 (3)	C109—H1091	1.000
C9—C10	1.520 (3)	C109—O111	1.407 (12)
C9—H91	0.985	C109—C114	1.543 (3)
C10—O11	1.421 (3)	C109—H1091	1.000
C10—C14	1.561 (3)	O110—C112	1.391 (12)
C10—H101	0.982	O111—C112	1.467 (11)
O11—C12	1.428 (3)	C112—O113	1.406 (4)
C12—O13	1.443 (3)	C112—C145	1.559 (9)
C12—C43	1.507 (4)	C112—C147	1.481 (13)
C12—C44	1.507 (4)	C112—O113	1.406 (4)
O13—C14	1.407 (3)	C112—C144	1.466 (11)
C14—C15	1.548 (3)	C112—C146	1.534 (15)
C14—H141	0.984	O113—C114	1.415 (3)
C15—N16	1.343 (3)	C114—C115	1.520 (4)
C15—O45	1.218 (3)	C114—H1141	0.988
N16—C17	1.470 (3)	C115—N116	1.459 (4)
N16—H2	0.876	C115—H1151	0.967
C17—C18	1.533 (4)	C115—H1152	0.973
C17—C46	1.532 (4)	N116—C117	1.326 (3)
C17—H171	0.973	N116—H3	0.858
C18—N19	1.326 (3)	C117—C118	1.537 (4)
C18—O53	1.237 (3)	C117—O148	1.236 (3)
N19—C20	1.463 (3)	C118—N119	1.461 (3)
N19—H5	0.850	C118—C149	1.539 (4)
C20—C21	1.525 (4)	C118—H1181	0.988
C20—H201	0.978	N119—C120	1.338 (3)
C20—H202	0.981	N119—H1	0.889
C21—O22	1.428 (3)	C120—C121	1.536 (3)
C21—C25	1.532 (4)	C120—O156	1.220 (3)
C21—H211	0.993	C121—O122	1.416 (3)
O22—C23	1.433 (4)	C121—C125	1.546 (3)
C23—O24	1.398 (3)	C121—H1211	0.989
C23—C54	1.516 (4)	O122—C123	1.449 (3)
C23—C55	1.516 (4)	C123—O124	1.417 (3)
O24—C25	1.436 (3)	C123—C157	1.504 (4)
C25—C26	1.516 (3)	C123—C158	1.505 (4)
C25—H251	0.978	O124—C125	1.423 (3)
C26—O27	1.429 (3)	C125—C126	1.520 (3)
C26—C30	1.544 (3)	C125—H1251	0.973
C26—H261	0.984	C126—O127	1.433 (3)
O27—C28	1.407 (3)	C126—C130	1.544 (3)
C28—O29	1.400 (3)	C126—H1261	0.981
C28—C56	1.682 (8)	O127—C128	1.408 (3)
C28—C58	1.393 (7)	C128—O129	1.425 (3)
C28—O29	1.400 (3)	C128—C159	1.512 (4)
C28—C57	1.440 (6)	C128—C160	1.511 (4)
C28—C59	1.628 (7)	O129—C130	1.428 (3)
O29—C30	1.419 (3)	C130—C131	1.520 (3)
C30—C31	1.534 (4)	C130—H1301	1.002
C30—H301	0.987	C131—N132	1.457 (3)
C31—N32	1.337 (3)	C131—H1311	0.978
C31—O60	1.222 (3)	C131—H1312	0.959
N32—H8	0.850	N132—C133	1.330 (3)
C33—C34	1.513 (4)	N132—H4	0.848
C33—H331	0.987	C133—O161	1.247 (3)
C33—H332	0.991	C134—C135	1.512 (4)
C34—C35	1.391 (4)	C134—H1341	0.944
C34—C39	1.391 (4)	C134—H1342	0.971
C35—C36	1.393 (4)	C135—C136	1.387 (4)
C35—H351	0.939	C135—C140	1.388 (4)
C36—C37	1.381 (5)	C136—C137	1.379 (5)
C36—H361	0.958	C136—H1361	0.943
C37—C38	1.378 (5)	C137—C138	1.383 (5)
C37—H371	0.926	C137—H1371	0.938
C38—C39	1.391 (4)	C138—C139	1.371 (5)
C38—H381	0.945	C138—H1381	0.940
C39—H391	0.943	C139—C140	1.395 (4)
C41—H411	0.974	C139—H1391	0.962
C41—H412	0.953	C140—H1401	0.955
C41—H413	0.963	C142—H1421	0.976
C42—H421	0.971	C142—H1422	0.971
C42—H422	0.955	C142—H1423	0.971
C42—H423	0.977	C143—H1431	0.968
C43—H431	0.967	C143—H1432	0.942
C43—H432	0.964	C143—H1433	0.944
C43—H433	0.974	C144—H1441	1.000
C44—H441	0.947	C144—H1442	1.000
C44—H442	0.951	C144—H1443	1.000
C44—H443	0.968	C145—H1451	1.000
C46—C47	1.509 (4)	C145—H1452	1.000
C46—H461	0.972	C145—H1453	1.000
C46—H462	0.979	C146—H1461	1.000
C47—C48	1.392 (4)	C146—H1462	1.000
C47—C52	1.395 (4)	C146—H1463	1.000
C48—C49	1.392 (4)	C147—H1471	1.000
C48—H481	0.936	C147—H1472	1.000
C49—C50	1.384 (5)	C147—H1473	1.000
C49—H491	0.933	C149—C150	1.499 (4)
C50—C51	1.365 (5)	C149—H1491	0.978
C50—H501	0.941	C149—H1492	0.991
C51—C52	1.390 (5)	C150—C151	1.392 (4)
C51—H511	0.938	C150—C155	1.395 (4)
C52—H521	0.946	C151—C152	1.390 (6)
C54—H541	0.969	C151—H1511	0.939
C54—H542	0.971	C152—C153	1.370 (7)
C54—H543	0.974	C152—H1521	0.924
C55—H551	0.976	C153—C154	1.385 (6)
C55—H552	0.988	C153—H1531	0.929
C55—H553	0.980	C154—C155	1.373 (5)
C56—H561	1.000	C154—H1541	0.971
C56—H562	1.000	C155—H1551	0.949
C56—H563	1.000	C157—H1571	0.964
C57—H571	1.000	C157—H1572	0.960
C57—H572	1.000	C157—H1573	0.963
C57—H573	1.000	C158—H1581	0.957
C58—H581	1.000	C158—H1582	0.964
C58—H582	1.000	C158—H1583	0.980
C58—H583	1.000	C159—H1591	0.988
C59—H591	1.000	C159—H1592	0.959
C59—H592	1.000	C159—H1593	0.976
C59—H593	1.000	C160—H1601	0.953
C101—N102	1.464 (3)	C160—H1602	0.963
C101—C133	1.522 (4)	C160—H1603	0.989

C2—C1—N32	108.49 (19)	C133—C101—H1011	110.1
C2—C1—C33	111.0 (2)	C134—C101—H1011	110.3
N32—C1—C33	107.9 (2)	C101—N102—C103	122.88 (19)
C2—C1—H11	109.2	C101—N102—H9	118.1
N32—C1—H11	110.1	C103—N102—H9	119.0
C33—C1—H11	110.1	N102—C103—C104	114.7 (2)
C1—C2—N3	117.8 (2)	N102—C103—O141	123.6 (2)
C1—C2—O40	120.3 (2)	C104—C103—O141	121.7 (2)
N3—C2—O40	121.9 (2)	C103—C104—O105	110.39 (19)
C2—N3—C4	120.5 (2)	C103—C104—C108	110.7 (2)
C2—N3—H7	119.8	O105—C104—C108	104.5 (2)
C4—N3—H7	119.7	C103—C104—H1041	111.3
N3—C4—C5	114.7 (2)	O105—C104—H1041	109.1
N3—C4—H41	109.0	C108—C104—H1041	110.6
C5—C4—H41	105.9	C104—O105—C106	109.7 (2)
N3—C4—H42	109.5	O105—C106—O107	104.8 (2)
C5—C4—H42	107.3	O105—C106—C142	110.1 (2)
H41—C4—H42	110.3	O107—C106—C142	111.6 (2)
C4—C5—O6	107.59 (19)	O105—C106—C143	108.2 (2)
C4—C5—C9	117.8 (2)	O107—C106—C143	108.3 (2)
O6—C5—C9	103.94 (19)	C142—C106—C143	113.4 (3)
C4—C5—H51	109.9	C106—O107—C108	107.07 (18)
O6—C5—H51	107.2	C104—C108—O107	102.5 (2)
C9—C5—H51	109.8	C104—C108—C109	116.6 (2)
C5—O6—C7	110.53 (18)	O107—C108—C109	110.7 (2)
O6—C7—O8	107.7 (2)	C104—C108—H1081	108.0
O6—C7—C41	108.0 (3)	O107—C108—H1081	108.8
O8—C7—C41	109.2 (3)	C109—C108—H1081	109.8
O6—C7—C42	109.7 (3)	C108—C109—O110	101.2 (4)
O8—C7—C42	108.4 (3)	C108—C109—C114	117.1 (2)
C41—C7—C42	113.6 (4)	O110—C109—C114	100.3 (5)
C7—O8—C9	110.21 (19)	C108—C109—H1091	112.3
C5—C9—O8	104.50 (19)	O110—C109—H1091	112.3
C5—C9—C10	116.2 (2)	C114—C109—H1091	112.3
O8—C9—C10	107.3 (2)	C108—C109—O111	114.1 (5)
C5—C9—H91	110.6	C108—C109—C114	117.1 (2)
O8—C9—H91	108.3	O111—C109—C114	107.0 (5)
C10—C9—H91	109.6	C108—C109—H1091	112.3
C9—C10—O11	110.69 (19)	O111—C109—H1091	90.9
C9—C10—C14	115.4 (2)	C114—C109—H1091	112.3
O11—C10—C14	102.98 (19)	C109—O110—C112	108.2 (7)
C9—C10—H101	109.3	C109—O111—C112	108.3 (7)
O11—C10—H101	109.5	O110—C112—O113	107.2 (5)
C14—C10—H101	108.8	O110—C112—C145	107.5 (5)
C10—O11—C12	106.91 (18)	O113—C112—C145	114.2 (4)
O11—C12—O13	103.94 (19)	O110—C112—C147	115.3 (6)
O11—C12—C43	108.6 (2)	O113—C112—C147	100.0 (6)
O13—C12—C43	108.4 (2)	C145—C112—C147	112.6 (6)
O11—C12—C44	111.5 (2)	O111—C112—O113	106.3 (5)
O13—C12—C44	111.1 (2)	O111—C112—C144	110.4 (6)
C43—C12—C44	112.9 (2)	O113—C112—C144	104.5 (5)
C12—O13—C14	108.87 (18)	O111—C112—C146	105.7 (7)
C10—C14—O13	104.86 (19)	O113—C112—C146	115.1 (6)
C10—C14—C15	110.9 (2)	C144—C112—C146	114.5 (6)
O13—C14—C15	112.45 (18)	C112—O113—C114	110.92 (19)
C10—C14—H141	109.5	C109—C114—O113	104.0 (2)
O13—C14—H141	109.2	C109—C114—C115	117.8 (2)
C15—C14—H141	109.8	O113—C114—C115	108.0 (2)
C14—C15—N16	112.46 (19)	C109—C114—H1141	109.9
C14—C15—O45	122.9 (2)	O113—C114—H1141	110.1
N16—C15—O45	124.6 (2)	C115—C114—H1141	106.9
C15—N16—C17	123.05 (19)	C114—C115—N116	115.9 (2)
C15—N16—H2	118.8	C114—C115—H1151	106.3
C17—N16—H2	118.1	N116—C115—H1151	106.8
N16—C17—C18	106.95 (18)	C114—C115—H1152	107.9
N16—C17—C46	109.4 (2)	N116—C115—H1152	109.6
C18—C17—C46	110.3 (2)	H1151—C115—H1152	110.2
N16—C17—H171	109.3	C115—N116—C117	120.0 (2)
C18—C17—H171	110.1	C115—N116—H3	119.4
C46—C17—H171	110.7	C117—N116—H3	120.6
C17—C18—N19	117.7 (2)	N116—C117—C118	119.0 (2)
C17—C18—O53	119.2 (2)	N116—C117—O148	121.8 (3)
N19—C18—O53	123.1 (2)	C118—C117—O148	119.2 (2)
C18—N19—C20	120.9 (2)	C117—C118—N119	108.31 (19)
C18—N19—H5	119.5	C117—C118—C149	107.6 (2)
C20—N19—H5	119.2	N119—C118—C149	111.0 (2)
N19—C20—C21	114.3 (2)	C117—C118—H1181	109.5
N19—C20—H201	107.9	N119—C118—H1181	107.8
C21—C20—H201	107.7	C149—C118—H1181	112.6
N19—C20—H202	109.2	C118—N119—C120	123.69 (19)
C21—C20—H202	108.4	C118—N119—H1	118.0
H201—C20—H202	109.3	C120—N119—H1	118.3
C20—C21—O22	109.19 (19)	N119—C120—C121	112.85 (18)
C20—C21—C25	118.4 (2)	N119—C120—O156	124.3 (2)
O22—C21—C25	104.69 (19)	C121—C120—O156	122.8 (2)
C20—C21—H211	110.2	C120—C121—O122	112.00 (18)
O22—C21—H211	105.5	C120—C121—C125	111.5 (2)
C25—C21—H211	108.0	O122—C121—C125	104.66 (18)
C21—O22—C23	109.85 (19)	C120—C121—H1211	109.9
O22—C23—O24	105.9 (2)	O122—C121—H1211	108.7
O22—C23—C54	109.2 (2)	C125—C121—H1211	110.0
O24—C23—C54	112.3 (3)	C121—O122—C123	109.31 (18)
O22—C23—C55	109.0 (3)	O122—C123—O124	104.24 (18)
O24—C23—C55	108.2 (3)	O122—C123—C157	110.0 (2)
C54—C23—C55	112.0 (3)	O124—C123—C157	111.5 (2)
C23—O24—C25	108.9 (2)	O122—C123—C158	108.7 (2)
C21—C25—O24	103.24 (19)	O124—C123—C158	108.3 (2)
C21—C25—C26	117.2 (2)	C157—C123—C158	113.7 (2)
O24—C25—C26	105.8 (2)	C123—O124—C125	107.54 (17)
C21—C25—H251	111.1	C121—C125—O124	102.89 (19)
O24—C25—H251	111.0	C121—C125—C126	115.61 (19)
C26—C25—H251	108.3	O124—C125—C126	109.67 (18)
C25—C26—O27	110.1 (2)	C121—C125—H1251	108.5
C25—C26—C30	116.0 (2)	O124—C125—H1251	109.8
O27—C26—C30	102.98 (19)	C126—C125—H1251	110.1
C25—C26—H261	108.3	C125—C126—O127	105.67 (19)
O27—C26—H261	109.7	C125—C126—C130	116.2 (2)
C30—C26—H261	109.5	O127—C126—C130	103.73 (18)
C26—O27—C28	108.62 (18)	C125—C126—H1261	108.2
O27—C28—O29	108.5 (2)	O127—C126—H1261	112.0
O27—C28—C56	98.5 (3)	C130—C126—H1261	110.9
O29—C28—C56	92.6 (3)	C126—O127—C128	108.58 (19)
O27—C28—C58	122.7 (5)	O127—C128—O129	106.44 (19)
O29—C28—C58	118.7 (4)	O127—C128—C159	108.1 (2)
C56—C28—C58	109.4 (6)	O129—C128—C159	109.9 (2)
O27—C28—O29	108.5 (2)	O127—C128—C160	110.7 (2)
O27—C28—C57	115.0 (3)	O129—C128—C160	109.3 (2)
O29—C28—C57	119.5 (4)	C159—C128—C160	112.2 (3)
O27—C28—C59	101.8 (3)	C128—O129—C130	110.60 (17)
O29—C28—C59	99.0 (3)	C126—C130—O129	103.85 (19)
C57—C28—C59	110.3 (4)	C126—C130—C131	117.4 (2)
C28—O29—C30	109.76 (19)	O129—C130—C131	108.84 (18)
C26—C30—O29	104.14 (19)	C126—C130—H1301	107.8
C26—C30—C31	112.3 (2)	O129—C130—H1301	109.7
O29—C30—C31	109.00 (19)	C131—C130—H1301	108.9
C26—C30—H301	111.2	C130—C131—N132	114.2 (2)
O29—C30—H301	112.3	C130—C131—H1311	107.5
C31—C30—H301	107.9	N132—C131—H1311	107.1
C30—C31—N32	113.6 (2)	C130—C131—H1312	109.1
C30—C31—O60	122.3 (2)	N132—C131—H1312	108.1
N32—C31—O60	124.1 (2)	H1311—C131—H1312	110.8
C1—N32—C31	124.94 (19)	C131—N132—C133	121.2 (2)
C1—N32—H8	119.0	C131—N132—H4	118.0
C31—N32—H8	116.0	C133—N132—H4	120.5
C1—C33—C34	115.0 (2)	C101—C133—N132	118.1 (2)
C1—C33—H331	107.3	C101—C133—O161	119.5 (2)
C34—C33—H331	108.9	N132—C133—O161	122.4 (2)
C1—C33—H332	106.9	C101—C134—C135	118.2 (2)
C34—C33—H332	107.9	C101—C134—H1341	107.3
H331—C33—H332	110.8	C135—C134—H1341	106.4
C33—C34—C35	119.9 (2)	C101—C134—H1342	106.0
C33—C34—C39	121.6 (2)	C135—C134—H1342	107.4
C35—C34—C39	118.5 (2)	H1341—C134—H1342	111.7
C34—C35—C36	121.0 (3)	C134—C135—C136	118.1 (2)
C34—C35—H351	118.0	C134—C135—C140	123.8 (2)
C36—C35—H351	121.0	C136—C135—C140	118.1 (2)
C35—C36—C37	119.8 (3)	C135—C136—C137	121.6 (3)
C35—C36—H361	120.1	C135—C136—H1361	120.6
C37—C36—H361	120.1	C137—C136—H1361	117.8
C36—C37—C38	119.7 (3)	C136—C137—C138	119.7 (3)
C36—C37—H371	121.2	C136—C137—H1371	119.6
C38—C37—H371	119.1	C138—C137—H1371	120.7
C37—C38—C39	120.7 (3)	C137—C138—C139	119.8 (3)
C37—C38—H381	118.9	C137—C138—H1381	120.1
C39—C38—H381	120.5	C139—C138—H1381	120.1
C34—C39—C38	120.3 (3)	C138—C139—C140	120.3 (3)
C34—C39—H391	119.2	C138—C139—H1391	119.3
C38—C39—H391	120.5	C140—C139—H1391	120.4
C7—C41—H411	110.1	C139—C140—C135	120.5 (2)
C7—C41—H412	107.7	C139—C140—H1401	118.7
H411—C41—H412	109.8	C135—C140—H1401	120.8
C7—C41—H413	108.6	C106—C142—H1421	108.3
H411—C41—H413	110.9	C106—C142—H1422	108.6
H412—C41—H413	109.5	H1421—C142—H1422	110.7
C7—C42—H421	108.4	C106—C142—H1423	112.0
C7—C42—H422	106.3	H1421—C142—H1423	107.7
H421—C42—H422	110.4	H1422—C142—H1423	109.5
C7—C42—H423	109.0	C106—C143—H1431	109.1
H421—C42—H423	112.5	C106—C143—H1432	109.6
H422—C42—H423	110.0	H1431—C143—H1432	110.0
C12—C43—H431	110.0	C106—C143—H1433	109.5
C12—C43—H432	108.5	H1431—C143—H1433	109.2
H431—C43—H432	109.2	H1432—C143—H1433	109.3
C12—C43—H433	108.8	C112—C144—H1441	109.6
H431—C43—H433	109.0	C112—C144—H1442	109.4
H432—C43—H433	111.4	H1441—C144—H1442	109.5
C12—C44—H441	111.7	C112—C144—H1443	109.4
C12—C44—H442	109.3	H1441—C144—H1443	109.5
H441—C44—H442	110.7	H1442—C144—H1443	109.5
C12—C44—H443	108.5	C112—C145—H1451	109.6
H441—C44—H443	106.9	C112—C145—H1452	109.3
H442—C44—H443	109.7	H1451—C145—H1452	109.5
C17—C46—C47	116.2 (2)	C112—C145—H1453	109.5
C17—C46—H461	108.3	H1451—C145—H1453	109.5
C47—C46—H461	109.3	H1452—C145—H1453	109.5
C17—C46—H462	107.5	C112—C146—H1461	109.2
C47—C46—H462	107.9	C112—C146—H1462	109.6
H461—C46—H462	107.4	H1461—C146—H1462	109.5
C46—C47—C48	122.9 (2)	C112—C146—H1463	109.6
C46—C47—C52	119.2 (2)	H1461—C146—H1463	109.5
C48—C47—C52	117.8 (3)	H1462—C146—H1463	109.5
C47—C48—C49	121.2 (3)	C112—C147—H1471	109.2
C47—C48—H481	120.1	C112—C147—H1472	109.6
C49—C48—H481	118.7	H1471—C147—H1472	109.5
C48—C49—C50	119.5 (3)	C112—C147—H1473	109.6
C48—C49—H491	119.6	H1471—C147—H1473	109.5
C50—C49—H491	121.0	H1472—C147—H1473	109.5
C49—C50—C51	120.3 (3)	C118—C149—C150	116.7 (2)
C49—C50—H501	120.9	C118—C149—H1491	106.4
C51—C50—H501	118.8	C150—C149—H1491	109.3
C50—C51—C52	120.3 (3)	C118—C149—H1492	107.0
C50—C51—H511	120.2	C150—C149—H1492	109.1
C52—C51—H511	119.5	H1491—C149—H1492	108.0
C47—C52—C51	120.8 (3)	C149—C150—C151	120.4 (3)
C47—C52—H521	118.9	C149—C150—C155	121.5 (2)
C51—C52—H521	120.3	C151—C150—C155	117.9 (3)
C23—C54—H541	109.4	C150—C151—C152	120.3 (4)
C23—C54—H542	110.4	C150—C151—H1511	120.0
H541—C54—H542	108.1	C152—C151—H1511	119.6
C23—C54—H543	107.9	C151—C152—C153	120.6 (4)
H541—C54—H543	110.3	C151—C152—H1521	118.7
H542—C54—H543	110.9	C153—C152—H1521	120.8
C23—C55—H551	111.0	C152—C153—C154	119.9 (4)
C23—C55—H552	108.8	C152—C153—H1531	119.1
H551—C55—H552	110.3	C154—C153—H1531	120.9
C23—C55—H553	109.2	C153—C154—C155	119.6 (4)
H551—C55—H553	107.7	C153—C154—H1541	120.1
H552—C55—H553	109.9	C155—C154—H1541	120.3
C28—C56—H561	109.4	C150—C155—C154	121.7 (3)
C28—C56—H562	109.4	C150—C155—H1551	119.8
H561—C56—H562	109.5	C154—C155—H1551	118.5
C28—C56—H563	109.5	C123—C157—H1571	109.0
H561—C56—H563	109.5	C123—C157—H1572	108.4
H562—C56—H563	109.5	H1571—C157—H1572	109.7
C28—C57—H571	109.6	C123—C157—H1573	108.4
C28—C57—H572	109.5	H1571—C157—H1573	111.3
H571—C57—H572	109.5	H1572—C157—H1573	109.9
C28—C57—H573	109.4	C123—C158—H1581	111.0
H571—C57—H573	109.5	C123—C158—H1582	111.2
H572—C57—H573	109.5	H1581—C158—H1582	107.4
C28—C58—H581	109.3	C123—C158—H1583	111.2
C28—C58—H582	109.6	H1581—C158—H1583	106.9
H581—C58—H582	109.5	H1582—C158—H1583	108.9
C28—C58—H583	109.5	C128—C159—H1591	105.9
H581—C58—H583	109.5	C128—C159—H1592	108.1
H582—C58—H583	109.5	H1591—C159—H1592	111.5
C28—C59—H591	109.5	C128—C159—H1593	109.8
C28—C59—H592	109.5	H1591—C159—H1593	111.4
H591—C59—H592	109.5	H1592—C159—H1593	109.9
C28—C59—H593	109.5	C128—C160—H1601	109.7
H591—C59—H593	109.5	C128—C160—H1602	110.9
H592—C59—H593	109.5	H1601—C160—H1602	107.4
N102—C101—C133	107.78 (19)	C128—C160—H1603	112.1
N102—C101—C134	112.2 (2)	H1601—C160—H1603	108.6
C133—C101—C134	108.8 (2)	H1602—C160—H1603	108.0
N102—C101—H1011	107.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N119—H1···O161	0.89	1.89	2.776 (2)	174
N16—H2···O40	0.88	1.95	2.813 (2)	170
N116—H3···O141ⁱ	0.86	2.08	2.883 (2)	155
N132—H4···O156ⁱⁱ	0.85	2.09	2.916 (2)	163
N19—H5···O60ⁱⁱ	0.85	2.15	2.966 (2)	160
N3—H7···O45ⁱ	0.85	2.08	2.897 (2)	159
N32—H8···O53	0.85	1.92	2.753 (2)	167
N102—H9···O148	0.85	1.96	2.798 (2)	167

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

Acknowledgements

Financial support from the EPSRC (AAE and SJH) is gratefully acknowledged.

References

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