Double-stranded helical twisted β-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids

Gramicidin S is a nonribosomally synthesized cyclic decapeptide antibiotic with twofold symmetry (Val-Orn-Leu-D-­Phe-Pro)₂; a natural source is Bacillus brevis. Gramicidin S is active against Gram-positive and some Gram-negative bacteria. However, its haemolytic toxicity in humans limits its use as an antibiotic to certain topical applications. Synthetically obtained gramicidin S was crystallized from a solution containing water, methanol, trifluoroacetic acid and hydrochloric acid. The structure was solved and refined at 0.95 Å resolution. The asymmetric unit contains 1.5 molecules of gramicidin S, two trifluoroacetic acid molecules and ten water molecules located and refined in 14 positions. One gramicidin S molecule has an exact twofold-symmetrical conformation; the other deviates from the molecular twofold symmetry. The cyclic peptide adopts an antiparallel β-sheet secondary structure with two type II′ β-turns. These turns have the residues D-Phe and Pro at positions i + 1 and i + 2, respectively. In the crystals, the gramicidin S molecules line up into double-stranded helical channels that differ from those observed previously. The implications of the supramolecular structure for several models of gramicidin S conformation and assembly in the membrane are discussed.

Computing details

Data collection: Collect (Bruker AXS BV, 1997-2004); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SnB2.2 (Weeks, C.M. & Miller, R., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: pyMOL 0.99 (DeLano,W.L. 2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(gramsn4n)

Crystal data

3(C60H94N12O10)·4(C2F3O2)·20(O)	Dx = 1.163 Mg m^−3
Mr = 4202.51	Cu Kα radiation, λ = 1.5418 Å
Trigonal, R32	Cell parameters from 7652 reflections
Hall symbol: R 3 2"	θ = 0.4–22.0°
a = 41.4764 (4) Å	µ = 0.78 mm^−1
c = 36.2358 (5) Å	T = 100 K
V = 53984.7 (10) Å^3	Prism, colourless
Z = 9	0.75 × 0.08 × 0.05 mm
F(000) = 20106

Data collection

Bruker Nonius FR591 KappaCCD2000 diffractometer	6577 reflections with I > 2σ(I)
Multilayer confocal monochromator	Rint = 0.111
CCD scans	θmax = 54.3°, θmin = 3.5°
Absorption correction: multi-scan SADABS: G.M. Sheldrick, Bruker AXS (1997)	h = −43→21
Tmin = 0.147, Tmax = 0.962	k = 0→43
104642 measured reflections	l = 0→38
7710 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.146	H-atom parameters constrained
wR(F^2) = 0.395	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.86	(Δ/σ)max = 0.036
7710 reflections	Δρmax = 0.67 e Å^−3
1273 parameters	Δρmin = −0.43 e Å^−3
1575 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881, 6937 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.1 (4)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N_1	0.4357 (2)	−0.0438 (2)	0.13062 (17)	0.0873 (19)
CA_1	0.4468 (3)	−0.0552 (2)	0.0970 (2)	0.093 (2)
HA_1	0.4630	−0.0660	0.1029	0.112*
CB_1	0.4088 (3)	−0.0851 (3)	0.0828 (3)	0.115 (3)
HB1_1	0.4010	−0.1092	0.0952	0.138*
HB2_1	0.4096	−0.0885	0.0558	0.138*
CG_1	0.3826 (3)	−0.0708 (3)	0.0921 (3)	0.109 (3)
HG1_1	0.3847	−0.0520	0.0740	0.131*
HG2_1	0.3564	−0.0914	0.0931	0.131*
CD_1	0.3965 (3)	−0.0535 (3)	0.1303 (2)	0.094 (3)
HD1_1	0.3942	−0.0310	0.1335	0.113*
HD2_1	0.3823	−0.0715	0.1501	0.113*
C_1	0.4653 (3)	−0.0244 (3)	0.0681 (2)	0.093 (2)
O_1	0.4765 (3)	−0.0302 (3)	0.03882 (17)	0.118 (3)
N_2	0.4690 (2)	0.0083 (2)	0.07429 (19)	0.0846 (19)
H0_2	0.4605	0.0114	0.0955	0.102*
CA_2	0.4856 (3)	0.0396 (3)	0.0499 (3)	0.108 (3)
HA_2	0.4785	0.0320	0.0236	0.129*
CB_2	0.4764 (5)	0.0711 (4)	0.0621 (4)	0.160 (5)
HB_2	0.4837	0.0776	0.0885	0.192*
CG1_2	0.4988 (7)	0.1058 (4)	0.0386 (5)	0.185 (8)
HG1A_2	0.5254	0.1144	0.0412	0.278*
HG1B_2	0.4939	0.1254	0.0469	0.278*
HG1C_2	0.4915	0.1000	0.0127	0.278*
CG2_2	0.4365 (5)	0.0567 (7)	0.0587 (6)	0.195 (8)
HG2A_2	0.4230	0.0342	0.0738	0.292*
HG2B_2	0.4290	0.0507	0.0328	0.292*
HG2C_2	0.4306	0.0756	0.0672	0.292*
C_2	0.5273 (3)	0.0628 (3)	0.0546 (2)	0.099 (3)
O_2	0.5397 (2)	0.0694 (3)	0.08624 (17)	0.125 (3)
N_3	0.5463 (2)	0.0749 (3)	0.02441 (19)	0.112 (3)
H0_3	0.5357	0.0655	0.0030	0.134*
CA_3	0.5855 (3)	0.1042 (4)	0.0256 (3)	0.166 (5)
HA_3	0.5910	0.1161	0.0505	0.200*
CB_3	0.6107 (4)	0.0877 (7)	0.0194 (7)	0.240 (9)
HB1_3	0.6072	0.0771	−0.0057	0.288*
HB2_3	0.6050	0.0677	0.0376	0.288*
CG_3	0.6507 (5)	0.1200 (8)	0.0245 (12)	0.293 (14)
HG1_3	0.6561	0.1393	0.0056	0.352*
HG2_3	0.6532	0.1314	0.0491	0.352*
CD_3	0.6785 (5)	0.1068 (8)	0.0211 (14)	0.340 (17)
HD1_3	0.6701	0.0839	0.0359	0.408*
HD2_3	0.6803	0.1008	−0.0050	0.408*
NZ_3	0.7162 (5)	0.1364 (7)	0.0343 (12)	0.323 (18)
HZ1_3	0.7283	0.1255	0.0449	0.485*
HZ2_3	0.7135	0.1510	0.0513	0.485*
HZ3_3	0.7298	0.1506	0.0149	0.485*
C_3	0.5946 (4)	0.1336 (4)	−0.0031 (2)	0.165 (6)
O_3	0.5833 (4)	0.1239 (5)	−0.0350 (2)	0.228 (9)
N_4	0.6146 (4)	0.1686 (4)	0.0073 (3)	0.181 (5)
H0_4	0.6198	0.1735	0.0309	0.217*
CA_4	0.6286 (4)	0.1996 (4)	−0.0187 (3)	0.174 (5)
HA_4	0.6296	0.1897	−0.0436	0.209*
CB_4	0.6050 (6)	0.2183 (7)	−0.0221 (5)	0.225 (8)
HB1_4	0.6069	0.2317	0.0011	0.270*
HB2_4	0.5786	0.1987	−0.0252	0.270*
CG_4	0.6162 (8)	0.2461 (8)	−0.0548 (6)	0.279 (12)
HG_4	0.6439	0.2625	−0.0543	0.334*
CD1_4	0.6057 (17)	0.2242 (13)	−0.0909 (6)	0.36 (2)
HD1A_4	0.6157	0.2072	−0.0910	0.538*
HD1B_4	0.6162	0.2415	−0.1117	0.538*
HD1C_4	0.5785	0.2099	−0.0932	0.538*
CD2_4	0.5990 (13)	0.2706 (12)	−0.0516 (9)	0.325 (18)
HD2A_4	0.6076	0.2884	−0.0721	0.488*
HD2B_4	0.6065	0.2842	−0.0281	0.488*
HD2C_4	0.5718	0.2552	−0.0525	0.488*
C_4	0.6686 (3)	0.2257 (4)	−0.0064 (3)	0.133 (4)
O_4	0.6746 (3)	0.2429 (3)	0.0220 (3)	0.145 (3)
N_5	0.6954 (3)	0.2272 (4)	−0.0275 (3)	0.167 (5)
H0_5	0.6897	0.2152	−0.0487	0.201*
CA_5	0.7343 (3)	0.2488 (4)	−0.0161 (3)	0.153 (5)
HA_5	0.7423	0.2759	−0.0167	0.183*
CB_5	0.7593 (3)	0.2415 (5)	−0.0423 (4)	0.170 (6)
HB1_5	0.7541	0.2156	−0.0391	0.204*
HB2_5	0.7539	0.2447	−0.0682	0.204*
CG_5	0.7999 (4)	0.2685 (5)	−0.0336 (3)	0.170 (6)
CD1_5	0.8253 (5)	0.2593 (6)	−0.0207 (4)	0.203 (6)
HD1_5	0.8177	0.2338	−0.0166	0.243*
CD2_5	0.8139 (5)	0.3066 (5)	−0.0393 (5)	0.192 (7)
HD2_5	0.7974	0.3138	−0.0495	0.231*
CE1_5	0.8626 (5)	0.2870 (5)	−0.0132 (4)	0.157 (5)
HE1_5	0.8803	0.2805	−0.0049	0.189*
CE2_5	0.8491 (5)	0.3341 (5)	−0.0315 (5)	0.172 (6)
HE2_5	0.8567	0.3596	−0.0352	0.207*
CZ_5	0.8724 (6)	0.3235 (6)	−0.0183 (5)	0.181 (6)
HZ_5	0.8970	0.3422	−0.0122	0.217*
C_5	0.7393 (3)	0.2384 (4)	0.0222 (3)	0.132 (4)
O_5	0.7292 (4)	0.2059 (3)	0.0293 (4)	0.180 (5)
N_6	0.7559 (3)	0.2655 (3)	0.0469 (2)	0.125 (3)
CA_6	0.7649 (3)	0.2593 (4)	0.0845 (3)	0.148 (4)
HA_6	0.7763	0.2431	0.0838	0.177*
CB_6	0.7945 (4)	0.2993 (5)	0.0957 (4)	0.182 (7)
HB1_6	0.7955	0.3025	0.1228	0.218*
HB2_6	0.8195	0.3055	0.0866	0.218*
CG_6	0.7813 (6)	0.3233 (5)	0.0772 (5)	0.181 (6)
HG1_6	0.7611	0.3235	0.0917	0.217*
HG2_6	0.8019	0.3492	0.0742	0.217*
CD_6	0.7673 (5)	0.3052 (4)	0.0409 (4)	0.145 (4)
HD1_6	0.7872	0.3164	0.0220	0.174*
HD2_6	0.7459	0.3077	0.0327	0.174*
C_6	0.7326 (3)	0.2438 (4)	0.1120 (3)	0.130 (4)
O_6	0.7388 (3)	0.2411 (5)	0.1442 (3)	0.177 (6)
N_7	0.6994 (2)	0.2348 (3)	0.0988 (2)	0.108 (3)
H0_7	0.6967	0.2377	0.0752	0.130*
CA_7	0.6674 (3)	0.2201 (3)	0.1234 (2)	0.103 (3)
HA_7	0.6764	0.2234	0.1494	0.123*
CB_7	0.6464 (3)	0.2418 (4)	0.1181 (4)	0.139 (4)
HB_7	0.6353	0.2367	0.0928	0.167*
CG1_7	0.6150 (4)	0.2277 (6)	0.1470 (4)	0.168 (7)
HG1A_7	0.5983	0.2009	0.1438	0.253*
HG1B_7	0.6008	0.2407	0.1436	0.253*
HG1C_7	0.6258	0.2327	0.1718	0.253*
CG2_7	0.6716 (6)	0.2829 (4)	0.1226 (7)	0.182 (8)
HG2A_7	0.6575	0.2957	0.1187	0.273*
HG2B_7	0.6919	0.2918	0.1046	0.273*
HG2C_7	0.6821	0.2881	0.1476	0.273*
C_7	0.6414 (3)	0.1792 (3)	0.1165 (2)	0.109 (3)
O_7	0.6293 (3)	0.1676 (3)	0.08579 (19)	0.164 (5)
N_8	0.6332 (2)	0.1576 (2)	0.14592 (19)	0.094 (2)
H0_8	0.6460	0.1673	0.1663	0.113*
CA_8	0.6042 (3)	0.1189 (3)	0.1464 (2)	0.100 (3)
HA_8	0.5939	0.1111	0.1209	0.120*
CB_8	0.6199 (4)	0.0944 (4)	0.1601 (4)	0.133 (4)
HB1_8	0.6394	0.0972	0.1424	0.160*	0.70
HB2_8	0.6324	0.1047	0.1840	0.160*	0.70
HB3_8	0.6335	0.1052	0.1834	0.160*	0.30
HB4_8	0.5986	0.0694	0.1660	0.160*	0.30
CGa_8	0.5938 (7)	0.0532 (5)	0.1655 (6)	0.153 (7)	0.70
HG1_8	0.6043	0.0436	0.1841	0.184*	0.70
HG2_8	0.5696	0.0491	0.1748	0.184*	0.70
CDa_8	0.5879 (6)	0.0328 (6)	0.1304 (7)	0.168 (9)	0.70
HD1_8	0.6122	0.0368	0.1214	0.201*	0.70
HD2_8	0.5781	0.0431	0.1118	0.201*	0.70
NZa_8	0.5617 (8)	−0.0080 (6)	0.1338 (9)	0.223 (13)	0.70
HZ1_8	0.5585	−0.0189	0.1113	0.334*	0.70
HZ2_8	0.5393	−0.0120	0.1423	0.334*	0.70
HZ3_8	0.5711	−0.0180	0.1499	0.334*	0.70
CGb_8	0.6452 (16)	0.0894 (15)	0.1347 (14)	0.157 (13)	0.30
HG3_8	0.6704	0.1117	0.1349	0.189*	0.30
HG4_8	0.6355	0.0850	0.1092	0.189*	0.30
CDb_8	0.6463 (15)	0.0555 (14)	0.1493 (18)	0.172 (15)	0.30
HD3_8	0.6477	0.0573	0.1766	0.206*	0.30
HD4_8	0.6223	0.0331	0.1430	0.206*	0.30
NZb_8	0.6765 (12)	0.0494 (12)	0.136 (2)	0.20 (2)	0.30
HZ4_8	0.6681	0.0245	0.1356	0.307*	0.30
HZ5_8	0.6960	0.0605	0.1524	0.307*	0.30
HZ6_8	0.6839	0.0594	0.1136	0.307*	0.30
C_8	0.5737 (2)	0.1152 (3)	0.1718 (2)	0.096 (3)
O_8	0.58115 (17)	0.1299 (2)	0.20234 (16)	0.099 (2)
N_9	0.53903 (19)	0.0946 (3)	0.15992 (19)	0.095 (2)
H0_9	0.5352	0.0847	0.1377	0.114*
CA_9	0.5066 (2)	0.0877 (2)	0.1825 (2)	0.087 (2)
HA_9	0.5137	0.0909	0.2092	0.104*
CB_9	0.4921 (3)	0.1136 (3)	0.1723 (2)	0.095 (2)
HB1_9	0.4921	0.1152	0.1450	0.114*
HB2_9	0.5102	0.1388	0.1815	0.114*
CG_9	0.4538 (3)	0.1044 (4)	0.1858 (4)	0.131 (4)
HG_9	0.4356	0.0792	0.1758	0.157*
CD1_9	0.4508 (6)	0.1017 (8)	0.2268 (4)	0.194 (10)
HD1A_9	0.4256	0.0954	0.2343	0.291*
HD1B_9	0.4690	0.1256	0.2377	0.291*
HD1C_9	0.4559	0.0822	0.2354	0.291*
CD2_9	0.4418 (5)	0.1314 (5)	0.1718 (4)	0.147 (5)
HD2A_9	0.4441	0.1331	0.1448	0.221*
HD2B_9	0.4578	0.1560	0.1826	0.221*
HD2C_9	0.4159	0.1225	0.1788	0.221*
C_9	0.4777 (2)	0.0474 (2)	0.1752 (2)	0.079 (2)
O_9	0.46154 (18)	0.03841 (18)	0.14519 (14)	0.0856 (16)
N_10	0.4725 (2)	0.0220 (2)	0.20149 (18)	0.0846 (19)
H0_10	0.4836	0.0290	0.2231	0.101*
CA_10	0.4481 (3)	−0.0169 (2)	0.1931 (2)	0.088 (2)
HA_10	0.4220	−0.0219	0.1903	0.106*
CB_10	0.4496 (3)	−0.0415 (3)	0.2240 (2)	0.102 (3)
HB1_10	0.4757	−0.0347	0.2287	0.122*
HB2_10	0.4393	−0.0374	0.2471	0.122*
CG_10	0.4270 (3)	−0.0825 (3)	0.2130 (2)	0.102 (3)
CD1_10	0.4434 (4)	−0.1015 (4)	0.1993 (3)	0.121 (3)
HD1_10	0.4698	−0.0893	0.1979	0.146*
CD2_10	0.3887 (3)	−0.1006 (3)	0.2152 (3)	0.109 (3)
HD2_10	0.3765	−0.0879	0.2242	0.131*
CE1_10	0.4227 (4)	−0.1380 (4)	0.1876 (3)	0.131 (4)
HE1_10	0.4349	−0.1505	0.1781	0.157*
CE2_10	0.3681 (4)	−0.1374 (3)	0.2041 (3)	0.112 (3)
HE2_10	0.3418	−0.1500	0.2067	0.135*
CZ_10	0.3845 (4)	−0.1563 (4)	0.1895 (3)	0.135 (4)
HZ_10	0.3699	−0.1812	0.1811	0.162*
C_10	0.4606 (3)	−0.0264 (3)	0.15738 (19)	0.084 (2)
O_10	0.4936 (2)	−0.0176 (3)	0.15414 (18)	0.111 (2)
N_21	0.48483 (19)	0.0519 (2)	0.36365 (18)	0.088 (2)
CA_21	0.4858 (3)	0.0381 (3)	0.3273 (2)	0.107 (3)
HA_21	0.4903	0.0166	0.3292	0.129*
CB_21	0.4460 (3)	0.0248 (4)	0.3138 (4)	0.150 (5)
HB1_21	0.4448	0.0242	0.2865	0.180*
HB2_21	0.4284	−0.0003	0.3234	0.180*
CG_21	0.4371 (3)	0.0532 (5)	0.3289 (3)	0.142 (4)
HG1_21	0.4099	0.0431	0.3301	0.170*
HG2_21	0.4485	0.0760	0.3135	0.170*
CD_21	0.4541 (2)	0.0613 (4)	0.3674 (2)	0.112 (4)
HD1_21	0.4356	0.0454	0.3862	0.134*
HD2_21	0.4643	0.0877	0.3741	0.134*
C_21	0.5135 (2)	0.0672 (2)	0.3004 (2)	0.080 (2)
O_21	0.5138 (2)	0.05806 (18)	0.26822 (16)	0.103 (2)
N_22	0.53573 (18)	0.10160 (19)	0.31362 (19)	0.0776 (18)
H0_22	0.5337	0.1063	0.3369	0.093*
CA_22	0.5628 (2)	0.1311 (2)	0.29058 (18)	0.0741 (18)
HA_22	0.5563	0.1249	0.2640	0.089*
CB_22	0.5647 (3)	0.1678 (2)	0.2998 (3)	0.101 (3)
HB_22	0.5680	0.1715	0.3271	0.121*
CG1_22	0.5970 (5)	0.2004 (3)	0.2815 (4)	0.141 (5)
HG1A_22	0.5972	0.2234	0.2882	0.211*
HG1B_22	0.5947	0.1972	0.2546	0.211*
HG1C_22	0.6203	0.2020	0.2896	0.211*
CG2_22	0.5273 (4)	0.1646 (4)	0.2894 (4)	0.130 (4)
HG2A_22	0.5070	0.1429	0.3017	0.194*
HG2B_22	0.5238	0.1619	0.2626	0.194*
HG2C_22	0.5271	0.1872	0.2974	0.194*
C_22	0.6008 (2)	0.1355 (3)	0.2984 (2)	0.083 (2)
O_22	0.61167 (18)	0.1367 (2)	0.33009 (16)	0.105 (2)
N_23	0.62133 (18)	0.1382 (2)	0.26940 (18)	0.085 (2)
H0_23	0.6113	0.1346	0.2473	0.102*
CA_23	0.6599 (2)	0.1469 (3)	0.2726 (2)	0.100 (3)
HA_23	0.6687	0.1548	0.2985	0.120*
CB_23	0.6620 (4)	0.1123 (4)	0.2633 (5)	0.145 (5)
HB1_23	0.6463	0.0924	0.2810	0.174*
HB2_23	0.6513	0.1036	0.2384	0.174*
CG_23	0.7005 (5)	0.1176 (8)	0.2640 (7)	0.227 (10)
HG1_23	0.7025	0.1027	0.2437	0.272*
HG2_23	0.7184	0.1441	0.2587	0.272*
CD_23	0.7125 (6)	0.1073 (9)	0.2989 (7)	0.227 (11)
HD1_23	0.6936	0.0820	0.3070	0.273*
HD2_23	0.7162	0.1252	0.3188	0.273*
NZ_23	0.7486 (5)	0.1086 (5)	0.2901 (8)	0.236 (11)
HZ1_23	0.7564	0.1012	0.3101	0.354*
HZ2_23	0.7661	0.1323	0.2839	0.354*
HZ3_23	0.7451	0.0931	0.2708	0.354*
C_23	0.6830 (2)	0.1786 (3)	0.2466 (2)	0.091 (3)
O_23	0.67375 (19)	0.1780 (3)	0.21499 (18)	0.121 (3)
N_24	0.7135 (2)	0.2067 (2)	0.2611 (2)	0.097 (2)
H0_24	0.7174	0.2054	0.2848	0.117*
CA_24	0.7408 (2)	0.2392 (3)	0.2414 (3)	0.105 (3)
HA_24	0.7362	0.2353	0.2143	0.126*
CB_24	0.7381 (4)	0.2734 (4)	0.2539 (5)	0.154 (5)
HB1_24	0.7454	0.2777	0.2802	0.185*	0.62 (2)
HB2_24	0.7575	0.2951	0.2401	0.185*	0.62 (2)
HB3_24	0.7161	0.2659	0.2698	0.185*	0.38 (2)
HB4_24	0.7607	0.2914	0.2675	0.185*	0.38 (2)
CGa_24	0.7025 (4)	0.2747 (5)	0.2505 (6)	0.136 (7)	0.62 (2)
HG_24	0.6812	0.2493	0.2559	0.164*	0.62 (2)
CD1a_24	0.6979 (9)	0.3027 (8)	0.2742 (8)	0.169 (11)	0.62 (2)
HD1A_24	0.6979	0.2967	0.3004	0.254*	0.62 (2)
HD1B_24	0.6743	0.3015	0.2681	0.254*	0.62 (2)
HD1C_24	0.7185	0.3279	0.2694	0.254*	0.62 (2)
CD2a_24	0.6996 (13)	0.2839 (14)	0.2104 (7)	0.202 (13)	0.62 (2)
HD2A_24	0.6768	0.2851	0.2070	0.303*	0.62 (2)
HD2B_24	0.6989	0.2645	0.1944	0.303*	0.62 (2)
HD2C_24	0.7212	0.3080	0.2041	0.303*	0.62 (2)
CGb_24	0.7345 (10)	0.2902 (8)	0.2175 (7)	0.161 (10)	0.38 (2)
HG1_24	0.7164	0.2698	0.2010	0.194*	0.38 (2)
CD1b_24	0.7213 (11)	0.3172 (11)	0.2245 (12)	0.139 (14)	0.38 (2)
HD1D_24	0.6970	0.3044	0.2367	0.208*	0.38 (2)
HD1E_24	0.7190	0.3276	0.2010	0.208*	0.38 (2)
HD1F_24	0.7392	0.3374	0.2404	0.208*	0.38 (2)
CD2b_24	0.7735 (15)	0.3069 (17)	0.2012 (16)	0.20 (2)	0.38 (2)
HD2D_24	0.7795	0.2871	0.1972	0.304*	0.38 (2)
HD2E_24	0.7916	0.3253	0.2184	0.304*	0.38 (2)
HD2F_24	0.7745	0.3189	0.1777	0.304*	0.38 (2)
C_24	0.7786 (2)	0.2441 (3)	0.2505 (2)	0.087 (2)
O_24	0.79524 (19)	0.2616 (2)	0.27804 (18)	0.0918 (17)
N_25	0.7926 (2)	0.2282 (3)	0.2288 (2)	0.103 (2)
H0_25	0.7811	0.2172	0.2082	0.123*
CA_25	0.8273 (3)	0.2292 (3)	0.2391 (2)	0.096 (3)
HA_25	0.8483	0.2556	0.2391	0.115*
CB_25	0.8355 (4)	0.2061 (4)	0.2109 (3)	0.115 (3)
HB1_25	0.8150	0.1798	0.2112	0.138*
HB2_25	0.8372	0.2161	0.1857	0.138*
CG_25	0.8720 (3)	0.2081 (4)	0.2211 (3)	0.116 (3)
CD1_25	0.8685 (5)	0.1766 (4)	0.2396 (5)	0.174 (6)
HD1_25	0.8447	0.1549	0.2420	0.209*
CD2_25	0.9064 (3)	0.2393 (4)	0.2167 (3)	0.130 (4)
HD2_25	0.9079	0.2605	0.2051	0.156*
CE1_25	0.9001 (5)	0.1774 (5)	0.2545 (6)	0.175 (6)
HE1_25	0.8983	0.1573	0.2686	0.211*
CE2_25	0.9387 (4)	0.2408 (5)	0.2287 (4)	0.145 (4)
HE2_25	0.9625	0.2620	0.2245	0.174*
CZ_25	0.9342 (5)	0.2092 (6)	0.2474 (6)	0.190 (7)
HZ_25	0.9560	0.2095	0.2559	0.228*
C_25	0.8233 (3)	0.2126 (3)	0.2773 (2)	0.090 (2)
O_25	0.7968 (2)	0.1811 (2)	0.2832 (2)	0.111 (2)
O1_51	1.0049 (6)	0.3383 (5)	0.4648 (6)	0.231 (7)*
O2_51	0.9708 (5)	0.2760 (5)	0.4618 (5)	0.208 (6)*
C1_51	0.9851 (4)	0.3070 (4)	0.4490 (4)	0.138 (5)*
C2_51	0.9840 (3)	0.3114 (3)	0.4083 (3)	0.114 (3)*
F1_51	0.9662 (3)	0.3281 (3)	0.3986 (3)	0.165 (3)*
F2_51	0.9727 (4)	0.2819 (4)	0.3884 (4)	0.217 (5)*
F3_51	1.0178 (4)	0.3325 (5)	0.3956 (5)	0.233 (6)*
O1_52	0.7820 (7)	0.0895 (7)	0.3424 (7)	0.253 (9)*
O2_52	0.7941 (11)	0.0761 (11)	0.3991 (10)	0.361 (17)*
C1_52	0.7816 (7)	0.0901 (7)	0.3780 (8)	0.31 (2)*
C2_52	0.7631 (9)	0.1106 (8)	0.3939 (7)	0.34 (2)*
F1_52	0.7788 (7)	0.1300 (7)	0.4236 (6)	0.287 (9)*
F2_52	0.7576 (5)	0.1319 (6)	0.3712 (5)	0.241 (7)*
F3_52	0.7300 (9)	0.0849 (10)	0.4054 (11)	0.44 (2)*
O_101	0.6748 (4)	0.1881 (4)	−0.0988 (5)	0.186 (5)*
O_102	0.7354 (6)	0.1701 (6)	0.1797 (6)	0.218 (6)*
O_103	0.6667	0.1808 (7)	−0.1667	0.221 (9)*
O_104	0.6951 (15)	0.2575 (15)	−0.1642 (15)	0.257 (18)*	0.50
O_105	0.7879 (9)	0.0781 (9)	0.2244 (9)	0.300 (12)*
O_106	0.5656 (11)	−0.0499 (10)	0.1957 (10)	0.318 (14)*
O_107	0.5152 (11)	−0.0860 (11)	0.0886 (10)	0.331 (15)*
O_108	0.6957 (13)	0.1502 (12)	−0.0697 (12)	0.355 (17)*
O_109	0.6056 (18)	0.0000	0.0000	0.40 (3)*
O_110	0.7636 (14)	0.1270 (15)	0.1637 (15)	0.253 (17)*	0.50
O_111	0.670 (3)	0.014 (3)	0.067 (2)	0.36 (4)*	0.50
O_112	0.5457 (19)	−0.0231 (19)	0.0555 (19)	0.30 (2)*	0.50
O_113	0.6484 (15)	0.1069 (15)	−0.1482 (15)	0.260 (18)*	0.50
O_114	0.6213 (16)	−0.0416 (16)	0.0528 (15)	0.266 (19)*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N_1	0.113 (5)	0.104 (5)	0.038 (3)	0.049 (4)	−0.003 (3)	−0.012 (3)
CA_1	0.147 (6)	0.100 (5)	0.040 (4)	0.067 (5)	−0.005 (4)	−0.011 (3)
CB_1	0.164 (8)	0.110 (7)	0.052 (6)	0.054 (5)	−0.001 (5)	−0.023 (5)
CG_1	0.130 (7)	0.113 (7)	0.056 (5)	0.040 (6)	−0.017 (5)	−0.012 (5)
CD_1	0.101 (5)	0.103 (6)	0.053 (5)	0.032 (5)	−0.003 (4)	−0.015 (4)
C_1	0.130 (7)	0.129 (6)	0.036 (4)	0.077 (6)	0.008 (4)	0.002 (4)
O_1	0.200 (8)	0.155 (6)	0.049 (4)	0.127 (6)	0.015 (4)	0.002 (4)
N_2	0.107 (5)	0.110 (4)	0.036 (4)	0.054 (4)	0.009 (3)	−0.002 (3)
CA_2	0.101 (5)	0.137 (7)	0.105 (8)	0.075 (5)	0.002 (5)	0.034 (6)
CB_2	0.215 (12)	0.152 (10)	0.146 (13)	0.117 (11)	0.026 (11)	0.013 (9)
CG1_2	0.31 (2)	0.147 (10)	0.131 (13)	0.136 (13)	0.017 (14)	−0.001 (9)
CG2_2	0.248 (13)	0.28 (2)	0.164 (16)	0.216 (16)	0.054 (14)	0.029 (16)
C_2	0.121 (6)	0.110 (6)	0.048 (5)	0.044 (5)	0.018 (4)	−0.020 (5)
O_2	0.130 (5)	0.155 (7)	0.039 (3)	0.032 (5)	0.015 (3)	−0.024 (4)
N_3	0.106 (5)	0.159 (7)	0.034 (4)	0.039 (5)	−0.003 (3)	−0.032 (4)
CA_3	0.114 (6)	0.243 (11)	0.044 (5)	0.015 (7)	0.009 (5)	−0.002 (6)
CB_3	0.123 (8)	0.36 (2)	0.185 (19)	0.087 (12)	−0.007 (12)	0.047 (18)
CG_3	0.144 (9)	0.32 (3)	0.36 (3)	0.077 (12)	−0.057 (16)	0.12 (2)
CD_3	0.123 (11)	0.31 (3)	0.53 (4)	0.060 (13)	−0.04 (2)	0.14 (3)
NZ_3	0.125 (10)	0.22 (2)	0.63 (6)	0.086 (12)	0.020 (18)	−0.02 (3)
C_3	0.144 (10)	0.229 (9)	0.027 (5)	0.021 (8)	0.019 (5)	−0.005 (6)
O_3	0.176 (9)	0.271 (14)	0.045 (4)	−0.033 (10)	−0.009 (5)	0.010 (6)
N_4	0.134 (8)	0.240 (9)	0.052 (6)	0.007 (8)	0.012 (5)	−0.002 (6)
CA_4	0.141 (7)	0.235 (11)	0.081 (8)	0.044 (8)	0.013 (7)	0.003 (8)
CB_4	0.170 (13)	0.38 (2)	0.103 (10)	0.125 (16)	−0.002 (11)	0.025 (13)
CG_4	0.31 (3)	0.40 (3)	0.150 (15)	0.19 (2)	−0.008 (19)	0.048 (16)
CD1_4	0.45 (6)	0.57 (6)	0.103 (11)	0.29 (5)	−0.01 (3)	0.04 (2)
CD2_4	0.33 (4)	0.53 (5)	0.21 (3)	0.28 (4)	−0.04 (3)	0.05 (3)
C_4	0.141 (6)	0.162 (10)	0.073 (7)	0.059 (7)	0.024 (6)	0.003 (6)
O_4	0.149 (7)	0.189 (9)	0.073 (5)	0.068 (6)	0.009 (5)	0.000 (5)
N_5	0.145 (6)	0.192 (12)	0.094 (7)	0.031 (8)	0.053 (5)	−0.010 (7)
CA_5	0.146 (6)	0.172 (11)	0.082 (6)	0.036 (8)	0.053 (6)	−0.014 (6)
CB_5	0.143 (7)	0.195 (13)	0.099 (8)	0.029 (8)	0.066 (7)	−0.014 (9)
CG_5	0.143 (7)	0.219 (11)	0.079 (9)	0.040 (8)	0.046 (7)	−0.002 (9)
CD1_5	0.210 (11)	0.276 (16)	0.104 (12)	0.107 (11)	0.012 (11)	−0.058 (13)
CD2_5	0.154 (10)	0.212 (12)	0.124 (12)	0.027 (8)	0.063 (9)	0.008 (11)
CE1_5	0.174 (9)	0.220 (13)	0.087 (9)	0.105 (11)	0.054 (8)	0.016 (10)
CE2_5	0.151 (10)	0.184 (11)	0.178 (17)	0.081 (7)	0.033 (11)	−0.009 (12)
CZ_5	0.213 (14)	0.238 (13)	0.129 (13)	0.141 (12)	0.047 (11)	0.006 (13)
C_5	0.138 (9)	0.152 (7)	0.104 (6)	0.071 (8)	0.072 (5)	0.015 (6)
O_5	0.184 (10)	0.151 (7)	0.182 (11)	0.066 (7)	0.113 (9)	0.021 (7)
N_6	0.122 (7)	0.168 (7)	0.081 (5)	0.070 (6)	0.047 (4)	0.020 (5)
CA_6	0.115 (7)	0.232 (11)	0.104 (6)	0.093 (8)	0.044 (5)	0.036 (7)
CB_6	0.088 (8)	0.289 (16)	0.106 (9)	0.047 (8)	0.017 (6)	0.021 (9)
CG_6	0.154 (13)	0.183 (10)	0.119 (11)	0.020 (10)	0.010 (9)	0.002 (9)
CD_6	0.133 (10)	0.150 (7)	0.120 (9)	0.047 (9)	0.012 (7)	0.008 (7)
C_6	0.110 (6)	0.207 (12)	0.085 (6)	0.087 (8)	0.027 (5)	0.040 (8)
O_6	0.124 (6)	0.308 (17)	0.096 (6)	0.107 (9)	0.031 (5)	0.073 (8)
N_7	0.100 (5)	0.149 (7)	0.064 (5)	0.054 (5)	0.028 (4)	0.006 (5)
CA_7	0.092 (5)	0.140 (6)	0.057 (6)	0.044 (5)	0.022 (4)	0.000 (5)
CB_7	0.101 (7)	0.197 (9)	0.125 (11)	0.080 (7)	0.047 (7)	0.027 (9)
CG1_7	0.121 (10)	0.272 (19)	0.126 (11)	0.107 (11)	0.061 (9)	0.058 (13)
CG2_7	0.177 (14)	0.177 (9)	0.21 (2)	0.099 (10)	0.060 (14)	0.060 (13)
C_7	0.092 (6)	0.159 (6)	0.044 (5)	0.038 (5)	0.007 (4)	−0.004 (5)
O_7	0.184 (9)	0.173 (8)	0.035 (4)	0.015 (7)	0.000 (4)	−0.003 (4)
N_8	0.082 (4)	0.134 (5)	0.038 (4)	0.033 (4)	0.005 (3)	−0.014 (4)
CA_8	0.093 (5)	0.131 (6)	0.056 (5)	0.039 (5)	0.013 (4)	−0.019 (5)
CB_8	0.124 (9)	0.156 (7)	0.116 (10)	0.067 (7)	0.007 (7)	−0.014 (7)
CGa_8	0.150 (15)	0.145 (8)	0.165 (17)	0.074 (10)	−0.019 (13)	−0.040 (10)
CDa_8	0.127 (14)	0.207 (15)	0.17 (2)	0.086 (13)	−0.016 (14)	−0.071 (15)
NZa_8	0.18 (2)	0.198 (15)	0.27 (3)	0.087 (15)	0.00 (2)	−0.12 (2)
CGb_8	0.15 (3)	0.16 (3)	0.17 (3)	0.08 (2)	0.03 (2)	−0.01 (3)
CDb_8	0.16 (3)	0.19 (3)	0.19 (4)	0.11 (3)	−0.03 (3)	−0.03 (3)
NZb_8	0.14 (3)	0.10 (2)	0.35 (7)	0.04 (2)	0.04 (4)	0.01 (3)
C_8	0.081 (4)	0.141 (8)	0.033 (4)	0.031 (5)	0.007 (3)	0.001 (4)
O_8	0.084 (4)	0.141 (5)	0.041 (3)	0.033 (4)	0.003 (3)	−0.021 (3)
N_9	0.083 (4)	0.133 (6)	0.040 (4)	0.033 (4)	0.000 (3)	−0.019 (4)
CA_9	0.081 (4)	0.114 (5)	0.037 (4)	0.027 (4)	0.007 (3)	−0.010 (4)
CB_9	0.120 (6)	0.106 (6)	0.040 (5)	0.043 (5)	0.017 (4)	−0.014 (4)
CG_9	0.127 (8)	0.156 (10)	0.105 (8)	0.067 (8)	0.018 (7)	−0.007 (8)
CD1_9	0.176 (15)	0.33 (3)	0.125 (9)	0.164 (18)	0.085 (11)	0.100 (15)
CD2_9	0.161 (12)	0.207 (16)	0.090 (9)	0.105 (11)	0.010 (8)	0.002 (9)
C_9	0.088 (5)	0.104 (4)	0.037 (4)	0.042 (4)	0.004 (4)	−0.017 (4)
O_9	0.099 (4)	0.108 (4)	0.038 (3)	0.043 (3)	−0.003 (3)	−0.017 (3)
N_10	0.086 (4)	0.109 (4)	0.035 (3)	0.030 (4)	−0.002 (3)	−0.010 (3)
CA_10	0.109 (6)	0.109 (5)	0.035 (4)	0.046 (5)	0.000 (4)	−0.008 (4)
CB_10	0.125 (7)	0.128 (5)	0.035 (4)	0.050 (5)	−0.002 (4)	0.002 (4)
CG_10	0.146 (7)	0.123 (5)	0.028 (4)	0.060 (5)	−0.009 (5)	0.000 (4)
CD1_10	0.164 (9)	0.154 (8)	0.065 (7)	0.094 (7)	−0.009 (6)	0.006 (6)
CD2_10	0.142 (6)	0.113 (6)	0.052 (5)	0.049 (6)	0.009 (6)	−0.008 (5)
CE1_10	0.201 (10)	0.158 (9)	0.071 (7)	0.118 (9)	−0.022 (8)	−0.004 (7)
CE2_10	0.154 (8)	0.108 (6)	0.060 (6)	0.054 (6)	−0.013 (6)	0.006 (5)
CZ_10	0.204 (10)	0.125 (8)	0.082 (8)	0.087 (8)	−0.031 (9)	−0.010 (6)
C_10	0.107 (5)	0.111 (6)	0.029 (4)	0.052 (5)	−0.001 (4)	0.002 (3)
O_10	0.113 (5)	0.160 (7)	0.061 (4)	0.071 (5)	0.009 (3)	0.010 (4)
N_21	0.088 (4)	0.099 (5)	0.044 (4)	0.021 (4)	0.015 (3)	0.007 (3)
CA_21	0.113 (6)	0.102 (6)	0.056 (5)	0.015 (5)	0.015 (4)	−0.012 (4)
CB_21	0.100 (6)	0.164 (11)	0.082 (7)	−0.012 (7)	0.010 (5)	−0.034 (7)
CG_21	0.083 (6)	0.214 (13)	0.073 (7)	0.033 (7)	−0.011 (5)	−0.021 (8)
CD_21	0.069 (5)	0.179 (10)	0.050 (5)	0.034 (5)	0.017 (4)	−0.002 (5)
C_21	0.082 (5)	0.092 (5)	0.045 (4)	0.027 (4)	0.003 (4)	−0.010 (4)
O_21	0.143 (6)	0.081 (4)	0.044 (3)	0.026 (4)	0.001 (3)	−0.010 (3)
N_22	0.079 (4)	0.090 (4)	0.048 (4)	0.030 (3)	0.012 (3)	−0.009 (3)
CA_22	0.086 (4)	0.088 (4)	0.031 (4)	0.030 (4)	0.001 (3)	−0.004 (3)
CB_22	0.137 (7)	0.094 (5)	0.060 (6)	0.049 (5)	−0.005 (5)	−0.005 (4)
CG1_22	0.169 (10)	0.097 (6)	0.114 (10)	0.036 (7)	0.023 (9)	0.012 (7)
CG2_22	0.154 (8)	0.138 (10)	0.118 (10)	0.090 (8)	−0.004 (8)	−0.009 (8)
C_22	0.078 (4)	0.104 (6)	0.041 (4)	0.025 (4)	−0.001 (3)	0.003 (4)
O_22	0.090 (4)	0.172 (7)	0.035 (3)	0.053 (4)	0.000 (3)	−0.001 (3)
N_23	0.078 (4)	0.116 (5)	0.037 (3)	0.031 (4)	−0.001 (3)	0.005 (3)
CA_23	0.083 (5)	0.141 (7)	0.060 (5)	0.043 (5)	−0.002 (4)	0.015 (5)
CB_23	0.140 (9)	0.171 (9)	0.141 (12)	0.090 (9)	0.018 (8)	0.042 (9)
CG_23	0.173 (12)	0.237 (19)	0.32 (2)	0.141 (14)	−0.004 (15)	0.089 (18)
CD_23	0.155 (14)	0.24 (2)	0.29 (3)	0.104 (15)	−0.014 (14)	0.07 (2)
NZ_23	0.172 (12)	0.165 (12)	0.41 (3)	0.115 (11)	−0.073 (16)	0.005 (17)
C_23	0.077 (4)	0.144 (7)	0.042 (4)	0.046 (4)	0.005 (3)	0.009 (4)
O_23	0.087 (4)	0.187 (8)	0.048 (4)	0.037 (4)	0.004 (3)	0.027 (4)
N_24	0.078 (4)	0.145 (6)	0.050 (4)	0.041 (4)	0.003 (3)	0.022 (4)
CA_24	0.092 (5)	0.142 (7)	0.085 (7)	0.062 (5)	0.013 (4)	0.038 (6)
CB_24	0.125 (8)	0.157 (8)	0.210 (14)	0.093 (8)	0.009 (9)	0.040 (10)
CGa_24	0.113 (11)	0.124 (13)	0.184 (17)	0.068 (10)	−0.054 (12)	−0.018 (11)
CD1a_24	0.16 (2)	0.16 (2)	0.23 (3)	0.116 (18)	−0.05 (2)	−0.02 (2)
CD2a_24	0.23 (3)	0.25 (3)	0.192 (18)	0.17 (3)	−0.02 (2)	0.03 (2)
CGb_24	0.16 (2)	0.137 (19)	0.20 (2)	0.090 (17)	0.001 (19)	0.031 (17)
CD1b_24	0.14 (3)	0.12 (2)	0.17 (4)	0.069 (19)	0.03 (2)	0.05 (2)
CD2b_24	0.22 (4)	0.21 (5)	0.22 (5)	0.14 (3)	0.07 (4)	0.03 (3)
C_24	0.088 (5)	0.122 (7)	0.056 (5)	0.057 (5)	0.008 (4)	0.022 (4)
O_24	0.099 (4)	0.123 (5)	0.060 (4)	0.061 (4)	0.013 (3)	0.023 (3)
N_25	0.104 (5)	0.156 (8)	0.061 (5)	0.076 (5)	0.010 (4)	0.016 (4)
CA_25	0.102 (6)	0.151 (8)	0.052 (5)	0.075 (6)	0.015 (4)	0.011 (5)
CB_25	0.144 (7)	0.172 (10)	0.054 (5)	0.097 (7)	−0.007 (6)	−0.016 (6)
CG_25	0.141 (6)	0.187 (9)	0.054 (6)	0.109 (7)	0.000 (5)	−0.024 (6)
CD1_25	0.171 (10)	0.151 (10)	0.232 (19)	0.103 (9)	−0.024 (12)	−0.014 (10)
CD2_25	0.142 (6)	0.216 (11)	0.066 (7)	0.115 (7)	0.048 (6)	0.041 (7)
CE1_25	0.179 (11)	0.189 (13)	0.209 (18)	0.129 (10)	−0.003 (12)	−0.007 (12)
CE2_25	0.138 (7)	0.199 (12)	0.142 (12)	0.117 (9)	0.016 (8)	−0.024 (9)
CZ_25	0.158 (10)	0.248 (17)	0.204 (19)	0.132 (10)	−0.003 (13)	0.023 (14)
C_25	0.110 (7)	0.124 (7)	0.055 (5)	0.071 (5)	0.013 (5)	0.008 (5)
O_25	0.128 (6)	0.130 (5)	0.079 (5)	0.067 (5)	0.014 (4)	0.001 (4)

Geometric parameters (Å, º)

N_1—C_10	1.334 (10)	N_9—H0_9	0.8800
N_1—CA_1	1.462 (10)	CA_9—CB_9	1.518 (12)
N_1—CD_1	1.468 (11)	CA_9—C_9	1.516 (11)
CA_1—CB_1	1.528 (13)	CA_9—HA_9	1.0000
CA_1—C_1	1.527 (11)	CB_9—CG_9	1.520 (13)
CA_1—HA_1	1.0000	CB_9—HB1_9	0.9900
CB_1—CG_1	1.517 (14)	CB_9—HB2_9	0.9900
CB_1—HB1_1	0.9900	CG_9—CD1_9	1.490 (15)
CB_1—HB2_1	0.9900	CG_9—CD2_9	1.523 (15)
CG_1—CD_1	1.532 (12)	CG_9—HG_9	1.0000
CG_1—HG1_1	0.9900	CD1_9—HD1A_9	0.9800
CG_1—HG2_1	0.9900	CD1_9—HD1B_9	0.9800
CD_1—HD1_1	0.9900	CD1_9—HD1C_9	0.9800
CD_1—HD2_1	0.9900	CD2_9—HD2A_9	0.9800
C_1—O_1	1.231 (10)	CD2_9—HD2B_9	0.9800
C_1—N_2	1.305 (11)	CD2_9—HD2C_9	0.9800
N_2—CA_2	1.429 (11)	C_9—O_9	1.232 (9)
N_2—H0_2	0.8800	C_9—N_10	1.356 (10)
CA_2—C_2	1.509 (12)	N_10—CA_10	1.444 (10)
CA_2—CB_2	1.593 (13)	N_10—H0_10	0.8800
CA_2—HA_2	1.0000	CA_10—C_10	1.518 (10)
CB_2—CG2_2	1.458 (16)	CA_10—CB_10	1.539 (11)
CB_2—CG1_2	1.524 (15)	CA_10—HA_10	1.0000
CB_2—HB_2	1.0000	CB_10—CG_10	1.526 (12)
CG1_2—HG1A_2	0.9800	CB_10—HB1_10	0.9900
CG1_2—HG1B_2	0.9800	CB_10—HB2_10	0.9900
CG1_2—HG1C_2	0.9800	CG_10—CD1_10	1.366 (13)
CG2_2—HG2A_2	0.9800	CG_10—CD2_10	1.380 (13)
CG2_2—HG2B_2	0.9800	CD1_10—CE1_10	1.383 (14)
CG2_2—HG2C_2	0.9800	CD1_10—HD1_10	0.9500
C_2—O_2	1.231 (11)	CD2_10—CE2_10	1.385 (13)
C_2—N_3	1.295 (11)	CD2_10—HD2_10	0.9500
N_3—CA_3	1.465 (12)	CE1_10—CZ_10	1.373 (15)
N_3—H0_3	0.8800	CE1_10—HE1_10	0.9500
CA_3—C_3	1.501 (14)	CE2_10—CZ_10	1.376 (15)
CA_3—CB_3	1.524 (16)	CE2_10—HE2_10	0.9500
CA_3—HA_3	1.0000	CZ_10—HZ_10	0.9500
CB_3—CG_3	1.54 (4)	C_10—O_10	1.233 (10)
CB_3—HB1_3	0.9900	N_21—C_25^i	1.347 (11)
CB_3—HB2_3	0.9900	N_21—CA_21	1.443 (10)
CG_3—CD_3	1.51 (4)	N_21—CD_21	1.513 (12)
CG_3—HG1_3	0.9900	CA_21—C_21	1.531 (11)
CG_3—HG2_3	0.9900	CA_21—CB_21	1.538 (13)
CD_3—NZ_3	1.50 (4)	CA_21—HA_21	1.0000
CD_3—HD1_3	0.9900	CB_21—CG_21	1.500 (16)
CD_3—HD2_3	0.9900	CB_21—HB1_21	0.9900
NZ_3—HZ1_3	0.9100	CB_21—HB2_21	0.9900
NZ_3—HZ2_3	0.9100	CG_21—CD_21	1.524 (13)
NZ_3—HZ3_3	0.9100	CG_21—HG1_21	0.9900
C_3—O_3	1.236 (12)	CG_21—HG2_21	0.9900
C_3—N_4	1.317 (14)	CD_21—HD1_21	0.9900
N_4—CA_4	1.460 (14)	CD_21—HD2_21	0.9900
N_4—H0_4	0.8800	C_21—O_21	1.228 (9)
CA_4—C_4	1.524 (14)	C_21—N_22	1.341 (10)
CA_4—CB_4	1.528 (16)	N_22—CA_22	1.443 (9)
CA_4—HA_4	1.0000	N_22—H0_22	0.8800
CB_4—CG_4	1.554 (16)	CA_22—CB_22	1.521 (11)
CB_4—HB1_4	0.9900	CA_22—C_22	1.521 (11)
CB_4—HB2_4	0.9900	CA_22—HA_22	1.0000
CG_4—CD2_4	1.51 (6)	CB_22—CG1_22	1.502 (13)
CG_4—CD1_4	1.53 (4)	CB_22—CG2_22	1.539 (14)
CG_4—HG_4	1.0000	CB_22—HB_22	1.0000
CD1_4—HD1A_4	0.9800	CG1_22—HG1A_22	0.9800
CD1_4—HD1B_4	0.9800	CG1_22—HG1B_22	0.9800
CD1_4—HD1C_4	0.9800	CG1_22—HG1C_22	0.9800
CD2_4—HD2A_4	0.9800	CG2_22—HG2A_22	0.9800
CD2_4—HD2B_4	0.9800	CG2_22—HG2B_22	0.9800
CD2_4—HD2C_4	0.9800	CG2_22—HG2C_22	0.9800
C_4—O_4	1.206 (12)	C_22—O_22	1.224 (9)
C_4—N_5	1.324 (13)	C_22—N_23	1.322 (10)
N_5—CA_5	1.460 (14)	N_23—CA_23	1.457 (11)
N_5—H0_5	0.8800	N_23—H0_23	0.8800
CA_5—C_5	1.498 (14)	CA_23—C_23	1.510 (12)
CA_5—CB_5	1.546 (14)	CA_23—CB_23	1.519 (14)
CA_5—HA_5	1.0000	CA_23—HA_23	1.0000
CB_5—CG_5	1.518 (15)	CB_23—CG_23	1.502 (16)
CB_5—HB1_5	0.9900	CB_23—HB1_23	0.9900
CB_5—HB2_5	0.9900	CB_23—HB2_23	0.9900
CG_5—CD1_5	1.372 (16)	CG_23—CD_23	1.50 (4)
CG_5—CD2_5	1.397 (17)	CG_23—HG1_23	0.9900
CD1_5—CE1_5	1.419 (16)	CG_23—HG2_23	0.9900
CD1_5—HD1_5	0.9500	CD_23—NZ_23	1.51 (4)
CD2_5—CE2_5	1.360 (16)	CD_23—HD1_23	0.9900
CD2_5—HD2_5	0.9500	CD_23—HD2_23	0.9900
CE1_5—CZ_5	1.369 (16)	NZ_23—HZ1_23	0.9100
CE1_5—HE1_5	0.9500	NZ_23—HZ2_23	0.9100
CE2_5—CZ_5	1.334 (16)	NZ_23—HZ3_23	0.9100
CE2_5—HE2_5	0.9500	C_23—O_23	1.202 (10)
CZ_5—HZ_5	0.9500	C_23—N_24	1.328 (11)
C_5—O_5	1.224 (13)	N_24—CA_24	1.443 (11)
C_5—N_6	1.328 (13)	N_24—H0_24	0.8800
N_6—CA_6	1.468 (13)	CA_24—C_24	1.513 (11)
N_6—CD_6	1.485 (14)	CA_24—CB_24	1.547 (14)
CA_6—C_6	1.529 (12)	CA_24—HA_24	1.0000
CA_6—CB_6	1.545 (15)	CB_24—CGa_24	1.511 (15)
CA_6—HA_6	1.0000	CB_24—CGb_24	1.533 (17)
CB_6—CG_6	1.511 (17)	CB_24—HB1_24	0.9900
CB_6—HB1_6	0.9900	CB_24—HB2_24	0.9900
CB_6—HB2_6	0.9900	CB_24—HB3_24	0.9900
CG_6—CD_6	1.482 (15)	CB_24—HB4_24	0.9900
CG_6—HG1_6	0.9900	CGa_24—CD2a_24	1.521 (17)
CG_6—HG2_6	0.9900	CGa_24—CD1a_24	1.533 (17)
CD_6—HD1_6	0.9900	CGa_24—HG_24	1.0000
CD_6—HD2_6	0.9900	CD1a_24—HD1A_24	0.9800
C_6—O_6	1.211 (12)	CD1a_24—HD1B_24	0.9800
C_6—N_7	1.323 (12)	CD1a_24—HD1C_24	0.9800
N_7—CA_7	1.454 (11)	CD2a_24—HD2A_24	0.9800
N_7—H0_7	0.8800	CD2a_24—HD2B_24	0.9800
CA_7—C_7	1.509 (12)	CD2a_24—HD2C_24	0.9800
CA_7—CB_7	1.544 (13)	CGb_24—CD1b_24	1.496 (18)
CA_7—HA_7	1.0000	CGb_24—CD2b_24	1.523 (18)
CB_7—CG2_7	1.498 (15)	CGb_24—HG1_24	1.0000
CB_7—CG1_7	1.541 (13)	CD1b_24—HD1D_24	0.9800
CB_7—HB_7	1.0000	CD1b_24—HD1E_24	0.9800
CG1_7—HG1A_7	0.9800	CD1b_24—HD1F_24	0.9800
CG1_7—HG1B_7	0.9800	CD2b_24—HD2D_24	0.9800
CG1_7—HG1C_7	0.9800	CD2b_24—HD2E_24	0.9800
CG2_7—HG2A_7	0.9800	CD2b_24—HD2F_24	0.9800
CG2_7—HG2B_7	0.9800	C_24—O_24	1.225 (10)
CG2_7—HG2C_7	0.9800	C_24—N_25	1.330 (11)
C_7—O_7	1.215 (11)	N_25—CA_25	1.469 (11)
C_7—N_8	1.323 (11)	N_25—H0_25	0.8800
N_8—CA_8	1.446 (11)	CA_25—C_25	1.516 (11)
N_8—H0_8	0.8800	CA_25—CB_25	1.552 (12)
CA_8—C_8	1.506 (11)	CA_25—HA_25	1.0000
CA_8—CB_8	1.541 (13)	CB_25—CG_25	1.523 (13)
CA_8—HA_8	1.0000	CB_25—HB1_25	0.9900
CB_8—CGb_8	1.485 (19)	CB_25—HB2_25	0.9900
CB_8—CGa_8	1.509 (17)	CG_25—CD2_25	1.372 (14)
CB_8—HB1_8	0.9900	CG_25—CD1_25	1.405 (15)
CB_8—HB2_8	0.9900	CD1_25—CE1_25	1.402 (16)
CB_8—HB3_8	0.9900	CD1_25—HD1_25	0.9500
CB_8—HB4_8	0.9900	CD2_25—CE2_25	1.380 (14)
CGa_8—CDa_8	1.478 (18)	CD2_25—HD2_25	0.9500
CGa_8—HG1_8	0.9900	CE1_25—CZ_25	1.394 (16)
CGa_8—HG2_8	0.9900	CE1_25—HE1_25	0.9500
CDa_8—NZa_8	1.489 (19)	CE2_25—CZ_25	1.404 (16)
CDa_8—HD1_8	0.9900	CE2_25—HE2_25	0.9500
CDa_8—HD2_8	0.9900	CZ_25—HZ_25	0.9500
NZa_8—HZ1_8	0.9100	C_25—O_25	1.236 (11)
NZa_8—HZ2_8	0.9100	C_25—N_21^i	1.347 (11)
NZa_8—HZ3_8	0.9100	O1_51—C1_51	1.276 (15)
CGb_8—CDb_8	1.52 (2)	O2_51—C1_51	1.205 (14)
CGb_8—HG3_8	0.9900	C1_51—C2_51	1.491 (14)
CGb_8—HG4_8	0.9900	C2_51—F1_51	1.288 (12)
CDb_8—NZb_8	1.47 (2)	C2_51—F2_51	1.290 (13)
CDb_8—HD3_8	0.9900	C2_51—F3_51	1.311 (14)
CDb_8—HD4_8	0.9900	O1_52—C1_52	1.290 (18)
NZb_8—HZ4_8	0.9100	O2_52—C1_52	1.222 (18)
NZb_8—HZ5_8	0.9100	C1_52—C2_52	1.515 (17)
NZb_8—HZ6_8	0.8900	C2_52—F1_52	1.307 (18)
C_8—O_8	1.226 (10)	C2_52—F2_52	1.308 (18)
C_8—N_9	1.326 (10)	C2_52—F3_52	1.315 (19)
N_9—CA_9	1.474 (10)
C_10—N_1—CA_1	119.7 (7)	HD1_8—CDa_8—HD2_8	107.7
C_10—N_1—CD_1	127.3 (7)	HZ1_8—NZa_8—HZ2_8	109.5
CA_1—N_1—CD_1	112.9 (7)	HZ1_8—NZa_8—HZ3_8	109.5
N_1—CA_1—CB_1	100.3 (7)	HZ2_8—NZa_8—HZ3_8	109.5
N_1—CA_1—C_1	114.1 (7)	CB_8—CGb_8—CDb_8	105 (2)
CB_1—CA_1—C_1	109.4 (7)	NZb_8—CDb_8—CGb_8	118 (3)
N_1—CA_1—HA_1	110.9	HZ4_8—NZb_8—HZ5_8	109.5
CB_1—CA_1—HA_1	110.9	HZ4_8—NZb_8—HZ6_8	111.1
C_1—CA_1—HA_1	110.9	HZ5_8—NZb_8—HZ6_8	109.5
CA_1—CB_1—CG_1	104.9 (8)	O_8—C_8—N_9	122.3 (7)
CA_1—CB_1—HB1_1	110.8	O_8—C_8—CA_8	120.8 (7)
CG_1—CB_1—HB1_1	110.8	N_9—C_8—CA_8	116.9 (7)
CA_1—CB_1—HB2_1	110.8	C_8—N_9—CA_9	122.4 (7)
CG_1—CB_1—HB2_1	110.8	C_8—N_9—H0_9	118.8
HB1_1—CB_1—HB2_1	108.8	CA_9—N_9—H0_9	118.8
CD_1—CG_1—CB_1	102.1 (8)	N_9—CA_9—CB_9	111.9 (7)
CD_1—CG_1—HG1_1	111.4	N_9—CA_9—C_9	105.0 (7)
CB_1—CG_1—HG1_1	111.4	CB_9—CA_9—C_9	111.2 (7)
CD_1—CG_1—HG2_1	111.4	N_9—CA_9—HA_9	109.5
CB_1—CG_1—HG2_1	111.4	CB_9—CA_9—HA_9	109.5
HG1_1—CG_1—HG2_1	109.2	C_9—CA_9—HA_9	109.5
N_1—CD_1—CG_1	104.0 (7)	CA_9—CB_9—CG_9	118.5 (8)
N_1—CD_1—HD1_1	111.0	CA_9—CB_9—HB1_9	107.7
CG_1—CD_1—HD1_1	111.0	CG_9—CB_9—HB1_9	107.7
N_1—CD_1—HD2_1	111.0	CA_9—CB_9—HB2_9	107.7
CG_1—CD_1—HD2_1	111.0	CG_9—CB_9—HB2_9	107.7
HD1_1—CD_1—HD2_1	109.0	HB1_9—CB_9—HB2_9	107.1
O_1—C_1—N_2	119.4 (8)	CD1_9—CG_9—CB_9	112.2 (10)
O_1—C_1—CA_1	120.5 (8)	CD1_9—CG_9—CD2_9	110.1 (12)
N_2—C_1—CA_1	120.1 (7)	CB_9—CG_9—CD2_9	113.0 (11)
C_1—N_2—CA_2	126.2 (7)	CD1_9—CG_9—HG_9	107.1
C_1—N_2—H0_2	116.9	CB_9—CG_9—HG_9	107.1
CA_2—N_2—H0_2	116.9	CD2_9—CG_9—HG_9	107.1
N_2—CA_2—C_2	112.8 (7)	CG_9—CD1_9—HD1A_9	109.5
N_2—CA_2—CB_2	111.7 (9)	CG_9—CD1_9—HD1B_9	109.5
C_2—CA_2—CB_2	96.6 (9)	HD1A_9—CD1_9—HD1B_9	109.5
N_2—CA_2—HA_2	111.7	CG_9—CD1_9—HD1C_9	109.5
C_2—CA_2—HA_2	111.7	HD1A_9—CD1_9—HD1C_9	109.5
CB_2—CA_2—HA_2	111.7	HD1B_9—CD1_9—HD1C_9	109.5
CG2_2—CB_2—CG1_2	111.7 (15)	CG_9—CD2_9—HD2A_9	109.5
CG2_2—CB_2—CA_2	109.3 (11)	CG_9—CD2_9—HD2B_9	109.5
CG1_2—CB_2—CA_2	109.8 (11)	HD2A_9—CD2_9—HD2B_9	109.5
CG2_2—CB_2—HB_2	108.6	CG_9—CD2_9—HD2C_9	109.5
CG1_2—CB_2—HB_2	108.7	HD2A_9—CD2_9—HD2C_9	109.5
CA_2—CB_2—HB_2	108.6	HD2B_9—CD2_9—HD2C_9	109.5
CB_2—CG1_2—HG1A_2	109.5	O_9—C_9—N_10	122.2 (7)
CB_2—CG1_2—HG1B_2	109.5	O_9—C_9—CA_9	120.0 (8)
HG1A_2—CG1_2—HG1B_2	109.5	N_10—C_9—CA_9	117.6 (7)
CB_2—CG1_2—HG1C_2	109.5	C_9—N_10—CA_10	118.0 (6)
HG1A_2—CG1_2—HG1C_2	109.5	C_9—N_10—H0_10	121.0
HG1B_2—CG1_2—HG1C_2	109.5	CA_10—N_10—H0_10	121.0
CB_2—CG2_2—HG2A_2	109.5	N_10—CA_10—C_10	109.4 (7)
CB_2—CG2_2—HG2B_2	109.5	N_10—CA_10—CB_10	110.5 (7)
HG2A_2—CG2_2—HG2B_2	109.5	C_10—CA_10—CB_10	108.4 (7)
CB_2—CG2_2—HG2C_2	109.5	N_10—CA_10—HA_10	109.5
HG2A_2—CG2_2—HG2C_2	109.5	C_10—CA_10—HA_10	109.5
HG2B_2—CG2_2—HG2C_2	109.5	CB_10—CA_10—HA_10	109.5
O_2—C_2—N_3	126.4 (9)	CG_10—CB_10—CA_10	110.1 (7)
O_2—C_2—CA_2	117.7 (8)	CG_10—CB_10—HB1_10	109.6
N_3—C_2—CA_2	115.9 (8)	CA_10—CB_10—HB1_10	109.6
C_2—N_3—CA_3	120.5 (7)	CG_10—CB_10—HB2_10	109.6
C_2—N_3—H0_3	119.7	CA_10—CB_10—HB2_10	109.6
CA_3—N_3—H0_3	119.8	HB1_10—CB_10—HB2_10	108.2
N_3—CA_3—C_3	112.1 (10)	CD1_10—CG_10—CD2_10	118.5 (10)
N_3—CA_3—CB_3	110.4 (12)	CD1_10—CG_10—CB_10	122.2 (11)
C_3—CA_3—CB_3	108.5 (12)	CD2_10—CG_10—CB_10	119.2 (9)
N_3—CA_3—HA_3	108.6	CG_10—CD1_10—CE1_10	121.9 (12)
C_3—CA_3—HA_3	108.6	CG_10—CD1_10—HD1_10	119.0
CB_3—CA_3—HA_3	108.6	CE1_10—CD1_10—HD1_10	119.0
CA_3—CB_3—CG_3	105.9 (16)	CG_10—CD2_10—CE2_10	119.4 (11)
CA_3—CB_3—HB1_3	110.6	CG_10—CD2_10—HD2_10	120.3
CG_3—CB_3—HB1_3	110.5	CE2_10—CD2_10—HD2_10	120.3
CA_3—CB_3—HB2_3	110.6	CZ_10—CE1_10—CD1_10	120.1 (12)
CG_3—CB_3—HB2_3	110.6	CZ_10—CE1_10—HE1_10	120.0
HB1_3—CB_3—HB2_3	108.7	CD1_10—CE1_10—HE1_10	120.0
CD_3—CG_3—CB_3	111.3 (19)	CZ_10—CE2_10—CD2_10	122.1 (12)
CD_3—CG_3—HG1_3	109.4	CZ_10—CE2_10—HE2_10	119.0
CB_3—CG_3—HG1_3	109.4	CD2_10—CE2_10—HE2_10	119.0
CD_3—CG_3—HG2_3	109.4	CE1_10—CZ_10—CE2_10	118.0 (12)
CB_3—CG_3—HG2_3	109.4	CE1_10—CZ_10—HZ_10	121.0
HG1_3—CG_3—HG2_3	108.0	CE2_10—CZ_10—HZ_10	121.0
NZ_3—CD_3—CG_3	110.5 (19)	O_10—C_10—N_1	122.4 (7)
NZ_3—CD_3—HD1_3	109.6	O_10—C_10—CA_10	118.4 (7)
CG_3—CD_3—HD1_3	109.5	N_1—C_10—CA_10	119.2 (8)
NZ_3—CD_3—HD2_3	109.5	C_25^i—N_21—CA_21	120.5 (8)
CG_3—CD_3—HD2_3	109.6	C_25^i—N_21—CD_21	127.2 (7)
HD1_3—CD_3—HD2_3	108.1	CA_21—N_21—CD_21	112.2 (7)
CD_3—NZ_3—HZ1_3	109.5	N_21—CA_21—C_21	115.3 (7)
CD_3—NZ_3—HZ2_3	109.5	N_21—CA_21—CB_21	101.3 (8)
HZ1_3—NZ_3—HZ2_3	109.5	C_21—CA_21—CB_21	109.1 (8)
CD_3—NZ_3—HZ3_3	109.5	N_21—CA_21—HA_21	110.3
HZ1_3—NZ_3—HZ3_3	109.5	C_21—CA_21—HA_21	110.3
HZ2_3—NZ_3—HZ3_3	109.5	CB_21—CA_21—HA_21	110.3
O_3—C_3—N_4	123.9 (12)	CG_21—CB_21—CA_21	104.0 (8)
O_3—C_3—CA_3	118.7 (12)	CG_21—CB_21—HB1_21	110.9
N_4—C_3—CA_3	117.4 (9)	CA_21—CB_21—HB1_21	110.9
C_3—N_4—CA_4	122.6 (10)	CG_21—CB_21—HB2_21	111.0
C_3—N_4—H0_4	118.7	CA_21—CB_21—HB2_21	111.0
CA_4—N_4—H0_4	118.7	HB1_21—CB_21—HB2_21	109.0
N_4—CA_4—C_4	104.4 (10)	CB_21—CG_21—CD_21	103.9 (11)
N_4—CA_4—CB_4	115.1 (12)	CB_21—CG_21—HG1_21	111.0
C_4—CA_4—CB_4	114.3 (13)	CD_21—CG_21—HG1_21	111.0
N_4—CA_4—HA_4	107.5	CB_21—CG_21—HG2_21	111.0
C_4—CA_4—HA_4	107.6	CD_21—CG_21—HG2_21	111.0
CB_4—CA_4—HA_4	107.5	HG1_21—CG_21—HG2_21	109.0
CA_4—CB_4—CG_4	114.1 (15)	CG_21—CD_21—N_21	102.5 (8)
CA_4—CB_4—HB1_4	108.7	CG_21—CD_21—HD1_21	111.3
CG_4—CB_4—HB1_4	108.7	N_21—CD_21—HD1_21	111.3
CA_4—CB_4—HB2_4	108.7	CG_21—CD_21—HD2_21	111.3
CG_4—CB_4—HB2_4	108.7	N_21—CD_21—HD2_21	111.3
HB1_4—CB_4—HB2_4	107.6	HD1_21—CD_21—HD2_21	109.2
CD2_4—CG_4—CD1_4	112 (2)	O_21—C_21—N_22	124.1 (7)
CD2_4—CG_4—CB_4	112.0 (19)	O_21—C_21—CA_21	118.7 (7)
CD1_4—CG_4—CB_4	108.7 (16)	N_22—C_21—CA_21	117.2 (7)
CD2_4—CG_4—HG_4	108.0	C_21—N_22—CA_22	121.7 (6)
CD1_4—CG_4—HG_4	108.0	C_21—N_22—H0_22	119.2
CB_4—CG_4—HG_4	107.9	CA_22—N_22—H0_22	119.2
CG_4—CD1_4—HD1A_4	109.5	N_22—CA_22—CB_22	110.5 (6)
CG_4—CD1_4—HD1B_4	109.5	N_22—CA_22—C_22	108.2 (6)
HD1A_4—CD1_4—HD1B_4	109.5	CB_22—CA_22—C_22	107.9 (7)
CG_4—CD1_4—HD1C_4	109.5	N_22—CA_22—HA_22	110.0
HD1A_4—CD1_4—HD1C_4	109.5	CB_22—CA_22—HA_22	110.0
HD1B_4—CD1_4—HD1C_4	109.5	C_22—CA_22—HA_22	110.0
CG_4—CD2_4—HD2A_4	109.5	CG1_22—CB_22—CA_22	112.4 (9)
CG_4—CD2_4—HD2B_4	109.5	CG1_22—CB_22—CG2_22	112.2 (11)
HD2A_4—CD2_4—HD2B_4	109.5	CA_22—CB_22—CG2_22	108.4 (9)
CG_4—CD2_4—HD2C_4	109.5	CG1_22—CB_22—HB_22	107.9
HD2A_4—CD2_4—HD2C_4	109.5	CA_22—CB_22—HB_22	107.9
HD2B_4—CD2_4—HD2C_4	109.5	CG2_22—CB_22—HB_22	107.9
O_4—C_4—N_5	123.0 (12)	CB_22—CG1_22—HG1A_22	109.5
O_4—C_4—CA_4	119.9 (11)	CB_22—CG1_22—HG1B_22	109.5
N_5—C_4—CA_4	117.1 (11)	HG1A_22—CG1_22—HG1B_22	109.5
C_4—N_5—CA_5	120.5 (11)	CB_22—CG1_22—HG1C_22	109.5
C_4—N_5—H0_5	119.7	HG1A_22—CG1_22—HG1C_22	109.5
CA_5—N_5—H0_5	119.7	HG1B_22—CG1_22—HG1C_22	109.5
N_5—CA_5—C_5	110.9 (9)	CB_22—CG2_22—HG2A_22	109.5
N_5—CA_5—CB_5	110.4 (10)	CB_22—CG2_22—HG2B_22	109.5
C_5—CA_5—CB_5	107.9 (10)	HG2A_22—CG2_22—HG2B_22	109.5
N_5—CA_5—HA_5	109.2	CB_22—CG2_22—HG2C_22	109.5
C_5—CA_5—HA_5	109.2	HG2A_22—CG2_22—HG2C_22	109.5
CB_5—CA_5—HA_5	109.2	HG2B_22—CG2_22—HG2C_22	109.5
CG_5—CB_5—CA_5	109.4 (10)	O_22—C_22—N_23	122.3 (8)
CG_5—CB_5—HB1_5	109.8	O_22—C_22—CA_22	121.2 (7)
CA_5—CB_5—HB1_5	109.8	N_23—C_22—CA_22	116.4 (6)
CG_5—CB_5—HB2_5	109.8	C_22—N_23—CA_23	122.5 (7)
CA_5—CB_5—HB2_5	109.8	C_22—N_23—H0_23	118.8
HB1_5—CB_5—HB2_5	108.2	CA_23—N_23—H0_23	118.8
CD1_5—CG_5—CD2_5	115.0 (14)	N_23—CA_23—C_23	107.8 (7)
CD1_5—CG_5—CB_5	125.9 (17)	N_23—CA_23—CB_23	108.8 (9)
CD2_5—CG_5—CB_5	119.1 (15)	C_23—CA_23—CB_23	111.9 (9)
CG_5—CD1_5—CE1_5	121.1 (17)	N_23—CA_23—HA_23	109.5
CG_5—CD1_5—HD1_5	119.5	C_23—CA_23—HA_23	109.5
CE1_5—CD1_5—HD1_5	119.5	CB_23—CA_23—HA_23	109.4
CE2_5—CD2_5—CG_5	125.8 (18)	CG_23—CB_23—CA_23	114.7 (15)
CE2_5—CD2_5—HD2_5	117.1	CG_23—CB_23—HB1_23	108.6
CG_5—CD2_5—HD2_5	117.1	CA_23—CB_23—HB1_23	108.6
CZ_5—CE1_5—CD1_5	118.1 (17)	CG_23—CB_23—HB2_23	108.6
CZ_5—CE1_5—HE1_5	120.9	CA_23—CB_23—HB2_23	108.6
CD1_5—CE1_5—HE1_5	120.9	HB1_23—CB_23—HB2_23	107.6
CZ_5—CE2_5—CD2_5	116.5 (18)	CD_23—CG_23—CB_23	117.0 (17)
CZ_5—CE2_5—HE2_5	121.7	CD_23—CG_23—HG1_23	108.1
CD2_5—CE2_5—HE2_5	121.8	CB_23—CG_23—HG1_23	108.0
CE2_5—CZ_5—CE1_5	123.4 (19)	CD_23—CG_23—HG2_23	108.0
CE2_5—CZ_5—HZ_5	118.3	CB_23—CG_23—HG2_23	108.0
CE1_5—CZ_5—HZ_5	118.3	HG1_23—CG_23—HG2_23	107.3
O_5—C_5—N_6	122.6 (13)	CG_23—CD_23—NZ_23	106.0 (16)
O_5—C_5—CA_5	119.5 (13)	CG_23—CD_23—HD1_23	110.5
N_6—C_5—CA_5	117.9 (11)	NZ_23—CD_23—HD1_23	110.5
C_5—N_6—CA_6	123.3 (11)	CG_23—CD_23—HD2_23	110.6
C_5—N_6—CD_6	125.6 (10)	NZ_23—CD_23—HD2_23	110.5
CA_6—N_6—CD_6	111.1 (10)	HD1_23—CD_23—HD2_23	108.7
N_6—CA_6—C_6	115.8 (9)	CD_23—NZ_23—HZ1_23	109.5
N_6—CA_6—CB_6	101.1 (10)	CD_23—NZ_23—HZ2_23	109.5
C_6—CA_6—CB_6	110.0 (10)	HZ1_23—NZ_23—HZ2_23	109.5
N_6—CA_6—HA_6	109.9	CD_23—NZ_23—HZ3_23	109.5
C_6—CA_6—HA_6	109.9	HZ1_23—NZ_23—HZ3_23	109.5
CB_6—CA_6—HA_6	109.9	HZ2_23—NZ_23—HZ3_23	109.5
CG_6—CB_6—CA_6	103.5 (11)	O_23—C_23—N_24	123.5 (8)
CG_6—CB_6—HB1_6	111.1	O_23—C_23—CA_23	121.3 (8)
CA_6—CB_6—HB1_6	111.1	N_24—C_23—CA_23	115.2 (7)
CG_6—CB_6—HB2_6	111.1	C_23—N_24—CA_24	125.5 (7)
CA_6—CB_6—HB2_6	111.1	C_23—N_24—H0_24	117.3
HB1_6—CB_6—HB2_6	109.0	CA_24—N_24—H0_24	117.3
CD_6—CG_6—CB_6	103.8 (13)	N_24—CA_24—C_24	107.1 (7)
CD_6—CG_6—HG1_6	111.0	N_24—CA_24—CB_24	109.2 (9)
CB_6—CG_6—HG1_6	111.0	C_24—CA_24—CB_24	111.0 (9)
CD_6—CG_6—HG2_6	111.0	N_24—CA_24—HA_24	109.8
CB_6—CG_6—HG2_6	111.0	C_24—CA_24—HA_24	109.8
HG1_6—CG_6—HG2_6	109.0	CB_24—CA_24—HA_24	109.8
CG_6—CD_6—N_6	105.0 (11)	CGa_24—CB_24—CA_24	122.0 (12)
CG_6—CD_6—HD1_6	110.7	CGb_24—CB_24—CA_24	103.5 (13)
N_6—CD_6—HD1_6	110.7	CB_24—CGa_24—CD2a_24	106.7 (16)
CG_6—CD_6—HD2_6	110.7	CB_24—CGa_24—CD1a_24	118.4 (14)
N_6—CD_6—HD2_6	110.8	CD2a_24—CGa_24—CD1a_24	106.9 (17)
HD1_6—CD_6—HD2_6	108.8	CD1b_24—CGb_24—CD2b_24	115 (2)
O_6—C_6—N_7	124.1 (9)	CD1b_24—CGb_24—CB_24	110.5 (18)
O_6—C_6—CA_6	119.1 (10)	CD2b_24—CGb_24—CB_24	102 (2)
N_7—C_6—CA_6	116.9 (9)	O_24—C_24—N_25	121.3 (8)
C_6—N_7—CA_7	120.1 (8)	O_24—C_24—CA_24	119.7 (8)
C_6—N_7—H0_7	119.9	N_25—C_24—CA_24	119.0 (8)
CA_7—N_7—H0_7	119.9	C_24—N_25—CA_25	119.9 (8)
N_7—CA_7—C_7	111.0 (8)	C_24—N_25—H0_25	120.0
N_7—CA_7—CB_7	110.1 (8)	CA_25—N_25—H0_25	120.0
C_7—CA_7—CB_7	110.0 (8)	N_25—CA_25—C_25	109.7 (7)
N_7—CA_7—HA_7	108.6	N_25—CA_25—CB_25	109.1 (8)
C_7—CA_7—HA_7	108.6	C_25—CA_25—CB_25	109.1 (8)
CB_7—CA_7—HA_7	108.6	N_25—CA_25—HA_25	109.6
CG2_7—CB_7—CG1_7	109.5 (13)	C_25—CA_25—HA_25	109.6
CG2_7—CB_7—CA_7	111.9 (11)	CB_25—CA_25—HA_25	109.6
CG1_7—CB_7—CA_7	108.1 (10)	CG_25—CB_25—CA_25	108.9 (8)
CG2_7—CB_7—HB_7	109.1	CG_25—CB_25—HB1_25	109.9
CG1_7—CB_7—HB_7	109.1	CA_25—CB_25—HB1_25	109.9
CA_7—CB_7—HB_7	109.1	CG_25—CB_25—HB2_25	109.9
CB_7—CG1_7—HG1A_7	109.5	CA_25—CB_25—HB2_25	109.9
CB_7—CG1_7—HG1B_7	109.5	HB1_25—CB_25—HB2_25	108.3
HG1A_7—CG1_7—HG1B_7	109.5	CD2_25—CG_25—CD1_25	120.5 (11)
CB_7—CG1_7—HG1C_7	109.5	CD2_25—CG_25—CB_25	124.0 (12)
HG1A_7—CG1_7—HG1C_7	109.5	CD1_25—CG_25—CB_25	115.1 (12)
HG1B_7—CG1_7—HG1C_7	109.5	CG_25—CD1_25—CE1_25	119.8 (14)
CB_7—CG2_7—HG2A_7	109.5	CG_25—CD1_25—HD1_25	120.1
CB_7—CG2_7—HG2B_7	109.5	CE1_25—CD1_25—HD1_25	120.1
HG2A_7—CG2_7—HG2B_7	109.5	CG_25—CD2_25—CE2_25	122.3 (13)
CB_7—CG2_7—HG2C_7	109.5	CG_25—CD2_25—HD2_25	118.9
HG2A_7—CG2_7—HG2C_7	109.5	CE2_25—CD2_25—HD2_25	118.9
HG2B_7—CG2_7—HG2C_7	109.5	CZ_25—CE1_25—CD1_25	116.5 (15)
O_7—C_7—N_8	123.8 (10)	CZ_25—CE1_25—HE1_25	121.7
O_7—C_7—CA_7	121.1 (9)	CD1_25—CE1_25—HE1_25	121.7
N_8—C_7—CA_7	115.1 (7)	CD2_25—CE2_25—CZ_25	115.8 (14)
C_7—N_8—CA_8	123.3 (7)	CD2_25—CE2_25—HE2_25	122.1
C_7—N_8—H0_8	118.3	CZ_25—CE2_25—HE2_25	122.1
CA_8—N_8—H0_8	118.3	CE1_25—CZ_25—CE2_25	124.8 (15)
N_8—CA_8—C_8	108.1 (7)	CE1_25—CZ_25—HZ_25	117.6
N_8—CA_8—CB_8	110.2 (8)	CE2_25—CZ_25—HZ_25	117.6
C_8—CA_8—CB_8	110.2 (8)	O_25—C_25—N_21^i	123.9 (8)
N_8—CA_8—HA_8	109.5	O_25—C_25—CA_25	118.6 (9)
C_8—CA_8—HA_8	109.5	N_21^i—C_25—CA_25	117.5 (8)
CB_8—CA_8—HA_8	109.5	O2_51—C1_51—O1_51	129.5 (17)
CGb_8—CB_8—CA_8	117.0 (17)	O2_51—C1_51—C2_51	118.9 (14)
CGa_8—CB_8—CA_8	119.2 (13)	O1_51—C1_51—C2_51	111.3 (14)
CGa_8—CB_8—HB1_8	107.5	F1_51—C2_51—F2_51	108.8 (12)
CA_8—CB_8—HB1_8	107.5	F1_51—C2_51—F3_51	104.8 (12)
CGb_8—CB_8—HB2_8	110.3	F2_51—C2_51—F3_51	101.3 (13)
CGa_8—CB_8—HB2_8	107.5	F1_51—C2_51—C1_51	113.5 (11)
CA_8—CB_8—HB2_8	107.5	F2_51—C2_51—C1_51	117.1 (12)
HB1_8—CB_8—HB2_8	107.0	F3_51—C2_51—C1_51	109.8 (12)
CGa_8—CB_8—HB3_8	108.0	O2_52—C1_52—O1_52	127 (3)
CGb_8—CB_8—HB3_8	108.0	O2_52—C1_52—C2_52	119 (2)
CA_8—CB_8—HB3_8	108.1	O1_52—C1_52—C2_52	114 (2)
HB1_8—CB_8—HB3_8	104.5	F1_52—C2_52—F2_52	108 (2)
CGb_8—CB_8—HB4_8	108.1	F1_52—C2_52—F3_52	104 (2)
CA_8—CB_8—HB4_8	108.1	F2_52—C2_52—F3_52	106 (2)
CDa_8—CGa_8—CB_8	111.0 (17)	F1_52—C2_52—C1_52	115 (2)
HG1_8—CGa_8—HG2_8	108.0	F2_52—C2_52—C1_52	117 (2)
CGa_8—CDa_8—NZa_8	113.5 (19)	F3_52—C2_52—C1_52	106 (2)

Symmetry code: (i) −x+4/3, −x+y+2/3, −z+2/3.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N_2—H0_2···O_9	0.88	2.11	2.939 (9)	157
N_3—H0_3···O_1^ii	0.88	2.03	2.889 (10)	164
NZ_3—HZ1_3···O_105^iii	0.91	2.45	3.14 (5)	133
NZ_3—HZ2_3···O_5	0.91	2.18	2.66 (3)	112
N_4—H0_4···O_7	0.88	2.06	2.912 (13)	161
N_5—H0_5···O_101	0.88	2.06	2.94 (2)	177
N_7—H0_7···O_4	0.88	2.19	3.045 (14)	163
N_8—H0_8···O_23	0.88	2.03	2.896 (10)	167
NZa_8—HZ1_8···O_112	0.91	2.08	2.91 (7)	152
NZa_8—HZ1_8···O_107	0.91	2.58	3.26 (4)	132
NZa_8—HZ2_8···O_10	0.91	1.84	2.75 (3)	173
NZa_8—HZ3_8···O_106	0.91	2.06	2.89 (5)	151
N_9—H0_9···O_2	0.88	2.01	2.872 (9)	166
N_10—H0_10···O_21	0.88	2.05	2.908 (9)	166
N_22—H0_22···O_24^i	0.88	2.14	2.994 (9)	164
N_23—H0_23···O_8	0.88	2.00	2.868 (9)	167
NZ_23—HZ1_23···O1_52	0.91	1.80	2.69 (3)	165
NZ_23—HZ1_23···F2_52	0.91	2.54	3.06 (4)	117
NZ_23—HZ2_23···O_25	0.91	1.77	2.66 (2)	165
NZ_23—HZ3_23···O_105	0.91	2.74	3.46 (4)	138
N_24—H0_24···O_22^i	0.88	1.99	2.861 (9)	169
N_25—H0_25···O_102	0.88	2.18	2.98 (2)	150

Symmetry codes: (i) −x+4/3, −x+y+2/3, −z+2/3; (ii) x−y, −y, −z; (iii) y+2/3, x−2/3, −z+1/3.