Boc-Pro-Hyp-Gly-OBzl and Boc-Ala-Hyp-Gly-OBzl, two repeating triplets found in collagen

The protected tripeptides benzyl N-{2-[N-(tert-butoxy­carbon­yl)­prol­yl]-4-hydroxy­prol­yl}glycinate or Boc-Pro-Hyp-Gly-OBzl, C₂₄H₃₃N₃O₇, and benzyl N-{2-[N-(tert-butoxy­carbon­yl)­alan­yl]-4-hydroxy­prol­yl}glycinate or Boc-Ala-Hyp-Gly-OBzl, C₂₂H₃₁N₃O₇, are the minimum repeating triplets found in collagen. Within the crystal structure of each are two independent peptide mol­ecules with similar structures. The peptides are arranged anti­parallel to one another and inter­act through hydrogen bonds involving the main chains and the 4-hydroxy­prolyl groups. The structures exhibit characteristics of a triple helix, but the peptides tend to assume a sheet-like structure.

S1. Comment

Collagen contains a characteristic amino acid sequence in which a Gly residue appears at every third position (X–Y–Gly). Moreover, the Pro–Hyp–Gly triplet (Hyp is 4-hydroxyproline) is frequently found as a repeating sequence, and earlier structural studies carried out with synthetic polypeptides [(Pro–Hyp–Gly)_n] indicate that this repeating sequence assumes a triple-helical structure (Okuyama et al., 1998; Berisio et al., 2001; Okuyama et al., 2004). Here the protected triplet tert-butyloxycarbonyl—Pro–Hyp–Gly benzyl ester or Boc–Pro–Hyp–Gly–OBzl, (I), was used to investigate the structural characteristics of the collagen minimum repeating sequence. In addition, because (Ala–Hyp–Gly)_n also shows collagen-like optical properties (Rao & Adams, 1979), the structure of Boc–Ala–Hyp–Gly–OBzl, (II), was used to investigate the contribution made by imino acids to the structure of the sequence.

For both (I) and (II), two independent peptide molecules (molecules A and B) are present in the crystal structure, where they are arranged antiparallel to one another and were slightly bent (Figs.1 and 2). Within the triple-helix of (Pro–Hyp–Gly)₁₀, the averaged (φ, ψ) are approximately (-70°, 162°), (-57°, 150°) and (-71°, 173°) for the Pro, Hyp and Gly residues, respectively (Okuyama et al., 2004). Neither (I) nor (II) assume a triple-helical structure, though the torsion angles suggest conformational similarity to a triple helix, despite slight differences at the Ala residues of (II) (Table 1). The torsion angles also show structural similarity among (IA), (IB), (IIA) and (IIB). Molecular fitting revealed large deviations at the terminal tert-butyloxycarbonyl and benzyl ester groups (Fig. 3), but the conformation of the main chain was conserved among the four molecules. In addition, Hyp is an imino acid showing ring-puckering with the amplitudes q₂ (Cremer & Pople, 1975) of 0.340 (5)–0.409 (5) Å. The ring-puckering parameter φ₂ (N30—C30—C31—C32—C33) of 80.6 (7)° in (IA) differs from that of the other three molecules (Table 1). Nevertheless, the main chain conformation around the Hyp unit of (IA) is similar to that of the other molecules.

These peptide molecules, with their similar conformations, make up a sheet-like structure in the solid state (Figs. 4 and 5). Within the packing of (I), four hydrogen bonds are formed (Table 2); two are formed between the main chains (N40A···O32B and N40B···O24A); the remaining two involve the 4-hydroxy groups (O32). Atom O32B interacts with atoms N40A and O34B, acting as a hydrogen-bond acceptor and donor, respectively. By contrast, atom O32A acts only as a donor. Such hydroxyl group-related interactions contribute to the stabilization of the sheet-like structure of (I) (Fig. 4). Within (II), on the other hand, amide groups are situated within hydrogen-bonding range of the Ala and Gly residues (N20 and N40), so that four of the six hydrogen bonds formed are between the main chains (Table 2), which stabilizes the sheet-like structure (Fig. 5). Increases in such main chain–main chain interactions might be expected to affect the peptide structure, but superimposition showed only a slight deviation between Pro of (I) and Ala of (II) (Fig. 3). A different hydrogen-bonding mode also is observed for the hydroxyl groups of (II) (O32A and O32B). Within the triple helix of (Pro–Hyp–Gly)₁₀, the 4-hydroxy groups of Hyp participate in hydrogen bonds with solvent molecules and intertriple helices, but not in interstrand interactions (Berisio et al., 2001; Kishimoto et al., 2005). It also was suggested that the 4-position of Hyp shows an inductive effect from 4-fluoroproline incorporated collagen-like peptide (Holmgren et al., 1998). It is noteworthy that the 4-hydroxy groups in both (I) and (II) play different roles in the hydrogen-bonding of molecules A and B.

S2. Experimental

Compounds (I) and (II) were synthesized by the conventional liquid phase method, and purified by silica gel column chromatography. Crystals were grown from methanol and ethyl acetate solutions.

S3. Refinement

H atoms were placed at calculated positions (C—H = 0.95–1.00 A and N—H = 0.88 A), with isotropic displacement parameters [U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(parent atom) for all other atoms], and included in the structure-factor calculation. H atoms of hydroxy groups were found in a differential Fourier map considering the hydrogen-bonding network, and refined. Restraints for displacement parameters were applied for (I) and (II) using SIMU and DELU instructions of SHELXL97 (Sheldrick, 1997). In the absence of significant anomalous scattering effects, Friedel pairs were merged, and the absolute configuration is assumed from that of the starting material.

Computing details

For both compounds, data collection: SMART (Bruker, 1998). Cell refinement: SAINT-Plus (Bruker, 1998) for (I); SMART for (II). For both compounds, data reduction: SAINT-Plus (Bruker, 1998). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for (I); SHELXD (Sheldrick & Gould, 1995) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Structures of Boc–Pro–Hyp–Gly–OBzl (I). Molecules A and B are present in an asymmetric unit. Displacement ellipsoids are drawn at the 40% probability level. Dotted lines represent hydrogen bonds.
	Fig. 2. Structures of Boc–Ala–Hyp–Gly–OBzl (II). Molecules A and B are present in an asymmetric unit. Displacement ellipsoids are drawn at the 40% probability level. Dotted lines represent hydrogen bonds.
	Fig. 3. Stereoview of superimposition of (IA), (IB), (IIA) and (IIB). Molecular fitting was performed for the main chains using ProFit (Martin, 1996). The figure was drawn using RasMol (Bernstein, 2000) and POV-RAY3.5 (POV-Team, 1991). Orange, red, green and blue, represent (IA), (IB), (IIA) and (IIB), respectively. The RMSD were 0.233–0.586 Å.
	Fig. 4. Sheet-like structure of (I). Hydrogen atoms are omitted for clarity. Dotted lines represent hydrogen bonds.
	Fig. 5. Sheet-like structure of (I). Hydrogen atoms are omitted for clarity. Dotted lines represent hydrogen bonds.

(I) benzyl N-{2-[N-(tert-butoxycarbonyl)prolyl]-4-hydroxyprolyl}glycinate

Crystal data

C24H33N3O7	F(000) = 1016
Mr = 475.53	Dx = 1.246 Mg m^−3
MonoclinicP21	Mo Kα radiation, λ = 0.71073 Å
a = 8.922 (2) Å	Cell parameters from 8042 reflections
b = 15.208 (3) Å	θ = 2.3–28.3°
c = 18.692 (4) Å	µ = 0.09 mm^−1
β = 91.523 (3)°	T = 200 K
V = 2535.1 (9) Å^3	Plate, colorless
Z = 4	0.45 × 0.30 × 0.08 mm

Data collection

Bruker SMART APEX area-detector diffractometer	5790 independent reflections
Radiation source: MacScience, M18XCE rotating anode	4804 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 8.366 pixels mm^-1	θmax = 27.1°, θmin = 2.2°
ω–scan	h = −11→11
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −19→19
Tmin = 0.883, Tmax = 0.993	l = −22→23
21865 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0823P)^2 + 1.2083P] where P = (Fo^2 + 2Fc^2)/3
5790 reflections	(Δ/σ)max = 0.004
627 parameters	Δρmax = 0.51 e Å^−3
279 restraints	Δρmin = −0.46 e Å^−3

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
C10A	0.1898 (7)	0.7171 (4)	0.8541 (3)	0.0615 (9)
C11A	0.2185 (10)	0.7811 (5)	0.9146 (4)	0.0784 (14)
H11A	0.3153	0.7677	0.9381	0.118*
H12A	0.1387	0.7759	0.9493	0.118*
H13A	0.2203	0.8411	0.8956	0.118*
C12A	0.1916 (9)	0.6225 (4)	0.8802 (4)	0.0721 (13)
H14A	0.1785	0.5828	0.8392	0.108*
H15A	0.1098	0.6136	0.9134	0.108*
H16A	0.2877	0.6102	0.9048	0.108*
C13A	0.0475 (8)	0.7352 (5)	0.8119 (4)	0.0743 (13)
H17A	0.0425	0.7979	0.7997	0.111*
H18A	−0.0389	0.7195	0.8405	0.111*
H19A	0.0461	0.7002	0.7678	0.111*
O10A	0.3186 (4)	0.7175 (2)	0.8062 (2)	0.0545 (7)
C14A	0.3547 (6)	0.7912 (3)	0.7710 (3)	0.0473 (9)
O14A	0.2909 (4)	0.8618 (2)	0.77444 (19)	0.0521 (9)
N20A	0.4764 (5)	0.7774 (3)	0.7314 (2)	0.0428 (7)
C20A	0.5264 (5)	0.8455 (3)	0.6829 (3)	0.0407 (7)
H20A	0.5411	0.9028	0.7084	0.049*
C21A	0.6771 (6)	0.8082 (3)	0.6573 (3)	0.0482 (8)
H21A	0.6996	0.8297	0.6088	0.058*
H22A	0.7607	0.8241	0.6906	0.058*
C22A	0.6494 (6)	0.7098 (4)	0.6571 (3)	0.0530 (8)
H23A	0.7452	0.6769	0.6600	0.064*
H24A	0.5926	0.6915	0.6134	0.064*
C23A	0.5581 (6)	0.6946 (3)	0.7236 (3)	0.0492 (8)
H25A	0.4882	0.6446	0.7168	0.059*
H26A	0.6241	0.6831	0.7660	0.059*
C24A	0.4190 (4)	0.8553 (3)	0.6189 (2)	0.0308 (8)
O24A	0.3301 (4)	0.7964 (2)	0.60153 (18)	0.0420 (7)
N30A	0.4309 (4)	0.9286 (2)	0.58009 (18)	0.0317 (7)
C30A	0.3524 (4)	0.9366 (3)	0.5105 (2)	0.0293 (8)
H30A	0.2442	0.9204	0.5138	0.035*
C31A	0.3711 (5)	1.0344 (3)	0.4919 (2)	0.0348 (9)
H33A	0.3724	1.0432	0.4395	0.042*
H34A	0.2891	1.0699	0.5118	0.042*
C32A	0.5211 (5)	1.0585 (3)	0.5267 (2)	0.0358 (9)
H35A	0.6044	1.0420	0.4946	0.043*
O32A	0.5263 (5)	1.1497 (2)	0.5416 (2)	0.0506 (9)
H32A	0.608 (9)	1.159 (6)	0.558 (4)	0.08 (2)*
C33A	0.5297 (5)	1.0032 (3)	0.5953 (2)	0.0378 (9)
H36A	0.6336	0.9832	0.6056	0.045*
H37A	0.4944	1.0373	0.6368	0.045*
C34A	0.4299 (4)	0.8809 (3)	0.4547 (2)	0.0314 (8)
O34A	0.5656 (3)	0.8718 (2)	0.45508 (18)	0.0442 (8)
N40A	0.3379 (4)	0.8482 (2)	0.40296 (18)	0.0323 (7)
H40A	0.2400	0.8505	0.4074	0.039*
C40A	0.4018 (5)	0.8091 (3)	0.3400 (2)	0.0352 (9)
H41A	0.3223	0.7772	0.3127	0.042*
H42A	0.4793	0.7658	0.3551	0.042*
C41A	0.4713 (5)	0.8767 (3)	0.2920 (2)	0.0376 (9)
O41A	0.4710 (4)	0.9544 (2)	0.30004 (18)	0.0460 (8)
C51A	0.6730 (7)	0.8343 (4)	0.1295 (3)	0.0631 (9)
C52A	0.6511 (8)	0.8494 (5)	0.0573 (3)	0.0724 (10)
H52A	0.5841	0.8940	0.0409	0.087*
C53A	0.7284 (9)	0.7985 (5)	0.0086 (4)	0.0793 (10)
H53A	0.7161	0.8100	−0.0411	0.095*
C54A	0.8207 (9)	0.7330 (5)	0.0308 (4)	0.0791 (10)
H54A	0.8724	0.6992	−0.0035	0.095*
C55A	0.8402 (8)	0.7150 (5)	0.1013 (4)	0.0756 (10)
H55A	0.9040	0.6683	0.1166	0.091*
C56A	0.7655 (8)	0.7658 (5)	0.1511 (4)	0.0685 (9)
H56A	0.7783	0.7532	0.2007	0.082*
C57A	0.6005 (7)	0.8920 (4)	0.1836 (3)	0.0593 (10)
H57A	0.6760	0.9316	0.2062	0.071*
H58A	0.5215	0.9285	0.1601	0.071*
O57A	0.5353 (4)	0.8356 (2)	0.23733 (18)	0.0507 (9)
C10B	0.3631 (8)	0.5902 (5)	0.1387 (4)	0.0745 (10)
C11B	0.3932 (10)	0.5070 (6)	0.0961 (5)	0.0968 (17)
H11B	0.3969	0.4563	0.1285	0.145*
H12B	0.4892	0.5126	0.0723	0.145*
H13B	0.3126	0.4985	0.0601	0.145*
C12B	0.4851 (8)	0.6046 (6)	0.1940 (4)	0.0790 (14)
H14B	0.4632	0.6576	0.2216	0.119*
H15B	0.5811	0.6118	0.1704	0.119*
H16B	0.4907	0.5538	0.2262	0.119*
C13B	0.3363 (10)	0.6696 (6)	0.0899 (4)	0.0915 (16)
H17B	0.2421	0.6617	0.0624	0.137*
H18B	0.4194	0.6750	0.0569	0.137*
H19B	0.3303	0.7230	0.1190	0.137*
O10B	0.2244 (5)	0.5675 (3)	0.1750 (2)	0.0666 (9)
C14B	0.1577 (7)	0.6243 (4)	0.2184 (3)	0.0568 (10)
O14B	0.1849 (5)	0.7025 (2)	0.22351 (19)	0.0548 (9)
N20B	0.0521 (5)	0.5825 (3)	0.2557 (2)	0.0493 (8)
C20B	−0.0284 (6)	0.6293 (4)	0.3101 (3)	0.0505 (8)
H20B	−0.0782	0.6832	0.2902	0.061*
C21B	−0.1448 (7)	0.5589 (4)	0.3304 (3)	0.0591 (9)
H21B	−0.1797	0.5682	0.3797	0.071*
H22B	−0.2324	0.5597	0.2968	0.071*
C22B	−0.0588 (7)	0.4737 (4)	0.3247 (3)	0.0608 (9)
H23B	0.0067	0.4641	0.3676	0.073*
H24B	−0.1277	0.4230	0.3189	0.073*
C23B	0.0321 (7)	0.4864 (4)	0.2593 (3)	0.0564 (8)
H25B	0.1300	0.4561	0.2642	0.068*
H26B	−0.0220	0.4641	0.2160	0.068*
C24B	0.0710 (4)	0.6507 (3)	0.3754 (2)	0.0310 (8)
O24B	0.1973 (3)	0.6196 (2)	0.38248 (17)	0.0379 (7)
N30B	0.0105 (4)	0.7009 (2)	0.42616 (18)	0.0284 (7)
C30B	0.0859 (4)	0.7103 (2)	0.4962 (2)	0.0261 (7)
H30B	0.1883	0.7356	0.4903	0.031*
C31B	−0.0138 (5)	0.7770 (3)	0.5351 (2)	0.0349 (9)
H33B	−0.0894	0.7467	0.5641	0.042*
H34B	0.0472	0.8162	0.5666	0.042*
C32B	−0.0877 (5)	0.8280 (3)	0.4740 (2)	0.0341 (9)
H35B	−0.1801	0.8592	0.4894	0.041*
O32B	0.0170 (3)	0.8873 (2)	0.44220 (18)	0.0361 (7)
H32B	−0.002 (7)	0.932 (5)	0.456 (3)	0.051 (17)*
C33B	−0.1240 (5)	0.7568 (3)	0.4193 (3)	0.0374 (9)
H36B	−0.2158	0.7241	0.4314	0.045*
H37B	−0.1360	0.7814	0.3704	0.045*
C34B	0.0976 (4)	0.6228 (3)	0.5362 (2)	0.0285 (8)
O34B	0.0298 (4)	0.55642 (18)	0.51501 (17)	0.0380 (7)
N40B	0.1823 (4)	0.6256 (2)	0.59588 (19)	0.0337 (7)
H40B	0.2316	0.6741	0.6067	0.040*
C40B	0.1953 (5)	0.5504 (3)	0.6437 (2)	0.0361 (9)
H41B	0.2729	0.5628	0.6812	0.043*
H42B	0.2283	0.4985	0.6163	0.043*
C41B	0.0480 (5)	0.5292 (3)	0.6791 (2)	0.0366 (9)
O41B	−0.0662 (4)	0.5669 (3)	0.6690 (2)	0.0581 (10)
C51B	−0.1203 (7)	0.4565 (4)	0.8193 (3)	0.0578 (8)
C52B	−0.2195 (7)	0.5258 (4)	0.8224 (3)	0.0623 (9)
H52B	−0.2551	0.5527	0.7793	0.075*
C53B	−0.2680 (8)	0.5568 (5)	0.8876 (3)	0.0690 (10)
H53B	−0.3355	0.6050	0.8889	0.083*
C54B	−0.2193 (8)	0.5182 (5)	0.9497 (4)	0.0726 (10)
H54B	−0.2581	0.5370	0.9940	0.087*
C55B	−0.1136 (9)	0.4519 (5)	0.9486 (4)	0.0746 (10)
H55B	−0.0743	0.4277	0.9921	0.089*
C56B	−0.0657 (8)	0.4210 (5)	0.8831 (3)	0.0686 (9)
H56B	0.0057	0.3746	0.8820	0.082*
C57B	−0.0745 (7)	0.4206 (4)	0.7481 (3)	0.0537 (9)
H57B	−0.0618	0.3562	0.7523	0.064*
H58B	−0.1561	0.4318	0.7124	0.064*
O57B	0.0647 (4)	0.4588 (2)	0.72201 (17)	0.0406 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C10A	0.0779 (19)	0.0504 (17)	0.0576 (18)	−0.0011 (17)	0.0255 (15)	0.0054 (15)
C11A	0.109 (4)	0.066 (3)	0.061 (3)	−0.008 (3)	0.029 (2)	−0.004 (2)
C12A	0.094 (3)	0.057 (2)	0.067 (3)	−0.010 (2)	0.025 (3)	0.013 (2)
C13A	0.072 (2)	0.064 (3)	0.087 (3)	0.000 (2)	0.021 (2)	0.002 (3)
O10A	0.0694 (16)	0.0428 (15)	0.0523 (15)	0.0063 (14)	0.0190 (13)	0.0108 (12)
C14A	0.059 (2)	0.0384 (18)	0.0454 (19)	0.0095 (17)	0.0130 (16)	0.0090 (15)
O14A	0.064 (2)	0.0401 (18)	0.054 (2)	0.0143 (16)	0.0202 (16)	0.0071 (15)
N20A	0.0444 (15)	0.0343 (14)	0.0501 (16)	0.0107 (12)	0.0063 (12)	0.0065 (12)
C20A	0.0393 (15)	0.0345 (14)	0.0486 (16)	0.0062 (13)	0.0058 (13)	0.0024 (13)
C21A	0.0424 (16)	0.0422 (16)	0.0605 (17)	0.0088 (14)	0.0083 (14)	0.0023 (15)
C22A	0.0504 (17)	0.0432 (16)	0.0661 (18)	0.0127 (14)	0.0107 (14)	0.0011 (15)
C23A	0.0499 (17)	0.0372 (15)	0.0608 (17)	0.0132 (14)	0.0063 (15)	0.0052 (14)
C24A	0.0289 (18)	0.0271 (18)	0.037 (2)	0.0000 (15)	0.0064 (15)	−0.0032 (16)
O24A	0.0449 (17)	0.0277 (14)	0.0532 (18)	−0.0100 (13)	−0.0017 (14)	0.0008 (13)
N30A	0.0326 (17)	0.0297 (17)	0.0327 (17)	−0.0085 (14)	−0.0006 (13)	−0.0022 (13)
C30A	0.0258 (17)	0.0254 (18)	0.037 (2)	−0.0039 (14)	0.0015 (15)	−0.0012 (15)
C31A	0.037 (2)	0.029 (2)	0.038 (2)	0.0003 (16)	0.0063 (17)	−0.0003 (16)
C32A	0.038 (2)	0.0250 (19)	0.045 (2)	−0.0049 (17)	0.0077 (18)	0.0007 (17)
O32A	0.057 (2)	0.0249 (15)	0.069 (2)	−0.0093 (15)	−0.0076 (19)	−0.0001 (15)
C33A	0.039 (2)	0.031 (2)	0.043 (2)	−0.0089 (17)	0.0005 (18)	0.0009 (17)
C34A	0.0302 (19)	0.0262 (18)	0.038 (2)	−0.0038 (15)	0.0021 (16)	−0.0011 (16)
O34A	0.0290 (15)	0.0468 (19)	0.0567 (19)	0.0025 (13)	0.0003 (13)	−0.0149 (15)
N40A	0.0292 (16)	0.0313 (17)	0.0365 (17)	−0.0044 (14)	0.0042 (13)	−0.0028 (14)
C40A	0.039 (2)	0.027 (2)	0.040 (2)	−0.0047 (16)	0.0063 (17)	−0.0049 (16)
C41A	0.035 (2)	0.036 (2)	0.042 (2)	−0.0028 (18)	0.0010 (17)	0.0007 (18)
O41A	0.055 (2)	0.0319 (17)	0.0516 (19)	−0.0058 (15)	0.0095 (15)	0.0024 (14)
C51A	0.074 (2)	0.0601 (18)	0.0557 (16)	−0.0069 (16)	0.0213 (15)	0.0031 (15)
C52A	0.091 (2)	0.070 (2)	0.0571 (17)	−0.0026 (18)	0.0205 (17)	0.0009 (17)
C53A	0.099 (2)	0.077 (2)	0.0625 (18)	−0.003 (2)	0.0242 (18)	−0.0038 (18)
C54A	0.092 (2)	0.075 (2)	0.0708 (19)	−0.0027 (19)	0.0276 (19)	−0.0079 (19)
C55A	0.083 (2)	0.072 (2)	0.0732 (19)	−0.0008 (18)	0.0221 (19)	−0.0056 (18)
C56A	0.076 (2)	0.066 (2)	0.0643 (18)	−0.0018 (17)	0.0181 (17)	−0.0007 (17)
C57A	0.070 (2)	0.056 (2)	0.0527 (19)	−0.0085 (19)	0.0224 (19)	0.0058 (18)
O57A	0.069 (2)	0.0378 (18)	0.0463 (18)	−0.0081 (16)	0.0245 (16)	−0.0007 (14)
C10B	0.085 (2)	0.079 (2)	0.0612 (19)	−0.0277 (19)	0.0275 (16)	−0.0165 (16)
C11B	0.103 (4)	0.103 (3)	0.086 (3)	−0.024 (3)	0.039 (3)	−0.038 (3)
C12B	0.080 (3)	0.081 (3)	0.077 (3)	−0.021 (3)	0.018 (2)	−0.011 (2)
C13B	0.102 (4)	0.109 (3)	0.065 (3)	−0.022 (3)	0.029 (3)	0.007 (2)
O10B	0.0814 (19)	0.0641 (19)	0.0554 (16)	−0.0307 (16)	0.0230 (14)	−0.0219 (14)
C14B	0.074 (2)	0.055 (2)	0.043 (2)	−0.0295 (19)	0.0145 (17)	−0.0153 (17)
O14B	0.078 (3)	0.0388 (18)	0.0476 (19)	−0.0198 (18)	0.0017 (17)	−0.0002 (15)
N20B	0.0562 (16)	0.0526 (17)	0.0394 (14)	−0.0184 (15)	0.0039 (13)	−0.0029 (13)
C20B	0.0505 (18)	0.0618 (18)	0.0391 (16)	−0.0172 (16)	0.0021 (14)	−0.0031 (14)
C21B	0.0563 (18)	0.073 (2)	0.0477 (17)	−0.0267 (16)	0.0047 (14)	−0.0055 (16)
C22B	0.0653 (19)	0.0660 (18)	0.0513 (17)	−0.0303 (16)	0.0041 (15)	−0.0003 (16)
C23B	0.0636 (18)	0.0562 (18)	0.0495 (17)	−0.0241 (16)	0.0047 (15)	−0.0023 (15)
C24B	0.0315 (19)	0.0231 (17)	0.038 (2)	−0.0019 (15)	0.0012 (16)	0.0033 (15)
O24B	0.0337 (15)	0.0347 (15)	0.0453 (16)	0.0058 (13)	0.0017 (12)	−0.0027 (13)
N30B	0.0265 (15)	0.0235 (15)	0.0351 (17)	0.0033 (12)	−0.0015 (13)	0.0020 (13)
C30B	0.0242 (17)	0.0197 (16)	0.0344 (19)	−0.0013 (13)	0.0035 (14)	0.0007 (14)
C31B	0.034 (2)	0.028 (2)	0.044 (2)	0.0048 (16)	0.0122 (17)	0.0013 (16)
C32B	0.0270 (18)	0.0231 (18)	0.053 (2)	0.0048 (15)	0.0087 (17)	0.0046 (17)
O32B	0.0345 (15)	0.0180 (13)	0.0565 (19)	0.0023 (12)	0.0104 (13)	0.0025 (13)
C33B	0.0255 (19)	0.029 (2)	0.057 (3)	0.0002 (16)	−0.0024 (18)	0.0043 (19)
C34B	0.0268 (17)	0.0223 (17)	0.037 (2)	0.0007 (14)	0.0054 (15)	0.0015 (15)
O34B	0.0461 (16)	0.0204 (13)	0.0475 (17)	−0.0084 (12)	−0.0018 (13)	0.0024 (12)
N40B	0.0373 (18)	0.0231 (16)	0.0405 (19)	−0.0050 (14)	−0.0036 (15)	0.0052 (14)
C40B	0.037 (2)	0.031 (2)	0.040 (2)	0.0005 (17)	−0.0014 (17)	0.0073 (17)
C41B	0.045 (2)	0.028 (2)	0.037 (2)	−0.0003 (18)	0.0009 (18)	0.0014 (16)
O41B	0.0464 (19)	0.061 (2)	0.067 (2)	0.0206 (18)	0.0162 (17)	0.0206 (19)
C51B	0.0679 (19)	0.0459 (16)	0.0605 (15)	0.0011 (15)	0.0196 (15)	0.0092 (14)
C52B	0.072 (2)	0.0528 (18)	0.0629 (17)	0.0062 (16)	0.0164 (17)	0.0040 (16)
C53B	0.081 (2)	0.060 (2)	0.0662 (18)	0.0068 (17)	0.0196 (17)	0.0005 (16)
C54B	0.089 (2)	0.066 (2)	0.0638 (17)	0.0031 (18)	0.0237 (18)	0.0048 (17)
C55B	0.094 (2)	0.068 (2)	0.0636 (17)	0.0064 (18)	0.0201 (18)	0.0122 (18)
C56B	0.085 (2)	0.0590 (19)	0.0632 (17)	0.0078 (17)	0.0194 (17)	0.0136 (16)
C57B	0.061 (2)	0.0389 (19)	0.0619 (18)	−0.0052 (18)	0.0202 (18)	0.0073 (17)
O57B	0.0419 (17)	0.0334 (16)	0.0468 (17)	−0.0010 (13)	0.0067 (13)	0.0088 (13)

Geometric parameters (Å, º)

C10A—O10A	1.475 (7)	C10B—O10B	1.468 (8)
C10A—C13A	1.502 (10)	C10B—C12B	1.497 (10)
C10A—C11A	1.508 (9)	C10B—C13B	1.529 (12)
C10A—C12A	1.518 (9)	C10B—C11B	1.522 (10)
C11A—H11A	0.9800	C11B—H11B	0.9800
C11A—H12A	0.9800	C11B—H12B	0.9800
C11A—H13A	0.9800	C11B—H13B	0.9800
C12A—H14A	0.9800	C12B—H14B	0.9800
C12A—H15A	0.9800	C12B—H15B	0.9800
C12A—H16A	0.9800	C12B—H16B	0.9800
C13A—H17A	0.9800	C13B—H17B	0.9800
C13A—H18A	0.9800	C13B—H18B	0.9800
C13A—H19A	0.9800	C13B—H19B	0.9800
O10A—C14A	1.343 (6)	O10B—C14B	1.337 (7)
C14A—O14A	1.218 (6)	C14B—O14B	1.217 (7)
C14A—N20A	1.347 (6)	C14B—N20B	1.346 (7)
N20A—C20A	1.454 (6)	N20B—C20B	1.447 (7)
N20A—C23A	1.464 (6)	N20B—C23B	1.475 (7)
C20A—C24A	1.520 (6)	C20B—C24B	1.525 (6)
C20A—C21A	1.547 (6)	C20B—C21B	1.546 (7)
C20A—H20A	1.0000	C20B—H20B	1.0000
C21A—C22A	1.517 (8)	C21B—C22B	1.511 (10)
C21A—H21A	0.9900	C21B—H21B	0.9900
C21A—H22A	0.9900	C21B—H22B	0.9900
C22A—C23A	1.521 (8)	C22B—C23B	1.499 (8)
C22A—H23A	0.9900	C22B—H23B	0.9900
C22A—H24A	0.9900	C22B—H24B	0.9900
C23A—H25A	0.9900	C23B—H25B	0.9900
C23A—H26A	0.9900	C23B—H26B	0.9900
C24A—O24A	1.234 (5)	C24B—O24B	1.226 (5)
C24A—N30A	1.336 (5)	C24B—N30B	1.342 (5)
N30A—C30A	1.466 (5)	N30B—C30B	1.463 (5)
N30A—C33A	1.460 (5)	N30B—C33B	1.473 (5)
C30A—C34A	1.523 (6)	C30B—C34B	1.529 (5)
C30A—C31A	1.537 (6)	C30B—C31B	1.544 (5)
C30A—H30A	1.0000	C30B—H30B	1.0000
C31A—C32A	1.518 (6)	C31B—C32B	1.517 (6)
C31A—H33A	0.9900	C31B—H33B	0.9900
C31A—H34A	0.9900	C31B—H34B	0.9900
C32A—O32A	1.414 (5)	C32B—O32B	1.438 (5)
C32A—C33A	1.534 (6)	C32B—C33B	1.519 (6)
C32A—H35A	1.0000	C32B—H35B	1.0000
O32A—H32A	0.80 (8)	O32B—H32B	0.75 (7)
C33A—H36A	0.9900	C33B—H36B	0.9900
C33A—H37A	0.9900	C33B—H37B	0.9900
C34A—O34A	1.218 (5)	C34B—O34B	1.236 (5)
C34A—N40A	1.348 (5)	C34B—N40B	1.332 (5)
N40A—C40A	1.449 (5)	N40B—C40B	1.455 (5)
N40A—H40A	0.8800	N40B—H40B	0.8800
C40A—C41A	1.508 (6)	C40B—C41B	1.521 (6)
C40A—H41A	0.9900	C40B—H41B	0.9900
C40A—H42A	0.9900	C40B—H42B	0.9900
C41A—O41A	1.192 (6)	C41B—O41B	1.180 (6)
C41A—O57A	1.339 (6)	C41B—O57B	1.345 (5)
C51A—C52A	1.378 (9)	C51B—C52B	1.378 (8)
C51A—C56A	1.383 (10)	C51B—C56B	1.386 (9)
C51A—C57A	1.499 (8)	C51B—C57B	1.504 (8)
C52A—C53A	1.391 (10)	C52B—C53B	1.386 (9)
C52A—H52A	0.9500	C52B—H52B	0.9500
C53A—C54A	1.350 (11)	C53B—C54B	1.363 (10)
C53A—H53A	0.9500	C53B—H53B	0.9500
C54A—C55A	1.352 (10)	C54B—C55B	1.380 (10)
C54A—H54A	0.9500	C54B—H54B	0.9500
C55A—C56A	1.393 (9)	C55B—C56B	1.390 (9)
C55A—H55A	0.9500	C55B—H55B	0.9500
C56A—H56A	0.9500	C56B—H56B	0.9500
C57A—O57A	1.454 (6)	C57B—O57B	1.466 (6)
C57A—H57A	0.9900	C57B—H57B	0.9900
C57A—H58A	0.9900	C57B—H58B	0.9900
O10A—C10A—C13A	110.0 (5)	O10B—C10B—C12B	108.8 (5)
O10A—C10A—C11A	109.4 (5)	O10B—C10B—C13B	109.9 (6)
C13A—C10A—C11A	113.6 (6)	C12B—C10B—C13B	113.3 (6)
O10A—C10A—C12A	101.4 (5)	O10B—C10B—C11B	102.1 (5)
C13A—C10A—C12A	110.1 (6)	C12B—C10B—C11B	110.4 (7)
C11A—C10A—C12A	111.7 (6)	C13B—C10B—C11B	111.8 (6)
C10A—C11A—H11A	109.5	C10B—C11B—H11B	109.5
C10A—C11A—H12A	109.5	C10B—C11B—H12B	109.5
H11A—C11A—H12A	109.5	H11B—C11B—H12B	109.5
C10A—C11A—H13A	109.5	C10B—C11B—H13B	109.5
H11A—C11A—H13A	109.5	H11B—C11B—H13B	109.5
H12A—C11A—H13A	109.5	H12B—C11B—H13B	109.5
C10A—C12A—H14A	109.5	C10B—C12B—H14B	109.5
C10A—C12A—H15A	109.5	C10B—C12B—H15B	109.5
H14A—C12A—H15A	109.5	H14B—C12B—H15B	109.5
C10A—C12A—H16A	109.5	C10B—C12B—H16B	109.5
H14A—C12A—H16A	109.5	H14B—C12B—H16B	109.5
H15A—C12A—H16A	109.5	H15B—C12B—H16B	109.5
C10A—C13A—H17A	109.5	C10B—C13B—H17B	109.5
C10A—C13A—H18A	109.5	C10B—C13B—H18B	109.5
H17A—C13A—H18A	109.5	H17B—C13B—H18B	109.5
C10A—C13A—H19A	109.5	C10B—C13B—H19B	109.5
H17A—C13A—H19A	109.5	H17B—C13B—H19B	109.5
H18A—C13A—H19A	109.5	H18B—C13B—H19B	109.5
C14A—O10A—C10A	120.1 (4)	C14B—O10B—C10B	121.5 (4)
O14A—C14A—O10A	126.2 (4)	O14B—C14B—O10B	126.0 (5)
O14A—C14A—N20A	123.5 (5)	O14B—C14B—N20B	124.2 (5)
O10A—C14A—N20A	110.3 (4)	O10B—C14B—N20B	109.8 (5)
C14A—N20A—C20A	119.7 (4)	C14B—N20B—C20B	119.9 (5)
C14A—N20A—C23A	126.9 (4)	C14B—N20B—C23B	125.3 (5)
C20A—N20A—C23A	112.9 (4)	C20B—N20B—C23B	113.1 (4)
N20A—C20A—C24A	111.3 (4)	N20B—C20B—C24B	112.2 (4)
N20A—C20A—C21A	102.4 (4)	N20B—C20B—C21B	100.5 (4)
C24A—C20A—C21A	109.0 (4)	C24B—C20B—C21B	109.4 (4)
N20A—C20A—H20A	111.3	N20B—C20B—H20B	111.4
C24A—C20A—H20A	111.3	C24B—C20B—H20B	111.4
C21A—C20A—H20A	111.3	C21B—C20B—H20B	111.4
C22A—C21A—C20A	102.7 (4)	C22B—C21B—C20B	103.3 (5)
C22A—C21A—H21A	111.2	C22B—C21B—H21B	111.1
C20A—C21A—H21A	111.2	C20B—C21B—H21B	111.1
C22A—C21A—H22A	111.2	C22B—C21B—H22B	111.1
C20A—C21A—H22A	111.2	C20B—C21B—H22B	111.1
H21A—C21A—H22A	109.1	H21B—C21B—H22B	109.1
C21A—C22A—C23A	103.8 (4)	C23B—C22B—C21B	103.5 (5)
C21A—C22A—H23A	111.0	C23B—C22B—H23B	111.1
C23A—C22A—H23A	111.0	C21B—C22B—H23B	111.1
C21A—C22A—H24A	111.0	C23B—C22B—H24B	111.1
C23A—C22A—H24A	111.0	C21B—C22B—H24B	111.1
H23A—C22A—H24A	109.0	H23B—C22B—H24B	109.0
N20A—C23A—C22A	103.3 (4)	N20B—C23B—C22B	103.5 (5)
N20A—C23A—H25A	111.1	N20B—C23B—H25B	111.1
C22A—C23A—H25A	111.1	C22B—C23B—H25B	111.1
N20A—C23A—H26A	111.1	N20B—C23B—H26B	111.1
C22A—C23A—H26A	111.1	C22B—C23B—H26B	111.1
H25A—C23A—H26A	109.1	H25B—C23B—H26B	109.0
O24A—C24A—N30A	121.5 (4)	O24B—C24B—N30B	121.9 (4)
O24A—C24A—C20A	121.6 (4)	O24B—C24B—C20B	121.2 (4)
N30A—C24A—C20A	116.8 (4)	N30B—C24B—C20B	116.8 (4)
C24A—N30A—C30A	120.5 (3)	C24B—N30B—C30B	120.3 (3)
C24A—N30A—C33A	126.8 (3)	C24B—N30B—C33B	127.5 (3)
C30A—N30A—C33A	112.4 (3)	C30B—N30B—C33B	112.1 (3)
N30A—C30A—C34A	110.3 (3)	N30B—C30B—C34B	112.0 (3)
N30A—C30A—C31A	103.2 (3)	N30B—C30B—C31B	103.2 (3)
C34A—C30A—C31A	109.2 (3)	C34B—C30B—C31B	112.0 (3)
N30A—C30A—H30A	111.3	N30B—C30B—H30B	109.8
C34A—C30A—H30A	111.3	C34B—C30B—H30B	109.8
C31A—C30A—H30A	111.3	C31B—C30B—H30B	109.8
C32A—C31A—C30A	103.7 (3)	C32B—C31B—C30B	103.0 (3)
C32A—C31A—H33A	111.0	C32B—C31B—H33B	111.2
C30A—C31A—H33A	111.0	C30B—C31B—H33B	111.2
C32A—C31A—H34A	111.0	C32B—C31B—H34B	111.2
C30A—C31A—H34A	111.0	C30B—C31B—H34B	111.2
H33A—C31A—H34A	109.0	H33B—C31B—H34B	109.1
O32A—C32A—C31A	110.2 (4)	O32B—C32B—C33B	107.4 (4)
O32A—C32A—C33A	111.9 (4)	O32B—C32B—C31B	110.9 (3)
C31A—C32A—C33A	104.4 (3)	C33B—C32B—C31B	102.9 (3)
O32A—C32A—H35A	110.0	O32B—C32B—H35B	111.7
C31A—C32A—H35A	110.0	C33B—C32B—H35B	111.7
C33A—C32A—H35A	110.0	C31B—C32B—H35B	111.7
C32A—O32A—H32A	106 (6)	C32B—O32B—H32B	106 (5)
N30A—C33A—C32A	104.3 (3)	N30B—C33B—C32B	101.2 (3)
N30A—C33A—H36A	110.9	N30B—C33B—H36B	111.5
C32A—C33A—H36A	110.9	C32B—C33B—H36B	111.5
N30A—C33A—H37A	110.9	N30B—C33B—H37B	111.5
C32A—C33A—H37A	110.9	C32B—C33B—H37B	111.5
H36A—C33A—H37A	108.9	H36B—C33B—H37B	109.3
O34A—C34A—N40A	123.3 (4)	O34B—C34B—N40B	123.8 (4)
O34A—C34A—C30A	121.9 (4)	O34B—C34B—C30B	121.9 (3)
N40A—C34A—C30A	114.7 (3)	N40B—C34B—C30B	114.3 (3)
C34A—N40A—C40A	119.3 (3)	C34B—N40B—C40B	121.6 (3)
C34A—N40A—H40A	120.4	C34B—N40B—H40B	119.2
C40A—N40A—H40A	120.4	C40B—N40B—H40B	119.2
N40A—C40A—C41A	112.4 (3)	N40B—C40B—C41B	112.2 (4)
N40A—C40A—H41A	109.1	N40B—C40B—H41B	109.2
C41A—C40A—H41A	109.1	C41B—C40B—H41B	109.2
N40A—C40A—H42A	109.1	N40B—C40B—H42B	109.2
C41A—C40A—H42A	109.1	C41B—C40B—H42B	109.2
H41A—C40A—H42A	107.9	H41B—C40B—H42B	107.9
O41A—C41A—O57A	124.2 (4)	O41B—C41B—O57B	124.3 (4)
O41A—C41A—C40A	126.8 (4)	O41B—C41B—C40B	125.5 (4)
O57A—C41A—C40A	109.1 (4)	O57B—C41B—C40B	110.2 (4)
C52A—C51A—C56A	118.7 (6)	C52B—C51B—C56B	118.2 (6)
C52A—C51A—C57A	120.7 (6)	C52B—C51B—C57B	120.3 (5)
C56A—C51A—C57A	120.6 (6)	C56B—C51B—C57B	121.5 (6)
C51A—C52A—C53A	119.2 (7)	C51B—C52B—C53B	120.9 (6)
C51A—C52A—H52A	120.4	C51B—C52B—H52B	119.6
C53A—C52A—H52A	120.4	C53B—C52B—H52B	119.6
C54A—C53A—C52A	121.2 (7)	C54B—C53B—C52B	120.2 (6)
C54A—C53A—H53A	119.4	C54B—C53B—H53B	119.9
C52A—C53A—H53A	119.4	C52B—C53B—H53B	119.9
C55A—C54A—C53A	120.7 (7)	C53B—C54B—C55B	120.3 (6)
C55A—C54A—H54A	119.7	C53B—C54B—H54B	119.9
C53A—C54A—H54A	119.7	C55B—C54B—H54B	119.9
C54A—C55A—C56A	119.2 (8)	C56B—C55B—C54B	119.1 (7)
C54A—C55A—H55A	120.4	C56B—C55B—H55B	120.5
C56A—C55A—H55A	120.4	C54B—C55B—H55B	120.5
C51A—C56A—C55A	121.0 (6)	C55B—C56B—C51B	121.1 (6)
C51A—C56A—H56A	119.5	C55B—C56B—H56B	119.4
C55A—C56A—H56A	119.5	C51B—C56B—H56B	119.4
O57A—C57A—C51A	108.0 (5)	O57B—C57B—C51B	113.8 (5)
O57A—C57A—H57A	110.1	O57B—C57B—H57B	108.8
C51A—C57A—H57A	110.1	C51B—C57B—H57B	108.8
O57A—C57A—H58A	110.1	O57B—C57B—H58B	108.8
C51A—C57A—H58A	110.1	C51B—C57B—H58B	108.8
H57A—C57A—H58A	108.4	H57B—C57B—H58B	107.7
C41A—O57A—C57A	116.0 (4)	C41B—O57B—C57B	115.6 (4)
C13A—C10A—O10A—C14A	62.8 (7)	C12B—C10B—O10B—C14B	63.8 (8)
C11A—C10A—O10A—C14A	−62.6 (7)	C13B—C10B—O10B—C14B	−60.8 (8)
C12A—C10A—O10A—C14A	179.3 (5)	C11B—C10B—O10B—C14B	−179.5 (6)
C10A—O10A—C14A—O14A	0.6 (9)	C10B—O10B—C14B—O14B	13.6 (10)
C10A—O10A—C14A—N20A	179.1 (5)	C10B—O10B—C14B—N20B	−167.6 (6)
O14A—C14A—N20A—C20A	−7.8 (8)	O14B—C14B—N20B—C20B	−5.5 (9)
O10A—C14A—N20A—C20A	173.6 (4)	O10B—C14B—N20B—C20B	175.7 (5)
O14A—C14A—N20A—C23A	−179.1 (5)	O14B—C14B—N20B—C23B	−170.0 (6)
O10A—C14A—N20A—C23A	2.4 (8)	O10B—C14B—N20B—C23B	11.2 (8)
C14A—N20A—C20A—C24A	−71.1 (6)	C14B—N20B—C20B—C24B	−69.9 (7)
C23A—N20A—C20A—C24A	101.3 (5)	C23B—N20B—C20B—C24B	96.4 (5)
C14A—N20A—C20A—C21A	172.6 (5)	C14B—N20B—C20B—C21B	174.0 (5)
C23A—N20A—C20A—C21A	−15.0 (5)	C23B—N20B—C20B—C21B	−19.7 (6)
N20A—C20A—C21A—C22A	32.7 (5)	N20B—C20B—C21B—C22B	35.9 (5)
C24A—C20A—C21A—C22A	−85.3 (5)	C24B—C20B—C21B—C22B	−82.3 (5)
C20A—C21A—C22A—C23A	−38.8 (5)	C20B—C21B—C22B—C23B	−39.9 (5)
C14A—N20A—C23A—C22A	162.9 (5)	C14B—N20B—C23B—C22B	161.0 (5)
C20A—N20A—C23A—C22A	−8.8 (6)	C20B—N20B—C23B—C22B	−4.4 (6)
C21A—C22A—C23A—N20A	29.6 (6)	C21B—C22B—C23B—N20B	27.4 (6)
N20A—C20A—C24A—O24A	−19.4 (6)	N20B—C20B—C24B—O24B	−9.4 (6)
C21A—C20A—C24A—O24A	92.8 (5)	C21B—C20B—C24B—O24B	101.2 (5)
N20A—C20A—C24A—N30A	164.0 (4)	N20B—C20B—C24B—N30B	174.2 (4)
C21A—C20A—C24A—N30A	−83.8 (5)	C21B—C20B—C24B—N30B	−75.2 (6)
O24A—C24A—N30A—C30A	−8.0 (6)	O24B—C24B—N30B—C30B	−8.4 (6)
C20A—C24A—N30A—C30A	168.6 (3)	C20B—C24B—N30B—C30B	168.0 (4)
O24A—C24A—N30A—C33A	179.1 (4)	O24B—C24B—N30B—C33B	166.2 (4)
C20A—C24A—N30A—C33A	−4.2 (6)	C20B—C24B—N30B—C33B	−17.4 (6)
C24A—N30A—C30A—C34A	−73.8 (4)	C24B—N30B—C30B—C34B	−63.1 (4)
C33A—N30A—C30A—C34A	100.0 (4)	C33B—N30B—C30B—C34B	121.6 (3)
C24A—N30A—C30A—C31A	169.6 (3)	C24B—N30B—C30B—C31B	176.2 (3)
C33A—N30A—C30A—C31A	−16.6 (4)	C33B—N30B—C30B—C31B	0.8 (4)
N30A—C30A—C31A—C32A	31.2 (4)	N30B—C30B—C31B—C32B	−25.5 (4)
C34A—C30A—C31A—C32A	−86.2 (4)	C34B—C30B—C31B—C32B	−146.3 (3)
C30A—C31A—C32A—O32A	−154.9 (4)	C30B—C31B—C32B—O32B	−74.0 (4)
C30A—C31A—C32A—C33A	−34.5 (4)	C30B—C31B—C32B—C33B	40.6 (4)
C24A—N30A—C33A—C32A	168.7 (4)	C24B—N30B—C33B—C32B	−151.0 (4)
C30A—N30A—C33A—C32A	−4.7 (5)	C30B—N30B—C33B—C32B	24.0 (4)
O32A—C32A—C33A—N30A	143.7 (4)	O32B—C32B—C33B—N30B	77.9 (4)
C31A—C32A—C33A—N30A	24.4 (4)	C31B—C32B—C33B—N30B	−39.2 (4)
N30A—C30A—C34A—O34A	−35.4 (5)	N30B—C30B—C34B—O34B	−10.3 (5)
C31A—C30A—C34A—O34A	77.3 (5)	C31B—C30B—C34B—O34B	105.1 (4)
N30A—C30A—C34A—N40A	148.8 (3)	N30B—C30B—C34B—N40B	171.7 (3)
C31A—C30A—C34A—N40A	−98.4 (4)	C31B—C30B—C34B—N40B	−72.9 (4)
O34A—C34A—N40A—C40A	−7.6 (6)	O34B—C34B—N40B—C40B	−3.3 (6)
C30A—C34A—N40A—C40A	168.0 (3)	C30B—C34B—N40B—C40B	174.6 (3)
C34A—N40A—C40A—C41A	−70.9 (5)	C34B—N40B—C40B—C41B	−66.2 (5)
N40A—C40A—C41A—O41A	−3.5 (7)	N40B—C40B—C41B—O41B	1.5 (7)
N40A—C40A—C41A—O57A	176.5 (4)	N40B—C40B—C41B—O57B	179.2 (3)
C56A—C51A—C52A—C53A	−3.3 (10)	C56B—C51B—C52B—C53B	−2.5 (10)
C57A—C51A—C52A—C53A	175.5 (6)	C57B—C51B—C52B—C53B	176.9 (6)
C51A—C52A—C53A—C54A	2.1 (11)	C51B—C52B—C53B—C54B	−0.8 (11)
C52A—C53A—C54A—C55A	0.1 (12)	C52B—C53B—C54B—C55B	4.3 (11)
C53A—C54A—C55A—C56A	−0.9 (12)	C53B—C54B—C55B—C56B	−4.4 (11)
C52A—C51A—C56A—C55A	2.5 (10)	C54B—C55B—C56B—C51B	1.1 (11)
C57A—C51A—C56A—C55A	−176.3 (6)	C52B—C51B—C56B—C55B	2.3 (10)
C54A—C55A—C56A—C51A	−0.4 (11)	C57B—C51B—C56B—C55B	−177.1 (6)
C52A—C51A—C57A—O57A	134.1 (6)	C52B—C51B—C57B—O57B	94.3 (7)
C56A—C51A—C57A—O57A	−47.2 (8)	C56B—C51B—C57B—O57B	−86.3 (7)
O41A—C41A—O57A—C57A	−3.3 (7)	O41B—C41B—O57B—C57B	9.6 (7)
C40A—C41A—O57A—C57A	176.7 (4)	C40B—C41B—O57B—C57B	−168.2 (4)
C51A—C57A—O57A—C41A	177.1 (5)	C51B—C57B—O57B—C41B	−92.5 (5)

(II) benzyl N-{2-[N-(tert-butoxycarbonyl)alanyl]-4-hydroxyprolyl}glycinate

Crystal data

C22H31N3O7	Z = 2
Mr = 449.50	F(000) = 480
TriclinicP1	Dx = 1.272 Mg m^−3
a = 5.8816 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6294 (6) Å	Cell parameters from 8664 reflections
c = 19.707 (1) Å	θ = 2.5–28.3°
α = 75.240 (1)°	µ = 0.10 mm^−1
β = 82.560 (1)°	T = 200 K
γ = 81.780 (1)°	Plate, colourless
V = 1173.6 (1) Å^3	0.45 × 0.35 × 0.20 mm

Data collection

Bruker AXS, SMART APEX CCD area detector diffractometer	5142 independent reflections
Radiation source: MacScience, M18XCE rotating anode	5049 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.366 pixels mm^-1	θmax = 27.1°, θmin = 2.0°
ω–scan	h = −7→7
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.927, Tmax = 0.981	l = −25→25
13595 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 0.1501P] where P = (Fo^2 + 2Fc^2)/3
5142 reflections	(Δ/σ)max = 0.002
593 parameters	Δρmax = 0.43 e Å^−3
245 restraints	Δρmin = −0.16 e Å^−3

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
C10A	0.7486 (10)	1.0329 (6)	−0.2855 (3)	0.0351 (11)
C11A	0.7676 (13)	1.1789 (7)	−0.3027 (4)	0.0500 (15)
H11A	0.6924	1.2151	−0.2634	0.075*
H12A	0.6920	1.2223	−0.3454	0.075*
H13A	0.9308	1.1934	−0.3105	0.075*
C12A	0.8714 (14)	0.9732 (8)	−0.3446 (3)	0.0513 (16)
H14A	1.0351	0.9863	−0.3507	0.077*
H15A	0.8015	1.0155	−0.3885	0.077*
H16A	0.8566	0.8792	−0.3327	0.077*
C13A	0.4979 (11)	1.0058 (7)	−0.2696 (4)	0.0455 (14)
H17A	0.4902	0.9113	−0.2599	0.068*
H18A	0.4132	1.0506	−0.3103	0.068*
H19A	0.4286	1.0381	−0.2284	0.068*
O10A	0.8736 (7)	0.9848 (4)	−0.2219 (2)	0.0344 (8)
C14A	0.8961 (9)	0.8555 (5)	−0.1890 (3)	0.0305 (10)
O14A	0.8158 (8)	0.7710 (4)	−0.2062 (2)	0.0415 (9)
N20A	1.0202 (8)	0.8364 (4)	−0.1335 (2)	0.0331 (9)
H20A	1.0618	0.9042	−0.1222	0.040*
C20A	1.0857 (9)	0.7053 (5)	−0.0921 (3)	0.0298 (10)
H21A	1.0728	0.6412	−0.1204	0.036*
C21A	1.3359 (10)	0.6911 (7)	−0.0747 (3)	0.0414 (13)
H22A	1.4389	0.7051	−0.1186	0.062*
H23A	1.3763	0.6030	−0.0456	0.062*
H24A	1.3525	0.7563	−0.0489	0.062*
C22A	0.9254 (8)	0.6736 (5)	−0.0233 (3)	0.0265 (9)
O22A	0.8313 (7)	0.7592 (4)	0.0058 (2)	0.0358 (8)
N30A	0.9017 (8)	0.5475 (4)	0.0056 (3)	0.0333 (10)
C30A	0.7548 (11)	0.5098 (6)	0.0715 (3)	0.0399 (13)
H30A	0.5930	0.5523	0.0662	0.048*
C31A	0.7655 (19)	0.3598 (7)	0.0834 (4)	0.067 (2)
H33A	0.8870	0.3141	0.1144	0.080*
H34A	0.6155	0.3292	0.1051	0.080*
C32A	0.8216 (12)	0.3357 (5)	0.0109 (4)	0.0490 (16)
H35A	0.8942	0.2440	0.0128	0.059*
O32A	0.6261 (9)	0.3667 (5)	−0.0275 (3)	0.0471 (11)
H32A	0.550 (13)	0.313 (8)	−0.009 (4)	0.034 (18)*
C33A	0.9885 (12)	0.4350 (6)	−0.0252 (6)	0.061 (2)
H36A	1.1487	0.4010	−0.0143	0.073*
H37A	0.9830	0.4590	−0.0769	0.073*
C34A	0.8474 (10)	0.5392 (5)	0.1340 (3)	0.0361 (11)
O34A	1.0538 (8)	0.5205 (4)	0.1411 (3)	0.0444 (10)
N40A	0.6882 (10)	0.5768 (6)	0.1821 (3)	0.0469 (12)
H40A	0.5464	0.6021	0.1705	0.056*
C40A	0.7364 (13)	0.5781 (6)	0.2518 (4)	0.0470 (14)
H41A	0.6064	0.6295	0.2734	0.056*
H42A	0.8768	0.6218	0.2481	0.056*
C41A	0.7718 (10)	0.4418 (6)	0.2987 (3)	0.0377 (12)
O41A	0.7138 (11)	0.3458 (5)	0.2900 (3)	0.0557 (12)
O50A	0.8804 (10)	0.4459 (6)	0.3530 (3)	0.0580 (13)
C50A	0.9054 (16)	0.3260 (11)	0.4082 (4)	0.0713 (15)
H50A	1.0460	0.3226	0.4316	0.086*
H51A	0.9223	0.2494	0.3873	0.086*
C51A	0.6981 (14)	0.3206 (8)	0.4614 (3)	0.0522 (11)
C52A	0.564 (2)	0.2194 (10)	0.4749 (5)	0.0719 (12)
H52A	0.6011	0.1513	0.4507	0.086*
C53A	0.371 (2)	0.2183 (14)	0.5250 (6)	0.0927 (14)
H53A	0.2771	0.1490	0.5352	0.111*
C54A	0.319 (2)	0.3179 (16)	0.5591 (6)	0.0983 (15)
H54A	0.1864	0.3181	0.5921	0.118*
C55A	0.454 (3)	0.4153 (14)	0.5466 (6)	0.0981 (15)
H55A	0.4179	0.4827	0.5713	0.118*
C56A	0.644 (2)	0.4166 (10)	0.4982 (5)	0.0754 (13)
H56A	0.7402	0.4848	0.4899	0.090*
C10B	0.9358 (11)	−0.1443 (7)	0.4336 (3)	0.0456 (15)
C11B	1.0680 (13)	−0.2573 (8)	0.4061 (4)	0.0570 (18)
H11B	0.9660	−0.2924	0.3817	0.085*
H12B	1.1244	−0.3262	0.4456	0.085*
H13B	1.1993	−0.2263	0.3731	0.085*
C12B	0.7312 (13)	−0.1857 (10)	0.4861 (4)	0.061 (2)
H14B	0.6437	−0.1085	0.4993	0.091*
H15B	0.7867	−0.2477	0.5282	0.091*
H16B	0.6311	−0.2276	0.4646	0.091*
C13B	1.0949 (13)	−0.0788 (10)	0.4659 (4)	0.059 (2)
H17B	1.2189	−0.0464	0.4302	0.089*
H18B	1.1618	−0.1426	0.5056	0.089*
H19B	1.0061	−0.0054	0.4826	0.089*
O10B	0.8562 (7)	−0.0356 (4)	0.3756 (2)	0.0386 (9)
C14B	0.6877 (9)	−0.0499 (6)	0.3378 (3)	0.0322 (10)
O14B	0.6252 (8)	−0.1529 (4)	0.3372 (3)	0.0457 (10)
N20B	0.5982 (8)	0.0677 (5)	0.3017 (2)	0.0336 (10)
H20B	0.6527	0.1394	0.3037	0.040*
C20B	0.4094 (9)	0.0750 (6)	0.2591 (3)	0.0318 (10)
H21B	0.2960	0.0149	0.2868	0.038*
C21B	0.2877 (12)	0.2139 (7)	0.2415 (4)	0.0477 (15)
H22B	0.2305	0.2408	0.2852	0.072*
H23B	0.1577	0.2170	0.2144	0.072*
H24B	0.3965	0.2734	0.2135	0.072*
C22B	0.4976 (8)	0.0335 (5)	0.1902 (3)	0.0266 (9)
O22B	0.6796 (6)	0.0650 (4)	0.1569 (2)	0.0334 (8)
N30B	0.3575 (7)	−0.0322 (4)	0.1672 (2)	0.0292 (9)
C30B	0.4132 (9)	−0.0670 (5)	0.0996 (3)	0.0285 (10)
H30B	0.5459	−0.1376	0.1019	0.034*
C31B	0.1897 (11)	−0.1180 (6)	0.0896 (3)	0.0413 (13)
H33B	0.0783	−0.0455	0.0668	0.050*
H34B	0.2232	−0.1837	0.0608	0.050*
C32B	0.0987 (10)	−0.1796 (6)	0.1646 (3)	0.0372 (12)
H35B	−0.0706	−0.1861	0.1681	0.045*
O32B	0.2234 (8)	−0.3050 (5)	0.1909 (3)	0.0459 (10)
H32B	0.16 (2)	−0.359 (12)	0.178 (6)	0.08 (3)*
C33B	0.1479 (10)	−0.0866 (6)	0.2063 (3)	0.0371 (12)
H36B	0.0179	−0.0165	0.2075	0.045*
H37B	0.1760	−0.1337	0.2552	0.045*
C34B	0.4595 (8)	0.0488 (5)	0.0382 (2)	0.0262 (9)
O34B	0.3609 (7)	0.1598 (4)	0.0343 (2)	0.0324 (8)
N40B	0.5990 (8)	0.0148 (4)	−0.0155 (2)	0.0324 (9)
H40B	0.6822	−0.0623	−0.0090	0.039*
C40B	0.6111 (10)	0.1054 (5)	−0.0836 (3)	0.0338 (11)
H41B	0.7199	0.0654	−0.1170	0.041*
H42B	0.6712	0.1855	−0.0799	0.041*
C41B	0.3765 (10)	0.1421 (5)	−0.1118 (3)	0.0330 (11)
O41B	0.2205 (8)	0.0759 (4)	−0.1001 (2)	0.0450 (10)
O50B	0.3724 (8)	0.2614 (4)	−0.1555 (2)	0.0419 (10)
C50B	0.1686 (12)	0.3123 (6)	−0.1912 (4)	0.0444 (11)
H50B	0.0336	0.3237	−0.1568	0.053*
H51B	0.1365	0.2518	−0.2187	0.053*
C51B	0.2166 (12)	0.4429 (6)	−0.2397 (3)	0.0429 (9)
C52B	0.0757 (15)	0.4990 (7)	−0.2936 (4)	0.0540 (10)
H52B	−0.0486	0.4559	−0.2994	0.065*
C53B	0.1186 (19)	0.6198 (9)	−0.3392 (5)	0.0694 (12)
H53B	0.0230	0.6583	−0.3762	0.083*
C54B	0.2972 (17)	0.6829 (8)	−0.3310 (5)	0.0659 (12)
H54B	0.3261	0.7640	−0.3627	0.079*
C55B	0.4339 (16)	0.6297 (8)	−0.2774 (6)	0.0653 (12)
H55B	0.5564	0.6742	−0.2715	0.078*
C56B	0.3929 (14)	0.5100 (7)	−0.2313 (5)	0.0559 (11)
H56B	0.4867	0.4738	−0.1937	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C10A	0.038 (3)	0.044 (3)	0.021 (2)	−0.002 (2)	−0.008 (2)	−0.004 (2)
C11A	0.060 (4)	0.045 (3)	0.038 (3)	−0.005 (3)	−0.015 (3)	0.006 (3)
C12A	0.058 (4)	0.068 (4)	0.026 (3)	−0.001 (3)	−0.002 (3)	−0.013 (3)
C13A	0.038 (3)	0.057 (4)	0.042 (3)	−0.002 (3)	−0.010 (2)	−0.012 (3)
O10A	0.043 (2)	0.0359 (19)	0.0240 (17)	−0.0069 (16)	−0.0094 (15)	−0.0017 (14)
C14A	0.031 (2)	0.037 (3)	0.023 (2)	−0.007 (2)	0.0001 (18)	−0.0063 (19)
O14A	0.049 (2)	0.042 (2)	0.038 (2)	−0.0104 (18)	−0.0124 (18)	−0.0092 (17)
N20A	0.043 (2)	0.031 (2)	0.026 (2)	−0.0110 (18)	−0.0080 (18)	−0.0012 (17)
C20A	0.033 (2)	0.030 (2)	0.025 (2)	−0.0030 (19)	−0.0034 (18)	−0.0044 (18)
C21A	0.030 (3)	0.051 (3)	0.039 (3)	−0.004 (2)	−0.001 (2)	−0.003 (3)
C22A	0.027 (2)	0.025 (2)	0.026 (2)	−0.0025 (18)	−0.0049 (17)	−0.0031 (17)
O22A	0.046 (2)	0.0253 (17)	0.0330 (19)	−0.0012 (15)	0.0028 (16)	−0.0063 (14)
N30A	0.034 (2)	0.024 (2)	0.039 (2)	−0.0036 (17)	−0.0012 (18)	−0.0034 (17)
C30A	0.041 (3)	0.038 (3)	0.036 (3)	−0.013 (2)	−0.007 (2)	0.009 (2)
C31A	0.109 (7)	0.036 (3)	0.057 (4)	−0.036 (4)	−0.035 (4)	0.013 (3)
C32A	0.048 (3)	0.021 (2)	0.076 (5)	−0.005 (2)	−0.016 (3)	−0.002 (3)
O32A	0.055 (3)	0.032 (2)	0.055 (3)	−0.009 (2)	−0.015 (2)	−0.0050 (19)
C33A	0.043 (3)	0.029 (3)	0.112 (7)	−0.005 (3)	0.012 (4)	−0.027 (4)
C34A	0.040 (3)	0.024 (2)	0.037 (3)	−0.003 (2)	−0.004 (2)	0.004 (2)
O34A	0.042 (2)	0.041 (2)	0.053 (3)	−0.0001 (18)	−0.0114 (19)	−0.0154 (19)
N40A	0.043 (3)	0.049 (3)	0.038 (3)	0.001 (2)	−0.003 (2)	0.006 (2)
C40A	0.057 (4)	0.036 (3)	0.042 (3)	−0.008 (3)	0.009 (3)	−0.004 (2)
C41A	0.036 (3)	0.041 (3)	0.033 (3)	−0.006 (2)	0.002 (2)	−0.005 (2)
O41A	0.078 (4)	0.037 (2)	0.052 (3)	−0.012 (2)	−0.014 (2)	−0.003 (2)
O50A	0.063 (3)	0.077 (4)	0.037 (2)	−0.023 (3)	−0.006 (2)	−0.010 (2)
C50A	0.062 (3)	0.102 (3)	0.037 (2)	0.010 (3)	−0.010 (2)	−0.001 (2)
C51A	0.061 (2)	0.057 (2)	0.0298 (18)	0.0057 (19)	−0.0099 (17)	0.0009 (17)
C52A	0.096 (3)	0.069 (3)	0.050 (2)	−0.010 (2)	−0.029 (2)	−0.001 (2)
C53A	0.084 (3)	0.120 (3)	0.062 (2)	−0.040 (2)	−0.028 (2)	0.026 (2)
C54A	0.070 (3)	0.143 (3)	0.051 (2)	0.010 (2)	0.002 (2)	0.016 (2)
C55A	0.119 (3)	0.097 (3)	0.055 (2)	0.026 (2)	0.017 (2)	−0.009 (2)
C56A	0.104 (3)	0.063 (3)	0.051 (2)	−0.003 (2)	0.006 (2)	−0.0073 (19)
C10B	0.037 (3)	0.063 (4)	0.030 (3)	−0.003 (3)	−0.011 (2)	0.005 (3)
C11B	0.050 (4)	0.056 (4)	0.051 (4)	0.005 (3)	−0.009 (3)	0.006 (3)
C12B	0.043 (3)	0.090 (6)	0.035 (3)	−0.005 (4)	−0.009 (3)	0.012 (3)
C13B	0.044 (3)	0.097 (6)	0.037 (3)	−0.007 (4)	−0.015 (3)	−0.011 (4)
O10B	0.039 (2)	0.045 (2)	0.0317 (19)	−0.0067 (17)	−0.0137 (16)	−0.0032 (16)
C14B	0.032 (2)	0.039 (3)	0.025 (2)	−0.006 (2)	−0.0047 (19)	−0.006 (2)
O14B	0.050 (2)	0.037 (2)	0.051 (3)	−0.0091 (18)	−0.017 (2)	−0.0017 (18)
N20B	0.041 (2)	0.034 (2)	0.029 (2)	−0.0075 (19)	−0.0117 (19)	−0.0066 (17)
C20B	0.032 (2)	0.039 (3)	0.024 (2)	−0.004 (2)	−0.0047 (19)	−0.006 (2)
C21B	0.048 (3)	0.052 (4)	0.042 (3)	0.014 (3)	−0.011 (3)	−0.017 (3)
C22B	0.026 (2)	0.027 (2)	0.025 (2)	−0.0020 (18)	−0.0064 (17)	−0.0021 (18)
O22B	0.0306 (18)	0.038 (2)	0.0324 (19)	−0.0112 (15)	−0.0005 (14)	−0.0078 (15)
N30B	0.029 (2)	0.037 (2)	0.0212 (19)	−0.0083 (17)	−0.0026 (16)	−0.0033 (16)
C30B	0.035 (2)	0.027 (2)	0.023 (2)	−0.0058 (18)	−0.0052 (18)	−0.0041 (18)
C31B	0.048 (3)	0.045 (3)	0.036 (3)	−0.021 (3)	−0.014 (2)	−0.005 (2)
C32B	0.032 (2)	0.040 (3)	0.039 (3)	−0.013 (2)	−0.010 (2)	−0.002 (2)
O32B	0.040 (2)	0.041 (2)	0.056 (3)	−0.0140 (18)	−0.014 (2)	0.000 (2)
C33B	0.029 (2)	0.048 (3)	0.035 (3)	−0.015 (2)	0.000 (2)	−0.008 (2)
C34B	0.028 (2)	0.028 (2)	0.023 (2)	−0.0039 (18)	−0.0064 (17)	−0.0042 (18)
O34B	0.0359 (18)	0.0282 (18)	0.0311 (18)	0.0012 (14)	−0.0029 (14)	−0.0061 (14)
N40B	0.041 (2)	0.027 (2)	0.026 (2)	0.0028 (18)	−0.0021 (17)	−0.0050 (17)
C40B	0.042 (3)	0.033 (3)	0.024 (2)	−0.003 (2)	−0.002 (2)	−0.0049 (19)
C41B	0.047 (3)	0.030 (2)	0.023 (2)	−0.004 (2)	−0.004 (2)	−0.0079 (18)
O41B	0.053 (3)	0.040 (2)	0.044 (2)	−0.0153 (19)	−0.0114 (19)	−0.0045 (18)
O50B	0.051 (2)	0.033 (2)	0.039 (2)	−0.0079 (17)	−0.0145 (18)	0.0027 (16)
C50B	0.051 (2)	0.038 (2)	0.044 (2)	−0.0026 (18)	−0.017 (2)	−0.0055 (17)
C51B	0.052 (2)	0.0357 (17)	0.0370 (18)	0.0080 (15)	−0.0070 (16)	−0.0073 (15)
C52B	0.069 (2)	0.047 (2)	0.045 (2)	0.0071 (18)	−0.0204 (18)	−0.0077 (17)
C53B	0.094 (3)	0.053 (2)	0.053 (2)	0.017 (2)	−0.027 (2)	−0.0015 (18)
C54B	0.080 (3)	0.041 (2)	0.064 (2)	0.0042 (18)	−0.003 (2)	0.0036 (19)
C55B	0.065 (2)	0.041 (2)	0.084 (3)	−0.0038 (18)	−0.010 (2)	−0.004 (2)
C56B	0.060 (2)	0.0393 (19)	0.064 (2)	−0.0007 (17)	−0.0207 (19)	−0.0001 (18)

Geometric parameters (Å, º)

C10A—O10A	1.475 (6)	C10B—O10B	1.474 (7)
C10A—C11A	1.518 (9)	C10B—C11B	1.515 (11)
C10A—C12A	1.520 (9)	C10B—C12B	1.520 (9)
C10A—C13A	1.521 (9)	C10B—C13B	1.528 (10)
C11A—H11A	0.9800	C11B—H11B	0.9800
C11A—H12A	0.9800	C11B—H12B	0.9800
C11A—H13A	0.9800	C11B—H13B	0.9800
C12A—H14A	0.9800	C12B—H14B	0.9800
C12A—H15A	0.9800	C12B—H15B	0.9800
C12A—H16A	0.9800	C12B—H16B	0.9800
C13A—H17A	0.9800	C13B—H17B	0.9800
C13A—H18A	0.9800	C13B—H18B	0.9800
C13A—H19A	0.9800	C13B—H19B	0.9800
O10A—C14A	1.357 (7)	O10B—C14B	1.360 (6)
C14A—O14A	1.210 (7)	C14B—O14B	1.207 (7)
C14A—N20A	1.350 (7)	C14B—N20B	1.342 (7)
N20A—C20A	1.451 (7)	N20B—C20B	1.458 (6)
N20A—H20A	0.8800	N20B—H20B	0.8800
C20A—C21A	1.532 (8)	C20B—C21B	1.521 (8)
C20A—C22A	1.538 (7)	C20B—C22B	1.538 (7)
C20A—H21A	1.0000	C20B—H21B	1.0000
C21A—H22A	0.9800	C21B—H22B	0.9800
C21A—H23A	0.9800	C21B—H23B	0.9800
C21A—H24A	0.9800	C21B—H24B	0.9800
C22A—O22A	1.227 (6)	C22B—O22B	1.223 (6)
C22A—N30A	1.336 (6)	C22B—N30B	1.340 (6)
N30A—C30A	1.461 (7)	N30B—C30B	1.457 (6)
N30A—C33A	1.474 (8)	N30B—C33B	1.476 (7)
C30A—C34A	1.526 (9)	C30B—C34B	1.519 (7)
C30A—C31A	1.545 (9)	C30B—C31B	1.545 (7)
C30A—H30A	1.0000	C30B—H30B	1.0000
C31A—C32A	1.503 (13)	C31B—C32B	1.519 (8)
C31A—H33A	0.9900	C31B—H33B	0.9900
C31A—H34A	0.9900	C31B—H34B	0.9900
C32A—O32A	1.412 (8)	C32B—O32B	1.431 (8)
C32A—C33A	1.522 (9)	C32B—C33B	1.514 (8)
C32A—H35A	1.0000	C32B—H35B	1.0000
O32A—H32A	0.76 (8)	O32B—H32B	0.85 (13)
C33A—H36A	0.9900	C33B—H36B	0.9900
C33A—H37A	0.9900	C33B—H37B	0.9900
C34A—O34A	1.222 (8)	C34B—O34B	1.226 (6)
C34A—N40A	1.337 (8)	C34B—N40B	1.345 (6)
N40A—C40A	1.441 (9)	N40B—C40B	1.438 (7)
N40A—H40A	0.8800	N40B—H40B	0.8800
C40A—C41A	1.510 (8)	C40B—C41B	1.517 (8)
C40A—H41A	0.9900	C40B—H41B	0.9900
C40A—H42A	0.9900	C40B—H42B	0.9900
C41A—O41A	1.179 (8)	C41B—O41B	1.199 (7)
C41A—O50A	1.329 (8)	C41B—O50B	1.339 (7)
O50A—C50A	1.453 (11)	O50B—C50B	1.437 (7)
C50A—C51A	1.500 (12)	C50B—C51B	1.512 (9)
C50A—H50A	0.9900	C50B—H50B	0.9900
C50A—H51A	0.9900	C50B—H51B	0.9900
C51A—C56A	1.375 (13)	C51B—C56B	1.389 (11)
C51A—C52A	1.376 (13)	C51B—C52B	1.390 (9)
C52A—C53A	1.401 (17)	C52B—C53B	1.403 (12)
C52A—H52A	0.9500	C52B—H52B	0.9500
C53A—C54A	1.37 (2)	C53B—C54B	1.372 (15)
C53A—H53A	0.9500	C53B—H53B	0.9500
C54A—C55A	1.35 (2)	C54B—C55B	1.367 (13)
C54A—H54A	0.9500	C54B—H54B	0.9500
C55A—C56A	1.373 (16)	C55B—C56B	1.395 (11)
C55A—H55A	0.9500	C55B—H55B	0.9500
C56A—H56A	0.9500	C56B—H56B	0.9500
O10A—C10A—C11A	101.8 (5)	O10B—C10B—C11B	111.4 (5)
O10A—C10A—C12A	110.1 (5)	O10B—C10B—C12B	109.5 (5)
C11A—C10A—C12A	110.6 (5)	C11B—C10B—C12B	112.4 (7)
O10A—C10A—C13A	111.2 (5)	O10B—C10B—C13B	101.4 (6)
C11A—C10A—C13A	111.1 (5)	C11B—C10B—C13B	111.0 (6)
C12A—C10A—C13A	111.7 (5)	C12B—C10B—C13B	110.5 (6)
C10A—C11A—H11A	109.5	C10B—C11B—H11B	109.5
C10A—C11A—H12A	109.5	C10B—C11B—H12B	109.5
H11A—C11A—H12A	109.5	H11B—C11B—H12B	109.5
C10A—C11A—H13A	109.5	C10B—C11B—H13B	109.5
H11A—C11A—H13A	109.5	H11B—C11B—H13B	109.5
H12A—C11A—H13A	109.5	H12B—C11B—H13B	109.5
C10A—C12A—H14A	109.5	C10B—C12B—H14B	109.5
C10A—C12A—H15A	109.5	C10B—C12B—H15B	109.5
H14A—C12A—H15A	109.5	H14B—C12B—H15B	109.5
C10A—C12A—H16A	109.5	C10B—C12B—H16B	109.5
H14A—C12A—H16A	109.5	H14B—C12B—H16B	109.5
H15A—C12A—H16A	109.5	H15B—C12B—H16B	109.5
C10A—C13A—H17A	109.5	C10B—C13B—H17B	109.5
C10A—C13A—H18A	109.5	C10B—C13B—H18B	109.5
H17A—C13A—H18A	109.5	H17B—C13B—H18B	109.5
C10A—C13A—H19A	109.5	C10B—C13B—H19B	109.5
H17A—C13A—H19A	109.5	H17B—C13B—H19B	109.5
H18A—C13A—H19A	109.5	H18B—C13B—H19B	109.5
C14A—O10A—C10A	120.6 (4)	C14B—O10B—C10B	120.0 (5)
O14A—C14A—N20A	125.4 (5)	O14B—C14B—N20B	124.6 (5)
O14A—C14A—O10A	125.5 (5)	O14B—C14B—O10B	125.2 (5)
N20A—C14A—O10A	109.2 (4)	N20B—C14B—O10B	110.1 (5)
C14A—N20A—C20A	120.7 (4)	C14B—N20B—C20B	119.1 (5)
C14A—N20A—H20A	119.7	C14B—N20B—H20B	120.4
C20A—N20A—H20A	119.7	C20B—N20B—H20B	120.4
N20A—C20A—C21A	110.4 (5)	N20B—C20B—C21B	110.1 (5)
N20A—C20A—C22A	110.9 (4)	N20B—C20B—C22B	111.2 (4)
C21A—C20A—C22A	109.5 (4)	C21B—C20B—C22B	109.1 (4)
N20A—C20A—H21A	108.7	N20B—C20B—H21B	108.8
C21A—C20A—H21A	108.7	C21B—C20B—H21B	108.8
C22A—C20A—H21A	108.7	C22B—C20B—H21B	108.8
C20A—C21A—H22A	109.5	C20B—C21B—H22B	109.5
C20A—C21A—H23A	109.5	C20B—C21B—H23B	109.5
H22A—C21A—H23A	109.5	H22B—C21B—H23B	109.5
C20A—C21A—H24A	109.5	C20B—C21B—H24B	109.5
H22A—C21A—H24A	109.5	H22B—C21B—H24B	109.5
H23A—C21A—H24A	109.5	H23B—C21B—H24B	109.5
O22A—C22A—N30A	120.9 (5)	O22B—C22B—N30B	122.5 (5)
O22A—C22A—C20A	121.8 (4)	O22B—C22B—C20B	121.4 (4)
N30A—C22A—C20A	117.2 (4)	N30B—C22B—C20B	116.0 (4)
C22A—N30A—C30A	120.2 (5)	C22B—N30B—C30B	121.0 (4)
C22A—N30A—C33A	127.3 (5)	C22B—N30B—C33B	126.7 (4)
C30A—N30A—C33A	112.1 (5)	C30B—N30B—C33B	112.1 (4)
N30A—C30A—C34A	112.8 (5)	N30B—C30B—C34B	113.7 (4)
N30A—C30A—C31A	103.2 (6)	N30B—C30B—C31B	102.8 (4)
C34A—C30A—C31A	108.6 (5)	C34B—C30B—C31B	108.3 (4)
N30A—C30A—H30A	110.7	N30B—C30B—H30B	110.6
C34A—C30A—H30A	110.7	C34B—C30B—H30B	110.6
C31A—C30A—H30A	110.7	C31B—C30B—H30B	110.6
C32A—C31A—C30A	104.5 (5)	C32B—C31B—C30B	102.8 (4)
C32A—C31A—H33A	110.9	C32B—C31B—H33B	111.2
C30A—C31A—H33A	110.9	C30B—C31B—H33B	111.2
C32A—C31A—H34A	110.9	C32B—C31B—H34B	111.2
C30A—C31A—H34A	110.9	C30B—C31B—H34B	111.2
H33A—C31A—H34A	108.9	H33B—C31B—H34B	109.1
O32A—C32A—C31A	111.7 (7)	O32B—C32B—C33B	108.4 (5)
O32A—C32A—C33A	106.9 (6)	O32B—C32B—C31B	111.5 (5)
C31A—C32A—C33A	103.5 (6)	C33B—C32B—C31B	103.7 (4)
O32A—C32A—H35A	111.5	O32B—C32B—H35B	111.0
C31A—C32A—H35A	111.5	C33B—C32B—H35B	111.0
C33A—C32A—H35A	111.5	C31B—C32B—H35B	111.0
C32A—O32A—H32A	104 (6)	C32B—O32B—H32B	106 (8)
N30A—C33A—C32A	102.7 (6)	N30B—C33B—C32B	103.5 (5)
N30A—C33A—H36A	111.2	N30B—C33B—H36B	111.1
C32A—C33A—H36A	111.2	C32B—C33B—H36B	111.1
N30A—C33A—H37A	111.2	N30B—C33B—H37B	111.1
C32A—C33A—H37A	111.2	C32B—C33B—H37B	111.1
H36A—C33A—H37A	109.1	H36B—C33B—H37B	109.0
O34A—C34A—N40A	123.0 (6)	O34B—C34B—N40B	122.8 (4)
O34A—C34A—C30A	121.0 (6)	O34B—C34B—C30B	123.6 (5)
N40A—C34A—C30A	115.8 (6)	N40B—C34B—C30B	113.1 (4)
C34A—N40A—C40A	123.6 (6)	C34B—N40B—C40B	119.4 (4)
C34A—N40A—H40A	118.2	C34B—N40B—H40B	120.3
C40A—N40A—H40A	118.2	C40B—N40B—H40B	120.3
N40A—C40A—C41A	112.1 (5)	N40B—C40B—C41B	111.6 (5)
N40A—C40A—H41A	109.2	N40B—C40B—H41B	109.3
C41A—C40A—H41A	109.2	C41B—C40B—H41B	109.3
N40A—C40A—H42A	109.2	N40B—C40B—H42B	109.3
C41A—C40A—H42A	109.2	C41B—C40B—H42B	109.3
H41A—C40A—H42A	107.9	H41B—C40B—H42B	108.0
O41A—C41A—O50A	124.4 (6)	O41B—C41B—O50B	124.2 (5)
O41A—C41A—C40A	126.8 (6)	O41B—C41B—C40B	127.2 (5)
O50A—C41A—C40A	108.9 (6)	O50B—C41B—C40B	108.5 (5)
C41A—O50A—C50A	116.5 (6)	C41B—O50B—C50B	117.6 (5)
O50A—C50A—C51A	110.1 (7)	O50B—C50B—C51B	106.3 (5)
O50A—C50A—H50A	109.6	O50B—C50B—H50B	110.5
C51A—C50A—H50A	109.6	C51B—C50B—H50B	110.5
O50A—C50A—H51A	109.6	O50B—C50B—H51B	110.5
C51A—C50A—H51A	109.6	C51B—C50B—H51B	110.5
H50A—C50A—H51A	108.2	H50B—C50B—H51B	108.7
C56A—C51A—C52A	119.7 (9)	C56B—C51B—C52B	118.9 (7)
C56A—C51A—C50A	119.5 (9)	C56B—C51B—C50B	122.3 (6)
C52A—C51A—C50A	120.8 (9)	C52B—C51B—C50B	118.8 (7)
C51A—C52A—C53A	119.0 (10)	C51B—C52B—C53B	119.5 (8)
C51A—C52A—H52A	120.5	C51B—C52B—H52B	120.3
C53A—C52A—H52A	120.5	C53B—C52B—H52B	120.3
C54A—C53A—C52A	119.7 (11)	C54B—C53B—C52B	120.6 (8)
C54A—C53A—H53A	120.2	C54B—C53B—H53B	119.7
C52A—C53A—H53A	120.2	C52B—C53B—H53B	119.7
C55A—C54A—C53A	121.0 (10)	C55B—C54B—C53B	120.3 (7)
C55A—C54A—H54A	119.5	C55B—C54B—H54B	119.8
C53A—C54A—H54A	119.5	C53B—C54B—H54B	119.8
C54A—C55A—C56A	119.7 (12)	C54B—C55B—C56B	119.8 (8)
C54A—C55A—H55A	120.1	C54B—C55B—H55B	120.1
C56A—C55A—H55A	120.1	C56B—C55B—H55B	120.1
C55A—C56A—C51A	120.9 (11)	C51B—C56B—C55B	120.8 (7)
C55A—C56A—H56A	119.6	C51B—C56B—H56B	119.6
C51A—C56A—H56A	119.6	C55B—C56B—H56B	119.6
C11A—C10A—O10A—C14A	179.9 (5)	C11B—C10B—O10B—C14B	69.3 (7)
C12A—C10A—O10A—C14A	−62.8 (7)	C12B—C10B—O10B—C14B	−55.7 (8)
C13A—C10A—O10A—C14A	61.5 (7)	C13B—C10B—O10B—C14B	−172.5 (5)
C10A—O10A—C14A—O14A	−1.9 (8)	C10B—O10B—C14B—O14B	−16.0 (9)
C10A—O10A—C14A—N20A	178.8 (4)	C10B—O10B—C14B—N20B	163.3 (5)
O14A—C14A—N20A—C20A	5.5 (8)	O14B—C14B—N20B—C20B	1.0 (8)
O10A—C14A—N20A—C20A	−175.2 (4)	O10B—C14B—N20B—C20B	−178.3 (4)
C14A—N20A—C20A—C21A	137.8 (5)	C14B—N20B—C20B—C21B	162.8 (5)
C14A—N20A—C20A—C22A	−100.6 (5)	C14B—N20B—C20B—C22B	−76.1 (6)
N20A—C20A—C22A—O22A	−29.1 (7)	N20B—C20B—C22B—O22B	−39.4 (7)
C21A—C20A—C22A—O22A	92.9 (6)	C21B—C20B—C22B—O22B	82.3 (6)
N20A—C20A—C22A—N30A	154.2 (4)	N20B—C20B—C22B—N30B	144.2 (5)
C21A—C20A—C22A—N30A	−83.7 (6)	C21B—C20B—C22B—N30B	−94.1 (6)
O22A—C22A—N30A—C30A	2.5 (8)	O22B—C22B—N30B—C30B	−1.6 (7)
C20A—C22A—N30A—C30A	179.1 (5)	C20B—C22B—N30B—C30B	174.7 (4)
O22A—C22A—N30A—C33A	175.0 (6)	O22B—C22B—N30B—C33B	173.2 (5)
C20A—C22A—N30A—C33A	−8.3 (8)	C20B—C22B—N30B—C33B	−10.4 (7)
C22A—N30A—C30A—C34A	−66.1 (7)	C22B—N30B—C30B—C34B	−53.8 (6)
C33A—N30A—C30A—C34A	120.3 (6)	C33B—N30B—C30B—C34B	130.7 (5)
C22A—N30A—C30A—C31A	176.9 (5)	C22B—N30B—C30B—C31B	−170.6 (5)
C33A—N30A—C30A—C31A	3.3 (7)	C33B—N30B—C30B—C31B	13.9 (6)
N30A—C30A—C31A—C32A	−25.1 (8)	N30B—C30B—C31B—C32B	−32.3 (6)
C34A—C30A—C31A—C32A	−145.1 (6)	C34B—C30B—C31B—C32B	−152.8 (5)
C30A—C31A—C32A—O32A	−77.4 (7)	C30B—C31B—C32B—O32B	−77.3 (6)
C30A—C31A—C32A—C33A	37.2 (8)	C30B—C31B—C32B—C33B	39.1 (6)
C22A—N30A—C33A—C32A	−153.7 (6)	C22B—N30B—C33B—C32B	−165.0 (5)
C30A—N30A—C33A—C32A	19.3 (8)	C30B—N30B—C33B—C32B	10.2 (6)
O32A—C32A—C33A—N30A	83.7 (8)	O32B—C32B—C33B—N30B	88.1 (5)
C31A—C32A—C33A—N30A	−34.4 (8)	C31B—C32B—C33B—N30B	−30.4 (6)
N30A—C30A—C34A—O34A	−39.9 (7)	N30B—C30B—C34B—O34B	−33.9 (7)
C31A—C30A—C34A—O34A	73.9 (7)	C31B—C30B—C34B—O34B	79.7 (6)
N30A—C30A—C34A—N40A	144.7 (5)	N30B—C30B—C34B—N40B	153.6 (4)
C31A—C30A—C34A—N40A	−101.5 (7)	C31B—C30B—C34B—N40B	−92.8 (5)
O34A—C34A—N40A—C40A	−10.8 (9)	O34B—C34B—N40B—C40B	−8.7 (8)
C30A—C34A—N40A—C40A	164.4 (5)	C30B—C34B—N40B—C40B	163.9 (4)
C34A—N40A—C40A—C41A	−73.1 (8)	C34B—N40B—C40B—C41B	−58.6 (6)
N40A—C40A—C41A—O41A	−18.6 (10)	N40B—C40B—C41B—O41B	−29.7 (8)
N40A—C40A—C41A—O50A	161.7 (6)	N40B—C40B—C41B—O50B	152.9 (4)
O41A—C41A—O50A—C50A	−6.7 (10)	O41B—C41B—O50B—C50B	−0.8 (8)
C40A—C41A—O50A—C50A	173.1 (6)	C40B—C41B—O50B—C50B	176.7 (5)
C41A—O50A—C50A—C51A	−87.9 (9)	C41B—O50B—C50B—C51B	−176.7 (5)
O50A—C50A—C51A—C56A	−60.6 (10)	O50B—C50B—C51B—C56B	−17.8 (9)
O50A—C50A—C51A—C52A	120.7 (9)	O50B—C50B—C51B—C52B	163.8 (6)
C56A—C51A—C52A—C53A	1.5 (12)	C56B—C51B—C52B—C53B	1.8 (11)
C50A—C51A—C52A—C53A	−179.8 (7)	C50B—C51B—C52B—C53B	−179.7 (7)
C51A—C52A—C53A—C54A	0.4 (14)	C51B—C52B—C53B—C54B	−0.3 (13)
C52A—C53A—C54A—C55A	−1.7 (16)	C52B—C53B—C54B—C55B	−1.0 (14)
C53A—C54A—C55A—C56A	1.2 (18)	C53B—C54B—C55B—C56B	0.7 (14)
C54A—C55A—C56A—C51A	0.7 (18)	C52B—C51B—C56B—C55B	−2.2 (12)
C52A—C51A—C56A—C55A	−2.0 (14)	C50B—C51B—C56B—C55B	179.4 (8)
C50A—C51A—C56A—C55A	179.2 (9)	C54B—C55B—C56B—C51B	0.9 (14)