Cyclo­echinulin, a Trp-Ala-derived alkaloid from the fungus Aspergillus ochraceus

The structure of the Trp-Ala-derived, non-basic alkaloid cyclo­echinulin from the mycelial mat of the fungus Aspergillus ochraceus is described; systematic name: (3S)-2,3,8,9-tetra­hydro-11-methoxy-3,8,8-tri­methyl­pyrazino[1',2':1,2]­azocino­[5,4-b]­indole-1,4-dione-methanol (4/1), C₂₀H₂₁N₃O₃·0.25CH₄O. There are four independent mol­ecules plus one methanol mol­ecule in the asymmetric unit. The conformations of mol­ecules 1-3 are almost identical, while mol­ecule 4 shows a different conformation in the fused 8-6 ring moiety.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.064
• wR factor = 0.209
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



SHFSU_01  Alert B The absolute value of parameter shift to su ratio > 0.10
          Absolute value of the parameter shift to su ratio given   0.121
          Additional refinement cycles may be required.

Author response: see _publ_section_exptl_refinement

PLAT_213  Alert B Atom  C119   has ADP max/min Ratio ...........       4.20

Author response: see _publ_section_exptl_refinement

 Alert Level C:



STRVAL_01
         From the CIF: _refine_ls_abs_structure_Flack    2.700
         From the CIF: _refine_ls_abs_structure_Flack_su    1.900
           Alert C Chirality of atom sites is inverted?

PLAT_213  Alert C Atom  O102   has ADP max/min Ratio ...........       3.40

PLAT_213  Alert C Atom  N116   has ADP max/min Ratio ...........       3.50

PLAT_213  Alert C Atom  C115   has ADP max/min Ratio ...........       3.70

PLAT_213  Alert C Atom  C121   has ADP max/min Ratio ...........       3.10

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.01
         From the CIF: _reflns_number_total              13028
         Count of symmetry unique reflns         6796
         Completeness (_total/calc)            191.70%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      6232
         Fraction of Friedel pairs measured     0.917
         Are heavy atom types Z>Si present           no
          ALERT: MoKa measured Friedel data cannot be used to
                 determine absolute structure in a light-atom
                 study EXCEPT under VERY special conditions.
                 It is preferred that Friedel data is merged in such cases.


 0 Alert Level A = Potentially serious problem

 2 Alert Level B = Potential problem

 5 Alert Level C = Please check

---

S1. Comment

Aspergillus ochraceus is known to produce a number of alkaloids constructed from various amino acids, such as Phe, Ala, Trp, and Pro (Merve et al., 1965; Rahbaek & Breinholt, 1999; Rahbaek et al., 1999). Cycloechinulin (I) was first isolated in 1992 in minute quantities, 1.1 mg, from the sclerotia of A. ochraceus by De Guzman et al. (1992). The Trp-Ala-derived structure was proposed on the basis of spectroscopic properties, but has not been established by X-ray diffraction. Cycloechinulin (I) is structurally related to the pentacyclic Trp-Pro-derived alkaloid (II) which was isolated from A. ustus by Steyn in 1973, and, more remotely, to those of the echinulin series of compounds, e.g. neoechinulin from A. amstelodami (Barbetta et al., 1969; Dossena et al., 1974; Quilico & Panizzi, 1943; Steyn, 1971; Yamamoto & Arai, 1986). Cycloechinulin (I) has been shown to excert moderate insecticidal activity against the lepidopteran crop pest Helicoverpa zea (De Guzman et al., 1992). Substantial amounts of cycloechinulin (I) has now been isolated from the mycelial mat of A. ochraceus and its structure confirmed by X-ray diffraction analysis.

The title compound crystallizes in the monoclinic non-centrosymmetric space group P2₁ with four molecules in the asymmetric unit. The crystal structure also includes one methanol molecule. The four independent molecules are shown in Figs. 1–4. The conformation of molecules 1–3 are almost identical, while molecule 4 is found in a different conformation in the eight-membered dihydroazocin moiety and six-membered 2,5-diketopiperazin part of the molecule (see Table 1 and Figs. 5–8). The indole part of all four molecules are planar and the atoms CX23, OX01, CX10 and CX19 (X = 1–4), are also in the same plane [largest deviation -0.138 (10) Å for atom C419]. A selection of bond lengths shows that these are all within the normal range of such bonds (Allen et al., 1986). The mean value for the C═ O bonds is 1.232 (15) Å, while the CX02═CX03 bonds have an average bond length of 1.38 (2) Å. The mean value of the CX10═CX11 and CX18═CX17 bonds is 1.32 (3) Å. The molecules are packed in the crystal through a series of intermolecular hydrogen bonds which also involve the methanol molecule (see Table 2).

S2. Experimental

Aspergillus ochraceus, an Australian isolate D2306 (Connole et al., 1981), was grown on Sabourauds agar plates (pH 5.9, 298 K, 10–14 d). The mycelial mat was washed with distilled water (4 × 5 ml). The extracts were combined, the volume reduced to ca 50%, filtered, centrifuged, and extracted with CHCl₃. Preparative TLC (silica gel) furnished ca 100 mg cycloechinulin per m² mycelial mat. Cycloechinulin (I) was spectroscopically characterized before recrystallization. Single crystals of (I) were obtained on slow evaporation of MeOH at room temperature.

S3. Refinement

The large s.u. value of the Flack (1983) parameter, 2.7 (19), indicates that the absolute structure cannot be determined with Mo radiation. The stereostructure of the asymmetric carbon, C114 (C214, C314 or C414) in the Scheme and Figs. 1–8 was just assumed tentatively. The value of (Δ/σ)_max is 0.121 (>0.10) and the C119 has ADP max/min ratio 4.20. These results may be due to the rough packing of four independent molecules.

Computing details

Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELLDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1993).

Figures

	Fig. 1. A view of molecule 1 of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 10% probability level.
	Fig. 2. A view of molecule 2 of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 10% probability level.
	Fig. 3. A view of molecule 3 of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 10% probability level.
	Fig. 4. A view of molecule 4 of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 10% probability level.
	Fig. 5. A sideview of molecule 1 of (I) with displacement ellipsoids drawn at the 10% probability level.
	Fig. 6. A sideview of molecule 2 of (I) with displacement ellipsoids drawn at the 10% probability level.
	Fig. 7. A sideview of molecule 3 of (I) with displacement ellipsoids drawn at the 10% probability level.
	Fig. 8. A sideview of molecule 4 of (I) with displacement ellipsoids drawn at the 10% probability level.

(I)

Crystal data

C20H21N3O3·0.25CH4O	F(000) = 1524
Mr = 359.41	Dx = 1.282 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
a = 15.222 (2) Å	Cell parameters from 25 reflections
b = 16.848 (2) Å	θ = 12–18°
c = 15.930 (2) Å	µ = 0.09 mm^−1
β = 114.27 (1)°	T = 298 K
V = 3724.3 (8) Å^3	Block, colourless
Z = 8	0.6 × 0.3 × 0.3 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.4°
Graphite monochromator	h = −18→18
ω–2θ scans	k = −19→19
14273 measured reflections	l = −18→18
13028 independent reflections	3 standard reflections every 120 min
4745 reflections with I > 2σ(I)	intensity decay: 12%

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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.209	w = 1/[σ^2(Fo^2) + (0.1209P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.83	(Δ/σ)max = 0.121
13028 reflections	Δρmax = 0.52 e Å^−3
973 parameters	Δρmin = −0.31 e Å^−3
43 restraints	Absolute structure: (Flack, 1983), 6232 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 2.7 (19)

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.5342 (0.0330) x + 0.2845 (0.0380) y + 9.3753 (0.0320) z = 12.3078 (0.0221)

* 0.0002 (0.0062) N101 * 0.0109 (0.0064) C102 * -0.0269 (0.0062) C103 * 0.0006 (0.0070) C104 * -0.0153 (0.0071) C105 * 0.0141 (0.0068) C106 * -0.0086 (0.0066) C107 * -0.0141 (0.0079) C108 * 0.0391 (0.0075) C109 - 0.0699 (0.0118) C110 - 0.1188 (0.0122) C119 - 0.0409 (0.0104) O101 0.0102 (0.0139) C123

Rms deviation of fitted atoms = 0.0185

5.9561 (0.0300) x - 1.8093 (0.0316) y + 10.7109 (0.0240) z = 5.6023 (0.0407)

Angle to previous plane (with approximate e.s.d.) = 9.64 (0.37)

* 0.0182 (0.0052) N201 * -0.0234 (0.0059) C202 * -0.0120 (0.0056) C203 * 0.0165 (0.0059) C204 * -0.0138 (0.0058) C205 * -0.0131 (0.0057) C206 * 0.0019 (0.0060) C207 * 0.0038 (0.0069) C208 * 0.0219 (0.0072) C209 0.0491 (0.0102) C210 - 0.0121 (0.0097) C219 - 0.0681 (0.0096) O201 - 0.0168 (0.0123) C223

Rms deviation of fitted atoms = 0.0155

10.4738 (0.0236) x - 0.5419 (0.0326) y + 6.0222 (0.0320) z = 7.6391 (0.0228)

Angle to previous plane (with approximate e.s.d.) = 20.73 (0.31)

* 0.0077 (0.0046) N301 * 0.0262 (0.0049) C302 * -0.0287 (0.0054) C303 * 0.0372 (0.0063) C304 * -0.0122 (0.0065) C305 * 0.0101 (0.0064) C306 * -0.0116 (0.0062) C307 * -0.0068 (0.0068) C308 * -0.0217 (0.0060) C309 - 0.1332 (0.0099) C310 0.0540 (0.0091) C319 - 0.0004 (0.0100) O301 0.2314 (0.0122) C323

Rms deviation of fitted atoms = 0.0207

11.6518 (0.0195) x - 1.0949 (0.0317) y + 4.2850 (0.0316) z = 10.4557 (0.0235)

Angle to previous plane (with approximate e.s.d.) = 6.84 (0.35)

* -0.0047 (0.0049) N401 * -0.0472 (0.0051) C402 * -0.0044 (0.0053) C403 * 0.0223 (0.0055) C404 * -0.0432 (0.0058) C405 * -0.0216 (0.0060) C406 * 0.0102 (0.0057) C407 * 0.0490 (0.0066) C408 * 0.0395 (0.0063) C409 0.0642 (0.0099) C410 - 0.1375 (0.0097) C419 - 0.0393 (0.0090) O401 - 0.1244 (0.0117) C423

Rms deviation of fitted atoms = 0.0319

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
N313	0.3176 (4)	0.8772 (3)	0.6824 (4)	0.0434 (15)
H313	0.3063	0.9069	0.7207	0.056*
O303	0.3073 (4)	0.7653 (3)	0.7550 (4)	0.0621 (16)
N301	0.4542 (4)	0.5291 (3)	0.5274 (4)	0.0443 (16)
H301	0.4756	0.5125	0.4882	0.058*
O302	0.4571 (4)	0.9263 (3)	0.5635 (4)	0.0664 (15)
N316	0.4327 (4)	0.8067 (3)	0.6135 (4)	0.0391 (14)
O301	0.3755 (5)	0.2854 (3)	0.6410 (5)	0.092 (2)
O203	0.7523 (3)	0.4610 (3)	0.2024 (4)	0.0548 (15)
N216	0.8783 (4)	0.4202 (3)	0.0567 (4)	0.0470 (16)
O201	0.9150 (5)	0.9362 (3)	0.1660 (4)	0.088 (2)
N201	1.0123 (4)	0.6886 (3)	0.0782 (4)	0.0537 (17)
H201	1.0553	0.7034	0.0596	0.070*
N213	0.8009 (4)	0.3453 (3)	0.1624 (4)	0.0536 (18)
H213	0.7569	0.3184	0.1703	0.070*
O202	0.9021 (4)	0.2999 (3)	0.0088 (4)	0.0704 (17)
O403	0.6676 (4)	0.0549 (3)	0.7304 (4)	0.0561 (14)
N416	0.5351 (4)	0.0198 (3)	0.8686 (4)	0.0367 (14)
N113	0.7739 (4)	−0.0177 (3)	0.6388 (4)	0.0526 (17)
H113	0.7348	0.0054	0.6575	0.068*
O103	0.7475 (3)	−0.1303 (3)	0.6971 (4)	0.0605 (15)
O401	0.6259 (4)	0.5364 (3)	0.8661 (5)	0.0719 (17)
N413	0.6438 (4)	−0.0569 (3)	0.7941 (4)	0.0430 (15)
H413	0.6597	−0.0843	0.7570	0.056*
N401	0.5617 (4)	0.2932 (3)	0.9864 (4)	0.0519 (17)
H401	0.5469	0.3107	1.0296	0.067*
O402	0.4924 (4)	−0.0983 (3)	0.9052 (4)	0.0575 (14)
N101	0.9706 (5)	−0.3650 (4)	0.5439 (5)	0.072 (2)
H101	1.0053	−0.3824	0.5168	0.094*
O102	0.9438 (6)	0.0326 (4)	0.5508 (7)	0.154 (4)
O101	0.8637 (4)	−0.6068 (3)	0.6327 (4)	0.0787 (18)
N116	0.9118 (6)	−0.0854 (4)	0.5950 (7)	0.114 (4)
O501	0.2435 (5)	0.2437 (4)	0.1973 (6)	0.114 (2)
H501	0.2379	0.2798	0.2293	0.159*
C102	0.9556 (6)	−0.2853 (4)	0.5547 (6)	0.058 (2)
C103	0.8956 (5)	−0.2812 (4)	0.5987 (6)	0.048 (2)
C104	0.8242 (6)	−0.3979 (5)	0.6626 (6)	0.068 (3)
H104	0.7904	−0.3663	0.6872	0.089*
C105	0.8190 (6)	−0.4786 (5)	0.6675 (7)	0.068 (3)
H105	0.7819	−0.5020	0.6948	0.089*
C106	0.8695 (6)	−0.5244 (4)	0.6315 (6)	0.062 (2)
C107	0.9206 (6)	−0.4950 (4)	0.5871 (6)	0.058 (2)
H107	0.9522	−0.5280	0.5615	0.076*
C108	0.9240 (6)	−0.4127 (5)	0.5813 (6)	0.060 (2)
C109	0.8793 (6)	−0.3619 (4)	0.6213 (6)	0.050 (2)
C110	0.8543 (5)	−0.2155 (5)	0.6254 (6)	0.058 (2)
H110	0.8159	−0.2336	0.6542	0.075*
C111	0.8525 (6)	−0.1360 (5)	0.6225 (6)	0.066 (3)
C112	0.7895 (5)	−0.0936 (4)	0.6572 (5)	0.046 (2)
C114	0.8157 (5)	0.0308 (4)	0.5904 (5)	0.0520 (19)
H114	0.7645	0.0432	0.5300	0.068*
C115	0.8919 (8)	−0.0057 (5)	0.5752 (10)	0.109 (5)
C122	0.8465 (9)	0.1067 (6)	0.6419 (10)	0.133 (5)
H12G	0.9117	0.1019	0.6869	0.186*
H12H	0.8051	0.1186	0.6723	0.186*
H12I	0.8425	0.1487	0.5997	0.186*
C119	0.9905 (6)	−0.2202 (5)	0.5108 (6)	0.062 (2)
C120	1.0611 (8)	−0.2543 (5)	0.4758 (8)	0.108 (4)
H12A	1.0818	−0.2132	0.4462	0.151*
H12B	1.0304	−0.2959	0.4324	0.151*
H12C	1.1159	−0.2754	0.5265	0.151*
C121	0.9032 (8)	−0.1752 (7)	0.4382 (6)	0.123 (5)
H12D	0.8744	−0.1420	0.4690	0.172*
H12E	0.8565	−0.2128	0.4000	0.172*
H12F	0.9248	−0.1428	0.4007	0.172*
C118	1.0484 (6)	−0.1660 (5)	0.5881 (7)	0.069 (3)
H118	1.1145	−0.1748	0.6139	0.090*
C117	1.0197 (6)	−0.1097 (6)	0.6233 (6)	0.088 (3)
H117	1.0664	−0.0803	0.6697	0.114*
C123	0.8131 (7)	−0.6425 (5)	0.6800 (7)	0.087 (3)
H12J	0.8367	−0.6220	0.7415	0.122*
H12K	0.8226	−0.6990	0.6821	0.122*
H12L	0.7456	−0.6309	0.6483	0.122*
C202	0.9826 (5)	0.6127 (4)	0.0780 (5)	0.0477 (19)
C203	0.9160 (5)	0.6106 (4)	0.1157 (5)	0.0420 (19)
C204	0.8478 (5)	0.7249 (4)	0.1756 (5)	0.0465 (19)
H204	0.8085	0.6934	0.1937	0.060*
C205	0.8481 (5)	0.8073 (5)	0.1865 (5)	0.057 (2)
H205	0.8082	0.8306	0.2107	0.074*
C206	0.9099 (5)	0.8556 (5)	0.1603 (5)	0.053 (2)
C207	0.9690 (5)	0.8201 (5)	0.1229 (5)	0.058 (2)
H207	1.0104	0.8497	0.1056	0.076*
C208	0.9623 (5)	0.7391 (4)	0.1132 (5)	0.048 (2)
C209	0.9049 (5)	0.6906 (4)	0.1386 (6)	0.054 (2)
C210	0.8668 (5)	0.5456 (4)	0.1378 (5)	0.0406 (18)
H210	0.8377	0.5620	0.1760	0.053*
C211	0.8516 (5)	0.4662 (4)	0.1174 (5)	0.042 (2)
C212	0.7964 (5)	0.4269 (5)	0.1632 (6)	0.055 (2)
C214	0.8778 (6)	0.3027 (4)	0.1485 (5)	0.054 (2)
H214	0.9384	0.3090	0.2032	0.071*
C215	0.8874 (5)	0.3408 (4)	0.0665 (6)	0.052 (2)
C222	0.8526 (9)	0.2154 (5)	0.1333 (9)	0.119 (5)
H22G	0.8331	0.1967	0.1801	0.167*
H22H	0.9079	0.1860	0.1365	0.167*
H22I	0.8007	0.2081	0.0738	0.167*
C219	1.0233 (5)	0.5434 (4)	0.0447 (5)	0.0451 (19)
C220	1.0910 (6)	0.5732 (5)	−0.0016 (6)	0.077 (3)
H22A	1.0565	0.6101	−0.0499	0.107*
H22B	1.1113	0.5287	−0.0269	0.107*
H22C	1.1464	0.5989	0.0437	0.107*
C221	1.0799 (5)	0.4864 (4)	0.1207 (5)	0.056 (2)
H22D	1.1396	0.5106	0.1606	0.078*
H22E	1.0929	0.4389	0.0945	0.078*
H22F	1.0431	0.4733	0.1555	0.078*
C218	0.9362 (5)	0.5069 (3)	−0.0349 (5)	0.0429 (19)
H218	0.9255	0.5231	−0.0941	0.056*
C217	0.8743 (4)	0.4542 (4)	−0.0272 (5)	0.0408 (17)
H217	0.8238	0.4381	−0.0815	0.053*
C223	0.8612 (7)	0.9760 (5)	0.2074 (7)	0.086 (3)
H22J	0.7940	0.9646	0.1737	0.120*
H22K	0.8716	1.0322	0.2068	0.120*
H22L	0.8816	0.9583	0.2699	0.120*
C302	0.4483 (4)	0.6068 (4)	0.5478 (5)	0.0335 (17)
C303	0.4075 (5)	0.6122 (4)	0.6101 (5)	0.0391 (19)
C304	0.3604 (5)	0.4960 (4)	0.6925 (6)	0.059 (2)
H304	0.3456	0.5273	0.7330	0.077*
C305	0.3510 (6)	0.4141 (5)	0.6933 (6)	0.066 (3)
H305	0.3240	0.3909	0.7302	0.086*
C306	0.3812 (5)	0.3676 (4)	0.6403 (6)	0.060 (3)
C307	0.4149 (6)	0.3994 (5)	0.5809 (6)	0.059 (2)
H307	0.4332	0.3674	0.5433	0.077*
C308	0.4209 (5)	0.4801 (4)	0.5785 (6)	0.048 (2)
C309	0.3920 (4)	0.5312 (4)	0.6309 (5)	0.0360 (18)
C310	0.3772 (5)	0.6781 (4)	0.6515 (5)	0.0407 (18)
H310	0.3467	0.6603	0.6879	0.053*
C311	0.3815 (5)	0.7571 (4)	0.6508 (5)	0.048 (2)
C312	0.3335 (5)	0.8001 (4)	0.7013 (6)	0.044 (2)
C314	0.3185 (5)	0.9129 (4)	0.6005 (5)	0.0459 (19)
H314	0.2612	0.8952	0.5473	0.060*
C315	0.4059 (5)	0.8837 (4)	0.5894 (5)	0.0454 (19)
C322	0.3158 (6)	1.0029 (4)	0.6059 (6)	0.071 (3)
H32G	0.2626	1.0186	0.6198	0.100*
H32H	0.3081	1.0253	0.5478	0.100*
H32I	0.3749	1.0216	0.6533	0.100*
C319	0.4804 (5)	0.6724 (4)	0.5025 (5)	0.0438 (19)
C320	0.5382 (7)	0.6385 (5)	0.4513 (7)	0.081 (3)
H32A	0.5922	0.6090	0.4935	0.114*
H32B	0.5609	0.6812	0.4255	0.114*
H32C	0.4977	0.6041	0.4028	0.114*
C321	0.3935 (5)	0.7178 (4)	0.4337 (5)	0.060 (2)
H32D	0.3616	0.6860	0.3796	0.084*
H32E	0.4149	0.7665	0.4171	0.084*
H32F	0.3495	0.7293	0.4613	0.084*
C318	0.5475 (5)	0.7260 (4)	0.5799 (5)	0.049 (2)
H318	0.6129	0.7176	0.5968	0.064*
C317	0.5272 (5)	0.7810 (4)	0.6253 (5)	0.050 (2)
H317	0.5791	0.8067	0.6705	0.065*
C323	0.3563 (6)	0.2467 (5)	0.7095 (7)	0.078 (3)
H32J	0.3973	0.2677	0.7687	0.109*
H32K	0.3682	0.1909	0.7079	0.109*
H32L	0.2901	0.2549	0.6987	0.109*
C402	0.5593 (5)	0.2135 (4)	0.9627 (5)	0.0439 (19)
C403	0.5895 (5)	0.2104 (4)	0.8897 (5)	0.0399 (19)
C404	0.6341 (5)	0.3265 (4)	0.8044 (4)	0.0397 (18)
H404	0.6489	0.2952	0.7638	0.052*
C405	0.6377 (5)	0.4076 (4)	0.8002 (5)	0.054 (2)
H405	0.6516	0.4313	0.7544	0.071*
C406	0.6207 (5)	0.4550 (5)	0.8634 (6)	0.054 (2)
C407	0.5955 (5)	0.4224 (4)	0.9312 (6)	0.049 (2)
H407	0.5828	0.4541	0.9727	0.064*
C408	0.5903 (5)	0.3398 (4)	0.9332 (5)	0.0401 (18)
C409	0.6082 (5)	0.2913 (4)	0.8699 (5)	0.048 (2)
C410	0.6063 (5)	0.1432 (4)	0.8431 (5)	0.046 (2)
H410	0.6379	0.1598	0.8071	0.059*
C411	0.5920 (4)	0.0652 (4)	0.8336 (5)	0.0358 (18)
C412	0.6371 (5)	0.0211 (4)	0.7827 (5)	0.0457 (19)
C414	0.6262 (5)	−0.0989 (4)	0.8641 (5)	0.0419 (18)
H414	0.6038	−0.1522	0.8403	0.054*
C415	0.5452 (5)	−0.0585 (4)	0.8810 (5)	0.0394 (17)
C422	0.7133 (6)	−0.1085 (5)	0.9521 (5)	0.082 (3)
H42G	0.7608	−0.1391	0.9412	0.115*
H42H	0.6960	−0.1353	0.9962	0.115*
H42I	0.7394	−0.0572	0.9755	0.115*
C419	0.5284 (5)	0.1488 (4)	1.0092 (5)	0.0437 (19)
C420	0.4890 (7)	0.1827 (5)	1.0757 (6)	0.075 (3)
H42A	0.5353	0.2186	1.1176	0.105*
H42B	0.4769	0.1402	1.1097	0.105*
H42C	0.4300	0.2106	1.0416	0.105*
C421	0.6106 (6)	0.0954 (5)	1.0622 (5)	0.065 (2)
H42D	0.6437	0.0810	1.0245	0.091*
H42E	0.5868	0.0484	1.0798	0.091*
H42F	0.6543	0.1224	1.1163	0.091*
C418	0.4491 (5)	0.1077 (4)	0.9325 (5)	0.0470 (19)
H418	0.3876	0.1238	0.9241	0.061*
C417	0.4506 (5)	0.0522 (4)	0.8739 (5)	0.0471 (19)
H417	0.3914	0.0326	0.8327	0.061*
C423	0.6467 (6)	0.5742 (5)	0.7993 (7)	0.080 (3)
H42J	0.7071	0.5551	0.8018	0.112*
H42K	0.6507	0.6304	0.8102	0.112*
H42L	0.5966	0.5633	0.7397	0.112*
C502	0.1553 (8)	0.2274 (6)	0.1279 (8)	0.138 (5)
H50A	0.1073	0.2258	0.1524	0.193*
H50B	0.1578	0.1769	0.1010	0.193*
H50C	0.1391	0.2679	0.0816	0.193*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N313	0.053 (3)	0.032 (3)	0.054 (4)	0.005 (3)	0.030 (3)	0.001 (3)
O303	0.080 (4)	0.044 (3)	0.098 (5)	0.002 (3)	0.073 (4)	0.006 (3)
N301	0.057 (4)	0.032 (4)	0.059 (4)	−0.004 (3)	0.040 (3)	−0.010 (3)
O302	0.087 (4)	0.046 (3)	0.089 (4)	−0.005 (3)	0.059 (4)	0.001 (3)
N316	0.044 (3)	0.035 (4)	0.054 (4)	0.004 (3)	0.035 (3)	0.004 (3)
O301	0.150 (6)	0.033 (4)	0.134 (6)	0.000 (4)	0.099 (5)	0.014 (4)
O203	0.061 (3)	0.041 (3)	0.087 (4)	0.007 (2)	0.055 (3)	0.011 (3)
N216	0.044 (4)	0.037 (4)	0.072 (5)	−0.004 (3)	0.036 (4)	0.000 (3)
O201	0.137 (6)	0.030 (3)	0.114 (5)	−0.008 (4)	0.068 (5)	−0.005 (3)
N201	0.054 (4)	0.042 (4)	0.085 (5)	−0.009 (3)	0.049 (4)	0.004 (3)
N213	0.065 (4)	0.041 (4)	0.084 (5)	−0.011 (3)	0.060 (4)	0.005 (3)
O202	0.089 (4)	0.049 (3)	0.108 (5)	−0.006 (3)	0.075 (4)	−0.013 (3)
O403	0.088 (4)	0.029 (3)	0.074 (4)	0.008 (3)	0.056 (3)	0.006 (3)
N416	0.036 (3)	0.018 (3)	0.063 (4)	−0.006 (2)	0.027 (3)	−0.001 (3)
N113	0.061 (4)	0.041 (4)	0.082 (5)	−0.003 (3)	0.054 (4)	0.002 (3)
O103	0.075 (3)	0.039 (3)	0.104 (4)	−0.011 (3)	0.074 (3)	0.000 (3)
O401	0.111 (4)	0.024 (3)	0.117 (5)	−0.008 (3)	0.083 (4)	−0.005 (3)
N413	0.063 (4)	0.026 (3)	0.048 (4)	0.003 (3)	0.031 (3)	−0.009 (3)
N401	0.069 (4)	0.030 (4)	0.074 (5)	−0.004 (3)	0.048 (4)	−0.008 (3)
O402	0.074 (3)	0.032 (3)	0.084 (4)	−0.005 (2)	0.050 (3)	0.005 (3)
N101	0.096 (5)	0.053 (4)	0.112 (6)	−0.001 (4)	0.088 (5)	−0.008 (4)
O102	0.217 (8)	0.058 (4)	0.313 (12)	0.010 (5)	0.236 (9)	0.030 (6)
O101	0.103 (4)	0.039 (4)	0.128 (5)	−0.005 (3)	0.082 (4)	0.001 (3)
N116	0.146 (8)	0.048 (5)	0.240 (11)	0.008 (4)	0.171 (8)	0.024 (6)
O501	0.109 (6)	0.090 (6)	0.138 (7)	0.008 (4)	0.046 (5)	−0.027 (4)
C102	0.071 (6)	0.026 (4)	0.090 (7)	0.001 (4)	0.046 (5)	−0.008 (4)
C103	0.055 (5)	0.029 (4)	0.081 (6)	0.006 (3)	0.049 (5)	0.002 (4)
C104	0.072 (6)	0.048 (6)	0.116 (8)	−0.002 (4)	0.068 (6)	−0.006 (5)
C105	0.078 (6)	0.043 (5)	0.114 (8)	−0.019 (4)	0.070 (6)	−0.021 (5)
C106	0.077 (6)	0.020 (4)	0.096 (7)	−0.002 (4)	0.042 (6)	−0.005 (4)
C107	0.071 (6)	0.037 (5)	0.089 (7)	0.004 (4)	0.055 (5)	−0.010 (4)
C108	0.062 (5)	0.050 (5)	0.084 (6)	0.005 (4)	0.046 (5)	−0.003 (4)
C109	0.073 (5)	0.031 (4)	0.071 (6)	0.007 (4)	0.056 (5)	0.000 (4)
C110	0.063 (5)	0.038 (5)	0.092 (7)	−0.004 (4)	0.053 (5)	−0.002 (4)
C111	0.071 (6)	0.060 (6)	0.094 (7)	0.003 (4)	0.061 (6)	0.014 (5)
C112	0.057 (5)	0.022 (4)	0.073 (6)	0.004 (3)	0.043 (4)	−0.007 (4)
C114	0.051 (4)	0.052 (5)	0.053 (5)	0.000 (4)	0.023 (4)	0.000 (4)
C115	0.115 (8)	0.049 (6)	0.232 (14)	−0.001 (5)	0.142 (9)	0.027 (7)
C122	0.210 (13)	0.050 (7)	0.212 (14)	−0.025 (7)	0.160 (12)	0.001 (8)
C119	0.097 (6)	0.059 (6)	0.074 (6)	−0.033 (5)	0.080 (6)	−0.028 (5)
C120	0.152 (9)	0.048 (6)	0.204 (12)	−0.015 (5)	0.155 (9)	−0.005 (6)
C121	0.160 (10)	0.154 (11)	0.028 (5)	−0.081 (9)	0.013 (6)	0.002 (6)
C118	0.086 (6)	0.051 (5)	0.105 (7)	0.006 (5)	0.075 (6)	0.003 (5)
C117	0.076 (6)	0.097 (7)	0.091 (7)	−0.021 (6)	0.036 (6)	−0.008 (6)
C123	0.107 (7)	0.048 (6)	0.122 (8)	−0.015 (5)	0.062 (7)	−0.001 (5)
C202	0.068 (5)	0.029 (4)	0.061 (5)	−0.001 (4)	0.042 (4)	−0.002 (4)
C203	0.043 (4)	0.043 (5)	0.048 (5)	−0.006 (3)	0.027 (4)	−0.001 (4)
C204	0.066 (5)	0.037 (5)	0.047 (5)	−0.005 (4)	0.033 (4)	−0.004 (4)
C205	0.058 (5)	0.065 (6)	0.051 (5)	0.005 (4)	0.026 (5)	−0.004 (4)
C206	0.065 (5)	0.064 (6)	0.043 (5)	0.002 (4)	0.034 (4)	0.006 (4)
C207	0.067 (5)	0.044 (5)	0.070 (6)	−0.012 (4)	0.034 (5)	0.005 (4)
C208	0.047 (5)	0.048 (5)	0.062 (5)	0.008 (4)	0.034 (4)	0.015 (4)
C209	0.053 (5)	0.042 (5)	0.076 (6)	0.000 (4)	0.037 (5)	−0.007 (4)
C210	0.039 (4)	0.046 (5)	0.051 (5)	0.002 (3)	0.032 (4)	−0.001 (4)
C211	0.040 (4)	0.032 (5)	0.073 (6)	0.009 (3)	0.041 (4)	0.010 (4)
C212	0.044 (5)	0.055 (6)	0.077 (6)	0.003 (4)	0.038 (5)	0.012 (5)
C214	0.065 (5)	0.056 (5)	0.063 (5)	0.008 (4)	0.048 (5)	0.012 (4)
C215	0.067 (5)	0.040 (5)	0.071 (6)	0.001 (4)	0.050 (5)	−0.007 (4)
C222	0.215 (13)	0.036 (5)	0.196 (12)	0.007 (6)	0.175 (11)	0.009 (7)
C219	0.049 (4)	0.035 (4)	0.055 (5)	0.003 (3)	0.025 (4)	0.007 (4)
C220	0.071 (6)	0.083 (7)	0.111 (8)	0.011 (5)	0.072 (6)	0.016 (6)
C221	0.048 (4)	0.047 (4)	0.070 (6)	0.004 (4)	0.023 (4)	0.011 (4)
C218	0.070 (5)	0.020 (4)	0.065 (5)	0.009 (3)	0.055 (5)	0.005 (3)
C217	0.047 (4)	0.038 (4)	0.044 (4)	0.001 (3)	0.025 (4)	0.013 (3)
C223	0.133 (8)	0.036 (5)	0.087 (7)	0.012 (5)	0.043 (7)	−0.013 (5)
C302	0.036 (4)	0.029 (4)	0.043 (4)	−0.005 (3)	0.023 (4)	−0.005 (3)
C303	0.054 (5)	0.025 (4)	0.049 (5)	0.007 (3)	0.032 (4)	0.004 (4)
C304	0.075 (6)	0.026 (5)	0.100 (7)	−0.010 (4)	0.058 (5)	−0.014 (4)
C305	0.087 (6)	0.057 (6)	0.096 (7)	−0.002 (4)	0.080 (6)	−0.010 (5)
C306	0.070 (5)	0.017 (4)	0.109 (8)	−0.003 (4)	0.053 (6)	0.006 (4)
C307	0.078 (6)	0.030 (5)	0.078 (6)	0.001 (4)	0.042 (5)	−0.009 (4)
C308	0.041 (4)	0.039 (5)	0.073 (6)	0.004 (3)	0.034 (4)	0.001 (4)
C309	0.032 (4)	0.046 (5)	0.035 (4)	0.005 (3)	0.018 (3)	0.004 (4)
C310	0.055 (5)	0.035 (5)	0.048 (5)	0.002 (3)	0.037 (4)	0.005 (4)
C311	0.066 (5)	0.036 (5)	0.059 (5)	0.004 (4)	0.044 (5)	0.004 (4)
C312	0.047 (4)	0.035 (5)	0.075 (6)	−0.009 (3)	0.048 (4)	−0.004 (4)
C314	0.050 (4)	0.037 (4)	0.056 (5)	0.003 (3)	0.027 (4)	−0.002 (4)
C315	0.046 (4)	0.045 (5)	0.051 (5)	−0.002 (4)	0.026 (4)	−0.009 (4)
C322	0.094 (6)	0.036 (4)	0.114 (7)	0.008 (4)	0.074 (6)	0.002 (4)
C319	0.042 (5)	0.043 (5)	0.054 (5)	0.004 (4)	0.028 (4)	0.006 (4)
C320	0.135 (8)	0.038 (5)	0.113 (8)	−0.009 (5)	0.093 (7)	−0.013 (5)
C321	0.082 (6)	0.043 (5)	0.045 (5)	−0.019 (4)	0.017 (5)	−0.015 (4)
C318	0.053 (5)	0.035 (4)	0.061 (5)	−0.004 (3)	0.025 (4)	−0.004 (4)
C317	0.043 (4)	0.052 (5)	0.061 (5)	−0.019 (4)	0.027 (4)	−0.026 (4)
C323	0.080 (6)	0.045 (6)	0.112 (8)	0.006 (4)	0.043 (6)	0.029 (5)
C402	0.050 (4)	0.038 (4)	0.041 (5)	0.005 (4)	0.016 (4)	−0.007 (4)
C403	0.057 (5)	0.019 (4)	0.051 (5)	−0.011 (3)	0.030 (4)	−0.009 (4)
C404	0.054 (4)	0.044 (5)	0.029 (4)	−0.003 (4)	0.025 (4)	0.000 (4)
C405	0.075 (6)	0.032 (5)	0.061 (5)	−0.017 (4)	0.033 (5)	0.001 (4)
C406	0.063 (5)	0.045 (6)	0.065 (6)	−0.008 (4)	0.038 (5)	−0.013 (4)
C407	0.054 (5)	0.035 (5)	0.076 (6)	−0.004 (3)	0.044 (4)	−0.018 (4)
C408	0.065 (5)	0.028 (4)	0.034 (4)	−0.004 (3)	0.029 (4)	−0.007 (3)
C409	0.056 (5)	0.039 (5)	0.052 (5)	−0.010 (4)	0.025 (4)	−0.016 (4)
C410	0.051 (5)	0.039 (5)	0.057 (5)	−0.003 (3)	0.032 (4)	−0.007 (4)
C411	0.026 (4)	0.035 (4)	0.043 (4)	−0.005 (3)	0.011 (3)	−0.016 (3)
C412	0.061 (5)	0.030 (4)	0.052 (5)	0.001 (3)	0.029 (4)	0.000 (4)
C414	0.063 (5)	0.028 (4)	0.053 (5)	0.003 (3)	0.043 (4)	0.008 (3)
C415	0.048 (4)	0.035 (4)	0.046 (4)	−0.004 (3)	0.030 (4)	0.012 (3)
C422	0.064 (5)	0.098 (7)	0.082 (7)	0.030 (5)	0.028 (5)	0.039 (6)
C419	0.059 (5)	0.021 (4)	0.053 (5)	0.001 (3)	0.025 (4)	0.001 (3)
C420	0.105 (7)	0.085 (7)	0.071 (6)	−0.026 (5)	0.071 (6)	−0.005 (5)
C421	0.093 (6)	0.048 (5)	0.051 (5)	−0.010 (5)	0.026 (5)	0.006 (4)
C418	0.050 (4)	0.042 (5)	0.063 (5)	−0.007 (4)	0.037 (4)	0.000 (4)
C417	0.045 (4)	0.035 (4)	0.064 (5)	−0.013 (3)	0.025 (4)	0.005 (4)
C423	0.088 (7)	0.038 (6)	0.141 (9)	−0.002 (4)	0.074 (7)	0.012 (6)
C502	0.127 (10)	0.092 (8)	0.133 (10)	−0.035 (7)	−0.010 (9)	−0.011 (7)

Geometric parameters (Å, º)

N313—C312	1.333 (9)	C208—C209	1.373 (10)
N313—C314	1.442 (8)	C210—C211	1.373 (9)
N313—H313	0.8600	C210—H210	0.9300
O303—C312	1.231 (8)	C211—C212	1.476 (10)
N301—C302	1.361 (8)	C214—C222	1.515 (11)
N301—C308	1.393 (9)	C214—C215	1.516 (10)
N301—H301	0.8600	C214—H214	0.9800
O302—C315	1.247 (8)	C222—H22G	0.9600
N316—C315	1.366 (9)	C222—H22H	0.9600
N316—C311	1.429 (8)	C222—H22I	0.9600
N316—C317	1.438 (8)	C219—C221	1.508 (9)
O301—C306	1.388 (9)	C219—C218	1.536 (10)
O301—C323	1.402 (10)	C219—C220	1.576 (9)
O203—C212	1.231 (9)	C220—H22A	0.9600
N216—C215	1.347 (8)	C220—H22B	0.9600
N216—C211	1.422 (9)	C220—H22C	0.9600
N216—C217	1.432 (8)	C221—H22D	0.9600
O201—C206	1.362 (9)	C221—H22E	0.9600
O201—C223	1.414 (10)	C221—H22F	0.9600
N201—C202	1.354 (8)	C218—C217	1.336 (8)
N201—C208	1.402 (9)	C218—H218	0.9300
N201—H201	0.8600	C217—H217	0.9300
N213—C212	1.377 (9)	C223—H22J	0.9600
N213—C214	1.466 (8)	C223—H22K	0.9600
N213—H213	0.8600	C223—H22L	0.9600
O202—C215	1.240 (8)	C302—C303	1.373 (9)
O403—C412	1.245 (8)	C302—C319	1.507 (9)
N416—C415	1.334 (8)	C303—C309	1.446 (9)
N416—C411	1.430 (8)	C303—C310	1.459 (9)
N416—C417	1.432 (8)	C304—C305	1.388 (10)
N113—C112	1.312 (8)	C304—C309	1.390 (10)
N113—C114	1.438 (8)	C304—H304	0.9300
N113—H113	0.8600	C305—C306	1.362 (10)
O103—C112	1.236 (8)	C305—H305	0.9300
O401—C406	1.374 (9)	C306—C307	1.359 (10)
O401—C423	1.383 (10)	C307—C308	1.364 (10)
N413—C412	1.326 (8)	C307—H307	0.9300
N413—C414	1.436 (7)	C308—C309	1.390 (10)
N413—H413	0.8600	C310—C311	1.332 (9)
N401—C408	1.352 (8)	C310—H310	0.9300
N401—C402	1.391 (9)	C311—C312	1.479 (10)
N401—H401	0.8600	C314—C315	1.495 (9)
O402—C415	1.223 (7)	C314—C322	1.519 (9)
N101—C108	1.360 (9)	C314—H314	0.9800
N101—C102	1.385 (9)	C322—H32G	0.9600
N101—H101	0.8600	C322—H32H	0.9600
O102—C115	1.200 (9)	C322—H32I	0.9600
O101—C106	1.391 (8)	C319—C321	1.530 (10)
O101—C123	1.414 (9)	C319—C318	1.530 (10)
N116—C115	1.384 (11)	C319—C320	1.536 (10)
N116—C111	1.435 (10)	C320—H32A	0.9600
N116—C117	1.568 (12)	C320—H32B	0.9600
O501—C502	1.372 (11)	C320—H32C	0.9600
O501—H501	0.8200	C321—H32D	0.9600
C102—C103	1.363 (10)	C321—H32E	0.9600
C102—C119	1.510 (11)	C321—H32F	0.9600
C103—C110	1.422 (10)	C318—C317	1.288 (9)
C103—C109	1.453 (10)	C318—H318	0.9300
C104—C105	1.366 (11)	C317—H317	0.9300
C104—C109	1.400 (10)	C323—H32J	0.9600
C104—H104	0.9300	C323—H32K	0.9600
C105—C106	1.371 (10)	C323—H32L	0.9600
C105—H105	0.9300	C402—C403	1.416 (10)
C106—C107	1.344 (10)	C402—C419	1.498 (10)
C107—C108	1.392 (10)	C403—C410	1.434 (9)
C107—H107	0.9300	C403—C409	1.452 (10)
C108—C109	1.401 (10)	C404—C405	1.371 (9)
C110—C111	1.339 (10)	C404—C409	1.391 (9)
C110—H110	0.9300	C404—H404	0.9300
C111—C112	1.474 (10)	C405—C406	1.389 (10)
C114—C115	1.420 (11)	C405—H405	0.9300
C114—C122	1.488 (12)	C406—C407	1.400 (10)
C114—H114	0.9800	C407—C408	1.394 (9)
C122—H12G	0.9600	C407—H407	0.9300
C122—H12H	0.9600	C408—C409	1.409 (9)
C122—H12I	0.9600	C410—C411	1.329 (9)
C119—C118	1.495 (12)	C410—H410	0.9300
C119—C120	1.513 (10)	C411—C412	1.462 (9)
C119—C121	1.554 (13)	C414—C422	1.491 (10)
C120—H12A	0.9600	C414—C415	1.526 (9)
C120—H12B	0.9600	C414—H414	0.9800
C120—H12C	0.9600	C422—H42G	0.9600
C121—H12D	0.9600	C422—H42H	0.9600
C121—H12E	0.9600	C422—H42I	0.9600
C121—H12F	0.9600	C419—C418	1.489 (10)
C118—C117	1.267 (11)	C419—C421	1.490 (10)
C118—H118	0.9300	C419—C420	1.526 (10)
C117—H117	0.9300	C420—H42A	0.9600
C123—H12J	0.9600	C420—H42B	0.9600
C123—H12K	0.9600	C420—H42C	0.9600
C123—H12L	0.9600	C421—H42D	0.9600
C202—C203	1.375 (9)	C421—H42E	0.9600
C202—C219	1.516 (10)	C421—H42F	0.9600
C203—C209	1.423 (10)	C418—C417	1.328 (9)
C203—C210	1.450 (9)	C418—H418	0.9300
C204—C209	1.363 (10)	C417—H417	0.9300
C204—C205	1.399 (10)	C423—H42J	0.9600
C204—H204	0.9300	C423—H42K	0.9600
C205—C206	1.430 (10)	C423—H42L	0.9600
C205—H205	0.9300	C502—H50A	0.9600
C206—C207	1.401 (10)	C502—H50B	0.9600
C207—C208	1.372 (10)	C502—H50C	0.9600
C207—H207	0.9300
C312—N313—C314	122.9 (6)	C219—C221—H22E	109.5
C312—N313—H313	118.5	H22D—C221—H22E	109.5
C314—N313—H313	118.5	C219—C221—H22F	109.5
C302—N301—C308	110.7 (6)	H22D—C221—H22F	109.5
C302—N301—H301	124.7	H22E—C221—H22F	109.5
C308—N301—H301	124.7	C217—C218—C219	126.3 (7)
C315—N316—C311	121.4 (6)	C217—C218—H218	116.9
C315—N316—C317	119.3 (6)	C219—C218—H218	116.9
C311—N316—C317	117.1 (6)	C218—C217—N216	126.2 (7)
C306—O301—C323	120.2 (8)	C218—C217—H217	116.9
C215—N216—C211	120.5 (7)	N216—C217—H217	116.9
C215—N216—C217	117.9 (6)	O201—C223—H22J	109.5
C211—N216—C217	120.1 (5)	O201—C223—H22K	109.5
C206—O201—C223	118.4 (7)	H22J—C223—H22K	109.5
C202—N201—C208	109.8 (6)	O201—C223—H22L	109.5
C202—N201—H201	125.1	H22J—C223—H22L	109.5
C208—N201—H201	125.1	H22K—C223—H22L	109.5
C212—N213—C214	122.4 (6)	N301—C302—C303	109.4 (6)
C212—N213—H213	118.8	N301—C302—C319	121.6 (6)
C214—N213—H213	118.8	C303—C302—C319	128.9 (6)
C415—N416—C411	122.4 (6)	C302—C303—C309	105.5 (6)
C415—N416—C417	114.8 (5)	C302—C303—C310	134.3 (6)
C411—N416—C417	121.5 (5)	C309—C303—C310	120.2 (6)
C112—N113—C114	126.4 (6)	C305—C304—C309	119.9 (8)
C112—N113—H113	116.8	C305—C304—H304	120.0
C114—N113—H113	116.8	C309—C304—H304	120.0
C406—O401—C423	117.6 (7)	C306—C305—C304	120.2 (8)
C412—N413—C414	124.5 (6)	C306—C305—H305	119.9
C412—N413—H413	117.8	C304—C305—H305	119.9
C414—N413—H413	117.8	C307—C306—C305	121.6 (7)
C408—N401—C402	111.7 (6)	C307—C306—O301	116.2 (8)
C408—N401—H401	124.1	C305—C306—O301	122.1 (8)
C402—N401—H401	124.1	C306—C307—C308	117.5 (8)
C108—N101—C102	112.2 (7)	C306—C307—H307	121.2
C108—N101—H101	123.9	C308—C307—H307	121.2
C102—N101—H101	123.9	C307—C308—C309	124.0 (8)
C106—O101—C123	118.9 (7)	C307—C308—N301	130.6 (8)
C115—N116—C111	122.8 (7)	C309—C308—N301	105.4 (6)
C115—N116—C117	115.0 (7)	C308—C309—C304	116.5 (7)
C111—N116—C117	118.2 (7)	C308—C309—C303	109.0 (6)
C502—O501—H501	109.5	C304—C309—C303	134.4 (7)
C103—C102—N101	106.9 (7)	C311—C310—C303	137.0 (7)
C103—C102—C119	129.8 (7)	C311—C310—H310	111.5
N101—C102—C119	122.7 (7)	C303—C310—H310	111.5
C102—C103—C110	131.6 (7)	C310—C311—N316	128.6 (7)
C102—C103—C109	107.4 (6)	C310—C311—C312	116.6 (7)
C110—C103—C109	120.9 (7)	N316—C311—C312	114.5 (6)
C105—C104—C109	121.1 (8)	O303—C312—N313	122.7 (7)
C105—C104—H104	119.4	O303—C312—C311	121.2 (7)
C109—C104—H104	119.4	N313—C312—C311	116.0 (7)
C104—C105—C106	118.9 (8)	N313—C314—C315	108.0 (6)
C104—C105—H105	120.6	N313—C314—C322	110.8 (6)
C106—C105—H105	120.6	C315—C314—C322	112.4 (6)
C107—C106—C105	123.9 (7)	N313—C314—H314	108.5
C107—C106—O101	115.4 (7)	C315—C314—H314	108.5
C105—C106—O101	120.5 (8)	C322—C314—H314	108.5
C106—C107—C108	116.6 (7)	O302—C315—N316	119.0 (6)
C106—C107—H107	121.7	O302—C315—C314	123.8 (7)
C108—C107—H107	121.7	N316—C315—C314	117.2 (6)
N101—C108—C107	131.1 (8)	C314—C322—H32G	109.5
N101—C108—C109	106.0 (7)	C314—C322—H32H	109.5
C107—C108—C109	122.7 (8)	H32G—C322—H32H	109.5
C104—C109—C108	116.6 (7)	C314—C322—H32I	109.5
C104—C109—C103	135.9 (7)	H32G—C322—H32I	109.5
C108—C109—C103	107.1 (7)	H32H—C322—H32I	109.5
C111—C110—C103	140.7 (8)	C302—C319—C321	110.8 (5)
C111—C110—H110	109.7	C302—C319—C318	106.7 (6)
C103—C110—H110	109.7	C321—C319—C318	112.1 (6)
C110—C111—N116	126.8 (8)	C302—C319—C320	110.5 (6)
C110—C111—C112	118.6 (7)	C321—C319—C320	108.7 (7)
N116—C111—C112	114.4 (7)	C318—C319—C320	108.0 (6)
O103—C112—N113	121.2 (7)	C319—C320—H32A	109.5
O103—C112—C111	120.3 (7)	C319—C320—H32B	109.5
N113—C112—C111	118.4 (7)	H32A—C320—H32B	109.5
C115—C114—N113	114.8 (7)	C319—C320—H32C	109.5
C115—C114—C122	111.8 (8)	H32A—C320—H32C	109.5
N113—C114—C122	107.6 (7)	H32B—C320—H32C	109.5
C115—C114—H114	107.5	C319—C321—H32D	109.5
N113—C114—H114	107.5	C319—C321—H32E	109.5
C122—C114—H114	107.5	H32D—C321—H32E	109.5
O102—C115—N116	119.0 (9)	C319—C321—H32F	109.5
O102—C115—C114	121.1 (9)	H32D—C321—H32F	109.5
N116—C115—C114	119.8 (7)	H32E—C321—H32F	109.5
C114—C122—H12G	109.5	C317—C318—C319	129.9 (7)
C114—C122—H12H	109.5	C317—C318—H318	115.1
H12G—C122—H12H	109.5	C319—C318—H318	115.1
C114—C122—H12I	109.5	C318—C317—N316	126.9 (7)
H12G—C122—H12I	109.5	C318—C317—H317	116.5
H12H—C122—H12I	109.5	N316—C317—H317	116.5
C118—C119—C102	105.2 (7)	O301—C323—H32J	109.5
C118—C119—C120	105.6 (7)	O301—C323—H32K	109.5
C102—C119—C120	109.5 (7)	H32J—C323—H32K	109.5
C118—C119—C121	110.4 (8)	O301—C323—H32L	109.5
C102—C119—C121	110.1 (7)	H32J—C323—H32L	109.5
C120—C119—C121	115.5 (8)	H32K—C323—H32L	109.5
C119—C120—H12A	109.5	N401—C402—C403	106.0 (6)
C119—C120—H12B	109.5	N401—C402—C419	123.2 (7)
H12A—C120—H12B	109.5	C403—C402—C419	130.8 (6)
C119—C120—H12C	109.5	C402—C403—C410	129.9 (6)
H12A—C120—H12C	109.5	C402—C403—C409	107.6 (6)
H12B—C120—H12C	109.5	C410—C403—C409	122.4 (6)
C119—C121—H12D	109.5	C405—C404—C409	119.4 (7)
C119—C121—H12E	109.5	C405—C404—H404	120.3
H12D—C121—H12E	109.5	C409—C404—H404	120.3
C119—C121—H12F	109.5	C404—C405—C406	121.0 (7)
H12D—C121—H12F	109.5	C404—C405—H405	119.5
H12E—C121—H12F	109.5	C406—C405—H405	119.5
C117—C118—C119	128.9 (8)	O401—C406—C405	124.9 (7)
C117—C118—H118	115.5	O401—C406—C407	113.4 (7)
C119—C118—H118	115.6	C405—C406—C407	121.7 (7)
C118—C117—N116	125.4 (9)	C408—C407—C406	116.5 (7)
C118—C117—H117	117.3	C408—C407—H407	121.8
N116—C117—H117	117.3	C406—C407—H407	121.8
O101—C123—H12J	109.5	N401—C408—C407	129.0 (7)
O101—C123—H12K	109.5	N401—C408—C409	108.5 (6)
H12J—C123—H12K	109.5	C407—C408—C409	122.2 (7)
O101—C123—H12L	109.5	C404—C409—C408	119.1 (7)
H12J—C123—H12L	109.5	C404—C409—C403	134.8 (7)
H12K—C123—H12L	109.5	C408—C409—C403	106.0 (6)
N201—C202—C203	109.2 (6)	C411—C410—C403	141.6 (7)
N201—C202—C219	122.9 (6)	C411—C410—H410	109.2
C203—C202—C219	127.8 (6)	C403—C410—H410	109.2
C202—C203—C209	105.9 (6)	C410—C411—N416	125.5 (6)
C202—C203—C210	132.3 (7)	C410—C411—C412	118.2 (7)
C209—C203—C210	121.7 (7)	N416—C411—C412	116.2 (6)
C209—C204—C205	120.3 (8)	O403—C412—N413	121.1 (7)
C209—C204—H204	119.9	O403—C412—C411	121.8 (7)
C205—C204—H204	119.9	N413—C412—C411	117.1 (7)
C204—C205—C206	119.9 (8)	N413—C414—C422	114.0 (6)
C204—C205—H205	120.1	N413—C414—C415	109.9 (5)
C206—C205—H205	120.1	C422—C414—C415	110.7 (6)
O201—C206—C207	115.2 (7)	N413—C414—H414	107.3
O201—C206—C205	125.1 (7)	C422—C414—H414	107.3
C207—C206—C205	119.7 (8)	C415—C414—H414	107.3
C208—C207—C206	116.2 (7)	O402—C415—N416	122.6 (6)
C208—C207—H207	121.9	O402—C415—C414	119.6 (6)
C206—C207—H207	121.9	N416—C415—C414	117.8 (6)
C207—C208—C209	125.9 (8)	C414—C422—H42G	109.5
C207—C208—N201	128.4 (7)	C414—C422—H42H	109.5
C209—C208—N201	105.7 (6)	H42G—C422—H42H	109.5
C204—C209—C208	118.1 (7)	C414—C422—H42I	109.5
C204—C209—C203	132.5 (7)	H42G—C422—H42I	109.5
C208—C209—C203	109.4 (7)	H42H—C422—H42I	109.5
C211—C210—C203	137.0 (7)	C418—C419—C421	113.1 (6)
C211—C210—H210	111.5	C418—C419—C402	104.2 (6)
C203—C210—H210	111.5	C421—C419—C402	110.9 (6)
C210—C211—N216	128.6 (6)	C418—C419—C420	109.1 (6)
C210—C211—C212	113.2 (7)	C421—C419—C420	108.1 (7)
N216—C211—C212	118.1 (7)	C402—C419—C420	111.3 (6)
O203—C212—N213	120.6 (7)	C419—C420—H42A	109.5
O203—C212—C211	125.6 (7)	C419—C420—H42B	109.5
N213—C212—C211	113.7 (7)	H42A—C420—H42B	109.5
N213—C214—C222	109.5 (7)	C419—C420—H42C	109.5
N213—C214—C215	106.8 (6)	H42A—C420—H42C	109.5
C222—C214—C215	112.4 (7)	H42B—C420—H42C	109.5
N213—C214—H214	109.4	C419—C421—H42D	109.5
C222—C214—H214	109.4	C419—C421—H42E	109.5
C215—C214—H214	109.4	H42D—C421—H42E	109.5
O202—C215—N216	120.5 (8)	C419—C421—H42F	109.5
O202—C215—C214	120.9 (7)	H42D—C421—H42F	109.5
N216—C215—C214	118.6 (7)	H42E—C421—H42F	109.5
C214—C222—H22G	109.5	C417—C418—C419	131.5 (7)
C214—C222—H22H	109.5	C417—C418—H418	114.3
H22G—C222—H22H	109.5	C419—C418—H418	114.3
C214—C222—H22I	109.5	C418—C417—N416	125.8 (6)
H22G—C222—H22I	109.5	C418—C417—H417	117.1
H22H—C222—H22I	109.5	N416—C417—H417	117.1
C221—C219—C202	113.0 (6)	O401—C423—H42J	109.5
C221—C219—C218	115.0 (6)	O401—C423—H42K	109.5
C202—C219—C218	105.0 (5)	H42J—C423—H42K	109.5
C221—C219—C220	108.1 (6)	O401—C423—H42L	109.5
C202—C219—C220	111.0 (6)	H42J—C423—H42L	109.5
C218—C219—C220	104.5 (6)	H42K—C423—H42L	109.5
C219—C220—H22A	109.5	O501—C502—H50A	109.5
C219—C220—H22B	109.5	O501—C502—H50B	109.5
H22A—C220—H22B	109.5	H50A—C502—H50B	109.5
C219—C220—H22C	109.5	O501—C502—H50C	109.5
H22A—C220—H22C	109.5	H50A—C502—H50C	109.5
H22B—C220—H22C	109.5	H50B—C502—H50C	109.5
C219—C221—H22D	109.5
C108—N101—C102—C103	−1.3 (10)	C308—N301—C302—C303	−2.4 (8)
C108—N101—C102—C119	−173.4 (8)	C308—N301—C302—C319	179.6 (6)
N101—C102—C103—C110	−178.1 (9)	N301—C302—C303—C309	2.6 (7)
C119—C102—C103—C110	−6.9 (15)	C319—C302—C303—C309	−179.6 (6)
N101—C102—C103—C109	4.2 (9)	N301—C302—C303—C310	−174.9 (7)
C119—C102—C103—C109	175.5 (8)	C319—C302—C303—C310	3.0 (13)
C109—C104—C105—C106	0.3 (14)	C309—C304—C305—C306	6.3 (13)
C104—C105—C106—C107	−3.4 (14)	C304—C305—C306—C307	−4.6 (13)
C104—C105—C106—O101	−178.1 (8)	C304—C305—C306—O301	178.2 (8)
C123—O101—C106—C107	178.5 (8)	C323—O301—C306—C307	169.9 (8)
C123—O101—C106—C105	−6.4 (13)	C323—O301—C306—C305	−12.7 (12)
C105—C106—C107—C108	2.4 (14)	C305—C306—C307—C308	2.4 (13)
O101—C106—C107—C108	177.3 (8)	O301—C306—C307—C308	179.8 (7)
C102—N101—C108—C107	−178.9 (9)	C306—C307—C308—C309	−2.0 (12)
C102—N101—C108—C109	−2.2 (10)	C306—C307—C308—N301	178.3 (7)
C106—C107—C108—N101	178.0 (9)	C302—N301—C308—C307	−179.1 (8)
C106—C107—C108—C109	1.8 (13)	C302—N301—C308—C309	1.1 (8)
C105—C104—C109—C108	3.4 (13)	C307—C308—C309—C304	3.7 (11)
C105—C104—C109—C103	174.8 (9)	N301—C308—C309—C304	−176.5 (6)
N101—C108—C109—C104	178.4 (8)	C307—C308—C309—C303	−179.3 (7)
C107—C108—C109—C104	−4.5 (13)	N301—C308—C309—C303	0.5 (8)
N101—C108—C109—C103	4.7 (9)	C305—C304—C309—C308	−5.7 (11)
C107—C108—C109—C103	−178.3 (8)	C305—C304—C309—C303	178.2 (8)
C102—C103—C109—C104	−177.5 (10)	C302—C303—C309—C308	−1.9 (8)
C110—C103—C109—C104	4.5 (15)	C310—C303—C309—C308	176.0 (6)
C102—C103—C109—C108	−5.6 (9)	C302—C303—C309—C304	174.4 (8)
C110—C103—C109—C108	176.5 (7)	C310—C303—C309—C304	−7.7 (12)
C102—C103—C110—C111	−0.3 (19)	C302—C303—C310—C311	−5.2 (15)
C109—C103—C110—C111	177.1 (11)	C309—C303—C310—C311	177.7 (8)
C103—C110—C111—N116	−9 (2)	C303—C310—C311—N316	−8.8 (15)
C103—C110—C111—C112	176.1 (10)	C303—C310—C311—C312	176.3 (8)
C115—N116—C111—C110	165.8 (11)	C315—N316—C311—C310	157.2 (8)
C117—N116—C111—C110	−37.8 (15)	C317—N316—C311—C310	−39.5 (11)
C115—N116—C111—C112	−19.1 (16)	C315—N316—C311—C312	−27.8 (9)
C117—N116—C111—C112	137.3 (8)	C317—N316—C311—C312	135.5 (7)
C114—N113—C112—O103	−178.0 (7)	C314—N313—C312—O303	−159.2 (7)
C114—N113—C112—C111	−2.8 (12)	C314—N313—C312—C311	18.4 (9)
C110—C111—C112—O103	7.8 (13)	C310—C311—C312—O303	13.4 (11)
N116—C111—C112—O103	−167.7 (8)	N316—C311—C312—O303	−162.2 (6)
C110—C111—C112—N113	−167.4 (8)	C310—C311—C312—N313	−164.3 (7)
N116—C111—C112—N113	17.1 (12)	N316—C311—C312—N313	20.1 (9)
C112—N113—C114—C115	−10.6 (12)	C312—N313—C314—C315	−46.5 (8)
C112—N113—C114—C122	−135.7 (9)	C312—N313—C314—C322	−170.0 (6)
C111—N116—C115—O102	−178.5 (12)	C311—N316—C315—O302	174.7 (7)
C117—N116—C115—O102	24.4 (18)	C317—N316—C315—O302	11.8 (10)
C111—N116—C115—C114	6.1 (19)	C311—N316—C315—C314	−2.3 (10)
C117—N116—C115—C114	−150.9 (10)	C317—N316—C315—C314	−165.3 (6)
N113—C114—C115—O102	−166.5 (12)	N313—C314—C315—O302	−140.2 (7)
C122—C114—C115—O102	−43.7 (17)	C322—C314—C315—O302	−17.7 (11)
N113—C114—C115—N116	8.7 (16)	N313—C314—C315—N316	36.7 (8)
C122—C114—C115—N116	131.6 (12)	C322—C314—C315—N316	159.2 (6)
C103—C102—C119—C118	63.5 (11)	N301—C302—C319—C321	108.0 (7)
N101—C102—C119—C118	−126.4 (8)	C303—C302—C319—C321	−69.7 (9)
C103—C102—C119—C120	176.6 (9)	N301—C302—C319—C318	−129.7 (6)
N101—C102—C119—C120	−13.3 (12)	C303—C302—C319—C318	52.6 (9)
C103—C102—C119—C121	−55.4 (12)	N301—C302—C319—C320	−12.5 (9)
N101—C102—C119—C121	114.7 (9)	C303—C302—C319—C320	169.8 (7)
C102—C119—C118—C117	−84.1 (11)	C302—C319—C318—C317	−80.2 (10)
C120—C119—C118—C117	160.1 (9)	C321—C319—C318—C317	41.2 (11)
C121—C119—C118—C117	34.6 (12)	C320—C319—C318—C317	161.0 (8)
C119—C118—C117—N116	2.8 (15)	C319—C318—C317—N316	−0.4 (14)
C115—N116—C117—C118	−128.8 (12)	C315—N316—C317—C318	−119.5 (9)
C111—N116—C117—C118	73.0 (13)	C311—N316—C317—C318	76.8 (10)
C208—N201—C202—C203	−2.4 (9)	C408—N401—C402—C403	0.5 (8)
C208—N201—C202—C219	−179.6 (7)	C408—N401—C402—C419	−178.8 (7)
N201—C202—C203—C209	0.7 (8)	N401—C402—C403—C410	175.6 (7)
C219—C202—C203—C209	177.8 (7)	C419—C402—C403—C410	−5.2 (12)
N201—C202—C203—C210	−175.1 (7)	N401—C402—C403—C409	−1.1 (7)
C219—C202—C203—C210	1.9 (14)	C419—C402—C403—C409	178.2 (7)
C209—C204—C205—C206	−1.2 (11)	C409—C404—C405—C406	3.4 (12)
C223—O201—C206—C207	−176.8 (7)	C423—O401—C406—C405	2.0 (12)
C223—O201—C206—C205	5.3 (12)	C423—O401—C406—C407	−177.5 (7)
C204—C205—C206—O201	178.6 (7)	C404—C405—C406—O401	177.8 (7)
C204—C205—C206—C207	0.8 (11)	C404—C405—C406—C407	−2.8 (12)
O201—C206—C207—C208	−177.5 (7)	O401—C406—C407—C408	−179.1 (7)
C205—C206—C207—C208	0.5 (11)	C405—C406—C407—C408	1.4 (11)
C206—C207—C208—C209	−1.5 (13)	C402—N401—C408—C407	175.1 (8)
C206—C207—C208—N201	−180.0 (7)	C402—N401—C408—C409	0.2 (8)
C202—N201—C208—C207	−178.3 (8)	C406—C407—C408—N401	−175.1 (7)
C202—N201—C208—C209	3.0 (9)	C406—C407—C408—C409	−0.8 (11)
C205—C204—C209—C208	0.3 (12)	C405—C404—C409—C408	−2.8 (11)
C205—C204—C209—C203	−176.6 (8)	C405—C404—C409—C403	174.1 (8)
C207—C208—C209—C204	1.1 (13)	N401—C408—C409—C404	176.9 (6)
N201—C208—C209—C204	179.8 (7)	C407—C408—C409—C404	1.5 (11)
C207—C208—C209—C203	178.7 (8)	N401—C408—C409—C403	−0.8 (8)
N201—C208—C209—C203	−2.5 (9)	C407—C408—C409—C403	−176.2 (7)
C202—C203—C209—C204	178.3 (9)	C402—C403—C409—C404	−176.0 (8)
C210—C203—C209—C204	−5.2 (13)	C410—C403—C409—C404	7.1 (13)
C202—C203—C209—C208	1.2 (9)	C402—C403—C409—C408	1.2 (8)
C210—C203—C209—C208	177.6 (7)	C410—C403—C409—C408	−175.7 (6)
C202—C203—C210—C211	−14.4 (15)	C402—C403—C410—C411	12.0 (15)
C209—C203—C210—C211	170.3 (8)	C409—C403—C410—C411	−171.8 (9)
C203—C210—C211—N216	−4.8 (14)	C403—C410—C411—N416	8.4 (15)
C203—C210—C211—C212	178.1 (8)	C403—C410—C411—C412	−172.1 (9)
C215—N216—C211—C210	157.9 (7)	C415—N416—C411—C410	−160.0 (7)
C217—N216—C211—C210	−36.4 (11)	C417—N416—C411—C410	33.6 (10)
C215—N216—C211—C212	−25.1 (10)	C415—N416—C411—C412	20.5 (9)
C217—N216—C211—C212	140.6 (6)	C417—N416—C411—C412	−145.9 (7)
C214—N213—C212—O203	−156.9 (7)	C414—N413—C412—O403	168.7 (6)
C214—N213—C212—C211	20.7 (11)	C414—N413—C412—C411	−11.7 (10)
C210—C211—C212—O203	12.6 (11)	C410—C411—C412—O403	−17.6 (11)
N216—C211—C212—O203	−164.8 (7)	N416—C411—C412—O403	161.9 (6)
C210—C211—C212—N213	−164.8 (7)	C410—C411—C412—N413	162.8 (7)
N216—C211—C212—N213	17.7 (10)	N416—C411—C412—N413	−17.7 (9)
C212—N213—C214—C222	−169.4 (8)	C412—N413—C414—C422	−89.6 (8)
C212—N213—C214—C215	−47.4 (10)	C412—N413—C414—C415	35.3 (9)
C211—N216—C215—O202	173.5 (7)	C411—N416—C415—O402	−175.1 (6)
C217—N216—C215—O202	7.5 (11)	C417—N416—C415—O402	−7.8 (10)
C211—N216—C215—C214	−5.7 (11)	C411—N416—C415—C414	5.0 (10)
C217—N216—C215—C214	−171.6 (6)	C417—N416—C415—C414	172.2 (6)
N213—C214—C215—O202	−140.6 (7)	N413—C414—C415—O402	149.2 (6)
C222—C214—C215—O202	−20.5 (12)	C422—C414—C415—O402	−84.0 (9)
N213—C214—C215—N216	38.6 (10)	N413—C414—C415—N416	−30.8 (9)
C222—C214—C215—N216	158.7 (8)	C422—C414—C415—N416	95.9 (7)
N201—C202—C219—C221	113.4 (8)	N401—C402—C419—C418	124.4 (7)
C203—C202—C219—C221	−63.3 (10)	C403—C402—C419—C418	−54.7 (9)
N201—C202—C219—C218	−120.5 (7)	N401—C402—C419—C421	−113.5 (8)
C203—C202—C219—C218	62.8 (10)	C403—C402—C419—C421	67.4 (10)
N201—C202—C219—C220	−8.3 (10)	N401—C402—C419—C420	7.0 (10)
C203—C202—C219—C220	175.0 (7)	C403—C402—C419—C420	−172.1 (7)
C221—C219—C218—C217	40.5 (9)	C421—C419—C418—C417	−38.3 (11)
C202—C219—C218—C217	−84.3 (8)	C402—C419—C418—C417	82.3 (9)
C220—C219—C218—C217	158.9 (6)	C420—C419—C418—C417	−158.7 (8)
C219—C218—C217—N216	−1.4 (10)	C419—C418—C417—N416	−3.3 (13)
C215—N216—C217—C218	−119.5 (8)	C415—N416—C417—C418	121.2 (8)
C211—N216—C217—C218	74.5 (9)	C411—N416—C417—C418	−71.4 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N313—H313···O203^i	0.86	2.01	2.847 (6)	165
N301—H301···O302^ii	0.86	2.13	2.919 (6)	153
N201—H201···O202^iii	0.86	2.20	2.936 (6)	144
N213—H213···O303^ii	0.86	2.03	2.834 (6)	155
N113—H113···O403	0.86	2.02	2.861 (6)	167
N413—H413···O103	0.86	2.08	2.900 (6)	158
N401—H401···O402^iv	0.86	2.07	2.859 (6)	152
N101—H101···O102^v	0.86	2.12	2.928 (6)	156
O501—H501···O103^i	0.82	1.87	2.677 (6)	167

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