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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 75| Part 3| March 2019| Pages 319-323
https://doi.org/10.1107/S2056989019001336

Crystal structure of a host–guest complex of the tris-urea receptor, 3-(4-nitro­phen­yl)-1,1-bis­­{2-[3-(4-nitro­phen­yl)ureido]eth­yl}urea, that encapsulates hydrogen-bonded chains of di­hydrogen phosphate anions with separate tetra-n-butyl­ammonium counter-ions

CROSSMARK_Color_square_no_text.svg
Ruyu Wang,a Xi Shu,a Yu Fan,a Shoujian Li,a Yongdong Jin,a Chuanqin Xiaa and Chao Huanga*

aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: chuang@scu.edu.cn

Edited by V. Khrustalev, Russian Academy of Sciences, Russia (Received 14 March 2018; accepted 24 January 2019; online 5 February 2019)

The title compound, C25H25N9O9·C16H36N+·H2PO4− (I) or (C25H25N9O9)·(n-Bu4N+)·(H2PO4−) (systematic name: 3-(4-nitro­phen­yl)-1,1-bis­{2-[3-(4-nitro­phen­yl)ureido]eth­yl}urea tetra­butyl­ammonium di­hydrogen phosphate), comprises a tris-urea receptor (R), a di­hydrogen phosphate anion and a tetra-n-butyl­ammonium cation. It crystallizes with two independent formula units in the asymmetric unit. The conformations of the two tris-urea receptors are stabilized by N—H⋯O and C—H⋯O intra­molecular hydrogen bonds. Each di­hydrogen phosphate anion has two O—H⋯O inter­molecular hydrogen-bonding inter­actions with the other di­hydrogen phosphate anion. Inversion-related di-anion units are linked by further O—H⋯O hydrogen bonds, forming a chain propagating along the a-axis direction. Each di­hydrogen phosphate anion makes a total of four N—H⋯O(H2PO4−) hydrogen bonds with two ureido subunits from two different tris-urea receptors, hence each tris-urea receptor provides the two ureido subunits for the encapsulation of the H2PO4− hydrogen-bonded chain. There are numerous inter­molecular C—H⋯O hydrogen bonds present involving both receptor mol­ecules and the tetra-n-butyl­ammonium cations, so forming a supra­molecular three-dimensional structure. One of the butyl groups and one of the nitro groups are disordered over two positions of equal occupancy.

CCDC reference: 1893140

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1. Chemical context

Anions play an important role in many chemical, catalysis, environmental and biological systems (Sessler et al., 2006[Sessler, J. L., Cho, D.-G. & Lynch, V. (2006). J. Am. Chem. Soc. 128, 16518-16519.]; Vickers & Beer, 2007[Vickers, M. S. & Beer, P. D. (2007). Chem. Soc. Rev. 36, 211-225.]; Beer & Gale, 2001[Beer, P. D. & Gale, P. A. (2001). Angew. Chem. Int. Ed. 40, 486-516.]). The use of urea-based receptors as hydrogen-bond donors in anion recognition has attracted much attention (Xu et al., 2017[Xu, Z., Ge, H., Han, X., Liu, S. H., Meng, X. G. & Yin, J. (2017). Tetrahedron, 73, 6386-6391.]; Amendola et al., 2006[Amendola, V., Esteban-Gómez, D., Fabbrizzi, L. & Licchelli, M. (2006). Acc. Chem. Res. 39, 343-353.]; Hoque & Das, 2017[Hoque, M. N. & Das, G. (2017). CrystEngComm, 19, 1343-1360.]; Bregović et al., 2015[Bregović, V. B., Basarić, N. & Mlinarić-Majerski, K. (2015). Coord. Chem. Rev. 295, 80-124.]; Li et al., 2010[Li, A. F., Wang, J. H., Wang, F. & Jiang, Y. B. (2010). Chem. Soc. Rev. 39, 3729-3745.]). In particular, considerable research efforts have been devoted to the designation of receptors containing a ureido subunit (which selectively recognizes fluoride ions), such as 1,3-bis­(4-nitro­phen­yl) urea (Boiocchi et al., 2004[Boiocchi, M., Del Boca, L., Gómez, D. E., Fabbrizzi, L., Licchelli, M. & Monzani, E. (2004). J. Am. Chem. Soc. 126, 16507-16514.]), or a urea subunit equipped with two naphthalenimide moieties (Esteban-Gómez et al., 2005[Esteban-Gómez, D., Fabbrizzi, L. & Licchelli, M. (2005). J. Org. Chem. 70, 5717-5720.]), and thio­urea or urea-based indole conjugated ligands (Bose & Ghosh, 2010[Bose, P. & Ghosh, P. (2010). Chem. Commun. 46, 2962-2964.]). Recently, tris­(2-amino­eth­yl)amine (tren)-based tripodal urea or thio­urea receptors for the recognition and separation of anions have been investigated (Arunachalam & Ghosh, 2011[Arunachalam, M. & Ghosh, P. (2011). Chem. Commun. 47, 8477-8492.]; Custelcean, 2013[Custelcean, R. (2013). Chem. Commun. 49, 2173-2182.]; Dey et al., 2016[Dey, S. K., Basu, A., Chutia, R. & Das, G. (2016). RSC Adv. 6, 26568-26589.]; Hay et al., 2005[Hay, B. P., Firman, T. K. & Moyer, B. A. (2005). J. Am. Chem. Soc. 127, 1810-1819.]). However, tris-urea receptors have been rarely studied to date. In our ongoing research on nitro­gen-rich organic ligands (Wang et al., 2015[Wang, J., Su, D., Wang, D., Ding, S., Huang, C., Huang, H., Hu, X., Wang, Z. & Li, S. (2015). Inorg. Chem. 54, 10648-10655.]) and the design and synthesis of ureido receptors (Huang et al., 2017[Huang, C., Wang, R., Shu, X., Fan, Y., Qi, Y., Li, S. & Xia, C. (2017). Acta Cryst. E73, 1316-1319.]), we report herein the synthesis of the title tris-urea receptor, 3-(4-nitro­phen­yl)-1,1-bis­{2-[3-(4-nitro­phen­yl)ureido]eth­yl}urea (R), based on p-nitro­phenyl substituents, and the crystal structure of its complex with tetra-n-butyl­ammonium di­hydrogen phosphate. Inter­estingly, a one-dimensional hydrogen-bonded polymeric structure is formed via hydrogen bonds between di­hydrogen phosphate anions, and this anionic polymer is surrounded by and linked to the tris-urea receptors through ureido N—H⋯O hydrogen bonds.

[Scheme 1]

2. Structural commentary

The title compound crystallizes with two independent formula units in the asymmetric unit. The mol­ecular structure of the two tris-urea receptors (R1 and R2) and the di­hydrogen phosphate anions (P1 and P2) are illustrated in Fig. 1[link]. In each receptor an intra­molecular N—H⋯O hydrogen bond is present (N8—H8N⋯O7 in R1 and N17—H17N⋯O16 in R2), each forming an S(9) ring motif,. Four intra­molecular C—H⋯O hydrogen bonds are also present in receptor R1 and three in R2 (Fig. 1[link] and Table 1[link]). Both receptors display a cis orientation of the urea subunits (N2/N3 and N5/N6 in R1, and N11/N12 and N14/N15 in R2). The urea subunits N5/N6 in R1 and N11/N12 in R2 are orientated towards the di­hydrogen phosphate ions (P1 and P2) forming a 2:2 adduct via N—H⋯O hydrogen bonds with anion P1 and enclosing R22(8) ring motifs (Table 1[link] and Fig. 1[link]). Both NH functions of each urea subunit are trans to the C=O group across the respective C—N bond. Anions P1 and P2 inter­act with each other via two O—H⋯O hydrogen bonds (O20—H20O⋯O24 and O23—H23O⋯O22), enclosing an R22(8) ring motif (Fig. 1[link] and Table 1[link]). The dihedral angle between the urea plane [N—C(=O)—N] and the benzene ring to which it is attached vary from 6.66 (14) to 18.96 (14)° in R1 and from 6.87 (14) to 13.82 (14)° in R2. The dihedral angle between the nitro group and the benzene ring to which it is attached also vary, from 7.1 (3) to 13.4 (4)° in R1 and from 8.3 (4) to 16.7 (7)° in R2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N8—H8N⋯O7 0.90 (3) 2.07 (3) 2.955 (3) 168 (3)
N17—H17N⋯O16 0.90 (2) 2.21 (2) 3.100 (3) 170 (2)
N5—H5N⋯O21 0.90 (2) 2.04 (2) 2.915 (3) 164 (3)
N6—H6N⋯O22 0.90 (2) 2.10 (2) 2.986 (3) 168 (2)
N11—H11N⋯O19 0.90 (2) 1.96 (2) 2.854 (3) 175 (2)
N12—H12N⋯O22 0.90 (2) 2.21 (2) 3.058 (3) 157 (3)
O20—H20O⋯O24 0.93 (2) 1.66 (2) 2.583 (2) 178 (3)
O23—H23O⋯O22 0.93 (2) 1.64 (2) 2.568 (2) 176 (2)
O21—H21O⋯O19i 0.93 (2) 1.61 (2) 2.528 (2) 173 (3)
O25—H25O⋯O26ii 0.93 (2) 1.59 (2) 2.501 (2) 166 (3)
N2—H2N⋯O26i 0.90 (2) 2.08 (2) 2.977 (3) 174 (2)
N3—H3N⋯O24i 0.90 (2) 2.09 (2) 2.931 (3) 155 (3)
N14—H14N⋯O25ii 0.90 (2) 2.03 (2) 2.930 (3) 175 (2)
N15—H15N⋯O24ii 0.90 (2) 2.10 (2) 2.986 (3) 168 (2)
C3—H3⋯O4 0.95 2.17 2.789 (4) 121
C5—H5⋯O7 0.95 2.53 3.279 (4) 136
C12—H12⋯O3 0.95 2.23 2.844 (3) 122
C21—H21⋯O7 0.95 2.31 2.872 (4) 118
C30—H30⋯O16 0.95 2.32 2.903 (4) 119
C43—H43⋯O12 0.95 2.32 2.910 (4) 120
C46—H46⋯O13 0.95 2.19 2.810 (3) 122
C18—H18A⋯O1iii 0.99 2.42 3.345 (4) 156
C30—H30⋯O6iv 0.95 2.58 3.265 (4) 129
C33—H33B⋯O11Aiii 0.99 2.58 3.235 (12) 123
C39—H39⋯O21i 0.95 2.52 3.446 (3) 164
C54—H54A⋯O15v 0.99 2.46 3.447 (4) 173
C63—H63A⋯O3 0.99 2.42 3.379 (4) 164
C63—H63B⋯O4 0.99 2.26 3.003 (4) 131
C64—H64B⋯O15v 0.99 2.46 3.348 (4) 149
C70—H70B⋯O10Aiii 0.98 2.47 3.289 (6) 141
C75—H75A⋯O13 0.99 2.31 3.158 (4) 143
C75—H75B⋯O1vi 0.99 2.58 3.514 (4) 157
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+1; (iii) x+1, y, z; (iv) -x+2, -y+1, -z+1; (v) x-1, y, z-1; (vi) x+1, y, z+1.
[Figure 1]
Figure 1
The mol­ecular structure of the title complex, with atom labellling. Displacement ellipsoids are drawn at the 30% probability level. For clarity, the tetra-n-butyl­ammonium cations, the disordered NO2 O atoms and the C-bound hydrogen atoms have been omitted.

3. Supra­molecular features

In the crystal, the two H2PO4− anions (P1 and P2), that are linked by O—H⋯O hydrogen bonds O20—H20O⋯O24 and O23—H23O⋯O22, are further linked to inversion-related anions via hydrogen bonds O21—H21O⋯O19i and O25—H25O⋯O26ii (Table 1[link]). This results in the formation of a polymer chain propagating along the a-axis direction (Fig. 2[link]). The receptor mol­ecules are linked to this chain via hydrogen bonds N5—H5N⋯O21, N6—H6N⋯O22, N11—H11N⋯O19, and N12—H12N⋯O22 (Fig. 1[link]), and by hydrogen bonds N2—H2N⋯O26i, N3—H3N⋯O24i, N14—H14N⋯O25ii and N15—H15N⋯O24ii (Table 1[link]). Finally, there are numerous inter­molecular C—H⋯O hydrogen bonds present involving both receptor mol­ecules and the tetra-n-butyl­ammonium cations, so forming a supra­molecular three-dimensional structure (Fig. 3[link] and Table 1[link]).

[Figure 2]
Figure 2
A partial view along the b axis of the crystal packing of the title complex. The receptors R1 and R2 are drawn in space-filling mode. The H atoms not involved in the O—H⋯O hydrogen bonds have been omitted.
[Figure 3]
Figure 3
Crystal packing of the title complex, viewed along the a axis. The tetra-n-butyl­ammonium cations are shown in blue (involving atom N19) and green (involving atom N20). The H atoms not involved in the O—H⋯O hydrogen bonds have been omitted.

4. Database survey

The crystal structure of the receptor R, with or without para-substitution of a nitro group, has not previously been reported. A search of the Cambridge Structural Database (Version 5.40, November 2018; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for tetra-n-butyl­ammonium di­hydrogen phosphate yielded four hits, essentially concerning the tris-urea receptor based on tris­(2-amino­eth­yl)amine (tren). One of these compounds, tetra-n-butyl­ammonium tris­(2-(N-perfluoro­phenyl­ureaylato)eth­yl)amine di­hydrogen phosphate di­methyl­formamide monosolvate, encapsulates a dimer of H2PO4− anions forming a pseudo-dimeric cage via sixteen hydrogen bonds and two weak anion⋯π inter­actions (CSD refcode CITYOU; Lakshminarayanan et al., 2007[Lakshminarayanan, P. S., Ravikumar, I., Suresh, E. & Ghosh, P. (2007). Chem. Commun. 48, 5214-5216.]). Another example is, N,N′,N′′-[nitrilo­tris­(ethane-2,1-di­yl)]tris­(N′-phenyl­urea) tetra-n-butyl­ammonium di­hydrogen phosphate (YICHUQ; Manna & Das, 2018[Manna, U. & Das, G. (2018). CrystEngComm, 20, 3741-3754.]). Here too, a dimer of H2PO4− anions is encapsulated by the receptor.

Chiral anion receptors with two enanti­omeric forms R,R and S,S based on a 1,2-cyclo­hexane moiety appended by two p-nitro­phenyl­urea subunits have been reported. One such compound is bis­(tetra-n-butyl­ammonium) bis­(di­hydrogen phosphate) (R,R)-1-(4-nitro­phen­yl)-3-{2-[3-(4-nitro­phen­yl)ureido]cyclo­hex­yl}urea aceto­nitrile monosolvate (DASNUH; Amendola et al., 2005[Amendola, V., Boiocchi, M., Esteban-Gómez, D., Fabbrizzi, L. & Monzani, E. (2005). Org. Biomol. Chem. 3, 2632-2639.]). The nature of the R,R-enanti­omer⋯H2PO4− inter­actions is characterized by infinite di­hydrogen phosphate chains along the a-axis direction, as observed in the crystal structure of the title complex. Specif­ically, each di­hydrogen phosphate ion inter­acts with two adjacent H2PO4− ions and with only one R,R-enanti­omer via two hydrogen bonds. The hydrogen bonds in this enanti­omeric complex are similar to those in the title complex, with the H⋯acceptor distance between the urea N—H group and the di­hydrogen phosphate oxygen atom varying between ca 1.98 and 2.19 Å in DASNUH compared to a range of 1.96 (2)–2.21 (2) Å in the title compound. The O—H⋯O hydrogen bonds involving the H2PO4− anions are also very similar: 1.62 (3) and 1.63 (4) Å in DASNUH, while they vary from 1.59 (2) to 1.66 (2) Å in the title complex.

5. Synthesis and crystallization

Synthesis of 3-(4-nitro­phen­yl)-1,1-bis­{2-[3-(4-nitro­phen­yl)ureido]eth­yl}urea (R): In a 250 ml round-bottom flask, di­ethyl­enetri­amine (0.32 ml, 2.97 mmol) dissolved in 100 ml of dry CH2Cl2 was added dropwise under vigorous stirring to a solution of 20 ml of dry CH2Cl2 containing p-nitro­benzene iso­cyanate (1.64 g, 9.98 mmol). Subsequently, the reaction mixture was allowed to reflux for 24 h. A yellowish solid was collected by filtration and washed using sequentially CH2Cl2 (3 × 70 ml), a solvent mixture (CH2Cl2/THF = 4:1, 3 × 70 ml) and diethyl ether (3 × 70 ml). The solid was then dried in vacuo overnight to afford the receptor R as a light-brown powder (yield: 1.52 g; 85.6%; m.p. 512.3–513.8 K). FT–IR (KBr, cm−1): 3339, 1679, 1606, 1559, 1501, 1330. 1H NMR (400 MHz, DMSO-d6) in ppm: δ = 9.42 (s, 2H), 9.23 (s, 1H), 8.10 (t, J = 9.9 Hz, 6H), 7.76 (d, J = 8.9 Hz, 2H), 7.59 (d, J = 8.9 Hz, 4H), 6.60 (t, J = 5.8 Hz, 2H), 3.51 (t, J = 6.5 Hz, 4H). 13C NMR (100 MHz, DMSO-d6) in ppm: δ = 154.99, 154.67, 147.34, 146.94, 140.72, 140.48, 125.09, 124.70, 118.13, 116.95, 46.63, 40.15–38.89, 38.19. HRMS (ESI+): calculated for C25H25N9O9Na [M + Na]+ 618.1673 found 618.1678.

Synthesis of the title complex (I)[link]: Tetra-n-butyl­ammonium di­hydrogen phosphate (1.68 mmol) was added to 5 ml of a DMF solution of R (0.168 mmol) and the mixture was stirred for 2 h. After filtration the solution was left to evaporate slowly and yielded colourless prismatic crystals of the title complex within three weeks.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. H atoms bonded to O and N were located in a difference-Fourier map and refined with distance restraints: O—H = 0.93 and N—H = 0.90 Å, with Uiso(H) = 1.5Ueq(O) and 1.2Ueq(N). The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.95–0.99 Å, with Uiso(H) = 1.5Ueq(C-meth­yl) and 1.2Ueq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula C25H25N9O9·C16H36N+·H2PO4−
Mr 934.98
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 179
a, b, c (Å) 15.2043 (3), 17.4555 (5), 18.1232 (4)
α, β, γ (°) 83.797 (2), 79.818 (2), 89.191 (2)
V (Å3) 4706.3 (2)
Z 4
Radiation type Cu Kα
μ (mm−1) 1.13
Crystal size (mm) 0.40 × 0.40 × 0.10
 
Data collection
Diffractometer Agilent New Gemini, Dual, Cu at zero, EosS2
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies. Yarnton, England.])
Tmin, Tmax 0.660, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections 50539, 18359, 15323
Rint 0.040
(sin θ/λ)max (Å−1) 0.619
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.160, 1.01
No. of reflections 18359
No. of parameters 1237
No. of restraints 26
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.96, −0.85
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies. Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

One of the butyl moieties (C79—C80—C81—C82) is disordered over two positions with equal occupancies. The C—C distances were refined with the restraint of 1.515 (4) Å. The displacement parameters of the C79A/C79B, C80A/C80B, C81A/C81B, and C82A/C82B atoms of the disordered fragment were restrained to be similar (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]). Also, one of the nitro groups (O11—N10—O10) was disordered over two positions with equal occupancies. The N—O distances were refined with the restraint of 1.230 (4) Å. The displacement parameters of the O10A/O11A and O10B/O11B atoms of the disordered fragment were restrained to be similar (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]).

Supporting information

CCDC reference: 1893140

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989019001336/kq2020sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019001336/kq2020Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019001336/kq2020Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-(4-Nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea tetrabutylammonium dihydrogen phosphate top
Crystal data top
C25H25N9O9·C16H36N+·H2PO4−Z = 4
Mr = 934.98F(000) = 1992
Triclinic, P1Dx = 1.320 Mg m−3
a = 15.2043 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 17.4555 (5) ÅCell parameters from 22142 reflections
c = 18.1232 (4) Åθ = 4.2–72.6°
α = 83.797 (2)°µ = 1.13 mm−1
β = 79.818 (2)°T = 179 K
γ = 89.191 (2)°Prism, colourless
V = 4706.3 (2) Å30.40 × 0.40 × 0.10 mm
Data collection top
Agilent New Gemini, Dual, Cu at zero, EosS2
diffractometer		18359 independent reflections
Radiation source: Enhance (Cu) X-ray Source15323 reflections with I > 2σ(I)
Detector resolution: 15.9595 pixels mm-1Rint = 0.040
ω scansθmax = 72.7°, θmin = 4.5°
Absorption correction: multi-scan
(CrysAlisPro; Agilent, 2014)		h = −12→18
Tmin = 0.660, Tmax = 0.880k = −21→21
50539 measured reflectionsl = −21→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: mixed
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.06P)2 + 6P]
where P = (Fo2 + 2Fc2)/3
18359 reflections(Δ/σ)max = 0.001
1237 parametersΔρmax = 0.96 e Å−3
26 restraintsΔρmin = −0.85 e Å−3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1−0.30049 (14)0.81991 (14)0.21069 (13)0.0558 (5)
O2−0.24548 (15)0.71532 (13)0.16732 (13)0.0563 (5)
O30.14525 (13)0.70324 (12)0.30808 (13)0.0499 (5)
O40.41981 (13)0.66636 (13)0.25280 (13)0.0541 (6)
O50.73924 (19)0.44154 (18)0.07252 (17)0.0814 (8)
O60.81027 (19)0.41318 (15)0.16481 (15)0.0741 (8)
O70.67230 (13)0.71270 (11)0.39515 (11)0.0431 (4)
O81.11079 (14)0.66722 (14)0.52832 (14)0.0590 (6)
O91.07222 (16)0.57359 (15)0.47126 (13)0.0639 (6)
N1−0.24296 (16)0.76864 (15)0.20575 (14)0.0456 (6)
N20.05445 (14)0.80478 (12)0.34212 (12)0.0349 (5)
H2N0.053 (2)0.8466 (10)0.3671 (15)0.042*
N30.18575 (14)0.78414 (13)0.38582 (13)0.0380 (5)
H3N0.173 (2)0.8242 (12)0.4129 (15)0.046*
N40.43055 (15)0.74282 (14)0.34333 (14)0.0433 (5)
N50.61267 (16)0.82824 (14)0.42129 (14)0.0437 (5)
H5N0.623 (2)0.8733 (10)0.4382 (18)0.052*
N60.73250 (14)0.78432 (13)0.47369 (13)0.0365 (5)
H6N0.722 (2)0.8271 (10)0.4972 (15)0.044*
N71.05762 (17)0.63522 (16)0.49814 (14)0.0479 (6)
N80.54553 (15)0.65876 (14)0.30550 (14)0.0413 (5)
H8N0.5769 (18)0.6786 (17)0.3366 (14)0.050*
N90.75357 (19)0.44901 (16)0.13596 (17)0.0575 (7)
C10.69928 (19)0.50461 (16)0.17902 (17)0.0454 (7)
C20.6241 (2)0.5329 (2)0.1551 (2)0.0576 (8)
H20.60870.51830.11000.069*
C30.5703 (2)0.5832 (2)0.19681 (19)0.0545 (8)
H30.51700.60230.18100.065*
C40.59415 (18)0.60564 (15)0.26166 (16)0.0399 (6)
C50.67121 (19)0.57639 (17)0.28422 (17)0.0449 (6)
H50.68790.59160.32860.054*
C60.7244 (2)0.52534 (17)0.24328 (18)0.0476 (7)
H60.77710.50510.25920.057*
C70.46280 (17)0.68813 (16)0.29743 (16)0.0411 (6)
C80.34579 (17)0.77955 (16)0.33457 (16)0.0398 (6)
H8A0.33350.77360.28360.048*
H8B0.35030.83530.33890.048*
C90.26874 (17)0.74518 (16)0.39328 (16)0.0392 (6)
H9A0.26240.68990.38760.047*
H9B0.28190.74920.44430.047*
C100.13050 (17)0.75938 (15)0.34299 (15)0.0359 (5)
C11−0.01842 (16)0.79138 (15)0.30923 (14)0.0342 (5)
C12−0.02853 (18)0.72636 (16)0.27224 (16)0.0400 (6)
H120.01610.68770.26940.048*
C13−0.10298 (18)0.71844 (16)0.24008 (16)0.0419 (6)
H13−0.10960.67450.21490.050*
C14−0.16814 (17)0.77457 (16)0.24457 (15)0.0382 (6)
C15−0.16132 (18)0.83798 (16)0.28272 (16)0.0412 (6)
H15−0.20740.87540.28680.049*
C16−0.08709 (18)0.84628 (16)0.31461 (15)0.0394 (6)
H16−0.08200.88990.34080.047*
C170.47607 (18)0.76651 (17)0.40141 (16)0.0424 (6)
H17A0.50190.72060.42660.051*
H17B0.43210.78940.43990.051*
C180.55022 (18)0.82489 (17)0.36954 (16)0.0421 (6)
H18A0.58260.81040.32070.051*
H18B0.52380.87640.36030.051*
C190.67255 (17)0.77080 (15)0.42772 (15)0.0376 (6)
C200.81048 (17)0.74344 (15)0.48085 (14)0.0342 (5)
C210.82524 (19)0.66802 (16)0.46242 (16)0.0424 (6)
H210.78000.64090.44580.051*
C220.9062 (2)0.63326 (16)0.46862 (16)0.0442 (6)
H220.91700.58240.45530.053*
C230.97117 (18)0.67192 (16)0.49395 (14)0.0392 (6)
C240.95747 (18)0.74567 (16)0.51434 (14)0.0386 (6)
H241.00230.77140.53280.046*
C250.87735 (17)0.78116 (15)0.50729 (14)0.0358 (5)
H250.86740.83210.52060.043*
O10A0.0479 (3)0.8828 (3)0.8867 (3)0.0689 (14)0.5
O11A0.0502 (7)0.9794 (7)0.8022 (6)0.0689 (14)0.5
O10B0.0574 (3)0.9139 (3)0.90363 (18)0.0515 (10)0.5
O11B0.0563 (6)0.9790 (6)0.7960 (4)0.0515 (10)0.5
O120.49661 (14)0.78528 (13)0.82348 (11)0.0516 (5)
O130.75401 (12)0.75789 (11)0.88681 (10)0.0390 (4)
O140.94784 (18)0.54938 (14)1.15633 (12)0.0654 (7)
O151.07221 (14)0.52318 (12)1.08658 (12)0.0483 (5)
O161.08082 (12)0.76689 (11)0.73581 (10)0.0381 (4)
O171.50576 (19)0.61542 (18)0.70411 (17)0.0847 (9)
O181.56917 (14)0.68624 (14)0.60480 (15)0.0620 (6)
N100.08998 (16)0.93022 (17)0.83676 (13)0.0572 (7)
N110.44803 (14)0.86420 (13)0.72873 (12)0.0362 (5)
H11N0.4688 (19)0.8905 (15)0.6837 (8)0.043*
N120.58895 (15)0.81643 (13)0.71123 (13)0.0392 (5)
H12N0.599 (2)0.8456 (15)0.6666 (9)0.047*
N130.81504 (13)0.79785 (12)0.76640 (11)0.0336 (4)
N141.03777 (14)0.86411 (13)0.65735 (12)0.0361 (5)
H14N1.0554 (19)0.9028 (12)0.6211 (12)0.043*
N151.17809 (14)0.81480 (12)0.62862 (12)0.0341 (4)
H15N1.181 (2)0.8486 (13)0.5873 (10)0.041*
N161.50353 (18)0.66548 (16)0.65167 (16)0.0543 (6)
N170.90190 (13)0.73247 (13)0.84589 (12)0.0339 (4)
H17N0.9496 (12)0.7446 (17)0.8097 (12)0.041*
N180.99925 (17)0.55484 (13)1.09594 (13)0.0407 (5)
C261.41791 (18)0.70288 (16)0.64585 (17)0.0429 (6)
C271.41575 (17)0.76631 (16)0.59423 (15)0.0385 (6)
H271.46890.78520.56200.046*
C281.33498 (17)0.80203 (15)0.59014 (14)0.0358 (5)
H281.33290.84630.55500.043*
C291.25603 (17)0.77435 (15)0.63674 (14)0.0340 (5)
C301.2600 (2)0.71000 (17)0.68850 (19)0.0514 (7)
H301.20710.69010.72040.062*
C311.3412 (2)0.67522 (19)0.6933 (2)0.0570 (8)
H311.34440.63200.72940.068*
C321.09771 (16)0.81194 (14)0.67801 (14)0.0324 (5)
C330.95254 (16)0.87103 (15)0.70682 (15)0.0354 (5)
H33A0.92420.92040.69190.042*
H33B0.96250.87160.75930.042*
C340.89019 (16)0.80453 (15)0.70328 (14)0.0339 (5)
H34A0.86690.81230.65530.041*
H34B0.92440.75580.70370.041*
C350.73043 (16)0.83373 (15)0.75436 (14)0.0341 (5)
H35A0.74270.87740.71420.041*
H35B0.70130.85460.80120.041*
C360.66706 (18)0.77744 (16)0.73211 (16)0.0403 (6)
H36A0.69850.75150.68910.048*
H36B0.64820.73750.77490.048*
C370.51073 (17)0.81871 (15)0.76007 (15)0.0368 (5)
C380.35982 (17)0.87685 (15)0.75916 (14)0.0357 (5)
C390.31353 (17)0.93099 (15)0.71747 (14)0.0361 (5)
H390.34380.95660.67120.043*
C400.22548 (18)0.94750 (16)0.74230 (15)0.0393 (6)
H400.19460.98350.71310.047*
C410.18252 (18)0.91135 (18)0.80989 (16)0.0444 (6)
C420.2256 (2)0.8569 (2)0.85174 (17)0.0523 (8)
H420.19430.83140.89770.063*
C430.31411 (19)0.83923 (18)0.82708 (16)0.0457 (7)
H430.34370.80190.85590.055*
C440.81967 (16)0.76260 (14)0.83621 (14)0.0320 (5)
C450.92141 (16)0.68865 (14)0.91061 (14)0.0323 (5)
C460.85796 (18)0.66579 (15)0.97486 (15)0.0379 (6)
H460.79710.67980.97660.045*
C470.88410 (18)0.62279 (15)1.03564 (15)0.0389 (6)
H470.84160.60821.07990.047*
C480.97190 (18)0.60118 (14)1.03184 (14)0.0348 (5)
C491.03608 (17)0.62206 (15)0.96873 (14)0.0358 (5)
H491.09640.60610.96690.043*
C501.01033 (17)0.66647 (15)0.90874 (14)0.0353 (5)
H501.05370.68230.86540.042*
N190.25010 (15)0.49825 (13)0.23222 (13)0.0388 (5)
C51−0.0401 (2)0.47538 (19)0.33601 (18)0.0553 (8)
H51A−0.10420.46340.34550.083*
H51B−0.02900.52390.30320.083*
H51C−0.02050.48040.38390.083*
C520.0109 (2)0.41156 (17)0.29828 (17)0.0466 (7)
H52A−0.00150.41310.24630.056*
H52B−0.01150.36160.32580.056*
C530.1128 (2)0.41542 (17)0.29455 (18)0.0490 (7)
H53A0.12640.40870.34630.059*
H53B0.14170.37300.26720.059*
C540.14972 (19)0.49192 (16)0.25485 (16)0.0419 (6)
H54A0.12310.50340.20890.050*
H54B0.12940.53240.28820.050*
C550.2823 (2)0.44540 (16)0.17047 (17)0.0441 (6)
H55A0.26510.39180.19090.053*
H55B0.25020.45960.12800.053*
C560.3813 (2)0.44747 (18)0.14002 (18)0.0501 (7)
H56A0.41410.42630.18020.060*
H56B0.40090.50150.12420.060*
C570.4029 (2)0.4010 (2)0.0735 (2)0.0617 (9)
H57A0.37460.42550.03180.074*
H57B0.37730.34860.08810.074*
C580.5029 (3)0.3949 (2)0.0461 (2)0.0718 (11)
H58A0.51360.36700.00120.108*
H58B0.53060.36690.08590.108*
H58C0.52900.44660.03350.108*
C590.2973 (2)0.47440 (17)0.29835 (17)0.0437 (6)
H59A0.28620.41870.31370.052*
H59B0.36240.48140.28070.052*
C600.2710 (2)0.51657 (19)0.36676 (18)0.0514 (7)
H60A0.20840.50360.39010.062*
H60B0.27470.57280.35150.062*
C610.3314 (3)0.4954 (2)0.4237 (2)0.0631 (9)
H61A0.32820.43890.43720.076*
H61B0.39360.50840.39930.076*
C620.3110 (4)0.5334 (3)0.4944 (2)0.0875 (14)
H62A0.35520.51780.52640.131*
H62B0.25120.51780.52140.131*
H62C0.31310.58940.48200.131*
C630.27396 (19)0.58148 (15)0.20295 (16)0.0415 (6)
H63A0.24450.61460.24100.050*
H63B0.33930.58790.19890.050*
C640.2492 (2)0.61080 (17)0.12773 (18)0.0501 (7)
H64A0.28550.58400.08750.060*
H64B0.18550.59910.12850.060*
C650.2646 (3)0.69612 (18)0.1108 (2)0.0595 (8)
H65A0.32540.70800.11890.071*
H65B0.22150.72260.14720.071*
C660.2553 (3)0.7282 (2)0.0323 (2)0.0682 (10)
H66A0.27100.78310.02460.102*
H66B0.19350.72190.02540.102*
H66C0.29540.7007−0.00430.102*
N200.72892 (17)0.93841 (15)1.01240 (14)0.0479 (6)
C670.8071 (2)0.93305 (19)1.05475 (17)0.0503 (7)
H67A0.83790.98371.04580.060*
H67B0.78290.92381.10940.060*
C680.8757 (2)0.8720 (2)1.03507 (18)0.0536 (8)
H68A0.89630.87710.97980.064*
H68B0.84780.82051.05020.064*
C690.9551 (2)0.8784 (2)1.07384 (18)0.0549 (8)
H69A0.98790.92671.05290.066*
H69B0.93340.88161.12820.066*
C701.0183 (2)0.8117 (2)1.0650 (2)0.0621 (9)
H70A1.06890.81951.09030.093*
H70B1.04040.80821.01130.093*
H70C0.98700.76381.08760.093*
C710.6633 (2)0.99719 (18)1.04517 (18)0.0527 (7)
H71A0.62001.00931.01070.063*
H71B0.69641.04521.04700.063*
C720.6114 (2)0.97207 (18)1.12398 (16)0.0494 (7)
H72A0.60210.91561.12970.059*
H72B0.64720.98421.16190.059*
C730.5216 (2)1.0113 (2)1.13913 (19)0.0559 (8)
H73A0.48761.00271.09890.067*
H73B0.53101.06751.13760.067*
C740.4670 (2)0.9813 (2)1.2154 (2)0.0633 (9)
H74A0.40891.00711.22230.095*
H74B0.49910.99201.25560.095*
H74C0.45800.92561.21730.095*
C750.6859 (2)0.86013 (17)1.01881 (17)0.0467 (7)
H75A0.72880.82560.99110.056*
H75B0.67500.83891.07260.056*
C760.5992 (2)0.85802 (19)0.98967 (18)0.0509 (7)
H76A0.61140.86590.93390.061*
H76B0.56030.90041.00810.061*
C770.5512 (2)0.7811 (2)1.0158 (2)0.0593 (8)
H77A0.50440.77540.98510.071*
H77B0.59460.73871.00710.071*
C780.5094 (3)0.7741 (3)1.0970 (3)0.0975 (16)
H78A0.48130.72321.11130.146*
H78B0.46400.81411.10550.146*
H78C0.55540.78031.12760.146*
C790.7611 (2)0.96494 (19)0.92815 (18)0.0598 (9)
H79A0.78760.92000.90360.072*0.5
H79B0.70800.98060.90550.072*0.5
H79C0.80930.93010.90820.072*0.5
H79D0.71090.95920.90100.072*0.5
C80A0.8284 (6)1.0305 (5)0.9088 (4)0.067 (3)0.5
H80A0.80511.07480.93590.080*0.5
H80B0.88491.01380.92560.080*0.5
C81A0.8466 (4)1.0550 (4)0.8248 (3)0.0606 (12)0.5
H81A0.88751.10000.81590.073*0.5
H81B0.87961.01270.80000.073*0.5
C82A0.7693 (6)1.0761 (7)0.7843 (6)0.090 (3)0.5
H82A0.78941.07650.72980.136*0.5
H82B0.74731.12740.79560.136*0.5
H82C0.72111.03820.80130.136*0.5
C80B0.7954 (6)1.0474 (3)0.9106 (4)0.067 (3)0.5
H80C0.76361.07780.95000.080*0.5
H80D0.85941.04720.91480.080*0.5
C81B0.7864 (5)1.0888 (4)0.8344 (3)0.0606 (12)0.5
H81C0.72311.10370.83550.073*0.5
H81D0.82241.13670.82590.073*0.5
C82B0.8152 (8)1.0424 (6)0.7690 (5)0.090 (3)0.5
H82D0.81661.07560.72160.136*0.5
H82E0.77291.00000.77160.136*0.5
H82F0.87501.02150.77110.136*0.5
P10.60995 (4)0.97408 (3)0.55144 (3)0.02832 (13)
O190.51551 (11)0.95514 (10)0.59024 (10)0.0354 (4)
O200.63474 (11)1.05356 (10)0.57479 (10)0.0344 (4)
H20O0.6934 (8)1.0670 (18)0.5542 (17)0.052*
O210.61479 (11)0.98453 (10)0.46370 (10)0.0333 (4)
H21O0.5645 (13)1.0068 (17)0.4480 (17)0.050*
O220.67758 (11)0.91334 (9)0.56726 (10)0.0327 (4)
P20.87010 (4)1.03192 (3)0.53218 (3)0.02841 (13)
O230.82990 (11)0.96052 (10)0.58748 (10)0.0338 (4)
H23O0.7761 (11)0.9427 (18)0.5783 (18)0.051*
O240.79916 (11)1.09098 (9)0.52118 (10)0.0335 (4)
O250.90787 (11)1.00351 (10)0.45455 (10)0.0332 (4)
H25O0.9644 (9)0.9823 (17)0.4529 (18)0.050*
O260.94470 (11)1.06344 (10)0.56654 (10)0.0363 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0425 (11)0.0716 (15)0.0544 (13)0.0122 (11)−0.0132 (9)−0.0063 (11)
O20.0513 (13)0.0562 (13)0.0662 (14)−0.0077 (10)−0.0194 (11)−0.0112 (11)
O30.0413 (11)0.0482 (12)0.0658 (13)0.0115 (9)−0.0135 (9)−0.0266 (10)
O40.0356 (10)0.0673 (14)0.0682 (14)0.0052 (9)−0.0164 (10)−0.0359 (11)
O50.0706 (17)0.097 (2)0.0833 (19)0.0183 (15)−0.0055 (14)−0.0533 (17)
O60.0820 (18)0.0580 (15)0.0704 (16)0.0327 (13)0.0133 (14)−0.0017 (12)
O70.0398 (10)0.0426 (10)0.0526 (11)0.0068 (8)−0.0151 (8)−0.0203 (9)
O80.0359 (11)0.0642 (14)0.0735 (15)0.0015 (10)−0.0116 (10)0.0110 (12)
O90.0655 (15)0.0680 (15)0.0571 (14)0.0338 (12)−0.0088 (11)−0.0101 (12)
N10.0373 (12)0.0530 (15)0.0434 (13)−0.0048 (11)−0.0037 (10)0.0035 (11)
N20.0308 (11)0.0336 (11)0.0405 (11)0.0023 (9)−0.0043 (9)−0.0076 (9)
N30.0324 (11)0.0358 (11)0.0468 (13)0.0048 (9)−0.0065 (9)−0.0107 (10)
N40.0320 (11)0.0535 (14)0.0479 (13)0.0067 (10)−0.0087 (10)−0.0200 (11)
N50.0424 (13)0.0403 (13)0.0554 (14)0.0086 (10)−0.0197 (11)−0.0189 (11)
N60.0356 (11)0.0352 (11)0.0418 (12)0.0043 (9)−0.0092 (9)−0.0141 (9)
N70.0406 (13)0.0557 (15)0.0413 (13)0.0100 (11)0.0003 (10)0.0085 (11)
N80.0321 (11)0.0448 (13)0.0506 (13)0.0014 (9)−0.0085 (10)−0.0194 (11)
N90.0563 (16)0.0452 (15)0.0639 (18)0.0001 (13)0.0136 (14)−0.0143 (13)
C10.0410 (15)0.0352 (14)0.0548 (17)0.0003 (11)0.0081 (12)−0.0088 (12)
C20.0508 (18)0.065 (2)0.061 (2)0.0011 (15)−0.0077 (15)−0.0305 (17)
C30.0390 (16)0.065 (2)0.066 (2)0.0095 (14)−0.0127 (14)−0.0300 (16)
C40.0345 (13)0.0362 (14)0.0482 (15)−0.0044 (11)−0.0007 (11)−0.0106 (11)
C50.0441 (15)0.0435 (15)0.0474 (16)0.0040 (12)−0.0064 (12)−0.0092 (12)
C60.0453 (16)0.0409 (15)0.0534 (17)0.0081 (12)−0.0018 (13)−0.0028 (13)
C70.0296 (13)0.0452 (15)0.0498 (15)−0.0024 (11)−0.0041 (11)−0.0156 (12)
C80.0336 (13)0.0435 (15)0.0445 (15)0.0042 (11)−0.0086 (11)−0.0127 (12)
C90.0337 (13)0.0360 (13)0.0496 (15)0.0034 (11)−0.0102 (11)−0.0078 (11)
C100.0298 (12)0.0346 (13)0.0410 (14)0.0020 (10)−0.0006 (10)−0.0036 (11)
C110.0313 (12)0.0351 (13)0.0333 (12)−0.0007 (10)−0.0004 (10)0.0005 (10)
C120.0361 (14)0.0365 (14)0.0465 (15)0.0034 (11)−0.0038 (11)−0.0064 (11)
C130.0390 (14)0.0397 (14)0.0459 (15)−0.0029 (11)−0.0044 (11)−0.0051 (12)
C140.0312 (13)0.0439 (15)0.0372 (13)−0.0040 (11)−0.0030 (10)0.0017 (11)
C150.0369 (14)0.0413 (15)0.0434 (14)0.0059 (11)−0.0036 (11)−0.0017 (12)
C160.0396 (14)0.0371 (14)0.0411 (14)0.0034 (11)−0.0052 (11)−0.0057 (11)
C170.0359 (14)0.0525 (16)0.0409 (14)0.0088 (12)−0.0067 (11)−0.0161 (12)
C180.0399 (14)0.0448 (15)0.0456 (15)0.0082 (12)−0.0134 (12)−0.0140 (12)
C190.0330 (13)0.0390 (14)0.0424 (14)0.0020 (10)−0.0070 (11)−0.0103 (11)
C200.0367 (13)0.0355 (13)0.0298 (12)0.0032 (10)−0.0041 (10)−0.0045 (10)
C210.0446 (15)0.0377 (14)0.0477 (15)0.0017 (12)−0.0129 (12)−0.0098 (12)
C220.0515 (16)0.0366 (14)0.0453 (15)0.0098 (12)−0.0086 (12)−0.0086 (12)
C230.0377 (14)0.0450 (15)0.0316 (12)0.0087 (11)−0.0015 (10)0.0019 (11)
C240.0364 (13)0.0458 (15)0.0337 (13)−0.0031 (11)−0.0081 (10)−0.0012 (11)
C250.0393 (14)0.0356 (13)0.0335 (12)0.0027 (10)−0.0070 (10)−0.0068 (10)
O10A0.043 (2)0.098 (3)0.065 (3)−0.001 (2)−0.002 (2)−0.017 (3)
O11A0.043 (2)0.098 (3)0.065 (3)−0.001 (2)−0.002 (2)−0.017 (3)
O10B0.038 (2)0.058 (2)0.056 (2)0.0010 (16)0.0051 (16)−0.0169 (18)
O11B0.038 (2)0.058 (2)0.056 (2)0.0010 (16)0.0051 (16)−0.0169 (18)
O120.0471 (11)0.0621 (13)0.0424 (11)0.0037 (10)−0.0108 (9)0.0127 (10)
O130.0315 (9)0.0488 (11)0.0337 (9)0.0046 (8)−0.0006 (7)0.0005 (8)
O140.0855 (17)0.0689 (15)0.0343 (11)0.0219 (13)−0.0013 (11)0.0100 (10)
O150.0469 (12)0.0517 (12)0.0498 (11)0.0020 (9)−0.0223 (9)0.0021 (9)
O160.0326 (9)0.0421 (10)0.0364 (9)0.0011 (7)−0.0039 (7)0.0060 (8)
O170.0686 (17)0.089 (2)0.087 (2)0.0363 (15)−0.0099 (14)0.0231 (16)
O180.0383 (12)0.0599 (14)0.0859 (17)0.0104 (10)−0.0055 (11)−0.0102 (12)
N100.0393 (14)0.084 (2)0.0456 (15)−0.0057 (14)0.0019 (11)−0.0091 (14)
N110.0310 (11)0.0421 (12)0.0339 (11)−0.0014 (9)−0.0063 (8)0.0042 (9)
N120.0318 (11)0.0423 (12)0.0429 (12)0.0022 (9)−0.0107 (9)0.0048 (10)
N130.0271 (10)0.0404 (11)0.0319 (10)0.0013 (8)−0.0045 (8)0.0007 (9)
N140.0322 (11)0.0359 (11)0.0366 (11)0.0002 (9)−0.0017 (9)0.0057 (9)
N150.0309 (10)0.0356 (11)0.0338 (11)−0.0003 (9)−0.0045 (8)0.0029 (9)
N160.0477 (15)0.0517 (15)0.0648 (17)0.0146 (12)−0.0133 (13)−0.0084 (13)
N170.0272 (10)0.0413 (12)0.0312 (10)0.0012 (9)−0.0034 (8)0.0014 (9)
N180.0530 (14)0.0345 (11)0.0365 (12)−0.0021 (10)−0.0141 (10)−0.0017 (9)
C260.0362 (14)0.0415 (15)0.0515 (16)0.0082 (11)−0.0081 (12)−0.0073 (12)
C270.0315 (13)0.0465 (15)0.0378 (13)−0.0002 (11)−0.0053 (10)−0.0070 (11)
C280.0354 (13)0.0394 (14)0.0328 (12)−0.0008 (11)−0.0088 (10)−0.0001 (10)
C290.0331 (13)0.0338 (13)0.0358 (13)0.0010 (10)−0.0069 (10)−0.0055 (10)
C300.0400 (15)0.0429 (16)0.0634 (19)0.0043 (12)0.0020 (13)0.0111 (14)
C310.0521 (18)0.0437 (17)0.068 (2)0.0091 (14)−0.0049 (15)0.0162 (15)
C320.0301 (12)0.0344 (12)0.0332 (12)−0.0031 (10)−0.0075 (10)−0.0022 (10)
C330.0323 (13)0.0349 (13)0.0371 (13)0.0036 (10)−0.0037 (10)−0.0002 (10)
C340.0320 (12)0.0395 (13)0.0297 (12)0.0044 (10)−0.0064 (9)−0.0005 (10)
C350.0316 (12)0.0351 (13)0.0348 (12)0.0045 (10)−0.0059 (10)−0.0012 (10)
C360.0364 (14)0.0374 (14)0.0491 (15)0.0041 (11)−0.0147 (12)−0.0017 (12)
C370.0339 (13)0.0375 (13)0.0398 (14)−0.0028 (10)−0.0111 (10)−0.0004 (11)
C380.0323 (13)0.0411 (14)0.0347 (13)−0.0048 (10)−0.0081 (10)−0.0045 (10)
C390.0339 (13)0.0400 (14)0.0332 (12)−0.0028 (10)−0.0036 (10)−0.0018 (10)
C400.0348 (13)0.0419 (14)0.0430 (14)−0.0008 (11)−0.0099 (11)−0.0074 (11)
C410.0328 (14)0.0601 (18)0.0411 (14)−0.0050 (12)−0.0055 (11)−0.0100 (13)
C420.0404 (16)0.076 (2)0.0365 (14)−0.0116 (15)−0.0004 (12)0.0055 (14)
C430.0394 (15)0.0570 (18)0.0391 (14)−0.0046 (13)−0.0094 (11)0.0066 (13)
C440.0304 (12)0.0325 (12)0.0338 (12)−0.0019 (10)−0.0065 (10)−0.0050 (10)
C450.0329 (12)0.0317 (12)0.0331 (12)−0.0006 (10)−0.0081 (10)−0.0035 (10)
C460.0336 (13)0.0390 (14)0.0393 (14)0.0003 (11)−0.0043 (10)0.0002 (11)
C470.0417 (14)0.0373 (14)0.0354 (13)−0.0029 (11)−0.0027 (11)0.0006 (11)
C480.0437 (14)0.0298 (12)0.0331 (12)−0.0016 (10)−0.0128 (10)−0.0031 (10)
C490.0328 (13)0.0392 (13)0.0373 (13)0.0016 (10)−0.0108 (10)−0.0059 (11)
C500.0343 (13)0.0400 (14)0.0310 (12)−0.0011 (10)−0.0048 (10)−0.0028 (10)
N190.0423 (12)0.0335 (11)0.0428 (12)−0.0016 (9)−0.0144 (10)−0.0027 (9)
C510.062 (2)0.0517 (18)0.0486 (17)0.0078 (15)−0.0042 (14)0.0006 (14)
C520.0503 (17)0.0413 (15)0.0474 (16)−0.0070 (13)−0.0065 (13)−0.0032 (12)
C530.0538 (17)0.0398 (15)0.0518 (17)0.0016 (13)−0.0064 (14)−0.0022 (13)
C540.0422 (15)0.0417 (15)0.0439 (15)0.0008 (12)−0.0125 (12)−0.0057 (12)
C550.0520 (17)0.0333 (14)0.0476 (16)−0.0013 (12)−0.0117 (13)−0.0025 (12)
C560.0531 (18)0.0451 (16)0.0514 (17)−0.0021 (13)−0.0068 (14)−0.0063 (13)
C570.072 (2)0.0525 (19)0.0550 (19)−0.0169 (17)0.0095 (16)−0.0122 (15)
C580.078 (3)0.055 (2)0.074 (2)−0.0113 (18)0.017 (2)−0.0163 (18)
C590.0438 (15)0.0395 (14)0.0500 (16)0.0046 (12)−0.0144 (12)−0.0051 (12)
C600.0599 (19)0.0481 (17)0.0492 (17)0.0090 (14)−0.0157 (14)−0.0102 (13)
C610.074 (2)0.068 (2)0.0519 (19)0.0132 (18)−0.0228 (17)−0.0063 (16)
C620.121 (4)0.084 (3)0.069 (3)0.029 (3)−0.046 (3)−0.015 (2)
C630.0415 (14)0.0342 (13)0.0506 (16)−0.0023 (11)−0.0120 (12)−0.0066 (12)
C640.0552 (18)0.0417 (16)0.0541 (17)−0.0067 (13)−0.0153 (14)0.0022 (13)
C650.074 (2)0.0414 (17)0.065 (2)−0.0048 (15)−0.0199 (17)0.0006 (15)
C660.091 (3)0.0472 (19)0.063 (2)0.0067 (18)−0.0140 (19)0.0076 (16)
N200.0531 (15)0.0519 (14)0.0406 (13)−0.0053 (11)−0.0087 (11)−0.0129 (11)
C670.0523 (17)0.0582 (18)0.0408 (15)−0.0126 (14)−0.0053 (13)−0.0096 (13)
C680.0475 (17)0.063 (2)0.0480 (17)−0.0132 (15)0.0014 (13)−0.0117 (15)
C690.0541 (18)0.061 (2)0.0472 (17)−0.0120 (15)−0.0005 (14)−0.0053 (14)
C700.057 (2)0.067 (2)0.060 (2)−0.0052 (17)−0.0065 (16)−0.0035 (17)
C710.067 (2)0.0455 (16)0.0501 (17)−0.0005 (14)−0.0205 (15)−0.0084 (13)
C720.0644 (19)0.0467 (16)0.0410 (15)0.0068 (14)−0.0159 (14)−0.0120 (13)
C730.0595 (19)0.0573 (19)0.0587 (19)0.0093 (15)−0.0258 (16)−0.0168 (15)
C740.060 (2)0.063 (2)0.069 (2)0.0039 (16)−0.0069 (17)−0.0198 (18)
C750.0505 (17)0.0475 (16)0.0407 (15)−0.0061 (13)−0.0014 (12)−0.0088 (12)
C760.0552 (18)0.0539 (18)0.0446 (16)−0.0024 (14)−0.0098 (13)−0.0079 (13)
C770.0534 (19)0.0545 (19)0.071 (2)−0.0091 (15)−0.0126 (16)−0.0060 (16)
C780.082 (3)0.115 (4)0.088 (3)−0.044 (3)−0.011 (2)0.017 (3)
C790.070 (2)0.068 (2)0.0420 (16)−0.0177 (18)−0.0090 (15)−0.0090 (15)
C80A0.053 (6)0.093 (4)0.052 (2)−0.034 (4)−0.006 (3)−0.003 (3)
C81A0.058 (3)0.063 (3)0.056 (3)−0.008 (2)0.006 (2)−0.006 (2)
C82A0.093 (7)0.100 (8)0.070 (4)−0.024 (5)−0.010 (5)0.025 (4)
C80B0.053 (6)0.093 (4)0.052 (2)−0.034 (4)−0.006 (3)−0.003 (3)
C81B0.058 (3)0.063 (3)0.056 (3)−0.008 (2)0.006 (2)−0.006 (2)
C82B0.093 (7)0.100 (8)0.070 (4)−0.024 (5)−0.010 (5)0.025 (4)
P10.0237 (3)0.0299 (3)0.0312 (3)−0.0007 (2)−0.0050 (2)−0.0017 (2)
O190.0295 (9)0.0420 (10)0.0336 (9)−0.0027 (7)−0.0072 (7)0.0043 (7)
O200.0240 (8)0.0358 (9)0.0435 (10)0.0032 (7)−0.0043 (7)−0.0080 (7)
O210.0270 (8)0.0365 (9)0.0352 (9)0.0010 (7)−0.0034 (7)−0.0015 (7)
O220.0303 (8)0.0308 (9)0.0375 (9)−0.0013 (7)−0.0079 (7)−0.0027 (7)
P20.0229 (3)0.0267 (3)0.0354 (3)0.0013 (2)−0.0054 (2)−0.0021 (2)
O230.0261 (8)0.0337 (9)0.0417 (9)0.0002 (7)−0.0101 (7)0.0030 (7)
O240.0271 (8)0.0296 (8)0.0425 (9)0.0008 (7)−0.0043 (7)−0.0006 (7)
O250.0258 (8)0.0340 (9)0.0405 (9)0.0022 (7)−0.0082 (7)−0.0032 (7)
O260.0292 (9)0.0341 (9)0.0475 (10)0.0042 (7)−0.0074 (7)−0.0117 (8)
Geometric parameters (Å, º) top
O1—N11.242 (3)C46—H460.9500
O2—N11.226 (3)C47—C481.374 (4)
O3—C101.220 (3)C47—H470.9500
O4—C71.219 (3)C48—C491.385 (4)
O5—N91.228 (4)C49—C501.377 (4)
O6—N91.217 (4)C49—H490.9500
O7—C191.228 (3)C50—H500.9500
O8—N71.225 (3)N19—C541.511 (4)
O9—N71.230 (3)N19—C631.518 (3)
N1—C141.450 (4)N19—C591.521 (3)
N2—C111.382 (3)N19—C551.536 (4)
N2—C101.394 (3)C51—C521.504 (4)
N2—H2N0.898 (5)C51—H51A0.9800
N3—C101.345 (3)C51—H51B0.9800
N3—C91.445 (3)C51—H51C0.9800
N3—H3N0.897 (5)C52—C531.541 (4)
N4—C71.363 (3)C52—H52A0.9900
N4—C171.455 (3)C52—H52B0.9900
N4—C81.457 (3)C53—C541.512 (4)
N5—C191.354 (3)C53—H53A0.9900
N5—C181.454 (3)C53—H53B0.9900
N5—H5N0.899 (5)C54—H54A0.9900
N6—C191.378 (3)C54—H54B0.9900
N6—C201.394 (3)C55—C561.509 (4)
N6—H6N0.897 (5)C55—H55A0.9900
N7—C231.464 (3)C55—H55B0.9900
N8—C71.377 (4)C56—C571.510 (4)
N8—C41.403 (3)C56—H56A0.9900
N8—H8N0.898 (5)C56—H56B0.9900
N9—C11.465 (4)C57—C581.520 (5)
C1—C21.361 (5)C57—H57A0.9900
C1—C61.373 (4)C57—H57B0.9900
C2—C31.385 (4)C58—H58A0.9800
C2—H20.9500C58—H58B0.9800
C3—C41.386 (4)C58—H58C0.9800
C3—H30.9500C59—C601.501 (4)
C4—C51.381 (4)C59—H59A0.9900
C5—C61.382 (4)C59—H59B0.9900
C5—H50.9500C60—C611.512 (4)
C6—H60.9500C60—H60A0.9900
C8—C91.518 (4)C60—H60B0.9900
C8—H8A0.9900C61—C621.488 (5)
C8—H8B0.9900C61—H61A0.9900
C9—H9A0.9900C61—H61B0.9900
C9—H9B0.9900C62—H62A0.9800
C11—C121.402 (4)C62—H62B0.9800
C11—C161.405 (4)C62—H62C0.9800
C12—C131.377 (4)C63—C641.512 (4)
C12—H120.9500C63—H63A0.9900
C13—C141.382 (4)C63—H63B0.9900
C13—H130.9500C64—C651.501 (4)
C14—C151.381 (4)C64—H64A0.9900
C15—C161.372 (4)C64—H64B0.9900
C15—H150.9500C65—C661.501 (5)
C16—H160.9500C65—H65A0.9900
C17—C181.523 (4)C65—H65B0.9900
C17—H17A0.9900C66—H66A0.9800
C17—H17B0.9900C66—H66B0.9800
C18—H18A0.9900C66—H66C0.9800
C18—H18B0.9900N20—C751.507 (4)
C20—C211.398 (4)N20—C711.515 (4)
C20—C251.399 (4)N20—C671.522 (4)
C21—C221.382 (4)N20—C791.541 (4)
C21—H210.9500C67—C681.507 (5)
C22—C231.374 (4)C67—H67A0.9900
C22—H220.9500C67—H67B0.9900
C23—C241.380 (4)C68—C691.511 (5)
C24—C251.379 (4)C68—H68A0.9900
C24—H240.9500C68—H68B0.9900
C25—H250.9500C69—C701.504 (5)
O10A—N101.250 (3)C69—H69A0.9900
O11A—N101.224 (4)C69—H69B0.9900
O10B—N101.230 (3)C70—H70A0.9800
O11B—N101.232 (3)C70—H70B0.9800
O12—C371.216 (3)C70—H70C0.9800
O13—C441.227 (3)C71—C721.527 (4)
O14—N181.223 (3)C71—H71A0.9900
O15—N181.225 (3)C71—H71B0.9900
O16—C321.231 (3)C72—C731.513 (4)
O17—N161.224 (4)C72—H72A0.9900
O18—N161.222 (4)C72—H72B0.9900
N10—C411.451 (4)C73—C741.524 (5)
N11—C381.381 (3)C73—H73A0.9900
N11—C371.391 (3)C73—H73B0.9900
N11—H11N0.899 (5)C74—H74A0.9800
N12—C371.354 (3)C74—H74B0.9800
N12—C361.448 (3)C74—H74C0.9800
N12—H12N0.897 (5)C75—C761.506 (4)
N13—C441.359 (3)C75—H75A0.9900
N13—C341.463 (3)C75—H75B0.9900
N13—C351.463 (3)C76—C771.526 (4)
N14—C321.350 (3)C76—H76A0.9900
N14—C331.451 (3)C76—H76B0.9900
N14—H14N0.898 (5)C77—C781.489 (6)
N15—C321.379 (3)C77—H77A0.9900
N15—C291.393 (3)C77—H77B0.9900
N15—H15N0.897 (5)C78—H78A0.9800
N16—C261.463 (4)C78—H78B0.9800
N17—C441.382 (3)C78—H78C0.9800
N17—C451.404 (3)C79—C80A1.516 (4)
N17—H17N0.898 (5)C79—C80B1.519 (4)
N18—C481.461 (3)C79—H79A0.9900
C26—C271.374 (4)C79—H79B0.9900
C26—C311.379 (4)C79—H79C0.9900
C27—C281.379 (4)C79—H79D0.9900
C27—H270.9500C80A—C81A1.514 (4)
C28—C291.399 (4)C80A—H80A0.9900
C28—H280.9500C80A—H80B0.9900
C29—C301.391 (4)C81A—C82A1.513 (4)
C30—C311.381 (4)C81A—H81A0.9900
C30—H300.9500C81A—H81B0.9900
C31—H310.9500C82A—H82A0.9800
C33—C341.523 (4)C82A—H82B0.9800
C33—H33A0.9900C82A—H82C0.9800
C33—H33B0.9900C80B—C81B1.515 (4)
C34—H34A0.9900C80B—H80C0.9900
C34—H34B0.9900C80B—H80D0.9900
C35—C361.519 (4)C81B—C82B1.506 (4)
C35—H35A0.9900C81B—H81C0.9900
C35—H35B0.9900C81B—H81D0.9900
C36—H36A0.9900C82B—H82D0.9800
C36—H36B0.9900C82B—H82E0.9800
C38—C431.402 (4)C82B—H82F0.9800
C38—C391.405 (4)P1—O221.5071 (17)
C39—C401.372 (4)P1—O191.5072 (17)
C39—H390.9500P1—O201.5632 (18)
C40—C411.374 (4)P1—O211.5695 (18)
C40—H400.9500O20—H20O0.928 (5)
C41—C421.383 (4)O21—H21O0.928 (5)
C42—C431.382 (4)P2—O241.5054 (17)
C42—H420.9500P2—O261.5226 (18)
C43—H430.9500P2—O251.5531 (18)
C45—C501.397 (4)P2—O231.5705 (18)
C45—C461.400 (4)O23—H23O0.927 (5)
C46—C471.379 (4)O25—H25O0.928 (5)
O2—N1—O1122.6 (3)C52—C51—H51B109.5
O2—N1—C14119.2 (2)H51A—C51—H51B109.5
O1—N1—C14118.1 (3)C52—C51—H51C109.5
C11—N2—C10127.4 (2)H51A—C51—H51C109.5
C11—N2—H2N118 (2)H51B—C51—H51C109.5
C10—N2—H2N115 (2)C51—C52—C53114.4 (3)
C10—N3—C9121.4 (2)C51—C52—H52A108.7
C10—N3—H3N123 (2)C53—C52—H52A108.7
C9—N3—H3N116 (2)C51—C52—H52B108.7
C7—N4—C17123.5 (2)C53—C52—H52B108.7
C7—N4—C8118.8 (2)H52A—C52—H52B107.6
C17—N4—C8117.8 (2)C54—C53—C52110.6 (2)
C19—N5—C18119.6 (2)C54—C53—H53A109.5
C19—N5—H5N118 (2)C52—C53—H53A109.5
C18—N5—H5N120 (2)C54—C53—H53B109.5
C19—N6—C20126.8 (2)C52—C53—H53B109.5
C19—N6—H6N115 (2)H53A—C53—H53B108.1
C20—N6—H6N118 (2)N19—C54—C53116.7 (2)
O8—N7—O9123.9 (3)N19—C54—H54A108.1
O8—N7—C23118.4 (3)C53—C54—H54A108.1
O9—N7—C23117.7 (3)N19—C54—H54B108.1
C7—N8—C4126.1 (2)C53—C54—H54B108.1
C7—N8—H8N120 (2)H54A—C54—H54B107.3
C4—N8—H8N113 (2)C56—C55—N19115.7 (2)
O6—N9—O5123.8 (3)C56—C55—H55A108.3
O6—N9—C1118.4 (3)N19—C55—H55A108.3
O5—N9—C1117.8 (3)C56—C55—H55B108.3
C2—C1—C6121.9 (3)N19—C55—H55B108.3
C2—C1—N9118.9 (3)H55A—C55—H55B107.4
C6—C1—N9119.2 (3)C55—C56—C57110.7 (3)
C1—C2—C3119.6 (3)C55—C56—H56A109.5
C1—C2—H2120.2C57—C56—H56A109.5
C3—C2—H2120.2C55—C56—H56B109.5
C2—C3—C4120.0 (3)C57—C56—H56B109.5
C2—C3—H3120.0H56A—C56—H56B108.1
C4—C3—H3120.0C56—C57—C58112.4 (3)
C5—C4—C3119.1 (3)C56—C57—H57A109.1
C5—C4—N8117.2 (3)C58—C57—H57A109.1
C3—C4—N8123.7 (3)C56—C57—H57B109.1
C4—C5—C6121.1 (3)C58—C57—H57B109.1
C4—C5—H5119.5H57A—C57—H57B107.9
C6—C5—H5119.5C57—C58—H58A109.5
C1—C6—C5118.4 (3)C57—C58—H58B109.5
C1—C6—H6120.8H58A—C58—H58B109.5
C5—C6—H6120.8C57—C58—H58C109.5
O4—C7—N4121.4 (3)H58A—C58—H58C109.5
O4—C7—N8122.6 (2)H58B—C58—H58C109.5
N4—C7—N8116.0 (2)C60—C59—N19116.4 (2)
N4—C8—C9112.0 (2)C60—C59—H59A108.2
N4—C8—H8A109.2N19—C59—H59A108.2
C9—C8—H8A109.2C60—C59—H59B108.2
N4—C8—H8B109.2N19—C59—H59B108.2
C9—C8—H8B109.2H59A—C59—H59B107.3
H8A—C8—H8B107.9C59—C60—C61111.0 (3)
N3—C9—C8111.5 (2)C59—C60—H60A109.4
N3—C9—H9A109.3C61—C60—H60A109.4
C8—C9—H9A109.3C59—C60—H60B109.4
N3—C9—H9B109.3C61—C60—H60B109.4
C8—C9—H9B109.3H60A—C60—H60B108.0
H9A—C9—H9B108.0C62—C61—C60115.8 (3)
O3—C10—N3123.7 (2)C62—C61—H61A108.3
O3—C10—N2123.2 (2)C60—C61—H61A108.3
N3—C10—N2113.1 (2)C62—C61—H61B108.3
N2—C11—C12124.3 (2)C60—C61—H61B108.3
N2—C11—C16117.3 (2)H61A—C61—H61B107.4
C12—C11—C16118.4 (2)C61—C62—H62A109.5
C13—C12—C11120.2 (3)C61—C62—H62B109.5
C13—C12—H12119.9H62A—C62—H62B109.5
C11—C12—H12119.9C61—C62—H62C109.5
C12—C13—C14119.9 (3)H62A—C62—H62C109.5
C12—C13—H13120.1H62B—C62—H62C109.5
C14—C13—H13120.1C64—C63—N19116.6 (2)
C15—C14—C13121.1 (3)C64—C63—H63A108.1
C15—C14—N1119.3 (2)N19—C63—H63A108.1
C13—C14—N1119.5 (3)C64—C63—H63B108.1
C16—C15—C14119.2 (3)N19—C63—H63B108.1
C16—C15—H15120.4H63A—C63—H63B107.3
C14—C15—H15120.4C65—C64—C63111.0 (3)
C15—C16—C11121.1 (3)C65—C64—H64A109.4
C15—C16—H16119.4C63—C64—H64A109.4
C11—C16—H16119.4C65—C64—H64B109.4
N4—C17—C18112.3 (2)C63—C64—H64B109.4
N4—C17—H17A109.2H64A—C64—H64B108.0
C18—C17—H17A109.2C64—C65—C66114.6 (3)
N4—C17—H17B109.2C64—C65—H65A108.6
C18—C17—H17B109.2C66—C65—H65A108.6
H17A—C17—H17B107.9C64—C65—H65B108.6
N5—C18—C17111.0 (2)C66—C65—H65B108.6
N5—C18—H18A109.4H65A—C65—H65B107.6
C17—C18—H18A109.4C65—C66—H66A109.5
N5—C18—H18B109.4C65—C66—H66B109.5
C17—C18—H18B109.4H66A—C66—H66B109.5
H18A—C18—H18B108.0C65—C66—H66C109.5
O7—C19—N5122.3 (2)H66A—C66—H66C109.5
O7—C19—N6124.2 (2)H66B—C66—H66C109.5
N5—C19—N6113.6 (2)C75—N20—C71111.4 (2)
N6—C20—C21123.7 (2)C75—N20—C67109.4 (2)
N6—C20—C25117.3 (2)C71—N20—C67108.7 (2)
C21—C20—C25119.0 (2)C75—N20—C79108.2 (2)
C22—C21—C20119.5 (3)C71—N20—C79108.4 (3)
C22—C21—H21120.3C67—N20—C79110.7 (2)
C20—C21—H21120.3C68—C67—N20116.6 (3)
C23—C22—C21120.3 (3)C68—C67—H67A108.1
C23—C22—H22119.8N20—C67—H67A108.1
C21—C22—H22119.8C68—C67—H67B108.1
C22—C23—C24121.4 (3)N20—C67—H67B108.1
C22—C23—N7119.7 (3)H67A—C67—H67B107.3
C24—C23—N7118.9 (3)C67—C68—C69111.7 (3)
C25—C24—C23118.6 (2)C67—C68—H68A109.3
C25—C24—H24120.7C69—C68—H68A109.3
C23—C24—H24120.7C67—C68—H68B109.3
C24—C25—C20121.2 (2)C69—C68—H68B109.3
C24—C25—H25119.4H68A—C68—H68B107.9
C20—C25—H25119.4C70—C69—C68113.2 (3)
O10B—N10—O11B121.8 (4)C70—C69—H69A108.9
O11A—N10—O10A120.6 (5)C68—C69—H69A108.9
O11A—N10—C41121.8 (5)C70—C69—H69B108.9
O10B—N10—C41119.6 (3)C68—C69—H69B108.9
O11B—N10—C41115.9 (4)H69A—C69—H69B107.8
O10A—N10—C41115.8 (3)C69—C70—H70A109.5
C38—N11—C37128.6 (2)C69—C70—H70B109.5
C38—N11—H11N116 (2)H70A—C70—H70B109.5
C37—N11—H11N115 (2)C69—C70—H70C109.5
C37—N12—C36122.4 (2)H70A—C70—H70C109.5
C37—N12—H12N122 (2)H70B—C70—H70C109.5
C36—N12—H12N115 (2)N20—C71—C72115.0 (3)
C44—N13—C34124.1 (2)N20—C71—H71A108.5
C44—N13—C35117.9 (2)C72—C71—H71A108.5
C34—N13—C35117.95 (19)N20—C71—H71B108.5
C32—N14—C33119.4 (2)C72—C71—H71B108.5
C32—N14—H14N120 (2)H71A—C71—H71B107.5
C33—N14—H14N118 (2)C73—C72—C71112.4 (3)
C32—N15—C29128.0 (2)C73—C72—H72A109.1
C32—N15—H15N115 (2)C71—C72—H72A109.1
C29—N15—H15N117 (2)C73—C72—H72B109.1
O18—N16—O17123.3 (3)C71—C72—H72B109.1
O18—N16—C26118.7 (3)H72A—C72—H72B107.9
O17—N16—C26118.0 (3)C72—C73—C74112.1 (3)
C44—N17—C45126.4 (2)C72—C73—H73A109.2
C44—N17—H17N118.8 (19)C74—C73—H73A109.2
C45—N17—H17N114.6 (19)C72—C73—H73B109.2
O14—N18—O15123.2 (2)C74—C73—H73B109.2
O14—N18—C48118.2 (2)H73A—C73—H73B107.9
O15—N18—C48118.6 (2)C73—C74—H74A109.5
C27—C26—C31121.1 (3)C73—C74—H74B109.5
C27—C26—N16119.2 (3)H74A—C74—H74B109.5
C31—C26—N16119.7 (3)C73—C74—H74C109.5
C26—C27—C28118.8 (2)H74A—C74—H74C109.5
C26—C27—H27120.6H74B—C74—H74C109.5
C28—C27—H27120.6C76—C75—N20115.8 (3)
C27—C28—C29121.3 (2)C76—C75—H75A108.3
C27—C28—H28119.4N20—C75—H75A108.3
C29—C28—H28119.4C76—C75—H75B108.3
C30—C29—N15124.3 (2)N20—C75—H75B108.3
C30—C29—C28118.9 (2)H75A—C75—H75B107.4
N15—C29—C28116.8 (2)C75—C76—C77110.9 (3)
C31—C30—C29119.7 (3)C75—C76—H76A109.5
C31—C30—H30120.2C77—C76—H76A109.5
C29—C30—H30120.2C75—C76—H76B109.5
C26—C31—C30120.3 (3)C77—C76—H76B109.5
C26—C31—H31119.8H76A—C76—H76B108.1
C30—C31—H31119.8C78—C77—C76112.7 (3)
O16—C32—N14122.2 (2)C78—C77—H77A109.1
O16—C32—N15124.3 (2)C76—C77—H77A109.1
N14—C32—N15113.6 (2)C78—C77—H77B109.1
N14—C33—C34111.3 (2)C76—C77—H77B109.1
N14—C33—H33A109.4H77A—C77—H77B107.8
C34—C33—H33A109.4C77—C78—H78A109.5
N14—C33—H33B109.4C77—C78—H78B109.5
C34—C33—H33B109.4H78A—C78—H78B109.5
H33A—C33—H33B108.0C77—C78—H78C109.5
N13—C34—C33112.3 (2)H78A—C78—H78C109.5
N13—C34—H34A109.2H78B—C78—H78C109.5
C33—C34—H34A109.2C80A—C79—N20117.2 (3)
N13—C34—H34B109.2C80B—C79—N20115.3 (4)
C33—C34—H34B109.2C80A—C79—H79A108.0
H34A—C34—H34B107.9N20—C79—H79A108.0
N13—C35—C36112.4 (2)C80A—C79—H79B108.0
N13—C35—H35A109.1N20—C79—H79B108.0
C36—C35—H35A109.1H79A—C79—H79B107.2
N13—C35—H35B109.1C80B—C79—H79C108.5
C36—C35—H35B109.1N20—C79—H79C108.5
H35A—C35—H35B107.9C80B—C79—H79D108.5
N12—C36—C35111.2 (2)N20—C79—H79D108.5
N12—C36—H36A109.4H79C—C79—H79D107.5
C35—C36—H36A109.4C81A—C80A—C79111.0 (5)
N12—C36—H36B109.4C81A—C80A—H80A109.4
C35—C36—H36B109.4C79—C80A—H80A109.4
H36A—C36—H36B108.0C81A—C80A—H80B109.4
O12—C37—N12124.5 (2)C79—C80A—H80B109.4
O12—C37—N11123.9 (2)H80A—C80A—H80B108.0
N12—C37—N11111.6 (2)C82A—C81A—C80A119.5 (7)
N11—C38—C43124.9 (2)C82A—C81A—H81A107.4
N11—C38—C39116.5 (2)C80A—C81A—H81A107.4
C43—C38—C39118.7 (2)C82A—C81A—H81B107.4
C40—C39—C38121.2 (2)C80A—C81A—H81B107.4
C40—C39—H39119.4H81A—C81A—H81B107.0
C38—C39—H39119.4C81A—C82A—H82A109.5
C39—C40—C41119.2 (3)C81A—C82A—H82B109.5
C39—C40—H40120.4H82A—C82A—H82B109.5
C41—C40—H40120.4C81A—C82A—H82C109.5
C40—C41—C42121.1 (3)H82A—C82A—H82C109.5
C40—C41—N10119.0 (3)H82B—C82A—H82C109.5
C42—C41—N10119.9 (3)C81B—C80B—C79117.2 (5)
C43—C42—C41120.3 (3)C81B—C80B—H80C108.0
C43—C42—H42119.9C79—C80B—H80C108.0
C41—C42—H42119.9C81B—C80B—H80D108.0
C42—C43—C38119.5 (3)C79—C80B—H80D108.0
C42—C43—H43120.3H80C—C80B—H80D107.2
C38—C43—H43120.3C82B—C81B—C80B114.5 (7)
O13—C44—N13121.2 (2)C82B—C81B—H81C108.6
O13—C44—N17122.9 (2)C80B—C81B—H81C108.6
N13—C44—N17115.9 (2)C82B—C81B—H81D108.6
C50—C45—C46119.2 (2)C80B—C81B—H81D108.6
C50—C45—N17116.4 (2)H81C—C81B—H81D107.6
C46—C45—N17124.3 (2)C81B—C82B—H82D109.5
C47—C46—C45119.8 (2)C81B—C82B—H82E109.5
C47—C46—H46120.1H82D—C82B—H82E109.5
C45—C46—H46120.1C81B—C82B—H82F109.5
C48—C47—C46119.6 (2)H82D—C82B—H82F109.5
C48—C47—H47120.2H82E—C82B—H82F109.5
C46—C47—H47120.2O22—P1—O19114.54 (10)
C47—C48—C49122.0 (2)O22—P1—O20111.33 (9)
C47—C48—N18119.6 (2)O19—P1—O20107.35 (10)
C49—C48—N18118.5 (2)O22—P1—O21106.44 (10)
C50—C49—C48118.3 (2)O19—P1—O21109.89 (9)
C50—C49—H49120.8O20—P1—O21107.06 (10)
C48—C49—H49120.8P1—O20—H20O111 (2)
C49—C50—C45121.0 (2)P1—O21—H21O115 (2)
C49—C50—H50119.5O24—P2—O26112.39 (10)
C45—C50—H50119.5O24—P2—O25108.25 (10)
C54—N19—C63108.4 (2)O26—P2—O25110.73 (10)
C54—N19—C59111.8 (2)O24—P2—O23110.98 (9)
C63—N19—C59108.9 (2)O26—P2—O23106.28 (10)
C54—N19—C55109.5 (2)O25—P2—O23108.14 (10)
C63—N19—C55110.2 (2)P2—O23—H23O114 (2)
C59—N19—C55108.1 (2)P2—O25—H25O113 (2)
C52—C51—H51A109.5
O6—N9—C1—C2−166.3 (3)C37—N12—C36—C35−97.3 (3)
O5—N9—C1—C214.0 (4)N13—C35—C36—N12−172.7 (2)
O6—N9—C1—C612.2 (4)C36—N12—C37—O12−4.5 (4)
O5—N9—C1—C6−167.5 (3)C36—N12—C37—N11175.5 (2)
C6—C1—C2—C3−1.0 (5)C38—N11—C37—O12−4.1 (5)
N9—C1—C2—C3177.5 (3)C38—N11—C37—N12175.9 (2)
C1—C2—C3—C41.4 (5)C37—N11—C38—C43−6.0 (4)
C2—C3—C4—C5−0.9 (5)C37—N11—C38—C39174.8 (3)
C2—C3—C4—N8177.3 (3)N11—C38—C39—C40179.6 (2)
C7—N8—C4—C5−172.6 (3)C43—C38—C39—C400.3 (4)
C7—N8—C4—C39.2 (5)C38—C39—C40—C411.2 (4)
C3—C4—C5—C6−0.1 (4)C39—C40—C41—C42−2.3 (4)
N8—C4—C5—C6−178.3 (3)C39—C40—C41—N10178.7 (3)
C2—C1—C6—C50.0 (5)O11A—N10—C41—C40−2.6 (11)
N9—C1—C6—C5−178.4 (3)O10B—N10—C41—C40−162.2 (4)
C4—C5—C6—C10.5 (4)O11B—N10—C41—C40−0.6 (9)
C17—N4—C7—O4175.2 (3)O10A—N10—C41—C40161.9 (4)
C8—N4—C7—O4−4.5 (4)O11A—N10—C41—C42178.3 (10)
C17—N4—C7—N8−4.0 (4)O10B—N10—C41—C4218.8 (5)
C8—N4—C7—N8176.4 (2)O11B—N10—C41—C42−179.6 (8)
C4—N8—C7—O44.9 (5)O10A—N10—C41—C42−17.2 (5)
C4—N8—C7—N4−176.0 (3)C40—C41—C42—C431.8 (5)
C7—N4—C8—C9100.0 (3)N10—C41—C42—C43−179.2 (3)
C17—N4—C8—C9−79.6 (3)C41—C42—C43—C38−0.2 (5)
C10—N3—C9—C891.6 (3)N11—C38—C43—C42180.0 (3)
N4—C8—C9—N3177.7 (2)C39—C38—C43—C42−0.8 (4)
C9—N3—C10—O30.3 (4)C34—N13—C44—O13−179.1 (2)
C9—N3—C10—N2−179.3 (2)C35—N13—C44—O133.2 (4)
C11—N2—C10—O36.3 (4)C34—N13—C44—N170.5 (4)
C11—N2—C10—N3−174.0 (2)C35—N13—C44—N17−177.3 (2)
C10—N2—C11—C122.1 (4)C45—N17—C44—O134.7 (4)
C10—N2—C11—C16−179.0 (2)C45—N17—C44—N13−174.8 (2)
N2—C11—C12—C13−179.0 (2)C44—N17—C45—C50−177.8 (2)
C16—C11—C12—C132.1 (4)C44—N17—C45—C463.1 (4)
C11—C12—C13—C14−0.3 (4)C50—C45—C46—C470.9 (4)
C12—C13—C14—C15−1.8 (4)N17—C45—C46—C47−179.9 (2)
C12—C13—C14—N1175.4 (2)C45—C46—C47—C48−1.6 (4)
O2—N1—C14—C15174.6 (3)C46—C47—C48—C490.8 (4)
O1—N1—C14—C15−2.7 (4)C46—C47—C48—N18−179.3 (2)
O2—N1—C14—C13−2.6 (4)O14—N18—C48—C47−14.2 (4)
O1—N1—C14—C13−179.9 (2)O15—N18—C48—C47165.5 (2)
C13—C14—C15—C162.0 (4)O14—N18—C48—C49165.7 (3)
N1—C14—C15—C16−175.2 (2)O15—N18—C48—C49−14.6 (3)
C14—C15—C16—C11−0.2 (4)C47—C48—C49—C500.7 (4)
N2—C11—C16—C15179.2 (2)N18—C48—C49—C50−179.3 (2)
C12—C11—C16—C15−1.8 (4)C48—C49—C50—C45−1.3 (4)
C7—N4—C17—C1881.5 (3)C46—C45—C50—C490.6 (4)
C8—N4—C17—C18−98.9 (3)N17—C45—C50—C49−178.7 (2)
C19—N5—C18—C1775.3 (3)C51—C52—C53—C54−56.8 (4)
N4—C17—C18—N5−161.0 (2)C63—N19—C54—C53−172.7 (2)
C18—N5—C19—O7−5.2 (4)C59—N19—C54—C53−52.7 (3)
C18—N5—C19—N6174.8 (2)C55—N19—C54—C5367.1 (3)
C20—N6—C19—O712.1 (4)C52—C53—C54—N19−167.5 (2)
C20—N6—C19—N5−167.8 (3)C54—N19—C55—C56178.0 (2)
C19—N6—C20—C21−22.3 (4)C63—N19—C55—C5658.9 (3)
C19—N6—C20—C25157.0 (3)C59—N19—C55—C56−59.9 (3)
N6—C20—C21—C22177.5 (3)N19—C55—C56—C57−173.0 (3)
C25—C20—C21—C22−1.8 (4)C55—C56—C57—C58−174.2 (3)
C20—C21—C22—C231.2 (4)C54—N19—C59—C60−56.1 (3)
C21—C22—C23—C240.5 (4)C63—N19—C59—C6063.6 (3)
C21—C22—C23—N7−178.2 (2)C55—N19—C59—C60−176.7 (3)
O8—N7—C23—C22−172.3 (3)N19—C59—C60—C61−172.1 (3)
O9—N7—C23—C227.3 (4)C59—C60—C61—C62−179.5 (4)
O8—N7—C23—C248.9 (4)C54—N19—C63—C64−70.4 (3)
O9—N7—C23—C24−171.4 (2)C59—N19—C63—C64167.8 (3)
C22—C23—C24—C25−1.4 (4)C55—N19—C63—C6449.4 (3)
N7—C23—C24—C25177.3 (2)N19—C63—C64—C65172.0 (3)
C23—C24—C25—C200.7 (4)C63—C64—C65—C66171.0 (3)
N6—C20—C25—C24−178.4 (2)C75—N20—C67—C6852.6 (3)
C21—C20—C25—C240.9 (4)C71—N20—C67—C68174.5 (3)
O18—N16—C26—C27−8.2 (4)C79—N20—C67—C68−66.5 (3)
O17—N16—C26—C27171.0 (3)N20—C67—C68—C69173.3 (3)
O18—N16—C26—C31173.4 (3)C67—C68—C69—C70171.4 (3)
O17—N16—C26—C31−7.5 (5)C75—N20—C71—C7249.7 (3)
C31—C26—C27—C28−0.4 (4)C67—N20—C71—C72−71.0 (3)
N16—C26—C27—C28−178.8 (3)C79—N20—C71—C72168.6 (3)
C26—C27—C28—C29−0.7 (4)N20—C71—C72—C73−153.1 (3)
C32—N15—C29—C3016.0 (4)C71—C72—C73—C74175.4 (3)
C32—N15—C29—C28−162.8 (2)C71—N20—C75—C7651.1 (3)
C27—C28—C29—C300.6 (4)C67—N20—C75—C76171.3 (2)
C27—C28—C29—N15179.6 (2)C79—N20—C75—C76−68.1 (3)
N15—C29—C30—C31−178.3 (3)N20—C75—C76—C77−166.4 (3)
C28—C29—C30—C310.5 (5)C75—C76—C77—C7874.3 (4)
C27—C26—C31—C301.5 (5)C75—N20—C79—C80A−163.3 (6)
N16—C26—C31—C30179.9 (3)C71—N20—C79—C80A75.7 (6)
C29—C30—C31—C26−1.5 (5)C67—N20—C79—C80A−43.4 (6)
C33—N14—C32—O163.9 (4)C75—N20—C79—C80B172.4 (5)
C33—N14—C32—N15−175.8 (2)C71—N20—C79—C80B51.4 (5)
C29—N15—C32—O16−6.2 (4)C67—N20—C79—C80B−67.8 (5)
C29—N15—C32—N14173.5 (2)C80B—C79—C80A—C81A−84.0 (13)
C32—N14—C33—C34−75.5 (3)N20—C79—C80A—C81A−174.5 (5)
C44—N13—C34—C33−81.5 (3)C79—C80A—C81A—C82A53.5 (12)
C35—N13—C34—C3396.2 (3)C80A—C79—C80B—C81B108.0 (17)
N14—C33—C34—N13164.1 (2)N20—C79—C80B—C81B−151.7 (6)
C44—N13—C35—C36−87.5 (3)C79—C80B—C81B—C82B−46.3 (11)
C34—N13—C35—C3694.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8N···O70.90 (3)2.07 (3)2.955 (3)168 (3)
N17—H17N···O160.90 (2)2.21 (2)3.100 (3)170 (2)
N5—H5N···O210.90 (2)2.04 (2)2.915 (3)164 (3)
N6—H6N···O220.90 (2)2.10 (2)2.986 (3)168 (2)
N11—H11N···O190.90 (2)1.96 (2)2.854 (3)175 (2)
N12—H12N···O220.90 (2)2.21 (2)3.058 (3)157 (3)
O20—H20O···O240.93 (2)1.66 (2)2.583 (2)178 (3)
O23—H23O···O220.93 (2)1.64 (2)2.568 (2)176 (2)
O21—H21O···O19i0.93 (2)1.61 (2)2.528 (2)173 (3)
O25—H25O···O26ii0.93 (2)1.59 (2)2.501 (2)166 (3)
N2—H2N···O26i0.90 (2)2.08 (2)2.977 (3)174 (2)
N3—H3N···O24i0.90 (2)2.09 (2)2.931 (3)155 (3)
N14—H14N···O25ii0.90 (2)2.03 (2)2.930 (3)175 (2)
N15—H15N···O24ii0.90 (2)2.10 (2)2.986 (3)168 (2)
C3—H3···O40.952.172.789 (4)121
C5—H5···O70.952.533.279 (4)136
C12—H12···O30.952.232.844 (3)122
C21—H21···O70.952.312.872 (4)118
C30—H30···O160.952.322.903 (4)119
C43—H43···O120.952.322.910 (4)120
C46—H46···O130.952.192.810 (3)122
C18—H18A···O1iii0.992.423.345 (4)156
C30—H30···O6iv0.952.583.265 (4)129
C33—H33B···O11Aiii0.992.583.235 (12)123
C39—H39···O21i0.952.523.446 (3)164
C54—H54A···O15v0.992.463.447 (4)173
C63—H63A···O30.992.423.379 (4)164
C63—H63B···O40.992.263.003 (4)131
C64—H64B···O15v0.992.463.348 (4)149
C70—H70B···O10Aiii0.982.473.289 (6)141
C75—H75A···O130.992.313.158 (4)143
C75—H75B···O1vi0.992.583.514 (4)157
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) x−1, y, z−1; (vi) x+1, y, z+1.
 

Acknowledgements

We are grateful to the Comprehensive Training Platform of Specialized Laboratory, College of Chemistry, Sichuan University, for the IR, NMR, HRMS and XRD analyses. We appreciate the help of Dr Yue Qi and Dr Meng Yang with the X-ray single-crystal measurements.

Funding information

Funding for this research was provided by: National Natural Science Foundation of China (grant No. 21501123).

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ISSN: 2056-9890
Volume 75| Part 3| March 2019| Pages 319-323
https://doi.org/10.1107/S2056989019001336
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