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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1936–o1937.
Published online 2008 September 13. doi:  10.1107/S1600536808028845
PMCID: PMC2959237

1,3,5-Tris{[3-(1H-benzotriazol-1-ylmeth­yl)phen­oxy]meth­yl}-2,4,6-trimethyl­benzene

Abstract

In the title compound, C51H45N9O3, three 1-(1H-benzotriazol-1-ylmeth­yl)-3-phen­yloxy (bmph) ligands are bonded to the central benzene ring in an asymmetric arrangement, two bmph located on one side of the central benzene ring and the other bmph located on the opposite side of the central benzene ring. The dihedral angles between the central benzene ring and the three pendant phenoxy rings are 76.71 (14), 67.81 (13) and 70.67 (16)°. In the crystal structure, one bmph is disordered over two sites in a 0.611 (5):0.389 (5) ratio. Some of the methyl H atoms are equally disordered over two sets of sites. Inter­molecular C—H(...)N hydrogen bonding is present in the crystal structure.

Related literature

For general background, see: Androsov & Neckers (2007 [triangle]); Blackman (2005 [triangle]); Fan et al. (2003 [triangle]); Fujita et al. (1995 [triangle]); Li et al. (2007 [triangle]); Zeng & Zimmerman (1997 [triangle]); Zhao et al. (2005 [triangle]). For related structures, see: Selvanayagam et al. (2004 [triangle]); Cai et al. (2004 [triangle]). For the synthesis, see: Gong et al. (2007 [triangle]); van der Made & van der Made (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1936-scheme1.jpg

Experimental

Crystal data

  • C51H45N9O3
  • M r = 831.96
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1936-efi1.jpg
  • a = 11.945 (3) Å
  • b = 13.524 (3) Å
  • c = 13.550 (3) Å
  • α = 83.913 (4)°
  • β = 80.629 (4)°
  • γ = 84.766 (4)°
  • V = 2141.4 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 (2) K
  • 0.23 × 0.19 × 0.18 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 16527 measured reflections
  • 7926 independent reflections
  • 3519 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.186
  • S = 1.01
  • 7926 reflections
  • 552 parameters
  • 60 restraints
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028845/xu2438sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028845/xu2438Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20872057) and the Natural Science Foundation of Henan Province, China (No. 082300420040).

supplementary crystallographic information

Comment

Tripodal ligands based on nitrogen heterocycles have been widely employed in many areas of inorganic chemistry (Blackman, 2005). For example, tripodal ligands with an arene core have been found to be one of the most useful organic building blocks in construction of metal-organic frameworks(MOFs) (Zeng & Zimmerman, 1997; Li et al., 2007). Especially in the case of flexible tripodal ligands such as 1,3,5-tris(4-pyridylmethyl)benzene (Fujita et al., 1995) and 1,3,5-tris(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene (Fan et al., 2003), which have many more possible coordination modes due to their flexibility, and they can adopt different conformations according to geometric requirements of different metal ions (Zhao et al., 2005). However, only a few examples of flexible tripodal benzotriazole ligands are reported (Androsov & Neckers, 2007). Herein we report the crystal structure of the title compound.

A view of the molecular structure of the title compound is given in Fig.1. IN the crystal structure the three 1-(1H-benzotriazol-1-ylmethyl)-3-phenyloxy (bmph) groups are bonded to the central benzene ring with an asymmetric arrangement, two bmph located on one side of the central benzene ring and the other bmph located on the opposite side of the central benzene ring. The dihedral angles between each benzotriazole moiety and the phenyloxy benzene rings are 86.1 (2), 91.8 (3) and 109.2 (2)°, respectively, and dihedral angles between mesitylene and phenyloxy benzene rings are 121.0 (2), 70.7 (3) and 112.2 (3)°. The N1-benzotriazole and N7-benzotriazole are approximately parallel to each other with a dihedral angle of 9.4 (2)°. All the bond distances and angles in the structure are within normal ranges, similar to those found in the related compound (Selvanayagam et al., 2004; Cai et al., 2004). Intermolecular C—H···N hydrogen bonding presents in the crystal structure (Table 1).

Experimental

1,3,5-Tris(bromomethyl)-2,4,6-trimethylbenzene and 1-(benzotriazol-1-ylmethyl)- 3-hydroxybenzene were synthesized according to the reported procedure was (van der Made et al., 1993; Gong et al., 2007). 1,3,5-Tris(bromomethyl)-2,4,6- trimethylbenzene (3 mmol), 1-(benzotriazol-1-ylmethyl)-3-hydroxybenzene (9 mmol) and NaH (27 mmol) were dissolved in dry dioxane (25 ml), then the resultant solution was refluxed for 6 h, removal of solvent resulted in a white powder that was recrystallized from dichloromethane-petroleum ether solution at room temperature to give the desired product as colorless crystals suitable for single-crystal X-ray diffraction (yield 55%; m.p > 573 K).

Refinement

The N4-containing benzotriazole is disordered over two sites, occupancies were refined and converged to 0.611 (5):0.389 (5). The rigid-group mode was used in refinement for the disordered components, and atomic displacement parameters were constrained for disordered components. H atoms were placed in geometrically idealized positions and treated as riding with C—H = 0.93 (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene), and constrained to ride on their parent atoms with Uiso(H) = 1.5Ueq(C) (for methyl) or 1.2Ueq(C) for others.

Figures

Fig. 1.
The molecular structure of the title compound with 30% displacement probability ellipsoids.

Crystal data

C51H45N9O3Z = 2
Mr = 831.96F(000) = 876
Triclinic, P1Dx = 1.290 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.945 (3) ÅCell parameters from 1969 reflections
b = 13.524 (3) Åθ = 2.5–20.4°
c = 13.550 (3) ŵ = 0.08 mm1
α = 83.913 (4)°T = 295 K
β = 80.629 (4)°Block, colourless
γ = 84.766 (4)°0.23 × 0.19 × 0.18 mm
V = 2141.4 (9) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
graphiteθmax = 25.5°, θmin = 2.5°
[var phi] and ω scansh = −14→14
16527 measured reflectionsk = −16→16
7926 independent reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0806P)2 + 0.0204P] where P = (Fo2 + 2Fc2)/3
7926 reflections(Δ/σ)max < 0.001
552 parametersΔρmax = 0.15 e Å3
60 restraintsΔρmin = −0.28 e Å3

Special details

Experimental. Analysis found: C 73.85, H 5.29, N 15.37%; requires: C 73.63, H 5.45, N 15.15%. IR data (v_max/ cm-1): 3425, 2924, 1593, 1489, 1451, 1257, 1158, 1089, 1009, 781, 747. NMR δ(H) 1.85(6H,brs), 2.32(9H,s), 4.99(6H,s), 5.84(6H,s), 6.90(6H,d), 6.95 (3H,d), 7.26(3H,s), 7.35–7.43(9H,s), 8.08(3H,s). MS-ESI+ [m/z]: 854.6(M+Na).
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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused when they are defined by crystal symmetry. An approximate (isotropic)treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/UeqOcc. (<1)
N60.8300 (6)1.4682 (5)0.5035 (4)0.0889 (13)0.611 (5)
N40.9689 (5)1.3866 (4)0.5597 (4)0.125 (2)0.611 (5)
N50.8893 (7)1.4545 (5)0.5804 (4)0.121 (2)0.611 (5)
C240.9686 (4)1.3515 (3)0.4672 (3)0.0935 (17)0.611 (5)
C251.0378 (4)1.2814 (4)0.4112 (4)0.114 (2)0.611 (5)
H251.10051.24560.43380.137*0.611 (5)
C261.0059 (5)1.2696 (4)0.3202 (4)0.125 (2)0.611 (5)
H261.04631.22090.28230.150*0.611 (5)
C270.9172 (5)1.3259 (5)0.2818 (4)0.112 (2)0.611 (5)
H270.90301.31690.21800.134*0.611 (5)
C280.8493 (5)1.3958 (5)0.3379 (4)0.0961 (15)0.611 (5)
H280.78881.43320.31330.115*0.611 (5)
C290.8757 (4)1.4072 (4)0.4326 (3)0.0780 (10)0.611 (5)
C300.7351 (8)1.5351 (7)0.5177 (6)0.1372 (18)0.611 (5)
H30A0.71041.55560.45340.165*0.611 (5)
H30B0.75581.59400.54360.165*0.611 (5)
C10.8340 (3)0.2950 (3)0.9635 (4)0.0977 (12)
N6'0.8453 (10)1.4436 (8)0.5142 (7)0.0889 (13)0.389 (5)
N4'0.9868 (9)1.3395 (7)0.5248 (6)0.125 (2)0.389 (5)
N5'0.9219 (11)1.4049 (8)0.5727 (6)0.121 (2)0.389 (5)
C24'0.9586 (6)1.3312 (5)0.4307 (6)0.0935 (17)0.389 (5)
C25'1.0041 (7)1.2740 (6)0.3510 (6)0.114 (2)0.389 (5)
H25'1.06731.22880.35330.137*0.389 (5)
C26'0.9478 (8)1.2901 (6)0.2689 (6)0.125 (2)0.389 (5)
H26'0.97181.25100.21590.150*0.389 (5)
C27'0.8575 (9)1.3611 (7)0.2605 (6)0.112 (2)0.389 (5)
H27'0.82621.37090.20140.134*0.389 (5)
C28'0.8132 (8)1.4179 (7)0.3401 (7)0.0961 (15)0.389 (5)
H28'0.75201.46490.33570.115*0.389 (5)
C29'0.8647 (7)1.4011 (6)0.4266 (6)0.0780 (10)0.389 (5)
C30'0.7393 (14)1.5328 (12)0.5253 (10)0.1372 (18)0.389 (5)
H30C0.76231.58820.55530.165*0.389 (5)
H30D0.72091.55710.45940.165*0.389 (5)
O10.52998 (17)0.80350 (16)0.79301 (16)0.0819 (7)
O20.50213 (17)1.26023 (15)0.64934 (17)0.0810 (6)
O30.22369 (16)0.99186 (17)0.46236 (15)0.0804 (7)
N10.8768 (4)0.3362 (4)1.0342 (3)0.1399 (15)
N20.8791 (3)0.4321 (4)1.0098 (3)0.1267 (13)
N30.8385 (2)0.4531 (2)0.9210 (3)0.0888 (9)
N7−0.1788 (3)0.9250 (3)0.0660 (2)0.0910 (9)
N8−0.1573 (2)0.9894 (2)0.1239 (2)0.0851 (8)
N9−0.1164 (2)0.9398 (2)0.20454 (19)0.0675 (7)
C20.8185 (5)0.1936 (4)0.9601 (5)0.140 (2)
H20.83920.14311.00730.168*
C30.7706 (5)0.1785 (5)0.8811 (7)0.172 (4)
H30.75570.11330.87510.207*
C40.7413 (4)0.2490 (5)0.8086 (5)0.145 (2)
H40.70800.23030.75660.174*
C50.7601 (3)0.3466 (3)0.8110 (3)0.1000 (12)
H50.74190.39560.76140.120*
C60.8075 (3)0.3680 (3)0.8913 (3)0.0755 (9)
C70.8255 (3)0.5545 (2)0.8760 (3)0.1036 (13)
H7A0.84350.55450.80350.124*
H7B0.87990.59340.89760.124*
C80.7072 (3)0.6044 (2)0.9025 (3)0.0732 (9)
C90.6679 (3)0.6814 (2)0.8388 (2)0.0693 (8)
H90.71350.70140.77890.083*
C100.5610 (3)0.7291 (2)0.8634 (2)0.0659 (8)
C110.4925 (3)0.7001 (2)0.9517 (2)0.0761 (9)
H110.42000.73130.96770.091*
C120.5323 (3)0.6247 (3)1.0157 (3)0.0876 (11)
H120.48700.60571.07610.105*
C130.6384 (3)0.5767 (3)0.9918 (3)0.0880 (11)
H130.66400.52541.03590.106*
C140.4173 (3)0.8535 (2)0.8129 (2)0.0791 (10)
H14A0.40530.87820.87870.095*
H14B0.36020.80720.81170.095*
C150.4073 (2)0.9381 (2)0.7340 (2)0.0626 (8)
C160.3786 (2)0.9206 (2)0.6416 (3)0.0638 (8)
C170.3626 (2)1.0009 (2)0.5703 (2)0.0610 (8)
C180.3663 (2)1.0990 (2)0.5952 (2)0.0627 (8)
C190.3975 (2)1.1159 (2)0.6862 (2)0.0602 (8)
C200.4227 (2)1.0347 (2)0.7532 (2)0.0618 (8)
C210.4674 (3)1.0522 (3)0.8487 (3)0.0912 (11)
H21A0.40451.06770.89990.137*
H21B0.51541.10670.83490.137*
H21C0.51030.99300.87140.137*
C220.3609 (3)0.8167 (2)0.6193 (3)0.0963 (11)
H22A0.37500.77020.67530.145*0.50
H22B0.41250.79980.56040.145*0.50
H22C0.28400.81410.60790.145*0.50
H22D0.33940.81920.55380.145*0.50
H22E0.30190.78960.66870.145*0.50
H22F0.43030.77520.62110.145*0.50
C230.3347 (3)1.1869 (3)0.5227 (3)0.0932 (11)
H23A0.31521.16280.46400.140*0.50
H23B0.39811.22740.50350.140*0.50
H23C0.27061.22620.55480.140*0.50
H23D0.34071.24810.55090.140*0.50
H23E0.25791.18350.51130.140*0.50
H23F0.38531.18470.46010.140*0.50
C310.6374 (3)1.4917 (3)0.5896 (3)0.0865 (10)
C320.5693 (4)1.5536 (3)0.6508 (3)0.0880 (11)
H320.58621.61940.65050.106*
C330.4763 (3)1.5194 (3)0.7124 (3)0.0913 (11)
H330.43041.56210.75410.110*
C340.4491 (3)1.4217 (3)0.7139 (3)0.0795 (9)
H340.38521.39910.75600.095*
C350.5171 (3)1.3589 (2)0.6528 (2)0.0692 (8)
C360.6102 (3)1.3938 (3)0.5901 (3)0.0850 (10)
H360.65551.35160.54750.102*
C370.4026 (3)1.2207 (2)0.7102 (3)0.0768 (9)
H37A0.33471.26080.69580.092*
H37B0.40741.22170.78090.092*
C38−0.1114 (2)0.8400 (3)0.1982 (2)0.0667 (8)
C39−0.0778 (3)0.7585 (3)0.2608 (3)0.0853 (10)
H39−0.05060.76540.32000.102*
C40−0.0876 (3)0.6666 (3)0.2290 (4)0.1050 (13)
H40−0.06560.60920.26750.126*
C41−0.1294 (4)0.6577 (4)0.1413 (4)0.1147 (15)
H41−0.13520.59420.12320.138*
C42−0.1626 (4)0.7386 (4)0.0797 (3)0.1080 (13)
H42−0.19080.73120.02110.130*
C43−0.1521 (3)0.8316 (3)0.1091 (3)0.0754 (9)
C44−0.0932 (2)0.9947 (3)0.2840 (2)0.0778 (9)
H44A−0.12200.95990.34820.093*
H44B−0.13451.05980.27970.093*
C450.0306 (2)1.0086 (2)0.2814 (2)0.0619 (8)
C460.0954 (3)1.0492 (2)0.1951 (2)0.0717 (9)
H460.06441.06350.13610.086*
C470.2056 (3)1.0681 (2)0.1973 (2)0.0779 (9)
H470.24921.09470.13900.094*
C480.2531 (3)1.0488 (2)0.2836 (2)0.0716 (9)
H480.32801.06260.28390.086*
C490.1888 (2)1.0089 (2)0.3698 (2)0.0618 (8)
C500.0784 (2)0.9872 (2)0.3678 (2)0.0641 (8)
H500.03600.95780.42530.077*
C540.3440 (2)0.9854 (3)0.4660 (2)0.0791 (10)
H54A0.38011.03570.41810.095*
H54B0.37790.92040.44840.095*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N60.098 (3)0.083 (4)0.089 (3)−0.033 (2)−0.024 (2)0.011 (2)
N40.123 (4)0.130 (5)0.124 (5)−0.022 (4)−0.034 (4)0.015 (4)
N50.128 (5)0.137 (6)0.102 (3)−0.037 (4)−0.031 (3)0.009 (3)
C240.089 (3)0.086 (3)0.102 (4)−0.014 (3)−0.011 (3)0.007 (3)
C250.103 (4)0.089 (3)0.140 (6)0.004 (3)0.002 (4)−0.002 (4)
C260.121 (5)0.087 (4)0.159 (6)−0.015 (4)0.003 (4)−0.012 (4)
C270.121 (6)0.100 (5)0.115 (4)−0.034 (4)−0.003 (4)−0.015 (3)
C280.094 (5)0.086 (4)0.111 (3)−0.019 (3)−0.018 (3)−0.006 (3)
C290.084 (2)0.070 (2)0.084 (2)−0.0271 (19)−0.020 (2)0.0054 (19)
C300.142 (4)0.069 (3)0.184 (5)−0.019 (3)0.037 (4)−0.024 (3)
C10.088 (3)0.082 (3)0.111 (3)0.019 (2)−0.007 (2)0.011 (3)
N6'0.098 (3)0.083 (4)0.089 (3)−0.033 (2)−0.024 (2)0.011 (2)
N4'0.123 (4)0.130 (5)0.124 (5)−0.022 (4)−0.034 (4)0.015 (4)
N5'0.128 (5)0.137 (6)0.102 (3)−0.037 (4)−0.031 (3)0.009 (3)
C24'0.089 (3)0.086 (3)0.102 (4)−0.014 (3)−0.011 (3)0.007 (3)
C25'0.103 (4)0.089 (3)0.140 (6)0.004 (3)0.002 (4)−0.002 (4)
C26'0.121 (5)0.087 (4)0.159 (6)−0.015 (4)0.003 (4)−0.012 (4)
C27'0.121 (6)0.100 (5)0.115 (4)−0.034 (4)−0.003 (4)−0.015 (3)
C28'0.094 (5)0.086 (4)0.111 (3)−0.019 (3)−0.018 (3)−0.006 (3)
C29'0.084 (2)0.070 (2)0.084 (2)−0.0271 (19)−0.020 (2)0.0054 (19)
C30'0.142 (4)0.069 (3)0.184 (5)−0.019 (3)0.037 (4)−0.024 (3)
O10.0603 (14)0.0778 (15)0.0961 (16)0.0050 (11)0.0009 (12)0.0168 (13)
O20.0683 (14)0.0627 (15)0.1113 (17)−0.0157 (11)0.0020 (13)−0.0201 (12)
O30.0506 (13)0.1262 (19)0.0672 (14)−0.0247 (12)−0.0066 (11)−0.0100 (12)
N10.151 (4)0.135 (4)0.128 (3)0.040 (3)−0.043 (3)0.005 (3)
N20.128 (3)0.123 (3)0.140 (3)0.017 (3)−0.058 (3)−0.030 (3)
N30.083 (2)0.067 (2)0.116 (3)0.0078 (15)−0.0247 (19)−0.0026 (18)
N70.096 (2)0.106 (3)0.075 (2)−0.0250 (19)−0.0233 (17)0.0031 (19)
N80.078 (2)0.091 (2)0.087 (2)−0.0187 (16)−0.0211 (17)0.0105 (18)
N90.0588 (16)0.079 (2)0.0680 (17)−0.0132 (13)−0.0170 (13)−0.0058 (15)
C20.091 (4)0.085 (4)0.208 (6)0.023 (3)0.026 (4)0.052 (4)
C30.087 (4)0.075 (4)0.334 (12)0.017 (3)0.019 (5)−0.021 (6)
C40.096 (4)0.127 (5)0.224 (7)−0.001 (3)−0.015 (4)−0.098 (5)
C50.083 (3)0.104 (3)0.116 (3)0.000 (2)−0.016 (2)−0.028 (3)
C60.066 (2)0.058 (2)0.096 (3)0.0031 (17)−0.004 (2)0.002 (2)
C70.077 (3)0.060 (2)0.166 (4)−0.0003 (18)−0.009 (2)0.003 (2)
C80.063 (2)0.0493 (19)0.106 (3)−0.0070 (16)−0.011 (2)−0.0034 (18)
C90.060 (2)0.0561 (19)0.089 (2)−0.0108 (16)−0.0023 (17)−0.0028 (17)
C100.061 (2)0.0575 (19)0.077 (2)−0.0105 (16)−0.0081 (18)0.0016 (17)
C110.061 (2)0.073 (2)0.086 (2)0.0013 (17)0.0001 (19)0.0042 (19)
C120.074 (2)0.088 (3)0.091 (3)−0.003 (2)0.000 (2)0.018 (2)
C130.081 (3)0.079 (2)0.099 (3)−0.007 (2)−0.017 (2)0.018 (2)
C140.059 (2)0.079 (2)0.089 (2)0.0016 (17)0.0027 (17)0.0127 (19)
C150.0456 (17)0.065 (2)0.073 (2)−0.0032 (14)−0.0016 (15)0.0032 (17)
C160.0449 (17)0.063 (2)0.083 (2)−0.0096 (14)−0.0028 (16)−0.0085 (18)
C170.0380 (16)0.080 (2)0.066 (2)−0.0111 (14)−0.0068 (14)−0.0110 (18)
C180.0421 (17)0.068 (2)0.075 (2)−0.0090 (14)−0.0055 (15)0.0083 (17)
C190.0480 (17)0.060 (2)0.073 (2)−0.0074 (14)−0.0072 (15)−0.0085 (17)
C200.0448 (17)0.077 (2)0.063 (2)−0.0041 (15)−0.0049 (14)−0.0082 (17)
C210.073 (2)0.117 (3)0.088 (3)−0.002 (2)−0.021 (2)−0.019 (2)
C220.087 (3)0.073 (2)0.131 (3)−0.0124 (19)−0.011 (2)−0.026 (2)
C230.075 (2)0.093 (3)0.108 (3)−0.0092 (19)−0.024 (2)0.023 (2)
C310.102 (3)0.062 (2)0.095 (3)−0.021 (2)−0.001 (2)−0.009 (2)
C320.106 (3)0.063 (2)0.098 (3)−0.006 (2)−0.021 (2)−0.012 (2)
C330.101 (3)0.072 (3)0.102 (3)0.003 (2)−0.015 (2)−0.020 (2)
C340.079 (2)0.068 (2)0.092 (2)−0.0046 (19)−0.012 (2)−0.0094 (19)
C350.070 (2)0.058 (2)0.084 (2)−0.0053 (17)−0.0175 (18)−0.0135 (18)
C360.083 (3)0.074 (2)0.096 (3)−0.0157 (19)0.006 (2)−0.0192 (19)
C370.061 (2)0.068 (2)0.099 (2)−0.0078 (16)−0.0021 (18)−0.0105 (18)
C380.0533 (19)0.073 (2)0.074 (2)−0.0151 (16)−0.0047 (16)−0.0031 (18)
C390.064 (2)0.098 (3)0.092 (3)−0.005 (2)−0.0127 (19)0.004 (2)
C400.081 (3)0.084 (3)0.146 (4)−0.002 (2)−0.012 (3)−0.005 (3)
C410.096 (3)0.094 (4)0.156 (5)−0.021 (3)0.000 (3)−0.042 (3)
C420.105 (3)0.120 (4)0.109 (3)−0.030 (3)−0.012 (3)−0.042 (3)
C430.071 (2)0.090 (3)0.068 (2)−0.0172 (19)−0.0101 (18)−0.012 (2)
C440.053 (2)0.101 (3)0.085 (2)−0.0101 (17)−0.0092 (17)−0.032 (2)
C450.0502 (18)0.069 (2)0.069 (2)−0.0087 (15)−0.0041 (16)−0.0224 (16)
C460.061 (2)0.085 (2)0.070 (2)−0.0075 (17)−0.0101 (17)−0.0101 (17)
C470.064 (2)0.100 (3)0.069 (2)−0.0247 (18)−0.0005 (18)−0.0050 (18)
C480.0545 (19)0.094 (2)0.068 (2)−0.0223 (17)−0.0070 (17)−0.0080 (18)
C490.0497 (18)0.077 (2)0.060 (2)−0.0137 (15)−0.0023 (15)−0.0155 (16)
C500.0510 (18)0.078 (2)0.064 (2)−0.0156 (15)0.0026 (15)−0.0175 (16)
C540.049 (2)0.114 (3)0.076 (2)−0.0111 (17)−0.0075 (16)−0.0170 (19)

Geometric parameters (Å, °)

N6—N51.3401C11—H110.9300
N6—C291.3481C12—C131.376 (4)
N6—C301.3851C12—H120.9300
N4—N51.2782C13—H130.9300
N4—C241.3871C14—C151.492 (4)
C24—C291.4007C14—H14A0.9700
C24—C251.4014C14—H14B0.9700
C25—C261.3775C15—C201.392 (4)
C25—H250.9300C15—C161.399 (4)
C26—C271.3855C16—C171.396 (4)
C26—H260.9300C16—C221.508 (4)
C27—C281.3936C17—C181.410 (4)
C27—H270.9300C17—C541.505 (4)
C28—C291.3972C18—C191.391 (4)
C28—H280.9300C18—C231.521 (4)
C30—C311.513 (13)C19—C201.392 (4)
C30—H30A0.9700C19—C371.497 (4)
C30—H30B0.9700C20—C211.526 (4)
C1—N11.347 (5)C21—H21A0.9600
C1—C61.367 (5)C21—H21B0.9600
C1—C21.407 (7)C21—H21C0.9600
N6'—N5'1.3420C22—H22A0.9600
N6'—C29'1.3500C22—H22B0.9600
N6'—C30'1.6672C22—H22C0.9600
N4'—N5'1.2800C22—H22D0.9600
N4'—C24'1.3891C22—H22E0.9600
C24'—C29'1.4027C22—H22F0.9600
C24'—C25'1.4034C23—H23A0.9600
C25'—C26'1.3795C23—H23B0.9600
C25'—H25'0.9300C23—H23C0.9600
C26'—C27'1.3875C23—H23D0.9600
C26'—H26'0.9300C23—H23E0.9600
C27'—C28'1.3956C23—H23F0.9600
C27'—H27'0.9300C31—C321.362 (5)
C28'—C29'1.3992C31—C361.390 (4)
C28'—H28'0.9300C32—C331.363 (5)
C30'—C311.49 (2)C32—H320.9300
C30'—H30C0.9700C33—C341.386 (4)
C30'—H30D0.9700C33—H330.9300
O1—C101.380 (3)C34—C351.368 (4)
O1—C141.447 (3)C34—H340.9300
O2—C351.369 (3)C35—C361.373 (4)
O2—C371.443 (3)C36—H360.9300
O3—C491.375 (3)C37—H37A0.9700
O3—C541.441 (3)C37—H37B0.9700
N1—N21.306 (5)C38—C391.389 (4)
N2—N31.363 (4)C38—C431.392 (4)
N3—C61.360 (4)C39—C401.379 (5)
N3—C71.446 (4)C39—H390.9300
N7—N81.301 (4)C40—C411.382 (6)
N7—C431.367 (4)C40—H400.9300
N8—N91.358 (3)C41—C421.374 (6)
N9—C381.356 (4)C41—H410.9300
N9—C441.447 (4)C42—C431.381 (5)
C2—C31.335 (8)C42—H420.9300
C2—H20.9300C44—C451.502 (4)
C3—C41.360 (8)C44—H44A0.9700
C3—H30.9300C44—H44B0.9700
C4—C51.364 (6)C45—C501.377 (4)
C4—H40.9300C45—C461.384 (4)
C5—C61.373 (5)C46—C471.369 (4)
C5—H50.9300C46—H460.9300
C7—C81.514 (4)C47—C481.372 (4)
C7—H7A0.9700C47—H470.9300
C7—H7B0.9700C48—C491.377 (4)
C8—C91.379 (4)C48—H480.9300
C8—C131.385 (4)C49—C501.381 (4)
C9—C101.383 (4)C50—H500.9300
C9—H90.9300C54—H54A0.9700
C10—C111.377 (4)C54—H54B0.9700
C11—C121.369 (4)
N5—N6—C29109.9C17—C18—C23119.8 (3)
N5—N6—C30114.4C18—C19—C20119.2 (3)
C29—N6—C30135.5C18—C19—C37119.4 (3)
N5—N4—C24112.7C20—C19—C37121.4 (3)
N4—N5—N6107.3C19—C20—C15120.7 (3)
N4—C24—C29102.9C19—C20—C21119.4 (3)
N4—C24—C25134.3C15—C20—C21119.9 (3)
C29—C24—C25122.8C20—C21—H21A109.5
C26—C25—C24114.8C20—C21—H21B109.5
C26—C25—H25122.6H21A—C21—H21B109.5
C24—C25—H25122.6C20—C21—H21C109.5
C25—C26—C27124.1H21A—C21—H21C109.5
C25—C26—H26118.0H21B—C21—H21C109.5
C27—C26—H26118.0C16—C22—H22A109.5
C26—C27—C28120.5C16—C22—H22B109.5
C26—C27—H27119.7H22A—C22—H22B109.5
C28—C27—H27119.7C16—C22—H22C109.5
C27—C28—C29117.3H22A—C22—H22C109.5
C27—C28—H28121.4H22B—C22—H22C109.5
C29—C28—H28121.4C16—C22—H22D109.5
N6—C29—C28132.4H22A—C22—H22D141.1
N6—C29—C24107.2H22B—C22—H22D56.3
C28—C29—C24120.4H22C—C22—H22D56.3
N6—C30—C31112.7 (4)C16—C22—H22E109.5
N6—C30—H30A109.0H22A—C22—H22E56.3
C31—C30—H30A109.0H22B—C22—H22E141.1
N6—C30—H30B109.0H22C—C22—H22E56.3
C31—C30—H30B109.0H22D—C22—H22E109.5
H30A—C30—H30B107.8C16—C22—H22F109.5
N1—C1—C6109.3 (4)H22A—C22—H22F56.3
N1—C1—C2127.4 (5)H22B—C22—H22F56.3
C6—C1—C2123.4 (5)H22C—C22—H22F141.1
N5'—N6'—C29'109.9H22D—C22—H22F109.5
N5'—N6'—C30'134.1H22E—C22—H22F109.5
C29'—N6'—C30'115.9C18—C23—H23A109.5
N5'—N4'—C24'112.7C18—C23—H23B109.5
N4'—N5'—N6'107.3H23A—C23—H23B109.5
N4'—C24'—C29'102.9C18—C23—H23C109.5
N4'—C24'—C25'134.3H23A—C23—H23C109.5
C29'—C24'—C25'122.8H23B—C23—H23C109.5
C26'—C25'—C24'114.8C18—C23—H23D109.5
C26'—C25'—H25'122.6H23A—C23—H23D141.1
C24'—C25'—H25'122.6H23B—C23—H23D56.3
C25'—C26'—C27'124.1H23C—C23—H23D56.3
C25'—C26'—H26'118.0C18—C23—H23E109.5
C27'—C26'—H26'118.0H23A—C23—H23E56.3
C26'—C27'—C28'120.5H23B—C23—H23E141.1
C26'—C27'—H27'119.7H23C—C23—H23E56.3
C28'—C27'—H27'119.7H23D—C23—H23E109.5
C27'—C28'—C29'117.3C18—C23—H23F109.5
C27'—C28'—H28'121.3H23A—C23—H23F56.3
C29'—C28'—H28'121.3H23B—C23—H23F56.3
N6'—C29'—C28'132.4H23C—C23—H23F141.1
N6'—C29'—C24'107.2H23D—C23—H23F109.5
C28'—C29'—C24'120.4H23E—C23—H23F109.5
C31—C30'—N6'109.4 (7)C32—C31—C36119.3 (3)
C31—C30'—H30C109.8C32—C31—C30'117.7 (5)
N6'—C30'—H30C109.8C36—C31—C30'123.0 (5)
C31—C30'—H30D109.8C32—C31—C30118.0 (4)
N6'—C30'—H30D109.8C36—C31—C30122.5 (4)
H30C—C30'—H30D108.2C31—C32—C33120.1 (4)
C10—O1—C14117.7 (2)C31—C32—H32120.0
C35—O2—C37117.5 (2)C33—C32—H32120.0
C49—O3—C54118.1 (2)C32—C33—C34121.0 (4)
N2—N1—C1108.9 (4)C32—C33—H33119.5
N1—N2—N3107.8 (4)C34—C33—H33119.5
C6—N3—N2109.4 (3)C35—C34—C33119.4 (3)
C6—N3—C7129.3 (4)C35—C34—H34120.3
N2—N3—C7121.2 (4)C33—C34—H34120.3
N8—N7—C43108.0 (3)C34—C35—O2125.3 (3)
N7—N8—N9109.0 (3)C34—C35—C36119.6 (3)
C38—N9—N8110.1 (3)O2—C35—C36115.1 (3)
C38—N9—C44130.1 (3)C35—C36—C31120.7 (3)
N8—N9—C44119.7 (3)C35—C36—H36119.6
C3—C2—C1111.9 (6)C31—C36—H36119.6
C3—C2—H2124.0O2—C37—C19108.0 (2)
C1—C2—H2124.0O2—C37—H37A110.1
C2—C3—C4126.6 (7)C19—C37—H37A110.1
C2—C3—H3116.7O2—C37—H37B110.1
C4—C3—H3116.7C19—C37—H37B110.1
C3—C4—C5120.8 (6)H37A—C37—H37B108.4
C3—C4—H4119.6N9—C38—C39132.6 (3)
C5—C4—H4119.6N9—C38—C43104.0 (3)
C4—C5—C6115.8 (5)C39—C38—C43123.4 (4)
C4—C5—H5122.1C40—C39—C38115.3 (4)
C6—C5—H5122.1C40—C39—H39122.3
N3—C6—C1104.6 (4)C38—C39—H39122.3
N3—C6—C5134.0 (4)C39—C40—C41121.5 (4)
C1—C6—C5121.4 (4)C39—C40—H40119.2
N3—C7—C8113.7 (3)C41—C40—H40119.2
N3—C7—H7A108.8C42—C41—C40122.9 (4)
C8—C7—H7A108.8C42—C41—H41118.6
N3—C7—H7B108.8C40—C41—H41118.6
C8—C7—H7B108.8C41—C42—C43116.7 (4)
H7A—C7—H7B107.7C41—C42—H42121.6
C9—C8—C13118.8 (3)C43—C42—H42121.6
C9—C8—C7119.9 (3)N7—C43—C42130.9 (4)
C13—C8—C7121.2 (3)N7—C43—C38109.0 (3)
C8—C9—C10120.4 (3)C42—C43—C38120.1 (4)
C8—C9—H9119.8N9—C44—C45114.2 (2)
C10—C9—H9119.8N9—C44—H44A108.7
C11—C10—O1124.3 (3)C45—C44—H44A108.7
C11—C10—C9120.5 (3)N9—C44—H44B108.7
O1—C10—C9115.2 (3)C45—C44—H44B108.7
C12—C11—C10119.1 (3)H44A—C44—H44B107.6
C12—C11—H11120.4C50—C45—C46119.3 (3)
C10—C11—H11120.4C50—C45—C44119.6 (3)
C11—C12—C13120.9 (3)C46—C45—C44120.9 (3)
C11—C12—H12119.6C47—C46—C45119.5 (3)
C13—C12—H12119.6C47—C46—H46120.3
C12—C13—C8120.3 (3)C45—C46—H46120.3
C12—C13—H13119.8C46—C47—C48121.5 (3)
C8—C13—H13119.8C46—C47—H47119.2
O1—C14—C15108.5 (2)C48—C47—H47119.2
O1—C14—H14A110.0C47—C48—C49119.2 (3)
C15—C14—H14A110.0C47—C48—H48120.4
O1—C14—H14B110.0C49—C48—H48120.4
C15—C14—H14B110.0O3—C49—C48125.0 (3)
H14A—C14—H14B108.4O3—C49—C50115.2 (3)
C20—C15—C16120.1 (3)C48—C49—C50119.7 (3)
C20—C15—C14120.2 (3)C45—C50—C49120.7 (3)
C16—C15—C14119.7 (3)C45—C50—H50119.7
C17—C16—C15119.4 (3)C49—C50—H50119.7
C17—C16—C22119.5 (3)O3—C54—C17109.3 (2)
C15—C16—C22121.0 (3)O3—C54—H54A109.8
C16—C17—C18119.7 (3)C17—C54—H54A109.8
C16—C17—C54121.5 (3)O3—C54—H54B109.8
C18—C17—C54118.8 (3)C17—C54—H54B109.8
C19—C18—C17120.4 (3)H54A—C54—H54B108.3
C19—C18—C23119.8 (3)
C24—N4—N5—N60.8O1—C14—C15—C1683.8 (3)
C29—N6—N5—N4−0.7C20—C15—C16—C17−1.6 (4)
C30—N6—N5—N4175.6C14—C15—C16—C17176.2 (2)
N5—N4—C24—C29−0.5C20—C15—C16—C22−179.7 (3)
N5—N4—C24—C25178.1C14—C15—C16—C22−1.9 (4)
N4—C24—C25—C26−179.8C15—C16—C17—C18−5.3 (4)
C29—C24—C25—C26−1.4C22—C16—C17—C18172.8 (3)
C24—C25—C26—C273.9C15—C16—C17—C54173.4 (2)
C25—C26—C27—C28−3.9C22—C16—C17—C54−8.5 (4)
C26—C27—C28—C291.0C16—C17—C18—C196.8 (4)
N5—N6—C29—C28−176.8C54—C17—C18—C19−171.9 (2)
C30—N6—C29—C287.9C16—C17—C18—C23−172.5 (3)
N5—N6—C29—C240.4C54—C17—C18—C238.9 (4)
C30—N6—C29—C24−174.8C17—C18—C19—C20−1.3 (4)
C27—C28—C29—N6178.3C23—C18—C19—C20177.9 (3)
C27—C28—C29—C241.4C17—C18—C19—C37179.0 (2)
N4—C24—C29—N60.1C23—C18—C19—C37−1.7 (4)
C25—C24—C29—N6−178.8C18—C19—C20—C15−5.7 (4)
N4—C24—C29—C28177.7C37—C19—C20—C15174.0 (3)
C25—C24—C29—C28−1.2C18—C19—C20—C21174.4 (3)
N5—N6—C30—C31−75.3 (4)C37—C19—C20—C21−5.9 (4)
C29—N6—C30—C3199.7 (4)C16—C15—C20—C197.2 (4)
C24'—N4'—N5'—N6'0.8C14—C15—C20—C19−170.6 (3)
C29'—N6'—N5'—N4'−0.7C16—C15—C20—C21−172.9 (3)
C30'—N6'—N5'—N4'−177.7C14—C15—C20—C219.3 (4)
N5'—N4'—C24'—C29'−0.5N6'—C30'—C31—C32145.2 (3)
N5'—N4'—C24'—C25'178.1N6'—C30'—C31—C36−34.2 (7)
N4'—C24'—C25'—C26'−179.8N6'—C30'—C31—C30−120 (8)
C29'—C24'—C25'—C26'−1.4N6—C30—C31—C32145.2 (3)
C24'—C25'—C26'—C27'4.0N6—C30—C31—C36−39.5 (5)
C25'—C26'—C27'—C28'−3.9N6—C30—C31—C30'58 (7)
C26'—C27'—C28'—C29'1.0C36—C31—C32—C330.7 (6)
N5'—N6'—C29'—C28'−176.8C30'—C31—C32—C33−178.8 (6)
C30'—N6'—C29'—C28'0.8C30—C31—C32—C33176.1 (4)
N5'—N6'—C29'—C24'0.4C31—C32—C33—C34−0.2 (6)
C30'—N6'—C29'—C24'178.0C32—C33—C34—C350.3 (5)
C27'—C28'—C29'—N6'178.3C33—C34—C35—O2177.7 (3)
C27'—C28'—C29'—C24'1.4C33—C34—C35—C36−0.9 (5)
N4'—C24'—C29'—N6'0.1C37—O2—C35—C344.1 (4)
C25'—C24'—C29'—N6'−178.8C37—O2—C35—C36−177.1 (3)
N4'—C24'—C29'—C28'177.7C34—C35—C36—C311.4 (5)
C25'—C24'—C29'—C28'−1.2O2—C35—C36—C31−177.4 (3)
N5'—N6'—C30'—C31−80.7 (7)C32—C31—C36—C35−1.3 (5)
C29'—N6'—C30'—C31102.5 (7)C30'—C31—C36—C35178.1 (6)
C6—C1—N1—N2−0.3 (5)C30—C31—C36—C35−176.5 (4)
C2—C1—N1—N2179.0 (4)C35—O2—C37—C19174.0 (3)
C1—N1—N2—N3−0.8 (5)C18—C19—C37—O2−73.4 (3)
N1—N2—N3—C61.6 (4)C20—C19—C37—O2107.0 (3)
N1—N2—N3—C7177.2 (3)N8—N9—C38—C39−179.1 (3)
C43—N7—N8—N90.1 (4)C44—N9—C38—C39−3.9 (5)
N7—N8—N9—C380.1 (3)N8—N9—C38—C43−0.3 (3)
N7—N8—N9—C44−175.7 (3)C44—N9—C38—C43175.0 (3)
N1—C1—C2—C3178.0 (5)N9—C38—C39—C40178.5 (3)
C6—C1—C2—C3−2.8 (7)C43—C38—C39—C40−0.2 (5)
C1—C2—C3—C41.8 (9)C38—C39—C40—C41−0.7 (5)
C2—C3—C4—C50.1 (10)C39—C40—C41—C420.7 (6)
C3—C4—C5—C6−1.2 (7)C40—C41—C42—C430.3 (6)
N2—N3—C6—C1−1.7 (4)N8—N7—C43—C42177.7 (4)
C7—N3—C6—C1−176.8 (3)N8—N7—C43—C38−0.3 (4)
N2—N3—C6—C5178.2 (4)C41—C42—C43—N7−178.9 (4)
C7—N3—C6—C53.1 (6)C41—C42—C43—C38−1.1 (5)
N1—C1—C6—N31.2 (4)N9—C38—C43—N70.4 (3)
C2—C1—C6—N3−178.0 (4)C39—C38—C43—N7179.3 (3)
N1—C1—C6—C5−178.7 (3)N9—C38—C43—C42−177.9 (3)
C2—C1—C6—C52.0 (6)C39—C38—C43—C421.1 (5)
C4—C5—C6—N3−179.8 (4)C38—N9—C44—C4582.8 (4)
C4—C5—C6—C10.1 (5)N8—N9—C44—C45−102.3 (3)
C6—N3—C7—C880.2 (5)N9—C44—C45—C50−131.3 (3)
N2—N3—C7—C8−94.4 (4)N9—C44—C45—C4653.2 (4)
N3—C7—C8—C9−154.6 (3)C50—C45—C46—C47−0.5 (5)
N3—C7—C8—C1327.8 (5)C44—C45—C46—C47174.9 (3)
C13—C8—C9—C10−0.7 (5)C45—C46—C47—C48−0.8 (5)
C7—C8—C9—C10−178.4 (3)C46—C47—C48—C490.5 (5)
C14—O1—C10—C11−0.8 (4)C54—O3—C49—C48−20.2 (4)
C14—O1—C10—C9177.7 (3)C54—O3—C49—C50162.8 (3)
C8—C9—C10—C11−0.2 (5)C47—C48—C49—O3−175.7 (3)
C8—C9—C10—O1−178.7 (3)C47—C48—C49—C501.1 (5)
O1—C10—C11—C12179.6 (3)C46—C45—C50—C492.1 (4)
C9—C10—C11—C121.2 (5)C44—C45—C50—C49−173.4 (3)
C10—C11—C12—C13−1.3 (5)O3—C49—C50—C45174.7 (2)
C11—C12—C13—C80.4 (6)C48—C49—C50—C45−2.4 (4)
C9—C8—C13—C120.6 (5)C49—O3—C54—C17161.4 (3)
C7—C8—C13—C12178.3 (3)C16—C17—C54—O394.9 (3)
C10—O1—C14—C15173.4 (3)C18—C17—C54—O3−86.4 (3)
O1—C14—C15—C20−98.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···N8i0.932.483.376 (7)163.
C27—H27···N1ii0.932.543.453 (7)166.

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2438).

References

  • Androsov, D. A. & Neckers, D. C. (2007). J. Org. Chem.72, 1148–1152. [PubMed]
  • Blackman, A. G. (2005). Polyhedron, 24, 1–39.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cai, Y.-P., Li, G.-B., He, G.-P., Su, C.-Y., Xu, A.-W. & Zhang, C. (2004). Acta Cryst. E60, o2062–o2064.
  • Fan, J., Zhu, H. F., Okamura, T., Sun, W. S., Tang, W. X. & Ueyama, N. (2003). Chem. Eur. J.9, 4724–4731. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Fujita, M., Nagao, S. & Ogura, K. (1995). J. Am. Chem. Soc.117, 1649–1650.
  • Gong, J. F., zhang, Y. H., Song, M. P. & Xu, C. (2007). Organometallics, 26, 6487–6492.
  • Li, X. P., Zhang, J. Y., Pan, M., Zheng, S. R., Liu, Y. & Su, C. Y. (2007). Inorg. Chem 46, 4617–4625. [PubMed]
  • Made, A. W. van der & van der Made, R. H. (1993). J. Org. Chem.58, 1262–1263.
  • Selvanayagam, S., Velmurugan, D., Ravikumar, K., Dhanasekaran, M. & Rajakumar, P. (2004). Acta Cryst. E60, o2165–o2167.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zeng, F. & Zimmerman, S. C. (1997). Chem. Rev.97, 1681–1712. [PubMed]
  • Zhao, W., Song, Y., Okamura, T., Fan, J., Sun, W. Y. & Ueyama, N. (2005). Inorg. Chem.44, 3330–3336. [PubMed]

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