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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 4| April 2010| Pages o729-o730

4,4′,4′′-(Methane­triyl)tri­phenyl tris­­(2,2,5,5-tetra­methyl-1-oxyl-3-pyrroline-3-carboxyl­ate) benzene tris­­olvate

aInstitut für Physikalische und Theoretische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany, and bInstitut für Organische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
*Correspondence e-mail: bats@chemie.uni-frankfurt.de

(Received 17 February 2010; accepted 25 February 2010; online 3 March 2010)

In the asymmetric unit of the title compound, C46H52N3O9·3C6H6, two of the benzene solvent mol­ecules are located in general positions and two are disposed about inversion centers. One of the benzene mol­ecules on an inversion center was grossly disordered and was excluded using the SQUEEZE subroutine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148–155]. In addition, one of the 2,2,5,5-tetra­methyl-1-oxyl-3-pyrrolin-3-ylcarbonyl groups is disordered over two orientations with refined occupancies of 0.506 (2) and 0.494 (2). The 1-oxyl-3-pyrroline-3-carboxyl­ate groups are essentially planar, with mean deviations from the planes of 0.026 (2), 0.012 (2), 0.034 (4) and 0.011 (4) Å. In the crystal structure, mol­ecules are connected by five weak inter­molecular C—H⋯O and four weak inter­molecular C—H⋯π(benzene) inter­actions.

Related literature

For the preparation of the title compound see: Godt et al. (2000[Godt, A., Franzen, C., Veit, S., Enkelmann, V., Pannier, M. & Jeschke, G. (2000). J. Org. Chem. 65, 7575-7582.]). For a related structure, see: Margraf et al. (2009[Margraf, D., Schuetz, D., Prisner, T. F. & Bats, J. W. (2009). Acta Cryst. E65, o1784.]). For the treatment of the disordered solvent, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C46H52N3O9·3C6H6

  • Mr = 1025.23

  • Triclinic, [P \overline 1]

  • a = 10.0810 (13) Å

  • b = 11.7372 (16) Å

  • c = 26.241 (4) Å

  • α = 98.324 (10)°

  • β = 92.765 (11)°

  • γ = 105.308 (10)°

  • V = 2951.1 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 164 K

  • 0.70 × 0.20 × 0.20 mm

Data collection
  • Siemens SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.878, Tmax = 0.985

  • 43135 measured reflections

  • 12901 independent reflections

  • 6172 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 0.194

  • S = 1.04

  • 12901 reflections

  • 667 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, and Cg3 are the centroids of the C47–C52, C17–C22 and C56–C61 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1A⋯O6i 1.00 2.49 3.448 (3) 160
C4—H4A⋯O9′ii 0.95 2.44 3.165 (5) 133
C25—H25A⋯O2iii 0.95 2.57 3.358 (4) 141
C37—H37A⋯O6i 0.95 2.57 3.442 (3) 153
C57—H57A⋯O6iv 0.95 2.58 3.514 (8) 168
C10—H10ACg1 0.95 2.84 3.752 (3) 161
C12—H12ACg2iv 0.98 2.94 3.726 (3) 138
C19—H19ACg1v 0.95 2.79 3.725 (3) 169
C34—H34ACg3 0.95 2.78 3.547 (4) 138
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y, -z; (iii) x, y+1, z; (iv) x, y-1, z; (v) x+1, y+1, z.

Data collection: SMART (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound was prepared as a reference compound for pulsed electron-electron double resonance measurements (Godt et al., 2000).

The molecular structure is shown in Fig. 1. The 2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carbonyl group attached to atom O7 is disordered over two orientations with equal occupancies. Short intermolecular contact distances [O8···O8(at 1-x,1-y,-z)=2.371 (5)Å and O8'···O8'(at 1-x,-y,-z)=2.354 (5) Å] show that adjacent groups should occupy alternating orientations along the b-direction, resulting in space group symmetry P 1 with Z'=2. A refinement as an ordered structure in P 1, however, resulted in much higher R-values, showing that the packing must be randomly disordered along at least one other direction.

Each of the 1-oxyl-3-pyrroline groups is approximately planar [mean deviation from plane: 0.026 (2), 0.012 (2), 0.034 (4) and 0.011 (4)Å respectively] and is coplanar with the carbonyloxy group to which it is bonded [torsion angles O1—C8—C9—C10: -0.7 (3)° , O4—C23—C24—C25: 2.4 (4)° , O7—C38—C39—C40: -4.5 (7)° and O7—C38'-C39'-C40': 10.5 (9)° ]. Planarity of this group also has been observed in a related crystal structure (Margraf et al., 2009). The acetoxyphenyl groups are non-planar [torsion angles: C8—O1—C5—C6=-68.2 (3)° , C23—O4—C20—C19=86.6 (3)° , C38—O7—C35—C34=-78.9 (5)° and C38'-O7—C35—C34=67.7 (5)° .

The crystal packing is shown in Fig. 2. The asymmetric unit contains a triphenylmethane-4,4',4"-triyl tris(2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carboxylate) molecule, two benzene solvent molecules in general positions and two benzene solvent molecules positioned about inversion centers. One of the latter groups was found to be seriously disordered and was included in the calculations by using program PLATON/SQUEEZE (Spek, 2009). There are five intermolecular C—H···O contacts with H···O distances between 2.44 and 2.58 Å and four intermolecular C—H···πbenzene contacts with H···Cg distances between 2.78 and 2.94 Å (Table 1, Cg represents the centroid of the benzene ring).

Related literature top

For the preparation of the title compound see: Godt et al. (2000). For a related structure, see: Margraf et al. (2009). For the treatment of the disordered solvent, see: Spek (2009).

Experimental top

The title compound was prepared from tris(4-hydroxyphenyl)methane in analogy to the procedure described by Godt et al. (2000). Single crystals were obtained by recrystallization of the compound from benzene.

Refinement top

The H atoms were positioned geometrically and treated as riding: Cprimary—H=1.00 Å, Cmethyl—H=0.98 Å, Cplanar—H=0.95 Å, Uiso(H)=1.2Ueq(Cnon-methyl) and Uiso(H)=1.5Ueq(Cmethyl). A benzene solvent molecule seriously disordered about the inversion center at (0, 0, 0) was accounted for by using the program PLATON/SQUEEZE (Spek, 2009). The electron density count in this region was found to be 42 electrons, in perfect agreement with the value expected for a benzene molecule and the contribution from the additional benzene molecule was added to the empirical formula. The 2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carbonyl group attached to atom O7 was found to be disordered over two possible orientations. Consequently, atoms in this group were refined as split atoms and treated as isotropic, except for the O atoms which were refined with anisotropic displacement parameters. The occupancy factor refined to 0.494 (2) for atoms, O8, O9, N3 and C38 C46 and to 0.506 (2) for atoms O8', O9', N3' and C38' C46'. A refinement as an ordered structure in space group P 1 converged at wR(F2)=0.295, R[F2>2σ(F2)]=0.107 and showed residual density up to 1.21 e.A-3 in the 2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carbonyl group, which was disordered in space group P 1. Thus an ordered structure can be excluded. Oxygen atom O7 could not be split to meaningful positions within the experimental resolution. As a result, the observed values of the C35-O7-C38 and C35-O7-C38' angles [128.4 (3) and 140.5 (3)° ] are too large.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound shown with 50% probability displacement ellipsoids. The H atoms are drawn as small spheres of arbitrary radius. Symmetry equivalent atoms are related by i: 2-x, 1-y, 1-z. A disorder component is shown with open bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. H atoms have been omitted. Along the b-direction adjacent molecules are shown with alternating orientations of the disordered side-chain.
4,4',4''-(Methanetriyl)triphenyl tris(2,2,5,5-tetramethyl-1-oxyl-3-pyrroline-3-carboxylate) benzene trisolvate top
Crystal data top
C46H52N3O9·3C6H6Z = 2
Mr = 1025.23F(000) = 1094
Triclinic, P1Dx = 1.154 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0810 (13) ÅCell parameters from 204 reflections
b = 11.7372 (16) Åθ = 3–23°
c = 26.241 (4) ŵ = 0.08 mm1
α = 98.324 (10)°T = 164 K
β = 92.765 (11)°Rod, yellow
γ = 105.308 (10)°0.70 × 0.20 × 0.20 mm
V = 2951.1 (7) Å3
Data collection top
Siemens SMART 1K CCD
diffractometer
12901 independent reflections
Radiation source: normal-focus sealed tube6172 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1313
Tmin = 0.878, Tmax = 0.985k = 1415
43135 measured reflectionsl = 3233
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)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.09P)2]
where P = (Fo2 + 2Fc2)/3
12901 reflections(Δ/σ)max = 0.002
667 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C46H52N3O9·3C6H6γ = 105.308 (10)°
Mr = 1025.23V = 2951.1 (7) Å3
Triclinic, P1Z = 2
a = 10.0810 (13) ÅMo Kα radiation
b = 11.7372 (16) ŵ = 0.08 mm1
c = 26.241 (4) ÅT = 164 K
α = 98.324 (10)°0.70 × 0.20 × 0.20 mm
β = 92.765 (11)°
Data collection top
Siemens SMART 1K CCD
diffractometer
12901 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
6172 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.985Rint = 0.054
43135 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.194H-atom parameters constrained
S = 1.04Δρmax = 0.41 e Å3
12901 reflectionsΔρmin = 0.40 e Å3
667 parameters
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.

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) top
xyzUiso*/UeqOcc. (<1)
O10.53115 (18)0.01253 (13)0.36733 (6)0.0452 (4)
O20.72796 (17)0.08878 (15)0.41627 (7)0.0503 (5)
O30.6843 (2)0.28486 (17)0.51844 (8)0.0653 (6)
O40.81097 (19)0.83869 (14)0.30718 (7)0.0582 (5)
O50.8868 (2)0.81827 (17)0.22723 (9)0.0745 (6)
O61.12533 (19)1.29224 (14)0.25223 (7)0.0590 (5)
O70.4972 (2)0.25906 (19)0.03656 (8)0.0798 (7)
O80.5327 (5)0.4303 (3)0.02292 (14)0.0667 (13)0.494 (2)
O90.5887 (5)0.2649 (4)0.17679 (13)0.0756 (15)0.494 (2)
O8'0.5441 (5)0.1012 (3)0.01896 (14)0.0781 (14)0.506 (2)
O9'0.5181 (7)0.1270 (5)0.18702 (15)0.122 (2)0.506 (2)
N10.6415 (2)0.24001 (18)0.48143 (8)0.0458 (5)
N21.0619 (2)1.20024 (17)0.27055 (8)0.0469 (6)
N30.5720 (5)0.2458 (5)0.13101 (17)0.0466 (12)*0.494 (2)
N3'0.5159 (6)0.1762 (6)0.1401 (2)0.0668 (15)*0.506 (2)
C10.4798 (2)0.35575 (19)0.25423 (9)0.0358 (6)
H1A0.38260.35720.25950.043*
C20.5085 (2)0.26105 (19)0.28438 (9)0.0327 (5)
C30.5311 (3)0.1558 (2)0.26070 (9)0.0453 (6)
H3A0.53870.14410.22450.054*
C40.5429 (3)0.0661 (2)0.28895 (9)0.0437 (6)
H4A0.55760.00630.27220.052*
C50.5329 (2)0.08435 (19)0.34088 (9)0.0381 (6)
C60.5110 (3)0.1883 (2)0.36585 (10)0.0483 (7)
H6A0.50290.19960.40200.058*
C70.5011 (3)0.2761 (2)0.33715 (10)0.0452 (7)
H7A0.48870.34910.35430.054*
C80.6331 (3)0.0003 (2)0.40459 (9)0.0367 (6)
C90.6121 (2)0.1091 (2)0.42854 (9)0.0348 (6)
C100.5068 (2)0.2069 (2)0.41613 (9)0.0372 (6)
H10A0.43560.21580.38960.045*
C110.5119 (3)0.3016 (2)0.44818 (10)0.0426 (6)
C120.5255 (3)0.4162 (2)0.41644 (11)0.0627 (8)
H12A0.60380.39740.39550.094*
H12B0.44060.45450.39370.094*
H12C0.54070.47080.43970.094*
C130.3917 (3)0.3261 (3)0.48212 (11)0.0567 (8)
H13A0.38620.25050.50210.085*
H13B0.40660.37980.50580.085*
H13C0.30530.36380.46020.085*
C140.7124 (2)0.1188 (2)0.47093 (9)0.0409 (6)
C150.8546 (3)0.1184 (3)0.45284 (12)0.0599 (8)
H15A0.84360.17760.42140.090*
H15B0.91020.13880.48000.090*
H15C0.90110.03870.44560.090*
C160.7252 (3)0.0275 (3)0.51980 (10)0.0613 (8)
H16A0.63290.02890.53030.092*
H16B0.77170.05260.51300.092*
H16C0.77910.04760.54750.092*
C170.5699 (2)0.4829 (2)0.27361 (9)0.0381 (6)
C180.7073 (2)0.5096 (2)0.29182 (9)0.0398 (6)
H18A0.74670.44640.29670.048*
C190.7888 (3)0.6274 (2)0.30317 (10)0.0444 (6)
H19A0.88330.64500.31550.053*
C200.7306 (3)0.7174 (2)0.29620 (11)0.0516 (7)
C210.5926 (3)0.6943 (2)0.28051 (15)0.0825 (11)
H21A0.55250.75800.27760.099*
C220.5140 (3)0.5773 (2)0.26915 (14)0.0728 (10)
H22A0.41880.56060.25800.087*
C230.8817 (3)0.8800 (2)0.26730 (13)0.0531 (7)
C240.9470 (3)1.0102 (2)0.27938 (11)0.0443 (6)
C250.9442 (3)1.0799 (2)0.32329 (11)0.0492 (7)
H25A0.90211.05080.35220.059*
C261.0145 (3)1.2103 (2)0.32310 (10)0.0470 (7)
C271.1365 (3)1.2618 (3)0.36340 (11)0.0623 (8)
H27A1.20061.21190.35970.093*
H27B1.10391.26360.39800.093*
H27C1.18401.34340.35860.093*
C280.9105 (3)1.2851 (2)0.32690 (13)0.0644 (8)
H28A0.83361.24920.30020.097*
H28B0.95621.36690.32180.097*
H28C0.87541.28700.36110.097*
C291.0226 (3)1.0784 (2)0.24016 (10)0.0535 (7)
C301.1532 (4)1.0425 (2)0.22696 (14)0.0836 (11)
H30A1.20971.04620.25890.125*
H30B1.20591.09740.20580.125*
H30C1.12790.96060.20770.125*
C310.9301 (5)1.0754 (3)0.19274 (13)0.1072 (15)
H31A0.84841.09980.20330.161*
H31B0.90130.99400.17300.161*
H31C0.98051.13060.17110.161*
C320.4854 (3)0.3272 (2)0.19600 (9)0.0384 (6)
C330.6103 (3)0.3336 (2)0.17411 (10)0.0512 (7)
H33A0.69370.35390.19600.061*
C340.6145 (3)0.3109 (2)0.12123 (11)0.0534 (7)
H34A0.70000.31620.10670.064*
C350.4927 (3)0.2805 (2)0.08983 (9)0.0479 (7)
C360.3685 (3)0.2738 (2)0.10991 (10)0.0508 (7)
H36A0.28560.25340.08770.061*
C370.3655 (3)0.2974 (2)0.16310 (10)0.0435 (6)
H37A0.27960.29300.17720.052*
C380.5259 (5)0.3267 (5)0.00924 (18)0.0342 (11)*0.494 (2)
C390.5383 (5)0.2737 (6)0.0439 (2)0.0372 (13)*0.494 (2)
C400.5269 (6)0.1600 (6)0.0584 (3)0.0435 (19)*0.494 (2)
H40A0.51230.10410.03500.052*0.494 (2)
C410.5385 (8)0.1254 (7)0.1142 (3)0.062 (2)*0.494 (2)
C420.6402 (8)0.0620 (7)0.1295 (3)0.088 (2)*0.494 (2)
H42A0.73130.10720.11230.131*0.494 (2)
H42B0.64380.05370.16710.131*0.494 (2)
H42C0.61410.01760.11940.131*0.494 (2)
C430.3930 (7)0.0497 (7)0.1432 (3)0.088 (2)*0.494 (2)
H43A0.40310.02830.18000.132*0.494 (2)
H43B0.32670.09750.13910.132*0.494 (2)
H43C0.35950.02340.12820.132*0.494 (2)
C440.5595 (5)0.3435 (5)0.0885 (2)0.0382 (12)*0.494 (2)
C450.6952 (6)0.4419 (5)0.0809 (2)0.0639 (17)*0.494 (2)
H45A0.77100.40840.07210.096*0.494 (2)
H45B0.69080.50520.05280.096*0.494 (2)
H45C0.71100.47540.11290.096*0.494 (2)
C460.4390 (6)0.3926 (5)0.1013 (2)0.0616 (17)*0.494 (2)
H46A0.35290.32790.10560.092*0.494 (2)
H46B0.45210.42570.13350.092*0.494 (2)
H46C0.43450.45570.07310.092*0.494 (2)
C38'0.5238 (5)0.1855 (5)0.00195 (19)0.0417 (13)*0.506 (2)
C39'0.5230 (6)0.2059 (8)0.0516 (2)0.0424 (16)*0.506 (2)
C40'0.5158 (5)0.3052 (5)0.0676 (2)0.0384 (12)*0.506 (2)
H40B0.51160.37480.04490.046*0.506 (2)
C41'0.5147 (5)0.2980 (5)0.1243 (2)0.0438 (13)*0.506 (2)
C42'0.6415 (7)0.3871 (6)0.1412 (3)0.082 (2)*0.506 (2)
H42D0.72650.37330.12690.123*0.506 (2)
H42E0.63990.46930.12820.123*0.506 (2)
H42F0.63820.37500.17900.123*0.506 (2)
C43'0.3833 (6)0.3192 (5)0.1471 (2)0.0643 (17)*0.506 (2)
H43D0.30280.26290.13660.096*0.506 (2)
H43E0.38100.30680.18490.096*0.506 (2)
H43F0.38140.40140.13430.096*0.506 (2)
C44'0.5244 (8)0.1077 (7)0.0966 (4)0.071 (3)*0.506 (2)
C45'0.6756 (9)0.0850 (9)0.0961 (4)0.119 (3)*0.506 (2)
H45D0.74630.16200.09200.178*0.506 (2)
H45E0.68320.03570.12870.178*0.506 (2)
H45F0.68910.04350.06720.178*0.506 (2)
C46'0.4074 (8)0.0006 (6)0.1012 (3)0.092 (2)*0.506 (2)
H46D0.32080.02230.10020.139*0.506 (2)
H46E0.41720.04320.07230.139*0.506 (2)
H46F0.40650.05290.13390.139*0.506 (2)
C470.2098 (3)0.3127 (3)0.28489 (12)0.0630 (8)
H47A0.23700.33130.25120.076*
C480.1703 (3)0.4011 (2)0.31486 (12)0.0572 (8)
H48A0.17030.48100.30180.069*
C490.1310 (3)0.3743 (3)0.36369 (12)0.0563 (7)
H49A0.10360.43550.38420.068*
C500.1314 (3)0.2589 (3)0.38264 (13)0.0654 (8)
H50A0.10490.24040.41640.078*
C510.1698 (3)0.1704 (3)0.35336 (16)0.0736 (10)
H51A0.16930.09080.36660.088*
C520.2094 (3)0.1976 (3)0.30418 (16)0.0753 (10)
H52A0.23640.13630.28370.090*
C530.9261 (6)0.5700 (5)0.4825 (2)0.1024 (15)
H53A0.87360.61840.47010.123*
C540.8921 (4)0.4510 (6)0.46383 (17)0.0996 (13)
H54A0.81640.41670.43830.119*
C550.9666 (7)0.3799 (4)0.4815 (2)0.1074 (17)
H55A0.94270.29650.46850.129*
C560.9982 (5)0.3708 (5)0.1088 (3)0.130 (2)
H56A1.02640.29920.10370.155*
C571.0004 (4)0.4293 (7)0.1570 (3)0.118 (2)
H57A1.02530.39700.18600.142*
C580.9666 (4)0.5348 (6)0.1639 (2)0.1088 (15)
H58A0.96960.57650.19800.131*
C590.9297 (5)0.5806 (5)0.1240 (3)0.1202 (17)
H59A0.90810.65520.12950.144*
C600.9229 (6)0.5220 (7)0.0763 (3)0.137 (2)
H60A0.89500.55530.04810.164*
C610.9551 (6)0.4146 (6)0.0666 (2)0.143 (2)
H61A0.94810.37230.03240.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0549 (11)0.0294 (9)0.0482 (10)0.0016 (8)0.0070 (9)0.0187 (8)
O20.0420 (11)0.0401 (11)0.0661 (12)0.0012 (9)0.0022 (9)0.0196 (9)
O30.0700 (13)0.0698 (13)0.0685 (13)0.0271 (11)0.0038 (10)0.0403 (11)
O40.0603 (12)0.0294 (10)0.0776 (14)0.0058 (9)0.0028 (10)0.0202 (9)
O50.0835 (16)0.0350 (11)0.0957 (17)0.0015 (10)0.0256 (13)0.0019 (11)
O60.0695 (13)0.0312 (10)0.0778 (13)0.0054 (9)0.0229 (10)0.0241 (9)
O70.1142 (19)0.0721 (15)0.0448 (13)0.0173 (13)0.0237 (12)0.0077 (11)
O80.126 (4)0.039 (2)0.044 (2)0.033 (2)0.021 (2)0.0153 (17)
O90.114 (4)0.114 (4)0.023 (2)0.054 (3)0.025 (2)0.039 (2)
O8'0.157 (4)0.048 (2)0.046 (2)0.051 (3)0.012 (2)0.0189 (18)
O9'0.267 (7)0.102 (4)0.031 (2)0.110 (5)0.033 (3)0.003 (2)
N10.0466 (13)0.0473 (13)0.0520 (14)0.0189 (11)0.0046 (11)0.0249 (11)
N20.0520 (14)0.0282 (12)0.0610 (15)0.0057 (10)0.0105 (11)0.0166 (10)
C10.0383 (14)0.0304 (13)0.0405 (14)0.0073 (11)0.0042 (11)0.0155 (10)
C20.0345 (13)0.0236 (12)0.0376 (14)0.0009 (10)0.0013 (10)0.0114 (10)
C30.0679 (18)0.0353 (15)0.0350 (14)0.0160 (13)0.0039 (13)0.0104 (11)
C40.0641 (18)0.0284 (13)0.0414 (16)0.0151 (12)0.0035 (13)0.0103 (11)
C50.0462 (15)0.0244 (13)0.0426 (15)0.0025 (11)0.0002 (12)0.0164 (11)
C60.0709 (19)0.0384 (15)0.0399 (15)0.0151 (13)0.0148 (13)0.0169 (12)
C70.0634 (18)0.0296 (14)0.0455 (16)0.0131 (12)0.0140 (13)0.0120 (11)
C80.0374 (15)0.0338 (14)0.0413 (15)0.0085 (12)0.0116 (12)0.0138 (11)
C90.0358 (14)0.0347 (14)0.0392 (14)0.0133 (11)0.0097 (11)0.0144 (11)
C100.0386 (14)0.0372 (14)0.0394 (14)0.0105 (12)0.0048 (11)0.0167 (11)
C110.0476 (16)0.0340 (14)0.0510 (16)0.0117 (12)0.0058 (13)0.0210 (12)
C120.086 (2)0.0397 (16)0.069 (2)0.0240 (15)0.0102 (17)0.0195 (14)
C130.0541 (18)0.0594 (18)0.0647 (19)0.0140 (14)0.0143 (14)0.0363 (15)
C140.0412 (15)0.0409 (15)0.0449 (15)0.0150 (12)0.0024 (12)0.0146 (12)
C150.0400 (16)0.066 (2)0.080 (2)0.0177 (14)0.0050 (15)0.0270 (16)
C160.076 (2)0.0577 (19)0.0503 (18)0.0206 (16)0.0059 (15)0.0069 (14)
C170.0392 (15)0.0290 (13)0.0473 (15)0.0054 (11)0.0017 (12)0.0184 (11)
C180.0418 (16)0.0321 (14)0.0496 (15)0.0128 (12)0.0045 (12)0.0156 (11)
C190.0373 (15)0.0381 (15)0.0586 (17)0.0074 (12)0.0060 (12)0.0153 (12)
C200.0487 (18)0.0263 (14)0.077 (2)0.0002 (12)0.0014 (14)0.0205 (13)
C210.064 (2)0.0321 (17)0.151 (3)0.0093 (15)0.027 (2)0.0321 (18)
C220.0427 (17)0.0339 (16)0.142 (3)0.0057 (13)0.0173 (18)0.0319 (17)
C230.0465 (17)0.0308 (15)0.082 (2)0.0053 (13)0.0054 (16)0.0195 (15)
C240.0418 (15)0.0304 (14)0.0622 (18)0.0090 (12)0.0054 (13)0.0137 (13)
C250.0439 (16)0.0367 (15)0.071 (2)0.0089 (12)0.0178 (14)0.0227 (14)
C260.0436 (16)0.0330 (14)0.0651 (18)0.0063 (12)0.0166 (14)0.0143 (12)
C270.0563 (19)0.0573 (19)0.066 (2)0.0076 (15)0.0022 (16)0.0045 (15)
C280.0548 (18)0.0371 (16)0.103 (2)0.0112 (14)0.0236 (17)0.0133 (15)
C290.078 (2)0.0296 (15)0.0514 (17)0.0084 (14)0.0068 (15)0.0124 (12)
C300.115 (3)0.0370 (17)0.106 (3)0.0186 (17)0.070 (2)0.0210 (16)
C310.178 (4)0.051 (2)0.074 (2)0.003 (2)0.039 (3)0.0182 (17)
C320.0457 (16)0.0292 (13)0.0434 (15)0.0080 (11)0.0057 (13)0.0195 (11)
C330.0536 (18)0.0550 (17)0.0491 (17)0.0151 (14)0.0057 (14)0.0210 (13)
C340.066 (2)0.0510 (17)0.0520 (18)0.0192 (15)0.0219 (16)0.0239 (13)
C350.084 (2)0.0296 (14)0.0330 (15)0.0169 (14)0.0055 (15)0.0118 (11)
C360.0592 (19)0.0459 (16)0.0475 (17)0.0124 (14)0.0038 (14)0.0129 (13)
C370.0508 (17)0.0393 (15)0.0421 (16)0.0095 (12)0.0064 (13)0.0162 (11)
C470.0531 (19)0.065 (2)0.071 (2)0.0108 (16)0.0041 (15)0.0203 (17)
C480.0491 (18)0.0398 (16)0.080 (2)0.0088 (13)0.0016 (16)0.0097 (15)
C490.0403 (16)0.0519 (19)0.075 (2)0.0052 (13)0.0040 (15)0.0204 (15)
C500.0527 (19)0.059 (2)0.083 (2)0.0197 (16)0.0031 (16)0.0030 (18)
C510.065 (2)0.047 (2)0.105 (3)0.0186 (16)0.021 (2)0.0022 (19)
C520.065 (2)0.053 (2)0.105 (3)0.0042 (17)0.021 (2)0.035 (2)
C530.119 (4)0.090 (4)0.130 (4)0.057 (3)0.074 (3)0.046 (3)
C540.079 (3)0.114 (4)0.107 (3)0.016 (3)0.051 (2)0.028 (3)
C550.134 (4)0.061 (3)0.132 (4)0.020 (3)0.085 (4)0.021 (3)
C560.112 (4)0.121 (4)0.202 (6)0.071 (3)0.083 (4)0.085 (5)
C570.055 (2)0.177 (6)0.145 (5)0.023 (3)0.019 (3)0.114 (5)
C580.058 (3)0.158 (5)0.102 (4)0.010 (3)0.011 (2)0.027 (3)
C590.092 (3)0.126 (4)0.166 (5)0.056 (3)0.031 (4)0.042 (4)
C600.147 (5)0.157 (6)0.146 (5)0.064 (4)0.040 (4)0.103 (5)
C610.157 (5)0.170 (6)0.119 (4)0.054 (4)0.089 (4)0.040 (4)
Geometric parameters (Å, º) top
O1—C81.348 (3)C31—H31A0.9800
O1—C51.412 (3)C31—H31B0.9800
O2—C81.205 (3)C31—H31C0.9800
O3—N11.279 (2)C32—C371.385 (3)
O4—C231.369 (3)C32—C331.398 (3)
O4—C201.419 (3)C33—C341.380 (4)
O5—C231.199 (3)C33—H33A0.9500
O6—N21.273 (2)C34—C351.379 (4)
O7—C381.137 (5)C34—H34A0.9500
O7—C38'1.250 (5)C35—C361.369 (4)
O7—C351.389 (3)C36—C371.387 (3)
O8—C381.200 (5)C36—H36A0.9500
O9—N31.264 (5)C37—H37A0.9500
O8'—C38'1.203 (6)C38—C391.466 (7)
O9'—N3'1.285 (6)C39—C401.306 (9)
N1—C111.483 (3)C39—C441.516 (8)
N1—C141.486 (3)C40—C411.481 (11)
N2—C291.476 (3)C40—H40A0.9500
N2—C261.480 (3)C41—C421.457 (10)
N3—C411.499 (10)C41—C431.590 (10)
N3—C441.515 (7)C42—H42A0.9800
N3'—C41'1.434 (8)C42—H42B0.9800
N3'—C44'1.500 (10)C42—H42C0.9800
C1—C321.523 (3)C43—H43A0.9800
C1—C171.527 (3)C43—H43B0.9800
C1—C21.532 (3)C43—H43C0.9800
C1—H1A1.0000C44—C461.518 (7)
C2—C71.379 (3)C44—C451.522 (8)
C2—C31.379 (3)C45—H45A0.9800
C3—C41.399 (3)C45—H45B0.9800
C3—H3A0.9500C45—H45C0.9800
C4—C51.361 (3)C46—H46A0.9800
C4—H4A0.9500C46—H46B0.9800
C5—C61.376 (3)C46—H46C0.9800
C6—C71.382 (3)C38'—C39'1.460 (8)
C6—H6A0.9500C39'—C40'1.313 (9)
C7—H7A0.9500C39'—C44'1.529 (11)
C8—C91.474 (3)C40'—C41'1.480 (8)
C9—C101.329 (3)C40'—H40B0.9500
C9—C141.504 (3)C41'—C43'1.521 (7)
C10—C111.498 (3)C41'—C42'1.550 (8)
C10—H10A0.9500C42'—H42D0.9800
C11—C121.518 (3)C42'—H42E0.9800
C11—C131.529 (3)C42'—H42F0.9800
C12—H12A0.9800C43'—H43D0.9800
C12—H12B0.9800C43'—H43E0.9800
C12—H12C0.9800C43'—H43F0.9800
C13—H13A0.9800C44'—C46'1.474 (10)
C13—H13B0.9800C44'—C45'1.615 (12)
C13—H13C0.9800C45'—H45D0.9800
C14—C161.524 (4)C45'—H45E0.9800
C14—C151.531 (3)C45'—H45F0.9800
C15—H15A0.9800C46'—H46D0.9800
C15—H15B0.9800C46'—H46E0.9800
C15—H15C0.9800C46'—H46F0.9800
C16—H16A0.9800C47—C521.374 (4)
C16—H16B0.9800C47—C481.379 (4)
C16—H16C0.9800C47—H47A0.9500
C17—C181.382 (3)C48—C491.377 (4)
C17—C221.385 (3)C48—H48A0.9500
C18—C191.390 (3)C49—C501.372 (4)
C18—H18A0.9500C49—H49A0.9500
C19—C201.367 (3)C50—C511.366 (4)
C19—H19A0.9500C50—H50A0.9500
C20—C211.375 (4)C51—C521.387 (5)
C21—C221.374 (4)C51—H51A0.9500
C21—H21A0.9500C52—H52A0.9500
C22—H22A0.9500C53—C55i1.347 (6)
C23—C241.475 (4)C53—C541.357 (6)
C24—C251.319 (4)C53—H53A0.9500
C24—C291.508 (3)C54—C551.373 (6)
C25—C261.508 (3)C54—H54A0.9500
C25—H25A0.9500C55—C53i1.347 (6)
C26—C271.515 (4)C55—H55A0.9500
C26—C281.532 (4)C56—C571.346 (7)
C27—H27A0.9800C56—C611.384 (7)
C27—H27B0.9800C56—H56A0.9500
C27—H27C0.9800C57—C581.358 (7)
C28—H28A0.9800C57—H57A0.9500
C28—H28B0.9800C58—C591.326 (6)
C28—H28C0.9800C58—H58A0.9500
C29—C311.509 (4)C59—C601.327 (7)
C29—C301.525 (4)C59—H59A0.9500
C30—H30A0.9800C60—C611.375 (7)
C30—H30B0.9800C60—H60A0.9500
C30—H30C0.9800C61—H61A0.9500
C8—O1—C5118.87 (18)C34—C33—C32121.1 (3)
C23—O4—C20115.0 (2)C34—C33—H33A119.4
C38—O7—C35128.4 (3)C32—C33—H33A119.4
C38'—O7—C35140.5 (3)C35—C34—C33118.9 (3)
O3—N1—C11122.38 (19)C35—C34—H34A120.5
O3—N1—C14122.5 (2)C33—C34—H34A120.5
C11—N1—C14115.02 (18)C36—C35—C34121.5 (2)
O6—N2—C29122.8 (2)C36—C35—O7119.6 (3)
O6—N2—C26121.55 (19)C34—C35—O7118.9 (3)
C29—N2—C26115.49 (18)C35—C36—C37119.1 (3)
O9—N3—C41125.6 (5)C35—C36—H36A120.5
O9—N3—C44121.5 (5)C37—C36—H36A120.5
C41—N3—C44112.1 (5)C32—C37—C36121.2 (2)
O9'—N3'—C41'125.1 (6)C32—C37—H37A119.4
O9'—N3'—C44'120.0 (6)C36—C37—H37A119.4
C41'—N3'—C44'114.8 (5)O7—C38—O8121.0 (5)
C32—C1—C17108.73 (17)O7—C38—C39114.1 (5)
C32—C1—C2114.44 (18)O8—C38—C39124.5 (5)
C17—C1—C2114.55 (19)C40—C39—C38123.7 (6)
C32—C1—H1A106.1C40—C39—C44112.4 (5)
C17—C1—H1A106.1C38—C39—C44123.8 (5)
C2—C1—H1A106.1C39—C40—C41114.6 (6)
C7—C2—C3117.7 (2)C39—C40—H40A122.7
C7—C2—C1119.1 (2)C41—C40—H40A122.7
C3—C2—C1123.0 (2)C42—C41—C40118.7 (8)
C2—C3—C4121.3 (2)C42—C41—N3111.0 (6)
C2—C3—H3A119.3C40—C41—N3100.5 (6)
C4—C3—H3A119.3C42—C41—C43107.8 (6)
C5—C4—C3118.8 (2)C40—C41—C43110.9 (6)
C5—C4—H4A120.6N3—C41—C43107.3 (7)
C3—C4—H4A120.6C41—C42—H42A109.5
C4—C5—C6121.5 (2)C41—C42—H42B109.5
C4—C5—O1117.3 (2)H42A—C42—H42B109.5
C6—C5—O1120.9 (2)C41—C42—H42C109.5
C5—C6—C7118.6 (2)H42A—C42—H42C109.5
C5—C6—H6A120.7H42B—C42—H42C109.5
C7—C6—H6A120.7C41—C43—H43A109.5
C2—C7—C6122.1 (2)C41—C43—H43B109.5
C2—C7—H7A119.0H43A—C43—H43B109.5
C6—C7—H7A119.0C41—C43—H43C109.5
O2—C8—O1123.6 (2)H43A—C43—H43C109.5
O2—C8—C9125.3 (2)H43B—C43—H43C109.5
O1—C8—C9111.1 (2)N3—C44—C3999.8 (4)
C10—C9—C8125.5 (2)N3—C44—C46111.7 (4)
C10—C9—C14112.9 (2)C39—C44—C46113.3 (5)
C8—C9—C14121.6 (2)N3—C44—C45107.8 (4)
C9—C10—C11113.2 (2)C39—C44—C45112.7 (4)
C9—C10—H10A123.4C46—C44—C45111.0 (4)
C11—C10—H10A123.4C44—C45—H45A109.5
N1—C11—C1099.52 (18)C44—C45—H45B109.5
N1—C11—C12110.3 (2)H45A—C45—H45B109.5
C10—C11—C12112.9 (2)C44—C45—H45C109.5
N1—C11—C13109.2 (2)H45A—C45—H45C109.5
C10—C11—C13112.6 (2)H45B—C45—H45C109.5
C12—C11—C13111.6 (2)C44—C46—H46A109.5
C11—C12—H12A109.5C44—C46—H46B109.5
C11—C12—H12B109.5H46A—C46—H46B109.5
H12A—C12—H12B109.5C44—C46—H46C109.5
C11—C12—H12C109.5H46A—C46—H46C109.5
H12A—C12—H12C109.5H46B—C46—H46C109.5
H12B—C12—H12C109.5O8'—C38'—O7111.5 (4)
C11—C13—H13A109.5O8'—C38'—C39'128.1 (6)
C11—C13—H13B109.5O7—C38'—C39'120.4 (5)
H13A—C13—H13B109.5C40'—C39'—C38'125.8 (7)
C11—C13—H13C109.5C40'—C39'—C44'112.0 (6)
H13A—C13—H13C109.5C38'—C39'—C44'122.2 (7)
H13B—C13—H13C109.5C39'—C40'—C41'113.3 (5)
N1—C14—C999.35 (19)C39'—C40'—H40B123.4
N1—C14—C16109.3 (2)C41'—C40'—H40B123.4
C9—C14—C16114.0 (2)N3'—C41'—C40'101.5 (4)
N1—C14—C15109.4 (2)N3'—C41'—C43'110.4 (5)
C9—C14—C15113.0 (2)C40'—C41'—C43'110.9 (4)
C16—C14—C15111.1 (2)N3'—C41'—C42'111.6 (5)
C14—C15—H15A109.5C40'—C41'—C42'113.1 (5)
C14—C15—H15B109.5C43'—C41'—C42'109.2 (5)
H15A—C15—H15B109.5C41'—C42'—H42D109.5
C14—C15—H15C109.5C41'—C42'—H42E109.5
H15A—C15—H15C109.5H42D—C42'—H42E109.5
H15B—C15—H15C109.5C41'—C42'—H42F109.5
C14—C16—H16A109.5H42D—C42'—H42F109.5
C14—C16—H16B109.5H42E—C42'—H42F109.5
H16A—C16—H16B109.5C41'—C43'—H43D109.5
C14—C16—H16C109.5C41'—C43'—H43E109.5
H16A—C16—H16C109.5H43D—C43'—H43E109.5
H16B—C16—H16C109.5C41'—C43'—H43F109.5
C18—C17—C22118.0 (2)H43D—C43'—H43F109.5
C18—C17—C1123.6 (2)H43E—C43'—H43F109.5
C22—C17—C1118.2 (2)C46'—C44'—N3'111.9 (6)
C17—C18—C19121.1 (2)C46'—C44'—C39'114.3 (7)
C17—C18—H18A119.5N3'—C44'—C39'98.4 (5)
C19—C18—H18A119.5C46'—C44'—C45'115.5 (7)
C20—C19—C18118.8 (2)N3'—C44'—C45'105.6 (7)
C20—C19—H19A120.6C39'—C44'—C45'109.4 (7)
C18—C19—H19A120.6C44'—C45'—H45D109.5
C19—C20—C21121.5 (2)C44'—C45'—H45E109.5
C19—C20—O4120.3 (2)H45D—C45'—H45E109.5
C21—C20—O4118.1 (2)C44'—C45'—H45F109.5
C22—C21—C20118.7 (3)H45D—C45'—H45F109.5
C22—C21—H21A120.6H45E—C45'—H45F109.5
C20—C21—H21A120.6C44'—C46'—H46D109.5
C21—C22—C17121.7 (3)C44'—C46'—H46E109.5
C21—C22—H22A119.2H46D—C46'—H46E109.5
C17—C22—H22A119.2C44'—C46'—H46F109.5
O5—C23—O4124.0 (2)H46D—C46'—H46F109.5
O5—C23—C24124.5 (3)H46E—C46'—H46F109.5
O4—C23—C24111.4 (3)C52—C47—C48119.4 (3)
C25—C24—C23125.7 (2)C52—C47—H47A120.3
C25—C24—C29112.7 (2)C48—C47—H47A120.3
C23—C24—C29121.5 (2)C49—C48—C47120.3 (3)
C24—C25—C26113.4 (2)C49—C48—H48A119.8
C24—C25—H25A123.3C47—C48—H48A119.8
C26—C25—H25A123.3C50—C49—C48119.8 (3)
N2—C26—C2598.93 (19)C50—C49—H49A120.1
N2—C26—C27110.5 (2)C48—C49—H49A120.1
C25—C26—C27113.5 (2)C51—C50—C49120.6 (3)
N2—C26—C28110.1 (2)C51—C50—H50A119.7
C25—C26—C28111.2 (2)C49—C50—H50A119.7
C27—C26—C28111.9 (2)C50—C51—C52119.5 (3)
C26—C27—H27A109.5C50—C51—H51A120.2
C26—C27—H27B109.5C52—C51—H51A120.2
H27A—C27—H27B109.5C47—C52—C51120.4 (3)
C26—C27—H27C109.5C47—C52—H52A119.8
H27A—C27—H27C109.5C51—C52—H52A119.8
H27B—C27—H27C109.5C55i—C53—C54120.5 (4)
C26—C28—H28A109.5C55i—C53—H53A119.7
C26—C28—H28B109.5C54—C53—H53A119.7
H28A—C28—H28B109.5C53—C54—C55120.4 (4)
C26—C28—H28C109.5C53—C54—H54A119.8
H28A—C28—H28C109.5C55—C54—H54A119.8
H28B—C28—H28C109.5C53i—C55—C54119.1 (4)
N2—C29—C2499.4 (2)C53i—C55—H55A120.5
N2—C29—C31109.2 (2)C54—C55—H55A120.5
C24—C29—C31112.9 (3)C57—C56—C61120.2 (5)
N2—C29—C30109.1 (2)C57—C56—H56A119.9
C24—C29—C30112.7 (2)C61—C56—H56A119.9
C31—C29—C30112.7 (3)C56—C57—C58119.6 (5)
C29—C30—H30A109.5C56—C57—H57A120.2
C29—C30—H30B109.5C58—C57—H57A120.2
H30A—C30—H30B109.5C59—C58—C57121.2 (5)
C29—C30—H30C109.5C59—C58—H58A119.4
H30A—C30—H30C109.5C57—C58—H58A119.4
H30B—C30—H30C109.5C58—C59—C60119.9 (5)
C29—C31—H31A109.5C58—C59—H59A120.1
C29—C31—H31B109.5C60—C59—H59A120.1
H31A—C31—H31B109.5C59—C60—C61121.9 (5)
C29—C31—H31C109.5C59—C60—H60A119.0
H31A—C31—H31C109.5C61—C60—H60A119.0
H31B—C31—H31C109.5C60—C61—C56117.1 (5)
C37—C32—C33118.2 (2)C60—C61—H61A121.4
C37—C32—C1120.1 (2)C56—C61—H61A121.4
C33—C32—C1121.7 (2)
C32—C1—C2—C7177.7 (2)C17—C1—C32—C37120.5 (2)
C17—C1—C2—C755.8 (3)C2—C1—C32—C37110.0 (2)
C32—C1—C2—C33.0 (3)C17—C1—C32—C3357.6 (3)
C17—C1—C2—C3129.5 (2)C2—C1—C32—C3371.9 (3)
C7—C2—C3—C41.4 (4)C37—C32—C33—C340.0 (4)
C1—C2—C3—C4173.3 (2)C1—C32—C33—C34178.1 (2)
C2—C3—C4—C50.6 (4)C32—C33—C34—C350.6 (4)
C3—C4—C5—C60.3 (4)C33—C34—C35—C360.8 (4)
C3—C4—C5—O1173.7 (2)C33—C34—C35—O7179.3 (2)
C8—O1—C5—C4118.3 (2)C38—O7—C35—C3699.6 (4)
C8—O1—C5—C668.2 (3)C38'—O7—C35—C36113.8 (5)
C4—C5—C6—C70.9 (4)C38—O7—C35—C3478.9 (5)
O1—C5—C6—C7174.1 (2)C38'—O7—C35—C3467.7 (5)
C3—C2—C7—C62.1 (4)C34—C35—C36—C370.5 (4)
C1—C2—C7—C6172.9 (2)O7—C35—C36—C37178.9 (2)
C5—C6—C7—C21.9 (4)C33—C32—C37—C360.3 (3)
C5—O1—C8—O21.2 (3)C1—C32—C37—C36178.4 (2)
C5—O1—C8—C9178.68 (19)C35—C36—C37—C320.1 (4)
O2—C8—C9—C10179.2 (2)C35—O7—C38—O814.1 (7)
O1—C8—C9—C100.7 (3)C35—O7—C38—C39172.1 (3)
O2—C8—C9—C140.6 (4)O7—C38—C39—C404.5 (7)
O1—C8—C9—C14179.4 (2)O8—C38—C39—C40178.1 (5)
C8—C9—C10—C11178.5 (2)O7—C38—C39—C44172.8 (5)
C14—C9—C10—C111.4 (3)O8—C38—C39—C440.8 (8)
O3—N1—C11—C10175.2 (2)C38—C39—C40—C41178.1 (5)
C14—N1—C11—C100.7 (2)C44—C39—C40—C410.6 (7)
O3—N1—C11—C1265.9 (3)C39—C40—C41—C42125.7 (7)
C14—N1—C11—C12118.2 (2)C39—C40—C41—N34.6 (7)
O3—N1—C11—C1357.1 (3)C39—C40—C41—C43108.7 (7)
C14—N1—C11—C13118.8 (2)O9—N3—C41—C4255.6 (9)
C9—C10—C11—N10.4 (3)C44—N3—C41—C42134.6 (6)
C9—C10—C11—C12117.3 (2)O9—N3—C41—C40177.9 (5)
C9—C10—C11—C13115.1 (2)C44—N3—C41—C408.1 (7)
O3—N1—C14—C9174.5 (2)O9—N3—C41—C4362.0 (7)
C11—N1—C14—C91.4 (2)C44—N3—C41—C43107.9 (6)
O3—N1—C14—C1654.8 (3)O9—N3—C44—C39178.7 (5)
C11—N1—C14—C16121.0 (2)C41—N3—C44—C398.3 (6)
O3—N1—C14—C1567.0 (3)O9—N3—C44—C4658.7 (7)
C11—N1—C14—C15117.2 (2)C41—N3—C44—C46111.7 (6)
C10—C9—C14—N11.6 (2)O9—N3—C44—C4563.5 (6)
C8—C9—C14—N1178.25 (19)C41—N3—C44—C45126.2 (5)
C10—C9—C14—C16117.7 (2)C40—C39—C44—N35.4 (6)
C8—C9—C14—C1662.2 (3)C38—C39—C44—N3177.1 (5)
C10—C9—C14—C15114.2 (2)C40—C39—C44—C46113.5 (5)
C8—C9—C14—C1565.9 (3)C38—C39—C44—C4664.1 (7)
C32—C1—C17—C1892.5 (3)C40—C39—C44—C45119.5 (5)
C2—C1—C17—C1837.0 (3)C38—C39—C44—C4562.9 (7)
C32—C1—C17—C2282.6 (3)C35—O7—C38'—O8'6.4 (7)
C2—C1—C17—C22148.0 (2)C35—O7—C38'—C39'175.6 (4)
C22—C17—C18—C192.8 (4)O8'—C38'—C39'—C40'171.8 (6)
C1—C17—C18—C19172.2 (2)O7—C38'—C39'—C40'10.5 (9)
C17—C18—C19—C200.3 (4)O8'—C38'—C39'—C44'10.9 (9)
C18—C19—C20—C212.9 (4)O7—C38'—C39'—C44'166.8 (5)
C18—C19—C20—O4179.7 (2)C38'—C39'—C40'—C41'179.1 (5)
C23—O4—C20—C1986.6 (3)C44'—C39'—C40'—C41'1.5 (7)
C23—O4—C20—C2195.9 (3)O9'—N3'—C41'—C40'178.7 (6)
C19—C20—C21—C223.3 (5)C44'—N3'—C41'—C40'2.7 (7)
O4—C20—C21—C22179.2 (3)O9'—N3'—C41'—C43'63.7 (8)
C20—C21—C22—C170.6 (5)C44'—N3'—C41'—C43'120.4 (6)
C18—C17—C22—C212.4 (5)O9'—N3'—C41'—C42'58.0 (8)
C1—C17—C22—C21172.9 (3)C44'—N3'—C41'—C42'118.0 (6)
C20—O4—C23—O56.1 (4)C39'—C40'—C41'—N3'2.6 (6)
C20—O4—C23—C24172.3 (2)C39'—C40'—C41'—C43'119.8 (5)
O5—C23—C24—C25179.2 (3)C39'—C40'—C41'—C42'117.1 (6)
O4—C23—C24—C252.4 (4)O9'—N3'—C44'—C46'61.3 (9)
O5—C23—C24—C292.6 (4)C41'—N3'—C44'—C46'122.5 (7)
O4—C23—C24—C29175.8 (2)O9'—N3'—C44'—C39'178.1 (6)
C23—C24—C25—C26177.2 (2)C41'—N3'—C44'—C39'1.9 (7)
C29—C24—C25—C261.2 (3)O9'—N3'—C44'—C45'65.1 (8)
O6—N2—C26—C25177.9 (2)C41'—N3'—C44'—C45'111.0 (7)
C29—N2—C26—C251.7 (3)C40'—C39'—C44'—C46'118.9 (7)
O6—N2—C26—C2762.8 (3)C38'—C39'—C44'—C46'58.7 (9)
C29—N2—C26—C27121.0 (2)C40'—C39'—C44'—N3'0.2 (7)
O6—N2—C26—C2861.3 (3)C38'—C39'—C44'—N3'177.5 (5)
C29—N2—C26—C28114.9 (2)C40'—C39'—C44'—C45'109.7 (7)
C24—C25—C26—N21.7 (3)C38'—C39'—C44'—C45'72.6 (8)
C24—C25—C26—C27118.7 (3)C52—C47—C48—C490.0 (4)
C24—C25—C26—C28114.0 (3)C47—C48—C49—C500.2 (4)
O6—N2—C29—C24177.2 (2)C48—C49—C50—C510.4 (4)
C26—N2—C29—C241.1 (3)C49—C50—C51—C520.4 (5)
O6—N2—C29—C3158.9 (3)C48—C47—C52—C510.0 (5)
C26—N2—C29—C31117.2 (3)C50—C51—C52—C470.2 (5)
O6—N2—C29—C3064.7 (3)C55i—C53—C54—C550.3 (6)
C26—N2—C29—C30119.2 (2)C53—C54—C55—C53i0.3 (6)
C25—C24—C29—N20.1 (3)C61—C56—C57—C583.3 (7)
C23—C24—C29—N2178.4 (2)C56—C57—C58—C590.9 (7)
C25—C24—C29—C31115.7 (3)C57—C58—C59—C601.2 (7)
C23—C24—C29—C3162.8 (3)C58—C59—C60—C610.9 (8)
C25—C24—C29—C30115.3 (3)C59—C60—C61—C561.4 (8)
C23—C24—C29—C3066.3 (3)C57—C56—C61—C603.5 (7)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, and Cg3 are the centroids of the C47–C52, C17–C22 and C56–C61 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1A···O6ii1.002.493.448 (3)160
C4—H4A···O9iii0.952.443.165 (5)133
C25—H25A···O2iv0.952.573.358 (4)141
C37—H37A···O6ii0.952.573.442 (3)153
C57—H57A···O6v0.952.583.514 (8)168
C10—H10A···Cg10.952.843.752 (3)161
C12—H12A···Cg2v0.982.943.726 (3)138
C19—H19A···Cg1vi0.952.793.725 (3)169
C34—H34A···Cg30.952.783.547 (4)138
Symmetry codes: (ii) x1, y1, z; (iii) x+1, y, z; (iv) x, y+1, z; (v) x, y1, z; (vi) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC46H52N3O9·3C6H6
Mr1025.23
Crystal system, space groupTriclinic, P1
Temperature (K)164
a, b, c (Å)10.0810 (13), 11.7372 (16), 26.241 (4)
α, β, γ (°)98.324 (10), 92.765 (11), 105.308 (10)
V3)2951.1 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.70 × 0.20 × 0.20
Data collection
DiffractometerSiemens SMART 1K CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.878, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
43135, 12901, 6172
Rint0.054
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.194, 1.04
No. of reflections12901
No. of parameters667
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.40

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, and Cg3 are the centroids of the C47–C52, C17–C22 and C56–C61 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C1—H1A···O6i1.002.493.448 (3)160
C4—H4A···O9'ii0.952.443.165 (5)133
C25—H25A···O2iii0.952.573.358 (4)141
C37—H37A···O6i0.952.573.442 (3)153
C57—H57A···O6iv0.952.583.514 (8)168
C10—H10A···Cg10.952.843.752 (3)161
C12—H12A···Cg2iv0.982.943.726 (3)138
C19—H19A···Cg1v0.952.793.725 (3)169
C34—H34A···Cg30.952.783.547 (4)138
Symmetry codes: (i) x1, y1, z; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x, y1, z; (v) x+1, y+1, z.
 

References

First citationGodt, A., Franzen, C., Veit, S., Enkelmann, V., Pannier, M. & Jeschke, G. (2000). J. Org. Chem. 65, 7575–7582.  Web of Science CSD CrossRef PubMed CAS
First citationMargraf, D., Schuetz, D., Prisner, T. F. & Bats, J. W. (2009). Acta Cryst. E65, o1784.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSiemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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Volume 66| Part 4| April 2010| Pages o729-o730
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