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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 10| October 2010| Pages o2570-o2571
doi:10.1107/S1600536810036275

2,9-Di-3-pentyl­anthra[1,9-def:6,5,10-d′e′f′]diiso­quinoline-1,3,8,10-tetrone

Waldemar Maniukiewicz,a* Joanna Bojarska,a Andrzej Olczak,a Ewa Dobruchowskab and Michał Wiatrowskib

aInstitute of General and Ecological Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland, and bDepartment of Molecular Physics, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland
*Correspondence e-mail: wmaniuk@p.lodz.pl

(Received 25 August 2010; accepted 9 September 2010; online 15 September 2010)

The asymmetric unit of the title compound, C34H30N2O4, contains four independent half-mol­ecules, the complete mol­ecules being generated by inversion symmetry. The mol­ecules each have planar (within 4σ) perylene­tetra­carb­oxy­lic diimide fragments with bent side chains. In one of the independent mol­ecules, each 3-pentyl fragment is disordered over two conformations in a 7:3 ratio. In the crystal, π–π inter­actions link mol­ecules into stacks propagated in [010]. The crystal packing also exhibits weak inter­molecular C—H⋯O hydrogen bonds.

Related literature

For the properties and applications of perylene derivatives, see: Tracz et al. (1981[Tracz, A., Ulański, J., Pakula, M. & Kryszewski, M. (1981). Pol. Patent 231177.]); Graser & Hädicke (1980[Graser, F. & Hädicke, E. (1980). Justus Liebigs Ann. Chem. pp. 1994-2001.], 1984[Graser, F. & Hädicke, E. (1984). Justus Liebigs Ann. Chem. pp. 483-494.]); Herbst & Hunger (1993[Herbst, W. & Hunger, K. (1993). Ind. Org. Pigm. 9, 447-463.]); Newman et al. (2004[Newman, C. R., Frisbie, D. A., Da Silvo Filho, D. A., Bredas, J. L., Ewback, P. C. & Mann, K. R. (2004). Chem. Mater. 16, 4436-4451.]); Wurthner (2004[Wurthner, F. (2004). Chem. Commun. 14, 1564-1579.]); Dodabalapur (2006[Dodabalapur, A. (2006). Mater. Today, 9, 24-30.]); Miśkiewicz et al. (2006[Miśkiewicz, P., Mas-Torrent, M., Jung, J., Kotarba, S., Glowacki, I., Gomar-Nadal, E., Amabilino, D. B., Veciana, J., Krause, B., Carbone, D., Rovira, C. & Ulanski, J. (2006). Chem. Mater. 18, 4724-4729.]); Wiatrowski et al. (2010[Wiatrowski, M., Dobruchowska, E., Maniukiewicz, W., Pietsch, U., Kowalski, J., Szamel, Z. & Ulański, J. (2010). Thin Solid Films, 518, 2266-2270.]). For related structures, see: Hädicke & Graser (1986a[Hädicke, E. & Graser, F. (1986a). Acta Cryst. C42, 189-195.],b[Hädicke, E. & Graser, F. (1986b). Acta Cryst. C42, 195-198.]); Mizuguchi (2003[Mizuguchi, J. (2003). Z. Kristallogr. New Cryst. Struct. 218, 131-132.]); Guillermet et al. (2006[Guillermet, O., Mossoyan-Deneux, M., Giorgi, M., Glachant, A. & Mossoyan, J. C. (2006). Thin Solid Films, 514, 25-32.]); Briseno et al. (2007[Briseno, A. L., Mannsfeld, S. C. B., Reese, C., Hancock, J., Xiong, Y., Jenekhe, S.A., Bao, Z., Xia, Y. (2007). Nano Lett. 7, 2847-2853.]).

[Scheme 1]

Experimental

Crystal data

  • C34H30N2O4

  • Mr = 530.60

  • Monoclinic, P 21 /c

  • a = 34.009 (4) Å

  • b = 7.5035 (10) Å

  • c = 21.248 (3) Å

  • β = 100.562 (2)°

  • V = 5330.3 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.40 × 0.05 × 0.05 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen. Germany.]) Tmin = 0.966, Tmax = 0.996

  • 85917 measured reflections

  • 9351 independent reflections

  • 6350 reflections with I > 2σ(I)

  • Rint = 0.051
Refinement

  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.166

  • S = 1.03

  • 9351 reflections

  • 760 parameters

  • 871 restraints

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Centroid–centroid distances (Å)

Cg1, Cg2, Cg3, Cg4, Cg5, Cg6, Cg7, Cg8, Cg9, Cg10, Cg11, Cg12, Cg13 and Cg14 are the centroids of the N4/C52–C56, C53/C54/C57–C60, C54/C55/C60–C63, C59–C61/C59d–C61d, C2/C3/C6–C9, C3/C4/C9–C12, C8–C10/C8a–C10a, N2/C18–C22, C19/C20/C23–C26, C25–C27/C25b–C27b, N3/C35–C39, C36/C37/C40–C43, C37/C38/C43–C46 and C42–C44/C42c–C44c, respectively. Symmetry codes: (a) 1-x, 2-y, 1-z; (b) 1-x, 1-y, 1-z; (c) -x, 2-y, -z; (d) -x, 1-y, -z.
Cg1⋯Cg13i 3.6863 (19)
Cg2⋯Cg11 3.7041 (19)
Cg2⋯Cg12i 3.6485 (18)
Cg2⋯Cg13i 3.6165 (18)
Cg3⋯Cg13 3.7245 (19)
Cg4⋯Cg13 3.6034 (18)
Cg4⋯Cg14i 3.7518 (18)
Cg5⋯Cg9ii 3.6604 (16)
Cg6⋯Cg10 3.5395 (15)
Cg6⋯Cg8ii 3.7743 (16)
Cg6⋯Cg9 3.7544 (16)
Cg7⋯Cg9ii 3.5613 (15)
Cg7⋯Cg10 3.7518 (14)
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7⋯O4iii 0.93 2.55 3.170 (4) 125
C15—H15B⋯O3ii 0.96 2.42 3.323 (5) 156
C32—H32C⋯O2 0.96 2.60 3.453 (5) 148
C41—H41⋯O8iv 0.93 2.49 3.343 (4) 153
C49—H49C⋯O7ii 0.96 2.56 3.481 (6) 162
Symmetry codes: (ii) x, y+1, z; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036275/cv2759sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036275/cv2759Isup2.hkl

checkCIF report


Comment top

The derivatives of perylene tetracarboxylic diimide (PTCDI) have long been a focus of research for their wide applications. These compounds are well known as industrially important organic pigments, which exhibit a variety of colours (Herbst & Hunger, 1993). The correlations between the colour of the crystals and the different arrangement of the molecules in the stacks were discussed in details by Graser and Hädicke (Graser and Hädicke,1980, 1984). Besides, the derivatives of perylenediimide are extremely robust, commercially available materials with high photo and thermal stability (Newman, 2004). More recently the PTCDI's are also of interest as the n-type semiconductors, in contrast to the more common p-type counterparts in organic semiconductors, making them attractive candidates for fabrication of various organic electronic elements (Wiatrowski et al., 2010; Dodabalapur, 2006; Miśkiewicz, 2006; Wurthner, 2004; Tracz, 1981). The cystal and molecular structure of the title compound reported here have been determined as part of an investigation on the charge transport properties of organic semiconductors caused by electronic coupling between stacking molecules. The unit structure of the PTCDI is illustrated in Fig. 1. Neighbouring molecules are arranged in stacks (Fig. 2), where the stacking distance is about 3.35 Å, with their long axes tilted in relation to the column grow direction. Typical hydrogen bonds are not observed.

Related literature top

For the properties and applications of perylene derivatives, see: Tracz et al. (1981); Graser & Hädicke (1980,1984); Herbst & Hunger (1993); Newman et al. (2004); Wurthner (2004); Dodabalapur (2006); Miśkiewicz et al. (2006); Wiatrowski et al. (2010). For related structures, see: Hädicke & Graser (1986a,b); Mizuguchi (2003); Guillermet et al. (2006); Briseno et al. (2007).

Experimental top

All chemicals used were commercially available. PTCDI-C5(3) was provided SynTech GmbH. The single crystals were grown by slow evaporation from a nitrobenzene solution of the title compound at room temperature. After several weeks poor quality, weakly diffracted dark red needle crystals were obtained. The structure was determined by single-crystal diffraction.

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 - 0.97 Å and with Uiso(H) = 1.2-1.5 Ueq(C). The terminal ethyl groups in one of the molecules were treated as disordered over two sets of positions using restraints on the anisotropic displacement, with the occupancies fixed to 0.7 and 0.3, respectively.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. One independent molecule of the title compound showing the atomic numbering and 30% probability displacement ellipsoids [symmetry code: (a) -x, 1 - y, -z]. All H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Molecular packing viewed down the b.
2,9-Di-3-pentylanthra[1,9-def:6,5,10-d'e'f'] diisoquinoline-1,3,8,10-tetrone top
Crystal data top
C34H30N2O4F(000) = 2240
Mr = 530.60Dx = 1.322 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9930 reflections
a = 34.009 (4) Åθ = 2.4–26.2°
b = 7.5035 (10) ŵ = 0.09 mm−1
c = 21.248 (3) ÅT = 296 K
β = 100.562 (2)°Needle, dark red
V = 5330.3 (12) Å30.40 × 0.05 × 0.05 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		9351 independent reflections
Radiation source: fine-focus sealed tube6350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scanθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		h = −40→40
Tmin = 0.966, Tmax = 0.996k = −8→8
85917 measured reflectionsl = −25→25
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0469P)2 + 6.5326P]
where P = (Fo2 + 2Fc2)/3
9351 reflections(Δ/σ)max < 0.001
760 parametersΔρmax = 0.24 e Å−3
871 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C34H30N2O4V = 5330.3 (12) Å3
Mr = 530.60Z = 8
Monoclinic, P21/cMo Kα radiation
a = 34.009 (4) ŵ = 0.09 mm−1
b = 7.5035 (10) ÅT = 296 K
c = 21.248 (3) Å0.40 × 0.05 × 0.05 mm
β = 100.562 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		9351 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)		6350 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.996Rint = 0.051
85917 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062871 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å−3
9351 reflectionsΔρmin = −0.21 e Å−3
760 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
O70.15032 (8)0.1736 (4)0.15767 (13)0.0912 (11)
O80.05685 (9)0.2928 (5)0.27973 (12)0.1039 (13)
N40.10523 (9)0.2440 (4)0.22107 (14)0.0698 (10)
C520.11766 (11)0.2356 (5)0.16172 (17)0.0672 (12)
C530.09065 (10)0.3063 (4)0.10547 (16)0.0593 (11)
C540.05202 (9)0.3650 (4)0.11002 (15)0.0543 (10)
C550.03954 (11)0.3581 (5)0.16981 (16)0.0641 (11)
C560.06682 (12)0.2964 (5)0.22741 (18)0.0745 (14)
C570.10337 (10)0.3144 (4)0.04753 (17)0.0622 (11)
C580.07854 (10)0.3848 (4)−0.00564 (16)0.0607 (11)
C590.03994 (9)0.4419 (4)−0.00431 (14)0.0518 (10)
C600.02605 (9)0.4311 (4)0.05535 (14)0.0508 (10)
C61−0.01339 (9)0.4882 (4)0.06022 (15)0.0546 (11)
C62−0.02436 (11)0.4748 (5)0.12051 (16)0.0675 (11)
C630.00152 (11)0.4127 (5)0.17361 (17)0.0743 (14)
C64A0.1356 (3)0.1883 (11)0.2766 (4)0.081 (3)0.700
C65A0.1658 (3)0.3118 (13)0.2996 (5)0.179 (5)0.700
C66A0.1864 (3)0.3551 (14)0.3593 (4)0.180 (5)0.700
C67A0.1251 (3)0.0055 (14)0.3020 (4)0.128 (4)0.700
C68A0.1542 (3)−0.0819 (14)0.3474 (4)0.142 (4)0.700
C64B0.1310 (8)0.204 (2)0.2901 (12)0.095 (5)0.300
C65B0.1457 (4)0.3684 (15)0.3128 (5)0.132 (6)0.300
C66B0.1875 (4)0.4319 (15)0.3069 (5)0.188 (9)0.300
C67B0.1426 (4)0.0054 (15)0.2839 (5)0.087 (6)0.300
C68B0.1231 (8)−0.110 (3)0.3206 (12)0.158 (13)0.300
O10.33801 (6)0.8756 (4)0.57655 (11)0.0825 (9)
O20.34231 (6)0.6514 (3)0.37896 (10)0.0623 (8)
N10.33851 (6)0.7642 (3)0.47692 (11)0.0493 (8)
C10.35654 (8)0.8479 (4)0.53397 (14)0.0531 (10)
C20.39920 (8)0.8984 (4)0.54060 (12)0.0420 (8)
C30.41964 (7)0.8790 (3)0.48919 (12)0.0365 (8)
C40.39983 (7)0.8014 (3)0.43157 (12)0.0384 (8)
C50.35849 (8)0.7328 (4)0.42623 (14)0.0469 (9)
C60.41887 (8)0.9708 (4)0.59704 (13)0.0467 (9)
C70.45877 (8)1.0237 (4)0.60401 (12)0.0433 (9)
C80.47981 (7)1.0109 (3)0.55426 (11)0.0353 (8)
C90.45979 (7)0.9384 (3)0.49465 (11)0.0340 (8)
C100.47885 (7)0.9254 (3)0.44059 (11)0.0356 (8)
C110.45780 (8)0.8520 (4)0.38439 (12)0.0413 (8)
C120.41902 (8)0.7882 (4)0.38058 (12)0.0420 (8)
C130.29580 (8)0.7047 (5)0.47125 (16)0.0606 (11)
C140.26833 (10)0.7838 (6)0.41446 (19)0.0830 (15)
C150.27052 (12)0.9843 (7)0.4094 (3)0.117 (2)
C160.29299 (10)0.5022 (5)0.47604 (18)0.0714 (11)
C170.31410 (11)0.4269 (6)0.53911 (17)0.0790 (16)
O30.34920 (6)0.1448 (3)0.35559 (9)0.0598 (8)
O40.43654 (7)0.2748 (4)0.22385 (9)0.0716 (9)
N20.39047 (7)0.2227 (3)0.28708 (10)0.0480 (8)
C180.38009 (8)0.2150 (4)0.34781 (13)0.0456 (9)
C190.40806 (7)0.2938 (3)0.40210 (12)0.0379 (8)
C200.44575 (7)0.3567 (3)0.39396 (12)0.0358 (8)
C210.45633 (8)0.3498 (4)0.33281 (12)0.0419 (8)
C220.42768 (8)0.2810 (4)0.27691 (13)0.0494 (10)
C230.39707 (7)0.3066 (4)0.46086 (12)0.0414 (8)
C240.42302 (7)0.3787 (4)0.51279 (12)0.0409 (8)
C250.46077 (7)0.4389 (3)0.50770 (12)0.0354 (8)
C260.47294 (7)0.4267 (3)0.44697 (11)0.0343 (8)
C270.51111 (7)0.4883 (3)0.43760 (12)0.0364 (8)
C280.52010 (8)0.4797 (4)0.37648 (13)0.0471 (9)
C290.49306 (8)0.4127 (4)0.32512 (13)0.0500 (10)
C300.36052 (9)0.1622 (4)0.23004 (14)0.0557 (10)
C310.32038 (10)0.2563 (5)0.22485 (17)0.0719 (14)
C320.32279 (13)0.4558 (6)0.2294 (2)0.0948 (17)
C330.35716 (10)−0.0399 (5)0.22768 (15)0.0641 (11)
C340.39376 (11)−0.1330 (5)0.21307 (17)0.0762 (16)
O50.17448 (7)0.8403 (4)−0.00898 (13)0.0895 (10)
O60.13990 (7)0.6532 (3)0.17751 (11)0.0713 (9)
N30.15775 (7)0.7338 (4)0.08308 (13)0.0601 (9)
C350.14885 (10)0.8186 (5)0.02337 (17)0.0622 (11)
C360.10703 (9)0.8746 (4)0.00049 (15)0.0521 (10)
C370.07921 (8)0.8713 (4)0.04216 (13)0.0448 (9)
C380.09080 (9)0.8051 (4)0.10487 (14)0.0498 (9)
C390.13092 (9)0.7255 (4)0.12528 (15)0.0543 (10)
C400.09541 (9)0.9339 (4)−0.06097 (15)0.0588 (11)
C410.05654 (9)0.9907 (4)−0.08285 (14)0.0531 (10)
C420.02842 (8)0.9957 (4)−0.04315 (12)0.0437 (9)
C430.03971 (8)0.9351 (4)0.02129 (12)0.0431 (8)
C440.01245 (8)0.9381 (4)0.06526 (13)0.0440 (9)
C450.02573 (9)0.8754 (4)0.12668 (13)0.0520 (10)
C460.06412 (9)0.8086 (4)0.14628 (14)0.0523 (10)
C470.19744 (10)0.6458 (5)0.10204 (19)0.0745 (14)
C480.23055 (11)0.7769 (7)0.1231 (2)0.101 (2)
C490.22923 (14)0.8710 (8)0.1838 (3)0.135 (3)
C500.20487 (12)0.5105 (6)0.0501 (2)0.0964 (18)
C510.23083 (16)0.3605 (7)0.0769 (3)0.139 (3)
H65A0.186700.284100.275700.2140*0.700
H65B0.154700.424700.282500.2140*0.700
H66A0.207200.438200.355400.2160*0.700
H66B0.197900.249300.380500.2160*0.700
H66C0.168400.408000.383900.2160*0.700
H67A0.101400.020500.320800.1530*0.700
H67B0.11800−0.073400.265500.1530*0.700
H68A0.14410−0.196100.357400.1710*0.700
H68B0.16000−0.011300.385600.1710*0.700
H68C0.17810−0.098000.330100.1710*0.700
H570.128600.272500.044200.0750*
H580.088200.39420−0.043800.0730*
H62−0.050000.509100.124800.0810*
H63−0.006900.407600.212800.0890*
H64A0.152100.132900.248700.0980*0.700
H64B0.109400.190100.314600.1140*0.300
H65C0.144300.371900.358000.1590*0.300
H65D0.127100.457300.292000.1590*0.300
H66D0.194100.536800.332500.2250*0.300
H66E0.188100.459300.262900.2250*0.300
H66F0.206600.339800.321400.2250*0.300
H67C0.13590−0.029600.239300.1050*0.300
H67D0.17130−0.007300.297500.1050*0.300
H68D0.13430−0.227400.320300.1870*0.300
H68E0.09510−0.114200.302600.1870*0.300
H68F0.12670−0.067000.363800.1870*0.300
H60.405400.984700.631100.0560*
H70.471601.068700.643200.0520*
H110.469900.845300.348600.0490*
H120.406000.735900.342800.0500*
H130.286700.752000.509100.0730*
H14A0.241000.750700.416700.0990*
H14B0.274700.731700.375800.0990*
H15A0.252301.023700.372000.1400*
H15B0.297201.018700.406000.1400*
H15C0.263401.037700.446800.1400*
H16A0.265000.468600.469600.0860*
H16B0.304300.449000.441800.0860*
H17A0.311200.299600.538700.0950*
H17B0.302600.476200.573300.0950*
H17C0.342000.456900.545400.0950*
H230.372000.266500.466000.0500*
H240.414800.386700.552100.0490*
H280.544900.519800.369900.0570*
H290.499900.410200.284700.0600*
H300.371300.197600.192200.0670*
H31A0.303800.224500.184300.0860*
H31B0.307200.212500.258600.0860*
H32A0.296300.504300.225700.1140*
H32B0.335000.501300.195400.1140*
H32C0.338500.489300.269900.1140*
H33A0.35210−0.082100.268600.0770*
H33B0.33430−0.072600.195300.0770*
H34A0.38950−0.259500.212300.0910*
H34B0.41650−0.104200.245500.0910*
H34C0.39860−0.094500.172100.0910*
H400.113800.93620−0.088400.0710*
H410.049101.02630−0.125300.0640*
H450.008400.878100.155800.0620*
H460.071800.765900.187800.0630*
H470.195500.574400.140000.0890*
H48A0.255900.714300.127600.1220*
H48B0.230000.865100.089600.1220*
H49A0.250800.955100.192200.1620*
H49B0.231800.786200.218100.1620*
H49C0.204200.932700.180400.1620*
H50A0.179400.463700.028400.1160*
H50B0.217200.572200.018600.1160*
H51A0.234700.281800.042900.1670*
H51B0.218400.296500.107100.1670*
H51C0.256200.405700.098000.1670*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O70.0821 (18)0.100 (2)0.0935 (19)0.0188 (16)0.0214 (15)0.0102 (16)
O80.123 (2)0.134 (3)0.0587 (15)0.025 (2)0.0270 (15)−0.0005 (17)
N40.0826 (19)0.0592 (18)0.0664 (17)−0.0051 (15)0.0103 (14)−0.0037 (14)
C520.078 (2)0.052 (2)0.073 (2)−0.0053 (18)0.0179 (18)−0.0009 (17)
C530.067 (2)0.0451 (18)0.0688 (19)−0.0071 (15)0.0201 (16)−0.0103 (15)
C540.0663 (19)0.0416 (17)0.0589 (18)−0.0083 (15)0.0215 (15)−0.0124 (14)
C550.080 (2)0.058 (2)0.0578 (18)−0.0048 (18)0.0222 (16)−0.0073 (16)
C560.093 (3)0.069 (2)0.064 (2)−0.002 (2)0.0209 (19)−0.0052 (19)
C570.0597 (19)0.055 (2)0.077 (2)−0.0027 (16)0.0259 (17)−0.0080 (17)
C580.066 (2)0.059 (2)0.0645 (19)−0.0056 (17)0.0318 (16)−0.0084 (16)
C590.0623 (18)0.0424 (17)0.0562 (17)−0.0101 (14)0.0256 (15)−0.0129 (14)
C600.0619 (18)0.0403 (16)0.0550 (17)−0.0087 (14)0.0236 (14)−0.0125 (14)
C610.0634 (19)0.0481 (18)0.0588 (18)−0.0104 (15)0.0282 (15)−0.0106 (15)
C620.072 (2)0.079 (2)0.0597 (19)0.0017 (19)0.0336 (17)−0.0037 (18)
C630.086 (2)0.087 (3)0.058 (2)0.003 (2)0.0347 (18)−0.0041 (19)
C64A0.089 (4)0.091 (5)0.063 (4)0.000 (4)0.011 (3)−0.007 (3)
C65A0.170 (9)0.137 (8)0.179 (9)−0.012 (6)−0.100 (7)−0.006 (7)
C66A0.148 (8)0.187 (10)0.172 (9)0.041 (7)−0.055 (7)−0.071 (8)
C67A0.141 (7)0.144 (7)0.095 (6)0.004 (6)0.015 (5)0.049 (6)
C68A0.115 (6)0.167 (9)0.133 (7)−0.004 (6)−0.008 (5)0.063 (6)
C64B0.106 (10)0.084 (7)0.089 (8)0.009 (7)−0.001 (9)0.026 (8)
C65B0.157 (13)0.122 (9)0.094 (10)0.062 (9)−0.041 (9)−0.064 (9)
C66B0.219 (16)0.115 (15)0.164 (17)−0.077 (13)−0.138 (14)0.050 (13)
C67B0.134 (13)0.087 (8)0.044 (7)0.023 (8)0.024 (7)0.010 (6)
C68B0.26 (3)0.085 (11)0.16 (2)0.034 (16)0.118 (18)0.032 (14)
O10.0543 (13)0.130 (2)0.0708 (15)−0.0224 (14)0.0317 (12)−0.0290 (15)
O20.0489 (12)0.0793 (16)0.0573 (13)−0.0139 (11)0.0058 (10)−0.0152 (12)
N10.0382 (12)0.0571 (16)0.0535 (14)−0.0060 (11)0.0110 (10)−0.0024 (12)
C10.0437 (15)0.062 (2)0.0556 (17)−0.0055 (14)0.0144 (13)−0.0041 (15)
C20.0412 (14)0.0451 (16)0.0412 (14)−0.0019 (12)0.0115 (11)0.0015 (12)
C30.0401 (13)0.0308 (14)0.0382 (13)0.0039 (11)0.0060 (11)0.0048 (11)
C40.0396 (14)0.0333 (14)0.0416 (14)0.0033 (11)0.0060 (11)0.0027 (11)
C50.0438 (15)0.0454 (17)0.0501 (16)−0.0001 (13)0.0047 (13)−0.0005 (14)
C60.0473 (15)0.0523 (18)0.0447 (15)−0.0047 (13)0.0192 (12)−0.0038 (13)
C70.0480 (15)0.0479 (17)0.0349 (13)−0.0040 (13)0.0099 (11)−0.0038 (12)
C80.0403 (14)0.0323 (14)0.0341 (13)0.0028 (11)0.0087 (10)0.0027 (11)
C90.0372 (13)0.0296 (13)0.0350 (13)0.0053 (10)0.0062 (10)0.0056 (10)
C100.0377 (13)0.0319 (14)0.0367 (13)0.0058 (11)0.0057 (10)0.0044 (11)
C110.0424 (14)0.0475 (16)0.0346 (13)0.0039 (13)0.0090 (11)−0.0009 (12)
C120.0423 (14)0.0426 (16)0.0388 (14)0.0018 (12)0.0017 (11)−0.0004 (12)
C130.0375 (15)0.076 (2)0.070 (2)−0.0088 (15)0.0140 (14)−0.0030 (17)
C140.0463 (19)0.108 (3)0.094 (3)0.003 (2)0.0111 (18)0.017 (2)
C150.063 (3)0.127 (4)0.163 (5)0.009 (3)0.030 (3)0.066 (4)
C160.0540 (19)0.078 (2)0.084 (2)−0.0181 (18)0.0174 (17)−0.003 (2)
C170.069 (2)0.089 (3)0.083 (3)−0.003 (2)0.0249 (19)0.011 (2)
O30.0469 (11)0.0778 (16)0.0546 (12)−0.0203 (11)0.0091 (9)−0.0026 (11)
O40.0716 (14)0.106 (2)0.0383 (11)−0.0311 (14)0.0130 (10)−0.0018 (12)
N20.0476 (13)0.0547 (15)0.0398 (12)−0.0105 (11)0.0029 (10)0.0031 (11)
C180.0389 (15)0.0470 (17)0.0499 (16)−0.0023 (13)0.0057 (12)0.0055 (13)
C190.0370 (13)0.0351 (14)0.0410 (14)0.0034 (11)0.0060 (11)0.0060 (11)
C200.0371 (13)0.0314 (14)0.0395 (13)0.0041 (11)0.0084 (11)0.0088 (11)
C210.0442 (14)0.0434 (16)0.0380 (13)−0.0021 (12)0.0073 (11)0.0059 (12)
C220.0488 (16)0.0577 (19)0.0409 (15)−0.0081 (14)0.0065 (12)0.0069 (14)
C230.0334 (13)0.0438 (16)0.0476 (15)−0.0002 (12)0.0088 (11)0.0053 (12)
C240.0377 (14)0.0470 (16)0.0396 (14)0.0014 (12)0.0113 (11)0.0030 (12)
C250.0329 (13)0.0339 (14)0.0407 (13)0.0042 (11)0.0103 (11)0.0061 (11)
C260.0329 (12)0.0312 (14)0.0388 (13)0.0051 (10)0.0067 (10)0.0071 (11)
C270.0354 (13)0.0336 (14)0.0409 (14)0.0037 (11)0.0089 (11)0.0064 (11)
C280.0411 (15)0.0574 (19)0.0448 (15)−0.0070 (13)0.0132 (12)0.0005 (14)
C290.0506 (16)0.064 (2)0.0379 (14)−0.0083 (14)0.0150 (12)0.0010 (14)
C300.0540 (17)0.066 (2)0.0433 (16)−0.0131 (15)−0.0007 (13)0.0020 (15)
C310.064 (2)0.084 (3)0.060 (2)−0.0042 (19)−0.0086 (16)0.0017 (19)
C320.110 (3)0.084 (3)0.080 (3)0.016 (3)−0.010 (2)−0.005 (2)
C330.064 (2)0.072 (2)0.0544 (19)−0.0141 (17)0.0055 (15)−0.0042 (17)
C340.088 (3)0.079 (3)0.066 (2)−0.009 (2)0.0259 (19)−0.0099 (19)
O50.0601 (14)0.118 (2)0.0986 (19)0.0159 (15)0.0362 (14)0.0347 (17)
O60.0661 (14)0.0791 (17)0.0674 (15)0.0113 (13)0.0090 (11)0.0141 (13)
N30.0519 (14)0.0584 (17)0.0712 (17)0.0066 (13)0.0142 (13)0.0075 (14)
C350.0567 (18)0.059 (2)0.074 (2)0.0039 (16)0.0202 (16)0.0069 (17)
C360.0516 (16)0.0481 (18)0.0603 (18)0.0021 (14)0.0197 (14)0.0011 (15)
C370.0506 (15)0.0377 (15)0.0477 (15)−0.0031 (13)0.0131 (12)−0.0050 (12)
C380.0515 (16)0.0443 (17)0.0527 (16)−0.0047 (13)0.0074 (13)−0.0022 (13)
C390.0566 (18)0.0470 (18)0.0580 (18)−0.0019 (14)0.0069 (14)−0.0016 (15)
C400.0592 (19)0.062 (2)0.0615 (19)0.0061 (16)0.0276 (15)0.0055 (16)
C410.0605 (18)0.0585 (19)0.0433 (15)0.0037 (15)0.0173 (13)0.0036 (14)
C420.0522 (16)0.0388 (15)0.0421 (14)−0.0043 (13)0.0141 (12)−0.0029 (12)
C430.0493 (15)0.0388 (15)0.0428 (14)−0.0057 (12)0.0129 (12)−0.0035 (12)
C440.0490 (16)0.0372 (15)0.0473 (15)−0.0050 (12)0.0126 (12)−0.0033 (12)
C450.0576 (18)0.0569 (19)0.0442 (15)−0.0032 (15)0.0166 (13)−0.0014 (14)
C460.0617 (18)0.0520 (18)0.0430 (15)−0.0020 (15)0.0094 (13)0.0013 (14)
C470.0539 (19)0.078 (2)0.091 (3)0.0098 (18)0.0121 (18)0.014 (2)
C480.054 (2)0.107 (4)0.140 (4)0.006 (2)0.011 (2)0.008 (3)
C490.079 (3)0.140 (5)0.180 (5)−0.006 (3)0.005 (3)−0.052 (4)
C500.072 (2)0.098 (3)0.126 (4)0.024 (2)0.036 (2)0.003 (3)
C510.136 (5)0.121 (4)0.174 (5)0.059 (4)0.062 (4)0.024 (4)
Geometric parameters (Å, º) top
O7—C521.222 (5)C13—C161.527 (5)
O8—C561.221 (5)C14—C151.511 (7)
O1—C11.212 (4)C16—C171.509 (5)
O2—C51.217 (4)C6—H60.9300
O3—C181.213 (4)C7—H70.9300
O4—C221.220 (3)C11—H110.9300
O5—C351.216 (4)C12—H120.9300
O6—C391.223 (4)C13—H130.9800
N4—C64B1.59 (3)C14—H14B0.9700
N4—C64A1.479 (9)C14—H14A0.9700
N4—C561.394 (5)C15—H15A0.9600
N4—C521.403 (5)C15—H15B0.9600
N1—C11.403 (4)C15—H15C0.9600
N1—C51.395 (4)C16—H16B0.9700
N1—C131.503 (4)C16—H16A0.9700
N2—C181.400 (3)C17—H17C0.9600
N2—C221.393 (4)C17—H17A0.9600
N2—C301.503 (4)C17—H17B0.9600
N3—C391.393 (4)C18—C191.478 (4)
N3—C351.402 (5)C19—C201.406 (3)
N3—C471.490 (4)C19—C231.371 (4)
C52—C531.467 (5)C20—C261.421 (3)
C53—C571.379 (5)C20—C211.411 (4)
C53—C541.406 (5)C21—C291.373 (4)
C54—C601.414 (4)C21—C221.484 (4)
C54—C551.412 (5)C23—C241.390 (4)
C55—C561.469 (5)C24—C251.384 (3)
C55—C631.373 (5)C25—C27iii1.469 (3)
C57—C581.385 (5)C25—C261.429 (3)
C58—C591.386 (5)C26—C271.426 (3)
C59—C601.434 (4)C27—C281.389 (4)
C59—C61i1.452 (4)C28—C291.386 (4)
C60—C611.430 (4)C30—C331.521 (5)
C61—C621.402 (5)C30—C311.523 (5)
C62—C631.379 (5)C31—C321.501 (6)
C64A—C65A1.403 (14)C33—C341.508 (5)
C64A—C67A1.540 (13)C23—H230.9300
C64B—C67B1.55 (2)C24—H240.9300
C64B—C65B1.38 (2)C28—H280.9300
C65A—C66A1.371 (14)C29—H290.9300
C65B—C66B1.526 (19)C30—H300.9800
C67A—C68A1.411 (13)C31—H31B0.9700
C67B—C68B1.41 (3)C31—H31A0.9700
C57—H570.9300C32—H32A0.9600
C58—H580.9300C32—H32C0.9600
C62—H620.9300C32—H32B0.9600
C63—H630.9300C33—H33A0.9700
C64A—H64A0.9800C33—H33B0.9700
C64B—H64B0.9800C34—H34B0.9600
C65A—H65A0.9700C34—H34C0.9600
C65A—H65B0.9700C34—H34A0.9600
C65B—H65D0.9700C35—C361.477 (5)
C65B—H65C0.9700C36—C371.410 (4)
C66A—H66A0.9600C36—C401.368 (4)
C66A—H66C0.9600C37—C381.409 (4)
C66A—H66B0.9600C37—C431.419 (4)
C66B—H66F0.9600C38—C391.480 (4)
C66B—H66D0.9600C38—C461.375 (4)
C66B—H66E0.9600C40—C411.386 (4)
C67A—H67B0.9700C41—C421.387 (4)
C67A—H67A0.9700C42—C431.427 (4)
C67B—H67D0.9700C42—C44iv1.470 (4)
C67B—H67C0.9700C43—C441.432 (4)
C68A—H68A0.9600C44—C451.383 (4)
C68A—H68C0.9600C45—C461.389 (4)
C68A—H68B0.9600C47—C481.500 (6)
C68B—H68D0.9600C47—C501.554 (6)
C68B—H68E0.9600C48—C491.478 (8)
C68B—H68F0.9600C50—C511.479 (7)
C1—C21.481 (4)C40—H400.9300
C2—C31.406 (4)C41—H410.9300
C2—C61.374 (4)C45—H450.9300
C3—C91.421 (3)C46—H460.9300
C3—C41.411 (3)C47—H470.9800
C4—C51.482 (4)C48—H48A0.9700
C4—C121.367 (4)C48—H48B0.9700
C6—C71.395 (4)C49—H49A0.9600
C7—C81.384 (4)C49—H49B0.9600
C8—C10ii1.470 (3)C49—H49C0.9600
C8—C91.431 (3)C50—H50A0.9700
C9—C101.422 (3)C50—H50B0.9700
C10—C111.389 (3)C51—H51A0.9600
C11—C121.391 (4)C51—H51B0.9600
C13—C141.506 (5)C51—H51C0.9600
Cg1···Cg13v3.6863 (19)Cg5···Cg9vi3.6604 (16)
Cg2···Cg113.7041 (19)Cg6···Cg103.5395 (15)
Cg2···Cg12v3.6485 (18)Cg6···Cg8vi3.7743 (16)
Cg2···Cg13v3.6165 (18)Cg6···Cg93.7544 (16)
Cg3···Cg133.7245 (19)Cg7···Cg9vi3.5613 (15)
Cg4···Cg133.6034 (18)Cg7···Cg103.7518 (14)
Cg4···Cg14v3.7518 (18)
C52—N4—C56122.8 (3)C15—C14—H14B109.00
C52—N4—C64A115.0 (5)H14A—C14—H14B108.00
C52—N4—C64B127.8 (10)C13—C14—H14B109.00
C56—N4—C64A122.2 (5)C15—C14—H14A109.00
C56—N4—C64B109.3 (10)C13—C14—H14A109.00
C1—N1—C13117.7 (2)H15B—C15—H15C110.00
C5—N1—C13119.2 (2)C14—C15—H15A109.00
C1—N1—C5123.1 (2)C14—C15—H15B109.00
C18—N2—C22123.1 (2)H15A—C15—H15C110.00
C18—N2—C30118.9 (2)H15A—C15—H15B109.00
C22—N2—C30118.1 (2)C14—C15—H15C109.00
C35—N3—C47118.7 (3)C13—C16—H16B109.00
C39—N3—C47118.3 (3)C13—C16—H16A109.00
C35—N3—C39123.0 (3)C17—C16—H16A109.00
O7—C52—C53121.5 (3)H16A—C16—H16B108.00
N4—C52—C53118.0 (3)C17—C16—H16B109.00
O7—C52—N4120.5 (3)C16—C17—H17C109.00
C52—C53—C57119.4 (3)H17A—C17—H17B110.00
C54—C53—C57119.9 (3)C16—C17—H17B110.00
C52—C53—C54120.7 (3)H17B—C17—H17C109.00
C55—C54—C60120.4 (3)H17A—C17—H17C109.00
C53—C54—C60120.3 (3)C16—C17—H17A109.00
C53—C54—C55119.3 (3)O3—C18—N2121.0 (2)
C56—C55—C63120.2 (3)O3—C18—C19121.1 (2)
C54—C55—C56120.9 (3)N2—C18—C19117.9 (2)
C54—C55—C63118.9 (3)C20—C19—C23119.7 (2)
O8—C56—N4120.2 (4)C18—C19—C23119.7 (2)
N4—C56—C55117.9 (3)C18—C19—C20120.6 (2)
O8—C56—C55121.8 (4)C21—C20—C26120.3 (2)
C53—C57—C58120.1 (3)C19—C20—C21119.5 (2)
C57—C58—C59122.6 (3)C19—C20—C26120.2 (2)
C58—C59—C61i123.0 (3)C20—C21—C22120.6 (2)
C60—C59—C61i119.2 (3)C20—C21—C29119.2 (2)
C58—C59—C60117.9 (3)C22—C21—C29120.2 (2)
C59—C60—C61120.8 (3)O4—C22—N2121.1 (3)
C54—C60—C61119.9 (3)O4—C22—C21121.1 (3)
C54—C60—C59119.3 (3)N2—C22—C21117.8 (2)
C59i—C61—C60120.0 (3)C19—C23—C24120.7 (2)
C59i—C61—C62122.9 (3)C23—C24—C25121.9 (2)
C60—C61—C62117.1 (3)C24—C25—C26118.4 (2)
C61—C62—C63122.4 (3)C24—C25—C27iii122.6 (2)
C55—C63—C62121.3 (3)C26—C25—C27iii119.0 (2)
C65A—C64A—C67A131.9 (8)C25—C26—C27121.8 (2)
N4—C64A—C65A116.8 (7)C20—C26—C25119.1 (2)
N4—C64A—C67A111.0 (7)C20—C26—C27119.1 (2)
C65B—C64B—C67B144 (2)C25iii—C27—C26119.2 (2)
N4—C64B—C67B102.0 (13)C26—C27—C28118.5 (2)
N4—C64B—C65B104.8 (12)C25iii—C27—C28122.3 (2)
C64A—C65A—C66A134.1 (10)C27—C28—C29121.7 (3)
C64B—C65B—C66B122.1 (15)C21—C29—C28121.2 (3)
C64A—C67A—C68A118.4 (9)C31—C30—C33113.5 (3)
C64B—C67B—C68B112.9 (16)N2—C30—C31112.6 (2)
C58—C57—H57120.00N2—C30—C33111.3 (2)
C53—C57—H57120.00C30—C31—C32114.8 (3)
C59—C58—H58119.00C30—C33—C34114.1 (3)
C57—C58—H58119.00C19—C23—H23120.00
C63—C62—H62119.00C24—C23—H23120.00
C61—C62—H62119.00C25—C24—H24119.00
C62—C63—H63119.00C23—C24—H24119.00
C55—C63—H63119.00C27—C28—H28119.00
N4—C64A—H64A92.00C29—C28—H28119.00
C67A—C64A—H64A92.00C28—C29—H29119.00
C65A—C64A—H64A92.00C21—C29—H29119.00
C67B—C64B—H64B100.00N2—C30—H30106.00
N4—C64B—H64B100.00C31—C30—H30106.00
C65B—C64B—H64B100.00C33—C30—H30106.00
C66A—C65A—H65A104.00C32—C31—H31B109.00
H65A—C65A—H65B105.00H31A—C31—H31B108.00
C66A—C65A—H65B104.00C30—C31—H31B109.00
C64A—C65A—H65A104.00C32—C31—H31A109.00
C64A—C65A—H65B104.00C30—C31—H31A109.00
H65C—C65B—H65D107.00C31—C32—H32A109.00
C66B—C65B—H65D107.00C31—C32—H32B109.00
C64B—C65B—H65D107.00H32B—C32—H32C110.00
C64B—C65B—H65C107.00H32A—C32—H32C109.00
C66B—C65B—H65C107.00C31—C32—H32C110.00
C65A—C66A—H66B109.00H32A—C32—H32B109.00
C65A—C66A—H66C109.00C30—C33—H33A109.00
C65A—C66A—H66A110.00C30—C33—H33B109.00
H66B—C66A—H66C109.00C34—C33—H33A109.00
H66A—C66A—H66C109.00C34—C33—H33B109.00
H66A—C66A—H66B110.00H33A—C33—H33B108.00
C65B—C66B—H66D110.00C33—C34—H34C109.00
H66E—C66B—H66F109.00H34A—C34—H34C109.00
H66D—C66B—H66E109.00H34B—C34—H34C109.00
H66D—C66B—H66F110.00H34A—C34—H34B109.00
C65B—C66B—H66F110.00C33—C34—H34A109.00
C65B—C66B—H66E109.00C33—C34—H34B110.00
C68A—C67A—H67B108.00O5—C35—N3120.9 (3)
C64A—C67A—H67A108.00O5—C35—C36121.5 (3)
C64A—C67A—H67B108.00N3—C35—C36117.5 (3)
C68A—C67A—H67A108.00C35—C36—C37120.3 (3)
H67A—C67A—H67B107.00C35—C36—C40119.9 (3)
C64B—C67B—H67C109.00C37—C36—C40119.7 (3)
C64B—C67B—H67D109.00C36—C37—C38119.8 (3)
H67C—C67B—H67D108.00C36—C37—C43120.3 (3)
C68B—C67B—H67D109.00C38—C37—C43120.0 (3)
C68B—C67B—H67C109.00C37—C38—C39120.2 (3)
H68A—C68A—H68C110.00C37—C38—C46119.7 (3)
C67A—C68A—H68C110.00C39—C38—C46120.1 (3)
H68B—C68A—H68C110.00O6—C39—N3121.3 (3)
H68A—C68A—H68B109.00O6—C39—C38120.6 (3)
C67A—C68A—H68B109.00N3—C39—C38118.1 (3)
C67A—C68A—H68A109.00C36—C40—C41120.8 (3)
C67B—C68B—H68E109.00C40—C41—C42121.7 (3)
H68E—C68B—H68F110.00C41—C42—C43118.7 (3)
H68D—C68B—H68E109.00C41—C42—C44iv122.1 (2)
C67B—C68B—H68F109.00C43—C42—C44iv119.1 (2)
C67B—C68B—H68D109.00C37—C43—C42118.7 (2)
H68D—C68B—H68F109.00C37—C43—C44119.4 (2)
O1—C1—N1121.2 (3)C42—C43—C44121.9 (2)
N1—C1—C2117.5 (2)C43—C44—C45118.2 (3)
O1—C1—C2121.3 (3)C42iv—C44—C43119.0 (2)
C3—C2—C6119.2 (2)C42iv—C44—C45122.9 (3)
C1—C2—C6119.7 (2)C44—C45—C46122.2 (3)
C1—C2—C3121.0 (2)C38—C46—C45120.6 (3)
C4—C3—C9120.0 (2)N3—C47—C48112.5 (3)
C2—C3—C4119.5 (2)N3—C47—C50110.8 (3)
C2—C3—C9120.6 (2)C48—C47—C50115.4 (3)
C3—C4—C12119.8 (2)C47—C48—C49115.6 (4)
C5—C4—C12119.9 (2)C47—C50—C51112.8 (4)
C3—C4—C5120.4 (2)C36—C40—H40120.00
N1—C5—C4118.2 (2)C41—C40—H40120.00
O2—C5—N1120.8 (3)C40—C41—H41119.00
O2—C5—C4121.1 (3)C42—C41—H41119.00
C2—C6—C7120.9 (3)C44—C45—H45119.00
C6—C7—C8121.9 (2)C46—C45—H45119.00
C7—C8—C9118.3 (2)C38—C46—H46120.00
C9—C8—C10ii118.9 (2)C45—C46—H46120.00
C7—C8—C10ii122.8 (2)N3—C47—H47106.00
C8—C9—C10121.9 (2)C48—C47—H47106.00
C3—C9—C10119.1 (2)C50—C47—H47106.00
C3—C9—C8119.1 (2)C47—C48—H48A108.00
C8ii—C10—C9119.3 (2)C47—C48—H48B108.00
C8ii—C10—C11121.9 (2)C49—C48—H48A108.00
C9—C10—C11118.8 (2)C49—C48—H48B108.00
C10—C11—C12121.4 (2)H48A—C48—H48B107.00
C4—C12—C11120.9 (2)C48—C49—H49A109.00
C14—C13—C16114.1 (3)C48—C49—H49B109.00
N1—C13—C16111.2 (3)C48—C49—H49C109.00
N1—C13—C14113.3 (3)H49A—C49—H49B110.00
C13—C14—C15114.7 (4)H49A—C49—H49C110.00
C13—C16—C17114.0 (3)H49B—C49—H49C109.00
C7—C6—H6120.00C47—C50—H50A109.00
C2—C6—H6120.00C47—C50—H50B109.00
C8—C7—H7119.00C51—C50—H50A109.00
C6—C7—H7119.00C51—C50—H50B109.00
C10—C11—H11119.00H50A—C50—H50B108.00
C12—C11—H11119.00C50—C51—H51A109.00
C11—C12—H12119.00C50—C51—H51B109.00
C4—C12—H12120.00C50—C51—H51C109.00
N1—C13—H13106.00H51A—C51—H51B109.00
C16—C13—H13106.00H51A—C51—H51C109.00
C14—C13—H13106.00H51B—C51—H51C109.00
C56—N4—C52—O7−173.3 (4)C12—C4—C5—N1−173.8 (2)
C56—N4—C52—C537.9 (5)C12—C4—C5—O26.1 (4)
C64A—N4—C52—O75.1 (6)C2—C6—C7—C82.0 (4)
C64A—N4—C52—C53−173.8 (4)C6—C7—C8—C10ii176.6 (3)
C52—N4—C56—O8176.3 (4)C6—C7—C8—C9−1.0 (4)
C52—N4—C56—C55−4.8 (5)C10ii—C8—C9—C3−179.1 (2)
C64A—N4—C56—O8−2.0 (7)C10ii—C8—C9—C100.4 (3)
C64A—N4—C56—C55176.9 (5)C7—C8—C9—C10178.1 (2)
C52—N4—C64A—C65A77.9 (8)C7—C8—C10ii—C11ii1.7 (4)
C52—N4—C64A—C67A−107.3 (7)C9—C8—C10ii—C11ii179.4 (2)
C56—N4—C64A—C65A−103.7 (8)C7—C8—C10ii—C9ii−178.0 (2)
C56—N4—C64A—C67A71.2 (8)C7—C8—C9—C3−1.4 (3)
C5—N1—C1—O1178.7 (3)C9—C8—C10ii—C9ii−0.4 (3)
C5—N1—C1—C2−2.2 (4)C3—C9—C10—C11−1.1 (3)
C13—N1—C1—O1−1.9 (4)C3—C9—C10—C8ii179.1 (2)
C13—N1—C1—C2177.1 (3)C8—C9—C10—C8ii−0.4 (3)
C1—N1—C5—O2176.1 (3)C8—C9—C10—C11179.4 (2)
C1—N1—C5—C4−3.9 (4)C9—C10—C11—C12−1.3 (4)
C13—N1—C5—O2−3.2 (4)C8ii—C10—C11—C12178.4 (2)
C13—N1—C5—C4176.8 (2)C10—C11—C12—C42.3 (4)
C1—N1—C13—C14122.8 (3)N1—C13—C14—C15−51.9 (4)
C1—N1—C13—C16−107.1 (3)C16—C13—C14—C15179.5 (3)
C5—N1—C13—C14−57.8 (4)N1—C13—C16—C1761.8 (4)
C5—N1—C13—C1672.3 (3)C14—C13—C16—C17−168.5 (3)
C30—N2—C18—O37.2 (4)O3—C18—C19—C20172.8 (3)
C30—N2—C18—C19−173.2 (2)O3—C18—C19—C23−7.6 (4)
C18—N2—C22—O4175.1 (3)N2—C18—C19—C20−6.8 (4)
C22—N2—C30—C31−127.0 (3)N2—C18—C19—C23172.9 (2)
C22—N2—C30—C33104.2 (3)C18—C19—C20—C26−177.9 (2)
C18—N2—C22—C21−4.5 (4)C23—C19—C20—C21−177.5 (2)
C30—N2—C22—O4−3.7 (4)C18—C19—C20—C212.2 (4)
C30—N2—C22—C21176.7 (2)C23—C19—C20—C262.5 (4)
C18—N2—C30—C3154.1 (3)C18—C19—C23—C24179.4 (3)
C18—N2—C30—C33−74.6 (3)C20—C19—C23—C24−1.0 (4)
C22—N2—C18—O3−171.6 (3)C26—C20—C21—C22−178.5 (2)
C22—N2—C18—C198.0 (4)C26—C20—C21—C29−0.5 (4)
C35—N3—C39—C382.0 (5)C19—C20—C26—C25−2.6 (3)
C35—N3—C47—C50−54.2 (4)C19—C20—C21—C221.5 (4)
C39—N3—C47—C48−104.2 (4)C19—C20—C21—C29179.5 (3)
C47—N3—C39—O62.3 (5)C21—C20—C26—C27−0.5 (3)
C47—N3—C39—C38−177.0 (3)C19—C20—C26—C27179.5 (2)
C35—N3—C47—C4876.7 (4)C21—C20—C26—C25177.4 (2)
C47—N3—C35—C36168.7 (3)C20—C21—C22—O4179.9 (3)
C35—N3—C39—O6−178.7 (3)C20—C21—C22—N2−0.5 (4)
C39—N3—C35—C36−10.3 (5)C29—C21—C22—O41.9 (5)
C47—N3—C35—O5−9.3 (5)C29—C21—C22—N2−178.5 (3)
C39—N3—C35—O5171.8 (3)C20—C21—C29—C281.2 (4)
C39—N3—C47—C50124.9 (3)C22—C21—C29—C28179.2 (3)
N4—C52—C53—C54−5.9 (5)C19—C23—C24—C25−0.5 (4)
N4—C52—C53—C57174.4 (3)C23—C24—C25—C27iii−178.6 (2)
O7—C52—C53—C57−4.5 (5)C23—C24—C25—C260.4 (4)
O7—C52—C53—C54175.3 (3)C27iii—C25—C26—C20−179.9 (2)
C52—C53—C57—C58−178.5 (3)C27iii—C25—C26—C27−2.0 (3)
C52—C53—C54—C60−179.3 (3)C24—C25—C26—C27179.0 (2)
C57—C53—C54—C55−179.2 (3)C24—C25—C26—C201.2 (3)
C54—C53—C57—C581.8 (5)C24—C25—C27iii—C26iii−179.1 (2)
C52—C53—C54—C551.0 (5)C24—C25—C27iii—C28iii1.9 (4)
C57—C53—C54—C600.5 (5)C26—C25—C27iii—C26iii1.9 (3)
C53—C54—C55—C562.1 (5)C26—C25—C27iii—C28iii−177.0 (2)
C53—C54—C60—C61179.1 (3)C20—C26—C27—C25iii179.9 (2)
C55—C54—C60—C61−1.2 (5)C25—C26—C27—C28−177.0 (2)
C60—C54—C55—C631.5 (5)C20—C26—C27—C280.9 (3)
C53—C54—C55—C63−178.9 (3)C25—C26—C27—C25iii2.0 (3)
C55—C54—C60—C59178.0 (3)C26—C27—C28—C29−0.2 (4)
C60—C54—C55—C56−177.5 (3)C25iii—C27—C28—C29−179.2 (3)
C53—C54—C60—C59−1.6 (4)C27—C28—C29—C21−0.8 (5)
C56—C55—C63—C62178.6 (4)N2—C30—C33—C34−69.0 (3)
C54—C55—C63—C62−0.5 (6)C31—C30—C33—C34162.8 (3)
C54—C55—C56—N4−0.4 (5)C33—C30—C31—C32177.9 (3)
C63—C55—C56—O8−0.5 (6)N2—C30—C31—C3250.3 (4)
C63—C55—C56—N4−179.4 (3)O5—C35—C36—C37−171.0 (3)
C54—C55—C56—O8178.5 (4)O5—C35—C36—C407.5 (5)
C53—C57—C58—C59−3.0 (5)N3—C35—C36—C3711.1 (5)
C57—C58—C59—C601.7 (5)N3—C35—C36—C40−170.5 (3)
C57—C58—C59—C61i−178.5 (3)C35—C36—C37—C38−3.5 (4)
C58—C59—C60—C540.6 (4)C35—C36—C37—C43176.2 (3)
C60—C59—C61i—C60i0.0 (4)C40—C36—C37—C38178.1 (3)
C58—C59—C60—C61179.8 (3)C40—C36—C37—C43−2.3 (4)
C61i—C59—C60—C54−179.3 (3)C35—C36—C40—C41−178.6 (3)
C60—C59—C61i—C62i−179.3 (3)C37—C36—C40—C41−0.1 (5)
C58—C59—C61i—C60i−179.8 (3)C36—C37—C38—C39−5.1 (4)
C58—C59—C61i—C62i0.9 (5)C36—C37—C38—C46177.4 (3)
C61i—C59—C60—C610.0 (4)C43—C37—C38—C39175.2 (3)
C59—C60—C61—C62−179.3 (3)C43—C37—C38—C46−2.3 (4)
C54—C60—C61—C62−0.1 (4)C36—C37—C43—C422.4 (4)
C59—C60—C61—C59i0.0 (4)C36—C37—C43—C44−177.2 (3)
C54—C60—C61—C59i179.3 (3)C38—C37—C43—C42−177.9 (3)
C60—C61—C62—C631.1 (5)C38—C37—C43—C442.5 (4)
C59i—C61—C62—C63−178.2 (3)C37—C38—C39—O6−173.3 (3)
C61—C62—C63—C55−0.9 (6)C37—C38—C39—N36.0 (4)
C65A—C64A—C67A—C68A−17.1 (15)C46—C38—C39—O64.2 (5)
C67A—C64A—C65A—C66A−29.2 (19)C46—C38—C39—N3−176.5 (3)
N4—C64A—C67A—C68A169.1 (7)C37—C38—C46—C450.6 (5)
N4—C64A—C65A—C66A144.4 (11)C39—C38—C46—C45−177.0 (3)
N1—C1—C2—C6−176.1 (3)C36—C40—C41—C422.3 (5)
O1—C1—C2—C3−174.9 (3)C40—C41—C42—C43−2.1 (4)
O1—C1—C2—C63.0 (5)C40—C41—C42—C44iv177.7 (3)
N1—C1—C2—C36.1 (4)C41—C42—C43—C37−0.3 (4)
C3—C2—C6—C7−0.5 (4)C41—C42—C43—C44179.3 (3)
C1—C2—C3—C9175.9 (2)C44iv—C42—C43—C37179.9 (3)
C1—C2—C3—C4−3.4 (4)C44iv—C42—C43—C44−0.5 (4)
C1—C2—C6—C7−178.4 (3)C41—C42—C44iv—C43iv−179.3 (3)
C6—C2—C3—C4178.7 (3)C41—C42—C44iv—C45iv−0.4 (5)
C6—C2—C3—C9−1.9 (4)C43—C42—C44iv—C43iv0.5 (4)
C2—C3—C4—C12177.6 (3)C43—C42—C44iv—C45iv179.4 (3)
C9—C3—C4—C5177.7 (2)C37—C43—C44—C45−1.0 (4)
C9—C3—C4—C12−1.8 (4)C37—C43—C44—C42iv−179.9 (3)
C2—C3—C9—C82.9 (3)C42—C43—C44—C45179.4 (3)
C2—C3—C9—C10−176.7 (2)C42—C43—C44—C42iv0.5 (4)
C4—C3—C9—C102.7 (3)C43—C44—C45—C46−0.8 (4)
C2—C3—C4—C5−3.0 (4)C42iv—C44—C45—C46178.1 (3)
C4—C3—C9—C8−177.8 (2)C44—C45—C46—C381.0 (5)
C3—C4—C12—C11−0.7 (4)N3—C47—C48—C4968.0 (5)
C3—C4—C5—O2−173.4 (3)C50—C47—C48—C49−163.5 (4)
C3—C4—C5—N16.7 (4)N3—C47—C50—C51−150.6 (4)
C5—C4—C12—C11179.9 (3)C48—C47—C50—C5180.0 (5)
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z; (v) x, y−1, z; (vi) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O4vii0.932.553.170 (4)125
C13—H13···O10.982.252.745 (4)110
C14—H14B···O20.972.372.930 (4)116
C15—H15B···O3vi0.962.423.323 (5)156
C16—H16B···O20.972.533.097 (4)117
C30—H30···O40.982.272.746 (4)109
C31—H31B···O30.972.342.895 (4)116
C32—H32C···O20.962.603.453 (5)148
C33—H33A···O30.972.533.107 (4)118
C41—H41···O8viii0.932.493.343 (4)153
C47—H47···O60.982.262.749 (4)109
C48—H48B···O50.972.563.127 (5)118
C49—H49C···O7vi0.962.563.481 (6)162
C50—H50B···O50.972.492.880 (5)104
C64A—H64A···O70.981.952.667 (9)128
C67A—H67A···O80.972.603.139 (11)116
Symmetry codes: (vi) x, y+1, z; (vii) x, −y+3/2, z+1/2; (viii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC34H30N2O4
Mr530.60
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)34.009 (4), 7.5035 (10), 21.248 (3)
β (°) 100.562 (2)
V (Å3)5330.3 (12)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.40 × 0.05 × 0.05
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.966, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections		85917, 9351, 6350
Rint0.051
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.166, 1.03
No. of reflections9351
No. of parameters760
No. of restraints871
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.21

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), publCIF (Westrip, 2010).

Selected interatomic distances (Å) top
Cg1···Cg13i3.6863 (19)Cg5···Cg9ii3.6604 (16)
Cg2···Cg113.7041 (19)Cg6···Cg103.5395 (15)
Cg2···Cg12i3.6485 (18)Cg6···Cg8ii3.7743 (16)
Cg2···Cg13i3.6165 (18)Cg6···Cg93.7544 (16)
Cg3···Cg133.7245 (19)Cg7···Cg9ii3.5613 (15)
Cg4···Cg133.6034 (18)Cg7···Cg103.7518 (14)
Cg4···Cg14i3.7518 (18)
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O4iii0.932.553.170 (4)125
C15—H15B···O3ii0.962.423.323 (5)156
C32—H32C···O20.962.603.453 (5)148
C41—H41···O8iv0.932.493.343 (4)153
C49—H49C···O7ii0.962.563.481 (6)162
Symmetry codes: (ii) x, y+1, z; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.
 

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ISSN: 2056-9890
Volume 66| Part 10| October 2010| Pages o2570-o2571
doi:10.1107/S1600536810036275
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