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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 64| Part 1| January 2008| Page o140
https://doi.org/10.1107/S1600536807063295

13b,13c-Di-2-pyridyl-5,7,12,13b,13c,14-hexa­hydro-6H,13H-5a,6a,12a,13a-tetra­azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione methanol hemisolvate

Lin Li,a Zhi-Guo Wangb and Yu-Zhou Wanga*

aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and bSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
*Correspondence e-mail: yutian830@yahoo.com.cn

(Received 22 October 2007; accepted 26 November 2007; online 6 December 2007)

The title compound, C30H24N6O2·0.5CH3OH, a glycoluril derivative with two pyridine substituents on the convex face of the glycoluril system, is an important inter­mediate for the synthesis of more complex glycoluril derivatives. The compound crystallizes with two independent mol­ecules in the asymmetric unit, one of which exhibits disorder of one benzene ring over two orientations with refined site occupancy factors 0.65 (4):0.35 (4). The crystal structure contains several short C—H⋯O contacts, and the methanol mol­ecule forms an O—H⋯O hydrogen bond to one of the glycoluril mol­ecules.

Related literature

For synthetic details, see: Wang et al. (2006[Wang, Z. G., Zhou, B. H., Chen, Y. F., Yin, G. D., Li, Y. T., Wu, A. X. & Isaacs, L. (2006). J. Org. Chem. 71, 4502-4508.]). For general related literature, see: Adrian & Wilcox (1989[Adrian, J. C. Jr & Wilcox, C. S. (1989). J. Am. Chem. Soc. 111, 8055-8057.]); Behrend et al. (1905[Behrend, R., Meyer, E. & Rusche, F. (1905). Liebigs Ann. Chem. 339, 1-37.]); Freeman et al. (1981[Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc. 103, 7367-7368.]); Rowan et al. (1999[Rowan, A. E., Elemans, J. A. A. W. & Nolte, R. J. M. (1999). Acc. Chem. Res. 32, 995-1006.]); Rebek (2005[Rebek, J. Jr (2005). Angew. Chem. Int. Ed. 44, 2068-2078.]); Sanderson et al. (1989[Sanderson, P. E. J., Kilburn, J. D. & Still, W. C. (1989). J. Am. Chem. Soc. 111, 8314-8315.]); Wu et al. (2002[Wu, A. X., Fettinger, J. C. & Isaacs, L. (2002). Tetrahedron, 58, 9769-9777.]).

[Scheme 1]

Experimental

Crystal data

  • C30H24N6O2·0.5CH4O

  • Mr = 516.57

  • Monoclinic, P 21 /c

  • a = 15.0063 (10) Å

  • b = 20.5919 (13) Å

  • c = 18.0864 (12) Å

  • β = 113.405 (1)°

  • V = 5129.0 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 292 (2) K

  • 0.30 × 0.30 × 0.20 mm
Data collection

  • Bruker SMART 4K CCD diffractometer

  • Absorption correction: none

  • 68334 measured reflections

  • 8988 independent reflections

  • 7325 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.208

  • S = 1.08

  • 8988 reflections

  • 734 parameters

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H5⋯O2 0.82 2.02 2.840 (8) 178
C2—H2A⋯O5i 0.93 2.35 3.279 (9) 174
C22—H22A⋯O2ii 0.93 2.57 3.462 (4) 160
C43—H43A⋯O3iii 0.93 2.60 3.249 (5) 128
C46—H46A⋯O1 0.93 2.59 3.340 (4) 138
C51—H51A⋯O2iv 0.93 2.52 3.419 (4) 164
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807063295/bi2258sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063295/bi2258Isup2.hkl

checkCIF report


Comment top

In 1905, Behrend synthesized an insoluble polymeric material now known as Behrend's polymer using an acid-induced condensation reaction of glycoluril and formaldehyde (Behrend et al., 1905). The molecular structure was characterized and named as cucurbituril by Mock and co-workers in 1981 (Freeman et al., 1981). Glycoluril and its derivatives have been widely used as building blocks for supramolecular chemistry, for example in the formation of molecular clefts, armatures, bowls, tweezers and clips (Adrian & Wilcox, 1989; Freeman et al., 1981; Rebek, 2005; Sanderson et al., 1989; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives, we report the crystal structure of the title compound.

The clip-shaped molecular structure is shown in Fig. 1. It has six fused rings and two pyridine rings. The crystal structure contains several short C—H···O contacts, and the methanol molecule forms an O—H···O hydrogen bond to one of the glycoluril molecules.

Related literature top

For synthesis details, see: Wang et al. (2006). For general related literature, see: Adrian & Wilcox (1989); Behrend et al. (1905); Freeman et al. (1981); Rowan et al. (1999); Rebek (2005); Sanderson et al. (1989); Wu et al. (2002).

Experimental top

The compound was synthesized according to a literature procedure (Wang et al., 2006) in 31% isolated yield. Crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform and methanol solution (20:1 v/v) at 293 K.

Refinement top

One phenyl ring of one molecule is disordered. It was modelled in two orientations, constrained to be regular hexagons, with refined site occupancy factors 0.35 (4):0.65 (4). H atoms bound to C were positioned geometrically and constrained to ride on their parent atoms, with d(C—H) = 0.93–0.97 Å and with Uiso(H) = 1.2 or 1.5Ueq(C). The H atom of the methanol molecule was placed along the O5···O2 vector with d(O5—H5) = 0.82 Å and refined as riding on O5 with Uiso(H) = 1.5Ueq(O).

Structure description top

In 1905, Behrend synthesized an insoluble polymeric material now known as Behrend's polymer using an acid-induced condensation reaction of glycoluril and formaldehyde (Behrend et al., 1905). The molecular structure was characterized and named as cucurbituril by Mock and co-workers in 1981 (Freeman et al., 1981). Glycoluril and its derivatives have been widely used as building blocks for supramolecular chemistry, for example in the formation of molecular clefts, armatures, bowls, tweezers and clips (Adrian & Wilcox, 1989; Freeman et al., 1981; Rebek, 2005; Sanderson et al., 1989; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives, we report the crystal structure of the title compound.

The clip-shaped molecular structure is shown in Fig. 1. It has six fused rings and two pyridine rings. The crystal structure contains several short C—H···O contacts, and the methanol molecule forms an O—H···O hydrogen bond to one of the glycoluril molecules.

For synthesis details, see: Wang et al. (2006). For general related literature, see: Adrian & Wilcox (1989); Behrend et al. (1905); Freeman et al. (1981); Rowan et al. (1999); Rebek (2005); Sanderson et al. (1989); Wu et al. (2002).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of the non-disordered molecule in the asymmetric unit, with displacement ellipsoids drawn at the 50% proability level for non-H atoms.
13b,13c-Di-2-pyridyl-5,7,12,13b,13c,14-hexahydro-6H,13H- 5a,6a,12a,13a-tetraazabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene- 6,13-dione methanol hemisolvate top
Crystal data top
C30H24N6O2·0.5CH4OF(000) = 2168
Mr = 516.57Dx = 1.338 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9377 reflections
a = 15.0063 (10) Åθ = 2.3–24.5°
b = 20.5919 (13) ŵ = 0.09 mm−1
c = 18.0864 (12) ÅT = 292 K
β = 113.405 (1)°Block, colourless
V = 5129.0 (6) Å30.30 × 0.30 × 0.20 mm
Z = 8
Data collection top
Bruker SMART 4K CCD
diffractometer		7325 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
φ and ω scansh = −17→17
68334 measured reflectionsk = −24→24
8988 independent reflectionsl = −21→21
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0999P)2 + 4.5477P]
where P = (Fo2 + 2Fc2)/3
8988 reflections(Δ/σ)max < 0.001
734 parametersΔρmax = 0.68 e Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C30H24N6O2·0.5CH4OV = 5129.0 (6) Å3
Mr = 516.57Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.0063 (10) ŵ = 0.09 mm−1
b = 20.5919 (13) ÅT = 292 K
c = 18.0864 (12) Å0.30 × 0.30 × 0.20 mm
β = 113.405 (1)°
Data collection top
Bruker SMART 4K CCD
diffractometer		7325 reflections with I > 2σ(I)
68334 measured reflectionsRint = 0.037
8988 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.208H-atom parameters constrained
S = 1.08Δρmax = 0.68 e Å−3
8988 reflectionsΔρmin = −0.56 e Å−3
734 parameters
Special details top

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

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)
O10.35883 (16)0.31312 (11)0.35693 (14)0.0567 (6)
O20.07810 (17)0.35765 (11)0.48148 (13)0.0545 (6)
O30.39873 (17)0.60364 (10)−0.02765 (13)0.0543 (6)
O40.19640 (17)0.56407 (12)0.16797 (17)0.0685 (7)
N10.20302 (17)0.35391 (11)0.29519 (14)0.0407 (5)
N20.09710 (19)0.37701 (11)0.36331 (14)0.0445 (6)
N30.22538 (17)0.25952 (11)0.35859 (14)0.0392 (5)
N40.09295 (18)0.27518 (11)0.40090 (14)0.0425 (6)
N50.0373 (2)0.35266 (15)0.14809 (18)0.0683 (8)
N60.0988 (2)0.20264 (13)0.21698 (16)0.0559 (7)
N70.41144 (16)0.52050 (10)0.06155 (13)0.0367 (5)
N80.30693 (16)0.50807 (11)0.13356 (14)0.0386 (5)
N90.42379 (18)0.62206 (11)0.10440 (14)0.0428 (6)
N100.35400 (18)0.60006 (12)0.20074 (15)0.0469 (6)
N110.45044 (18)0.43855 (11)0.24979 (14)0.0436 (6)
N120.6039 (2)0.60347 (15)0.22005 (18)0.0622 (8)
C10.1993 (2)0.47681 (13)0.39507 (18)0.0459 (7)
C20.2288 (3)0.51885 (16)0.4606 (2)0.0591 (9)
H2A0.18780.52730.48680.071*
C30.3195 (3)0.54821 (18)0.4871 (2)0.0719 (11)
H3A0.33860.57670.53050.086*
C40.3810 (3)0.53545 (19)0.4495 (3)0.0751 (11)
H4A0.44140.55550.46680.090*
C50.3524 (3)0.49261 (17)0.3858 (2)0.0619 (9)
H5A0.39470.48330.36110.074*
C60.2621 (2)0.46312 (14)0.35764 (18)0.0467 (7)
C70.2320 (2)0.41998 (14)0.28440 (18)0.0456 (7)
H7A0.17810.44050.24110.055*
H7B0.28560.41720.26740.055*
C80.0980 (2)0.44777 (14)0.36560 (19)0.0490 (7)
H8A0.06700.46220.40060.059*
H8B0.06010.46410.31190.059*
C90.2722 (2)0.30936 (14)0.34003 (16)0.0402 (6)
C100.0892 (2)0.33885 (14)0.42135 (17)0.0416 (6)
C110.1102 (2)0.34124 (13)0.29936 (16)0.0388 (6)
C120.0234 (2)0.35063 (13)0.21877 (18)0.0439 (7)
C13−0.0634 (2)0.35483 (15)0.2217 (2)0.0498 (7)
H13A−0.07010.35380.27060.060*
C14−0.1411 (3)0.3606 (2)0.1518 (3)0.0805 (12)
H14A−0.20220.36320.15330.097*
C15−0.1345 (3)0.36297 (19)0.0794 (3)0.0781 (13)
H15A−0.19000.36700.03210.094*
C16−0.0452 (3)0.35929 (18)0.0773 (2)0.0694 (11)
H16A−0.03920.36120.02810.083*
C170.1225 (2)0.26936 (13)0.33361 (16)0.0382 (6)
C180.0639 (2)0.21802 (13)0.27268 (17)0.0431 (7)
C19−0.0185 (2)0.19128 (17)0.2750 (2)0.0594 (9)
H19A−0.04090.20330.31410.071*
C20−0.0675 (3)0.1451 (2)0.2162 (3)0.0824 (13)
H20A−0.12340.12530.21560.099*
C21−0.0318 (3)0.12943 (19)0.1588 (3)0.0781 (13)
H21A−0.06310.09870.11930.094*
C220.0484 (3)0.15912 (17)0.1608 (2)0.0681 (10)
H22A0.07050.14900.12090.082*
C230.1178 (2)0.22462 (15)0.46324 (19)0.0509 (8)
H23A0.10130.18270.43680.061*
H23B0.07770.23080.49350.061*
C240.2763 (2)0.20382 (14)0.40696 (18)0.0458 (7)
H24A0.33690.19750.40060.055*
H24B0.23700.16520.38700.055*
C250.2223 (2)0.22286 (14)0.52156 (18)0.0484 (7)
C260.2459 (3)0.22988 (16)0.6038 (2)0.0607 (9)
H26A0.19680.23730.62190.073*
C270.3410 (3)0.22604 (18)0.6590 (2)0.0715 (11)
H27A0.35550.23040.71370.086*
C280.4138 (3)0.21574 (18)0.6329 (2)0.0690 (11)
H28A0.47790.21330.67000.083*
C290.3925 (3)0.20886 (16)0.5515 (2)0.0583 (9)
H29A0.44260.20220.53440.070*
C300.2977 (2)0.21183 (13)0.49543 (18)0.0457 (7)
C310.2024 (2)0.46144 (13)0.00128 (17)0.0417 (7)
C320.1017 (2)0.46010 (15)−0.0412 (2)0.0533 (8)
H32A0.06160.4563−0.01330.064*
C330.0610 (3)0.46441 (16)−0.1245 (2)0.0631 (10)
H33A−0.00600.4626−0.15220.076*
C340.1189 (3)0.47125 (17)−0.1659 (2)0.0621 (9)
H34A0.09140.4740−0.22180.075*
C350.2192 (3)0.47408 (14)−0.12473 (18)0.0519 (8)
H35A0.25820.4795−0.15340.062*
C360.2618 (2)0.46896 (13)−0.04157 (17)0.0419 (7)
C370.3715 (2)0.46951 (13)0.00118 (17)0.0406 (6)
H37A0.39230.42780.02720.049*
H37B0.39890.4742−0.03890.049*
C380.2450 (2)0.45412 (14)0.09123 (17)0.0436 (7)
H38A0.19250.45000.10940.052*
H38B0.28260.41430.10530.052*
C390.4092 (2)0.58470 (13)0.03871 (17)0.0387 (6)
C400.2763 (2)0.55784 (14)0.16627 (18)0.0446 (7)
C410.40525 (19)0.51493 (13)0.13935 (16)0.0356 (6)
C420.47331 (19)0.46232 (12)0.19148 (16)0.0352 (6)
C430.5554 (2)0.44407 (15)0.18015 (18)0.0480 (7)
H43A0.56800.46070.13750.058*
C440.6183 (2)0.40048 (17)0.2335 (2)0.0569 (8)
H44A0.67470.38770.22780.068*
C450.5969 (2)0.37631 (15)0.29470 (19)0.0534 (8)
H45A0.63860.34730.33180.064*
C460.5128 (2)0.39569 (15)0.30031 (18)0.0506 (8)
H46A0.49780.37830.34140.061*
C470.43119 (19)0.58581 (12)0.17507 (16)0.0368 (6)
C480.5309 (2)0.59353 (13)0.24317 (18)0.0432 (7)
C490.5433 (3)0.58788 (17)0.3217 (2)0.0641 (10)
H49A0.49070.58010.33540.077*
C500.6374 (4)0.5941 (2)0.3814 (2)0.0857 (14)
H50A0.64850.59090.43570.103*
C510.7112 (3)0.6047 (2)0.3587 (3)0.0900 (15)
H51A0.77420.60930.39720.108*
C520.6927 (3)0.6086 (2)0.2786 (3)0.0837 (13)
H52A0.74480.61530.26400.100*
C530.3372 (3)0.66679 (18)0.2196 (3)0.0716 (11)
H53A0.30090.66350.25350.086*
H53B0.40050.68390.25360.086*
C540.4285 (3)0.69218 (14)0.1041 (2)0.0551 (8)
H54A0.43630.70710.05610.066*
H54B0.48360.70730.15090.066*
C550.2959 (10)0.7108 (7)0.1688 (15)0.044 (4)0.35 (4)
C560.2138 (12)0.7415 (6)0.170 (2)0.080 (6)0.35 (4)
H56A0.19450.73410.21170.096*0.35 (4)
C570.1606 (8)0.7833 (6)0.107 (3)0.093 (8)0.35 (4)
H57A0.10560.80380.10780.111*0.35 (4)
C580.1894 (11)0.7943 (7)0.0442 (19)0.081 (9)0.35 (4)
H58A0.15380.82230.00250.098*0.35 (4)
C590.2715 (16)0.7636 (8)0.0434 (12)0.063 (6)0.35 (4)
H59A0.29080.77100.00120.075*0.35 (4)
C600.3248 (12)0.7219 (9)0.1057 (11)0.049 (5)0.35 (4)
C55'0.2892 (6)0.7118 (4)0.1367 (10)0.055 (3)0.65 (4)
C56'0.2005 (6)0.7420 (4)0.1204 (15)0.087 (5)0.65 (4)
H56B0.16680.73390.15280.104*0.65 (4)
C57'0.1622 (5)0.7843 (4)0.0555 (15)0.102 (7)0.65 (4)
H57B0.10290.80450.04450.122*0.65 (4)
C58'0.2126 (11)0.7965 (4)0.0070 (11)0.104 (5)0.65 (4)
H58B0.18700.8248−0.03650.125*0.65 (4)
C59'0.3013 (11)0.7663 (5)0.0233 (8)0.084 (3)0.65 (4)
H59B0.33500.7745−0.00920.100*0.65 (4)
C60'0.3396 (6)0.7240 (5)0.0882 (7)0.052 (2)0.65 (4)
O5−0.0697 (6)0.4504 (5)0.4616 (6)0.258 (4)
H5−0.02620.42410.46820.387*
C61−0.1370 (6)0.4555 (6)0.3734 (6)0.212 (5)
H61A−0.20310.45170.36790.318*
H61B−0.12270.42130.34380.318*
H61C−0.12790.49680.35270.318*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0433 (13)0.0615 (14)0.0635 (14)−0.0031 (10)0.0194 (11)0.0080 (11)
O20.0630 (14)0.0619 (14)0.0436 (12)0.0062 (11)0.0264 (11)−0.0034 (10)
O30.0763 (15)0.0461 (12)0.0429 (12)0.0023 (10)0.0260 (11)0.0108 (10)
O40.0515 (14)0.0611 (15)0.105 (2)−0.0080 (11)0.0435 (14)−0.0164 (14)
N10.0454 (13)0.0360 (12)0.0385 (13)−0.0021 (10)0.0144 (11)0.0030 (10)
N20.0605 (16)0.0339 (12)0.0416 (13)0.0004 (11)0.0230 (12)−0.0023 (10)
N30.0423 (13)0.0357 (12)0.0378 (12)0.0014 (10)0.0140 (10)0.0041 (10)
N40.0514 (14)0.0398 (13)0.0399 (13)0.0016 (11)0.0218 (11)0.0047 (10)
N50.087 (2)0.0580 (18)0.0514 (17)0.0009 (15)0.0179 (16)0.0024 (14)
N60.0739 (19)0.0483 (15)0.0435 (15)0.0020 (13)0.0210 (14)−0.0044 (12)
N70.0405 (12)0.0330 (11)0.0322 (12)0.0002 (9)0.0097 (10)0.0026 (9)
N80.0357 (12)0.0348 (12)0.0433 (13)−0.0040 (9)0.0135 (10)−0.0010 (10)
N90.0537 (14)0.0300 (12)0.0423 (13)−0.0022 (10)0.0164 (11)0.0037 (10)
N100.0496 (14)0.0411 (13)0.0553 (15)−0.0076 (11)0.0264 (12)−0.0116 (11)
N110.0489 (14)0.0401 (13)0.0392 (13)−0.0025 (11)0.0146 (11)0.0071 (11)
N120.0423 (15)0.0643 (18)0.0726 (19)−0.0092 (13)0.0149 (14)−0.0130 (15)
C10.0575 (18)0.0294 (14)0.0404 (16)0.0046 (12)0.0085 (14)0.0043 (12)
C20.073 (2)0.0465 (18)0.0454 (18)0.0114 (16)0.0101 (16)−0.0056 (14)
C30.075 (3)0.057 (2)0.058 (2)−0.0013 (19)−0.001 (2)−0.0200 (17)
C40.065 (2)0.063 (2)0.083 (3)−0.0108 (19)0.013 (2)−0.018 (2)
C50.059 (2)0.0515 (19)0.072 (2)−0.0100 (16)0.0225 (18)−0.0065 (17)
C60.0570 (18)0.0340 (15)0.0443 (16)−0.0008 (13)0.0152 (14)0.0050 (12)
C70.0538 (17)0.0419 (15)0.0413 (16)−0.0046 (13)0.0191 (14)0.0066 (13)
C80.0604 (19)0.0369 (15)0.0481 (17)0.0089 (13)0.0196 (15)−0.0010 (13)
C90.0455 (17)0.0406 (15)0.0349 (15)−0.0006 (12)0.0163 (13)−0.0001 (12)
C100.0410 (15)0.0448 (16)0.0371 (15)0.0021 (12)0.0135 (12)−0.0022 (13)
C110.0452 (15)0.0348 (14)0.0353 (14)−0.0004 (12)0.0147 (12)−0.0011 (11)
C120.0532 (18)0.0300 (14)0.0423 (16)0.0023 (12)0.0125 (14)0.0001 (12)
C130.0404 (17)0.0543 (18)0.0531 (18)0.0045 (13)0.0171 (15)−0.0012 (14)
C140.050 (2)0.066 (2)0.111 (4)0.0054 (18)0.018 (2)−0.006 (2)
C150.069 (3)0.055 (2)0.071 (3)0.0021 (18)−0.013 (2)−0.0084 (19)
C160.097 (3)0.057 (2)0.0376 (18)0.001 (2)0.0095 (19)−0.0014 (15)
C170.0431 (15)0.0342 (14)0.0366 (14)−0.0007 (11)0.0153 (12)0.0014 (11)
C180.0454 (16)0.0349 (14)0.0417 (16)0.0003 (12)0.0095 (13)0.0045 (12)
C190.0473 (18)0.059 (2)0.068 (2)−0.0096 (15)0.0185 (16)0.0004 (17)
C200.052 (2)0.065 (2)0.104 (3)−0.0199 (18)0.004 (2)0.013 (2)
C210.088 (3)0.049 (2)0.061 (2)−0.003 (2)−0.009 (2)−0.0051 (18)
C220.097 (3)0.0494 (19)0.0464 (19)0.006 (2)0.0160 (19)−0.0099 (16)
C230.065 (2)0.0446 (17)0.0488 (18)0.0008 (14)0.0285 (16)0.0108 (14)
C240.0520 (17)0.0369 (15)0.0465 (17)0.0068 (13)0.0175 (14)0.0041 (13)
C250.068 (2)0.0330 (14)0.0429 (17)0.0021 (14)0.0203 (15)0.0084 (12)
C260.094 (3)0.0449 (18)0.0457 (19)0.0077 (17)0.0307 (19)0.0088 (14)
C270.109 (3)0.053 (2)0.0367 (18)0.009 (2)0.013 (2)0.0074 (15)
C280.079 (3)0.054 (2)0.049 (2)0.0058 (18)−0.0007 (19)0.0093 (16)
C290.060 (2)0.0464 (18)0.057 (2)0.0100 (15)0.0111 (17)0.0105 (15)
C300.0580 (19)0.0316 (14)0.0410 (16)0.0053 (13)0.0128 (14)0.0059 (12)
C310.0425 (15)0.0289 (13)0.0448 (16)−0.0042 (11)0.0081 (13)−0.0024 (12)
C320.0455 (17)0.0415 (16)0.063 (2)−0.0067 (13)0.0107 (15)−0.0044 (14)
C330.0502 (19)0.0500 (19)0.062 (2)0.0000 (15)−0.0062 (17)−0.0052 (16)
C340.066 (2)0.056 (2)0.0421 (18)0.0001 (17)−0.0025 (17)−0.0024 (15)
C350.065 (2)0.0390 (16)0.0425 (17)−0.0024 (14)0.0113 (15)−0.0031 (13)
C360.0479 (16)0.0279 (13)0.0406 (16)−0.0001 (11)0.0078 (13)−0.0012 (11)
C370.0467 (16)0.0342 (14)0.0390 (15)0.0028 (12)0.0148 (13)0.0000 (11)
C380.0432 (16)0.0380 (15)0.0468 (16)−0.0082 (12)0.0151 (13)0.0014 (12)
C390.0383 (15)0.0376 (14)0.0392 (16)0.0033 (11)0.0142 (12)0.0079 (12)
C400.0399 (16)0.0428 (16)0.0517 (17)−0.0038 (12)0.0187 (14)−0.0024 (13)
C410.0358 (14)0.0333 (13)0.0345 (14)−0.0035 (11)0.0105 (11)0.0018 (11)
C420.0379 (14)0.0303 (13)0.0330 (14)−0.0017 (11)0.0094 (11)0.0006 (11)
C430.0475 (17)0.0503 (17)0.0453 (17)0.0058 (14)0.0176 (14)0.0098 (14)
C440.0470 (18)0.060 (2)0.056 (2)0.0154 (15)0.0132 (15)0.0068 (16)
C450.0540 (19)0.0443 (17)0.0456 (18)0.0077 (14)0.0026 (15)0.0093 (14)
C460.061 (2)0.0446 (17)0.0381 (16)−0.0054 (14)0.0115 (14)0.0094 (13)
C470.0370 (14)0.0319 (13)0.0378 (14)−0.0006 (11)0.0109 (12)0.0016 (11)
C480.0457 (16)0.0310 (14)0.0438 (16)−0.0021 (12)0.0080 (13)0.0001 (12)
C490.076 (2)0.056 (2)0.0451 (19)−0.0144 (17)0.0075 (17)0.0062 (15)
C500.101 (4)0.063 (2)0.053 (2)−0.009 (2)−0.012 (2)0.0104 (18)
C510.064 (3)0.064 (3)0.093 (4)−0.005 (2)−0.020 (3)−0.010 (2)
C520.041 (2)0.085 (3)0.104 (4)−0.0090 (19)0.007 (2)−0.024 (3)
C530.067 (2)0.053 (2)0.112 (3)−0.0120 (18)0.053 (2)−0.030 (2)
C540.073 (2)0.0297 (15)0.0549 (19)−0.0029 (15)0.0171 (17)0.0048 (13)
C550.037 (6)0.033 (5)0.048 (10)−0.002 (4)0.002 (6)−0.020 (6)
C560.055 (7)0.049 (7)0.122 (17)0.000 (5)0.022 (10)−0.022 (9)
C570.050 (7)0.059 (8)0.15 (2)0.022 (6)0.024 (10)0.017 (11)
C580.051 (8)0.044 (8)0.104 (19)0.012 (6)−0.017 (10)0.014 (9)
C590.062 (10)0.029 (6)0.057 (9)0.008 (6)−0.019 (6)0.005 (5)
C600.052 (9)0.031 (7)0.051 (9)0.015 (7)0.007 (7)−0.006 (6)
C55'0.049 (4)0.040 (4)0.059 (8)0.003 (3)0.003 (4)−0.021 (4)
C56'0.048 (4)0.056 (4)0.142 (13)0.003 (3)0.023 (5)−0.028 (6)
C57'0.054 (5)0.060 (6)0.153 (17)0.011 (4)0.002 (7)−0.004 (6)
C58'0.087 (7)0.054 (4)0.118 (9)0.003 (4)−0.017 (7)0.013 (5)
C59'0.093 (7)0.043 (4)0.080 (6)−0.007 (5)−0.002 (5)0.002 (4)
C60'0.058 (4)0.029 (3)0.052 (5)−0.007 (3)0.003 (3)−0.007 (3)
O50.199 (7)0.350 (11)0.249 (9)0.050 (7)0.115 (7)−0.061 (8)
C610.123 (6)0.364 (16)0.150 (7)0.087 (8)0.056 (6)0.070 (9)
Geometric parameters (Å, º) top
O1—C91.213 (3)C25—C301.408 (4)
O2—C101.227 (3)C26—C271.381 (6)
O3—C391.211 (3)C26—H26A0.930
O4—C401.219 (4)C27—C281.368 (6)
N1—C91.382 (4)C27—H27A0.930
N1—C111.449 (4)C28—C291.383 (5)
N1—C71.465 (4)C28—H28A0.930
N2—C101.353 (4)C29—C301.382 (5)
N2—C111.449 (4)C29—H29A0.930
N2—C81.458 (4)C31—C321.397 (4)
N3—C91.360 (4)C31—C361.402 (4)
N3—C171.440 (4)C31—C381.501 (4)
N3—C241.461 (4)C32—C331.384 (5)
N4—C101.369 (4)C32—H32A0.930
N4—C171.456 (4)C33—C341.361 (6)
N4—C231.470 (4)C33—H33A0.930
N5—C121.375 (4)C34—C351.390 (5)
N5—C161.390 (5)C34—H34A0.930
N6—C221.340 (4)C35—C361.385 (4)
N6—C181.345 (4)C35—H35A0.930
N7—C391.381 (3)C36—C371.515 (4)
N7—C411.451 (3)C37—H37A0.970
N7—C371.461 (3)C37—H37B0.970
N8—C401.352 (4)C38—H38A0.970
N8—C411.444 (3)C38—H38B0.970
N8—C381.456 (3)C41—C421.530 (4)
N9—C391.358 (4)C41—C471.581 (4)
N9—C541.446 (4)C42—C431.378 (4)
N9—C471.446 (3)C43—C441.380 (4)
N10—C401.388 (4)C43—H43A0.930
N10—C471.439 (4)C44—C451.363 (5)
N10—C531.462 (4)C44—H44A0.930
N11—C421.326 (3)C45—C461.365 (5)
N11—C461.346 (4)C45—H45A0.930
N12—C481.335 (4)C46—H46A0.930
N12—C521.337 (5)C47—C481.522 (4)
C1—C61.390 (5)C48—C491.362 (5)
C1—C21.391 (4)C49—C501.402 (6)
C1—C81.519 (5)C49—H49A0.930
C2—C31.389 (5)C50—C511.343 (7)
C2—H2A0.9300C50—H50A0.930
C3—C41.372 (6)C51—C521.365 (7)
C3—H3A0.930C51—H51A0.930
C4—C51.377 (5)C52—H52A0.930
C4—H4A0.930C53—C551.264 (19)
C5—C61.384 (5)C53—C55'1.664 (15)
C5—H5A0.930C53—H53A0.970
C6—C71.507 (4)C53—H53B0.970
C7—H7A0.970C54—C60'1.409 (10)
C7—H7B0.970C54—C601.683 (17)
C8—H8A0.970C54—H54A0.970
C8—H8B0.970C54—H54B0.970
C11—C121.533 (4)C55—C561.390
C11—C171.587 (4)C55—C601.390
C12—C131.327 (4)C56—C571.390
C13—C141.341 (5)C56—H56A0.930
C13—H13A0.930C57—C581.390
C14—C151.353 (7)C57—H57A0.930
C14—H14A0.930C58—C591.390
C15—C161.358 (6)C58—H58A0.930
C15—H15A0.930C59—C601.390
C16—H16A0.930C59—H59A0.930
C17—C181.528 (4)C55'—C56'1.390
C18—C191.369 (4)C55'—C60'1.390
C19—C201.398 (6)C56'—C57'1.390
C19—H19A0.930C56'—H56B0.930
C20—C211.382 (7)C57'—C58'1.390
C20—H20A0.930C57'—H57B0.930
C21—C221.338 (6)C58'—C59'1.390
C21—H21A0.930C58'—H58B0.930
C22—H22A0.930C59'—C60'1.390
C23—C251.503 (5)C59'—H59B0.930
C23—H23A0.970O5—C611.515 (10)
C23—H23B0.970O5—H50.820
C24—C301.511 (4)C61—H61A0.960
C24—H24A0.970C61—H61B0.960
C24—H24B0.970C61—H61C0.960
C25—C261.393 (4)
C9—N1—C11111.4 (2)C36—C31—C38121.3 (3)
C9—N1—C7120.1 (2)C33—C32—C31120.7 (3)
C11—N1—C7121.1 (2)C33—C32—H32A119.7
C10—N2—C11113.9 (2)C31—C32—H32A119.7
C10—N2—C8124.1 (2)C34—C33—C32120.2 (3)
C11—N2—C8121.9 (2)C34—C33—H33A119.9
C9—N3—C17114.3 (2)C32—C33—H33A119.9
C9—N3—C24122.8 (2)C33—C34—C35120.1 (3)
C17—N3—C24122.6 (2)C33—C34—H34A120.0
C10—N4—C17111.3 (2)C35—C34—H34A120.0
C10—N4—C23119.7 (2)C36—C35—C34120.9 (3)
C17—N4—C23121.0 (2)C36—C35—H35A119.6
C12—N5—C16116.9 (3)C34—C35—H35A119.6
C22—N6—C18117.0 (3)C35—C36—C31119.2 (3)
C39—N7—C41111.2 (2)C35—C36—C37119.5 (3)
C39—N7—C37120.7 (2)C31—C36—C37121.2 (2)
C41—N7—C37120.2 (2)N7—C37—C36115.3 (2)
C40—N8—C41114.1 (2)N7—C37—H37A108.5
C40—N8—C38123.5 (2)C36—C37—H37A108.5
C41—N8—C38122.2 (2)N7—C37—H37B108.5
C39—N9—C54123.6 (2)C36—C37—H37B108.5
C39—N9—C47114.2 (2)H37A—C37—H37B107.5
C54—N9—C47122.2 (2)N8—C38—C31113.7 (2)
C40—N10—C47111.6 (2)N8—C38—H38A108.8
C40—N10—C53120.1 (3)C31—C38—H38A108.8
C47—N10—C53120.2 (2)N8—C38—H38B108.8
C42—N11—C46116.9 (3)C31—C38—H38B108.8
C48—N12—C52116.6 (4)H38A—C38—H38B107.7
C6—C1—C2119.6 (3)O3—C39—N9126.6 (3)
C6—C1—C8121.8 (3)O3—C39—N7125.6 (3)
C2—C1—C8118.7 (3)N9—C39—N7107.7 (2)
C3—C2—C1120.1 (4)O4—C40—N8126.8 (3)
C3—C2—H2A119.9O4—C40—N10125.6 (3)
C1—C2—H2A119.9N8—C40—N10107.5 (2)
C4—C3—C2120.4 (3)N8—C41—N7113.2 (2)
C4—C3—H3A119.8N8—C41—C42112.8 (2)
C2—C3—H3A119.8N7—C41—C42111.7 (2)
C3—C4—C5119.3 (4)N8—C41—C47101.5 (2)
C3—C4—H4A120.3N7—C41—C47102.9 (2)
C5—C4—H4A120.3C42—C41—C47114.0 (2)
C4—C5—C6121.6 (4)N11—C42—C43123.1 (3)
C4—C5—H5A119.2N11—C42—C41115.5 (2)
C6—C5—H5A119.2C43—C42—C41121.2 (2)
C5—C6—C1119.1 (3)C42—C43—C44118.5 (3)
C5—C6—C7119.3 (3)C42—C43—H43A120.8
C1—C6—C7121.5 (3)C44—C43—H43A120.8
N1—C7—C6115.6 (2)C45—C44—C43119.3 (3)
N1—C7—H7A108.4C45—C44—H44A120.4
C6—C7—H7A108.4C43—C44—H44A120.4
N1—C7—H7B108.4C44—C45—C46118.5 (3)
C6—C7—H7B108.4C44—C45—H45A120.8
H7A—C7—H7B107.5C46—C45—H45A120.8
N2—C8—C1113.6 (2)N11—C46—C45123.7 (3)
N2—C8—H8A108.8N11—C46—H46A118.1
C1—C8—H8A108.8C45—C46—H46A118.1
N2—C8—H8B108.8N10—C47—N9113.0 (2)
C1—C8—H8B108.8N10—C47—C48112.1 (2)
H8A—C8—H8B107.7N9—C47—C48111.5 (2)
O1—C9—N3126.4 (3)N10—C47—C41102.8 (2)
O1—C9—N1125.9 (3)N9—C47—C41101.3 (2)
N3—C9—N1107.7 (2)C48—C47—C41115.5 (2)
O2—C10—N2126.1 (3)N12—C48—C49123.4 (3)
O2—C10—N4125.2 (3)N12—C48—C47115.3 (3)
N2—C10—N4108.7 (2)C49—C48—C47121.2 (3)
N1—C11—N2112.8 (2)C48—C49—C50118.3 (4)
N1—C11—C12113.5 (2)C48—C49—H49A120.8
N2—C11—C12111.2 (2)C50—C49—H49A120.8
N1—C11—C17102.9 (2)C51—C50—C49118.7 (4)
N2—C11—C17101.2 (2)C51—C50—H50A120.7
C12—C11—C17114.3 (2)C49—C50—H50A120.7
C13—C12—N5123.2 (3)C50—C51—C52119.3 (4)
C13—C12—C11116.5 (3)C50—C51—H51A120.4
N5—C12—C11120.2 (3)C52—C51—H51A120.4
C12—C13—C14117.9 (4)N12—C52—C51123.7 (4)
C12—C13—H13A121.0N12—C52—H52A118.1
C14—C13—H13A121.0C51—C52—H52A118.1
C13—C14—C15123.0 (4)C55—C53—N10125.7 (10)
C13—C14—H14A118.5N10—C53—C55'111.5 (5)
C15—C14—H14A118.5C55—C53—H53A105.9
C14—C15—C16118.5 (4)N10—C53—H53A105.9
C14—C15—H15A120.7C55'—C53—H53A117.2
C16—C15—H15A120.7C55—C53—H53B105.9
C15—C16—N5120.4 (4)N10—C53—H53B105.9
C15—C16—H16A119.8C55'—C53—H53B109.4
N5—C16—H16A119.8H53A—C53—H53B106.2
N3—C17—N4113.2 (2)C60'—C54—N9114.9 (5)
N3—C17—C18111.5 (2)N9—C54—C60108.4 (8)
N4—C17—C18112.4 (2)C60'—C54—H54A96.4
N3—C17—C11101.4 (2)N9—C54—H54A110.0
N4—C17—C11102.9 (2)C60—C54—H54A110.0
C18—C17—C11114.8 (2)C60'—C54—H54B116.0
N6—C18—C19123.6 (3)N9—C54—H54B110.0
N6—C18—C17114.8 (3)C60—C54—H54B110.0
C19—C18—C17121.6 (3)H54A—C54—H54B108.4
C18—C19—C20117.2 (4)C53—C55—C56119.9 (10)
C18—C19—H19A121.4C53—C55—C60119.5 (10)
C20—C19—H19A121.4C56—C55—C60120.0
C21—C20—C19119.2 (4)C57—C56—C55120.0
C21—C20—H20A120.4C57—C56—H56A120.0
C19—C20—H20A120.4C55—C56—H56A120.0
C22—C21—C20119.0 (4)C56—C57—C58120.0
C22—C21—H21A120.5C56—C57—H57A120.0
C20—C21—H21A120.5C58—C57—H57A120.0
C21—C22—N6123.9 (4)C59—C58—C57120.0
C21—C22—H22A118.1C59—C58—H58A120.0
N6—C22—H22A118.1C57—C58—H58A120.0
N4—C23—C25115.6 (2)C60—C59—C58120.0
N4—C23—H23A108.4C60—C59—H59A120.0
C25—C23—H23A108.4C58—C59—H59A120.0
N4—C23—H23B108.4C59—C60—C55120.0
C25—C23—H23B108.4C59—C60—C54116.6 (8)
H23A—C23—H23B107.5C55—C60—C54123.1 (7)
N3—C24—C30112.9 (2)C56'—C55'—C60'120.0
N3—C24—H24A109.0C56'—C55'—C53118.4 (5)
C30—C24—H24A109.0C60'—C55'—C53121.3 (5)
N3—C24—H24B109.0C57'—C56'—C55'120.0
C30—C24—H24B109.0C57'—C56'—H56B120.0
H24A—C24—H24B107.8C55'—C56'—H56B120.0
C26—C25—C30118.5 (3)C56'—C57'—C58'120.0
C26—C25—C23120.0 (3)C56'—C57'—H57B120.0
C30—C25—C23121.5 (3)C58'—C57'—H57B120.0
C27—C26—C25121.2 (4)C59'—C58'—C57'120.0
C27—C26—H26A119.4C59'—C58'—H58B120.0
C25—C26—H26A119.4C57'—C58'—H58B120.0
C28—C27—C26119.8 (3)C58'—C59'—C60'120.0
C28—C27—H27A120.1C58'—C59'—H59B120.0
C26—C27—H27A120.1C60'—C59'—H59B120.0
C27—C28—C29120.3 (4)C59'—C60'—C55'120.0
C27—C28—H28A119.8C59'—C60'—C54120.3 (6)
C29—C28—H28A119.8C55'—C60'—C54119.7 (6)
C30—C29—C28120.7 (4)C61—O5—H5111.1
C30—C29—H29A119.6O5—C61—H61A109.5
C28—C29—H29A119.6O5—C61—H61B109.5
C29—C30—C25119.4 (3)H61A—C61—H61B109.5
C29—C30—C24119.8 (3)O5—C61—H61C109.5
C25—C30—C24120.8 (3)H61A—C61—H61C109.5
C32—C31—C36118.9 (3)H61B—C61—H61C109.5
C32—C31—C38119.8 (3)
C6—C1—C2—C31.7 (5)C31—C36—C37—N7−59.5 (3)
C8—C1—C2—C3−177.5 (3)C40—N8—C38—C3197.9 (3)
C1—C2—C3—C4−0.7 (5)C41—N8—C38—C31−77.9 (3)
C2—C3—C4—C5−0.8 (6)C32—C31—C38—N8−122.8 (3)
C3—C4—C5—C61.4 (6)C36—C31—C38—N857.9 (4)
C4—C5—C6—C1−0.5 (5)C54—N9—C39—O30.4 (5)
C4—C5—C6—C7176.1 (3)C47—N9—C39—O3178.4 (3)
C2—C1—C6—C5−1.0 (4)C54—N9—C39—N7178.5 (3)
C8—C1—C6—C5178.1 (3)C47—N9—C39—N7−3.5 (3)
C2—C1—C6—C7−177.5 (3)C41—N7—C39—O3−168.4 (3)
C8—C1—C6—C71.6 (4)C37—N7—C39—O3−19.4 (4)
C9—N1—C7—C6−72.6 (3)C41—N7—C39—N913.5 (3)
C11—N1—C7—C674.7 (3)C37—N7—C39—N9162.5 (2)
C5—C6—C7—N1124.6 (3)C41—N8—C40—O4178.8 (3)
C1—C6—C7—N1−59.0 (4)C38—N8—C40—O42.7 (5)
C10—N2—C8—C198.7 (3)C41—N8—C40—N10−3.5 (3)
C11—N2—C8—C1−77.8 (3)C38—N8—C40—N10−179.5 (2)
C6—C1—C8—N256.8 (4)C47—N10—C40—O4−168.9 (3)
C2—C1—C8—N2−124.1 (3)C53—N10—C40—O4−20.3 (5)
C17—N3—C9—O1177.6 (3)C47—N10—C40—N813.3 (3)
C24—N3—C9—O13.6 (4)C53—N10—C40—N8161.9 (3)
C17—N3—C9—N1−5.0 (3)C40—N8—C41—N7−115.9 (3)
C24—N3—C9—N1−179.0 (2)C38—N8—C41—N760.2 (3)
C11—N1—C9—O1−169.0 (3)C40—N8—C41—C42116.0 (3)
C7—N1—C9—O1−18.8 (4)C38—N8—C41—C42−67.9 (3)
C11—N1—C9—N313.6 (3)C40—N8—C41—C47−6.4 (3)
C7—N1—C9—N3163.8 (2)C38—N8—C41—C47169.7 (2)
C11—N2—C10—O2179.8 (3)C39—N7—C41—N891.7 (3)
C8—N2—C10—O23.1 (5)C37—N7—C41—N8−57.5 (3)
C11—N2—C10—N4−2.0 (3)C39—N7—C41—C42−139.6 (2)
C8—N2—C10—N4−178.7 (3)C37—N7—C41—C4271.2 (3)
C17—N4—C10—O2−170.7 (3)C39—N7—C41—C47−16.9 (3)
C23—N4—C10—O2−21.6 (4)C37—N7—C41—C47−166.1 (2)
C17—N4—C10—N211.0 (3)C46—N11—C42—C431.4 (4)
C23—N4—C10—N2160.1 (3)C46—N11—C42—C41−175.3 (2)
C9—N1—C11—N292.4 (3)N8—C41—C42—N11−29.2 (3)
C7—N1—C11—N2−57.4 (3)N7—C41—C42—N11−158.1 (2)
C9—N1—C11—C12−139.9 (2)C47—C41—C42—N1185.8 (3)
C7—N1—C11—C1270.3 (3)N8—C41—C42—C43154.1 (3)
C9—N1—C11—C17−15.8 (3)N7—C41—C42—C4325.2 (3)
C7—N1—C11—C17−165.6 (2)C47—C41—C42—C43−90.9 (3)
C10—N2—C11—N1−116.0 (3)N11—C42—C43—C44−2.1 (5)
C8—N2—C11—N160.8 (3)C41—C42—C43—C44174.4 (3)
C10—N2—C11—C12115.1 (3)C42—C43—C44—C450.9 (5)
C8—N2—C11—C12−68.1 (3)C43—C44—C45—C460.8 (5)
C10—N2—C11—C17−6.7 (3)C42—N11—C46—C450.4 (4)
C8—N2—C11—C17170.0 (3)C44—C45—C46—N11−1.5 (5)
C16—N5—C12—C13−0.2 (5)C40—N10—C47—N991.8 (3)
C16—N5—C12—C11178.1 (3)C53—N10—C47—N9−56.8 (4)
N1—C11—C12—C13−164.8 (3)C40—N10—C47—C48−141.1 (2)
N2—C11—C12—C13−36.2 (3)C53—N10—C47—C4870.2 (4)
C17—C11—C12—C1377.6 (3)C40—N10—C47—C41−16.5 (3)
N1—C11—C12—N516.9 (4)C53—N10—C47—C41−165.1 (3)
N2—C11—C12—N5145.4 (3)C39—N9—C47—N10−115.9 (3)
C17—C11—C12—N5−100.7 (3)C54—N9—C47—N1062.2 (3)
N5—C12—C13—C140.7 (5)C39—N9—C47—C48116.7 (3)
C11—C12—C13—C14−177.6 (3)C54—N9—C47—C48−65.2 (3)
C12—C13—C14—C15−0.6 (6)C39—N9—C47—C41−6.6 (3)
C13—C14—C15—C16−0.1 (6)C54—N9—C47—C41171.4 (3)
C14—C15—C16—N50.6 (6)N8—C41—C47—N1013.1 (2)
C12—N5—C16—C15−0.5 (5)N7—C41—C47—N10130.5 (2)
C9—N3—C17—N4−114.1 (3)C42—C41—C47—N10−108.4 (2)
C24—N3—C17—N460.0 (3)N8—C41—C47—N9−103.9 (2)
C9—N3—C17—C18118.1 (3)N7—C41—C47—N913.5 (2)
C24—N3—C17—C18−67.9 (3)C42—C41—C47—N9134.6 (2)
C9—N3—C17—C11−4.6 (3)N8—C41—C47—C48135.5 (2)
C24—N3—C17—C11169.5 (2)N7—C41—C47—C48−107.2 (3)
C10—N4—C17—N394.1 (3)C42—C41—C47—C4813.9 (3)
C23—N4—C17—N3−54.6 (3)C52—N12—C48—C49−0.8 (5)
C10—N4—C17—C18−138.5 (2)C52—N12—C48—C47−178.2 (3)
C23—N4—C17—C1872.8 (3)N10—C47—C48—N12−157.8 (2)
C10—N4—C17—C11−14.5 (3)N9—C47—C48—N12−29.9 (3)
C23—N4—C17—C11−163.2 (2)C41—C47—C48—N1285.0 (3)
N1—C11—C17—N311.7 (2)N10—C47—C48—C4924.7 (4)
N2—C11—C17—N3−105.1 (2)N9—C47—C48—C49152.6 (3)
C12—C11—C17—N3135.2 (2)C41—C47—C48—C49−92.5 (3)
N1—C11—C17—N4129.0 (2)N12—C48—C49—C501.3 (5)
N2—C11—C17—N412.1 (3)C47—C48—C49—C50178.6 (3)
C12—C11—C17—N4−107.5 (3)C48—C49—C50—C51−0.6 (6)
N1—C11—C17—C18−108.7 (3)C49—C50—C51—C52−0.5 (6)
N2—C11—C17—C18134.5 (2)C48—N12—C52—C51−0.4 (6)
C12—C11—C17—C1814.9 (3)C50—C51—C52—N121.0 (7)
C22—N6—C18—C190.7 (5)C40—N10—C53—C55−68.9 (10)
C22—N6—C18—C17−178.2 (3)C47—N10—C53—C5577.0 (10)
N3—C17—C18—N6−40.7 (3)C40—N10—C53—C55'−73.7 (5)
N4—C17—C18—N6−169.0 (2)C47—N10—C53—C55'72.2 (5)
C11—C17—C18—N673.9 (3)C39—N9—C54—C60'93.1 (7)
N3—C17—C18—C19140.3 (3)C47—N9—C54—C60'−84.8 (7)
N4—C17—C18—C1912.0 (4)C39—N9—C54—C60105.9 (7)
C11—C17—C18—C19−105.1 (3)C47—N9—C54—C60−71.9 (7)
N6—C18—C19—C200.6 (5)N10—C53—C55—C56122.1 (8)
C17—C18—C19—C20179.4 (3)C55'—C53—C55—C56140 (4)
C18—C19—C20—C21−0.7 (5)N10—C53—C55—C60−49.0 (14)
C19—C20—C21—C22−0.4 (6)C55'—C53—C55—C60−31 (4)
C20—C21—C22—N61.8 (6)C53—C55—C56—C57−171.1 (15)
C18—N6—C22—C21−1.9 (5)C60—C55—C56—C570.0
C10—N4—C23—C25−72.3 (4)C55—C56—C57—C580.0
C17—N4—C23—C2573.8 (4)C56—C57—C58—C590.0
C9—N3—C24—C3094.1 (3)C57—C58—C59—C600.0
C17—N3—C24—C30−79.5 (3)C58—C59—C60—C550.0
N4—C23—C25—C26121.6 (3)C58—C59—C60—C54−174.7 (14)
N4—C23—C25—C30−60.8 (4)C53—C55—C60—C59171.1 (15)
C30—C25—C26—C27−0.1 (5)C56—C55—C60—C590.0
C23—C25—C26—C27177.6 (3)C53—C55—C60—C54−14.6 (18)
C25—C26—C27—C280.6 (5)C56—C55—C60—C54174.3 (15)
C26—C27—C28—C29−0.3 (5)C60'—C54—C60—C59−2 (4)
C27—C28—C29—C30−0.4 (5)N9—C54—C60—C59−123.3 (8)
C28—C29—C30—C250.9 (5)C60'—C54—C60—C55−177 (5)
C28—C29—C30—C24−179.7 (3)N9—C54—C60—C5562.2 (11)
C26—C25—C30—C29−0.6 (4)C55—C53—C55'—C56'−42 (4)
C23—C25—C30—C29−178.2 (3)N10—C53—C55'—C56'122.1 (5)
C26—C25—C30—C24180.0 (3)C55—C53—C55'—C60'132 (4)
C23—C25—C30—C242.3 (4)N10—C53—C55'—C60'−63.4 (6)
N3—C24—C30—C29−121.8 (3)C60'—C55'—C56'—C57'0.0
N3—C24—C30—C2557.6 (4)C53—C55'—C56'—C57'174.6 (7)
C36—C31—C32—C331.7 (4)C55'—C56'—C57'—C58'0.0
C38—C31—C32—C33−177.7 (3)C56'—C57'—C58'—C59'0.0
C31—C32—C33—C34−1.2 (5)C57'—C58'—C59'—C60'0.0
C32—C33—C34—C35−0.1 (5)C58'—C59'—C60'—C55'0.0
C33—C34—C35—C361.1 (5)C58'—C59'—C60'—C54178.6 (8)
C34—C35—C36—C31−0.6 (4)C56'—C55'—C60'—C59'0.0
C34—C35—C36—C37177.6 (3)C53—C55'—C60'—C59'−174.4 (7)
C32—C31—C36—C35−0.7 (4)C56'—C55'—C60'—C54−178.6 (8)
C38—C31—C36—C35178.6 (3)C53—C55'—C60'—C546.9 (8)
C32—C31—C36—C37−178.9 (3)N9—C54—C60'—C59'−121.8 (5)
C38—C31—C36—C370.4 (4)C60—C54—C60'—C59'174 (5)
C39—N7—C37—C36−70.8 (3)N9—C54—C60'—C55'56.8 (7)
C41—N7—C37—C3675.5 (3)C60—C54—C60'—C55'−7 (4)
C35—C36—C37—N7122.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O20.822.022.840 (8)178
C2—H2A···O5i0.932.353.279 (9)174
C22—H22A···O2ii0.932.573.462 (4)160
C43—H43A···O3iii0.932.603.249 (5)128
C46—H46A···O10.932.593.340 (4)138
C51—H51A···O2iv0.932.523.419 (4)164
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC30H24N6O2·0.5CH4O
Mr516.57
Crystal system, space groupMonoclinic, P21/c
Temperature (K)292
a, b, c (Å)15.0063 (10), 20.5919 (13), 18.0864 (12)
β (°) 113.405 (1)
V (Å3)5129.0 (6)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerBruker SMART 4K CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		68334, 8988, 7325
Rint0.037
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.208, 1.08
No. of reflections8988
No. of parameters734
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.68, −0.56

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O20.822.022.840 (8)178.1
C2—H2A···O5i0.932.353.279 (9)173.5
C22—H22A···O2ii0.932.573.462 (4)160.2
C43—H43A···O3iii0.932.603.249 (5)127.7
C46—H46A···O10.932.593.340 (4)138.4
C51—H51A···O2iv0.932.523.419 (4)164.2
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1.
 

Acknowledgements

The authors are grateful to Central China Normal University.

References

First citationAdrian, J. C. Jr & Wilcox, C. S. (1989). J. Am. Chem. Soc. 111, 8055–8057.  CSD CrossRef CAS Web of Science Google Scholar
 First citationBehrend, R., Meyer, E. & Rusche, F. (1905). Liebigs Ann. Chem. 339, 1–37.  CrossRef Google Scholar
 First citationBruker (2001). SMART (Version 5.628) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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 First citationSanderson, P. E. J., Kilburn, J. D. & Still, W. C. (1989). J. Am. Chem. Soc. 111, 8314–8315.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, Z. G., Zhou, B. H., Chen, Y. F., Yin, G. D., Li, Y. T., Wu, A. X. & Isaacs, L. (2006). J. Org. Chem. 71, 4502–4508.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationWu, A. X., Fettinger, J. C. & Isaacs, L. (2002). Tetrahedron, 58, 9769–9777.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o140
https://doi.org/10.1107/S1600536807063295
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