supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

bq2055 scheme

Acta Cryst. (2008). E64, o386    [ doi:10.1107/S1600536807068481 ]

3-(2-Pyridyl)-N-p-tolylindolizin-1-amine

F.-F. Jian, M.-N. Jiang, X.-Y. Ren and L.-H. Huang

Abstract top

In the title compound, C20H17N3, there are four molecules in the asymmetric unit. The dihedral angles between the indolizine ring system and the pyridyl ring are 6.6 (2), 7.4 (1), 4.0 (1) and 10.1 (4) in the four molecules. There are no further important differences between the independent molecules. In each molecule, there is an intramolecular C-H...N hydrogen bond. The whole structure is stabilized by N-H...[pi] and C-H...[pi] interactions.

Comment top

Chemists are attracted by indolizines and their derivatives because of their importance as pharmaceutical drugs, such as potential central nervous system depressants, cardiovascular agents, calcium entry blockers, spectral sensitizers and novel dyes (Hema et al., 2003). Due to the diverse properties of indolizine derivatives, the structure determination of the title compound, (I), was performed.

Scheme I

The asymmetric unit of (I) contains four crystallographic independent molecules (A, B, C and D) as shown in Fig. 1. The corresponding bond lengths and angles in the independent molecules agree with each other and are comparable to those in related structures (Hema et al., 2003, 2004). For A, the indolizine ring makes dihedral angels of 6.6 (2)° and 66.6 (1)°, respectively, with the pyridine ring and phenyl ring. (7.4 (1)° and 66.2 (1)° for B, 4.0 (1)° and 67.6 (1)° for C and 10.1 (4)° and 66.0 (1)° for D). The crystal packing is stabilized by N—H···Π and C—H···Π interactions (Table 1). The shortest N—H···Π interaction is H7B···Cg1i = 2.827 (2) Å, N7—H7B···Cg1i = 168.5 (2)°; and the shortest C—H···Π interaction is H57A···Cg2ii = 2.977 (2) Å, C57—H57A···Cg2ii = 157.4 (1)°. Cg1 is the centroid of the benzene ring C2–C7; Cg2 is the centroid of the 5-membered ring N2/C9/C8/C15/C14. [symmetry code: (i) -1/2+X,-1/2+Y,Z; (ii) X,-1+Y,Z]

Related literature top

For related literature, see: Hema et al. (2003, 2004).

Experimental top

The mixture of ethyl 1,3-di(pyridin-2-yl)prop-2-en-1-one (5 mmol/1.044 g) and p-toluidine (6 mmol/0.643 g) in toluene (20 ml) was stirred and refluxed, then the phosphotungstic acid (0.01 g) in water (10 ml) was added dropwise. After two hours, the insoluble materials were removed by filtration, and the filtrate was separated. Finally the organic layer was kept at room temperature about two days. Yellow-colored and block shaped single crystals suitable for x-ray measurements were obtained.

Refinement top

All the H atoms were discernable in a difference Fourier map. The N—H distance was 0.86 Å and C—H distances were constrained to 0.93 to 0.98 Å, respectively, while Uiso(H) = 1.2Ueq(C). 3423 Friedel pairs were averaged before the final refinement as the absolute could not be determined unambiguously.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART [SAINT?] (Bruker, 2001); data reduction: SMART [SAINT?] (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The four independent molecules in the asymetric unit of (I) and atom-labeling scheme with the displacement ellipsoids drawn at the 30% probability level.
3-(2-Pyridyl)-N-p-tolylindolizin-1-amine top
Crystal data top
C20H17N3F000 = 2528
Mr = 299.37Dx = 1.267 Mg m−3
Monoclinic, CcMo Kα radiation
λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 25 reflections
a = 11.090 (4) Åθ = 1.6–28.4º
b = 11.140 (2) ŵ = 0.08 mm−1
c = 51.061 (3) ÅT = 295 (2) K
β = 95.41 (3)ºBlock, yellow
V = 6280 (3) Å30.40 × 0.30 × 0.12 mm
Z = 16
Data collection top
Bruker SMART CCD area-detector
diffractometer		3417 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Monochromator: graphiteθmax = 25.0º
T = 295(2) Kθmin = 1.6º
φ and ω scansh = −12→13
Absorption correction: nonek = −13→12
16297 measured reflectionsl = −58→60
5538 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051  w = 1/[σ2(Fo2) + (0.0637P)2 + 0.1752P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136(Δ/σ)max = 0.011
S = 1.01Δρmax = 0.15 e Å−3
5538 reflectionsΔρmin = −0.14 e Å−3
831 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.00080 (13)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 3423 Friedel pairs
Secondary atom site location: difference Fourier map
Crystal data top
C20H17N3V = 6280 (3) Å3
Mr = 299.37Z = 16
Monoclinic, CcMo Kα
a = 11.090 (4) ŵ = 0.08 mm−1
b = 11.140 (2) ÅT = 295 (2) K
c = 51.061 (3) Å0.40 × 0.30 × 0.12 mm
β = 95.41 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		5538 independent reflections
Absorption correction: none3417 reflections with I > 2σ(I)
16297 measured reflectionsRint = 0.050
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.136Δρmax = 0.15 e Å−3
S = 1.01Δρmin = −0.14 e Å−3
5538 reflectionsAbsolute structure: Flack (1983), with 3423 Friedel pairs
831 parametersFlack parameter: ?
2 restraints
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*/Ueq
N10.8702 (4)0.3215 (4)0.31351 (9)0.0787 (14)
H1A0.87200.39330.31970.094*
N20.7012 (4)0.3065 (4)0.24985 (9)0.0608 (12)
N30.7434 (5)0.2041 (5)0.19954 (11)0.0841 (15)
C11.0319 (7)−0.0574 (6)0.38255 (12)0.110 (2)
H1B1.0706−0.02450.39860.164*
H1C1.0886−0.10640.37430.164*
H1D0.9640−0.10550.38640.164*
C20.9890 (6)0.0429 (6)0.36437 (11)0.0741 (17)
C31.0091 (6)0.1596 (6)0.37080 (11)0.0738 (16)
H3B1.04950.17760.38710.089*
C40.9724 (5)0.2527 (6)0.35424 (10)0.0696 (16)
H4A0.98870.33160.35940.083*
C50.9113 (5)0.2286 (5)0.33001 (10)0.0602 (14)
C60.8902 (5)0.1097 (5)0.32329 (11)0.0662 (15)
H6A0.84980.09060.30700.079*
C70.9284 (6)0.0197 (5)0.34038 (11)0.0748 (16)
H7A0.9125−0.05960.33550.090*
C80.8258 (5)0.3041 (5)0.28723 (11)0.0663 (15)
C90.7111 (5)0.3368 (5)0.27655 (11)0.0621 (15)
C100.6124 (6)0.3899 (5)0.28682 (13)0.0725 (17)
H10A0.61700.40960.30460.087*
C110.5097 (6)0.4132 (5)0.27125 (15)0.0812 (18)
H11A0.44420.44970.27820.097*
C120.5030 (5)0.3819 (5)0.24475 (14)0.0784 (17)
H12A0.43190.39720.23410.094*
C130.5964 (5)0.3301 (5)0.23408 (12)0.0697 (15)
H13A0.59010.31050.21630.084*
C140.8086 (4)0.2530 (4)0.24408 (11)0.0579 (13)
C150.8842 (5)0.2535 (5)0.26710 (11)0.0651 (15)
H15A0.96310.22420.26890.078*
C160.8322 (5)0.2028 (5)0.21916 (11)0.0599 (14)
C170.9428 (5)0.1527 (5)0.21541 (12)0.0744 (16)
H17A1.00490.15430.22900.089*
C180.9618 (7)0.1007 (6)0.19205 (13)0.0900 (19)
H18A1.03650.06700.18950.108*
C190.8697 (8)0.0989 (6)0.17249 (13)0.092 (2)
H19A0.87920.06200.15650.111*
C200.7651 (8)0.1517 (7)0.17686 (15)0.100 (2)
H20A0.70330.15190.16320.120*
N40.5455 (4)0.5425 (4)−0.00222 (8)0.0746 (14)
H4B0.54230.6132−0.00900.090*
N50.7094 (4)0.5371 (3)0.06191 (8)0.0518 (11)
N60.6644 (5)0.4385 (4)0.11294 (10)0.0770 (14)
C210.3945 (8)0.1527 (7)−0.06943 (13)0.121 (3)
H21A0.35300.1839−0.08530.181*
H21B0.34090.1014−0.06080.181*
H21C0.46400.1076−0.07360.181*
C220.4350 (6)0.2556 (6)−0.05135 (11)0.0741 (16)
C230.4128 (6)0.3724 (6)−0.05887 (12)0.0801 (18)
H23A0.37300.3882−0.07540.096*
C240.4486 (5)0.4670 (5)−0.04242 (10)0.0715 (16)
H24A0.43180.5454−0.04790.086*
C250.5086 (5)0.4468 (5)−0.01808 (10)0.0543 (13)
C260.5321 (5)0.3307 (5)−0.01034 (10)0.0625 (14)
H26A0.57260.31510.00610.075*
C270.4957 (6)0.2366 (5)−0.02691 (10)0.0748 (17)
H27A0.51270.1584−0.02140.090*
C280.5886 (5)0.5302 (4)0.02476 (10)0.0579 (13)
C290.7024 (5)0.5647 (5)0.03511 (11)0.0577 (14)
C300.8009 (6)0.6197 (5)0.02489 (12)0.0718 (16)
H30A0.79720.63870.00710.086*
C310.9021 (6)0.6454 (5)0.04093 (14)0.0813 (17)
H31A0.96850.68080.03420.098*
C320.9057 (5)0.6185 (5)0.06769 (13)0.0740 (16)
H32A0.97450.63800.07870.089*
C330.8120 (5)0.5650 (5)0.07788 (11)0.0639 (14)
H33A0.81670.54700.09570.077*
C340.6026 (5)0.4835 (4)0.06768 (10)0.0529 (13)
C350.5289 (5)0.4805 (4)0.04439 (10)0.0608 (13)
H35A0.45080.44950.04230.073*
C360.5768 (5)0.4394 (4)0.09291 (11)0.0576 (14)
C370.4624 (5)0.3957 (5)0.09660 (11)0.0669 (15)
H37A0.40120.39910.08290.080*
C380.4389 (6)0.3478 (6)0.12013 (12)0.0831 (18)
H38A0.36280.31650.12240.100*
C390.5289 (7)0.3466 (6)0.14023 (12)0.087 (2)
H39A0.51580.31500.15660.105*
C400.6374 (7)0.3924 (6)0.13573 (12)0.087 (2)
H40A0.69820.39170.14960.105*
N70.2351 (4)0.1835 (4)0.31743 (8)0.0784 (14)
H7B0.16740.18410.32440.094*
N80.2036 (4)0.3160 (4)0.25301 (8)0.0551 (11)
N90.2663 (4)0.2453 (4)0.20166 (9)0.0754 (13)
C410.6583 (7)0.0627 (8)0.38309 (13)0.127 (3)
H41A0.63620.02990.39940.191*
H41B0.70680.13320.38660.191*
H41C0.70370.00420.37430.191*
C420.5462 (6)0.0949 (5)0.36591 (11)0.0718 (17)
C430.4346 (6)0.0748 (5)0.37313 (11)0.0762 (18)
H43A0.42660.04000.38940.091*
C440.3328 (6)0.1037 (5)0.35743 (10)0.0695 (15)
H44A0.25740.08950.36340.083*
C450.3385 (5)0.1526 (5)0.33324 (10)0.0555 (13)
C460.4528 (5)0.1748 (5)0.32533 (10)0.0633 (15)
H46A0.46100.20990.30910.076*
C470.5528 (5)0.1449 (5)0.34158 (11)0.0713 (15)
H47A0.62880.15890.33590.086*
C480.2342 (5)0.2138 (5)0.29083 (11)0.0616 (14)
C490.1925 (5)0.3227 (5)0.28004 (11)0.0618 (15)
C500.1451 (5)0.4263 (6)0.29006 (13)0.0742 (16)
H50A0.13770.43210.30800.089*
C510.1101 (6)0.5176 (5)0.27438 (16)0.0846 (18)
H51A0.07800.58660.28130.102*
C520.1219 (5)0.5090 (5)0.24722 (14)0.0779 (17)
H52A0.09770.57320.23630.093*
C530.1670 (5)0.4110 (5)0.23683 (12)0.0684 (15)
H53A0.17380.40660.21880.082*
C540.2545 (5)0.2072 (5)0.24732 (10)0.0553 (13)
C550.2706 (4)0.1438 (5)0.27082 (10)0.0599 (13)
H55A0.30120.06630.27270.072*
C560.2838 (5)0.1672 (5)0.22142 (10)0.0598 (15)
C570.3280 (6)0.0552 (5)0.21804 (12)0.0764 (16)
H57A0.33780.00230.23220.092*
C580.3581 (7)0.0202 (7)0.19380 (15)0.099 (2)
H58A0.3901−0.05560.19130.119*
C590.3398 (7)0.0992 (9)0.17338 (15)0.103 (2)
H59A0.35890.07850.15660.124*
C600.2935 (6)0.2077 (8)0.17817 (14)0.096 (2)
H60A0.27950.26030.16410.116*
N100.1844 (4)0.4090 (5)−0.00098 (10)0.0818 (14)
H10B0.25290.4104−0.00760.098*
N110.2016 (4)0.5450 (4)0.06290 (9)0.0580 (12)
N120.1146 (5)0.4780 (4)0.11300 (11)0.0838 (15)
C61−0.2288 (7)0.2740 (8)−0.06922 (14)0.119 (3)
H61A−0.29970.2754−0.05980.178*
H61B−0.21770.1947−0.07590.178*
H61C−0.23870.3299−0.08360.178*
C62−0.1199 (6)0.3084 (6)−0.05100 (12)0.0759 (17)
C63−0.0037 (6)0.2915 (6)−0.05796 (11)0.0797 (18)
H63A0.00720.2581−0.07430.096*
C640.0966 (6)0.3231 (5)−0.04131 (11)0.0741 (16)
H64A0.17380.3092−0.04630.089*
C650.0825 (5)0.3754 (4)−0.01716 (10)0.0595 (14)
C66−0.0325 (5)0.3933 (5)−0.01056 (11)0.0657 (16)
H66A−0.04440.42770.00560.079*
C67−0.1307 (6)0.3614 (5)−0.02736 (11)0.0771 (17)
H67A−0.20780.3766−0.02240.093*
C680.1821 (5)0.4409 (5)0.02563 (11)0.0645 (14)
C690.2190 (5)0.5481 (5)0.03640 (11)0.0613 (14)
C700.2701 (5)0.6524 (6)0.02631 (14)0.0796 (18)
H70A0.28220.65710.00860.096*
C710.3014 (5)0.7460 (6)0.04260 (15)0.0811 (18)
H71A0.33410.81550.03600.097*
C720.2844 (5)0.7370 (5)0.06911 (14)0.0791 (17)
H72A0.30740.80080.08020.095*
C730.2363 (5)0.6400 (5)0.07914 (12)0.0663 (15)
H73A0.22610.63640.09700.080*
C740.1514 (5)0.4339 (4)0.06860 (10)0.0569 (13)
C750.1399 (5)0.3708 (5)0.04535 (11)0.0631 (14)
H75A0.10880.29350.04320.076*
C760.1158 (5)0.3981 (5)0.09363 (11)0.0645 (14)
C770.0773 (6)0.2824 (5)0.09707 (12)0.0790 (17)
H77A0.07770.22790.08330.095*
C780.0385 (7)0.2461 (6)0.12032 (13)0.0912 (19)
H78A0.01260.16760.12250.109*
C790.0382 (7)0.3279 (6)0.14059 (12)0.087 (2)
H79A0.01280.30720.15680.105*
C800.0775 (7)0.4408 (7)0.13548 (13)0.101 (2)
H80A0.07810.49660.14900.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.107 (4)0.058 (3)0.068 (3)0.001 (3)−0.011 (3)−0.009 (2)
N20.046 (3)0.049 (3)0.086 (3)−0.002 (2)0.000 (2)0.008 (2)
N30.085 (4)0.086 (4)0.078 (4)0.008 (3)−0.008 (3)−0.008 (3)
C10.148 (7)0.097 (5)0.084 (4)0.030 (5)0.012 (4)0.023 (4)
C20.082 (5)0.076 (4)0.066 (4)0.020 (3)0.019 (3)0.000 (3)
C30.074 (4)0.083 (5)0.063 (3)0.003 (3)−0.004 (3)−0.010 (3)
C40.066 (4)0.075 (4)0.066 (4)−0.006 (3)−0.002 (3)−0.022 (3)
C50.054 (3)0.057 (3)0.070 (3)−0.003 (3)0.008 (3)−0.006 (3)
C60.066 (4)0.063 (4)0.070 (4)−0.002 (3)0.004 (3)−0.015 (3)
C70.094 (5)0.059 (4)0.072 (4)−0.005 (3)0.012 (3)−0.004 (3)
C80.065 (4)0.051 (3)0.083 (4)−0.006 (3)0.008 (3)−0.001 (3)
C90.065 (4)0.044 (3)0.078 (4)−0.009 (3)0.011 (3)0.004 (3)
C100.067 (4)0.051 (4)0.102 (5)−0.004 (3)0.023 (4)−0.002 (3)
C110.057 (4)0.072 (4)0.118 (5)−0.005 (3)0.025 (4)−0.001 (4)
C120.053 (4)0.066 (4)0.117 (5)0.002 (3)0.008 (4)0.021 (4)
C130.055 (4)0.055 (3)0.098 (4)0.002 (3)0.004 (3)0.015 (3)
C140.046 (3)0.052 (3)0.075 (4)−0.002 (2)−0.002 (3)0.011 (3)
C150.051 (3)0.058 (3)0.084 (4)0.003 (3)−0.004 (3)0.005 (3)
C160.061 (4)0.051 (3)0.065 (3)−0.011 (3)−0.008 (3)0.011 (3)
C170.056 (4)0.081 (4)0.086 (4)0.003 (3)0.005 (3)0.008 (3)
C180.092 (5)0.099 (5)0.082 (4)0.002 (4)0.024 (4)−0.001 (4)
C190.118 (6)0.092 (5)0.068 (4)−0.013 (5)0.010 (5)−0.010 (4)
C200.099 (6)0.097 (5)0.099 (6)0.008 (5)−0.014 (5)−0.013 (4)
N40.108 (4)0.052 (3)0.061 (3)0.002 (2)−0.009 (3)0.009 (2)
N50.048 (3)0.042 (2)0.065 (3)0.004 (2)0.001 (2)−0.009 (2)
N60.071 (3)0.085 (3)0.071 (3)−0.012 (3)−0.016 (3)0.001 (3)
C210.162 (8)0.107 (6)0.091 (5)−0.024 (5)0.006 (5)−0.023 (4)
C220.076 (4)0.072 (4)0.075 (4)−0.008 (3)0.011 (3)0.000 (3)
C230.077 (4)0.099 (5)0.062 (4)−0.010 (4)−0.004 (3)0.006 (4)
C240.078 (4)0.071 (4)0.064 (4)0.006 (3)−0.001 (3)0.013 (3)
C250.053 (3)0.055 (3)0.054 (3)0.003 (3)0.004 (3)0.013 (3)
C260.070 (4)0.061 (4)0.056 (3)0.003 (3)0.003 (3)0.004 (3)
C270.106 (5)0.060 (4)0.058 (3)−0.001 (3)0.006 (3)0.008 (3)
C280.061 (4)0.052 (3)0.060 (3)0.004 (3)0.001 (3)0.002 (2)
C290.062 (4)0.046 (3)0.065 (4)0.006 (3)0.007 (3)0.002 (2)
C300.077 (4)0.053 (4)0.089 (4)0.003 (3)0.026 (4)−0.002 (3)
C310.075 (4)0.064 (4)0.108 (5)−0.003 (3)0.025 (4)−0.005 (4)
C320.054 (4)0.060 (4)0.107 (5)0.000 (3)0.004 (3)−0.009 (3)
C330.049 (3)0.058 (3)0.083 (4)0.003 (3)0.003 (3)−0.010 (3)
C340.049 (3)0.054 (3)0.055 (3)0.001 (3)−0.003 (3)−0.005 (2)
C350.056 (3)0.052 (3)0.074 (4)0.003 (3)−0.002 (3)−0.003 (3)
C360.049 (4)0.051 (3)0.071 (4)0.004 (2)0.000 (3)−0.011 (3)
C370.060 (4)0.074 (4)0.066 (4)0.010 (3)0.004 (3)0.002 (3)
C380.065 (4)0.104 (5)0.082 (4)−0.005 (4)0.014 (4)0.005 (4)
C390.087 (5)0.111 (5)0.062 (4)−0.007 (4)0.000 (4)0.005 (3)
C400.084 (5)0.108 (5)0.066 (4)−0.012 (4)−0.016 (4)0.004 (4)
N70.059 (3)0.119 (4)0.058 (3)0.001 (3)0.013 (2)0.013 (3)
N80.044 (3)0.052 (3)0.068 (3)−0.007 (2)−0.001 (2)0.004 (2)
N90.079 (3)0.085 (3)0.063 (3)0.007 (3)0.013 (3)0.014 (3)
C410.099 (6)0.195 (8)0.082 (5)0.036 (6)−0.022 (4)0.005 (5)
C420.080 (5)0.079 (4)0.055 (4)0.008 (3)0.000 (3)−0.004 (3)
C430.090 (5)0.080 (4)0.059 (4)0.015 (4)0.010 (4)0.018 (3)
C440.068 (4)0.080 (4)0.063 (3)−0.002 (3)0.021 (3)0.008 (3)
C450.053 (4)0.062 (3)0.051 (3)−0.003 (3)0.004 (3)−0.001 (2)
C460.065 (4)0.076 (4)0.051 (3)0.001 (3)0.014 (3)0.005 (3)
C470.057 (4)0.091 (4)0.067 (4)0.001 (3)0.010 (3)−0.003 (3)
C480.050 (3)0.073 (4)0.063 (3)−0.001 (3)0.007 (3)0.005 (3)
C490.047 (3)0.065 (4)0.074 (4)−0.011 (3)0.005 (3)0.000 (3)
C500.060 (4)0.068 (4)0.095 (4)−0.011 (3)0.008 (3)−0.021 (4)
C510.067 (4)0.056 (4)0.132 (6)−0.004 (3)0.011 (4)−0.012 (4)
C520.060 (4)0.060 (4)0.112 (5)−0.004 (3)0.001 (4)0.006 (3)
C530.056 (3)0.054 (4)0.094 (4)−0.001 (3)0.000 (3)0.014 (3)
C540.054 (3)0.048 (3)0.065 (3)−0.002 (2)0.008 (3)0.008 (3)
C550.054 (3)0.059 (3)0.066 (3)−0.005 (3)−0.001 (3)0.011 (3)
C560.054 (3)0.062 (4)0.061 (3)−0.013 (3)−0.007 (3)0.013 (3)
C570.089 (4)0.064 (4)0.078 (4)−0.002 (3)0.012 (3)−0.001 (3)
C580.115 (6)0.088 (5)0.096 (5)−0.001 (4)0.019 (5)−0.019 (4)
C590.104 (6)0.129 (7)0.078 (5)−0.013 (5)0.014 (4)−0.013 (5)
C600.086 (5)0.125 (7)0.077 (5)−0.005 (5)0.003 (4)0.012 (4)
N100.053 (3)0.111 (4)0.083 (3)−0.006 (3)0.014 (3)−0.014 (3)
N110.042 (3)0.052 (3)0.078 (3)0.001 (2)−0.004 (2)−0.001 (2)
N120.105 (4)0.063 (3)0.083 (4)−0.017 (3)0.008 (3)−0.014 (3)
C610.088 (5)0.168 (8)0.098 (5)−0.024 (5)−0.003 (4)−0.004 (5)
C620.070 (4)0.081 (4)0.075 (4)−0.019 (3)0.004 (3)0.002 (3)
C630.082 (5)0.090 (5)0.068 (4)−0.006 (4)0.017 (4)−0.004 (3)
C640.062 (4)0.083 (4)0.079 (4)0.002 (3)0.018 (3)−0.006 (3)
C650.058 (4)0.056 (3)0.066 (3)−0.004 (3)0.012 (3)0.002 (3)
C660.059 (4)0.077 (4)0.062 (3)0.003 (3)0.010 (3)−0.006 (3)
C670.064 (4)0.093 (5)0.074 (4)−0.002 (3)0.009 (3)0.012 (3)
C680.047 (3)0.072 (4)0.074 (4)0.001 (3)0.000 (3)−0.005 (3)
C690.047 (3)0.061 (4)0.076 (4)0.005 (3)0.001 (3)0.005 (3)
C700.052 (4)0.080 (5)0.108 (5)0.015 (3)0.015 (4)0.016 (4)
C710.069 (4)0.057 (4)0.118 (5)−0.003 (3)0.009 (4)0.009 (4)
C720.066 (4)0.053 (4)0.116 (5)−0.003 (3)−0.004 (4)−0.007 (3)
C730.053 (3)0.053 (3)0.090 (4)−0.003 (3)−0.009 (3)−0.010 (3)
C740.052 (3)0.044 (3)0.072 (4)0.006 (2)−0.005 (3)−0.003 (3)
C750.053 (3)0.054 (3)0.083 (4)0.000 (3)0.011 (3)−0.016 (3)
C760.058 (3)0.053 (4)0.080 (4)0.002 (3)−0.006 (3)0.000 (3)
C770.102 (5)0.056 (4)0.080 (4)−0.002 (3)0.013 (4)−0.005 (3)
C780.115 (6)0.068 (4)0.092 (5)−0.003 (4)0.014 (4)0.010 (4)
C790.108 (6)0.085 (5)0.069 (4)−0.013 (4)0.010 (4)0.007 (4)
C800.134 (7)0.100 (6)0.071 (4)−0.022 (5)0.016 (4)−0.023 (4)
Geometric parameters (Å, °) top
N1—C51.384 (6)N7—C451.382 (6)
N1—C81.398 (7)N7—C481.399 (7)
N1—H1A0.8600N7—H7B0.8600
N2—C131.376 (6)N8—C541.379 (6)
N2—C141.388 (6)N8—C531.380 (6)
N2—C91.399 (7)N8—C491.399 (6)
N3—C161.337 (7)N9—C601.332 (8)
N3—C201.339 (8)N9—C561.332 (6)
C1—C21.501 (8)C41—C421.496 (9)
C1—H1B0.9600C41—H41A0.9600
C1—H1C0.9600C41—H41B0.9600
C1—H1D0.9600C41—H41C0.9600
C2—C31.355 (8)C42—C431.343 (8)
C2—C71.365 (8)C42—C471.369 (7)
C3—C41.375 (8)C43—C441.360 (8)
C3—H3B0.9300C43—H43A0.9300
C4—C51.380 (7)C44—C451.357 (7)
C4—H4A0.9300C44—H44A0.9300
C5—C61.384 (7)C45—C461.388 (7)
C6—C71.369 (7)C46—C471.363 (7)
C6—H6A0.9300C46—H46A0.9300
C7—H7A0.9300C47—H47A0.9300
C8—C151.385 (7)C48—C551.376 (7)
C8—C91.386 (7)C48—C491.393 (8)
C9—C101.390 (8)C49—C501.386 (8)
C10—C111.351 (8)C50—C511.329 (8)
C10—H10A0.9300C50—H50A0.9300
C11—C121.393 (8)C51—C521.409 (8)
C11—H11A0.9300C51—H51A0.9300
C12—C131.344 (8)C52—C531.332 (7)
C12—H12A0.9300C52—H52A0.9300
C13—H13A0.9300C53—H53A0.9300
C14—C151.378 (7)C54—C551.389 (7)
C14—C161.437 (7)C54—C561.461 (7)
C15—H15A0.9300C55—H55A0.9300
C16—C171.377 (8)C56—C571.358 (7)
C17—C181.360 (8)C57—C581.369 (8)
C17—H17A0.9300C57—H57A0.9300
C18—C191.359 (9)C58—C591.365 (10)
C18—H18A0.9300C58—H58A0.9300
C19—C201.338 (10)C59—C601.345 (10)
C19—H19A0.9300C59—H59A0.9300
C20—H20A0.9300C60—H60A0.9300
N4—C251.378 (6)N10—C651.387 (7)
N4—C281.422 (6)N10—C681.407 (7)
N4—H4B0.8600N10—H10B0.8600
N5—C331.371 (6)N11—C731.377 (6)
N5—C341.383 (6)N11—C691.385 (6)
N5—C291.397 (6)N11—C741.399 (6)
N6—C401.332 (7)N12—C801.322 (8)
N6—C361.343 (6)N12—C761.332 (7)
C21—C221.513 (8)C61—C621.504 (8)
C21—H21A0.9600C61—H61A0.9600
C21—H21B0.9600C61—H61B0.9600
C21—H21C0.9600C61—H61C0.9600
C22—C231.372 (8)C62—C671.359 (8)
C22—C271.377 (8)C62—C631.381 (8)
C23—C241.383 (8)C63—C641.380 (8)
C23—H23A0.9300C63—H63A0.9300
C24—C251.372 (7)C64—C651.386 (7)
C24—H24A0.9300C64—H64A0.9300
C25—C261.369 (7)C65—C661.365 (7)
C26—C271.383 (7)C66—C671.368 (8)
C26—H26A0.9300C66—H66A0.9300
C27—H27A0.9300C67—H67A0.9300
C28—C351.369 (7)C68—C691.361 (7)
C28—C291.376 (7)C68—C751.390 (7)
C29—C301.397 (8)C69—C701.411 (8)
C30—C311.356 (8)C70—C711.358 (9)
C30—H30A0.9300C70—H70A0.9300
C31—C321.396 (8)C71—C721.388 (9)
C31—H31A0.9300C71—H71A0.9300
C32—C331.345 (7)C72—C731.329 (8)
C32—H32A0.9300C72—H72A0.9300
C33—H33A0.9300C73—H73A0.9300
C34—C351.378 (7)C74—C751.375 (7)
C34—C361.432 (7)C74—C761.430 (7)
C35—H35A0.9300C75—H75A0.9300
C36—C371.388 (7)C76—C771.374 (7)
C37—C381.362 (8)C77—C781.362 (8)
C37—H37A0.9300C77—H77A0.9300
C38—C391.363 (8)C78—C791.379 (8)
C38—H38A0.9300C78—H78A0.9300
C39—C401.347 (9)C79—C801.364 (9)
C39—H39A0.9300C79—H79A0.9300
C40—H40A0.9300C80—H80A0.9300
C5—N1—C8123.1 (4)C45—N7—C48123.9 (5)
C5—N1—H1A118.4C45—N7—H7B118.1
C8—N1—H1A118.4C48—N7—H7B118.1
C13—N2—C14130.8 (5)C54—N8—C53130.6 (5)
C13—N2—C9120.5 (5)C54—N8—C49109.3 (4)
C14—N2—C9108.7 (5)C53—N8—C49120.1 (5)
C16—N3—C20117.6 (6)C60—N9—C56116.6 (6)
C2—C1—H1B109.5C42—C41—H41A109.5
C2—C1—H1C109.5C42—C41—H41B109.5
H1B—C1—H1C109.5H41A—C41—H41B109.5
C2—C1—H1D109.5C42—C41—H41C109.5
H1B—C1—H1D109.5H41A—C41—H41C109.5
H1C—C1—H1D109.5H41B—C41—H41C109.5
C3—C2—C7117.0 (5)C43—C42—C47116.5 (6)
C3—C2—C1122.0 (6)C43—C42—C41122.4 (6)
C7—C2—C1121.0 (6)C47—C42—C41121.1 (7)
C2—C3—C4122.8 (5)C42—C43—C44122.3 (5)
C2—C3—H3B118.6C42—C43—H43A118.9
C4—C3—H3B118.6C44—C43—H43A118.9
C3—C4—C5119.8 (5)C45—C44—C43121.6 (6)
C3—C4—H4A120.1C45—C44—H44A119.2
C5—C4—H4A120.1C43—C44—H44A119.2
C4—C5—C6117.7 (5)C44—C45—N7121.6 (5)
C4—C5—N1120.4 (5)C44—C45—C46117.3 (5)
C6—C5—N1121.8 (5)N7—C45—C46121.0 (5)
C7—C6—C5120.5 (5)C47—C46—C45119.5 (5)
C7—C6—H6A119.7C47—C46—H46A120.3
C5—C6—H6A119.7C45—C46—H46A120.3
C2—C7—C6122.0 (5)C46—C47—C42122.8 (6)
C2—C7—H7A119.0C46—C47—H47A118.6
C6—C7—H7A119.0C42—C47—H47A118.6
C15—C8—C9106.9 (5)C55—C48—C49108.0 (5)
C15—C8—N1128.5 (5)C55—C48—N7127.5 (5)
C9—C8—N1124.6 (6)C49—C48—N7124.5 (5)
C8—C9—C10133.7 (6)C50—C49—C48134.6 (6)
C8—C9—N2107.7 (5)C50—C49—N8118.7 (5)
C10—C9—N2118.6 (6)C48—C49—N8106.7 (5)
C11—C10—C9120.7 (6)C51—C50—C49120.9 (6)
C11—C10—H10A119.7C51—C50—H50A119.5
C9—C10—H10A119.7C49—C50—H50A119.5
C10—C11—C12119.2 (6)C50—C51—C52119.5 (6)
C10—C11—H11A120.4C50—C51—H51A120.3
C12—C11—H11A120.4C52—C51—H51A120.3
C13—C12—C11121.9 (6)C53—C52—C51121.4 (6)
C13—C12—H12A119.0C53—C52—H52A119.3
C11—C12—H12A119.0C51—C52—H52A119.3
C12—C13—N2119.0 (6)C52—C53—N8119.4 (6)
C12—C13—H13A120.5C52—C53—H53A120.3
N2—C13—H13A120.5N8—C53—H53A120.3
C15—C14—N2106.4 (5)N8—C54—C55106.7 (5)
C15—C14—C16127.6 (5)N8—C54—C56126.1 (5)
N2—C14—C16125.9 (5)C55—C54—C56127.2 (5)
C14—C15—C8110.2 (5)C48—C55—C54109.3 (5)
C14—C15—H15A124.9C48—C55—H55A125.4
C8—C15—H15A124.9C54—C55—H55A125.4
N3—C16—C17120.2 (6)N9—C56—C57122.2 (6)
N3—C16—C14118.5 (5)N9—C56—C54117.2 (5)
C17—C16—C14121.3 (5)C57—C56—C54120.6 (5)
C18—C17—C16120.5 (6)C56—C57—C58119.9 (6)
C18—C17—H17A119.7C56—C57—H57A120.1
C16—C17—H17A119.7C58—C57—H57A120.1
C19—C18—C17118.9 (7)C59—C58—C57118.4 (7)
C19—C18—H18A120.6C59—C58—H58A120.8
C17—C18—H18A120.6C57—C58—H58A120.8
C20—C19—C18118.3 (7)C60—C59—C58118.2 (7)
C20—C19—H19A120.8C60—C59—H59A120.9
C18—C19—H19A120.8C58—C59—H59A120.9
C19—C20—N3124.4 (7)N9—C60—C59124.7 (7)
C19—C20—H20A117.8N9—C60—H60A117.7
N3—C20—H20A117.8C59—C60—H60A117.7
C25—N4—C28123.3 (4)C65—N10—C68123.8 (5)
C25—N4—H4B118.3C65—N10—H10B118.1
C28—N4—H4B118.3C68—N10—H10B118.1
C33—N5—C34130.6 (5)C73—N11—C69120.8 (5)
C33—N5—C29119.9 (5)C73—N11—C74130.5 (5)
C34—N5—C29109.5 (4)C69—N11—C74108.7 (4)
C40—N6—C36117.5 (5)C80—N12—C76117.4 (6)
C22—C21—H21A109.5C62—C61—H61A109.5
C22—C21—H21B109.5C62—C61—H61B109.5
H21A—C21—H21B109.5H61A—C61—H61B109.5
C22—C21—H21C109.5C62—C61—H61C109.5
H21A—C21—H21C109.5H61A—C61—H61C109.5
H21B—C21—H21C109.5H61B—C61—H61C109.5
C23—C22—C27117.3 (5)C67—C62—C63116.8 (6)
C23—C22—C21120.8 (6)C67—C62—C61121.8 (6)
C27—C22—C21121.9 (6)C63—C62—C61121.4 (6)
C22—C23—C24121.3 (6)C64—C63—C62121.6 (6)
C22—C23—H23A119.3C64—C63—H63A119.2
C24—C23—H23A119.3C62—C63—H63A119.2
C25—C24—C23120.8 (5)C63—C64—C65120.2 (6)
C25—C24—H24A119.6C63—C64—H64A119.9
C23—C24—H24A119.6C65—C64—H64A119.9
C26—C25—C24118.7 (5)C66—C65—C64117.9 (5)
C26—C25—N4121.5 (5)C66—C65—N10122.8 (5)
C24—C25—N4119.8 (5)C64—C65—N10119.3 (5)
C25—C26—C27120.1 (5)C65—C66—C67120.9 (5)
C25—C26—H26A119.9C65—C66—H66A119.5
C27—C26—H26A119.9C67—C66—H66A119.5
C22—C27—C26121.9 (5)C62—C67—C66122.6 (6)
C22—C27—H27A119.1C62—C67—H67A118.7
C26—C27—H27A119.1C66—C67—H67A118.7
C35—C28—C29108.7 (5)C69—C68—C75108.0 (5)
C35—C28—N4127.4 (5)C69—C68—N10125.4 (6)
C29—C28—N4123.9 (5)C75—C68—N10126.5 (5)
C28—C29—C30134.5 (6)C68—C69—N11107.9 (5)
C28—C29—N5106.2 (5)C68—C69—C70133.7 (6)
C30—C29—N5119.3 (5)N11—C69—C70118.4 (5)
C31—C30—C29119.9 (6)C71—C70—C69119.8 (7)
C31—C30—H30A120.0C71—C70—H70A120.1
C29—C30—H30A120.0C69—C70—H70A120.1
C30—C31—C32119.5 (6)C70—C71—C72119.4 (6)
C30—C31—H31A120.3C70—C71—H71A120.3
C32—C31—H31A120.3C72—C71—H71A120.3
C33—C32—C31121.4 (6)C73—C72—C71122.1 (6)
C33—C32—H32A119.3C73—C72—H72A119.0
C31—C32—H32A119.3C71—C72—H72A119.0
C32—C33—N5119.9 (5)C72—C73—N11119.5 (6)
C32—C33—H33A120.0C72—C73—H73A120.2
N5—C33—H33A120.0N11—C73—H73A120.2
C35—C34—N5106.0 (4)C75—C74—N11106.2 (5)
C35—C34—C36128.0 (5)C75—C74—C76128.2 (5)
N5—C34—C36126.0 (4)N11—C74—C76125.6 (5)
C28—C35—C34109.5 (5)C74—C75—C68109.1 (5)
C28—C35—H35A125.2C74—C75—H75A125.4
C34—C35—H35A125.2C68—C75—H75A125.4
N6—C36—C37119.9 (5)N12—C76—C77120.5 (6)
N6—C36—C34119.7 (5)N12—C76—C74120.0 (5)
C37—C36—C34120.3 (5)C77—C76—C74119.4 (5)
C38—C37—C36120.7 (5)C78—C77—C76121.2 (6)
C38—C37—H37A119.6C78—C77—H77A119.4
C36—C37—H37A119.6C76—C77—H77A119.4
C37—C38—C39118.7 (6)C77—C78—C79118.8 (6)
C37—C38—H38A120.6C77—C78—H78A120.6
C39—C38—H38A120.6C79—C78—H78A120.6
C40—C39—C38118.1 (6)C80—C79—C78116.2 (6)
C40—C39—H39A121.0C80—C79—H79A121.9
C38—C39—H39A121.0C78—C79—H79A121.9
N6—C40—C39125.0 (6)N12—C80—C79125.9 (6)
N6—C40—H40A117.5N12—C80—H80A117.0
C39—C40—H40A117.5C79—C80—H80A117.0
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···N30.932.302.878 (8)120 (1)
C33—H33A···N60.932.322.902 (8)121 (1)
C53—H53A···N90.932.292.867 (7)120 (1)
C73—H73A···N120.932.352.917 (8)119 (1)
N7—H7B···Cg1i0.862.83 (1)3.673 (2)169 (1)
C57—H57A···Cg2ii0.932.98 (1)3.852 (3)157 (1)
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···N30.932.302.878 (8)120 (1)
C33—H33A···N60.932.322.902 (8)121 (1)
C53—H53A···N90.932.292.867 (7)120 (1)
C73—H73A···N120.932.352.917 (8)119 (1)
N7—H7B···Cg1i0.862.83 (1)3.673 (2)169 (1)
C57—H57A···Cg2ii0.932.98 (1)3.852 (3)157 (1)
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x, y−1, z.
Acknowledgements top

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005B04).

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Hema, R., Parthasarathi, V., Ravikumar, K., Sarkunam, K. & Nallu, M. (2004). Acta Cryst. E60, o479–o480.

Hema, R., Parthasarathi, V., Sarkunam, K., Nallu, M. & Linden, A. (2003). Acta Cryst. C59, o703–o705.

Sheldrick, G. M. (1990). SHELXTLPC. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.