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Acta Cryst. (2009). E65, o295    [ doi:10.1107/S160053680900110X ]

(E)-N'-(4-Pyridylmethylene)-4-(8-quinolyloxy)butanohydrazide 0.25-hydrate

M.-E. Chen and J.-M. Li

Abstract top

The asymmetric unit of the title compound, C19H18N4O2·0.25H2O, contains two organic molecules and a solvent water molecule with 50% occupancy. The two molecules differ in their conformations: in one molecule it is (+)gauche-trans-trans-(+)gauche-trans, whereas in the other it is (-)gauche-trans-trans-(-)gauche-trans. The dihedral angles between the pyridine ring and the quinoline ring system are 67.4 (3) and 68.0 (2)°. Molecules are linked into a supramolecular two-dimensional array via N-H...N hydrogen bonds, with each partially occupied water molecule connected via an O-H...O hydrogen bond. C-H...O interactions are also present.

Comment top

The coordination chemistry of 8-hydroxyquinoline and its derivatives is well studied (Cai et al., 2003; Chen et al., 2005; Park et al., 2006; Karmakar et al. 2007). In the course of our studies searching for good extractants of metal ions, the title compound, (I), was synthesized and its crystal structure determined. The asymmetric unit comprises two independent molecules which differ in conformation and a water molecule with a 50% site occupancy factor. In one molecule, the conformation along the O1—C10—C11—C12—C13—N2—N3—C14 bond sequence is (+)gauche-trans-trans-(+)gauche-trans, whereas in the second molecule the conformation is (-)gauche-trans-trans-(-)gauche-trans along the corresponding O3—C29—C30—C31—C32—N6—N7—C33 bond sequence. Despite these differences, the dihedral angles between the mean planes of the pyridine and quinoline rings are not very different, i.e. 67.4 (3)° and 68.0 (2)° for the molecules containing atoms O1 and O3, respectively. The two independent molecules are linked to a supermolecular 2D array via N—H···N hydrogen bonds supported by C—H···O contacts, Table 1. Each partially occupied water molecules is connected to a layer via a O—H···O hydrogen bond.

Related literature top

For general background, see: Cai et al. (2003); Chen et al. (2005); Park et al. (2006); Karmakar et al. (2007). For related structures, see: Zheng et al. (2006, 2007, 2008); Xie et al. (2008).

Experimental top

4-(Quinolin-8-yloxy)butanohydrazide (0.01 mol), 4-pyridylaldehyde (0.01 mol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 8 h. After cooling to room temperature, the mixture was filtered. Colourless crystals were obtained by slow evaporation of a tetrahydrofuran solution over a period of 2 days; m.p. 438 K. Analysis found: C 67.34, H 5.50, N 16.53; C76H74N16O9 requires: C 67.30, H 5.54, N 16.51.

Refinement top

All H atoms were placed in idealized positions (C—H = 0.93–0.97 Å, N—H = 0.86 Å and O—H = 0.85 Å) and refined in the riding model approximation with Uiso(H) = 1.2Ueq(C or N) and Uiso(H) = 1.5Ueq(O). The water molecule was included in the model with a 50% site occupancy factor based on elemental analysis and refinement. In the absence of significant anomalous scattering effects, X Friedel pairs were averaged in the final refinement.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008.

Figures top
[Figure 1] Fig. 1. The molecular structures of the two independent molecules and the water molecule of crystallization (50% site occupancy) in (I), showing atom numbering scheme and displacement ellipsoids at the 30% probability level.
(E)-N'-(4-Pyridylmethylene)-4-(8-quinolyloxy)butanohydrazide 0.25-hydrate top
Crystal data top
C19H18N4O2·0.25H2OF(000) = 714
Mr = 1355.51Dx = 1.303 Mg m−3
Monoclinic, P21Melting point: 438 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 8.8816 (13) ÅCell parameters from 1165 reflections
b = 17.420 (2) Åθ = 2.2–20.0°
c = 11.3624 (17) ŵ = 0.09 mm−1
β = 100.765 (3)°T = 295 K
V = 1727.0 (4) Å3Block, colorless
Z = 10.32 × 0.26 × 0.22 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3169 independent reflections
Radiation source: fine-focus sealed tube1927 reflections with I > 2σ(I)
graphiteRint = 0.050
φ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.972, Tmax = 0.981k = −13→20
9142 measured reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.0877P)2 + 0.001P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3169 reflectionsΔρmax = 0.32 e Å−3
460 parametersΔρmin = −0.21 e Å−3
0 restraintsAbsolute structure: nd
Primary atom site location: structure-invariant direct methods
Crystal data top
C19H18N4O2·0.25H2OV = 1727.0 (4) Å3
Mr = 1355.51Z = 1
Monoclinic, P21Mo Kα radiation
a = 8.8816 (13) ŵ = 0.09 mm−1
b = 17.420 (2) ÅT = 295 K
c = 11.3624 (17) Å0.32 × 0.26 × 0.22 mm
β = 100.765 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3169 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1927 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.981Rint = 0.050
9142 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.162Δρmax = 0.32 e Å−3
S = 1.01Δρmin = −0.21 e Å−3
3169 reflectionsAbsolute structure: nd
460 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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)
N11.1571 (5)0.0923 (3)0.6124 (4)0.0478 (12)
N20.7191 (6)0.1522 (3)0.1045 (4)0.0566 (14)
H20.72110.14600.02970.068*
N30.6437 (6)0.1008 (3)0.1636 (4)0.0510 (13)
N40.3307 (7)−0.1253 (4)0.2546 (6)0.0817 (18)
N50.6503 (5)0.1139 (3)0.8355 (4)0.0495 (12)
N61.0930 (6)0.0735 (3)1.3512 (4)0.0510 (13)
H61.09090.08101.42570.061*
N71.1691 (6)0.1246 (3)1.2916 (4)0.0474 (12)
N81.4779 (7)0.3522 (3)1.1941 (6)0.0674 (15)
O10.9800 (4)0.2139 (2)0.5363 (3)0.0497 (10)
O20.8522 (6)0.2626 (3)0.1125 (4)0.0769 (14)
O30.8302 (5)−0.0034 (2)0.9236 (3)0.0511 (10)
O40.9623 (6)−0.0348 (2)1.3516 (4)0.0707 (14)
O50.2645 (9)0.3398 (5)0.6539 (8)0.072 (3)0.50
H390.21240.38050.63570.107*0.50
H400.27940.33620.72970.107*0.50
C11.0067 (7)0.1999 (3)0.6560 (5)0.0430 (14)
C20.9470 (7)0.2422 (3)0.7384 (5)0.0491 (15)
H10.88400.28400.71340.059*
C30.9807 (7)0.2225 (4)0.8599 (5)0.0557 (16)
H30.93890.25140.91470.067*
C41.0719 (7)0.1628 (4)0.8992 (5)0.0569 (17)
H41.09320.15150.98060.068*
C51.1361 (7)0.1168 (3)0.8187 (5)0.0478 (15)
C61.2298 (7)0.0529 (4)0.8537 (5)0.0583 (17)
H51.25340.03890.93400.070*
C71.2853 (8)0.0120 (4)0.7713 (6)0.0662 (18)
H71.3495−0.02980.79380.079*
C81.2449 (8)0.0333 (4)0.6505 (6)0.0608 (17)
H81.28240.00390.59400.073*
C91.1020 (6)0.1352 (3)0.6951 (4)0.0391 (13)
C100.8914 (7)0.2810 (3)0.4948 (5)0.0508 (15)
H10A0.94160.32680.53180.061*
H10B0.79030.27760.51520.061*
C110.8788 (7)0.2845 (3)0.3596 (5)0.0537 (16)
H11A0.82700.33150.32950.064*
H11B0.98080.28540.34060.064*
C120.7917 (7)0.2168 (3)0.2986 (4)0.0498 (15)
H12A0.68670.21920.31100.060*
H12B0.83700.16990.33530.060*
C130.7914 (7)0.2139 (4)0.1658 (5)0.0517 (15)
C140.5817 (7)0.0439 (4)0.1021 (5)0.0523 (15)
H140.59150.03890.02240.063*
C150.4960 (7)−0.0130 (3)0.1556 (5)0.0491 (15)
C160.4348 (7)−0.0766 (4)0.0895 (6)0.0593 (16)
H160.4488−0.08320.01100.071*
C170.3533 (8)−0.1299 (4)0.1419 (7)0.075 (2)
H170.3116−0.17150.09600.090*
C180.3892 (9)−0.0646 (5)0.3151 (7)0.076 (2)
H180.3749−0.06000.39380.091*
C190.4703 (7)−0.0070 (4)0.2711 (5)0.0581 (17)
H190.50680.03500.31860.070*
C200.8106 (7)0.0064 (3)0.8035 (5)0.0442 (14)
C210.8736 (7)−0.0391 (4)0.7273 (5)0.0558 (16)
H210.9340−0.08070.75770.067*
C220.8485 (8)−0.0239 (4)0.6043 (6)0.0649 (19)
H220.8948−0.05460.55430.078*
C230.7566 (8)0.0355 (4)0.5573 (5)0.0649 (19)
H230.73960.04460.47520.078*
C240.6872 (7)0.0832 (4)0.6320 (5)0.0512 (16)
C250.5906 (8)0.1436 (4)0.5884 (6)0.070 (2)
H250.57010.15420.50680.084*
C260.5250 (8)0.1879 (4)0.6658 (6)0.070 (2)
H260.45890.22800.63780.083*
C270.5617 (8)0.1702 (4)0.7890 (6)0.0663 (18)
H270.51940.20100.84120.080*
C280.7132 (7)0.0686 (3)0.7572 (5)0.0455 (14)
C290.9213 (7)−0.0686 (3)0.9732 (5)0.0523 (15)
H29A1.0227−0.06590.95330.063*
H29B0.8731−0.11610.94140.063*
C300.9317 (7)−0.0652 (3)1.1079 (5)0.0472 (14)
H30A0.8291−0.06491.12590.057*
H30B0.9839−0.11071.14410.057*
C311.0176 (7)0.0060 (3)1.1622 (5)0.0479 (14)
H31A1.12170.00441.14770.057*
H31B0.96840.05141.12320.057*
C321.0214 (7)0.0116 (3)1.2951 (5)0.0492 (14)
C331.2327 (7)0.1813 (4)1.3530 (5)0.0517 (15)
H331.22560.18601.43330.062*
C341.3162 (6)0.2387 (3)1.2971 (5)0.0448 (14)
C351.3416 (7)0.2328 (4)1.1804 (5)0.0580 (17)
H351.30530.19041.13390.070*
C361.4204 (8)0.2895 (4)1.1339 (6)0.071 (2)
H361.43470.28401.05530.085*
C371.4515 (8)0.3568 (4)1.3043 (6)0.0665 (19)
H371.48790.40021.34820.080*
C381.3756 (7)0.3035 (4)1.3600 (6)0.0603 (17)
H381.36400.31071.43890.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.053 (3)0.049 (3)0.043 (3)0.012 (2)0.012 (2)0.000 (2)
N20.068 (4)0.063 (4)0.042 (3)−0.004 (3)0.017 (3)0.005 (2)
N30.052 (3)0.061 (3)0.041 (3)0.000 (3)0.010 (2)0.001 (3)
N40.084 (5)0.072 (5)0.091 (5)−0.008 (4)0.020 (4)0.010 (4)
N50.051 (3)0.052 (3)0.045 (3)−0.006 (3)0.005 (2)0.000 (2)
N60.070 (4)0.050 (3)0.036 (3)−0.004 (3)0.019 (3)0.003 (2)
N70.056 (3)0.042 (3)0.045 (3)0.000 (2)0.012 (2)0.004 (2)
N80.069 (4)0.059 (4)0.075 (4)−0.009 (3)0.016 (3)0.007 (3)
O10.067 (3)0.046 (2)0.036 (2)0.013 (2)0.0091 (18)0.0019 (17)
O20.110 (4)0.072 (3)0.055 (3)−0.020 (3)0.031 (3)0.010 (2)
O30.066 (3)0.054 (3)0.033 (2)0.010 (2)0.0065 (18)0.0019 (17)
O40.111 (4)0.060 (3)0.048 (2)−0.026 (3)0.032 (3)0.002 (2)
O50.059 (6)0.055 (5)0.102 (7)0.002 (4)0.018 (5)−0.020 (5)
C10.057 (4)0.037 (3)0.035 (3)−0.005 (3)0.009 (3)−0.001 (2)
C20.063 (4)0.041 (3)0.047 (4)−0.002 (3)0.017 (3)−0.011 (3)
C30.073 (4)0.055 (4)0.043 (3)−0.006 (4)0.021 (3)−0.013 (3)
C40.068 (4)0.069 (5)0.031 (3)−0.019 (4)0.002 (3)−0.004 (3)
C50.049 (4)0.050 (4)0.041 (3)0.000 (3)0.000 (3)−0.001 (3)
C60.057 (4)0.074 (5)0.039 (4)0.003 (4)−0.003 (3)0.009 (3)
C70.064 (4)0.070 (5)0.062 (4)0.019 (4)0.004 (3)0.014 (4)
C80.069 (4)0.058 (4)0.058 (4)0.016 (4)0.018 (3)0.002 (3)
C90.046 (3)0.037 (3)0.034 (3)−0.001 (3)0.006 (2)0.000 (2)
C100.061 (4)0.039 (3)0.050 (4)0.003 (3)0.004 (3)−0.002 (3)
C110.065 (4)0.049 (4)0.047 (4)0.001 (3)0.010 (3)0.006 (3)
C120.062 (4)0.051 (4)0.036 (3)0.004 (3)0.007 (3)0.008 (3)
C130.057 (4)0.054 (4)0.044 (3)0.002 (3)0.011 (3)0.007 (3)
C140.060 (4)0.059 (4)0.039 (3)0.010 (3)0.013 (3)0.002 (3)
C150.046 (4)0.049 (4)0.049 (4)0.003 (3)0.003 (3)0.004 (3)
C160.068 (4)0.048 (4)0.061 (4)0.009 (3)0.009 (3)−0.006 (3)
C170.078 (5)0.052 (5)0.093 (6)−0.003 (4)0.007 (4)−0.006 (4)
C180.075 (5)0.084 (6)0.069 (5)0.006 (5)0.017 (4)0.006 (4)
C190.068 (4)0.060 (4)0.046 (4)−0.003 (4)0.009 (3)0.003 (3)
C200.051 (3)0.048 (3)0.033 (3)−0.006 (3)0.003 (3)−0.004 (3)
C210.063 (4)0.064 (4)0.041 (3)−0.003 (3)0.010 (3)−0.011 (3)
C220.072 (5)0.077 (5)0.050 (4)−0.019 (4)0.023 (3)−0.019 (4)
C230.072 (4)0.087 (5)0.036 (3)−0.023 (4)0.010 (3)−0.004 (4)
C240.053 (4)0.062 (4)0.037 (3)−0.021 (3)0.005 (3)0.004 (3)
C250.071 (5)0.080 (5)0.053 (4)−0.017 (4)−0.004 (4)0.015 (4)
C260.065 (5)0.065 (5)0.070 (5)−0.006 (4)−0.009 (4)0.020 (4)
C270.067 (5)0.060 (4)0.071 (5)0.007 (4)0.013 (4)0.006 (4)
C280.046 (3)0.055 (4)0.035 (3)−0.013 (3)0.008 (3)−0.006 (3)
C290.067 (4)0.040 (3)0.048 (3)0.001 (3)0.005 (3)−0.002 (3)
C300.058 (4)0.036 (3)0.045 (3)0.003 (3)0.004 (3)0.010 (3)
C310.058 (4)0.044 (3)0.042 (3)−0.004 (3)0.010 (3)0.007 (3)
C320.064 (4)0.045 (3)0.040 (3)−0.001 (3)0.013 (3)0.002 (3)
C330.054 (4)0.055 (4)0.045 (4)−0.001 (3)0.005 (3)−0.001 (3)
C340.047 (3)0.039 (3)0.049 (4)0.005 (3)0.011 (3)0.000 (3)
C350.060 (4)0.056 (4)0.057 (4)−0.011 (3)0.007 (3)−0.009 (3)
C360.079 (5)0.080 (5)0.057 (4)−0.018 (4)0.023 (4)0.004 (4)
C370.071 (5)0.050 (4)0.075 (5)−0.005 (4)0.005 (4)−0.008 (4)
C380.062 (4)0.060 (4)0.059 (4)−0.002 (4)0.012 (3)0.000 (3)
Geometric parameters (Å, °) top
N1—C81.314 (7)C12—H12A0.9700
N1—C91.361 (6)C12—H12B0.9700
N2—C131.373 (8)C14—C151.451 (8)
N2—N31.368 (6)C14—H140.9300
N2—H20.8600C15—C191.378 (8)
N3—C141.277 (7)C15—C161.391 (8)
N4—C181.314 (9)C16—C171.378 (9)
N4—C171.335 (9)C16—H160.9300
N5—C271.306 (8)C17—H170.9300
N5—C281.381 (7)C18—C191.382 (9)
N6—C321.349 (7)C18—H180.9300
N6—N71.371 (6)C19—H190.9300
N6—H60.8600C20—C211.368 (7)
N7—C331.278 (7)C20—C281.425 (8)
N8—C371.317 (8)C21—C221.398 (8)
N8—C361.339 (9)C21—H210.9300
O1—C11.359 (6)C22—C231.364 (9)
O1—C101.438 (6)C22—H220.9300
O2—C131.224 (7)C23—C241.411 (8)
O3—C201.354 (6)C23—H230.9300
O3—C291.445 (7)C24—C251.389 (9)
O4—C321.212 (7)C24—C281.421 (7)
O5—H390.8500C25—C261.377 (9)
O5—H400.8499C25—H250.9300
C1—C21.373 (7)C26—C271.410 (9)
C1—C91.429 (7)C26—H260.9300
C2—C31.400 (8)C27—H270.9300
C2—H10.9300C29—C301.518 (7)
C3—C41.342 (9)C29—H29A0.9700
C3—H30.9300C29—H29B0.9700
C4—C51.414 (8)C30—C311.524 (8)
C4—H40.9300C30—H30A0.9700
C5—C61.402 (8)C30—H30B0.9700
C5—C91.417 (7)C31—C321.507 (8)
C6—C71.343 (9)C31—H31A0.9700
C6—H50.9300C31—H31B0.9700
C7—C81.402 (9)C33—C341.460 (8)
C7—H70.9300C33—H330.9300
C8—H80.9300C34—C381.386 (8)
C10—C111.521 (7)C34—C351.389 (8)
C10—H10A0.9700C35—C361.373 (8)
C10—H10B0.9700C35—H350.9300
C11—C121.506 (8)C36—H360.9300
C11—H11A0.9700C37—C381.370 (9)
C11—H11B0.9700C37—H370.9300
C12—C131.509 (7)C38—H380.9300
C8—N1—C9118.0 (5)C16—C17—H17118.0
C13—N2—N3119.3 (5)N4—C18—C19125.2 (7)
C13—N2—H2120.4N4—C18—H18117.4
N3—N2—H2120.4C19—C18—H18117.4
C14—N3—N2116.1 (5)C15—C19—C18118.6 (6)
C18—N4—C17115.7 (6)C15—C19—H19120.7
C27—N5—C28117.0 (5)C18—C19—H19120.7
C32—N6—N7121.2 (4)O3—C20—C21125.0 (5)
C32—N6—H6119.4O3—C20—C28115.0 (5)
N7—N6—H6119.4C21—C20—C28119.9 (5)
C33—N7—N6116.2 (5)C20—C21—C22121.0 (6)
C37—N8—C36114.6 (6)C20—C21—H21119.5
C1—O1—C10117.2 (4)C22—C21—H21119.5
C20—O3—C29116.7 (4)C23—C22—C21120.5 (6)
H39—O5—H40106.4C23—C22—H22119.8
O1—C1—C2124.6 (5)C21—C22—H22119.8
O1—C1—C9115.8 (4)C22—C23—C24120.6 (6)
C2—C1—C9119.5 (5)C22—C23—H23119.7
C1—C2—C3120.2 (6)C24—C23—H23119.7
C1—C2—H1119.9C25—C24—C23122.8 (6)
C3—C2—H1119.9C25—C24—C28117.8 (6)
C4—C3—C2121.4 (5)C23—C24—C28119.3 (6)
C4—C3—H3119.3C24—C25—C26120.2 (6)
C2—C3—H3119.3C24—C25—H25119.9
C3—C4—C5121.1 (6)C26—C25—H25119.9
C3—C4—H4119.5C25—C26—C27117.7 (7)
C5—C4—H4119.5C25—C26—H26121.2
C6—C5—C9117.8 (5)C27—C26—H26121.2
C6—C5—C4123.8 (6)N5—C27—C26125.2 (7)
C9—C5—C4118.4 (5)N5—C27—H27117.4
C7—C6—C5120.0 (6)C26—C27—H27117.4
C7—C6—H5120.0N5—C28—C24122.2 (6)
C5—C6—H5120.0N5—C28—C20119.1 (5)
C6—C7—C8118.8 (6)C24—C28—C20118.7 (5)
C6—C7—H7120.6O3—C29—C30106.6 (4)
C8—C7—H7120.6O3—C29—H29A110.4
N1—C8—C7123.9 (6)C30—C29—H29A110.4
N1—C8—H8118.1O3—C29—H29B110.4
C7—C8—H8118.1C30—C29—H29B110.4
N1—C9—C5121.5 (5)H29A—C29—H29B108.6
N1—C9—C1119.2 (5)C31—C30—C29111.8 (5)
C5—C9—C1119.4 (5)C31—C30—H30A109.2
O1—C10—C11107.2 (4)C29—C30—H30A109.2
O1—C10—H10A110.3C31—C30—H30B109.2
C11—C10—H10A110.3C29—C30—H30B109.2
O1—C10—H10B110.3H30A—C30—H30B107.9
C11—C10—H10B110.3C32—C31—C30112.0 (5)
H10A—C10—H10B108.5C32—C31—H31A109.2
C12—C11—C10111.7 (5)C30—C31—H31A109.2
C12—C11—H11A109.3C32—C31—H31B109.2
C10—C11—H11A109.3C30—C31—H31B109.2
C12—C11—H11B109.3H31A—C31—H31B107.9
C10—C11—H11B109.3O4—C32—N6119.7 (5)
H11A—C11—H11B107.9O4—C32—C31123.8 (6)
C11—C12—C13113.1 (5)N6—C32—C31116.5 (5)
C11—C12—H12A109.0N7—C33—C34120.0 (5)
C13—C12—H12A109.0N7—C33—H33120.0
C11—C12—H12B109.0C34—C33—H33120.0
C13—C12—H12B109.0C38—C34—C35116.0 (5)
H12A—C12—H12B107.8C38—C34—C33120.6 (5)
O2—C13—N2120.0 (5)C35—C34—C33123.4 (5)
O2—C13—C12123.5 (6)C36—C35—C34119.9 (6)
N2—C13—C12116.5 (5)C36—C35—H35120.0
N3—C14—C15120.5 (5)C34—C35—H35120.0
N3—C14—H14119.8N8—C36—C35124.3 (6)
C15—C14—H14119.8N8—C36—H36117.9
C19—C15—C16117.3 (6)C35—C36—H36117.9
C19—C15—C14122.7 (5)N8—C37—C38126.1 (6)
C16—C15—C14120.0 (5)N8—C37—H37117.0
C17—C16—C15119.1 (6)C38—C37—H37117.0
C17—C16—H16120.5C37—C38—C34119.0 (6)
C15—C16—H16120.5C37—C38—H38120.5
N4—C17—C16124.0 (7)C34—C38—H38120.5
N4—C17—H17118.0
C13—N2—N3—C14−178.6 (5)N4—C18—C19—C15−1.3 (11)
C32—N6—N7—C33179.8 (5)C29—O3—C20—C21−1.9 (8)
C10—O1—C1—C24.5 (8)C29—O3—C20—C28176.6 (5)
C10—O1—C1—C9−176.7 (5)O3—C20—C21—C22−179.2 (6)
O1—C1—C2—C3179.5 (5)C28—C20—C21—C222.3 (8)
C9—C1—C2—C30.7 (8)C20—C21—C22—C23−1.9 (9)
C1—C2—C3—C40.4 (9)C21—C22—C23—C240.9 (9)
C2—C3—C4—C5−0.8 (9)C22—C23—C24—C25−178.9 (6)
C3—C4—C5—C6−178.7 (6)C22—C23—C24—C28−0.3 (9)
C3—C4—C5—C90.1 (9)C23—C24—C25—C26179.4 (6)
C9—C5—C6—C70.8 (9)C28—C24—C25—C260.9 (9)
C4—C5—C6—C7179.6 (6)C24—C25—C26—C271.0 (10)
C5—C6—C7—C8−1.5 (10)C28—N5—C27—C260.3 (9)
C9—N1—C8—C7−0.1 (9)C25—C26—C27—N5−1.7 (11)
C6—C7—C8—N11.3 (11)C27—N5—C28—C241.7 (8)
C8—N1—C9—C5−0.7 (8)C27—N5—C28—C20−179.9 (6)
C8—N1—C9—C1179.8 (5)C25—C24—C28—N5−2.3 (8)
C6—C5—C9—N10.4 (8)C23—C24—C28—N5179.1 (5)
C4—C5—C9—N1−178.5 (5)C25—C24—C28—C20179.3 (5)
C6—C5—C9—C1179.9 (5)C23—C24—C28—C200.7 (8)
C4—C5—C9—C11.0 (8)O3—C20—C28—N51.2 (7)
O1—C1—C9—N1−0.8 (7)C21—C20—C28—N5179.9 (5)
C2—C1—C9—N1178.1 (5)O3—C20—C28—C24179.6 (5)
O1—C1—C9—C5179.7 (5)C21—C20—C28—C24−1.7 (8)
C2—C1—C9—C5−1.4 (8)C20—O3—C29—C30177.7 (5)
C1—O1—C10—C11179.5 (5)O3—C29—C30—C31−64.3 (6)
O1—C10—C11—C1263.8 (6)C29—C30—C31—C32177.2 (5)
C10—C11—C12—C13−173.9 (5)N7—N6—C32—O4176.0 (5)
N3—N2—C13—O2−176.0 (5)N7—N6—C32—C31−5.4 (8)
N3—N2—C13—C124.5 (8)C30—C31—C32—O4−0.4 (8)
C11—C12—C13—O2−1.8 (8)C30—C31—C32—N6−179.0 (5)
C11—C12—C13—N2177.7 (5)N6—N7—C33—C34180.0 (5)
N2—N3—C14—C15−178.6 (5)N7—C33—C34—C38175.0 (6)
N3—C14—C15—C193.4 (9)N7—C33—C34—C35−5.0 (9)
N3—C14—C15—C16−177.0 (6)C38—C34—C35—C36−0.5 (9)
C19—C15—C16—C17−0.2 (9)C33—C34—C35—C36179.5 (6)
C14—C15—C16—C17−179.8 (5)C37—N8—C36—C35−0.9 (11)
C18—N4—C17—C161.3 (11)C34—C35—C36—N80.5 (11)
C15—C16—C17—N4−1.2 (10)C36—N8—C37—C381.4 (10)
C17—N4—C18—C190.0 (11)N8—C37—C38—C34−1.5 (10)
C16—C15—C19—C181.4 (9)C35—C34—C38—C370.9 (9)
C14—C15—C19—C18−179.1 (6)C33—C34—C38—C37−179.1 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C31—H31B···O30.972.552.908 (7)102
C22—H22···O4i0.932.513.224 (7)134
C12—H12B···O10.972.522.900 (7)103
C7—H7···N8ii0.932.553.466 (9)167
C3—H3···O2iii0.932.523.353 (7)150
C2—H1···N4iv0.932.553.390 (9)150
O5—H39···O4v0.852.172.964 (10)156
N6—H6···N1iii0.862.102.934 (6)163
N2—H2···N5i0.862.253.077 (7)161
Symmetry codes: (i) x, y, z−1; (ii) −x+3, y−1/2, −z+2; (iii) x, y, z+1; (iv) −x+1, y+1/2, −z+1; (v) −x+1, y+1/2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O4i0.932.513.224 (7)134
C7—H7···N8ii0.932.553.466 (9)167
C3—H3···O2iii0.932.523.353 (7)150
C2—H1···N4iv0.932.553.390 (9)150
O5—H39···O4v0.852.172.964 (10)156
N6—H6···N1iii0.862.102.934 (6)163
N2—H2···N5i0.862.253.077 (7)161
Symmetry codes: (i) x, y, z−1; (ii) −x+3, y−1/2, −z+2; (iii) x, y, z+1; (iv) −x+1, y+1/2, −z+1; (v) −x+1, y+1/2, −z+2.
Acknowledgements top

This work was supported by grants from Qinzhou University Foundation and the Young Key Teacher's Plan of Guangxi Zhuang Autonomous Region of the People's Republic of China [grant Nos. 2008XJKY-10B and 2008 (30)].

references
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