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Acta Cryst. (2007). E63, m1909    [ doi:10.1107/S1600536807028693 ]

(1,10-Phenanthroline)tri(3-phenylpropanoato)lanthanum(III)

H. Zhong, X.-M. Yang, Q.-Y. Luo and Y.-P. Xu

Abstract top

The LaIII atom in the title complex, [La(C9H9O2)3(C12H8N2)], is coordinated by two N atoms of a 1,10-phenanthroline (phen) ligand and four O atoms of three phenylpropanoate ligands. This mononuclear complex is further extended into a supramolecular network structure via nonclassical hydrogen bonds between CH groups of 1,10-phenanthroline or phenylpropanoate and O atoms of neighbouring phenylpropanoate ligands.

Comment top

In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Deborah et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The six-coordinate environment of the La atom is completed by The two N atoms of 1,10-phenanthroline ligand and four O atoms of three benzenepropanoic acid ligands (Table 1). The La—O bond lengths are in the range 2.478 (4) to 2.908 (6) Å. The La—N bond lengths are in the range 2.717 (6) to 2.749 (5) Å. C—H···O non-classical hydrogen bonds between C—H groups of 1,10-phenanthroline or benzenepropanoic acid and O atoms of neighbouring benzenepropanoic acid molecules, with an average C···O distances of 3.235 (10) Å, generate a layered hydrogen-bonded network (Fig. 2 and Table 2). The non-classical hydrogen-bonding interactions link the mononuclear complex into a supramolecular network structure.

Related literature top

For related literature, see: Allen et al. (1987); Deborah et al. (2000); Farrugia et al. (2000); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Starynowicz (1991, 1993); Tsukube & Shinoda (2002); Zhang et al. (2005); Zeng et al. (2000).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Lanthanum (III) chloride hexahydrate (106.1 mg, 0.3 mmol), phen (59.4 mg, 0.3 mmol), benzenepropanoic acid (90.1 mg, 0.6 mmol) and distilled water (3.5 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 423 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colourless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 − 0.97 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonding interactions are shown as dashed lines.
(1,10-Phenanthroline)tri(3-phenylpropanoato)lanthanum(III) top
Crystal data top
[La(C9H9O2)3(C12H8N2)]F(000) = 1552
Mr = 766.60Dx = 1.443 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9043 reflections
a = 19.904 (3) Åθ = 2.5–26.9°
b = 8.783 (5) ŵ = 1.26 mm−1
c = 21.012 (2) ÅT = 273 K
β = 106.163 (2)°Plane, colourless
V = 3528 (2) Å30.33 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker APE XII area-detector
diffractometer		7231 independent reflections
Radiation source: fine-focus sealed tube4916 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 26.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −25→24
Tmin = 0.682, Tmax = 0.907k = −10→11
26367 measured reflectionsl = −26→26
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.1521P)2 + 0.285P]
where P = (Fo2 + 2Fc2)/3
7231 reflections(Δ/σ)max = 0.003
373 parametersΔρmax = 1.05 e Å−3
4 restraintsΔρmin = −1.18 e Å−3
Crystal data top
[La(C9H9O2)3(C12H8N2)]V = 3528 (2) Å3
Mr = 766.60Z = 4
Monoclinic, P21/nMo Kα radiation
a = 19.904 (3) ŵ = 1.26 mm−1
b = 8.783 (5) ÅT = 273 K
c = 21.012 (2) Å0.33 × 0.12 × 0.08 mm
β = 106.163 (2)°
Data collection top
Bruker APE XII area-detector
diffractometer		7231 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4916 reflections with I > 2σ(I)
Tmin = 0.682, Tmax = 0.907Rint = 0.042
26367 measured reflectionsθmax = 26.6°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.171Δρmax = 1.05 e Å−3
S = 0.96Δρmin = −1.18 e Å−3
7231 reflectionsAbsolute structure: ?
373 parametersFlack parameter: ?
4 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*/Ueq
La10.931195 (16)0.19073 (4)0.964267 (15)0.04126 (16)
O10.9710 (2)0.0605 (5)0.8751 (2)0.0567 (11)
O21.0666 (2)−0.0830 (6)0.9217 (2)0.0606 (12)
O40.9402 (2)0.4212 (5)1.0342 (2)0.0565 (11)
O51.0078 (3)0.6126 (6)1.0912 (2)0.0669 (13)
O70.8464 (2)−0.0365 (5)0.9192 (2)0.0536 (10)
O80.9469 (2)−0.1380 (6)0.9773 (2)0.0588 (11)
N10.7968 (3)0.2345 (7)0.9665 (3)0.0577 (13)
N20.8346 (3)0.3067 (6)0.8549 (3)0.0562 (14)
C10.7780 (4)0.1909 (9)1.0205 (4)0.073 (2)
H10.81260.16831.05920.088*
C20.7095 (5)0.1790 (11)1.0201 (5)0.096 (3)
H20.69740.14871.05780.115*
C30.6579 (5)0.2135 (12)0.9613 (6)0.103 (4)
H30.61110.20530.96050.123*
C40.6744 (4)0.2596 (13)0.9041 (5)0.088 (3)
C50.7461 (4)0.2671 (8)0.9093 (4)0.0613 (17)
C60.6192 (6)0.2951 (16)0.8423 (7)0.137 (6)
H60.57200.28590.83980.165*
C70.6419 (5)0.3449 (14)0.7854 (5)0.111 (4)
H70.60910.37110.74590.133*
C80.7127 (5)0.3529 (11)0.7907 (4)0.083 (3)
C90.7658 (4)0.3097 (7)0.8501 (4)0.0601 (19)
C100.7367 (6)0.4012 (12)0.7367 (4)0.096 (3)
H100.70480.43180.69750.116*
C110.8049 (6)0.4030 (11)0.7419 (4)0.092 (3)
H110.82100.44030.70740.110*
C120.8525 (5)0.3479 (9)0.8001 (4)0.072 (2)
H120.89930.33950.80070.086*
C131.0282 (3)0.0026 (7)0.8772 (3)0.0506 (14)
C141.0520 (3)0.0495 (8)0.8169 (3)0.0573 (9)
H14A1.01790.01630.77670.069*
H14B1.05570.15950.81550.069*
C151.1171 (3)−0.0166 (8)0.8208 (3)0.0573 (9)
H15A1.14990.01680.86170.069*
H15B1.1124−0.12610.82360.069*
C161.1455 (3)0.0142 (8)0.7698 (3)0.0573 (9)
C171.2069 (5)−0.0559 (12)0.7763 (5)0.095 (3)
H171.2272−0.11530.81330.113*
C181.2400 (5)−0.0370 (14)0.7251 (6)0.108 (3)
H181.2821−0.08580.72760.129*
C191.2087 (7)0.0555 (13)0.6709 (7)0.119 (4)
H191.23100.06830.63770.142*
C201.1488 (7)0.1251 (15)0.6652 (6)0.122 (4)
H201.12880.18440.62810.146*
C211.1144 (5)0.1094 (12)0.7162 (5)0.096 (3)
H211.07290.16070.71390.115*
C220.9691 (3)0.4986 (7)1.0859 (3)0.0522 (15)
C230.9485 (4)0.4458 (8)1.1470 (3)0.0543 (9)
H23B0.89870.46101.13970.065*
H23A0.95800.33771.15350.065*
C240.9861 (4)0.5271 (8)1.2062 (3)0.0543 (9)
H24A1.03570.51491.21100.065*
H24B0.97550.63451.19860.065*
C250.9745 (4)0.4892 (7)1.2653 (3)0.0543 (9)
C260.9276 (4)0.3793 (12)1.2714 (4)0.084 (2)
H260.90160.32571.23460.101*
C270.9198 (7)0.3499 (16)1.3343 (5)0.126 (5)
H270.89000.27241.33970.151*
C280.9559 (6)0.4345 (15)1.3892 (5)0.115 (4)
H280.94700.41871.42990.137*
C291.0048 (5)0.5416 (13)1.3838 (4)0.102 (3)
H291.03050.59451.42100.122*
C301.0153 (4)0.5697 (10)1.3218 (4)0.082 (2)
H301.04850.64031.31740.099*
C310.8838 (3)−0.1527 (8)0.9391 (3)0.0517 (15)
C320.8576 (4)−0.3131 (8)0.9188 (4)0.0626 (19)
H32A0.8759−0.34520.88270.075*
H32B0.8769−0.38080.95590.075*
C330.7861 (6)−0.3313 (11)0.8993 (6)0.1096 (14)
H33A0.7668−0.25890.86410.132*
H33B0.7760−0.43240.88060.132*
C340.7529 (7)−0.3143 (9)0.9451 (7)0.1096 (14)
C350.7848 (7)−0.2738 (12)1.0127 (7)0.1096 (14)
H350.8325−0.25471.02880.132*
C360.7374 (6)−0.2645 (13)1.0548 (7)0.1096 (14)
H360.7530−0.23901.09950.132*
C370.6703 (7)−0.2950 (11)1.0249 (7)0.1096 (14)
H370.6403−0.28761.05170.132*
C380.6407 (7)−0.3338 (12)0.9634 (7)0.1096 (14)
H380.5934−0.35840.94910.132*
C390.6811 (6)−0.3370 (12)0.9211 (7)0.1096 (14)
H390.6609−0.35440.87620.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.0460 (2)0.0376 (2)0.0358 (2)−0.00143 (13)0.00419 (15)0.00054 (13)
O10.064 (3)0.057 (3)0.052 (2)0.005 (2)0.019 (2)0.003 (2)
O20.068 (3)0.066 (3)0.050 (3)0.008 (2)0.019 (2)0.014 (2)
O40.074 (3)0.047 (3)0.047 (2)−0.003 (2)0.014 (2)−0.008 (2)
O50.091 (4)0.067 (3)0.045 (3)−0.029 (3)0.021 (2)0.000 (2)
O70.049 (2)0.047 (3)0.057 (3)−0.003 (2)0.0016 (19)−0.003 (2)
O80.056 (3)0.061 (3)0.053 (3)−0.003 (2)0.002 (2)0.007 (2)
N10.054 (3)0.056 (3)0.058 (3)0.005 (3)0.006 (3)−0.005 (3)
N20.066 (4)0.054 (4)0.042 (3)0.004 (3)0.003 (3)0.002 (2)
C10.064 (5)0.094 (7)0.062 (5)0.009 (4)0.017 (4)−0.002 (4)
C20.057 (5)0.147 (10)0.087 (7)−0.003 (5)0.025 (5)−0.016 (6)
C30.054 (5)0.123 (10)0.129 (10)−0.005 (5)0.023 (6)−0.013 (7)
C40.057 (5)0.105 (7)0.088 (7)0.007 (5)−0.005 (4)−0.022 (6)
C50.062 (4)0.042 (4)0.073 (5)0.007 (3)0.007 (3)−0.007 (3)
C60.055 (6)0.207 (17)0.137 (12)−0.001 (7)0.004 (6)−0.023 (10)
C70.074 (6)0.153 (10)0.079 (6)0.043 (6)−0.022 (5)0.007 (6)
C80.082 (6)0.081 (5)0.062 (5)0.020 (5)−0.018 (4)−0.010 (4)
C90.067 (4)0.049 (4)0.050 (4)0.001 (3)−0.009 (3)−0.007 (3)
C100.119 (8)0.091 (7)0.055 (5)0.016 (6)−0.015 (5)−0.002 (4)
C110.130 (8)0.090 (7)0.043 (4)0.001 (6)0.003 (5)0.014 (4)
C120.091 (6)0.060 (5)0.055 (4)−0.003 (4)0.006 (4)0.009 (3)
C130.054 (4)0.045 (4)0.050 (4)−0.005 (3)0.012 (3)0.001 (3)
C140.061 (2)0.063 (3)0.053 (2)0.0072 (19)0.0242 (18)0.0129 (18)
C150.061 (2)0.063 (3)0.053 (2)0.0072 (19)0.0242 (18)0.0129 (18)
C160.061 (2)0.063 (3)0.053 (2)0.0072 (19)0.0242 (18)0.0129 (18)
C170.093 (6)0.121 (8)0.083 (6)0.008 (6)0.047 (5)−0.001 (5)
C180.093 (7)0.125 (10)0.121 (8)−0.009 (6)0.057 (6)−0.007 (7)
C190.151 (10)0.096 (8)0.151 (10)−0.015 (7)0.111 (9)−0.004 (7)
C200.165 (11)0.123 (9)0.107 (8)0.021 (9)0.087 (9)0.038 (7)
C210.113 (7)0.099 (7)0.098 (7)0.000 (6)0.066 (6)0.017 (6)
C220.064 (4)0.039 (4)0.053 (4)−0.002 (3)0.016 (3)0.001 (3)
C230.074 (2)0.052 (2)0.0390 (18)−0.0157 (18)0.0188 (17)−0.0037 (15)
C240.074 (2)0.052 (2)0.0390 (18)−0.0157 (18)0.0188 (17)−0.0037 (15)
C250.074 (2)0.052 (2)0.0390 (18)−0.0157 (18)0.0188 (17)−0.0037 (15)
C260.084 (5)0.110 (7)0.063 (5)−0.039 (5)0.026 (4)−0.013 (5)
C270.157 (11)0.167 (11)0.066 (6)−0.065 (9)0.052 (7)−0.010 (7)
C280.132 (9)0.155 (11)0.069 (6)−0.014 (8)0.049 (6)0.016 (7)
C290.130 (8)0.117 (8)0.053 (5)−0.017 (7)0.018 (5)−0.002 (5)
C300.092 (6)0.092 (6)0.060 (5)−0.030 (5)0.016 (4)−0.014 (4)
C310.050 (3)0.062 (4)0.039 (3)0.002 (3)0.005 (3)−0.001 (3)
C320.060 (4)0.061 (5)0.060 (4)0.011 (3)0.007 (3)−0.006 (3)
C330.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
C340.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
C350.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
C360.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
C370.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
C380.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
C390.108 (3)0.091 (3)0.135 (4)0.000 (2)0.044 (3)0.017 (3)
Geometric parameters (Å, º) top
La1—O12.504 (4)C15—H15B0.9700
La1—O42.478 (4)C16—C171.341 (11)
La1—O72.615 (4)C16—C211.401 (11)
La1—O82.908 (6)C17—C181.419 (13)
La1—N12.717 (6)C17—H170.9300
La1—N22.749 (5)C18—C191.396 (16)
La1—O8i2.440 (5)C18—H180.9300
La1—O2i2.566 (4)C19—C201.317 (15)
La1—O5ii2.570 (4)C19—H190.9300
O1—C131.237 (7)C20—C211.429 (12)
O2—C131.276 (7)C20—H200.9300
O2—La1i2.566 (4)C21—H210.9300
O4—C221.275 (8)C22—C231.524 (8)
O5—C221.250 (8)C23—C241.448 (8)
O5—La1ii2.570 (4)C23—H23B0.9700
O7—C311.263 (8)C23—H23A0.9700
O8—C311.295 (8)C24—C251.366 (8)
O8—La1i2.440 (5)C24—H24A0.9700
N1—C11.344 (10)C24—H24B0.9700
N1—C51.367 (9)C25—C261.374 (10)
N2—C91.345 (10)C25—C301.425 (9)
N2—C121.346 (9)C26—C271.397 (12)
C1—C21.365 (11)C26—H260.9300
C1—H10.9300C27—C281.391 (15)
C2—C31.402 (15)C27—H270.9300
C2—H20.9300C28—C291.381 (14)
C3—C41.390 (14)C28—H280.9300
C3—H30.9300C29—C301.397 (11)
C4—C51.404 (11)C29—H290.9300
C4—C61.483 (15)C30—H300.9300
C5—C91.453 (11)C31—C321.521 (10)
C6—C71.458 (16)C32—C331.376 (13)
C6—H60.9300C32—H32A0.9700
C7—C81.385 (14)C32—H32B0.9700
C7—H70.9300C33—C341.319 (16)
C8—C101.412 (13)C33—H33A0.9700
C8—C91.444 (10)C33—H33B0.9700
C10—C111.332 (12)C34—C391.390 (16)
C10—H100.9300C34—C351.430 (18)
C11—C121.407 (11)C35—C361.467 (15)
C11—H110.9300C35—H350.9300
C12—H120.9300C36—C371.335 (15)
C13—C141.527 (8)C36—H360.9300
C14—C151.400 (8)C37—C381.309 (16)
C14—H14A0.9700C37—H370.9300
C14—H14B0.9700C38—C391.354 (15)
C15—C161.370 (8)C38—H380.9300
C15—H15A0.9700C39—H390.9300
O1—La1—O4146.17 (15)C13—C14—H14B109.7
O1—La1—O771.74 (14)H14A—C14—H14B108.2
O1—La1—O864.45 (14)C16—C15—C14116.7 (6)
O4—La1—O7140.47 (15)C16—C15—H15A108.1
O4—La1—O8140.10 (13)C14—C15—H15A108.1
O7—La1—O847.01 (13)C16—C15—H15B108.1
O1—La1—N1126.56 (16)C14—C15—H15B108.1
O4—La1—N177.48 (16)H15A—C15—H15B107.3
O7—La1—N164.84 (16)C17—C16—C15113.1 (7)
O8—La1—N1102.67 (16)C17—C16—C21122.8 (7)
O1—La1—N280.59 (16)C15—C16—C21124.1 (7)
O4—La1—N296.40 (15)C16—C17—C18118.1 (10)
O7—La1—N275.47 (15)C16—C17—H17121.0
O8—La1—N2118.56 (14)C18—C17—H17121.0
N1—La1—N259.97 (18)C19—C18—C17119.4 (10)
O8i—La1—O487.64 (17)C19—C18—H18120.3
O8i—La1—O179.22 (15)C17—C18—H18120.3
O8i—La1—O2i72.78 (15)C20—C19—C18122.0 (10)
O4—La1—O2i76.59 (15)C20—C19—H19119.0
O1—La1—O2i127.14 (16)C18—C19—H19119.0
O8i—La1—O5ii80.04 (17)C19—C20—C21119.9 (11)
O4—La1—O5ii75.77 (15)C19—C20—H20120.1
O1—La1—O5ii71.35 (15)C21—C20—H20120.1
O2i—La1—O5ii141.66 (15)C16—C21—C20117.6 (9)
O8i—La1—O7119.25 (17)C16—C21—H21121.2
O2i—La1—O784.17 (15)C20—C21—H21121.2
O5ii—La1—O7133.41 (14)O5—C22—O4128.5 (6)
O8i—La1—N1149.81 (16)O5—C22—C23118.2 (6)
O2i—La1—N178.24 (16)O4—C22—C23113.2 (5)
O5ii—La1—N1120.31 (18)C24—C23—C22112.2 (5)
O8i—La1—N2149.02 (17)C24—C23—H23B109.2
O2i—La1—N2138.05 (17)C22—C23—H23B109.2
O5ii—La1—N271.35 (17)C24—C23—H23A109.2
O8i—La1—O872.45 (18)C22—C23—H23A109.2
O2i—La1—O864.71 (14)H23B—C23—H23A107.9
O5ii—La1—O8131.14 (15)C25—C24—C23118.9 (6)
C13—O1—La1129.9 (4)C25—C24—H24A107.6
C13—O2—La1i138.8 (4)C23—C24—H24A107.6
C22—O4—La1151.8 (4)C25—C24—H24B107.6
C22—O5—La1ii148.9 (4)C23—C24—H24B107.6
C31—O7—La1103.6 (4)H24A—C24—H24B107.0
C31—O8—La1i161.9 (5)C24—C25—C26123.2 (6)
C31—O8—La188.9 (4)C24—C25—C30115.9 (6)
La1i—O8—La1107.55 (18)C26—C25—C30121.0 (6)
C1—N1—C5119.5 (6)C25—C26—C27118.4 (8)
C1—N1—La1118.8 (5)C25—C26—H26120.8
C5—N1—La1120.1 (5)C27—C26—H26120.8
C9—N2—C12115.9 (6)C28—C27—C26121.2 (10)
C9—N2—La1122.0 (4)C28—C27—H27119.4
C12—N2—La1121.7 (5)C26—C27—H27119.4
N1—C1—C2121.9 (8)C29—C28—C27120.6 (9)
N1—C1—H1119.0C29—C28—H28119.7
C2—C1—H1119.0C27—C28—H28119.7
C1—C2—C3118.3 (9)C28—C29—C30119.2 (9)
C1—C2—H2120.9C28—C29—H29120.4
C3—C2—H2120.9C30—C29—H29120.4
C4—C3—C2122.2 (9)C29—C30—C25119.4 (8)
C4—C3—H3118.9C29—C30—H30120.3
C2—C3—H3118.9C25—C30—H30120.3
C3—C4—C5115.3 (8)O7—C31—O8120.3 (6)
C3—C4—C6121.5 (9)O7—C31—C32122.1 (6)
C5—C4—C6123.2 (10)O8—C31—C32117.6 (6)
N1—C5—C4122.9 (8)C33—C32—C31115.8 (7)
N1—C5—C9119.9 (6)C33—C32—H32A108.3
C4—C5—C9117.2 (7)C31—C32—H32A108.3
C7—C6—C4117.3 (9)C33—C32—H32B108.3
C7—C6—H6121.3C31—C32—H32B108.3
C4—C6—H6121.3H32A—C32—H32B107.4
C8—C7—C6119.4 (8)C34—C33—C32117.2 (12)
C8—C7—H7120.3C34—C33—H33A108.0
C6—C7—H7120.3C32—C33—H33A108.0
C7—C8—C10121.0 (9)C34—C33—H33B108.0
C7—C8—C9122.7 (9)C32—C33—H33B108.0
C10—C8—C9116.3 (8)H33A—C33—H33B107.2
N2—C9—C8123.7 (8)C33—C34—C39113.2 (14)
N2—C9—C5116.3 (6)C33—C34—C35125.2 (13)
C8—C9—C5120.1 (8)C39—C34—C35121.6 (12)
C11—C10—C8120.2 (8)C34—C35—C36115.5 (12)
C11—C10—H10119.9C34—C35—H35122.2
C8—C10—H10119.9C36—C35—H35122.2
C10—C11—C12119.4 (9)C37—C36—C35115.6 (13)
C10—C11—H11120.3C37—C36—H36122.2
C12—C11—H11120.3C35—C36—H36122.2
N2—C12—C11124.2 (9)C38—C37—C36129.3 (13)
N2—C12—H12117.9C38—C37—H37115.3
C11—C12—H12117.9C36—C37—H37115.3
O1—C13—O2128.8 (6)C37—C38—C39117.9 (13)
O1—C13—C14110.8 (5)C37—C38—H38121.1
O2—C13—C14120.3 (6)C39—C38—H38121.1
C15—C14—C13109.6 (5)C38—C39—C34119.8 (14)
C15—C14—H14A109.7C38—C39—H39120.1
C13—C14—H14A109.7C34—C39—H39120.1
C15—C14—H14B109.7
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.932.443.138 (10)132
C12—H12···O5ii0.932.533.087 (9)119
C32—H32B···O4iii0.972.483.435 (9)167
C10—H10···O7iv0.932.393.279 (9)159
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.932.443.138 (10)132
C12—H12···O5ii0.932.533.087 (9)119
C32—H32B···O4iii0.972.483.435 (9)167
C10—H10···O7iv0.932.393.279 (9)159
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+3/2.
Acknowledgements top

This work was supported by the Science and Technology Bureau of Jian, Jiangxi Province of China (grant No. 20052817).

references
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