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Acta Cryst. (2008). E64, o965    [ doi:10.1107/S1600536808009793 ]

3,3'-{1,1'-Methylenebis[naphthalene-2,1-diylbis(oxymethylene)]}dibenzonitrile

J. Xiao and H. Zhao

Abstract top

The title compound, C37H26N2O2, was synthesized from 1,1'-methylenedinaphthalen-2-ol and 3-(bromomethyl)benzonitrile. The two naphthyl systems are almost perpendicular to each other [dihedral angle 83.3 (9)°] and the two cyanobenzyloxy rings approximately parallel to each other [dihedral angle 15.5 (2)°].

Comment top

Nitrile derivatives are important materials in the synthesis of some heterocyclic molecules (Radl et al., 2000). Recently, we have reported a few benzonitrile compounds (Fu & Zhao, 2007). As an extension of our work on the structural characterization of nitrile compounds the structure of the title compound is reported here.

As shown in Fig. 1, the two naphthyl rings in the title compound are bridged by one C atom (C1) and are approximately perpendicular to each other with an dihedral angle of 83.3 (9)°. The two 3-cyanobenzyloxy rings, on the other hand are almost parallel to each other with a dihedral angle of 15.53 (0.23) °.

Related literature top

For the application of nitrile derivatives in the synthesis of some heterocyclic molecules, see: Radl et al. (2000). Fu & Zhao (2007) have reported benzonitrile compounds related to the title compound.

Experimental top

1,1'-Methylenedinaphthalen-2-ol (0.3 g, 1 mmol) and 3-(bromomethyl)benzonitrile (0.392 g, 2 mmol) were dissolved in acetone in the presence of K2CO3 (0.138 g, 1 mmol) and heated under reflux for 3 days. After the mixture was cooled to room temperature, the solution was filtered and the solvents removed in vacuum to afford a white precipitate of the title compound. Colourless crystals suitable for X-ray diffraction were obtained from a solution of 100 mg in 15 ml diethylether by slow evaporation after 3 days.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and the H atoms were set to ride on the C and N atoms to which they are bonded, with Uiso(H) = 1.2Ueq(C or N).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
3,3'-{1,1'-Methylenebis[naphthalene-2,1-diylbis(oxymethylene)]}dibenzonitrile top
Crystal data top
C37H26N2O2Z = 2
Mr = 530.60F000 = 556.0
Triclinic, P1Dx = 1.252 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.3123 (19) ÅCell parameters from 7383 reflections
b = 12.130 (2) Åθ = 3.2–27.5º
c = 12.682 (3) ŵ = 0.08 mm−1
α = 79.71 (3)ºT = 293 (2) K
β = 86.58 (3)ºBlock, colourless
γ = 87.10 (3)º0.40 × 0.20 × 0.20 mm
V = 1405.9 (5) Å3
Data collection top
Rigaku Mercury2
diffractometer		5505 independent reflections
Radiation source: fine-focus sealed tube2197 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.074
Detector resolution: 13.6612 pixels mm-1θmax = 26.0º
T = 293(2) Kθmin = 3.2º
CCD_Profile_fitting scansh = −11→11
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −14→14
Tmin = 0.929, Tmax = 0.976l = −15→15
13073 measured reflections
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)] = 0.069H-atom parameters constrained
wR(F2) = 0.170  w = 1/[σ2(Fo2) + (0.0621P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max = 0.001
5505 reflectionsΔρmax = 0.18 e Å−3
370 parametersΔρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C37H26N2O2γ = 87.10 (3)º
Mr = 530.60V = 1405.9 (5) Å3
Triclinic, P1Z = 2
a = 9.3123 (19) ÅMo Kα
b = 12.130 (2) ŵ = 0.08 mm−1
c = 12.682 (3) ÅT = 293 (2) K
α = 79.71 (3)º0.40 × 0.20 × 0.20 mm
β = 86.58 (3)º
Data collection top
Rigaku Mercury2
diffractometer		5505 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2197 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.976Rint = 0.074
13073 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069370 parameters
wR(F2) = 0.170H-atom parameters constrained
S = 0.92Δρmax = 0.18 e Å−3
5505 reflectionsΔρmin = −0.18 e Å−3
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
C10.3027 (3)0.9398 (2)0.0249 (2)0.0608 (9)
H1A0.27691.01880.00420.073*
H1B0.36520.9178−0.03250.073*
C20.1670 (3)0.8741 (2)0.0352 (2)0.0523 (8)
C30.1464 (4)0.7897 (3)−0.0270 (2)0.0607 (9)
C40.2492 (4)0.7613 (3)−0.1054 (3)0.0763 (10)
H40.33560.7980−0.11710.092*
C50.2242 (6)0.6817 (4)−0.1637 (3)0.1065 (14)
H50.29350.6650−0.21510.128*
C60.0968 (7)0.6243 (4)−0.1482 (4)0.1182 (17)
H60.08200.5695−0.18870.142*
C7−0.0061 (5)0.6482 (3)−0.0739 (3)0.0988 (13)
H7−0.09060.6091−0.06370.119*
C80.0143 (4)0.7320 (3)−0.0121 (3)0.0692 (9)
C9−0.0890 (4)0.7570 (3)0.0656 (3)0.0763 (10)
H9−0.17280.71700.07740.092*
C10−0.0707 (3)0.8378 (3)0.1242 (2)0.0689 (9)
H10−0.14110.85400.17500.083*
C110.0578 (3)0.8971 (3)0.1065 (2)0.0537 (8)
C12−0.0149 (3)1.0114 (3)0.2408 (2)0.0720 (10)
H12A−0.11221.01190.21730.086*
H12B0.00251.08640.25230.086*
C13−0.0040 (3)0.9310 (2)0.3465 (2)0.0552 (8)
C140.1197 (3)0.8661 (2)0.3723 (2)0.0545 (8)
H140.19720.86810.32240.065*
C150.1290 (4)0.7982 (2)0.4718 (2)0.0585 (8)
C160.0151 (4)0.7942 (3)0.5460 (3)0.0792 (11)
H160.02100.74740.61240.095*
C17−0.1075 (4)0.8592 (4)0.5223 (3)0.0910 (12)
H17−0.18420.85770.57290.109*
C18−0.1164 (3)0.9276 (3)0.4220 (3)0.0742 (10)
H18−0.19960.97150.40600.089*
C190.2585 (5)0.7344 (3)0.5006 (3)0.0772 (10)
C200.3869 (3)0.9240 (2)0.1264 (2)0.0533 (8)
C210.4046 (3)1.0118 (3)0.1852 (2)0.0561 (8)
C220.3464 (3)1.1227 (3)0.1556 (3)0.0714 (9)
H220.29431.14040.09400.086*
C230.3649 (4)1.2042 (3)0.2149 (3)0.0846 (11)
H230.32501.27600.19350.102*
C240.4431 (4)1.1805 (3)0.3075 (3)0.0841 (11)
H240.45611.23650.34700.101*
C250.4999 (3)1.0755 (3)0.3396 (3)0.0777 (10)
H250.55111.06000.40170.093*
C260.4827 (3)0.9889 (3)0.2803 (3)0.0624 (9)
C270.5416 (4)0.8801 (3)0.3132 (3)0.0774 (10)
H270.59170.86470.37580.093*
C280.5275 (3)0.7970 (3)0.2567 (3)0.0739 (10)
H280.56840.72590.27970.089*
C290.4503 (3)0.8193 (3)0.1627 (3)0.0596 (8)
C300.4664 (4)0.6241 (3)0.1401 (3)0.0855 (11)
H30A0.56410.61530.16360.103*
H30B0.46090.58140.08280.103*
C310.3651 (4)0.5757 (3)0.2329 (3)0.0658 (9)
C320.2190 (4)0.6039 (3)0.2314 (2)0.0680 (9)
H320.18280.65480.17450.082*
C330.1263 (4)0.5558 (3)0.3156 (3)0.0626 (8)
C340.1783 (4)0.4822 (3)0.4006 (3)0.0774 (10)
H340.11580.45160.45700.093*
C350.3224 (5)0.4532 (3)0.4027 (3)0.0867 (12)
H350.35770.40180.45970.104*
C360.4153 (4)0.5011 (3)0.3195 (3)0.0812 (11)
H360.51330.48260.32210.097*
C37−0.0261 (5)0.5865 (3)0.3164 (3)0.0762 (10)
N1−0.1484 (4)0.6073 (3)0.3198 (3)0.1080 (12)
N20.3622 (4)0.6844 (3)0.5255 (3)0.1119 (12)
O10.0827 (2)0.98473 (17)0.15795 (15)0.0632 (6)
O20.4363 (2)0.74029 (18)0.09827 (17)0.0715 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.063 (2)0.063 (2)0.0519 (19)−0.0079 (17)0.0066 (17)0.0001 (15)
C20.058 (2)0.061 (2)0.0338 (16)−0.0052 (16)−0.0026 (15)0.0048 (14)
C30.077 (2)0.060 (2)0.0403 (18)0.0011 (19)−0.0095 (18)0.0054 (16)
C40.102 (3)0.074 (2)0.054 (2)−0.001 (2)−0.005 (2)−0.0130 (19)
C50.140 (4)0.106 (4)0.078 (3)0.009 (3)−0.009 (3)−0.030 (3)
C60.169 (5)0.089 (3)0.103 (4)−0.009 (4)−0.040 (4)−0.024 (3)
C70.113 (4)0.096 (3)0.088 (3)−0.026 (3)−0.031 (3)−0.005 (3)
C80.083 (3)0.069 (2)0.053 (2)−0.011 (2)−0.023 (2)0.0061 (18)
C90.069 (2)0.088 (3)0.065 (2)−0.018 (2)−0.020 (2)0.016 (2)
C100.055 (2)0.093 (3)0.051 (2)−0.002 (2)−0.0088 (17)0.0085 (19)
C110.058 (2)0.061 (2)0.0388 (17)0.0039 (17)−0.0137 (16)0.0025 (15)
C120.063 (2)0.091 (3)0.060 (2)0.0176 (19)−0.0102 (19)−0.0102 (19)
C130.0423 (18)0.075 (2)0.0481 (18)0.0035 (16)−0.0009 (15)−0.0132 (16)
C140.0498 (19)0.066 (2)0.0461 (18)0.0036 (16)−0.0017 (15)−0.0074 (15)
C150.062 (2)0.062 (2)0.0524 (19)−0.0055 (17)−0.0116 (18)−0.0072 (17)
C160.093 (3)0.089 (3)0.053 (2)−0.024 (2)−0.004 (2)−0.0009 (19)
C170.068 (3)0.133 (4)0.072 (3)−0.023 (3)0.017 (2)−0.020 (2)
C180.047 (2)0.104 (3)0.075 (2)−0.0034 (19)−0.0025 (19)−0.024 (2)
C190.096 (3)0.071 (2)0.064 (2)0.008 (2)−0.024 (2)−0.0060 (18)
C200.0409 (18)0.059 (2)0.0536 (19)−0.0040 (16)0.0058 (15)0.0047 (16)
C210.0402 (18)0.065 (2)0.060 (2)−0.0108 (16)0.0035 (16)−0.0036 (17)
C220.062 (2)0.075 (2)0.074 (2)−0.0013 (19)−0.0087 (19)−0.003 (2)
C230.081 (3)0.075 (3)0.100 (3)0.000 (2)−0.007 (2)−0.022 (2)
C240.064 (3)0.102 (3)0.094 (3)−0.009 (2)−0.001 (2)−0.038 (2)
C250.051 (2)0.103 (3)0.084 (3)−0.015 (2)−0.0081 (19)−0.025 (2)
C260.0375 (18)0.075 (2)0.073 (2)−0.0094 (17)−0.0015 (17)−0.0056 (19)
C270.056 (2)0.092 (3)0.083 (3)−0.013 (2)−0.0246 (19)−0.002 (2)
C280.048 (2)0.073 (2)0.097 (3)−0.0018 (18)−0.021 (2)0.002 (2)
C290.0405 (18)0.066 (2)0.071 (2)−0.0077 (17)0.0068 (17)−0.0100 (19)
C300.077 (3)0.070 (3)0.105 (3)0.011 (2)0.007 (2)−0.011 (2)
C310.068 (2)0.056 (2)0.070 (2)0.0080 (18)0.0004 (19)−0.0091 (17)
C320.077 (3)0.067 (2)0.054 (2)0.0040 (19)−0.0086 (19)0.0052 (16)
C330.072 (2)0.057 (2)0.058 (2)0.0037 (18)−0.0107 (19)−0.0052 (17)
C340.101 (3)0.066 (2)0.059 (2)0.011 (2)0.002 (2)−0.0009 (18)
C350.122 (4)0.065 (2)0.066 (3)0.021 (2)−0.007 (3)0.0030 (19)
C360.089 (3)0.060 (2)0.091 (3)0.027 (2)−0.024 (2)−0.007 (2)
C370.087 (3)0.084 (3)0.051 (2)−0.002 (2)−0.002 (2)0.0059 (17)
N10.078 (2)0.142 (3)0.088 (2)0.003 (2)0.005 (2)0.018 (2)
N20.131 (3)0.099 (3)0.106 (3)0.038 (2)−0.054 (2)−0.015 (2)
O10.0631 (14)0.0748 (15)0.0488 (12)0.0082 (12)−0.0002 (11)−0.0070 (11)
O20.0707 (15)0.0648 (15)0.0739 (15)0.0050 (12)0.0047 (12)−0.0038 (12)
Geometric parameters (Å, °) top
C1—C21.515 (4)C18—H180.9300
C1—C201.525 (4)C19—N21.144 (4)
C1—H1A0.9700C20—C291.386 (4)
C1—H1B0.9700C20—C211.427 (4)
C2—C111.372 (4)C21—C221.419 (4)
C2—C31.425 (4)C21—C261.423 (4)
C3—C41.414 (4)C22—C231.369 (4)
C3—C81.432 (4)C22—H220.9300
C4—C51.354 (5)C23—C241.397 (5)
C4—H40.9300C23—H230.9300
C5—C61.392 (6)C24—C251.357 (4)
C5—H50.9300C24—H240.9300
C6—C71.360 (5)C25—C261.417 (4)
C6—H60.9300C25—H250.9300
C7—C81.417 (5)C26—C271.405 (4)
C7—H70.9300C27—C281.352 (4)
C8—C91.397 (4)C27—H270.9300
C9—C101.355 (4)C28—C291.407 (4)
C9—H90.9300C28—H280.9300
C10—C111.413 (4)C29—O21.381 (3)
C10—H100.9300C30—O21.434 (3)
C11—O11.379 (3)C30—C311.515 (4)
C12—O11.418 (3)C30—H30A0.9700
C12—C131.516 (4)C30—H30B0.9700
C12—H12A0.9700C31—C361.382 (4)
C12—H12B0.9700C31—C321.387 (4)
C13—C181.373 (4)C32—C331.394 (4)
C13—C141.384 (4)C32—H320.9300
C14—C151.382 (4)C33—C341.367 (4)
C14—H140.9300C33—C371.449 (5)
C15—C161.373 (4)C34—C351.370 (5)
C15—C191.429 (5)C34—H340.9300
C16—C171.371 (5)C35—C361.386 (4)
C16—H160.9300C35—H350.9300
C17—C181.394 (4)C36—H360.9300
C17—H170.9300C37—N11.154 (4)
C2—C1—C20114.8 (2)C17—C18—H18119.5
C2—C1—H1A108.6N2—C19—C15178.6 (4)
C20—C1—H1A108.6C29—C20—C21118.5 (3)
C2—C1—H1B108.6C29—C20—C1118.3 (3)
C20—C1—H1B108.6C21—C20—C1123.2 (3)
H1A—C1—H1B107.6C22—C21—C26116.8 (3)
C11—C2—C3118.1 (3)C22—C21—C20123.8 (3)
C11—C2—C1119.0 (3)C26—C21—C20119.4 (3)
C3—C2—C1122.9 (3)C23—C22—C21121.8 (3)
C4—C3—C2123.2 (3)C23—C22—H22119.1
C4—C3—C8117.7 (3)C21—C22—H22119.1
C2—C3—C8119.1 (3)C22—C23—C24120.6 (4)
C5—C4—C3121.2 (4)C22—C23—H23119.7
C5—C4—H4119.4C24—C23—H23119.7
C3—C4—H4119.4C25—C24—C23119.8 (4)
C4—C5—C6121.2 (4)C25—C24—H24120.1
C4—C5—H5119.4C23—C24—H24120.1
C6—C5—H5119.4C24—C25—C26121.2 (3)
C7—C6—C5120.3 (4)C24—C25—H25119.4
C7—C6—H6119.9C26—C25—H25119.4
C5—C6—H6119.9C27—C26—C25121.4 (3)
C6—C7—C8120.6 (4)C27—C26—C21118.9 (3)
C6—C7—H7119.7C25—C26—C21119.8 (3)
C8—C7—H7119.7C28—C27—C26122.0 (3)
C9—C8—C7121.6 (4)C28—C27—H27119.0
C9—C8—C3119.2 (3)C26—C27—H27119.0
C7—C8—C3119.1 (4)C27—C28—C29119.3 (3)
C10—C9—C8121.9 (4)C27—C28—H28120.3
C10—C9—H9119.1C29—C28—H28120.3
C8—C9—H9119.1O2—C29—C20115.3 (3)
C9—C10—C11118.5 (3)O2—C29—C28122.8 (3)
C9—C10—H10120.7C20—C29—C28121.9 (3)
C11—C10—H10120.7O2—C30—C31114.0 (3)
C2—C11—O1114.2 (3)O2—C30—H30A108.7
C2—C11—C10123.0 (3)C31—C30—H30A108.7
O1—C11—C10122.7 (3)O2—C30—H30B108.7
O1—C12—C13114.0 (2)C31—C30—H30B108.7
O1—C12—H12A108.7H30A—C30—H30B107.6
C13—C12—H12A108.7C36—C31—C32118.5 (3)
O1—C12—H12B108.7C36—C31—C30121.1 (3)
C13—C12—H12B108.7C32—C31—C30120.4 (3)
H12A—C12—H12B107.6C31—C32—C33119.8 (3)
C18—C13—C14118.7 (3)C31—C32—H32120.1
C18—C13—C12119.2 (3)C33—C32—H32120.1
C14—C13—C12122.0 (3)C34—C33—C32120.7 (3)
C15—C14—C13120.6 (3)C34—C33—C37118.9 (3)
C15—C14—H14119.7C32—C33—C37120.4 (3)
C13—C14—H14119.7C33—C34—C35120.1 (3)
C16—C15—C14120.2 (3)C33—C34—H34120.0
C16—C15—C19118.9 (3)C35—C34—H34120.0
C14—C15—C19120.9 (3)C34—C35—C36119.6 (3)
C17—C16—C15120.0 (3)C34—C35—H35120.2
C17—C16—H16120.0C36—C35—H35120.2
C15—C16—H16120.0C31—C36—C35121.3 (3)
C16—C17—C18119.6 (3)C31—C36—H36119.3
C16—C17—H17120.2C35—C36—H36119.3
C18—C17—H17120.2N1—C37—C33177.5 (4)
C13—C18—C17121.0 (3)C11—O1—C12120.4 (3)
C13—C18—H18119.5C29—O2—C30119.5 (3)
C20—C1—C2—C1162.9 (3)C1—C20—C21—C22−0.2 (4)
C20—C1—C2—C3−117.8 (3)C29—C20—C21—C26−1.7 (4)
C11—C2—C3—C4177.9 (3)C1—C20—C21—C26178.9 (2)
C1—C2—C3—C4−1.4 (4)C26—C21—C22—C230.3 (5)
C11—C2—C3—C8−0.5 (4)C20—C21—C22—C23179.4 (3)
C1—C2—C3—C8−179.8 (3)C21—C22—C23—C240.3 (5)
C2—C3—C4—C5−179.0 (3)C22—C23—C24—C25−0.7 (5)
C8—C3—C4—C5−0.6 (5)C23—C24—C25—C260.6 (5)
C3—C4—C5—C6−0.4 (6)C24—C25—C26—C27179.9 (3)
C4—C5—C6—C70.5 (7)C24—C25—C26—C210.0 (5)
C5—C6—C7—C80.5 (7)C22—C21—C26—C27179.6 (3)
C6—C7—C8—C9−179.2 (4)C20—C21—C26—C270.5 (4)
C6—C7—C8—C3−1.5 (5)C22—C21—C26—C25−0.4 (4)
C4—C3—C8—C9179.3 (3)C20—C21—C26—C25−179.6 (3)
C2—C3—C8—C9−2.3 (4)C25—C26—C27—C28−179.2 (3)
C4—C3—C8—C71.5 (4)C21—C26—C27—C280.7 (5)
C2—C3—C8—C7180.0 (3)C26—C27—C28—C29−0.7 (5)
C7—C8—C9—C10−179.4 (3)C21—C20—C29—O2−176.2 (2)
C3—C8—C9—C102.9 (5)C1—C20—C29—O23.3 (4)
C8—C9—C10—C11−0.8 (5)C21—C20—C29—C281.7 (4)
C3—C2—C11—O1−175.9 (2)C1—C20—C29—C28−178.8 (3)
C1—C2—C11—O13.5 (3)C27—C28—C29—O2177.3 (3)
C3—C2—C11—C102.8 (4)C27—C28—C29—C20−0.5 (5)
C1—C2—C11—C10−177.9 (3)O2—C30—C31—C36−140.6 (3)
C9—C10—C11—C2−2.2 (4)O2—C30—C31—C3240.7 (4)
C9—C10—C11—O1176.4 (3)C36—C31—C32—C33−0.9 (5)
O1—C12—C13—C18−161.5 (3)C30—C31—C32—C33177.8 (3)
O1—C12—C13—C1423.0 (4)C31—C32—C33—C340.9 (5)
C18—C13—C14—C150.8 (4)C31—C32—C33—C37178.6 (3)
C12—C13—C14—C15176.4 (3)C32—C33—C34—C35−1.2 (5)
C13—C14—C15—C160.2 (5)C37—C33—C34—C35−178.9 (3)
C13—C14—C15—C19−177.4 (3)C33—C34—C35—C361.5 (5)
C14—C15—C16—C17−1.1 (5)C32—C31—C36—C351.2 (5)
C19—C15—C16—C17176.5 (3)C30—C31—C36—C35−177.5 (3)
C15—C16—C17—C181.1 (5)C34—C35—C36—C31−1.5 (5)
C14—C13—C18—C17−0.8 (5)C2—C11—O1—C12−174.4 (2)
C12—C13—C18—C17−176.6 (3)C10—C11—O1—C127.0 (4)
C16—C17—C18—C13−0.1 (5)C13—C12—O1—C1175.5 (3)
C2—C1—C20—C2966.3 (3)C20—C29—O2—C30−165.0 (2)
C2—C1—C20—C21−114.2 (3)C28—C29—O2—C3017.0 (4)
C29—C20—C21—C22179.2 (3)C31—C30—O2—C2964.3 (4)
Acknowledgements top

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.

references
References top

Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.

Radl, S., Hezky, P., Konvicka, P. & Krejgi, J. (2000). Collect. Czech. Chem. Commun. 65, 1093–1108.

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.