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Acta Cryst. (2008). E64, o761    [ doi:10.1107/S1600536808007629 ]

4,4'-{[1,1'-Methylenebis(naphthalene-2,1-diyl)]bis(oxymethylene)}dibenzonitrile

Y.-Y. Zhao

Abstract top

There are two independent molecules in the asymmetric unit of the title compound, C37H26N2O2. The crystal structure is stabilized by a weak intramolecular hydrogen bond as well as C-H...[pi] interactions.

Comment top

The synthesis of new azoles has been a very active area of research and one important aspect has been the incorporation of functional units, such as the cyanomethyl group in ravuconazol (Urbina et al., 2001). Nitrile derivatives have found many industrial applications. For example, phthalonitriles have been used as starting materials for phthalocyanines (Jin et al., 1994), which are important components for dyes, pigments, gas sensors, optical limiters and liquid crystals, and which are also used in medicine, as singlet oxygen photosensitisers for photodynamic therapy (PDT; Brewis et al., 2003). Recently, we have reported a few benzonitrile compounds (Fu & Zhao, 2007). As an extension of our work on the structural characterization, the title compound, is reported here.

The crystal data show that in the title compound, the two naphthyl rings are almost perpendicular to each other and the dihedral angle is 83.25 (7)°. However, the two cyanobenzyloxy rings are approximately parallel with a dihedral angle of 11.27 (1)°. The crystal structure of the title compound, is stabilized by a weak intramolecular hydrogen bond [H73A···.O4 2.44, C73···O4 2.763 (5) Å, O4—H73A···C73 100] as well as C—H -π interactions (Table 1 and Table 2).

Related literature top

For the application of nitrile compounds in industry, see: Urbina et al. (2001); Jin et al. (1994); Brewis et al. (2003); For the structure of one example of a nitrile compound, see: Fu & Zhao (2007).

Experimental top

1,1'-methylenedinaphthalen-2-ol (0.3 g,1 mmol) and 4-(bromomethyl)benzonitrile (0.392 g,2 mmol) were dissolved in acetone in the presence of K2CO3 (0.138 g,1 mmol) and refluxed for 3 days. After the mixture was cooled to room temperature, the solution was filtered and rotated in vacuum affording a white precipitate of compound. Colourless crystals of the title compound suitable for X-ray diffraction were obtained from a solution of 100 mg in 15 ml diethylether after 3 days.

Refinement top

All the C—H hydrogen atoms were calculated geometrically and with C—H distances ranging from 0.93 to 0.97Å and were allowed to ride on the C and O atoms to which they are bonded. With which Uiso(H) = 1.2Ueq(C).

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 and all hydrogen atoms were omitted for clarity.
4,4'-{[1,1'-Methylenebis(naphthalene-2,1-diyl)]bis(oxymethylene)}dibenzonitrile top
Crystal data top
C37H26N2O2Z = 4
Mr = 530.60F000 = 1112
Triclinic, P1Dx = 1.269 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 14.3054 (10) ÅCell parameters from 19582 reflections
b = 14.4363 (8) Åθ = 3.0–27.5º
c = 15.2974 (7) ŵ = 0.08 mm−1
α = 67.7010 (10)ºT = 293 (2) K
β = 83.5890 (10)ºBlock, colorless
γ = 71.7840 (10)º0.20 × 0.20 × 0.12 mm
V = 2776.4 (3) Å3
Data collection top
Rigaku Mercury2
diffractometer		10903 independent reflections
Radiation source: fine-focus sealed tube5107 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.076
Detector resolution: 13.6612 pixels mm-1θmax = 26.0º
T = 293(2) Kθmin = 3.0º
CCD_Profile_fitting scansh = −17→17
Absorption correction: multi-scan
CrystalClear (Rigaku, 2005)		k = −17→17
Tmin = 0.799, Tmax = 1.000l = −18→18
25739 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.070  w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.206(Δ/σ)max = 0.001
S = 0.92Δρmax = 0.20 e Å−3
10903 reflectionsΔρmin = −0.20 e Å−3
740 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (9)
Secondary atom site location: difference Fourier map
Crystal data top
C37H26N2O2γ = 71.7840 (10)º
Mr = 530.60V = 2776.4 (3) Å3
Triclinic, P1Z = 4
a = 14.3054 (10) ÅMo Kα
b = 14.4363 (8) ŵ = 0.08 mm−1
c = 15.2974 (7) ÅT = 293 (2) K
α = 67.7010 (10)º0.20 × 0.20 × 0.12 mm
β = 83.5890 (10)º
Data collection top
Rigaku Mercury2
diffractometer		10903 independent reflections
Absorption correction: multi-scan
CrystalClear (Rigaku, 2005)		5107 reflections with I > 2σ(I)
Tmin = 0.799, Tmax = 1.000Rint = 0.076
25739 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.070740 parameters
wR(F2) = 0.206H-atom parameters constrained
S = 0.92Δρmax = 0.20 e Å−3
10903 reflectionsΔρmin = −0.20 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
O30.26966 (14)0.69880 (16)0.21213 (13)0.0634 (6)
O40.36207 (15)0.81079 (15)−0.03224 (14)0.0669 (6)
C390.4200 (2)0.6345 (2)0.14721 (19)0.0509 (7)
C400.3698 (2)0.6810 (2)0.2090 (2)0.0554 (7)
C430.5749 (2)0.6332 (2)0.2048 (2)0.0603 (8)
C480.5251 (2)0.6063 (2)0.1465 (2)0.0560 (8)
C660.2736 (2)0.7897 (2)−0.0247 (2)0.0555 (7)
C570.2725 (2)0.6903 (2)0.03295 (19)0.0538 (7)
C670.3682 (2)0.9119 (2)−0.0901 (2)0.0630 (8)
H67A0.32050.9640−0.06950.076*
H67B0.35270.9264−0.15500.076*
C580.1841 (2)0.6625 (3)0.0399 (2)0.0621 (8)
C650.1899 (2)0.8644 (3)−0.0758 (2)0.0669 (9)
H65A0.19210.9316−0.11330.080*
C680.4692 (2)0.9192 (2)−0.0850 (2)0.0566 (8)
C410.4189 (2)0.7046 (2)0.2687 (2)0.0643 (8)
H41A0.38340.73510.31060.077*
C550.1075 (2)0.7667 (3)0.2586 (2)0.0657 (9)
C710.6543 (2)0.9396 (2)−0.0771 (2)0.0626 (8)
C630.1008 (2)0.7371 (3)−0.0159 (2)0.0690 (9)
C440.6786 (2)0.6109 (3)0.1998 (2)0.0746 (10)
H44A0.71100.63000.23660.090*
C380.3664 (2)0.6112 (2)0.0819 (2)0.0645 (8)
H38A0.41220.59820.03320.077*
H38B0.35120.54620.11810.077*
C640.1056 (2)0.8380 (3)−0.0703 (2)0.0730 (10)
H64A0.05000.8882−0.10340.088*
C470.5846 (2)0.5528 (2)0.0903 (2)0.0679 (9)
H47A0.55470.53140.05350.081*
C420.5186 (2)0.6828 (2)0.2650 (2)0.0672 (9)
H42A0.55030.70110.30310.081*
C51−0.0371 (3)0.8383 (3)0.1622 (2)0.0794 (10)
H51A−0.06810.87630.10350.095*
C500.0612 (3)0.8243 (3)0.1709 (2)0.0781 (10)
H50A0.09680.85320.11850.094*
C53−0.0442 (3)0.7411 (3)0.3275 (3)0.0812 (10)
H53A−0.07970.71430.38090.097*
C490.2141 (2)0.7550 (3)0.2686 (3)0.0812 (10)
H49A0.22440.82350.24800.097*
H49B0.23460.71740.33420.097*
C52−0.0907 (2)0.7957 (3)0.2409 (3)0.0694 (9)
C740.7501 (3)0.9521 (3)−0.0743 (2)0.0781 (10)
C690.4996 (3)0.9965 (3)−0.1545 (2)0.0836 (11)
H69A0.45811.0423−0.20540.100*
C450.7312 (3)0.5622 (3)0.1420 (3)0.0814 (11)
H45A0.79910.54940.13870.098*
C730.5313 (3)0.8544 (3)−0.0114 (3)0.0875 (11)
H73A0.51110.80250.03740.105*
C720.6233 (3)0.8633 (3)−0.0071 (3)0.0910 (12)
H72A0.66470.81710.04390.109*
C460.6847 (3)0.5314 (3)0.0881 (2)0.0823 (11)
H46A0.72160.49590.05020.099*
C540.0543 (3)0.7262 (3)0.3350 (2)0.0756 (10)
H54A0.08540.68760.39350.091*
N40.8261 (2)0.9621 (3)−0.0730 (2)0.1071 (11)
C590.1737 (3)0.5637 (3)0.0984 (3)0.0874 (11)
H59A0.22560.51440.13780.105*
C56−0.1935 (3)0.8123 (3)0.2335 (3)0.0918 (12)
C700.5908 (3)1.0077 (3)−0.1503 (2)0.0857 (11)
H70A0.60951.0620−0.19740.103*
C620.0143 (3)0.7080 (4)−0.0128 (3)0.0978 (13)
H62A−0.04010.7563−0.04940.117*
C600.0895 (4)0.5395 (4)0.0981 (4)0.1178 (16)
H60A0.08530.47320.13630.141*
N3−0.2756 (3)0.8256 (3)0.2266 (3)0.1319 (15)
C610.0098 (4)0.6113 (5)0.0424 (4)0.1282 (18)
H61A−0.04700.59280.04290.154*
O20.29159 (14)0.81321 (14)0.44137 (13)0.0600 (5)
O10.37325 (14)0.70793 (16)0.69447 (14)0.0655 (6)
C110.2878 (2)0.6880 (2)0.68556 (19)0.0519 (7)
C200.4363 (2)0.6956 (2)0.52235 (18)0.0474 (7)
C20.28969 (19)0.6397 (2)0.62340 (18)0.0469 (7)
C80.1210 (2)0.6324 (2)0.6724 (2)0.0567 (8)
C210.5381 (2)0.6702 (2)0.54265 (19)0.0500 (7)
C30.2070 (2)0.6061 (2)0.61961 (19)0.0503 (7)
C10.38052 (19)0.6150 (2)0.56354 (19)0.0537 (7)
H1A0.42620.54990.60220.064*
H1B0.36000.60270.51160.064*
C290.3902 (2)0.7936 (2)0.45917 (19)0.0514 (7)
C310.1278 (2)0.9257 (2)0.4002 (2)0.0571 (7)
C90.1215 (2)0.6889 (2)0.7301 (2)0.0636 (8)
H9A0.06530.70860.76360.076*
C280.4413 (2)0.8665 (2)0.4126 (2)0.0645 (8)
H28A0.40820.93220.37030.077*
C120.3762 (2)0.7579 (3)0.7566 (2)0.0748 (9)
H12A0.36150.71680.82040.090*
H12B0.32810.82660.73770.090*
C100.2034 (2)0.7150 (2)0.7375 (2)0.0624 (8)
H10A0.20320.75070.77690.075*
C300.2349 (2)0.9191 (2)0.3947 (2)0.0689 (9)
H30A0.25450.94380.32910.083*
H30B0.24650.96310.42450.083*
C50.1268 (3)0.5111 (3)0.5683 (2)0.0770 (10)
H5A0.12920.46890.53440.092*
C260.5902 (2)0.7451 (2)0.4935 (2)0.0593 (8)
C320.0666 (2)0.9902 (2)0.3234 (2)0.0676 (9)
H32A0.09271.02650.26710.081*
C130.4781 (2)0.7679 (3)0.7527 (2)0.0613 (8)
C40.2055 (2)0.5444 (2)0.5673 (2)0.0613 (8)
H4A0.26000.52610.53130.074*
C220.5912 (2)0.5769 (2)0.6124 (2)0.0659 (8)
H22A0.55930.52700.64630.079*
C360.0884 (2)0.8711 (2)0.4832 (2)0.0647 (8)
H36A0.12920.82730.53530.078*
C70.0396 (2)0.5987 (3)0.6694 (2)0.0761 (10)
H7A−0.01680.61810.70270.091*
C33−0.0319 (2)1.0010 (2)0.3292 (2)0.0704 (9)
H33A−0.07261.04530.27720.084*
C35−0.0101 (2)0.8811 (2)0.4894 (2)0.0693 (9)
H35A−0.03600.84390.54550.083*
C160.6661 (2)0.7860 (3)0.7443 (3)0.0688 (9)
C140.5408 (3)0.7126 (3)0.8278 (2)0.0744 (9)
H14A0.51970.66840.88290.089*
C150.6343 (3)0.7201 (3)0.8244 (3)0.0818 (10)
H15A0.67610.68060.87640.098*
C270.5380 (2)0.8428 (3)0.4282 (2)0.0710 (9)
H27A0.57110.89180.39540.085*
C34−0.0714 (2)0.9465 (2)0.4122 (2)0.0650 (8)
C180.5096 (3)0.8351 (3)0.6723 (2)0.0743 (9)
H18A0.46710.87500.62090.089*
C230.6873 (3)0.5573 (3)0.6319 (3)0.0803 (10)
H23A0.71990.49440.67830.096*
C250.6896 (2)0.7216 (3)0.5146 (3)0.0766 (10)
H25A0.72380.76940.48110.092*
C240.7376 (3)0.6300 (3)0.5835 (3)0.0856 (11)
H24A0.80310.61650.59780.103*
C60.0417 (3)0.5386 (3)0.6190 (3)0.0867 (11)
H6A−0.01230.51610.61810.104*
C190.7637 (3)0.7936 (3)0.7400 (3)0.0975 (13)
C170.6033 (3)0.8437 (3)0.6675 (3)0.0784 (10)
H17A0.62440.88820.61260.094*
C37−0.1753 (3)0.9587 (3)0.4192 (3)0.0902 (12)
N1−0.2582 (3)0.9711 (3)0.4230 (3)0.1288 (14)
N20.8419 (3)0.7993 (3)0.7366 (4)0.1477 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0591 (13)0.0789 (15)0.0610 (13)−0.0161 (11)0.0038 (10)−0.0394 (12)
O40.0672 (14)0.0583 (14)0.0702 (14)−0.0220 (11)0.0007 (11)−0.0152 (11)
C390.0581 (18)0.0440 (16)0.0450 (16)−0.0112 (13)−0.0009 (14)−0.0131 (14)
C400.0576 (19)0.0544 (18)0.0520 (18)−0.0158 (14)−0.0053 (15)−0.0160 (15)
C430.062 (2)0.0501 (18)0.0533 (19)−0.0126 (15)−0.0068 (16)−0.0039 (15)
C480.066 (2)0.0438 (17)0.0470 (17)−0.0146 (14)−0.0018 (15)−0.0054 (14)
C660.0531 (19)0.064 (2)0.0522 (18)−0.0177 (16)0.0011 (14)−0.0239 (16)
C570.0615 (19)0.060 (2)0.0451 (17)−0.0192 (15)0.0059 (14)−0.0254 (15)
C670.077 (2)0.054 (2)0.0571 (19)−0.0201 (16)0.0017 (16)−0.0178 (16)
C580.066 (2)0.082 (2)0.0522 (19)−0.0289 (18)0.0149 (16)−0.0383 (18)
C650.065 (2)0.074 (2)0.0549 (19)−0.0164 (18)0.0005 (16)−0.0206 (17)
C680.071 (2)0.0521 (19)0.0490 (18)−0.0206 (16)0.0041 (16)−0.0203 (16)
C410.068 (2)0.065 (2)0.062 (2)−0.0130 (16)−0.0043 (16)−0.0293 (17)
C550.063 (2)0.074 (2)0.071 (2)−0.0142 (17)−0.0005 (18)−0.0432 (19)
C710.067 (2)0.064 (2)0.059 (2)−0.0223 (17)0.0048 (17)−0.0240 (18)
C630.059 (2)0.101 (3)0.061 (2)−0.028 (2)0.0092 (17)−0.044 (2)
C440.067 (2)0.063 (2)0.072 (2)−0.0175 (17)−0.0169 (18)0.0029 (18)
C380.074 (2)0.060 (2)0.062 (2)−0.0173 (16)−0.0022 (17)−0.0253 (17)
C640.069 (2)0.096 (3)0.0494 (19)−0.013 (2)−0.0049 (16)−0.028 (2)
C470.072 (2)0.065 (2)0.0538 (19)−0.0091 (17)−0.0032 (17)−0.0151 (17)
C420.077 (2)0.064 (2)0.062 (2)−0.0214 (17)−0.0155 (18)−0.0186 (17)
C510.078 (3)0.095 (3)0.065 (2)−0.012 (2)−0.0061 (19)−0.037 (2)
C500.074 (2)0.107 (3)0.062 (2)−0.027 (2)0.0119 (19)−0.043 (2)
C530.073 (2)0.068 (2)0.087 (3)−0.0241 (19)0.007 (2)−0.010 (2)
C490.069 (2)0.099 (3)0.088 (3)−0.0132 (19)0.0066 (19)−0.059 (2)
C520.061 (2)0.060 (2)0.086 (3)−0.0101 (16)−0.0047 (19)−0.030 (2)
C740.081 (3)0.084 (3)0.069 (2)−0.028 (2)0.010 (2)−0.0269 (19)
C690.070 (2)0.080 (3)0.070 (2)−0.0226 (19)0.0020 (18)0.0069 (19)
C450.059 (2)0.074 (2)0.076 (3)−0.0087 (19)0.004 (2)0.000 (2)
C730.101 (3)0.076 (3)0.080 (3)−0.050 (2)−0.023 (2)0.003 (2)
C720.104 (3)0.074 (3)0.082 (3)−0.043 (2)−0.030 (2)0.007 (2)
C460.074 (3)0.080 (3)0.064 (2)−0.002 (2)0.0036 (19)−0.014 (2)
C540.079 (3)0.068 (2)0.066 (2)−0.0145 (18)−0.0033 (19)−0.0138 (18)
N40.082 (2)0.123 (3)0.118 (3)−0.044 (2)0.006 (2)−0.036 (2)
C590.091 (3)0.094 (3)0.089 (3)−0.050 (2)0.026 (2)−0.035 (2)
C560.069 (3)0.086 (3)0.121 (3)−0.020 (2)−0.006 (2)−0.040 (2)
C700.074 (2)0.086 (3)0.071 (2)−0.031 (2)0.009 (2)0.005 (2)
C620.070 (3)0.135 (4)0.108 (3)−0.040 (3)0.011 (2)−0.060 (3)
C600.112 (4)0.127 (4)0.128 (4)−0.073 (3)0.043 (3)−0.043 (3)
N30.074 (2)0.126 (3)0.184 (4)−0.022 (2)−0.020 (3)−0.043 (3)
C610.090 (4)0.167 (6)0.160 (5)−0.072 (4)0.034 (4)−0.075 (4)
O20.0603 (13)0.0508 (13)0.0619 (13)−0.0136 (10)−0.0079 (10)−0.0127 (10)
O10.0646 (13)0.0876 (16)0.0647 (14)−0.0324 (11)0.0146 (11)−0.0454 (12)
C110.0532 (18)0.0522 (18)0.0495 (17)−0.0158 (14)0.0067 (14)−0.0193 (14)
C200.0566 (18)0.0490 (17)0.0414 (15)−0.0194 (14)0.0091 (13)−0.0210 (14)
C20.0528 (17)0.0421 (16)0.0400 (15)−0.0121 (13)0.0044 (13)−0.0114 (13)
C80.0553 (19)0.0473 (18)0.0538 (18)−0.0127 (14)−0.0003 (15)−0.0053 (15)
C210.0542 (18)0.0563 (19)0.0450 (16)−0.0155 (14)0.0034 (14)−0.0257 (15)
C30.0515 (17)0.0439 (16)0.0476 (17)−0.0166 (13)0.0000 (13)−0.0061 (14)
C10.0555 (18)0.0493 (17)0.0538 (18)−0.0152 (14)0.0042 (14)−0.0175 (14)
C290.0531 (18)0.0534 (19)0.0475 (17)−0.0159 (14)−0.0036 (14)−0.0170 (15)
C310.063 (2)0.0485 (18)0.0542 (19)−0.0136 (14)−0.0005 (15)−0.0148 (15)
C90.060 (2)0.060 (2)0.061 (2)−0.0140 (16)0.0150 (16)−0.0173 (16)
C280.073 (2)0.059 (2)0.0549 (19)−0.0288 (17)0.0006 (16)−0.0067 (16)
C120.079 (2)0.092 (3)0.074 (2)−0.0311 (19)0.0112 (18)−0.050 (2)
C100.064 (2)0.062 (2)0.061 (2)−0.0156 (16)0.0117 (16)−0.0274 (17)
C300.069 (2)0.055 (2)0.070 (2)−0.0132 (16)0.0013 (17)−0.0136 (17)
C50.086 (3)0.078 (2)0.079 (2)−0.037 (2)−0.001 (2)−0.030 (2)
C260.058 (2)0.065 (2)0.0586 (19)−0.0217 (16)0.0026 (16)−0.0253 (17)
C320.075 (2)0.065 (2)0.0475 (18)−0.0105 (17)−0.0009 (16)−0.0122 (16)
C130.064 (2)0.070 (2)0.065 (2)−0.0228 (17)0.0056 (17)−0.0400 (18)
C40.067 (2)0.064 (2)0.0585 (19)−0.0261 (16)0.0027 (16)−0.0226 (16)
C220.061 (2)0.064 (2)0.065 (2)−0.0114 (16)−0.0002 (16)−0.0211 (18)
C360.069 (2)0.053 (2)0.061 (2)−0.0094 (16)−0.0079 (17)−0.0138 (16)
C70.056 (2)0.076 (2)0.084 (3)−0.0247 (18)0.0075 (18)−0.014 (2)
C330.069 (2)0.069 (2)0.058 (2)−0.0077 (17)−0.0107 (17)−0.0143 (18)
C350.076 (2)0.055 (2)0.065 (2)−0.0172 (17)0.0019 (18)−0.0108 (17)
C160.064 (2)0.067 (2)0.085 (3)−0.0210 (18)0.007 (2)−0.039 (2)
C140.071 (2)0.079 (2)0.071 (2)−0.0245 (19)0.0036 (19)−0.0241 (19)
C150.073 (2)0.084 (3)0.079 (3)−0.016 (2)−0.011 (2)−0.022 (2)
C270.071 (2)0.076 (2)0.067 (2)−0.0402 (19)0.0097 (18)−0.0160 (19)
C340.064 (2)0.054 (2)0.073 (2)−0.0085 (16)−0.0065 (18)−0.0247 (18)
C180.080 (2)0.084 (3)0.062 (2)−0.029 (2)−0.0035 (18)−0.0247 (19)
C230.065 (2)0.080 (3)0.088 (3)−0.009 (2)−0.006 (2)−0.030 (2)
C250.059 (2)0.090 (3)0.089 (3)−0.0289 (19)0.0112 (19)−0.039 (2)
C240.055 (2)0.101 (3)0.108 (3)−0.011 (2)−0.005 (2)−0.054 (3)
C60.067 (2)0.087 (3)0.112 (3)−0.034 (2)−0.003 (2)−0.034 (2)
C190.075 (3)0.087 (3)0.141 (4)−0.026 (2)0.005 (3)−0.054 (3)
C170.101 (3)0.072 (2)0.072 (2)−0.045 (2)0.016 (2)−0.025 (2)
C370.074 (3)0.076 (3)0.117 (3)−0.019 (2)−0.009 (2)−0.030 (2)
N10.082 (2)0.106 (3)0.177 (4)−0.021 (2)−0.014 (3)−0.030 (3)
N20.083 (3)0.128 (3)0.244 (5)−0.043 (2)0.005 (3)−0.073 (3)
Geometric parameters (Å, °) top
O3—C401.373 (3)O2—C291.386 (3)
O3—C491.419 (3)O2—C301.425 (3)
O4—C661.375 (3)O1—C111.372 (3)
O4—C671.416 (3)O1—C121.405 (3)
C39—C401.374 (4)C11—C21.370 (3)
C39—C481.429 (4)C11—C101.402 (4)
C39—C381.513 (4)C20—C291.376 (4)
C40—C411.404 (4)C20—C211.426 (4)
C43—C441.417 (4)C20—C11.516 (3)
C43—C421.409 (4)C2—C31.426 (3)
C43—C481.425 (4)C2—C11.532 (3)
C48—C471.411 (4)C8—C91.413 (4)
C66—C571.374 (4)C8—C71.406 (4)
C66—C651.403 (4)C8—C31.425 (4)
C57—C581.423 (4)C21—C221.407 (4)
C57—C381.512 (4)C21—C261.431 (4)
C67—C681.494 (4)C3—C41.411 (4)
C67—H67A0.9700C1—H1A0.9700
C67—H67B0.9700C1—H1B0.9700
C58—C631.427 (4)C29—C281.396 (4)
C58—C591.411 (4)C31—C361.383 (4)
C65—C641.358 (4)C31—C321.380 (4)
C65—H65A0.9300C31—C301.500 (4)
C68—C731.355 (4)C9—C101.365 (4)
C68—C691.366 (4)C9—H9A0.9300
C41—C421.360 (4)C28—C271.342 (4)
C41—H41A0.9300C28—H28A0.9300
C55—C541.360 (4)C12—C131.502 (4)
C55—C501.392 (4)C12—H12A0.9700
C55—C491.500 (4)C12—H12B0.9700
C71—C701.370 (4)C10—H10A0.9300
C71—C721.364 (4)C30—H30A0.9700
C71—C741.444 (5)C30—H30B0.9700
C63—C641.396 (4)C5—C41.352 (4)
C63—C621.417 (5)C5—C61.401 (5)
C44—C451.354 (5)C5—H5A0.9300
C44—H44A0.9300C26—C251.401 (4)
C38—H38A0.9700C26—C271.408 (4)
C38—H38B0.9700C32—C331.364 (4)
C64—H64A0.9300C32—H32A0.9300
C47—C461.366 (4)C13—C181.378 (4)
C47—H47A0.9300C13—C141.359 (4)
C42—H42A0.9300C4—H4A0.9300
C51—C501.370 (4)C22—C231.359 (4)
C51—C521.395 (4)C22—H22A0.9300
C51—H51A0.9300C36—C351.368 (4)
C50—H50A0.9300C36—H36A0.9300
C53—C541.368 (4)C7—C61.354 (5)
C53—C521.377 (4)C7—H7A0.9300
C53—H53A0.9300C33—C341.383 (4)
C49—H49A0.9700C33—H33A0.9300
C49—H49B0.9700C35—C341.386 (4)
C52—C561.425 (5)C35—H35A0.9300
C74—N41.144 (4)C16—C151.369 (4)
C69—C701.375 (4)C16—C171.381 (5)
C69—H69A0.9300C16—C191.427 (5)
C45—C461.382 (5)C14—C151.369 (4)
C45—H45A0.9300C14—H14A0.9300
C73—C721.373 (4)C15—H15A0.9300
C73—H73A0.9300C27—H27A0.9300
C72—H72A0.9300C34—C371.437 (5)
C46—H46A0.9300C18—C171.376 (4)
C54—H54A0.9300C18—H18A0.9300
C59—C601.356 (5)C23—C241.390 (5)
C59—H59A0.9300C23—H23A0.9300
C56—N31.139 (4)C25—C241.366 (5)
C70—H70A0.9300C25—H25A0.9300
C62—C611.348 (6)C24—H24A0.9300
C62—H62A0.9300C6—H6A0.9300
C60—C611.382 (6)C19—N21.141 (4)
C60—H60A0.9300C17—H17A0.9300
C61—H61A0.9300C37—N11.141 (4)
C40—O3—C49118.1 (2)C29—O2—C30118.0 (2)
C66—O4—C67119.2 (2)C11—O1—C12119.2 (2)
C40—C39—C48118.8 (3)C2—C11—O1116.2 (2)
C40—C39—C38121.4 (3)C2—C11—C10121.8 (3)
C48—C39—C38119.9 (3)O1—C11—C10122.0 (3)
O3—C40—C39116.4 (2)C29—C20—C21118.6 (2)
O3—C40—C41121.9 (3)C29—C20—C1119.8 (2)
C39—C40—C41121.7 (3)C21—C20—C1121.4 (2)
C44—C43—C42121.9 (3)C11—C2—C3118.4 (2)
C44—C43—C48119.5 (3)C11—C2—C1121.5 (2)
C42—C43—C48118.5 (3)C3—C2—C1119.9 (2)
C39—C48—C43119.5 (3)C9—C8—C7121.5 (3)
C39—C48—C47123.9 (3)C9—C8—C3118.4 (3)
C43—C48—C47116.6 (3)C7—C8—C3120.1 (3)
C57—C66—O4116.3 (3)C22—C21—C20124.0 (3)
C57—C66—C65121.8 (3)C22—C21—C26116.7 (3)
O4—C66—C65121.8 (3)C20—C21—C26119.2 (3)
C66—C57—C58118.8 (3)C4—C3—C8116.6 (3)
C66—C57—C38119.5 (3)C4—C3—C2123.4 (3)
C58—C57—C38121.6 (3)C8—C3—C2120.0 (3)
O4—C67—C68110.4 (2)C20—C1—C2118.0 (2)
O4—C67—H67A109.6C20—C1—H1A107.8
C68—C67—H67A109.6C2—C1—H1A107.8
O4—C67—H67B109.6C20—C1—H1B107.8
C68—C67—H67B109.6C2—C1—H1B107.8
H67A—C67—H67B108.1H1A—C1—H1B107.1
C63—C58—C57119.1 (3)C20—C29—O2116.0 (2)
C63—C58—C59117.2 (3)C20—C29—C28121.6 (3)
C57—C58—C59123.7 (3)O2—C29—C28122.4 (3)
C64—C65—C66119.7 (3)C36—C31—C32119.2 (3)
C64—C65—H65A120.1C36—C31—C30120.5 (3)
C66—C65—H65A120.1C32—C31—C30120.2 (3)
C73—C68—C69118.0 (3)C10—C9—C8120.9 (3)
C73—C68—C67122.5 (3)C10—C9—H9A119.5
C69—C68—C67119.5 (3)C8—C9—H9A119.5
C42—C41—C40119.8 (3)C27—C28—C29120.7 (3)
C42—C41—H41A120.1C27—C28—H28A119.7
C40—C41—H41A120.1C29—C28—H28A119.7
C54—C55—C50119.5 (3)O1—C12—C13107.4 (2)
C54—C55—C49120.8 (3)O1—C12—H12A110.2
C50—C55—C49119.6 (3)C13—C12—H12A110.2
C70—C71—C72118.4 (3)O1—C12—H12B110.2
C70—C71—C74119.7 (3)C13—C12—H12B110.2
C72—C71—C74121.9 (3)H12A—C12—H12B108.5
C64—C63—C58119.2 (3)C9—C10—C11120.1 (3)
C64—C63—C62121.5 (4)C9—C10—H10A120.0
C58—C63—C62119.3 (4)C11—C10—H10A120.0
C45—C44—C43120.9 (3)O2—C30—C31109.4 (2)
C45—C44—H44A119.6O2—C30—H30A109.8
C43—C44—H44A119.6C31—C30—H30A109.8
C57—C38—C39119.8 (2)O2—C30—H30B109.8
C57—C38—H38A107.4C31—C30—H30B109.8
C39—C38—H38A107.4H30A—C30—H30B108.2
C57—C38—H38B107.4C4—C5—C6121.8 (3)
C39—C38—H38B107.4C4—C5—H5A119.1
H38A—C38—H38B106.9C6—C5—H5A119.1
C65—C64—C63121.3 (3)C25—C26—C27121.8 (3)
C65—C64—H64A119.4C25—C26—C21119.5 (3)
C63—C64—H64A119.4C27—C26—C21118.6 (3)
C46—C47—C48122.3 (3)C33—C32—C31120.7 (3)
C46—C47—H47A118.9C33—C32—H32A119.7
C48—C47—H47A118.9C31—C32—H32A119.7
C41—C42—C43121.5 (3)C18—C13—C14118.5 (3)
C41—C42—H42A119.3C18—C13—C12120.2 (3)
C43—C42—H42A119.3C14—C13—C12121.3 (3)
C50—C51—C52120.2 (3)C5—C4—C3121.5 (3)
C50—C51—H51A119.9C5—C4—H4A119.2
C52—C51—H51A119.9C3—C4—H4A119.2
C51—C50—C55119.8 (3)C23—C22—C21122.2 (3)
C51—C50—H50A120.1C23—C22—H22A118.9
C55—C50—H50A120.1C21—C22—H22A118.9
C54—C53—C52120.0 (3)C31—C36—C35120.4 (3)
C54—C53—H53A120.0C31—C36—H36A119.8
C52—C53—H53A120.0C35—C36—H36A119.8
O3—C49—C55108.1 (2)C6—C7—C8121.4 (3)
O3—C49—H49A110.1C6—C7—H7A119.3
C55—C49—H49A110.1C8—C7—H7A119.3
O3—C49—H49B110.1C32—C33—C34120.2 (3)
C55—C49—H49B110.1C32—C33—H33A119.9
H49A—C49—H49B108.4C34—C33—H33A119.9
C53—C52—C51119.2 (3)C36—C35—C34120.1 (3)
C53—C52—C56119.9 (4)C36—C35—H35A119.9
C51—C52—C56120.8 (3)C34—C35—H35A119.9
N4—C74—C71179.2 (4)C15—C16—C17119.3 (3)
C68—C69—C70121.0 (3)C15—C16—C19120.2 (4)
C68—C69—H69A119.5C17—C16—C19120.5 (4)
C70—C69—H69A119.5C15—C14—C13121.7 (3)
C44—C45—C46120.5 (3)C15—C14—H14A119.1
C44—C45—H45A119.8C13—C14—H14A119.1
C46—C45—H45A119.8C14—C15—C16119.9 (3)
C68—C73—C72121.7 (3)C14—C15—H15A120.0
C68—C73—H73A119.1C16—C15—H15A120.0
C72—C73—H73A119.1C28—C27—C26121.3 (3)
C71—C72—C73120.3 (3)C28—C27—H27A119.4
C71—C72—H72A119.8C26—C27—H27A119.4
C73—C72—H72A119.8C33—C34—C35119.4 (3)
C47—C46—C45120.2 (3)C33—C34—C37120.4 (3)
C47—C46—H46A119.9C35—C34—C37120.2 (3)
C45—C46—H46A119.9C13—C18—C17120.6 (3)
C55—C54—C53121.3 (3)C13—C18—H18A119.7
C55—C54—H54A119.4C17—C18—H18A119.7
C53—C54—H54A119.4C22—C23—C24120.8 (3)
C60—C59—C58121.2 (4)C22—C23—H23A119.6
C60—C59—H59A119.4C24—C23—H23A119.6
C58—C59—H59A119.4C24—C25—C26121.5 (3)
N3—C56—C52179.3 (5)C24—C25—H25A119.3
C71—C70—C69120.5 (3)C26—C25—H25A119.3
C71—C70—H70A119.7C25—C24—C23119.3 (3)
C69—C70—H70A119.7C25—C24—H24A120.4
C61—C62—C63120.8 (4)C23—C24—H24A120.4
C61—C62—H62A119.6C7—C6—C5118.6 (3)
C63—C62—H62A119.6C7—C6—H6A120.7
C59—C60—C61121.4 (5)C5—C6—H6A120.7
C59—C60—H60A119.3N2—C19—C16179.8 (5)
C61—C60—H60A119.3C18—C17—C16119.9 (3)
C62—C61—C60120.1 (5)C18—C17—H17A120.0
C62—C61—H61A119.9C16—C17—H17A120.0
C60—C61—H61A119.9N1—C37—C34178.2 (5)
C49—O3—C40—C39−174.5 (3)C12—O1—C11—C2179.6 (3)
C49—O3—C40—C418.4 (4)C12—O1—C11—C10−0.7 (4)
C48—C39—C40—O3−174.9 (2)O1—C11—C2—C3172.8 (2)
C38—C39—C40—O34.0 (4)C10—C11—C2—C3−6.9 (4)
C48—C39—C40—C412.2 (4)O1—C11—C2—C1−3.2 (4)
C38—C39—C40—C41−178.9 (3)C10—C11—C2—C1177.1 (2)
C40—C39—C48—C43−4.2 (4)C29—C20—C21—C22173.6 (3)
C38—C39—C48—C43176.9 (2)C1—C20—C21—C22−10.7 (4)
C40—C39—C48—C47176.2 (3)C29—C20—C21—C26−3.1 (4)
C38—C39—C48—C47−2.8 (4)C1—C20—C21—C26172.7 (2)
C44—C43—C48—C39−176.2 (3)C9—C8—C3—C4176.4 (2)
C42—C43—C48—C392.9 (4)C7—C8—C3—C4−1.1 (4)
C44—C43—C48—C473.5 (4)C9—C8—C3—C2−2.0 (4)
C42—C43—C48—C47−177.4 (3)C7—C8—C3—C2−179.5 (3)
C67—O4—C66—C57−179.7 (2)C11—C2—C3—C4−171.9 (3)
C67—O4—C66—C652.7 (4)C1—C2—C3—C44.2 (4)
O4—C66—C57—C58−177.0 (2)C11—C2—C3—C86.3 (4)
C65—C66—C57—C580.6 (4)C1—C2—C3—C8−177.6 (2)
O4—C66—C57—C38−1.2 (4)C29—C20—C1—C2−62.2 (3)
C65—C66—C57—C38176.5 (3)C21—C20—C1—C2122.1 (3)
C66—O4—C67—C68177.6 (2)C11—C2—C1—C20−39.5 (4)
C66—C57—C58—C632.5 (4)C3—C2—C1—C20144.5 (2)
C38—C57—C58—C63−173.2 (2)C21—C20—C29—O2179.1 (2)
C66—C57—C58—C59−178.5 (3)C1—C20—C29—O23.3 (4)
C38—C57—C58—C595.7 (4)C21—C20—C29—C282.3 (4)
C57—C66—C65—C64−1.4 (4)C1—C20—C29—C28−173.6 (2)
O4—C66—C65—C64176.1 (3)C30—O2—C29—C20165.7 (2)
O4—C67—C68—C73−22.2 (4)C30—O2—C29—C28−17.5 (4)
O4—C67—C68—C69160.6 (3)C7—C8—C9—C10175.5 (3)
O3—C40—C41—C42178.0 (3)C3—C8—C9—C10−2.0 (4)
C39—C40—C41—C421.0 (4)C20—C29—C28—C270.1 (4)
C57—C58—C63—C64−4.9 (4)O2—C29—C28—C27−176.6 (3)
C59—C58—C63—C64176.0 (3)C11—O1—C12—C13179.3 (2)
C57—C58—C63—C62176.8 (3)C8—C9—C10—C111.6 (4)
C59—C58—C63—C62−2.3 (4)C2—C11—C10—C93.0 (4)
C42—C43—C44—C45179.3 (3)O1—C11—C10—C9−176.6 (3)
C48—C43—C44—C45−1.6 (4)C29—O2—C30—C31−168.4 (2)
C66—C57—C38—C3958.2 (4)C36—C31—C30—O242.6 (4)
C58—C57—C38—C39−126.0 (3)C32—C31—C30—O2−140.2 (3)
C40—C39—C38—C5741.0 (4)C22—C21—C26—C251.6 (4)
C48—C39—C38—C57−140.1 (3)C20—C21—C26—C25178.5 (3)
C66—C65—C64—C63−1.1 (5)C22—C21—C26—C27−175.2 (3)
C58—C63—C64—C654.3 (5)C20—C21—C26—C271.7 (4)
C62—C63—C64—C65−177.5 (3)C36—C31—C32—C330.7 (5)
C39—C48—C47—C46176.9 (3)C30—C31—C32—C33−176.5 (3)
C43—C48—C47—C46−2.8 (4)O1—C12—C13—C1869.1 (4)
C40—C41—C42—C43−2.4 (5)O1—C12—C13—C14−111.7 (3)
C44—C43—C42—C41179.4 (3)C6—C5—C4—C31.8 (5)
C48—C43—C42—C410.4 (4)C8—C3—C4—C5−0.7 (4)
C52—C51—C50—C550.5 (5)C2—C3—C4—C5177.6 (3)
C54—C55—C50—C51−1.0 (5)C20—C21—C22—C23−177.5 (3)
C49—C55—C50—C51−177.7 (3)C26—C21—C22—C23−0.9 (4)
C40—O3—C49—C55178.5 (3)C32—C31—C36—C35−0.3 (5)
C54—C55—C49—O3119.6 (3)C30—C31—C36—C35176.9 (3)
C50—C55—C49—O3−63.8 (4)C9—C8—C7—C6−175.6 (3)
C54—C53—C52—C51−2.1 (5)C3—C8—C7—C61.9 (5)
C54—C53—C52—C56−179.2 (3)C31—C32—C33—C34−0.7 (5)
C50—C51—C52—C531.0 (5)C31—C36—C35—C34−0.2 (5)
C50—C51—C52—C56178.1 (3)C18—C13—C14—C15−1.7 (5)
C73—C68—C69—C700.5 (5)C12—C13—C14—C15179.2 (3)
C67—C68—C69—C70177.7 (3)C13—C14—C15—C161.0 (5)
C43—C44—C45—C46−1.3 (5)C17—C16—C15—C14−0.4 (5)
C69—C68—C73—C72−1.7 (5)C19—C16—C15—C14−179.4 (3)
C67—C68—C73—C72−178.9 (3)C29—C28—C27—C26−1.5 (5)
C70—C71—C72—C731.3 (5)C25—C26—C27—C28−176.1 (3)
C74—C71—C72—C73179.2 (3)C21—C26—C27—C280.7 (5)
C68—C73—C72—C710.8 (6)C32—C33—C34—C350.2 (5)
C48—C47—C46—C450.0 (5)C32—C33—C34—C37179.1 (3)
C44—C45—C46—C472.1 (5)C36—C35—C34—C330.2 (5)
C50—C55—C54—C53−0.1 (5)C36—C35—C34—C37−178.7 (3)
C49—C55—C54—C53176.5 (3)C14—C13—C18—C171.8 (5)
C52—C53—C54—C551.7 (5)C12—C13—C18—C17−179.1 (3)
C63—C58—C59—C602.9 (5)C21—C22—C23—C240.5 (5)
C57—C58—C59—C60−176.1 (3)C27—C26—C25—C24174.6 (3)
C72—C71—C70—C69−2.5 (5)C21—C26—C25—C24−2.1 (5)
C74—C71—C70—C69179.6 (3)C26—C25—C24—C231.7 (5)
C68—C69—C70—C711.7 (6)C22—C23—C24—C25−0.9 (5)
C64—C63—C62—C61−177.9 (4)C8—C7—C6—C5−0.8 (5)
C58—C63—C62—C610.3 (6)C4—C5—C6—C7−1.1 (5)
C58—C59—C60—C61−1.5 (7)C13—C18—C17—C16−1.2 (5)
C63—C62—C61—C601.1 (7)C15—C16—C17—C180.5 (5)
C59—C60—C61—C62−0.5 (8)C19—C16—C17—C18179.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O73—H73A···O40.932.442.763 (5)100
C22—H22A···Cg1i0.932.883.755 (3)158
C36—H36A···Cg20.932.573.454 (3)159
C73—H73A···Cg10.932.783.698 (4)168
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O73—H73A···O40.932.442.763 (5)100
C22—H22A···Cg1i0.932.883.755 (3)158
C36—H36A···Cg20.932.573.454 (3)159
C73—H73A···Cg10.932.783.698 (4)168
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

This work was supported by a Start-up Grant from SEU.

references
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