supplementary materials


lh5509 scheme

Acta Cryst. (2012). E68, o2694    [ doi:10.1107/S1600536812034575 ]

4-{(E)-2-[4-(Diethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium tetraphenylborate

D.-D. Li, R. Li and S.-L. Li

Abstract top

In the cation of the title salt, C18H23N2+·C24H20B-, the pyridine ring forms a dihedral angle of 14.23 (6)° with the benzene ring. One of the ethyl groups of the cation was refined as disordered over two sets of sites with equal occupancies.

Comment top

The use of stilbazolium compounds as nonlinear optical materials is a newly emerging field that has already exhibited potential applications in upconverted lasing and biological imaging because of their high stability and tailor-ability (Hao et al., 2009; Zhou et al., 2011). The importance of the structures of pyridinium derivatives has already been reported (Li et al., 2000). We have synthesized title compound and it's crystal structure is presented herein. The asymmetric unit of the title compound (I) is shown in Fig.1. In the cation, the pyridine ring makes a dihedral angle of 14.23 (6) ° with the benzene ring and the CC bond is 1.353 (4) Å. While in a similar cation (Li et al., 2000), the corresponding value of the dihedral angle is 19.94 (4) ° and the CC bond is 1.226 (4) Å. This may indicate that the π-electron delocalization in the title cation is enhanced compared to the literature structure. This feature is a necessary condition for the cation to bear a large two-photon absorption (TPA) cross-section.

Related literature top

For the use of stilbazolium compounds as non-linear optical materials, see: Hao et al. (2009); Zhou et al. (2011). For the crystal structure of a related pyridinium derivative, see: Li et al. (2000).

Experimental top

A 100 mL round-buttom flask was charged with a magnetic stirrer and a reflux condenser, 1.77 g (0.01 mol) of 4-(N,N-diethylamino)-benzaldehyde, 2.36 g (0.01 mol) of 1,4-dimethylpyridinium iodide and 30 mL of absolute ethanol and mixed. Five drops of piperidine were added into the mixture. The solution was then heated to reflux for 4 h. The solution was kept warm and filtered into an ethanol solution of sodium tetraphenylborate (3.46 g, 0.01 mol) with stirring. A red precipitate appeared, the solution was filtered and the solid was washed with ethanol three times and dried over vacuum. 1H NMR: (400 Hz, CD3COCD3), d(p.p.m.): 8.62(d, 2H) 8.04(d, 2H) 7.89(d, 1H) 7.60(d, 2H) 7.35(s, 8H) 7.15(d, 1H) 6.94–6.91(t, 8H) 6.79–6.77(q, 6H) 4.35(s, 3H) 3.53–3.48(q, 4H) 1.22–1.18(t, 6H). Single crystals were obtained from slow evaporation over several days of an acetonitrile solution of the title compound at room temperature.

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å, Uiso(H) = 1.2 Ueq(C) or 1.5Ueq(C). Atoms C17 and C18 atoms of an ethyl group were refined as disordered over two sets of sites (C17/C17',C18/C18') with the equall occupancies.

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 structure of the title compound (I) showing 30% probability displacement ellipsoids.
4-{(E)-2-[4-(Diethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium tetraphenylborate top
Crystal data top
C18H23N2+·C24H20BF(000) = 2512
Mr = 586.59Dx = 1.065 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4692 reflections
a = 38.59 (8) Åθ = 2.2–21.1°
b = 11.35 (2) ŵ = 0.06 mm1
c = 17.04 (3) ÅT = 298 K
β = 101.43 (5)°Block, red
V = 7314 (25) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
6411 independent reflections
Radiation source: fine-focus sealed tube4032 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SABADS; Bruker, 2007)
h = 4545
Tmin = 0.982, Tmax = 0.988k = 1313
24610 measured reflectionsl = 1920
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.199 w = 1/[σ2(Fo2) + (0.1058P)2 + 2.2113P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
6411 reflectionsΔρmax = 0.38 e Å3
429 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0026 (4)
Crystal data top
C18H23N2+·C24H20BV = 7314 (25) Å3
Mr = 586.59Z = 8
Monoclinic, C2/cMo Kα radiation
a = 38.59 (8) ŵ = 0.06 mm1
b = 11.35 (2) ÅT = 298 K
c = 17.04 (3) Å0.30 × 0.20 × 0.20 mm
β = 101.43 (5)°
Data collection top
Bruker SMART CCD
diffractometer
6411 independent reflections
Absorption correction: multi-scan
(SABADS; Bruker, 2007)
4032 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.988Rint = 0.038
24610 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.199Δρmax = 0.38 e Å3
S = 1.03Δρmin = 0.18 e Å3
6411 reflectionsAbsolute structure: ?
429 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)
C10.29481 (8)0.8332 (3)0.11485 (18)0.0922 (9)
H1A0.28510.85070.06850.138*
H1B0.27680.79890.15550.138*
H1C0.30320.90450.13490.138*
C20.35515 (7)0.7803 (2)0.03925 (15)0.0774 (7)
H20.35670.85580.01770.093*
C30.32304 (8)0.6360 (3)0.12374 (16)0.0856 (8)
H30.30270.61310.15950.103*
C40.35039 (8)0.5567 (2)0.10350 (17)0.0850 (8)
H40.34820.48200.12640.102*
C50.38180 (7)0.5866 (2)0.04856 (14)0.0709 (7)
C60.38307 (7)0.7036 (2)0.01714 (15)0.0774 (7)
H60.40310.72840.01890.093*
C70.41081 (8)0.4997 (2)0.02579 (16)0.0827 (8)
H70.40860.42810.05280.099*
C80.44025 (7)0.5163 (2)0.03111 (16)0.0794 (7)
H80.44220.58960.05590.095*
C90.46976 (7)0.4341 (2)0.05928 (16)0.0762 (7)
C100.47528 (9)0.3258 (3)0.02145 (19)0.1020 (10)
H100.45940.30400.02470.122*
C110.49640 (8)0.4644 (3)0.12557 (18)0.0949 (9)
H110.49520.53760.14930.114*
C120.50366 (9)0.2509 (3)0.0509 (2)0.1056 (10)
H120.50650.18220.02310.127*
C130.52850 (8)0.2777 (3)0.12316 (18)0.0884 (8)
C140.52439 (8)0.3898 (3)0.15717 (18)0.0999 (10)
H140.54080.41420.20170.120*
C150.56172 (10)0.0850 (3)0.1121 (3)0.1197 (12)
H15A0.55770.09740.05470.144*
H15B0.58590.05810.12980.144*
C160.53722 (11)0.0051 (4)0.1305 (3)0.1550 (18)
H16A0.54330.02500.18630.233*
H16B0.53880.07420.09890.233*
H16C0.51350.02490.11820.233*
C170.5724 (3)0.2030 (8)0.2461 (8)0.109 (3)0.50
H17A0.55600.23930.27530.130*0.50
H17B0.57730.12330.26590.130*0.50
C180.6061 (3)0.2736 (8)0.2563 (8)0.139 (4)0.50
H18A0.62280.23280.23120.209*0.50
H18B0.61580.28340.31230.209*0.50
H18C0.60110.34950.23170.209*0.50
B10.34219 (6)0.77574 (19)0.22741 (14)0.0468 (5)
C190.29162 (9)1.0842 (2)0.16706 (17)0.0832 (8)
H190.29361.16100.18640.100*
C200.26494 (8)1.0558 (3)0.10160 (18)0.0845 (9)
H200.24881.11260.07790.101*
C210.26295 (7)0.9405 (3)0.07249 (16)0.0798 (8)
H210.24570.92050.02830.096*
C220.28725 (6)0.8532 (2)0.11015 (14)0.0638 (6)
H220.28540.77730.08920.077*
C230.31413 (5)0.87685 (17)0.17827 (12)0.0501 (5)
C250.33930 (7)0.5731 (2)0.13919 (16)0.0762 (7)
H250.35940.60000.12220.091*
C260.32598 (5)0.64056 (17)0.19768 (12)0.0507 (5)
C270.29573 (6)0.5909 (2)0.22178 (15)0.0672 (6)
H270.28630.62980.26080.081*
C280.27940 (8)0.4855 (2)0.18919 (19)0.0871 (9)
H280.25950.45740.20650.105*
C290.29290 (9)0.4229 (2)0.1309 (2)0.0944 (10)
H290.28210.35380.10920.113*
C300.32320 (10)0.4665 (2)0.10577 (19)0.0977 (10)
H300.33260.42580.06750.117*
C310.31225 (6)0.8110 (2)0.35908 (14)0.0685 (6)
H310.29050.80520.32400.082*
C320.34388 (5)0.79782 (16)0.32660 (12)0.0486 (5)
C330.37542 (6)0.8111 (2)0.38470 (13)0.0660 (6)
H330.39690.80490.36820.079*
C340.31223 (8)0.8322 (2)0.44106 (16)0.0788 (7)
H340.29090.83830.45850.095*
C350.34419 (8)0.8441 (2)0.49558 (15)0.0793 (8)
H350.34450.85870.54940.095*
C360.37584 (8)0.8334 (3)0.46701 (15)0.0863 (8)
H360.39740.84110.50250.104*
C370.41046 (6)0.7081 (2)0.23451 (14)0.0640 (6)
H370.40540.64450.26470.077*
C380.38276 (5)0.79148 (17)0.20609 (12)0.0491 (5)
C390.39338 (6)0.88629 (18)0.16085 (12)0.0556 (5)
H390.37690.94440.14150.067*
C400.42829 (7)0.8960 (2)0.14391 (14)0.0690 (7)
H400.43380.95860.11330.083*
C410.45417 (7)0.8112 (3)0.17342 (16)0.0786 (8)
H410.47680.81700.16290.094*
C420.44500 (6)0.7175 (2)0.21912 (16)0.0749 (7)
H420.46190.66110.23950.090*
C17'0.5865 (3)0.2476 (10)0.2149 (5)0.104 (2)0.50
H17C0.59060.32960.20340.125*0.50
H17D0.60770.20340.21200.125*0.50
C18'0.5784 (4)0.2371 (11)0.3013 (6)0.152 (4)0.50
H18D0.56040.29270.30740.228*0.50
H18E0.59950.25340.34010.228*0.50
H18F0.57040.15870.30940.228*0.50
N10.32500 (5)0.74767 (19)0.09248 (12)0.0713 (6)
N20.55643 (8)0.2019 (2)0.15412 (17)0.1149 (10)
C240.31557 (7)0.99717 (19)0.20423 (14)0.0670 (6)
H240.33311.01900.24750.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.093 (2)0.100 (2)0.0819 (19)0.0139 (17)0.0135 (16)0.0148 (16)
C20.0921 (19)0.0679 (16)0.0677 (16)0.0060 (14)0.0048 (14)0.0120 (12)
C30.0823 (19)0.095 (2)0.0708 (17)0.0091 (16)0.0058 (14)0.0178 (15)
C40.090 (2)0.0755 (17)0.0819 (18)0.0042 (15)0.0005 (15)0.0246 (14)
C50.0828 (17)0.0685 (15)0.0588 (14)0.0055 (13)0.0074 (13)0.0088 (12)
C60.0829 (18)0.0726 (17)0.0691 (16)0.0076 (14)0.0036 (13)0.0100 (13)
C70.099 (2)0.0670 (16)0.0756 (17)0.0034 (14)0.0022 (16)0.0142 (13)
C80.0918 (19)0.0707 (16)0.0737 (17)0.0045 (14)0.0113 (15)0.0114 (13)
C90.0857 (18)0.0695 (16)0.0704 (16)0.0048 (14)0.0085 (14)0.0049 (13)
C100.120 (2)0.0785 (19)0.090 (2)0.0057 (18)0.0204 (18)0.0089 (16)
C110.098 (2)0.091 (2)0.087 (2)0.0181 (17)0.0002 (17)0.0305 (16)
C120.131 (3)0.0734 (18)0.099 (2)0.0153 (18)0.010 (2)0.0166 (16)
C130.094 (2)0.0807 (19)0.0825 (19)0.0094 (16)0.0018 (16)0.0072 (15)
C140.098 (2)0.108 (2)0.083 (2)0.0186 (18)0.0081 (16)0.0300 (17)
C150.098 (2)0.104 (3)0.153 (3)0.020 (2)0.016 (2)0.012 (2)
C160.115 (3)0.142 (3)0.195 (4)0.002 (3)0.003 (3)0.069 (3)
C170.134 (7)0.093 (6)0.099 (8)0.003 (5)0.024 (6)0.023 (5)
C180.140 (8)0.135 (7)0.123 (8)0.023 (6)0.023 (7)0.003 (6)
B10.0486 (13)0.0428 (12)0.0484 (13)0.0010 (10)0.0080 (10)0.0038 (10)
C190.124 (2)0.0582 (15)0.0749 (18)0.0348 (15)0.0375 (18)0.0174 (13)
C200.098 (2)0.085 (2)0.0785 (19)0.0445 (16)0.0369 (17)0.0408 (15)
C210.0647 (16)0.096 (2)0.0751 (17)0.0156 (14)0.0063 (13)0.0314 (15)
C220.0619 (14)0.0625 (14)0.0649 (14)0.0053 (11)0.0074 (11)0.0139 (11)
C230.0547 (12)0.0485 (11)0.0493 (12)0.0041 (9)0.0159 (10)0.0099 (9)
C250.0962 (19)0.0550 (14)0.0789 (17)0.0105 (13)0.0210 (14)0.0106 (12)
C260.0545 (12)0.0434 (11)0.0499 (12)0.0041 (9)0.0002 (9)0.0090 (9)
C270.0602 (14)0.0637 (14)0.0743 (16)0.0065 (11)0.0052 (12)0.0095 (12)
C280.0756 (18)0.0677 (17)0.105 (2)0.0261 (14)0.0145 (16)0.0215 (16)
C290.119 (3)0.0469 (14)0.096 (2)0.0167 (15)0.0298 (19)0.0119 (15)
C300.140 (3)0.0559 (16)0.093 (2)0.0069 (17)0.013 (2)0.0153 (14)
C310.0647 (15)0.0825 (16)0.0597 (14)0.0083 (12)0.0155 (12)0.0005 (12)
C320.0561 (12)0.0394 (10)0.0505 (12)0.0042 (9)0.0111 (10)0.0059 (8)
C330.0608 (14)0.0801 (16)0.0567 (14)0.0035 (12)0.0106 (11)0.0058 (12)
C340.0900 (19)0.0884 (18)0.0656 (16)0.0106 (15)0.0339 (15)0.0018 (13)
C350.109 (2)0.0811 (17)0.0509 (14)0.0028 (15)0.0235 (15)0.0057 (12)
C360.0862 (19)0.112 (2)0.0551 (15)0.0046 (16)0.0001 (14)0.0115 (14)
C370.0587 (14)0.0638 (14)0.0705 (15)0.0087 (11)0.0152 (11)0.0022 (11)
C380.0543 (12)0.0458 (11)0.0471 (11)0.0005 (9)0.0099 (9)0.0053 (9)
C390.0612 (13)0.0528 (12)0.0530 (12)0.0058 (10)0.0118 (10)0.0061 (10)
C400.0732 (16)0.0746 (16)0.0654 (15)0.0207 (13)0.0285 (13)0.0107 (12)
C410.0543 (15)0.104 (2)0.0803 (18)0.0088 (14)0.0207 (13)0.0248 (16)
C420.0547 (14)0.0897 (18)0.0803 (17)0.0141 (13)0.0129 (12)0.0071 (14)
C17'0.098 (6)0.114 (7)0.089 (6)0.032 (5)0.009 (5)0.007 (5)
C18'0.224 (12)0.151 (8)0.081 (6)0.046 (8)0.033 (7)0.013 (6)
N10.0780 (14)0.0769 (14)0.0572 (12)0.0009 (11)0.0092 (10)0.0008 (10)
N20.120 (2)0.0963 (18)0.109 (2)0.0327 (16)0.0254 (17)0.0195 (16)
C240.0902 (17)0.0544 (13)0.0586 (14)0.0135 (12)0.0202 (12)0.0087 (11)
Geometric parameters (Å, º) top
C1—N11.506 (4)C19—H190.9300
C1—H1A0.9600C20—C211.396 (5)
C1—H1B0.9600C20—H200.9300
C1—H1C0.9600C21—C221.426 (4)
C2—N11.376 (4)C21—H210.9300
C2—C61.378 (4)C22—C231.421 (4)
C2—H20.9300C22—H220.9300
C3—N11.371 (4)C23—C241.433 (4)
C3—C41.378 (4)C25—C301.426 (4)
C3—H30.9300C25—C261.430 (4)
C4—C51.418 (4)C25—H250.9300
C4—H40.9300C26—C271.428 (4)
C5—C61.428 (4)C27—C281.413 (4)
C5—C71.485 (4)C27—H270.9300
C6—H60.9300C28—C291.403 (5)
C7—C81.353 (4)C28—H280.9300
C7—H70.9300C29—C301.412 (5)
C8—C91.476 (4)C29—H290.9300
C8—H80.9300C30—H300.9300
C9—C111.411 (4)C31—C341.418 (4)
C9—C101.424 (4)C31—C321.444 (4)
C10—C121.399 (5)C31—H310.9300
C10—H100.9300C32—C331.417 (4)
C11—C141.394 (4)C33—C361.422 (4)
C11—H110.9300C33—H330.9300
C12—C131.435 (4)C34—C351.396 (4)
C12—H120.9300C34—H340.9300
C13—N21.398 (4)C35—C361.407 (5)
C13—C141.420 (4)C35—H350.9300
C14—H140.9300C36—H360.9300
C15—C161.468 (5)C37—C421.413 (4)
C15—N21.539 (5)C37—C381.437 (3)
C15—H15A0.9700C37—H370.9300
C15—H15B0.9700C38—C391.430 (3)
C16—H16A0.9600C39—C401.437 (4)
C16—H16B0.9600C39—H390.9300
C16—H16C0.9600C40—C411.406 (4)
C17—C181.508 (14)C40—H400.9300
C17—N21.567 (12)C41—C421.403 (4)
C17—H17A0.9700C41—H410.9300
C17—H17B0.9700C42—H420.9300
C18—H18A0.9600C17'—N21.486 (11)
C18—H18B0.9600C17'—C18'1.569 (14)
C18—H18C0.9600C17'—H17C0.9700
B1—C231.682 (4)C17'—H17D0.9700
B1—C381.686 (4)C18'—H18D0.9600
B1—C261.696 (4)C18'—H18E0.9600
B1—C321.697 (4)C18'—H18F0.9600
C19—C201.397 (5)C24—H240.9300
C19—C241.413 (4)
N1—C1—H1A109.5C22—C23—C24114.18 (19)
N1—C1—H1B109.5C22—C23—B1124.9 (2)
H1A—C1—H1B109.5C24—C23—B1121.0 (2)
N1—C1—H1C109.5C30—C25—C26122.9 (3)
H1A—C1—H1C109.5C30—C25—H25118.5
H1B—C1—H1C109.5C26—C25—H25118.5
N1—C2—C6121.6 (3)C27—C26—C25114.6 (2)
N1—C2—H2119.2C27—C26—B1123.03 (19)
C6—C2—H2119.2C25—C26—B1122.0 (2)
N1—C3—C4121.7 (3)C28—C27—C26123.2 (3)
N1—C3—H3119.1C28—C27—H27118.4
C4—C3—H3119.1C26—C27—H27118.4
C3—C4—C5121.4 (3)C29—C28—C27120.5 (3)
C3—C4—H4119.3C29—C28—H28119.7
C5—C4—H4119.3C27—C28—H28119.7
C4—C5—C6115.5 (2)C28—C29—C30118.9 (3)
C4—C5—C7121.0 (2)C28—C29—H29120.6
C6—C5—C7123.5 (2)C30—C29—H29120.6
C2—C6—C5121.2 (2)C29—C30—C25119.8 (3)
C2—C6—H6119.4C29—C30—H30120.1
C5—C6—H6119.4C25—C30—H30120.1
C8—C7—C5125.3 (3)C34—C31—C32124.1 (2)
C8—C7—H7117.4C34—C31—H31117.9
C5—C7—H7117.4C32—C31—H31117.9
C7—C8—C9129.0 (3)C33—C32—C31113.3 (2)
C7—C8—H8115.5C33—C32—B1124.7 (2)
C9—C8—H8115.5C31—C32—B1121.90 (19)
C11—C9—C10115.0 (3)C32—C33—C36123.3 (2)
C11—C9—C8120.0 (3)C32—C33—H33118.4
C10—C9—C8124.9 (3)C36—C33—H33118.4
C12—C10—C9122.6 (3)C35—C34—C31120.0 (3)
C12—C10—H10118.7C35—C34—H34120.0
C9—C10—H10118.7C31—C34—H34120.0
C14—C11—C9123.2 (3)C34—C35—C36118.3 (3)
C14—C11—H11118.4C34—C35—H35120.8
C9—C11—H11118.4C36—C35—H35120.8
C10—C12—C13121.5 (3)C35—C36—C33121.0 (2)
C10—C12—H12119.3C35—C36—H36119.5
C13—C12—H12119.3C33—C36—H36119.5
N2—C13—C14122.5 (3)C42—C37—C38123.6 (2)
N2—C13—C12121.8 (3)C42—C37—H37118.2
C14—C13—C12115.5 (3)C38—C37—H37118.2
C11—C14—C13121.8 (3)C39—C38—C37113.8 (2)
C11—C14—H14119.1C39—C38—B1125.01 (18)
C13—C14—H14119.1C37—C38—B1121.2 (2)
C16—C15—N2110.5 (4)C38—C39—C40123.1 (2)
C16—C15—H15A109.5C38—C39—H39118.4
N2—C15—H15A109.5C40—C39—H39118.4
C16—C15—H15B109.5C41—C40—C39120.2 (2)
N2—C15—H15B109.5C41—C40—H40119.9
H15A—C15—H15B108.1C39—C40—H40119.9
C15—C16—H16A109.5C42—C41—C40118.5 (3)
C15—C16—H16B109.5C42—C41—H41120.7
H16A—C16—H16B109.5C40—C41—H41120.7
C15—C16—H16C109.5C41—C42—C37120.7 (2)
H16A—C16—H16C109.5C41—C42—H42119.6
H16B—C16—H16C109.5C37—C42—H42119.6
C18—C17—N2106.1 (11)N2—C17'—C18'110.8 (13)
C18—C17—H17A110.5N2—C17'—H17C109.5
N2—C17—H17A110.5C18'—C17'—H17C109.5
C18—C17—H17B110.5N2—C17'—H17D109.5
N2—C17—H17B110.5C18'—C17'—H17D109.5
H17A—C17—H17B108.7H17C—C17'—H17D108.1
C23—B1—C38110.74 (19)C17'—C18'—H18D109.5
C23—B1—C26107.8 (2)C17'—C18'—H18E109.5
C38—B1—C26109.56 (16)H18D—C18'—H18E109.5
C23—B1—C32106.80 (17)C17'—C18'—H18F109.5
C38—B1—C32110.19 (17)H18D—C18'—H18F109.5
C26—B1—C32111.73 (16)H18E—C18'—H18F109.5
C20—C19—C24120.6 (3)C3—N1—C2118.6 (2)
C20—C19—H19119.7C3—N1—C1121.1 (2)
C24—C19—H19119.7C2—N1—C1120.3 (2)
C21—C20—C19118.6 (2)C13—N2—C17'118.9 (4)
C21—C20—H20120.7C13—N2—C15121.2 (3)
C19—C20—H20120.7C17'—N2—C15117.9 (4)
C20—C21—C22120.4 (3)C13—N2—C17119.5 (5)
C20—C21—H21119.8C15—N2—C17114.2 (4)
C22—C21—H21119.8C19—C24—C23123.0 (3)
C23—C22—C21123.0 (2)C19—C24—H24118.5
C23—C22—H22118.5C23—C24—H24118.5
C21—C22—H22118.5
N1—C3—C4—C50.7 (5)C23—B1—C32—C33128.5 (2)
C3—C4—C5—C60.8 (4)C38—B1—C32—C338.2 (3)
C3—C4—C5—C7178.7 (3)C26—B1—C32—C33113.9 (2)
N1—C2—C6—C50.2 (4)C23—B1—C32—C3148.2 (2)
C4—C5—C6—C20.5 (4)C38—B1—C32—C31168.52 (18)
C7—C5—C6—C2178.9 (3)C26—B1—C32—C3169.4 (2)
C4—C5—C7—C8173.8 (3)C31—C32—C33—C360.9 (3)
C6—C5—C7—C85.6 (4)B1—C32—C33—C36177.8 (2)
C5—C7—C8—C9178.0 (3)C32—C31—C34—C351.3 (4)
C7—C8—C9—C11173.3 (3)C31—C34—C35—C360.5 (4)
C7—C8—C9—C1010.8 (5)C34—C35—C36—C330.0 (4)
C11—C9—C10—C124.2 (5)C32—C33—C36—C350.2 (4)
C8—C9—C10—C12179.7 (3)C42—C37—C38—C390.4 (3)
C10—C9—C11—C145.9 (5)C42—C37—C38—B1179.4 (2)
C8—C9—C11—C14177.8 (3)C23—B1—C38—C397.4 (3)
C9—C10—C12—C131.9 (6)C26—B1—C38—C39126.2 (2)
C10—C12—C13—N2178.4 (3)C32—B1—C38—C39110.5 (2)
C10—C12—C13—C146.4 (5)C23—B1—C38—C37173.75 (18)
C9—C11—C14—C131.5 (5)C26—B1—C38—C3755.0 (3)
N2—C13—C14—C11180.0 (3)C32—B1—C38—C3768.3 (2)
C12—C13—C14—C114.7 (5)C37—C38—C39—C401.3 (3)
C24—C19—C20—C211.5 (4)B1—C38—C39—C40179.83 (19)
C19—C20—C21—C221.3 (4)C38—C39—C40—C411.2 (3)
C20—C21—C22—C230.5 (4)C39—C40—C41—C420.2 (3)
C21—C22—C23—C242.1 (3)C40—C41—C42—C370.6 (4)
C21—C22—C23—B1177.0 (2)C38—C37—C42—C410.5 (4)
C38—B1—C23—C22105.1 (2)C4—C3—N1—C20.3 (4)
C26—B1—C23—C2214.7 (3)C4—C3—N1—C1179.7 (3)
C32—B1—C23—C22134.9 (2)C6—C2—N1—C30.1 (4)
C38—B1—C23—C2475.7 (3)C6—C2—N1—C1179.4 (2)
C26—B1—C23—C24164.43 (18)C14—C13—N2—C17'11.6 (8)
C32—B1—C23—C2444.2 (2)C12—C13—N2—C17'163.4 (6)
C30—C25—C26—C271.6 (3)C14—C13—N2—C15175.3 (3)
C30—C25—C26—B1171.7 (2)C12—C13—N2—C150.4 (5)
C23—B1—C26—C2772.8 (3)C14—C13—N2—C1731.2 (7)
C38—B1—C26—C27166.66 (18)C12—C13—N2—C17153.8 (6)
C32—B1—C26—C2744.3 (2)C18'—C17'—N2—C1386.4 (9)
C23—B1—C26—C25100.0 (3)C18'—C17'—N2—C15109.3 (6)
C38—B1—C26—C2520.5 (3)C18'—C17'—N2—C1715.3 (8)
C32—B1—C26—C25142.9 (2)C16—C15—N2—C1378.9 (5)
C25—C26—C27—C281.8 (3)C16—C15—N2—C17'117.1 (7)
B1—C26—C27—C28171.5 (2)C16—C15—N2—C1775.8 (6)
C26—C27—C28—C290.8 (4)C18—C17—N2—C13101.2 (8)
C27—C28—C29—C300.4 (4)C18—C17—N2—C17'1.2 (7)
C28—C29—C30—C250.5 (4)C18—C17—N2—C15103.6 (7)
C26—C25—C30—C290.6 (4)C20—C19—C24—C230.3 (4)
C34—C31—C32—C331.5 (3)C22—C23—C24—C192.0 (3)
C34—C31—C32—B1178.5 (2)B1—C23—C24—C19177.2 (2)
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Education Committee of Anhui Province (grant No. KJ2010A030) and the Natural Science Foundation of Anhui Provincce (grant No. 1208085MB22).

references
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