organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

A third polymorph of 1,4-bis­­(1H-benzimid­azol-2-yl)benzene

aKey Laboratory of Functional Organometallic Materials of General Colleges and Universities in Hunan Province, Department of Chemistry and Materials Science, Hengyang Normal University, Hengyang 421008, People's Republic of China
*Correspondence e-mail: w.w.fu@hotmail.com

(Received 30 April 2014; accepted 15 May 2014; online 24 May 2014)

The title compound, C20H14N4, is a new polymorph of the previously reported structures, which were ortho­rhom­bic, space group Pbca [Bei et al. (2000). Acta Cryst. C56, 718–719] and monoclinic, space group P21/c [Dudd et al. (2003). Green Chem. 5, 187–192]. The asymmetric unit consists of two independent mol­ecules in which the dihedral angels between the central benzene ring and the outer benzimidazole ring systems are 16.81 (10) and 14.23 (10)° in one molecule and 26.09 (10) and 37.29 (10)° in the other. In the crystal, mol­ecules are linked by N—H⋯N and C—H⋯N hydrogen bonds into a tape running along the c-axis direction.

Related literature

For the synthesis of the title compound, see: Alcalde et al. (1992[Alcalde, E., Dinarés, I., Pérez-Garcïa, L. & Roca, T. (1992). Synthesis, 1992, 395-398.]); Zhao et al. (2012[Zhao, W. X., Wang, B., Jiang, H. B. & Wang, X. D. (2012). Appl. Chem. Ind. 41, 539-545.]); Zhuang et al. (2011[Zhuang, J. T., Qian, Y., Wu, L., Wang, J. J., Gong, J. & Yang, H. (2011). Appl. Chem. Ind. 40, 2075-2079.]). For the previously reported structures of the title compound, see: Bei et al. (2000[Bei, F., Jian, F., Yang, X., Lu, L., Wang, X., Shanmuga Sundara Raj, S. & Fun, H.-K. (2000). Acta Cryst. C56, 718-719.]); Dudd et al. (2003[Dudd, L. M., Venardou, E., Garcia-Verdugo, E., Licence, P., Blake, A. J., Wilson, C. & Poliakoff, M. (2003). Green Chem. 5, 187-192.]). For the structures of the title compound with solvent mol­ecules, see: Wu & Hu (2009[Wu, D.-H. & Hu, L. (2009). Acta Cryst. E65, o522.]); Su et al. (2011[Su, J.-B., Lin, S., Chen, L.-J., Yang, M.-X. & Huang, H. (2011). Acta Cryst. E67, o90.]).

[Scheme 1]

Experimental

Crystal data
  • C20H14N4

  • Mr = 310.35

  • Monoclinic, P 21 /c

  • a = 16.196 (3) Å

  • b = 20.174 (3) Å

  • c = 9.9010 (16) Å

  • β = 106.733 (3)°

  • V = 3098.1 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.26 × 0.22 × 0.17 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.986

  • 15697 measured reflections

  • 5451 independent reflections

  • 3197 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.126

  • S = 1.02

  • 5451 reflections

  • 450 parameters

  • 5 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯N5 0.91 (2) 2.06 (2) 2.947 (3) 164 (2)
N4—H4⋯N3i 0.93 (2) 1.91 (2) 2.837 (3) 172 (2)
N6—H6⋯N1ii 0.92 (2) 2.00 (2) 2.910 (3) 171 (2)
N8—H8⋯N7i 0.90 (2) 2.15 (2) 3.041 (3) 174 (2)
C12—H12⋯N3i 0.93 2.57 3.396 (3) 148
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z-1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2008[Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Benzimidazole and their derivatives have been widely researched for their potential applications in medicinal chemistry, biochemistry and material chemistry. 1,4-bis(benzimidazol-2-yl)benzene has been synthesized with many methods in different groups. Zhuang have synthesized 1,4-bis(benzimidazol-2-yl)benzene with microwave method (Zhuang et al., 2011). Zhao have synthesized it using phosphoric acid as a catalyst (Zhao et al., 2012) instead of polyphosphoric acid which are commonly used in synthesis of benzimidazole (Alcalde et al., 1992). Its crystal structure has been determined by Bei et al. (2000) and Dudd et al. (2003). Recently, its crystal structures with solvent molecules DMF or methanol have also been reported (Wu & Hu, 2009; Su et al., 2011). Here, we report a new crystal structure of 1,4-bis(benzimidazol-2-yl)benzene.

In the crystal, the asymmetric unit contains two independent 1,4-bis(benzimidazol-2-yl)benzene molecules. The bond lengths are similar with those in literature (Bei et al., 2000; Dudd et al., 2003; Wu & Hu, 2009; Su et al., 2011). The angles between benzimidazole rings (r.m.s. deviations of 0.0028 Å for molecule contain N1 and 0.0140 Å for molecule contain N3) and benzene rings (r.m.s. deviations of 0.0140 Å for C8–C13) are 16.8 and 14.2°. In the other molecule, the angles between benzimidazole rings (r.m.s. deviations of 0.0065 Å for molecule contain N5 and 0.0127 Å for molecule contain N7) and benzene rings (r.m.s. deviations of 0.0045 Å for C28–C33) are 26.1 and 37.3°. These angles are different with those reported by other researchers (31.0°, Bei et al., 2000; Dudd et al., 2003; 9.1°, Wu & Hu, 2009; 24.0° and 11. 6°, Su et al., 2011). There are five kinds of hydrogen bonds which result in one dimensional network as that shown in Fig. 2 and Table 1.

Related literature top

For the synthesis of the title compound, see: Alcalde et al. (1992); Zhao et al. (2012); Zhuang et al. (2011). For the previously reported structures of the title compound, see: Bei et al. (2000); Dudd et al. (2003). For the structures of the title compound with solvent molecules, see: Wu & Hu (2009); Su et al. (2011).

Experimental top

1,4-Bis(benzimidazol-2-yl)benzene was synthesized according to literature method (Alcalde et al., 1992; Zhao et al., 2012) and single crystals suitable for X-ray diffraction were obtained by slow evaporation of DMF solution at room temperature.

Refinement top

N-bound H atoms were located in a difference Fourier map and were refined with bond-length restraints of N—H = 0.86 (2) Å. C-bound H atoms were positioned geometrically and treated as riding atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C). Rigid-bond restraints (DELU) were applied for atoms C11 and C14.

Computing details top

Data collection: APEX2 (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) and DIAMOND (Brandenburg, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. An ORTEP drawing for the asymmetric unit of the title compound with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound viewed along c direction. The hydrogen bonds are highlighted by dashed lines.
1,4-Bis(1H-benzimidazol-2-yl)benzene top
Crystal data top
C20H14N4F(000) = 1296
Mr = 310.35Dx = 1.331 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1697 reflections
a = 16.196 (3) Åθ = 2.4–22.0°
b = 20.174 (3) ŵ = 0.08 mm1
c = 9.9010 (16) ÅT = 296 K
β = 106.733 (3)°Block, yellow
V = 3098.1 (8) Å30.26 × 0.22 × 0.17 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer
5451 independent reflections
Radiation source: fine-focus sealed tube3197 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1619
Tmin = 0.979, Tmax = 0.986k = 2323
15697 measured reflectionsl = 118
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.042P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5451 reflectionsΔρmax = 0.21 e Å3
450 parametersΔρmin = 0.21 e Å3
5 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0018 (3)
Crystal data top
C20H14N4V = 3098.1 (8) Å3
Mr = 310.35Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.196 (3) ŵ = 0.08 mm1
b = 20.174 (3) ÅT = 296 K
c = 9.9010 (16) Å0.26 × 0.22 × 0.17 mm
β = 106.733 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
5451 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
3197 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.986Rint = 0.062
15697 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0535 restraints
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.21 e Å3
5451 reflectionsΔρmin = 0.21 e Å3
450 parameters
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
N10.29247 (12)0.04939 (9)0.8970 (2)0.0422 (5)
N20.27746 (13)0.04637 (9)0.6655 (2)0.0449 (5)
N30.07524 (11)0.26679 (8)0.8390 (2)0.0400 (5)
N40.06709 (12)0.27094 (9)0.6109 (2)0.0409 (5)
N50.21368 (12)0.03614 (9)0.3559 (2)0.0457 (5)
N60.25379 (13)0.06306 (9)0.1650 (2)0.0447 (5)
N70.38516 (11)0.29079 (8)0.3466 (2)0.0429 (5)
N80.39950 (13)0.27194 (9)0.1317 (2)0.0430 (5)
C10.32991 (14)0.10557 (10)0.8589 (3)0.0419 (6)
C20.37149 (15)0.15816 (11)0.9408 (3)0.0523 (7)
H2A0.37760.15991.03710.063*
C30.40316 (16)0.20745 (12)0.8745 (3)0.0572 (7)
H30.43150.24320.92730.069*
C40.39416 (16)0.20559 (12)0.7306 (3)0.0585 (7)
H4A0.41660.24010.68970.070*
C50.35302 (15)0.15420 (12)0.6475 (3)0.0551 (7)
H50.34690.15290.55120.066*
C60.32114 (14)0.10441 (10)0.7147 (3)0.0416 (6)
C70.26227 (14)0.01539 (10)0.7780 (3)0.0404 (6)
C80.22036 (14)0.04919 (10)0.7669 (2)0.0380 (6)
C90.18877 (15)0.07285 (10)0.8733 (3)0.0463 (6)
H90.19410.04700.95310.056*
C100.14979 (15)0.13358 (11)0.8634 (3)0.0483 (6)
H100.13000.14860.93720.058*
C110.13940 (13)0.17303 (10)0.7452 (2)0.0366 (5)
C120.17413 (15)0.15063 (11)0.6412 (3)0.0504 (7)
H120.17040.17700.56270.061*
C130.21410 (16)0.08991 (12)0.6522 (3)0.0549 (7)
H130.23730.07600.58130.066*
C140.09418 (14)0.23666 (10)0.7334 (2)0.0379 (6)
C150.03436 (14)0.32525 (11)0.7812 (3)0.0425 (6)
C160.00158 (16)0.37657 (12)0.8445 (3)0.0597 (7)
H160.00400.37480.93950.072*
C170.03427 (19)0.42969 (13)0.7627 (4)0.0739 (9)
H170.05550.46500.80320.089*
C180.03965 (18)0.43187 (13)0.6192 (4)0.0740 (9)
H180.06480.46860.56650.089*
C190.00906 (15)0.38159 (12)0.5539 (3)0.0579 (7)
H190.01330.38300.45820.069*
C200.02871 (14)0.32833 (11)0.6384 (3)0.0428 (6)
C210.19204 (14)0.10180 (11)0.3204 (3)0.0441 (6)
C220.15135 (16)0.14810 (12)0.3834 (3)0.0582 (7)
H220.13350.13710.46190.070*
C230.13831 (17)0.21025 (13)0.3267 (3)0.0627 (8)
H230.11100.24190.36700.075*
C240.16497 (17)0.22720 (12)0.2103 (3)0.0637 (8)
H240.15610.27030.17560.076*
C250.20405 (16)0.18225 (11)0.1449 (3)0.0587 (7)
H250.22100.19360.06580.070*
C260.21713 (14)0.11937 (11)0.2019 (3)0.0440 (6)
C270.24929 (14)0.01533 (10)0.2595 (2)0.0396 (6)
C280.28177 (14)0.05166 (10)0.2531 (2)0.0371 (6)
C290.34685 (14)0.06484 (10)0.1920 (3)0.0447 (6)
H290.37040.03020.15310.054*
C300.37728 (15)0.12830 (11)0.1877 (3)0.0458 (6)
H300.42120.13620.14660.055*
C310.34253 (14)0.18036 (10)0.2446 (2)0.0372 (5)
C320.27666 (14)0.16773 (10)0.3045 (2)0.0428 (6)
H320.25290.20240.34270.051*
C330.24615 (14)0.10442 (10)0.3080 (2)0.0427 (6)
H330.20130.09670.34730.051*
C340.37521 (14)0.24779 (10)0.2431 (3)0.0391 (6)
C350.41685 (14)0.34739 (10)0.2989 (3)0.0400 (6)
C360.43613 (14)0.40958 (11)0.3605 (3)0.0493 (6)
H360.42920.41830.44880.059*
C370.46551 (16)0.45757 (11)0.2884 (3)0.0559 (7)
H370.47840.49950.32810.067*
C380.47638 (18)0.44489 (13)0.1577 (3)0.0677 (8)
H380.49730.47830.11180.081*
C390.45718 (16)0.38443 (12)0.0935 (3)0.0606 (7)
H390.46450.37620.00520.073*
C400.42666 (14)0.33628 (10)0.1652 (3)0.0412 (6)
H20.2599 (15)0.0344 (12)0.5728 (19)0.069 (9)*
H40.0751 (15)0.2586 (10)0.5247 (19)0.059 (8)*
H60.2687 (15)0.0543 (12)0.084 (2)0.070 (8)*
H80.3954 (16)0.2505 (11)0.051 (2)0.069 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0531 (12)0.0402 (11)0.0389 (13)0.0030 (9)0.0219 (11)0.0027 (9)
N20.0578 (13)0.0460 (12)0.0346 (14)0.0063 (10)0.0192 (12)0.0028 (11)
N30.0488 (11)0.0394 (11)0.0365 (12)0.0025 (9)0.0195 (10)0.0018 (9)
N40.0485 (12)0.0412 (11)0.0381 (14)0.0025 (9)0.0204 (11)0.0002 (10)
N50.0574 (12)0.0460 (12)0.0421 (13)0.0083 (10)0.0277 (11)0.0020 (10)
N60.0608 (13)0.0405 (11)0.0409 (14)0.0066 (10)0.0277 (12)0.0020 (10)
N70.0562 (12)0.0356 (10)0.0433 (13)0.0040 (9)0.0249 (11)0.0006 (9)
N80.0548 (12)0.0417 (12)0.0379 (14)0.0039 (9)0.0217 (11)0.0011 (10)
C10.0443 (13)0.0400 (13)0.0443 (17)0.0018 (11)0.0175 (13)0.0019 (12)
C20.0614 (15)0.0470 (15)0.0520 (18)0.0081 (13)0.0218 (15)0.0081 (13)
C30.0599 (16)0.0444 (15)0.069 (2)0.0109 (13)0.0207 (17)0.0033 (14)
C40.0586 (16)0.0531 (16)0.066 (2)0.0107 (13)0.0209 (17)0.0101 (15)
C50.0618 (16)0.0547 (16)0.0511 (19)0.0094 (13)0.0197 (15)0.0104 (14)
C60.0454 (13)0.0388 (13)0.0437 (16)0.0015 (11)0.0178 (13)0.0022 (12)
C70.0473 (14)0.0398 (13)0.0382 (16)0.0010 (11)0.0190 (13)0.0013 (12)
C80.0439 (13)0.0386 (13)0.0350 (15)0.0021 (10)0.0167 (12)0.0023 (11)
C90.0632 (15)0.0428 (14)0.0396 (16)0.0090 (12)0.0257 (14)0.0068 (11)
C100.0663 (16)0.0468 (14)0.0414 (16)0.0093 (12)0.0304 (14)0.0006 (12)
C110.0411 (12)0.0356 (12)0.0361 (15)0.0007 (10)0.0161 (12)0.0001 (11)
C120.0674 (16)0.0507 (15)0.0415 (17)0.0156 (13)0.0288 (15)0.0092 (12)
C130.0757 (18)0.0563 (16)0.0413 (17)0.0196 (14)0.0305 (15)0.0058 (13)
C140.0443 (13)0.0396 (13)0.0340 (15)0.0063 (11)0.0177 (12)0.0005 (11)
C150.0432 (13)0.0404 (13)0.0476 (17)0.0009 (11)0.0191 (13)0.0013 (12)
C160.0655 (17)0.0596 (17)0.062 (2)0.0130 (14)0.0310 (16)0.0032 (15)
C170.084 (2)0.0598 (18)0.083 (3)0.0289 (16)0.033 (2)0.0013 (18)
C180.081 (2)0.0575 (18)0.084 (3)0.0277 (15)0.026 (2)0.0120 (17)
C190.0630 (16)0.0552 (16)0.059 (2)0.0122 (13)0.0232 (15)0.0148 (14)
C200.0419 (13)0.0395 (13)0.0504 (18)0.0022 (11)0.0185 (13)0.0022 (12)
C210.0498 (14)0.0458 (14)0.0390 (16)0.0079 (11)0.0162 (13)0.0009 (12)
C220.0701 (17)0.0579 (16)0.0534 (19)0.0156 (14)0.0287 (15)0.0026 (14)
C230.0642 (17)0.0567 (17)0.069 (2)0.0192 (14)0.0215 (17)0.0094 (15)
C240.0701 (18)0.0433 (15)0.081 (2)0.0116 (13)0.0264 (18)0.0039 (15)
C250.0723 (17)0.0469 (15)0.064 (2)0.0089 (13)0.0310 (16)0.0103 (14)
C260.0479 (14)0.0420 (14)0.0440 (17)0.0039 (11)0.0164 (13)0.0019 (12)
C270.0466 (14)0.0399 (13)0.0353 (15)0.0014 (11)0.0166 (12)0.0011 (11)
C280.0436 (13)0.0394 (13)0.0331 (14)0.0002 (10)0.0189 (12)0.0015 (11)
C290.0536 (14)0.0385 (13)0.0516 (17)0.0020 (11)0.0304 (14)0.0060 (12)
C300.0518 (14)0.0473 (14)0.0487 (17)0.0041 (11)0.0309 (13)0.0061 (12)
C310.0420 (13)0.0383 (13)0.0346 (15)0.0028 (10)0.0163 (12)0.0023 (11)
C320.0497 (14)0.0408 (13)0.0448 (16)0.0074 (11)0.0245 (13)0.0008 (11)
C330.0453 (13)0.0430 (14)0.0465 (16)0.0001 (11)0.0240 (13)0.0009 (12)
C340.0441 (13)0.0407 (13)0.0363 (15)0.0014 (11)0.0174 (12)0.0005 (12)
C350.0455 (13)0.0384 (13)0.0398 (16)0.0005 (11)0.0180 (12)0.0021 (11)
C360.0610 (16)0.0428 (14)0.0475 (17)0.0050 (12)0.0210 (14)0.0061 (12)
C370.0678 (17)0.0432 (14)0.059 (2)0.0135 (13)0.0220 (16)0.0018 (14)
C380.094 (2)0.0559 (17)0.059 (2)0.0259 (15)0.0307 (19)0.0058 (15)
C390.0809 (19)0.0634 (17)0.0452 (18)0.0196 (15)0.0305 (16)0.0002 (14)
C400.0458 (13)0.0400 (13)0.0415 (16)0.0051 (11)0.0183 (13)0.0008 (11)
Geometric parameters (Å, º) top
N1—C71.329 (3)C15—C161.392 (3)
N1—C11.388 (3)C16—C171.368 (3)
N2—H20.912 (17)C16—H160.9300
N3—C141.319 (3)C17—H170.9300
N3—C151.392 (3)C18—C171.400 (4)
N4—C141.355 (3)C18—H180.9300
N4—C201.378 (3)C19—C181.370 (3)
N4—H40.933 (16)C19—H190.9300
N5—C271.318 (3)C20—C191.391 (3)
N5—C211.389 (3)C20—C151.392 (3)
N6—C271.359 (3)C21—C221.391 (3)
N6—C261.379 (3)C21—C261.393 (3)
N6—H60.916 (16)C22—C231.365 (3)
N7—C341.316 (3)C22—H220.9300
N7—C351.389 (3)C23—H230.9300
N8—C341.363 (3)C24—C231.385 (4)
N8—C401.380 (3)C24—H240.9300
N8—H80.898 (16)C25—C241.370 (3)
C1—C21.386 (3)C25—H250.9300
C2—C31.370 (3)C26—C251.380 (3)
C2—H2A0.9300C28—C291.384 (3)
C3—C41.391 (4)C28—C331.393 (3)
C3—H30.9300C28—C271.458 (3)
C4—H4A0.9300C29—H290.9300
C5—C41.371 (3)C30—C291.377 (3)
C5—H50.9300C30—H300.9300
C6—N21.382 (3)C31—C301.385 (3)
C6—C51.384 (3)C31—C321.386 (3)
C6—C11.393 (3)C32—H320.9300
C7—N21.360 (3)C33—C321.373 (3)
C7—C81.459 (3)C33—H330.9300
C8—C131.381 (3)C34—C311.461 (3)
C9—C101.369 (3)C35—C361.391 (3)
C9—C81.381 (3)C35—C401.396 (3)
C9—H90.9300C36—C371.367 (3)
C10—H100.9300C36—H360.9300
C11—C121.384 (3)C37—C381.379 (4)
C11—C101.385 (3)C37—H370.9300
C11—C141.466 (3)C38—H380.9300
C12—C131.375 (3)C39—C381.369 (3)
C12—H120.9300C39—H390.9300
C13—H130.9300C40—C391.376 (3)
C7—N1—C1104.99 (19)C29—C30—H30120.0
C7—N2—C6107.2 (2)C31—C30—H30120.0
C7—N2—H2128.7 (16)N6—C26—C25132.6 (2)
C6—N2—H2123.9 (16)N6—C26—C21105.4 (2)
C14—N3—C15104.86 (19)C25—C26—C21122.0 (2)
C14—N4—C20107.5 (2)N5—C27—N6113.21 (19)
C14—N4—H4126.0 (14)N5—C27—C28124.4 (2)
C20—N4—H4126.5 (14)N6—C27—C28122.4 (2)
C27—N6—C26106.80 (19)C20—C15—N3109.85 (19)
C27—N6—H6122.9 (15)C20—C15—C16120.2 (2)
C26—N6—H6129.2 (16)N3—C15—C16130.0 (2)
C34—N7—C35104.58 (19)C12—C13—C8121.1 (2)
C34—N8—C40106.7 (2)C12—C13—H13119.4
C34—N8—H8126.0 (16)C8—C13—H13119.4
C40—N8—H8127.2 (16)C3—C2—C1117.5 (2)
N1—C7—N2112.4 (2)C3—C2—H2A121.3
N1—C7—C8124.9 (2)C1—C2—H2A121.3
N2—C7—C8122.6 (2)C33—C32—C31120.6 (2)
N7—C34—N8113.25 (19)C33—C32—H32119.7
N7—C34—C31124.7 (2)C31—C32—H32119.7
N8—C34—C31122.0 (2)C30—C29—C28121.1 (2)
C12—C11—C10117.7 (2)C30—C29—H29119.5
C12—C11—C14121.8 (2)C28—C29—H29119.5
C10—C11—C14120.5 (2)C38—C39—C40117.2 (2)
C27—N5—C21104.58 (18)C38—C39—H39121.4
C10—C9—C8121.3 (2)C40—C39—H39121.4
C10—C9—H9119.4C4—C5—C6116.4 (2)
C8—C9—H9119.4C4—C5—H5121.8
N4—C20—C19132.5 (2)C6—C5—H5121.8
N4—C20—C15105.2 (2)C37—C36—C35118.5 (2)
C19—C20—C15122.3 (2)C37—C36—H36120.7
N2—C6—C5132.0 (2)C35—C36—H36120.7
N2—C6—C1105.44 (19)C36—C37—C38121.1 (2)
C5—C6—C1122.6 (2)C36—C37—H37119.5
C9—C10—C11121.1 (2)C38—C37—H37119.5
C9—C10—H10119.5C2—C3—C4121.9 (2)
C11—C10—H10119.5C2—C3—H3119.1
C29—C28—C33118.47 (19)C4—C3—H3119.1
C29—C28—C27121.76 (19)C18—C19—C20116.4 (3)
C33—C28—C27119.76 (19)C18—C19—H19121.8
C2—C1—N1130.0 (2)C20—C19—H19121.8
C2—C1—C6120.1 (2)C5—C4—C3121.6 (2)
N1—C1—C6109.9 (2)C5—C4—H4A119.2
C13—C8—C9117.7 (2)C3—C4—H4A119.2
C13—C8—C7121.0 (2)C17—C16—C15117.9 (3)
C9—C8—C7121.2 (2)C17—C16—H16121.0
N7—C35—C36130.6 (2)C15—C16—H16121.0
N7—C35—C40110.15 (19)C23—C22—C21118.0 (2)
C36—C35—C40119.2 (2)C23—C22—H22121.0
N3—C14—N4112.65 (19)C21—C22—H22121.0
N3—C14—C11124.4 (2)C24—C25—C26116.9 (2)
N4—C14—C11122.9 (2)C24—C25—H25121.5
C13—C12—C11121.0 (2)C26—C25—H25121.5
C13—C12—H12119.5C25—C24—C23121.8 (2)
C11—C12—H12119.5C25—C24—H24119.1
C32—C33—C28120.6 (2)C23—C24—H24119.1
C32—C33—H33119.7C19—C18—C17122.1 (3)
C28—C33—H33119.7C19—C18—H18119.0
C30—C31—C32119.19 (19)C17—C18—H18119.0
C30—C31—C34120.74 (19)C22—C23—C24121.4 (2)
C32—C31—C34120.06 (19)C22—C23—H23119.3
N5—C21—C22130.1 (2)C24—C23—H23119.3
N5—C21—C26110.01 (19)C39—C38—C37121.8 (2)
C22—C21—C26119.9 (2)C39—C38—H38119.1
C39—C40—N8132.6 (2)C37—C38—H38119.1
C39—C40—C35122.1 (2)C16—C17—C18121.2 (3)
N8—C40—C35105.26 (19)C16—C17—H17119.4
C29—C30—C31120.1 (2)C18—C17—H17119.4
C1—N1—C7—N20.4 (3)C27—N6—C26—C210.1 (3)
C1—N1—C7—C8177.3 (2)N5—C21—C26—N60.5 (3)
C35—N7—C34—N81.0 (3)C22—C21—C26—N6179.2 (2)
C35—N7—C34—C31179.7 (2)N5—C21—C26—C25179.3 (2)
C40—N8—C34—N70.7 (3)C22—C21—C26—C250.9 (4)
C40—N8—C34—C31179.96 (19)C21—N5—C27—N61.1 (3)
C14—N4—C20—C19179.1 (2)C21—N5—C27—C28179.4 (2)
C14—N4—C20—C150.4 (2)C26—N6—C27—N50.8 (3)
C8—C9—C10—C111.1 (4)C26—N6—C27—C28179.7 (2)
C12—C11—C10—C93.6 (4)C29—C28—C27—N5153.5 (2)
C14—C11—C10—C9177.3 (2)C33—C28—C27—N527.4 (3)
C7—N1—C1—C2179.8 (2)C29—C28—C27—N626.0 (3)
C7—N1—C1—C60.2 (2)C33—C28—C27—N6153.2 (2)
N2—C6—C1—C2179.97 (19)N4—C20—C15—N30.2 (2)
C5—C6—C1—C20.4 (4)C19—C20—C15—N3179.8 (2)
N2—C6—C1—N10.1 (2)N4—C20—C15—C16179.6 (2)
C5—C6—C1—N1179.6 (2)C19—C20—C15—C160.0 (4)
C10—C9—C8—C132.3 (4)C14—N3—C15—C200.8 (2)
C10—C9—C8—C7179.7 (2)C14—N3—C15—C16179.0 (2)
N1—C7—C8—C13160.4 (2)C11—C12—C13—C80.4 (4)
N2—C7—C8—C1317.1 (3)C9—C8—C13—C123.0 (4)
N1—C7—C8—C916.9 (3)C7—C8—C13—C12179.6 (2)
N2—C7—C8—C9165.6 (2)N1—C1—C2—C3179.6 (2)
C34—N7—C35—C36177.0 (2)C6—C1—C2—C30.4 (3)
C34—N7—C35—C400.9 (3)C28—C33—C32—C311.0 (3)
N1—C7—N2—C60.4 (3)C30—C31—C32—C330.1 (3)
C8—C7—N2—C6177.33 (19)C34—C31—C32—C33179.2 (2)
C5—C6—N2—C7179.4 (2)C31—C30—C29—C280.3 (4)
C1—C6—N2—C70.3 (2)C33—C28—C29—C301.3 (3)
C15—N3—C14—N41.1 (2)C27—C28—C29—C30179.5 (2)
C15—N3—C14—C11179.01 (19)N8—C40—C39—C38178.1 (2)
C20—N4—C14—N31.0 (3)C35—C40—C39—C381.2 (4)
C20—N4—C14—C11179.10 (19)N2—C6—C5—C4179.7 (2)
C12—C11—C14—N3165.6 (2)C1—C6—C5—C40.1 (4)
C10—C11—C14—N313.4 (3)N7—C35—C36—C37178.8 (2)
C12—C11—C14—N414.5 (3)C40—C35—C36—C371.0 (3)
C10—C11—C14—N4166.5 (2)C35—C36—C37—C380.3 (4)
C10—C11—C12—C132.9 (4)C1—C2—C3—C40.2 (4)
C14—C11—C12—C13178.1 (2)N4—C20—C19—C18178.6 (2)
C29—C28—C33—C321.7 (3)C15—C20—C19—C180.9 (4)
C27—C28—C33—C32179.2 (2)C6—C5—C4—C30.1 (4)
N7—C34—C31—C30141.3 (2)C2—C3—C4—C50.0 (4)
N8—C34—C31—C3038.0 (3)C20—C15—C16—C171.2 (4)
N7—C34—C31—C3238.0 (3)N3—C15—C16—C17178.6 (2)
N8—C34—C31—C32142.7 (2)N5—C21—C22—C23179.6 (2)
C27—N5—C21—C22178.7 (3)C26—C21—C22—C230.8 (4)
C27—N5—C21—C261.0 (3)N6—C26—C25—C24179.8 (2)
C34—N8—C40—C39179.4 (3)C21—C26—C25—C240.0 (4)
C34—N8—C40—C350.0 (3)C26—C25—C24—C231.1 (4)
N7—C35—C40—C39180.0 (2)C20—C19—C18—C170.7 (4)
C36—C35—C40—C391.8 (4)C21—C22—C23—C240.3 (4)
N7—C35—C40—N80.6 (3)C25—C24—C23—C221.3 (5)
C36—C35—C40—N8177.6 (2)C40—C39—C38—C370.2 (4)
C32—C31—C30—C290.5 (3)C36—C37—C38—C391.0 (5)
C34—C31—C30—C29178.9 (2)C15—C16—C17—C181.4 (4)
C27—N6—C26—C25180.0 (3)C19—C18—C17—C160.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N50.91 (2)2.06 (2)2.947 (3)164 (2)
N4—H4···N3i0.93 (2)1.91 (2)2.837 (3)172 (2)
N6—H6···N1ii0.92 (2)2.00 (2)2.910 (3)171 (2)
N8—H8···N7i0.90 (2)2.15 (2)3.041 (3)174 (2)
C12—H12···N3i0.932.573.396 (3)148
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N50.912 (17)2.061 (18)2.947 (3)164 (2)
N4—H4···N3i0.933 (16)1.909 (17)2.837 (3)172 (2)
N6—H6···N1ii0.916 (16)2.002 (17)2.910 (3)171 (2)
N8—H8···N7i0.898 (16)2.146 (17)3.041 (3)174 (2)
C12—H12···N3i0.932.573.396 (3)148
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y, z1.
 

Acknowledgements

Financial support by the key discipline project of Hunan Province is gratefully acknowledged.

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