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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o345-o346
https://doi.org/10.1107/S2056989015007975

Crystal structure of 9-butyl-6-[2-(pyridin-4-yl)ethen­yl]carbazol-3-amine

Ping Zhang,a Xiang-Yang Baib and Ting Zhanga*

aDeparment of Chemistry, Anhui Science and Technolgy University, Fengyang 233100, People's Republic of China, and bCollege of Chemistry & Chemical Engineering, Anhui University, Hefei 230039, People's Republic of China, Key Laboratory of Functional Inorganic Materials of Anhui Province, Hefei 230039, People's Republic of China
*Correspondence e-mail: zhangt@ahstu.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 March 2015; accepted 22 April 2015; online 25 April 2015)

The asymmetric unit of the title compound, C23H23N3, consists of two mol­ecules, A and B, with different conformations. In mol­ecule A, the dihedral angle between the carbazole ring system (r.m.s. deviation = 0.028 Å) and the pyridine ring is 20.28 (9)° and the N—C—C—C torsion angle of the butyl side chain is −63.4 (3)°. The equivalent data for mol­ecule B are 0.065 Å, 48.28 (11)° and 61.0 (3)°, respectively. In the crystal, the components are connected by weak N—H⋯N hydrogen bonds, generating [030] C(14) chains of alternating A and B mol­ecules.

CCDC reference: 1061103

Similar articles

1. Related literature

For background to the applications of carbazoles, see: Wang et al. (2013[Wang, H. W., Chen, Y., Ye, W. B., Xu, J. K., Liu, D. F., Yang, J. X., Kong, L., Zhou, H. P., Tian, Y. P. & Tao, X. T. (2013). Dyes Pigments, 96, 738-747.]); Feng et al. (2013[Feng, X. J., Tian, P. Z., Xu, Z., Chen, S. F. & Wong, M. S. (2013). J. Org. Chem. 78, 11318-11325.]); Park et al. (2015[Park, Y. I., Postupna, O., Zhugayevych, A., Shin, H., Park, Y. S., Kim, B., Yen, H. J., Cheruku, P., Martinez, J. S., Park, J. W., Tretiak, S. & Wang, H. L. (2015). Chem. Sci. 6, 789-797.]). For further synthetic details, see: Zhang et al. (2014[Zhang, P., Liu, J., Huang, J. Y. & Yang, J. X. (2014). Chin. J. Appl. Chem. 31, 1171-1176.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C23H23N3

  • Mr = 341.44

  • Monoclinic, P 21 /c

  • a = 11.296 (4) Å

  • b = 18.719 (7) Å

  • c = 17.829 (7) Å

  • β = 95.362 (5)°

  • V = 3753 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

2.2. Data collection

  • Bruker SMART CCD diffractometer

  • 26552 measured reflections

  • 6604 independent reflections

  • 4780 reflections with I > 2σ(I)

  • Rint = 0.029

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.166

  • S = 1.14

  • 6604 reflections

  • 471 parameters

  • 5 restraints

  • H-atom parameters constrained

  • Δρmax = 0.66 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2D⋯N6 0.86 2.56 3.154 (3) 128
N5—H5B⋯N3i 0.86 2.36 3.163 (3) 156
Symmetry code: (i) [-x+1, y+{\script{3\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1061103

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989015007975/hb7392sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007975/hb7392Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015007975/hb7392Isup3.cml

checkCIF report


Comment top

The title compound is a carbazole derivative with an amine group and a pyridine group. Carbazole is usually utilized in organic functional materials due to it is a large conjugated system with prominent hole-transporting(Wang et al., 2013). The pyridine group havebeen used as heavy metal sensors (Feng et al., 2013) and the amino groupcan be regulated by acid-base based on intermolecular charge transfer(Park et al., 2015). The title compound might be able to get multiple application fields.

In (I) (Fig.1),

The bond distances of C15—N2 is not equal to the bond distance of C31—N5, which are 1.403 Å and 1.395 Å. The torsion angle of C8–C17—C18–C19 are similiar to C36–C40—C41–C42, but the dihedral angles of the phenyl group and pyridine group is different in the two molecular, which are 18.97° and 45.44°, respectively.

The crystal packing shows that the related molecules are linking by N6···H2D—N2, N5···H16—C16 hydrogen bonds.

Related literature top

For background to the applications of carbazoles, see: Wang et al. (2013); Feng et al. (2013); Park et al. (2015). For further synthetic details, see: Zhang et al. (2014).

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq.

Structure description top

The title compound is a carbazole derivative with an amine group and a pyridine group. Carbazole is usually utilized in organic functional materials due to it is a large conjugated system with prominent hole-transporting(Wang et al., 2013). The pyridine group havebeen used as heavy metal sensors (Feng et al., 2013) and the amino groupcan be regulated by acid-base based on intermolecular charge transfer(Park et al., 2015). The title compound might be able to get multiple application fields.

In (I) (Fig.1),

The bond distances of C15—N2 is not equal to the bond distance of C31—N5, which are 1.403 Å and 1.395 Å. The torsion angle of C8–C17—C18–C19 are similiar to C36–C40—C41–C42, but the dihedral angles of the phenyl group and pyridine group is different in the two molecular, which are 18.97° and 45.44°, respectively.

The crystal packing shows that the related molecules are linking by N6···H2D—N2, N5···H16—C16 hydrogen bonds.

For background to the applications of carbazoles, see: Wang et al. (2013); Feng et al. (2013); Park et al. (2015). For further synthetic details, see: Zhang et al. (2014).

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.
9-Butyl-6-[2-(pyridin-4-yl)ethenyl]carbazol-3-amine top
Crystal data top
C23H23N3F(000) = 1456
Mr = 341.44Dx = 1.209 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.296 (4) ÅCell parameters from 7036 reflections
b = 18.719 (7) Åθ = 2.3–24.3°
c = 17.829 (7) ŵ = 0.07 mm−1
β = 95.362 (5)°T = 296 K
V = 3753 (2) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer		4780 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
ω scansh = −13→12
26552 measured reflectionsk = −20→22
6604 independent reflectionsl = −21→21
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0773P)2 + 0.9436P]
where P = (Fo2 + 2Fc2)/3
6604 reflections(Δ/σ)max < 0.001
471 parametersΔρmax = 0.66 e Å−3
5 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C23H23N3V = 3753 (2) Å3
Mr = 341.44Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.296 (4) ŵ = 0.07 mm−1
b = 18.719 (7) ÅT = 296 K
c = 17.829 (7) Å0.30 × 0.20 × 0.20 mm
β = 95.362 (5)°
Data collection top
Bruker SMART CCD
diffractometer		4780 reflections with I > 2σ(I)
26552 measured reflectionsRint = 0.029
6604 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0535 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 1.14Δρmax = 0.66 e Å−3
6604 reflectionsΔρmin = −0.28 e Å−3
471 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
C80.1402 (2)0.18126 (11)0.33640 (12)0.0506 (5)
C100.07484 (18)0.28290 (11)0.26009 (11)0.0439 (5)
C110.06577 (18)0.33974 (11)0.20495 (11)0.0434 (5)
C180.3040 (2)0.09517 (12)0.31670 (12)0.0526 (6)
H180.31480.11760.27130.063*
C170.2208 (2)0.12164 (12)0.35622 (13)0.0526 (5)
H170.21250.09970.40220.063*
C12−0.04171 (18)0.37514 (11)0.21275 (11)0.0457 (5)
C160.14005 (19)0.36372 (11)0.15188 (12)0.0471 (5)
H160.21160.34050.14650.057*
C150.10675 (19)0.42226 (11)0.10720 (12)0.0470 (5)
C5−0.02863 (19)0.28735 (11)0.29917 (12)0.0488 (5)
C90.15800 (19)0.22968 (11)0.27827 (12)0.0492 (5)
H90.22520.22600.25210.059*
C190.38121 (18)0.03355 (11)0.33784 (12)0.0464 (5)
C70.0385 (2)0.18909 (13)0.37517 (13)0.0577 (6)
H70.02780.15780.41450.069*
C13−0.0760 (2)0.43368 (12)0.16804 (13)0.0526 (5)
H13−0.14740.45710.17320.063*
C200.3807 (2)−0.00335 (13)0.40535 (13)0.0559 (6)
H200.32870.01020.44030.067*
C340.5999 (2)1.02101 (12)0.11976 (11)0.0492 (5)
C330.57620 (19)1.09595 (12)0.12853 (12)0.0482 (5)
C14−0.0013 (2)0.45628 (12)0.11577 (12)0.0520 (5)
H14−0.02360.49530.08540.062*
C280.6780 (2)1.12522 (12)0.16791 (12)0.0525 (5)
C210.4568 (2)−0.05970 (13)0.42064 (14)0.0608 (6)
H210.4538−0.08330.46630.073*
C230.4605 (2)0.00853 (13)0.28947 (13)0.0568 (6)
H230.46440.03050.24300.068*
C370.7160 (2)1.00873 (12)0.15361 (12)0.0532 (6)
C350.5315 (2)0.96430 (12)0.09044 (13)0.0554 (6)
H350.45610.97290.06650.066*
C360.5740 (2)0.89555 (13)0.09647 (14)0.0635 (6)
C6−0.0456 (2)0.24026 (13)0.35797 (13)0.0582 (6)
H6−0.11230.24370.38460.070*
C310.4804 (2)1.21038 (13)0.12857 (15)0.0608 (6)
C450.2326 (3)0.66774 (13)−0.00112 (15)0.0666 (7)
H450.17960.6703−0.04420.080*
C4−0.2165 (2)0.36238 (13)0.28986 (14)0.0601 (6)
H4A−0.24990.32220.31500.072*
H4B−0.26730.37150.24390.072*
C320.4770 (2)1.13893 (13)0.10920 (13)0.0557 (6)
H320.40911.11960.08340.067*
C220.5335 (2)−0.04822 (13)0.30896 (15)0.0630 (6)
H220.5850−0.06340.27450.076*
C390.6912 (3)0.88488 (14)0.12855 (15)0.0710 (7)
H390.72130.83860.13110.085*
C260.9762 (2)1.09499 (16)0.16513 (17)0.0767 (8)
H26A1.05321.09880.19390.092*
H26B0.97871.05380.13240.092*
C420.3969 (2)0.71893 (14)0.07683 (16)0.0705 (6)
C270.8826 (2)1.08206 (15)0.21935 (15)0.0713 (7)
H27A0.90451.04000.24930.086*
H27B0.88191.12240.25340.086*
C410.4903 (3)0.77281 (15)0.09790 (17)0.0784 (8)
H410.55410.75930.13170.094*
C400.4888 (3)0.83625 (14)0.07270 (16)0.0747 (7)
H400.42840.84730.03540.090*
C3−0.2190 (2)0.42683 (15)0.33998 (15)0.0681 (7)
H3A−0.18550.46710.31500.082*
H3B−0.30110.43830.34650.082*
C380.7640 (2)0.94025 (13)0.15659 (14)0.0647 (7)
H380.84180.93190.17660.078*
C290.6807 (2)1.19679 (13)0.18829 (14)0.0644 (6)
H290.74801.21640.21460.077*
C460.3153 (3)0.72233 (14)0.01270 (15)0.0739 (7)
H460.31640.7607−0.02030.089*
C300.5828 (2)1.23771 (14)0.16907 (15)0.0659 (7)
H300.58401.28550.18330.079*
C440.3030 (3)0.61135 (15)0.10490 (18)0.0750 (8)
H440.29910.57310.13780.090*
C430.3871 (3)0.66132 (15)0.12302 (17)0.0759 (7)
H430.43810.65660.16680.091*
C2−0.1533 (3)0.41786 (17)0.41516 (16)0.0815 (8)
H2A−0.06910.41360.40930.098*
H2B−0.17870.37390.43750.098*
C250.9563 (3)1.16126 (16)0.11666 (18)0.0816 (8)
H25A0.88371.15520.08370.098*
H25B0.94511.20180.14910.098*
C1−0.1724 (3)0.48013 (19)0.46861 (17)0.0927 (10)
H1A−0.16300.52450.44290.139*
H1B−0.11500.47740.51180.139*
H1C−0.25110.47750.48460.139*
C241.0568 (3)1.1780 (2)0.0689 (2)0.1101 (12)
H24A1.13031.18050.10050.165*
H24B1.04191.22290.04390.165*
H24C1.06201.14100.03200.165*
N20.17911 (18)0.44634 (10)0.05257 (10)0.0597 (5)
H2C0.24480.42470.04660.072*
H2D0.15780.48270.02510.072*
N1−0.09916 (16)0.34248 (10)0.26974 (10)0.0521 (5)
N40.76339 (18)1.07204 (10)0.18222 (11)0.0597 (5)
N30.53538 (18)−0.08319 (11)0.37428 (12)0.0618 (5)
N60.2259 (2)0.61214 (11)0.04444 (13)0.0665 (6)
N50.38357 (19)1.25534 (13)0.11005 (17)0.0895 (8)
H5A0.31991.23870.08600.107*
H5B0.38751.29970.12270.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C80.0577 (14)0.0424 (12)0.0510 (12)−0.0030 (10)0.0014 (10)0.0007 (10)
C100.0447 (12)0.0384 (11)0.0484 (11)−0.0009 (9)0.0029 (9)−0.0021 (9)
C110.0433 (11)0.0396 (11)0.0469 (11)0.0006 (9)0.0023 (9)−0.0047 (9)
C180.0575 (14)0.0531 (13)0.0472 (12)−0.0038 (11)0.0055 (10)0.0053 (10)
C170.0592 (14)0.0469 (12)0.0517 (12)−0.0023 (11)0.0052 (11)0.0043 (10)
C120.0450 (12)0.0457 (12)0.0463 (11)−0.0003 (10)0.0034 (9)−0.0060 (9)
C160.0465 (12)0.0435 (12)0.0521 (12)0.0041 (9)0.0084 (10)−0.0023 (10)
C150.0537 (13)0.0432 (12)0.0442 (11)−0.0033 (10)0.0039 (10)−0.0037 (9)
C50.0495 (12)0.0458 (12)0.0517 (12)−0.0032 (10)0.0082 (10)−0.0044 (10)
C90.0482 (12)0.0468 (12)0.0529 (12)−0.0031 (10)0.0069 (10)−0.0020 (10)
C190.0463 (12)0.0451 (12)0.0477 (12)−0.0054 (9)0.0040 (9)0.0005 (9)
C70.0666 (15)0.0529 (14)0.0554 (13)−0.0031 (12)0.0159 (12)0.0036 (11)
C130.0456 (12)0.0516 (13)0.0602 (13)0.0111 (10)0.0026 (10)−0.0018 (11)
C200.0542 (14)0.0591 (14)0.0556 (13)0.0034 (11)0.0127 (11)0.0019 (11)
C340.0555 (13)0.0504 (13)0.0429 (11)−0.0032 (10)0.0107 (10)0.0069 (10)
C330.0518 (13)0.0491 (13)0.0451 (11)−0.0030 (10)0.0122 (10)0.0058 (9)
C140.0584 (14)0.0448 (12)0.0512 (12)0.0052 (10)−0.0030 (11)0.0024 (10)
C280.0568 (14)0.0522 (13)0.0481 (12)−0.0015 (11)0.0024 (10)0.0037 (10)
C210.0619 (15)0.0604 (15)0.0609 (14)−0.0030 (12)0.0092 (12)0.0149 (12)
C230.0659 (15)0.0548 (14)0.0516 (13)0.0012 (12)0.0158 (11)0.0046 (11)
C370.0654 (15)0.0493 (13)0.0453 (12)−0.0020 (11)0.0068 (10)0.0081 (10)
C350.0597 (14)0.0535 (14)0.0547 (13)−0.0080 (11)0.0152 (11)0.0005 (11)
C360.0759 (16)0.0565 (15)0.0606 (14)−0.0040 (12)0.0200 (12)0.0012 (11)
C60.0616 (15)0.0543 (14)0.0615 (14)0.0003 (12)0.0206 (12)0.0030 (11)
C310.0526 (14)0.0551 (15)0.0768 (16)0.0021 (11)0.0180 (12)−0.0005 (12)
C450.0809 (18)0.0550 (15)0.0648 (15)0.0013 (13)0.0117 (13)−0.0078 (13)
C40.0469 (13)0.0658 (15)0.0693 (15)0.0013 (11)0.0150 (11)−0.0054 (12)
C320.0472 (13)0.0582 (15)0.0630 (14)−0.0043 (11)0.0116 (11)0.0018 (11)
C220.0651 (15)0.0582 (15)0.0689 (16)0.0053 (12)0.0229 (12)0.0004 (12)
C390.097 (2)0.0438 (14)0.0740 (17)0.0070 (14)0.0186 (15)0.0115 (12)
C260.0597 (16)0.081 (2)0.0854 (19)−0.0030 (14)−0.0156 (14)−0.0105 (16)
C420.0752 (16)0.0636 (15)0.0761 (15)−0.0041 (12)0.0255 (12)−0.0201 (11)
C270.0724 (17)0.0723 (17)0.0637 (16)0.0049 (14)−0.0221 (14)−0.0032 (13)
C410.0883 (19)0.0602 (17)0.0870 (19)0.0006 (13)0.0085 (16)0.0007 (14)
C400.100 (2)0.0579 (16)0.0699 (17)−0.0029 (13)0.0281 (15)−0.0027 (13)
C30.0584 (15)0.0798 (18)0.0683 (16)0.0086 (13)0.0166 (12)−0.0035 (13)
C380.0719 (16)0.0569 (15)0.0645 (15)0.0077 (13)0.0023 (13)0.0149 (12)
C290.0673 (16)0.0580 (15)0.0661 (15)−0.0050 (13)−0.0032 (12)−0.0074 (12)
C460.104 (2)0.0522 (15)0.0692 (15)−0.0013 (15)0.0285 (13)0.0020 (13)
C300.0719 (17)0.0514 (14)0.0755 (17)−0.0023 (13)0.0124 (14)−0.0075 (12)
C440.085 (2)0.0575 (16)0.083 (2)0.0022 (15)0.0112 (17)0.0012 (14)
C430.0782 (18)0.0707 (17)0.0793 (18)0.0019 (15)0.0096 (15)−0.0049 (13)
C20.0763 (19)0.093 (2)0.0745 (18)0.0062 (16)0.0033 (15)−0.0016 (16)
C250.080 (2)0.0744 (19)0.087 (2)−0.0147 (15)−0.0064 (16)−0.0077 (16)
C10.086 (2)0.121 (3)0.0722 (18)−0.0024 (19)0.0110 (16)−0.0261 (18)
C240.106 (3)0.107 (3)0.118 (3)−0.028 (2)0.015 (2)0.000 (2)
N20.0712 (13)0.0541 (11)0.0558 (11)0.0035 (10)0.0176 (10)0.0101 (9)
N10.0462 (10)0.0529 (11)0.0588 (11)0.0045 (9)0.0130 (9)0.0007 (9)
N40.0630 (12)0.0545 (12)0.0589 (12)0.0016 (10)−0.0094 (10)0.0037 (9)
N30.0599 (12)0.0514 (12)0.0753 (14)0.0026 (9)0.0130 (11)0.0063 (10)
N60.0704 (14)0.0531 (13)0.0771 (15)−0.0013 (10)0.0119 (12)−0.0038 (11)
N50.0544 (13)0.0635 (14)0.151 (2)0.0097 (11)0.0119 (14)−0.0127 (15)
Geometric parameters (Å, º) top
C8—C71.403 (3)C45—C461.391 (4)
C8—C91.405 (3)C45—H450.9300
C8—C171.462 (3)C4—N11.454 (3)
C10—C91.387 (3)C4—C31.503 (3)
C10—C51.418 (3)C4—H4A0.9700
C10—C111.446 (3)C4—H4B0.9700
C11—C161.396 (3)C32—H320.9300
C11—C121.401 (3)C22—N31.334 (3)
C18—C171.323 (3)C22—H220.9300
C18—C191.474 (3)C39—C381.387 (4)
C18—H180.9300C39—H390.9300
C17—H170.9300C26—C251.517 (4)
C12—C131.389 (3)C26—C271.517 (4)
C12—N11.397 (3)C26—H26A0.9700
C16—C151.386 (3)C26—H26B0.9700
C16—H160.9300C42—C431.368 (4)
C15—C141.398 (3)C42—C461.402 (4)
C15—N21.403 (3)C42—C411.482 (4)
C5—N11.377 (3)C27—N41.456 (3)
C5—C61.396 (3)C27—H27A0.9700
C9—H90.9300C27—H27B0.9700
C19—C231.382 (3)C41—C401.269 (4)
C19—C201.388 (3)C41—H410.9300
C7—C61.363 (3)C40—H400.9300
C7—H70.9300C3—C21.480 (4)
C13—C141.380 (3)C3—H3A0.9700
C13—H130.9300C3—H3B0.9700
C20—C211.372 (3)C38—H380.9300
C20—H200.9300C29—C301.362 (4)
C34—C351.386 (3)C29—H290.9300
C34—C371.410 (3)C46—H460.9300
C34—C331.439 (3)C30—H300.9300
C33—C321.396 (3)C44—N61.321 (4)
C33—C281.402 (3)C44—C431.350 (4)
C14—H140.9300C44—H440.9300
C28—C291.388 (3)C43—H430.9300
C28—N41.393 (3)C2—C11.534 (4)
C21—N31.342 (3)C2—H2A0.9700
C21—H210.9300C2—H2B0.9700
C23—C221.369 (3)C25—C241.514 (5)
C23—H230.9300C25—H25A0.9700
C37—N41.378 (3)C25—H25B0.9700
C37—C381.391 (3)C1—H1A0.9600
C35—C361.374 (3)C1—H1B0.9600
C35—H350.9300C1—H1C0.9600
C36—C391.407 (4)C24—H24A0.9600
C36—C401.503 (4)C24—H24B0.9600
C6—H60.9300C24—H24C0.9600
C31—C321.381 (3)N2—H2C0.8600
C31—N51.395 (3)N2—H2D0.8600
C31—C301.402 (4)N5—H5A0.8600
C45—N61.327 (3)N5—H5B0.8600
C7—C8—C9118.4 (2)N3—C22—H22117.9
C7—C8—C17118.7 (2)C23—C22—H22117.9
C9—C8—C17122.8 (2)C38—C39—C36123.0 (2)
C9—C10—C5119.92 (19)C38—C39—H39118.5
C9—C10—C11133.71 (19)C36—C39—H39118.5
C5—C10—C11106.36 (18)C25—C26—C27114.7 (2)
C16—C11—C12119.76 (19)C25—C26—H26A108.6
C16—C11—C10133.52 (19)C27—C26—H26A108.6
C12—C11—C10106.71 (18)C25—C26—H26B108.6
C17—C18—C19126.2 (2)C27—C26—H26B108.6
C17—C18—H18116.9H26A—C26—H26B107.6
C19—C18—H18116.9C43—C42—C46116.3 (3)
C18—C17—C8127.9 (2)C43—C42—C41118.7 (3)
C18—C17—H17116.0C46—C42—C41125.1 (3)
C8—C17—H17116.0N4—C27—C26113.6 (2)
C13—C12—N1129.8 (2)N4—C27—H27A108.8
C13—C12—C11120.9 (2)C26—C27—H27A108.8
N1—C12—C11109.33 (18)N4—C27—H27B108.8
C15—C16—C11119.7 (2)C26—C27—H27B108.8
C15—C16—H16120.1H27A—C27—H27B107.7
C11—C16—H16120.1C40—C41—C42124.1 (3)
C16—C15—C14119.4 (2)C40—C41—H41117.9
C16—C15—N2120.6 (2)C42—C41—H41117.9
C14—C15—N2120.1 (2)C41—C40—C36127.2 (3)
N1—C5—C6130.1 (2)C41—C40—H40116.4
N1—C5—C10109.32 (18)C36—C40—H40116.4
C6—C5—C10120.6 (2)C2—C3—C4114.3 (2)
C10—C9—C8119.7 (2)C2—C3—H3A108.7
C10—C9—H9120.2C4—C3—H3A108.7
C8—C9—H9120.2C2—C3—H3B108.7
C23—C19—C20115.3 (2)C4—C3—H3B108.7
C23—C19—C18120.56 (19)H3A—C3—H3B107.6
C20—C19—C18124.1 (2)C39—C38—C37117.3 (2)
C6—C7—C8123.2 (2)C39—C38—H38121.3
C6—C7—H7118.4C37—C38—H38121.3
C8—C7—H7118.4C30—C29—C28118.7 (2)
C14—C13—C12118.3 (2)C30—C29—H29120.7
C14—C13—H13120.8C28—C29—H29120.7
C12—C13—H13120.8C45—C46—C42119.4 (3)
C21—C20—C19120.1 (2)C45—C46—H46120.3
C21—C20—H20119.9C42—C46—H46120.3
C19—C20—H20119.9C29—C30—C31122.4 (2)
C35—C34—C37120.0 (2)C29—C30—H30118.8
C35—C34—C33133.2 (2)C31—C30—H30118.8
C37—C34—C33106.7 (2)N6—C44—C43125.6 (3)
C32—C33—C28120.0 (2)N6—C44—H44117.2
C32—C33—C34133.5 (2)C43—C44—H44117.2
C28—C33—C34106.4 (2)C44—C43—C42119.8 (3)
C13—C14—C15121.9 (2)C44—C43—H43120.1
C13—C14—H14119.0C42—C43—H43120.1
C15—C14—H14119.0C3—C2—C1112.9 (3)
C29—C28—N4130.1 (2)C3—C2—H2A109.0
C29—C28—C33120.4 (2)C1—C2—H2A109.0
N4—C28—C33109.5 (2)C3—C2—H2B109.0
N3—C21—C20124.6 (2)C1—C2—H2B109.0
N3—C21—H21117.7H2A—C2—H2B107.8
C20—C21—H21117.7C24—C25—C26114.2 (3)
C22—C23—C19121.0 (2)C24—C25—H25A108.7
C22—C23—H23119.5C26—C25—H25A108.7
C19—C23—H23119.5C24—C25—H25B108.7
N4—C37—C38129.9 (2)C26—C25—H25B108.7
N4—C37—C34109.4 (2)H25A—C25—H25B107.6
C38—C37—C34120.7 (2)C2—C1—H1A109.5
C36—C35—C34120.6 (2)C2—C1—H1B109.5
C36—C35—H35119.7H1A—C1—H1B109.5
C34—C35—H35119.7C2—C1—H1C109.5
C35—C36—C39118.2 (2)H1A—C1—H1C109.5
C35—C36—C40117.4 (2)H1B—C1—H1C109.5
C39—C36—C40124.3 (2)C25—C24—H24A109.5
C7—C6—C5118.1 (2)C25—C24—H24B109.5
C7—C6—H6120.9H24A—C24—H24B109.5
C5—C6—H6120.9C25—C24—H24C109.5
C32—C31—N5121.5 (2)H24A—C24—H24C109.5
C32—C31—C30119.0 (2)H24B—C24—H24C109.5
N5—C31—C30119.5 (2)C15—N2—H2C120.0
N6—C45—C46122.9 (3)C15—N2—H2D120.0
N6—C45—H45118.5H2C—N2—H2D120.0
C46—C45—H45118.5C5—N1—C12108.27 (17)
N1—C4—C3114.8 (2)C5—N1—C4127.33 (19)
N1—C4—H4A108.6C12—N1—C4124.32 (19)
C3—C4—H4A108.6C37—N4—C28107.96 (19)
N1—C4—H4B108.6C37—N4—C27126.1 (2)
C3—C4—H4B108.6C28—N4—C27125.9 (2)
H4A—C4—H4B107.5C22—N3—C21114.8 (2)
C31—C32—C33119.6 (2)C44—N6—C45115.9 (2)
C31—C32—H32120.2C31—N5—H5A120.0
C33—C32—H32120.2C31—N5—H5B120.0
N3—C22—C23124.2 (2)H5A—N5—H5B120.0
C9—C10—C11—C16−3.2 (4)C10—C5—C6—C7−1.7 (3)
C5—C10—C11—C16178.0 (2)N5—C31—C32—C33179.7 (2)
C9—C10—C11—C12178.4 (2)C30—C31—C32—C33−1.6 (3)
C5—C10—C11—C12−0.4 (2)C28—C33—C32—C310.5 (3)
C19—C18—C17—C8−178.2 (2)C34—C33—C32—C31177.2 (2)
C7—C8—C17—C18163.1 (2)C19—C23—C22—N3−0.4 (4)
C9—C8—C17—C18−14.6 (4)C35—C36—C39—C382.3 (4)
C16—C11—C12—C130.4 (3)C40—C36—C39—C38−173.6 (2)
C10—C11—C12—C13179.04 (19)C25—C26—C27—N461.0 (3)
C16—C11—C12—N1−178.96 (18)C43—C42—C41—C40−160.0 (3)
C10—C11—C12—N1−0.3 (2)C46—C42—C41—C4019.3 (4)
C12—C11—C16—C15−0.2 (3)C42—C41—C40—C36174.1 (2)
C10—C11—C16—C15−178.4 (2)C35—C36—C40—C41−151.0 (3)
C11—C16—C15—C14−0.3 (3)C39—C36—C40—C4124.9 (4)
C11—C16—C15—N2−178.79 (19)N1—C4—C3—C2−63.4 (3)
C9—C10—C5—N1−177.99 (18)C36—C39—C38—C371.4 (4)
C11—C10—C5—N11.0 (2)N4—C37—C38—C39174.3 (2)
C9—C10—C5—C62.5 (3)C34—C37—C38—C39−3.2 (3)
C11—C10—C5—C6−178.5 (2)N4—C28—C29—C30−178.0 (2)
C5—C10—C9—C8−1.2 (3)C33—C28—C29—C30−0.2 (4)
C11—C10—C9—C8−179.9 (2)N6—C45—C46—C420.8 (4)
C7—C8—C9—C10−0.8 (3)C43—C42—C46—C45−1.4 (4)
C17—C8—C9—C10176.8 (2)C41—C42—C46—C45179.3 (2)
C17—C18—C19—C23176.3 (2)C28—C29—C30—C31−0.9 (4)
C17—C18—C19—C20−3.5 (4)C32—C31—C30—C291.8 (4)
C9—C8—C7—C61.7 (3)N5—C31—C30—C29−179.4 (3)
C17—C8—C7—C6−176.0 (2)N6—C44—C43—C420.1 (4)
N1—C12—C13—C14179.1 (2)C46—C42—C43—C440.9 (4)
C11—C12—C13—C14−0.1 (3)C41—C42—C43—C44−179.7 (3)
C23—C19—C20—C210.9 (3)C4—C3—C2—C1−171.7 (2)
C18—C19—C20—C21−179.3 (2)C27—C26—C25—C24173.8 (3)
C35—C34—C33—C32−1.8 (4)C6—C5—N1—C12178.2 (2)
C37—C34—C33—C32−177.7 (2)C10—C5—N1—C12−1.2 (2)
C35—C34—C33—C28175.2 (2)C6—C5—N1—C4−5.0 (4)
C37—C34—C33—C28−0.7 (2)C10—C5—N1—C4175.5 (2)
C12—C13—C14—C15−0.3 (3)C13—C12—N1—C5−178.3 (2)
C16—C15—C14—C130.5 (3)C11—C12—N1—C50.9 (2)
N2—C15—C14—C13179.1 (2)C13—C12—N1—C44.8 (4)
C32—C33—C28—C290.4 (3)C11—C12—N1—C4−175.9 (2)
C34—C33—C28—C29−177.1 (2)C3—C4—N1—C5103.0 (3)
C32—C33—C28—N4178.61 (19)C3—C4—N1—C12−80.8 (3)
C34—C33—C28—N41.2 (2)C38—C37—N4—C28−176.9 (2)
C19—C20—C21—N30.3 (4)C34—C37—N4—C280.7 (2)
C20—C19—C23—C22−0.9 (3)C38—C37—N4—C274.4 (4)
C18—C19—C23—C22179.3 (2)C34—C37—N4—C27−178.0 (2)
C35—C34—C37—N4−176.53 (19)C29—C28—N4—C37176.8 (2)
C33—C34—C37—N40.0 (2)C33—C28—N4—C37−1.2 (2)
C35—C34—C37—C381.4 (3)C29—C28—N4—C27−4.5 (4)
C33—C34—C37—C38177.9 (2)C33—C28—N4—C27177.5 (2)
C37—C34—C35—C362.4 (3)C26—C27—N4—C3784.9 (3)
C33—C34—C35—C36−173.0 (2)C26—C27—N4—C28−93.6 (3)
C34—C35—C36—C39−4.2 (3)C23—C22—N3—C211.6 (4)
C34—C35—C36—C40172.0 (2)C20—C21—N3—C22−1.5 (4)
C8—C7—C6—C5−0.5 (4)C43—C44—N6—C45−0.7 (4)
N1—C5—C6—C7179.0 (2)C46—C45—N6—C440.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2D···N60.862.563.154 (3)128
N5—H5B···N3i0.862.363.163 (3)156
Symmetry code: (i) −x+1, y+3/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2D···N60.862.563.154 (3)128
N5—H5B···N3i0.862.363.163 (3)156
Symmetry code: (i) −x+1, y+3/2, −z+1/2.
 

Acknowledgements

We gratefully acknowledge the Natural Science Foundation of Anhui Province (grant No. 1508085QB41) for supporting this study.

References

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 First citationFeng, X. J., Tian, P. Z., Xu, Z., Chen, S. F. & Wong, M. S. (2013). J. Org. Chem. 78, 11318–11325.  CrossRef CAS PubMed Google Scholar
 First citationPark, Y. I., Postupna, O., Zhugayevych, A., Shin, H., Park, Y. S., Kim, B., Yen, H. J., Cheruku, P., Martinez, J. S., Park, J. W., Tretiak, S. & Wang, H. L. (2015). Chem. Sci. 6, 789–797.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, H. W., Chen, Y., Ye, W. B., Xu, J. K., Liu, D. F., Yang, J. X., Kong, L., Zhou, H. P., Tian, Y. P. & Tao, X. T. (2013). Dyes Pigments, 96, 738–747.  CSD CrossRef CAS Google Scholar
 First citationZhang, P., Liu, J., Huang, J. Y. & Yang, J. X. (2014). Chin. J. Appl. Chem. 31, 1171–1176.  CAS Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 71| Part 5| May 2015| Pages o345-o346
https://doi.org/10.1107/S2056989015007975
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