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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4-Ethynyl-N,N-di­phenyl­aniline

aCollege of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053, People's Republic of China
*Correspondence e-mail: wqwang2008@163.com

(Received 16 October 2013; accepted 22 October 2013; online 31 October 2013)

The asymmetric unit of the title compound, C20H15N, comprises two crystallographically independent mol­ecules (A and B). In each mol­ecule, the N atom adopts an approximately trigonal planar geometry, lying 0.009 (1) or 0.003 (1) Å from the plane defined by the C atoms of the aromatic substituents to which it is attached. In the crystal, mol­ecules are linked via C—H⋯π inter­actions, forming a three-dimensional structure.

Related literature

For the synthesis and applications of the title compound, see: Onitsuka et al. (2006[Onitsuka, K., Ohara, N., Takei, F. & Takahashi, S. (2006). Dalton Trans. pp. 3693-3698.]); Li et al. (2012[Li, Q. T., Guo, H. M., Ma, L. H., Wu, W. H., Liu, Y. F. & Zhao, J. Z. (2012). J. Mater. Chem. 22, 5319-5329.]). For the crystal structures of related compounds, see: Zhang et al. (2012[Zhang, Z.-W., Liu, Y.-Q., Zhu, Y.-C. & Wu, J.-Y. (2012). Acta Cryst. E68, o1933.]); Narayanan et al. (2012[Narayanan, P., Sethusankar, K., Nandakumar, M. & Mohanakrishnan, A. K. (2012). Acta Cryst. E68, o2035.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15N

  • Mr = 269.33

  • Orthorhombic, P c a 21

  • a = 9.0532 (8) Å

  • b = 16.8067 (15) Å

  • c = 19.2508 (18) Å

  • V = 2929.1 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.10 × 0.10 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.993, Tmax = 0.999

  • 29115 measured reflections

  • 8489 independent reflections

  • 8095 reflections with I > 2σ(I)

  • Rint = 0.103

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.02

  • 8489 reflections

  • 379 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C1–C6, C15–C21, C21–C26, C29–C34 and C35–C40 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯Cg6 0.95 2.80 3.5375 (12) 136
C8—H8⋯Cg3i 0.95 2.66 3.5938 (15) 166
C12—H12⋯Cg5ii 0.95 2.77 3.6064 (15) 148
C20—H20⋯Cg4iii 0.95 2.72 3.5647 (12) 148
C28—H28⋯Cg5iv 0.95 2.92 3.5494 (17) 124
C34—H34⋯Cg1 0.95 2.88 3.6659 (13) 141
Symmetry codes: (i) [-x+2, -y, z+{\script{1\over 2}}]; (ii) [-x+{\script{5\over 2}}, y, z-{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]; (iv) [-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2001[Bruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound is an important intermediate in the synthesis of conjugated compounds used in materials chemistry (Li et al., 2012). It has also been used as a bridging ligand in supramolecular chemistry (Onitsuka et al., 2006). We herein report on its crystal structure.

The asymmetric unit of the title compound comprises two crystallographically independent molecules (A and B), as shown in Fig. 1. Its structure is analogous to that of 4-(2-Benzoylbenzoyl)-N,N-diphenylaniline (Narayanan et al., 2012), and 4-(4-Nitrostyryl)-N,N-diphenylaniline (Zhang et al., 2012). The distance between the two N atoms, N1 and N2, in the asymmetric unit is 5.973 (2) Å. The N atoms adopt approximate trigonal-planar geometry; in molecule A atom N1 lies 0.009 (1) Å out of the plane defined by atoms C1/C9/C15, while in molecule B atom N2 lies 0.003 (1) Å out of the plane defined by atoms C21/C29/C35.

In the crystal, molecules are linked by weak C—H···π interactions (Table 1) forming a three-dimensional structure.

Related literature top

For the synthesis and applications of the title compound, see: Onitsuka et al. (2006); Li et al. (2012). For the crystal structures of related compounds, see: Zhang et al. (2012); Narayanan et al. (2012).

Experimental top

The title compound was synthesized according to the literature procedure (Onitsuka et al., 2006). Yellow block-like crystals suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of a solution in hexane-ethanol (6:1).

Refinement top

All the H atoms were positioned geometrically and refined as riding: C-H = 0.95 Å with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 two independent molecules (A and B) of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.
4-Ethynyl-N,N-diphenylaniline top
Crystal data top
C20H15NF(000) = 1136
Mr = 269.33Dx = 1.221 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 9954 reflections
a = 9.0532 (8) Åθ = 2.4–32.0°
b = 16.8067 (15) ŵ = 0.07 mm1
c = 19.2508 (18) ÅT = 100 K
V = 2929.1 (5) Å3Block, yellow
Z = 80.10 × 0.10 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
8489 independent reflections
Radiation source: fine-focus sealed tube8095 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.103
ϕ and ω scansθmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.993, Tmax = 0.999k = 2023
29115 measured reflectionsl = 2627
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0869P)2 + 0.0915P]
where P = (Fo2 + 2Fc2)/3
8489 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.52 e Å3
1 restraintΔρmin = 0.30 e Å3
Crystal data top
C20H15NV = 2929.1 (5) Å3
Mr = 269.33Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 9.0532 (8) ŵ = 0.07 mm1
b = 16.8067 (15) ÅT = 100 K
c = 19.2508 (18) Å0.10 × 0.10 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
8489 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
8095 reflections with I > 2σ(I)
Tmin = 0.993, Tmax = 0.999Rint = 0.103
29115 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.121H-atom parameters constrained
S = 1.02Δρmax = 0.52 e Å3
8489 reflectionsΔρmin = 0.30 e Å3
379 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
N10.97215 (10)0.15515 (6)0.18829 (5)0.0151 (2)
C11.01994 (11)0.12696 (6)0.25330 (6)0.0131 (3)
C20.92032 (11)0.11708 (6)0.30842 (6)0.0154 (3)
C30.96683 (12)0.08555 (7)0.37137 (6)0.0161 (3)
C41.11491 (12)0.06340 (6)0.38145 (6)0.0161 (3)
C51.21537 (12)0.07606 (7)0.32717 (6)0.0161 (3)
C61.16903 (11)0.10742 (6)0.26407 (6)0.0145 (3)
C71.16134 (13)0.02747 (7)0.44568 (6)0.0195 (3)
C81.19981 (16)0.00400 (9)0.49830 (7)0.0265 (3)
C91.07362 (11)0.19681 (7)0.14450 (6)0.0149 (3)
C101.15056 (13)0.26243 (7)0.16999 (6)0.0184 (3)
C111.24849 (14)0.30312 (7)0.12685 (7)0.0227 (3)
C121.26630 (12)0.27978 (8)0.05795 (7)0.0222 (3)
C131.18980 (13)0.21450 (8)0.03265 (7)0.0214 (3)
C141.09451 (12)0.17223 (7)0.07592 (6)0.0185 (3)
C150.82610 (11)0.14234 (6)0.16355 (6)0.0132 (3)
C160.74983 (13)0.07233 (6)0.17946 (6)0.0156 (3)
C170.60599 (12)0.06106 (7)0.15513 (6)0.0181 (3)
C180.53783 (12)0.11803 (8)0.11378 (6)0.0195 (3)
C190.61546 (12)0.18698 (7)0.09708 (7)0.0196 (3)
C200.75783 (12)0.19974 (6)0.12192 (6)0.0164 (3)
N20.82287 (10)0.34489 (6)0.44105 (5)0.0163 (3)
C210.76463 (12)0.37345 (6)0.50402 (6)0.0144 (3)
C220.61135 (12)0.38236 (7)0.51185 (6)0.0162 (3)
C230.55195 (12)0.40957 (7)0.57389 (6)0.0176 (3)
C240.64336 (13)0.42858 (7)0.63045 (6)0.0192 (3)
C250.79684 (13)0.42029 (7)0.62215 (6)0.0185 (3)
C260.85630 (12)0.39351 (7)0.56026 (6)0.0174 (3)
C270.58063 (15)0.45285 (8)0.69544 (7)0.0249 (3)
C280.52423 (19)0.47117 (11)0.74931 (8)0.0366 (4)
C290.97123 (11)0.35937 (6)0.41982 (6)0.0146 (3)
C301.03888 (11)0.43314 (7)0.43085 (6)0.0155 (3)
C311.18418 (12)0.44555 (7)0.40952 (7)0.0196 (3)
C321.26298 (13)0.38519 (8)0.37653 (7)0.0217 (3)
C331.19565 (13)0.31226 (8)0.36518 (7)0.0216 (3)
C341.05057 (13)0.29914 (7)0.38670 (7)0.0187 (3)
C350.73086 (11)0.29881 (7)0.39602 (6)0.0155 (3)
C360.66127 (13)0.23020 (7)0.42044 (6)0.0178 (3)
C370.56952 (13)0.18673 (7)0.37672 (7)0.0216 (3)
C380.54757 (13)0.21097 (8)0.30816 (7)0.0221 (3)
C390.61849 (13)0.27850 (8)0.28360 (7)0.0224 (3)
C400.70958 (13)0.32294 (7)0.32706 (7)0.0197 (3)
H20.819900.132100.302600.0180*
H30.897700.078900.408100.0190*
H51.316500.063000.333600.0190*
H61.238700.115700.227900.0170*
H81.230400.029000.540100.0320*
H101.136300.279400.216600.0220*
H111.303200.346900.144500.0270*
H121.330900.308600.028300.0270*
H131.202300.198500.014300.0260*
H141.043900.126800.058800.0220*
H160.795900.032400.206800.0190*
H170.554100.013800.167000.0220*
H180.440100.110100.097200.0230*
H190.570400.225900.068300.0240*
H200.808700.247500.110600.0200*
H220.547600.369600.474300.0190*
H230.448000.415400.578200.0210*
H250.860700.433300.659600.0220*
H260.960400.388600.555700.0210*
H280.479400.485700.792100.0440*
H300.985700.474800.452900.0190*
H311.229900.495600.417500.0230*
H321.361900.393900.362000.0260*
H331.248700.270900.342600.0260*
H341.005500.248900.378800.0220*
H360.676600.213200.466900.0210*
H370.521500.140300.393600.0260*
H380.484300.181400.278400.0270*
H390.604800.294600.236700.0270*
H400.757100.369400.310000.0240*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0120 (4)0.0179 (4)0.0153 (4)0.0025 (3)0.0018 (3)0.0052 (3)
C10.0138 (4)0.0115 (4)0.0139 (5)0.0012 (3)0.0011 (3)0.0007 (3)
C20.0141 (4)0.0158 (5)0.0162 (5)0.0006 (3)0.0002 (4)0.0007 (4)
C30.0178 (4)0.0153 (4)0.0151 (5)0.0001 (4)0.0003 (4)0.0005 (4)
C40.0194 (5)0.0123 (4)0.0167 (5)0.0002 (3)0.0025 (4)0.0002 (4)
C50.0160 (4)0.0148 (5)0.0174 (5)0.0001 (4)0.0023 (4)0.0006 (4)
C60.0132 (4)0.0136 (4)0.0166 (5)0.0007 (4)0.0003 (3)0.0010 (4)
C70.0234 (5)0.0188 (5)0.0163 (5)0.0022 (4)0.0006 (4)0.0006 (4)
C80.0326 (6)0.0287 (6)0.0181 (5)0.0082 (5)0.0011 (5)0.0017 (5)
C90.0126 (4)0.0158 (5)0.0164 (5)0.0008 (4)0.0003 (4)0.0039 (4)
C100.0203 (5)0.0181 (5)0.0167 (5)0.0030 (4)0.0020 (4)0.0029 (4)
C110.0191 (5)0.0214 (5)0.0276 (6)0.0058 (4)0.0035 (4)0.0063 (5)
C120.0137 (4)0.0269 (6)0.0259 (6)0.0021 (4)0.0023 (4)0.0101 (5)
C130.0182 (5)0.0277 (6)0.0184 (5)0.0014 (4)0.0034 (4)0.0029 (5)
C140.0165 (4)0.0197 (5)0.0192 (5)0.0016 (4)0.0013 (4)0.0009 (4)
C150.0115 (4)0.0148 (5)0.0134 (5)0.0001 (3)0.0001 (3)0.0003 (4)
C160.0158 (4)0.0151 (5)0.0159 (5)0.0011 (4)0.0005 (4)0.0008 (4)
C170.0164 (5)0.0189 (5)0.0191 (5)0.0046 (4)0.0001 (4)0.0003 (4)
C180.0136 (4)0.0235 (6)0.0214 (6)0.0020 (4)0.0028 (4)0.0004 (4)
C190.0169 (4)0.0207 (5)0.0213 (5)0.0015 (4)0.0025 (4)0.0035 (4)
C200.0156 (4)0.0150 (5)0.0185 (5)0.0001 (4)0.0010 (4)0.0026 (4)
N20.0132 (4)0.0187 (5)0.0169 (4)0.0054 (3)0.0007 (3)0.0042 (3)
C210.0160 (4)0.0117 (4)0.0155 (5)0.0017 (4)0.0005 (4)0.0001 (4)
C220.0153 (4)0.0149 (5)0.0183 (5)0.0006 (4)0.0010 (4)0.0010 (4)
C230.0174 (4)0.0152 (5)0.0202 (5)0.0019 (4)0.0030 (4)0.0025 (4)
C240.0242 (5)0.0155 (5)0.0179 (5)0.0024 (4)0.0016 (4)0.0011 (4)
C250.0213 (5)0.0174 (5)0.0169 (5)0.0002 (4)0.0024 (4)0.0003 (4)
C260.0168 (4)0.0172 (5)0.0181 (5)0.0003 (4)0.0012 (4)0.0000 (4)
C270.0292 (6)0.0262 (6)0.0193 (6)0.0086 (5)0.0002 (5)0.0010 (5)
C280.0411 (8)0.0499 (9)0.0187 (6)0.0187 (7)0.0034 (5)0.0016 (6)
C290.0127 (4)0.0155 (5)0.0155 (5)0.0011 (3)0.0005 (3)0.0002 (4)
C300.0143 (4)0.0139 (5)0.0182 (5)0.0015 (3)0.0000 (4)0.0024 (4)
C310.0158 (4)0.0204 (5)0.0226 (6)0.0050 (4)0.0000 (4)0.0014 (4)
C320.0133 (4)0.0304 (6)0.0214 (6)0.0006 (4)0.0005 (4)0.0038 (5)
C330.0187 (5)0.0241 (6)0.0221 (6)0.0035 (4)0.0012 (4)0.0059 (4)
C340.0195 (5)0.0155 (5)0.0212 (5)0.0010 (4)0.0011 (4)0.0039 (4)
C350.0133 (4)0.0158 (5)0.0173 (5)0.0024 (4)0.0004 (4)0.0030 (4)
C360.0178 (4)0.0175 (5)0.0182 (5)0.0029 (4)0.0008 (4)0.0012 (4)
C370.0163 (4)0.0206 (5)0.0278 (6)0.0059 (4)0.0031 (4)0.0064 (5)
C380.0139 (4)0.0279 (6)0.0246 (6)0.0021 (4)0.0017 (4)0.0103 (5)
C390.0208 (5)0.0287 (6)0.0176 (5)0.0009 (4)0.0026 (4)0.0027 (5)
C400.0201 (5)0.0206 (5)0.0185 (5)0.0021 (4)0.0003 (4)0.0000 (4)
Geometric parameters (Å, º) top
N1—C11.4064 (15)C18—H180.9500
N1—C91.4300 (15)C19—H190.9500
N1—C151.4218 (14)C20—H200.9500
N2—C351.4301 (15)C21—C221.4039 (15)
N2—C211.4064 (15)C21—C261.4052 (16)
N2—C291.4249 (14)C22—C231.3873 (16)
C1—C21.4025 (15)C23—C241.4044 (16)
C1—C61.4045 (14)C24—C251.4056 (17)
C2—C31.3880 (16)C24—C271.4332 (18)
C3—C41.4048 (15)C25—C261.3827 (16)
C4—C71.4388 (16)C27—C281.196 (2)
C4—C51.4015 (16)C29—C301.3991 (15)
C5—C61.3890 (16)C29—C341.3954 (16)
C7—C81.1946 (18)C30—C311.3937 (15)
C9—C141.3962 (16)C31—C321.3933 (18)
C9—C101.3937 (16)C32—C331.3862 (19)
C10—C111.3941 (17)C33—C341.3948 (17)
C11—C121.3925 (19)C35—C361.3956 (16)
C12—C131.3859 (18)C35—C401.4014 (18)
C13—C141.3938 (17)C36—C371.3900 (17)
C15—C201.3982 (15)C37—C381.3955 (19)
C15—C161.3982 (15)C38—C391.3871 (19)
C16—C171.3968 (16)C39—C401.3921 (18)
C17—C181.3897 (17)C22—H220.9500
C18—C191.3929 (17)C23—H230.9500
C19—C201.3914 (16)C25—H250.9500
C2—H20.9500C26—H260.9500
C3—H30.9500C28—H280.9500
C5—H50.9500C30—H300.9500
C6—H60.9500C31—H310.9500
C8—H80.9500C32—H320.9500
C10—H100.9500C33—H330.9500
C11—H110.9500C34—H340.9500
C12—H120.9500C36—H360.9500
C13—H130.9500C37—H370.9500
C14—H140.9500C38—H380.9500
C16—H160.9500C39—H390.9500
C17—H170.9500C40—H400.9500
C1—N1—C9119.47 (9)C20—C19—H19120.00
C1—N1—C15122.22 (9)C15—C20—H20120.00
C9—N1—C15118.30 (9)C19—C20—H20120.00
C21—N2—C29122.84 (9)N2—C21—C22119.97 (10)
C21—N2—C35119.27 (9)N2—C21—C26121.64 (10)
C29—N2—C35117.89 (9)C22—C21—C26118.39 (10)
N1—C1—C2121.02 (9)C21—C22—C23120.71 (10)
N1—C1—C6120.38 (10)C22—C23—C24120.93 (10)
C2—C1—C6118.60 (10)C23—C24—C25118.15 (10)
C1—C2—C3120.71 (9)C23—C24—C27120.53 (11)
C2—C3—C4120.75 (10)C25—C24—C27121.28 (11)
C3—C4—C7120.58 (10)C24—C25—C26121.00 (11)
C3—C4—C5118.43 (10)C21—C26—C25120.80 (10)
C5—C4—C7120.99 (10)C24—C27—C28177.63 (15)
C4—C5—C6120.91 (10)N2—C29—C30121.36 (9)
C1—C6—C5120.54 (10)N2—C29—C34119.50 (9)
C4—C7—C8178.53 (13)C30—C29—C34119.14 (10)
C10—C9—C14119.96 (10)C29—C30—C31120.07 (10)
N1—C9—C14119.97 (10)C30—C31—C32120.57 (11)
N1—C9—C10120.07 (10)C31—C32—C33119.37 (11)
C9—C10—C11119.76 (11)C32—C33—C34120.47 (12)
C10—C11—C12120.19 (11)C29—C34—C33120.38 (11)
C11—C12—C13119.99 (12)N2—C35—C36120.41 (10)
C12—C13—C14120.18 (12)N2—C35—C40119.84 (10)
C9—C14—C13119.88 (11)C36—C35—C40119.75 (10)
C16—C15—C20119.20 (10)C35—C36—C37120.01 (11)
N1—C15—C16120.88 (10)C36—C37—C38120.29 (11)
N1—C15—C20119.91 (9)C37—C38—C39119.69 (12)
C15—C16—C17120.07 (10)C38—C39—C40120.56 (12)
C16—C17—C18120.84 (10)C35—C40—C39119.70 (11)
C17—C18—C19118.78 (10)C21—C22—H22120.00
C18—C19—C20121.09 (11)C23—C22—H22120.00
C15—C20—C19120.01 (10)C22—C23—H23120.00
C1—C2—H2120.00C24—C23—H23120.00
C3—C2—H2120.00C24—C25—H25120.00
C4—C3—H3120.00C26—C25—H25119.00
C2—C3—H3120.00C21—C26—H26120.00
C4—C5—H5120.00C25—C26—H26120.00
C6—C5—H5120.00C27—C28—H28180.00
C1—C6—H6120.00C29—C30—H30120.00
C5—C6—H6120.00C31—C30—H30120.00
C7—C8—H8180.00C30—C31—H31120.00
C11—C10—H10120.00C32—C31—H31120.00
C9—C10—H10120.00C31—C32—H32120.00
C10—C11—H11120.00C33—C32—H32120.00
C12—C11—H11120.00C32—C33—H33120.00
C11—C12—H12120.00C34—C33—H33120.00
C13—C12—H12120.00C29—C34—H34120.00
C14—C13—H13120.00C33—C34—H34120.00
C12—C13—H13120.00C35—C36—H36120.00
C13—C14—H14120.00C37—C36—H36120.00
C9—C14—H14120.00C36—C37—H37120.00
C15—C16—H16120.00C38—C37—H37120.00
C17—C16—H16120.00C37—C38—H38120.00
C16—C17—H17120.00C39—C38—H38120.00
C18—C17—H17120.00C38—C39—H39120.00
C19—C18—H18121.00C40—C39—H39120.00
C17—C18—H18121.00C35—C40—H40120.00
C18—C19—H19119.00C39—C40—H40120.00
C9—N1—C1—C2152.80 (10)C9—C10—C11—C121.86 (18)
C15—N1—C1—C228.48 (15)C10—C11—C12—C131.89 (18)
C9—N1—C1—C627.76 (15)C11—C12—C13—C140.24 (18)
C15—N1—C1—C6150.96 (10)C12—C13—C14—C91.42 (18)
C1—N1—C15—C1634.25 (16)N1—C15—C16—C17179.51 (10)
C9—N1—C15—C16144.49 (11)N1—C15—C20—C19179.36 (11)
C1—N1—C15—C20146.66 (11)C20—C15—C16—C171.39 (17)
C1—N1—C9—C1053.62 (15)C16—C15—C20—C190.25 (17)
C15—N1—C9—C10127.61 (11)C15—C16—C17—C181.37 (17)
C1—N1—C9—C14127.04 (11)C16—C17—C18—C190.19 (17)
C15—N1—C9—C1451.73 (14)C17—C18—C19—C200.97 (18)
C9—N1—C15—C2034.61 (15)C18—C19—C20—C150.94 (18)
C29—N2—C35—C4056.40 (14)N2—C21—C22—C23179.24 (10)
C21—N2—C29—C3039.77 (16)N2—C21—C26—C25178.96 (11)
C29—N2—C21—C22157.71 (10)C22—C21—C26—C250.91 (17)
C21—N2—C35—C40123.98 (11)C26—C21—C22—C230.63 (17)
C29—N2—C21—C2622.42 (16)C21—C22—C23—C240.25 (18)
C35—N2—C21—C26157.17 (10)C22—C23—C24—C27176.87 (12)
C21—N2—C35—C3655.59 (15)C22—C23—C24—C250.84 (17)
C29—N2—C35—C36124.03 (11)C27—C24—C25—C26177.14 (12)
C21—N2—C29—C34140.89 (12)C23—C24—C25—C260.56 (17)
C35—N2—C29—C3438.72 (15)C24—C25—C26—C210.32 (18)
C35—N2—C21—C2222.70 (15)N2—C29—C30—C31180.00 (11)
C35—N2—C29—C30140.63 (11)C34—C29—C30—C310.66 (17)
N1—C1—C6—C5176.97 (10)N2—C29—C34—C33179.65 (11)
C2—C1—C6—C52.48 (15)C30—C29—C34—C330.29 (18)
C6—C1—C2—C32.65 (15)C29—C30—C31—C320.61 (19)
N1—C1—C2—C3176.81 (10)C30—C31—C32—C330.2 (2)
C1—C2—C3—C40.49 (17)C31—C32—C33—C340.2 (2)
C2—C3—C4—C7177.22 (10)C32—C33—C34—C290.1 (2)
C2—C3—C4—C51.85 (16)N2—C35—C36—C37178.62 (10)
C7—C4—C5—C6177.05 (10)C40—C35—C36—C370.95 (17)
C3—C4—C5—C62.01 (16)N2—C35—C40—C39179.21 (10)
C4—C5—C6—C10.16 (17)C36—C35—C40—C390.37 (17)
C10—C9—C14—C131.45 (17)C35—C36—C37—C380.58 (18)
N1—C9—C14—C13177.89 (10)C36—C37—C38—C390.38 (18)
N1—C9—C10—C11179.53 (10)C37—C38—C39—C400.97 (19)
C14—C9—C10—C110.19 (17)C38—C39—C40—C350.60 (18)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C1–C6, C15–C21, C21–C26, C29–C34 and C35–C40 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg60.952.803.5375 (12)136
C8—H8···Cg3i0.952.663.5938 (15)166
C12—H12···Cg5ii0.952.773.6064 (15)148
C20—H20···Cg4iii0.952.723.5647 (12)148
C28—H28···Cg5iv0.952.923.5494 (17)124
C34—H34···Cg10.952.883.6659 (13)141
Symmetry codes: (i) x+2, y, z+1/2; (ii) x+5/2, y, z1/2; (iii) x+3/2, y, z1/2; (iv) x+3/2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg4, Cg5 and Cg6 are the centroids of the C1–C6, C15–C21, C21–C26, C29–C34 and C35–C40 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg60.952.803.5375 (12)136
C8—H8···Cg3i0.952.663.5938 (15)166
C12—H12···Cg5ii0.952.773.6064 (15)148
C20—H20···Cg4iii0.952.723.5647 (12)148
C28—H28···Cg5iv0.952.923.5494 (17)124
C34—H34···Cg10.952.883.6659 (13)141
Symmetry codes: (i) x+2, y, z+1/2; (ii) x+5/2, y, z1/2; (iii) x+3/2, y, z1/2; (iv) x+3/2, y, z+1/2.
 

Acknowledgements

The authors are grateful to Hubei University of Arts and Science for financial support.

References

First citationBruker (2001). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationLi, Q. T., Guo, H. M., Ma, L. H., Wu, W. H., Liu, Y. F. & Zhao, J. Z. (2012). J. Mater. Chem. 22, 5319-5329.  Web of Science CrossRef CAS
First citationNarayanan, P., Sethusankar, K., Nandakumar, M. & Mohanakrishnan, A. K. (2012). Acta Cryst. E68, o2035.  CSD CrossRef IUCr Journals
First citationOnitsuka, K., Ohara, N., Takei, F. & Takahashi, S. (2006). Dalton Trans. pp. 3693–3698.  Web of Science CrossRef
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZhang, Z.-W., Liu, Y.-Q., Zhu, Y.-C. & Wu, J.-Y. (2012). Acta Cryst. E68, o1933.  CSD CrossRef IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds