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organic compounds
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
The 20H15N, 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.
of the title compound, CCCDC reference: 967741
Related literature
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
Crystal data
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|
Data collection: APEX2 (Bruker, 2001); cell SAINT (Bruker, 2001
); data reduction: SAINT; 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.
Supporting information
CCDC reference: 967741
10.1107/S1600536813029036/su2660sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813029036/su2660Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813029036/su2660Isup3.cml
The title compound was synthesized according to the literature procedure (Onitsuka et al., 2006). Yellow block-like crystals suitable for single-crystal X-ray
were grown by slow evaporation of a solution in hexane-ethanol (6:1).All the H atoms were positioned geometrically and refined as riding: C-H = 0.95 Å with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2001); cell
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). ![]() | 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. |
C20H15N | F(000) = 1136 |
Mr = 269.33 | Dx = 1.221 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 9954 reflections |
a = 9.0532 (8) Å | θ = 2.4–32.0° |
b = 16.8067 (15) Å | µ = 0.07 mm−1 |
c = 19.2508 (18) Å | T = 100 K |
V = 2929.1 (5) Å3 | Block, yellow |
Z = 8 | 0.10 × 0.10 × 0.10 mm |
Bruker APEXII CCD diffractometer | 8489 independent reflections |
Radiation source: fine-focus sealed tube | 8095 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.103 |
ϕ and ω scans | θmax = 30.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.993, Tmax = 0.999 | k = −20→23 |
29115 measured reflections | l = −26→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-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 parameters | Δρmax = 0.52 e Å−3 |
1 restraint | Δρmin = −0.30 e Å−3 |
C20H15N | V = 2929.1 (5) Å3 |
Mr = 269.33 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 9.0532 (8) Å | µ = 0.07 mm−1 |
b = 16.8067 (15) Å | T = 100 K |
c = 19.2508 (18) Å | 0.10 × 0.10 × 0.10 mm |
Bruker APEXII CCD diffractometer | 8489 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 8095 reflections with I > 2σ(I) |
Tmin = 0.993, Tmax = 0.999 | Rint = 0.103 |
29115 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 1 restraint |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.52 e Å−3 |
8489 reflections | Δρmin = −0.30 e Å−3 |
379 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.97215 (10) | 0.15515 (6) | 0.18829 (5) | 0.0151 (2) | |
C1 | 1.01994 (11) | 0.12696 (6) | 0.25330 (6) | 0.0131 (3) | |
C2 | 0.92032 (11) | 0.11708 (6) | 0.30842 (6) | 0.0154 (3) | |
C3 | 0.96683 (12) | 0.08555 (7) | 0.37137 (6) | 0.0161 (3) | |
C4 | 1.11491 (12) | 0.06340 (6) | 0.38145 (6) | 0.0161 (3) | |
C5 | 1.21537 (12) | 0.07606 (7) | 0.32717 (6) | 0.0161 (3) | |
C6 | 1.16903 (11) | 0.10742 (6) | 0.26407 (6) | 0.0145 (3) | |
C7 | 1.16134 (13) | 0.02747 (7) | 0.44568 (6) | 0.0195 (3) | |
C8 | 1.19981 (16) | −0.00400 (9) | 0.49830 (7) | 0.0265 (3) | |
C9 | 1.07362 (11) | 0.19681 (7) | 0.14450 (6) | 0.0149 (3) | |
C10 | 1.15056 (13) | 0.26243 (7) | 0.16999 (6) | 0.0184 (3) | |
C11 | 1.24849 (14) | 0.30312 (7) | 0.12685 (7) | 0.0227 (3) | |
C12 | 1.26630 (12) | 0.27978 (8) | 0.05795 (7) | 0.0222 (3) | |
C13 | 1.18980 (13) | 0.21450 (8) | 0.03265 (7) | 0.0214 (3) | |
C14 | 1.09451 (12) | 0.17223 (7) | 0.07592 (6) | 0.0185 (3) | |
C15 | 0.82610 (11) | 0.14234 (6) | 0.16355 (6) | 0.0132 (3) | |
C16 | 0.74983 (13) | 0.07233 (6) | 0.17946 (6) | 0.0156 (3) | |
C17 | 0.60599 (12) | 0.06106 (7) | 0.15513 (6) | 0.0181 (3) | |
C18 | 0.53783 (12) | 0.11803 (8) | 0.11378 (6) | 0.0195 (3) | |
C19 | 0.61546 (12) | 0.18698 (7) | 0.09708 (7) | 0.0196 (3) | |
C20 | 0.75783 (12) | 0.19974 (6) | 0.12192 (6) | 0.0164 (3) | |
N2 | 0.82287 (10) | 0.34489 (6) | 0.44105 (5) | 0.0163 (3) | |
C21 | 0.76463 (12) | 0.37345 (6) | 0.50402 (6) | 0.0144 (3) | |
C22 | 0.61135 (12) | 0.38236 (7) | 0.51185 (6) | 0.0162 (3) | |
C23 | 0.55195 (12) | 0.40957 (7) | 0.57389 (6) | 0.0176 (3) | |
C24 | 0.64336 (13) | 0.42858 (7) | 0.63045 (6) | 0.0192 (3) | |
C25 | 0.79684 (13) | 0.42029 (7) | 0.62215 (6) | 0.0185 (3) | |
C26 | 0.85630 (12) | 0.39351 (7) | 0.56026 (6) | 0.0174 (3) | |
C27 | 0.58063 (15) | 0.45285 (8) | 0.69544 (7) | 0.0249 (3) | |
C28 | 0.52423 (19) | 0.47117 (11) | 0.74931 (8) | 0.0366 (4) | |
C29 | 0.97123 (11) | 0.35937 (6) | 0.41982 (6) | 0.0146 (3) | |
C30 | 1.03888 (11) | 0.43314 (7) | 0.43085 (6) | 0.0155 (3) | |
C31 | 1.18418 (12) | 0.44555 (7) | 0.40952 (7) | 0.0196 (3) | |
C32 | 1.26298 (13) | 0.38519 (8) | 0.37653 (7) | 0.0217 (3) | |
C33 | 1.19565 (13) | 0.31226 (8) | 0.36518 (7) | 0.0216 (3) | |
C34 | 1.05057 (13) | 0.29914 (7) | 0.38670 (7) | 0.0187 (3) | |
C35 | 0.73086 (11) | 0.29881 (7) | 0.39602 (6) | 0.0155 (3) | |
C36 | 0.66127 (13) | 0.23020 (7) | 0.42044 (6) | 0.0178 (3) | |
C37 | 0.56952 (13) | 0.18673 (7) | 0.37672 (7) | 0.0216 (3) | |
C38 | 0.54757 (13) | 0.21097 (8) | 0.30816 (7) | 0.0221 (3) | |
C39 | 0.61849 (13) | 0.27850 (8) | 0.28360 (7) | 0.0224 (3) | |
C40 | 0.70958 (13) | 0.32294 (7) | 0.32706 (7) | 0.0197 (3) | |
H2 | 0.81990 | 0.13210 | 0.30260 | 0.0180* | |
H3 | 0.89770 | 0.07890 | 0.40810 | 0.0190* | |
H5 | 1.31650 | 0.06300 | 0.33360 | 0.0190* | |
H6 | 1.23870 | 0.11570 | 0.22790 | 0.0170* | |
H8 | 1.23040 | −0.02900 | 0.54010 | 0.0320* | |
H10 | 1.13630 | 0.27940 | 0.21660 | 0.0220* | |
H11 | 1.30320 | 0.34690 | 0.14450 | 0.0270* | |
H12 | 1.33090 | 0.30860 | 0.02830 | 0.0270* | |
H13 | 1.20230 | 0.19850 | −0.01430 | 0.0260* | |
H14 | 1.04390 | 0.12680 | 0.05880 | 0.0220* | |
H16 | 0.79590 | 0.03240 | 0.20680 | 0.0190* | |
H17 | 0.55410 | 0.01380 | 0.16700 | 0.0220* | |
H18 | 0.44010 | 0.11010 | 0.09720 | 0.0230* | |
H19 | 0.57040 | 0.22590 | 0.06830 | 0.0240* | |
H20 | 0.80870 | 0.24750 | 0.11060 | 0.0200* | |
H22 | 0.54760 | 0.36960 | 0.47430 | 0.0190* | |
H23 | 0.44800 | 0.41540 | 0.57820 | 0.0210* | |
H25 | 0.86070 | 0.43330 | 0.65960 | 0.0220* | |
H26 | 0.96040 | 0.38860 | 0.55570 | 0.0210* | |
H28 | 0.47940 | 0.48570 | 0.79210 | 0.0440* | |
H30 | 0.98570 | 0.47480 | 0.45290 | 0.0190* | |
H31 | 1.22990 | 0.49560 | 0.41750 | 0.0230* | |
H32 | 1.36190 | 0.39390 | 0.36200 | 0.0260* | |
H33 | 1.24870 | 0.27090 | 0.34260 | 0.0260* | |
H34 | 1.00550 | 0.24890 | 0.37880 | 0.0220* | |
H36 | 0.67660 | 0.21320 | 0.46690 | 0.0210* | |
H37 | 0.52150 | 0.14030 | 0.39360 | 0.0260* | |
H38 | 0.48430 | 0.18140 | 0.27840 | 0.0270* | |
H39 | 0.60480 | 0.29460 | 0.23670 | 0.0270* | |
H40 | 0.75710 | 0.36940 | 0.31000 | 0.0240* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0120 (4) | 0.0179 (4) | 0.0153 (4) | −0.0025 (3) | −0.0018 (3) | 0.0052 (3) |
C1 | 0.0138 (4) | 0.0115 (4) | 0.0139 (5) | −0.0012 (3) | −0.0011 (3) | 0.0007 (3) |
C2 | 0.0141 (4) | 0.0158 (5) | 0.0162 (5) | −0.0006 (3) | −0.0002 (4) | −0.0007 (4) |
C3 | 0.0178 (4) | 0.0153 (4) | 0.0151 (5) | 0.0001 (4) | 0.0003 (4) | −0.0005 (4) |
C4 | 0.0194 (5) | 0.0123 (4) | 0.0167 (5) | −0.0002 (3) | −0.0025 (4) | 0.0002 (4) |
C5 | 0.0160 (4) | 0.0148 (5) | 0.0174 (5) | 0.0001 (4) | −0.0023 (4) | 0.0006 (4) |
C6 | 0.0132 (4) | 0.0136 (4) | 0.0166 (5) | −0.0007 (4) | −0.0003 (3) | 0.0010 (4) |
C7 | 0.0234 (5) | 0.0188 (5) | 0.0163 (5) | 0.0022 (4) | −0.0006 (4) | −0.0006 (4) |
C8 | 0.0326 (6) | 0.0287 (6) | 0.0181 (5) | 0.0082 (5) | −0.0011 (5) | 0.0017 (5) |
C9 | 0.0126 (4) | 0.0158 (5) | 0.0164 (5) | −0.0008 (4) | −0.0003 (4) | 0.0039 (4) |
C10 | 0.0203 (5) | 0.0181 (5) | 0.0167 (5) | −0.0030 (4) | −0.0020 (4) | 0.0029 (4) |
C11 | 0.0191 (5) | 0.0214 (5) | 0.0276 (6) | −0.0058 (4) | −0.0035 (4) | 0.0063 (5) |
C12 | 0.0137 (4) | 0.0269 (6) | 0.0259 (6) | −0.0021 (4) | 0.0023 (4) | 0.0101 (5) |
C13 | 0.0182 (5) | 0.0277 (6) | 0.0184 (5) | 0.0014 (4) | 0.0034 (4) | 0.0029 (5) |
C14 | 0.0165 (4) | 0.0197 (5) | 0.0192 (5) | −0.0016 (4) | 0.0013 (4) | 0.0009 (4) |
C15 | 0.0115 (4) | 0.0148 (5) | 0.0134 (5) | −0.0001 (3) | −0.0001 (3) | 0.0003 (4) |
C16 | 0.0158 (4) | 0.0151 (5) | 0.0159 (5) | −0.0011 (4) | −0.0005 (4) | 0.0008 (4) |
C17 | 0.0164 (5) | 0.0189 (5) | 0.0191 (5) | −0.0046 (4) | −0.0001 (4) | −0.0003 (4) |
C18 | 0.0136 (4) | 0.0235 (6) | 0.0214 (6) | −0.0020 (4) | −0.0028 (4) | −0.0004 (4) |
C19 | 0.0169 (4) | 0.0207 (5) | 0.0213 (5) | 0.0015 (4) | −0.0025 (4) | 0.0035 (4) |
C20 | 0.0156 (4) | 0.0150 (5) | 0.0185 (5) | 0.0001 (4) | −0.0010 (4) | 0.0026 (4) |
N2 | 0.0132 (4) | 0.0187 (5) | 0.0169 (4) | −0.0054 (3) | 0.0007 (3) | −0.0042 (3) |
C21 | 0.0160 (4) | 0.0117 (4) | 0.0155 (5) | −0.0017 (4) | 0.0005 (4) | 0.0001 (4) |
C22 | 0.0153 (4) | 0.0149 (5) | 0.0183 (5) | −0.0006 (4) | −0.0010 (4) | 0.0010 (4) |
C23 | 0.0174 (4) | 0.0152 (5) | 0.0202 (5) | 0.0019 (4) | 0.0030 (4) | 0.0025 (4) |
C24 | 0.0242 (5) | 0.0155 (5) | 0.0179 (5) | 0.0024 (4) | 0.0016 (4) | 0.0011 (4) |
C25 | 0.0213 (5) | 0.0174 (5) | 0.0169 (5) | −0.0002 (4) | −0.0024 (4) | −0.0003 (4) |
C26 | 0.0168 (4) | 0.0172 (5) | 0.0181 (5) | −0.0003 (4) | −0.0012 (4) | 0.0000 (4) |
C27 | 0.0292 (6) | 0.0262 (6) | 0.0193 (6) | 0.0086 (5) | −0.0002 (5) | 0.0010 (5) |
C28 | 0.0411 (8) | 0.0499 (9) | 0.0187 (6) | 0.0187 (7) | 0.0034 (5) | 0.0016 (6) |
C29 | 0.0127 (4) | 0.0155 (5) | 0.0155 (5) | −0.0011 (3) | −0.0005 (3) | −0.0002 (4) |
C30 | 0.0143 (4) | 0.0139 (5) | 0.0182 (5) | −0.0015 (3) | 0.0000 (4) | −0.0024 (4) |
C31 | 0.0158 (4) | 0.0204 (5) | 0.0226 (6) | −0.0050 (4) | 0.0000 (4) | −0.0014 (4) |
C32 | 0.0133 (4) | 0.0304 (6) | 0.0214 (6) | −0.0006 (4) | 0.0005 (4) | −0.0038 (5) |
C33 | 0.0187 (5) | 0.0241 (6) | 0.0221 (6) | 0.0035 (4) | −0.0012 (4) | −0.0059 (4) |
C34 | 0.0195 (5) | 0.0155 (5) | 0.0212 (5) | 0.0010 (4) | −0.0011 (4) | −0.0039 (4) |
C35 | 0.0133 (4) | 0.0158 (5) | 0.0173 (5) | −0.0024 (4) | −0.0004 (4) | −0.0030 (4) |
C36 | 0.0178 (4) | 0.0175 (5) | 0.0182 (5) | −0.0029 (4) | 0.0008 (4) | −0.0012 (4) |
C37 | 0.0163 (4) | 0.0206 (5) | 0.0278 (6) | −0.0059 (4) | 0.0031 (4) | −0.0064 (5) |
C38 | 0.0139 (4) | 0.0279 (6) | 0.0246 (6) | −0.0021 (4) | −0.0017 (4) | −0.0103 (5) |
C39 | 0.0208 (5) | 0.0287 (6) | 0.0176 (5) | 0.0009 (4) | −0.0026 (4) | −0.0027 (5) |
C40 | 0.0201 (5) | 0.0206 (5) | 0.0185 (5) | −0.0021 (4) | −0.0003 (4) | 0.0000 (4) |
N1—C1 | 1.4064 (15) | C18—H18 | 0.9500 |
N1—C9 | 1.4300 (15) | C19—H19 | 0.9500 |
N1—C15 | 1.4218 (14) | C20—H20 | 0.9500 |
N2—C35 | 1.4301 (15) | C21—C22 | 1.4039 (15) |
N2—C21 | 1.4064 (15) | C21—C26 | 1.4052 (16) |
N2—C29 | 1.4249 (14) | C22—C23 | 1.3873 (16) |
C1—C2 | 1.4025 (15) | C23—C24 | 1.4044 (16) |
C1—C6 | 1.4045 (14) | C24—C25 | 1.4056 (17) |
C2—C3 | 1.3880 (16) | C24—C27 | 1.4332 (18) |
C3—C4 | 1.4048 (15) | C25—C26 | 1.3827 (16) |
C4—C7 | 1.4388 (16) | C27—C28 | 1.196 (2) |
C4—C5 | 1.4015 (16) | C29—C30 | 1.3991 (15) |
C5—C6 | 1.3890 (16) | C29—C34 | 1.3954 (16) |
C7—C8 | 1.1946 (18) | C30—C31 | 1.3937 (15) |
C9—C14 | 1.3962 (16) | C31—C32 | 1.3933 (18) |
C9—C10 | 1.3937 (16) | C32—C33 | 1.3862 (19) |
C10—C11 | 1.3941 (17) | C33—C34 | 1.3948 (17) |
C11—C12 | 1.3925 (19) | C35—C36 | 1.3956 (16) |
C12—C13 | 1.3859 (18) | C35—C40 | 1.4014 (18) |
C13—C14 | 1.3938 (17) | C36—C37 | 1.3900 (17) |
C15—C20 | 1.3982 (15) | C37—C38 | 1.3955 (19) |
C15—C16 | 1.3982 (15) | C38—C39 | 1.3871 (19) |
C16—C17 | 1.3968 (16) | C39—C40 | 1.3921 (18) |
C17—C18 | 1.3897 (17) | C22—H22 | 0.9500 |
C18—C19 | 1.3929 (17) | C23—H23 | 0.9500 |
C19—C20 | 1.3914 (16) | C25—H25 | 0.9500 |
C2—H2 | 0.9500 | C26—H26 | 0.9500 |
C3—H3 | 0.9500 | C28—H28 | 0.9500 |
C5—H5 | 0.9500 | C30—H30 | 0.9500 |
C6—H6 | 0.9500 | C31—H31 | 0.9500 |
C8—H8 | 0.9500 | C32—H32 | 0.9500 |
C10—H10 | 0.9500 | C33—H33 | 0.9500 |
C11—H11 | 0.9500 | C34—H34 | 0.9500 |
C12—H12 | 0.9500 | C36—H36 | 0.9500 |
C13—H13 | 0.9500 | C37—H37 | 0.9500 |
C14—H14 | 0.9500 | C38—H38 | 0.9500 |
C16—H16 | 0.9500 | C39—H39 | 0.9500 |
C17—H17 | 0.9500 | C40—H40 | 0.9500 |
C1—N1—C9 | 119.47 (9) | C20—C19—H19 | 120.00 |
C1—N1—C15 | 122.22 (9) | C15—C20—H20 | 120.00 |
C9—N1—C15 | 118.30 (9) | C19—C20—H20 | 120.00 |
C21—N2—C29 | 122.84 (9) | N2—C21—C22 | 119.97 (10) |
C21—N2—C35 | 119.27 (9) | N2—C21—C26 | 121.64 (10) |
C29—N2—C35 | 117.89 (9) | C22—C21—C26 | 118.39 (10) |
N1—C1—C2 | 121.02 (9) | C21—C22—C23 | 120.71 (10) |
N1—C1—C6 | 120.38 (10) | C22—C23—C24 | 120.93 (10) |
C2—C1—C6 | 118.60 (10) | C23—C24—C25 | 118.15 (10) |
C1—C2—C3 | 120.71 (9) | C23—C24—C27 | 120.53 (11) |
C2—C3—C4 | 120.75 (10) | C25—C24—C27 | 121.28 (11) |
C3—C4—C7 | 120.58 (10) | C24—C25—C26 | 121.00 (11) |
C3—C4—C5 | 118.43 (10) | C21—C26—C25 | 120.80 (10) |
C5—C4—C7 | 120.99 (10) | C24—C27—C28 | 177.63 (15) |
C4—C5—C6 | 120.91 (10) | N2—C29—C30 | 121.36 (9) |
C1—C6—C5 | 120.54 (10) | N2—C29—C34 | 119.50 (9) |
C4—C7—C8 | 178.53 (13) | C30—C29—C34 | 119.14 (10) |
C10—C9—C14 | 119.96 (10) | C29—C30—C31 | 120.07 (10) |
N1—C9—C14 | 119.97 (10) | C30—C31—C32 | 120.57 (11) |
N1—C9—C10 | 120.07 (10) | C31—C32—C33 | 119.37 (11) |
C9—C10—C11 | 119.76 (11) | C32—C33—C34 | 120.47 (12) |
C10—C11—C12 | 120.19 (11) | C29—C34—C33 | 120.38 (11) |
C11—C12—C13 | 119.99 (12) | N2—C35—C36 | 120.41 (10) |
C12—C13—C14 | 120.18 (12) | N2—C35—C40 | 119.84 (10) |
C9—C14—C13 | 119.88 (11) | C36—C35—C40 | 119.75 (10) |
C16—C15—C20 | 119.20 (10) | C35—C36—C37 | 120.01 (11) |
N1—C15—C16 | 120.88 (10) | C36—C37—C38 | 120.29 (11) |
N1—C15—C20 | 119.91 (9) | C37—C38—C39 | 119.69 (12) |
C15—C16—C17 | 120.07 (10) | C38—C39—C40 | 120.56 (12) |
C16—C17—C18 | 120.84 (10) | C35—C40—C39 | 119.70 (11) |
C17—C18—C19 | 118.78 (10) | C21—C22—H22 | 120.00 |
C18—C19—C20 | 121.09 (11) | C23—C22—H22 | 120.00 |
C15—C20—C19 | 120.01 (10) | C22—C23—H23 | 120.00 |
C1—C2—H2 | 120.00 | C24—C23—H23 | 120.00 |
C3—C2—H2 | 120.00 | C24—C25—H25 | 120.00 |
C4—C3—H3 | 120.00 | C26—C25—H25 | 119.00 |
C2—C3—H3 | 120.00 | C21—C26—H26 | 120.00 |
C4—C5—H5 | 120.00 | C25—C26—H26 | 120.00 |
C6—C5—H5 | 120.00 | C27—C28—H28 | 180.00 |
C1—C6—H6 | 120.00 | C29—C30—H30 | 120.00 |
C5—C6—H6 | 120.00 | C31—C30—H30 | 120.00 |
C7—C8—H8 | 180.00 | C30—C31—H31 | 120.00 |
C11—C10—H10 | 120.00 | C32—C31—H31 | 120.00 |
C9—C10—H10 | 120.00 | C31—C32—H32 | 120.00 |
C10—C11—H11 | 120.00 | C33—C32—H32 | 120.00 |
C12—C11—H11 | 120.00 | C32—C33—H33 | 120.00 |
C11—C12—H12 | 120.00 | C34—C33—H33 | 120.00 |
C13—C12—H12 | 120.00 | C29—C34—H34 | 120.00 |
C14—C13—H13 | 120.00 | C33—C34—H34 | 120.00 |
C12—C13—H13 | 120.00 | C35—C36—H36 | 120.00 |
C13—C14—H14 | 120.00 | C37—C36—H36 | 120.00 |
C9—C14—H14 | 120.00 | C36—C37—H37 | 120.00 |
C15—C16—H16 | 120.00 | C38—C37—H37 | 120.00 |
C17—C16—H16 | 120.00 | C37—C38—H38 | 120.00 |
C16—C17—H17 | 120.00 | C39—C38—H38 | 120.00 |
C18—C17—H17 | 120.00 | C38—C39—H39 | 120.00 |
C19—C18—H18 | 121.00 | C40—C39—H39 | 120.00 |
C17—C18—H18 | 121.00 | C35—C40—H40 | 120.00 |
C18—C19—H19 | 119.00 | C39—C40—H40 | 120.00 |
C9—N1—C1—C2 | 152.80 (10) | C9—C10—C11—C12 | 1.86 (18) |
C15—N1—C1—C2 | −28.48 (15) | C10—C11—C12—C13 | −1.89 (18) |
C9—N1—C1—C6 | −27.76 (15) | C11—C12—C13—C14 | 0.24 (18) |
C15—N1—C1—C6 | 150.96 (10) | C12—C13—C14—C9 | 1.42 (18) |
C1—N1—C15—C16 | −34.25 (16) | N1—C15—C16—C17 | 179.51 (10) |
C9—N1—C15—C16 | 144.49 (11) | N1—C15—C20—C19 | 179.36 (11) |
C1—N1—C15—C20 | 146.66 (11) | C20—C15—C16—C17 | −1.39 (17) |
C1—N1—C9—C10 | −53.62 (15) | C16—C15—C20—C19 | 0.25 (17) |
C15—N1—C9—C10 | 127.61 (11) | C15—C16—C17—C18 | 1.37 (17) |
C1—N1—C9—C14 | 127.04 (11) | C16—C17—C18—C19 | −0.19 (17) |
C15—N1—C9—C14 | −51.73 (14) | C17—C18—C19—C20 | −0.97 (18) |
C9—N1—C15—C20 | −34.61 (15) | C18—C19—C20—C15 | 0.94 (18) |
C29—N2—C35—C40 | −56.40 (14) | N2—C21—C22—C23 | 179.24 (10) |
C21—N2—C29—C30 | −39.77 (16) | N2—C21—C26—C25 | −178.96 (11) |
C29—N2—C21—C22 | 157.71 (10) | C22—C21—C26—C25 | 0.91 (17) |
C21—N2—C35—C40 | 123.98 (11) | C26—C21—C22—C23 | −0.63 (17) |
C29—N2—C21—C26 | −22.42 (16) | C21—C22—C23—C24 | −0.25 (18) |
C35—N2—C21—C26 | 157.17 (10) | C22—C23—C24—C27 | −176.87 (12) |
C21—N2—C35—C36 | −55.59 (15) | C22—C23—C24—C25 | 0.84 (17) |
C29—N2—C35—C36 | 124.03 (11) | C27—C24—C25—C26 | 177.14 (12) |
C21—N2—C29—C34 | 140.89 (12) | C23—C24—C25—C26 | −0.56 (17) |
C35—N2—C29—C34 | −38.72 (15) | C24—C25—C26—C21 | −0.32 (18) |
C35—N2—C21—C22 | −22.70 (15) | N2—C29—C30—C31 | 180.00 (11) |
C35—N2—C29—C30 | 140.63 (11) | C34—C29—C30—C31 | −0.66 (17) |
N1—C1—C6—C5 | −176.97 (10) | N2—C29—C34—C33 | 179.65 (11) |
C2—C1—C6—C5 | 2.48 (15) | C30—C29—C34—C33 | 0.29 (18) |
C6—C1—C2—C3 | −2.65 (15) | C29—C30—C31—C32 | 0.61 (19) |
N1—C1—C2—C3 | 176.81 (10) | C30—C31—C32—C33 | −0.2 (2) |
C1—C2—C3—C4 | 0.49 (17) | C31—C32—C33—C34 | −0.2 (2) |
C2—C3—C4—C7 | −177.22 (10) | C32—C33—C34—C29 | 0.1 (2) |
C2—C3—C4—C5 | 1.85 (16) | N2—C35—C36—C37 | 178.62 (10) |
C7—C4—C5—C6 | 177.05 (10) | C40—C35—C36—C37 | −0.95 (17) |
C3—C4—C5—C6 | −2.01 (16) | N2—C35—C40—C39 | −179.21 (10) |
C4—C5—C6—C1 | −0.16 (17) | C36—C35—C40—C39 | 0.37 (17) |
C10—C9—C14—C13 | −1.45 (17) | C35—C36—C37—C38 | 0.58 (18) |
N1—C9—C14—C13 | 177.89 (10) | C36—C37—C38—C39 | 0.38 (18) |
N1—C9—C10—C11 | −179.53 (10) | C37—C38—C39—C40 | −0.97 (19) |
C14—C9—C10—C11 | −0.19 (17) | C38—C39—C40—C35 | 0.60 (18) |
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 | D···A | 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+1/2; (ii) −x+5/2, y, z−1/2; (iii) −x+3/2, y, z−1/2; (iv) −x+3/2, y, z+1/2. |
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 | D···A | 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+1/2; (ii) −x+5/2, y, z−1/2; (iii) −x+3/2, y, z−1/2; (iv) −x+3/2, y, z+1/2. |
Acknowledgements
The authors are grateful to Hubei University of Arts and Science for financial support.
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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.
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.