Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017515/at2270sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017515/at2270Isup2.hkl |
CCDC reference: 647585
To a solution of 1,3-diphenyl-propenone (1 mmol) in dichloromethane (5 ml), N,N-diethyl-2-bromoacetamide (2 mmol), zinc powder (3 mmol) and a trace amount of iodine were added to the mixture in order. The reaction mixture was refluxed with stirring for 5 h and then quenched with a saturated solution of ammonium chloride (8 ml). The mixture was filtered and extracted with dichloromethane, dried over magnesium sulfate. After evaporation of the solvent, a white solid was obtained (0.236 g, yield 73%) by column chromatography (silica gel/petroleum ether-ethyl acetate = 7/3, v/v). The colorless single crystals of compound was obtained through the evaporation of ethyl acetate-petroleum ether. Spectroscopic analysis: IR (KBr, νcm-1):3293, 1613; 1H NMR (CDCl3, δ, p.p.m.): 7.54–7.18 (m, 10H), 6.82 (s, 1H), 6.67 (d, 1H), 6.47 (d, 1H), 3.29 (m, 4H), 2.99 (d, 1H), 2.90 (d, 1H), 1.16 (t, 3H), 0.98 (t, 3H).
All carbon H atoms were positioned geometrically and refined as riding (C—H = 0.93 - 0.97 Å). For the CH and CH2 groups, Uiso(H) values were set equal to 1.2Ueq(C) and for the methyl groups, they were set equal to 1.5Ueq(C). Atom H1 was refined with O1—H1 = 0.82 Å and Uiso(H) = 1.5Ueq(O).
The Reformatsky reaction provides a good strategy of carbon-carbon bond formation (Ocamp & Doliber, 2004). In our study on the Reformatsky-type reaction of α-bromoacetamide with α,β-unsaturated ketone, we found that the most attractive feature of the reaction is its chemoselectivity, and a new compound, (I), has been synthesized by reaction of 1,3-diphenyl-propenone with N,N-diethyl-2-bromoacetamide. The structure determination of compound (I) was undertaken and the results are presented here.
The bond distances and angles are in good agreement with those respective normal values. In compound (I), the dihedral angle between the two phenyl rings is 113.9 (1)°, and the carbon-carbon double bond adopts E-configuration, which is also confirmed by the respective coupling constant (J = 16 Hz) in the 1H NMR spectroscopy of compound (I). The torsion angle of C6—C7—C8 —C9 is -179.3 (3) °, which indicates that they are approximately coplannar. The bond distance of C17—N1 [1.334 (4) Å] is significantly shorter than those of C18—N1 [1.482 (4) Å] and C20—N1 [1.487 (5) Å] because of \p-π conjugation.
For related literature, see: Ocamp & Doliber (2004).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C21H25NO2 | Dx = 1.149 Mg m−3 |
Mr = 323.42 | Melting point: 318 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1542 reflections |
a = 10.156 (3) Å | θ = 2.3–20.5° |
b = 10.339 (4) Å | µ = 0.07 mm−1 |
c = 35.621 (12) Å | T = 294 K |
V = 3741 (2) Å3 | Needle, colourless |
Z = 8 | 0.22 × 0.20 × 0.16 mm |
F(000) = 1392 |
Bruker SMART CCD area-detector diffractometer | 3271 independent reflections |
Radiation source: fine-focus sealed tube | 1480 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 25.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.984, Tmax = 0.988 | k = −12→5 |
11761 measured reflections | l = −42→34 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1641P] where P = (Fo2 + 2Fc2)/3 |
3271 reflections | (Δ/σ)max < 0.001 |
220 parameters | Δρmax = 0.14 e Å−3 |
12 restraints | Δρmin = −0.15 e Å−3 |
C21H25NO2 | V = 3741 (2) Å3 |
Mr = 323.42 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.156 (3) Å | µ = 0.07 mm−1 |
b = 10.339 (4) Å | T = 294 K |
c = 35.621 (12) Å | 0.22 × 0.20 × 0.16 mm |
Bruker SMART CCD area-detector diffractometer | 3271 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1480 reflections with I > 2σ(I) |
Tmin = 0.984, Tmax = 0.988 | Rint = 0.060 |
11761 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 12 restraints |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.14 e Å−3 |
3271 reflections | Δρmin = −0.15 e Å−3 |
220 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0108 (2) | 0.4384 (2) | 0.34952 (6) | 0.0708 (7) | |
H1 | −0.0179 | 0.4120 | 0.3279 | 0.106* | |
O2 | 0.0823 (3) | 0.2997 (3) | 0.29268 (6) | 0.0793 (8) | |
N1 | 0.2939 (3) | 0.2396 (3) | 0.29241 (7) | 0.0690 (9) | |
C1 | 0.1788 (4) | 0.5408 (4) | 0.48042 (10) | 0.0810 (12) | |
H1A | 0.2237 | 0.4649 | 0.4747 | 0.097* | |
C2 | 0.2020 (4) | 0.6018 (5) | 0.51398 (11) | 0.0945 (14) | |
H2 | 0.2622 | 0.5666 | 0.5308 | 0.113* | |
C3 | 0.1385 (5) | 0.7126 (5) | 0.52296 (12) | 0.0944 (14) | |
H3 | 0.1554 | 0.7532 | 0.5458 | 0.113* | |
C4 | 0.0503 (5) | 0.7645 (4) | 0.49870 (13) | 0.0993 (15) | |
H4 | 0.0064 | 0.8406 | 0.5048 | 0.119* | |
C5 | 0.0261 (4) | 0.7036 (4) | 0.46502 (10) | 0.0831 (12) | |
H5 | −0.0348 | 0.7394 | 0.4485 | 0.100* | |
C6 | 0.0898 (3) | 0.5906 (3) | 0.45503 (8) | 0.0592 (9) | |
C7 | 0.0603 (3) | 0.5289 (4) | 0.41901 (8) | 0.0621 (9) | |
H7 | 0.0076 | 0.5752 | 0.4024 | 0.074* | |
C8 | 0.1004 (3) | 0.4155 (4) | 0.40781 (8) | 0.0586 (9) | |
H8 | 0.1524 | 0.3686 | 0.4244 | 0.070* | |
C9 | 0.0707 (3) | 0.3528 (3) | 0.37033 (8) | 0.0546 (9) | |
C10 | 0.0025 (3) | 0.2238 (3) | 0.37714 (8) | 0.0536 (9) | |
C11 | 0.0664 (4) | 0.1252 (4) | 0.39667 (10) | 0.0740 (11) | |
H11 | 0.1530 | 0.1382 | 0.4043 | 0.089* | |
C12 | 0.0074 (6) | 0.0114 (5) | 0.40498 (12) | 0.0988 (14) | |
H12 | 0.0531 | −0.0519 | 0.4182 | 0.119* | |
C13 | −0.1177 (7) | −0.0099 (5) | 0.39410 (13) | 0.1073 (17) | |
H13 | −0.1579 | −0.0882 | 0.3999 | 0.129* | |
C14 | −0.1873 (4) | 0.0831 (6) | 0.37449 (12) | 0.0945 (15) | |
H14 | −0.2736 | 0.0679 | 0.3670 | 0.113* | |
C15 | −0.1249 (4) | 0.2011 (4) | 0.36615 (9) | 0.0746 (11) | |
H15 | −0.1707 | 0.2645 | 0.3530 | 0.089* | |
C16 | 0.2026 (3) | 0.3355 (4) | 0.34956 (8) | 0.0631 (10) | |
H16A | 0.2484 | 0.4178 | 0.3492 | 0.076* | |
H16B | 0.2566 | 0.2747 | 0.3634 | 0.076* | |
C17 | 0.1878 (4) | 0.2876 (3) | 0.30959 (9) | 0.0565 (9) | |
C18 | 0.2871 (4) | 0.2085 (4) | 0.25183 (9) | 0.0767 (11) | |
H18A | 0.2266 | 0.2676 | 0.2396 | 0.092* | |
H18B | 0.3733 | 0.2203 | 0.2407 | 0.092* | |
C19 | 0.2427 (5) | 0.0740 (4) | 0.24549 (13) | 0.1223 (17) | |
H19A | 0.3028 | 0.0152 | 0.2574 | 0.183* | |
H19B | 0.2400 | 0.0567 | 0.2190 | 0.183* | |
H19C | 0.1563 | 0.0627 | 0.2560 | 0.183* | |
C20 | 0.4265 (5) | 0.2287 (5) | 0.30977 (11) | 0.1050 (17) | |
H20A | 0.4744 | 0.1586 | 0.2979 | 0.126* | |
H20B | 0.4170 | 0.2078 | 0.3362 | 0.126* | |
C21 | 0.5042 (5) | 0.3523 (7) | 0.30588 (13) | 0.133 (2) | |
H21A | 0.5124 | 0.3741 | 0.2798 | 0.199* | |
H21B | 0.5902 | 0.3406 | 0.3165 | 0.199* | |
H21C | 0.4595 | 0.4208 | 0.3188 | 0.199* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0724 (17) | 0.0813 (17) | 0.0586 (13) | 0.0152 (13) | −0.0094 (13) | −0.0002 (12) |
O2 | 0.0540 (16) | 0.129 (2) | 0.0554 (13) | −0.0034 (15) | −0.0014 (12) | −0.0159 (14) |
N1 | 0.065 (2) | 0.088 (2) | 0.0539 (16) | 0.0176 (17) | 0.0032 (16) | −0.0027 (14) |
C1 | 0.083 (3) | 0.098 (3) | 0.062 (2) | 0.011 (2) | −0.008 (2) | −0.019 (2) |
C2 | 0.098 (4) | 0.124 (4) | 0.062 (2) | 0.000 (3) | −0.009 (2) | −0.020 (3) |
C3 | 0.103 (4) | 0.114 (4) | 0.067 (3) | −0.033 (3) | 0.016 (3) | −0.028 (3) |
C4 | 0.124 (4) | 0.079 (3) | 0.095 (3) | −0.002 (3) | 0.008 (3) | −0.030 (3) |
C5 | 0.102 (3) | 0.073 (3) | 0.075 (2) | 0.002 (2) | −0.005 (2) | −0.010 (2) |
C6 | 0.061 (2) | 0.066 (2) | 0.0509 (18) | −0.0086 (19) | 0.0087 (18) | −0.0026 (17) |
C7 | 0.062 (2) | 0.070 (3) | 0.0534 (19) | −0.003 (2) | −0.0007 (17) | 0.0001 (18) |
C8 | 0.054 (2) | 0.073 (3) | 0.0491 (18) | −0.0012 (19) | 0.0007 (15) | −0.0031 (17) |
C9 | 0.0411 (19) | 0.075 (2) | 0.0479 (17) | 0.0050 (18) | −0.0027 (15) | −0.0011 (16) |
C10 | 0.045 (2) | 0.072 (2) | 0.0440 (16) | −0.0017 (19) | 0.0070 (16) | −0.0115 (17) |
C11 | 0.072 (3) | 0.080 (3) | 0.070 (2) | −0.008 (2) | 0.001 (2) | −0.002 (2) |
C12 | 0.121 (4) | 0.092 (4) | 0.083 (3) | −0.014 (3) | 0.001 (3) | −0.002 (3) |
C13 | 0.153 (6) | 0.101 (4) | 0.067 (3) | −0.036 (4) | 0.029 (3) | −0.006 (3) |
C14 | 0.070 (3) | 0.135 (4) | 0.078 (3) | −0.044 (3) | 0.019 (2) | −0.036 (3) |
C15 | 0.054 (2) | 0.107 (3) | 0.063 (2) | −0.004 (2) | 0.0058 (19) | −0.017 (2) |
C16 | 0.050 (2) | 0.087 (3) | 0.0518 (18) | −0.0079 (19) | 0.0039 (16) | −0.0057 (17) |
C17 | 0.049 (2) | 0.068 (2) | 0.0527 (19) | −0.0041 (19) | 0.0037 (18) | 0.0024 (17) |
C18 | 0.082 (3) | 0.086 (3) | 0.062 (2) | 0.011 (2) | 0.009 (2) | −0.002 (2) |
C19 | 0.182 (5) | 0.084 (3) | 0.101 (3) | 0.009 (3) | −0.002 (3) | −0.015 (3) |
C20 | 0.099 (4) | 0.151 (5) | 0.065 (2) | 0.061 (4) | 0.006 (3) | 0.000 (3) |
C21 | 0.080 (3) | 0.210 (6) | 0.108 (3) | −0.008 (4) | −0.001 (3) | −0.037 (4) |
O1—C9 | 1.421 (4) | C10—C11 | 1.395 (5) |
O1—H1 | 0.8200 | C11—C12 | 1.353 (6) |
O2—C17 | 1.235 (4) | C11—H11 | 0.9300 |
N1—C17 | 1.334 (4) | C12—C13 | 1.347 (6) |
N1—C18 | 1.482 (4) | C12—H12 | 0.9300 |
N1—C20 | 1.487 (5) | C13—C14 | 1.382 (6) |
C1—C2 | 1.372 (5) | C13—H13 | 0.9300 |
C1—C6 | 1.378 (5) | C14—C15 | 1.406 (6) |
C1—H1A | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.353 (6) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—C17 | 1.515 (4) |
C3—C4 | 1.356 (6) | C16—H16A | 0.9700 |
C3—H3 | 0.9300 | C16—H16B | 0.9700 |
C4—C5 | 1.377 (5) | C18—C19 | 1.480 (5) |
C4—H4 | 0.9300 | C18—H18A | 0.9700 |
C5—C6 | 1.382 (5) | C18—H18B | 0.9700 |
C5—H5 | 0.9300 | C19—H19A | 0.9600 |
C6—C7 | 1.464 (4) | C19—H19B | 0.9600 |
C7—C8 | 1.303 (4) | C19—H19C | 0.9600 |
C7—H7 | 0.9300 | C20—C21 | 1.508 (7) |
C8—C9 | 1.515 (4) | C20—H20A | 0.9700 |
C8—H8 | 0.9300 | C20—H20B | 0.9700 |
C9—C10 | 1.521 (5) | C21—H21A | 0.9600 |
C9—C16 | 1.540 (4) | C21—H21B | 0.9600 |
C10—C15 | 1.373 (5) | C21—H21C | 0.9600 |
C9—O1—H1 | 109.5 | C12—C13—C14 | 120.9 (5) |
C17—N1—C18 | 119.3 (3) | C12—C13—H13 | 119.5 |
C17—N1—C20 | 124.7 (3) | C14—C13—H13 | 119.5 |
C18—N1—C20 | 115.6 (3) | C13—C14—C15 | 118.7 (4) |
C2—C1—C6 | 120.8 (4) | C13—C14—H14 | 120.7 |
C2—C1—H1A | 119.6 | C15—C14—H14 | 120.7 |
C6—C1—H1A | 119.6 | C10—C15—C14 | 120.9 (4) |
C3—C2—C1 | 120.9 (4) | C10—C15—H15 | 119.6 |
C3—C2—H2 | 119.6 | C14—C15—H15 | 119.6 |
C1—C2—H2 | 119.6 | C17—C16—C9 | 113.8 (3) |
C2—C3—C4 | 120.0 (4) | C17—C16—H16A | 108.8 |
C2—C3—H3 | 120.0 | C9—C16—H16A | 108.8 |
C4—C3—H3 | 120.0 | C17—C16—H16B | 108.8 |
C3—C4—C5 | 119.5 (4) | C9—C16—H16B | 108.8 |
C3—C4—H4 | 120.2 | H16A—C16—H16B | 107.7 |
C5—C4—H4 | 120.2 | O2—C17—N1 | 120.9 (3) |
C4—C5—C6 | 121.8 (4) | O2—C17—C16 | 120.7 (3) |
C4—C5—H5 | 119.1 | N1—C17—C16 | 118.2 (3) |
C6—C5—H5 | 119.1 | C19—C18—N1 | 111.6 (3) |
C1—C6—C5 | 117.0 (3) | C19—C18—H18A | 109.3 |
C1—C6—C7 | 123.1 (3) | N1—C18—H18A | 109.3 |
C5—C6—C7 | 119.9 (3) | C19—C18—H18B | 109.3 |
C8—C7—C6 | 126.6 (3) | N1—C18—H18B | 109.3 |
C8—C7—H7 | 116.7 | H18A—C18—H18B | 108.0 |
C6—C7—H7 | 116.7 | C18—C19—H19A | 109.5 |
C7—C8—C9 | 126.4 (3) | C18—C19—H19B | 109.5 |
C7—C8—H8 | 116.8 | H19A—C19—H19B | 109.5 |
C9—C8—H8 | 116.8 | C18—C19—H19C | 109.5 |
O1—C9—C8 | 108.0 (3) | H19A—C19—H19C | 109.5 |
O1—C9—C10 | 111.3 (3) | H19B—C19—H19C | 109.5 |
C8—C9—C10 | 109.0 (2) | N1—C20—C21 | 111.8 (4) |
O1—C9—C16 | 109.2 (2) | N1—C20—H20A | 109.3 |
C8—C9—C16 | 107.4 (2) | C21—C20—H20A | 109.3 |
C10—C9—C16 | 111.8 (3) | N1—C20—H20B | 109.3 |
C15—C10—C11 | 117.1 (4) | C21—C20—H20B | 109.3 |
C15—C10—C9 | 122.3 (3) | H20A—C20—H20B | 107.9 |
C11—C10—C9 | 120.6 (3) | C20—C21—H21A | 109.5 |
C12—C11—C10 | 122.6 (4) | C20—C21—H21B | 109.5 |
C12—C11—H11 | 118.7 | H21A—C21—H21B | 109.5 |
C10—C11—H11 | 118.7 | C20—C21—H21C | 109.5 |
C13—C12—C11 | 119.8 (5) | H21A—C21—H21C | 109.5 |
C13—C12—H12 | 120.1 | H21B—C21—H21C | 109.5 |
C11—C12—H12 | 120.1 | ||
C6—C1—C2—C3 | −0.2 (6) | C9—C10—C11—C12 | 176.7 (3) |
C1—C2—C3—C4 | 0.2 (7) | C10—C11—C12—C13 | 0.3 (6) |
C2—C3—C4—C5 | 0.0 (7) | C11—C12—C13—C14 | 0.0 (6) |
C3—C4—C5—C6 | −0.3 (7) | C12—C13—C14—C15 | −0.2 (6) |
C2—C1—C6—C5 | 0.0 (5) | C11—C10—C15—C14 | 0.1 (5) |
C2—C1—C6—C7 | −179.4 (3) | C9—C10—C15—C14 | −176.8 (3) |
C4—C5—C6—C1 | 0.3 (6) | C13—C14—C15—C10 | 0.1 (5) |
C4—C5—C6—C7 | 179.7 (4) | O1—C9—C16—C17 | −56.6 (4) |
C1—C6—C7—C8 | 8.0 (6) | C8—C9—C16—C17 | −173.4 (3) |
C5—C6—C7—C8 | −171.4 (4) | C10—C9—C16—C17 | 67.0 (4) |
C6—C7—C8—C9 | −179.3 (3) | C18—N1—C17—O2 | 4.0 (5) |
C7—C8—C9—O1 | −0.9 (5) | C20—N1—C17—O2 | 176.3 (4) |
C7—C8—C9—C10 | −122.0 (4) | C18—N1—C17—C16 | −171.8 (3) |
C7—C8—C9—C16 | 116.7 (4) | C20—N1—C17—C16 | 0.5 (5) |
O1—C9—C10—C15 | −4.0 (4) | C9—C16—C17—O2 | 20.4 (5) |
C8—C9—C10—C15 | 115.1 (3) | C9—C16—C17—N1 | −163.8 (3) |
C16—C9—C10—C15 | −126.3 (3) | C17—N1—C18—C19 | −89.5 (4) |
O1—C9—C10—C11 | 179.2 (3) | C20—N1—C18—C19 | 97.5 (4) |
C8—C9—C10—C11 | −61.8 (4) | C17—N1—C20—C21 | −85.4 (4) |
C16—C9—C10—C11 | 56.8 (4) | C18—N1—C20—C21 | 87.2 (4) |
C15—C10—C11—C12 | −0.3 (5) |
Experimental details
Crystal data | |
Chemical formula | C21H25NO2 |
Mr | 323.42 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 294 |
a, b, c (Å) | 10.156 (3), 10.339 (4), 35.621 (12) |
V (Å3) | 3741 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.22 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.984, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11761, 3271, 1480 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.202, 1.03 |
No. of reflections | 3271 |
No. of parameters | 220 |
No. of restraints | 12 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997, SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
The Reformatsky reaction provides a good strategy of carbon-carbon bond formation (Ocamp & Doliber, 2004). In our study on the Reformatsky-type reaction of α-bromoacetamide with α,β-unsaturated ketone, we found that the most attractive feature of the reaction is its chemoselectivity, and a new compound, (I), has been synthesized by reaction of 1,3-diphenyl-propenone with N,N-diethyl-2-bromoacetamide. The structure determination of compound (I) was undertaken and the results are presented here.
The bond distances and angles are in good agreement with those respective normal values. In compound (I), the dihedral angle between the two phenyl rings is 113.9 (1)°, and the carbon-carbon double bond adopts E-configuration, which is also confirmed by the respective coupling constant (J = 16 Hz) in the 1H NMR spectroscopy of compound (I). The torsion angle of C6—C7—C8 —C9 is -179.3 (3) °, which indicates that they are approximately coplannar. The bond distance of C17—N1 [1.334 (4) Å] is significantly shorter than those of C18—N1 [1.482 (4) Å] and C20—N1 [1.487 (5) Å] because of \p-π conjugation.