![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
(Z)-Ethyl 2,4-diphenyl-3-(propylamino)but-2-enoate
aDepartment of Pharmaceuticals, Tianjin Medical College, Tianjin 300222, People's Republic of China
*Correspondence e-mail: huiminjin@yahoo.cn
The title compound, C21H25NO2, adopts a Z conformation about the C=C double bond. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond and the dihedral angle between the aromatic ring planes is 76.04 (12)°. The atoms of the ethyl substituent are disordered over two sets of sites in a 0.60 (2):0.40 (2) ratio.
Related literature
For the synthesis, see: Du et al. (2006). For background, see: Xue et al. (2007
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; 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
10.1107/S160053680804395X/hb2886sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680804395X/hb2886Isup2.hkl
The title compound was prepared according to the method of the literature (Du, et al., 2006). Colourless blocks of (I) were grown from a mixture of ethyl actate and petroleum ether.
The non-N H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(CH and CH2) or 1.5Ueq(CH3). The N—H distance was refined with the restraint of 0.90 (1) Å, and the C19—C20, C20—C21, C9—C10 and C9—C10' with the restraint of 1.54 (1) Å. The ethyl radical of the ester moiety was found to be disordered, with the site occupancy ratio of 0.40 (2):0.60 (2).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (I) with 50% probability displacement ellipsoids. The dashed line indicates the intramolecular N—H···O hydrogen bond. |
C21H25NO2 | F(000) = 696 |
Mr = 323.42 | Dx = 1.136 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4099 reflections |
a = 12.186 (2) Å | θ = 2.2–27.1° |
b = 8.4771 (17) Å | µ = 0.07 mm−1 |
c = 19.080 (4) Å | T = 293 K |
β = 106.33 (3)° | Block, colourless |
V = 1891.4 (7) Å3 | 0.28 × 0.22 × 0.18 mm |
Z = 4 |
Rigaku Saturn diffractometer | 3323 independent reflections |
Radiation source: rotating anode | 2290 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.034 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −9→10 |
Tmin = 0.980, Tmax = 0.987 | l = −21→22 |
12325 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.198 | w = 1/[σ2(Fo2) + (0.1207P)2 + 0.019P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3323 reflections | Δρmax = 0.24 e Å−3 |
232 parameters | Δρmin = −0.19 e Å−3 |
5 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.079 (13) |
C21H25NO2 | V = 1891.4 (7) Å3 |
Mr = 323.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.186 (2) Å | µ = 0.07 mm−1 |
b = 8.4771 (17) Å | T = 293 K |
c = 19.080 (4) Å | 0.28 × 0.22 × 0.18 mm |
β = 106.33 (3)° |
Rigaku Saturn diffractometer | 3323 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 2290 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.987 | Rint = 0.034 |
12325 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 5 restraints |
wR(F2) = 0.198 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.24 e Å−3 |
3323 reflections | Δρmin = −0.19 e Å−3 |
232 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 | Occ. (<1) | |
O1 | 0.98880 (16) | 0.7415 (2) | 0.24987 (10) | 0.0936 (6) | |
O2 | 1.07264 (14) | 0.97745 (19) | 0.24972 (8) | 0.0791 (5) | |
N1 | 0.95170 (17) | 1.1941 (2) | 0.16036 (11) | 0.0710 (6) | |
C1 | 0.7770 (2) | 0.7362 (3) | 0.07667 (13) | 0.0723 (7) | |
H1 | 0.8213 | 0.7655 | 0.0463 | 0.087* | |
C2 | 0.6935 (2) | 0.6239 (3) | 0.05278 (16) | 0.0864 (8) | |
H2A | 0.6812 | 0.5794 | 0.0067 | 0.104* | |
C3 | 0.6286 (2) | 0.5778 (3) | 0.09719 (18) | 0.0906 (8) | |
H3A | 0.5719 | 0.5018 | 0.0814 | 0.109* | |
C4 | 0.6473 (2) | 0.6434 (4) | 0.16427 (18) | 0.0977 (9) | |
H4A | 0.6038 | 0.6115 | 0.1947 | 0.117* | |
C5 | 0.7302 (2) | 0.7568 (3) | 0.18764 (14) | 0.0829 (8) | |
H5A | 0.7415 | 0.8007 | 0.2338 | 0.099* | |
C6 | 0.79728 (17) | 0.8072 (2) | 0.14437 (11) | 0.0591 (6) | |
C7 | 0.88662 (17) | 0.9301 (2) | 0.16911 (10) | 0.0572 (6) | |
C8 | 0.99038 (19) | 0.8903 (3) | 0.22513 (12) | 0.0654 (6) | |
C9 | 1.0852 (3) | 0.6899 (4) | 0.30878 (18) | 0.1159 (11) | 0.60 (2) |
H9A | 1.1075 | 0.5855 | 0.2971 | 0.139* | 0.60 (2) |
H9B | 1.1489 | 0.7602 | 0.3112 | 0.139* | 0.60 (2) |
C10 | 1.0665 (11) | 0.684 (2) | 0.3778 (4) | 0.133 (4) | 0.60 (2) |
H10A | 1.1353 | 0.6512 | 0.4133 | 0.199* | 0.60 (2) |
H10B | 1.0063 | 0.6106 | 0.3770 | 0.199* | 0.60 (2) |
H10C | 1.0450 | 0.7871 | 0.3904 | 0.199* | 0.60 (2) |
C9' | 1.0852 (3) | 0.6899 (4) | 0.30878 (18) | 0.1159 (11) | 0.40 (2) |
H9'A | 1.1328 | 0.7787 | 0.3306 | 0.139* | 0.40 (2) |
H9'B | 1.1314 | 0.6146 | 0.2913 | 0.139* | 0.40 (2) |
C10' | 1.0339 (12) | 0.616 (2) | 0.3618 (8) | 0.111 (4) | 0.40 (2) |
H10D | 1.0935 | 0.5788 | 0.4030 | 0.166* | 0.40 (2) |
H10E | 0.9871 | 0.5285 | 0.3392 | 0.166* | 0.40 (2) |
H10F | 0.9879 | 0.6918 | 0.3779 | 0.166* | 0.40 (2) |
C11 | 0.87065 (17) | 1.0815 (2) | 0.14123 (11) | 0.0588 (6) | |
C12 | 0.75990 (17) | 1.1280 (2) | 0.08755 (11) | 0.0618 (6) | |
H12A | 0.7336 | 1.2250 | 0.1045 | 0.074* | |
H12B | 0.7036 | 1.0471 | 0.0876 | 0.074* | |
C13 | 0.76341 (16) | 1.1525 (2) | 0.00975 (11) | 0.0565 (5) | |
C14 | 0.6757 (2) | 1.2334 (3) | −0.03842 (14) | 0.0745 (7) | |
H14A | 0.6150 | 1.2716 | −0.0228 | 0.089* | |
C15 | 0.6773 (3) | 1.2584 (3) | −0.11014 (15) | 0.0918 (8) | |
H15A | 0.6185 | 1.3148 | −0.1419 | 0.110* | |
C16 | 0.7651 (2) | 1.2003 (3) | −0.13433 (14) | 0.0849 (8) | |
H16A | 0.7663 | 1.2175 | −0.1822 | 0.102* | |
C17 | 0.8495 (2) | 1.1182 (3) | −0.08805 (14) | 0.0803 (7) | |
H17A | 0.9085 | 1.0766 | −0.1045 | 0.096* | |
C18 | 0.84946 (18) | 1.0953 (3) | −0.01624 (12) | 0.0706 (6) | |
H18A | 0.9093 | 1.0397 | 0.0151 | 0.085* | |
C19 | 0.9397 (2) | 1.3609 (3) | 0.14108 (16) | 0.0837 (8) | |
H19A | 0.9085 | 1.4167 | 0.1755 | 0.100* | |
H19B | 0.8867 | 1.3728 | 0.0928 | 0.100* | |
C20 | 1.0546 (3) | 1.4324 (3) | 0.14196 (19) | 0.1120 (11) | |
H20A | 1.0446 | 1.5452 | 0.1344 | 0.134* | |
H20B | 1.1070 | 1.4167 | 0.1902 | 0.134* | |
C21 | 1.1081 (3) | 1.3697 (4) | 0.0878 (3) | 0.1381 (14) | |
H21A | 1.1817 | 1.4177 | 0.0946 | 0.207* | |
H21B | 1.0605 | 1.3929 | 0.0396 | 0.207* | |
H21C | 1.1169 | 1.2576 | 0.0937 | 0.207* | |
H1A | 1.0180 (11) | 1.163 (2) | 0.1924 (9) | 0.065 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0861 (12) | 0.0898 (12) | 0.0851 (13) | 0.0094 (9) | −0.0083 (10) | 0.0275 (9) |
O2 | 0.0732 (11) | 0.0914 (11) | 0.0625 (10) | 0.0011 (8) | 0.0026 (8) | −0.0069 (8) |
N1 | 0.0710 (13) | 0.0671 (11) | 0.0688 (13) | −0.0032 (9) | 0.0099 (11) | 0.0003 (9) |
C1 | 0.0817 (16) | 0.0716 (13) | 0.0667 (15) | −0.0068 (11) | 0.0257 (13) | −0.0040 (11) |
C2 | 0.0884 (17) | 0.0779 (15) | 0.0873 (18) | −0.0122 (13) | 0.0156 (15) | −0.0051 (13) |
C3 | 0.0755 (16) | 0.0790 (16) | 0.107 (2) | −0.0092 (12) | 0.0090 (16) | 0.0195 (15) |
C4 | 0.0823 (18) | 0.119 (2) | 0.094 (2) | −0.0134 (16) | 0.0297 (17) | 0.0302 (18) |
C5 | 0.0798 (17) | 0.1103 (19) | 0.0628 (15) | −0.0056 (14) | 0.0270 (14) | 0.0115 (13) |
C6 | 0.0591 (12) | 0.0645 (12) | 0.0522 (12) | 0.0079 (9) | 0.0132 (10) | 0.0094 (10) |
C7 | 0.0629 (12) | 0.0659 (12) | 0.0428 (11) | 0.0084 (9) | 0.0148 (9) | 0.0027 (9) |
C8 | 0.0712 (14) | 0.0745 (13) | 0.0487 (12) | 0.0090 (11) | 0.0138 (11) | −0.0020 (11) |
C9 | 0.096 (2) | 0.133 (2) | 0.094 (2) | 0.0225 (18) | −0.0132 (18) | 0.040 (2) |
C10 | 0.102 (6) | 0.194 (10) | 0.081 (5) | 0.043 (6) | −0.010 (4) | −0.022 (5) |
C9' | 0.096 (2) | 0.133 (2) | 0.094 (2) | 0.0225 (18) | −0.0132 (18) | 0.040 (2) |
C10' | 0.119 (8) | 0.129 (9) | 0.060 (6) | −0.016 (7) | −0.015 (5) | 0.041 (6) |
C11 | 0.0645 (12) | 0.0669 (12) | 0.0475 (11) | 0.0055 (9) | 0.0197 (10) | −0.0032 (9) |
C12 | 0.0585 (12) | 0.0668 (12) | 0.0617 (13) | 0.0101 (9) | 0.0196 (10) | 0.0044 (10) |
C13 | 0.0568 (12) | 0.0509 (10) | 0.0576 (12) | −0.0005 (8) | 0.0092 (10) | 0.0023 (9) |
C14 | 0.0717 (15) | 0.0751 (14) | 0.0690 (16) | 0.0136 (11) | 0.0071 (12) | 0.0039 (12) |
C15 | 0.095 (2) | 0.0952 (18) | 0.0692 (17) | 0.0136 (14) | −0.0033 (15) | 0.0173 (14) |
C16 | 0.0953 (19) | 0.0984 (18) | 0.0556 (14) | −0.0162 (15) | 0.0123 (14) | 0.0129 (13) |
C17 | 0.0747 (16) | 0.1049 (18) | 0.0626 (15) | 0.0008 (13) | 0.0213 (13) | 0.0083 (13) |
C18 | 0.0618 (13) | 0.0874 (15) | 0.0608 (14) | 0.0117 (11) | 0.0144 (11) | 0.0121 (11) |
C19 | 0.0904 (17) | 0.0636 (14) | 0.099 (2) | −0.0011 (12) | 0.0290 (15) | −0.0085 (13) |
C20 | 0.129 (3) | 0.0726 (16) | 0.138 (3) | −0.0143 (16) | 0.044 (2) | −0.0030 (17) |
C21 | 0.136 (3) | 0.100 (2) | 0.205 (4) | −0.006 (2) | 0.092 (3) | −0.004 (2) |
O1—C8 | 1.349 (3) | C10'—H10E | 0.9600 |
O1—C9 | 1.446 (3) | C10'—H10F | 0.9600 |
O2—C8 | 1.227 (3) | C11—C12 | 1.499 (3) |
N1—C11 | 1.348 (3) | C12—C13 | 1.511 (3) |
N1—C19 | 1.458 (3) | C12—H12A | 0.9700 |
N1—H1A | 0.905 (10) | C12—H12B | 0.9700 |
C1—C2 | 1.374 (3) | C13—C18 | 1.369 (3) |
C1—C6 | 1.383 (3) | C13—C14 | 1.381 (3) |
C1—H1 | 0.9300 | C14—C15 | 1.390 (4) |
C2—C3 | 1.369 (4) | C14—H14A | 0.9300 |
C2—H2A | 0.9300 | C15—C16 | 1.370 (4) |
C3—C4 | 1.355 (4) | C15—H15A | 0.9300 |
C3—H3A | 0.9300 | C16—C17 | 1.346 (3) |
C4—C5 | 1.375 (4) | C16—H16A | 0.9300 |
C4—H4A | 0.9300 | C17—C18 | 1.384 (3) |
C5—C6 | 1.383 (3) | C17—H17A | 0.9300 |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C6—C7 | 1.485 (3) | C19—C20 | 1.522 (3) |
C7—C11 | 1.381 (3) | C19—H19A | 0.9700 |
C7—C8 | 1.448 (3) | C19—H19B | 0.9700 |
C9—C10 | 1.399 (7) | C20—C21 | 1.467 (4) |
C9—H9A | 0.9700 | C20—H20A | 0.9700 |
C9—H9B | 0.9700 | C20—H20B | 0.9700 |
C10—H10A | 0.9600 | C21—H21A | 0.9600 |
C10—H10B | 0.9600 | C21—H21B | 0.9600 |
C10—H10C | 0.9600 | C21—H21C | 0.9600 |
C10'—H10D | 0.9600 | ||
C8—O1—C9 | 117.8 (2) | N1—C11—C12 | 116.66 (18) |
C11—N1—C19 | 127.2 (2) | C7—C11—C12 | 120.63 (19) |
C11—N1—H1A | 114.9 (13) | C11—C12—C13 | 116.00 (16) |
C19—N1—H1A | 117.5 (13) | C11—C12—H12A | 108.3 |
C2—C1—C6 | 122.2 (2) | C13—C12—H12A | 108.3 |
C2—C1—H1 | 118.9 | C11—C12—H12B | 108.3 |
C6—C1—H1 | 118.9 | C13—C12—H12B | 108.3 |
C3—C2—C1 | 119.7 (3) | H12A—C12—H12B | 107.4 |
C3—C2—H2A | 120.2 | C18—C13—C14 | 117.6 (2) |
C1—C2—H2A | 120.2 | C18—C13—C12 | 122.92 (19) |
C4—C3—C2 | 119.6 (3) | C14—C13—C12 | 119.44 (18) |
C4—C3—H3A | 120.2 | C13—C14—C15 | 120.5 (2) |
C2—C3—H3A | 120.2 | C13—C14—H14A | 119.7 |
C3—C4—C5 | 120.4 (2) | C15—C14—H14A | 119.7 |
C3—C4—H4A | 119.8 | C16—C15—C14 | 120.4 (2) |
C5—C4—H4A | 119.8 | C16—C15—H15A | 119.8 |
C4—C5—C6 | 121.8 (2) | C14—C15—H15A | 119.8 |
C4—C5—H5A | 119.1 | C17—C16—C15 | 119.3 (2) |
C6—C5—H5A | 119.1 | C17—C16—H16A | 120.3 |
C1—C6—C5 | 116.3 (2) | C15—C16—H16A | 120.3 |
C1—C6—C7 | 121.66 (17) | C16—C17—C18 | 120.6 (2) |
C5—C6—C7 | 122.1 (2) | C16—C17—H17A | 119.7 |
C11—C7—C8 | 120.0 (2) | C18—C17—H17A | 119.7 |
C11—C7—C6 | 121.21 (19) | C13—C18—C17 | 121.5 (2) |
C8—C7—C6 | 118.74 (18) | C13—C18—H18A | 119.2 |
O2—C8—O1 | 121.3 (2) | C17—C18—H18A | 119.2 |
O2—C8—C7 | 126.3 (2) | N1—C19—C20 | 110.9 (2) |
O1—C8—C7 | 112.4 (2) | N1—C19—H19A | 109.5 |
C10—C9—O1 | 115.5 (5) | C20—C19—H19A | 109.5 |
C10—C9—H9A | 108.4 | N1—C19—H19B | 109.5 |
O1—C9—H9A | 108.4 | C20—C19—H19B | 109.5 |
C10—C9—H9B | 108.4 | H19A—C19—H19B | 108.0 |
O1—C9—H9B | 108.4 | C21—C20—C19 | 115.9 (3) |
H9A—C9—H9B | 107.5 | C21—C20—H20A | 108.3 |
C9—C10—H10A | 109.5 | C19—C20—H20A | 108.3 |
C9—C10—H10B | 109.5 | C21—C20—H20B | 108.3 |
H10A—C10—H10B | 109.5 | C19—C20—H20B | 108.3 |
C9—C10—H10C | 109.5 | H20A—C20—H20B | 107.4 |
H10A—C10—H10C | 109.5 | C20—C21—H21A | 109.5 |
H10B—C10—H10C | 109.5 | C20—C21—H21B | 109.5 |
H10D—C10'—H10E | 109.5 | H21A—C21—H21B | 109.5 |
H10D—C10'—H10F | 109.5 | C20—C21—H21C | 109.5 |
H10E—C10'—H10F | 109.5 | H21A—C21—H21C | 109.5 |
N1—C11—C7 | 122.7 (2) | H21B—C21—H21C | 109.5 |
C6—C1—C2—C3 | −0.9 (4) | C19—N1—C11—C12 | 7.4 (3) |
C1—C2—C3—C4 | 0.0 (4) | C8—C7—C11—N1 | 4.6 (3) |
C2—C3—C4—C5 | 0.6 (4) | C6—C7—C11—N1 | −177.32 (17) |
C3—C4—C5—C6 | −0.3 (4) | C8—C7—C11—C12 | −175.14 (16) |
C2—C1—C6—C5 | 1.2 (3) | C6—C7—C11—C12 | 2.9 (3) |
C2—C1—C6—C7 | −179.1 (2) | N1—C11—C12—C13 | 71.9 (2) |
C4—C5—C6—C1 | −0.5 (4) | C7—C11—C12—C13 | −108.3 (2) |
C4—C5—C6—C7 | 179.7 (2) | C11—C12—C13—C18 | 17.9 (3) |
C1—C6—C7—C11 | 74.3 (3) | C11—C12—C13—C14 | −163.29 (19) |
C5—C6—C7—C11 | −105.9 (2) | C18—C13—C14—C15 | −1.5 (3) |
C1—C6—C7—C8 | −107.6 (2) | C12—C13—C14—C15 | 179.6 (2) |
C5—C6—C7—C8 | 72.1 (3) | C13—C14—C15—C16 | 1.2 (4) |
C9—O1—C8—O2 | 2.7 (3) | C14—C15—C16—C17 | 0.3 (4) |
C9—O1—C8—C7 | −176.8 (2) | C15—C16—C17—C18 | −1.4 (4) |
C11—C7—C8—O2 | −3.9 (3) | C14—C13—C18—C17 | 0.4 (3) |
C6—C7—C8—O2 | 178.02 (18) | C12—C13—C18—C17 | 179.3 (2) |
C11—C7—C8—O1 | 175.63 (17) | C16—C17—C18—C13 | 1.1 (4) |
C6—C7—C8—O1 | −2.5 (2) | C11—N1—C19—C20 | −154.4 (2) |
C8—O1—C9—C10 | 103.2 (10) | N1—C19—C20—C21 | 64.4 (4) |
C19—N1—C11—C7 | −172.39 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.91 (2) | 1.93 (2) | 2.653 (3) | 136 (1) |
Experimental details
Crystal data | |
Chemical formula | C21H25NO2 |
Mr | 323.42 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 12.186 (2), 8.4771 (17), 19.080 (4) |
β (°) | 106.33 (3) |
V (Å3) | 1891.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.28 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Rigaku Saturn diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.980, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12325, 3323, 2290 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.198, 1.06 |
No. of reflections | 3323 |
No. of parameters | 232 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.19 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.905 (16) | 1.925 (17) | 2.653 (3) | 136.3 (14) |
Acknowledgements
We thank the Technology Fund of Tianjin Bureau of Public Health (grant No. 04KY36) for financial support.
References
Du, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919–5922. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xue, J. Y., Xiao, Z. P., Shi, L., Tan, S. H., Li, H. Q. & Zhu, H. L. (2007). Aust. J. Chem. 60, 957–962. Web of Science CrossRef CAS Google Scholar
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.
Enamine compounds have been considered to be potential antibacterial agents (Xue et al., 2007) and found important application in the synthesis of N-containint heterocylcles (Du et al., 2006). To further study the structure and activity relationship, we determine the crystal structure of the title compound, (I).
In the molecular structure (Fig. 1), the torsion angles of N1—C11—C7—C6 and C8—C7—C11—C12 are -177.32 (17) and -175.14 (16)°, respectively. Furthermore, the distances C7—C11 and C11—N1 are 1.381 (3), 1.348 (3)Å, respectively. Both of these features confirm the enamine structure formation. The two phenyl rings constructed an angle of 76.04 (12)°. The molecule adopts a Z-conformation, being stabilised by an intramolecular N—H···O hydrogen bond (Table 1).