Literature DB >> 21578334

3-Anilino-1,3-di-2-pyridylpropan-1-one.

Hai-Xing Liu1.   

Abstract

The title compound, C(19)H(17)N(3)O, was prepared by the 1,4-addition reaction of 1,3-di-2-pyridylprop-2-en-1-one with aniline, and includes one chiral C atom of the methine group with an R configuration. The crystal structure is stabilized by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds. The crystal structure also exhibits weak inter-molecular C-H⋯π inter-actions between a pyridyl H atom and the phenyl ring of adjacent mol-ecules.

Entities:  

Year:  2009        PMID： 21578334      PMCID： PMC2971067          DOI： 10.1107/S160053680904121X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For properties of binucleating ligand coordination compounds, see: Casalino et al. (2009 ▶); Clare et al. (2004 ▶); Lam et al. (1996 ▶). For multiple pyridyl compounds, see: Huang et al. (2008 ▶). For related structures, see: Champouret et al. (2006 ▶); Murthy et al. (2001 ▶).

Experimental

Crystal data

C19H17N3O M = 303.36 Orthorhombic, a = 9.316 (2) Å b = 10.275 (2) Å c = 16.652 (3) Å V = 1594.0 (5) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.35 × 0.30 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick (2000 ▶) T min = 0.950, T max = 0.976 7562 measured reflections 1961 independent reflections 1040 reflections with I > 2σ(I) R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.118 S = 1.00 1961 reflections 208 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.13 e Å−3 Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904121X/lx2115sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680904121X/lx2115Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H17N3ODx = 1.264 Mg m−3
Mr = 303.36Melting point: 400 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ac 2abCell parameters from 1025 reflections
a = 9.316 (2) Åθ = 2.3–27.0°
b = 10.275 (2) ŵ = 0.08 mm−1
c = 16.652 (3) ÅT = 293 K
V = 1594.0 (5) Å3Block, yellow
Z = 40.35 × 0.30 × 0.24 mm
F(000) = 640
Bruker SMART CCD diffractometer1961 independent reflections
Radiation source: fine-focus sealed tube1040 reflections with I > 2σ(I)
graphiteRint = 0.077
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 2.3°
φ and ω scansh = −11→10
Absorption correction: multi-scan (SADABS; Sheldrick (2000)k = −13→13
Tmin = 0.950, Tmax = 0.976l = −13→21
7562 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.118H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0005P)2 + 0.0531P] where P = (Fo2 + 2Fc2)/3
1961 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.13 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
O10.5253 (4)0.4411 (3)0.5808 (2)0.0934 (11)
N10.6804 (4)0.1340 (3)0.5653 (2)0.0659 (9)
N20.6078 (3)0.4744 (3)0.8480 (2)0.0551 (8)
N30.3789 (3)0.2540 (3)0.7351 (2)0.0628 (9)
H3N0.39710.18510.70760.075*
C10.7052 (5)0.0421 (5)0.5109 (3)0.0828 (14)
H10.7626−0.02770.52600.099*
C20.6530 (5)0.0426 (5)0.4350 (3)0.0841 (14)
H20.6734−0.02520.39970.101*
C30.5700 (5)0.1446 (5)0.4115 (3)0.0754 (13)
H30.53240.14800.35980.090*
C40.5428 (5)0.2424 (4)0.4655 (3)0.0693 (12)
H40.48680.31350.45080.083*
C50.5998 (4)0.2338 (3)0.5418 (2)0.0531 (10)
C60.5753 (4)0.3385 (4)0.6019 (3)0.0612 (11)
C70.6147 (4)0.3152 (4)0.6885 (2)0.0614 (11)
H7A0.69770.36770.70210.074*
H7B0.64050.22450.69560.074*
C80.4910 (4)0.3490 (3)0.7454 (2)0.0512 (10)
H80.45270.43400.72930.061*
C90.5452 (4)0.3607 (3)0.8309 (2)0.0493 (9)
C100.5356 (4)0.2627 (4)0.8858 (3)0.0660 (11)
H100.49120.18460.87260.079*
C110.5924 (5)0.2811 (5)0.9609 (3)0.0828 (14)
H11A0.58570.21560.99920.099*
C120.6590 (5)0.3961 (6)0.9794 (3)0.0842 (15)
H120.70000.41011.02960.101*
C130.6627 (4)0.4886 (4)0.9215 (3)0.0701 (13)
H130.70650.56740.93390.084*
C140.2431 (4)0.2689 (3)0.7675 (2)0.0504 (9)
C150.1444 (4)0.1682 (3)0.7591 (2)0.0552 (10)
H150.17200.09070.73480.066*
C160.0075 (5)0.1827 (4)0.7863 (3)0.0652 (11)
H16−0.05740.11490.77940.078*
C17−0.0373 (4)0.2942 (4)0.8235 (3)0.0654 (11)
H17−0.13120.30270.84170.078*
C180.0597 (4)0.3928 (4)0.8330 (3)0.0611 (11)
H180.03120.46900.85860.073*
C190.2000 (4)0.3816 (3)0.8054 (2)0.0545 (10)
H190.26440.44980.81240.065*
U11U22U33U12U13U23
O10.135 (3)0.0631 (17)0.082 (2)0.0240 (19)−0.001 (2)0.0020 (17)
N10.071 (2)0.067 (2)0.060 (2)0.0110 (19)−0.0054 (18)−0.008 (2)
N20.0545 (19)0.0534 (19)0.057 (2)−0.0029 (16)0.0051 (16)−0.0056 (17)
N30.0509 (19)0.0561 (19)0.082 (2)−0.0027 (16)0.0062 (17)−0.0321 (19)
C10.098 (4)0.081 (3)0.069 (3)0.023 (3)−0.011 (3)−0.011 (3)
C20.096 (4)0.083 (3)0.073 (3)0.008 (3)0.002 (3)−0.020 (3)
C30.094 (4)0.082 (3)0.050 (3)−0.007 (3)0.007 (2)0.000 (3)
C40.084 (3)0.066 (3)0.057 (3)−0.002 (2)0.002 (2)0.019 (2)
C50.055 (2)0.047 (2)0.057 (3)−0.005 (2)0.0043 (19)0.008 (2)
C60.066 (3)0.056 (2)0.062 (3)0.001 (2)0.006 (2)0.002 (2)
C70.064 (3)0.065 (2)0.055 (3)0.002 (2)0.005 (2)−0.009 (2)
C80.050 (2)0.0438 (19)0.060 (3)−0.0032 (18)0.0016 (18)−0.0048 (19)
C90.046 (2)0.0425 (19)0.060 (2)0.0001 (18)0.0037 (19)−0.002 (2)
C100.068 (3)0.052 (2)0.077 (3)0.001 (2)0.009 (2)0.012 (2)
C110.091 (4)0.087 (3)0.069 (3)0.028 (3)0.015 (3)0.028 (3)
C120.084 (4)0.110 (4)0.058 (3)0.025 (3)−0.007 (3)−0.008 (3)
C130.063 (3)0.076 (3)0.071 (3)−0.001 (2)0.002 (2)−0.021 (3)
C140.052 (2)0.046 (2)0.054 (2)0.0035 (18)−0.0036 (19)−0.007 (2)
C150.060 (3)0.048 (2)0.058 (2)−0.001 (2)−0.002 (2)−0.0083 (19)
C160.064 (3)0.064 (3)0.068 (3)−0.013 (2)0.005 (2)0.001 (2)
C170.050 (2)0.079 (3)0.067 (3)0.009 (2)0.006 (2)0.000 (2)
C180.065 (3)0.059 (2)0.059 (3)0.015 (2)−0.003 (2)−0.005 (2)
C190.055 (3)0.051 (2)0.058 (2)0.0027 (18)−0.006 (2)−0.0078 (19)
O1—C61.205 (4)C8—C91.516 (5)
N1—C51.329 (4)C8—H80.9800
N1—C11.330 (5)C9—C101.363 (5)
N2—C131.335 (5)C10—C111.370 (7)
N2—C91.336 (4)C10—H100.9300
N3—C141.384 (4)C11—C121.370 (6)
N3—C81.440 (4)C11—H11A0.9300
N3—H3N0.8600C12—C131.354 (6)
C1—C21.354 (7)C12—H120.9300
C1—H10.9300C13—H130.9300
C2—C31.359 (6)C14—C191.379 (5)
C2—H20.9300C14—C151.390 (5)
C3—C41.372 (6)C15—C161.362 (5)
C3—H30.9300C15—H150.9300
C4—C51.380 (6)C16—C171.367 (5)
C4—H40.9300C16—H160.9300
C5—C61.487 (5)C17—C181.366 (5)
C6—C71.506 (6)C17—H170.9300
C7—C81.531 (5)C18—C191.391 (5)
C7—H7A0.9700C18—H180.9300
C7—H7B0.9700C19—H190.9300
C5—N1—C1116.4 (4)C7—C8—H8107.9
C13—N2—C9117.2 (4)N2—C9—C10122.1 (4)
C14—N3—C8122.8 (3)N2—C9—C8114.5 (3)
C14—N3—H3N118.6C10—C9—C8123.4 (3)
C8—N3—H3N118.6C9—C10—C11119.0 (4)
N1—C1—C2124.8 (5)C9—C10—H10120.5
N1—C1—H1117.6C11—C10—H10120.5
C2—C1—H1117.6C12—C11—C10119.9 (4)
C1—C2—C3118.4 (5)C12—C11—H11A120.0
C1—C2—H2120.8C10—C11—H11A120.0
C3—C2—H2120.8C13—C12—C11117.2 (4)
C2—C3—C4118.8 (4)C13—C12—H12121.4
C2—C3—H3120.6C11—C12—H12121.4
C4—C3—H3120.6N2—C13—C12124.5 (4)
C3—C4—C5119.0 (4)N2—C13—H13117.7
C3—C4—H4120.5C12—C13—H13117.7
C5—C4—H4120.5C19—C14—N3122.5 (3)
N1—C5—C4122.5 (4)C19—C14—C15118.6 (3)
N1—C5—C6116.5 (4)N3—C14—C15118.9 (3)
C4—C5—C6121.0 (4)C16—C15—C14120.3 (3)
O1—C6—C5119.8 (4)C16—C15—H15119.9
O1—C6—C7120.8 (4)C14—C15—H15119.9
C5—C6—C7119.5 (3)C15—C16—C17121.9 (4)
C6—C7—C8111.9 (3)C15—C16—H16119.0
C6—C7—H7A109.2C17—C16—H16119.0
C8—C7—H7A109.2C18—C17—C16118.1 (4)
C6—C7—H7B109.2C18—C17—H17120.9
C8—C7—H7B109.2C16—C17—H17120.9
H7A—C7—H7B107.9C17—C18—C19121.5 (4)
N3—C8—C9114.0 (3)C17—C18—H18119.3
N3—C8—C7108.5 (3)C19—C18—H18119.3
C9—C8—C7110.4 (3)C14—C19—C18119.6 (4)
N3—C8—H8107.9C14—C19—H19120.2
C9—C8—H8107.9C18—C19—H19120.2
C5—N1—C1—C2−1.0 (7)N3—C8—C9—N2−157.1 (3)
N1—C1—C2—C30.7 (8)C7—C8—C9—N280.3 (4)
C1—C2—C3—C40.0 (7)N3—C8—C9—C1024.8 (5)
C2—C3—C4—C5−0.3 (7)C7—C8—C9—C10−97.7 (4)
C1—N1—C5—C40.7 (6)N2—C9—C10—C11−0.2 (6)
C1—N1—C5—C6−178.4 (4)C8—C9—C10—C11177.7 (4)
C3—C4—C5—N1−0.1 (6)C9—C10—C11—C12−0.8 (7)
C3—C4—C5—C6179.0 (4)C10—C11—C12—C131.3 (7)
N1—C5—C6—O1167.1 (4)C9—N2—C13—C120.0 (6)
C4—C5—C6—O1−12.0 (6)C11—C12—C13—N2−0.9 (7)
N1—C5—C6—C7−12.3 (5)C8—N3—C14—C196.6 (5)
C4—C5—C6—C7168.6 (4)C8—N3—C14—C15−175.7 (3)
O1—C6—C7—C851.2 (5)C19—C14—C15—C161.5 (6)
C5—C6—C7—C8−129.4 (3)N3—C14—C15—C16−176.3 (4)
C14—N3—C8—C967.7 (4)C14—C15—C16—C17−1.0 (6)
C14—N3—C8—C7−168.8 (3)C15—C16—C17—C180.0 (6)
C6—C7—C8—N369.9 (4)C16—C17—C18—C190.6 (6)
C6—C7—C8—C9−164.4 (3)N3—C14—C19—C18176.7 (4)
C13—N2—C9—C100.6 (5)C15—C14—C19—C18−0.9 (5)
C13—N2—C9—C8−177.4 (3)C17—C18—C19—C14−0.1 (6)
D—H···AD—HH···AD···AD—H···A
N3—H3N···N2i0.862.353.191 (4)164
C10—H10···O1i0.932.623.398 (5)141
C3—H3···Cgii0.932.773.548 (5)142
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H3N⋯N2i0.862.353.191 (4)164
C10—H10⋯O1i0.932.623.398 (5)141
C3—H3⋯Cgii0.932.773.548 (5)142

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C14–C19 phenyl ring.

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