Literature DB >> 21580940

4-{Eth-yl[(E)-4-(4-pyridylvin-yl)phenyl]-amino}benzaldehyde.

Dao-Fu Liu, Yong-Hong Chen, Feng-Wu Wang.   

Abstract

In the title mol-ecule, C(22)H(20)N(2)O, the central aromatic ring forms dihedral angles of 45.30 (2) and 69.43 (2)°, respectively, with the outer pyridine and benzene rings. In the crystal structure, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into layers parallel to the ab plane.

Entities:  

Year:  2008        PMID： 21580940      PMCID： PMC2959691          DOI： 10.1107/S1600536808031358

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


Related literature

For related structure information, see: Allen et al. (1987 ▶). For general background, see: Marder (2006 ▶).

Experimental

Crystal data

C22H20N2O M = 328.40 Triclinic, a = 8.8338 (14) Å b = 9.5747 (18) Å c = 10.472 (2) Å α = 86.621 (2)° β = 84.276 (1)° γ = 83.886 (1)° V = 875.3 (3) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 298 (2) K 0.50 × 0.40 × 0.36 mm

Data collection

Bruker SMART area-dectector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.963, T max = 0.973 4562 measured reflections 3036 independent reflections 2092 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.067 wR(F 2) = 0.209 S = 1.02 3036 reflections 228 parameters H-atom parameters constrained Δρmax = 0.59 e Å−3 Δρmin = −0.21 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031358/cv2455sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031358/cv2455Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H20N2OZ = 2
Mr = 328.40F(000) = 348
Triclinic, P1Dx = 1.246 Mg m−3
a = 8.8338 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5747 (18) ÅCell parameters from 1751 reflections
c = 10.472 (2) Åθ = 2.3–27.2°
α = 86.621 (2)°µ = 0.08 mm−1
β = 84.276 (1)°T = 298 K
γ = 83.886 (1)°Block, yellow
V = 875.3 (3) Å30.50 × 0.40 × 0.36 mm
Bruker APEX area-dectector diffractometer3036 independent reflections
Radiation source: fine-focus sealed tube2092 reflections with I > 2σ(I)
graphiteRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −10→10
Tmin = 0.963, Tmax = 0.973k = −11→11
4562 measured reflectionsl = −12→9
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.210w = 1/[σ2(Fo2) + (0.0993P)2 + 0.5822P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3036 reflectionsΔρmax = 0.59 e Å−3
228 parametersΔρmin = −0.21 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.053 (9)
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.
xyzUiso*/Ueq
N10.6686 (3)0.5962 (2)0.8163 (2)0.0589 (7)
N20.8199 (3)−0.3738 (3)0.3196 (3)0.0651 (7)
O1−0.0027 (3)0.9357 (3)0.8369 (3)0.0855 (8)
C10.1224 (4)0.9637 (3)0.8579 (3)0.0670 (9)
H10.12991.05400.88310.080*
C20.2628 (3)0.8680 (3)0.8471 (3)0.0543 (7)
C30.4016 (4)0.9124 (3)0.8714 (3)0.0637 (9)
H30.40351.00410.89560.076*
C40.5361 (4)0.8255 (3)0.8609 (3)0.0610 (8)
H40.62690.85890.87740.073*
C50.5362 (3)0.6866 (3)0.8254 (3)0.0502 (7)
C60.3954 (3)0.6420 (3)0.8015 (3)0.0503 (7)
H60.39210.55010.77870.060*
C70.2630 (3)0.7309 (3)0.8109 (2)0.0509 (7)
H70.17200.69890.79280.061*
C80.6755 (3)0.4681 (3)0.7520 (3)0.0502 (7)
C90.6535 (3)0.4731 (3)0.6235 (3)0.0496 (7)
H90.62910.55940.58100.060*
C100.6671 (3)0.3521 (3)0.5574 (3)0.0522 (7)
H100.64990.35770.47100.063*
C110.7055 (3)0.2228 (3)0.6162 (3)0.0518 (7)
C120.7281 (4)0.2186 (3)0.7447 (3)0.0635 (8)
H120.75440.13240.78670.076*
C130.7127 (4)0.3398 (3)0.8128 (3)0.0633 (8)
H130.72750.33430.89970.076*
C140.7174 (3)0.0976 (3)0.5376 (3)0.0604 (8)
H140.66890.10840.46220.073*
C150.7878 (3)−0.0247 (3)0.5623 (3)0.0611 (8)
H150.8373−0.03810.63710.073*
C160.7031 (4)−0.2750 (3)0.3192 (3)0.0608 (8)
H160.6279−0.28370.26490.073*
C170.6865 (3)−0.1606 (3)0.3941 (3)0.0600 (8)
H170.6028−0.09360.38820.072*
C180.7943 (3)−0.1442 (3)0.4789 (3)0.0545 (7)
C190.9135 (3)−0.2486 (3)0.4816 (3)0.0643 (8)
H190.9882−0.24580.53780.077*
C200.9211 (4)−0.3565 (3)0.4006 (3)0.0676 (9)
H201.0050−0.42380.40270.081*
C210.8183 (4)0.6392 (3)0.8480 (3)0.0650 (8)
H21A0.90100.57500.81060.078*
H21B0.83130.73270.81020.078*
C220.8276 (5)0.6394 (4)0.9886 (4)0.0863 (11)
H22A0.74730.70451.02570.129*
H22B0.92490.66711.00490.129*
H22C0.81650.54671.02620.129*
U11U22U33U12U13U23
N10.0578 (15)0.0496 (14)0.0732 (16)0.0037 (11)−0.0218 (12)−0.0252 (12)
N20.0703 (17)0.0542 (16)0.0700 (17)−0.0036 (13)0.0055 (14)−0.0210 (13)
O10.0712 (16)0.0721 (16)0.112 (2)0.0133 (13)−0.0176 (14)−0.0154 (14)
C10.078 (2)0.0516 (18)0.071 (2)0.0061 (16)−0.0103 (17)−0.0125 (15)
C20.0678 (19)0.0442 (16)0.0501 (15)0.0073 (13)−0.0110 (13)−0.0101 (12)
C30.083 (2)0.0386 (16)0.072 (2)0.0053 (15)−0.0229 (17)−0.0201 (14)
C40.0686 (19)0.0464 (17)0.0721 (19)−0.0005 (14)−0.0229 (16)−0.0194 (14)
C50.0638 (18)0.0415 (15)0.0471 (15)0.0014 (13)−0.0145 (13)−0.0127 (11)
C60.0606 (17)0.0398 (15)0.0516 (15)−0.0025 (12)−0.0052 (13)−0.0142 (12)
C70.0568 (17)0.0490 (16)0.0468 (15)−0.0011 (13)−0.0048 (12)−0.0100 (12)
C80.0500 (15)0.0428 (15)0.0591 (17)0.0025 (12)−0.0129 (13)−0.0148 (12)
C90.0467 (15)0.0452 (15)0.0567 (16)0.0033 (12)−0.0089 (12)−0.0077 (12)
C100.0503 (16)0.0568 (18)0.0496 (15)0.0012 (13)−0.0050 (12)−0.0145 (13)
C110.0479 (15)0.0506 (17)0.0574 (17)−0.0021 (12)−0.0007 (12)−0.0187 (13)
C120.073 (2)0.0423 (16)0.073 (2)0.0076 (14)−0.0090 (16)−0.0042 (14)
C130.082 (2)0.0547 (18)0.0540 (17)0.0067 (16)−0.0181 (15)−0.0105 (14)
C140.0536 (17)0.0574 (19)0.0694 (19)−0.0020 (14)0.0002 (14)−0.0120 (15)
C150.0547 (17)0.061 (2)0.0684 (19)−0.0023 (15)−0.0059 (15)−0.0121 (15)
C160.0619 (19)0.0567 (18)0.0651 (18)−0.0082 (15)−0.0029 (15)−0.0167 (15)
C170.0506 (17)0.0494 (17)0.077 (2)0.0035 (13)0.0046 (15)−0.0106 (15)
C180.0506 (16)0.0512 (17)0.0626 (17)−0.0125 (13)0.0054 (13)−0.0165 (13)
C190.0490 (17)0.071 (2)0.073 (2)−0.0028 (15)−0.0025 (14)−0.0155 (16)
C200.0600 (19)0.060 (2)0.078 (2)0.0078 (15)0.0071 (16)−0.0132 (17)
C210.0648 (19)0.0600 (19)0.071 (2)−0.0030 (15)−0.0064 (15)−0.0157 (15)
C220.098 (3)0.084 (3)0.081 (2)−0.003 (2)−0.033 (2)−0.012 (2)
N1—C51.378 (3)C11—C121.377 (4)
N1—C81.426 (3)C11—C141.483 (4)
N1—C211.500 (4)C12—C131.385 (4)
N2—C201.321 (4)C12—H120.9300
N2—C161.323 (4)C13—H130.9300
O1—C11.208 (4)C14—C151.291 (4)
C1—C21.461 (4)C14—H140.9300
C1—H10.9300C15—C181.473 (4)
C2—C71.388 (4)C15—H150.9300
C2—C31.391 (4)C16—C171.372 (4)
C3—C41.374 (4)C16—H160.9300
C3—H30.9300C17—C181.391 (4)
C4—C51.402 (4)C17—H170.9300
C4—H40.9300C18—C191.374 (4)
C5—C61.408 (4)C19—C201.367 (4)
C6—C71.370 (4)C19—H190.9300
C6—H60.9300C20—H200.9300
C7—H70.9300C21—C221.482 (5)
C8—C131.373 (4)C21—H21A0.9700
C8—C91.375 (4)C21—H21B0.9700
C9—C101.373 (4)C22—H22A0.9600
C9—H90.9300C22—H22B0.9600
C10—C111.375 (4)C22—H22C0.9600
C10—H100.9300
C5—N1—C8120.6 (2)C11—C12—H12119.3
C5—N1—C21122.0 (2)C13—C12—H12119.3
C8—N1—C21116.3 (2)C8—C13—C12120.0 (3)
C20—N2—C16115.0 (3)C8—C13—H13120.0
O1—C1—C2125.7 (3)C12—C13—H13120.0
O1—C1—H1117.2C15—C14—C11127.0 (3)
C2—C1—H1117.2C15—C14—H14116.5
C7—C2—C3117.8 (3)C11—C14—H14116.5
C7—C2—C1121.4 (3)C14—C15—C18123.7 (3)
C3—C2—C1120.8 (3)C14—C15—H15118.1
C4—C3—C2122.3 (3)C18—C15—H15118.1
C4—C3—H3118.9N2—C16—C17123.9 (3)
C2—C3—H3118.9N2—C16—H16118.1
C3—C4—C5120.0 (3)C17—C16—H16118.1
C3—C4—H4120.0C16—C17—C18120.3 (3)
C5—C4—H4120.0C16—C17—H17119.8
N1—C5—C4121.4 (3)C18—C17—H17119.8
N1—C5—C6121.1 (2)C19—C18—C17115.8 (3)
C4—C5—C6117.5 (3)C19—C18—C15119.7 (3)
C7—C6—C5121.6 (3)C17—C18—C15124.5 (3)
C7—C6—H6119.2C20—C19—C18119.2 (3)
C5—C6—H6119.2C20—C19—H19120.4
C6—C7—C2120.8 (3)C18—C19—H19120.4
C6—C7—H7119.6N2—C20—C19125.8 (3)
C2—C7—H7119.6N2—C20—H20117.1
C13—C8—C9118.8 (3)C19—C20—H20117.1
C13—C8—N1121.8 (3)C22—C21—N1112.0 (3)
C9—C8—N1119.3 (3)C22—C21—H21A109.2
C10—C9—C8120.7 (3)N1—C21—H21A109.2
C10—C9—H9119.6C22—C21—H21B109.2
C8—C9—H9119.6N1—C21—H21B109.2
C9—C10—C11121.4 (3)H21A—C21—H21B107.9
C9—C10—H10119.3C21—C22—H22A109.5
C11—C10—H10119.3C21—C22—H22B109.5
C10—C11—C12117.6 (3)H22A—C22—H22B109.5
C10—C11—C14117.8 (3)C21—C22—H22C109.5
C12—C11—C14124.6 (3)H22A—C22—H22C109.5
C11—C12—C13121.5 (3)H22B—C22—H22C109.5
O1—C1—C2—C7−0.4 (5)C9—C10—C11—C120.8 (4)
O1—C1—C2—C3178.8 (3)C9—C10—C11—C14179.9 (3)
C7—C2—C3—C4−0.2 (5)C10—C11—C12—C130.1 (5)
C1—C2—C3—C4−179.4 (3)C14—C11—C12—C13−178.9 (3)
C2—C3—C4—C5−0.4 (5)C9—C8—C13—C120.3 (5)
C8—N1—C5—C4−165.1 (3)N1—C8—C13—C12−175.7 (3)
C21—N1—C5—C42.2 (4)C11—C12—C13—C8−0.7 (5)
C8—N1—C5—C615.9 (4)C10—C11—C14—C15160.8 (3)
C21—N1—C5—C6−176.8 (3)C12—C11—C14—C15−20.1 (5)
C3—C4—C5—N1−178.9 (3)C11—C14—C15—C18180.0 (3)
C3—C4—C5—C60.1 (4)C20—N2—C16—C171.2 (5)
N1—C5—C6—C7179.7 (3)N2—C16—C17—C18−1.3 (5)
C4—C5—C6—C70.7 (4)C16—C17—C18—C19−0.3 (4)
C5—C6—C7—C2−1.3 (4)C16—C17—C18—C15179.3 (3)
C3—C2—C7—C61.0 (4)C14—C15—C18—C19154.8 (3)
C1—C2—C7—C6−179.8 (3)C14—C15—C18—C17−24.9 (5)
C5—N1—C8—C13−122.4 (3)C17—C18—C19—C201.9 (4)
C21—N1—C8—C1369.6 (4)C15—C18—C19—C20−177.8 (3)
C5—N1—C8—C961.7 (4)C16—N2—C20—C190.5 (5)
C21—N1—C8—C9−106.4 (3)C18—C19—C20—N2−2.1 (5)
C13—C8—C9—C100.6 (4)C5—N1—C21—C2276.9 (4)
N1—C8—C9—C10176.6 (2)C8—N1—C21—C22−115.3 (3)
C8—C9—C10—C11−1.1 (4)
D—H···AD—HH···AD···AD—H···A
C21—H21B···O1i0.972.603.384 (4)138
C15—H15···O1ii0.932.633.553 (4)175
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C21—H21B⋯O1i0.972.603.384 (4)138
C15—H15⋯O1ii0.932.633.553 (4)175

Symmetry codes: (i) ; (ii) .

  2 in total

Review 1.  Organic nonlinear optical materials: where we have been and where we are going.

Authors:  Seth R Marder
Journal:  Chem Commun (Camb)       Date:  2005-11-24       Impact factor: 6.222

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total

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