(2E)-1-{4-[(1E)-Benzyl­ideneamino]phenyl}-3-phenyl­prop-2-en-1-one

Harrison, W.T.A.; Ravindra, H.J.; Kumar, M.R.S.; Dharmaprakash, S.M.

doi:10.1107/S160053680705684X

(2E)-1-{4-[(1E)-Benzylideneamino]phenyl}-3-phenylprop-2-en-1-one

W. T. A. Harrison, H. J. Ravindra, M. R. S. Kumar and S. M. Dharmaprakash

In the title compound, C₂₂H₁₇NO, the dihedral angles between the central benzene ring and the two terminal phenyl rings are 48.20 (4) and 49.62 (4)°, resulting in a substantially twisted molecular conformation. Weak C—H

π interactions help to consolidate the centrosymmetric crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705684X/lh2557sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680705684X/lh2557Isup2.hkl Contains datablock I

CCDC reference: 672916

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C)= 0.002 Å
R factor = 0.038
wR factor = 0.100
Data-to-parameter ratio = 14.8

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No syntax errors found


No errors found in this datablock

Comment top

As part of our ongoing studies of organic nonlinear optical materials derived from substituted chalcones (Harrison et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1). It is centrosymmetric, therefore it does not display any second harmonic generation response.

The dihedral angle between the central (C10—C15) and terminal (C1—C6 and C17—C22) aromatic rings are 49.62 (4)° and 48.20 (4)°, respectively. The dihedral angles for the enone (C7/C8/C9/O1) fragment with respect to C1—C6 and C10—C15 are 25.47 (9)° and 24.37 (8)°, respectively. Overall, the molecule of (I) is substantially twisted.

The only possible directional interactions in (I) are weak C—H···π links (Table 1), with each of the three benzene rings accepting one such bond (Fig. 2).

Related literature top

For background, see: Harrison et al. (2007).

Cg1 is the centroid of atoms C1–C6, Cg2 is the centroid of atoms C10–C15 and Cg3 is the centroid of atoms C17–C22.

Experimental top

A solution of 10% aqueous NaOH (10 ml) and 30 ml me thanol was taken in a conical flask. Benzaldehyde (0.02 mol) and p-amino acetophenone (0.01 mol) were dissolved in 30 ml me thanol and the mixture was added to the conical flask with vigorous stirring. After stirring the solution for 90 minutes, the content were poured into a beaker containing ice cold water and allowed stand for overnight. The resulting precipitate was washed with excess of water, filtered and dried. The compound was purified by successive recrystallization from acetone. Yellow chunks of (I) were obtained by slow evaporation of an acetone solution.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (H atoms are drawn as spheres of arbitrary radius).
	Fig. 2. Unit cell packing for (I) with hydrogen atoms not involved in C—H···π links omitted for clarity

(2E)-1-{4-[(1E)-Benzylideneamino]phenyl}-3-phenylprop-2-en-1-one top

Crystal data top

C₂₂H₁₇NO	F(000) = 656
M_r = 311.37	D_x = 1.249 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6120 reflections
a = 16.8172 (15) Å	θ = 4.4–26.0°
b = 5.9146 (4) Å	µ = 0.08 mm⁻¹
c = 16.6777 (15) Å	T = 291 K
β = 93.501 (1)°	Chunk, yellow
V = 1655.8 (2) Å³	0.49 × 0.43 × 0.31 mm
Z = 4

Data collection top

Bruker SMART1000 CCD diffractometer	2371 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 26.0°, θ_min = 4.4°
ω scans	h = −20→18
8346 measured reflections	k = −7→4
3232 independent reflections	l = −20→20

Refinement top

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0485P)² + 0.1191P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3232 reflections	Δρ_max = 0.12 e Å⁻³
218 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0044 (9)

Crystal data top

C₂₂H₁₇NO	V = 1655.8 (2) Å³
M_r = 311.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8172 (15) Å	µ = 0.08 mm⁻¹
b = 5.9146 (4) Å	T = 291 K
c = 16.6777 (15) Å	0.49 × 0.43 × 0.31 mm
β = 93.501 (1)°

Data collection top

Bruker SMART1000 CCD diffractometer	2371 reflections with I > 2σ(I)
8346 measured reflections	R_int = 0.037
3232 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
3232 reflections	Δρ_min = −0.12 e Å⁻³
218 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.22678 (8)	0.2767 (2)	0.58028 (8)	0.0475 (3)
H1	0.2367	0.4183	0.6030	0.057*
C2	0.16855 (8)	0.1416 (3)	0.60961 (9)	0.0571 (4)
H2	0.1404	0.1906	0.6527	0.068*
C3	0.15194 (9)	−0.0658 (3)	0.57527 (10)	0.0635 (4)
H3	0.1123	−0.1565	0.5948	0.076*
C4	0.19421 (9)	−0.1390 (2)	0.51180 (10)	0.0586 (4)
H4	0.1825	−0.2786	0.4882	0.070*
C5	0.25364 (8)	−0.0068 (2)	0.48311 (8)	0.0494 (3)
H5	0.2823	−0.0587	0.4408	0.059*
C6	0.27113 (7)	0.2047 (2)	0.51708 (7)	0.0424 (3)
C7	0.33125 (8)	0.3563 (2)	0.48715 (8)	0.0464 (3)
H7	0.3290	0.5054	0.5046	0.056*
C8	0.38872 (8)	0.3101 (2)	0.43830 (8)	0.0466 (3)
H8	0.3969	0.1616	0.4224	0.056*
C9	0.43976 (8)	0.4922 (2)	0.40893 (8)	0.0462 (3)
C10	0.51183 (7)	0.4348 (2)	0.36626 (7)	0.0411 (3)
C11	0.55233 (8)	0.2297 (2)	0.37675 (8)	0.0450 (3)
H11	0.5319	0.1180	0.4089	0.054*
C12	0.62236 (8)	0.1911 (2)	0.33977 (8)	0.0459 (3)
H12	0.6493	0.0549	0.3481	0.055*
C13	0.65306 (7)	0.3551 (2)	0.28991 (8)	0.0426 (3)
C14	0.61208 (8)	0.5581 (2)	0.27870 (8)	0.0471 (3)
H14	0.6318	0.6685	0.2455	0.057*
C15	0.54268 (8)	0.5977 (2)	0.31622 (8)	0.0443 (3)
H15	0.5161	0.7345	0.3081	0.053*
C16	0.74793 (8)	0.1473 (2)	0.22590 (8)	0.0475 (3)
H16	0.7121	0.0275	0.2251	0.057*
C17	0.82613 (8)	0.1113 (2)	0.19330 (8)	0.0458 (3)
C18	0.84178 (9)	−0.0890 (2)	0.15418 (9)	0.0555 (4)
H18	0.8034	−0.2024	0.1509	0.067*
C19	0.91353 (10)	−0.1226 (3)	0.12000 (10)	0.0685 (5)
H19	0.9230	−0.2566	0.0930	0.082*
C20	0.97104 (10)	0.0432 (3)	0.12605 (11)	0.0746 (5)
H20	1.0193	0.0222	0.1026	0.090*
C21	0.95689 (10)	0.2413 (3)	0.16705 (12)	0.0755 (5)
H21	0.9962	0.3517	0.1722	0.091*
C22	0.88512 (9)	0.2756 (3)	0.20010 (10)	0.0602 (4)
H22	0.8759	0.4096	0.2272	0.072*
N1	0.72731 (6)	0.33426 (19)	0.25502 (7)	0.0490 (3)
O1	0.42194 (6)	0.69165 (17)	0.41848 (7)	0.0684 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0461 (7)	0.0471 (8)	0.0494 (8)	0.0043 (6)	0.0043 (6)	−0.0034 (6)
C2	0.0505 (8)	0.0672 (10)	0.0551 (9)	0.0042 (7)	0.0156 (7)	0.0037 (7)
C3	0.0541 (9)	0.0618 (10)	0.0758 (11)	−0.0096 (8)	0.0123 (8)	0.0118 (9)
C4	0.0620 (9)	0.0446 (8)	0.0690 (10)	−0.0073 (7)	0.0034 (8)	0.0008 (7)
C5	0.0527 (8)	0.0459 (8)	0.0500 (8)	0.0028 (7)	0.0076 (6)	−0.0016 (6)
C6	0.0392 (7)	0.0424 (7)	0.0454 (7)	0.0028 (6)	0.0017 (6)	0.0031 (6)
C7	0.0466 (7)	0.0427 (7)	0.0502 (8)	0.0010 (6)	0.0046 (6)	−0.0017 (6)
C8	0.0466 (7)	0.0427 (7)	0.0513 (8)	0.0013 (6)	0.0089 (6)	−0.0018 (6)
C9	0.0465 (7)	0.0449 (8)	0.0474 (8)	0.0008 (6)	0.0050 (6)	−0.0024 (6)
C10	0.0414 (7)	0.0408 (7)	0.0410 (7)	−0.0032 (6)	0.0023 (5)	−0.0020 (6)
C11	0.0487 (8)	0.0405 (7)	0.0462 (7)	−0.0020 (6)	0.0065 (6)	0.0047 (6)
C12	0.0462 (7)	0.0406 (7)	0.0509 (8)	0.0031 (6)	0.0030 (6)	0.0039 (6)
C13	0.0370 (7)	0.0443 (7)	0.0465 (7)	−0.0050 (6)	0.0023 (5)	−0.0031 (6)
C14	0.0487 (8)	0.0410 (7)	0.0521 (8)	−0.0051 (6)	0.0072 (6)	0.0055 (6)
C15	0.0455 (7)	0.0374 (7)	0.0501 (7)	0.0006 (6)	0.0030 (6)	0.0017 (6)
C16	0.0442 (7)	0.0487 (8)	0.0497 (8)	−0.0066 (6)	0.0035 (6)	0.0001 (6)
C17	0.0447 (7)	0.0463 (8)	0.0464 (7)	0.0011 (6)	0.0040 (6)	0.0027 (6)
C18	0.0571 (9)	0.0499 (8)	0.0594 (9)	0.0000 (7)	0.0031 (7)	−0.0041 (7)
C19	0.0715 (11)	0.0599 (10)	0.0750 (11)	0.0164 (9)	0.0113 (9)	−0.0103 (8)
C20	0.0528 (9)	0.0749 (12)	0.0985 (13)	0.0134 (9)	0.0239 (9)	0.0007 (10)
C21	0.0494 (9)	0.0637 (10)	0.1154 (15)	−0.0027 (8)	0.0208 (9)	−0.0049 (10)
C22	0.0500 (8)	0.0501 (8)	0.0815 (11)	−0.0006 (7)	0.0126 (7)	−0.0076 (8)
N1	0.0421 (6)	0.0480 (7)	0.0576 (7)	−0.0015 (5)	0.0081 (5)	−0.0009 (6)
O1	0.0734 (7)	0.0434 (6)	0.0920 (8)	0.0057 (5)	0.0340 (6)	−0.0004 (5)

Geometric parameters (Å, º) top

C1—C2	1.3764 (19)	C12—C13	1.3969 (18)
C1—C6	1.3945 (18)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.3917 (18)
C2—C3	1.375 (2)	C13—N1	1.4148 (16)
C2—H2	0.9300	C14—C15	1.3776 (18)
C3—C4	1.380 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3774 (19)	C16—N1	1.2648 (17)
C4—H4	0.9300	C16—C17	1.4688 (18)
C5—C6	1.3974 (19)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.3859 (19)
C6—C7	1.4618 (18)	C17—C22	1.3881 (19)
C7—C8	1.3299 (18)	C18—C19	1.380 (2)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.4794 (18)	C19—C20	1.377 (2)
C8—H8	0.9300	C19—H19	0.9300
C9—O1	1.2296 (16)	C20—C21	1.385 (2)
C9—C10	1.4820 (18)	C20—H20	0.9300
C10—C15	1.3952 (17)	C21—C22	1.372 (2)
C10—C11	1.3972 (17)	C21—H21	0.9300
C11—C12	1.3813 (18)	C22—H22	0.9300
C11—H11	0.9300

C2—C1—C6	121.10 (13)	C11—C12—H12	119.8
C2—C1—H1	119.4	C13—C12—H12	119.8
C6—C1—H1	119.4	C14—C13—C12	118.76 (12)
C3—C2—C1	120.03 (14)	C14—C13—N1	117.53 (12)
C3—C2—H2	120.0	C12—C13—N1	123.50 (12)
C1—C2—H2	120.0	C15—C14—C13	120.79 (12)
C2—C3—C4	119.88 (14)	C15—C14—H14	119.6
C2—C3—H3	120.1	C13—C14—H14	119.6
C4—C3—H3	120.1	C14—C15—C10	120.71 (12)
C5—C4—C3	120.45 (14)	C14—C15—H15	119.6
C5—C4—H4	119.8	C10—C15—H15	119.6
C3—C4—H4	119.8	N1—C16—C17	122.78 (12)
C4—C5—C6	120.44 (13)	N1—C16—H16	118.6
C4—C5—H5	119.8	C17—C16—H16	118.6
C6—C5—H5	119.8	C18—C17—C22	118.79 (13)
C1—C6—C5	118.07 (12)	C18—C17—C16	119.88 (13)
C1—C6—C7	118.95 (12)	C22—C17—C16	121.33 (13)
C5—C6—C7	122.93 (12)	C19—C18—C17	120.89 (14)
C8—C7—C6	128.81 (13)	C19—C18—H18	119.6
C8—C7—H7	115.6	C17—C18—H18	119.6
C6—C7—H7	115.6	C20—C19—C18	119.70 (15)
C7—C8—C9	120.74 (12)	C20—C19—H19	120.1
C7—C8—H8	119.6	C18—C19—H19	120.1
C9—C8—H8	119.6	C19—C20—C21	119.85 (15)
O1—C9—C8	120.31 (12)	C19—C20—H20	120.1
O1—C9—C10	119.66 (12)	C21—C20—H20	120.1
C8—C9—C10	120.02 (11)	C22—C21—C20	120.35 (16)
C15—C10—C11	118.57 (12)	C22—C21—H21	119.8
C15—C10—C9	118.29 (12)	C20—C21—H21	119.8
C11—C10—C9	123.07 (12)	C21—C22—C17	120.38 (15)
C12—C11—C10	120.66 (12)	C21—C22—H22	119.8
C12—C11—H11	119.7	C17—C22—H22	119.8
C10—C11—H11	119.7	C16—N1—C13	120.24 (12)
C11—C12—C13	120.48 (12)

C6—C1—C2—C3	−1.6 (2)	C11—C12—C13—C14	0.41 (18)
C1—C2—C3—C4	0.5 (2)	C11—C12—C13—N1	175.06 (12)
C2—C3—C4—C5	0.7 (2)	C12—C13—C14—C15	0.27 (19)
C3—C4—C5—C6	−1.0 (2)	N1—C13—C14—C15	−174.70 (11)
C2—C1—C6—C5	1.35 (19)	C13—C14—C15—C10	−0.09 (19)
C2—C1—C6—C7	178.86 (12)	C11—C10—C15—C14	−0.75 (18)
C4—C5—C6—C1	−0.06 (19)	C9—C10—C15—C14	176.29 (11)
C4—C5—C6—C7	−177.47 (12)	N1—C16—C17—C18	−172.78 (13)
C1—C6—C7—C8	167.12 (13)	N1—C16—C17—C22	6.6 (2)
C5—C6—C7—C8	−15.5 (2)	C22—C17—C18—C19	−2.3 (2)
C6—C7—C8—C9	174.54 (12)	C16—C17—C18—C19	177.14 (13)
C7—C8—C9—O1	−11.7 (2)	C17—C18—C19—C20	1.2 (2)
C7—C8—C9—C10	169.53 (12)	C18—C19—C20—C21	0.7 (3)
O1—C9—C10—C15	−20.47 (18)	C19—C20—C21—C22	−1.5 (3)
C8—C9—C10—C15	158.27 (12)	C20—C21—C22—C17	0.5 (3)
O1—C9—C10—C11	156.43 (13)	C18—C17—C22—C21	1.4 (2)
C8—C9—C10—C11	−24.84 (18)	C16—C17—C22—C21	−177.99 (14)
C15—C10—C11—C12	1.43 (18)	C17—C16—N1—C13	−176.22 (11)
C9—C10—C11—C12	−175.46 (11)	C14—C13—N1—C16	−143.44 (13)
C10—C11—C12—C13	−1.27 (19)	C12—C13—N1—C16	41.85 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg3ⁱ	0.93	2.89	3.603 (3)	135
C12—H12···Cg1ⁱⁱ	0.93	2.94	3.626 (2)	132
C15—H15···Cg2ⁱⁱⁱ	0.93	2.89	3.559 (2)	130

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇NO
M_r	311.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	16.8172 (15), 5.9146 (4), 16.6777 (15)
β (°)	93.501 (1)
V (Å³)	1655.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.49 × 0.43 × 0.31

Data collection
Diffractometer	Bruker SMART1000 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8346, 3232, 2371
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.100, 1.02
No. of reflections	3232
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXL97.