(E)-1-{4-[(E)-3-Chloro­benzyl­idene­amino]­phen­yl}-3-(3-chloro­phen­yl)prop-2-en-1-one

Cheng, J.-M.; Zheng, Y.-F.; Peng, G.-P.

doi:10.1107/S1600536811013778

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1217

doi:10.1107/S1600536811013778

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(E)-1-{4-[(E)-3-Chlorobenzylideneamino]phenyl}-3-(3-chlorophenyl)prop-2-en-1-one

Jian-Ming Cheng,^a ^* Yun-Feng Zheng ^a and Guo-Ping Peng ^a

^aCollege of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210029, People's Republic of China
^*Correspondence e-mail: cjm7895@163.com

(Received 10 April 2011; accepted 12 April 2011; online 29 April 2011)

In the title molecule, C₂₂H₁₅Cl₂NO, the dihedral angles between the central aromatic ring and the N- and C=O-bonded rings are 43.13 (13) and 0.80 (14)°, respectively. The dihedral angle between the terminal rings is 43.15 (14)°. The major twist occurs about the C_ar—N bond [C_ar—C_ar—N=C = 42.3 (4)°; ar is aromatic].

Related literature

For background to Schiff bases, see: Chimenti et al. (2009 ); Shi et al. (2007 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₁₅Cl₂NO
M_r = 380.25
Monoclinic, P 2₁ /c
a = 17.454 (4) Å
b = 6.1110 (12) Å
c = 17.179 (3) Å
β = 100.32 (3)°
V = 1802.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.866, T_max = 0.964
3659 measured reflections
3539 independent reflections
2367 reflections with I > 2σ(I)
R_int = 0.021
200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.145
S = 1.06
3539 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013778/hb5842sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013778/hb5842Isup2.hkl

checkCIF report

Comment top

There has been much research interest in Schiff base and chalcone compounds due to their biological activities (Shi et al., 2007; Chimenti et al., 2009). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1).

Related literature top

For background to Schiff bases, see: Chimenti et al. (2009); Shi et al. (2007). For reference bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared by stirring a mixture of 3-chlorobenzaldehyde (280 mg, 2 mmol) and 1-(4-aminophenyl)ethanone (135 mg, 1 mmol) in methanol (10 ml) for 4 h. After keeping the filtrate in air for 5 d, colorless block-shaped crystals of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).

Figures top

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.

(E)-1-{4-[(E)-3-Chlorobenzylideneamino]phenyl}- 3-(3-chlorophenyl)prop-2-en-1-one top

Crystal data top

C₂₂H₁₅Cl₂NO	F(000) = 784
M_r = 380.25	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.454 (4) Å	θ = 9–12°
b = 6.1110 (12) Å	µ = 0.37 mm⁻¹
c = 17.179 (3) Å	T = 293 K
β = 100.32 (3)°	Block, colorless
V = 1802.7 (6) Å³	0.40 × 0.30 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2367 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 26.0°, θ_min = 1.2°
ω/2θ scans	h = −21→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.866, T_max = 0.964	l = −20→21
3659 measured reflections	200 standard reflections every 3 reflections
3539 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0633P)² + 0.6746P] where P = (F_o² + 2F_c²)/3
3539 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₂H₁₅Cl₂NO	V = 1802.7 (6) Å³
M_r = 380.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.454 (4) Å	µ = 0.37 mm⁻¹
b = 6.1110 (12) Å	T = 293 K
c = 17.179 (3) Å	0.40 × 0.30 × 0.10 mm
β = 100.32 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2367 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.021
T_min = 0.866, T_max = 0.964	200 standard reflections every 3 reflections
3659 measured reflections	intensity decay: 1%
3539 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.06	Δρ_max = 0.26 e Å⁻³
3539 reflections	Δρ_min = −0.37 e Å⁻³
235 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	0.82827 (15)	−0.0032 (5)	−0.05196 (15)	0.0486 (7)
C2	0.87296 (15)	−0.1135 (5)	−0.09848 (16)	0.0524 (7)
H2	0.8585	−0.2535	−0.1167	0.063*
C3	0.93831 (17)	−0.0187 (6)	−0.11798 (18)	0.0617 (8)
C4	0.96089 (19)	0.1871 (6)	−0.0928 (2)	0.0732 (9)
H4	1.0054	0.2501	−0.1058	0.088*
C5	0.9159 (2)	0.2994 (6)	−0.0476 (2)	0.0802 (10)
H5	0.9301	0.4405	−0.0307	0.096*
C6	0.85060 (18)	0.2070 (5)	−0.02714 (19)	0.0652 (8)
H6	0.8213	0.2855	0.0035	0.078*
C7	0.76114 (15)	−0.1165 (5)	−0.03071 (15)	0.0515 (7)
H7	0.7557	−0.2622	−0.0462	0.062*
C8	0.70704 (15)	−0.0416 (5)	0.00740 (15)	0.0515 (7)
H8	0.7078	0.1040	0.0232	0.062*
C9	0.64549 (16)	−0.1899 (5)	0.02472 (15)	0.0498 (7)
C10	0.58642 (15)	−0.1109 (4)	0.07094 (14)	0.0428 (6)
C11	0.58854 (15)	0.0934 (4)	0.10662 (15)	0.0488 (7)
H11	0.6285	0.1902	0.1017	0.059*
C12	0.53180 (15)	0.1548 (5)	0.14945 (15)	0.0475 (6)
H12	0.5344	0.2910	0.1740	0.057*
C13	0.47135 (15)	0.0137 (4)	0.15568 (14)	0.0429 (6)
C14	0.46980 (17)	−0.1910 (4)	0.12070 (17)	0.0551 (7)
H14	0.4299	−0.2884	0.1254	0.066*
C15	0.52654 (16)	−0.2513 (5)	0.07917 (16)	0.0525 (7)
H15	0.5246	−0.3893	0.0561	0.063*
C16	0.37984 (14)	0.2508 (4)	0.18899 (14)	0.0441 (6)
H16	0.4007	0.3531	0.1586	0.053*
C17	0.31366 (15)	0.3162 (4)	0.22540 (14)	0.0435 (6)
C18	0.28087 (16)	0.5218 (5)	0.20967 (16)	0.0515 (7)
H18	0.3023	0.6187	0.1777	0.062*
C19	0.21688 (17)	0.5833 (5)	0.24099 (18)	0.0591 (8)
H19	0.1958	0.7223	0.2307	0.071*
C20	0.18380 (17)	0.4406 (5)	0.28750 (18)	0.0598 (8)
H20	0.1405	0.4819	0.3087	0.072*
C21	0.21605 (16)	0.2352 (5)	0.30206 (16)	0.0522 (7)
C22	0.28056 (15)	0.1702 (4)	0.27221 (14)	0.0456 (6)
H22	0.3017	0.0315	0.2831	0.055*
Cl1	0.99327 (5)	−0.1679 (2)	−0.17471 (6)	0.0968 (4)
Cl2	0.17205 (5)	0.05098 (15)	0.35786 (5)	0.0771 (3)
N1	0.40982 (12)	0.0634 (4)	0.19679 (12)	0.0468 (5)
O1	0.64304 (12)	−0.3797 (4)	0.00131 (13)	0.0693 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0474 (15)	0.0542 (17)	0.0434 (14)	−0.0010 (13)	0.0060 (12)	−0.0006 (13)
C2	0.0494 (15)	0.0540 (17)	0.0555 (16)	−0.0054 (13)	0.0142 (13)	−0.0054 (14)
C3	0.0508 (17)	0.073 (2)	0.0626 (18)	−0.0045 (16)	0.0147 (14)	0.0011 (16)
C4	0.0557 (18)	0.076 (2)	0.088 (2)	−0.0150 (18)	0.0127 (17)	0.004 (2)
C5	0.080 (2)	0.056 (2)	0.101 (3)	−0.0187 (19)	0.008 (2)	−0.006 (2)
C6	0.0644 (19)	0.058 (2)	0.074 (2)	−0.0058 (16)	0.0129 (16)	−0.0152 (16)
C7	0.0545 (16)	0.0551 (17)	0.0463 (15)	−0.0052 (14)	0.0128 (13)	−0.0080 (13)
C8	0.0561 (16)	0.0539 (17)	0.0465 (15)	−0.0015 (14)	0.0147 (13)	−0.0061 (13)
C9	0.0544 (16)	0.0524 (18)	0.0433 (14)	−0.0001 (14)	0.0105 (12)	−0.0051 (13)
C10	0.0476 (14)	0.0451 (15)	0.0367 (13)	0.0012 (12)	0.0101 (11)	−0.0005 (11)
C11	0.0463 (15)	0.0496 (17)	0.0521 (15)	−0.0084 (13)	0.0134 (12)	−0.0080 (13)
C12	0.0504 (15)	0.0467 (15)	0.0462 (15)	−0.0026 (13)	0.0112 (12)	−0.0085 (13)
C13	0.0509 (15)	0.0417 (15)	0.0379 (13)	0.0044 (12)	0.0127 (11)	0.0077 (12)
C14	0.0620 (17)	0.0414 (16)	0.0688 (18)	−0.0072 (14)	0.0305 (15)	0.0025 (14)
C15	0.0658 (17)	0.0367 (15)	0.0588 (17)	−0.0037 (13)	0.0216 (14)	−0.0044 (13)
C16	0.0491 (14)	0.0444 (15)	0.0410 (14)	−0.0059 (13)	0.0145 (11)	0.0018 (12)
C17	0.0463 (14)	0.0418 (15)	0.0432 (13)	−0.0053 (12)	0.0102 (11)	−0.0051 (12)
C18	0.0541 (16)	0.0446 (16)	0.0576 (17)	−0.0030 (13)	0.0151 (13)	−0.0005 (13)
C19	0.0590 (17)	0.0460 (17)	0.074 (2)	0.0038 (14)	0.0155 (15)	−0.0092 (15)
C20	0.0563 (17)	0.059 (2)	0.070 (2)	−0.0035 (15)	0.0259 (15)	−0.0166 (16)
C21	0.0573 (17)	0.0535 (18)	0.0505 (16)	−0.0132 (14)	0.0218 (13)	−0.0090 (13)
C22	0.0502 (15)	0.0432 (15)	0.0455 (14)	−0.0051 (12)	0.0141 (12)	−0.0026 (12)
Cl1	0.0694 (6)	0.1239 (9)	0.1101 (8)	−0.0134 (6)	0.0507 (5)	−0.0227 (7)
Cl2	0.0919 (6)	0.0759 (6)	0.0763 (5)	−0.0213 (5)	0.0496 (5)	−0.0045 (4)
N1	0.0545 (13)	0.0444 (13)	0.0452 (12)	0.0037 (11)	0.0192 (10)	0.0070 (10)
O1	0.0787 (15)	0.0571 (13)	0.0810 (15)	−0.0079 (11)	0.0379 (12)	−0.0226 (11)

Geometric parameters (Å, º) top

C1—C6	1.387 (4)	C12—C13	1.382 (4)
C1—C2	1.387 (4)	C12—H12	0.9300
C1—C7	1.462 (4)	C13—C14	1.386 (4)
C2—C3	1.373 (4)	C13—N1	1.420 (3)
C2—H2	0.9300	C14—C15	1.370 (4)
C3—C4	1.365 (5)	C14—H14	0.9300
C3—Cl1	1.742 (3)	C15—H15	0.9300
C4—C5	1.382 (5)	C16—N1	1.256 (3)
C4—H4	0.9300	C16—C17	1.464 (3)
C5—C6	1.373 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.387 (4)
C6—H6	0.9300	C17—C22	1.394 (3)
C7—C8	1.323 (4)	C18—C19	1.376 (4)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.476 (4)	C19—C20	1.377 (4)
C8—H8	0.9300	C19—H19	0.9300
C9—O1	1.225 (3)	C20—C21	1.380 (4)
C9—C10	1.490 (3)	C20—H20	0.9300
C10—C15	1.379 (4)	C21—C22	1.377 (4)
C10—C11	1.388 (4)	C21—Cl2	1.743 (3)
C11—C12	1.387 (3)	C22—H22	0.9300
C11—H11	0.9300

C6—C1—C2	118.1 (3)	C13—C12—H12	120.0
C6—C1—C7	123.7 (3)	C11—C12—H12	120.0
C2—C1—C7	118.2 (3)	C12—C13—C14	119.1 (2)
C3—C2—C1	120.8 (3)	C12—C13—N1	124.1 (2)
C3—C2—H2	119.6	C14—C13—N1	116.8 (2)
C1—C2—H2	119.6	C15—C14—C13	120.5 (3)
C4—C3—C2	121.1 (3)	C15—C14—H14	119.7
C4—C3—Cl1	120.2 (2)	C13—C14—H14	119.7
C2—C3—Cl1	118.7 (3)	C14—C15—C10	121.2 (3)
C3—C4—C5	118.3 (3)	C14—C15—H15	119.4
C3—C4—H4	120.8	C10—C15—H15	119.4
C5—C4—H4	120.8	N1—C16—C17	123.3 (2)
C6—C5—C4	121.4 (3)	N1—C16—H16	118.4
C6—C5—H5	119.3	C17—C16—H16	118.4
C4—C5—H5	119.3	C18—C17—C22	119.5 (2)
C5—C6—C1	120.2 (3)	C18—C17—C16	119.6 (2)
C5—C6—H6	119.9	C22—C17—C16	120.8 (2)
C1—C6—H6	119.9	C19—C18—C17	120.5 (3)
C8—C7—C1	129.4 (3)	C19—C18—H18	119.8
C8—C7—H7	115.3	C17—C18—H18	119.8
C1—C7—H7	115.3	C18—C19—C20	120.5 (3)
C7—C8—C9	119.8 (3)	C18—C19—H19	119.8
C7—C8—H8	120.1	C20—C19—H19	119.8
C9—C8—H8	120.1	C19—C20—C21	118.8 (3)
O1—C9—C8	119.9 (2)	C19—C20—H20	120.6
O1—C9—C10	119.7 (3)	C21—C20—H20	120.6
C8—C9—C10	120.4 (2)	C22—C21—C20	121.9 (3)
C15—C10—C11	118.3 (2)	C22—C21—Cl2	119.3 (2)
C15—C10—C9	117.6 (2)	C20—C21—Cl2	118.8 (2)
C11—C10—C9	124.1 (2)	C21—C22—C17	118.8 (3)
C12—C11—C10	120.8 (2)	C21—C22—H22	120.6
C12—C11—H11	119.6	C17—C22—H22	120.6
C10—C11—H11	119.6	C16—N1—C13	118.7 (2)
C13—C12—C11	120.0 (2)

C6—C1—C2—C3	1.3 (4)	C11—C12—C13—C14	1.9 (4)
C7—C1—C2—C3	−177.6 (3)	C11—C12—C13—N1	−178.7 (2)
C1—C2—C3—C4	−0.6 (5)	C12—C13—C14—C15	−1.3 (4)
C1—C2—C3—Cl1	178.6 (2)	N1—C13—C14—C15	179.3 (3)
C2—C3—C4—C5	−0.6 (5)	C13—C14—C15—C10	−0.1 (4)
Cl1—C3—C4—C5	−179.7 (3)	C11—C10—C15—C14	0.7 (4)
C3—C4—C5—C6	0.9 (6)	C9—C10—C15—C14	−179.9 (3)
C4—C5—C6—C1	−0.2 (5)	N1—C16—C17—C18	−175.9 (3)
C2—C1—C6—C5	−0.9 (4)	N1—C16—C17—C22	0.6 (4)
C7—C1—C6—C5	177.9 (3)	C22—C17—C18—C19	1.1 (4)
C6—C1—C7—C8	6.8 (5)	C16—C17—C18—C19	177.6 (3)
C2—C1—C7—C8	−174.4 (3)	C17—C18—C19—C20	−0.9 (4)
C1—C7—C8—C9	−177.9 (3)	C18—C19—C20—C21	0.0 (4)
C7—C8—C9—O1	−2.6 (4)	C19—C20—C21—C22	0.7 (4)
C7—C8—C9—C10	177.1 (2)	C19—C20—C21—Cl2	−177.7 (2)
O1—C9—C10—C15	−5.9 (4)	C20—C21—C22—C17	−0.5 (4)
C8—C9—C10—C15	174.4 (2)	Cl2—C21—C22—C17	177.81 (19)
O1—C9—C10—C11	173.4 (3)	C18—C17—C22—C21	−0.4 (4)
C8—C9—C10—C11	−6.2 (4)	C16—C17—C22—C21	−176.9 (2)
C15—C10—C11—C12	0.0 (4)	C17—C16—N1—C13	176.9 (2)
C9—C10—C11—C12	−179.4 (2)	C12—C13—N1—C16	42.3 (4)
C10—C11—C12—C13	−1.3 (4)	C14—C13—N1—C16	−138.3 (3)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅Cl₂NO
M_r	380.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.454 (4), 6.1110 (12), 17.179 (3)
β (°)	100.32 (3)
V (Å³)	1802.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.866, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	3659, 3539, 2367
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.145, 1.06
No. of reflections	3539
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.37

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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