(2E)-1-(4-Amino-phen-yl)-3-(2,4-dichloro-phen-yl)prop-2-en-1-one.

The title compound, C(15)H(11)Cl(2)NO, is approximately planar (r.m.s. deviation = 0.062 Å) and contains a single C=C double bond in a trans (E) configuration. The crystal packing is stabilized by intermolecular N-H⋯N and N-H⋯O inter-molecular hydrogen bonding.

Related literature

For related flavonoids, see: Bargellini & Marini-Bettolo (1940 ▶). For isoflavonoids, see: Nógrádi & Szöllösy (1996 ▶). For the biological activities of chalcones, see: Go et al. (2005 ▶); Hans et al. (2010 ▶); Trivedi et al. (2007 ▶); Nielsen et al. (2004 ▶). For anti­malarial activity, see: Mishra et al. (2008 ▶). For anti­filarial activity, see: Awasthi, Mishra, Dixit et al. (2009 ▶). For other chalcone crystal structures and small mol­ecules, see: Fun et al. (2008 ▶); Li et al. (2009 ▶); Singh et al. (2011 ▶). For the synthesis, see: Migrdichian (1957 ▶); Awasthi, Mishra, Kumar et al. (2009 ▶). For inter­molecular N—H⋯N and N—H⋯O hydrogen bonding, see: Fonar et al. (2001 ▶).

Experimental

Crystal data

C15H11Cl2NO

M = 292.15

Monoclinic,

a = 22.771 (2) Å

b = 3.9889 (5) Å

c = 14.7848 (18) Å

β = 92.401 (12)°

V = 1341.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 293 K

0.23 × 0.11 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.597, T max = 1.000

5765 measured reflections

2625 independent reflections

1733 reflections with I > 2σ(I)

R int = 0.047

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.159

S = 0.98

2625 reflections

216 parameters

All H-atom parameters refined

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020460/zj2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020460/zj2011Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020460/zj2011Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H11Cl2NO	F(000) = 600
Mr = 292.15	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1458 reflections
a = 22.771 (2) Å	θ = 3.0–29.0°
b = 3.9889 (5) Å	µ = 0.47 mm−1
c = 14.7848 (18) Å	T = 293 K
β = 92.401 (12)°	Rod, yellow
V = 1341.7 (3) Å3	0.23 × 0.11 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	1733 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −25→28
Tmin = 0.597, Tmax = 1.000	k = −3→4
5765 measured reflections	l = −17→18

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) = 0.159	All H-atom parameters refined
S = 0.98	w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3
2625 reflections	(Δ/σ)max = 0.003
216 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
C1	0.85377 (14)	0.5099 (8)	0.5485 (2)	0.0466 (8)
C2	0.91136 (15)	0.6162 (9)	0.5505 (2)	0.0496 (8)
C3	0.93472 (13)	0.7698 (8)	0.6273 (2)	0.0454 (8)
C4	0.90165 (14)	0.8197 (8)	0.7010 (2)	0.0465 (8)
C5	0.84351 (14)	0.7060 (8)	0.6984 (2)	0.0440 (7)
C6	0.81845 (12)	0.5488 (7)	0.62200 (19)	0.0376 (7)
C7	0.75725 (13)	0.4285 (8)	0.6200 (2)	0.0434 (8)
C8	0.72868 (14)	0.2879 (9)	0.5517 (2)	0.0452 (8)
C9	0.66735 (13)	0.1629 (7)	0.5571 (2)	0.0403 (7)
C10	0.63905 (12)	−0.0047 (7)	0.47851 (18)	0.0334 (6)
C11	0.66507 (13)	−0.0353 (8)	0.3948 (2)	0.0408 (7)
C12	0.63760 (13)	−0.1948 (8)	0.3229 (2)	0.0421 (7)
C13	0.58122 (12)	−0.3296 (7)	0.33087 (19)	0.0344 (7)
C14	0.55456 (13)	−0.2959 (8)	0.4125 (2)	0.0384 (7)
C15	0.58231 (13)	−0.1377 (8)	0.4847 (2)	0.0392 (7)
N1	0.55305 (14)	−0.4825 (8)	0.2576 (2)	0.0443 (7)
O1	0.64210 (10)	0.1991 (6)	0.62783 (15)	0.0604 (7)
Cl1	1.00725 (4)	0.9059 (2)	0.63141 (7)	0.0648 (3)
Cl2	0.80366 (5)	0.7782 (3)	0.79390 (6)	0.0786 (4)
H1	0.8413 (15)	0.404 (8)	0.482 (2)	0.057 (9)*
H1N1	0.5731 (15)	−0.545 (9)	0.220 (2)	0.041 (10)*
H2	0.9359 (16)	0.602 (9)	0.509 (2)	0.058 (10)*
H2N1	0.5329 (19)	−0.618 (10)	0.275 (3)	0.067 (15)*
H4	0.9136 (16)	0.923 (9)	0.749 (3)	0.065 (11)*
H7	0.7369 (18)	0.430 (10)	0.674 (3)	0.078 (12)*
H8	0.7462 (17)	0.234 (9)	0.505 (3)	0.065 (12)*
H11	0.7039 (18)	0.068 (10)	0.384 (3)	0.075 (11)*
H12	0.6574 (14)	−0.213 (7)	0.271 (2)	0.042 (8)*
H14	0.5245 (17)	−0.397 (9)	0.422 (2)	0.060 (11)*
H15	0.5611 (13)	−0.119 (7)	0.537 (2)	0.038 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0408 (17)	0.055 (2)	0.0431 (18)	−0.0017 (16)	−0.0039 (14)	−0.0028 (16)
C2	0.0424 (18)	0.056 (2)	0.051 (2)	−0.0029 (16)	0.0079 (16)	−0.0013 (17)
C3	0.0372 (15)	0.0416 (17)	0.056 (2)	−0.0002 (14)	−0.0094 (15)	0.0068 (15)
C4	0.0461 (18)	0.0424 (19)	0.050 (2)	−0.0059 (15)	−0.0119 (16)	−0.0010 (16)
C5	0.0446 (17)	0.0468 (18)	0.0400 (16)	−0.0010 (15)	−0.0043 (14)	−0.0017 (14)
C6	0.0349 (15)	0.0369 (16)	0.0403 (16)	−0.0002 (13)	−0.0054 (13)	0.0005 (13)
C7	0.0380 (16)	0.0498 (19)	0.0424 (17)	−0.0030 (15)	−0.0007 (14)	−0.0002 (15)
C8	0.0368 (16)	0.057 (2)	0.0421 (18)	−0.0077 (15)	0.0036 (15)	−0.0031 (16)
C9	0.0370 (15)	0.0422 (18)	0.0414 (17)	0.0001 (14)	−0.0004 (14)	0.0033 (14)
C10	0.0268 (13)	0.0373 (16)	0.0361 (15)	0.0007 (12)	−0.0003 (11)	0.0033 (12)
C11	0.0286 (14)	0.0513 (19)	0.0426 (17)	−0.0049 (14)	0.0017 (13)	0.0028 (15)
C12	0.0338 (15)	0.057 (2)	0.0362 (16)	0.0001 (15)	0.0057 (13)	−0.0007 (15)
C13	0.0303 (14)	0.0349 (16)	0.0374 (15)	0.0042 (12)	−0.0043 (12)	0.0009 (12)
C14	0.0275 (15)	0.0425 (18)	0.0452 (17)	−0.0054 (14)	0.0007 (13)	0.0031 (14)
C15	0.0333 (15)	0.0470 (19)	0.0378 (16)	0.0013 (14)	0.0068 (13)	0.0016 (14)
N1	0.0372 (15)	0.054 (2)	0.0409 (16)	−0.0038 (15)	−0.0023 (13)	−0.0097 (15)
O1	0.0515 (13)	0.0868 (19)	0.0436 (13)	−0.0177 (13)	0.0096 (11)	−0.0133 (12)
Cl1	0.0387 (5)	0.0691 (6)	0.0857 (7)	−0.0114 (4)	−0.0079 (4)	0.0039 (5)
Cl2	0.0705 (6)	0.1094 (9)	0.0565 (6)	−0.0218 (6)	0.0104 (5)	−0.0299 (6)

C1—C2	1.377 (5)	C9—O1	1.223 (4)
C1—C6	1.388 (4)	C9—C10	1.466 (4)
C1—H1	1.10 (3)	C10—C11	1.399 (4)
C2—C3	1.377 (5)	C10—C15	1.403 (4)
C2—H2	0.85 (4)	C11—C12	1.368 (4)
C3—C4	1.365 (5)	C11—H11	0.99 (4)
C3—Cl1	1.737 (3)	C12—C13	1.401 (4)
C4—C5	1.399 (5)	C12—H12	0.91 (3)
C4—H4	0.86 (4)	C13—C14	1.381 (4)
C5—C6	1.393 (4)	C13—N1	1.378 (4)
C5—Cl2	1.734 (3)	C14—C15	1.371 (4)
C6—C7	1.473 (4)	C14—H14	0.81 (4)
C7—C8	1.305 (4)	C15—H15	0.93 (3)
C7—H7	0.94 (4)	N1—H1N1	0.78 (4)
C8—C9	1.488 (4)	N1—H2N1	0.76 (4)
C8—H8	0.84 (4)
C2—C1—C6	122.1 (3)	O1—C9—C10	121.7 (3)
C2—C1—H1	110.2 (18)	O1—C9—C8	118.8 (3)
C6—C1—H1	127.6 (18)	C10—C9—C8	119.5 (3)
C3—C2—C1	119.3 (3)	C11—C10—C15	116.7 (3)
C3—C2—H2	113 (2)	C11—C10—C9	123.5 (3)
C1—C2—H2	128 (2)	C15—C10—C9	119.7 (3)
C4—C3—C2	121.1 (3)	C12—C11—C10	122.1 (3)
C4—C3—Cl1	118.8 (2)	C12—C11—H11	117 (2)
C2—C3—Cl1	120.1 (3)	C10—C11—H11	121 (2)
C3—C4—C5	119.0 (3)	C11—C12—C13	120.2 (3)
C3—C4—H4	125 (3)	C11—C12—H12	117.7 (19)
C5—C4—H4	116 (3)	C13—C12—H12	122.0 (19)
C6—C5—C4	121.5 (3)	C14—C13—N1	121.6 (3)
C6—C5—Cl2	121.6 (2)	C14—C13—C12	118.3 (3)
C4—C5—Cl2	116.8 (2)	N1—C13—C12	120.1 (3)
C1—C6—C5	117.0 (3)	C15—C14—C13	121.4 (3)
C1—C6—C7	121.8 (3)	C15—C14—H14	117 (3)
C5—C6—C7	121.2 (3)	C13—C14—H14	120 (3)
C8—C7—C6	126.6 (3)	C14—C15—C10	121.2 (3)
C8—C7—H7	114 (2)	C14—C15—H15	116.4 (18)
C6—C7—H7	119 (2)	C10—C15—H15	122.4 (18)
C7—C8—C9	122.8 (3)	C13—N1—H1N1	116 (2)
C7—C8—H8	120 (3)	C13—N1—H2N1	109 (3)
C9—C8—H8	116 (3)	H1N1—N1—H2N1	113 (4)
C6—C1—C2—C3	−0.8 (5)	C7—C8—C9—O1	1.5 (5)
C1—C2—C3—C4	−0.4 (5)	C7—C8—C9—C10	−177.5 (3)
C1—C2—C3—Cl1	180.0 (2)	O1—C9—C10—C11	176.4 (3)
C2—C3—C4—C5	1.3 (5)	C8—C9—C10—C11	−4.6 (4)
Cl1—C3—C4—C5	−179.1 (2)	O1—C9—C10—C15	−2.1 (4)
C3—C4—C5—C6	−1.2 (5)	C8—C9—C10—C15	176.8 (3)
C3—C4—C5—Cl2	−179.8 (2)	C15—C10—C11—C12	−1.8 (4)
C2—C1—C6—C5	0.9 (5)	C9—C10—C11—C12	179.7 (3)
C2—C1—C6—C7	−178.8 (3)	C10—C11—C12—C13	1.0 (5)
C4—C5—C6—C1	0.1 (5)	C11—C12—C13—C14	0.2 (4)
Cl2—C5—C6—C1	178.6 (2)	C11—C12—C13—N1	178.3 (3)
C4—C5—C6—C7	179.7 (3)	N1—C13—C14—C15	−178.7 (3)
Cl2—C5—C6—C7	−1.7 (4)	C12—C13—C14—C15	−0.6 (4)
C1—C6—C7—C8	−2.6 (5)	C13—C14—C15—C10	−0.2 (5)
C5—C6—C7—C8	177.8 (3)	C11—C10—C15—C14	1.4 (4)
C6—C7—C8—C9	177.8 (3)	C9—C10—C15—C14	180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.78 (3)	2.210	2.977 (4)	171 (3)
N1—H2N1···N1ii	0.76 (4)	2.469	3.134 (5)	147 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.78 (3)	2.210	2.977 (4)	171 (3)
N1—H2N1⋯N1ii	0.76 (4)	2.469	3.134 (5)	147 (4)

Symmetry codes: (i) ; (ii) .