1-(2,4-Dichloro-phen-yl)-3-[4-(dimethyl-amino)phen-yl]prop-2-enone.

In the title compound, C(17)H(15)Cl(2)NO, the dimethyl-amino-phenyl group is close to coplanar with the central propenone group [dihedral angle = 13.1 (1)° between the mean planes], while the dichloro-phenyl group is twisted from the plane [dihedral angle = 64.0 (1)°]. In the crystal, C-H⋯O and weak C-H⋯π inter-actions are formed between mol-ecules.

Related literature

For related structures, see: Murafuji et al. (1999 ▶); Liu et al. (2002 ▶); Patil et al. (2007a ▶,b ▶); Rosli et al. (2007 ▶).

Experimental

Crystal data

C17H15Cl2NO

M = 320.20

Monoclinic,

a = 8.5741 (19) Å

b = 12.706 (3) Å

c = 14.671 (3) Å

β = 102.645 (4)°

V = 1559.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 290 K

0.25 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.972

11540 measured reflections

2908 independent reflections

2039 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.03

2908 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015177/bi2360sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015177/bi2360Isup2.hkl

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

C17H15Cl2NO	F(000) = 664
Mr = 320.20	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3980 reflections
a = 8.5741 (19) Å	θ = 2.0–26.0°
b = 12.706 (3) Å	µ = 0.41 mm−1
c = 14.671 (3) Å	T = 290 K
β = 102.645 (4)°	Block, orange
V = 1559.5 (6) Å3	0.25 × 0.15 × 0.07 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2908 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.923, Tmax = 0.972	k = −15→15
11540 measured reflections	l = −16→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1972P] where P = (Fo2 + 2Fc2)/3
2908 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.17 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
Cl1	0.42606 (8)	−0.03118 (5)	0.21634 (5)	0.0704 (2)
Cl2	0.33039 (10)	0.29372 (6)	0.42942 (5)	0.0851 (3)
C13	0.2618 (2)	0.71607 (15)	−0.03057 (14)	0.0421 (5)
C10	0.1972 (2)	0.54646 (15)	0.08139 (14)	0.0414 (5)
C9	0.1721 (2)	0.45849 (17)	0.13874 (15)	0.0461 (5)
H9	0.2244	0.3964	0.1299	0.055*
C15	0.2754 (2)	0.53119 (16)	0.00809 (15)	0.0459 (5)
H15	0.3078	0.4636	−0.0037	0.055*
C8	0.0829 (3)	0.45512 (17)	0.20297 (16)	0.0508 (6)
H8	0.0247	0.5151	0.2101	0.061*
N1	0.2898 (2)	0.79802 (13)	−0.08543 (13)	0.0518 (5)
C12	0.1844 (3)	0.73163 (16)	0.04341 (14)	0.0481 (5)
H12	0.1548	0.7993	0.0568	0.058*
C6	0.1595 (2)	0.26655 (16)	0.25224 (16)	0.0469 (5)
C3	0.3204 (3)	0.08209 (17)	0.23089 (17)	0.0509 (6)
C14	0.3057 (2)	0.61262 (16)	−0.04685 (14)	0.0456 (5)
H14	0.3561	0.599	−0.0957	0.055*
C4	0.3608 (3)	0.13662 (17)	0.31339 (16)	0.0519 (6)
H4	0.4425	0.1129	0.3616	0.062*
C11	0.1517 (2)	0.64926 (17)	0.09597 (15)	0.0476 (5)
H11	0.0972	0.6622	0.1431	0.057*
C7	0.0693 (3)	0.36611 (18)	0.26236 (17)	0.0547 (6)
O1	−0.0115 (2)	0.37083 (15)	0.32101 (14)	0.0849 (6)
C5	0.2780 (3)	0.22710 (17)	0.32357 (15)	0.0501 (5)
C2	0.2015 (3)	0.11710 (19)	0.15886 (17)	0.0576 (6)
H2	0.1737	0.079	0.1036	0.069*
C17	0.2722 (3)	0.90604 (18)	−0.05879 (18)	0.0685 (7)
H17A	0.1625	0.9193	−0.0574	0.103*
H17B	0.304	0.9521	−0.1033	0.103*
H17C	0.3383	0.9185	0.0021	0.103*
C16	0.3630 (3)	0.77905 (19)	−0.16414 (17)	0.0665 (7)
H16A	0.4725	0.7587	−0.1417	0.1*
H16B	0.3584	0.8422	−0.2006	0.1*
H16C	0.3064	0.7238	−0.2022	0.1*
C1	0.1244 (3)	0.20911 (18)	0.16968 (17)	0.0577 (6)
H1	0.046	0.2339	0.1202	0.069*

	U11	U22	U33	U12	U13	U23
Cl1	0.0823 (5)	0.0539 (4)	0.0800 (5)	0.0084 (3)	0.0288 (4)	0.0038 (3)
Cl2	0.1090 (6)	0.0798 (5)	0.0577 (4)	0.0164 (4)	−0.0008 (4)	−0.0118 (3)
C13	0.0447 (12)	0.0425 (12)	0.0377 (11)	−0.0018 (9)	0.0062 (9)	0.0013 (9)
C10	0.0437 (11)	0.0407 (12)	0.0406 (12)	0.0008 (9)	0.0110 (10)	0.0024 (9)
C9	0.0442 (12)	0.0439 (12)	0.0499 (13)	0.0026 (9)	0.0098 (10)	0.0023 (10)
C15	0.0531 (13)	0.0363 (11)	0.0508 (13)	0.0034 (10)	0.0166 (11)	−0.0031 (10)
C8	0.0476 (12)	0.0472 (13)	0.0604 (15)	0.0057 (10)	0.0178 (11)	0.0116 (11)
N1	0.0671 (12)	0.0415 (10)	0.0496 (11)	−0.0017 (9)	0.0187 (9)	0.0063 (8)
C12	0.0629 (14)	0.0365 (11)	0.0466 (13)	0.0078 (10)	0.0158 (11)	0.0002 (9)
C6	0.0451 (12)	0.0426 (12)	0.0546 (14)	−0.0054 (10)	0.0142 (11)	0.0104 (10)
C3	0.0543 (14)	0.0443 (13)	0.0585 (15)	−0.0036 (10)	0.0219 (12)	0.0083 (11)
C14	0.0524 (13)	0.0448 (12)	0.0430 (12)	0.0010 (10)	0.0176 (10)	−0.0010 (10)
C4	0.0545 (13)	0.0502 (13)	0.0496 (14)	0.0017 (11)	0.0081 (11)	0.0124 (11)
C11	0.0556 (13)	0.0496 (13)	0.0413 (12)	0.0050 (10)	0.0189 (10)	0.0009 (10)
C7	0.0451 (12)	0.0573 (14)	0.0645 (15)	−0.0020 (11)	0.0181 (12)	0.0118 (12)
O1	0.0906 (13)	0.0778 (13)	0.1068 (15)	0.0194 (10)	0.0665 (12)	0.0326 (11)
C5	0.0550 (13)	0.0484 (13)	0.0480 (13)	−0.0035 (11)	0.0135 (11)	0.0069 (10)
C2	0.0610 (15)	0.0550 (15)	0.0539 (14)	−0.0095 (12)	0.0061 (12)	−0.0027 (11)
C17	0.0926 (19)	0.0432 (14)	0.0702 (17)	−0.0039 (13)	0.0186 (15)	0.0076 (12)
C16	0.0852 (18)	0.0624 (16)	0.0571 (15)	−0.0086 (13)	0.0268 (14)	0.0111 (12)
C1	0.0508 (13)	0.0598 (15)	0.0562 (15)	−0.0032 (12)	−0.0019 (11)	0.0079 (12)

Cl1—C3	1.738 (2)	C6—C1	1.389 (3)
Cl2—C5	1.739 (2)	C6—C7	1.507 (3)
C13—N1	1.369 (2)	C3—C4	1.372 (3)
C13—C14	1.402 (3)	C3—C2	1.372 (3)
C13—C12	1.405 (3)	C14—H14	0.930
C10—C11	1.393 (3)	C4—C5	1.376 (3)
C10—C15	1.400 (3)	C4—H4	0.9300
C10—C9	1.443 (3)	C11—H11	0.930
C9—C8	1.338 (3)	C7—O1	1.218 (3)
C9—H9	0.930	C2—C1	1.369 (3)
C15—C14	1.371 (3)	C2—H2	0.930
C15—H15	0.930	C17—H17A	0.960
C8—C7	1.448 (3)	C17—H17B	0.960
C8—H8	0.930	C17—H17C	0.960
N1—C17	1.444 (3)	C16—H16A	0.960
N1—C16	1.450 (3)	C16—H16B	0.960
C12—C11	1.365 (3)	C16—H16C	0.960
C12—H12	0.930	C1—H1	0.930
C6—C5	1.383 (3)
N1—C13—C14	121.63 (18)	C3—C4—C5	118.8 (2)
N1—C13—C12	121.38 (18)	C3—C4—H4	120.6
C14—C13—C12	116.97 (18)	C5—C4—H4	120.6
C11—C10—C15	116.45 (18)	C12—C11—C10	122.21 (19)
C11—C10—C9	123.63 (19)	C12—C11—H11	118.9
C15—C10—C9	119.89 (18)	C10—C11—H11	118.9
C8—C9—C10	128.1 (2)	O1—C7—C8	121.3 (2)
C8—C9—H9	116.0	O1—C7—C6	119.6 (2)
C10—C9—H9	116.0	C8—C7—C6	119.03 (19)
C14—C15—C10	122.09 (19)	C4—C5—C6	122.1 (2)
C14—C15—H15	119.0	C4—C5—Cl2	117.72 (18)
C10—C15—H15	119.0	C6—C5—Cl2	120.17 (18)
C9—C8—C7	125.7 (2)	C1—C2—C3	118.9 (2)
C9—C8—H8	117.2	C1—C2—H2	120.5
C7—C8—H8	117.2	C3—C2—H2	120.5
C13—N1—C17	121.42 (18)	N1—C17—H17A	109.5
C13—N1—C16	120.27 (18)	N1—C17—H17B	109.5
C17—N1—C16	117.56 (18)	H17A—C17—H17B	109.5
C11—C12—C13	121.25 (19)	N1—C17—H17C	109.5
C11—C12—H12	119.4	H17A—C17—H17C	109.5
C13—C12—H12	119.4	H17B—C17—H17C	109.5
C5—C6—C1	116.9 (2)	N1—C16—H16A	109.5
C5—C6—C7	122.5 (2)	N1—C16—H16B	109.5
C1—C6—C7	120.6 (2)	H16A—C16—H16B	109.5
C4—C3—C2	121.1 (2)	N1—C16—H16C	109.5
C4—C3—Cl1	119.27 (18)	H16A—C16—H16C	109.5
C2—C3—Cl1	119.55 (19)	H16B—C16—H16C	109.5
C15—C14—C13	120.99 (19)	C2—C1—C6	122.1 (2)
C15—C14—H14	119.5	C2—C1—H1	118.9
C13—C14—H14	119.5	C6—C1—H1	118.9
C11—C10—C9—C8	11.4 (4)	C9—C10—C11—C12	176.6 (2)
C15—C10—C9—C8	−170.5 (2)	C9—C8—C7—O1	177.9 (2)
C11—C10—C15—C14	−0.1 (3)	C9—C8—C7—C6	−0.9 (3)
C9—C10—C15—C14	−178.3 (2)	C5—C6—C7—O1	−61.9 (3)
C10—C9—C8—C7	−176.3 (2)	C1—C6—C7—O1	117.2 (3)
C14—C13—N1—C17	−168.4 (2)	C5—C6—C7—C8	117.0 (2)
C12—C13—N1—C17	13.1 (3)	C1—C6—C7—C8	−64.0 (3)
C14—C13—N1—C16	1.6 (3)	C3—C4—C5—C6	−2.3 (3)
C12—C13—N1—C16	−177.0 (2)	C3—C4—C5—Cl2	179.29 (16)
N1—C13—C12—C11	177.7 (2)	C1—C6—C5—C4	1.5 (3)
C14—C13—C12—C11	−0.9 (3)	C7—C6—C5—C4	−179.42 (19)
C10—C15—C14—C13	1.2 (3)	C1—C6—C5—Cl2	179.91 (16)
N1—C13—C14—C15	−179.3 (2)	C7—C6—C5—Cl2	−1.0 (3)
C12—C13—C14—C15	−0.7 (3)	C4—C3—C2—C1	1.1 (3)
C2—C3—C4—C5	0.9 (3)	Cl1—C3—C2—C1	−176.93 (17)
Cl1—C3—C4—C5	178.95 (16)	C3—C2—C1—C6	−1.9 (3)
C13—C12—C11—C10	2.1 (3)	C5—C6—C1—C2	0.6 (3)
C15—C10—C11—C12	−1.5 (3)	C7—C6—C1—C2	−178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.93	2.55	3.252 (3)	132
C4—H4···Cg1ii	0.93	2.95	3.784 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.55	3.252 (3)	132
C4—H4⋯Cg1ii	0.93	2.95	3.784 (3)	150

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C10–C15 ring.