1-(2,4-Dichloro­phen­yl)-3-[4-(dimethyl­amino)phen­yl]prop-2-enone

Bappalige, N.N.; Brinda; Narayana, Y.; Upadyaya, V.

doi:10.1107/S1600536809015177

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1266

doi:10.1107/S1600536809015177

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1-(2,4-Dichlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-enone

Navin N. Bappalige,^a Brinda,^b ^* Y. Narayana ^a and V. Upadyaya ^c

^aDepartment of Physics, Mangalore University, Mangalagangothri, Mangalore 574 199, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India, and ^cDepartment of Physics, Manipal Institute of Technology, Manipal 576 104, India
^*Correspondence e-mail: brinda@sscu.iisc.ernet.in

(Received 16 March 2009; accepted 23 April 2009; online 14 May 2009)

In the title compound, C₁₇H₁₅Cl₂NO, the dimethylaminophenyl group is close to coplanar with the central propenone group [dihedral angle = 13.1 (1)° between the mean planes], while the dichlorophenyl group is twisted from the plane [dihedral angle = 64.0 (1)°]. In the crystal, C—H⋯O and weak C—H⋯π interactions are formed between molecules.

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_r = 320.20
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.106
S = 1.03
2908 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C10–C15 ring.

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 ).

Supporting information

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

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

checkCIF report

Related literature top

For related structures, see: Murafuji et al. (1999); Liu et al. (2002); Patil et al. (2007a,b); Rosli et al. (2007). Cg1 is the centroid of the C10–C15 ring.

Experimental top

A solution of potassium hydroxide (6.25 g, 0.11 mol) in ethanol (25 ml) was added slowly to a mixture of dichloroacetophenone (18.8 g, 0.01 mol) and N-dimethyl benzaldehyde (14.9 g, 0.01 mol) in a conical flask. After stirring for two hours, the precipitate was filtered and recrystallized from ethanol to give pale orange crystals.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level for non-H atoms. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Packing diagram. The dotted lines indicate intermolecular C—H···O and C—H···π interactions.

1-(2,4-Dichlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-enone top

Crystal data top

C₁₇H₁₅Cl₂NO	F(000) = 664
M_r = 320.20	D_x = 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

Data collection top

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

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0505P)² + 0.1972P] where P = (F_o² + 2F_c²)/3
2908 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₅Cl₂NO	V = 1559.5 (6) Å³
M_r = 320.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5741 (19) Å	µ = 0.41 mm⁻¹
b = 12.706 (3) Å	T = 290 K
c = 14.671 (3) Å	0.25 × 0.15 × 0.07 mm
β = 102.645 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2908 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2039 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.972	R_int = 0.031
11540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
2908 reflections	Δρ_min = −0.17 e Å⁻³
192 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅Cl₂NO
M_r	320.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	8.5741 (19), 12.706 (3), 14.671 (3)
β (°)	102.645 (4)
V (Å³)	1559.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.25 × 0.15 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	11540, 2908, 2039
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.106, 1.03
No. of reflections	2908
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA-DST program at IISc.

References

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