(E)-1-(4-Chloro­phen­yl)-3-[4-(dimethyl­amino)phen­yl]prop-2-en-1-one

Lei, X.; Bai, X.

doi:10.1107/S1600536809007430

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o739

doi:10.1107/S1600536809007430

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(E)-1-(4-Chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Xinyou Lei ^a ^* and Xiaohua Bai ^a

^aCollege of Life Sciences and Chemistry, Tianshui Normal University, Tianshu 741000, People's Republic of China
^*Correspondence e-mail: lei_xinyou@163.com

(Received 20 December 2008; accepted 28 February 2009; online 11 March 2009)

The title compound, C₁₇H₁₆ClNO, was synthesized using a solvent-free method by reaction of 4-(dimethylamino)benzaldehyde with 4-chloroacetophenone and NaOH. The chlorophenyl ring makes a dihedral angle of 18.1 (3)° with the central propenone unit, while the (dimethylamino)phenyl group is disordered over two orientations of equal occupancies, which make dihedral angles with the central propenone unit of 32.9 (3) and 57.4 (3)°, respectively.

Related literature

For a related structure, see: Li et al. (1992 ).

Experimental

Crystal data

C₁₇H₁₆ClNO
M_r = 285.76
Monoclinic, P 2₁ /c
a = 16.792 (2) Å
b = 14.5602 (16) Å
c = 6.1160 (8) Å
β = 98.333 (2)°
V = 1479.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.42 × 0.20 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.901, T_max = 0.968
7357 measured reflections
2605 independent reflections
1066 reflections with I > 2˘I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.170
S = 0.90
2605 reflections
237 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536809007430/bi2339sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007430/bi2339Isup2.hkl

checkCIF report

Comment top

This paper discloses a user-friendly, solvent-free protocol for the synthesis of chalcones, starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH. The method can be considered to be a general route for chalcone synthesis, and the title compound was prepared in this way.

The bond lengths and angles of the molecule (Fig. 1) are normal and comparable to those observed in the related compound (Li et al., 1992). The (dimethylamino)phenyl group exhibits rotational disorder, with one orientation including atoms C10, C11, C12, C13, C14 and C15, and another orientation including C10, C11', C12', C13, C14' and C15'. The refined site occupancy factors for the two orientations is 0.500 (5).

Related literature top

For a related structure, see: Li et al. (1992).

Experimental top

4-(Dimethylamino)benzaldehyde (0.5 mmol) and 4-chloroacetophenone (0.5 mmol), NaOH (0.5 mmol) were mixed in 50 ml flask under solvent-free conditions After stirring for 6 min at 373 K, the mixture was slowly solidified to give the title compound. Recrystallization from ethanol gave a yellow crystalline solid. Elemental analysis calculated: C 71.45, H 5.64, N 4.90%; found: C 71.53, H 5.56, N 4.95%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 molecular structure showing 30% probability displacement ellipsoids for non-H atoms.

(E)-1-(4-Chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one top

Crystal data top

C₁₇H₁₆ClNO	F(000) = 600
M_r = 285.76	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 987 reflections
a = 16.792 (2) Å	θ = 2.5–19.9°
b = 14.5602 (16) Å	µ = 0.25 mm⁻¹
c = 6.1160 (8) Å	T = 298 K
β = 98.333 (2)°	Needle, yellow
V = 1479.5 (3) Å³	0.42 × 0.20 × 0.13 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2605 independent reflections
Radiation source: fine-focus sealed tube	1066 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.068
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −19→19
T_min = 0.901, T_max = 0.968	k = −17→12
7357 measured reflections	l = −7→7

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0749P)²] where P = (F_o² + 2F_c²)/3
2605 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.16 e Å⁻³
4 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₇H₁₆ClNO	V = 1479.5 (3) Å³
M_r = 285.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.792 (2) Å	µ = 0.25 mm⁻¹
b = 14.5602 (16) Å	T = 298 K
c = 6.1160 (8) Å	0.42 × 0.20 × 0.13 mm
β = 98.333 (2)°

Data collection top

Bruker SMART CCD diffractometer	2605 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1066 reflections with I > 2˘I)
T_min = 0.901, T_max = 0.968	R_int = 0.068
7357 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	4 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 0.90	Δρ_max = 0.16 e Å⁻³
2605 reflections	Δρ_min = −0.12 e Å⁻³
237 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	Occ. (<1)
Cl1	1.12683 (6)	0.14642 (9)	1.2060 (3)	0.1285 (7)
N1	0.34724 (18)	0.1225 (2)	0.8419 (7)	0.0891 (11)
O1	0.80650 (17)	0.1009 (2)	0.4377 (6)	0.1225 (12)
C1	0.8071 (2)	0.1135 (2)	0.6344 (8)	0.0739 (11)
C2	0.8853 (2)	0.1192 (2)	0.7831 (7)	0.0683 (10)
C3	0.8921 (2)	0.1538 (2)	0.9959 (7)	0.0742 (11)
H3	0.8460	0.1712	1.0530	0.089*
C4	0.9663 (2)	0.1627 (2)	1.1247 (7)	0.0801 (11)
H4	0.9701	0.1868	1.2666	0.096*
C5	1.0345 (2)	0.1356 (3)	1.0416 (9)	0.0831 (12)
C6	1.0292 (3)	0.0990 (3)	0.8348 (9)	0.0889 (13)
H6	1.0755	0.0792	0.7816	0.107*
C7	0.9552 (2)	0.0914 (2)	0.7048 (7)	0.0792 (11)
H7	0.9520	0.0673	0.5629	0.095*
C8	0.7314 (2)	0.1221 (2)	0.7236 (7)	0.0754 (11)
H8	0.7343	0.1272	0.8762	0.090*
C9	0.6615 (2)	0.1233 (3)	0.6088 (7)	0.0872 (12)
H9	0.6617	0.1225	0.4568	0.105*
C10	0.5811 (2)	0.1255 (3)	0.6741 (6)	0.0639 (9)
C11	0.5655 (5)	0.0979 (6)	0.8724 (14)	0.055 (2)	0.500 (5)
H11	0.6076	0.0821	0.9821	0.065*	0.500 (5)
C12	0.4860 (5)	0.0928 (6)	0.9147 (13)	0.059 (2)	0.500 (5)
H12	0.4773	0.0651	1.0463	0.070*	0.500 (5)
C13	0.4234 (2)	0.1232 (2)	0.7863 (7)	0.0639 (10)
C14	0.4419 (4)	0.1658 (5)	0.5679 (11)	0.057 (2)	0.500 (5)
H14	0.4007	0.1885	0.4641	0.068*	0.500 (5)
C15	0.5208 (4)	0.1695 (5)	0.5295 (12)	0.059 (2)	0.500 (5)
H15	0.5339	0.2012	0.4075	0.070*	0.500 (5)
C16	0.2783 (5)	0.0794 (8)	0.7432 (18)	0.103 (4)	0.500 (5)
H16A	0.2583	0.1102	0.6074	0.154*	0.510 (7)
H16B	0.2383	0.0815	0.8404	0.154*	0.510 (7)
H16C	0.2902	0.0166	0.7128	0.154*	0.510 (7)
C17	0.3364 (5)	0.1683 (7)	1.0661 (13)	0.106 (4)	0.500 (5)
H17A	0.3811	0.1526	1.1758	0.158*	0.510 (7)
H17B	0.2874	0.1466	1.1123	0.158*	0.510 (7)
H17C	0.3338	0.2337	1.0483	0.158*	0.510 (7)
C11'	0.5658 (5)	0.1596 (6)	0.8637 (16)	0.060 (2)	0.500 (5)
H11'	0.6089	0.1842	0.9581	0.073*	0.500 (5)
C12'	0.4923 (4)	0.1618 (6)	0.9327 (12)	0.060 (2)	0.500 (5)
H12'	0.4859	0.1870	1.0688	0.072*	0.500 (5)
C14'	0.4368 (4)	0.0774 (5)	0.6145 (12)	0.059 (2)	0.500 (5)
H14'	0.3949	0.0445	0.5344	0.070*	0.500 (5)
C15'	0.5112 (4)	0.0760 (5)	0.5472 (12)	0.064 (2)	0.500 (5)
H15'	0.5184	0.0436	0.4203	0.076*	0.500 (5)
C16'	0.2804 (4)	0.1498 (7)	0.6472 (14)	0.090 (3)	0.500 (5)
H16D	0.2919	0.2095	0.5931	0.135*	0.490 (7)
H16E	0.2290	0.1509	0.6988	0.135*	0.490 (7)
H16F	0.2791	0.1056	0.5302	0.135*	0.490 (7)
C17'	0.3231 (5)	0.0619 (6)	0.9866 (13)	0.079 (3)	0.500 (5)
H17D	0.3431	0.0019	0.9590	0.119*	0.490 (7)
H17E	0.2654	0.0604	0.9688	0.119*	0.490 (7)
H17F	0.3437	0.0804	1.1347	0.119*	0.490 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0640 (8)	0.1472 (12)	0.1697 (14)	−0.0010 (6)	0.0012 (8)	−0.0022 (9)
N1	0.053 (2)	0.084 (2)	0.132 (3)	0.0039 (18)	0.021 (2)	−0.008 (3)
O1	0.085 (2)	0.211 (4)	0.078 (2)	0.001 (2)	0.0324 (18)	0.006 (2)
C1	0.069 (3)	0.072 (3)	0.087 (3)	−0.0025 (19)	0.033 (2)	0.000 (2)
C2	0.061 (2)	0.061 (2)	0.089 (3)	−0.0045 (18)	0.032 (2)	0.003 (2)
C3	0.059 (3)	0.080 (3)	0.087 (3)	0.0014 (18)	0.024 (2)	−0.003 (2)
C4	0.074 (3)	0.075 (3)	0.094 (3)	−0.001 (2)	0.022 (2)	−0.003 (2)
C5	0.060 (3)	0.074 (3)	0.118 (4)	0.003 (2)	0.023 (3)	0.007 (3)
C6	0.071 (3)	0.084 (3)	0.120 (4)	0.003 (2)	0.043 (3)	−0.005 (3)
C7	0.074 (3)	0.074 (3)	0.097 (3)	0.001 (2)	0.037 (3)	−0.007 (2)
C8	0.062 (2)	0.090 (3)	0.077 (3)	−0.010 (2)	0.021 (2)	−0.015 (2)
C9	0.071 (3)	0.130 (3)	0.063 (3)	0.021 (2)	0.018 (2)	0.019 (2)
C10	0.058 (2)	0.075 (2)	0.059 (3)	0.007 (2)	0.0076 (19)	0.001 (2)
C11	0.050 (5)	0.057 (5)	0.056 (6)	0.007 (4)	0.003 (4)	0.004 (5)
C12	0.069 (6)	0.057 (5)	0.052 (5)	−0.006 (5)	0.013 (4)	0.000 (4)
C13	0.050 (2)	0.054 (2)	0.087 (3)	0.0039 (19)	0.005 (2)	−0.008 (2)
C14	0.057 (5)	0.051 (5)	0.058 (5)	0.002 (3)	0.000 (3)	0.008 (3)
C15	0.066 (5)	0.053 (5)	0.058 (5)	−0.007 (4)	0.012 (4)	0.003 (3)
C16	0.076 (6)	0.114 (8)	0.118 (10)	−0.024 (6)	0.015 (6)	−0.030 (7)
C17	0.071 (6)	0.151 (9)	0.098 (8)	−0.002 (5)	0.025 (5)	−0.002 (6)
C11'	0.053 (5)	0.058 (6)	0.067 (6)	−0.005 (5)	−0.001 (4)	−0.012 (5)
C12'	0.058 (5)	0.072 (6)	0.051 (5)	−0.008 (5)	0.011 (4)	−0.008 (4)
C14'	0.047 (4)	0.060 (6)	0.067 (5)	−0.005 (3)	0.000 (4)	−0.011 (4)
C15'	0.067 (5)	0.064 (6)	0.060 (5)	0.005 (4)	0.008 (4)	−0.006 (4)
C16'	0.049 (5)	0.111 (8)	0.105 (8)	−0.001 (5)	−0.001 (5)	0.014 (6)
C17'	0.076 (5)	0.094 (7)	0.071 (7)	0.011 (5)	0.023 (5)	0.011 (5)

Geometric parameters (Å, º) top

Cl1—C5	1.729 (4)	C11—H11	0.930
N1—C17'	1.353 (7)	C12—C13	1.296 (8)
N1—C13	1.370 (4)	C12—H12	0.930
N1—C16	1.377 (7)	C13—C14'	1.292 (7)
N1—C17	1.559 (7)	C13—C12'	1.468 (8)
N1—C16'	1.565 (7)	C13—C14	1.545 (8)
O1—C1	1.215 (4)	C14—C15	1.379 (8)
C1—C8	1.460 (5)	C14—H14	0.930
C1—C2	1.486 (5)	C15—H15	0.930
C2—C3	1.385 (5)	C16—H16A	0.960
C2—C7	1.391 (4)	C16—H16B	0.960
C3—C4	1.379 (5)	C16—H16C	0.960
C3—H3	0.930	C17—H17A	0.960
C4—C5	1.376 (5)	C17—H17B	0.960
C4—H4	0.930	C17—H17C	0.960
C5—C6	1.364 (5)	C11'—C12'	1.362 (10)
C6—C7	1.380 (5)	C11'—H11'	0.930
C6—H6	0.930	C12'—H12'	0.930
C7—H7	0.930	C14'—C15'	1.372 (9)
C8—C9	1.278 (5)	C14'—H14'	0.930
C8—H8	0.930	C15'—H15'	0.930
C9—C10	1.463 (5)	C16'—H16D	0.960
C9—H9	0.930	C16'—H16E	0.960
C10—C11'	1.320 (9)	C16'—H16F	0.960
C10—C11	1.339 (9)	C17'—H17D	0.960
C10—C15	1.399 (8)	C17'—H17E	0.960
C10—C15'	1.495 (8)	C17'—H17F	0.960
C11—C12	1.398 (10)

C17'—N1—C13	123.1 (5)	N1—C13—C12'	122.2 (5)
C13—N1—C16	130.6 (5)	C12—C13—C14	114.4 (5)
C13—N1—C17	116.6 (4)	N1—C13—C14	122.0 (4)
C16—N1—C17	112.5 (5)	C15—C14—C13	118.8 (6)
C17'—N1—C16'	114.4 (6)	C15—C14—H14	120.6
C13—N1—C16'	113.7 (5)	C13—C14—H14	120.6
O1—C1—C8	120.0 (4)	C14—C15—C10	119.9 (6)
O1—C1—C2	119.6 (3)	C14—C15—H15	120.0
C8—C1—C2	120.4 (4)	C10—C15—H15	120.0
C3—C2—C7	118.0 (4)	N1—C16—H16A	109.5
C3—C2—C1	122.8 (3)	N1—C16—H16B	109.5
C7—C2—C1	119.2 (4)	H16A—C16—H16B	109.5
C4—C3—C2	121.1 (4)	N1—C16—H16C	109.5
C4—C3—H3	119.5	H16A—C16—H16C	109.5
C2—C3—H3	119.5	H16B—C16—H16C	109.5
C5—C4—C3	119.5 (4)	N1—C17—H17A	109.5
C5—C4—H4	120.2	N1—C17—H17B	109.5
C3—C4—H4	120.2	H17A—C17—H17B	109.5
C6—C5—C4	120.6 (4)	N1—C17—H17C	109.5
C6—C5—Cl1	120.5 (3)	H17A—C17—H17C	109.5
C4—C5—Cl1	118.9 (4)	H17B—C17—H17C	109.5
C5—C6—C7	119.8 (4)	C10—C11'—C12'	125.5 (7)
C5—C6—H6	120.1	C10—C11'—H11'	117.2
C7—C6—H6	120.1	C12'—C11'—H11'	117.2
C6—C7—C2	120.9 (4)	C11'—C12'—C13	118.2 (7)
C6—C7—H7	119.6	C11'—C12'—H12'	120.9
C2—C7—H7	119.6	C13—C12'—H12'	120.9
C9—C8—C1	125.2 (4)	C13—C14'—C15'	121.8 (6)
C9—C8—H8	117.4	C13—C14'—H14'	119.1
C1—C8—H8	117.4	C15'—C14'—H14'	119.1
C8—C9—C10	131.4 (4)	C14'—C15'—C10	121.1 (6)
C8—C9—H9	114.3	C14'—C15'—H15'	119.4
C10—C9—H9	114.3	C10—C15'—H15'	119.4
C11—C10—C15	119.4 (5)	N1—C16'—H16D	109.5
C11—C10—C9	123.4 (4)	N1—C16'—H16E	109.5
C15—C10—C9	116.7 (4)	H16D—C16'—H16E	109.5
C9—C10—C15'	122.2 (4)	N1—C16'—H16F	109.5
C10—C11—C12	120.1 (6)	H16D—C16'—H16F	109.5
C10—C11—H11	120.0	H16E—C16'—H16F	109.5
C12—C11—H11	120.0	N1—C17'—H17D	109.5
C13—C12—C11	125.6 (7)	N1—C17'—H17E	109.5
C13—C12—H12	117.2	H17D—C17'—H17E	109.5
C11—C12—H12	117.2	N1—C17'—H17F	109.5
C14'—C13—N1	118.5 (4)	H17D—C17'—H17F	109.5
C12—C13—N1	123.5 (5)	H17E—C17'—H17F	109.5
C14'—C13—C12'	118.6 (5)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆ClNO
M_r	285.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.792 (2), 14.5602 (16), 6.1160 (8)
β (°)	98.333 (2)
V (Å³)	1479.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.42 × 0.20 × 0.13

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.901, 0.968
No. of measured, independent and observed [I > 2˘I)] reflections	7357, 2605, 1066
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.170, 0.90
No. of reflections	2605
No. of parameters	237
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.12

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Foundation of Tianshui Normal University.

References

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