(E)-1-(5-Bromo-2-hy­droxy­phen­yl)-3-[4-(dimethyl­amino)­phen­yl]prop-2-en-1-one

Li, G.-B.; Li, L.; Wang, G.-X.

doi:10.1107/S1600536812016327

organic compounds

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Volume 68| Part 5| May 2012| Page o1446

doi:10.1107/S1600536812016327

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(E)-1-(5-Bromo-2-hydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Guang-Bing Li,^a Lu Li ^a and Guo-Xi Wang ^a ^*

^aDepartment of Chemical & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
^*Correspondence e-mail: aywgx@yahoo.com.cn

(Received 14 April 2012; accepted 15 April 2012; online 21 April 2012)

In the title compound, C₁₇H₁₆BrNO₂, the two benzene rings make a dihedral angle of 7.4 (3)°; the hydroxy group links to the carbonyl group via an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O interactions link the molecules into a supramolecular chain running along the c axis.

Related literature

For related compounds and structures, see: Dai & Chen (2011 ); Xu et al. (2011 ); Fu et al. (2011 ); Zheng et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₆BrNO₂
M_r = 346.22
Monoclinic, P 2₁ /c
a = 15.1905 (5) Å
b = 5.4501 (2) Å
c = 19.7569 (9) Å
β = 106.00 (2)°
V = 1572.34 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.62 mm⁻¹
T = 123 K
0.30 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
8044 measured reflections
2736 independent reflections
1538 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.089
wR(F²) = 0.287
S = 1.09
2736 reflections
193 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.58 e Å⁻³
Δρ_min = −1.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.82	2.543 (7)	146
C17—H17A⋯O2ⁱ	0.98	2.55	3.503 (10)	164
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016327/xu5515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016327/xu5515Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016327/xu5515Isup3.cml

checkCIF report

Comment top

Organic amine derivatives are becoming increasingly important as new molecule-based crystalline materials with the potential optimal physical properties (Dai & Chen, 2011; Xu et al., 2011). In addition, the amino compounds have found a wide range of applications in coordination chemistry as ligands to construct novel crystal structures (Fu et al., 2011; Zheng, 2011). Herein, we report the crystal structure of the title compound, (E)-1-(5-bromo-2-hydroxyphenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one.

The asymmetric unit is composed of one whole amine molecule. The two benzene rings are nearly coplanar and twisted from each other by a dihedral of 7.4 (3)°. The hydroxy H2 atom was involved in intramolecular O—H···O hydrogen bonds interaction (Table 1 and Fig. 1).

Related literature top

For related compounds and structures, see: Dai & Chen (2011); Xu et al. (2011); Fu et al. (2011); Zheng et al. (2011).

Experimental top

The title compound (2.0 mmol) was solved in 50 mL methanol. Then the solution was evaporated slowly in the air. Red block crystals suitable for X-ray analysis were obtained after one week.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

(E)-1-(5-Bromo-2-hydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop- 2-en-1-one top

Crystal data top

C₁₇H₁₆BrNO₂	F(000) = 704
M_r = 346.22	D_x = 1.463 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2736 reflections
a = 15.1905 (5) Å	θ = 2.2–27.5°
b = 5.4501 (2) Å	µ = 2.62 mm⁻¹
c = 19.7569 (9) Å	T = 123 K
β = 106.00 (2)°	Needle, red
V = 1572.34 (11) Å³	0.30 × 0.05 × 0.05 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	2736 independent reflections
Radiation source: fine-focus sealed tube	1538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
CCD profile fitting scans	h = −18→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −6→6
T_min = 0.910, T_max = 1.000	l = −23→23
8044 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.089	H-atom parameters constrained
wR(F²) = 0.287	w = 1/[σ²(F_o²) + (0.141P)² + 0.6743P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2736 reflections	Δρ_max = 1.58 e Å⁻³
193 parameters	Δρ_min = −1.11 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.002

Crystal data top

C₁₇H₁₆BrNO₂	V = 1572.34 (11) Å³
M_r = 346.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1905 (5) Å	µ = 2.62 mm⁻¹
b = 5.4501 (2) Å	T = 123 K
c = 19.7569 (9) Å	0.30 × 0.05 × 0.05 mm
β = 106.00 (2)°

Data collection top

Rigaku Mercury2 diffractometer	2736 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1538 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.075
8044 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.089	1 restraint
wR(F²) = 0.287	H-atom parameters constrained
S = 1.09	Δρ_max = 1.58 e Å⁻³
2736 reflections	Δρ_min = −1.11 e Å⁻³
193 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	1.08032 (7)	−0.2556 (2)	0.57680 (7)	0.1050 (7)
O1	0.6988 (3)	0.0521 (10)	0.6480 (2)	0.0469 (13)
C7	0.7599 (4)	0.0665 (12)	0.6153 (3)	0.0329 (15)
N1	0.5880 (3)	1.1541 (11)	0.3308 (3)	0.0355 (14)
O2	0.7796 (4)	−0.3021 (10)	0.7239 (3)	0.0600 (16)
H2	0.7357	−0.2242	0.7002	0.090*
C10	0.6627 (4)	0.6074 (12)	0.4911 (3)	0.0307 (14)
C9	0.6821 (4)	0.4141 (13)	0.5444 (3)	0.0331 (15)
H9A	0.6394	0.3991	0.5714	0.040*
C14	0.5541 (4)	0.9164 (12)	0.4255 (3)	0.0339 (15)
H14A	0.4969	0.9979	0.4183	0.041*
C13	0.6124 (4)	0.9790 (12)	0.3830 (3)	0.0331 (15)
C5	0.8429 (5)	−0.2911 (12)	0.6878 (4)	0.0386 (17)
C12	0.6988 (4)	0.8490 (12)	0.3966 (3)	0.0362 (16)
H12A	0.7404	0.8867	0.3699	0.043*
C1	0.9105 (4)	−0.1047 (14)	0.6015 (3)	0.0412 (17)
H1A	0.9106	0.0160	0.5669	0.049*
C6	0.8391 (4)	−0.1080 (12)	0.6344 (3)	0.0307 (14)
C2	0.9802 (5)	−0.2758 (13)	0.6193 (4)	0.0446 (19)
C15	0.5789 (5)	0.7398 (12)	0.4769 (4)	0.0342 (16)
H15A	0.5380	0.7044	0.5043	0.041*
C11	0.7207 (4)	0.6699 (12)	0.4483 (3)	0.0364 (16)
H11A	0.7772	0.5849	0.4555	0.044*
C4	0.9150 (5)	−0.4652 (14)	0.7037 (4)	0.0483 (19)
H4A	0.9168	−0.5864	0.7387	0.058*
C8	0.7530 (4)	0.2529 (11)	0.5605 (3)	0.0294 (15)
H8A	0.7987	0.2610	0.5360	0.035*
C16	0.5060 (5)	1.3053 (13)	0.3242 (4)	0.0429 (18)
H16A	0.4515	1.2004	0.3123	0.064*
H16B	0.5012	1.4277	0.2871	0.064*
H16C	0.5105	1.3887	0.3690	0.064*
C3	0.9833 (4)	−0.4609 (14)	0.6688 (4)	0.0438 (18)
H3A	1.0306	−0.5806	0.6784	0.053*
C17	0.6536 (6)	1.2333 (13)	0.2900 (4)	0.0441 (18)
H17A	0.6841	1.0888	0.2775	0.066*
H17B	0.6994	1.3444	0.3190	0.066*
H17C	0.6197	1.3183	0.2470	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0628 (9)	0.1585 (14)	0.1133 (11)	0.0652 (8)	0.0570 (8)	0.0639 (8)
O1	0.038 (3)	0.055 (3)	0.057 (3)	0.006 (2)	0.029 (2)	0.010 (2)
C7	0.024 (3)	0.036 (4)	0.041 (4)	−0.005 (3)	0.012 (3)	−0.004 (3)
N1	0.029 (3)	0.041 (3)	0.039 (3)	0.008 (2)	0.014 (3)	−0.003 (2)
O2	0.049 (4)	0.063 (4)	0.069 (4)	0.005 (3)	0.020 (3)	0.029 (3)
C10	0.026 (3)	0.032 (3)	0.034 (3)	0.002 (3)	0.008 (3)	−0.004 (3)
C9	0.024 (3)	0.043 (4)	0.034 (3)	0.000 (3)	0.011 (3)	−0.006 (3)
C14	0.026 (3)	0.033 (3)	0.047 (4)	0.006 (3)	0.017 (3)	−0.009 (3)
C13	0.030 (3)	0.036 (4)	0.033 (3)	−0.002 (3)	0.008 (3)	−0.008 (3)
C5	0.034 (4)	0.040 (4)	0.045 (4)	−0.007 (3)	0.016 (3)	0.001 (3)
C12	0.027 (4)	0.040 (4)	0.045 (4)	0.000 (3)	0.016 (3)	0.002 (3)
C1	0.038 (4)	0.050 (4)	0.039 (4)	0.010 (3)	0.016 (3)	0.012 (3)
C6	0.026 (3)	0.036 (4)	0.027 (3)	−0.003 (3)	0.003 (3)	0.001 (3)
C2	0.032 (4)	0.053 (5)	0.052 (5)	0.011 (3)	0.015 (4)	0.005 (3)
C15	0.028 (4)	0.041 (4)	0.037 (4)	−0.003 (3)	0.015 (3)	−0.006 (3)
C11	0.024 (3)	0.046 (4)	0.043 (4)	0.006 (3)	0.016 (3)	−0.002 (3)
C4	0.044 (4)	0.044 (4)	0.046 (4)	−0.004 (3)	−0.005 (4)	0.004 (3)
C8	0.021 (3)	0.035 (3)	0.033 (4)	−0.001 (3)	0.009 (3)	−0.003 (3)
C16	0.046 (5)	0.044 (4)	0.038 (4)	0.016 (3)	0.011 (3)	0.006 (3)
C3	0.030 (4)	0.043 (4)	0.049 (4)	0.008 (3)	−0.003 (3)	−0.001 (3)
C17	0.054 (5)	0.038 (4)	0.046 (4)	0.000 (3)	0.025 (4)	0.005 (3)

Geometric parameters (Å, º) top

Br1—C2	1.933 (8)	C5—C6	1.441 (9)
O1—C7	1.271 (7)	C12—C11	1.386 (9)
C7—C8	1.468 (9)	C12—H12A	0.9500
C7—C6	1.499 (9)	C1—C2	1.382 (9)
N1—C13	1.380 (8)	C1—C6	1.409 (9)
N1—C16	1.469 (8)	C1—H1A	0.9500
N1—C17	1.506 (9)	C2—C3	1.396 (10)
O2—C5	1.347 (9)	C15—H15A	0.9500
O2—H2	0.8200	C11—H11A	0.9500
C10—C11	1.421 (9)	C4—C3	1.397 (9)
C10—C15	1.423 (9)	C4—H4A	0.9500
C10—C9	1.461 (9)	C8—H8A	0.9500
C9—C8	1.358 (9)	C16—H16A	0.9800
C9—H9A	0.9500	C16—H16B	0.9800
C14—C15	1.374 (9)	C16—H16C	0.9800
C14—C13	1.419 (8)	C3—H3A	0.9500
C14—H14A	0.9500	C17—H17A	0.9800
C13—C12	1.450 (9)	C17—H17B	0.9800
C5—C4	1.417 (10)	C17—H17C	0.9800

O1—C7—C8	120.3 (6)	C1—C2—C3	122.8 (7)
O1—C7—C6	118.8 (6)	C1—C2—Br1	119.4 (6)
C8—C7—C6	120.9 (5)	C3—C2—Br1	117.8 (5)
C13—N1—C16	120.0 (5)	C14—C15—C10	123.3 (6)
C13—N1—C17	121.2 (5)	C14—C15—H15A	118.3
C16—N1—C17	117.5 (6)	C10—C15—H15A	118.3
C5—O2—H2	105.1	C12—C11—C10	123.1 (6)
C11—C10—C15	115.4 (6)	C12—C11—H11A	118.5
C11—C10—C9	124.6 (6)	C10—C11—H11A	118.5
C15—C10—C9	120.0 (6)	C3—C4—C5	120.9 (7)
C8—C9—C10	128.6 (6)	C3—C4—H4A	119.6
C8—C9—H9A	115.7	C5—C4—H4A	119.6
C10—C9—H9A	115.7	C9—C8—C7	120.7 (6)
C15—C14—C13	121.1 (6)	C9—C8—H8A	119.7
C15—C14—H14A	119.5	C7—C8—H8A	119.7
C13—C14—H14A	119.5	N1—C16—H16A	109.5
N1—C13—C14	121.7 (6)	N1—C16—H16B	109.5
N1—C13—C12	121.2 (5)	H16A—C16—H16B	109.5
C14—C13—C12	117.0 (6)	N1—C16—H16C	109.5
O2—C5—C4	118.2 (6)	H16A—C16—H16C	109.5
O2—C5—C6	121.8 (6)	H16B—C16—H16C	109.5
C4—C5—C6	119.9 (7)	C2—C3—C4	118.1 (6)
C11—C12—C13	120.1 (6)	C2—C3—H3A	120.9
C11—C12—H12A	119.9	C4—C3—H3A	120.9
C13—C12—H12A	119.9	N1—C17—H17A	109.5
C2—C1—C6	120.5 (6)	N1—C17—H17B	109.5
C2—C1—H1A	119.8	H17A—C17—H17B	109.5
C6—C1—H1A	119.8	N1—C17—H17C	109.5
C1—C6—C5	117.7 (6)	H17A—C17—H17C	109.5
C1—C6—C7	122.8 (6)	H17B—C17—H17C	109.5
C5—C6—C7	119.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.82	2.543 (7)	146
C17—H17A···O2ⁱ	0.98	2.55	3.503 (10)	164

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆BrNO₂
M_r	346.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	15.1905 (5), 5.4501 (2), 19.7569 (9)
β (°)	106.00 (2)
V (Å³)	1572.34 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.62
Crystal size (mm)	0.30 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8044, 2736, 1538
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.089, 0.287, 1.09
No. of reflections	2736
No. of parameters	193
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.58, −1.11

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.82	2.543 (7)	146
C17—H17A···O2ⁱ	0.98	2.55	3.503 (10)	164

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the start-up fund of Anyang Institute of Technology, China.

References

Dai, J. & Chen, X.-Y. (2011). Acta Cryst. E67, o287. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fu, D.-W., Zhao, M.-M. & Ge, J.-Z. (2011). J. Mol. Struct. 1006, 227–233. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, R.-J., Fu, D.-W., Dai, J., Zhang, Y., Ge, J.-Z. & Ye, H.-Y. (2011). Inorg. Chem. Commun. 14, 1093–1096. Web of Science CSD CrossRef CAS Google Scholar
Zheng, W.-N. (2011). Acta Cryst. E67, m344. Web of Science CSD CrossRef IUCr Journals Google Scholar

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(E)-1-(5-Bromo-2-hy­dr­oxy­phen­yl)-3-[4-(di­methyl­amino)­phen­yl]prop-2-en-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-1-(5-Bromo-2-hydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one