(2E)-3-(3-Bromo-4-meth-oxy-phen-yl)-1-(pyridin-2-yl)prop-2-en-1-one.

The mean planes of the benzene and pyridine rings in the title compound, C(15)H(12)BrNO(2), are nearly coplanar, subtending an angle of 2.8 (8)°. The prop-2-en-1-one group is also in the plane of these rings with an N-C-C-O torsion angle of 179.6 (3)°. A weak C-H⋯Br inter-molecular inter-action contributes to the crystal packing, creating a chain-like structure along the a axis.

Related literature

For the pharmacological activity of chalcones, see: Dhar (1981 ▶); Dimmock et al. (1999 ▶); Satyanarayana et al. (2004 ▶). For their ability to block voltage-dependent potassium channels, see: Yarishkin et al. (2008 ▶). For their applications as organic non-linear optical materials due to their SHG conversion efficiency, see: Sarojini et al. (2006 ▶) and excellent blue light transmittance and good crystallization ability, see: Goto et al. (1991 ▶); Indira et al. (2002 ▶); Uchida et al. (1998 ▶). For the use of chalcones in the synthesis of various biodynamic heterocyclic compounds such as cyclo­hexenone and pyrazoline derivatives, see: Ashalatha et al. (2009 ▶); Sreevidya et al. (2010 ▶); Samshuddin et al. (2010 ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010a ▶,b ▶). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999 ▶). For related structures, see: Bibila Mayaya Bisseyou et al. (2007 ▶); Liu et al. (2005 ▶).

Experimental

Crystal data

C15H12BrNO2

M = 318.17

Monoclinic,

a = 26.3402 (13) Å

b = 3.8906 (2) Å

c = 27.5826 (17) Å

β = 113.892 (5)°

V = 2584.4 (2) Å3

Z = 8

Cu Kα radiation

μ = 4.31 mm−1

T = 123 K

0.49 × 0.21 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.535, T max = 1.000

3978 measured reflections

2556 independent reflections

2431 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.08

2556 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.64 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000353/ng5098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000353/ng5098Isup2.hkl

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

C15H12BrNO2	F(000) = 1280
Mr = 318.17	Dx = 1.635 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 3510 reflections
a = 26.3402 (13) Å	θ = 4.7–74.0°
b = 3.8906 (2) Å	µ = 4.31 mm−1
c = 27.5826 (17) Å	T = 123 K
β = 113.892 (5)°	Needle, colorless
V = 2584.4 (2) Å3	0.49 × 0.21 × 0.16 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2556 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2431 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 10.5081 pixels mm-1	θmax = 74.1°, θmin = 6.0°
ω scans	h = −29→32
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −4→2
Tmin = 0.535, Tmax = 1.000	l = −34→33
3978 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0704P)2 + 6.6225P] where P = (Fo2 + 2Fc2)/3
2556 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.64 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
Br1	0.046034 (12)	0.06121 (9)	0.063358 (11)	0.03852 (15)
O1	0.36895 (11)	0.4707 (8)	0.17800 (10)	0.0507 (6)
O2	0.04309 (8)	0.3262 (7)	0.16281 (8)	0.0431 (5)
N1	0.30803 (11)	0.0395 (8)	0.05431 (11)	0.0410 (6)
C1	0.34866 (11)	0.1894 (9)	0.09571 (12)	0.0359 (6)
C2	0.40303 (12)	0.2175 (8)	0.10013 (13)	0.0382 (6)
H2A	0.4308	0.3251	0.1300	0.046*
C3	0.41559 (13)	0.0837 (9)	0.05953 (15)	0.0441 (8)
H3A	0.4523	0.0956	0.0614	0.053*
C4	0.37382 (15)	−0.0664 (9)	0.01663 (15)	0.0451 (8)
H4A	0.3812	−0.1569	−0.0119	0.054*
C5	0.32078 (15)	−0.0833 (9)	0.01567 (14)	0.0442 (8)
H5A	0.2922	−0.1875	−0.0140	0.053*
C6	0.33420 (13)	0.3330 (10)	0.13914 (12)	0.0420 (7)
C7	0.27542 (13)	0.3026 (9)	0.13151 (12)	0.0410 (7)
H7A	0.2503	0.1747	0.1023	0.049*
C8	0.25712 (14)	0.4531 (9)	0.16526 (13)	0.0404 (7)
H8A	0.2833	0.5857	0.1931	0.048*
C9	0.20072 (13)	0.4324 (9)	0.16324 (12)	0.0389 (7)
C10	0.15685 (12)	0.2790 (9)	0.12093 (11)	0.0359 (6)
H10A	0.1628	0.1909	0.0915	0.043*
C11	0.10531 (11)	0.2558 (7)	0.12193 (11)	0.0311 (6)
C12	0.09521 (12)	0.3743 (8)	0.16536 (11)	0.0335 (6)
C13	0.13844 (13)	0.5282 (9)	0.20707 (13)	0.0374 (7)
H13A	0.1327	0.6135	0.2367	0.045*
C14	0.19004 (14)	0.5571 (9)	0.20544 (13)	0.0395 (7)
H14A	0.2192	0.6660	0.2341	0.047*
C15	0.03317 (15)	0.4373 (11)	0.20775 (14)	0.0489 (9)
H15A	−0.0049	0.3784	0.2024	0.073*
H15B	0.0383	0.6868	0.2118	0.073*
H15C	0.0594	0.3227	0.2398	0.073*

	U11	U22	U33	U12	U13	U23
Br1	0.0377 (2)	0.0436 (2)	0.0325 (2)	−0.00132 (12)	0.01247 (15)	−0.00231 (12)
O1	0.0427 (13)	0.0683 (16)	0.0394 (13)	−0.0095 (12)	0.0149 (11)	−0.0008 (11)
O2	0.0317 (10)	0.0681 (15)	0.0339 (10)	0.0021 (11)	0.0177 (8)	−0.0024 (11)
N1	0.0317 (13)	0.0494 (16)	0.0400 (14)	−0.0043 (11)	0.0124 (11)	0.0067 (12)
C1	0.0283 (13)	0.0413 (16)	0.0366 (14)	−0.0025 (12)	0.0116 (11)	0.0114 (13)
C2	0.0291 (13)	0.0392 (16)	0.0450 (16)	−0.0025 (12)	0.0136 (12)	0.0083 (13)
C3	0.0343 (16)	0.0416 (19)	0.060 (2)	0.0050 (13)	0.0231 (15)	0.0099 (15)
C4	0.0501 (19)	0.0388 (18)	0.0502 (19)	0.0078 (14)	0.0241 (16)	0.0077 (14)
C5	0.0418 (17)	0.0439 (19)	0.0430 (17)	−0.0038 (13)	0.0130 (14)	0.0025 (14)
C6	0.0341 (14)	0.0554 (19)	0.0385 (16)	0.0013 (14)	0.0168 (13)	0.0130 (15)
C7	0.0378 (15)	0.0466 (18)	0.0381 (15)	−0.0029 (14)	0.0149 (12)	−0.0003 (14)
C8	0.0409 (16)	0.0433 (18)	0.0346 (15)	−0.0030 (13)	0.0130 (13)	0.0018 (13)
C9	0.0340 (15)	0.0511 (19)	0.0322 (15)	0.0061 (13)	0.0141 (12)	0.0104 (13)
C10	0.0342 (13)	0.0466 (17)	0.0288 (13)	0.0082 (13)	0.0147 (11)	0.0069 (12)
C11	0.0319 (13)	0.0315 (14)	0.0289 (12)	0.0025 (11)	0.0113 (10)	0.0037 (11)
C12	0.0301 (13)	0.0391 (15)	0.0325 (14)	0.0051 (12)	0.0140 (11)	0.0040 (12)
C13	0.0385 (16)	0.0416 (16)	0.0326 (14)	0.0069 (13)	0.0149 (13)	0.0001 (12)
C14	0.0354 (15)	0.0464 (18)	0.0322 (15)	0.0004 (13)	0.0092 (12)	0.0028 (13)
C15	0.0409 (17)	0.074 (3)	0.0398 (17)	0.0117 (16)	0.0243 (15)	0.0033 (16)

Br1—C11	1.892 (3)	C7—C8	1.344 (5)
O1—C6	1.216 (4)	C7—H7A	0.9500
O2—C12	1.359 (3)	C8—C9	1.466 (4)
O2—C15	1.433 (4)	C8—H8A	0.9500
N1—C5	1.329 (5)	C9—C14	1.391 (5)
N1—C1	1.341 (4)	C9—C10	1.400 (5)
C1—C2	1.391 (4)	C10—C11	1.372 (4)
C1—C6	1.504 (5)	C10—H10A	0.9500
C2—C3	1.391 (5)	C11—C12	1.406 (4)
C2—H2A	0.9500	C12—C13	1.385 (4)
C3—C4	1.377 (5)	C13—C14	1.383 (5)
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.388 (5)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9800
C5—H5A	0.9500	C15—H15B	0.9800
C6—C7	1.480 (4)	C15—H15C	0.9800
C12—O2—C15	116.6 (3)	C9—C8—H8A	116.8
C5—N1—C1	117.7 (3)	C14—C9—C10	117.9 (3)
N1—C1—C2	123.1 (3)	C14—C9—C8	119.6 (3)
N1—C1—C6	117.9 (3)	C10—C9—C8	122.4 (3)
C2—C1—C6	119.0 (3)	C11—C10—C9	120.0 (3)
C3—C2—C1	118.2 (3)	C11—C10—H10A	120.0
C3—C2—H2A	120.9	C9—C10—H10A	120.0
C1—C2—H2A	120.9	C10—C11—C12	121.7 (3)
C4—C3—C2	118.9 (3)	C10—C11—Br1	119.4 (2)
C4—C3—H3A	120.6	C12—C11—Br1	118.9 (2)
C2—C3—H3A	120.6	O2—C12—C13	125.2 (3)
C3—C4—C5	118.9 (3)	O2—C12—C11	116.5 (3)
C3—C4—H4A	120.5	C13—C12—C11	118.3 (3)
C5—C4—H4A	120.5	C14—C13—C12	119.8 (3)
N1—C5—C4	123.2 (3)	C14—C13—H13A	120.1
N1—C5—H5A	118.4	C12—C13—H13A	120.1
C4—C5—H5A	118.4	C13—C14—C9	122.2 (3)
O1—C6—C7	122.1 (3)	C13—C14—H14A	118.9
O1—C6—C1	121.5 (3)	C9—C14—H14A	118.9
C7—C6—C1	116.4 (3)	O2—C15—H15A	109.5
C8—C7—C6	121.0 (3)	O2—C15—H15B	109.5
C8—C7—H7A	119.5	H15A—C15—H15B	109.5
C6—C7—H7A	119.5	O2—C15—H15C	109.5
C7—C8—C9	126.3 (3)	H15A—C15—H15C	109.5
C7—C8—H8A	116.8	H15B—C15—H15C	109.5
C5—N1—C1—C2	−0.8 (5)	C7—C8—C9—C10	−7.5 (5)
C5—N1—C1—C6	179.2 (3)	C14—C9—C10—C11	0.1 (5)
N1—C1—C2—C3	0.1 (5)	C8—C9—C10—C11	177.7 (3)
C6—C1—C2—C3	−179.9 (3)	C9—C10—C11—C12	−1.8 (5)
C1—C2—C3—C4	0.8 (5)	C9—C10—C11—Br1	178.0 (2)
C2—C3—C4—C5	−0.9 (5)	C15—O2—C12—C13	−1.6 (5)
C1—N1—C5—C4	0.7 (5)	C15—O2—C12—C11	178.1 (3)
C3—C4—C5—N1	0.1 (5)	C10—C11—C12—O2	−177.6 (3)
N1—C1—C6—O1	179.6 (3)	Br1—C11—C12—O2	2.7 (4)
C2—C1—C6—O1	−0.4 (5)	C10—C11—C12—C13	2.2 (5)
N1—C1—C6—C7	−1.4 (4)	Br1—C11—C12—C13	−177.6 (2)
C2—C1—C6—C7	178.6 (3)	O2—C12—C13—C14	178.9 (3)
O1—C6—C7—C8	5.8 (6)	C11—C12—C13—C14	−0.9 (5)
C1—C6—C7—C8	−173.2 (3)	C12—C13—C14—C9	−0.8 (5)
C6—C7—C8—C9	−177.7 (3)	C10—C9—C14—C13	1.2 (5)
C7—C8—C9—C14	170.1 (3)	C8—C9—C14—C13	−176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Br1i	0.95	3.04	3.870 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Br1i	0.95	3.04	3.870 (3)	146

Symmetry code: (i) .