(2E)-3-(4-Methyl-phen-yl)-1-(pyridin-3-yl)prop-2-en-1-one.

The title compound, C(15)H(13)NO, has two crystallographically independent mol-ecules in the asymmetric unit which differ principally in the periplanar angle formed by the benzene and pyridine rings [41.41 (3) and 17.92 (5)°]. The mol-ecules exhibit an E conformation between the keto group with respect to the olefin double bond.

Related literature

For background to related compounds, see: Katsori & Hadjipavlou-Litina (2011 ▶). For biological and medicinal applications of chalcones, see: Bandgar et al. (2010 ▶); Juvale et al. (2012 ▶); Liu et al. (2003 ▶); Sivakumar et al. (2011 ▶); Trivedi et al. (2007 ▶); Viana et al. (2003 ▶). For the synthesis of chalcones, see: Patil et al. (2009 ▶).

Experimental

Crystal data

C15H13NO

M = 223.26

Triclinic,

a = 5.9026 (7) Å

b = 14.2199 (16) Å

c = 14.6772 (17) Å

α = 69.654 (2)°

β = 84.231 (2)°

γ = 81.280 (2)°

V = 1140.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.19 × 0.08 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: numerical (SADABS; Bruker, 2012 ▶) T min = 0.988, T max = 0.997

23125 measured reflections

4692 independent reflections

3684 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.03

4692 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: POV-RAY (Cason, 2003 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032746/nk2177sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032746/nk2177Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032746/nk2177Isup3.cml

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

C15H13NO	Z = 4
Mr = 223.26	F(000) = 472
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9026 (7) Å	Cell parameters from 6635 reflections
b = 14.2199 (16) Å	θ = 2.5–26.4°
c = 14.6772 (17) Å	µ = 0.08 mm−1
α = 69.654 (2)°	T = 120 K
β = 84.231 (2)°	Block, colourless
γ = 81.280 (2)°	0.19 × 0.08 × 0.05 mm
V = 1140.2 (2) Å3

Bruker APEXII diffractometer	4692 independent reflections
Radiation source: fine-focus sealed tube	3684 reflections with I > 2σ(I)
Bruker TRIUMPH curved-graphite monochromator	Rint = 0.027
Detector resolution: 8.33 pixels mm-1	θmax = 26.5°, θmin = 1.5°
combination of ω and φ–scans	h = −7→7
Absorption correction: numerical (SADABS; Bruker, 2012	k = −17→17
Tmin = 0.988, Tmax = 0.997	l = −18→18
23125 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.4373P] where P = (Fo2 + 2Fc2)/3
4692 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 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
O1	1.21189 (17)	0.89124 (8)	0.50027 (8)	0.0260 (3)
N1	1.0864 (2)	0.99097 (10)	0.21022 (9)	0.0252 (3)
C1	0.8702 (3)	1.02931 (11)	0.18543 (11)	0.0231 (3)
H1	0.8425	1.0611	0.1183	0.028*
C2	0.6856 (2)	1.02514 (11)	0.25204 (11)	0.0226 (3)
H2	0.5355	1.0531	0.2307	0.027*
C3	0.7227 (2)	0.97950 (11)	0.35032 (11)	0.0209 (3)
H3	0.5986	0.9750	0.3976	0.025*
C4	0.9451 (2)	0.94052 (10)	0.37837 (10)	0.0185 (3)
C5	1.1185 (2)	0.94819 (11)	0.30519 (11)	0.0217 (3)
H5	1.2704	0.9210	0.3244	0.026*
C6	1.0128 (2)	0.89387 (10)	0.48122 (11)	0.0199 (3)
C7	0.8380 (2)	0.85094 (11)	0.55766 (10)	0.0207 (3)
H7	0.6911	0.8455	0.5402	0.025*
C8	0.8858 (2)	0.81970 (10)	0.65125 (11)	0.0199 (3)
H8	1.0316	0.8309	0.6647	0.024*
C9	0.7396 (2)	0.77026 (10)	0.73542 (10)	0.0188 (3)
C10	0.5392 (2)	0.73304 (11)	0.72701 (11)	0.0211 (3)
H10	0.4936	0.7400	0.6645	0.025*
C11	0.4071 (2)	0.68613 (11)	0.80912 (11)	0.0219 (3)
H11	0.2719	0.6612	0.8019	0.026*
C12	0.4676 (3)	0.67463 (11)	0.90202 (11)	0.0224 (3)
C13	0.6673 (3)	0.71086 (11)	0.91037 (11)	0.0238 (3)
H13	0.7127	0.7034	0.9730	0.029*
C14	0.8011 (2)	0.75763 (11)	0.82884 (11)	0.0219 (3)
H14	0.9372	0.7816	0.8365	0.026*
C15	0.3179 (3)	0.62614 (13)	0.99064 (12)	0.0319 (4)
H15A	0.2129	0.5881	0.9739	0.048*
H15B	0.2290	0.6787	1.0131	0.048*
H15C	0.4146	0.5801	1.0425	0.048*
O2	1.03753 (17)	0.70034 (8)	0.34296 (8)	0.0276 (3)
N2	0.9368 (2)	0.84417 (10)	0.05356 (9)	0.0258 (3)
C16	0.7218 (3)	0.87995 (11)	0.02547 (11)	0.0244 (3)
H16	0.7003	0.9168	−0.0414	0.029*
C17	0.5298 (3)	0.86595 (11)	0.08880 (11)	0.0241 (3)
H17	0.3807	0.8919	0.0654	0.029*
C18	0.5586 (2)	0.81352 (11)	0.18673 (10)	0.0205 (3)
H18	0.4295	0.8028	0.2316	0.025*
C19	0.7788 (2)	0.77691 (10)	0.21845 (10)	0.0179 (3)
C20	0.9597 (2)	0.79400 (11)	0.14810 (11)	0.0225 (3)
H20	1.1105	0.7679	0.1693	0.027*
C21	0.8356 (2)	0.72037 (10)	0.32200 (10)	0.0193 (3)
C22	0.6481 (2)	0.68910 (11)	0.39596 (10)	0.0207 (3)
H22	0.4946	0.7185	0.3817	0.025*
C23	0.6925 (2)	0.61986 (11)	0.48271 (10)	0.0195 (3)
H23	0.8487	0.5924	0.4928	0.023*
C24	0.5285 (2)	0.58134 (10)	0.56403 (10)	0.0182 (3)
C25	0.2975 (2)	0.62264 (11)	0.56456 (10)	0.0200 (3)
H25	0.2401	0.6759	0.5089	0.024*
C26	0.1526 (2)	0.58659 (11)	0.64536 (11)	0.0213 (3)
H26	−0.0032	0.6159	0.6444	0.026*
C27	0.2294 (3)	0.50814 (11)	0.72827 (10)	0.0208 (3)
C28	0.4577 (3)	0.46570 (11)	0.72671 (10)	0.0222 (3)
H28	0.5134	0.4112	0.7818	0.027*
C29	0.6049 (2)	0.50143 (11)	0.64645 (10)	0.0208 (3)
H29	0.7600	0.4713	0.6473	0.025*
C30	0.0694 (3)	0.47278 (12)	0.81652 (11)	0.0287 (4)
H30A	−0.0431	0.5297	0.8204	0.043*
H30B	0.1578	0.4463	0.8752	0.043*
H30C	−0.0106	0.4194	0.8114	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0183 (5)	0.0319 (6)	0.0242 (6)	−0.0048 (4)	−0.0003 (4)	−0.0046 (5)
N1	0.0232 (6)	0.0308 (7)	0.0206 (7)	−0.0072 (5)	0.0043 (5)	−0.0073 (6)
C1	0.0272 (8)	0.0238 (7)	0.0171 (7)	−0.0070 (6)	−0.0004 (6)	−0.0042 (6)
C2	0.0204 (7)	0.0219 (7)	0.0238 (8)	−0.0026 (6)	−0.0011 (6)	−0.0057 (6)
C3	0.0185 (7)	0.0222 (7)	0.0213 (8)	−0.0042 (6)	0.0041 (6)	−0.0072 (6)
C4	0.0202 (7)	0.0161 (7)	0.0192 (7)	−0.0056 (5)	0.0019 (6)	−0.0055 (6)
C5	0.0171 (7)	0.0240 (7)	0.0231 (8)	−0.0036 (6)	0.0011 (6)	−0.0070 (6)
C6	0.0196 (7)	0.0179 (7)	0.0218 (8)	−0.0019 (5)	0.0008 (6)	−0.0067 (6)
C7	0.0191 (7)	0.0218 (7)	0.0202 (8)	−0.0043 (6)	0.0010 (6)	−0.0054 (6)
C8	0.0178 (7)	0.0181 (7)	0.0232 (8)	−0.0026 (5)	−0.0003 (6)	−0.0064 (6)
C9	0.0200 (7)	0.0168 (7)	0.0186 (7)	−0.0011 (5)	−0.0006 (6)	−0.0054 (6)
C10	0.0231 (7)	0.0237 (7)	0.0187 (7)	−0.0043 (6)	−0.0007 (6)	−0.0092 (6)
C11	0.0210 (7)	0.0236 (7)	0.0229 (8)	−0.0068 (6)	0.0023 (6)	−0.0093 (6)
C12	0.0238 (7)	0.0205 (7)	0.0210 (8)	−0.0026 (6)	0.0033 (6)	−0.0058 (6)
C13	0.0267 (8)	0.0270 (8)	0.0173 (8)	−0.0021 (6)	−0.0031 (6)	−0.0071 (6)
C14	0.0200 (7)	0.0227 (7)	0.0232 (8)	−0.0033 (6)	−0.0030 (6)	−0.0074 (6)
C15	0.0324 (9)	0.0383 (9)	0.0219 (9)	−0.0096 (7)	0.0070 (7)	−0.0065 (7)
O2	0.0176 (5)	0.0349 (6)	0.0241 (6)	−0.0022 (4)	−0.0027 (4)	−0.0023 (5)
N2	0.0243 (7)	0.0301 (7)	0.0195 (7)	−0.0064 (5)	0.0032 (5)	−0.0037 (6)
C16	0.0293 (8)	0.0244 (8)	0.0162 (8)	−0.0045 (6)	−0.0005 (6)	−0.0025 (6)
C17	0.0211 (7)	0.0268 (8)	0.0210 (8)	−0.0016 (6)	−0.0031 (6)	−0.0037 (6)
C18	0.0185 (7)	0.0222 (7)	0.0192 (8)	−0.0034 (6)	0.0028 (6)	−0.0058 (6)
C19	0.0194 (7)	0.0161 (7)	0.0183 (7)	−0.0037 (5)	0.0002 (5)	−0.0058 (6)
C20	0.0174 (7)	0.0250 (8)	0.0231 (8)	−0.0038 (6)	0.0003 (6)	−0.0054 (6)
C21	0.0194 (7)	0.0175 (7)	0.0204 (8)	−0.0020 (6)	−0.0005 (6)	−0.0057 (6)
C22	0.0190 (7)	0.0237 (7)	0.0183 (8)	−0.0025 (6)	−0.0006 (6)	−0.0059 (6)
C23	0.0185 (7)	0.0215 (7)	0.0197 (7)	−0.0025 (6)	−0.0014 (6)	−0.0086 (6)
C24	0.0221 (7)	0.0189 (7)	0.0158 (7)	−0.0053 (6)	−0.0020 (5)	−0.0070 (6)
C25	0.0231 (7)	0.0197 (7)	0.0161 (7)	−0.0029 (6)	−0.0032 (6)	−0.0038 (6)
C26	0.0209 (7)	0.0230 (7)	0.0214 (8)	−0.0044 (6)	0.0006 (6)	−0.0091 (6)
C27	0.0278 (8)	0.0206 (7)	0.0166 (7)	−0.0093 (6)	0.0006 (6)	−0.0073 (6)
C28	0.0302 (8)	0.0196 (7)	0.0154 (7)	−0.0057 (6)	−0.0050 (6)	−0.0019 (6)
C29	0.0211 (7)	0.0200 (7)	0.0213 (8)	−0.0020 (6)	−0.0036 (6)	−0.0065 (6)
C30	0.0337 (9)	0.0303 (8)	0.0210 (8)	−0.0112 (7)	0.0042 (7)	−0.0057 (7)

O1—C6	1.2269 (17)	C25—C26	1.381 (2)
N1—C5	1.3332 (19)	C26—C27	1.395 (2)
N1—C1	1.3427 (19)	C27—C28	1.392 (2)
C1—C2	1.383 (2)	C27—C30	1.506 (2)
C2—C3	1.385 (2)	C28—C29	1.383 (2)
C3—C4	1.389 (2)	C1—H1	0.9500
C4—C5	1.395 (2)	C2—H2	0.9500
C4—C6	1.491 (2)	C3—H3	0.9500
C6—C7	1.4758 (19)	C5—H5	0.9500
C7—C8	1.334 (2)	C7—H7	0.9500
C8—C9	1.4596 (19)	C8—H8	0.9500
C9—C14	1.397 (2)	C10—H10	0.9500
C9—C10	1.400 (2)	C11—H11	0.9500
C10—C11	1.384 (2)	C13—H13	0.9500
C11—C12	1.392 (2)	C14—H14	0.9500
C12—C13	1.388 (2)	C15—H15A	0.9800
C12—C15	1.509 (2)	C15—H15B	0.9800
C13—C14	1.383 (2)	C15—H15C	0.9800
O2—C21	1.2270 (17)	C16—H16	0.9500
N2—C20	1.3315 (19)	C17—H17	0.9500
N2—C16	1.342 (2)	C18—H18	0.9500
C16—C17	1.384 (2)	C20—H20	0.9500
C17—C18	1.384 (2)	C22—H22	0.9500
C18—C19	1.387 (2)	C23—H23	0.9500
C19—C20	1.395 (2)	C25—H25	0.9500
C19—C21	1.497 (2)	C26—H26	0.9500
C21—C22	1.4742 (19)	C28—H28	0.9500
C22—C23	1.333 (2)	C29—H29	0.9500
C23—C24	1.4614 (19)	C30—H30A	0.9800
C24—C29	1.399 (2)	C30—H30B	0.9800
C24—C25	1.401 (2)	C30—H30C	0.9800
C5—N1—C1	116.27 (13)	C3—C2—H2	120.5
N1—C1—C2	123.74 (14)	C2—C3—H3	120.7
C1—C2—C3	118.99 (14)	C4—C3—H3	120.7
C2—C3—C4	118.63 (13)	N1—C5—H5	117.7
C3—C4—C5	117.69 (13)	C4—C5—H5	117.7
C3—C4—C6	124.68 (13)	C8—C7—H7	119.9
C5—C4—C6	117.60 (12)	C6—C7—H7	119.9
N1—C5—C4	124.67 (13)	C7—C8—H8	116.3
O1—C6—C7	121.61 (13)	C9—C8—H8	116.3
O1—C6—C4	119.53 (13)	C11—C10—H10	119.8
C7—C6—C4	118.86 (12)	C9—C10—H10	119.8
C8—C7—C6	120.17 (13)	C10—C11—H11	119.2
C7—C8—C9	127.43 (13)	C12—C11—H11	119.2
C14—C9—C10	117.80 (13)	C14—C13—H13	119.5
C14—C9—C8	119.54 (13)	C12—C13—H13	119.5
C10—C9—C8	122.65 (13)	C13—C14—H14	119.4
C11—C10—C9	120.46 (14)	C9—C14—H14	119.4
C10—C11—C12	121.58 (14)	C12—C15—H15A	109.5
C13—C12—C11	117.93 (13)	C12—C15—H15B	109.5
C13—C12—C15	121.11 (14)	H15A—C15—H15B	109.5
C11—C12—C15	120.95 (14)	C12—C15—H15C	109.5
C14—C13—C12	121.01 (14)	H15A—C15—H15C	109.5
C13—C14—C9	121.21 (14)	H15B—C15—H15C	109.5
C20—N2—C16	116.36 (13)	N2—C16—H16	118.2
N2—C16—C17	123.51 (14)	C17—C16—H16	118.2
C16—C17—C18	118.90 (14)	C16—C17—H17	120.5
C17—C18—C19	119.07 (13)	C18—C17—H17	120.5
C18—C19—C20	117.21 (13)	C17—C18—H18	120.5
C18—C19—C21	124.84 (13)	C19—C18—H18	120.5
C20—C19—C21	117.95 (12)	N2—C20—H20	117.5
N2—C20—C19	124.94 (13)	C19—C20—H20	117.5
O2—C21—C19	119.07 (13)	C26—C25—H25	119.8
C22—C21—C19	119.23 (12)	C23—C22—H22	119.8
C23—C22—C21	120.45 (13)	C21—C22—H22	119.8
O2—C21—C22	121.69 (13)	C22—C23—H23	116.3
C22—C23—C24	127.46 (13)	C24—C23—H23	116.3
C29—C24—C25	117.97 (13)	C24—C25—H25	119.8
C29—C24—C23	119.10 (13)	C25—C26—H26	119.2
C25—C24—C23	122.92 (13)	C27—C26—H26	119.2
C26—C25—C24	120.50 (13)	C29—C28—H28	119.4
C25—C26—C27	121.60 (14)	C27—C28—H28	119.4
C28—C27—C26	117.77 (13)	C28—C29—H29	119.5
C28—C27—C30	121.84 (13)	C24—C29—H29	119.5
C26—C27—C30	120.38 (14)	C27—C30—H30A	109.5
C29—C28—C27	121.19 (13)	C27—C30—H30B	109.5
C28—C29—C24	120.94 (13)	H30A—C30—H30B	109.5
N1—C1—H1	118.1	C27—C30—H30C	109.5
C2—C1—H1	118.1	H30A—C30—H30C	109.5
C1—C2—H2	120.5	H30B—C30—H30C	109.5
C5—N1—C1—C2	−0.9 (2)	C20—N2—C16—C17	−0.8 (2)
N1—C1—C2—C3	0.3 (2)	N2—C16—C17—C18	0.9 (2)
C1—C2—C3—C4	0.7 (2)	C16—C17—C18—C19	0.2 (2)
C2—C3—C4—C5	−1.1 (2)	C17—C18—C19—C20	−1.2 (2)
C2—C3—C4—C6	176.94 (13)	C17—C18—C19—C21	179.11 (14)
C1—N1—C5—C4	0.4 (2)	C16—N2—C20—C19	−0.3 (2)
C3—C4—C5—N1	0.5 (2)	C18—C19—C20—N2	1.3 (2)
C6—C4—C5—N1	−177.64 (13)	C21—C19—C20—N2	−178.99 (14)
C3—C4—C6—O1	−156.74 (14)	C18—C19—C21—O2	−172.83 (14)
C5—C4—C6—O1	21.3 (2)	C20—C19—C21—O2	7.5 (2)
C3—C4—C6—C7	23.9 (2)	C18—C19—C21—C22	7.9 (2)
C5—C4—C6—C7	−158.09 (13)	C20—C19—C21—C22	−171.81 (13)
O1—C6—C7—C8	8.6 (2)	O2—C21—C22—C23	−14.8 (2)
C4—C6—C7—C8	−171.99 (13)	C19—C21—C22—C23	164.46 (13)
C6—C7—C8—C9	−176.07 (13)	C21—C22—C23—C24	179.32 (13)
C7—C8—C9—C14	−169.49 (14)	C22—C23—C24—C29	173.98 (14)
C7—C8—C9—C10	11.4 (2)	C22—C23—C24—C25	−7.7 (2)
C14—C9—C10—C11	0.5 (2)	C29—C24—C25—C26	1.6 (2)
C8—C9—C10—C11	179.57 (13)	C23—C24—C25—C26	−176.72 (13)
C9—C10—C11—C12	0.2 (2)	C24—C25—C26—C27	−0.4 (2)
C10—C11—C12—C13	−0.7 (2)	C25—C26—C27—C28	−1.0 (2)
C10—C11—C12—C15	178.11 (14)	C25—C26—C27—C30	177.93 (14)
C11—C12—C13—C14	0.5 (2)	C26—C27—C28—C29	1.3 (2)
C15—C12—C13—C14	−178.31 (14)	C30—C27—C28—C29	−177.61 (14)
C12—C13—C14—C9	0.2 (2)	C27—C28—C29—C24	−0.2 (2)
C10—C9—C14—C13	−0.7 (2)	C25—C24—C29—C28	−1.3 (2)
C8—C9—C14—C13	−179.79 (13)	C23—C24—C29—C28	177.09 (13)