(E)-5,6-Dimeth-oxy-2-(pyridin-4-yl-methyl-idene)-2,3-dihydro-1H-inden-1-one.

The mol-ecule of the title compound, C(17)H(15)NO(3), is slightly twisted, with a dihedral angle of 12.12 (3)° between the dihydro-indenone group and the pyridine ring. In the crystal, mol-ecules are connected into layers parallel to the ab plane via inter-molecular C-H⋯O hydrogen bonds. Weak π-π [centroid-centroid distance = 3.5680 (6) Å] inter-actions are also observed.

Related literature

For general background and the biological activity of chalcone derivatives, see: Nowakowska (2008 ▶); Akihisa et al. (2006 ▶); Narender et al. (2005 ▶); Zhang et al. (2006 ▶); Dicarlo et al. (1999 ▶); Heidenreich et al. (2008 ▶); Syed et al. (2008 ▶); D’Archivio et al. (2008 ▶). For a related structure, see: Ali et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H15NO3

M = 281.30

Monoclinic,

a = 10.7572 (14) Å

b = 8.6057 (11) Å

c = 17.2961 (17) Å

β = 123.394 (6)°

V = 1336.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.45 × 0.32 × 0.23 mm

Data collection

Bruker APEXII Duo CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.979

21745 measured reflections

5874 independent reflections

5138 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.132

S = 1.10

5874 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039486/rz2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039486/rz2492Isup2.hkl

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

C17H15NO3	F(000) = 592
Mr = 281.30	Dx = 1.398 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9933 reflections
a = 10.7572 (14) Å	θ = 2.8–35.1°
b = 8.6057 (11) Å	µ = 0.10 mm−1
c = 17.2961 (17) Å	T = 100 K
β = 123.394 (6)°	Block, yellow
V = 1336.8 (3) Å3	0.45 × 0.32 × 0.23 mm
Z = 4

Bruker APEXII Duo CCD area-detector diffractometer	5874 independent reflections
Radiation source: fine-focus sealed tube	5138 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 35.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.958, Tmax = 0.979	k = −13→13
21745 measured reflections	l = −17→27

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0783P)2 + 0.2242P] where P = (Fo2 + 2Fc2)/3
5874 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.32457 (7)	0.81081 (8)	−0.16256 (4)	0.02006 (13)
O2	0.80183 (6)	0.43182 (7)	−0.05682 (4)	0.01665 (11)
O3	0.92680 (6)	0.42839 (7)	0.11848 (4)	0.01546 (11)
N1	0.16589 (8)	1.13656 (9)	0.15678 (5)	0.01914 (13)
C1	0.41258 (8)	0.78448 (8)	−0.07968 (5)	0.01273 (12)
C2	0.54736 (7)	0.68903 (7)	−0.03693 (4)	0.01082 (11)
C3	0.60522 (8)	0.60592 (8)	−0.08026 (4)	0.01211 (12)
H3A	0.5587	0.6093	−0.1442	0.015*
C4	0.73270 (7)	0.51920 (8)	−0.02574 (4)	0.01175 (12)
C5	0.80361 (7)	0.51765 (8)	0.07250 (4)	0.01137 (11)
C6	0.74738 (7)	0.60432 (8)	0.11466 (4)	0.01135 (11)
H6A	0.7955	0.6055	0.1787	0.014*
C7	0.61696 (7)	0.68941 (7)	0.05839 (4)	0.01039 (11)
C8	0.53304 (8)	0.78599 (8)	0.08831 (4)	0.01196 (12)
H8A	0.5018	0.7233	0.1213	0.014*
H8B	0.5934	0.8717	0.1275	0.014*
C9	0.40070 (7)	0.84391 (8)	−0.00227 (4)	0.01164 (11)
C10	0.28495 (8)	0.93423 (8)	−0.02118 (5)	0.01312 (12)
H10A	0.2176	0.9567	−0.0835	0.016*
C11	0.24992 (7)	1.00219 (8)	0.04230 (5)	0.01233 (12)
C12	0.31954 (9)	0.96061 (10)	0.13540 (5)	0.01933 (15)
H12A	0.3965	0.8883	0.1618	0.023*
C13	0.27285 (10)	1.02821 (11)	0.18809 (6)	0.02310 (17)
H13A	0.3188	0.9962	0.2493	0.028*
C14	0.10022 (8)	1.17804 (9)	0.06768 (5)	0.01567 (13)
H14A	0.0262	1.2536	0.0440	0.019*
C15	0.13705 (8)	1.11388 (8)	0.00888 (5)	0.01385 (12)
H15A	0.0866	1.1453	−0.0527	0.017*
C16	0.74321 (9)	0.43840 (10)	−0.15362 (5)	0.01808 (14)
H16A	0.8014	0.3730	−0.1670	0.027*
H16B	0.7471	0.5435	−0.1708	0.027*
H16C	0.6418	0.4032	−0.1881	0.027*
C17	1.00081 (9)	0.41893 (10)	0.21693 (5)	0.01939 (14)
H17A	1.0849	0.3505	0.2415	0.029*
H17B	0.9330	0.3794	0.2319	0.029*
H17C	1.0342	0.5205	0.2434	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0204 (3)	0.0275 (3)	0.0098 (2)	0.0087 (2)	0.0067 (2)	0.00324 (19)
O2	0.0182 (2)	0.0220 (3)	0.0120 (2)	0.00551 (19)	0.00975 (19)	−0.00182 (18)
O3	0.0142 (2)	0.0200 (2)	0.0111 (2)	0.00625 (18)	0.00627 (18)	0.00077 (17)
N1	0.0189 (3)	0.0226 (3)	0.0175 (3)	0.0056 (2)	0.0109 (2)	−0.0015 (2)
C1	0.0138 (3)	0.0142 (3)	0.0106 (3)	0.0021 (2)	0.0070 (2)	0.0008 (2)
C2	0.0119 (2)	0.0118 (2)	0.0096 (2)	0.00066 (19)	0.0065 (2)	−0.00052 (19)
C3	0.0132 (3)	0.0140 (3)	0.0095 (2)	0.0003 (2)	0.0065 (2)	−0.00105 (19)
C4	0.0130 (3)	0.0135 (3)	0.0106 (2)	0.0005 (2)	0.0076 (2)	−0.00177 (19)
C5	0.0115 (2)	0.0128 (3)	0.0104 (2)	0.00140 (19)	0.0064 (2)	−0.00031 (19)
C6	0.0122 (2)	0.0129 (3)	0.0095 (2)	0.00100 (19)	0.0063 (2)	−0.00042 (19)
C7	0.0118 (2)	0.0111 (2)	0.0094 (2)	0.00076 (19)	0.0066 (2)	−0.00013 (18)
C8	0.0136 (3)	0.0131 (3)	0.0101 (2)	0.0024 (2)	0.0071 (2)	0.00030 (19)
C9	0.0131 (3)	0.0122 (3)	0.0105 (2)	0.0015 (2)	0.0071 (2)	0.00038 (19)
C10	0.0138 (3)	0.0144 (3)	0.0115 (3)	0.0024 (2)	0.0072 (2)	0.0007 (2)
C11	0.0121 (3)	0.0128 (3)	0.0129 (3)	0.0015 (2)	0.0074 (2)	−0.0003 (2)
C12	0.0212 (3)	0.0241 (3)	0.0141 (3)	0.0106 (3)	0.0105 (3)	0.0025 (2)
C13	0.0249 (4)	0.0309 (4)	0.0149 (3)	0.0132 (3)	0.0118 (3)	0.0027 (3)
C14	0.0146 (3)	0.0147 (3)	0.0185 (3)	0.0023 (2)	0.0096 (3)	−0.0008 (2)
C15	0.0131 (3)	0.0139 (3)	0.0154 (3)	0.0019 (2)	0.0083 (2)	0.0009 (2)
C16	0.0212 (3)	0.0235 (3)	0.0127 (3)	0.0006 (3)	0.0113 (3)	−0.0035 (2)
C17	0.0184 (3)	0.0259 (4)	0.0118 (3)	0.0083 (3)	0.0070 (2)	0.0035 (2)

O1—C1	1.2283 (8)	C8—H8A	0.9700
O2—C4	1.3593 (8)	C8—H8B	0.9700
O2—C16	1.4289 (9)	C9—C10	1.3465 (9)
O3—C5	1.3486 (8)	C10—C11	1.4646 (10)
O3—C17	1.4310 (9)	C10—H10A	0.9300
N1—C13	1.3419 (10)	C11—C12	1.3980 (10)
N1—C14	1.3427 (10)	C11—C15	1.3999 (10)
C1—C2	1.4640 (10)	C12—C13	1.3874 (11)
C1—C9	1.5029 (9)	C12—H12A	0.9300
C2—C7	1.3857 (9)	C13—H13A	0.9300
C2—C3	1.4050 (9)	C14—C15	1.3928 (10)
C3—C4	1.3796 (9)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.4291 (9)	C16—H16A	0.9600
C5—C6	1.3926 (9)	C16—H16B	0.9600
C6—C7	1.3959 (9)	C16—H16C	0.9600
C6—H6A	0.9300	C17—H17A	0.9600
C7—C8	1.5124 (9)	C17—H17B	0.9600
C8—C9	1.5081 (9)	C17—H17C	0.9600
C4—O2—C16	117.18 (6)	C1—C9—C8	108.57 (5)
C5—O3—C17	117.17 (6)	C9—C10—C11	129.30 (6)
C13—N1—C14	116.14 (7)	C9—C10—H10A	115.3
O1—C1—C2	127.28 (6)	C11—C10—H10A	115.3
O1—C1—C9	126.02 (6)	C12—C11—C15	116.38 (6)
C2—C1—C9	106.69 (5)	C12—C11—C10	124.44 (6)
C7—C2—C3	121.87 (6)	C15—C11—C10	119.16 (6)
C7—C2—C1	109.63 (5)	C13—C12—C11	119.41 (7)
C3—C2—C1	128.51 (6)	C13—C12—H12A	120.3
C4—C3—C2	118.44 (6)	C11—C12—H12A	120.3
C4—C3—H3A	120.8	N1—C13—C12	124.49 (7)
C2—C3—H3A	120.8	N1—C13—H13A	117.8
O2—C4—C3	125.68 (6)	C12—C13—H13A	117.8
O2—C4—C5	114.52 (6)	N1—C14—C15	123.45 (7)
C3—C4—C5	119.80 (6)	N1—C14—H14A	118.3
O3—C5—C6	124.43 (6)	C15—C14—H14A	118.3
O3—C5—C4	114.50 (6)	C14—C15—C11	120.09 (7)
C6—C5—C4	121.07 (6)	C14—C15—H15A	120.0
C5—C6—C7	118.39 (6)	C11—C15—H15A	120.0
C5—C6—H6A	120.8	O2—C16—H16A	109.5
C7—C6—H6A	120.8	O2—C16—H16B	109.5
C2—C7—C6	120.38 (6)	H16A—C16—H16B	109.5
C2—C7—C8	112.02 (6)	O2—C16—H16C	109.5
C6—C7—C8	127.58 (6)	H16A—C16—H16C	109.5
C9—C8—C7	103.07 (5)	H16B—C16—H16C	109.5
C9—C8—H8A	111.1	O3—C17—H17A	109.5
C7—C8—H8A	111.1	O3—C17—H17B	109.5
C9—C8—H8B	111.1	H17A—C17—H17B	109.5
C7—C8—H8B	111.1	O3—C17—H17C	109.5
H8A—C8—H8B	109.1	H17A—C17—H17C	109.5
C10—C9—C1	120.04 (6)	H17B—C17—H17C	109.5
C10—C9—C8	131.39 (6)
O1—C1—C2—C7	179.48 (7)	C5—C6—C7—C2	−1.08 (10)
C9—C1—C2—C7	−1.11 (8)	C5—C6—C7—C8	177.43 (6)
O1—C1—C2—C3	−0.64 (12)	C2—C7—C8—C9	0.57 (7)
C9—C1—C2—C3	178.78 (7)	C6—C7—C8—C9	−178.05 (7)
C7—C2—C3—C4	1.86 (10)	O1—C1—C9—C10	0.39 (12)
C1—C2—C3—C4	−178.02 (7)	C2—C1—C9—C10	−179.04 (6)
C16—O2—C4—C3	4.42 (10)	O1—C1—C9—C8	−179.11 (7)
C16—O2—C4—C5	−175.13 (6)	C2—C1—C9—C8	1.46 (7)
C2—C3—C4—O2	179.51 (6)	C7—C8—C9—C10	179.35 (7)
C2—C3—C4—C5	−0.96 (10)	C7—C8—C9—C1	−1.23 (7)
C17—O3—C5—C6	2.22 (10)	C1—C9—C10—C11	178.89 (7)
C17—O3—C5—C4	−178.48 (6)	C8—C9—C10—C11	−1.74 (13)
O2—C4—C5—O3	−0.69 (9)	C9—C10—C11—C12	−12.38 (13)
C3—C4—C5—O3	179.73 (6)	C9—C10—C11—C15	169.28 (7)
O2—C4—C5—C6	178.64 (6)	C15—C11—C12—C13	1.08 (12)
C3—C4—C5—C6	−0.94 (10)	C10—C11—C12—C13	−177.30 (8)
O3—C5—C6—C7	−178.78 (6)	C14—N1—C13—C12	1.08 (14)
C4—C5—C6—C7	1.96 (10)	C11—C12—C13—N1	−1.95 (15)
C3—C2—C7—C6	−0.83 (10)	C13—N1—C14—C15	0.58 (12)
C1—C2—C7—C6	179.06 (6)	N1—C14—C15—C11	−1.33 (12)
C3—C2—C7—C8	−179.56 (6)	C12—C11—C15—C14	0.43 (11)
C1—C2—C7—C8	0.33 (8)	C10—C11—C15—C14	178.90 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2i	0.93	2.57	3.4787 (12)	167
C14—H14A···O3i	0.93	2.57	3.2708 (12)	133
C16—H16A···O1ii	0.96	2.53	3.0486 (11)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O2i	0.93	2.57	3.4787 (12)	167
C14—H14A⋯O3i	0.93	2.57	3.2708 (12)	133
C16—H16A⋯O1ii	0.96	2.53	3.0486 (11)	114

Symmetry codes: (i) ; (ii) .