3-(3-Meth-oxy-benzyl-idene)chroman-4-one.

In the title compound, C(17)H(14)O(3), the dihedral angle between the meth-oxy-benzene unit and the benzene ring of the chromanone system is 64.12 (3)°. The crystal structure is stabilized by weak C-H⋯O inter-actions.

Related literature

For the preparation, see: Shaikh et al. (2011 ▶). For related structures, see: Kirkiacharian et al. (1984 ▶); Marx et al. (2008 ▶); Suresh et al. (2007 ▶); Chantrapromma et al. (2006 ▶); Augustine et al. (2008 ▶). For the biological activity of this class of compound, see: du Toit et al. (2010 ▶).

Experimental

Crystal data

C17H14O3

M = 266.28

Monoclinic,

a = 12.4143 (9) Å

b = 6.7141 (5) Å

c = 16.0031 (10) Å

β = 98.658 (4)°

V = 1318.67 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 446 K

0.28 × 0.21 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

4414 measured reflections

2315 independent reflections

1662 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.00

2315 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200949X/fj2528sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200949X/fj2528Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200949X/fj2528Isup3.cml

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

C17H14O3	F(000) = 560
Mr = 266.28	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5379 reflections
a = 12.4143 (9) Å	θ = 2.6–25°
b = 6.7141 (5) Å	µ = 0.09 mm−1
c = 16.0031 (10) Å	T = 446 K
β = 98.658 (4)°	Block, colourless
V = 1318.67 (16) Å3	0.28 × 0.21 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	Rint = 0.023
Graphite monochromator	θmax = 25°, θmin = 2.6°
φ and ω scans	h = −14→14
4414 measured reflections	k = −7→7
2315 independent reflections	l = −19→18
1662 reflections with I > 2σ(I)

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) = 0.112	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0753P)2] where P = (Fo2 + 2Fc2)/3
2315 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.96 Å for Me H atoms, 0.97 Å for Methylene H atoms and 0.93 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation.

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. The following ALERTS were generated. Each ALERT has the format test-name_ALERT_alert-type_alert-level. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ···.. 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 3 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ···. 3 PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 46 Perc. Noted

	x	y	z	Uiso*/Ueq
C1	0.67104 (13)	−0.0244 (2)	0.41235 (9)	0.0308 (4)
C2	0.48754 (13)	0.0872 (2)	0.36955 (9)	0.0345 (4)
H2A	0.4209	0.0984	0.3941	0.041*
H2B	0.47	0.0197	0.3156	0.041*
C3	0.52909 (12)	0.2927 (2)	0.35484 (8)	0.0311 (4)
C4	0.64423 (13)	0.3033 (2)	0.33980 (9)	0.0334 (4)
C5	0.71355 (12)	0.1319 (2)	0.36945 (9)	0.0309 (4)
C6	0.82476 (13)	0.1305 (2)	0.36328 (9)	0.0384 (4)
H6	0.8537	0.2318	0.3338	0.046*
C7	0.89190 (15)	−0.0181 (2)	0.40005 (10)	0.0431 (4)
H7	0.9659	−0.0166	0.3963	0.052*
C8	0.84792 (14)	−0.1708 (2)	0.44296 (10)	0.0425 (4)
H8	0.8933	−0.2712	0.4681	0.051*
C9	0.73865 (13)	−0.1761 (2)	0.44890 (9)	0.0368 (4)
H9	0.7102	−0.2801	0.4771	0.044*
C10	0.47198 (13)	0.4614 (2)	0.35582 (8)	0.0332 (4)
H10	0.5096	0.578	0.3479	0.04*
C11	0.35772 (13)	0.4872 (2)	0.36769 (9)	0.0319 (4)
C12	0.27627 (12)	0.3537 (2)	0.33279 (8)	0.0302 (4)
H12	0.2937	0.2466	0.3005	0.036*
C13	0.16990 (12)	0.3818 (2)	0.34652 (8)	0.0307 (4)
C14	0.14246 (14)	0.5448 (2)	0.39277 (9)	0.0360 (4)
H14	0.0707	0.5638	0.4012	0.043*
C15	0.22209 (14)	0.6782 (2)	0.42606 (9)	0.0387 (4)
H15	0.2038	0.787	0.457	0.046*
C16	0.32907 (14)	0.6509 (2)	0.41361 (9)	0.0364 (4)
H16	0.3822	0.7419	0.4359	0.044*
C18	0.11018 (14)	0.0863 (2)	0.27058 (10)	0.0392 (4)
H18A	0.1373	0.1281	0.2203	0.059*
H18B	0.0455	0.008	0.2554	0.059*
H18C	0.1645	0.0078	0.3048	0.059*
O1	0.68030 (9)	0.45005 (16)	0.30738 (7)	0.0461 (3)
O2	0.56502 (9)	−0.03170 (14)	0.42472 (6)	0.0357 (3)
O3	0.08530 (8)	0.25717 (14)	0.31708 (6)	0.0377 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0339 (10)	0.0333 (8)	0.0255 (7)	−0.0017 (7)	0.0053 (7)	−0.0052 (6)
C2	0.0318 (9)	0.0358 (9)	0.0349 (8)	−0.0019 (7)	0.0023 (7)	0.0042 (7)
C3	0.0340 (10)	0.0331 (8)	0.0250 (7)	−0.0038 (7)	0.0010 (7)	0.0028 (6)
C4	0.0364 (10)	0.0350 (8)	0.0284 (8)	−0.0060 (7)	0.0033 (7)	0.0012 (7)
C5	0.0338 (10)	0.0342 (8)	0.0246 (7)	−0.0045 (7)	0.0043 (6)	−0.0018 (6)
C6	0.0393 (11)	0.0442 (9)	0.0328 (8)	−0.0033 (8)	0.0095 (7)	0.0036 (7)
C7	0.0347 (10)	0.0541 (10)	0.0421 (9)	0.0034 (8)	0.0115 (8)	0.0024 (8)
C8	0.0436 (12)	0.0450 (10)	0.0395 (9)	0.0096 (8)	0.0082 (8)	0.0036 (7)
C9	0.0440 (11)	0.0340 (8)	0.0331 (8)	0.0016 (8)	0.0086 (7)	0.0027 (7)
C10	0.0371 (10)	0.0318 (8)	0.0295 (8)	−0.0079 (7)	0.0014 (7)	0.0039 (6)
C11	0.0369 (10)	0.0295 (8)	0.0285 (7)	−0.0001 (7)	0.0031 (7)	0.0063 (6)
C12	0.0357 (10)	0.0273 (8)	0.0272 (7)	0.0025 (7)	0.0033 (7)	0.0006 (6)
C13	0.0327 (10)	0.0304 (8)	0.0279 (7)	−0.0003 (7)	0.0012 (7)	0.0029 (7)
C14	0.0376 (10)	0.0369 (9)	0.0337 (8)	0.0075 (7)	0.0058 (7)	−0.0005 (7)
C15	0.0505 (12)	0.0320 (8)	0.0328 (8)	0.0067 (8)	0.0036 (8)	−0.0029 (7)
C16	0.0459 (11)	0.0281 (8)	0.0331 (8)	−0.0049 (7)	−0.0006 (7)	0.0016 (7)
C18	0.0399 (10)	0.0356 (9)	0.0414 (9)	−0.0022 (7)	0.0035 (8)	−0.0060 (7)
O1	0.0398 (7)	0.0450 (7)	0.0544 (7)	−0.0050 (5)	0.0104 (6)	0.0163 (6)
O2	0.0322 (7)	0.0353 (6)	0.0399 (6)	−0.0008 (5)	0.0064 (5)	0.0092 (5)
O3	0.0320 (7)	0.0366 (6)	0.0442 (6)	0.0002 (5)	0.0051 (5)	−0.0072 (5)

C1—O2	1.3610 (18)	C9—H9	0.93
C1—C9	1.391 (2)	C10—C11	1.469 (2)
C1—C5	1.400 (2)	C10—H10	0.93
C2—O2	1.4443 (18)	C11—C16	1.397 (2)
C2—C3	1.504 (2)	C11—C12	1.403 (2)
C2—H2A	0.97	C12—C13	1.384 (2)
C2—H2B	0.97	C12—H12	0.93
C3—C10	1.337 (2)	C13—O3	1.3697 (18)
C3—C4	1.487 (2)	C13—C14	1.392 (2)
C4—O1	1.2290 (16)	C14—C15	1.380 (2)
C4—C5	1.472 (2)	C14—H14	0.93
C5—C6	1.399 (2)	C15—C16	1.384 (2)
C6—C7	1.375 (2)	C15—H15	0.93
C6—H6	0.93	C16—H16	0.93
C7—C8	1.391 (2)	C18—O3	1.4264 (16)
C7—H7	0.93	C18—H18A	0.96
C8—C9	1.374 (2)	C18—H18B	0.96
C8—H8	0.93	C18—H18C	0.96
O2—C1—C9	116.60 (12)	C3—C10—C11	128.70 (13)
O2—C1—C5	122.87 (13)	C3—C10—H10	115.6
C9—C1—C5	120.44 (14)	C11—C10—H10	115.6
O2—C2—C3	112.97 (13)	C16—C11—C12	119.11 (14)
O2—C2—H2A	109	C16—C11—C10	119.20 (14)
C3—C2—H2A	109	C12—C11—C10	121.68 (13)
O2—C2—H2B	109	C13—C12—C11	119.85 (13)
C3—C2—H2B	109	C13—C12—H12	120.1
H2A—C2—H2B	107.8	C11—C12—H12	120.1
C10—C3—C4	119.08 (13)	O3—C13—C12	124.26 (13)
C10—C3—C2	125.45 (14)	O3—C13—C14	115.26 (13)
C4—C3—C2	115.46 (13)	C12—C13—C14	120.48 (14)
O1—C4—C5	122.03 (14)	C15—C14—C13	119.80 (15)
O1—C4—C3	121.80 (13)	C15—C14—H14	120.1
C5—C4—C3	116.12 (12)	C13—C14—H14	120.1
C6—C5—C1	118.60 (14)	C14—C15—C16	120.36 (14)
C6—C5—C4	121.17 (13)	C14—C15—H15	119.8
C1—C5—C4	119.92 (13)	C16—C15—H15	119.8
C7—C6—C5	121.05 (14)	C15—C16—C11	120.37 (15)
C7—C6—H6	119.5	C15—C16—H16	119.8
C5—C6—H6	119.5	C11—C16—H16	119.8
C6—C7—C8	119.27 (15)	O3—C18—H18A	109.5
C6—C7—H7	120.4	O3—C18—H18B	109.5
C8—C7—H7	120.4	H18A—C18—H18B	109.5
C9—C8—C7	121.20 (15)	O3—C18—H18C	109.5
C9—C8—H8	119.4	H18A—C18—H18C	109.5
C7—C8—H8	119.4	H18B—C18—H18C	109.5
C8—C9—C1	119.43 (14)	C1—O2—C2	117.43 (10)
C8—C9—H9	120.3	C13—O3—C18	117.11 (11)
C1—C9—H9	120.3
O2—C2—C3—C10	−136.04 (14)	C5—C1—C9—C8	0.3 (2)
O2—C2—C3—C4	42.74 (17)	C4—C3—C10—C11	178.71 (13)
C10—C3—C4—O1	−19.0 (2)	C2—C3—C10—C11	−2.6 (2)
C2—C3—C4—O1	162.15 (13)	C3—C10—C11—C16	143.03 (15)
C10—C3—C4—C5	158.36 (13)	C3—C10—C11—C12	−38.1 (2)
C2—C3—C4—C5	−20.50 (18)	C16—C11—C12—C13	−2.14 (19)
O2—C1—C5—C6	177.14 (12)	C10—C11—C12—C13	179.04 (12)
C9—C1—C5—C6	0.8 (2)	C11—C12—C13—O3	−178.24 (12)
O2—C1—C5—C4	3.5 (2)	C11—C12—C13—C14	1.8 (2)
C9—C1—C5—C4	−172.79 (13)	O3—C13—C14—C15	179.26 (12)
O1—C4—C5—C6	1.2 (2)	C12—C13—C14—C15	−0.8 (2)
C3—C4—C5—C6	−176.16 (12)	C13—C14—C15—C16	0.1 (2)
O1—C4—C5—C1	174.63 (13)	C14—C15—C16—C11	−0.4 (2)
C3—C4—C5—C1	−2.72 (19)	C12—C11—C16—C15	1.5 (2)
C1—C5—C6—C7	−1.5 (2)	C10—C11—C16—C15	−179.69 (13)
C4—C5—C6—C7	172.06 (14)	C9—C1—O2—C2	−163.08 (12)
C5—C6—C7—C8	0.9 (2)	C5—C1—O2—C2	20.46 (18)
C6—C7—C8—C9	0.3 (2)	C3—C2—O2—C1	−43.00 (16)
C7—C8—C9—C1	−0.9 (2)	C12—C13—O3—C18	1.11 (19)
O2—C1—C9—C8	−176.20 (13)	C14—C13—O3—C18	−178.95 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1i	0.97	2.54	3.3808 (19)	145
C18—H18B···O3ii	0.96	2.50	3.4227 (19)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1i	0.97	2.54	3.3808 (19)	145
C18—H18B⋯O3ii	0.96	2.50	3.4227 (19)	161

Symmetry codes: (i) ; (ii) .