3-Meth­oxy-2-p-tolyl-4H-chromen-4-one

In the title compound, C₁₇H₁₄O₃, the methyl-substituted benzene ring is twisted relative to the 4H-chromenon skeleton by 51.5 (2)°. The C atom of the meth­oxy group of the 4H-chromenon unit is displaced from the ring plane by 1.225 (2) Å. In the crystal, C—H—O inter­actions connect the mol­ecules into (001) sheets.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

3-Methoxy-2-p-tolyl-4H-chromen-4-one

Crystal data

C17H14O3	F(000) = 560
Mr = 266.28	Dx = 1.311 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9141 reflections
a = 6.2439 (2) Å	θ = 2.7–27.0°
b = 7.9982 (3) Å	µ = 0.09 mm^−1
c = 27.0113 (10) Å	T = 223 K
V = 1348.94 (8) Å^3	Block, colourless
Z = 4	0.22 × 0.14 × 0.07 mm

Data collection

PHOTON 100 CMOS diffractometer	2520 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 28.3°, θmin = 2.7°
φ and ω scans	h = −8→8
21647 measured reflections	k = −10→10
3356 independent reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0451P)^2 + 0.2725P] where P = (Fo^2 + 2Fc^2)/3
3356 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8605 (3)	0.2938 (2)	0.91222 (6)	0.0330 (4)
O1	0.9374 (2)	0.42547 (15)	0.92802 (5)	0.0426 (3)
C2	0.9379 (3)	0.1291 (2)	0.92751 (6)	0.0326 (4)
C3	1.1101 (3)	0.1115 (2)	0.96055 (7)	0.0416 (5)
H3	1.1757	0.2070	0.9740	0.050*
C4	1.1831 (4)	−0.0452 (3)	0.97322 (7)	0.0477 (5)
H4	1.3004	−0.0564	0.9948	0.057*
C5	1.0840 (3)	−0.1870 (2)	0.95420 (7)	0.0423 (5)
H5	1.1335	−0.2934	0.9635	0.051*
C6	0.9149 (3)	−0.1736 (2)	0.92205 (6)	0.0370 (4)
H6	0.8478	−0.2695	0.9093	0.044*
C7	0.8453 (3)	−0.0147 (2)	0.90884 (6)	0.0326 (4)
O2	0.68193 (19)	−0.00843 (14)	0.87466 (4)	0.0343 (3)
C8	0.6107 (3)	0.1430 (2)	0.85826 (6)	0.0315 (4)
C9	0.6885 (3)	0.2892 (2)	0.87624 (6)	0.0319 (4)
C10	0.4456 (3)	0.1239 (2)	0.81962 (6)	0.0319 (4)
C11	0.2745 (3)	0.0167 (2)	0.82682 (7)	0.0385 (4)
H11	0.2629	−0.0433	0.8566	0.046*
C12	0.1211 (3)	−0.0028 (2)	0.79056 (7)	0.0390 (4)
H12	0.0022	−0.0717	0.7968	0.047*
C13	0.1381 (3)	0.0767 (2)	0.74513 (7)	0.0360 (4)
C14	0.3115 (3)	0.1827 (2)	0.73797 (7)	0.0376 (4)
H14	0.3268	0.2380	0.7075	0.045*
C15	0.4623 (3)	0.2085 (2)	0.77474 (6)	0.0365 (4)
H15	0.5762	0.2833	0.7694	0.044*
C16	−0.0256 (3)	0.0460 (3)	0.70531 (7)	0.0458 (5)
H16A	−0.1641	0.0869	0.7162	0.069*
H16B	−0.0349	−0.0729	0.6987	0.069*
H16C	0.0165	0.1043	0.6754	0.069*
O3	0.6097 (2)	0.43757 (14)	0.85849 (5)	0.0406 (3)
C17	0.4490 (3)	0.5098 (3)	0.88908 (8)	0.0525 (5)
H17A	0.5034	0.5214	0.9225	0.079*
H17B	0.3236	0.4382	0.8893	0.079*
H17C	0.4105	0.6190	0.8763	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0369 (9)	0.0283 (8)	0.0339 (9)	−0.0017 (8)	0.0067 (8)	−0.0018 (7)
O1	0.0476 (8)	0.0290 (6)	0.0512 (8)	−0.0034 (6)	−0.0014 (7)	−0.0076 (5)
C2	0.0385 (10)	0.0298 (8)	0.0295 (8)	−0.0004 (8)	0.0043 (7)	−0.0012 (7)
C3	0.0495 (12)	0.0367 (10)	0.0385 (10)	−0.0031 (9)	−0.0041 (9)	−0.0046 (8)
C4	0.0543 (12)	0.0468 (11)	0.0419 (11)	0.0046 (11)	−0.0117 (10)	0.0040 (9)
C5	0.0525 (12)	0.0333 (9)	0.0411 (10)	0.0063 (9)	0.0000 (9)	0.0068 (8)
C6	0.0436 (11)	0.0279 (9)	0.0395 (10)	−0.0006 (8)	0.0036 (9)	0.0037 (7)
C7	0.0354 (9)	0.0324 (9)	0.0299 (8)	0.0007 (8)	0.0029 (7)	0.0006 (7)
O2	0.0370 (7)	0.0257 (6)	0.0401 (7)	−0.0008 (6)	−0.0042 (5)	−0.0002 (5)
C8	0.0308 (9)	0.0296 (8)	0.0342 (9)	0.0011 (7)	0.0049 (8)	0.0033 (7)
C9	0.0350 (9)	0.0258 (8)	0.0348 (9)	0.0013 (8)	0.0043 (7)	0.0019 (7)
C10	0.0320 (9)	0.0288 (8)	0.0349 (9)	0.0014 (8)	0.0034 (7)	−0.0023 (7)
C11	0.0400 (10)	0.0395 (10)	0.0362 (9)	−0.0046 (9)	0.0047 (8)	0.0027 (8)
C12	0.0317 (9)	0.0402 (10)	0.0452 (10)	−0.0061 (9)	0.0032 (8)	−0.0006 (8)
C13	0.0331 (9)	0.0362 (9)	0.0387 (10)	0.0063 (8)	0.0009 (8)	−0.0047 (8)
C14	0.0392 (10)	0.0377 (10)	0.0357 (9)	0.0014 (9)	0.0041 (8)	0.0038 (7)
C15	0.0337 (9)	0.0343 (9)	0.0415 (10)	−0.0042 (9)	0.0053 (8)	0.0018 (8)
C16	0.0400 (11)	0.0518 (12)	0.0456 (11)	0.0002 (10)	−0.0041 (9)	−0.0046 (9)
O3	0.0454 (7)	0.0281 (6)	0.0483 (7)	0.0057 (6)	0.0056 (7)	0.0046 (5)
C17	0.0445 (11)	0.0524 (12)	0.0606 (13)	0.0154 (11)	0.0038 (10)	−0.0006 (10)

Geometric parameters (Å, º)

C1—O1	1.233 (2)	C10—C11	1.383 (3)
C1—C9	1.449 (3)	C10—C15	1.392 (2)
C1—C2	1.463 (2)	C11—C12	1.379 (3)
C2—C7	1.382 (2)	C11—H11	0.9400
C2—C3	1.404 (3)	C12—C13	1.386 (3)
C3—C4	1.377 (3)	C12—H12	0.9400
C3—H3	0.9400	C13—C14	1.388 (3)
C4—C5	1.391 (3)	C13—C16	1.504 (3)
C4—H4	0.9400	C14—C15	1.384 (3)
C5—C6	1.371 (3)	C14—H14	0.9400
C5—H5	0.9400	C15—H15	0.9400
C6—C7	1.390 (2)	C16—H16A	0.9700
C6—H6	0.9400	C16—H16B	0.9700
C7—O2	1.377 (2)	C16—H16C	0.9700
O2—C8	1.364 (2)	O3—C17	1.422 (2)
C8—C9	1.357 (2)	C17—H17A	0.9700
C8—C10	1.475 (2)	C17—H17B	0.9700
C9—O3	1.371 (2)	C17—H17C	0.9700
O1—C1—C9	122.85 (16)	C15—C10—C8	120.88 (16)
O1—C1—C2	122.85 (17)	C12—C11—C10	120.43 (17)
C9—C1—C2	114.29 (15)	C12—C11—H11	119.8
C7—C2—C3	117.98 (17)	C10—C11—H11	119.8
C7—C2—C1	120.52 (16)	C11—C12—C13	121.59 (18)
C3—C2—C1	121.49 (17)	C11—C12—H12	119.2
C4—C3—C2	120.16 (18)	C13—C12—H12	119.2
C4—C3—H3	119.9	C12—C13—C14	117.58 (17)
C2—C3—H3	119.9	C12—C13—C16	120.41 (17)
C3—C4—C5	120.21 (19)	C14—C13—C16	122.00 (17)
C3—C4—H4	119.9	C15—C14—C13	121.45 (17)
C5—C4—H4	119.9	C15—C14—H14	119.3
C6—C5—C4	120.87 (18)	C13—C14—H14	119.3
C6—C5—H5	119.6	C14—C15—C10	120.05 (18)
C4—C5—H5	119.6	C14—C15—H15	120.0
C5—C6—C7	118.34 (17)	C10—C15—H15	120.0
C5—C6—H6	120.8	C13—C16—H16A	109.5
C7—C6—H6	120.8	C13—C16—H16B	109.5
O2—C7—C2	121.64 (16)	H16A—C16—H16B	109.5
O2—C7—C6	115.91 (15)	C13—C16—H16C	109.5
C2—C7—C6	122.43 (16)	H16A—C16—H16C	109.5
C8—O2—C7	119.44 (13)	H16B—C16—H16C	109.5
C9—C8—O2	122.18 (15)	C9—O3—C17	113.67 (14)
C9—C8—C10	126.34 (16)	O3—C17—H17A	109.5
O2—C8—C10	111.47 (14)	O3—C17—H17B	109.5
C8—C9—O3	119.52 (16)	H17A—C17—H17B	109.5
C8—C9—C1	121.84 (15)	O3—C17—H17C	109.5
O3—C9—C1	118.58 (15)	H17A—C17—H17C	109.5
C11—C10—C15	118.81 (17)	H17B—C17—H17C	109.5
C11—C10—C8	120.28 (16)
O1—C1—C2—C7	179.68 (17)	C10—C8—C9—C1	−176.22 (16)
C9—C1—C2—C7	−1.4 (2)	O1—C1—C9—C8	177.99 (18)
O1—C1—C2—C3	−1.6 (3)	C2—C1—C9—C8	−0.9 (2)
C9—C1—C2—C3	177.25 (16)	O1—C1—C9—O3	0.9 (3)
C7—C2—C3—C4	0.5 (3)	C2—C1—C9—O3	−178.00 (15)
C1—C2—C3—C4	−178.26 (19)	C9—C8—C10—C11	−131.6 (2)
C2—C3—C4—C5	−1.4 (3)	O2—C8—C10—C11	48.8 (2)
C3—C4—C5—C6	1.1 (3)	C9—C8—C10—C15	50.6 (3)
C4—C5—C6—C7	0.1 (3)	O2—C8—C10—C15	−128.94 (17)
C3—C2—C7—O2	−177.20 (15)	C15—C10—C11—C12	−1.5 (3)
C1—C2—C7—O2	1.5 (2)	C8—C10—C11—C12	−179.29 (17)
C3—C2—C7—C6	0.7 (3)	C10—C11—C12—C13	3.3 (3)
C1—C2—C7—C6	179.49 (17)	C11—C12—C13—C14	−2.5 (3)
C5—C6—C7—O2	177.00 (15)	C11—C12—C13—C16	176.76 (18)
C5—C6—C7—C2	−1.1 (3)	C12—C13—C14—C15	−0.1 (3)
C2—C7—O2—C8	0.8 (2)	C16—C13—C14—C15	−179.32 (17)
C6—C7—O2—C8	−177.31 (16)	C13—C14—C15—C10	1.8 (3)
C7—O2—C8—C9	−3.2 (2)	C11—C10—C15—C14	−1.0 (3)
C7—O2—C8—C10	176.35 (13)	C8—C10—C15—C14	176.76 (16)
O2—C8—C9—O3	−179.63 (15)	C8—C9—O3—C17	97.8 (2)
C10—C8—C9—O3	0.9 (3)	C1—C9—O3—C17	−85.1 (2)
O2—C8—C9—C1	3.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.94	2.48	3.249 (2)	138
C6—H6···O1^ii	0.94	2.55	3.214 (2)	128

Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x, y−1, z.