3-(3,4-Dimeth-oxy-benz-yl)chroman-4-one.

In the title compound, C(18)H(18)O(4), the six-membered chroman-4-one ring adopts an envelope conformation with the C atom bonded to the bridging CH(2) atom as the flap. The dihedral angle between the mean plane of the fused pyranone ring and the dimeth-oxy-substituted benzene ring is 89.72 (2)°. In the crystal, adjacent molecules are linked via C-H⋯π inter-actions.

Related literature

For the biological activity and pharmaceutical properties of chromenes(benzopyrans) and a similar structure, see: Jasinski et al. (2010 ▶). For bond-length data see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶)

Experimental

Crystal data

C18H18O4

M = 298.33

Monoclinic,

a = 30.414 (4) Å

b = 5.453 (3) Å

c = 20.661 (5) Å

β = 118.568 (3)°

V = 3009.4 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.954, T max = 0.991

13379 measured reflections

2802 independent reflections

1955 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.142

S = 1.03

2802 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000925/hg5275sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000925/hg5275Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000925/hg5275Isup3.cml

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

C18H18O4	F(000) = 1264
Mr = 298.33	Dx = 1.317 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 575 reflections
a = 30.414 (4) Å	θ = 2.0–25.0°
b = 5.453 (3) Å	µ = 0.09 mm−1
c = 20.661 (5) Å	T = 295 K
β = 118.568 (3)°	Block, colourless
V = 3009.4 (19) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2802 independent reflections
Radiation source: fine-focus sealed tube	1955 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→34
Tmin = 0.954, Tmax = 0.991	k = −6→6
13379 measured reflections	l = −13→25

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0617P)2 + 1.6626P] where P = (Fo2 + 2Fc2)/3
2802 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.14 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	0.29295 (5)	−0.2335 (3)	0.08927 (7)	0.0703 (4)
O2	0.32093 (6)	0.1349 (3)	0.27652 (7)	0.0795 (5)
O3	0.03885 (6)	0.2688 (3)	−0.10089 (8)	0.0857 (5)
O4	0.05593 (6)	−0.0630 (3)	−0.00297 (9)	0.0828 (5)
C1	0.26773 (8)	−0.0139 (4)	0.08851 (10)	0.0695 (6)
H1A	0.2353	−0.0109	0.0445	0.083*
H1B	0.2869	0.125	0.0862	0.083*
C2	0.26030 (7)	0.0125 (4)	0.15473 (10)	0.0591 (5)
H2	0.2423	−0.1338	0.1569	0.071*
C3	0.31104 (7)	0.0101 (4)	0.22267 (10)	0.0576 (5)
C4	0.34695 (7)	−0.1611 (4)	0.21878 (10)	0.0558 (5)
C5	0.39185 (8)	−0.2207 (4)	0.28105 (12)	0.0743 (6)
H5	0.4002	−0.1446	0.3257	0.089*
C6	0.42394 (9)	−0.3901 (5)	0.27737 (16)	0.0874 (8)
H6	0.4537	−0.4293	0.3193	0.105*
C7	0.41172 (10)	−0.5014 (5)	0.21116 (17)	0.0926 (8)
H7	0.4336	−0.6151	0.2085	0.111*
C8	0.36811 (9)	−0.4479 (4)	0.14941 (15)	0.0809 (7)
H8	0.3602	−0.5257	0.1051	0.097*
C9	0.33563 (8)	−0.2773 (4)	0.15279 (11)	0.0598 (5)
C10	0.22947 (8)	0.2319 (4)	0.15249 (12)	0.0725 (6)
H10A	0.2481	0.3796	0.1555	0.087*
H10B	0.2245	0.2278	0.1955	0.087*
C11	0.17901 (7)	0.2453 (4)	0.08429 (11)	0.0604 (5)
C12	0.16944 (8)	0.4179 (4)	0.03117 (12)	0.0681 (6)
H12	0.1945	0.5279	0.0371	0.082*
C13	0.12308 (9)	0.4315 (4)	−0.03128 (12)	0.0692 (6)
H13	0.1172	0.5511	−0.0666	0.083*
C14	0.08591 (8)	0.2697 (4)	−0.04133 (11)	0.0626 (5)
C15	0.09518 (7)	0.0896 (4)	0.01179 (11)	0.0602 (5)
C16	0.14145 (7)	0.0798 (4)	0.07368 (11)	0.0608 (5)
H16	0.1477	−0.04	0.1091	0.073*
C17	0.02452 (12)	0.4796 (6)	−0.14567 (14)	0.1180 (11)
H17A	0.0302	0.6225	−0.1155	0.177*
H17B	−0.0103	0.4689	−0.1811	0.177*
H17C	0.044	0.4912	−0.1709	0.177*
C18	0.06175 (10)	−0.2336 (5)	0.05250 (14)	0.0907 (8)
H18A	0.0881	−0.3467	0.0606	0.136*
H18B	0.031	−0.322	0.037	0.136*
H18C	0.0701	−0.1475	0.0974	0.136*

	U11	U22	U33	U12	U13	U23
O1	0.0715 (9)	0.0778 (10)	0.0596 (8)	0.0033 (8)	0.0297 (7)	−0.0169 (7)
O2	0.0778 (10)	0.0985 (12)	0.0547 (8)	−0.0048 (9)	0.0257 (7)	−0.0235 (8)
O3	0.0705 (10)	0.1063 (13)	0.0663 (9)	0.0163 (9)	0.0214 (8)	0.0078 (9)
O4	0.0645 (10)	0.0931 (12)	0.0908 (11)	−0.0091 (8)	0.0372 (8)	0.0017 (9)
C1	0.0716 (14)	0.0771 (14)	0.0552 (12)	0.0045 (11)	0.0266 (10)	−0.0073 (10)
C2	0.0586 (12)	0.0636 (12)	0.0540 (11)	−0.0042 (9)	0.0259 (9)	−0.0108 (9)
C3	0.0601 (12)	0.0652 (12)	0.0491 (10)	−0.0107 (9)	0.0275 (9)	−0.0071 (9)
C4	0.0520 (11)	0.0580 (11)	0.0575 (11)	−0.0085 (9)	0.0262 (9)	0.0008 (9)
C5	0.0647 (14)	0.0821 (15)	0.0700 (13)	−0.0081 (12)	0.0272 (11)	0.0052 (11)
C6	0.0614 (14)	0.0860 (17)	0.1025 (19)	0.0083 (13)	0.0293 (13)	0.0242 (15)
C7	0.0870 (18)	0.0789 (17)	0.120 (2)	0.0132 (14)	0.0564 (17)	0.0066 (16)
C8	0.0863 (17)	0.0707 (15)	0.0970 (17)	0.0048 (13)	0.0530 (15)	−0.0066 (13)
C9	0.0632 (12)	0.0564 (11)	0.0660 (12)	−0.0073 (9)	0.0359 (10)	−0.0035 (9)
C10	0.0687 (14)	0.0697 (14)	0.0707 (13)	0.0027 (11)	0.0264 (11)	−0.0177 (11)
C11	0.0624 (12)	0.0570 (12)	0.0642 (12)	0.0038 (10)	0.0321 (10)	−0.0080 (10)
C12	0.0704 (14)	0.0621 (13)	0.0795 (14)	−0.0028 (10)	0.0419 (12)	−0.0047 (11)
C13	0.0846 (16)	0.0658 (13)	0.0666 (13)	0.0117 (12)	0.0438 (12)	0.0099 (10)
C14	0.0615 (12)	0.0734 (14)	0.0552 (11)	0.0108 (11)	0.0297 (10)	−0.0025 (10)
C15	0.0589 (12)	0.0649 (12)	0.0665 (12)	0.0031 (10)	0.0378 (10)	−0.0032 (10)
C16	0.0662 (13)	0.0614 (12)	0.0594 (11)	0.0086 (10)	0.0338 (10)	0.0024 (9)
C17	0.128 (2)	0.112 (2)	0.0697 (16)	0.0409 (19)	0.0112 (15)	0.0049 (16)
C18	0.1060 (19)	0.0895 (18)	0.1038 (18)	−0.0211 (15)	0.0720 (16)	−0.0050 (15)

O1—C9	1.355 (2)	C7—H7	0.93
O1—C1	1.418 (3)	C8—C9	1.383 (3)
O2—C3	1.213 (2)	C8—H8	0.93
O3—C14	1.371 (2)	C10—C11	1.509 (3)
O3—C17	1.408 (3)	C10—H10A	0.97
O4—C15	1.365 (2)	C10—H10B	0.97
O4—C18	1.420 (3)	C11—C12	1.368 (3)
C1—C2	1.496 (3)	C11—C16	1.388 (3)
C1—H1A	0.97	C12—C13	1.385 (3)
C1—H1B	0.97	C12—H12	0.93
C2—C10	1.507 (3)	C13—C14	1.369 (3)
C2—C3	1.510 (3)	C13—H13	0.93
C2—H2	0.98	C14—C15	1.397 (3)
C3—C4	1.468 (3)	C15—C16	1.377 (3)
C4—C9	1.389 (3)	C16—H16	0.93
C4—C5	1.395 (3)	C17—H17A	0.96
C5—C6	1.372 (3)	C17—H17B	0.96
C5—H5	0.93	C17—H17C	0.96
C6—C7	1.375 (4)	C18—H18A	0.96
C6—H6	0.93	C18—H18B	0.96
C7—C8	1.362 (3)	C18—H18C	0.96
C9—O1—C1	114.98 (15)	C2—C10—C11	114.02 (16)
C14—O3—C17	116.7 (2)	C2—C10—H10A	108.7
C15—O4—C18	117.46 (17)	C11—C10—H10A	108.7
O1—C1—C2	112.85 (17)	C2—C10—H10B	108.7
O1—C1—H1A	109	C11—C10—H10B	108.7
C2—C1—H1A	109	H10A—C10—H10B	107.6
O1—C1—H1B	109	C12—C11—C16	118.52 (19)
C2—C1—H1B	109	C12—C11—C10	120.9 (2)
H1A—C1—H1B	107.8	C16—C11—C10	120.57 (19)
C10—C2—C3	112.31 (16)	C11—C12—C13	121.0 (2)
C10—C2—C1	114.33 (18)	C11—C12—H12	119.5
C3—C2—C1	108.37 (16)	C13—C12—H12	119.5
C10—C2—H2	107.2	C14—C13—C12	120.4 (2)
C3—C2—H2	107.2	C14—C13—H13	119.8
C1—C2—H2	107.2	C12—C13—H13	119.8
O2—C3—C4	122.84 (18)	C13—C14—C15	119.46 (19)
O2—C3—C2	122.88 (19)	C13—C14—O3	124.8 (2)
C4—C3—C2	114.26 (16)	C15—C14—O3	115.75 (19)
C9—C4—C5	118.2 (2)	O4—C15—C16	125.46 (19)
C9—C4—C3	120.14 (17)	O4—C15—C14	115.26 (18)
C5—C4—C3	121.58 (18)	C16—C15—C14	119.28 (19)
C6—C5—C4	121.0 (2)	C15—C16—C11	121.32 (19)
C6—C5—H5	119.5	C15—C16—H16	119.3
C4—C5—H5	119.5	C11—C16—H16	119.3
C5—C6—C7	119.4 (2)	O3—C17—H17A	109.5
C5—C6—H6	120.3	O3—C17—H17B	109.5
C7—C6—H6	120.3	H17A—C17—H17B	109.5
C8—C7—C6	121.1 (2)	O3—C17—H17C	109.5
C8—C7—H7	119.5	H17A—C17—H17C	109.5
C6—C7—H7	119.5	H17B—C17—H17C	109.5
C7—C8—C9	119.7 (2)	O4—C18—H18A	109.5
C7—C8—H8	120.1	O4—C18—H18B	109.5
C9—C8—H8	120.1	H18A—C18—H18B	109.5
O1—C9—C8	116.51 (19)	O4—C18—H18C	109.5
O1—C9—C4	122.91 (18)	H18A—C18—H18C	109.5
C8—C9—C4	120.6 (2)	H18B—C18—H18C	109.5
C9—O1—C1—C2	−49.8 (2)	C3—C4—C9—C8	−176.84 (19)
O1—C1—C2—C10	−174.62 (16)	C3—C2—C10—C11	178.29 (17)
O1—C1—C2—C3	59.3 (2)	C1—C2—C10—C11	54.3 (3)
C10—C2—C3—O2	16.4 (3)	C2—C10—C11—C12	−108.8 (2)
C1—C2—C3—O2	143.6 (2)	C2—C10—C11—C16	70.3 (3)
C10—C2—C3—C4	−165.23 (17)	C16—C11—C12—C13	1.3 (3)
C1—C2—C3—C4	−38.0 (2)	C10—C11—C12—C13	−179.64 (19)
O2—C3—C4—C9	−172.37 (19)	C11—C12—C13—C14	−0.6 (3)
C2—C3—C4—C9	9.2 (3)	C12—C13—C14—C15	−0.4 (3)
O2—C3—C4—C5	10.7 (3)	C12—C13—C14—O3	179.69 (18)
C2—C3—C4—C5	−167.68 (18)	C17—O3—C14—C13	−14.9 (3)
C9—C4—C5—C6	−0.2 (3)	C17—O3—C14—C15	165.1 (2)
C3—C4—C5—C6	176.79 (19)	C18—O4—C15—C16	5.3 (3)
C4—C5—C6—C7	0.4 (4)	C18—O4—C15—C14	−174.00 (18)
C5—C6—C7—C8	−0.6 (4)	C13—C14—C15—O4	179.99 (18)
C6—C7—C8—C9	0.6 (4)	O3—C14—C15—O4	0.0 (3)
C1—O1—C9—C8	−162.74 (19)	C13—C14—C15—C16	0.7 (3)
C1—O1—C9—C4	17.7 (3)	O3—C14—C15—C16	−179.39 (17)
C7—C8—C9—O1	−179.9 (2)	O4—C15—C16—C11	−179.27 (18)
C7—C8—C9—C4	−0.4 (3)	C14—C15—C16—C11	0.0 (3)
C5—C4—C9—O1	179.68 (18)	C12—C11—C16—C15	−0.9 (3)
C3—C4—C9—O1	2.7 (3)	C10—C11—C16—C15	179.95 (18)
C5—C4—C9—C8	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cgi	0.96	2.87	3.755 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯Cg i	0.96	2.87	3.755 (4)	154

Symmetry code: (i) .