(E)-6-Methyl-3-(2-methyl-benzyl-idene)-chroman-2-one.

In the title compound, C(18)H(16)O(2), the heterocyclic ring of the chroman-2-one system adopts a slightly distorted screw-boat conformation. The dihedral angle between the least-squares planes of the coumarin ring system and the benzene ring is 67.5 (1)°. The crystal packing features C-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric R(2) (2)(8) dimers, and C-H⋯π inter-actions.

Related literature

For the biological activity of coumarins, see: Sharma et al. (2005 ▶); Iqbal et al. (2009 ▶); Siddiqui et al. (2009 ▶); Vyas et al. (2009 ▶); Rollinger et al. (2004 ▶); Brühlmann et al. (2001 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For closely related structures, see: Choi & Kim (2010 ▶); Peng et al. (2012 ▶).

Experimental

Crystal data

C18H16O2

M = 264.31

Monoclinic,

a = 9.1331 (2) Å

b = 17.8838 (5) Å

c = 9.6443 (3) Å

β = 118.056 (1)°

V = 1390.14 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.21 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.987

17986 measured reflections

4246 independent reflections

2882 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.152

S = 1.00

4246 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.17 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: 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005624/gk2454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005624/gk2454Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005624/gk2454Isup3.cml

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

C18H16O2	F(000) = 560
Mr = 264.31	Dx = 1.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4254 reflections
a = 9.1331 (2) Å	θ = 2.3–30.6°
b = 17.8838 (5) Å	µ = 0.08 mm−1
c = 9.6443 (3) Å	T = 293 K
β = 118.056 (1)°	Block, colourless
V = 1390.14 (7) Å3	0.21 × 0.18 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	4246 independent reflections
Radiation source: fine-focus sealed tube	2882 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 30.6°, θmin = 2.3°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −25→24
Tmin = 0.983, Tmax = 0.987	l = −13→13
17986 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0777P)2 + 0.1937P] where P = (Fo2 + 2Fc2)/3
4246 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.53567 (17)	0.64217 (8)	0.67561 (18)	0.0510 (3)
H1	0.5781	0.6520	0.7823	0.061*
C2	0.59366 (19)	0.68218 (9)	0.5898 (2)	0.0591 (4)
H2	0.6741	0.7188	0.6381	0.071*
C3	0.53207 (19)	0.66771 (9)	0.4322 (2)	0.0600 (4)
H3	0.5697	0.6950	0.3732	0.072*
C4	0.41464 (18)	0.61275 (9)	0.36193 (17)	0.0556 (4)
H4	0.3749	0.6030	0.2555	0.067*
C5	0.35357 (16)	0.57122 (7)	0.44610 (15)	0.0457 (3)
C6	0.41463 (15)	0.58712 (7)	0.60612 (15)	0.0426 (3)
C7	0.35620 (16)	0.54362 (7)	0.69924 (15)	0.0440 (3)
H7	0.3418	0.4926	0.6783	0.053*
C8	0.32126 (15)	0.56882 (7)	0.81078 (15)	0.0426 (3)
C9	0.26659 (17)	0.51217 (7)	0.88834 (15)	0.0470 (3)
C10	0.12384 (16)	0.61012 (7)	0.94804 (14)	0.0428 (3)
C11	0.00149 (17)	0.62388 (8)	0.99062 (16)	0.0507 (3)
H11	−0.0461	0.5848	1.0190	0.061*
C12	−0.04862 (17)	0.69606 (8)	0.99036 (17)	0.0506 (3)
H12	−0.1301	0.7056	1.0200	0.061*
C13	0.01926 (16)	0.75525 (8)	0.94698 (16)	0.0468 (3)
C14	0.14082 (16)	0.73905 (7)	0.90318 (16)	0.0456 (3)
H14	0.1866	0.7780	0.8724	0.055*
C15	0.19582 (15)	0.66685 (7)	0.90391 (14)	0.0407 (3)
C16	0.33081 (18)	0.64851 (7)	0.86226 (17)	0.0477 (3)
H16A	0.3215	0.6813	0.7784	0.057*
H16B	0.4379	0.6573	0.9528	0.057*
C17	−0.0374 (2)	0.83405 (9)	0.9463 (2)	0.0661 (4)
H17A	−0.1247	0.8461	0.8435	0.099*
H17B	0.0540	0.8677	0.9733	0.099*
H17C	−0.0777	0.8388	1.0216	0.099*
C18	0.22451 (19)	0.51259 (9)	0.36486 (18)	0.0593 (4)
H18A	0.2632	0.4656	0.4177	0.089*
H18B	0.2034	0.5080	0.2579	0.089*
H18C	0.1240	0.5265	0.3668	0.089*
O1	0.17722 (13)	0.53607 (5)	0.95982 (12)	0.0540 (3)
O2	0.29341 (16)	0.44612 (6)	0.89344 (14)	0.0657 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0488 (7)	0.0557 (8)	0.0530 (8)	−0.0030 (6)	0.0276 (6)	−0.0087 (6)
C2	0.0545 (8)	0.0572 (9)	0.0757 (10)	−0.0044 (6)	0.0391 (8)	−0.0037 (7)
C3	0.0585 (8)	0.0652 (10)	0.0695 (10)	0.0134 (7)	0.0409 (8)	0.0153 (8)
C4	0.0566 (8)	0.0666 (9)	0.0459 (7)	0.0176 (7)	0.0260 (7)	0.0064 (7)
C5	0.0444 (6)	0.0468 (7)	0.0454 (7)	0.0118 (5)	0.0206 (6)	−0.0015 (5)
C6	0.0424 (6)	0.0421 (6)	0.0455 (7)	0.0048 (5)	0.0225 (5)	−0.0027 (5)
C7	0.0457 (6)	0.0388 (6)	0.0448 (7)	−0.0012 (5)	0.0190 (5)	−0.0038 (5)
C8	0.0449 (6)	0.0395 (6)	0.0417 (6)	−0.0049 (5)	0.0189 (5)	−0.0025 (5)
C9	0.0544 (7)	0.0410 (7)	0.0426 (7)	−0.0061 (5)	0.0204 (6)	−0.0018 (5)
C10	0.0501 (7)	0.0405 (7)	0.0382 (6)	−0.0091 (5)	0.0211 (5)	−0.0002 (5)
C11	0.0533 (7)	0.0544 (8)	0.0502 (7)	−0.0131 (6)	0.0290 (6)	0.0035 (6)
C12	0.0442 (7)	0.0598 (8)	0.0527 (8)	−0.0078 (6)	0.0268 (6)	−0.0023 (6)
C13	0.0427 (6)	0.0479 (7)	0.0484 (7)	−0.0060 (5)	0.0202 (6)	−0.0031 (6)
C14	0.0494 (7)	0.0411 (7)	0.0506 (7)	−0.0103 (5)	0.0271 (6)	−0.0034 (5)
C15	0.0459 (6)	0.0403 (6)	0.0389 (6)	−0.0108 (5)	0.0224 (5)	−0.0048 (5)
C16	0.0566 (7)	0.0412 (7)	0.0552 (8)	−0.0116 (5)	0.0344 (6)	−0.0090 (5)
C17	0.0584 (9)	0.0547 (9)	0.0922 (13)	0.0011 (7)	0.0413 (9)	−0.0017 (8)
C18	0.0586 (8)	0.0602 (9)	0.0509 (8)	0.0047 (7)	0.0190 (7)	−0.0121 (7)
O1	0.0731 (7)	0.0412 (5)	0.0592 (6)	−0.0058 (4)	0.0407 (5)	0.0045 (4)
O2	0.0869 (8)	0.0406 (6)	0.0736 (7)	−0.0014 (5)	0.0413 (7)	0.0036 (5)

C1—C2	1.375 (2)	C10—C11	1.3819 (19)
C1—C6	1.3941 (18)	C10—O1	1.3972 (16)
C1—H1	0.9300	C11—C12	1.369 (2)
C2—C3	1.374 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3871 (19)
C3—C4	1.375 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.3914 (18)
C4—C5	1.396 (2)	C13—C17	1.500 (2)
C4—H4	0.9300	C14—C15	1.3844 (18)
C5—C6	1.4014 (18)	C14—H14	0.9300
C5—C18	1.495 (2)	C15—C16	1.5016 (17)
C6—C7	1.4655 (18)	C16—H16A	0.9700
C7—C8	1.3360 (18)	C16—H16B	0.9700
C7—H7	0.9300	C17—H17A	0.9600
C8—C9	1.4788 (18)	C17—H17B	0.9600
C8—C16	1.4981 (17)	C17—H17C	0.9600
C9—O2	1.2025 (16)	C18—H18A	0.9600
C9—O1	1.3615 (17)	C18—H18B	0.9600
C10—C15	1.3804 (16)	C18—H18C	0.9600
C2—C1—C6	121.40 (14)	C10—C11—H11	120.5
C2—C1—H1	119.3	C11—C12—C13	121.58 (13)
C6—C1—H1	119.3	C11—C12—H12	119.2
C3—C2—C1	119.64 (15)	C13—C12—H12	119.2
C3—C2—H2	120.2	C12—C13—C14	117.79 (13)
C1—C2—H2	120.2	C12—C13—C17	121.07 (13)
C2—C3—C4	119.89 (14)	C14—C13—C17	121.13 (12)
C2—C3—H3	120.1	C15—C14—C13	122.15 (12)
C4—C3—H3	120.1	C15—C14—H14	118.9
C3—C4—C5	121.73 (14)	C13—C14—H14	118.9
C3—C4—H4	119.1	C10—C15—C14	117.57 (12)
C5—C4—H4	119.1	C10—C15—C16	119.47 (12)
C4—C5—C6	118.14 (13)	C14—C15—C16	122.95 (11)
C4—C5—C18	120.06 (13)	C8—C16—C15	111.67 (10)
C6—C5—C18	121.79 (13)	C8—C16—H16A	109.3
C1—C6—C5	119.18 (12)	C15—C16—H16A	109.3
C1—C6—C7	121.02 (12)	C8—C16—H16B	109.3
C5—C6—C7	119.74 (12)	C15—C16—H16B	109.3
C8—C7—C6	127.45 (12)	H16A—C16—H16B	107.9
C8—C7—H7	116.3	C13—C17—H17A	109.5
C6—C7—H7	116.3	C13—C17—H17B	109.5
C7—C8—C9	116.20 (12)	H17A—C17—H17B	109.5
C7—C8—C16	126.09 (12)	C13—C17—H17C	109.5
C9—C8—C16	117.71 (11)	H17A—C17—H17C	109.5
O2—C9—O1	116.54 (12)	H17B—C17—H17C	109.5
O2—C9—C8	125.65 (13)	C5—C18—H18A	109.5
O1—C9—C8	117.80 (11)	C5—C18—H18B	109.5
C15—C10—C11	121.98 (13)	H18A—C18—H18B	109.5
C15—C10—O1	121.54 (12)	C5—C18—H18C	109.5
C11—C10—O1	116.40 (11)	H18A—C18—H18C	109.5
C12—C11—C10	118.93 (12)	H18B—C18—H18C	109.5
C12—C11—H11	120.5	C9—O1—C10	121.72 (10)
C6—C1—C2—C3	−0.3 (2)	O1—C10—C11—C12	176.16 (12)
C1—C2—C3—C4	−0.8 (2)	C10—C11—C12—C13	0.7 (2)
C2—C3—C4—C5	0.8 (2)	C11—C12—C13—C14	0.1 (2)
C3—C4—C5—C6	0.3 (2)	C11—C12—C13—C17	179.65 (14)
C3—C4—C5—C18	179.28 (13)	C12—C13—C14—C15	−0.8 (2)
C2—C1—C6—C5	1.4 (2)	C17—C13—C14—C15	179.56 (13)
C2—C1—C6—C7	178.65 (13)	C11—C10—C15—C14	−0.14 (19)
C4—C5—C6—C1	−1.40 (18)	O1—C10—C15—C14	−176.75 (11)
C18—C5—C6—C1	179.66 (12)	C11—C10—C15—C16	178.69 (12)
C4—C5—C6—C7	−178.68 (12)	O1—C10—C15—C16	2.07 (19)
C18—C5—C6—C7	2.38 (18)	C13—C14—C15—C10	0.9 (2)
C1—C6—C7—C8	42.3 (2)	C13—C14—C15—C16	−177.90 (12)
C5—C6—C7—C8	−140.44 (14)	C7—C8—C16—C15	144.14 (13)
C6—C7—C8—C9	−179.09 (12)	C9—C8—C16—C15	−35.18 (17)
C6—C7—C8—C16	1.6 (2)	C10—C15—C16—C8	23.76 (17)
C7—C8—C9—O2	21.8 (2)	C14—C15—C16—C8	−157.48 (12)
C16—C8—C9—O2	−158.81 (14)	O2—C9—O1—C10	−173.36 (12)
C7—C8—C9—O1	−157.79 (12)	C8—C9—O1—C10	6.27 (18)
C16—C8—C9—O1	21.60 (17)	C15—C10—O1—C9	−18.82 (19)
C15—C10—C11—C12	−0.6 (2)	C11—C10—O1—C9	164.39 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.53	3.437 (2)	167
C14—H14···Cgii	0.93	2.88	3.611 (2)	137
C18—H18A···Cgiii	0.96	2.74	3.490 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.53	3.437 (2)	167
C14—H14⋯Cgii	0.93	2.88	3.611 (2)	137
C18—H18A⋯Cgiii	0.96	2.74	3.490 (2)	136

Symmetry codes: (i) ; (ii) ; (iii) .