3-Benzyl-idene-6-methoxy-chroman-4-one.

In the title compound, C(17)H(14)O(3), the dihedral angle between the phenyl ring and the benzene ring of the chromanone moiety is 67.78 (3)°. The six-membered heterocyclic ring of the chromanone moiety adopts a half-chair conformation. The structure is stabilized by weak inter-molecular C-H⋯O inter-actions that link the mol-ecules into inversion dimers.

Related literature

For background literature, see: Finch & Tamm (1970 ▶); Geen et al.(1996 ▶); Tietze & Gerlitzer (1997 ▶); Cremer & Pople (1975 ▶). For a related structure, see: Suresh et al. (2007 ▶).

Experimental

Crystal data

C17H14O3

M = 266.28

Triclinic,

a = 7.2678 (2) Å

b = 8.3151 (2) Å

c = 11.7999 (4) Å

α = 95.964 (1)°

β = 103.828 (1)°

γ = 104.042 (1)°

V = 661.74 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.45 × 0.42 × 0.38 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.960, T max = 0.966

8868 measured reflections

3041 independent reflections

2404 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.04

3041 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 (Bruker, 2004 ▶); data reduction: SAINT-Plus (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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031541/fl2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031541/fl2222Isup2.hkl

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

C17H14O3	Z = 2
Mr = 266.28	F(000) = 280
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2678 (2) Å	Cell parameters from 4851 reflections
b = 8.3151 (2) Å	θ = 2.6–28.3°
c = 11.7999 (4) Å	µ = 0.09 mm−1
α = 95.964 (1)°	T = 298 K
β = 103.828 (1)°	Block, colourless
γ = 104.042 (1)°	0.45 × 0.42 × 0.38 mm
V = 661.74 (3) Å3

Bruker APEXII CCD area-detector diffractometer	3041 independent reflections
Radiation source: fine-focus sealed tube	2404 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→9
Tmin = 0.960, Tmax = 0.966	k = −10→11
8868 measured reflections	l = −15→15

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) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.1403P] where P = (Fo2 + 2Fc2)/3
3041 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	−0.38800 (18)	0.42099 (15)	0.12980 (11)	0.0357 (3)
C2	−0.49675 (19)	0.45875 (16)	0.20631 (12)	0.0413 (3)
H2	−0.4480	0.5584	0.2610	0.050*
C3	−0.6764 (2)	0.34969 (18)	0.20189 (13)	0.0469 (3)
H3	−0.7484	0.3771	0.2527	0.056*
C4	−0.7491 (2)	0.20056 (18)	0.12250 (14)	0.0499 (3)
H4	−0.8689	0.1265	0.1205	0.060*
C5	−0.6433 (2)	0.16181 (18)	0.04615 (13)	0.0526 (4)
H5	−0.6916	0.0606	−0.0069	0.063*
C6	−0.4668 (2)	0.27146 (17)	0.04756 (12)	0.0448 (3)
H6	−0.3995	0.2458	−0.0066	0.054*
C7	−0.19833 (18)	0.53387 (16)	0.12988 (12)	0.0384 (3)
C8	−0.04981 (18)	0.62292 (15)	0.22311 (11)	0.0366 (3)
C9	0.12813 (18)	0.73207 (16)	0.20106 (11)	0.0375 (3)
C10	0.47891 (18)	0.89529 (15)	0.29540 (11)	0.0370 (3)
H10	0.4781	0.9476	0.2294	0.044*
C11	0.64996 (18)	0.92856 (15)	0.38626 (11)	0.0390 (3)
C12	0.65136 (19)	0.84577 (17)	0.48305 (12)	0.0439 (3)
H12	0.7679	0.8659	0.5429	0.053*
C13	0.4833 (2)	0.73495 (18)	0.49135 (12)	0.0439 (3)
H13	0.4862	0.6800	0.5562	0.053*
C14	−0.03927 (19)	0.62083 (18)	0.35174 (11)	0.0427 (3)
H14A	−0.0509	0.7271	0.3874	0.051*
H14B	−0.1486	0.5319	0.3584	0.051*
C15	0.30664 (17)	0.78222 (14)	0.30322 (10)	0.0336 (3)
C16	0.30814 (18)	0.70497 (15)	0.40210 (11)	0.0362 (3)
C17	0.8268 (3)	1.1358 (3)	0.29888 (18)	0.0764 (6)
H17A	0.8124	1.0644	0.2261	0.115*
H17B	0.9493	1.2225	0.3186	0.115*
H17C	0.7195	1.1861	0.2896	0.115*
O1	0.13097 (14)	0.77364 (14)	0.10531 (9)	0.0566 (3)
O2	0.14409 (13)	0.59397 (12)	0.41471 (8)	0.0454 (2)
O3	0.82540 (14)	1.03993 (13)	0.38987 (9)	0.0540 (3)
H7	−0.175 (2)	0.5435 (19)	0.0546 (15)	0.051 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0311 (6)	0.0373 (6)	0.0357 (6)	0.0073 (5)	0.0046 (5)	0.0092 (5)
C2	0.0344 (6)	0.0382 (6)	0.0475 (7)	0.0079 (5)	0.0088 (5)	0.0016 (5)
C3	0.0365 (7)	0.0516 (8)	0.0538 (8)	0.0108 (6)	0.0158 (6)	0.0100 (6)
C4	0.0349 (7)	0.0470 (7)	0.0587 (9)	−0.0018 (6)	0.0082 (6)	0.0122 (6)
C5	0.0497 (8)	0.0431 (7)	0.0504 (8)	−0.0009 (6)	0.0048 (6)	−0.0030 (6)
C6	0.0426 (7)	0.0480 (7)	0.0384 (7)	0.0072 (6)	0.0091 (5)	0.0016 (5)
C7	0.0339 (6)	0.0423 (6)	0.0378 (6)	0.0081 (5)	0.0092 (5)	0.0087 (5)
C8	0.0310 (6)	0.0403 (6)	0.0380 (6)	0.0084 (5)	0.0097 (5)	0.0074 (5)
C9	0.0321 (6)	0.0423 (6)	0.0353 (6)	0.0069 (5)	0.0071 (5)	0.0079 (5)
C10	0.0331 (6)	0.0381 (6)	0.0375 (6)	0.0086 (5)	0.0064 (5)	0.0066 (5)
C11	0.0297 (6)	0.0386 (6)	0.0444 (7)	0.0081 (5)	0.0059 (5)	0.0025 (5)
C12	0.0347 (7)	0.0539 (8)	0.0385 (7)	0.0150 (6)	0.0006 (5)	0.0039 (6)
C13	0.0413 (7)	0.0551 (8)	0.0352 (6)	0.0154 (6)	0.0067 (5)	0.0111 (5)
C14	0.0321 (6)	0.0548 (8)	0.0392 (7)	0.0076 (6)	0.0114 (5)	0.0059 (6)
C15	0.0298 (6)	0.0357 (6)	0.0334 (6)	0.0087 (5)	0.0067 (5)	0.0032 (4)
C16	0.0334 (6)	0.0401 (6)	0.0349 (6)	0.0101 (5)	0.0100 (5)	0.0047 (5)
C17	0.0437 (9)	0.0871 (13)	0.0821 (13)	−0.0091 (9)	0.0049 (8)	0.0372 (10)
O1	0.0392 (5)	0.0764 (7)	0.0416 (5)	−0.0049 (5)	0.0035 (4)	0.0223 (5)
O2	0.0369 (5)	0.0580 (6)	0.0403 (5)	0.0077 (4)	0.0104 (4)	0.0173 (4)
O3	0.0305 (5)	0.0574 (6)	0.0614 (6)	−0.0006 (4)	−0.0003 (4)	0.0152 (5)

C1—C2	1.3932 (18)	C10—C11	1.3805 (17)
C1—C6	1.3978 (17)	C10—C15	1.4007 (17)
C1—C7	1.4671 (17)	C10—H10	0.9300
C2—C3	1.3830 (19)	C11—O3	1.3704 (15)
C2—H2	0.9300	C11—C12	1.3927 (19)
C3—C4	1.378 (2)	C12—C13	1.371 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.377 (2)	C13—C16	1.3938 (17)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.377 (2)	C14—O2	1.4434 (16)
C5—H5	0.9300	C14—H14A	0.9700
C6—H6	0.9300	C14—H14B	0.9700
C7—C8	1.3412 (17)	C15—C16	1.3883 (17)
C7—H7	0.950 (16)	C16—O2	1.3693 (15)
C8—C9	1.4846 (18)	C17—O3	1.403 (2)
C8—C14	1.5036 (18)	C17—H17A	0.9600
C9—O1	1.2187 (15)	C17—H17B	0.9600
C9—C15	1.4818 (16)	C17—H17C	0.9600
C2—C1—C6	118.20 (12)	O3—C11—C10	124.75 (12)
C2—C1—C7	122.70 (11)	O3—C11—C12	115.45 (11)
C6—C1—C7	119.07 (12)	C10—C11—C12	119.80 (12)
C3—C2—C1	120.72 (12)	C13—C12—C11	120.93 (12)
C3—C2—H2	119.6	C13—C12—H12	119.5
C1—C2—H2	119.6	C11—C12—H12	119.5
C4—C3—C2	120.26 (13)	C12—C13—C16	119.70 (12)
C4—C3—H3	119.9	C12—C13—H13	120.1
C2—C3—H3	119.9	C16—C13—H13	120.1
C5—C4—C3	119.63 (13)	O2—C14—C8	111.15 (10)
C5—C4—H4	120.2	O2—C14—H14A	109.4
C3—C4—H4	120.2	C8—C14—H14A	109.4
C6—C5—C4	120.64 (13)	O2—C14—H14B	109.4
C6—C5—H5	119.7	C8—C14—H14B	109.4
C4—C5—H5	119.7	H14A—C14—H14B	108.0
C5—C6—C1	120.49 (13)	C16—C15—C10	120.07 (11)
C5—C6—H6	119.8	C16—C15—C9	119.69 (11)
C1—C6—H6	119.8	C10—C15—C9	119.96 (11)
C8—C7—C1	128.33 (12)	O2—C16—C15	122.60 (11)
C8—C7—H7	115.3 (9)	O2—C16—C13	117.53 (11)
C1—C7—H7	116.4 (9)	C15—C16—C13	119.83 (12)
C7—C8—C9	118.66 (11)	O3—C17—H17A	109.5
C7—C8—C14	126.65 (12)	O3—C17—H17B	109.5
C9—C8—C14	114.65 (10)	H17A—C17—H17B	109.5
O1—C9—C15	121.81 (11)	O3—C17—H17C	109.5
O1—C9—C8	123.09 (11)	H17A—C17—H17C	109.5
C15—C9—C8	115.06 (11)	H17B—C17—H17C	109.5
C11—C10—C15	119.58 (12)	C16—O2—C14	113.85 (10)
C11—C10—H10	120.2	C11—O3—C17	117.35 (11)
C15—C10—H10	120.2
C6—C1—C2—C3	0.93 (19)	C11—C12—C13—C16	−0.3 (2)
C7—C1—C2—C3	179.01 (12)	C7—C8—C14—O2	129.37 (13)
C1—C2—C3—C4	0.9 (2)	C9—C8—C14—O2	−48.50 (15)
C2—C3—C4—C5	−1.0 (2)	C11—C10—C15—C16	0.33 (18)
C3—C4—C5—C6	−0.7 (2)	C11—C10—C15—C9	−173.63 (11)
C4—C5—C6—C1	2.6 (2)	O1—C9—C15—C16	−166.84 (12)
C2—C1—C6—C5	−2.7 (2)	C8—C9—C15—C16	10.83 (17)
C7—C1—C6—C5	179.18 (12)	O1—C9—C15—C10	7.14 (19)
C2—C1—C7—C8	41.2 (2)	C8—C9—C15—C10	−175.19 (10)
C6—C1—C7—C8	−140.74 (14)	C10—C15—C16—O2	179.75 (11)
C1—C7—C8—C9	−178.86 (12)	C9—C15—C16—O2	−6.28 (18)
C1—C7—C8—C14	3.3 (2)	C10—C15—C16—C13	−2.59 (18)
C7—C8—C9—O1	16.3 (2)	C9—C15—C16—C13	171.39 (11)
C14—C8—C9—O1	−165.66 (13)	C12—C13—C16—O2	−179.65 (11)
C7—C8—C9—C15	−161.35 (11)	C12—C13—C16—C15	2.57 (19)
C14—C8—C9—C15	16.71 (16)	C15—C16—O2—C14	−27.22 (16)
C15—C10—C11—O3	−178.13 (11)	C13—C16—O2—C14	155.06 (11)
C15—C10—C11—C12	1.94 (18)	C8—C14—O2—C16	53.73 (14)
O3—C11—C12—C13	178.09 (12)	C10—C11—O3—C17	5.0 (2)
C10—C11—C12—C13	−2.0 (2)	C12—C11—O3—C17	−175.11 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.53	3.4293 (18)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.53	3.4293 (18)	163

Symmetry code: (i) .