6-Benzyl-oxycoumarin.

In the title compound, 6-benz-yloxy-2H-1-benzopyran-2-one, C(16)H(12)O(3), the coumarin unit and benzyl plane in the mol-ecule are perpendicular to each other [86.92 (7)°]. The crystal packing is stabilized by π-π stacking inter-actions, with an inter-planar separation between inversion-related coumarin units of 3.618 (3) Å. The crystal structure shows inter-molecular C-H⋯O hydrogen bonding between neighboring mol-ecules.

Related literature

For general background to coumarin, see: Adfa et al. (2010 ▶); Gunnewegh et al. (1995 ▶); Li et al. (1998 ▶); Murray et al. (1982 ▶); Schönberg & Latif (1954 ▶). For related compounds, see: Chinnakali et al. (1998 ▶); Jasinski et al. (2003 ▶).

Experimental

Crystal data

C16H12O3

M = 252.26

Monoclinic,

a = 20.391 (12) Å

b = 6.732 (4) Å

c = 18.844 (11) Å

β = 94.833 (8)°

V = 2578 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.10 × 0.10 mm

Data collection

Rigaku AFC7R Mercury CCD diffractometer

10197 measured reflections

2912 independent reflections

2070 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.190

S = 1.20

2912 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: Yadokari-XG 2009 (Wakita, 2001 ▶; Kabuto et al., 2009 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Yadokari-XG 2009 and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, General. DOI: 10.1107/S1600536810029430/zl2289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029430/zl2289Isup2.hkl

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

C16H12O3	F(000) = 1056
Mr = 252.26	Dx = 1.300 Mg m−3
Monoclinic, C2/c	Melting point: 385 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71070 Å
a = 20.391 (12) Å	Cell parameters from 2417 reflections
b = 6.732 (4) Å	θ = 3.1–27.5°
c = 18.844 (11) Å	µ = 0.09 mm−1
β = 94.833 (8)°	T = 296 K
V = 2578 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.10 × 0.10 mm

Rigaku AFC7R Mercury CCD diffractometer	2070 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.039
graphite	θmax = 27.5°, θmin = 3.1°
Detector resolution: 14.6199 pixels mm-1	h = −23→26
dtintegrate.ref scans	k = −7→8
10197 measured reflections	l = −24→24
2912 independent 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0813P)2 + 0.4589P] where P = (Fo2 + 2Fc2)/3
2912 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 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	0.08714 (7)	−0.28238 (19)	0.06726 (8)	0.0517 (4)
C1	0.14413 (11)	−0.2635 (3)	0.03418 (12)	0.0499 (5)
O2	0.17437 (9)	−0.4146 (2)	0.02481 (10)	0.0698 (5)
C2	0.16227 (12)	−0.0660 (3)	0.01380 (13)	0.0565 (6)
H2	0.1997	−0.0486	−0.0105	0.068*
C3	0.12678 (11)	0.0923 (3)	0.02892 (13)	0.0545 (6)
H3	0.1395	0.2176	0.0145	0.065*
C4	0.06915 (10)	0.0725 (3)	0.06722 (11)	0.0441 (5)
C5	0.03075 (11)	0.2315 (3)	0.08766 (12)	0.0499 (6)
H5	0.0418	0.3605	0.0757	0.060*
C6	−0.02290 (11)	0.1989 (3)	0.12518 (13)	0.0505 (5)
C7	−0.04011 (11)	0.0050 (3)	0.14279 (13)	0.0586 (6)
H7	−0.0765	−0.0173	0.1683	0.070*
C8	−0.00300 (11)	−0.1532 (3)	0.12231 (13)	0.0552 (6)
H8	−0.0144	−0.2823	0.1338	0.066*
C9	0.05060 (10)	−0.1191 (3)	0.08502 (11)	0.0438 (5)
O3	−0.05721 (8)	0.3649 (2)	0.14299 (11)	0.0687 (5)
C10	−0.11309 (13)	0.3365 (3)	0.18242 (16)	0.0676 (7)
H10A	−0.0995	0.2785	0.2284	0.081*
H10B	−0.1438	0.2461	0.1570	0.081*
C11	−0.14576 (11)	0.5327 (3)	0.19239 (12)	0.0512 (6)
C12	−0.13279 (13)	0.6408 (3)	0.25384 (13)	0.0612 (6)
H12	−0.1017	0.5947	0.2889	0.073*
C13	−0.16522 (14)	0.8164 (3)	0.26425 (14)	0.0652 (7)
H13	−0.1561	0.8872	0.3063	0.078*
C14	−0.21066 (13)	0.8871 (3)	0.21321 (14)	0.0609 (7)
H14	−0.2326	1.0056	0.2204	0.073*
C15	−0.22378 (13)	0.7825 (4)	0.15136 (14)	0.0676 (7)
H15	−0.2546	0.8303	0.1163	0.081*
C16	−0.19132 (14)	0.6060 (3)	0.14083 (13)	0.0633 (7)
H16	−0.2003	0.5361	0.0986	0.076*

	U11	U22	U33	U12	U13	U23
O1	0.0507 (9)	0.0364 (7)	0.0700 (10)	0.0055 (6)	0.0165 (7)	0.0010 (6)
C1	0.0495 (13)	0.0468 (11)	0.0544 (13)	0.0074 (9)	0.0111 (10)	−0.0030 (9)
O2	0.0723 (12)	0.0497 (9)	0.0911 (13)	0.0141 (8)	0.0283 (10)	−0.0049 (8)
C2	0.0532 (14)	0.0518 (12)	0.0673 (15)	0.0009 (10)	0.0221 (11)	0.0011 (10)
C3	0.0528 (14)	0.0423 (11)	0.0710 (15)	−0.0025 (9)	0.0213 (11)	0.0034 (10)
C4	0.0417 (12)	0.0379 (10)	0.0530 (12)	−0.0008 (8)	0.0064 (9)	0.0019 (8)
C5	0.0471 (13)	0.0324 (9)	0.0716 (15)	−0.0010 (8)	0.0139 (11)	0.0032 (9)
C6	0.0444 (12)	0.0366 (10)	0.0719 (15)	0.0018 (8)	0.0132 (10)	−0.0017 (9)
C7	0.0472 (13)	0.0428 (11)	0.0891 (17)	0.0001 (9)	0.0253 (12)	0.0079 (11)
C8	0.0497 (13)	0.0350 (10)	0.0832 (16)	−0.0009 (8)	0.0201 (11)	0.0081 (10)
C9	0.0428 (12)	0.0329 (9)	0.0559 (12)	0.0027 (8)	0.0062 (9)	0.0009 (8)
O3	0.0594 (11)	0.0386 (8)	0.1138 (14)	0.0039 (7)	0.0417 (10)	0.0007 (8)
C10	0.0616 (16)	0.0473 (12)	0.099 (2)	0.0020 (11)	0.0363 (14)	0.0014 (12)
C11	0.0481 (13)	0.0437 (11)	0.0648 (14)	0.0003 (9)	0.0223 (11)	−0.0001 (10)
C12	0.0580 (15)	0.0583 (13)	0.0663 (16)	0.0040 (11)	−0.0015 (12)	−0.0023 (11)
C13	0.0728 (18)	0.0573 (13)	0.0664 (15)	0.0008 (12)	0.0112 (13)	−0.0144 (12)
C14	0.0550 (15)	0.0485 (12)	0.0829 (18)	0.0063 (10)	0.0280 (13)	0.0006 (11)
C15	0.0596 (16)	0.0721 (16)	0.0709 (17)	0.0104 (12)	0.0045 (13)	0.0135 (13)
C16	0.0697 (17)	0.0645 (14)	0.0568 (14)	0.0001 (12)	0.0115 (12)	−0.0070 (11)

O1—C1	1.370 (3)	C8—H8	0.9300
O1—C9	1.385 (2)	O3—C10	1.425 (3)
C1—O2	1.210 (2)	C10—C11	1.499 (3)
C1—C2	1.440 (3)	C10—H10A	0.9700
C2—C3	1.333 (3)	C10—H10B	0.9700
C2—H2	0.9300	C11—C12	1.374 (3)
C3—C4	1.436 (3)	C11—C16	1.378 (3)
C3—H3	0.9300	C12—C13	1.377 (3)
C4—C9	1.393 (3)	C12—H12	0.9300
C4—C5	1.399 (3)	C13—C14	1.364 (4)
C5—C6	1.369 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.369 (4)
C6—O3	1.375 (2)	C14—H14	0.9300
C6—C7	1.399 (3)	C15—C16	1.382 (3)
C7—C8	1.380 (3)	C15—H15	0.9300
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.368 (3)
C1—O1—C9	122.04 (15)	O1—C9—C4	120.94 (18)
O2—C1—O1	116.78 (18)	C6—O3—C10	117.63 (16)
O2—C1—C2	126.2 (2)	O3—C10—C11	109.29 (17)
O1—C1—C2	116.97 (17)	O3—C10—H10A	109.8
C3—C2—C1	121.7 (2)	C11—C10—H10A	109.8
C3—C2—H2	119.2	O3—C10—H10B	109.8
C1—C2—H2	119.2	C11—C10—H10B	109.8
C2—C3—C4	121.00 (18)	H10A—C10—H10B	108.3
C2—C3—H3	119.5	C12—C11—C16	118.4 (2)
C4—C3—H3	119.5	C12—C11—C10	121.1 (2)
C9—C4—C5	118.17 (19)	C16—C11—C10	120.5 (2)
C9—C4—C3	117.23 (17)	C11—C12—C13	120.9 (2)
C5—C4—C3	124.61 (18)	C11—C12—H12	119.5
C6—C5—C4	120.65 (18)	C13—C12—H12	119.5
C6—C5—H5	119.7	C14—C13—C12	120.3 (2)
C4—C5—H5	119.7	C14—C13—H13	119.8
C5—C6—O3	116.17 (17)	C12—C13—H13	119.8
C5—C6—C7	119.94 (19)	C13—C14—C15	119.6 (2)
O3—C6—C7	123.9 (2)	C13—C14—H14	120.2
C8—C7—C6	119.9 (2)	C15—C14—H14	120.2
C8—C7—H7	120.0	C14—C15—C16	120.2 (2)
C6—C7—H7	120.0	C14—C15—H15	119.9
C9—C8—C7	119.67 (18)	C16—C15—H15	119.9
C9—C8—H8	120.2	C11—C16—C15	120.6 (2)
C7—C8—H8	120.2	C11—C16—H16	119.7
C8—C9—O1	117.41 (16)	C15—C16—H16	119.7
C8—C9—C4	121.62 (18)
C9—O1—C1—O2	175.73 (19)	C5—C4—C9—C8	−0.9 (3)
C9—O1—C1—C2	−4.4 (3)	C3—C4—C9—C8	179.1 (2)
O2—C1—C2—C3	−177.5 (3)	C5—C4—C9—O1	−179.01 (18)
O1—C1—C2—C3	2.7 (3)	C3—C4—C9—O1	1.0 (3)
C1—C2—C3—C4	0.8 (4)	C5—C6—O3—C10	−179.6 (2)
C2—C3—C4—C9	−2.7 (3)	C7—C6—O3—C10	0.7 (4)
C2—C3—C4—C5	177.3 (2)	C6—O3—C10—C11	−176.5 (2)
C9—C4—C5—C6	1.1 (3)	O3—C10—C11—C12	−96.5 (3)
C3—C4—C5—C6	−178.9 (2)	O3—C10—C11—C16	85.6 (3)
C4—C5—C6—O3	179.72 (19)	C16—C11—C12—C13	1.0 (4)
C4—C5—C6—C7	−0.6 (4)	C10—C11—C12—C13	−176.9 (2)
C5—C6—C7—C8	0.0 (4)	C11—C12—C13—C14	−0.5 (4)
O3—C6—C7—C8	179.6 (2)	C12—C13—C14—C15	−0.2 (4)
C6—C7—C8—C9	0.2 (4)	C13—C14—C15—C16	0.2 (4)
C7—C8—C9—O1	178.4 (2)	C12—C11—C16—C15	−1.0 (4)
C7—C8—C9—C4	0.3 (4)	C10—C11—C16—C15	177.0 (2)
C1—O1—C9—C8	−175.6 (2)	C14—C15—C16—C11	0.3 (4)
C1—O1—C9—C4	2.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.62	3.472 (3)	153
C3—H3···O2ii	0.93	2.58	3.461 (3)	159
C5—H5···O1ii	0.93	2.59	3.501 (3)	168
C8—H8···O3iii	0.93	2.54	3.460 (3)	170
C16—H16···O2iv	0.93	2.56	3.421 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.62	3.472 (3)	153
C3—H3⋯O2ii	0.93	2.58	3.461 (3)	159
C5—H5⋯O1ii	0.93	2.59	3.501 (3)	168
C8—H8⋯O3iii	0.93	2.54	3.460 (3)	170
C16—H16⋯O2iv	0.93	2.56	3.421 (3)	154

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