3-Phenyl-coumarin.

In the title compound, C(15)H(10)O(2), a 3-phenyl derivative of the coumarin (also known as 2H-chromen-2-one or 2H-1-benzopyran-2-one) scaffold, the C(p)-C(p)-C(c)-C(c) torsion angle between the coumarin (c) ring system and the phenyl (p) ring is -47.6 (2)°.

Related literature

For the synthesis of the title compound, see: Matos, Santana et al.. et al. (2011 ▶); Matos, Terán et al.. et al. (2011 ▶). For examples of biological activity of coumarin derivatives, see: Borges et al. (2009 ▶); Matos et al. (2009 ▶, 2010 ▶); Matos, Santana et al.. et al. (2011 ▶); Matos, Terán et al.. et al. (2011 ▶); Viña, Matos, Ferino et al. (2012 ▶); Viña, Matos Yáñez et al. (2012 ▶).

Experimental

Crystal data

C15H10O2

M = 222.23

Monoclinic,

a = 18.469 (4) Å

b = 5.9596 (12) Å

c = 19.274 (4) Å

β = 99.079 (3)°

V = 2094.9 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.27 × 0.22 × 0.09 mm

Data collection

Bruker SMART CCD 1000 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.876, T max = 1

9021 measured reflections

1924 independent reflections

1492 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.03

1924 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034277/zj2091sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034277/zj2091Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034277/zj2091Isup3.cml

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

C15H10O2	F(000) = 928
Mr = 222.23	F(000) = 928
Monoclinic, C2/c	Dx = 1.409 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.7107 Å
a = 18.469 (4) Å	Cell parameters from 1813 reflections
b = 5.9596 (12) Å	θ = 2.8–26.2°
c = 19.274 (4) Å	µ = 0.09 mm−1
β = 99.079 (3)°	T = 100 K
V = 2094.9 (7) Å3	Prism, colourless
Z = 8	0.27 × 0.22 × 0.09 mm

Bruker SMART CCD 1000 diffractometer	1924 independent reflections
Radiation source: fine-focus sealed tube	1492 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 25.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −22→21
Tmin = 0.876, Tmax = 1	k = 0→7
9021 measured reflections	l = 0→23

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0528P)2 + 1.3579P] where P = (Fo2 + 2Fc2)/3
1924 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.21370 (8)	0.2410 (3)	0.36971 (8)	0.0168 (4)
H1	0.219	0.3712	0.3985	0.02*
C2	0.15672 (9)	0.2280 (3)	0.31395 (8)	0.0184 (4)
H2	0.1223	0.3472	0.3054	0.022*
C3	0.14979 (9)	0.0409 (3)	0.27041 (8)	0.0192 (4)
H3	0.1115	0.0337	0.2313	0.023*
C4	0.19876 (9)	−0.1348 (3)	0.28427 (8)	0.0188 (4)
H4	0.1939	−0.263	0.2546	0.023*
C5	0.25492 (9)	−0.1254 (3)	0.34124 (8)	0.0166 (4)
H5	0.2876	−0.2485	0.3511	0.02*
C6	0.26348 (8)	0.0646 (3)	0.38409 (8)	0.0145 (4)
C7	0.32522 (8)	0.0774 (3)	0.44333 (8)	0.0146 (3)
C8	0.34288 (8)	−0.0903 (3)	0.49004 (8)	0.0145 (3)
H8	0.3139	−0.2228	0.4858	0.017*
C9	0.40398 (8)	−0.0744 (3)	0.54588 (8)	0.0145 (4)
C10	0.42315 (8)	−0.2408 (3)	0.59681 (8)	0.0168 (4)
H10	0.3949	−0.3744	0.5955	0.02*
C11	0.48286 (9)	−0.2116 (3)	0.64877 (8)	0.0201 (4)
H11	0.4954	−0.3246	0.6834	0.024*
C12	0.52497 (9)	−0.0168 (3)	0.65072 (8)	0.0206 (4)
H12	0.5664	0.001	0.6863	0.025*
C13	0.50708 (9)	0.1506 (3)	0.60137 (8)	0.0190 (4)
H13	0.5357	0.2835	0.6026	0.023*
C14	0.44646 (8)	0.1196 (3)	0.55016 (8)	0.0152 (4)
C15	0.37106 (8)	0.2799 (3)	0.44882 (8)	0.0161 (4)
O1	0.42953 (6)	0.29055 (18)	0.50224 (5)	0.0177 (3)
O2	0.36238 (6)	0.43926 (18)	0.40948 (6)	0.0220 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0191 (8)	0.0165 (8)	0.0160 (8)	0.0006 (7)	0.0062 (7)	−0.0010 (7)
C2	0.0167 (8)	0.0186 (9)	0.0206 (8)	0.0025 (7)	0.0050 (7)	0.0052 (7)
C3	0.0166 (8)	0.0250 (9)	0.0156 (8)	−0.0040 (7)	0.0013 (6)	0.0034 (7)
C4	0.0215 (9)	0.0188 (9)	0.0167 (8)	−0.0050 (7)	0.0051 (7)	−0.0029 (7)
C5	0.0188 (8)	0.0134 (8)	0.0182 (8)	0.0012 (7)	0.0050 (7)	0.0020 (6)
C6	0.0144 (8)	0.0156 (8)	0.0144 (8)	−0.0023 (6)	0.0054 (6)	0.0004 (6)
C7	0.0149 (8)	0.0147 (8)	0.0152 (8)	0.0012 (6)	0.0055 (6)	−0.0020 (6)
C8	0.0154 (8)	0.0132 (8)	0.0160 (8)	0.0001 (6)	0.0058 (6)	−0.0028 (6)
C9	0.0138 (8)	0.0167 (8)	0.0140 (8)	0.0030 (6)	0.0056 (6)	−0.0019 (6)
C10	0.0174 (8)	0.0166 (8)	0.0177 (8)	0.0012 (7)	0.0066 (7)	0.0003 (7)
C11	0.0216 (9)	0.0225 (9)	0.0163 (8)	0.0063 (7)	0.0037 (7)	0.0017 (7)
C12	0.0158 (8)	0.0283 (10)	0.0171 (8)	0.0035 (7)	0.0010 (6)	−0.0041 (7)
C13	0.0174 (8)	0.0201 (9)	0.0199 (9)	−0.0013 (7)	0.0046 (7)	−0.0057 (7)
C14	0.0168 (8)	0.0162 (8)	0.0136 (8)	0.0038 (7)	0.0057 (6)	−0.0005 (6)
C15	0.0154 (8)	0.0161 (8)	0.0171 (8)	0.0020 (7)	0.0038 (6)	−0.0025 (7)
O1	0.0202 (6)	0.0138 (6)	0.0185 (6)	−0.0026 (5)	0.0011 (5)	0.0000 (5)
O2	0.0239 (6)	0.0148 (6)	0.0265 (6)	−0.0003 (5)	0.0017 (5)	0.0053 (5)

C1—C2	1.382 (2)	C8—H8	0.95
C1—C6	1.395 (2)	C9—C14	1.392 (2)
C1—H1	0.95	C9—C10	1.401 (2)
C2—C3	1.390 (2)	C10—C11	1.379 (2)
C2—H2	0.95	C10—H10	0.95
C3—C4	1.382 (2)	C11—C12	1.395 (2)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.387 (2)	C12—C13	1.382 (2)
C4—H4	0.95	C12—H12	0.95
C5—C6	1.396 (2)	C13—C14	1.383 (2)
C5—H5	0.95	C13—H13	0.95
C6—C7	1.483 (2)	C14—O1	1.3776 (18)
C7—C8	1.350 (2)	C15—O2	1.2102 (19)
C7—C15	1.468 (2)	C15—O1	1.3709 (19)
C8—C9	1.434 (2)
C2—C1—C6	120.61 (15)	C9—C8—H8	119
C2—C1—H1	119.7	C14—C9—C10	117.94 (14)
C6—C1—H1	119.7	C14—C9—C8	117.93 (14)
C1—C2—C3	120.03 (15)	C10—C9—C8	124.13 (15)
C1—C2—H2	120	C11—C10—C9	120.29 (15)
C3—C2—H2	120	C11—C10—H10	119.9
C4—C3—C2	119.76 (15)	C9—C10—H10	119.9
C4—C3—H3	120.1	C10—C11—C12	120.22 (15)
C2—C3—H3	120.1	C10—C11—H11	119.9
C3—C4—C5	120.48 (15)	C12—C11—H11	119.9
C3—C4—H4	119.8	C13—C12—C11	120.71 (15)
C5—C4—H4	119.8	C13—C12—H12	119.6
C4—C5—C6	120.11 (15)	C11—C12—H12	119.6
C4—C5—H5	119.9	C12—C13—C14	118.25 (15)
C6—C5—H5	119.9	C12—C13—H13	120.9
C1—C6—C5	118.96 (14)	C14—C13—H13	120.9
C1—C6—C7	121.09 (14)	O1—C14—C13	116.88 (14)
C5—C6—C7	119.94 (14)	O1—C14—C9	120.55 (14)
C8—C7—C15	118.97 (14)	C13—C14—C9	122.57 (14)
C8—C7—C6	123.41 (14)	O2—C15—O1	116.41 (14)
C15—C7—C6	117.56 (14)	O2—C15—C7	125.59 (15)
C7—C8—C9	122.02 (15)	O1—C15—C7	117.99 (14)
C7—C8—H8	119	C15—O1—C14	122.53 (12)
C6—C1—C2—C3	−1.8 (2)	C9—C10—C11—C12	−0.5 (2)
C1—C2—C3—C4	1.9 (2)	C10—C11—C12—C13	0.8 (2)
C2—C3—C4—C5	−0.2 (2)	C11—C12—C13—C14	0.0 (2)
C3—C4—C5—C6	−1.6 (2)	C12—C13—C14—O1	179.25 (13)
C2—C1—C6—C5	0.0 (2)	C12—C13—C14—C9	−1.2 (2)
C2—C1—C6—C7	179.41 (14)	C10—C9—C14—O1	−178.93 (13)
C4—C5—C6—C1	1.6 (2)	C8—C9—C14—O1	0.4 (2)
C4—C5—C6—C7	−177.73 (14)	C10—C9—C14—C13	1.5 (2)
C1—C6—C7—C8	133.05 (16)	C8—C9—C14—C13	−179.15 (13)
C5—C6—C7—C8	−47.6 (2)	C8—C7—C15—O2	178.09 (15)
C1—C6—C7—C15	−49.86 (19)	C6—C7—C15—O2	0.9 (2)
C5—C6—C7—C15	129.50 (15)	C8—C7—C15—O1	−0.9 (2)
C15—C7—C8—C9	1.5 (2)	C6—C7—C15—O1	−178.17 (12)
C6—C7—C8—C9	178.59 (14)	O2—C15—O1—C14	−179.01 (13)
C7—C8—C9—C14	−1.3 (2)	C7—C15—O1—C14	0.1 (2)
C7—C8—C9—C10	178.02 (14)	C13—C14—O1—C15	179.72 (13)
C14—C9—C10—C11	−0.6 (2)	C9—C14—O1—C15	0.1 (2)
C8—C9—C10—C11	−179.96 (14)