7-Hy-droxy-4-methyl-8-(3-methyl-benzo-yl)-2H-chromen-2-one ethanol monosolvate.

In the title compound, C(18)H(14)O(4)·C(2)H(6)O, the coumarin ring system is approximately planar with a maximum deviation of 0.037 (3) Å and is nearly perpendicular to the benzene ring, making a dihedral angle of 86.55 (9)°. In the crystal, mol-ecules are linked by classical O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For the biological activity of coumarins, see: Sharma et al. (2005 ▶); Xiao et al. (2010 ▶); Iqbal et al. (2009 ▶); Siddiqui et al. (2009 ▶); Rollinger et al. (2004 ▶); Brühlmann et al. (2001 ▶). For a related structure, see: Yang et al. (2010 ▶).

Experimental

Crystal data

C18H14O4·C2H6O

M = 340.36

Monoclinic,

a = 12.4562 (6) Å

b = 10.0341 (5) Å

c = 14.8999 (7) Å

β = 111.980 (3)°

V = 1726.93 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.972, T max = 0.982

12216 measured reflections

3021 independent reflections

1762 reflections with I > 2σ(I)

R int = 0.119

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.188

S = 1.05

3021 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046630/xu5373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046630/xu5373Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046630/xu5373Isup3.cml

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

C18H14O4·C2H6O	F(000) = 720
Mr = 340.36	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1087 reflections
a = 12.4562 (6) Å	θ = 2.5–27.8°
b = 10.0341 (5) Å	µ = 0.09 mm−1
c = 14.8999 (7) Å	T = 298 K
β = 111.980 (3)°	Prism, colourless
V = 1726.93 (14) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3021 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
graphite	Rint = 0.119
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→8
Tmin = 0.972, Tmax = 0.982	k = −11→8
12216 measured reflections	l = −15→17

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0767P)2 + 0.8164P] where P = (Fo2 + 2Fc2)/3
3021 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.5042 (3)	0.6046 (3)	0.3838 (2)	0.0487 (8)
C2	0.3975 (3)	0.5458 (3)	0.3794 (2)	0.0547 (9)
H2	0.3386	0.6016	0.3809	0.066*
C3	0.3789 (3)	0.4140 (3)	0.3734 (2)	0.0498 (8)
C4	0.4702 (2)	0.3271 (3)	0.3715 (2)	0.0439 (7)
C5	0.4632 (3)	0.1883 (3)	0.3652 (2)	0.0538 (8)
H5	0.3943	0.1467	0.3595	0.065*
C6	0.5548 (3)	0.1119 (3)	0.3673 (2)	0.0523 (8)
H6	0.5474	0.0197	0.3626	0.063*
C7	0.6596 (3)	0.1722 (3)	0.3765 (2)	0.0460 (8)
C8	0.6708 (2)	0.3099 (3)	0.38248 (19)	0.0395 (7)
C9	0.5751 (2)	0.3841 (3)	0.37894 (18)	0.0400 (7)
C10	0.2669 (3)	0.3553 (4)	0.3712 (3)	0.0717 (11)
H10A	0.2202	0.4242	0.3828	0.108*
H10B	0.2828	0.2882	0.4205	0.108*
H10C	0.2261	0.3159	0.3090	0.108*
C11	0.7839 (2)	0.3780 (3)	0.3970 (2)	0.0409 (7)
C12	0.8089 (2)	0.4124 (3)	0.31036 (19)	0.0389 (7)
C13	0.9089 (2)	0.4854 (3)	0.3207 (2)	0.0445 (7)
H13	0.9614	0.5062	0.3823	0.053*
C14	0.9305 (3)	0.5269 (3)	0.2408 (2)	0.0524 (8)
C15	0.8528 (3)	0.4895 (4)	0.1505 (3)	0.0639 (10)
H15	0.8668	0.5149	0.0959	0.077*
C16	0.7554 (3)	0.4160 (4)	0.1391 (2)	0.0637 (10)
H16	0.7050	0.3917	0.0775	0.076*
C17	0.7327 (3)	0.3784 (3)	0.2191 (2)	0.0489 (8)
H17	0.6661	0.3301	0.2115	0.059*
C18	1.0332 (3)	0.6147 (4)	0.2514 (3)	0.0744 (11)
H18A	1.0066	0.7024	0.2278	0.112*
H18B	1.0751	0.5776	0.2147	0.112*
H18C	1.0833	0.6197	0.3184	0.112*
O1	0.59052 (16)	0.51973 (19)	0.38378 (14)	0.0455 (5)
O2	0.52656 (19)	0.7229 (2)	0.38776 (17)	0.0622 (7)
O3	0.75312 (19)	0.1018 (2)	0.37973 (17)	0.0611 (6)
H3	0.7378	0.0220	0.3759	0.092*
O4	0.84811 (18)	0.4066 (2)	0.47834 (15)	0.0611 (7)
C19	0.8207 (4)	0.7597 (4)	0.4184 (4)	0.0976 (15)
H19A	0.8036	0.6926	0.3680	0.117*
H19B	0.8307	0.7144	0.4785	0.117*
C20	0.9288 (4)	0.8253 (4)	0.4285 (4)	0.0938 (14)
H20A	0.9239	0.8584	0.3667	0.141*
H20B	0.9914	0.7626	0.4523	0.141*
H20C	0.9425	0.8981	0.4732	0.141*
O5	0.7296 (2)	0.8436 (2)	0.3963 (3)	0.1013 (11)
H5A	0.6743	0.8040	0.4008	0.152*

	U11	U22	U33	U12	U13	U23
C1	0.0388 (18)	0.049 (2)	0.0555 (19)	0.0084 (15)	0.0140 (14)	0.0061 (15)
C2	0.0376 (18)	0.060 (2)	0.065 (2)	0.0087 (16)	0.0180 (15)	0.0060 (17)
C3	0.0358 (17)	0.062 (2)	0.0499 (18)	−0.0011 (16)	0.0140 (13)	0.0072 (15)
C4	0.0359 (16)	0.049 (2)	0.0452 (17)	−0.0037 (14)	0.0129 (13)	0.0039 (14)
C5	0.0417 (18)	0.058 (2)	0.061 (2)	−0.0136 (16)	0.0182 (15)	0.0034 (16)
C6	0.052 (2)	0.0435 (19)	0.062 (2)	−0.0063 (16)	0.0216 (16)	0.0020 (15)
C7	0.0421 (18)	0.0450 (19)	0.0511 (18)	0.0015 (15)	0.0177 (14)	0.0041 (14)
C8	0.0384 (16)	0.0392 (17)	0.0408 (16)	−0.0007 (13)	0.0148 (12)	0.0016 (13)
C9	0.0401 (17)	0.0388 (17)	0.0398 (15)	−0.0019 (14)	0.0135 (13)	0.0038 (13)
C10	0.041 (2)	0.085 (3)	0.092 (3)	−0.0007 (19)	0.0287 (18)	0.011 (2)
C11	0.0358 (16)	0.0378 (17)	0.0459 (17)	0.0044 (13)	0.0117 (14)	0.0010 (13)
C12	0.0319 (15)	0.0361 (16)	0.0486 (16)	0.0030 (13)	0.0149 (13)	−0.0006 (13)
C13	0.0358 (16)	0.0409 (18)	0.0566 (18)	0.0009 (13)	0.0170 (14)	−0.0052 (14)
C14	0.050 (2)	0.0468 (19)	0.069 (2)	0.0021 (15)	0.0332 (17)	0.0032 (16)
C15	0.067 (2)	0.075 (3)	0.060 (2)	0.004 (2)	0.0343 (19)	0.0069 (18)
C16	0.058 (2)	0.083 (3)	0.0475 (19)	−0.005 (2)	0.0169 (16)	−0.0057 (17)
C17	0.0451 (18)	0.0514 (19)	0.0493 (18)	−0.0030 (15)	0.0167 (14)	−0.0027 (14)
C18	0.063 (2)	0.071 (3)	0.103 (3)	−0.010 (2)	0.048 (2)	0.005 (2)
O1	0.0357 (11)	0.0407 (12)	0.0602 (13)	0.0028 (9)	0.0179 (10)	0.0051 (9)
O2	0.0485 (14)	0.0451 (14)	0.0929 (18)	0.0074 (11)	0.0262 (12)	0.0043 (12)
O3	0.0509 (14)	0.0423 (13)	0.0938 (17)	0.0020 (11)	0.0314 (12)	−0.0004 (12)
O4	0.0472 (14)	0.0809 (17)	0.0482 (13)	−0.0111 (12)	0.0098 (11)	−0.0003 (11)
C19	0.097 (3)	0.059 (3)	0.171 (5)	0.012 (3)	0.088 (3)	0.017 (3)
C20	0.071 (3)	0.081 (3)	0.131 (4)	0.006 (2)	0.040 (3)	−0.009 (3)
O5	0.0615 (17)	0.0419 (15)	0.203 (3)	0.0025 (13)	0.052 (2)	0.0129 (17)

C1—O2	1.216 (4)	C12—C17	1.379 (4)
C1—O1	1.372 (4)	C12—C13	1.403 (4)
C1—C2	1.433 (4)	C13—C14	1.379 (4)
C2—C3	1.340 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.384 (5)
C3—C4	1.441 (4)	C14—C18	1.512 (4)
C3—C10	1.503 (4)	C15—C16	1.375 (5)
C4—C9	1.393 (4)	C15—H15	0.9300
C4—C5	1.397 (4)	C16—C17	1.376 (4)
C5—C6	1.364 (4)	C16—H16	0.9300
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.399 (4)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—O3	1.348 (3)	C18—H18C	0.9600
C7—C8	1.387 (4)	O3—H3	0.8200
C8—C9	1.390 (4)	C19—O5	1.352 (5)
C8—C11	1.507 (4)	C19—C20	1.454 (6)
C9—O1	1.372 (3)	C19—H19A	0.9700
C10—H10A	0.9600	C19—H19B	0.9700
C10—H10B	0.9600	C20—H20A	0.9600
C10—H10C	0.9600	C20—H20B	0.9600
C11—O4	1.211 (3)	C20—H20C	0.9600
C11—C12	1.478 (4)	O5—H5A	0.8200
O2—C1—O1	116.1 (3)	C13—C12—C11	119.7 (2)
O2—C1—C2	126.6 (3)	C14—C13—C12	121.0 (3)
O1—C1—C2	117.3 (3)	C14—C13—H13	119.5
C3—C2—C1	122.9 (3)	C12—C13—H13	119.5
C3—C2—H2	118.5	C13—C14—C15	117.8 (3)
C1—C2—H2	118.5	C13—C14—C18	121.1 (3)
C2—C3—C4	118.7 (3)	C15—C14—C18	121.1 (3)
C2—C3—C10	121.6 (3)	C16—C15—C14	122.0 (3)
C4—C3—C10	119.7 (3)	C16—C15—H15	119.0
C9—C4—C5	116.6 (3)	C14—C15—H15	119.0
C9—C4—C3	118.3 (3)	C15—C16—C17	119.8 (3)
C5—C4—C3	125.1 (3)	C15—C16—H16	120.1
C6—C5—C4	121.9 (3)	C17—C16—H16	120.1
C6—C5—H5	119.0	C16—C17—C12	119.8 (3)
C4—C5—H5	119.0	C16—C17—H17	120.1
C5—C6—C7	120.1 (3)	C12—C17—H17	120.1
C5—C6—H6	120.0	C14—C18—H18A	109.5
C7—C6—H6	120.0	C14—C18—H18B	109.5
O3—C7—C8	117.1 (3)	H18A—C18—H18B	109.5
O3—C7—C6	122.6 (3)	C14—C18—H18C	109.5
C8—C7—C6	120.3 (3)	H18A—C18—H18C	109.5
C7—C8—C9	117.9 (3)	H18B—C18—H18C	109.5
C7—C8—C11	121.8 (3)	C1—O1—C9	121.4 (2)
C9—C8—C11	120.3 (2)	C7—O3—H3	109.5
O1—C9—C8	115.4 (2)	O5—C19—C20	113.8 (3)
O1—C9—C4	121.3 (3)	O5—C19—H19A	108.8
C8—C9—C4	123.3 (3)	C20—C19—H19A	108.8
C3—C10—H10A	109.5	O5—C19—H19B	108.8
C3—C10—H10B	109.5	C20—C19—H19B	108.8
H10A—C10—H10B	109.5	H19A—C19—H19B	107.7
C3—C10—H10C	109.5	C19—C20—H20A	109.5
H10A—C10—H10C	109.5	C19—C20—H20B	109.5
H10B—C10—H10C	109.5	H20A—C20—H20B	109.5
O4—C11—C12	122.8 (3)	C19—C20—H20C	109.5
O4—C11—C8	118.9 (2)	H20A—C20—H20C	109.5
C12—C11—C8	118.2 (2)	H20B—C20—H20C	109.5
C17—C12—C13	119.5 (3)	C19—O5—H5A	109.5
C17—C12—C11	120.7 (3)
O2—C1—C2—C3	178.8 (3)	C3—C4—C9—C8	176.9 (3)
O1—C1—C2—C3	−1.5 (4)	C7—C8—C11—O4	−94.5 (3)
C1—C2—C3—C4	0.2 (5)	C9—C8—C11—O4	82.6 (3)
C1—C2—C3—C10	178.6 (3)	C7—C8—C11—C12	88.2 (3)
C2—C3—C4—C9	1.9 (4)	C9—C8—C11—C12	−94.7 (3)
C10—C3—C4—C9	−176.5 (3)	O4—C11—C12—C17	−179.6 (3)
C2—C3—C4—C5	−179.9 (3)	C8—C11—C12—C17	−2.4 (4)
C10—C3—C4—C5	1.7 (4)	O4—C11—C12—C13	−2.3 (4)
C9—C4—C5—C6	0.7 (4)	C8—C11—C12—C13	174.8 (2)
C3—C4—C5—C6	−177.6 (3)	C17—C12—C13—C14	1.8 (4)
C4—C5—C6—C7	0.4 (5)	C11—C12—C13—C14	−175.5 (3)
C5—C6—C7—O3	179.5 (3)	C12—C13—C14—C15	−2.6 (4)
C5—C6—C7—C8	−0.8 (4)	C12—C13—C14—C18	175.2 (3)
O3—C7—C8—C9	179.8 (2)	C13—C14—C15—C16	1.4 (5)
C6—C7—C8—C9	0.0 (4)	C18—C14—C15—C16	−176.3 (3)
O3—C7—C8—C11	−3.1 (4)	C14—C15—C16—C17	0.5 (6)
C6—C7—C8—C11	177.2 (3)	C15—C16—C17—C12	−1.3 (5)
C7—C8—C9—O1	−179.1 (2)	C13—C12—C17—C16	0.1 (5)
C11—C8—C9—O1	3.6 (3)	C11—C12—C17—C16	177.4 (3)
C7—C8—C9—C4	1.2 (4)	O2—C1—O1—C9	−179.6 (2)
C11—C8—C9—C4	−176.1 (2)	C2—C1—O1—C9	0.6 (4)
C5—C4—C9—O1	178.8 (2)	C8—C9—O1—C1	−178.2 (2)
C3—C4—C9—O1	−2.8 (4)	C4—C9—O1—C1	1.5 (4)
C5—C4—C9—C8	−1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5i	0.82	1.82	2.629 (3)	166.
O5—H5A···O2	0.82	1.95	2.764 (3)	169.
C17—H17···O2ii	0.93	2.54	3.398 (4)	154.
C20—H20B···O4iii	0.96	2.53	3.489 (5)	177.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5i	0.82	1.82	2.629 (3)	166
O5—H5A⋯O2	0.82	1.95	2.764 (3)	169
C17—H17⋯O2ii	0.93	2.54	3.398 (4)	154
C20—H20B⋯O4iii	0.96	2.53	3.489 (5)	177

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