8-Benzoyl-7-hy-droxy-4-methyl-2H-1-benzopyran-2-one monohydrate.

In the title compound, C(17)H(12)O(4)·H(2)O, the coumarin ring system is approximately planar with a maximum atomic deviation of 0.011 (2) Å, and is nearly perpendicular to the phenyl ring at a dihedral angle of 86.63 (9)°. In the crystal, mol-ecules are linked by classical O-H⋯O and weak C-H⋯O hydrogen bonds. π-π stacking is also present [centroid-centroid distance = 3.6898 (12) Å].

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 related structures, see: Yang et al. (2006 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C17H12O4·H2O

M = 298.28

Monoclinic,

a = 14.8912 (15) Å

b = 9.6768 (11) Å

c = 20.644 (2) Å

β = 104.275 (2)°

V = 2882.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.49 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.979

7271 measured reflections

2549 independent reflections

1706 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.05

2549 reflections

255 parameters

All H-atom parameters refined

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046350/xu5087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046350/xu5087Isup2.hkl

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

C17H12O4·H2O	F(000) = 1248
Mr = 298.28	Dx = 1.374 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2106 reflections
a = 14.8912 (15) Å	θ = 2.6–26.3°
b = 9.6768 (11) Å	µ = 0.10 mm−1
c = 20.644 (2) Å	T = 298 K
β = 104.275 (2)°	Prism, colorless
V = 2882.9 (5) Å3	0.49 × 0.24 × 0.21 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2549 independent reflections
Radiation source: fine-focus sealed tube	1706 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→14
Tmin = 0.952, Tmax = 0.979	k = −11→11
7271 measured reflections	l = −24→24

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) = 0.110	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0463P)2 + 1.197P] where P = (Fo2 + 2Fc2)/3
2549 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 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	0.17438 (9)	0.30443 (14)	0.31197 (6)	0.0429 (4)
O2	0.13299 (12)	0.09551 (16)	0.27504 (8)	0.0590 (5)
O3	0.27345 (10)	0.73405 (18)	0.40667 (7)	0.0516 (4)
H3	0.2699 (19)	0.830 (3)	0.4027 (13)	0.093 (10)*
O4	0.23351 (10)	0.42720 (19)	0.46551 (7)	0.0621 (5)
C1	0.12717 (15)	0.2185 (2)	0.26211 (10)	0.0443 (5)
C2	0.07607 (15)	0.2814 (2)	0.20096 (10)	0.0453 (6)
H2	0.0427 (14)	0.218 (2)	0.1671 (10)	0.050 (6)*
C3	0.07320 (13)	0.4192 (2)	0.19106 (9)	0.0397 (5)
C4	0.12370 (13)	0.5072 (2)	0.24429 (9)	0.0367 (5)
C5	0.12629 (15)	0.6515 (2)	0.24161 (11)	0.0436 (5)
H5	0.0918 (13)	0.697 (2)	0.2017 (10)	0.042 (5)*
C6	0.17489 (14)	0.7290 (2)	0.29421 (11)	0.0438 (5)
H6	0.1748 (14)	0.829 (2)	0.2898 (10)	0.050 (6)*
C7	0.22368 (14)	0.6637 (2)	0.35315 (10)	0.0395 (5)
C8	0.22316 (13)	0.5202 (2)	0.35827 (9)	0.0364 (5)
C9	0.17343 (13)	0.4459 (2)	0.30380 (9)	0.0359 (5)
C10	0.01805 (19)	0.4821 (3)	0.12713 (12)	0.0522 (6)
H10A	−0.0231 (17)	0.414 (3)	0.0985 (12)	0.074 (8)*
H10B	−0.0219 (17)	0.555 (3)	0.1356 (12)	0.071 (8)*
H10C	0.0575 (16)	0.525 (3)	0.1039 (12)	0.064 (8)*
C11	0.27364 (14)	0.4473 (2)	0.42133 (9)	0.0390 (5)
C12	0.37057 (13)	0.4036 (2)	0.42734 (9)	0.0360 (5)
H13	0.3868 (14)	0.308 (2)	0.5173 (11)	0.056 (7)*
C13	0.41872 (16)	0.3316 (2)	0.48382 (11)	0.0484 (6)
C14	0.51066 (17)	0.2977 (3)	0.49076 (13)	0.0568 (7)
H14	0.5453 (14)	0.250 (2)	0.5300 (11)	0.057 (6)*
C15	0.55516 (17)	0.3334 (3)	0.44212 (12)	0.0552 (6)
H15	0.6208 (17)	0.309 (2)	0.4484 (11)	0.063 (7)*
C16	0.50801 (16)	0.4022 (3)	0.38535 (12)	0.0523 (6)
H16	0.5390 (16)	0.430 (2)	0.3503 (12)	0.070 (7)*
C17	0.41556 (15)	0.4371 (2)	0.37787 (10)	0.0417 (5)
H17	0.3830 (13)	0.483 (2)	0.3384 (10)	0.046 (6)*
O5	0.25946 (14)	0.00677 (18)	0.39756 (10)	0.0631 (5)
H5A	0.220 (2)	0.049 (4)	0.3623 (17)	0.125 (13)*
H5B	0.258 (2)	0.045 (3)	0.4355 (16)	0.101 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0533 (9)	0.0359 (9)	0.0360 (8)	0.0039 (7)	0.0042 (6)	0.0021 (6)
O2	0.0815 (12)	0.0410 (10)	0.0500 (9)	0.0009 (9)	0.0076 (8)	0.0008 (8)
O3	0.0539 (10)	0.0458 (11)	0.0477 (9)	−0.0017 (8)	−0.0015 (7)	−0.0047 (8)
O4	0.0535 (10)	0.0921 (13)	0.0436 (9)	0.0117 (9)	0.0173 (8)	0.0148 (8)
C1	0.0524 (14)	0.0411 (14)	0.0403 (12)	0.0011 (11)	0.0133 (10)	−0.0015 (10)
C2	0.0499 (14)	0.0491 (15)	0.0357 (12)	−0.0010 (11)	0.0086 (10)	−0.0057 (10)
C3	0.0376 (12)	0.0496 (14)	0.0324 (10)	0.0032 (10)	0.0095 (9)	0.0010 (10)
C4	0.0360 (11)	0.0409 (13)	0.0327 (10)	0.0051 (9)	0.0078 (9)	0.0034 (9)
C5	0.0431 (13)	0.0445 (14)	0.0393 (12)	0.0072 (11)	0.0031 (10)	0.0094 (11)
C6	0.0454 (13)	0.0354 (13)	0.0479 (13)	0.0045 (10)	0.0065 (10)	0.0046 (10)
C7	0.0366 (12)	0.0425 (13)	0.0383 (11)	0.0014 (10)	0.0074 (9)	−0.0020 (10)
C8	0.0351 (11)	0.0401 (13)	0.0339 (10)	0.0035 (9)	0.0080 (9)	0.0017 (9)
C9	0.0373 (11)	0.0340 (12)	0.0374 (11)	0.0049 (9)	0.0108 (9)	0.0027 (9)
C10	0.0494 (15)	0.0626 (18)	0.0403 (13)	0.0049 (14)	0.0029 (12)	0.0046 (12)
C11	0.0427 (12)	0.0404 (12)	0.0329 (11)	−0.0018 (10)	0.0076 (9)	−0.0017 (9)
C12	0.0390 (11)	0.0333 (12)	0.0329 (10)	−0.0020 (9)	0.0039 (9)	−0.0018 (9)
C13	0.0480 (14)	0.0536 (15)	0.0419 (12)	0.0010 (11)	0.0079 (11)	0.0088 (11)
C14	0.0501 (15)	0.0607 (17)	0.0526 (15)	0.0086 (12)	−0.0007 (12)	0.0109 (12)
C15	0.0391 (14)	0.0596 (16)	0.0636 (16)	0.0030 (12)	0.0064 (12)	−0.0049 (13)
C16	0.0473 (14)	0.0588 (16)	0.0534 (14)	−0.0038 (12)	0.0176 (12)	−0.0056 (12)
C17	0.0464 (13)	0.0402 (13)	0.0363 (11)	−0.0016 (10)	0.0065 (10)	0.0000 (10)
O5	0.0828 (13)	0.0548 (12)	0.0488 (11)	0.0045 (9)	0.0106 (10)	−0.0027 (9)

O1—C1	1.374 (2)	C8—C11	1.509 (3)
O1—C9	1.379 (2)	C10—H10A	0.99 (3)
O2—C1	1.218 (2)	C10—H10B	0.96 (3)
O3—C7	1.352 (2)	C10—H10C	0.94 (2)
O3—H3	0.93 (3)	C11—C12	1.479 (3)
O4—C11	1.223 (2)	C12—C17	1.391 (3)
C1—C2	1.438 (3)	C12—C13	1.395 (3)
C2—C3	1.348 (3)	C13—C14	1.381 (3)
C2—H2	0.97 (2)	C13—H13	0.96 (2)
C3—C4	1.446 (3)	C14—C15	1.376 (3)
C3—C10	1.501 (3)	C14—H14	0.96 (2)
C4—C5	1.398 (3)	C15—C16	1.380 (3)
C4—C9	1.400 (3)	C15—H15	0.98 (2)
C5—C6	1.370 (3)	C16—C17	1.389 (3)
C5—H5	0.96 (2)	C16—H16	0.99 (2)
C6—C7	1.404 (3)	C17—H17	0.95 (2)
C6—H6	0.97 (2)	O5—H5A	0.91 (4)
C7—C8	1.393 (3)	O5—H5B	0.87 (3)
C8—C9	1.385 (3)
C1—O1—C9	121.41 (15)	C3—C10—H10A	112.3 (14)
C7—O3—H3	114.9 (17)	C3—C10—H10B	111.4 (15)
O2—C1—O1	115.56 (19)	H10A—C10—H10B	106 (2)
O2—C1—C2	126.8 (2)	C3—C10—H10C	110.6 (14)
O1—C1—C2	117.6 (2)	H10A—C10—H10C	111 (2)
C3—C2—C1	122.8 (2)	H10B—C10—H10C	105 (2)
C3—C2—H2	121.6 (12)	O4—C11—C12	122.57 (18)
C1—C2—H2	115.7 (12)	O4—C11—C8	119.13 (18)
C2—C3—C4	118.45 (18)	C12—C11—C8	118.30 (16)
C2—C3—C10	121.6 (2)	C17—C12—C13	119.26 (19)
C4—C3—C10	119.9 (2)	C17—C12—C11	120.57 (18)
C5—C4—C9	116.35 (19)	C13—C12—C11	120.15 (17)
C5—C4—C3	124.92 (19)	C14—C13—C12	119.8 (2)
C9—C4—C3	118.73 (19)	C14—C13—H13	121.6 (13)
C6—C5—C4	122.0 (2)	C12—C13—H13	118.6 (13)
C6—C5—H5	119.5 (12)	C15—C14—C13	120.5 (2)
C4—C5—H5	118.5 (12)	C15—C14—H14	118.6 (12)
C5—C6—C7	120.0 (2)	C13—C14—H14	120.8 (12)
C5—C6—H6	118.9 (12)	C14—C15—C16	120.3 (2)
C7—C6—H6	121.1 (12)	C14—C15—H15	119.2 (13)
O3—C7—C8	116.86 (18)	C16—C15—H15	120.5 (13)
O3—C7—C6	123.0 (2)	C15—C16—C17	119.7 (2)
C8—C7—C6	120.16 (19)	C15—C16—H16	121.4 (14)
C9—C8—C7	117.90 (18)	C17—C16—H16	118.9 (14)
C9—C8—C11	120.69 (19)	C16—C17—C12	120.4 (2)
C7—C8—C11	121.40 (18)	C16—C17—H17	119.5 (12)
O1—C9—C8	115.39 (16)	C12—C17—H17	120.1 (12)
O1—C9—C4	121.00 (17)	H5A—O5—H5B	112 (3)
C8—C9—C4	123.60 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5i	0.93 (3)	1.72 (3)	2.650 (2)	177 (3)
O5—H5A···O2	0.91 (4)	2.00 (4)	2.887 (3)	166 (3)
O5—H5B···O4ii	0.87 (3)	2.03 (3)	2.875 (2)	162 (3)
C17—H17···O2iii	0.95 (2)	2.54 (2)	3.422 (3)	154.7 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5i	0.93 (3)	1.72 (3)	2.650 (2)	177 (3)
O5—H5A⋯O2	0.91 (4)	2.00 (4)	2.887 (3)	166 (3)
O5—H5B⋯O4ii	0.87 (3)	2.03 (3)	2.875 (2)	162 (3)
C17—H17⋯O2iii	0.95 (2)	2.54 (2)	3.422 (3)	154.7 (16)

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