6-Butyryl-5-hy-droxy-4-phenyl-seselin.

IN THE TITLE COUMARIN COMPOUND (SYSTEMATIC NAME: 6-butyryl-5-hy-droxy-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b;3,4-b']dipyran-2-one), C(24)H(22)O(5), also known as mammea A/AC cyclo D, the chromene and pyran rings are almost coplanar with a maximum deviation from the mean plane of 0.295 (2) Å. The attached phenyl group is inclined at 53.49 (8)° with respect to the chromene ring. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are linked into sheets parallel to (101) by inter-molecular C-H⋯O hydrogen bonds. Adjacent sheets are sustained by inter-molecular C-H⋯π and π-π [centroid-centroid distance = 4.471 (2) Å] inter-actions.

Related literature

For the structural characterization of mammea A/AC cyclo D, see: Thebtaranonth et al. (1981 ▶); Morel et al. (1999 ▶); Kaweetripob et al. (2000 ▶). For its anti-HIV activity, see: Márquez et al. (2005 ▶); Bedoya et al. (2005 ▶) and for its anti­cancer activity, see: Reyes-Chilpa et al. (2004 ▶). For related coumarins, see: Mahidol et al. (2002 ▶). For a review on the cytotoxic activity of coumarins, see: Kostova (2005 ▶).

Experimental

Crystal data

C24H22O5

M = 390.42

Monoclinic,

a = 17.0746 (4) Å

b = 13.4170 (4) Å

c = 8.7607 (3) Å

β = 90.341 (1)°

V = 2006.95 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.32 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.986

5484 measured reflections

2115 independent reflections

1714 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.03

2115 reflections

265 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al. 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003415X/ds2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003415X/ds2051Isup2.hkl

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

C24H22O5	F(000) = 824
Mr = 390.42	Dx = 1.292 Mg m−3
Monoclinic, Cc	Melting point = 412–413 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.0746 (4) Å	Cell parameters from 2083 reflections
b = 13.4170 (4) Å	θ = 2.4–24.3°
c = 8.7607 (3) Å	µ = 0.09 mm−1
β = 90.341 (1)°	T = 298 K
V = 2006.95 (10) Å3	Block, light yellow
Z = 4	0.40 × 0.32 × 0.16 mm

Bruker SMART APEXII CCD area-detector diffractometer	2115 independent reflections
Radiation source: fine-focus sealed tube	1714 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 26.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
Tmin = 0.965, Tmax = 0.986	k = −16→12
5484 measured reflections	l = −11→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.3001P] where P = (Fo2 + 2Fc2)/3
2115 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.13 e Å−3
2 restraints	Δρmin = −0.14 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	0.37812 (12)	0.33800 (15)	0.0704 (2)	0.0539 (5)
C2	0.33746 (18)	0.2581 (2)	0.1325 (4)	0.0585 (8)
C3	0.26471 (17)	0.2825 (2)	0.2042 (4)	0.0527 (7)
H3	0.2335	0.2304	0.2382	0.063*
C4	0.23882 (15)	0.3763 (2)	0.2253 (3)	0.0417 (6)
C4A	0.28947 (13)	0.4585 (2)	0.1797 (3)	0.0381 (6)
C5	0.27705 (14)	0.5596 (2)	0.2138 (3)	0.0401 (6)
C6	0.32418 (15)	0.6360 (2)	0.1496 (3)	0.0418 (6)
C7	0.38818 (14)	0.6053 (2)	0.0584 (3)	0.0430 (6)
C8	0.40587 (14)	0.5060 (2)	0.0336 (3)	0.0426 (6)
C8A	0.35629 (14)	0.4350 (2)	0.0958 (3)	0.0413 (6)
O2	0.36629 (16)	0.17743 (18)	0.1167 (4)	0.0866 (8)
O3	0.22095 (11)	0.58102 (16)	0.3131 (2)	0.0545 (5)
H3O	0.2187	0.6415	0.3254	0.065*
C1'	0.15739 (15)	0.3906 (2)	0.2792 (3)	0.0423 (6)
C2'	0.12989 (18)	0.3393 (2)	0.4053 (3)	0.0517 (7)
H2'	0.1639	0.2998	0.4623	0.062*
C3'	0.0518 (2)	0.3467 (3)	0.4467 (3)	0.0634 (9)
H3'	0.0335	0.3115	0.5307	0.076*
C4'	0.00155 (18)	0.4058 (3)	0.3643 (4)	0.0651 (9)
H4'	−0.0505	0.4115	0.3936	0.078*
C5'	0.02778 (17)	0.4563 (2)	0.2394 (4)	0.0613 (8)
H5'	−0.0066	0.4958	0.1831	0.074*
C6'	0.10527 (16)	0.4491 (2)	0.1961 (3)	0.0518 (7)
H6'	0.1227	0.4836	0.1107	0.062*
O1"	0.43245 (11)	0.67654 (16)	−0.0081 (2)	0.0583 (6)
C2"	0.51443 (16)	0.6551 (2)	−0.0456 (3)	0.0512 (7)
C3"	0.52184 (19)	0.5511 (3)	−0.1026 (4)	0.0659 (9)
H3"	0.5624	0.5355	−0.1689	0.079*
C4"	0.47252 (17)	0.4806 (3)	−0.0619 (3)	0.0590 (8)
H4"	0.4802	0.4152	−0.0938	0.071*
C5"	0.5349 (2)	0.7323 (4)	−0.1653 (5)	0.0883 (13)
H51"	0.5019	0.7234	−0.2533	0.132*
H53"	0.5887	0.7246	−0.1941	0.132*
H52"	0.5271	0.7979	−0.1242	0.132*
C6"	0.56228 (19)	0.6696 (3)	0.0983 (4)	0.0650 (9)
H61"	0.5531	0.7352	0.1383	0.098*
H62"	0.6169	0.6621	0.0754	0.098*
H63"	0.5473	0.6207	0.1726	0.098*
O1"'	0.25223 (16)	0.75871 (17)	0.2771 (3)	0.0754 (7)
C1"'	0.30374 (18)	0.7407 (2)	0.1820 (4)	0.0534 (7)
C2"'	0.3419 (2)	0.8263 (2)	0.1013 (5)	0.0707 (9)
H21	0.3395	0.8142	−0.0078	0.085*
H22	0.3968	0.8285	0.1306	0.085*
C3"'	0.3056 (3)	0.9268 (3)	0.1337 (8)	0.1047 (16)
H31	0.2988	0.9338	0.2430	0.126*
H32	0.3413	0.9786	0.1007	0.126*
C4"'	0.2279 (3)	0.9421 (4)	0.0562 (8)	0.131 (2)
H41	0.2350	0.9428	−0.0524	0.197*
H42	0.2059	1.0045	0.0882	0.197*
H43	0.1931	0.8889	0.0832	0.197*

	U11	U22	U33	U12	U13	U23
O1	0.0436 (10)	0.0447 (11)	0.0734 (13)	−0.0010 (8)	0.0108 (9)	−0.0126 (9)
C2	0.0485 (16)	0.0413 (17)	0.086 (2)	−0.0067 (13)	0.0061 (16)	−0.0075 (15)
C3	0.0431 (15)	0.0435 (15)	0.0716 (19)	−0.0084 (12)	0.0022 (13)	0.0007 (14)
C4	0.0370 (13)	0.0426 (14)	0.0456 (15)	−0.0053 (11)	−0.0006 (11)	0.0026 (11)
C4A	0.0330 (13)	0.0428 (14)	0.0386 (13)	−0.0045 (11)	−0.0004 (10)	−0.0006 (11)
C5	0.0347 (12)	0.0447 (15)	0.0410 (13)	−0.0012 (11)	−0.0023 (10)	−0.0002 (12)
C6	0.0329 (12)	0.0441 (15)	0.0482 (14)	−0.0034 (11)	−0.0063 (10)	0.0018 (11)
C7	0.0322 (12)	0.0518 (16)	0.0450 (14)	−0.0107 (11)	−0.0031 (10)	0.0063 (12)
C8	0.0368 (12)	0.0485 (15)	0.0426 (13)	−0.0060 (11)	0.0001 (10)	−0.0046 (12)
C8A	0.0357 (14)	0.0437 (15)	0.0444 (14)	−0.0024 (11)	0.0000 (11)	−0.0062 (11)
O2	0.0718 (15)	0.0470 (14)	0.141 (2)	0.0045 (12)	0.0231 (15)	−0.0142 (15)
O3	0.0476 (11)	0.0509 (12)	0.0652 (13)	−0.0020 (9)	0.0161 (9)	−0.0061 (10)
C1'	0.0368 (13)	0.0457 (15)	0.0445 (13)	−0.0097 (11)	0.0020 (10)	−0.0001 (12)
C2'	0.0556 (17)	0.0551 (18)	0.0443 (15)	−0.0095 (14)	−0.0012 (12)	0.0048 (13)
C3'	0.0620 (19)	0.082 (2)	0.0466 (17)	−0.0215 (17)	0.0152 (14)	0.0053 (16)
C4'	0.0436 (16)	0.083 (2)	0.069 (2)	−0.0096 (15)	0.0154 (14)	−0.0080 (18)
C5'	0.0419 (15)	0.071 (2)	0.071 (2)	0.0020 (14)	−0.0005 (14)	0.0055 (16)
C6'	0.0408 (14)	0.0583 (18)	0.0564 (16)	−0.0082 (12)	0.0040 (11)	0.0115 (13)
O1"	0.0438 (11)	0.0547 (13)	0.0765 (14)	−0.0081 (9)	0.0076 (10)	0.0172 (10)
C2"	0.0376 (14)	0.0625 (18)	0.0537 (17)	−0.0125 (12)	0.0047 (11)	0.0103 (14)
C3"	0.0513 (17)	0.086 (3)	0.0604 (18)	−0.0193 (16)	0.0220 (14)	−0.0193 (17)
C4"	0.0473 (16)	0.066 (2)	0.0637 (19)	−0.0107 (15)	0.0178 (13)	−0.0189 (16)
C5"	0.059 (2)	0.117 (3)	0.089 (3)	−0.016 (2)	0.0098 (18)	0.045 (2)
C6"	0.0623 (19)	0.066 (2)	0.067 (2)	−0.0040 (15)	−0.0097 (15)	−0.0067 (16)
O1"'	0.0721 (15)	0.0505 (13)	0.1036 (19)	0.0059 (11)	0.0179 (14)	−0.0090 (12)
C1"'	0.0393 (14)	0.0468 (16)	0.0739 (19)	−0.0003 (12)	−0.0069 (14)	0.0006 (15)
C2"'	0.0588 (19)	0.0437 (18)	0.110 (3)	−0.0058 (14)	−0.0009 (18)	0.0087 (18)
C3"'	0.089 (3)	0.047 (2)	0.178 (5)	0.001 (2)	0.006 (3)	0.011 (3)
C4"'	0.107 (4)	0.086 (4)	0.200 (6)	0.037 (3)	−0.002 (4)	0.023 (4)

O1—C8A	1.372 (3)	C5'—C6'	1.382 (4)
O1—C2	1.389 (4)	C5'—H5'	0.9300
C2—O2	1.198 (4)	C6'—H6'	0.9300
C2—C3	1.433 (4)	O1"—C2"	1.468 (3)
C3—C4	1.347 (4)	C2"—C3"	1.488 (5)
C3—H3	0.9300	C2"—C6"	1.510 (4)
C4—C4A	1.458 (3)	C2"—C5"	1.516 (5)
C4—C1'	1.483 (4)	C3"—C4"	1.317 (4)
C4A—C8A	1.397 (3)	C3"—H3"	0.9300
C4A—C5	1.406 (3)	C4"—H4"	0.9300
C5—O3	1.329 (3)	C5"—H51"	0.9600
C5—C6	1.421 (4)	C5"—H53"	0.9600
C6—C7	1.418 (4)	C5"—H52"	0.9600
C6—C1"'	1.476 (4)	C6"—H61"	0.9600
C7—O1"	1.353 (3)	C6"—H62"	0.9600
C7—C8	1.385 (4)	C6"—H63"	0.9600
C8—C8A	1.388 (4)	O1"'—C1"'	1.239 (4)
C8—C4"	1.457 (4)	C1"'—C2"'	1.500 (5)
O3—H3O	0.8200	C2"'—C3"'	1.511 (6)
C1'—C2'	1.385 (4)	C2"'—H21	0.9700
C1'—C6'	1.389 (4)	C2"'—H22	0.9700
C2'—C3'	1.387 (4)	C3"'—C4"'	1.501 (7)
C2'—H2'	0.9300	C3"'—H31	0.9700
C3'—C4'	1.371 (5)	C3"'—H32	0.9700
C3'—H3'	0.9300	C4"'—H41	0.9600
C4'—C5'	1.365 (4)	C4"'—H42	0.9600
C4'—H4'	0.9300	C4"'—H43	0.9600
C8A—O1—C2	122.1 (2)	C7—O1"—C2"	119.6 (2)
O2—C2—O1	116.5 (3)	O1"—C2"—C3"	110.0 (2)
O2—C2—C3	127.9 (3)	O1"—C2"—C6"	107.5 (2)
O1—C2—C3	115.6 (3)	C3"—C2"—C6"	110.7 (3)
C4—C3—C2	124.1 (3)	O1"—C2"—C5"	104.2 (3)
C4—C3—H3	118.0	C3"—C2"—C5"	112.8 (3)
C2—C3—H3	118.0	C6"—C2"—C5"	111.3 (3)
C3—C4—C4A	118.2 (2)	C4"—C3"—C2"	121.8 (3)
C3—C4—C1'	118.3 (2)	C4"—C3"—H3"	119.1
C4A—C4—C1'	123.2 (2)	C2"—C3"—H3"	119.1
C8A—C4A—C5	117.0 (2)	C3"—C4"—C8	119.4 (3)
C8A—C4A—C4	117.5 (2)	C3"—C4"—H4"	120.3
C5—C4A—C4	125.5 (2)	C8—C4"—H4"	120.3
O3—C5—C4A	117.2 (2)	C2"—C5"—H51"	109.5
O3—C5—C6	121.0 (2)	C2"—C5"—H53"	109.5
C4A—C5—C6	121.7 (2)	H51"—C5"—H53"	109.5
C7—C6—C5	117.0 (2)	C2"—C5"—H52"	109.5
C7—C6—C1"'	124.6 (3)	H51"—C5"—H52"	109.5
C5—C6—C1"'	118.4 (3)	H53"—C5"—H52"	109.5
O1"—C7—C8	119.3 (2)	C2"—C6"—H61"	109.5
O1"—C7—C6	118.2 (2)	C2"—C6"—H62"	109.5
C8—C7—C6	122.5 (2)	H61"—C6"—H62"	109.5
C7—C8—C8A	117.7 (2)	C2"—C6"—H63"	109.5
C7—C8—C4"	119.1 (3)	H61"—C6"—H63"	109.5
C8A—C8—C4"	123.1 (3)	H62"—C6"—H63"	109.5
O1—C8A—C8	114.8 (2)	O1"'—C1"'—C6	119.0 (3)
O1—C8A—C4A	121.5 (2)	O1"'—C1"'—C2"'	118.7 (3)
C8—C8A—C4A	123.7 (2)	C6—C1"'—C2"'	122.3 (3)
C5—O3—H3O	109.5	C1"'—C2"'—C3"'	114.5 (3)
C2'—C1'—C6'	118.6 (2)	C1"'—C2"'—H21	108.6
C2'—C1'—C4	120.8 (3)	C3"'—C2"'—H21	108.6
C6'—C1'—C4	120.3 (2)	C1"'—C2"'—H22	108.6
C1'—C2'—C3'	120.2 (3)	C3"'—C2"'—H22	108.6
C1'—C2'—H2'	119.9	H21—C2"'—H22	107.6
C3'—C2'—H2'	119.9	C4"'—C3"'—C2"'	113.6 (4)
C4'—C3'—C2'	120.2 (3)	C4"'—C3"'—H31	108.9
C4'—C3'—H3'	119.9	C2"'—C3"'—H31	108.9
C2'—C3'—H3'	119.9	C4"'—C3"'—H32	108.9
C5'—C4'—C3'	120.1 (3)	C2"'—C3"'—H32	108.9
C5'—C4'—H4'	119.9	H31—C3"'—H32	107.7
C3'—C4'—H4'	119.9	C3"'—C4"'—H41	109.5
C4'—C5'—C6'	120.3 (3)	C3"'—C4"'—H42	109.5
C4'—C5'—H5'	119.9	H41—C4"'—H42	109.5
C6'—C5'—H5'	119.9	C3"'—C4"'—H43	109.5
C5'—C6'—C1'	120.5 (3)	H41—C4"'—H43	109.5
C5'—C6'—H6'	119.8	H42—C4"'—H43	109.5
C1'—C6'—H6'	119.8
C8A—O1—C2—O2	−172.2 (3)	C4—C4A—C8A—O1	−6.5 (3)
C8A—O1—C2—C3	9.4 (4)	C5—C4A—C8A—C8	−6.3 (3)
O2—C2—C3—C4	175.7 (4)	C4—C4A—C8A—C8	174.1 (2)
O1—C2—C3—C4	−6.1 (5)	C3—C4—C1'—C2'	50.3 (4)
C2—C3—C4—C4A	−3.2 (4)	C4A—C4—C1'—C2'	−136.1 (3)
C2—C3—C4—C1'	170.7 (3)	C3—C4—C1'—C6'	−124.1 (3)
C3—C4—C4A—C8A	9.5 (3)	C4A—C4—C1'—C6'	49.6 (4)
C1'—C4—C4A—C8A	−164.1 (2)	C6'—C1'—C2'—C3'	0.0 (4)
C3—C4—C4A—C5	−170.0 (2)	C4—C1'—C2'—C3'	−174.5 (3)
C1'—C4—C4A—C5	16.3 (4)	C1'—C2'—C3'—C4'	−0.8 (5)
C8A—C4A—C5—O3	−169.6 (2)	C2'—C3'—C4'—C5'	1.1 (5)
C4—C4A—C5—O3	9.9 (3)	C3'—C4'—C5'—C6'	−0.7 (5)
C8A—C4A—C5—C6	8.1 (3)	C4'—C5'—C6'—C1'	−0.2 (5)
C4—C4A—C5—C6	−172.4 (2)	C2'—C1'—C6'—C5'	0.5 (4)
O3—C5—C6—C7	173.0 (2)	C4—C1'—C6'—C5'	175.0 (3)
C4A—C5—C6—C7	−4.6 (3)	C8—C7—O1"—C2"	−27.2 (3)
O3—C5—C6—C1"'	−6.8 (3)	C6—C7—O1"—C2"	153.9 (2)
C4A—C5—C6—C1"'	175.5 (2)	C7—O1"—C2"—C3"	38.7 (3)
C5—C6—C7—O1"	177.9 (2)	C7—O1"—C2"—C6"	−81.9 (3)
C1"'—C6—C7—O1"	−2.3 (4)	C7—O1"—C2"—C5"	159.9 (3)
C5—C6—C7—C8	−1.1 (3)	O1"—C2"—C3"—C4"	−27.0 (4)
C1"'—C6—C7—C8	178.8 (2)	C6"—C2"—C3"—C4"	91.7 (4)
O1"—C7—C8—C8A	−176.1 (2)	C5"—C2"—C3"—C4"	−142.8 (3)
C6—C7—C8—C8A	2.9 (4)	C2"—C3"—C4"—C8	4.1 (5)
O1"—C7—C8—C4"	0.9 (4)	C7—C8—C4"—C3"	10.7 (4)
C6—C7—C8—C4"	179.8 (2)	C8A—C8—C4"—C3"	−172.5 (3)
C2—O1—C8A—C8	176.2 (3)	C7—C6—C1"'—O1"'	−171.8 (3)
C2—O1—C8A—C4A	−3.2 (4)	C5—C6—C1"'—O1"'	8.1 (4)
C7—C8—C8A—O1	−178.4 (2)	C7—C6—C1"'—C2"'	9.6 (4)
C4"—C8—C8A—O1	4.7 (3)	C5—C6—C1"'—C2"'	−170.5 (3)
C7—C8—C8A—C4A	0.9 (4)	O1"'—C1"'—C2"'—C3"'	−6.7 (5)
C4"—C8—C8A—C4A	−175.9 (2)	C6—C1"'—C2"'—C3"'	171.9 (3)
C5—C4A—C8A—O1	173.1 (2)	C1"'—C2"'—C3"'—C4"'	−73.8 (6)

Cg1 is the centroid of the C1'–C6'ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1"'	0.82	1.73	2.464 (3)	149.
C3"'—H32···O2i	0.97	2.71	3.522 (5)	142.
C4'—H4'···O2ii	0.93	2.70	3.396 (4)	132.
C6"—H61"···Cg1iii	0.96	2.75	3.646 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1′–C6′ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O1"′	0.82	1.73	2.464 (3)	149
C3"′—H32⋯O2i	0.97	2.71	3.522 (5)	142
C4′—H4′⋯O2ii	0.93	2.70	3.396 (4)	132
C6"—H61"⋯Cg1iii	0.96	2.75	3.646 (4)	156

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