(±)-4,12,15,18,26-Penta-hydroxy-13,17-dioxahepta-cyclo-[14.10.0.0(3,14).0(4,12).0(6,11).0(18,26).0(19,24)]hexa-cosa-1,3(14),6(11),7,9,15,19,21,23-nona-ene-5,25-dione methanol disolvate.

The title compound, C24H14O9·2CH3OH, displays a chair-shaped form. The two di-hydro-indenone ring systems are located above and below the central fused-ring system, the dihedral angles between the mean planes of di-hydro-indenone ring systems and the mean plane of central fused-ring system are 67.91 (5) and 73.52 (4)°, respectively. In the crystal, extensive O-H⋯O hydrogen bonds, weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions link the mol-ecules into a three-dimensional supra-molecular architecture.

Related literature

For an isomer of the title compound possessing a cup-shaped form, see: Mahmood et al. (2011 ▶). For a related structure, see: Almog et al. (2009 ▶).

Experimental

Crystal data

C24H14O9·2CH4O

M = 510.44

Triclinic,

a = 8.8243 (13) Å

b = 10.3974 (16) Å

c = 14.348 (2) Å

α = 72.936 (3)°

β = 74.639 (2)°

γ = 75.792 (3)°

V = 1193.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.20 × 0.13 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

13982 measured reflections

5549 independent reflections

3395 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.153

S = 1.01

5549 reflections

345 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (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: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814006643/xu5780sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006643/xu5780Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006643/xu5780Isup3.cml

CCDC reference: 993652

Additional supporting information: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 3

C24H14O9·2CH4O	Z = 2
Mr = 510.44	F(000) = 532
Triclinic, P1	Dx = 1.421 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8243 (13) Å	Cell parameters from 3395 reflections
b = 10.3974 (16) Å	θ = 2.1–28.0°
c = 14.348 (2) Å	µ = 0.11 mm−1
α = 72.936 (3)°	T = 295 K
β = 74.639 (2)°	Block, colorless
γ = 75.792 (3)°	0.20 × 0.13 × 0.08 mm
V = 1193.3 (3) Å3

Bruker SMART CCD area-detector diffractometer	3395 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 28.0°, θmin = 2.1°
Detector resolution: 8.36 pixels mm-1	h = −11→11
phi and ω scans	k = −13→13
13982 measured reflections	l = −18→18
5549 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0681P)2] where P = (Fo2 + 2Fc2)/3
5549 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.30 e Å−3
2 restraints	Δρmin = −0.33 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	0.6380 (3)	0.6944 (2)	0.75601 (17)	0.0271 (5)
C2	0.6617 (3)	0.7483 (2)	0.65384 (17)	0.0251 (5)
C3	0.5721 (3)	0.7275 (2)	0.59507 (16)	0.0242 (5)
C4	0.4448 (3)	0.6583 (2)	0.63721 (16)	0.0253 (5)
H4	0.3822	0.6465	0.5985	0.030*
C5	0.4155 (2)	0.6076 (2)	0.74000 (16)	0.0237 (5)
C6	0.5131 (3)	0.6235 (2)	0.79557 (16)	0.0259 (5)
C7	0.7762 (3)	0.8563 (2)	0.49645 (17)	0.0271 (5)
C8	0.9267 (3)	0.7759 (3)	0.44871 (18)	0.0313 (6)
C9	1.0816 (3)	0.7894 (3)	0.4420 (2)	0.0453 (7)
H9	1.1021	0.8543	0.4676	0.054*
C10	1.2044 (3)	0.7035 (3)	0.3962 (2)	0.0520 (8)
H10	1.3096	0.7102	0.3912	0.062*
C11	1.1739 (3)	0.6066 (3)	0.3571 (2)	0.0492 (8)
H11	1.2589	0.5511	0.3253	0.059*
C12	1.0206 (3)	0.5921 (3)	0.3650 (2)	0.0420 (7)
H12	1.0003	0.5264	0.3401	0.050*
C13	0.8956 (3)	0.6787 (2)	0.41145 (18)	0.0304 (6)
C14	0.7229 (3)	0.6854 (2)	0.42804 (16)	0.0278 (5)
C15	0.6364 (3)	0.7924 (2)	0.48880 (16)	0.0251 (5)
C16	0.3270 (3)	0.5121 (3)	0.91425 (17)	0.0277 (5)
C17	0.1959 (3)	0.6094 (3)	0.96265 (17)	0.0289 (6)
C18	0.1819 (3)	0.6424 (3)	1.05147 (19)	0.0417 (7)
H18	0.2568	0.6003	1.0912	0.050*
C19	0.0530 (4)	0.7400 (3)	1.0794 (2)	0.0501 (8)
H19	0.0401	0.7623	1.1396	0.060*
C20	−0.0564 (3)	0.8047 (3)	1.0201 (2)	0.0512 (8)
H32	−0.1408	0.8712	1.0402	0.061*
C21	−0.0430 (3)	0.7726 (3)	0.9319 (2)	0.0425 (7)
H21	−0.1171	0.8163	0.8918	0.051*
C22	0.0840 (3)	0.6733 (3)	0.90383 (18)	0.0315 (6)
C23	0.1240 (3)	0.6198 (3)	0.81479 (17)	0.0287 (6)
C24	0.2903 (3)	0.5289 (2)	0.80993 (16)	0.0258 (5)
C25	0.7395 (5)	1.0380 (4)	0.2088 (3)	0.0889 (13)
H25A	0.7409	1.0880	0.2551	0.133*
H25B	0.6977	1.0999	0.1534	0.133*
H25C	0.8462	0.9938	0.1854	0.133*
C26	0.6111 (6)	0.1071 (5)	0.8833 (4)	0.1277 (19)
H26A	0.6181	0.1204	0.9453	0.192*
H26B	0.6683	0.1680	0.8290	0.192*
H26C	0.6568	0.0142	0.8803	0.192*
O1	0.72441 (18)	0.7100 (2)	0.81690 (12)	0.0381 (5)
H1O	0.8184	0.7067	0.7882	0.057*
O2	0.77457 (18)	0.82605 (17)	0.60350 (12)	0.0322 (4)
O3	0.76792 (19)	0.99359 (17)	0.45672 (13)	0.0354 (4)
H3O	0.6807	1.0345	0.4802	0.053*
O4	0.6535 (2)	0.62199 (19)	0.39918 (13)	0.0409 (5)
O5	0.51468 (19)	0.88543 (17)	0.44504 (12)	0.0332 (4)
H5O	0.5481	0.9108	0.3848	0.050*
O6	0.47605 (18)	0.56300 (18)	0.89531 (11)	0.0317 (4)
O7	0.3494 (2)	0.37741 (17)	0.96603 (12)	0.0387 (5)
H7O	0.3369	0.3731	1.0255	0.058*
O8	0.0433 (2)	0.6403 (2)	0.75343 (13)	0.0455 (5)
O9	0.2920 (2)	0.40219 (17)	0.79333 (12)	0.0381 (5)
H9O	0.3109	0.4088	0.7332	0.057*
O10	0.6448 (4)	0.9415 (3)	0.25526 (18)	0.1024 (11)
H10O	0.604 (5)	0.909 (4)	0.224 (3)	0.123*
O11	0.4543 (4)	0.1337 (3)	0.8764 (2)	0.0857 (8)
H11O	0.420 (5)	0.2163 (14)	0.873 (3)	0.103*

	U11	U22	U33	U12	U13	U23
C1	0.0177 (12)	0.0415 (15)	0.0265 (13)	−0.0033 (10)	−0.0055 (10)	−0.0161 (11)
C2	0.0164 (11)	0.0343 (14)	0.0257 (13)	−0.0045 (10)	−0.0013 (9)	−0.0121 (11)
C3	0.0193 (11)	0.0301 (13)	0.0236 (12)	−0.0020 (10)	−0.0040 (9)	−0.0094 (10)
C4	0.0207 (12)	0.0355 (14)	0.0236 (12)	−0.0055 (10)	−0.0068 (10)	−0.0109 (10)
C5	0.0160 (11)	0.0313 (13)	0.0249 (12)	−0.0036 (10)	−0.0035 (9)	−0.0098 (10)
C6	0.0189 (12)	0.0376 (14)	0.0189 (12)	−0.0010 (10)	−0.0012 (9)	−0.0096 (10)
C7	0.0257 (13)	0.0330 (14)	0.0245 (13)	−0.0107 (10)	−0.0005 (10)	−0.0097 (11)
C8	0.0279 (13)	0.0345 (14)	0.0280 (13)	−0.0067 (11)	0.0000 (10)	−0.0065 (11)
C9	0.0314 (15)	0.0555 (19)	0.0541 (18)	−0.0093 (13)	−0.0039 (13)	−0.0244 (15)
C10	0.0236 (14)	0.067 (2)	0.063 (2)	−0.0049 (14)	0.0007 (14)	−0.0242 (17)
C11	0.0341 (16)	0.0509 (19)	0.0534 (19)	0.0045 (14)	0.0028 (14)	−0.0195 (15)
C12	0.0406 (17)	0.0414 (16)	0.0436 (16)	−0.0045 (13)	−0.0008 (13)	−0.0193 (13)
C13	0.0289 (14)	0.0326 (14)	0.0276 (13)	−0.0054 (11)	−0.0021 (10)	−0.0080 (11)
C14	0.0338 (14)	0.0323 (14)	0.0171 (12)	−0.0117 (11)	0.0002 (10)	−0.0058 (10)
C15	0.0227 (12)	0.0317 (13)	0.0222 (12)	−0.0052 (10)	−0.0047 (10)	−0.0085 (10)
C16	0.0219 (12)	0.0394 (15)	0.0239 (12)	−0.0086 (10)	−0.0047 (10)	−0.0083 (11)
C17	0.0240 (13)	0.0385 (14)	0.0253 (13)	−0.0118 (11)	0.0016 (10)	−0.0106 (11)
C18	0.0420 (16)	0.0548 (18)	0.0312 (15)	−0.0054 (14)	−0.0071 (12)	−0.0182 (13)
C19	0.0463 (18)	0.071 (2)	0.0414 (17)	−0.0076 (16)	−0.0050 (14)	−0.0331 (16)
C20	0.0318 (16)	0.066 (2)	0.061 (2)	0.0022 (14)	−0.0057 (14)	−0.0372 (17)
C21	0.0236 (14)	0.0600 (19)	0.0489 (17)	−0.0031 (13)	−0.0084 (12)	−0.0240 (15)
C22	0.0191 (12)	0.0465 (16)	0.0329 (14)	−0.0104 (11)	−0.0008 (10)	−0.0160 (12)
C23	0.0168 (12)	0.0465 (16)	0.0245 (13)	−0.0134 (11)	−0.0022 (10)	−0.0069 (11)
C24	0.0243 (12)	0.0344 (14)	0.0209 (12)	−0.0078 (10)	−0.0024 (10)	−0.0100 (10)
C25	0.134 (4)	0.069 (3)	0.058 (2)	−0.043 (3)	0.014 (2)	−0.017 (2)
C26	0.081 (4)	0.129 (4)	0.168 (5)	−0.004 (3)	−0.036 (4)	−0.031 (4)
O1	0.0209 (9)	0.0731 (13)	0.0273 (9)	−0.0157 (9)	−0.0045 (7)	−0.0174 (9)
O2	0.0262 (9)	0.0483 (11)	0.0274 (9)	−0.0165 (8)	−0.0019 (7)	−0.0124 (8)
O3	0.0291 (10)	0.0322 (10)	0.0437 (11)	−0.0098 (8)	−0.0002 (8)	−0.0107 (8)
O4	0.0412 (11)	0.0536 (12)	0.0368 (10)	−0.0186 (9)	0.0001 (8)	−0.0237 (9)
O5	0.0283 (9)	0.0418 (10)	0.0269 (9)	−0.0046 (8)	−0.0067 (7)	−0.0053 (8)
O6	0.0216 (9)	0.0537 (11)	0.0208 (9)	−0.0113 (8)	−0.0050 (7)	−0.0064 (8)
O7	0.0511 (12)	0.0408 (11)	0.0235 (9)	−0.0113 (9)	−0.0083 (8)	−0.0041 (8)
O8	0.0255 (10)	0.0782 (15)	0.0389 (11)	−0.0064 (9)	−0.0104 (8)	−0.0225 (10)
O9	0.0518 (12)	0.0409 (11)	0.0273 (9)	−0.0193 (9)	−0.0059 (8)	−0.0099 (8)
O10	0.159 (3)	0.127 (2)	0.0380 (14)	−0.096 (2)	−0.0015 (16)	−0.0037 (15)
O11	0.083 (2)	0.0627 (17)	0.119 (2)	0.0077 (15)	−0.0398 (17)	−0.0354 (17)

C1—O1	1.367 (3)	C16—C17	1.502 (3)
C1—C6	1.379 (3)	C16—C24	1.566 (3)
C1—C2	1.386 (3)	C17—C18	1.382 (3)
C2—O2	1.356 (3)	C17—C22	1.386 (3)
C2—C3	1.388 (3)	C18—C19	1.384 (4)
C3—C4	1.388 (3)	C18—H18	0.9300
C3—C15	1.492 (3)	C19—C20	1.375 (4)
C4—C5	1.389 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.371 (4)
C5—C6	1.384 (3)	C20—H32	0.9300
C5—C24	1.507 (3)	C21—C22	1.385 (3)
C6—O6	1.369 (3)	C21—H21	0.9300
C7—O3	1.364 (3)	C22—C23	1.466 (3)
C7—O2	1.472 (3)	C23—O8	1.215 (3)
C7—C8	1.497 (3)	C23—C24	1.534 (3)
C7—C15	1.579 (3)	C24—O9	1.402 (3)
C8—C13	1.383 (3)	C25—O10	1.369 (4)
C8—C9	1.384 (3)	C25—H25A	0.9600
C9—C10	1.377 (4)	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600
C10—C11	1.395 (4)	C26—O11	1.367 (5)
C10—H10	0.9300	C26—H26A	0.9600
C11—C12	1.369 (4)	C26—H26B	0.9600
C11—H11	0.9300	C26—H26C	0.9600
C12—C13	1.395 (3)	O1—H1O	0.8200
C12—H12	0.9300	O3—H3O	0.8200
C13—C14	1.467 (3)	O5—H5O	0.8200
C14—O4	1.214 (3)	O7—H7O	0.8194
C14—C15	1.543 (3)	O9—H9O	0.8194
C15—O5	1.405 (3)	O10—H10O	0.820 (10)
C16—O7	1.373 (3)	O11—H11O	0.828 (10)
C16—O6	1.467 (3)
O1—C1—C6	120.2 (2)	C17—C16—C24	105.47 (18)
O1—C1—C2	125.2 (2)	C18—C17—C22	120.5 (2)
C6—C1—C2	114.6 (2)	C18—C17—C16	128.1 (2)
O2—C2—C1	122.4 (2)	C22—C17—C16	111.3 (2)
O2—C2—C3	114.8 (2)	C17—C18—C19	118.0 (3)
C1—C2—C3	122.9 (2)	C17—C18—H18	121.0
C4—C3—C2	121.2 (2)	C19—C18—H18	121.0
C4—C3—C15	130.4 (2)	C20—C19—C18	121.4 (3)
C2—C3—C15	108.38 (19)	C20—C19—H19	119.3
C3—C4—C5	116.7 (2)	C18—C19—H19	119.3
C3—C4—H4	121.6	C21—C20—C19	120.9 (3)
C5—C4—H4	121.6	C21—C20—H32	119.5
C6—C5—C4	120.4 (2)	C19—C20—H32	119.5
C6—C5—C24	108.21 (19)	C20—C21—C22	118.3 (3)
C4—C5—C24	131.3 (2)	C20—C21—H21	120.9
O6—C6—C1	121.4 (2)	C22—C21—H21	120.9
O6—C6—C5	114.6 (2)	C21—C22—C17	121.0 (2)
C1—C6—C5	124.0 (2)	C21—C22—C23	129.0 (2)
O3—C7—O2	109.01 (18)	C17—C22—C23	110.0 (2)
O3—C7—C8	111.65 (19)	O8—C23—C22	127.9 (2)
O2—C7—C8	107.93 (19)	O8—C23—C24	123.6 (2)
O3—C7—C15	116.6 (2)	C22—C23—C24	108.51 (19)
O2—C7—C15	105.89 (17)	O9—C24—C5	115.82 (18)
C8—C7—C15	105.35 (19)	O9—C24—C23	112.00 (18)
C13—C8—C9	121.3 (2)	C5—C24—C23	110.43 (19)
C13—C8—C7	111.8 (2)	O9—C24—C16	111.61 (19)
C9—C8—C7	126.9 (2)	C5—C24—C16	102.36 (17)
C10—C9—C8	117.9 (3)	C23—C24—C16	103.53 (17)
C10—C9—H9	121.1	O10—C25—H25A	109.5
C8—C9—H9	121.1	O10—C25—H25B	109.5
C9—C10—C11	121.2 (3)	H25A—C25—H25B	109.5
C9—C10—H10	119.4	O10—C25—H25C	109.5
C11—C10—H10	119.4	H25A—C25—H25C	109.5
C12—C11—C10	120.9 (3)	H25B—C25—H25C	109.5
C12—C11—H11	119.6	O11—C26—H26A	109.5
C10—C11—H11	119.6	O11—C26—H26B	109.5
C11—C12—C13	118.2 (3)	H26A—C26—H26B	109.5
C11—C12—H12	120.9	O11—C26—H26C	109.5
C13—C12—H12	120.9	H26A—C26—H26C	109.5
C8—C13—C12	120.6 (2)	H26B—C26—H26C	109.5
C8—C13—C14	110.5 (2)	C1—O1—H1O	109.5
C12—C13—C14	128.9 (2)	C2—O2—C7	108.05 (16)
O4—C14—C13	128.1 (2)	C7—O3—H3O	109.5
O4—C14—C15	123.4 (2)	C15—O5—H5O	109.5
C13—C14—C15	108.41 (19)	C6—O6—C16	107.45 (16)
O5—C15—C3	110.68 (19)	C16—O7—H11O	116.6 (9)
O5—C15—C14	111.54 (18)	C16—O7—H7O	109.4
C3—C15—C14	112.18 (19)	H11O—O7—H7O	134.0
O5—C15—C7	115.65 (19)	C24—O9—H11O	120.8 (10)
C3—C15—C7	102.74 (18)	C24—O9—H9O	109.2
C14—C15—C7	103.64 (18)	H11O—O9—H9O	112.8
O7—C16—O6	108.50 (18)	C25—O10—H5O	124.0
O7—C16—C17	117.07 (19)	C25—O10—H10O	123 (3)
O6—C16—C17	107.07 (19)	H5O—O10—H10O	111.0
O7—C16—C24	111.54 (19)	C26—O11—H11O	108 (3)
O6—C16—C24	106.64 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O8i	0.82	1.92	2.702 (2)	160
O3—H3O···O5ii	0.82	1.91	2.725 (2)	171
O5—H5O···O10	0.82	1.80	2.610 (3)	171
O7—H7O···O1iii	0.82	2.14	2.916 (2)	158
O9—H9O···O4iv	0.82	1.95	2.751 (2)	166
O10—H10O···O11iv	0.82 (1)	1.85 (2)	2.650 (4)	163 (5)
O11—H11O···O7	0.83 (1)	2.31 (3)	3.010 (3)	142 (4)
O11—H11O···O9	0.83 (1)	2.15 (3)	2.873 (3)	145 (4)
C18—H18···O6iii	0.93	2.56	3.370 (3)	146
C21—H21···O1v	0.93	2.57	3.231 (3)	129
C11—H11···Cgvi	0.93	2.63	3.501 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O8i	0.82	1.92	2.702 (2)	160
O3—H3O⋯O5ii	0.82	1.91	2.725 (2)	171
O5—H5O⋯O10	0.82	1.80	2.610 (3)	171
O7—H7O⋯O1iii	0.82	2.14	2.916 (2)	158
O9—H9O⋯O4iv	0.82	1.95	2.751 (2)	166
O10—H10O⋯O11iv	0.82 (1)	1.85 (2)	2.650 (4)	163 (5)
O11—H11O⋯O7	0.83 (1)	2.31 (3)	3.010 (3)	142 (4)
O11—H11O⋯O9	0.83 (1)	2.15 (3)	2.873 (3)	145 (4)
C18—H18⋯O6iii	0.93	2.56	3.370 (3)	146
C21—H21⋯O1v	0.93	2.57	3.231 (3)	129
C11—H11⋯Cg vi	0.93	2.63	3.501 (3)	156

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