Pallidol hexa-acetate ethyl acetate monosolvate.

The entire mol-ecule of pallidol hexa-acetate {systematic name: (±)-(4bR,5R,9bR,10R)-5,10-bis-[4-(acet-yloxy)phen-yl]-4b,5,9b,10-tetra-hydro-indeno-[2,1-a]indene-1,3,6,8-tetrayl tetra-acetate} is completed by the application of twofold rotational symmetry in the title ethyl acetate solvate, C40H34O12·C4H8O2. The ethyl acetate mol-ecule was highly disordered and was treated with the SQUEEZE routine [Spek (2009 ▶). Acta Cryst. D65, 148-155]; the crystallographic data take into account the presence of the solvent. In pallidol hexa-acetate, the dihedral angle between the fused five-membered rings (r.m.s. deviation = 0.100 Å) is 54.73 (6)°, indicating a significant fold in the mol-ecule. Significant twists between residues are also evident as seen in the dihedral angle of 80.70 (5)° between the five-membered ring and the pendent benzene ring to which it is attached. Similarly, the acetate residues are twisted with respect to the benzene ring to which they are attached [C-O(carb-oxy)-C-C torsion angles = -70.24 (14), -114.43 (10) and -72.54 (13)°]. In the crystal, a three-dimensional architecture is sustained by C-H⋯O inter-actions which encompass channels in which the disordered ethyl acetate mol-ecules reside.

Related literature

For synthetic protocols, see: Takaya et al. (2005 ▶); Moss et al. (2013 ▶). For the spectroscopic characteristics of pallidol hexa­acetate, see: Khan et al. (1986 ▶).

Experimental

Crystal data

C40H34O12·C4H8O2

M = 794.78

Monoclinic,

a = 13.1495 (1) Å

b = 12.7439 (1) Å

c = 24.0386 (2) Å

β = 97.186 (1)°

V = 3996.65 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.83 mm−1

T = 100 K

0.30 × 0.10 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.790, T max = 0.922

27173 measured reflections

4029 independent reflections

3714 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.02

4029 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301708X/su2614sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301708X/su2614Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301708X/su2614Isup3.cml

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

C40H34O12·C4H8O2	F(000) = 1672
Mr = 794.78	Dx = 1.321 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 19786 reflections
a = 13.1495 (1) Å	θ = 3.7–74.3°
b = 12.7439 (1) Å	µ = 0.83 mm−1
c = 24.0386 (2) Å	T = 100 K
β = 97.186 (1)°	Prism, colourless
V = 3996.65 (5) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4029 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3714 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 3.7°
ω scan	h = −16→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = 0→15
Tmin = 0.790, Tmax = 0.922	l = 0→29
27173 measured 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0505P)2 + 2.699P] where P = (Fo2 + 2Fc2)/3
4029 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.22 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.

	x	y	z	Uiso*/Ueq
O1	0.23221 (6)	0.46511 (7)	0.48061 (3)	0.0295 (2)
O2	0.35408 (8)	0.41673 (8)	0.54965 (4)	0.0408 (2)
O3	0.56127 (6)	0.19610 (6)	0.42147 (3)	0.02298 (17)
O4	0.63350 (6)	0.31813 (7)	0.48240 (3)	0.02886 (19)
O5	0.88454 (6)	0.23900 (7)	0.35088 (3)	0.02608 (19)
O6	0.86993 (7)	0.10847 (7)	0.28727 (4)	0.0331 (2)
C1	0.20807 (11)	0.51331 (11)	0.57260 (5)	0.0374 (3)
H1A	0.2441	0.5165	0.6108	0.056*
H1B	0.1442	0.4737	0.5727	0.056*
H1C	0.1924	0.5846	0.5589	0.056*
C2	0.27454 (9)	0.46003 (9)	0.53515 (5)	0.0287 (3)
C3	0.28958 (8)	0.41950 (9)	0.44109 (4)	0.0244 (2)
C4	0.37948 (8)	0.46632 (9)	0.42947 (4)	0.0238 (2)
H4	0.4048	0.5278	0.4489	0.029*
C5	0.43189 (8)	0.42139 (8)	0.38878 (4)	0.0215 (2)
H5	0.4939	0.4526	0.3805	0.026*
C6	0.39535 (8)	0.33136 (8)	0.35982 (4)	0.0194 (2)
C7	0.30498 (8)	0.28622 (9)	0.37288 (4)	0.0238 (2)
H7	0.2793	0.2248	0.3536	0.029*
C8	0.25172 (8)	0.32971 (10)	0.41377 (5)	0.0270 (2)
H8	0.1904	0.2982	0.4227	0.032*
C9	0.45295 (8)	0.28440 (8)	0.31499 (4)	0.0184 (2)
H9	0.4240	0.2132	0.3052	0.022*
C10	0.44581 (7)	0.35182 (8)	0.25998 (4)	0.0185 (2)
H10	0.4247	0.4252	0.2678	0.022*
C11	0.56755 (8)	0.27379 (8)	0.33139 (4)	0.0188 (2)
C12	0.62362 (8)	0.30738 (8)	0.28902 (4)	0.0191 (2)
C13	0.72954 (8)	0.29618 (8)	0.29446 (4)	0.0218 (2)
H13	0.7679	0.3192	0.2658	0.026*
C14	0.77742 (8)	0.25032 (9)	0.34309 (4)	0.0220 (2)
C15	0.72490 (8)	0.21823 (8)	0.38658 (4)	0.0218 (2)
H15	0.7599	0.1880	0.4197	0.026*
C16	0.61939 (8)	0.23177 (8)	0.38003 (4)	0.0207 (2)
C17	0.57259 (8)	0.24896 (9)	0.47149 (4)	0.0229 (2)
C18	0.49717 (9)	0.20992 (11)	0.50834 (5)	0.0318 (3)
H18A	0.5242	0.2217	0.5477	0.048*
H18B	0.4856	0.1347	0.5019	0.048*
H18C	0.4322	0.2477	0.4996	0.048*
C19	0.92348 (9)	0.16363 (9)	0.31875 (4)	0.0255 (2)
C20	1.03744 (9)	0.16233 (11)	0.32956 (5)	0.0334 (3)
H20A	1.0641	0.1074	0.3068	0.050*
H20B	1.0589	0.1480	0.3694	0.050*
H20C	1.0643	0.2306	0.3197	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0263 (4)	0.0399 (5)	0.0223 (4)	0.0058 (3)	0.0037 (3)	−0.0057 (3)
O2	0.0498 (6)	0.0482 (6)	0.0237 (4)	0.0166 (5)	0.0015 (4)	0.0032 (4)
O3	0.0252 (4)	0.0263 (4)	0.0168 (3)	−0.0011 (3)	0.0004 (3)	0.0028 (3)
O4	0.0302 (4)	0.0337 (4)	0.0223 (4)	−0.0028 (3)	0.0017 (3)	−0.0036 (3)
O5	0.0180 (4)	0.0374 (5)	0.0217 (4)	0.0034 (3)	−0.0021 (3)	−0.0062 (3)
O6	0.0350 (5)	0.0312 (4)	0.0323 (4)	0.0066 (4)	0.0001 (3)	−0.0058 (4)
C1	0.0450 (7)	0.0404 (7)	0.0289 (6)	−0.0006 (6)	0.0127 (5)	−0.0086 (5)
C2	0.0362 (6)	0.0282 (6)	0.0221 (5)	−0.0005 (5)	0.0055 (5)	−0.0006 (4)
C3	0.0235 (5)	0.0311 (6)	0.0185 (5)	0.0061 (4)	0.0020 (4)	−0.0013 (4)
C4	0.0260 (5)	0.0242 (5)	0.0201 (5)	0.0012 (4)	−0.0013 (4)	−0.0026 (4)
C5	0.0219 (5)	0.0220 (5)	0.0202 (5)	−0.0012 (4)	0.0013 (4)	0.0008 (4)
C6	0.0195 (5)	0.0219 (5)	0.0159 (5)	0.0017 (4)	−0.0015 (4)	0.0018 (4)
C7	0.0221 (5)	0.0264 (5)	0.0222 (5)	−0.0031 (4)	−0.0004 (4)	−0.0031 (4)
C8	0.0203 (5)	0.0359 (6)	0.0247 (5)	−0.0022 (4)	0.0025 (4)	−0.0012 (5)
C9	0.0205 (5)	0.0173 (5)	0.0167 (5)	−0.0008 (4)	−0.0009 (4)	0.0004 (4)
C10	0.0205 (5)	0.0172 (5)	0.0172 (5)	0.0009 (4)	0.0003 (4)	0.0005 (4)
C11	0.0206 (5)	0.0165 (5)	0.0186 (5)	0.0005 (4)	0.0002 (4)	−0.0015 (4)
C12	0.0215 (5)	0.0182 (5)	0.0167 (5)	−0.0010 (4)	−0.0011 (4)	−0.0023 (4)
C13	0.0223 (5)	0.0251 (5)	0.0179 (5)	−0.0013 (4)	0.0017 (4)	−0.0034 (4)
C14	0.0179 (5)	0.0260 (5)	0.0209 (5)	0.0014 (4)	−0.0023 (4)	−0.0058 (4)
C15	0.0242 (5)	0.0227 (5)	0.0172 (5)	0.0032 (4)	−0.0025 (4)	−0.0024 (4)
C16	0.0241 (5)	0.0202 (5)	0.0172 (5)	0.0003 (4)	0.0012 (4)	−0.0005 (4)
C17	0.0240 (5)	0.0270 (5)	0.0166 (5)	0.0054 (4)	−0.0014 (4)	0.0028 (4)
C18	0.0305 (6)	0.0432 (7)	0.0220 (5)	0.0002 (5)	0.0043 (4)	0.0066 (5)
C19	0.0282 (6)	0.0289 (6)	0.0193 (5)	0.0082 (4)	0.0026 (4)	0.0045 (4)
C20	0.0254 (6)	0.0429 (7)	0.0321 (6)	0.0093 (5)	0.0044 (5)	0.0073 (5)

O1—C2	1.3603 (14)	C9—C11	1.5152 (14)
O1—C3	1.4103 (13)	C9—C10	1.5697 (13)
O2—C2	1.1953 (15)	C9—H9	1.0000
O3—C17	1.3700 (13)	C10—C12i	1.5076 (14)
O3—C16	1.4049 (13)	C10—C10i	1.560 (2)
O4—C17	1.1978 (14)	C10—H10	1.0000
O5—C19	1.3712 (13)	C11—C16	1.3854 (14)
O5—C14	1.4050 (13)	C11—C12	1.3972 (14)
O6—C19	1.1955 (14)	C12—C13	1.3900 (15)
C1—C2	1.4941 (16)	C12—C10i	1.5076 (13)
C1—H1A	0.9800	C13—C14	1.3857 (15)
C1—H1B	0.9800	C13—H13	0.9500
C1—H1C	0.9800	C14—C15	1.3849 (15)
C3—C8	1.3807 (16)	C15—C16	1.3873 (15)
C3—C4	1.3835 (16)	C15—H15	0.9500
C4—C5	1.3886 (15)	C17—C18	1.4951 (15)
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.3957 (15)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.3910 (15)	C19—C20	1.4886 (16)
C6—C9	1.5158 (14)	C20—H20A	0.9800
C7—C8	1.3915 (15)	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
C8—H8	0.9500
C2—O1—C3	116.15 (9)	C12i—C10—H10	110.1
C17—O3—C16	117.01 (8)	C10i—C10—H10	110.1
C19—O5—C14	115.82 (8)	C9—C10—H10	110.1
C2—C1—H1A	109.5	C16—C11—C12	119.00 (9)
C2—C1—H1B	109.5	C16—C11—C9	128.50 (9)
H1A—C1—H1B	109.5	C12—C11—C9	112.41 (9)
C2—C1—H1C	109.5	C13—C12—C11	120.93 (9)
H1A—C1—H1C	109.5	C13—C12—C10i	127.87 (9)
H1B—C1—H1C	109.5	C11—C12—C10i	111.20 (9)
O2—C2—O1	122.74 (11)	C14—C13—C12	117.83 (10)
O2—C2—C1	126.19 (11)	C14—C13—H13	121.1
O1—C2—C1	111.06 (10)	C12—C13—H13	121.1
C8—C3—C4	121.86 (10)	C15—C14—C13	122.99 (10)
C8—C3—O1	118.07 (10)	C15—C14—O5	117.09 (9)
C4—C3—O1	120.05 (10)	C13—C14—O5	119.86 (10)
C3—C4—C5	118.44 (10)	C14—C15—C16	117.63 (10)
C3—C4—H4	120.8	C14—C15—H15	121.2
C5—C4—H4	120.8	C16—C15—H15	121.2
C4—C5—C6	121.34 (10)	C11—C16—C15	121.55 (10)
C4—C5—H5	119.3	C11—C16—O3	118.01 (9)
C6—C5—H5	119.3	C15—C16—O3	120.29 (9)
C7—C6—C5	118.55 (10)	O4—C17—O3	123.38 (10)
C7—C6—C9	120.94 (9)	O4—C17—C18	126.17 (10)
C5—C6—C9	120.51 (9)	O3—C17—C18	110.43 (10)
C6—C7—C8	120.95 (10)	C17—C18—H18A	109.5
C6—C7—H7	119.5	C17—C18—H18B	109.5
C8—C7—H7	119.5	H18A—C18—H18B	109.5
C3—C8—C7	118.86 (10)	C17—C18—H18C	109.5
C3—C8—H8	120.6	H18A—C18—H18C	109.5
C7—C8—H8	120.6	H18B—C18—H18C	109.5
C11—C9—C6	114.79 (8)	O6—C19—O5	122.45 (10)
C11—C9—C10	102.76 (8)	O6—C19—C20	127.18 (11)
C6—C9—C10	113.59 (8)	O5—C19—C20	110.37 (10)
C11—C9—H9	108.5	C19—C20—H20A	109.5
C6—C9—H9	108.5	C19—C20—H20B	109.5
C10—C9—H9	108.5	H20A—C20—H20B	109.5
C12i—C10—C10i	104.29 (9)	C19—C20—H20C	109.5
C12i—C10—C9	114.78 (8)	H20A—C20—H20C	109.5
C10i—C10—C9	107.37 (8)	H20B—C20—H20C	109.5
C3—O1—C2—O2	−2.36 (17)	C10—C9—C11—C12	−11.21 (11)
C3—O1—C2—C1	178.50 (10)	C16—C11—C12—C13	1.96 (15)
C2—O1—C3—C8	111.57 (12)	C9—C11—C12—C13	−174.97 (9)
C2—O1—C3—C4	−70.24 (14)	C16—C11—C12—C10i	−179.25 (9)
C8—C3—C4—C5	0.54 (17)	C9—C11—C12—C10i	3.83 (12)
O1—C3—C4—C5	−177.59 (9)	C11—C12—C13—C14	0.27 (15)
C3—C4—C5—C6	0.24 (16)	C10i—C12—C13—C14	−178.31 (10)
C4—C5—C6—C7	−0.59 (15)	C12—C13—C14—C15	−1.81 (16)
C4—C5—C6—C9	179.16 (9)	C12—C13—C14—O5	−178.90 (9)
C5—C6—C7—C8	0.18 (16)	C19—O5—C14—C15	110.20 (11)
C9—C6—C7—C8	−179.57 (9)	C19—O5—C14—C13	−72.54 (13)
C4—C3—C8—C7	−0.94 (17)	C13—C14—C15—C16	1.04 (16)
O1—C3—C8—C7	177.22 (10)	O5—C14—C15—C16	178.20 (9)
C6—C7—C8—C3	0.57 (17)	C12—C11—C16—C15	−2.79 (15)
C7—C6—C9—C11	−133.77 (10)	C9—C11—C16—C15	173.58 (10)
C5—C6—C9—C11	46.49 (13)	C12—C11—C16—O3	−178.43 (9)
C7—C6—C9—C10	108.39 (11)	C9—C11—C16—O3	−2.06 (16)
C5—C6—C9—C10	−71.36 (12)	C14—C15—C16—C11	1.32 (16)
C11—C9—C10—C12i	129.45 (9)	C14—C15—C16—O3	176.87 (9)
C6—C9—C10—C12i	−105.94 (10)	C17—O3—C16—C11	−114.43 (10)
C11—C9—C10—C10i	14.02 (9)	C17—O3—C16—C15	69.87 (13)
C6—C9—C10—C10i	138.64 (8)	C16—O3—C17—O4	−5.04 (15)
C6—C9—C11—C16	48.41 (14)	C16—O3—C17—C18	173.34 (9)
C10—C9—C11—C16	172.23 (10)	C14—O5—C19—O6	−2.25 (15)
C6—C9—C11—C12	−135.02 (9)	C14—O5—C19—C20	178.01 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O6ii	1.00	2.51	3.5053 (14)	179
C15—H15···O4iii	0.95	2.59	3.4834 (12)	158
C20—H20A···O6iv	0.98	2.52	3.2708 (15)	133
C20—H20B···O2iii	0.98	2.28	3.2318 (16)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O6i	1.00	2.51	3.5053 (14)	179
C15—H15⋯O4ii	0.95	2.59	3.4834 (12)	158
C20—H20A⋯O6iii	0.98	2.52	3.2708 (15)	133
C20—H20B⋯O2ii	0.98	2.28	3.2318 (16)	162

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