Tetra­methyl anthracene-2,3,6,7-tetra­carboxyl­ate–tetra­methyl 9,10-dihydro-9,10-dioxoanthracene-2,3,6,7-tetra­carboxyl­ate (1/1)

Drake, B.L.; Morris, J.L.; McLaughlin, M.L.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536812032424

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2540-o2541

https://doi.org/10.1107/S1600536812032424

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Tetramethyl anthracene-2,3,6,7-tetracarboxylate–tetramethyl 9,10-dihydro-9,10-dioxoanthracene-2,3,6,7-tetracarboxylate (1/1)¹

Brenton L. Drake,^a J. Larry Morris,^b Mark L. McLaughlin,^c Frank R. Fronczek ^a ^* and Steven F. Watkins ^a

^aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA, ^bGEO Specialty Chemicals, WTC Process Technology Laboratory, Louisiana Business and Technology Center, 8000 GSRI Avenue, Building 3100, Baton Rouge, LA 70820, USA, and ^cDepartment of Chemistry, 4202 E. Fowler Avenue, CHE 205, University of South Florida, Tampa, Florida 33620, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 11 July 2012; accepted 16 July 2012; online 25 July 2012)

In the title co-crystal, C₂₂H₁₆O₁₀·C₂₂H₁₈O₈, the independent tetramethyl 9,10-dihydro-9,10-dioxoanthracene-2,3,6,7-tetracarboxylate, (I), and tetramethyl anthracene-2,3,6,7-tetracarboxylate, (II), components occupy separate crystallographic inversion centers. In (II), the dihedral angles between the mean aromatic plane and the two independent carboxylate planes are 41.32 (10) and −38.35 (10)°. The methylcarboxylate groups of (I) are disordered, with each resolvable into two groups. In the least disordered carboxylate, the apparent angles between the mean aromatic plane and the two partial carboxylate planes [site occupations = 0.510 (3) and 0.490 (3)] are 16.8 (3) and 23.3 (3)°. In the highly disordered group, the apparent angles between the mean aromatic plane and the two partial carboxylate planes [site occupations = 0.510 (3) and 0.490 (3)] are 78.3 (3) and −74.1 (3)°. In addition, this extreme disorder leads to an artificially elongated C(aromatic)—C(carboxyl) bond.

Related literature

For (I), see: Tarnchompoo et al. (1987 ). For (II), see: Luo & Hart (1988 ); Morris et al. (1994 ); Yanagimoto et al. (2006 ).

Experimental

Crystal data

C₂₂H₁₆O₁₀·C₂₂H₁₈O₈
M_r = 850.71
Triclinic, $[P \overline 1]$
a = 8.2110 (3) Å
b = 9.5965 (3) Å
c = 12.0886 (5) Å
α = 86.281 (2)°
β = 81.514 (2)°
γ = 81.705 (2)°
V = 931.34 (6) Å³
Z = 1
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 90 K
0.40 × 0.24 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.954, T_max = 0.984
12654 measured reflections
7048 independent reflections
4579 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.154
S = 1.03
7048 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812032424/pv2569sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032424/pv2569Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032424/pv2569Isup3.cml

checkCIF report

Comment top

The room temperature crystal structure of anthracene dedrivative (II) was determined by Morris et al. (1994). Along with pure crystals of (II), they obtained the co-crystalled product reported here. It is presumed that the anthraquinone derivative ((I)) was formed as an air oxidation product of (II).

The structure exhibits little aromatic ring stacking, with closest contacts C4···C18(at -x, -y, -z) 3.486 (2) and C2···C16(at -x, -y, -z) 3.575 (2) Å.

Related literature top

For (I), see: Tarnchompoo et al. (1987). For (II), see: Luo & Hart (1988); Morris et al. (1994); Yanagimoto et al. (2006).

Experimental top

The synthesis of (II) was reported by Morris et al. (1994). It is presumed that the anthraquinone derivative ((I)) was formed as an air oxidation product of (II).

Structure description top

The structure exhibits little aromatic ring stacking, with closest contacts C4···C18(at -x, -y, -z) 3.486 (2) and C2···C16(at -x, -y, -z) 3.575 (2) Å.

For (I), see: Tarnchompoo et al. (1987). For (II), see: Luo & Hart (1988); Morris et al. (1994); Yanagimoto et al. (2006).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with the atom numbering scheme showing disorder. Displacement ellipsoids are drawn at the 30% probability level. H atoms were omitted for clarity.
	Fig. 2. The molecular structure of (I) with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms were omitted for clarity.

Tetramethyl anthracene-2,3,6,7-tetracarboxylate– tetramethyl 9,10-dihydro-9,10-dioxoanthracene-2,3,6,7-tetracarboxylate (1/1) top

Crystal data top

C₂₂H₁₆O₁₀·C₂₂H₁₈O₈	Z = 1
M_r = 850.71	F(000) = 442
Triclinic, P1	D_x = 1.517 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2110 (3) Å	Cell parameters from 6290 reflections
b = 9.5965 (3) Å	θ = 2.6–33.1°
c = 12.0886 (5) Å	µ = 0.12 mm⁻¹
α = 86.281 (2)°	T = 90 K
β = 81.514 (2)°	Plate, yellow
γ = 81.705 (2)°	0.40 × 0.24 × 0.14 mm
V = 931.34 (6) Å³

Data collection top

Nonius KappaCCD diffractometer	7048 independent reflections
Radiation source: sealed tube	4579 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.030
Detector resolution: 9 pixels mm^-1	θ_max = 33.1°, θ_min = 2.7°
CCD rotation images, thick slices scans	h = −11→12
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −14→14
T_min = 0.954, T_max = 0.984	l = −18→18
12654 measured reflections

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0865P)²] where P = (F_o² + 2F_c²)/3
7048 reflections	(Δ/σ)_max = 0.001
326 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³
3 constraints

Crystal data top

C₂₂H₁₆O₁₀·C₂₂H₁₈O₈	γ = 81.705 (2)°
M_r = 850.71	V = 931.34 (6) Å³
Triclinic, P1	Z = 1
a = 8.2110 (3) Å	Mo Kα radiation
b = 9.5965 (3) Å	µ = 0.12 mm⁻¹
c = 12.0886 (5) Å	T = 90 K
α = 86.281 (2)°	0.40 × 0.24 × 0.14 mm
β = 81.514 (2)°

Data collection top

Nonius KappaCCD diffractometer	7048 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	4579 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.984	R_int = 0.030
12654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	Δρ_max = 0.45 e Å⁻³
7048 reflections	Δρ_min = −0.30 e Å⁻³
326 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.17551 (13)	−0.04598 (11)	0.45522 (9)	0.0160 (2)
C2	0.03630 (13)	−0.08672 (11)	0.40307 (9)	0.0146 (2)
C3	0.07556 (13)	−0.17164 (11)	0.31043 (9)	0.0165 (2)
H3	0.1885	−0.198	0.28	0.02*
C4	−0.05059 (14)	−0.21760 (12)	0.26265 (10)	0.0185 (2)
C5	−0.21709 (14)	−0.17679 (13)	0.30674 (11)	0.0231 (3)
C6	−0.25640 (14)	−0.08911 (13)	0.39726 (11)	0.0228 (3)
H6	−0.3694	−0.0592	0.4256	0.027*
C7	−0.12956 (13)	−0.04518 (11)	0.44636 (9)	0.0160 (2)
C8	−0.00953 (15)	−0.31246 (14)	0.16572 (11)	0.0256 (3)
O2A	−0.1090 (3)	−0.3944 (3)	0.1466 (2)	0.0274 (4)	0.510 (3)
O2B	−0.1136 (3)	−0.3369 (3)	0.1098 (2)	0.0274 (4)	0.490 (3)
C9	0.20164 (16)	−0.42773 (13)	0.03751 (11)	0.0258 (3)
H9A	0.1959	−0.5242	0.0682	0.039*
H9B	0.316	−0.4188	0.0039	0.039*
H9C	0.1277	−0.4063	−0.0198	0.039*
C10A	−0.3594 (5)	−0.2057 (4)	0.2470 (3)	0.0179 (7)	0.490 (3)
O4A	−0.4377 (3)	−0.1268 (3)	0.18701 (17)	0.0208 (5)	0.490 (3)
O5A	−0.3849 (4)	−0.3372 (3)	0.2787 (3)	0.0264 (5)	0.490 (3)
C11A	−0.4895 (4)	−0.3982 (3)	0.2144 (3)	0.0336 (8)	0.490 (3)
H11A	−0.6012	−0.3958	0.2568	0.05*	0.490 (3)
H11B	−0.4424	−0.496	0.1996	0.05*	0.490 (3)
H11C	−0.496	−0.344	0.1433	0.05*	0.490 (3)
C10B	−0.3558 (5)	−0.2516 (4)	0.2748 (4)	0.0188 (7)	0.510 (3)
O4B	−0.4236 (3)	−0.3413 (3)	0.3294 (2)	0.0263 (5)	0.510 (3)
O5B	−0.3920 (3)	−0.1937 (3)	0.17661 (18)	0.0219 (5)	0.510 (3)
C11B	−0.4997 (3)	−0.2659 (3)	0.1233 (2)	0.0274 (6)	0.510 (3)
H11D	−0.5511	−0.3327	0.1774	0.041*	0.510 (3)
H11E	−0.4345	−0.317	0.0602	0.041*	0.510 (3)
H11F	−0.5866	−0.197	0.0959	0.041*	0.510 (3)
O1	0.31995 (10)	−0.08674 (9)	0.41989 (8)	0.0246 (2)
O3	0.15036 (10)	−0.32984 (9)	0.12660 (7)	0.02195 (19)
C12	−0.16785 (13)	0.04142 (11)	0.04459 (9)	0.0160 (2)
H12	−0.2806	0.0698	0.0743	0.019*
C13	−0.12949 (13)	−0.04723 (11)	−0.04583 (9)	0.0151 (2)
C14	−0.25614 (13)	−0.09921 (12)	−0.09405 (10)	0.0178 (2)
H14	−0.3693	−0.0725	−0.0644	0.021*
C15	−0.21832 (13)	−0.18678 (12)	−0.18222 (9)	0.0163 (2)
C16	−0.04783 (13)	−0.22772 (11)	−0.22822 (9)	0.0147 (2)
C17	0.07649 (13)	−0.17920 (11)	−0.18403 (9)	0.0155 (2)
H17	0.1889	−0.2062	−0.2154	0.019*
C18	0.04030 (13)	−0.08847 (11)	−0.09143 (9)	0.0145 (2)
C19	−0.36209 (14)	−0.23079 (12)	−0.22755 (10)	0.0192 (2)
C20	−0.46657 (16)	−0.28536 (17)	−0.38791 (12)	0.0338 (3)
H20A	−0.4857	−0.3776	−0.3528	0.051*
H20B	−0.4317	−0.2946	−0.4685	0.051*
H20C	−0.5695	−0.2192	−0.3756	0.051*
C21	−0.00127 (13)	−0.33641 (12)	−0.31496 (9)	0.0167 (2)
C22	0.19237 (15)	−0.41180 (12)	−0.47134 (10)	0.0221 (2)
H22A	0.2222	−0.5027	−0.4325	0.033*
H22B	0.2911	−0.3838	−0.5185	0.033*
H22C	0.1069	−0.4203	−0.5183	0.033*
O6	−0.48764 (10)	−0.25750 (10)	−0.16986 (8)	0.0285 (2)
O7	−0.33807 (10)	−0.23321 (10)	−0.33907 (7)	0.0266 (2)
O8	−0.06719 (12)	−0.44073 (9)	−0.31555 (8)	0.0276 (2)
O9	0.12862 (9)	−0.30601 (8)	−0.38957 (7)	0.01791 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0173 (5)	0.0168 (5)	0.0150 (5)	−0.0030 (4)	−0.0027 (4)	−0.0062 (4)
C2	0.0171 (5)	0.0146 (5)	0.0131 (5)	−0.0021 (4)	−0.0038 (4)	−0.0047 (4)
C3	0.0179 (5)	0.0170 (5)	0.0150 (5)	0.0007 (4)	−0.0041 (4)	−0.0058 (4)
C4	0.0210 (5)	0.0191 (5)	0.0164 (5)	−0.0013 (4)	−0.0041 (4)	−0.0086 (4)
C5	0.0193 (5)	0.0290 (6)	0.0238 (6)	−0.0032 (4)	−0.0061 (4)	−0.0145 (5)
C6	0.0173 (5)	0.0296 (6)	0.0235 (6)	−0.0025 (4)	−0.0039 (4)	−0.0153 (5)
C7	0.0178 (5)	0.0155 (5)	0.0157 (5)	−0.0017 (4)	−0.0032 (4)	−0.0069 (4)
C8	0.0228 (6)	0.0311 (6)	0.0244 (6)	0.0008 (5)	−0.0061 (5)	−0.0164 (5)
O2A	0.0273 (6)	0.0296 (11)	0.0287 (12)	−0.0019 (9)	−0.0094 (8)	−0.0177 (7)
O2B	0.0273 (6)	0.0296 (11)	0.0287 (12)	−0.0019 (9)	−0.0094 (8)	−0.0177 (7)
C9	0.0321 (6)	0.0267 (6)	0.0190 (6)	−0.0009 (5)	−0.0019 (5)	−0.0130 (5)
C10A	0.0212 (13)	0.0160 (17)	0.018 (2)	−0.0030 (14)	−0.0031 (13)	−0.0074 (12)
O4A	0.0196 (9)	0.0201 (11)	0.0237 (10)	−0.0005 (8)	−0.0080 (7)	−0.0024 (8)
O5A	0.0400 (15)	0.0175 (10)	0.0285 (14)	−0.0119 (9)	−0.0197 (12)	0.0009 (10)
C11A	0.0434 (17)	0.0230 (13)	0.0428 (18)	−0.0121 (11)	−0.0256 (14)	−0.0032 (12)
C10B	0.0191 (12)	0.022 (2)	0.0170 (18)	−0.0014 (15)	−0.0046 (12)	−0.0077 (13)
O4B	0.0326 (11)	0.0298 (11)	0.0209 (12)	−0.0155 (8)	−0.0054 (10)	−0.0043 (10)
O5B	0.0216 (10)	0.0268 (12)	0.0208 (10)	−0.0071 (9)	−0.0112 (7)	−0.0003 (8)
C11B	0.0249 (12)	0.0382 (14)	0.0236 (13)	−0.0110 (10)	−0.0096 (10)	−0.0052 (10)
O1	0.0178 (4)	0.0311 (5)	0.0257 (5)	−0.0031 (3)	−0.0004 (3)	−0.0152 (4)
O3	0.0260 (4)	0.0240 (4)	0.0168 (4)	−0.0049 (3)	0.0000 (3)	−0.0115 (3)
C12	0.0122 (5)	0.0204 (5)	0.0159 (5)	−0.0019 (4)	−0.0008 (4)	−0.0067 (4)
C13	0.0145 (5)	0.0173 (5)	0.0140 (5)	−0.0025 (4)	−0.0014 (4)	−0.0053 (4)
C14	0.0144 (5)	0.0226 (5)	0.0174 (5)	−0.0038 (4)	−0.0014 (4)	−0.0076 (4)
C15	0.0156 (5)	0.0192 (5)	0.0153 (5)	−0.0047 (4)	−0.0016 (4)	−0.0051 (4)
C16	0.0172 (5)	0.0152 (5)	0.0120 (5)	−0.0029 (4)	−0.0009 (4)	−0.0039 (4)
C17	0.0146 (5)	0.0178 (5)	0.0140 (5)	−0.0019 (4)	−0.0008 (4)	−0.0046 (4)
C18	0.0146 (5)	0.0167 (5)	0.0129 (5)	−0.0028 (4)	−0.0016 (4)	−0.0046 (4)
C19	0.0170 (5)	0.0224 (5)	0.0196 (6)	−0.0032 (4)	−0.0029 (4)	−0.0098 (4)
C20	0.0235 (6)	0.0548 (9)	0.0280 (7)	−0.0077 (6)	−0.0098 (5)	−0.0189 (6)
C21	0.0187 (5)	0.0183 (5)	0.0137 (5)	−0.0024 (4)	−0.0030 (4)	−0.0041 (4)
C22	0.0260 (6)	0.0225 (5)	0.0171 (6)	−0.0007 (4)	0.0006 (4)	−0.0104 (4)
O6	0.0196 (4)	0.0419 (5)	0.0265 (5)	−0.0119 (4)	0.0014 (3)	−0.0144 (4)
O7	0.0222 (4)	0.0437 (5)	0.0180 (4)	−0.0107 (4)	−0.0054 (3)	−0.0107 (4)
O8	0.0393 (5)	0.0219 (4)	0.0228 (5)	−0.0140 (4)	0.0054 (4)	−0.0093 (3)
O9	0.0181 (4)	0.0202 (4)	0.0160 (4)	−0.0039 (3)	0.0007 (3)	−0.0089 (3)

Geometric parameters (Å, º) top

C1—O1	1.2166 (13)	O5B—C11B	1.442 (3)
C1—C2	1.4934 (14)	C11B—H11D	0.98
C1—C7ⁱ	1.4935 (14)	C11B—H11E	0.98
C2—C7	1.3956 (15)	C11B—H11F	0.98
C2—C3	1.3994 (14)	C12—C13	1.3998 (14)
C3—C4	1.3938 (15)	C12—C18ⁱⁱ	1.4021 (14)
C3—H3	0.95	C12—H12	0.95
C4—C5	1.4015 (16)	C13—C14	1.4270 (14)
C4—C8	1.4995 (15)	C13—C18	1.4305 (15)
C5—C6	1.3951 (16)	C14—C15	1.3718 (15)
C5—C10A	1.527 (4)	C14—H14	0.95
C5—C10B	1.537 (4)	C15—C16	1.4364 (15)
C6—C7	1.3987 (15)	C15—C19	1.4957 (15)
C6—H6	0.95	C16—C17	1.3691 (14)
C7—C1ⁱ	1.4935 (14)	C16—C21	1.4974 (14)
C8—O2B	1.221 (3)	C17—C18	1.4329 (14)
C8—O2A	1.267 (3)	C17—H17	0.95
C8—O3	1.3187 (14)	C18—C12ⁱⁱ	1.4021 (14)
C9—O3	1.4501 (13)	C19—O6	1.2064 (14)
C9—H9A	0.98	C19—O7	1.3346 (15)
C9—H9B	0.98	C20—O7	1.4446 (13)
C9—H9C	0.98	C20—H20A	0.98
C10A—O4A	1.199 (4)	C20—H20B	0.98
C10A—O5A	1.331 (4)	C20—H20C	0.98
O5A—C11A	1.444 (3)	C21—O8	1.2056 (13)
C11A—H11A	0.98	C21—O9	1.3445 (13)
C11A—H11B	0.98	C22—O9	1.4512 (13)
C11A—H11C	0.98	C22—H22A	0.98
C10B—O4B	1.201 (4)	C22—H22B	0.98
C10B—O5B	1.333 (4)	C22—H22C	0.98

O1—C1—C2	121.43 (9)	C8—O3—C9	115.83 (9)
O1—C1—C7ⁱ	121.49 (9)	C13—C12—C18ⁱⁱ	120.19 (10)
C2—C1—C7ⁱ	117.08 (9)	C13—C12—H12	119.9
C7—C2—C3	120.05 (9)	C18ⁱⁱ—C12—H12	119.9
C7—C2—C1	121.57 (9)	C12—C13—C14	121.62 (9)
C3—C2—C1	118.37 (9)	C12—C13—C18	119.87 (9)
C4—C3—C2	120.16 (10)	C14—C13—C18	118.51 (9)
C4—C3—H3	119.9	C15—C14—C13	121.55 (10)
C2—C3—H3	119.9	C15—C14—H14	119.2
C3—C4—C5	119.74 (10)	C13—C14—H14	119.2
C3—C4—C8	120.53 (10)	C14—C15—C16	119.90 (9)
C5—C4—C8	119.72 (10)	C14—C15—C19	116.52 (10)
C6—C5—C4	120.10 (10)	C16—C15—C19	123.55 (9)
C6—C5—C10A	117.66 (17)	C17—C16—C15	119.93 (9)
C4—C5—C10A	121.49 (17)	C17—C16—C21	118.53 (9)
C6—C5—C10B	117.84 (17)	C15—C16—C21	121.13 (9)
C4—C5—C10B	120.72 (16)	C16—C17—C18	121.24 (10)
C5—C6—C7	120.05 (10)	C16—C17—H17	119.4
C5—C6—H6	120	C18—C17—H17	119.4
C7—C6—H6	120	C12ⁱⁱ—C18—C13	119.93 (9)
C2—C7—C6	119.86 (10)	C12ⁱⁱ—C18—C17	121.20 (10)
C2—C7—C1ⁱ	121.33 (9)	C13—C18—C17	118.86 (9)
C6—C7—C1ⁱ	118.81 (9)	O6—C19—O7	123.75 (10)
O2B—C8—O3	121.61 (16)	O6—C19—C15	123.71 (11)
O2A—C8—O3	123.52 (14)	O7—C19—C15	112.51 (10)
O2B—C8—C4	122.73 (15)	O7—C20—H20A	109.5
O2A—C8—C4	121.19 (15)	O7—C20—H20B	109.5
O3—C8—C4	112.55 (9)	H20A—C20—H20B	109.5
O3—C9—H9A	109.5	O7—C20—H20C	109.5
O3—C9—H9B	109.5	H20A—C20—H20C	109.5
H9A—C9—H9B	109.5	H20B—C20—H20C	109.5
O3—C9—H9C	109.5	O8—C21—O9	124.17 (10)
H9A—C9—H9C	109.5	O8—C21—C16	124.51 (10)
H9B—C9—H9C	109.5	O9—C21—C16	111.26 (9)
O4A—C10A—O5A	126.1 (4)	O9—C22—H22A	109.5
O4A—C10A—C5	128.3 (3)	O9—C22—H22B	109.5
O5A—C10A—C5	105.6 (3)	H22A—C22—H22B	109.5
C10A—O5A—C11A	115.2 (3)	O9—C22—H22C	109.5
O4B—C10B—O5B	126.2 (3)	H22A—C22—H22C	109.5
O4B—C10B—C5	126.9 (3)	H22B—C22—H22C	109.5
O5B—C10B—C5	106.9 (3)	C19—O7—C20	115.38 (10)
C10B—O5B—C11B	115.1 (2)	C21—O9—C22	115.34 (8)

O1—C1—C2—C7	177.20 (11)	C10A—C5—C10B—O4B	−161.3 (11)
C7ⁱ—C1—C2—C7	−1.92 (18)	C6—C5—C10B—O5B	110.9 (3)
O1—C1—C2—C3	−1.13 (17)	C4—C5—C10B—O5B	−82.3 (3)
C7ⁱ—C1—C2—C3	179.75 (10)	C10A—C5—C10B—O5B	16.0 (6)
C7—C2—C3—C4	−1.43 (17)	O4B—C10B—O5B—C11B	−12.7 (5)
C1—C2—C3—C4	176.91 (10)	C5—C10B—O5B—C11B	169.9 (2)
C2—C3—C4—C5	0.90 (18)	O2B—C8—O3—C9	−23.4 (2)
C2—C3—C4—C8	−178.00 (11)	O2A—C8—O3—C9	14.7 (2)
C3—C4—C5—C6	0.8 (2)	C4—C8—O3—C9	176.06 (10)
C8—C4—C5—C6	179.69 (12)	C18ⁱⁱ—C12—C13—C14	178.77 (11)
C3—C4—C5—C10A	170.7 (2)	C18ⁱⁱ—C12—C13—C18	−0.79 (18)
C8—C4—C5—C10A	−10.4 (3)	C12—C13—C14—C15	−179.59 (11)
C3—C4—C5—C10B	−165.8 (2)	C18—C13—C14—C15	−0.04 (17)
C8—C4—C5—C10B	13.2 (3)	C13—C14—C15—C16	−0.19 (18)
C4—C5—C6—C7	−1.9 (2)	C13—C14—C15—C19	−178.28 (10)
C10A—C5—C6—C7	−172.2 (2)	C14—C15—C16—C17	−0.04 (17)
C10B—C5—C6—C7	165.0 (2)	C19—C15—C16—C17	177.91 (11)
C3—C2—C7—C6	0.28 (17)	C14—C15—C16—C21	172.59 (11)
C1—C2—C7—C6	−178.01 (11)	C19—C15—C16—C21	−9.46 (17)
C3—C2—C7—C1ⁱ	−179.70 (10)	C15—C16—C17—C18	0.50 (17)
C1—C2—C7—C1ⁱ	2.00 (18)	C21—C16—C17—C18	−172.32 (10)
C5—C6—C7—C2	1.40 (19)	C12—C13—C18—C12ⁱⁱ	0.79 (18)
C5—C6—C7—C1ⁱ	−178.62 (12)	C14—C13—C18—C12ⁱⁱ	−178.78 (10)
C3—C4—C8—O2B	−167.8 (2)	C12—C13—C18—C17	−179.96 (10)
C5—C4—C8—O2B	13.3 (3)	C14—C13—C18—C17	0.48 (16)
C3—C4—C8—O2A	154.37 (19)	C16—C17—C18—C12ⁱⁱ	178.53 (11)
C5—C4—C8—O2A	−24.5 (2)	C16—C17—C18—C13	−0.72 (17)
C3—C4—C8—O3	−7.51 (18)	C14—C15—C19—O6	−37.99 (17)
C5—C4—C8—O3	173.58 (12)	C16—C15—C19—O6	143.99 (13)
C6—C5—C10A—O4A	71.8 (4)	C14—C15—C19—O7	140.16 (11)
C4—C5—C10A—O4A	−98.4 (4)	C16—C15—C19—O7	−37.85 (16)
C10B—C5—C10A—O4A	167.6 (11)	C17—C16—C21—O8	134.54 (13)
C6—C5—C10A—O5A	−105.8 (3)	C15—C16—C21—O8	−38.19 (17)
C4—C5—C10A—O5A	84.1 (3)	C17—C16—C21—O9	−42.72 (14)
C10B—C5—C10A—O5A	−9.9 (6)	C15—C16—C21—O9	144.55 (11)
O4A—C10A—O5A—C11A	15.1 (6)	O6—C19—O7—C20	−6.45 (18)
C5—C10A—O5A—C11A	−167.3 (3)	C15—C19—O7—C20	175.39 (10)
C6—C5—C10B—O4B	−66.5 (4)	O8—C21—O9—C22	−2.47 (17)
C4—C5—C10B—O4B	100.4 (4)	C16—C21—O9—C22	174.80 (9)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆O₁₀·C₂₂H₁₈O₈
M_r	850.71
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	8.2110 (3), 9.5965 (3), 12.0886 (5)
α, β, γ (°)	86.281 (2), 81.514 (2), 81.705 (2)
V (Å³)	931.34 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.24 × 0.14

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.954, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	12654, 7048, 4579
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.769

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.154, 1.03
No. of reflections	7048
No. of parameters	326
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.30

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Footnotes

¹CAS 116896-77-6 and 113431-17-7.

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

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