Diethyl 4,7-dimethoxy­indan-2,2-dicarboxylate

Hammershøj, P.; Christensen, J.B.

doi:10.1107/S1600536805030217

Buy article online - an online subscription or single-article purchase is required to access this article.

Diethyl 4,7-dimethoxyindan-2,2-dicarboxylate

P. Hammershøj and J. B. Christensen

The title compound, C₁₇H₂₂O₆, crystallizes with two independent molecules in the asymmetric unit. The bond lengths and angles are generally within the normal ranges. The crystal packing is stabilized by weak intermolecular C—H

O hydrogen bonds and weak C—H

π(arene) interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030217/ci6634sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030217/ci6634Isup2.hkl Contains datablock I

CCDC reference: 287507

checkCIF report

Key indicators

Single-crystal X-ray study
T = 122 K
Mean (C-C) = 0.001 Å
R factor = 0.061
wR factor = 0.149
Data-to-parameter ratio = 48.6

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.650
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.02
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.65 e/A   3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         40

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), was prepared for use as a building block in the syntheses of single-walled carbon nanotube (SWNT) interacting compounds. It crystallizes in the monoclinic space group P2₁/c with two independent molecules in the asymmetric unit (Fig. 1). The corresponding bond lengths and angles of the two molecules agree with each other, but the molecules differ in the orientation of an ester group (Table 1). In both molecules, the methoxy groups are almost coplanar with the benzene ring and the five-membered rings of the indane ring system adopt envelope conformations. The crystal packing of (I) is stabilized mainly by weak intermolecular C—H···O hydrogen bonds and weak C—H ··· π(arene) interactions (Table 2 and Fig. 2). In Table 2, Cg1 and Cg2 denote the centroids of rings C1A—C6A and C1B—C6B, respectively.

Experimental top

Diethyl 5-bromo-4,7-dimethoxyindan-2,2-dicarboxylate (10 g, 24.9 mmol), prepared as described by Hammershøj & Christensen (2005), was dissolved in methanol (300 ml) and Pd/C 10% (cat. amount) was added. The mixture was hydrogenated (5.8 p.s.i.) at room temperature for 20 h. The reaction mixture was filtered and evaporated to dryness in vacuo, yielding an off-white solid. Purification by crystallization in ethanol yielded compound (I) as a white powder (yield 63%, m.p. 362–364 K). ¹H NMR (300 MHz, CDCl₃): δ 6.7 (2H, s), 4.2 (4H, q, J = 7.3 Hz), 3.41 (4H, s), 1.25 (6H, t, J = 6.23 Hz); ¹³C NMR (100 MHz, CDCl₃): δ 171.5, 149.7, 129.5, 109.2, 61.5, 59.7, 55.5, 37.9, 13.9; m/e: 322 (62), 248 (83.5), 175 (100) and 161 (40%); analysis calculated for C₁₇H₂₂O₆: C 63.3, H 6.8%; found: C 63.1, H 6.8%.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996).

Figures top

	Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. The crystal packing of (I).

4,7-Dimethoxy-indan-2,2-dicarboxylic acid diethyl ester top

Crystal data top

C₁₇H₂₂O₆	F(000) = 1376
M_r = 322.35	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 89–91 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.569 (1) Å	Cell parameters from 37980 reflections
b = 8.033 (1) Å	θ = 1.2–40.0°
c = 24.643 (3) Å	µ = 0.10 mm⁻¹
β = 90.232 (7)°	T = 122 K
V = 3279.9 (6) Å³	Prism, white
Z = 8	0.4 × 0.31 × 0.25 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	20169 independent reflections
Radiation source: fine-focus sealed tube	12472 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ω and ϕ scans	θ_max = 40.0°, θ_min = 1.2°
Absorption correction: integration Gaussian integration (Coppens, 1970)	h = −29→29
T_min = 0.977, T_max = 0.988	k = −14→14
141916 measured reflections	l = −43→44

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0458P)² + 1.6487P] where P = (F_o² + 2F_c²)/3
20169 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₇H₂₂O₆	V = 3279.9 (6) Å³
M_r = 322.35	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.569 (1) Å	µ = 0.10 mm⁻¹
b = 8.033 (1) Å	T = 122 K
c = 24.643 (3) Å	0.4 × 0.31 × 0.25 mm
β = 90.232 (7)°

Data collection top

Nonius KappaCCD area-detector diffractometer	20169 independent reflections
Absorption correction: integration Gaussian integration (Coppens, 1970)	12472 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.988	R_int = 0.079
141916 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.08	Δρ_max = 0.65 e Å⁻³
20169 reflections	Δρ_min = −0.32 e Å⁻³
415 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.

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.

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

	x	y	z	U_iso*/U_eq
O4A	0.20679 (4)	0.02074 (9)	0.14428 (3)	0.01754 (14)
O6A	0.22760 (4)	0.25356 (10)	0.04459 (3)	0.01592 (13)
O2A	0.12138 (5)	0.56579 (10)	0.27136 (3)	0.01918 (14)
C15A	0.21874 (5)	0.33738 (11)	0.09126 (3)	0.01170 (14)
C8A	0.14460 (5)	0.27318 (12)	0.12166 (3)	0.01201 (15)
C6A	0.04851 (5)	0.49335 (12)	0.13400 (4)	0.01317 (15)
O5A	0.26120 (4)	0.45082 (10)	0.10572 (3)	0.01879 (14)
O1A	−0.04205 (5)	0.62979 (10)	0.07525 (3)	0.02082 (15)
C7A	0.06894 (5)	0.35552 (12)	0.09522 (4)	0.01372 (15)
H7AA	0.0815	0.3999	0.0587	0.016*
H7AB	0.0239	0.2750	0.0921	0.016*
O3A	0.09540 (5)	0.00340 (10)	0.09150 (3)	0.02273 (16)
C5A	0.09015 (5)	0.47810 (12)	0.18247 (4)	0.01336 (15)
C4A	0.07798 (6)	0.59239 (12)	0.22464 (4)	0.01504 (16)
C12A	0.14426 (5)	0.08394 (12)	0.11657 (4)	0.01366 (15)
C9A	0.14608 (6)	0.33060 (12)	0.18189 (3)	0.01412 (16)
H9AA	0.1263	0.2415	0.2062	0.017*
H9AB	0.2013	0.3629	0.1933	0.017*
C2A	−0.01702 (6)	0.73953 (13)	0.16671 (4)	0.01848 (18)
H2A	−0.0532	0.8299	0.1614	0.022*
C3A	0.02404 (6)	0.72295 (13)	0.21627 (4)	0.01808 (18)
H3A	0.0150	0.8016	0.2444	0.022*
C1A	−0.00533 (5)	0.62478 (12)	0.12523 (4)	0.01547 (16)
C13A	0.21703 (7)	−0.15930 (13)	0.14312 (4)	0.01989 (19)
H13AA	0.2450	−0.1934	0.1095	0.024*
H13AB	0.1638	−0.2151	0.1442	0.024*
C16A	0.29430 (6)	0.30090 (14)	0.00920 (4)	0.01825 (18)
H16AA	0.2998	0.4236	0.0091	0.022*
H16AB	0.2823	0.2647	−0.0284	0.022*
C14A	0.26637 (7)	−0.20705 (14)	0.19192 (5)	0.0248 (2)
H14AA	0.2744	−0.3279	0.1923	0.030*
H14AB	0.2380	−0.1731	0.2249	0.030*
H14AC	0.3189	−0.1512	0.1904	0.030*
C11A	−0.08171 (7)	0.78205 (15)	0.06158 (5)	0.0240 (2)
H11AA	−0.1056	0.7725	0.0253	0.029*
H11AB	−0.0425	0.8733	0.0620	0.029*
H11AC	−0.1243	0.8047	0.0881	0.029*
C10A	0.10645 (8)	0.67788 (17)	0.31499 (4)	0.0275 (2)
H10AA	0.1404	0.6477	0.3461	0.033*
H10AB	0.0495	0.6714	0.3254	0.033*
H10AC	0.1192	0.7917	0.3035	0.033*
C17A	0.37225 (7)	0.22424 (19)	0.02761 (5)	0.0303 (3)
H17AA	0.4157	0.2585	0.0032	0.036*
H17AB	0.3673	0.1027	0.0271	0.036*
H17AC	0.3847	0.2614	0.0646	0.036*
O6B	0.29724 (4)	0.93312 (9)	0.35140 (3)	0.01548 (13)
O1B	0.38817 (5)	0.38524 (10)	0.23316 (3)	0.01809 (14)
C6B	0.45305 (5)	0.46235 (12)	0.37207 (4)	0.01250 (15)
C9B	0.35823 (5)	0.62229 (12)	0.32035 (3)	0.01304 (15)
H9BA	0.3040	0.5890	0.3072	0.016*
H9BB	0.3796	0.7108	0.2964	0.016*
O2B	0.53934 (5)	0.32663 (10)	0.43389 (3)	0.01889 (14)
C15B	0.28040 (5)	0.61118 (11)	0.40822 (3)	0.01246 (15)
C5B	0.41456 (5)	0.47547 (12)	0.32217 (3)	0.01259 (15)
O5B	0.39392 (5)	0.95328 (10)	0.41568 (3)	0.01969 (15)
C8B	0.35523 (5)	0.68226 (11)	0.38045 (3)	0.01105 (14)
C7B	0.42998 (5)	0.60342 (12)	0.40924 (3)	0.01347 (15)
H7BA	0.4745	0.6852	0.4126	0.016*
H7BB	0.4159	0.5618	0.4458	0.016*
C4B	0.42922 (6)	0.35997 (12)	0.28104 (4)	0.01408 (16)
C12B	0.35277 (5)	0.87118 (12)	0.38541 (3)	0.01239 (15)
O4B	0.25208 (5)	0.71425 (10)	0.44604 (3)	0.02013 (15)
O3B	0.25196 (5)	0.47647 (10)	0.39833 (3)	0.02214 (16)
C2B	0.51995 (6)	0.21413 (13)	0.34218 (4)	0.01749 (18)
H2B	0.5556	0.1237	0.3489	0.021*
C1B	0.50577 (5)	0.33063 (12)	0.38289 (4)	0.01434 (16)
C3B	0.48218 (6)	0.22939 (13)	0.29142 (4)	0.01734 (18)
H3B	0.4929	0.1497	0.2639	0.021*
C13B	0.28283 (7)	1.11178 (12)	0.35446 (4)	0.01805 (18)
H13BA	0.3348	1.1725	0.3561	0.022*
H13BB	0.2514	1.1390	0.3874	0.022*
C11B	0.57929 (7)	0.17583 (15)	0.44875 (4)	0.0243 (2)
H11BA	0.6010	0.1863	0.4856	0.029*
H11BB	0.6235	0.1543	0.4234	0.029*
H11BC	0.5408	0.0834	0.4474	0.029*
C14B	0.23644 (7)	1.16071 (14)	0.30426 (4)	0.0225 (2)
H14BA	0.2257	1.2806	0.3050	0.027*
H14BB	0.1852	1.0998	0.3031	0.027*
H14BC	0.2682	1.1335	0.2720	0.027*
C16B	0.18071 (7)	0.65951 (14)	0.47581 (5)	0.0236 (2)
H16BA	0.1957	0.5742	0.5030	0.028*
H16BB	0.1407	0.6106	0.4505	0.028*
C10B	0.40371 (8)	0.27010 (16)	0.19072 (4)	0.0265 (2)
H10BA	0.3716	0.3001	0.1587	0.032*
H10BB	0.3891	0.1577	0.2026	0.032*
H10BC	0.4612	0.2732	0.1815	0.032*
C17B	0.14587 (7)	0.80945 (15)	0.50322 (5)	0.0247 (2)
H17BA	0.0975	0.7772	0.5235	0.030*
H17BB	0.1314	0.8930	0.4759	0.030*
H17BC	0.1859	0.8563	0.5283	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4A	0.0194 (3)	0.0097 (3)	0.0235 (3)	0.0016 (2)	−0.0030 (3)	0.0003 (2)
O6A	0.0159 (3)	0.0190 (3)	0.0129 (3)	−0.0033 (3)	0.0034 (2)	−0.0031 (2)
O2A	0.0250 (4)	0.0194 (4)	0.0131 (3)	0.0037 (3)	0.0023 (2)	−0.0021 (2)
C15A	0.0123 (3)	0.0106 (4)	0.0122 (3)	0.0020 (3)	0.0005 (3)	0.0009 (3)
C8A	0.0125 (3)	0.0108 (4)	0.0127 (3)	0.0008 (3)	0.0018 (3)	−0.0002 (3)
C6A	0.0123 (3)	0.0117 (4)	0.0156 (4)	0.0015 (3)	0.0026 (3)	0.0008 (3)
O5A	0.0190 (3)	0.0166 (3)	0.0208 (3)	−0.0053 (3)	0.0024 (3)	−0.0036 (3)
O1A	0.0195 (3)	0.0190 (4)	0.0239 (3)	0.0077 (3)	−0.0059 (3)	−0.0027 (3)
C7A	0.0129 (3)	0.0132 (4)	0.0150 (3)	0.0024 (3)	0.0004 (3)	−0.0009 (3)
O3A	0.0231 (4)	0.0147 (4)	0.0303 (4)	−0.0025 (3)	−0.0064 (3)	−0.0018 (3)
C5A	0.0145 (4)	0.0113 (4)	0.0144 (3)	0.0012 (3)	0.0040 (3)	0.0003 (3)
C4A	0.0171 (4)	0.0142 (4)	0.0139 (3)	0.0006 (3)	0.0040 (3)	−0.0002 (3)
C12A	0.0147 (4)	0.0113 (4)	0.0150 (4)	0.0005 (3)	0.0028 (3)	0.0002 (3)
C9A	0.0176 (4)	0.0130 (4)	0.0117 (3)	0.0031 (3)	0.0017 (3)	0.0006 (3)
C2A	0.0179 (4)	0.0154 (4)	0.0221 (4)	0.0056 (3)	0.0033 (3)	−0.0013 (3)
C3A	0.0209 (4)	0.0147 (4)	0.0187 (4)	0.0037 (3)	0.0057 (3)	−0.0029 (3)
C1A	0.0121 (4)	0.0148 (4)	0.0195 (4)	0.0022 (3)	0.0014 (3)	−0.0001 (3)
C13A	0.0277 (5)	0.0097 (4)	0.0223 (4)	0.0031 (4)	−0.0009 (4)	−0.0008 (3)
C16A	0.0168 (4)	0.0244 (5)	0.0135 (4)	−0.0028 (4)	0.0046 (3)	0.0003 (3)
C14A	0.0292 (5)	0.0158 (5)	0.0295 (5)	0.0041 (4)	−0.0059 (4)	0.0020 (4)
C11A	0.0200 (4)	0.0219 (5)	0.0299 (5)	0.0090 (4)	−0.0071 (4)	−0.0008 (4)
C10A	0.0353 (6)	0.0291 (6)	0.0181 (4)	0.0059 (5)	−0.0001 (4)	−0.0088 (4)
C17A	0.0213 (5)	0.0425 (8)	0.0271 (5)	0.0099 (5)	0.0058 (4)	−0.0019 (5)
O6B	0.0192 (3)	0.0095 (3)	0.0176 (3)	0.0025 (2)	−0.0044 (2)	−0.0010 (2)
O1B	0.0227 (3)	0.0193 (4)	0.0122 (3)	0.0043 (3)	−0.0002 (2)	−0.0031 (2)
C6B	0.0128 (3)	0.0120 (4)	0.0127 (3)	0.0012 (3)	0.0013 (3)	0.0002 (3)
C9B	0.0152 (4)	0.0129 (4)	0.0110 (3)	0.0031 (3)	0.0003 (3)	−0.0002 (3)
O2B	0.0217 (3)	0.0185 (4)	0.0164 (3)	0.0083 (3)	−0.0044 (3)	0.0001 (3)
C15B	0.0138 (3)	0.0103 (4)	0.0133 (3)	0.0005 (3)	0.0014 (3)	0.0004 (3)
C5B	0.0133 (4)	0.0119 (4)	0.0126 (3)	0.0010 (3)	0.0019 (3)	0.0000 (3)
O5B	0.0245 (4)	0.0132 (3)	0.0213 (3)	−0.0031 (3)	−0.0072 (3)	−0.0007 (3)
C8B	0.0121 (3)	0.0102 (4)	0.0108 (3)	0.0008 (3)	0.0002 (3)	0.0003 (3)
C7B	0.0142 (4)	0.0140 (4)	0.0122 (3)	0.0028 (3)	−0.0009 (3)	−0.0006 (3)
C4B	0.0159 (4)	0.0143 (4)	0.0120 (3)	0.0006 (3)	0.0021 (3)	−0.0004 (3)
C12B	0.0135 (3)	0.0115 (4)	0.0121 (3)	−0.0007 (3)	0.0010 (3)	0.0012 (3)
O4B	0.0239 (3)	0.0156 (3)	0.0210 (3)	−0.0058 (3)	0.0122 (3)	−0.0057 (3)
O3B	0.0237 (4)	0.0142 (3)	0.0286 (4)	−0.0060 (3)	0.0078 (3)	−0.0051 (3)
C2B	0.0183 (4)	0.0160 (4)	0.0182 (4)	0.0066 (3)	0.0022 (3)	−0.0007 (3)
C1B	0.0135 (4)	0.0157 (4)	0.0139 (3)	0.0026 (3)	0.0003 (3)	0.0012 (3)
C3B	0.0207 (4)	0.0160 (4)	0.0154 (4)	0.0047 (3)	0.0040 (3)	−0.0018 (3)
C13B	0.0269 (5)	0.0092 (4)	0.0180 (4)	0.0033 (3)	−0.0030 (3)	−0.0007 (3)
C11B	0.0282 (5)	0.0227 (5)	0.0219 (5)	0.0120 (4)	−0.0050 (4)	0.0017 (4)
C14B	0.0299 (5)	0.0150 (5)	0.0227 (5)	0.0046 (4)	−0.0060 (4)	0.0020 (4)
C16B	0.0255 (5)	0.0190 (5)	0.0266 (5)	−0.0060 (4)	0.0148 (4)	−0.0034 (4)
C10B	0.0323 (6)	0.0308 (6)	0.0163 (4)	0.0088 (5)	−0.0020 (4)	−0.0094 (4)
C17B	0.0258 (5)	0.0218 (5)	0.0267 (5)	0.0021 (4)	0.0098 (4)	−0.0017 (4)

Geometric parameters (Å, º) top

O4A—C12A	1.3385 (12)	O6B—C12B	1.3380 (11)
O4A—C13A	1.4565 (12)	O6B—C13B	1.4569 (12)
O6A—C15A	1.3412 (11)	O1B—C4B	1.3745 (11)
O6A—C16A	1.4609 (11)	O1B—C10B	1.4204 (12)
O2A—C4A	1.3717 (12)	C6B—C5B	1.3870 (12)
O2A—C10A	1.4249 (13)	C6B—C1B	1.3971 (13)
C15A—O5A	1.2042 (12)	C6B—C7B	1.5073 (13)
C15A—C8A	1.5309 (12)	C9B—C5B	1.5046 (13)
C8A—C12A	1.5253 (13)	C9B—C8B	1.5586 (12)
C8A—C9A	1.5543 (12)	C9B—H9BA	0.99
C8A—C7A	1.5579 (12)	C9B—H9BB	0.99
C6A—C5A	1.3824 (13)	O2B—C1B	1.3727 (11)
C6A—C1A	1.3984 (13)	O2B—C11B	1.4275 (13)
C6A—C7A	1.5020 (13)	C15B—O3B	1.2047 (12)
O1A—C1A	1.3720 (12)	C15B—O4B	1.3334 (11)
O1A—C11A	1.4282 (13)	C15B—C8B	1.5291 (12)
C7A—H7AA	0.99	C5B—C4B	1.3962 (13)
C7A—H7AB	0.99	O5B—C12B	1.2051 (12)
O3A—C12A	1.2050 (12)	C8B—C12B	1.5231 (13)
C5A—C4A	1.4018 (13)	C8B—C7B	1.5593 (12)
C5A—C9A	1.5043 (13)	C7B—H7BA	0.99
C4A—C3A	1.3928 (14)	C7B—H7BB	0.99
C9A—H9AA	0.99	C4B—C3B	1.3907 (14)
C9A—H9AB	0.99	O4B—C16B	1.4619 (12)
C2A—C1A	1.3906 (14)	C2B—C1B	1.3926 (13)
C2A—C3A	1.4019 (14)	C2B—C3B	1.4016 (14)
C2A—H2A	0.95	C2B—H2B	0.95
C3A—H3A	0.95	C3B—H3B	0.95
C13A—C14A	1.5011 (15)	C13B—C14B	1.5059 (14)
C13A—H13AA	0.99	C13B—H13BA	0.99
C13A—H13AB	0.99	C13B—H13BB	0.99
C16A—C17A	1.4996 (16)	C11B—H11BA	0.98
C16A—H16AA	0.99	C11B—H11BB	0.98
C16A—H16AB	0.99	C11B—H11BC	0.98
C14A—H14AA	0.98	C14B—H14BA	0.98
C14A—H14AB	0.98	C14B—H14BB	0.98
C14A—H14AC	0.98	C14B—H14BC	0.98
C11A—H11AA	0.98	C16B—C17B	1.4978 (16)
C11A—H11AB	0.98	C16B—H16BA	0.99
C11A—H11AC	0.98	C16B—H16BB	0.99
C10A—H10AA	0.98	C10B—H10BA	0.98
C10A—H10AB	0.98	C10B—H10BB	0.98
C10A—H10AC	0.98	C10B—H10BC	0.98
C17A—H17AA	0.98	C17B—H17BA	0.98
C17A—H17AB	0.98	C17B—H17BB	0.98
C17A—H17AC	0.98	C17B—H17BC	0.98

C12A—O4A—C13A	117.17 (8)	C12B—O6B—C13B	116.51 (8)
C15A—O6A—C16A	117.83 (8)	C4B—O1B—C10B	116.44 (8)
C4A—O2A—C10A	116.30 (8)	C5B—C6B—C1B	120.76 (8)
O5A—C15A—O6A	124.59 (8)	C5B—C6B—C7B	111.40 (8)
O5A—C15A—C8A	125.39 (8)	C1B—C6B—C7B	127.83 (8)
O6A—C15A—C8A	109.96 (7)	C5B—C9B—C8B	103.65 (7)
C12A—C8A—C15A	107.35 (7)	C5B—C9B—H9BA	111.1
C12A—C8A—C9A	111.99 (7)	C8B—C9B—H9BA	111.2
C15A—C8A—C9A	110.97 (7)	C5B—C9B—H9BB	110.9
C12A—C8A—C7A	112.71 (8)	C8B—C9B—H9BB	110.9
C15A—C8A—C7A	107.35 (7)	H9BA—C9B—H9BB	109.0
C9A—C8A—C7A	106.43 (7)	C1B—O2B—C11B	116.14 (8)
C5A—C6A—C1A	121.08 (9)	O3B—C15B—O4B	124.10 (8)
C5A—C6A—C7A	111.80 (8)	O3B—C15B—C8B	124.20 (8)
C1A—C6A—C7A	127.12 (8)	O4B—C15B—C8B	111.66 (8)
C1A—O1A—C11A	116.04 (8)	C6B—C5B—C4B	120.83 (8)
C6A—C7A—C8A	103.30 (7)	C6B—C5B—C9B	111.65 (8)
C6A—C7A—H7AA	111.2	C4B—C5B—C9B	127.51 (8)
C8A—C7A—H7AA	111.2	C12B—C8B—C15B	108.32 (7)
C6A—C7A—H7AB	111.1	C12B—C8B—C9B	112.65 (7)
C8A—C7A—H7AB	111.1	C15B—C8B—C9B	109.80 (7)
H7AA—C7A—H7AB	109.0	C12B—C8B—C7B	112.93 (7)
C6A—C5A—C4A	120.64 (9)	C15B—C8B—C7B	106.78 (7)
C6A—C5A—C9A	111.53 (8)	C9B—C8B—C7B	106.17 (7)
C4A—C5A—C9A	127.83 (8)	C6B—C7B—C8B	103.40 (7)
O2A—C4A—C3A	125.13 (9)	C6B—C7B—H7BA	111.0
O2A—C4A—C5A	116.34 (8)	C8B—C7B—H7BA	111.0
C3A—C4A—C5A	118.52 (9)	C6B—C7B—H7BB	111.1
O3A—C12A—O4A	125.10 (9)	C8B—C7B—H7BB	111.2
O3A—C12A—C8A	125.42 (9)	H7BA—C7B—H7BB	109.0
O4A—C12A—C8A	109.48 (8)	O1B—C4B—C3B	125.38 (8)
C5A—C9A—C8A	103.62 (7)	O1B—C4B—C5B	115.99 (8)
C5A—C9A—H9AA	111.0	C3B—C4B—C5B	118.62 (9)
C8A—C9A—H9AA	111.0	O5B—C12B—O6B	124.76 (9)
C5A—C9A—H9AB	111.0	O5B—C12B—C8B	125.43 (8)
C8A—C9A—H9AB	111.1	O6B—C12B—C8B	109.81 (7)
H9AA—C9A—H9AB	109.0	C15B—O4B—C16B	116.86 (8)
C1A—C2A—C3A	120.59 (9)	C1B—C2B—C3B	120.53 (9)
C1A—C2A—H2A	119.7	C1B—C2B—H2B	119.7
C3A—C2A—H2A	119.7	C3B—C2B—H2B	119.8
C4A—C3A—C2A	120.62 (9)	O2B—C1B—C2B	125.09 (9)
C4A—C3A—H3A	119.7	O2B—C1B—C6B	116.30 (8)
C2A—C3A—H3A	119.7	C2B—C1B—C6B	118.61 (8)
O1A—C1A—C2A	125.29 (9)	C4B—C3B—C2B	120.62 (9)
O1A—C1A—C6A	116.18 (8)	C4B—C3B—H3B	119.7
C2A—C1A—C6A	118.52 (9)	C2B—C3B—H3B	119.7
O4A—C13A—C14A	107.53 (9)	O6B—C13B—C14B	107.33 (8)
O4A—C13A—H13AA	110.2	O6B—C13B—H13BA	110.2
C14A—C13A—H13AA	110.2	C14B—C13B—H13BA	110.2
O4A—C13A—H13AB	110.2	O6B—C13B—H13BB	110.3
C14A—C13A—H13AB	110.2	C14B—C13B—H13BB	110.3
H13AA—C13A—H13AB	108.5	H13BA—C13B—H13BB	108.5
O6A—C16A—C17A	111.42 (9)	O2B—C11B—H11BA	109.5
O6A—C16A—H16AA	109.3	O2B—C11B—H11BB	109.5
C17A—C16A—H16AA	109.3	H11BA—C11B—H11BB	109.5
O6A—C16A—H16AB	109.4	O2B—C11B—H11BC	109.5
C17A—C16A—H16AB	109.4	H11BA—C11B—H11BC	109.5
H16AA—C16A—H16AB	108.0	H11BB—C11B—H11BC	109.5
C13A—C14A—H14AA	109.5	C13B—C14B—H14BA	109.4
C13A—C14A—H14AB	109.4	C13B—C14B—H14BB	109.4
H14AA—C14A—H14AB	109.5	H14BA—C14B—H14BB	109.5
C13A—C14A—H14AC	109.5	C13B—C14B—H14BC	109.5
H14AA—C14A—H14AC	109.5	H14BA—C14B—H14BC	109.5
H14AB—C14A—H14AC	109.5	H14BB—C14B—H14BC	109.5
O1A—C11A—H11AA	109.4	O4B—C16B—C17B	107.37 (9)
O1A—C11A—H11AB	109.5	O4B—C16B—H16BA	110.4
H11AA—C11A—H11AB	109.5	C17B—C16B—H16BA	110.3
O1A—C11A—H11AC	109.5	O4B—C16B—H16BB	110.1
H11AA—C11A—H11AC	109.5	C17B—C16B—H16BB	110.2
H11AB—C11A—H11AC	109.5	H16BA—C16B—H16BB	108.5
O2A—C10A—H10AA	109.5	O1B—C10B—H10BA	109.4
O2A—C10A—H10AB	109.5	O1B—C10B—H10BB	109.5
H10AA—C10A—H10AB	109.5	H10BA—C10B—H10BB	109.5
O2A—C10A—H10AC	109.5	O1B—C10B—H10BC	109.4
H10AA—C10A—H10AC	109.5	H10BA—C10B—H10BC	109.5
H10AB—C10A—H10AC	109.5	H10BB—C10B—H10BC	109.5
C16A—C17A—H17AA	109.4	C16B—C17B—H17BA	109.5
C16A—C17A—H17AB	109.5	C16B—C17B—H17BB	109.5
H17AA—C17A—H17AB	109.5	H17BA—C17B—H17BB	109.5
C16A—C17A—H17AC	109.5	C16B—C17B—H17BC	109.4
H17AA—C17A—H17AC	109.5	H17BA—C17B—H17BC	109.5
H17AB—C17A—H17AC	109.5	H17BB—C17B—H17BC	109.5

C11A—O1A—C1A—C2A	13.47 (14)	C7A—C8A—C15A—O6A	−79.95 (9)
C11A—O1A—C1A—C6A	−165.90 (9)	C9A—C8A—C15A—O5A	−18.69 (12)
C10A—O2A—C4A—C3A	2.88 (15)	C9A—C8A—C15A—O6A	164.13 (7)
C10A—O2A—C4A—C5A	−177.45 (9)	C12A—C8A—C15A—O5A	−141.35 (9)
C13A—O4A—C12A—O3A	1.10 (14)	C15A—C8A—C12A—O3A	−112.36 (10)
C13A—O4A—C12A—C8A	−178.86 (7)	C15A—C8A—C12A—O4A	67.60 (9)
C12A—O4A—C13A—C14A	−157.88 (9)	C7A—C8A—C15A—O5A	97.23 (10)
C16A—O6A—C15A—O5A	1.19 (13)	C7A—C8A—C9A—C5A	−16.93 (9)
C16A—O6A—C15A—C8A	178.39 (8)	C12A—C8A—C15A—O6A	41.47 (9)
C15A—O6A—C16A—C17A	81.15 (11)	C15A—C8A—C9A—C5A	99.55 (8)
C10B—O1B—C4B—C5B	178.94 (9)	O2B—C1B—C6B—C7B	1.61 (14)
C10B—O1B—C4B—C3B	−1.98 (15)	C2B—C1B—C6B—C5B	1.06 (13)
C11B—O2B—C1B—C2B	−12.14 (14)	C2B—C1B—C6B—C7B	−178.82 (9)
C11B—O2B—C1B—C6B	167.39 (9)	C6B—C1B—C2B—C3B	0.17 (14)
C16B—O4B—C15B—O3B	−1.71 (13)	O2B—C1B—C6B—C5B	−178.51 (8)
C16B—O4B—C15B—C8B	−179.60 (8)	O2B—C1B—C2B—C3B	179.70 (9)
C15B—O4B—C16B—C17B	−163.66 (9)	C1B—C2B—C3B—C4B	−0.74 (15)
C13B—O6B—C12B—O5B	−4.22 (13)	C2B—C3B—C4B—O1B	−178.99 (9)
C13B—O6B—C12B—C8B	175.15 (7)	C2B—C3B—C4B—C5B	0.07 (15)
C12B—O6B—C13B—C14B	165.24 (8)	O1B—C4B—C5B—C9B	1.02 (14)
O1A—C1A—C6A—C7A	−1.50 (14)	C3B—C4B—C5B—C6B	1.17 (14)
C2A—C1A—C6A—C5A	−0.77 (14)	O1B—C4B—C5B—C6B	−179.69 (8)
C2A—C1A—C6A—C7A	179.08 (9)	C3B—C4B—C5B—C9B	−178.13 (9)
O1A—C1A—C2A—C3A	−179.68 (9)	C4B—C5B—C6B—C1B	−1.75 (14)
C6A—C1A—C2A—C3A	−0.33 (14)	C4B—C5B—C6B—C7B	178.15 (8)
O1A—C1A—C6A—C5A	178.64 (8)	C6B—C5B—C9B—C8B	−9.82 (10)
C1A—C2A—C3A—C4A	0.75 (15)	C4B—C5B—C9B—C8B	169.52 (9)
C2A—C3A—C4A—C5A	−0.08 (15)	C9B—C5B—C6B—C1B	177.64 (8)
C2A—C3A—C4A—O2A	179.59 (9)	C9B—C5B—C6B—C7B	−2.46 (10)
O2A—C4A—C5A—C9A	−0.94 (14)	C5B—C6B—C7B—C8B	13.59 (9)
C3A—C4A—C5A—C9A	178.75 (9)	C1B—C6B—C7B—C8B	−166.52 (9)
O2A—C4A—C5A—C6A	179.29 (9)	C6B—C7B—C8B—C9B	−18.96 (9)
C3A—C4A—C5A—C6A	−1.02 (14)	C6B—C7B—C8B—C12B	−142.89 (7)
C4A—C5A—C6A—C7A	−178.41 (8)	C6B—C7B—C8B—C15B	98.17 (7)
C4A—C5A—C9A—C8A	−170.03 (9)	C7B—C8B—C15B—O4B	97.02 (8)
C4A—C5A—C6A—C1A	1.46 (14)	C9B—C8B—C15B—O3B	33.83 (11)
C9A—C5A—C6A—C1A	−178.34 (8)	C9B—C8B—C15B—O4B	−148.28 (7)
C6A—C5A—C9A—C8A	9.75 (10)	C12B—C8B—C15B—O3B	157.23 (8)
C9A—C5A—C6A—C7A	1.79 (11)	C12B—C8B—C15B—O4B	−24.88 (9)
C1A—C6A—C7A—C8A	167.68 (9)	C7B—C8B—C9B—C5B	17.67 (9)
C5A—C6A—C7A—C8A	−12.45 (10)	C12B—C8B—C9B—C5B	141.78 (7)
C6A—C7A—C8A—C9A	17.84 (9)	C15B—C8B—C9B—C5B	−97.41 (8)
C6A—C7A—C8A—C12A	140.97 (7)	C7B—C8B—C12B—O5B	−12.83 (12)
C6A—C7A—C8A—C15A	−101.03 (8)	C7B—C8B—C12B—O6B	167.81 (7)
C9A—C8A—C12A—O3A	125.61 (10)	C9B—C8B—C12B—O5B	−133.12 (9)
C9A—C8A—C12A—O4A	−54.43 (10)	C9B—C8B—C12B—O6B	47.52 (9)
C7A—C8A—C12A—O4A	−174.41 (7)	C15B—C8B—C12B—O5B	105.21 (10)
C7A—C8A—C12A—O3A	5.63 (13)	C15B—C8B—C12B—O6B	−74.15 (8)
C12A—C8A—C9A—C5A	−140.51 (7)	C7B—C8B—C15B—O3B	−80.86 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AB···O3A	0.99	2.48	2.8639 (13)	102
C9A—H9AB···O5A	0.99	2.48	2.8501 (12)	102
C11A—H11AC···O3Bⁱ	0.98	2.55	3.3757 (15)	142
C7B—H7BA···O5B	0.99	2.54	2.8778 (13)	100
C10B—H10BA···O5A	0.98	2.55	3.4685 (15)	156
C13A—H13AB···Cg1ⁱⁱ	0.99	2.65	3.615 (1)	164
C13B—H13BA···Cg2ⁱⁱⁱ	0.99	2.67	3.633 (1)	165

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, y−1, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₂O₆
M_r	322.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	122
a, b, c (Å)	16.569 (1), 8.033 (1), 24.643 (3)
β (°)	90.232 (7)
V (Å³)	3279.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.4 × 0.31 × 0.25

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Integration Gaussian integration (Coppens, 1970)
T_min, T_max	0.977, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	141916, 20169, 12472
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.904

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.149, 1.08
No. of reflections	20169
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.32

Computer programs: COLLECT (Nonius, 1999), DIRAX (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).

Selected torsion angles (º) top

C11A—O1A—C1A—C2A	13.47 (14)	C10B—O1B—C4B—C3B	−1.98 (15)
C10A—O2A—C4A—C3A	2.88 (15)	C11B—O2B—C1B—C2B	−12.14 (14)
C15A—O6A—C16A—C17A	81.15 (11)	C15B—O4B—C16B—C17B	−163.66 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AB···O3A	0.99	2.48	2.8639 (13)	102
C9A—H9AB···O5A	0.99	2.48	2.8501 (12)	102
C11A—H11AC···O3Bⁱ	0.98	2.55	3.3757 (15)	142
C7B—H7BA···O5B	0.99	2.54	2.8778 (13)	100
C10B—H10BA···O5A	0.98	2.55	3.4685 (15)	156
C13A—H13AB···Cg1ⁱⁱ	0.99	2.65	3.615 (1)	164
C13B—H13BA···Cg2ⁱⁱⁱ	0.99	2.67	3.633 (1)	165

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, y−1, z; (iii) x, y+1, z.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page